This story happened when I was 22, the summer immediately following my college graduation (4 years ago). I attended a pretty good school in Boston and, like many people in my stage of life, I was trying to figure out what to do next. I had a liberal arts degree that, while interesting, wasn’t the most practical in terms of finding a job. So, in the mean time, I had taken a temporary position in the public school system while I tried to figure my life out. I had an income, a nice apartment, and was enjoying bachelorhood. I had been in a semi-serious relationship over the last few months before graduating, but that had ended as school did so I was enjoying bachelorhood.
I had been using the usual gambit of dating apps to try and meet some new people (Tinder/Bumble, you know the deal). Anyone who has been in these situations knows that those apps can bring some amount of success, the occasional ONS or something along those lines. But it is far from a guarantee, as most conversations just die out over time.
Enter Anita. To be honest, I had matched with her without looking over her profile all that closely. She was in very good shape, with a cute smile and eyes that really popped, even through a screen. Most of her pictures were of her in a cheerleading outfit, which I had just assumed was a college team. Upon closer inspection, I realized that it was her high school team.
We got to chatting, and I discovered that she had just graduated high school and was off to college in California in the fall. We had some common interests, and the conversation was going surprisingly well given the platform. I got her number and her snapchat, and we switched over to conversing that way. She was surprisingly naughty, often sending me unprompted teaser pictures. Nothing too revealing, but some very suggestive poses. And she would often send them without acknowledging what she was doing, which drove me wild.
After a few days of back and forth, she confessed that she was a virgin. She had dated a guy in school, and given and received oral, but have never actually gone all the way. She was nervous about going off to college having never been fucked, but was very hesitant about how to go about it. I think she knew that she was extremely attractive and could have gotten it whenever she wanted, but she wanted her first time to be special. Someone who would take it slowly, understanding her comfort level and not pushing too far or too fast.
We met up for coffee and walked around a park not too far from my house. She was just as cool in person as she had been virtually. We connected over our love of the outdoors, some hikes we had both done, trips we had both taken. We also connected over some of our favorite movies. Overall, we just had a really good time. So I suggested we walk back to my apartment, and watch one of the movies we had discussed.
Before I get into the sexy time, let me do a couple of quick physical descriptions
Me: White, 5’11 about 160lbs. I was ran cross country/track in college, and have that type of build. Toned, but by no means “big” or “jacked”, tending towards the slimmer side. Two tattoos, short hair. The two features most commented on are my eyes and (sorry to be like this but) my size. I’m 8″ hard, not super girthy but long enough that it draws attention.
Her: 5’4 (won’t guess the weight lol). Not petite, but in good shape due to cheerleading and dance. Long brown hair and HUGE brown eyes, very very easy to get lost in. A nose ring and a fresh tattoo on her shoulder. Tits were nice, but really her ass was her best feature. Big enough to grab a full handful, but perky enough and she knew how to work it.
So we got back to my house and climbed into my bed with the movie on. It didn’t take long, of course, before she had a leg up over me, arm around my waist, nestled into my shoulder. I kissed her forehead and would stroke her forearm as we watched. Soon enough, we were making out and she climbed on top of me. She slowly grinded on top of me, feeling me get hard underneath her. My hands explored her back, climbing up her shirt and sliding it over her head. I then moved to unhook her bra and before you knew it, this beautiful girl was topless and I couldn’t help but drink in the sight. She was stunning, with her hair flowing behind her, that cute smile, and those huge eyes looking innocent and seductive at the same time.
I paused for a moment to ask her how far she wanted to go. She had been very clear that she did want to lose her virginity, but wasn’t sure the first time meeting up was the right time. She told me that we could just start playing with each other, and if she felt like she wanted to stop she would say so.
I agreed, then deftly twisted my body and switched our positions so that she was now on her back, wearing only leggings. I got my shirt off and slowly started kissing my way down her body. I started with her neck, down to her chest with a brief stop on each nipple. Then down her stomach, past her belly button until I was at the top of her pants. Slowly, I took both hands and slid the leggings down, revealing an adorable pink thong underneath. I rubbed her clit slowly as I kissed the inside of her legs, just enough so that I could feel the wetness seeping through. Not wanting to totally ruin her panties, I slide them to the side and put a finger in. Slowly, massaging, exploring, feeling her clench around me and toss her head back as I put a second finger in, and got my tongue involved. She was very aroused, and it didn’t take long before two fingers and a tongue had her convulsing, as I felt her orgasm when she shuddered.
She looked at me, out of breath and sweaty, and said “Omg thank you, now its your turn”. So, kissing her as we switched roles, she undid my belt like a pro, taking down my pants and underwear in one move. When my cock popped out, I registered the surprise in her eyes although she didn’t say anything. I was bigger than she was expecting, but the hesitation only lasted a moment as she got down to it. She was shy with it, not hungry as some girls are. She went slowly, kissing and licking she shaft or swirling her tongue around the tip for a while before even putting it in her mouth. That drove me wild, and I clenched my hips. She started blowing me, taking me little by little. She definitely didn’t deepthroat, but she had more skills than her shy nature let on and before I knew it, I was on the edge of cumming.
Not wanting the fun to be over so soon, I had her stop and motioned her back to sit on my lap. I looked deep in those brown eyes and said “do you want to do this? If not, you can finish me with your mouth”.
She pondered it a moment, just for a moment, before saying “put it in me daddy”
I had never been called daddy. I wasn’t sure it was something I liked or wanted. But when that word crossed her lips, I knew she was something special. I sat up, with my back against the headboard and her straddling me. Not even taking time to put a wrapper on (not smart, but I was lost in the moment), we gazed into each other eyes as I reached around to grab my dick and slowly slide it into her. She was so tight, so I went slowly, watching her eyes roll back just a little as a soft moan escaped her lips and her grip on my shoulder tightened. She took it all, and it was euphoria for me. I placed one hand on her ass, the other in her hair, and started to thrust. I love this position (think the way you would do cowboy if you were on a couch), and it feels so good. But it wasn’t ideal for a girl who was still just learning what riding was. So after a couple minutes, I got tired and had her climb off.
I put her on her back and we fucked in missionary for a bit. Missionary gets a bad rap, and I definitely missed out on watching and feeling her ass, but there was some deep connection as we stared into each other eyes as I came in and out, and it allowed me to have control. I loved watching her, feeling her breath on my chest.
To finish, I moved us into another of my favorite positions: spooning. I got behind her, with one arm supporting her head and the other wrapped around, able to feel her tits, her stomach, her neck, or play with her clit as I fucked her good from behind. I kissed her neck and her hair while her moans grew steadily louder and louder. I felt her cum once more, this time on my cock, and I knew it was time to finish. I pulled out, rolled her onto her stomach and let loose all over her impeccable ass. After a few seconds of just staring at it, I quickly jumped off the bed, got some tissues and cleaned her up.
Afterwards, we lay in my bed: naked, sweaty, exhausted, but satisfied. We finished the movie, falling asleep in each others arms.
Yes we did meet up a number of more times that summer before she left. But this was the first time I had ever taken a virginity and it was special.
Source: reddit.com/r/gonewildstories/comments/mvijfe/first_time_virginity_taker_mf
Nice story!
Nicely done making sure she was comfortable every step of the way and making sure her first time could be condomless like nature intended.