This story is completely true, at least to the best of my memory. It *was* a few years ago, around this time of year, so I’m sure I’m misremembering some of it, but a lot of it I remember incredibly vividly. It came to mind last night, when out at a brewery, I saw a girl that reminded me of her and I was reminiscing *hard* the rest of the night. It’s long on situational stuff, so I put a break in when it gets good.
(Name changed obviously) Becca was a friend of a friend, and recently started hanging out with our extended friend group. It didn’t take long to find out why she was coming around, even though she had been in our city for a few years/worked with people I knew friends the entire time. At 24, she had gotten married to the guy she dated all the way through college, the only guy she had ever been with, and less than a year later (or as I found out recently, also on their honeymoon! Douche), he was cheating on her, got caught and was moving in with the other woman. So we welcomed her into our group with open arms. As one of the few single guys in the group (after getting out of my own long relationship), I was happy to have a other single girl around, and flirted with her liberally, even if I didn’t think it would go anywhere. She was incredibly cute – a super petite, blonde/blue eyed, an adorable girl next door fantasy.
I hosted a New Years (pre)party that year, and somehow everyone I knew was staying in town for NYE that year, so it turned into a massive one. 70 people, lots of good food and good booze and tons of girls in sexy dresses. That night, I hooked up with a different girl, Kristy, that I had been talking to for a bit. I had gone into the night knowing that was a likely sure thing and nothing else got in the way, so we made out while dancing, then went and hooked up. Apparently, our soon-to-be divorced heroine took notice and was a little jealous.
New Years Day rolled around and a bunch of us dragged their hungover asses out of bed and to a friend’s house for brunch and football and general laziness. The good news was this was a year that Jan 2 fell on a weekend, which meant nobody had to work the next day, so mimosas, Irish coffees, etc all flowed slowly but consistently throughout the day.
Becca was there, looking cute as always, as the night set in. I went to make myself another drink as everyone moved back into the living room to settle in for the last half of football, when Becca caught me completely off guard with a comment. “You know, I was pretty jealous when you and Kristy were making out last night. Did you go home with her?” I didn’t even know what to say. I don’t know what I said, but I’m sure it wasn’t suave or slick. But through the quick conversation, I acknowledged that we did, that it was the first time we had hooked up, and I had no idea if there was any future in it, since it was really just a very drunken one time hookup. I did recover enough to tell her that I didn’t know she felt that way and that we should talk more about it when we had a chance. She suggested after the football game ended and everyone was leaving the house we were at, I could drive her home (she had walked over earlier).
When we got in the car to head home, she suggested that instead of trying to find parking near her place, we just head to mine (a few blocks away from hers), where I had parking. So we returned back to my place, where it all started 24 hours prior, and cuddled up on the couch together. It was the first time I had heard some of the details of her real story, little by little. We both acknowledged being attracted to each other, although she was a bit hung up on the fact that I had hooked up with Kristy the night prior still. We stripped off the sheets on my bed, only to realize my other ones were also dirty because a night or two pryor to NYE, my long term ex had stopped by for a little no strings attached fun. Not my finest moment, obviously, and something that might have doomed longer term chances in advance. We made it work with comforters and blankets, and curled up in bed for some passionate making out and more talking. She said (in more words) that she felt ugly and not wanted, given the shit her ex pulled, and I tried to reassure her that she was effing gorgeous and that most of the single guys in the city would throw themselves at her if they had a chance (I was later proven right). Trying to make her comfortable, I told her she was completely in charge and could tell me to do more or less or none of everything/anything, but I promised to do my best to make her feel good.
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As we made out, we slowly stripped each other down to underwear and slowly pulled those off, too. It quickly turned into one of those passionate, rolling all over the bed, hands exploring each other’s bodies, incredibly hot makout sessions that had both of us dialed up to 11. I kissed my way down her body, making sure to spend time with my hands and lips at every spot I’ve ever known a girl to like. Ears, chin, neck, collar bone, chest, all sides of her breasts *except* her nipples, her flat, toned stomach, hips, lower inner thighs. I kept returning to her lips to kiss her and tell her how sexy she was. Each time I kissed down her body, I got closer to the her nipples and vagina. When I licked and sucked on her nipples for the first time, the squeak/moan she let out was incredible and let me know I had done a good job on the build up. When I moved down to her pussy, however, she immediately stopped me and pulled me back up. It was then that I got (some of) the rest of the story (pieces that I learned later are also included, cause when I learned everything is a bit fuzzy).
It turns out her (soon to be) ex husband (since the divorce wasn’t even final yet) was an absolute douchebag in bed. He was well endowed, but that was about it for positives. He didn’t like oral and the idea of him lick her pussy was disgusting. He didn’t like getting head either. He wouldn’t cuddle at all, and all the sex was missionary position, at most about once a week, often way less. Generally seemed like the most boring sexual person ever (except for, ya know, the rampant cheating). She pulled me up because she didn’t want me to “have to do that” to her. I was kinda floored. I learned to like eating pussy many girlfriends ago, and love the idea of making my parter lose control with my hands/tongue. It took me a few minutes to convince her that it was something I *wanted* to do to her and that I didn’t find it disgusting at all. I’m still not sure if she believed me right away (although I convinced her before long!) After reiterating the “stop me at any time” rules, I moved back down her body and began slowly, gently licking at her clit. It didn’t take long before she was panting and letting out these sexy high pitched moans, in line with her tiny frame.
After a while she pulled me back up to her and told me how incredible it felt, that she didn’t know it could be that good or what she was missing. I asked her if she orgasmed, and that was when the next revelation hit – she told me “I don’t know? I guess?” to which I told her “if you don’t know, then the answer is probably no.” A little more discussion led to the knowledge that she had probably not, ever, orgasmed. Of course this just gave me a new goal. This time, I slid in behind her, spooning her and moving my hands over her body while still in a position to kiss her. I moved one hand lower and alternated between my fingers sliding over her clit and into her very tight pussy. It didn’t take long until she was moaning/squeaking again, and I could feel her body tensing up. I tried to coach her to relax and continued kissing her, and before long her body was quivering in my arms as she panted for breath. She never swore much before or after that, but hearing her say “Holy crap. Holy crap. Ahhh…. Holy crap that was intense” was insanely adorable.
Once she caught her breath, she basically jumped me. Despite, at the beginning of our time at my place, saying she didn’t want to have sex that night, she relented and told me she wanted it, but I resisted. I told her she should stay strong in that, that we can have plenty of fun making out and letting our hands roam tonight, and if she still thinks having sex with me the next day was a good idea, that I’d gladly oblige. She kept saying that it was my turn to get off and after some convincing, ended up using her hands to get me off. The rest of that night was a lot of kissing, groping and cuddling into the next morning.
We went our separate ways for a bit, after I dropped her off, but she texted me later about coming over to her place, that she’d make me dinner. So we reconviened at her place later that night, and after dinner/dishes we couldn’t keep our hands off each other. Before we got down to business, though, we had a long talk about us having sex. Talk about whether me and Kristy were going to see each other again, talk about what she needed in her life after douche bag left. I was/am a firm believer in that she needed to date multiple guys and see what was out there, not just pickup a new exclusive boyfriend 2 months after the husband was gone. I told her I wanted to date her and spend time with her, but she needed a few months of freedom to make sure her head was right, and that after those few months, I really hope she still wanted me. In hindsight, I was way to nice because that conversation ultimately ended being my downfall, but not before some fun, first.
We crawled back in bed that night. I entered her first missionary, then pulled her to the side of the bed where I could stand with her laying face up. She was incredibly tight and I didn’t last very long, but she was so sexy and cute that it didn’t take me long to get hard again. That first night, we must have had sex 3-4 times. She told me it was the first time she had sex doggy style and the curve of my cock sent her over the edge almost immediately, which she claimed was the first orgasm she had from sex, ever. Her ass fit her petite little frame perfect and looked great on display up in the air. She’d have been a r/cutelittlebutts (or petitegonewild) superstar. I ate her out again, earning another orgasm and she tried sucking my cock. I’m sure she had tried on her ex a few times, but clearly not much, so it was a learning experience. Like the rest of her, the effort was super cute, as she just kept saying she wanted to learn how to make me feel like I made her feel with my tongue and hands. We cuddled and fell asleep together. The next morning, I moved in tight to her, spooning her and putting my top leg over her bottom one, between her legs and started kissing her neck. I’ve never felt someone get so wet just from some morning cuddling. I guess it just backed up the whole “my husband never cuddled with me” thing. I’m talking “drip down her leg onto mine” levels of wetness. It was so hot. It didn’t take long before I entered her from the spooning position. We fucked there, then got up and fucked in the bathroom where she could watch in the mirror, then in the shower.
The next few weeks were a whirlwind, with each of us staying at each other’s place, making out, licking and kissing every inch of her body and multiple rounds of sex per day we spent together. We had sex on every surface of her/her ex’s large condo, taught her to give head, made her cum on my tongue repeatedly and generally taught her what hot, passionate, wild sex could be like. It was fucking incredible. She genuinely wanted to do anything that would make me happy in bed. Facials, toys, beginning anal play (needed to work up to my cock), even talked briefly about 3somes.
Unfortunately, the story ended before it could get even more fun, as my encouragement for her to date around a bit led her to a guy who pulled out all the stops to make her his and only his. Within 3-4 weeks, she was gone, in a committed relationship and re-married less than 9 months later (yes, really). That short tryst still crosses my mind once in a while (like when I see a girl that looks like her) and makes me think about how damn cute she was and how fun she was to teach/corrupt. And what could have been…
Source: reddit.com/r/gonewildstories/comments/a7rlga/mf_new_years_fling_and_teachingcorrupting_the