Where it happened: see below
Langauge: English
Sex: Male
Rating: 2
Category: Straight
All this is true. The names have been changed. It does get confusing. No made up mini-skirts without panties, etc. I live in a city with about a million people. Here are the major players:
“A” was almost 17, I was 20. She came into the place where I was working; and I asked her out; she NEVER wore a bra and was maybe 32B. After a few weeks, I felt brave enough to feel her thru her tank top, and she was mighty fine. A few nights later, she wore shorts and what was essentially a triangle bikini top; we went miniature golfing, then watched some TV at her house, then went for a walk in a nearby park. We began kissing, and I took her top off, and I was in absolute heaven, feeling and sucking on her hard, exposed nipples. A few days later, on her birthday, her father bought her a used car, and she drove over that night to show it to me. She wore a denim overall dress with a tee shirt, and we went parking. I started feeling her thru her tee shirt, and “A” surprised me by pulling some of her shirt out, so I took that as a sign and pulled up her shirt to enjoy the touch and the view. After a few minutes I got brave, and put my hand between her knees, and she surprised me again by spreading her legs, so I moved my hand up
to feel her thru her panties, then moved underneath them and into her. She was really getting excited, and so was I. Not wanting to press my luck, I didn’t try to go further. Maybe a few weeks later, we went parking again; she was wearing tee shirt and cut-off overalls. After feeling and kissing her breasts for a while, I moved my hand down to touch her pussy again. She started rubbing my crotch thru my Levis, and I got harder than ever. I unbuckled my belt, then she took control and started unbuttoning my Levis, exposing me. Then all of a sudden, her cut-off overalls and panties were down around one of her ankles, and she was on top of me, “dry-humping” or more. I came about a minute later, all over her. About a week later, we went about an hour away, into the woods for a picnic, which soon turned into a necking session. Again
wearing cut-off bib overalls, she unbuckled the straps, took off her shirt exposing her nice boobs, then buckled the suspenders again (as if that provided coverage). We dry-humped twice in the woods, then once more back at her house. Soon after, she admitted that she had lied about her
age, and had just turned 16, not 17, so I was actually glad that we had not actually had full sex. We went together for a few more months, and she gave me my first, and subsequent BJs in my car.
I met “B” at a party, she was 18, a college student, and also never, ever wore a bra, about 32A. Our second time out, I felt her breasts and crotch thru her clothes, but we really didn’t progress further physically than that, but became good friends.
“C” was 19, and also never wore a bra, and was smaller than 32A. She was okay, but I was only mildly attracted to her, and she was a virgin. I got her shirt off after about a week, but there wasn’t much there. A few weeks later we were giving each hand jobs, she would do me once, then again about 15 minutes later. She seemed to like me a lot more than I liked her, and was pretty possessive, interfering somewhat with my friendship with “B” by tying up too much of my time. After about 4 months, I dumped “C” because of that, but I was okay that we never went further because I felt that she would’ve hated me even more, and I didn’t like her enough to want her to be my first.
Within a few weeks, out of the blue, “A” called me up, and told me that a new movie was out, and she couldn’t think of seeing it with someone else but me (I had seen it a week earlier with “B”), so I went with her. The next week, “A” and I went parking; she wore a red one-strap tank top which didn’t stay on that long. A week alter, I was playing in a sports tournament, and she came over to my new apartment then along to watch. When we got back, I was hot and sweaty, and needed a shower, so I said “you may join me if you like”, so she did (that was my first shower). The shower was very memorable, and she remarked that it was the first time we had been completely naked together, so I replied that I hoped it wouldn’t be the last. So after the
shower, we lay on the bed, feeling each other, giving hand jobs and BJ. She said that she had since gotten on birth control pills, and we agreed to wait to have full sex until she turned 18, in three months. We saw each other semi-regularly the next few months, and when her parents and sister went away for a week, leaving her alone (parents: don’t do this!) I spent several nights staying over with her. We slept naked, in her parents’ bed, and did everything but full sex.
But I few weeks after the shower with “A”, I met “D”, a beautiful 19 year old college student, and was smitten immediately. She had everything, and I had never felt this way about anyone before. I knew I wanted “D” to be my first; three weeks after first going out, I got her shirt and bra off (she always wore one, and I confirmed hers at 34B) but didn’t try anything more. So I was seeing both “D” and “A” at the same time. About two weeks later, “D” borrowed a camper, her other friends backed out, so we went camping alone (we really had never really discussed sex
specifically, but there was anticipation in the air, me remaining hopeful). After we arrived at the campground, she had on a tee shirt and panties, and I had on boxers and a tee shirt, and we climbed into bed. After a few minutes of kissing and feeling/kissing/sucking her breasts, I was
feeling warm, so I took off my shirt. She then took off her shirt, and also took her panties off. So off came my boxers, she said she was on birth control pill for period regulation, and I proceeded to make love to her. It lasted about 15 or 20 minutes, and was great; I loved her so much, and was so glad to have waited for a special person like her. We made love many times that weekend, and after. I asked her if she would marry me someday, and she said maybe, as she was not sure then if she would ever want to be married or have children. Then she went away to
her second year of college, about 120 miles away. The first weekend I went to visit her, as her roommate was away.
But the next weekend, sleaze as I was, I slept with “A” (who had just turned 18), and slept with her regularly, but still considered “D” to be my real girlfriend, and would be with “D” when she came back to visit me and her family. “A” got her own apartment, and I continued seeing her for
about half a year. I was still seeing “D”, but she wanted to take things a little slower.
I met “E” at work where she was a contract worker. She was 21, and about 15 pounds overweight, and a bunch from work went to a bar one Friday night. After a sports victory
Monday, she came to my apartment, and I went for a short swim while she sat by the pool, then we kissed. The next day, after work, after practice, “E” and I went to play tennis. After tennis we decided to take a swim, but she declined my offer to help her change into her swimsuit. She
came out in a green Speedo one piece, cross-straps in back, practically see-thru, and her hooters were very large (38D). In the pool, I felt her breasts thru her swimsuit, but she was getting a little cold, so we went into her studio apartment. I started feeling her thru the swimsuit,
but couldn’t really figure out how to get it off of her, but she felt a little cold, so I suggested she take off her wet swimsuit, which she did, slowly, as I watched, and she crawled into bed. So off came my trunks, and we did it. I still considered “D” to be my girlfriend; the relationship with “E” lasted about three months, until “E” went back to college, about 100 miles away; I never saw her again.
I met “F” at a party; she was a little blonde, 19, and had a child. We went to a film, then I got her shirt and bra off (she had almost no chest at all), but she wouldn’t let me unbutton her Levis (no one ever stopped me before). We were together maybe two months but never went further.
Once we ran into “C”, but when I tried to introduce everyone, I couldn’t remember “C’s” name.
“G” was about a year older than me, and I met her in my apartment parking lot after coming home from my sports on a Friday evening (she lived in the next building). She accepted to go to a party with me the next evening, and I drank a little too much there. She talked a lot about her
roomate’s sex life, and I started feeling her when we got back to the apartments. We went to her place, and I took off her shirt and bra, not much was there, then unbuttoned her Levis, then suggested we go upstairs. She didn’t have any protection, and was afraid to wake her roommate, so she led me into the living room. She gave me a blowjob on the floor, and I came in her mouth and she swallowed everything (this hadn’t happened to me before). This went on for a few months.
I traveled 500 miles to spend some vacation with “B”; we slept in the same room, and didn’t do anything, knowing that the physical distance between us would always be a barrier, but I did entertain thoughts of just “surprising” her in the shower one morning.
I met “H” in the same parking lot, after coming home “a little under the influence” following some drinking after sports practiceone afternoon, so I asked her if she wanted to join a group of us that evening. She declined. “H” was almost 20, strawberry blonde, and chesty (later confirmed as
38C). A few weeks later, after some prodding, I was able to get her to go out with me. Within a few weeks, I got her shirt/bra off and enjoyed her ample assets, but she stopped me when I tried to unbutton her Levis. A few weeks later she came over so we could go to a party. But before, I got her shirt/bra off and started on her Levis, and she agreed, but first I had to turn off the light. She was inexperienced, and we didn’t have any birth control, so we just felt each other, then we went to the party, exchanging secret smiles. Two weeks later, after a film, we went to my
apartment, got naked in the bed, and she gave me a hand job. We woke the next morning, naked, and she felt real embarrassed to still be there, and I had to coax her repeatedly to shower with me (as I would actually see her). She started staying over each weekend for the same
activities, and we soon went camping. Naked in my tent, I told her she could suck on it if she liked, but she said she wasn’t comfortable with doing that. But she did (without asking) the next night. She had gone to a doctor to get on the pill, but had to wait a couple months before she could start it because of hormone levels. She agreed to try condoms, so I bought some, and we used them for two months evening and morning when she stayed over; then she flew back to her old city for two weeks.
Then I met “J”; she did business with the company I worked for, and had just moved here from another state. She was dark blond, 21, and 34C, and I asked her out. We spent the day together, went swimming at her place (she looked good, in a black one-piece), went to my apartment (where she saw a picture of “H”), and went to dinner. Three days later, we ended up at her apartment, and I got her shirt and bra off, but before that she had made me promise not to try to go further, but hinted that she would’ve, and would in the future, depending on what the situation was with “H”. The next day I picked up “H” at the airport, and we made love for the first time without the condoms, and I told her that I was going to start hanging out with “friends” on Fridays after work. Well, Friday I went to “J’s” apartment (she was wearing a dress as she had returned from a distant relative’s wedding), and, while standing, I reached up and felt her buns over her panties for the first time. She visited the restroom, then did I, and when I emerged she
was naked in the bed. I took my clothes off, and joined her, and climaxed in about one minute (to date, the only time I ever came that quickly). She asked me when I would be ready again (which surprised me), and I stayed overnight. But of course the next evening and following
morning, I was doing “H”. “J” was not real pleased with me continuing to see “H”, and “H” had no idea I was seeing “J”. Once at one of my leagues (I had invited “H”) “J” showed up unannounced, sat next to “H”, and “H” even asked “J” if she was there to watch anyone special (she replied no). I continued to sleepover doing “J” Friday night and Saturday morning, and “H” Saturday night and Sunday morning for five months; other days, it was just flip of the coin, and I was having sex about a dozen times a week. One Saturday morning, I slipped out of “J’s” bed, went home to visit with “D”, and had “H” over that night. I went away for the weekend once with “J”, and took a 10 day vacation with “H”. When back, one night when I was out with “J”, we ran into “C”, who called me the next day at work to invite me to a party. I told her I would go, but with someone
else, and I took “H” (I even thought about inviting “C” over sometime so I could try to sleep with her, but decided not to even try). However, later, when it got close to late November, I realized that Thanksgiving, Christmas, and New Year’s were going to get me hung out to dry, impossible
to continue this. So I broke up with “J”.
Six months later “H” moved in with me, and a year after that (after “D” decided she didn’t think she was ready now or ever to get married) “H” and I got married. About two years later, as I was showering to get ready for “D’s” wedding, “H” asked me if I felt that it should have been me
marrying “D”, and I told her no, but was not sure that it was the truth. About a year later, “H” and I divorced. “D” was on the outs with her husband, but I told her that I didn’t feel right about causing a couple to split up, and we could discuss the situation if they split up.
Not long after that, after a group sports activity, I invited “J” over for dinner. Since we were somewhat sweaty, I talked her into going for a swim at my apartment pool. It was drizzling, and I gave her a yellow tee shirt and gym shorts to wear in the pool. In the pool I started kissing her, then feeling her chest; when she remarked that she could win a wet tee shirt contest, I agreed. I asked her if she could stay over, and she paused, then agreed. We walked back to my apartment, and she went to change. When she didn’t appear for a few minutes, I went in to
check on her, and she was standing there topless. I went over and kissed and felt her, then she put on her bra and shirt, then took off the gym shorts, nonchalantly showing me the first pussy since my marriage, then she put on her shorts. We made dinner and ate, then went to bed, and
did it again in the morning (we never did it again, but she was the last before my marriage and the first after).
After a string of brief relationships I met “K”, she also worked for a company that did business with where I worked. She was divorced, and lived with her teenage stepdaughter and small son, and just wanted to “be friends”. A few weeks later, at her house, she wasn’t wearing a bra, and I kissed her and felt her 34B top; she felt pretty good, but didn’t go further because her
stepdaughter was there. The next week, I unbuttoned her shirt and her bra (“front closure”, she instructed me), and we went into the bedroom. So began our relationship as friends who just happened to sleep together Friday night/Saturday morning (as that was when her ex-husband
took the kids).
I had met “L” a few years before, but I decided to ask her out, as “K” couldn’t spend any additional time with me, and I felt alone on all but Friday evening/Saturday morning after a few months with “K”. We started seeing each other, and after a few weeks, I got her shirt and bra unbuttoned (34B). I went to see her the next evening, and got her shirt and bra off, but couldn’t get her to take her gym shorts off (I was surprised at that). This went on for a few weeks, sleeping with “K” Friday evening/Saturday morning and getting “L’s” top but not pants off on
Saturday evenings.
I decided to take the patient, but not too patient approach with “L”. One Saturday morning, maybe anticipating, I didn’t sleep with “K”; that night, while fondling “L”, she told me she was ready, so we went back to her place. I took her shirt and bra off again, and she took off my shirt,
then took off her pants and laid down on her bed wearing panties only, so my pants came off, and I crawled onto the bed with her. I massaged her and pulled off her panties, my boxers came off, then she rolled over onto her back, and I entered her. We didn’t get much sleep that night,
doing it three times, and the next morning, after substantial prodding, I got her to shower with me
(I never slept with “K” again). “L” must’ve had a good time, because she invited to stay over again a few nights later (and I broke off with “K”, not wanting to repeat my past history, and risk screwing up everything). A year later, we moved in together, and had sex about a dozen times a week. We got married a year later, doing it three times on our wedding night. This was 10 years ago, and we have a boy and a girl (named “D”). I have physically been faithful to “L” ever since, but I get tempted, and, oh, those memories…….
Updates:
I went to the weddings of “B”, “D” (both times), and “J”; “J” and “K” came to my second wedding.
“A” still lives in town, I heard; haven’t seen or heard from her directly in 20 years.
“B” lives in another state and our families and kids are friends.
“C” once sent me her wedding announcement, haven’t seen her in 20 years.
“E” married the guy she went with after me, haven’t seen her in 20 years.
“D” got divorced a few years after reconciling, then remarried, and we see her occasionally.
“H” got remarried and lives in another state, haven’t seen her in 15 years.
“J” moved away, got married, and has moved back here, and she and “L” are friends.
“K” got remarried, I ran into her once at a restaurant.
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