Monday, December 31, 2012

An Unexpected Thrill

February 11, 2011 --

In the several days between fucking Zen and meeting with Kyra, I got a text from Dale, one of the girls I'd really hoped to meet, but who hadn't responded to my messages.  Never really liked this sort of thing with the girls.  If it takes you a week to respond to a message, then you're probably a flake.  Still, Dale was fucking hot, with big tits and a really cute face.  She was mid-twenties, somewhat tall, and lived alone in an upscale part of town.  She worked only part time in event management.  I asked Dale to meet me for lunch at a mall near her apartment.

Dale was dressed in khakis and a white button down blouse, open to reveal a striped tube top that accentuated her big tits.  She had wavy/curly hair and green eyes that had me feeling warm right away.

We went to a restaurant that appeared fairly quiet and sat down for our meal.  She had many surprises for me: she was a homeowner, having bought a home two years earlier in her home state, but had come out to the west coast a year later and was renting it out to a friend of hers; she was very politically active, and a strong liberal, which I found very exciting in a girl so young; and she had been a competitive athlete in her younger years.  With the curves she was rocking, though, I had a tough time imagining her as a hard body.

As we left the restaurant after lunch, I noticed a table of middle aged housewife types giving me That Look.  You know the one: older guy, young girl.  Pervert!  Anyway, we walked over to a bookstore where I needed to buy my mother a birthday gift.  She was game and even had some choice comments for me when I'd settled on a book by a very conservative TV commentator.  I reminded her that this was a gift for her, not for me; I was as liberal as she was.

Once outside again, it was time to say goodbye.  She leaned in for a nice kiss on the lips.  I felt a little exposed out there in public, but I went for it anyway.  We made plans to get together the next week.


Zen and the Art of Getting It Up Again

February 2011 --

After the total disappointment of Paulina, I needed to have good sex right away.  I called Zen (she didn't like texting because she had such a limited texting plan on her phone) and made a date.  Her apartment was about half an hour from my office, and we made a plan for late afternoon so that I could be home for dinner.

Her building was large and complicated, and she had to come down to the front door both to let me in and to guide me to her apartment.

Once inside, I was struck by how clean and orderly everything was.  Not one stray article of clothing.  No dishes left out.  She either cleaned up before I got there, or she was a very neat girl.  Either way, major points for her!

Her bedroom had plenty of floor space for the queen bed, two chairs and a little table.  All of it impeccably furnished.  We talked a little while and then got busy.

Zen had a typical Asian girl's body.  Small breasted, relatively flat bottom, and short legs.  No matter, since I liked her.  Her kissing was pretty good, and I was hard right away.  She had recently shaved her pussy since it was so smooth when I licked her there.  She also moaned and sort of cried out when she was excited, a lot like the Asian girls I'd seen in porn videos.  Almost like a little girl.  I found it a little off-putting, especially since her eyes were closed a lot of the time.

She gave me a long, slow blow job, which felt nice.  But soon it was time to fuck.  For someone so young, I found her pussy to be an unusually loose fit for my thick dick.  It was interesting to me, and while I fucked her I found myself recalling the visual of tying a board around my waist so that I wouldn't fall in. Hee hee!  Sure kept me from coming too soon, that's for sure.  She liked to kiss a lot, which was fine with me!    After she had several orgasms, I let go and unloaded inside her.

We snuggled in her bed for a long time after finishing up.  She asked me, "How were my BJ skills?"  I've never had a girl ask me that before, so it caught me off guard.  "Um, uh," I stammered, "they were good!  No complaints from me!"  She seemed relieved to hear that, since she most likely had given less than 10 blow jobs in her life.  She revealed to me that she'd only had one boyfriend, in her home state, and hadn't had sex with anyone special in months.  So now I'm special?  Her arms around me while we were in bed sort of gave that away.

She started stroking my cock, which grew to life again.  Not wasting the opportunity, I slipped on another condom and we fucked some more.  I didn't come, but she did again.  Then I showered up and kissed her lightly before saying good night.

In the car, I decided to hold off on saying she was my girl until I'd fucked Kyra.  But I thought I could be satisfied with Zen for a little while.

Another Disappointment

February 2011 --

I met Paulina for our first encounter early in February, less than a week after deciding after lunch with Kyra that Paulina was the one.

I booked a room at the high-rise hotel that I really enjoyed with Hayden.  I'd asked Paulina to dress conservatively.  The idea was that we'd meet in the lobby first as though it were a business meeting.  I'd slip her the room key and have her go upstairs and prepare herself.

Paulina showed up about 10 minutes late, not too bad.  As she walked over to the couch where I'd been sitting, I noticed she wore some pretty funky high-heeled shoes and a very short dress.  It was not a flattering look for her, as her legs were not particularly shapely and the dress did not accentuate any curves.  Plus, for some reason, she looked not as pretty today as she did when we first met.

After smiles and a little hug, we sat on the couch and made small talk.  I slipped her the room key in a file folder to make it look more discreet, and told her I'd be up in about five minutes.  I finished a couple of emails, then headed upstairs.

Paulina, although she had led me to believe she was experienced with arrangements, did not give off that impression this time.  When she let me in the room, she was still in her dress and shoes, and it didn't look as though she'd freshened up.  In the dim light of the room, which seemed a little cold temperature-wise, I got the feeling from the look on her face that she was very nervous indeed.  We chatted a little while longer.  She was agreeable, but didn't really have much to say unless I prompted her.  Yeah, she was nervous.  I asked if she was alright, and she didn't hesitate to tell me she was fine.

We kissed, we fooled around, and I started undressing her.  Her body, while lean, was not all that wonderful.  Breasts were small, no big deal, but she was not proportional either.  Flat stomach was nice. She was shaved too.  She was so quiet as I went down on her that I thought she was somewhere else.  Her oral skills were actually pretty lame, and I simply stopped her after a minute or two.

We fucked in various positions, but nothing was spectacularly wonderful.  I got off, and I think she did too.  We cleaned up and she hurried out before I did.

What a disappointment.  This woman was a terrible lay!  Well, moving onto Zen now.

Kyra is Now an Escort

Over the weekend I was online looking at porn.  I'd heard that so many porn stars, because they were no longer making the kind of money they used to make shooting scenes, were turning to prostitution in order to make more money.  I saw one particular starlet, named Amia Miley, who I'd always thought was fucking cute, fun, and sexy as shit.  I googled "Amia Miley Escort" and got a hit on a website.  There was a whole photo list of porn stars who any schlub like me could have if he wanted to pay for it.  And who did I see there but Kyra, who I'd fucked about two years ago after meeting her on the Sugar website.  I wanted to see what she was charging for a "session" (which, according to the website, could vary wildly from a straight hookup to shooting a scene together, complete with cameras and lighting).  But, before I could do that I had to verify that 1) I was of age, and 2) had a reference.  A reference?  For a hookup with a porn star?  I guess that must've meant I needed to fuck a porn star before I could fuck a porn star.  Had I not already fucked Kyra before, I wouldn't have proceeded, but since I had, I filled out the little online form and submitted it.  I made sure to state that I'd been with Kyra before.

A couple of days later, I got an email that she confirmed knowing me.  So, I decided to see what was up with my old gonzo fuck-buddy.  I texted her and asked if she truly remembered me.  After a few minutes of joking around to stall me, she named the hotel where we'd met up.  Long story short, however, she wrote that she was not interested in seeing me for less than $1,000, to which, of course, I was never going to agree.  I asked if she'd be flexible, and she said no, so that was the end of that.

Looking at her pictures now, though, it was clear that she'd gotten new tits since we'd met, so I guess she needed to pay for them somehow. 

Thursday, December 27, 2012

What a Stupid Mistake I Made

I located Hayden's Facebook page.  She used a combination of her first and middle names that would have been tricky for me to locate, but I knew her boyfriend's full name and found her through him.

Recent photographs of them and their new apartment with a city view, the Christmas Tree, their holiday card, as well as travel pictures from this year with him, most of them taken after our last time together in August.

How stupid I was to do that!  To torture myself by looking at pictures of this woman I love, this girl who still has hooks in my heart, enjoying her life, chatting with friends about how happy she is, looking so beautiful.  Nearly brought tears to my eyes.

Part of the healing process here needs to involve completely letting go.  I remember the end of my first marriage and my therapist telling me that eventually I'd have to completely let go of her and never see or speak to her again.  While we still have some very incidental contact through social media, I haven't seen her face more than twice in the last 14 years.  We've spoken on the phone perhaps a dozen times, the last time more than three years ago.  I rarely think about her anymore.  The pain of that divorce is no longer strong enough to hurt me.  But the breakup with Hayden is still fresh and I'm still stinging from it.  And I have to cut myself off from her for good.

All of this confirms for me that I need to put down the Sugar life for a while.  After the new year, I'm going to see Wanda one more time (she reminds me of Hayden because Hayden introduced us) and then I'll end it and stop looking for mistresses.  I simply have no choice now.

Foolish.

Kyra

January 2011 --

The day after Zen, I met Kyra for lunch at the same restaurant near my office.  Kyra had told me before we met that she was a retired porn actress.  During lunch, however, she'd revealed that she wasn't quite retired from porn, but just from porn with men.  She revealed to me her porn star name and told me she'd done mostly interracial, anal, and other gonzo stuff for about a year, but was starting her own website to do lesbian and solo stuff.  She sort of asked me not to go online and look her up until we'd slept together once because she didn't want to create expectations.  I was fine with that, I said, but I knew that I'd be online later than night jerking off to her performing.  She knew it too.

She was fully bisexual, and had just left a three-year arrangement with another woman, an older Asian woman.  She told me that she thought all Asian women were crazy.  Having had lunch the day before with Zen in the same restaurant and at the same table, I thought differently, but everyone was entitled to an opinion.

We agreed to terms, and we discussed the philosophy of the arrangement culture.  My favorite line of hers, which I'll never forget, was, "You're not paying me to be your girlfriend.  You're paying me to leave." 

I really liked her and kept her in the top three, along with Paulina and Zen.

Later that night, I went home and checked Kyra out online.  Indeed, she had some freaky videos out there, and she definitely took it up the ass.  She had a great body with natural tits, but she had a bit of an underbite which made her chin jut out just a little, which wasn't the most attractive thing I'd seen.  Still, the prospect of sex with a porn star was too good to pass up, so I made sure she knew I was interested.

My mind was made up.  Paulina was #1, followed by Zen, then Kyra.  I texted Paulina and made plans to see her the next week.  I booked a hotel that Hayden and I had used our second time together.

Zen

January 2011 --

A couple of days after Tasha and The Artist, I scheduled a lunch with Zen near my office.  She was a cute Chinese woman who'd grown up in the southwest.  Weird thing about her: she had a speech impediment on top of her Chinese accent.  She had some tongue issue which made both her Ls and Rs sound like Ws.  She was a reserved type, who worked as a web designer for an online merchandiser.  She had her own place, no roommates, and had a little help from her parents.  She was definitely cute and I was willing to give her a go, but she wasn't my number one.  Paulina was still in the lead.

Tasha and The Artist

January 2011 --

I made a lunch date mid-week, when I was working from home, to meet Tasha.  She was nearly six feet tall  and in her very early twenties.  She was not as cute in person as she was in her pictures.  She was thinner, for one thing.  For another, as she had warned me, she'd had a long night the night before and wasn't looking her best.  I picked her up at her office and drove her to the restaurant she'd picked, a middle eastern one.  Reminded me of Hayden and the meal we'd never managed to have together.  The restaurant people knew her well, so we were treated very well.  To them I looked like a co-worker of hers. 

We talked about a lot of things, among them her very eventful life.  She'd modeled and traveled the world since being on her own at 14.  She lived with her manager, an aunt, etc., but had no relationship with either of her parents.  She currently lived between her office and mine, with a boyfriend who was totally OK with the arrangement thing.  I found her to be very articulate, and she grew prettier as the meal progressed.

When I drove her back to her office, she leaned in and gave me a nice kiss on the lips.  I was sort of thinking she was the one.  However, when she turned around to exit my car, I noticed that she had two open sores at the base of her back, just above her belt line.  I had no idea what these sores were, but that was it for me.  I was no longer attracted to her.  Glad I didn't find this out after giving her $500.  I texted her later to say she was both too young for me and that her schedule (unable to meet daytimes) wasn't compatible with mine.

Since my day had some time left, I called The Artist and invited her to coffee in the next 30 minutes.  We met near her studio.  She was definitely not as attractive in person as in her very sexy photographs.  Heavier.  A much squarer face/jaw than I'd noticed.  Not as great a set of legs as the pics indicated.  She was a fun girl who smiled a lot, but I was not attracted to her.  I texted her later and said sorry, but no.

Georgie

January 2011 --

Before my canceled date with India, I scheduled a lunch with Georgie.  Unfortunately it was not without some drama.  Georgie was a little upset that I was married and wanted to back out of the lunch.  After some cajoling, I'd convinced her that she shouldn't decide until after we'd met, and at least she'd get a free lunch.

She was extremely cute in an offbeat way.  Thin and wiry, tall, she coached girl's gymnastics nearby.  Over lunch we talked about the sexy pictures she sent me and who took them, had she modeled before (no), and what her expectations were from the arrangement.  We had a nice chemistry, but I could tell this was going nowhere.  After coffee I walked her to her car and kissed her goodbye, knowing that she'd never go for it.

India

January 2011 --

A couple of days after meeting Paulina, I had lunch with India, who lived within walking distance of my office, at a pricey restaurant in between.

India was even more beautiful in person than in her pictures.  She had huge dark eyes, highlights in her very dark hair, and perfectly large natural tits, which she gladly showed off with the clothes she wore.  She said she was born in India, but grew up most of her life in another country, where her parents owned a business.  She'd lived in the US for less than five years, and showed no trace of any accent. She said that she knew a lot of American expats growing up and learned how to speak American english that way.  She was well-read, worked from her apartment, and didn't really need the money, but wanted a regular sexual outlet.  My kinda girl!  I liked her better than Paulina, which was going to rule Paulina out.  I decided to make an exception and fuck her before deciding on everyone else.

We made a date for the next week, but she flaked, texting me that morning that she'd gone out of town the night before and didn't know when she'd be back.  Done!  Paulina back in the lead.

Paulina

January 2011 --

Met Paulina for dinner after work at a sushi place in her neighborhood I'd always wanted to try.  We sat at the bar, ordered beer and sake, and chatted quietly.  She came across very sweet, very agreeable.  Her financial demands were $500 per visit and I was willing to go there since no one responded to less than that.  She had light brown hair, brown eyes, and a big smile.  She was tall.  She worked in retail, but didn't really need to work since her parents were very wealthy and supported her.  She also had a serious boyfriend who lived about an hour away.  She saw him every weekend.  Her schedule was very flexible.  I liked her a lot, especially since she came across as sexy as she did sweet.  At the end of dinner, she asked if I wanted to see her that night.  No, I told her, I wanted to wait until I'd met everyone I wanted to meet first before sleeping with anyone.  I did it the other way last time and didn't want to sleep with a bunch of different girls this time.  She was fine with that, didn't seem worried at all.  I walked her to her car -- a new Mercedes -- and gave her a little kiss.  We would keep in touch over the next several weeks as my search continued.

Jackpot!

January 2011 --

There were so many girls to choose from this time, I didn't know where to start.  I had email conversations with so many of them, a couple of text conversations, and one or two phone conversations.  It was seriously eating into my work time, but I didn't care at this point.  Money was pouring in and I didn't need to work much.

In no particular order, here is a sample of the girls I thought were very possible:

Paulina -- mid-twenties, rich white girl living off Daddy's money in an expensive apartment.  Fantastic picture in her profile, which I later learned was just something she'd found online and posted to avoid putting up her own face.  Made me worry until she emailed me pictures of her which were really cute.
India -- mid-twenties, gorgeous, busty, well-traveled woman who'd grownup in a different country.
Tasha -- early twenties (I know, too young), fucking beautiful white girl with a great job who worked close to my house
The Artist -- great body in her pictures, mid/late twenties, never had a serious boyfriend, lived about 10 miles from my home
Zen -- mid-twenties, Chinese, internet specialist.  Lived alone in a nice part of town.  Grew up in Texas
Georgie -- mid-twenties, gymnastics coach.  Shared a single apartment with a roommate and desperately needed to move.  Unbelievable body and a great personality to boot
Kyra -- mid-twenties, retired porn star, working on a nursing degree.  Not the prettiest face I'd ever seen, but bisexual and very game.  Shared an apartment with a gay man who was never there.
Allison -- mid-twenties, Asian, from the next county.  Only considered her because she was so well read.  She'd chickened out before any meetings could be set up.

I explained to each of these girls that I wouldn't be sleeping with any of them until I'd made my decision on one girl.  They were all OK with it, and no one wanted up front money just to meet.

A New Approach

Early January 2011 --

Now that things with Hayden were officially over, there were some lessons that needed to be learned if I was ever going to be successful at this again.

First, I had to zero in on the age range of the girl I wanted.  Her age was crucial.  After thinking it over, here is how I narrowed the age range down: 

Over 40: no way. I didn't want anyone near DW's age.  Also, since I didn't want anyone with children or anyone married, most of the women this age were off limits anyway. 
Under 40/Over 35: Least desirable age range.  Again, a lot of women who were divorced or married with kids, but also it was clear to me that anyone in this age range who hadn't been married had some serious character defect.  I'd thought of Space Cadet from the the summer of 2009, who had a screw loose although she was a monster in the sack.
30-35: Getting to a better age range, but I reasoned that women in this range were in that frame of mind to start setting down some permanent roots -- getting married, having kids, etc.  Women in this age range trolling for Sugar Daddies would more likely have a motive to find someone for a long-term relationship, for which, of course, I was completely unavailable.  Also, more likely to have kids or be married, but not as much as the older ones.
25-30: Ideal.  Still wants to play before setting down roots, more than likely will have had a serious boyfriend or be divorced with no kids.  Not really ready for anything serious.
22-25: Best bodies overall, but with the most immaturity to go with it.  Hayden, as the example, was a flighty party girl who couldn't make time work for her most of the time, and just went by the seat of her pants too often.  Girls who can't plan well are girls who will create drama even when they don't want to do so.
Under 22: Out of the question, too young.

Second, I had to be picky, or else I'd invest thousands of bucks on girls who just weren't worth it.  Ethnically, I was attracted most to Asian girls, but also wanted someone who was not just a whitebread, all-American girl.  I wasn't into black women all that much, so I decided to rule them out completely.  No one too heavy, no one into drugs, no smokers, no heavy drinkers, no one more than 10 miles away from my office, no one within five miles of my home.  Essentially, I wasn't going to fuck a bunch of girls and then pick.  I was going to be a better chooser and wasn't going to be swayed by pretty faces or seductive personalities.  So no sex with anyone until I'd made my selection, with hedging for one or two more in case the first one didn't work out.

Third, and most importantly, I had to do my best not to compare any of these girls with Hayden.  That was a special time but it was over.  I had to move on and evaluate each girl on her own merits.

I reviewed my profile ad and determined it was perfect!  I was going to catch a lot of fish with this one.

Struggling With the End of Things

January 2011 --

Hayden and I had 17 great months together, only to see it fall spectacularly apart over three cancellations in a row and my dishonest handling of my own feelings about it.  After she'd told me to lose her number, I was angry at how easily she'd turned, but I was missing her too much to confront her about it.  I wanted her back and would do what I needed to convince her to try again.

I texted her shortly after the New Yearand invited her to lunch, just to talk.  I said I wanted to apologize in person and that I owed it to her to give her a full explanation of what had happened.  I admitted that I'd overreacted to the third cancellation and that I'd lied.  I was confused and hurt and couldn't bring myself to be honest with her.  She agreed to lunch the next day.  Well, I thought, there was a little hope I guess.

However, the next day Hayden texted me and said she was cancelling lunch.  Our time together was "fun, but over."  Fun, but over.  Three words and I no longer exist.  I begged her to reconsider, but knew after a few minutes it was useless.  At that point, I decided to suck it up and take the high road.  "OK, Angel," I texted.  "I had a magical time with you!  I wish you the best, my love, and I'll never ever forget you!  Take care!"

A quick email follow up to thank her again and to tell her that I would not be doing this again for quite some time.  She'd "ruined me" for anyone else.  Needless to say, however, that was not the truth, and I was on the sugar website again within a few days, looking for someone new.

The Fall-Out of My Email

Late December 2010 --

Hayden wrote back the next day: "I understand completely.  I really had a great time with you, Porter.  It was a good 18 month run.  I wish you all the best.  Good luck to you."

I had made a terrible mistake!  Again!  How could I approach her this time and not have her flip out on me.  I realized it wasn't going to happen.  She would flip out and I might not succeed in repairing the damage.  I'd lied in the email.  I didn't give a shit about the money, but I used it as a reasonable excuse to hide that I was really hurt by the cancellations.

When I approached Hayden about it, she was having none of it.  "Really mad at you for doing this babe!"  I apologized over and over, but she realized I'd lied to her and told me to lose her number and that she'd be deleting mine from her phone.  I'd betrayed her trust for real.

This time it was truly over.

Worst. Day. Ever.

Pre-Christmas 2010 --

I remember this day because it was a month since the last date I'd been with Hayden.  It started out rough.  Raining pretty steadily.  Driving my regular route to work, I was at a red light that was unusually backed up.  While attempting to brake, my calf cramped up and I hit the accelerator instead, which cause me to rear end the SUV in front of me.  There was nothing I could do; my foot and leg were stuck and I couldn't lift it up.  I was going probably 10 miles an hour at the time of collision.  My car was munched up front, but his looked barely damaged.  We exchanged information in the rain, I apologized and checked to see if he was injured (he wasn't), and I drove my car into a parking lot just off the street to call for a tow.  The tow truck came and I was towed straight to the body shop, and they called my insurer so I could file the claim.  I got put into a rental car and I set off for work, pissed off that my premiums would go up over a fucking leg cramp. 

Work was a horrible day.  Although I was only going to be there a few hours before leaving to see Hayden, I had huge setbacks.  Now, the only good thing that was going to happen that day was seeing Hayden before Christmas.  I'd bought a nice little gift and was looking forward to giving it to her.

The rain had not let up, but had in fact gotten worse.  I texted Hayden once I got to my car and said, "On the way, see u in 30."  "OK," came the response. 

Once I arrived and parked my car, I texted her again.  In response:

"OMG I have to cancel.  My ceiling is leaking from the rain."

"I'm here though."

"I know, I'm so sorry.  There's a repair guy in my apt. right now. 

"How long is he gonna be there?"

"He said he'd be at least another hr."

"This is the third time in a row, Angel.  I told u we should've skipped this month."

"I know, babe, I'm sorry!"

"So sad right now.  This has been the worst day ever.  Let's just see each other next month."

"You could get a hotel nearby and I could meet you there..."

"No.  Too sad right now.  Just going home."

"Aww.  I got you a gift for Christmas too."

"Me too.  Hold onto it."

"OK, babe.  Merry Christmas!  :-("

I didn't respond to that.  I just started the car and headed home.

I wasn't so much sad as I was angry.  I'd gotten my hopes up and was bitterly disappointed, three weeks in a row.  The third time when I was practically at her door.  All night I stewed about it, couldn't sleep, wasn't sure what I was going to do.

I woke up the next day knowing what to do.  I had to end this.  I was too mad at her for being a flake, and besides, I'd spent about $10,000 during the past year and was feeling like I could've given that money to my family instead of to someone who didn't bring enough of herself to the relationship and wasn't respecting my time.

I emailed her a long, sad note that wished her well and said goodbye.  I was done with Hayden.

Cancellation No. 2

Mid-December 2010 --

After the previous week's cancellation, I hadn't really been too upset.  Can't get upset when a girl gets her monthly, so we rescheduled for the following week.

On the day before our date, I texted her and she said she was going to be up late studying for a final she had the next morning.  I held my comments and told her I'd get in touch with her the next morning, but I was sure she'd bail.

Sure enough, next morning I got a text from her.  She'd been up all night studying, had taken a pill to stay awake, and was exhausted and too tired to get together.  She felt bad and wanted to reschedule for the next week.  I was hesitant.  She pleaded and said she promised she wouldn't cancel the next week.

We would see.

A Cancellation

Early December 2010 --

It was the first week in December, and we hadn't spoken since before Thanksgiving.  Hayden was gearing up for exams.  I had told her the last time that I would prefer to take December off, given that she has exams, then the holidays when she'd be out of town, etc.  We could avoid cancellations, which tended to happen all the time around the end of her terms.  She resisted, telling me, "But I really want to see you, babe!  I can't go that long without fucking you."  Fair enough, I said, but let's just do once.  She agreed.

On the day in question, I got the text.  It was a "red day," and she was out of commission for the week.  She suggested the next week.  "You have tests next week, Angel," I said.  She said she'd make time for me.

First Time Out in Public Together

October 2010 --

Until now, the only times Hayden and I had been out in public together, interacting with other human beings, was the two or so times we went out to have meals.  I don't really count these as being out in public together, however, as we really never dealt with anyone other than food servers and valet parking attendants.  One hardly spends a minute or two talking to them most of the time, and the times we were out we were at exotic restaurants where not much English was spoken anyway.

This time Hayden and I finally made time to get together at a trashy lingerie store to shop (late) for her birthday present.  We decided to make a date of it: meet at the store, shop, then retire to her apartment. 

By this time, Hayden has moved to an upper-floor unit in a much more secure building.  She still didn't have access to the front buzzer through her cell phone, but from her balcony she was able to open the garage so I could slip in and climb the stairs to her place.  The apartment was fairly close to the store where we were going to shop so I was glad we wouldn't have to spend a lot of time in traffic.

I arrived a few minutes early at the store and started browsing.  The place was decked out for Halloween, and "sexy Halloween" costumes were all over the place.  Not that I was interested in those, but I'd leave it up to Hayden to decide what she wanted.  There was also a gigantic assortment of toys and porn DVDs.  We were going to have a great time playing here.

Hayden arrived about 10 minutes later, dressed in a gray short-sleeved T-shirt, black leggings, and black suede boots with no heels.  In her big oversized sunglasses, she looked like a movie star, so sexy!  I gave her a kiss on the cheek (remember, no PDA!) and we started browsing.  It was obvious that we looked like a sugar daddy and his mistress, although I so wanted to look 35 and like a boyfriend.  Sadly, my appearance gave me away completely.  Luckily I'd removed my wedding ring before setting foot in the store (like that was going to make things harder to figure out!).

We spent our first few minutes with a salesperson (a gay Mexican guy) in the toy section.  I suggested a glass dildo, much like the one CC had stashed in her freezer.  Hayden had the irrational fear that it would break while she was using it, even when I had her hold it and even after the salesman assured her it was pretty much indestructible.  We ended up with this battery operated vibrator/dildo that twirled around and had bumps and bulges to simulate a real penis.  It cost over $100, but no big deal.  Next, we looked for a toy for me.  We settled on a vibrating, soft cock ring.  The salesman showed me how to use it (I had never used one before), but it seemed like an awful lot of work to get my cock and both balls through this tiny opening, just so that the vibrating piece sat right at the base of my cock.  It would still work just fine wrapped around my cock alone.

Now it was time to shop for lingerie.  After about 30 minutes, we'd settled on 4 different outfits, and she disappeared into the changing room to start trying them on.  She wouldn't let me come in to watch her change, but it was worth the wait when she had me come in afterward.  I don't gape much around beautiful women.  Where I live, they are everywhere, including in my own home.  But when Hayden tried on the first one I was stunned.  It was a black number that was entirely form fitting and cut out in just the right places (at her waist, bustline, low back, and high thighs -- like a swimsuit).  I just stood there with my jaw dropped.  "Angel, I'm speechless," I said. "You're so beautiful."  She loved it too, and it was a keeper.  She tried on the three others, and each one was devastating to me.  I had to buy them all.  At this point, the bill was over $250 and I thought it was perhaps enough.  We didn't see any porn we liked, and we really wanted to get back to her apartment so she could play dress up and we could try out the new toys.

The sex that day was unbelievable.  She had at least four orgasms.  After the third one, I was wiped out and hadn't come yet, so we took a break.  I removed the condom and lay back on her bed, catching my breath, talking, holding each other (which we rarely did because we'd always be so sweaty).  Once we were done talking, I sat up and said let's go again.  She sucked on me some more and got me hard again.  I lay her flat on her stomach with her legs together and entered her from behind.  She was still so wet, I slipped right in.  After a few minutes I reached around and started rubbing her clit with my hand.  She arched her back and pointed her ass up in the air, moaning loudly.  The more I rubbed, the louder she got, till she came.  I was close and I pulled out removing the condom and jerking off till I unloaded on her behind.  Such a beautiful sight!

Hayden said she'd model a different outfit for me each time we were together.  I couldn't think of a more wonderful way to guarantee more times together.

Every Man's Wish, and Other Reflections

Late August through late October 2010 --

My birthday approached, and Hayden and I discussed her gift to me.  I wanted a threesome -- there was no hesitation about it.  Hayden said she knew of at least three girls who might be available for it.  I was over the moon excited about it happening, and knew that it would be the most memorable sexual event  of my life.  She said she'd get it handled and make it happen.  When we had sex that day, we were both so turned on we came together for the first time.

The next time we got together in early September, she showed me pictures of a girl named Wanda.  Wanda was a young model, and a "really sweet girl."  She'd been talking to Wanda about a threesome with her for some time.  Apparently, Wanda also had a Sugar Daddy.  I asked, how does this subject come up, that you're both in "arrangements?"  Hayden explained that there were quite a few girls she knew who were doing it, both as a way to make money and live the high life, plus to have all the benefits of a sexual relationship without the drama of a romantic one.  I had to think that there was something a bit strange about that.  I'm all for women who want the same thing I do: namely, a no-strings-attached involvement with a lover, but that it was a common thread in her circle of friends just struck me as a deep commentary about how people in her generation are evolving around romance and long-term commitments.  Hayden had said she wanted to get married and have children someday ("when I'm 29," she'd say), but it wasn't even close to being on her radar at her tender age.  Fine with me: this was one of the reasons why I preferred sugar partners who were in Hayden's age range.  The older they get, the more they want out of life, the more the desire for permanence becomes, well, permanent.  A Sugar Daddy lesson was emerging here.

Hayden tried to schedule it, but it wasn't coming together with Wanda.  There was another girl -- Jamie -- who had just turned 19(!) and who was an active porn star.  I saw photos -- a vaguely Latina-looking girl, busty and curvy, with a huge colorful tat.  Gorgeous, and I told Hayden, "I can't believe you're going to be OK with my fucking this girl in front of you."  Hayden was far more sexually open and uninhibited than I was.  Apparently she'd done this threesome thing a couple of times before.

Unfortunately, Jamie was hardly ever around and she wanted three times as much money as Wanda did.  The third girl I never got to see, but she lived in Hayden's hometown and needed a plane trip to join us.  Pass.  Looks like my birthday present would not happen.  Oh well, I rationalized, no worries.  I was still happy with Hayden and could wait until it made sense for both of us.

Hayden's Birthday and Our One Year Anniversary

Late July 2010 --

Hayden and I have been together for a year now, and she just celebrated a birthday.  The time has flown by for me.  Forget about the fact that we were apart for a month during this time.  She's been in my life for a year.

I texted Hayden one afternoon to tell her that I wanted to take her shopping for the two occasions.  I was thinking something adult and hardcore, like toys and lingerie from some skanky store, perhaps even some porn we could watch together.  She liked the idea, but for some reason was a bit hesitant to make a plan to do it.  She would never quite tell me why, but she did suggest at one point that I just give her the money to do the shopping.  I explained that part of the gift needed to involve my watching her try stuff on and modeling it for me.  She finally got it, but it would be awhile before we got to actually find time to go shopping.

For me, the biggest benefit to having Hayden be in my life for this long was that I was able to become familiar with her sexuality so that there was no more awkwardness in bed.  We each knew exactly what the other liked and disliked, so there was no mystery once we were naked that we were going to make each other feel really good.  We were attracted to each other, we got along well, and there was definitely mutual benefit.  The earlier feelings of "love" that I'd been feeling had essentially faded, and I was content to be in this sort of Friends With Benefits relationship with her.  Still, as I got older, I started looking at things in my life through the filter of how much time I had left on earth.  I was satisfied with the quality and quantity of time I got to spend with my family, although this year was not going to involve a family trip.  I had been living the sugar lifestyle now for two years and felt like it was a good fit for me.  The sexual outlet satisfied me, and Hayden's companionship brought me a lot of happiness. 

Still, I felt the beginnings of a longing for something more.  I didn't want to be sneaking around like this every time I wanted to get laid.  I wanted all of this to be out in the open and to deal with whatever consequences materialized.  The "cheating" thing was starting to get a little old.  But, so long as DW did not possess the emotional strength to deal with this issue directly, I would have to be satisfied with it as it was.

Wednesday, December 26, 2012

Can I "Make Love" to My Mistress?

Late Spring-2010 --

Time with Hayden continued to be wonderful on all accounts.  We sorted out her scheduling issues with final exams, her period, trips out of town, etc.  And we were settled into a good routine.  We were both excited to see each other every two weeks.  Hayden told me in the Spring that she'd ended her arrangement with the other guy who'd paid for her surgery.  So I was her only  regular partner.  She said she still hooked up occasionally with other men, but nothing meaningful. 

I asked her once if, when we had sex, she thought we were fucking or making love.  She said it depended on the circumstances or the day, and she liked it either way anyway.  I wondered: was it possible for two people in our situation -- an older, married man providing financial gifts to a young, single woman in exchange for regular sexual liaisons -- to be making love?  In my mind, "fucking" was just the animal sexual act for the purposes of sexual release.  And there was no shortage of fucking in our relationship!  But, we spent more time talking and getting to know each other than fucking.  And the talking and laughing and good times, at least for me, enhanced the fucking to the point where it felt like making love.  And I told her that I didn't want us to use the terms "Sugar Daddy" or "Sugar Baby" to describe what we had.  She was now my mistress, and I was her lover.  And even in those moments when I felt doubt that she was sincere in how she felt about me, I knew that we were lovers.

Hotel Fun and a Three-Day Binge

Late March 2010 --

With Hayden and I back together, I felt more at ease with life.  Things with DW were the same as always: sex every three weeks or so, a general glossing-over of the major issues we were dealing with -- money, parenting, and sex.  With a regular sexual outlet, I always felt like I could come home at the end of my day and be completely attentive to the family.

The end of March brought an opportunity for me to get away from home.  My employer was paying for me to attend a leadership seminar for four nights, and they would put me up at a hotel located about an hour away.  There was no point in going home each night, as classes began at 8 am sharp and dinners were being sponsored all week.  I would get time away, and I immediately got in touch with Hayden to make plans for her to come visit (and perhaps stay over?) on my first night.  She shot the overnight thing down right away (and always did), but said she'd love to come by late one night and fuck my brains out.

An ATM machine in the lobby became my good friend, as I didn't have the time to go to the bank before leaving and wouldn't have time during my first day to leave the hotel for such a trip.  Hayden showed up at about 10:30 pm and stayed for two hours, as usual.  She had classes the next day and had to get back, which is why she wouldn't stay the night (plus she had her dog who needed her attention).  She was fully recovered from her surgery, and her tits, once released from their confines, were huge on her slim frame.  "This is a C-cup?" I asked.  "I went from a small B to a large C," she said.  "Got that right!" I said.  "I love them, and they feel so good," as I gave them a nice squeeze.  The skin was still a bit tight, but she didn't complain of any discomfort.  The scars were also very visible along the underside of each breast, but those would fade over time.  Having a king-size bed to play on for a change was nice, and we took full advantage of that.  Since it was late and I was a bit tired, however, we didn't go full out, but instead we had a comfortable time.  We even did the "lazy dog" position of fucking side by side, a position favored by DW.  Hayden joked about my energy level at that time of night, so I did make sure she came twice before we were done. 

The next day I received an email from Jill, who saw my profile on the sugar website and wanted to meet.  She was in her mid-twenties, an artsy type, and seemed very chill over the phone.  I thought, I'm out here, why not have her come by?  I told her where I was staying and she said she be there after school, which let out about 7 pm.  After dinner, I took a shower, hit up my friend the ATM for the $400, and went back upstairs to wait for her call.   When that came, I told her to meet me down in the lobby and I'd come fetch her.  She was a purple-haired emo girl, who dressed very hip, but showed no visible outward signs of craziness.  We talked a few minutes then walked together to the escalator to take us up to the guest elevators.  While walking to the elevator, I saw a colleague of mine from the seminar eyeing the two of us.  I'd been spotted.  I waved to him and made no mention of Jill. 

Jill and I had an OK time.  She was pretty quiet in bed, but she had two orgasms.  Her body was delicious, although covered in tats.  It was unremarkable for the most part, but I had fun and thanked her when she left.

The next day, the colleague who'd spotted us asked me, "Is your wife with you on this trip?"  I fully understood that he knew I'd probably fucked that girl, but I played dumb.  "No, why?"  "Just wondering," he said.  We didn't speak again that week.  I kept clear of him, and every time I saw him after that he gave me a dirty look.  Fuck that guy, I thought.  He'd kill to have the balls I have and would love to live the life I'm living, fucking beautiful young girls as often as I can.

That day, Sha called me and wanted to get together.  I told her where I was and, to my surprise, she said she'd like to come out to visit.  Three different girls over three nights: could this get any better?  Again, we set a date for about 8 pm or so.  She was late, but it was OK.  I told her to park in the parking lot and wait for me to come to her.  I wasn't going to get spotted again.  She parked pretty far away from the main entrance, which was smart.  When I saw her, we hugged and kissed, and I handed her my room key.  Told her to let herself in, get comfortable, and text me when she was ready for me.  I waited outside for about 10 minutes before she texted me that my key didn't work.  Fuck!  I went inside and she was standing outside my room waiting for me.  I hurried her to the elevator and had her wait in the lobby until I got the key replaced.  She then went up to the room, let herself in, and texted me right away.  It was a warm spring night and my window was open.  We kissed on the bed and were naked pretty quickly.  She did not shave her pussy, but it wasn't common with Asians, I found out.  She had a cute little body.  However, while making out on the bed naked, I detected a faint body odor on her that I didn't like.  I decided I wasn't going down on her unless she asked me to, and then I'd find a subtle way to say that I didn't feel all that clean, would she join me in the shower?  But she didn't ask. 

She had rudimentary oral sex skills.  For someone who exuded all this sexual self-confidence, I gathered that she must have been with men who didn't much give a shit about her skills and just wanted someone young and cute and Asian.  While on top of her, my cock was positioned at her opening, and I just slipped in without protection.  I promised her I'd pull out in a minute, but just wanted to feel her pussy first.  She didn't object, and in fact moaned loudly as I fucked her.  With the window open, I wondered who might be listening, but then I didn't care. 

For most of the time we fucked, which was far longer than one minute, I did not use the condom.  At one point, my cock twitched and I knew I'd released a little semen inside her, but I didn't say a thing.  I just pulled out and said, "Time for the condom."  She smiled and said, "I want you to finish in my mouth."  No problem!

After a few minutes I pulled out and she caught my load in her mouth at the last possible second.  Hot ending. 

Three nights, three girls.  Hayden by far was the best, but Sha was fun too.  Maybe if she cleaned up a little I'd fuck her again.  Jill, on the other hand, was not to be.  I texted her early the next week and said I didn't want to continue and wished her good luck in her search.  She texted that she'd already found someone else.  A lie, I suppose, but a necessary defense mechanism.

The Pitfalls of Admitting Error

Early March 2010 --

I had ended things with Hayden, and had gone out there looking for someone new, but wasn't finding much success.  Cha-Cha was about as close as I was going to get, and she refused to go down on me, so it simply wasn't going to happen.

Late in February I'd had coffee with a Chinese woman I'll call Sha.  She was a petite thing who lived on my side of town, was a graduate student, and lived alone.  She drove a Mercedes, so money wasn't really an issue.  She didn't want a boyfriend, but she wanted regular sex with an uncomplicated guy.  She was cute, though not as cute as I'd hoped she'd be.  Still she radiated self-confidence, which I found attractive.  I kept suggesting we retire to her apartment nearby to try each other out, but she wasn't going for it.  I knew she liked me though, because with all the prodding I was doing, she wasn't trying to end the conversation and get away from me.  At the end of the meeting, I walked her to her car and asked her to drive me to mine, which was a couple of blocks away.  Once we got to where I was parked, I made my move and kissed her, reaching into her blouse and giving her breast a squeeze.  She liked that, so I pressed my luck and stuck a finger under her bra and stroked and pinched her nipple.  No objections.  I then went for her pussy, and she opened her legs for me to stroke her over her jeans. I was hard.  We smiled and she said time for me to go.  I kissed her and stepped out of her car and walked to mine, fully erect.  Fun way to strut about the neighborhood in broad daylight!

A few days later, though, I had really come to grips with my regret at having ended things with Hayden.  A month had passed, and I really missed her.  It was the beginning of my real emotional attachment to her and our relationship.

One afternoon while at work, I sent her a brief text to say hi and to tell her, "I think I've made a terrible mistake.  I want to see you again.  I'm so sorry I ended things!"  Hayden's response did not surprise me; she was annoyed and angry.  However, she didn't shut the door on me.  She asked me to call her later once she was done with classes for the day.  I called her on my way home from work and ate some pretty large slices of humble pie.  I was wrong, I said, to end things because of some arbitrary timetable I'd set for myself.  I liked her, liked having sex with her, and I knew we had a good thing going.  She said she'd start seeing me again, but if I ever did this again, we'd be completely over.   Of course, I agreed and promised I'd do my best.

We made a date for the next week.  She'd already had her boob job, but was still in the process of recovering from the surgery when we met.  Her breasts were off limits and she could not take off her bra when we had sex, which had to be very slow and gentle.  No problem there.  I got her off with my tongue as usual, and she was grateful for that.  "You're so good at doing that," she would say over and over. 

When I hugged her goodbye, I said, "Yay, we're back together again!" and she laughed.  It felt good to be with her again.  Hayden not only was a fantastic lover, she was a great companion.  For the two hours we hung out, I felt relaxed, unhurried, cared for, desired, and sexy.  She would always call me "sexy."  Considering how old and un-sexy I felt in my own marriage, her words offered me comfort and reassurance that I was still desirable.  When we talked about it, I would reason it like this: I'm not giving her a ton of financial support, and I'm not demanding too much of her attention.  We make the most of the time we have together, we both get what we want, and we connect very strongly on a sexual level.  She could have any man she wanted, and she chose me.  We're a good sugar "couple."

But in the back of my mind I was keenly aware that I'd done something to damage the trust we'd built in the previous six months.  I would have to work pretty hard to earn it back.

Friday, December 21, 2012

Backing Up -- Revealing My Secrets

December 2009 --

Before the holidays, some old co-workers and I had arranged a dinner to get together and catch up.  I picked the place, and it was the Korean BBQ place that Hayden and I had eaten at a few months before.  There was supposed to be eight of us, but four guys canceled.

Once we were seated, the four of us, read the menu, ordered, and had a few beers too many.  During dinner, the subject of sex with our wives came up.  I decided I trusted these guys enough and, after complaining that sex with DW was for shit and that we'd had the "why don't you find a mistress" talk, I went ahead and did just that.  Ka-BOOM!  The three guys were floored, and for the next two hours, they peppered me with a million questions.  Of course!!!

I showed them pictures of Hayden.  More questions, particularly about what she was like in bed.  I relished the attention, and realized that I needed to tell someone about what a great time I'd been having with Hayden.  It was actually hard not having anyone to talk to about it.  I had mentioned that to Hayden, that she was the only one I could talk to about our affair, which was one reason I never shut up about it with her!

Since I trusted these guys, I knew that they'd never tell anyone else.  And to this day, they never have.  But the questions have never stopped.  Amazing to me that these married men, who say they still enjoy sex with their wives, didn't have the balls to admit that they'd jump at the chance to fuck a young model if they could figure out how not to get caught.

Going All-Out Ethnic, Part Two

February 2010 --

With Hayden now a former mistress, it was time to find someone new.  After the first two failures with Juju and Mami, I needed a sure thing.

First try was Cha-cha, a Latina in her mid-twenties.  We met for drinks one afternoon at a bar in her neighborhood which was close to my office. Good sign.  She was very cute. She worked in the "healing arts," basically another way of saying she was an aspiring coach but didn't make a lot of money. She had her own guest house behind her landlord, and eventually she'd accept me at her place, but the first time had to be a hotel.  No problem.  I liked her.  We set up a date and had lunch first, at a great Mexican restaurant, where we each had a margarita.  After lunch, she followed me to the hotel, a clean little two-star place down the street from the restaurant.  I had condoms and lube with me.  The room was big and clean. 

The sex was unremarkable other than two things: one, she loved my oral skills, and she had a big, but quick orgasm.  Two, she refused to go down on me.  This would be a deal breaker, but I fucked her anyway.  She was fun but this was a one-time thing.  I texted her the next week that I hit a financial snag and would have to wait a while before getting together again.  Not for $400 that was for sure!

Next was Lauren, a white girl, also mid-twenties.  We met at a wine bar.  She had a cold and looked like she felt miserable. She was game though and we had a decent convo.  She lived with a male roommate near her work, and he was away a lot so getting together would not be a problem.  Although I liked her personality, and although I could not faze her with my sexual talk, she was a little plain-Jane for me.  It was true that Hayden had ruined me for the girl-next-door type!

Then there was Mary J, an African-American beauty, again in her mid-twenties.  When I had told her that I'd never been with a black girl before, she took that as a challenge and said she wanted to be my first black girl!  She accepted my $300 offer, and we made a date for the next week.

Although I gave myself an hour to get there, her apartment ended up being only about 30 minutes, mid-day, from my office.  This wasn't bad, but Hayden's was closer.  I was definitely wondering what the fuck I was doing, as I waited in my car for the time to arrive, fucking another girl when I missed Hayden.  Yes, I missed her.  Was I getting involved with someone else too soon?  Perhaps.  But, I was here, and she was cute, and she had her own place, and she only wanted $300.

At the appointed time, I rang her doorbell. She was a petite, busty girl with dark skin, a sweet smile, and medium length hair.  She had a roommate in her two-story apartment, but the roommate was in her room and wouldn't care what she was doing, she said, so I didn't worry about it.  After the allowance was securely in her hands, she said she wasn't much into kissing.  No problem, I said, we'll figure it out.  I kissed her.  She seemed to like it, and she kissed me back.  We started getting undressed.  Once I was naked, she went straight for my cock.  I wasn't ready for that yet.  I wasn't in a rush.  I said hold on, let me do you first.  As I undressed her, her fucking hotness just got hotter and hotter.  What a great body she had!  Kissing her some more, I went down on her sweet pussy and she came.  Then I let her suck my dick.  She had full lips, and she was able to suck down most of me.  It was awesome!

We fucked in a number of positions, and she got off again.  At one point, I had her in my lap, as I sat at the corner of her bed with my feet on the floor, lifting her up and down on my cock.  Man, she matched me stroke for stroke.  This was a fucking thrill!  I finally came inside her, missionary position, kissing her whole time.  I remarked how, for someone who didn't much like kissing, she was sure into kissing me.  "Yeah," she said, "you're a good kisser!"  "Did you cum?" I asked.  "Twice," she replied, "once when you were down on me and once when I was on top of you.  I'm quiet when I orgasm."

During our conversation, she revealed that she was an aspiring singer.  I was intrigued to hear her.  She produced her demo CD and we listened for a few minutes to the first tune.  Holy shit, she was good!  She had a producer (with whom she was also sleeping) and had a deal in the making.  I was skeptical, since she was fucking me for $300, but I said "Great!"

I showered up and left.  Although I really enjoyed her, Mary J was only going to be a one-time deal.  I knew I was missing Hayden a lot, and I was beginning to think I'd made a mistake.

Bye, bye Hayden!

Early February 2010 --

I made a date with Hayden, but didn't tell her that I was planning to end our relationship.  I was so nervous, but I figured, hey, six months, it was a good run, and the emotions were an obstacle.

I got to her apartment, and she greeted me in a sexy bra and panties number.  I kissed her and we sat down on the couch.  I didn't waste any time.  "I'm not staying, babe.  I just came to say goodbye."

"Oh."

"Yeah, I figured it was time after six months, plus I was thinking that my feelings had gotten too strong."

"Yeah," she said, "can't let those feelings get in the way. I feel silly here in my underwear.  I'm gonna get dressed."

I told her to wait, and that I'd be gone soon.  We talked for a few more minutes, then she got up to get dressed.  "OK," she said.  "Well, I'll miss you."

"Me too, babe. Bye."

It was that quick and she was out of my life.

I knew it was the right thing to do, but why did it feel so wrong?

Going All-Out Ethnic, Part One

January-February 2010 --

My web search had yielded some pretty good results, across the racial spectrum.  First there was Juju, an Asian girl of 21 who was a college student, who'd had three years of experience as a "courtesan," as she put it.  I found her to be very articulate, and had one phone conversation with her on the way home from work one day, and we were discussing where to meet, and we picked a very upscale hotel near her school.  She basically expected me to book the room and meet her the next day.

I asked what allowance she preferred.  She said, "Starting to sound too business-y for me."  This was new for me.  "So you don't want to discuss an allowance?" I asked.  "We can talk about that tomorrow."  Needless to say, we didn't make it happen.

Next was Mami, a Latina of 18 years old, also a college student who I met at a local Starbucks close to her school.  She was extremely cute.  She was the first in her family to go to college.  She had a two year old son and was working a job plus going to school.  She'd never done an arrangement before.  She lived with her parents, so we'd have to do a hotel.  I knew this was wrong for a couple of reasons: one, her age; and two, her kid.  I deliberately steered the conversation into extremely sexual territory to see where her limits were.  She was reserved and sweet, but I knew it was a no-go for her.  I told her to think about it and get back to me.  She texted me three days later to say thanks but no thanks.

As I had a few more to meet, it was time to end things with Hayden.

Fallout

Early January 2010 --

I now had uttered the L word.  I had always told myself that if I'd gotten too emotionally connected to a girl, or if she'd developed feelings for me, that would be the end of things.  There was no unsaying what I'd said; besides, it was true.  I loved her.

Six months was approaching, and I knew what to do.  I went back to searching for a new girl.

I saw Hayden early in the month and we had a fine time.  I didn't tell her anything and we didn't discuss what had happened.  There wasn't anything hanging over us or me, but I was clear that I would need to do something to move on. 

"Red Days" -- and the L Word Appears

December 2009 --

Hayden and I had only one chance to get together in December between her exams and the holidays.  On the morning of our date, however, she texted me that she had to cancel.  She'd gotten her period.  I had already purchased her gift, and I didn't want to wait until January to give it to her, so I told her that I was OK with no sex because I had her Christmas gift.  She was actually disappointed not to be fucking me, so I suggested she take care of me orally if she wanted to make it up to me.  I told her I'd make it up to her another time.   "OK," she said.  "Come over soon, sexy, I want to see you."

When I got there, she was in some seriously sexy lingerie.  I sat on her couch and we kissed for a few minutes.  She said that when she was on her period she didn't feel particularly sexy, but my cock couldn't tell the difference.  I was hard as a rock.  (She would frequently comment about how my cock seemed to get even bigger when she'd go down on me.  Whether or not that was true, I always smiled and said, "That's what you do to me, baby.")

I handed her the gift I'd purchased, wrapped nicely with a bow and a sentimental Christmas card.  I'd been keeping it in the trunk of my car for a couple of weeks, and it was not easy to conceal from my wife.  It was a cute little docking station for her iPhone, with colored lights that changed with the music that was being played.  She loved it!  I was thrilled.  I gave her a huge kiss.

She got down on her knees and worked on me perfectly.  She gave head like a girl who loves to suck cock.  It wasn't exactly like a porn star, since most of the time they gag themselves, use a lot of spit, and have this motion with rotating their hand while stroking and gripping the cock that, I have to say, is extremely fucking hot!  Even though she was on her period, I still wanted her to enjoy herself, so I reached down and took off her bra to play with her tits.  She liked that.  Then I asked if she'd come up on the couch because I wanted to rub her pussy.  She declined that request, reminding me that she didn't feel very sexy.

It took her about 15 minutes, and I had a wonderful orgasm, my first from her that was from oral sex.  She took my load in her mouth but didn't swallow.  She then got up and tried to kiss me with a mouthful of my cum!  Hah!  Cute, babe, I said, now go spit!  She excused herself and cleaned up, then came back to sit with me.

"See?" I said.  "We can have a great time just with oral.  If you hadn't been on your period, I'd return the favor."  "Yeah, but I love your cock.  It feels so good inside me."  I thought about what she said: she loved my cock.  Was that code for she loved me?

"Listen," I said, getting serious.  "I know that we have a short-term, recreational relationship going here.  That's all it's ever going to be.  And one day it'll be over."

"Yeah, I know."

"But," I continued, "that doesn't mean that there isn't room for emotions between us.  I think it's entirely appropriate to feel love, or something like it."  Pause.  "You're so great, Hayden.  You're like an angel to me.  I know I'm not giving you tons of money or extravagant gifts, but you seem to be completely cool with what I give you.  And I gave you this gift because I wanted you to see that I notice you and the things you have in your life.  I'm paying attention; I didn't see anything in your apartment for playing music, so I wanted to get this little thing for you."

"It's so cute!"

"Just like you, baby.  And you're so sweet to hang out with.  I'm feeling happier than I have for a long time, and I love you for that!"

The L word had appeared.

She could've told me not to say that, but she didn't.  She could've said she couldn't return my feelings, but she didn't.  Instead, she just smiled,  giggled a little, gave me a hug, and thanked me for the gift and for being such a good guy to her.  I think that was just the best thing she could have done other than tell me she loved me.

Miraculously, I was hard again.  She stroked me and said she couldn't go down on me again.  I suggested a hand job.  She got some lubricant and played with me for about 20 minutes before I came again.  I always have much more intense orgasms the second time, and my sperm flew everywhere, all over both of us, making us both crack up. 

I was spent, and I was in heaven with this girl. 

The Pitfalls of a College Girl, and Financial Woes

Late November 2009 --

Hayden had just returned from a trip to visit her family for Thanksgiving and we had plans to be together.  However, we hit a snag: she had final exams and projects in the works.  Her time was very limited.

On top of that, I hit a snag of my own.  Business had dropped, and my cash flow was impacted.  I also had a big legal settlement hit me and I had to draw down nearly all my savings to pay for it.  I told Hayden, and she was fine with waiting until January to see me, but I wanted to see her once before Christmas.  I had a gift for her!  She was touched and we made a date to get together.

Intimacy Growing with Hayden

November 2009 --

After more than three months together, Hayden and I had a good rhythm going.  I'd show up late afternoon around 3:30 or 4, text her, she'd leave the side gate unlocked, and I'd find her apartment door unlocked.  Most of the time, she'd be in her bedroom already naked, or in lingerie.  Sometimes she'd be masturbating with her fingers, or with a vibrator.  Since I was such a sick voyeur, this was always a thrill for me to watch her. 

During the last month, I'd learned a few more things about Hayden.  One, she was a seriously hardcore party girl.  She told me about trips she'd taken to Vegas with her girlfriends, of taking MDMA (Ecstacy) at a party, of getting falling down drunk, and of fucking random guys.  When I'd hear these tales, I'd always ask if she'd used condoms.  "Always," she said, "I keep them with me in my purse all the time.  I don't take the pill, so this is what I have to do.  I'm never too drunk to forget these."  She said she got tested twice a year and has always been clean.  I had a doctor's appointment coming up, so I supposed it was time to get tested too.

I also asked her about the other guy she was seeing and how the dating was going.  She said that she wasn't really dating him, but that he would take her on a trip now and then, and he wanted to have a relationship with her like a boyfriend/girlfriend thing.  She said she wasn't really interested in that.  "But, he's going to pay for my new boobs," she said.  "You're getting a boob job?" I said.  "Why?"  "To be more proportional.  I don't like having wide hips and small boobs."  "Oh, angel," I said, "please think hard about this.  Your breasts are so beautiful, it would be awful to get them augmented."  "I'm a B now, I'll just be going up one cup size to a C."

My first wife had also had her breasts enhanced, going from a B to a C.  They went from perfect to near-perfect (as enhanced boobs go), but the transition in size wasn't overly dramatic, so Hayden's news started to rest easier with me.  I told her I was looking forward to massaging them, and demonstrated how my first wife and I had engaged in that particular activity.  I had Hayden straddle me and I took hold of her breasts (oh, they were so wonderful!) and massaged them.  "This is hot," she said.  Too bad I'd already had an orgasm.  At my age, one was my limit.

Changing the subject, I asked, "What do you want for Christmas?"  "Oh, I don't know," she said, "a new car?"  "I'd like to get you something for your apartment that you need."  She couldn't think of anything, but I looked around and got a few ideas.

Sharing Might Not Work

October 2009 --

From the beginning, Hayden and I agreed that we would not be exclusive.  I knew my monthly "allowance" would not be enough to satisfy all her needs.  She had student loans taking care of tuition and books, but she had rent, a car, and lifestyle needs.  She lived alone in an expensive neighborhood.  I did not object to her having another benefactor, so long as it didn't impact my access to her as often as we agreed to meet.

At the end of September, we'd met again at her apartment and had, as usual, a great time together.  I asked her about her other guy -- his age, career, etc. -- and she produced a few details.  He was considerably younger than I was.  At the time I didn't consider this as any sort of obstacle to our arrangement.

A week or so later, however, I texted her to plan our next meeting, and she didn't respond.  In fact the whole weekend went by and I didn't get a return to a couple of follow up texts either.  When she finally did respond, she apologized, and said she'd been in Vegas with her other guy.  "We're sort of dating," she wrote. 

At our first meeting at the coffee joint, I told Hayden that I ended the prior arrangement (with CC) because she'd found a boyfriend.  I lied because I didn't want to tell her that I found CC to be boring, as I didn't want Hayden thinking that I'd perhaps get bored with her too.  I know that the boyfriend story doesn't seem much different, but it is, because if she finds a boyfriend, then the catalyst for the end of the arrangement is from outside our relationship.  Subtle, but very different than forming a subjective opinion about her ability to keep me entertained.

"Hmm... maybe I should just end this now," I texted back.

"What???" she wrote.

"If ur dating someone, it's going to get in the way eventually.  Better to stop now b4 that happens."

"Babe, the sex is just so amazing between us, it would be a total shame to stop it now."  Well, it was very nice to know that she felt the same way I did!  "We're not serious or anything," she continued. 

Now, here was one of those moments where I look back and wonder what would have happened had I moved on.  If I'd left, I'd have eventually found someone else.  But she was right that the sex was totally amazing, and I was having a fantastic time.  Better than anyone in the 15 months I'd been living the sugar life.  And here she was, calling me "babe" and pleading with me not to go. 

"OK," I texted, "but you'll let me know if things get more serious, right?"

"Of course.  So we're on for next week?"

"Can't wait. :-)"

"Yay!! :-)))"

(Mini-rant: I hate texting, by the way.  It is virtually impossible to convey emotion, context, or mood.  Voice texting is better, but why not just have a conversation?)

We made plans, got together, and had a great time.  We had now been together six times, and were well on our way to a long time together.  I figured another three months, at least.

Thursday, December 20, 2012

"Merry Everything!"

I haven't seen Hayden in over four months, haven't spoken to her in nearly three months, and other than one or two short emails, haven't communicated with her in over two months.  Even though I've moved on, and have accepted that we're not getting together again, but I still miss her a lot.

Today I emailed her a Christmas greeting, wishing her peace, love, joy, success and good health.  I am so happy that she has found a good man and seems to be settling into her new life.  But I still miss her.  A lot.  I wrote, "I hope that before I'm too old and senile I'll get to see you again."  I closed the email saying that I'd die a happy man if the Mayans were right and the world was ending tomorrow because I'd gotten to spend time with her for three wonderful years.  God, I'm so pathetic.  Even though I know she'll probably never see me again, I still throw out the line to see if she'll bite my hook.  This better get easier as time goes on.  But I am pretty sure it will be years before I have completely recovered from our relationship.

Behind the Veil of Privacy -- Her Apartment

Mid-September 2009 --

Today I would enter Hayden's apartment and have sex with her in her private world.  I arrived a few minutes early and texted her that I was parked a block or so away.  "Too early," she wrote, "I'm not quite ready.  I'll text you when to come in."  "Do I come to the front door?"  "No, I left the side gate open at the other end of my building.  My apt. number is XXX."

Once I got the text, I went to the side gate, but found it locked.  "Locked," I texted.  "Damn," she wrote.  She came to the gate and opened the gate, but told me to wait a minute before I entered.  She was wearing a robe, so I knew that she was in lingerie (or nothing!) underneath. 

Her apartment was a typical young person's pad.  Assorted furnishings thrown together, lots of crap strewn about the floor.  A small kitchen.  A door leading to a short hallway that was flanked on either end by the bathroom and bedroom.  She also had a tiny little dog, with a very feminine name.  She was a cute little thing, but she yipped something awful until I paid her attention.  We became almost instant friends. 

Hayden and I chatted on her couch, with the dog between us.  We developed an easy rapport, and I felt very comfortable in her place.  She, on the other hand, seemed nervous, and I asked her why.  I learned that she was naturally paranoid about being found out and exposed for being a "Sugar Baby."  "You're not a Sugar Baby to me," I said.  "More like a mistress."  Does a young college student get the distinction?  Not sure, but like many of the other things we discussed, it didn't seem to matter once we started kissing.  Yes, she was wearing very sexy lingerie under her robe.  We went into the bedroom, which was a mess, and she apologized for it.  Clothes were piled up everywhere.  She simply had more than what her closets would fit.  I didn't care, and never did at any time. 

Our sex had started to become a pattern of acts.  Kissing, disrobing, oral on each other, her having an orgasm, condom, intercourse (missionary and cowgirl), then my orgasm.  It was an exquisite pattern, and I would never get bored with it!  We threw in a 69 this time, which is usually a sure thing to make me climax. 

Nothing earth-shattering happened during this encounter, except I started the practice of leaving her allowance in unusual places.  At hotels I'd always just left it on a bedside table in a white envelope.  Now that I was in her apartment, and because she didn't have a bedside table, I considered slipping it into her purse when she would be in the bathroom.  But I wanted to play with her a bit, so the first time, I snuck out to the kitchen and placed it in her fridge.  I wrote the words, "Cat Food" on the envelope.  When I got to my car, I texted her, "Hey do you have any cat food?"  "???"  "Check the fridge."  A minute later.  "haha, thx, babe!"  "Have a great weekend, angel!" I wrote.  "Angel" became my nickname for her.  She would always know it was me when she got a text or a phone message and heard "Angel."

Know Your Limits

Early September 2009 --

I had so enjoyed my last encounter with Hayden, I just wanted to see her more and more!  Since she was so sexual and so passionate, we seemed to be on the same page when it came to the things that turned us on.  It was clear that she had blown the lid off of what "my type" was.  In truth, my type had changed to anyone who was like Hayden!

For our next visit, I chose the same small hotel as the previous encounter.  I had planned to ask her if we could meet from that point forward at her apartment, since I thought we had established a baseline of trust with each other.  In fact, I posed the suggestion while I was inside her.  She said, "Let's wait till we both cum, and then we'll talk about it."  Heh.

Afterward, she said she guarded her privacy very carefully, not only because she preferred it that way, but because the manager of her apartment building lived right down the hall from her and was sort of a friend.  She didn't want him knowing her business and seeing some older guy going down the hall and leaving two hours later.  On top of that, the building's intercom was supposed to be connected to her land line, which she didn't have.  If I was at the door, she'd have to physically let me in.  But she said she'd figure something out.

I took her out to sushi after sex, at a little hole in the wall down the street from the hotel.  It was a great dinner, and the place was full, which told me it was a pretty good place.  We sat at the bar and ordered sake (my first time) and split a few dishes.  I told her about my encounter with "Alexis," and how I handled it. She was flabbergasted that anyone would do something like that, but it was certainly a reality check that trust was so vitally important in this relationship. 

She and I were having a great time!  I took a risk and leaned in to her face and lightly kissed her in front of everyone.  She kissed me back and didn't say anything, but she looked around and did get quiet for the rest of the dinner.  Then, on the way back to the hotel, I took her hand as we crossed the street.  Once we got across, she took her hand back. 

Without her saying a word, I took this to mean that public displays of affection were over the line for her.  From that point forward, I would not attempt anything more than a hug or a peck on the cheek in public with her.


Transfer Complete -- and a Major Scare

Early September 2009 --

My office had moved.  The facilities were crude; no desks or cubicles, just a few long hotel-ballroom-seminar-type tables with a bunch of those Aeron chairs and some phones, along with a few ethernet cables to hook up to the network.  The two boxes full of my shit from the other office were stashed under the table in front of me.

While driving to my first official day at this office, I received a text from someone who identified herself as Alexis.  She said she had gotten my note from the Sugar Daddy website (one that I had probably sent weeks before) and that she was interested in getting together.  She was Asian, a model, and "very hot, baby!" 

Since Hayden and I were non-exclusive, I didn't feel any obligation to shut her down at this point, so I texted her, "Where are you located?"  Geographic convenience is always a top priority with me.  She texted back that she lived more than an hour away, but often stayed in town for a couple of days at a hotel when she had modeling jobs.  "OK, well," I replied, "I'm already involved with someone closer to home, but thanks for your note! :-)"

What happened next was the beginning of what would be the first major scare of my time in the sugar lifestyle.  Alexis, for lack of a better phrase, went ballistic.  She started by accusing me of lying that I was even interested in a sugar relationship.  I took the high road in response and texted, "Of course I'm interested, hun, but like I said I'm already involved with someone for over a month now.  She lives close to where I work.  It's simple and it works and I don't see a reason to change.  Have a great day, hun!"  This response, unfortunately, did not have the desired effect.  Her language, punctuation, and demeanor got worse at this point.  She let loose with all sorts of crazy shit about how hot she was, how I was a fucking idiot for not hooking up with her.  I ignored most of it, but sent one text that said something like, "I don't know what you hope to accomplish with all these texts, but you aren't going to change my mind.  I think we are done.  Please stop texting me."

A few minutes before I arrived at my office, I got the following text:  "Well, Mr. [my real name] who works at [my employer], I've copied your profile page and I'm going to send it to your wife.  How do you think she'd react to see that you're cheating on her?"  She actually named my wife.  She must have Googled my phone number and found who I was, then found my social network page and saw my whole life laid out.  My mouth went dry and I started to sweat.  I needed to get to the office quickly, shut down my profile, and fix it so that DW could never get an email from this freak. Maddeningly, none of the other drivers on the highway were remotely aware of my urgent need to arrive at my office, and they couldn't move fast enough!  I texted back, "Why the fuck are you doing this?  I've been nothing but upfront and polite with you!"  The response was nearly immediate: "I want $1,000 cash or I'm sending the profile right now."  This was an intentional scam; but I stood firm: "I'm not sending you anything."

Once I finally arrived, I hooked up my computer, logged into the Sugar Daddy website and immediately deleted my profile.  Then I contacted their customer service department and alerted them to this person who was trying to extort money from me.  They would later apologize and tell me that they had taken down this person's profile.  I was pretty sure at that point that it was not a woman, but some asshole using the internet's anonymity to shake down vulnerable men like me who were risking exposure.

Once that was done, I logged into DW's email -- luckily I knew her password -- and looked for any signs of strange emails either through the social networking site or directly to her.  I looked in Spam and Trash, but nothing.  I then adjusted her settings so that she would never see any email that was from anyone who was not one of her existing contacts.  They would immediately go to Spam, and Spam was immediately deleted.  She'd never even know anything would come in.  I also had her social network password and logged in as her, and adjusted her Settings so that she'd get no messages from anyone she didn't know.  I knew I'd need to monitor things for a few weeks until I figured the thing had blown over.  I also updated my email and my social network settings so that no one but people I knew had access to me or any detail of my life.

Being new to the Sugar Life, I never really gave a lot of thought to someone trying to extort money out of me, but I realized that there were a lot of crazy people out there.  I am very good at recognizing them and most of the time I'm able to avoid any of that stuff.  But once in a while, I guess someone would slip through my defenses and catch me off guard.  Nothing ever came of this episode, but my guard was way up after that. 

Wednesday, December 19, 2012

Oh, Hayden!

Late August 2009 ---

For our third visit, I booked a much less expensive hotel a few blocks from the last one.  This was more along the lines of a Ramada than a four-star place.  But, so long as the rooms were clean and the beds comfortable, I didn't care.  I didn't think she'd mind either.  The online reviews of the place were decent too.  Also, I invited her to join me for dinner afterward, to which she happily agreed.  I picked a Korean BBQ place not far away that I'd heard a lot of good things about.

Hayden arrived on time.  I checked her face for any sign that the room was not to her liking, but found none.  After a few pleasant minutes kissing and catching up, she excused herself to the bathroom.  I got undressed down to my underwear and stood at the foot of the bed, waiting for her to emerge.  When she came out, she was wearing a teddy, thigh-high mesh stockings, very high heels, and one absolutely beautiful smile.  She came over and kissed me, reaching into my underwear and stroking me gently.  I was instantly hard.

She had another explosive orgasm when I went down on her.  "Like that?" I smiled.  "Yes," she purred, "you give the best Os!"  I climbed up on the bed and kissed her passionately.  As she went down on me, I watched her and stroked her shoulders and hair.  She started caressing my balls, which I absolutely love! 

As we fucked, we were constantly talking to each other about things we liked and wanted to do with each other.  As it turned out, both of us had threesome fantasies. She wasn't bisexual, but she was open to another girl.  I asked if she'd like to have two guys at once.  She enthusiastically said, "Yes!"  "Which guy do you want me to be, the guy you suck or the guy you fuck?"  "Yes," she said again.

When I came I pulled out and exploded on her chest.  I asked her if Hayden was her real name, and she said no, no one uses their real names.  She told me her real name, but she confessed she liked her fake name better.  I absolutely loved her real name -- it was beautiful and suited her perfectly.

We soon both cleaned up, separately, and then dressed for dinner.  I walked her to my car.  She was in my car; this was like a date now!  We were seated at a table in the middle of the dining room.  Not inconspicuous at all, but we were somewhere where I knew we would not be spotted.  Dinner was amazing and we shared a few beers together.  Afterwards we went back to the hotel.  I was hoping to fuck her again, but found I was too full, so we kissed for a few minutes and held each other.  I asked if we could out to dinner again the next time, and she said yes.  Then we went our separate ways.

Three times together now, and each time the sex got better.  We were both opening up to each other about our lives, just a little, and we were clearly enjoying each other's company.  We had another date planned.  This was feeling different from CC for sure.  And I couldn't have been happier.

My Type?

August 2009 --

One of the things I always hated about this arrangement stuff was that I had financial limitations that rendered me unable to see my girls more often than every other week.  And after seeing Hayden the first time, I sort of wanted to see her again as soon as I could.  I made a date with her by text for about 10 days later, and booked the hotel a few days later.  The hotel, as it turned out, was really close to her place, and she was able to walk there.  It was a nice, classy high-rise, but the rate was less than the last one since I'd gotten a deal online, so I liked that.

Again, she was late, about 45 minutes this time.  I said, "Do I have to tell you the time is 30 minutes earlier just so that you'll be here on time?"  She laughed, which was good, because I certainly didn't want her mad at me for being a clock Nazi.   She said she wasn't really good with time, but that she'd try to be on time next time.  Luckily I didn't have to be anywhere by a certain time.  I had texted DW that I'd be home late, and not to wait on dinner for me.  (This was, incidentally, a practice that I tried to avoid most of the time.  I learned that it was important that these liaisons not interrupt my regular home schedule.  If I usually got home at six, then I'd back up the time of our meeting so I'd be home on time.)

UPDATE 12/8/2016 -- I just noticed that I used the word "time" ten times in the previous paragraph! That has to be a record or something.

The sex this time was different.  First of all, Hayden wore really cute matching underwear so that when I undressed her she'd be coordinated.  "Nice touch!" I told her.  I was wearing my typical white briefs!  Second, I was determined to learn a lot about her in bed this time, so I deliberately tried every position I liked to see where her limits were.  I was flipping her all over the bed every couple of minutes.  "What position do you want?" she asked, a little frustrated, a little bemused.  "Just want to try all these with you," I replied, "to see what feels good and what doesn't."  Before we got to fucking, though, I went down on her again, and she had an orgasm.  Took about 15 minutes.  Just before she came, she started breathing really heavy, her hips rocked a little, and she moaned, "Yeah, yeah, YEAH!"  And then she simply exploded.  Unlike some women I'd been with, she didn't lock her legs around my head, which was always uncomfortable for me.  She just kept them open, as if she didn't want it to end.  Incredibly hot!

I started realizing that I was really attracted to this young woman.  I noticed more about her this time.  Her nose, which was typically Middle Eastern, made her face beautifully assymetrical.  She had no tattoos anywhere, which I loved since I think tats are just unattractive no matter how beautiful they are.  Her body felt warm whenever I touched her.  Her kisses were hungrier, more passionate this time.  And when she was turned on, she bit her lip a little in a way I found so sexy.  Her long legs and curves were different from all the other petite girls I was so typically attracted too (like DW).  Her dark skin, dark hair, and very dark eyes contrasted completely with the girl-next-door look I preferred.  She was exotic, tall, and really, really beautiful. 

On top of her obvious physical beauty, I truly appreciated how articulate she was.  Clearly she liked to party, loved to fuck (she'd had sex just two days before seeing me), and was a bit flighty, but she was a college student studying business and had clear career goals.  Plus, she'd overcome divorce and other issues to get herself into college and make it on her own.  Impressive. 

Other than CC, this was the only girl I'd seen more than once, and I liked Hayden enough to keep this going for as long as it made sense.

Hayden Life

Late July 2009 --

When the day came, I left work early to make the drive across town.  I had texted her earlier to pick up condoms and lube, and she happily agreed.  Parking was scarce near the hotel, but I got there on time.  I checked in, made my way up to the room.  The hotel was modern, but small and intimate.  There was a small restaurant/bar on the ground floor.  The room was very modern, with a walk-in shower, and dark furniture.  I decided to bring my laptop with me so I could get a little work done in case she was late.  Which she was.

Hayden showed up about half an hour late.  Not too bad, but since I'm such a stickler for time, I did mention that I appreciated it when people showed up on time.  We talked for a bit about how the week was going.  She sometimes went to classes on campus, but some of her classes were online so she did them from home.  She sat on the bed while I stayed in the desk chair.  I wasn't rushing.  Like I said, she wasn't really my type.  She wore a white top and dark leggings, and looked really pretty.  I made my way over to the bed after about ten minutes and kissed her.  She had soft lips, a little thin, but she was a good kisser, and I told her so.  Smiles.  More kissing, some tongue, and then we slowly got horizontal.

I asked her the last time she'd had sex.  She said she'd had sex a few days before with some random guy she'd met at a club.  Kind of a turn-on for me, actually.  She seemed a bit reserved, so it was cool to know that Hayden sort of had a darker side to her that was very sexual.

I won't really go into too much detail about the sex we had, but it was nice.  Not spectacular, just nice.  Awkward at times.  My oral skills were unsuccessful at getting her off, and she was a bit tentative on me, mostly because I think she was nervous because I am large.  She did reveal one surprise though. She had a tongue stud and she used it to great effect on me.

She had very dark skin, and it felt like dark porcelain, so deliciously smooth.  Her breasts, though small, were gorgeous and firm.  She was not particularly toned, but she wasn't even a little flabby.  The benefits of youth, I guess.  I definitely enjoyed myself with her. 

Afterward, we hung out for about an hour longer, getting to know each other.  She had two siblings, a brother and sister.  She grew up in northern Cal and her parents were divorced.  We talked a little about her ex-boyfriend.  He was her age and she said that she much preferred older men because they were more stable and mature.  I agreed wholeheartedly, of course.  We older guys are masters of stability and maturity! 

Eventually, she got up and dressed, then left without washing up.  Sort of surprising to me, but no problem.  We had agreed to see each other again in a couple of weeks and would stay in touch.  She said she preferred text to phone calls because usually she was in class or busy studying.  No worries, I said, and told her to feel free to reach out anytime.

I showered up and left the hotel.  I would not use this hotel ever again due to the cost, so I was now on the hunt for a new one.  Although Hayden was not my type physically, she was a sweet girl and we had fun.  I was willing to try again with her.  Next time should be better!