Inspired by one of the recent stories, I can definitely relate to the repressed religious girls out there. My own experience is with Stephanie, whom I met a few years back on OKCupid. She was a single Mom, fresh out of a horrible relationship and recently moved to the neighboring city I was in. Standing about 5’4”, her frame was fairly curvy with perky small tits but a thick ass that rode all the way up. She had brown straight hair the length of her mid-back. Kept in a business bun most of the time, but a high pony when she came to visit. Dimples when she smiled and a mild New York accent to boot. Her smile was contagious but it was her ass that was my favorite feature on her. I myself, was eager to get back into the dating game but not exactly ready for a full relationship at that time. I say all of this because we started out dull and about as anti-gonewild as one could get. It took a while for things to heat up but eventually they turned into some of the hottest sex I’ve ever had. A bit of backstory first. We went on a few dates early on but didn’t fully connect for reasons too complicated to explain. She thought I was funny and entertaining while I saw her as cute but too reserved for my tastes. During the early days, we swapped stories to pass the time and to be honest, I have no idea why I stuck around. I wanted to get laid and she had no interest in it every time the topic shifted to sex. It took a while for her to come around but eventually, rough sex where the guy took control got her interests going.
Her being a full time Mom made it hard to get time away from her kid so we just texted a lot. I thought sex was never going to happen so it came as a surprise, that when she got the evening off, she texted she was coming over. That first time we fucked, it was fun, stress relieving and fairly bland. It was good mind you, just not amazing or epic and I’ll leave it at that. Gentle, romantic making love like one would do while in love. Not the rough sex she said she talked about. Officially we became friends-with-benefits as we couldn’t see dating each other at that time. The second and third nights of sex were better but nothing gonewild material. I was just happy to get getting some while Stephanie seemed to want the basics. She talked a big game in our texts but when it came to doing anything rough or kinky, she declined every advance or effort I made.
All that changed on our fourth date night. I started off vastly different from our previous encounters because she cut loose with a large amount of alcohol and a bit of weed. Stephanie was practically a whole other woman that night and it showed in her enthusiasm. We didn’t make love, we fucked like animals! Trying several positions where she got to let go and orgasm hard. In our previous nights, doggystyle hurt her knees/hips, but this night she didn’t complain at all. I slapped her ass, pounded away in her pussy and fucked her good multiple times. The night ended and we had weeks of texting back and forth to go on. I got her riled up with what I was going to do to her next time and she felt at ease in telling me what she wanted to do. I discovered Stephanie was far more adventurous than she originally led on. She was into some kinky shit with her ex-husband and I was eager to try to do the same things she liked. The next night we got together was the true first night of our gonewild adventures. The night started off with me giving her oral and she ended up cumming hard (a first for her). Her body ended up spasming so hard that it took a while for her to calm down. She thanked me by sucking my cock, something she wasn’t into with her ex. The night continued with lots of different types of sex. The most surprising part of the evening was her willingness to use a plug in her ass while I fucked her pussy. We didn’t do anal that night but the fact she opened up enough to show me her wild side was fucking hot.
The most memorable night of sex we ever had was about 2-3 months after we started seeing each other. We had been sexting each other non-stop all week and we were both sex crazed by the time Friday night arrived. Stephanie arrived at my place in a skin-tight top that complimented her frame. She wasn’t wearing a bra so her nipples were pert through the top. Something I would have never envisioned her wearing, let alone for me. Her tight jeans hugged her ample ass and I could tell she spent hours getting herself ready for our night. We ate the dinner I prepared, got some wine into her and we settle down to watch some Netflix and Chill. Not even 5 minutes into the show, she was grabbing my crotch through my jeans and looking at me with those hungry “fuck-me” eyes. My hand dipped down to feel her crotch and she was steamy hot down there. Fully ready to go, we made out on the couch for a while and she let me take charge of where the night headed. Because we had texted all week what we were going to do to each other, I knew I was getting everything I wanted that night if I played things slow and steady.
She got up off the couch, stripped off her tight jeans, commented on her ugly belly for the 30th time, finally took off her top and stood before me completely naked. Something she didn’t like to do because of her low body image. I reassured her that it was a gorgeous body and guided her back to the couch where I proceeded to eat her out. Her pussy tasted sweet and I sucked and tongued her clit for what seemed like hours. Stephanie grabbed my hair and shoved my face into her shaved crotch (another first, just for me). Her orgasm built until I felt her about to cum and I pulled away. She whimpered in frustration. I made her promise me that I get to do anything I want to her tonight. She moaned and squirmed knowing my hands kept hers pinned to the cushions. I could tell the lust in her eyes that I could do anything to her and she would agree. Finally she moaned, “anything… just fuck me”.
I pulled my pants down while kneeling, coated my dick in her pussy juices and slide into her. Her hands, now free, grabbed my ass cheeks and she gripped hard so that I couldn’t move while inside. My rock-hard cock was fully to the hilt, just resting there and occasionally throbbing. Within moments, Stephanie began to visibly shudder. She came just from me inserting inside her and it was hot to watch her move around and gasp in breaths of air. Free to start fucking her normally now, I started slow. She grabbed the inside of her already spread legs up in the air, and pulled them back further so that I could get added length inside. This position was hard to fuck her fast so I compensated by going long deep strokes in a steady rhythm. From this angle, I was hitting her g-spot with the head of my cock and each time it brushed that spongy surface, she moaned with pleasure. Stephanie came once again just minutes after cumming hard from earlier. She had told me that she didn’t have multiple orgasms so this was a special moment for both of us.
I couldn’t cum so we stopped for a while. We talked about her multiple orgasm and it was something she wanted to do again and again. Something she would improve on later in months to come. She recovered and I got my second wind. We took things to the bedroom and she sucked my cock for a bit. Still not the best at it but good enough to get me hard. Stephanie wanted to try doggystyle again. I placed the puffy couch cushion under her hips so it wasn’t as hard on her physically and she said she wanted to try the plug again. Being prepared this time around, I got out the lube and applied a generous amount. I was fairly inexperienced with anal but I knew enough to know that when the plug slid in with minimal effort, she was ready to go. I wasted no time in getting myself hard again and using some of the lube to get her pussy ready. I slid in and fucked her hard and fast within moments.
Stephanie gripped the top of the sheets and took every inch of me with a moaning pleasure. She was so horny that it took her only a few more minutes of fucking to get her to cum once more. 3 times and I hadn’t even cum yet and I was far from needing too. Even with the cushion, she couldn’t last in that position so we changed to missionary with legs up. Butt plug still firmly embedded in her ass, she was craving more orgasms. Another big one hit her hard and she tensed up and latched her legs around my torso. She pulled me down with her arms around my neck so she could passionately kiss me. As if I lit a torch under her sexual fire, she was writhing around in an almost violent manner. Making sure to keep up the “take-charge” persona, I used her energy and desire to follow up with whatever she wanted to do. If she moved her hips to change positions, I would take over and push her into a new one making it seem like I was the one that wanted it. This heightened her sexual desire and she was all grunts and groans with pleasure.
Anal sex was something she had done infrequently with her ex-husband but it was more a curiosity with her. I was determined to do it with her but I knew to take it VERY slow and with lots of lube. I figured she was ready to try it now because she was relaxed, horny and in the mood. She was still on her back with legs up, so I slowly pulled out the butt plug. She cooed with pleasure at the pop of the removal. I tossed it aside, looked her in the eyes and told her that I was going to fuck her ass hard. Not an ounce of hesitation in her eyes, she just told me to go slow. I applied the lube to my fingers, applied it in and around her ass, even fingered her butt a bit as I dripped more lube into her forbidden hole. The cushion now back under her back, I took one of her legs with one hand and made her hold her other up and out of the way. My cock was now rock hard again as I placed my tip up against her asshole. I pushed slowly and she gasped. I told her to breath out and push out like she was trying to prevent me from entering. I don’t know which part of the preparation worked but my dick popped her butt muscle and she winced with pain. I didn’t go any further until she was ready for me to continue. After a few long moments, I ever so slowly pushed in further. Going just an inch in and then back out. Every few strokes I would go in a little bit more. After what seemed forever, I felt her previously tensed body melt to a fully relaxed form.
I began to now fully slide my cock in and out of her well lubed ass. Stephanie had her eyes closed, focusing on the moment. She had this smirk of content on her face that could only come from someone enjoying the moment. My strokes where long and deliberate as she took my full length deep into her butt and back out to the very entrance. I repositioned my angle while still inside her so that I could get a better angle. She took the leg I was holding up back with her other hand so that she was fully controlling her own spread legs and in turn the depth in which I was able to reach. I wasn’t planning on going any harder but she urged me to fuck her hard. I picked up the pace. She was moaning audibly now, but it wasn’t enough. A moment or two later, she was grunting out commands of more. I grabbed her already spread legs with both hands, thrusted my hips into her backside and fucked her hard. I was giving her every bit of strength I could muster. Slamming my cock into her creamy lubed ass. She came harder than I ever saw her before. Screaming out a continuous moan of ecstasy thrust after thrust. I exploded a stream of cum so hard that I got lightheaded from the rush. I slowed my pace and we let our orgasm ride it out for all it was worth.
Collapsing onto her, we gasped for breath and my now dirty cock stained the sheets. We didn’t care, just cuddled each other for a while in each other’s arms. We talked for a while, reliving the moment that we just played out. Her butt was very sore and it would be a while before she was ready to try that again.
Stephanie and I remained FWB for close to a year and a half. We experimented with kinks we both wanted to try, but nothing would be as memorable as that first real night she got to let loose.
Source: reddit.com/r/gonewildstories/comments/blj502/mf_okcupid_mild_date_turns_gonewild
Nice work.