To preface: This story is from some years back. I was a junior in college and life was great. The setting? winter break and I was back in my hometown. My only real goal for the break was to see which girls from my high school I could sleep with. College really is the best time of your life..
On this particular night, it was cold and windy, and there was not much going on. So, like any horny young college guy would do, I decided to make some moves on social media.
A little about me. I’m an attractive guy who likes to exercise. This was especially true back then. I was definitely one of the attractive ones back in school and never had a problem getting girls. (I don’t say this to brag, but I want to give you an accurate picture as you read along). I’ve always had a nice face, strong jawline, and short hair, which works well on me.
As I’m scrolling through Instagram I notice a girl I used to date (we’ll call her Stephanie) posted a new photo. Stephanie was beautiful. Any guy that saw her would be lying through their teeth if they didn’t think she was attractive. She was, and is, very pretty. She was thin, had long dark hair, and is classically pretty. She looks like she could be in an old black and white film and she would fit right in. Her face was stunning in an innocent, yet pretty way. Out of any celebrity I would say she most resembles Audrey Hepburn. Thin, pretty, and a classy vibe to her.
Now, me and Stephanie had dated for about a month the year before. Our short relationship was interesting, to say the least. We went to high school together but weren’t friends back then. After freshman year of college ended I had DM’d her. We started hanging out that summer and went on a few dates. I remember noticing right away that she was very innocent. As pretty as she was I got the feeling that she hadn’t had much experience with guys. Also, she was still a virgin. I’m pretty sure her parents had sheltered her growing up and were very religious.
When we hungout we would usually go back to my parents house and “watch a movie.” This usually meant that we put on a movie for 10 minutes then had a furious and heated makeout session for the rest of the movie. Although we couldn’t go much further, it was always very hot. For one, she was absolutely stunning. Also, since she was so inexperienced she would get so wet that I could feel it through her leggings when I would play with her. She was very strict about me going any further than that and would only let me do it for a few seconds before she would cut it off. I could tell she loved it but wouldn’t allow herself to give into the pleasure. I always found that so hot. We would makeout for hours. It was a real workout. And such a tease… We would dry hump. Then I would flip her over and dry hump her from behind. Then I would flip her back and tease her with my fingers. She would moan for a bit then push me off. Then we would do it again and again. But each session would end before either of us were able to get the release we so desperately craved.
She was very submissive and would usually wait for me to make a move before things happened. When I did make a move, her inner freak would come out and she would be all over me, grinding her vagina up against my throbbing cock, both of us still in our clothes. As hot as it was, the end of the night was always sexually frustrating for us. I could tell she wanted more, but was conflicted.
One time we were “watching a movie” and doing the usual things – grinding, teasing, then dry humping. Then, all of a sudden she reached down my pants and pulled out my dick. I was pretty sure this was the first time she had ever held one and I nearly came right there. Before her I had been with a few girls and had gotten laid pretty frequently. So I shouldn’t have been so turned on by a girl grabbing my cock, but I was. She then proceeded to bury her head in my chest and gave me one of the fastest hand-jobs I’ve ever had. Her hand went from 0 to 100 real quick.. I came shortly after. I stood no chance.
Anyways, a few weeks later I was back off to college and things ended between us. It was probably a combination of the distance and the fact that she was beginning to explore her sexual side, and was clearly pretty conflicted about it. I remember noticing a few months later that she seemed to be with a new guy.
Back to the present and all those thoughts flash through my mind. I decide to “like” her picture and sent her a DM saying I hope she was doing well. I was just putting some feelers out there and didn’t expect much. She responded almost instantly and seemed to be very happy I messaged her. I looked through her profile and noticed all the pics with the guy were gone. “Perfect,” I thought.
We DM’d back and forth for a little then she asked for my snapchat and we moved the conversation over there. We sent some pretty innocuous snaps back and forth. Then things took a turn. She sent me a snap – a picture of her with the message “so I’m guessing you’ve had sex since we dated?” Pretty stunned, I was getting ready to reply when she hit me with another one, almost immediately after. It was another picture message and it said “sorry! Had a lot of caffeine today. You don’t need to respond!”
I would’ve been the biggest idiot in the world if I was going to let this chance slip through my fingers. I wasn’t sure where this would go because she was never this forward, but I wanted to find out. “haha yea, I have actually. And you?” I responded.
She responds. “yes”
Then another snapchat from her. “so… I was thinking..”
“bad girl” she points at herself.
“bad boy” pointing her finger towards the camera, at me.
“it could happen?”
My jaw dropped. Was this real life? Is this girl, the same girl who last year wouldn’t let me get past second base, asking me to have sex with her?
“It definitely could happen” I replied.
“when” I followed up with.
“when are you free” she responds.
“Tonight?” I reply.
“sure”
I couldn’t believe this was real. I was thrilled and nervous as hell at the same time. I showered, got ready, then drove over to her house to pick her up.
Sitting outside her house in my car the nerves really started to creep up. “Was this really happening?” “Is she really going to come out or is this some kind of crazy prank?” And just when I felt like I was going to lose it, I see her front door open. She begins to walk out and closes the door behind her. I can see she’s wearing leggings and her hair is up in a bun. She’s looking great as she always does. “I can’t believe it. This girl is about to get fucked” I say to myself. She walks down her driveway and straight up to my car. She doesn’t look up at me until she opens the door to get in. We hadn’t spoken in over a year but we made some pretty good small talk on the way back to my house. Neither of us mentioned what we were about to do, but you could cut the tension with a knife. There was always sexual tension between us but it was amplified by a hundred this night.
We get back to my house and snuck into my bedroom. She walks over to my bed, takes off her long winter coat and sits down. She’s wearing tight leggings that really highlight how sexy her legs are. A little nervous, I ask her what movie we should put on. “It doesn’t matter” she responds, leaning back and opening her legs as she says it.
I could have cum right there. I take the hint and walk over to the edge of the bed. Before I get in bed with her, feeling bold, I drop my pants to the ground, exposing my throbbing cock. I was curious to see how she’d respond. She doesn’t miss a beat. She leans in and begins sucking on it. It was great head and she was really into it. Her eyes were closed and she was going back and forth, slowly, like she was taking it all in. After a few minutes of that I notice her hand making its way down her body as she begins to play with herself while she’s sucking me off. She must have been really turned on because shortly after playing with herself she tensed up and let out a little quiver.
“I’m going to fuck you now” I say to her. She lifts her head up slowly, looking at me and nods. She then lets go of my cock and lays back. I climb on top of her and slowly enter her. She lets out a long moan and shudder as I enter her. “It’s about time” I think to myself.
I was too horny to last long with her. So I rotated between fucking her with my cock and pulling out and playing with her pussy. I think she really like combination and it felt like she was quivering every few minutes. Eventually I couldn’t take it anymore and had to cum. I came for what felt like 5 minutes before I collapsed on top of her.
We laid there for a few minutes before we cleaned up, got dressed and I drove her back home.
Source: reddit.com/r/gonewildstories/comments/a52to1/naughty_girl_naughty_boy_it_could_happen_mf