This story is true, and is a tribute to [this fantastic story](https://www.reddit.com/r/gonewildstories/comments/el4zrv/the_first_time_i_let_a_guy_cum_inside_fm/) about a woman and her first cum inside by a guy. Plus a couple of people messaged me to ask for more details. In no way do I intend to steal that author’s thunder… in particular because there was a *lot* of thunder in her writing. :-)
Update 2020-01-09 : Looks like they deleted the story. That’s a shame!
Note that names have been changed.
Between the time I was 28 and 33/34 I went through this phase where *all* of my relationships were sexual in nature. I was a late bloomer; what can I say? Even though I’d had relationships that involved sex, it was not until I was honest with myself about having sexual interests that were against the norm that I was able to relax and enjoy this part of myself.
Adult websites such as Adultfriendfinder and SwingLifeStyle as well as the craigslist “casual encounters” had come online a few years earlier, and brought a lot of bounty in terms of meeting couples for threesomes or for MILF hunting (there was a time in my life where MILFs and I *weren’t* the same age ;-) ).
I was reaching out to some new people when I saw her ad. It was in the regular craigslist personals and it said that a tall, pretty, athletic blonde female was “bored” and was looking for a chat. How fortuitous! I was also “bored” and enjoyed chatting. So I sent a quick email and got a response back in 15 minutes along with her AOL IM name. 16 years ago when this happened I was a lot less wary of things like Russian bot nets, catfishing, swatting, and other crappy stuff that we have to deal with on the internet now, so I just went into this whole thing head first.
Our IM correspondence started cordially enough. Kayla was (virtually) charming and our back and forth was fun. She was tall, as noted earlier, and she was also excited that I was tall, had a house of my own, etc. Inevitably she asked if we could exchange pictures, and sent two of hers along. I responded in kind, and was surprised when the AOL IM door didn’t swing shut on her end. Instead the conversation veered into a 101 course in cyber sex. Somewhere along the way I asked her how old she was, and she said that she was 18. I was aghast, even though her pictures did give me a clear indication that she was not 33 like me. Why did I proceed with this? It was new and I was really curious if anything would happen; I hadn’t slept with an 18 year old… since I was 18. Why was she wasting time with the likes of me?
6 hours into our sexually charged chat I had to call it a night as I had to work the next day. I figured that was the end of our correspondence, but my head was filled with sweet dreams on that night.
I logged into IM later on Monday night and Kayla pinged me out of the gate. It was every bit as sexually charged as the previous night. Every night was the same for the next couple of weeks. And then she disappeared. Maybe since it was the end of May, she packed up and headed home after her freshman year of college? Maybe we reached a saturation point? Whatever, she was super pretty with her big “deer in the headlights” eyes and her pouty lips, and I enjoyed this all while it lasted. I started re-engaging with some other people I’d met on the adult sites and started trying to setup some dates with them. It was all good.
And then it all started again one night about three weeks later. I’d been hanging out on AOL IM trying to hash out a date with a couple who were interested in a meet ‘n’ greet then possibly going upstairs to their hotel room for a threesome — when Kayla chimed in with a message.
She apologized for her absence and said that her computer was broken. I asked her if she was typing this message from her computer and she said that she was. I asked her what was wrong with her computer, and she said that it was slow and that things crashed a lot. Then she disappeared from IM again. 18 year olds… *OY*!
Then she returned and said that maybe her laptop computer had a virus or something — and was wondering if she could drop by that weekend so that I could look at her computer because I “worked in computers” or something to that extent. Well, yeah, I work in “computers” but I use Windows XP while pinching my nose (again, this was 16 years ago), and I do this devops and Linux shit that’s uninteresting to practically everybody. Why people like my dad and Kayla thought that I could fix their most esoteric problems with Windows was beyond me.
So we made a date (her words). I’d hopefully fix her computer and make us some lunch. She had some requests for food and I did my best to oblige. I didn’t want to over-commit because I wasn’t sure that she was going to show up on Saturday at 11am. But she did, to my surprise.
I greeted her at the door after a doorbell ring, and she looked super hot in her light-colored sundress with straps over her shoulders, and high-heeled summer sandals.
She had muscular legs and curvy hips, and she was busty beyond belief (her pictures did not call out this little, or not so little, fact). Both her fingernails and toenails had a subtle color to them, and she was immaculately ‘cured. She had obviously taken a lot of time to curl her long, blonde hair (I absolutely fucking die with lust when a women does this shit) so that it was perfect. And she wore these small hoop earrings that just accentuated her hotness. She was even prettier in person. My god. We hugged and she kept remarking and emphasizing about how tall I was, and mused repeatedly about how often I worked out. She never said that I was attractive (and that’s what made this game so much more interesting — since most people I had played with would mention at attractiveness at some point along the line), but it was all just tall, tall, tall with Kayla.
After some more pleasantries I offered her water or a soda (I was drinking white wine — I had a two drink limit before any prospective play time — just to limit my inhibitions enough to go forward with whatever might happen), and while she asked for a drink-drink, I demurred. There was no way that I was going to serve an 18 year old girl alcohol in my house, well, unless she was going to stay over. And even then I would proceed with caution; I would not serve/over-serve anybody alcohol as a precursor to a sexual event. She pouted a bit, but it was what it was.
Finally after a dizzying array of reinstalling dlls, updating Windows, and figuring out that she had a virus (and fixing it), she stopped pacing behind me. It was then that she disclosed that her massive porn collection (!!!) might be the problem. Well, no shit it was the problem. All of those files got quarantined by anti-virus protection. But, again, my god. She’s 18 and had a porn collection like this. I admit that it made me feel all warm inside. If only I hadn’t been raised by evangelicals! I would’ve done this same exact thing 15 years sooner! The fuq?!
I wondered why Kayla kept pacing around behind me, in particular after I fixed her computer issue, and she said that she needed to pee and asked where the nearest bathroom was. I pointed her in the direction of the bathroom up the hall next to the kitchen and started getting lunch going. It was 2pm at this point. I heard her aggressive pee stream hit the porcelain bowl. It seemed to go on forever. But then it stopped. I almost yelled out, “hey, are you taking a shit in there?” but I said nothing. And that was a good idea on my part because now the sex part starts.
I heard the click of her high-heeled sandals on the tile floors of the hallway. “That smells great!” she exclaimed, and I turned my head to nod to her. That’s when I realized that she was wearing nothing but her sandals. I know that my jaw dropped at this point. Big woman, a freshman-15 paunch on the belly, tall, nice wide hips with 18 year old tits that didn’t sag, two nipple piercings with rings, a nicely trimmed bush, and that ever sexy thigh gap between her pussy and her knees. Holy fuck. Why didn’t I remember my first time when I was 19 and she was 18?
I shut off the burners on the stove and approached Kayla. I grabbed her and kissed her hard. I held her body close to mine and grabbed her left ass cheek close to me as my hand snaked down her crack and to her pussy. Kayla was soaking wet. I pulled away from her and pinched at her pierced nipples and I could see the wetness as well on the pouting and sagging lips of her labia. This is only the second woman I had seen whose body behaved this way. Man, women are so sexy and their bodies do super-sexy things.
My mouth dropped immediately to her pussy and I pushed her against a wall as I started to tongue at her labia. She asked me what I was doing, her juices running down my cheeks, and I pulled away and put my index finger to my mouth. She asked me if we could go to my bedroom and we made out and fondled each other as we headed towards the staircase to the upstairs.
I spun her around and pushed her down on the third step, the whole staircase featuring a runner from the foyer to the landing upstairs. Kayla kept trying to push herself up with her arms and by digging her heels into the runner. My mouth was on her clit and I had a finger in her pussy. Then I started tonguing around her asshole before forcing it in.
“What the fuck are you doing?!” Kayla squealed. “Holy fucking SHIIIIIT!”
I took off my shirt and t-shirt and freed my cock from its confines. My fat, dark, ugly cock was engorged and I nearly fucked Kayla right there as she writhed her way up to the landing at the top of the stairs. But condoms. Man, oh man. Condoms. I had about half dozen in the nightstand and had hidden dozens of others in one of the guest bedrooms. Just in case our “computer fixing” rendezvous led to sex I did not want to turn her off by having her see probably 60 condoms in the drawer of my nightstand — when I opened up the drawer to pull a condom out.
I knew that she came the first time at the top of the landing. Her long legs were wrapped around my head, and her heels crashed against my scapula while her thighs pulsated around my ears. When she squeezed her thighs tight around my ears without letting go, she screaming like she was being knifed to death, then letting her grip glow with a *plop*, I knew that I had done my job.
She did a reverse crab walk away from me in her sexy sandals, and said, “no more of this bullshit. I want you to fuck me.” That’s verbatim what she said. She stood up and grabbed my previously mentioned fat, dark, and ugly penis and pulled me towards the open door to her left: my bedroom. I waddled in my dropped pants as my pre-cum dripped down her hand.
I kicked off my pants and shoes and my hand manipulated the drawer of my nightstand to grab a condom as Kayla and I continued to make out. My cock was just outside of her most precious entrance and my body writhed between her open legs. We had never talked about protection, and it had been a long time since I’d gone bare, so I sheathed up and entered her missionary style. Nothing. No “O” look on face. No nothing. I was wearing the thinnest of condoms and I could feel her slickness and heat. Yet nothing.
On my dozenth or so stroke she told me to stop, and I pulled out. I stayed in position between her spread legs and she grabbed my cock and pulled the condom off, tossing it to the side of the room. “I want it just like this,” she said, guiding me back to her entrance. When I inserted this time she gasped and I did as well. Holy motherfucking fuck. She was tight. And hot. And wet.
I pulled out again and plunged back into her. She let out another blood curdling scream. I did it again and to the same effect. And she went along with whatever my body and cock was doing once we went bare together. I’d manipulate her body so that I went in sideways, but the real capper was when I went doggy with her and knotted her hair around my fist as I pounded her. I nearly came about a dozen times as this continued but I kept talking myself down by thinking about Linux (Linus Torvalds is a hell of a guy but definitely one to think about if you want to last), troops in the Middle East, the stock market, if the Red Sox were going to repeat (very short in my mind, because them repeating excited me greatly), and Bill Gates/Windows XP and fixing dlls (yup, that was what lead to the length of our first fuck).
Finally I said that I was getting close and her hands slapped my thighs. She got on her back again and we went back to missionary. I told her that I was getting closer. She locked her legs around me and told me repeatedly, “in me! in me!” I thrust my hips aggressively with each push and unleashed rope after rope inside of her.
We kissed a bit then disengaged and laid next to one another. She said that she was hungry and asked if I had anything she could wear. I put her in a t-shirt of mine and Kayla wearing my t-shirt and her sexy sandals had my finger back in her pussy before I finished making “lunch”. I was able to go a second round just about when things were ready to be plated. The rest of Saturday and half of Sunday was like that.
She asked me on Sunday evening if I would be a summer romance for her and I agreed. She worked at a video store to save money for her next semesters at college, and almost every night we would fuck and fuck. She was super precious, submissive, and extremely willing. I told her that I was going to breed her but it didn’t take. She later fessed up that she was on the pill. Ah, that would explain it.
Great summer though. Yay for me.
Source: reddit.com/r/gonewildstories/comments/gff7wn/mf_i_had_a_summer_romance_with_an_18_year_old
Good read, I dated a mature student when I was at college. She was 14 years older and fucked like a energizer bunny
That’s a great story. I love younger women.
Yours is very similar in ways to my own, from about 10 years ago.
[https://www.reddit.com/r/sexstories/comments/g3oqa6/the_older_man_long/](https://www.reddit.com/r/sexstories/comments/g3oqa6/the_older_man_long/)
You can access that story here:
https://www.removeddit.com/r/gonewildstories/comments/el4zrv/the_first_time_i_let_a_guy_cum_inside_fm/
By the time you’re 30, 18 year olds seem like little girls, not women. FTFY.
Fantastic story! I loved the difference in her reactions between having you wrapped vs bare. So hot that not knowing if she was on bc that you told her you wanted to knock her up.