I used to be like a lot like many of you, dear readers: Jealous of all the incredibly hot sounding hookups, and confident that every guy involved must be a solid hunk of handsome or well-endowed. Well, I’m neither of those things, and I still pulled it off.
Sexy bits will start after the ~~~~~ line.
My girlfriend and I had been together for over 7 years, and the time had come for her to move out to start the next phase of her life and career. Only problem was: I was still a broke NEET, and totally unprepared to move cross-country to live with her, like we would’ve liked to. This wasn’t a problem, our plan just changed to have me move out to catch up with her, rather than to move with her. We agreed on a long-distance relationship (nothing new for us in this relationship), established our boundraries, we said our farewells, and that was it.
She and I are totally inseparable, so we’ve been texting and calling a lot. Only trouble is, I’ve got quite a high sex drive, and she simply… doesn’t. We would sate my desires with sexting, photos, and even the occasional video, but I was left wanting more. Wanting real sex. After a while, I popped the question that had been lurking in my mind for weeks, if not months:
“Would you be cool with me just sleeping with other people?”
Now, call me what you like, but I’m a greedy son-of-a-bitch. So, my stipulations were that I still wanted total monogamy on her part. However, if she accepted, she has full disclosure and “remote control rights”, ie she can pause, stop, and turn off the deal at any time, no questions asked. In addition, I promised that if she didn’t accept, I wouldn’t badger her or hold it against her in any way: this was truly her decision, and she only needed to take into consideration her own feelings.
This wasn’t a decision either of us took lightly, as we had both been monogamous to each other for the whole relationship, and we were each other’s first partners (even taking each other’s virginities). So, we discussed. I left her alone when she didn’t want to talk about it, and talked when she did. After a few long, arduous days, she came to her decision:
Now, based on the subreddit you’re reading this story on, she accepted! Granted, I wanted to be really, really sure she was okay with everything, so I asked enough times for the question to grate a bit, then once or twice more. But now, opportunity in hand, I took to tinder.
I’d already had a tinder before, just to chat with strangers, but now that I was looking for a hook-up/FWB, I needed to try a bit harder. So, I updated my photos and bio, and proceeded to try out my favorite, “never fails” strat for easy matches:
I swiped right on everyone. I didn’t even take the time to check for bots or ads; this shit was like cookie clicker for cute girls.
Granted, not every match led to anything. Some girls I didn’t message, some didn’t reply to mine, and others still just weren’t interested in meeting up. But, then I found her. At first, she didn’t really stand out much, but then she asked me if I’d like to snapchat with her. I wasn’t sure where this was going, but the fact that she asked me told me it was going somewhere I definitely wanted it to. I quickly accepted, and reinstalled the app.
Things definitely went where I wanted them to. We chatted for a while, before she sent me an image, chock full of questions to ask, each with their own number. Now, I had seen these before: what really intrigued me was that over half of these were dirty in some level, and ended with “send nudes” (in more pleasing words). I went for it, and we begun.
In a show of restraint that surprises even me, I decided to bide my time until I knew she was into me. It didn’t take long before she asked magical question #18, “Do you think I’m attractive?” I replied with an emphatic “Yes” about how hot her tinder pictures were, and then we were off to the races. I didn’t jump straight to the most racy questions; I still wanted to escalate things, but I made them escalate a fair bit more quickly. (Side note: she later ended up telling me how much she loved how aggressively I’d pursue her. I guess being a horny, thirsty SoB is worth something after all!) By the end of the hour, we were swapping nudes, and talking about how badly we wanted to fuck each other. Issue was, we were both living with our parents at the time.
But this wasn’t going to stop our horny young adult selves, and we kept swapping nudes, videos, and sexting each other, even going so far as to get some sexy roleplay involved, once we figured out which kinks we both shared. We discussed protection, and we agreed I could go raw after she told me she’d always used protection with everyone else, but I still had to pull out. Not a problem, I’m an absolute pull-out champ, I thought to myself. We also talked a bit about how we liked it, and she let me know she really enjoys cervix stimulation. Also not a problem, I thought. My cock is average length at best, but with the right position I could bottom out in nearly anyone.
~~~~~
But, you can only keep two horny people away from each other for so long, and eventually, we found a day that I had the house to myself and she had time available. She drove up to the house, I let her in, and we snuggled up on my bed.
I was admittedly pretty nervous, so I just held her in my arms before making a move. I tilted her head up by her chin, and started a kiss, while I slid a hand down to one of her tits, and gently pinched, twisted, and otherwise played with her nipples. Her nipples being very sensitive, that drove her crazy. She repaid me by rubbing her cupped hand over my dick, and kissing me back harder. Not looking to tease one another, I moved my hand down her pants, past the panties she wasn’t wearing, and started playing with her pussy directly. Her clit was so small that I wasn’t really sure if I was actually rubbing it, so I just rubbed in the general area where it would be, and that did the trick for her. Then, I stuck a pair of fingers in her pussy, and started performing the tricks I’d learned with my sweetheart gf. I was twisting and curling my fingers while gently sliding in and out, rather than just pounding like my fingers were some kind of makeshift dildo. She returned the favor by sliding her hand under my boxers, and rubbing my cock directly.
Eventually, I’d had enough of the build-up, so I pulled my fingers out of her, and slid them into her mouth. She cleaned her pussy juices off me quite thoroughly, while I undressed myself with my other hand. Then, I gave her a hand with getting undressed, rolled her on her back, climbed between her legs, and got ready for the main event.
I lined myself up with her cute innie pussy, and fully appreciated the moment where I’d be the first man to feel her raw. I slid inside, and her pussy was so wet, I was in heaven again. She responded by throwing her head back in bliss and letting out a heavy groan. (As it turns out, despite my average size, I was the biggest man she had ever taken, most notably in thickness. She never knew what she was missing until she tried out a thick cock.) I like to treat any ladies who decide to fuck with me, so I was sure to take time rubbing her clit and pinching her nipples while I slid in and out of her. Her pussy was so damn tight and rippled on the inside, that it was extraordinarily difficult to not pop before she was done, or so I thought. Turns out, she’s not only multi-orgasmic, but also immensely sensitive. I slowed down, savoring every inch of every thrust, and before I knew it, she was close to cumming on my cock. I reached up to gently choke her, and that sent her right over the edge, combined with my other hand playing with her nipple and my slow, deep, hard fucking. The pulsing and squeezing of her pussy was practically begging me for my load, but I wasn’t ready to cum yet.
I wanted a look at her big, round ass, so I pulled out, and rolled her onto her side, straddled her bottom leg, and slipped back in. She felt even tighter than before, if that was even possible. I grabbed her hip with one hand and reached back up for more nipple play with the other, and decided it was time to make myself cum. I started pounding harder and faster, escalating more and more quickly, and almost to my shock, she beat me to an orgasm again. This time, I helped her along with a flurry of spankings while I continued to ram her.
Not long after, I told her I was ready to cum, so I quickly rolled her back into missionary, and pounded her with every ounce of strength and energy my hips had left. I quickly put myself to the edge, pulled out, and finished myself off all over her. And when I say “all over her”, I mean it. She’s half a foot (~15cm) taller than me, but even as I squatted near her pussy, didn’t stop my cock from shooting all over her stomach, tits, face, and even past her entirely, hitting my pillow. Cumming that hard is incredibly rare for me, so it’s nice that my dick decided to be a bro and really impress her right at the finale. I grabbed a towel from my laundry basket, wiped her off, and snuggled up before round 2 began. BUT here’s where this story will have to end, for now.
~~~~~
This wouldn’t be even close to our last time, as we’re still FWB today. We’re both attending school and have jobs in towns separated by a half hour, so it’s hard to find time to bone, but she’s always down to swap a few pics. I’ve gotten to try all sorts of fun things with her, from eating her out to having her ride me and even experimenting with anal and car sex.
I’ll be keeping an eye on my notifications for a while before I switch back to my main account, so feel free to ask any questions! She’s also fond of me showing her off to my friends, so I’ll quickly ask if she’s okay with me posting some of her nudes here too. ;)
Source: reddit.com/r/gonewildstories/comments/f6hghi/my_sweetheart_let_me_see_other_people_i_didnt
Best story I’ve read.
Nicely played, man!