[MF] Sex with plain Jane from college

This happened 30+ years ago, but I will never forget my first night having sex with Carrie.

Carrie and I were both students at a small midwestern college. We were pretty good friends there and she was a fun companion — a great conversationalist, smart, and available and up for adventure. I thought she might have a thing for me, but I didn’t really have the hots for her. Carrie was plain looking and shy. She dressed conservatively and seemed inexperienced, so I didn’t think of her sexually. I was more interested in her roommate, who was seductive and sexy and damn good looking, but I never got anywhere with her roommate.

Still, Carrie and I kept in touch over the years after college. She eventually landed in graduate school a few hours away from me, and we’d write letters or call each other, and she even came to visit me a couple of times. During one visit she and I had dinner with another couple (who had more brains than me) and they liked her and could tell that she was interested in me. They privately asked me if we were dating, and when I said I wasn’t, they said “that’s too bad”. Instead, I was trying to get back with an old girlfriend named Rachel — Rachel was experienced and great in bed, and I wanted to be with Rachel again — so I just treated Carrie like a friend during that visit.

Still, that comment by the couple might have started me thinking, and as time went on I started thinking more about sex with Carrie. She was really small — under five feet — and slightly built, and I knew I could physically dominate her, which was (and is) a turn on for me. And while her manner and dress was conservative, and while she never flirted in the conventional sense, at some point she told me a story of how she’d fucked a guy who already had a girlfriend. Although Carrie really liked this guy, he just saw her as a friend, yet somehow one wild night she had a threesome with him and his girlfriend. She described the night as really hot and let me know she was totally turned on and had a huge orgasm while being fucked by the guy with his girlfriend right there. If she was trying to pique my interest by telling me that story, she sure succeeded, because after she told me the story, I definitely thought about her as a sexual person. I realized she was more adventurous than I gave her credit for (the old sexy librarian thing) and that she might well be exciting in bed. I also knew she had protection — she used a diaphragm — and I trusted her to use it.

So, when Carrie came up for her next visit, I was seeing her in a different light. I fantasized about sex with her and taking control. I figured she would be submissive and would do whatever I wanted. I imagined fucking her roughly and gagging her. I even had a bandanna ready by the side of the bed in case she was into it. But when she arrived, she wasn’t wearing sexier clothing, she wasn’t flirtatious, and when I asked her the first night if she would like to sleep with me (rather than on the couch), she said no. I didn’t push the issue. The fact is that she wasn’t the only hesitant one — at that time of my life I didn’t have the balls to show my sexual desires, I talked way too much, and I chickened out like I’d done many times before. While we did sleep together the second night, I wouldn’t make the first move because she had said she wasn’t sure about having sex. I think she was shy and was waiting for me to take control and to show some desire myself. But I didn’t, so we just cuddled, which was OK, but not at all what I had really hoped for.

Still, we had fun over the weekend, and she wrote me to tell me how much she liked me and how much she enjoyed our time together. Not long after that we made plans for another weekend visit — but she’d host me this time. I hadn’t gotten laid for a while, nothing was happening with me and Rachel, and unlike Rachel, Carrie was glad to see me. Even though Carrie had said she was hesitant about sex, I also knew she hadn’t ruled out the idea.

I arrived into town and Carrie and I went out for a late lunch. I thought she looked nice, and I told her so. We were having fun together, and I anticipated that when we went to her apartment, Carrie and I would jump into bed and have some great sex. I didn’t work out that way, however. Her roommate was around, and Carrie had schoolwork to do, so I just hung out and read. Carrie seemed blue about graduate school, and that was kind of a downer — any sexual tension that might have been there seemed to melt away. The evening was oddly flat.

But then her roommate went out, leaving the coast clear for us. It was getting late, she said she wanted to go to bed, but once again she said she was hesitant about sex. We talked about it. Fact is, we talked too much about it. She said I could sleep in the same bed as her, but that we wouldn’t have sex.

It was awkward. For a bit we just were in bed, lying there stiffly, not touching each other, not making a sound. I thought I was being “considerate” of her (yeah, I know). Once again, I didn’t make any moves. Eventually we went to sleep.

But at 3:00 a.m. I woke up and I was horny and something snapped in me. As I was lying next to her I decided to stop playing it so safe, to make a move, and decided that I was going fuck her. No chaste cuddling. No discussions. Without saying a word, I moved over and kissed her brought her close to me. I touched and stroked her back, her legs, her hair, held her cute little ass, went under her panties, then removed them. She didn’t draw away at all — instead, she responded, tentatively at first, then with enthusiasm. Our kisses grew longer and deeper, our breathing quickened, we were exploring each other all over. She felt good. I liked the way her small body felt.

We didn’t talk. I took control, and she responded. I didn’t ask for her permission at any point and I didn’t ask what she wanted. I simply acted and moved forward.

Still saying nothing, I rolled her onto her back, I got on top and mounted her and began fucking her missionary. She was plenty wet. After a few thrusts I moved her arms over her head and pinned her hands and wrists down while I pumped in and out. That’s a position I love — it’s dominant and intimate at the same time. She squirmed under me and thrust back. The feeling of holding Carrie down, her small hands pressing back on mine, her squirming under me, was so exciting.

Her pussy was tight — it felt wonderful. Her pussy was the tightest and best of all the women I’ve fucked and looking back I’m amazed I didn’t cum into her right away. But I didn’t — I had a fair amount of staying power then.

After fucking missionary for a while, I told her to get on her hands and knees. She complied immediately. I wanted to fuck her from behind and see her back and hair while I thrust into her. I don’t have a porn star sized cock, but I think it’s bigger than average. As I entered her doggy style, she said “you’re very well endowed”, which I of course loved to hear.

She did everything that I wanted her to do. She was submissive yet enthusiastic just as I’d fantasized. She came at least once, and eventually I came in her. I liked that I didn’t have to wear a condom and that I could shoot my cum directly into her tight womb. It was a great night of sex.

In the morning we slept in, fucked again, and then decided to go out for lunch. While we were getting dressed she said “would you like me to wear a leotard?”. What a turn on — she knew that I found leotards hot but she had never worn one for me. I of course wanted her to wear a leotard, so she put one on, and while we walked down the busy street, I kept a bit behind her so I could watch the guys coming toward us checking her out. She must have had that “just fucked” look to her. It was cool to see her looking sexy and cool to see guys looking at her sexually.

We had a nice lunch and we agreed that the night had been fun and that it didn’t have to change our relationship (of course it did, at least in the short term, but that’s another story). I had to get back home that afternoon and we went back to her apartment so I could pack up. I remember we didn’t have much time before the bus left but I was horny and wanted to fuck her again. I remember her below me on the couch, her shirt still on, her jeans off, her panties off, her legs up and spread, her pussy open there for me. I’d like to say we had another great screw, but I’d be lying — I had to use a condom and I wasn’t very good with them, so I’d get soft. In the end I couldn’t enter her and we laughed and gave up.

She walked with me to see me off. I took a picture of her at the stop, she was laughing, with a big but somehow shy smile on her face. The picture is a big turn on to me even to this day.

Carrie and I continued to see each other for a while and we had good times in and out of bed. I remember another night where she wasn’t in the mood when we went to bed, but at 2:30 in the morning, she must have been pretty horny because she woke me up and seduced me without a word and we had another great screw. I guess the middle of the night was the right time.

Later that fall I got back together with my old girlfriend Rachel, and I stopped seeing Carrie. That was a mistake. Things didn’t work out at all with Rachel (they almost never do with exes, but I didn’t know that then). However, I met my wife Lori soon after Rachel dumped me, and Lori and I been happily married for over 25 years.

Carrie also is happily married as far as I know. She lives far away, and while we’ve kept in touch a bit over the years, we haven’t seen each other for a long time.

Even though my affair with Carrie was brief (and shorter than it should have been), I’ve never forgotten her. Yes, she was plain looking, but she was a kind person and the sex with her was wonderful. She was small and tight and submissive and enthusiastic and many times I’ve fantasized about banging her again. Sometimes when my wife sucks me off I fantasize that she’s Carrie and it almost always gets me harder, and as I cum, I fantasize I am shooting my wad into Carrie’s mouth and that it’s Carrie who is swallowing my load down her throat. Sometimes when my wife and I are having sex in the missionary position, I’ll pin her wrists down, and I’ll fantasize that I am holding Carrie down and fucking Carrie as I did that first night so long ago.

Source: reddit.com/r/gonewildstories/comments/5trdfb/mf_sex_with_plain_jane_from_college