[M]y [F] that got away

My senior year of college I lived alone. Every previous semester, including my study-abroad term, I had roommates. In fact, my freshman year and study abroad semester I actually shared a bedroom with another dude. So finally, I was living completely alone. I had my own bedroom. My own kitchen, den. I could come and go as I pleased and if I were lucky enough to bring a girl back with me, there was never any distractions from a roommate/suitemate or their respective guests. By far I got the most action my senior year, but the funny thing is, as often as I hooked up that year, there were quite a few rejections I’d experienced. It was a numbers game and I tried making a move on every girl I thought I had an opportunity with … every girl except one.

Sara was also living alone in the same apartment building. I did not know this at first. I had met her in a journalism class I was taking. Once we got to talking, it was revealed that we lived in the same place. I asked if I could stop by and she was cool with that. So I did and we really enjoyed each other’s company. However, the first time I stopped by I learned that she had a boyfriend who went to another school in Wisconsin. I always drew the line with hooking up with gals who had boyfriends. What can I say, I always thought, ‘What if I were in their shoes and my girlfriend cheated on me with some other guy.’ Well, before any of you give me credit for being so noble, you’ll have to read the next section of this anecdote …

Sara and I were openly quite attracted to one another. She had raven colored hair, great facial bone structure, wide, pretty eyes, and a thin, tight body. Somehow, though we never should have even gone this far, we got to talking about our ‘private parts.’ I touted what I described as my “large penis;” she was equally proud of her “perky breasts.” I dared to make the ‘I’ll show you mine if you show me yours’ offer, and son-of-a-bitch, she accepted it. I remember going into her bathroom to get myself a hard-on to make the best impression. I came out, unbuttoned my jeans, unzipped my fly, and dropped my pants exposing my pubic hair, fully erect penis and testicles. Sara remarked, “Wow, you are huge,” and true to her word, she removed her top and bra. Also true to her word, her breasts were terrific. They were probably B-cups, extremely perky and had the most beautiful maroon concentric nipples/aureolas you could hope for. I am certain that if I made a move, she would have accepted the gesture, but I just didn’t want to make Sara a cheater. She was such a nice girl, and it took every ounce of my will power, but I couldn’t make a move on a girl who already had a boyfriend, no matter how long it had been since he was last able to visit.

I continued to stop by, and, yes, we continued our sexual joking around. I’d expose my erect penis. She actually went as far as removing both her bra and pants. So I was able to see her in her underwear and see that she had a lovely set of delicately curving hips and a pretty ass. Neither big nor bony. I was even able to see a little bit of her black pubic hair sneaking out from the edges of her panties. I remarked that I liked that she didn’t shave all of her pubic hair off like so many girls were doing these days. This would have been late 1998 after all. She thanked me and remarked that she too thought it looked nice with some womanly hair around it. Again, after that line – a hairy pussy love like me – it took all of my will power not to make a move. It was clear she was really putting me to the test.

One time I went over and she had a friend over to her apartment. She remarked that I had a big cock and I was never shy about showing it. So now her friend said, “Okay, let’s see it.” Once again I went to Sara’s bathroom and came out with a raging hard-on. The friend said, “Yeah, that it pretty big, especially on such a skinny guy.” She actually proceeded to graze her finger along my shaft. I was hoping she would give me a hand job or a blow job and I thought how cool it would be to show Sara my cumshot, but that tease of a finger graze was all I got!

Then, lo and behold, her boyfriend – I think his name was Ryan – was going to visit the next weekend. I had met another one of Sara’s friends (not the penis grazer), Kim. In fact, I happened to run into Sara and Kim on the street, so I had not shown my cock to Kim, but I wondered if Sara had mentioned it to her. Sara suggested the four of us go on a double date when her boyfriend came to campus. I had liked Kim’s looks. She had long blond hair, a pretty face. Truthfully, I could never really tell what her body looked like, but I’d hoped to find out that night. We went out and I was so glad I didn’t make a move on Sara. Ryan was a genuinely nice guy. Not only was he a devoted boyfriend to Sara, he was very agreeable to me. He was either completely aloof to the heavy flirting his girlfriend and I had been engaged in, didn’t care, or was clever enough to not evince any reaction/hostility. All in all, he struck me as someone I would be friends with, so I was happy that I never betrayed him (beyond the indecent exposure silliness in which Sara and I engaged).

Kim and I hit it off when we previously met and we got on even better now that we had more time to get to know each other. The evening ended with Ryan and Sara going back to her apartment for I’m sure some much-missed love-making while I walked Kim back to her place. Kim invited me in and it was on! She also lived alone. We went right into her bedroom and started making out. As stated earlier, I had not shown Kim my penis before, but I figured now was an appropriate time. So I took off my pants and underwear, and Kim took off the rest of her clothing. Kim had one of those bodies that lent itself very well to clothes, but when the clothing was removed she was a lot larger than she appeared while dressed. I didn’t care. She still had big tits that I enjoyed licking and sucking. She had very bulbous labia majora, and closely shorn hair on her outer lips and above her clit. The bulbousness of her labia majora made it difficult to get at the ‘fruit’ of her pussy, but I managed and pretty soon I was eating her out. We ended up 69-ing on our sides. She gave me a nice blow job and I showed my appreciation by cumming in her mouth. Kim was generous and swallowed my load.

I was certainly interested in seeing Kim again. Though I wasn’t as attracted to her physically or intellectually as I was to Sara, Sara was off limits especially now that I actually met her boyfriend and he was good to her. However, though we talked on the phone subsequently, I could never nail Kim down for a second date. I think to this day Kim was Sara’s proxy. Sara knew the two of us could not hook up as long as she was dating Ryan, but she was curious what it would be like. So the closest she could get would be to do so vicariously through Kim. I certainly never posited this theory to Sara, but I often wondered if Sara knew Kim was an up-for-anything girl and she put Kim up to the idea of going on an ‘exploratory mission’ for her.

Source: reddit.com/r/gonewildstories/comments/u3apgq/my_f_that_got_away