Hello everybody! First time posting on here so please bear with me. I’ve come to enjoy a lot of your stories and I figured I’d share one of mine. This is a story from years ago when I was in high school. If you want to skip to the sexual stuff go to the *.
A little about me at the time, I was 18. I was a senior in high school and I was about 6’2 and around 160 lbs. I was an athletic kid, did sports in school. I have dark brown hair and green eyes.
She was the same age and was about 5’6, brown hair that she normally dyed black and light-blue eyes, and had a very full figure. Looking back now, I didn’t realize how amazing her body was. She had a tight waist, round ass and huge breasts. They had to be a D-cup which for her figure was very large. Let’s call her Ally. (not a real name of course)
The only issue is… her face… Not be a jerk but this girl was a classic butter-face. Now, I’m a decent looking guy myself, nothing that would land me a job in front of a camera, but the differences in our looks was enough to make me self-conscience about being with her. You see, we both lived in the same neighborhood and I was friends with all the kids on our street. For whatever reason, it was only boys on our street. There weren’t any girls, except for Ally. A lot of the boys in my neighborhood were mean to her because she had a super tomboy attitude alongside her looks. She probably developed the tomboy behavior from being around us all the time. They would talk about her when she wasn’t around and there was always the joke about dating her. I never liked to make jokes about her because I felt bad. We were some of her close friends and she really liked us and I felt it wasn’t right the way the guys were treating her. While a lot of them would make fun of her, I would just be quiet and try to change the subject. I think she knew this about me and she always had a crush on me because of this.
Her and I never really spent much time together and especially never together alone. She would normally ride her yellow mountain bike to my house which was about half a mile away from hers. I was always super embarrassed to be around her because I know if my friends saw me with her, I would never hear the end of it. (Another friend of ours, we’ll call him Jay, tried hooking up with her and every lit him up about it for months) So when she came over, we would normally hang out in the wooded area behind my house. You couldn’t see anything back there. I remember being so paranoid that I had her bring her bike too. We would normally just talk about schools, people we liked, the cliché stuff that high school kids talk about. She would also drop very subtle hints to me that she liked me. She told me about a couple guys she liked and then she asked me if I liked anyone. I knew she had a crush on me so I told her that I wasn’t interested in anybody because I would be leaving for college soon. I also figured this would be a way to protect her emotions from me telling her I wasn’t interested in her.
Things were like this for a number of months. She would come over almost bi-weekly and I would hang out with her in my backyard. Nothing happened between us but we did start to develop an actual friendship. Eventually my father asked me about her:
Dad: So Ally has been coming around to the house a lot.
Me: Yeah. I guess she just wants to hang out more.
Dad: Is there anything going on between you two? I don’t think she hangs out with the kids in the neighborhood the way she does with you.
Me: What? No way. I mean.. I’m not really interested in her at all. I don’t really want to date her or anything..
Dad: Well she is a very good looking girl. I don’t think it would be a bad idea..
I’m not sure if my dad actually thought she was cute or was just being nice. Maybe he was just trying to support his son. I’ve never asked him about it but I think that was the first time that anyone told me that this girl was cute. I definitely thought about his advice and just thought of the torment my friends would give me if I were to actually date her. Never really came to a conclusion about what to do about her. That was until, the next time she came over. She came to my home the usual way, riding her bike to come visit me and we hung out in the backyard. It was the same conversations as always, school, crushes, etc. It was all normal until she came and sat on my lap. She made the power move on trying to see what would happen if she did that. I just let her and didn’t say anything about it but I could feel my blood start flowing. The way she sat on my lap also let me look down her tank-top and see the huge amount of cleavage that she was wielding.
***Now I’ve always been a big flirt. I flirt with everyone: guys, girls, teachers, etc. It’s never really in a sexual manner but I’ve always been one to try and charm people. I’ve been told that by many people and half the time I don’t realize because its second nature for me. So when Ally sat on my lap, I did start to act more like my flirtatious self. I started to say things to make her laugh and giggle. I could tell she was getting really into me. After a couple more minutes, the conversation started to have some sexual undertones. She started to ask me questions like “are you a good kisser?” and the other questions that inexperienced people have. (not taking a jab at her. I was just as inexperienced.) I would answer something like “you’d have to find out.” She started to get really into me and asked “What is your favorite feature of mine?” I didn’t even have time to think if she meant physical or her personality or anything. I just said “Your boobs.” She started to laugh. “Every guy likes my boobs. I don’t get why!” she said in disbelief. “Well, they are pretty big. I mean, I really like them!” I said to try and recover and see what would happen next.
“You can touch them if you want.” She says to me in a very soft and sexy voice. I feel myself take a big gulp and I slowly put my hand over her tank-top. I start to gently rub them as she leaned back into me. With her still on my lap, I could feel her head start to nuzzle into my chest. “Is this okay?” I asked nervously. “You can go under my bra if you want.” I was getting really hard at this point and I’m sure she could probably feel me as she was sitting right on my hard cock. I reached under her tank-top and bra and started to feel the soft skin of her breasts. They were so soft and warm. I could fit her breasts in each one of my hands. I started to rub her nipples and I could hear her moan in my ear. After about another minute of this I asked her if she wanted to go inside. My parents weren’t home at the time and I knew they wouldn’t be getting home for another a hour at least. She nodded her head complying.
I hold her hand as I guide her through my house into my bedroom. This was the first time she was ever in my room and we both sat down on the bed. I ask her if it’s okay if I could play with her breasts again and she said of course. With us sitting on the same side of the bed together it was a bit awkward reaching over her tank-top and under her bra. Realizing how awkward this was, I suggested to her if she could take off her shirt. She said yes. She soon took off her shirt and undid her bra. They were amazing. I remember how big and perky they were. They didn’t hang at all. I went back to fondling her breasts and I asked her if we wanted to lie down. We both laid on the bed together and I am feeling her up as she begins to kiss me. We start making out. HARD.
She pulls away from me for a second and says “So what is this going to be?” She was referring to our relationship. “I don’t know. What do you want?” I say in response. “Well we could date.. but you are leaving soon. So I don’t mind this being a secret.” “What do you mean a secret?” I said questioning. “Well this can be a one-time thing but you can’t tell anybody. I don’t want people thinking I’m a slut!” I chuckled and agreed to keep this a secret. Before we go back to making out, I ask her if it’s alright if I take off my pants. “I’m not having sex with you.” She said. “But you can take them off.” I quickly undid my belt, unbuttoned my pants, and ripped them off. With me just in my boxers now, I asked her how much she’s done before. “Well I haven’t had sex. But I’ve done other things.” “Like what?” I said inquisitively. “I’ve given a few handjobs if that’s what you want to know.” I think she said that knowing specifically that I wanted to cum. “Would you be willing to give another?” I said jokingly. Without saying anything she slid her hand down my boxers and started to tease my cock. I could feel her hands slide up and down my cock. “You’re pretty big.” She said grinning. She pulled my boxers off my legs and looked at my cock. “It goes past your belly-button!” she said while giggling. I didn’t think much of this at the time since I’ve only had about 2 other sexual experiences that involved my dick. Both of which weren’t really exciting. She reaches for it with both hands. “You’ll make someone very happy with this!” she said.
At this point I’m lying on my back and she is on her side kissing me and stroking me. I ask her if she was willing to give me a blowjob and she said not while she has her braces. I didn’t really press my luck since I was already having the time of my life. “There is one thing I want to try..” I say to her. “What is it?” She asks . “well I don’t know the name, but lie on your back for me.” I knew it was called tittyfucking but I’m sure if I presented it with that name, it would have sounded awful and would be shot down before I got a chance to explain it. Listening to my instructions, she gets on her back and I start to get on top of her. “hold your breasts together.” I move her hands to show her how to push them together. I then, while on top of her, slide my dick between her tits. She lays there waiting for her next command as I start to selfishly thrust my dick between her breasts. She turned her head to the side as to avoid me poking her in the face with my dick. I keep thrusting for about a full two minutes and I begin to bust all over her neck, face, and tits. It was a massive load and she shouts “what the fuck!” as I am covering her with my cum. Immediately after cumming, I go to the bathroom to get her a towel to wipe off. As I come back in the room I see her lying on my bed covered with my cum. It was quite a dominating sight to see.
She looks a little annoyed that I came on her so much without telling her. I apologize for making a mess and she said it’s okay and we both begin to get dressed. After getting dressed, we talk for about five minutes where we confirm that this will be our secret. Ally stopped coming around for a while after this and her family eventually moved to a different state. I did get to see her again once before I left for college and I asked her if she wanted to fool around again. She said that was looking for something more official and passed.
So that is one of my stories. I hope you all enjoyed it. If you like it, let me know as I have many other stories to share with everyone!
Source: reddit.com/r/gonewildstories/comments/biblss/my_first_time_tittyfucking_long_post