My Complete (Slightly Edited) Dating and Sexual History, PART 4

[just some guy]

This is the fourth part of the story I was inspired to tell by another member's similar confessions on this site. I started the story in the "Relationships, Discrimination, and Jealousy" part of the forum and you can find the first three parts there.

This part overlaps part 3, which detailed my second long term relationship. That's because I cheated on my second girlfriend a lot.

This is not a complete romantic history. There are tons of girls that I liked or had crushes on that I was never actually involved with that I won't mention here. It also won't include any random encounter I had with a girl that didn't really feel like a date, or didn't result in sexual activity of any kind. I might include some, but not all.

It's also not a complete relationship history, as I'm going to focus primarily on first dates and memorable sexual encounters; I won't focus so much on the details of how each relationship was over the course of months or years and/or how they ended, unless this somehow ties into other relationships or sexual encounters. Maybe I will comment on this in passing.

I might omit some things when I come to certain illegal activities, or things that I would rather not post, but when I do I'll make a note of it. For the most part, this will be completely raw, uncensored, and uninhibited. I have no stake in this site, as it is my first post, so I'm not trying to impress anyone or win any points. I won't be trying to make myself sound good, and I won't be covering up my faults or mistakes. I'm laying it all bare in the name of science.

I'm going to get very specific... but.... please rest assured ALL PERSONS NAMES HAVE BEEN CHANGED. ALL PLACE NAMES HAVE BEEN CHANGED. In each case, I tried to use a similar name with a similar etymology and ethnic or connotative history to preserve the flavor of the story.

I would say don't judge me.. but... that's your prerogative. Judge away!!

If this generates a lot of responses, I'll post more.

 

[just some guy]

Jasmine from Market Street (c. December 2000)
A gorgeous stripper I met downtown in San Francisco. I forget what I was doing there. I had had one previous experience in a strip club at that point, and it was a very erotic and arousing experience for me, so I went again in San Francisco. I was sexually frustrated in my relationship with Alisha at the time.
Jasmine was beautiful, probably of Hispanic or middle-eastern descent, and presumably took her stripper name from the Disney princess she resembled. She had long black hair and gorgeous skin. I paid her for a private dance and drooled over her flawless petite body for a while.


Mary Jane (c. December 2000)
The same night that I got a private dance from the hot mocha stripper Jasmine, I also got a dance from a perfect blond going by the name of Mary Jane. I saw her dancing on stage and was flabbergasted at how perfect she was. Long golden blond hair, amazing body, dancing provocatively in thigh-high white stockings and nothing else. She was a vision straight out of every man's fantasies.
I got several private dances with her in a back room, where she let me suck on her nipples and put my fingers just inside her soft moist pussy. If I wasn't so poor I might have gone back to visit her more, as she hinted that if we got to know each other she'd be up for coming back to my place for a more intimate private dance, but regrettably that never happened.

 

[just some guy]

“Thai” (c. January 2001)
Officially almost two years into my relationship with Alisha, I was living out in California to be closer to her but things in our relationship were not going very well. After my ideals and worldview had been shattered by high school and during the aftermath of my breakup with Jenni, I had started to change a lot as a person and continued to change while I was dating Alisha. My views on love and commitment and monogamy were changing considerably as I started to regret spending all of my teens and the first part of my twenties in years-long committed monogamous relationships. I started becoming curious about polyamory and open relationships but thus far Alisha was not having any of that. Alisha and I were not having sex very often at all, sometimes once a month or less, a result of Alisha's sexual neuroses and other problems in the relationship that had not been resolved; I was becoming extremely sexually frustrated and antsy. I still had that unfulfilled Asian girl fetish that I had been harboring since Lisa Han in junior high school, and living out in Davis, a college town full of young hot Asian coeds, was exacerbating that problem tremendously.
All of this combined toward me taking the steps that would lead to my cheating on Alisha with a prostitute for the first or second time, depending on your individual reckoning. I started looking for Asian escorts online, of which there are many in the San Francisco and Sacramento areas, and though I couldn't find any that really looked that much like Lisa I finally settled on one nicknamed “Thai” that I found through the website CityVibe.com.
I drove down to meet Thai at her hotel in the east bay area and met her in her room. The girl that answered the door was short, dark-skinned, toned and curvy. About 23 years old, 5'0” tall, with long jet black hair and a few tattoos dotting her otherwise delectable skin. She had full lips, wide hips, and nice perky breasts. I think she was Filipino by ancestry but obviously had grown up in California. She answered the door in skimpy see-through negligee and high heels, and looking very slutty which was a turn-on for my sex starved self.
I was extremely nervous, and I guess she could tell. She was a little impatient with me but not unkind. She sat me down on the bed and asked if I'd like her to dance for me, which she did to some hip-hop music, rubbing her terrific firm round ass in circles around my crotch. My cock was rock hard after a few seconds of that, and Thai told me to lay down on the bed. She fished my dick out of my then-too-tight underwear and put a condom on before starting a blowjob. I enjoyed pulling her dark black hair back to watch my cock getting sucked by that pretty Asian face.
When she mounted me and started fucking me cowgirl style, I was still nervous and not used to using condoms since I had been having sex with Alisha for two years without any. I was having trouble keeping an erection. Thai unmounted me and jerked me off with her hand for a while to try to make me hard. She looked a little disappointed, and said that she could finish me off with a blowjob but if she changed condoms to do that, it would be the last one.
I talked her into letting me finish missionary style, which made my dick hard again watching it slide in and out of her taught little body and hairless brown cunt. Thai seemed a little bored during this, which reminded me of my first experience with a prostitute in London, but I was still getting off on fucking an Asian girl- something I had fantasized about for so long. I blew my load, got dressed, and was on my way.
I went to go see Alisha immediately after that, still smelling of Thai's strong perfume and with her pussy smell on my dick and fingers... but Alisha didn't notice. Actually I believe it was that night that we wandered off to a field of grass right next to a busy road and had sex under the stars in a patch of deep shade.

 

[just some guy]

Kathleen “Asia” (c. March 2001)
I enjoyed my first experience with an Asian prostitute a couple months prior, was still sexually frustrated in my relationship with Alisha, and was still experiencing a bit of yellow fever living in Davis with so many hot Asian college girls walking around... so I decided to give it another go that Spring.
I found Kathleen on CityVibe in Sacramento, going by the alias “Asia.” The picture on the website was of a slim girl with a nice body- not Kathleen.
Her incall location was in a townhouse that she shared with a couple other prostitutes and their young children, which I got to walk by on the way to Kathleen's bedroom. The room was cramped and a little messy and we ended up doing the deed on a mattress on the ground.
Kathleen was from Sacramento but said she was 100% Filipina. She was very petite, but not as slim as in the photo. About 4'11”, 100 lbs, cute face, long nails on her fingers and toes. 19 years old with long wavy black hair. She started giving me a covered blowjob with her top on. When I asked her to take her top off, she was shy and reluctant to do so, saying her body wasn't the same since she had her baby. I assured her I was cool with it, I just wanted to see her naked, so she took her top off revealing a pair of soft tits that had obviously been used in breast feeding and a saggy tummy with a lot of stretch marks.
She continued sucking on me, and when I asked if I could fuck her she apologized and said that she really couldn't because she just had her clit pierced. I was very nice about this, said it was okay, and let her finish me off with her mouth.
Kathleen was very gracious for me being so cool, was talking about it when I was on the way out, and she and her hooker friends all wanted to know if I had a girlfriend. I sheepishly lied and said that I did not. I never saw any of them again but it made me wonder what it would be like having a prostitute for a girlfriend.

 

[just some guy]

Jennifer Morehouse (c.2001)
Jennifer was a girl that I worked with at the Denny's in Dixon who claimed to be younger than me but who I was always pretty positive was lying about her age and probably at least 28 or so. She had dirty dyed blond crimped and curly hair, blue eyes, tan skin, and wore a lot of makeup. Her personality was very spunky and energetic and I enjoyed her raunchy sense of humor and the colorful exchanges we would always have at work.
I was involved with Alisha at the time that I started flirting with Jennifer, and I'm not even sure exactly when that was since I never wrote about it anywhere. She and I flirted back and forth a lot at work, and went out once for lunch, but I think after she realized that I was mostly interested in a physical relationship (as a means of relieving extreme sexual frustration in my current relationship with Alisha), Jennifer became offended and we didn't go out anymore after that.

 

[just some guy]

Susan Mannish (c. April 28, 2001)
Susan is the only sex partner I ever met from the website Adult Friend Finder. Their advertising lies: Susan looked nothing at all like Shay Laren.
I was with Alisha at the time, more sexually frustrated all the time, and using Adult Friend Finder regularly to try and find someone to cheat with since I couldn't afford to visit prostitutes regularly. I met Susan in one of the chat rooms. She was significantly older than me, 39 at the time that we started talking, and the picture she sent me of herself was not very flattering. Still, I was extremely horny, desperate for sex, and I had never really been with an older woman before. I thought perhaps it would be worth it just for the experience. After Susan I decided never to have sex with someone I was not attracted to solely for the experience of it.
Susan seemed interesting to me. She was intelligent. She had worked in the video game industry, an industry that I was trying to get into at the time. She was going through a separation and had not been with any men since her husband.
I told her that I couldn't meet at my apartment because I had a roommate (a lie), and we agreed to meet halfway and get a hotel. After dinner, I was having strong second thoughts. Susan very much looked her age. She had brown hair that was turning silvery, a dumpy untoned body, and damaged skin. I almost drove off after dinner instead of going to the hotel to meet her as we had agreed upon, but I couldn't bring myself to be that cruel.
When Susan got naked up in our hotel room, she looked even worse. She was 6'0”, at least 150 lbs and probably significantly more, and balding a bit. She had very sparse thinning pubic hair, blond in color. She tried to relax me with some red wine, but that was also a turn off as she tasted like wine after drinking it.
She gave me a blow job and we had sex a few times. She had some kind of contraceptive film so we didn't use condoms. She was very sexually sensitive and came multiple times, as did I though it wasn't easy because her body was so disgusting to me and her pussy was loose and droopy. I just tried to imagine something else and focus on the feeling. Still the experience left a very bad taste in my mouth and I vowed not to repeat it.

 

[just some guy]

Johannah Ruth Barrister (May 2001)
Johannah was a bit like a Jewish chihuahua... very little... very loud... a little hyperactive and always seeking to be the center of attention. She was about 5'1”, 128 lbs, chubby but not fat with large breasts for her size. Her skin was light and freckled. Aside from her curvaceousness she was petite all over, with short arms and legs and stubby little toes. When I knew her in high school she had long wavy brown hair, but when we had sex it had been cut and was only chin-length. Her father was British and her mother Jewish and she had traits that ended up a strong mix of both. At the time we had sex, she was 20 years old.
Johannah was a good friend of mine from high school that I was always curious about because she was so extremely oversexed and promiscuous. I learned a lot of things about sex talking to Johannah and had a lot of my naiveté shattered by her. When I was in high school I was still devoutly Christian, still strongly opposed to abortion, still somewhat opposed to pre-marital sex,and still pretty sheltered even though I had had sexual experiences when I was as young as five years old. I was not particularly attracted to Johannah during high school, just somewhat curious because of who she was, and even if I had been attracted I wouldn't have acted on it since I was still with Jenni at the time. I graduated in 1997, a year before Johannah, and had not seen her since then though we continued to communicate online.
In May of 2001 I was home from California visiting family for my birthday. It was in the twilight of my relationship with Alisha, I was more frustrated than ever, and I was looking to cheat on her more and more. Because Johannah and I were talking so much online we agreed to meet up at Starbucks, which we did. Before we even met I was planning on having sex with her. I knew what a slut she was and I assumed it would be easy.
After coffee we went back to my parents' house, which was empty at the time, and went up to my bedroom to talk. We were lying on my bed, talking about I don't remember what, and my head was resting on Johannah's legs. My fingers, behind my head, started creeping up Johannah's thigh. She figured out what was going on and just asked me straight up if I wanted to fool around. I confessed that it had crossed my mind. We agreed to have sex but that it wouldn't mean anything.
I got a condom from my parents' collection above the refrigerator, and Johannah and I fucked in a few different positions. I told Johannah that it was great because it satisfied a curiosity that I had had for a long time, and eliminated any sexual tension in our relationship. She seemed kind of surprised that I was interested in her at all, and afterward a little anxious to just forget about it happening, though she seemed to enjoy my penis while we were copulating and got off at least once.
We were never sexual after that, though I did watch her have sex with her boyfriend in a hot tub along with a crowd of other onlookers on New Year's Eve of that same year.


Veronica (May 2001)
The same week that I was back in Virginia and had sex with my friend Johannah I sampled a local working girl I found online going by the name Veronica. Veronica was 18, 5'6”, only 100 lbs, with long wavy bleached blond hair. Her face was blurred out in her ad online, but I had to go see her because she had such an amazing body. I get stiff just thinking about her body. I think either she was a former stripper or was going to be a stripper, I forget which, and it was obvious by looking at her naked. She had a very tiny little waist which accentuated her amazing curves. Her great hourglass figure's crowning grace were a pair of absolutely perfect tits. Everything about her amazing body just screamed that this was a girl who took really good care of herself. Her skin was impossibly soft, like a downy satin pillow. Her cute little toes were perfectly manicured. Her breasts, good god those breasts! Large, shapely, pert and perky, sooo soft to the touch, with big pink plump soft nipples... like sucking on an overripe peach. She made sure I didn't suck too hard- taking care of her body again, I guess.
I brought a camera hoping to take pictures but she wouldn't let me. She came in to her bedroom wearing a bikini and looking awesome. She sucked my dick with her soft wet lips and then I fucked her missionary style with her soft little feet resting on my hips. I only paid for a half hour and Veronica was rushing me to come, but it didn't really take much urging for me to blow my load staring at the gorgeous body that I was drilling. I held out as long as I could and then emptied my load inside of her tight pink pussy.

 

[just some guy]

stupid bitch (c. May 18, 2001)
Whenever I looked at CityVibe to find prostitutes around San Francisco I always noted that there were a lot more working down in Los Angeles and many of them were very hot. So when I had a chance to go down to L.A. I decided to try and find some fresh meat while I was there. Originally I was going to go by myself, then Alisha was coming with me, but I still wanted to try the local working girls.
My first attempt to cheat on Alisha during our trip to Los Angeles was with a prostitute I found through the internet that pulled a bait and switch move on me, taking my money and then refusing to have sex with me or even get naked. If we had actually had sex, she would have been the first Hispanic girl I had intercourse with. Instead I got one of the most half-assed massages I've ever had in my life and then she laid on top of me in her underwear.


Soo (c. May 18, 2001)
After the disappointing rip-off that was my first experience with a prostitute in Los Angeles I was hornier than before and still unsatisfied so I called up Soo, a 25 year old half-Japanese half-Korean girl. Soo was 25, about 5'3” and 125 lbs, very curvy for an Asian girl and pretty, too. She had long straight black hair and a shaved pussy. Her tits were plump and her nipples thick and meaty like many Korean and Japanese girls'.
Soo answered the door to her apartment in transparent green negligee and high heels, looking extremely sexy. Her personality was warm and accommodating and she put me at ease right away. She started giving me a back massage on her bed, but, I was in a hurry and already very turned on by her hot body so I turned over on my back and started kissing her large soft breasts. She gave me a nice bareback blowjob and then we switched to missionary position to commence fucking.
She really seemed to enjoy her work. She had many orgasms, one after the other in rapid succession. She even apologized for cumming so many times before I had once but I said it was perfectly fine. She seemed to really love getting fucked. Appropriate that her ad online had the headline: “Soo needs it!” I had to rush off at the end which was a real shame because she was encouraging me to stay longer, but I had to go pick up my girlfriend.


Peter and Claire (May 25, 2001)
Peter and Claire were a couple I met through the AdultFriendFinder chat rooms when I was looking for an outlet for my sexual frustration with my relationship to Alisha. At the same time I was also starting to feel like I was wasting my youth being in years-long committed relationships and was starting to desperately want a greater scope of sexual experience. I wasn't ready to break up with Alisha, though, so I started obsessing about threesomes and the swinger lifestyle. Peter and Claire introduced me to the concept of polyamory, which was very appealing to me because I preferred having some intimate connection with sexual partners over anonymous sex.
I never talked Alisha into actually engaging in any of these things, though she and I talked about it a lot. I did go to visit Peter and Claire on my own, though. They were a youngish to middle-aged couple living in the Bay area. Peter was “white” and his significant other Claire was Asian. Their policy was to invite friends to their home and if something sexual happened as a result, so be it, but they didn't like to try and force the matter.
I went hoping that something sexual would happen, as Claire was an attractive woman and I was fascinated by this polyamory concept, but nothing did. We played the board game Settlers of Cataan and ate fruit and cheese and watched movies. The second time I went down there I ended up in a game of Magic cards with Peter and another of his friends. Nothing sexual ever happened.

 

[just some guy]

Kira Spears (c. September 2001)
I met Kira through the AdultFriendFinder chat rooms. She was a young girl with long red hair that lived in Sacramento. I told Alisha that I was going to go see her and some of her friends, though I denied that I was hoping to eventually have sex with her.
Nothing sexual ever happened. I met Kira, who was less attractive in person than in the picture online, and her friends at a Jamba Juice. We talked about music and the vampire card game Jyhad. I never saw her again after that.


“Passion” (c. September 19, 2001)
Still very sexually frustrated and still suffering from acute yellow fever, I arranged to meet up with Vietnamese prostitute “Passion” in the suburbs northeast of San Francisco.
Passion was extremely petite, which turned me on, about 4'11” and 98 lbs. 22 years old. She had a tight shaved snatch, and a cute little butt. She had a pretty face and short black hair. Vietnamese-American, obviously raised in California as she sounded like any other girl from the ghetto. Her pretty skin was dotted with tattoos here and there, including at least one name I think, I forget if it was her baby or her ex-boyfriend. If the former, then there was nothing else about her beautiful body that would suggest she had given birth.
She remarked about how big my dick was, and had a little trouble taking me when she rode me cowgirl. She let me try doggy style, which I enjoyed as I had a great view of my big dick sliding into her small tight body, but she was struggling a bit in that position as well.
Overall a satisfying experience, and the last time that I would cheat on Alisha with a prostitute.


Chika Shizuoka (September 29, 2001)
Chika was an impossibly cute Japanese foreign exchange student at UC Davis, the school where my girlfriend Alisha was attending and where I was working. I saw her eating at the student union building, and after ten or fifteen minutes of watching her and trying to build up the nerve I managed to approach and talk to her. We talked about the English idioms that she was studying and I got contact information from her.
She was so cute and I was so thrilled to have talked to her I had a perpetual case of butterflies until I saw her again and I sang her name happily in the shower. Our next date I met her and some of her friends for smoothies or ice cream I can't remember which. I brought her a box of chocolates which I guess tipped my hand that I really liked her, because after that she sent me an e-mail saying that she had a very jealous boyfriend and she couldn't talk to me anymore. I would have left Alisha for her if I had had the opportunity, and she was the first girl I cheated on Alisha with (after a fashion) that I was interested in for any reason other than sex.