AOLGeneration, Author at NSFW story — Page 4 of 5

[M]y strip poker loss with three [F]’s.

As luck would have it, my senior year of college (1998-99), I along with two other guys, got the opportunity to play strip poker with three girls we had been platonic friends with for the previous 3-4 years. I was really excited because one of the girls, Traci, who I happened to know the least, blossomed the most from when I first met her freshman year. As a freshman, Traci did not have the best complexion, she was heavy in a way that lent her body little definition, and her curly hair was too long and unruly. By her senior year, however, Traci’s complexion had vastly improved, she lost just enough weight to gain that definition accentuating her still ample breast and ass, and she cut her hair so that it was no longer the ‘grunge’ look so popular when we first entered college. She now had a stylish do that complemented her face very well.

The fact that we always got along but never spent that much time together, I felt, made it more likely that we could ‘hook up.’ Basically, I felt I was not so entrenched in any ‘friend zone,’ as I was with the other two girls. Finally, senior year we were both living sans roommates in the same apartment building. Read more »

The one time I [M] did not announce before a [F] got me off from a blow job

If you’ve read my earlier post entitled ‘My go-to move when performing cunnilingus,’ you know that I would subtly turn my body to cum somewhere on my partner’s body when getting a hand job while going down on her. Perhaps that was sneaky and ungentlemanly, but where I always tried to be a gentleman was with head. If I were getting a blow job, either on its own or in conjunction with 69, I would always announce before ejaculation, except this one time …

I [M] once got head on Lake Shore Drive from a [F] date on the ride back to her apartment.

If you read my gonewildstory about my platonic female friend who set me up on a date with her younger sister, and through that one date I ended up hooking up with two of the sister’s friends, the platonic friend is the same gal who fixed me up with this woman. My friend was working at her first job after college, and was kind enough to set me up with her co-worker, Becky.

The date I took Becky on went well. We had a nice dinner of tapas and though she was friendly and seemed interested I did not expect her to start blowing me as I drove her back to her apartment via Lake Shore Drive (in Chicago). Eventually, I had to ask her to stop because I was getting close to cumming, and I wanted to extend the evening at her apartment. I recall saying, “As good as this feels I have to ask you to take a break because there’s some things I want to do to you at your apartment.” She laughed and complied. Read more »

[M]y fetish in college [f]or smelly vaginas

A lot of it has to do with my burgeoning desire to perform oral sex once I got to college. I didn’t have the guts to really try going down all that much before that point. If you read some of my previous posts, you’d know I was quite the late bloomer, having never even kissed a girl by the time I got to college.

However, my sophomore year of college I overcame my fear or rejection and showing my inexperience. The first time I kissed a girl I got my first blow job! The only reason I didn’t go down on her was because she was on her period. But the second girl I hooked up with, I did go down on her. It’s probably deeply psychological, but I think because this girl had a rather musky, even gamey, pussy odor, it kind of conditioned me to appreciate the stronger smelling varieties of vagina. Beyond the erotic smell, she had a huge triangle of black hair that I found sexy and womanly. Like, ‘Yepp, this is a lady’s vagina, not some little girl, she’s ready for you to lick it all over.’ Read more »

E[m]barrassing [f]ingering story

In December of 1996, I was on winter break from college. I returned home to Chicago and I met a cute Latina girl named Faith at the bar of a restaurant that I’m sure is quite well-known, the Cheesecake Factory. Faith went to a local college whose break had not yet started. So we went out the next night and ended up at her sorority house. I wasn’t being loud, but I was fingering Faith who seemed to enjoy it as she was moaning softly – but moaning nonetheless. I think those sounds plus the lamp light visible below the base of the closed door was enough to get the house mom awake and investigating. The house mom really wanted to catch me ‘pink handed,’ because there was no warning! No audible footsteps. Just a door suddenly swung open with poor Faith’s thighs spread apart facing that door and some random dude finger blasting her. Read more »

[M]y go-to move when per[f]orming cunnilingus

Admittedly, this is less an individual story than a routine, sexual practice. However, I thought it would apply because it was an element with so many of my hook-ups in college and meeting women off of AOL post-college.

As some of you know from reading my earlier gonewildstories, while I did not have a lot of intercourse during and after college, I was always eager to go down on gals, and as luck would have it, I got the opportunity to go down on many partners. I actually have an exhaustive list in one of my diaries from my single days, and the number of vaginas I ate between 1996 and 2003 when I met my girlfriend-turned-wife, was upwards of 30. My go-to position for cunnilingus was to lie of my back with my feet next to my partner’s head. Her right leg would be straddled over my torso, my face in her crotch. This position allowed the female easy access with her right hand to stroke my erection, and in all but two instances, they immediately started giving me a hand job when I started ‘eating.’ It was like a reflex, My tongue on their clits would automatically cause their hands to jerk my cock. Read more »

Breaking in new [m]attress with [F] who contacted me on dating site

In early 2002, I was on a Jewish dating website from which a nice girl contacted me after reading my profile. She was just about to start a lease in a newly constructed apartment building in Chicago. From the picture (of really only her face) on her profile, she didn’t look all that attractive, but not everyone takes great pictures, right? Also, I made it a point never to ignore a woman who takes the initiative to contact me. I hated it when I’d send messages only to be ignored, so I could not do the same to someone who messaged me.

We set up a date for the very evening she would be moving into her new apartment. The plan was to pick her up there and take her out to dinner. When she opened the door I noticed that she did look better than her photo. Not astoundingly so, but better. But now I got to take a look at her body (unseen in the earlier photo). And if I was lukewarm about her face, I was sold by her figure. Not the conventionally sought after physique, but right up my alley. Somewhat tall – maybe 5’6, athletic. Broad shoulders, probably C-cup breasts, and a nice round ass. Her ass was so wide it lent her a pear-shaped figure. Athletic legs and thighs. I distinctly remember thinking, ‘I’m gonna’ lick this girl’s pussy tonight.’ Read more »

Wisconsin [F]s introduced [m]e to the world of sex.

I have to warn you, this is not an individual ‘gone wild’ story as much as it is the story of how I had finally ‘gone wild.’ I felt it belonged here because it is the truth – my truth. Rarely is the whole truth glorious. It is often embarrassing, regrettable, or possesses some element one would prefer to ignore or forget. The truth of my sexual development is no exception to that rule.

The fact is I was an extreme late bloomer. I was shy around girls in high school in the early-mid ’90’s. When I tried to talk to them I had no game. Even if I became friends with girls, I was never able to seal the deal and hook up. I played out the textbook psychological defense mechanisms like: having crushes on girls that I would have no chance of getting; the moment a girl expressed or indicated interest in me I’d assume there must be something wrong/unattractive about her; and adopting the ridiculous rule of only hooking up if/when I was in a committed relationship. Hell, I went to my senior prom with an old friend, and thinking back, I’m certain she would have hooked up with me had I made a move, but, of course, I was too much of a pussy. Read more »

[M]eeting a [F] visiting my hometown with her friends, then flying to Ohio for sex

Despite my profile message, here’s an experience that did result in my having intercourse … technically. It was early 2001; I was 23. I was living in the Chicago suburbs with my folks saving money after college. My buddies and I would regularly carpool down to the city on weekends and go to bars and clubs. One night we went to a brewery/restaurant and met three women 2-3 years younger than us. They were visiting from Ohio and staying at a Homewood Suites around the corner from the brewery.

We ended up going to their hotel and hanging out in the hospitality suite on their floor. I was really hitting it off with Sara, a doe-eyed beauty, standing about 5’6″, far and away the best looking one of the three. If it were the other way around and one of my buddies was hitting it off with Sara, I certainly wouldn’t have blamed at getting to know either of the other two, but my friends were not as flexible. Read more »

Awesome night visiting [M]y alma mater with current [F] student

This would be spring of 1999. My second semester senior year at the University of Wisconsin I met a sophomore named Becky. I had already completed all of the coursework for my psych. major, and I was this semester completing my second major in journalism. She was just beginning in that major. It was just bad timing because it was clear to both of us that we would have been a great couple had we met earlier in our college careers. It was such a shame because, though there were no shortage of attractive females in the journalism school, oddly enough I never got any dates/hook-ups out of that major. Finally, I meet a cute, so so sweet girl who sees me as a mentor of sorts in the area she’s majoring, and I’m graduating in May.

There was just enough time before graduation for a pleasant hook-up. She and her roommates threw a party that she invited me to attend. As the evening wore on and most people left, we started making out on the couch. The lights were off so no one really saw us doing anything, and all there was to speak of was kissing, my fondling her rather round breasts over her blouse, and rubbing her vagina over her black, rayon pants (remember those relics of the mid-late ’90’s?). Read more »