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Awkward Memories, Untouched Mammaries

Posted by: Age: 25 Posted on: 4 comments
0 likes 1816 views Category: Masturbation Male Solo Tags: Awkwardness, high school, memories
A Young Man Remembers

High school was an interesting time for me. I started off shy, but grew so fed up with the drudgery of having to go somewhere everyday that I was uncomfortable with, that I felt a prisoner in, that I broke out of my shell with a theatrical sense of humor. I became an eccentric entertainer who socialized with as many people as possible. I didn't develop too many deeply close or personal relationships in the grand scheme of the years, though, just a handful that have mostly faded out by now. It was very fun and exciting for me during my high school years though, at that very time, to engage as many people in conversation on a daily basis as possible. It was a large school, and my peers were-a-plenty, there were a many strangers to meet, and I broke the ice with as many as I could and caught people off guard and told jokes and sang unexpectedly at the spur of a moment. While killing time in the hallways, either during a free period, or after school while waiting for a ride, I came across a couple of girls one day. They were a year older than me. One was named Stephanie. She was the one I was attracted to. I don't remember her fat ugly friend's name. But Stephanie was a white girl with long brown hair, very pale, soft-looking skin, glasses, and beautifully-sized-and-shaped breasts. I was friendly to her, and she reciprocated, and she would look at me in such a way, and crinkle her face in approval and tilt her head and make certain facial expressions that made me feel appreciated, but that also had an air of flirtatiousness to them, and I got a wonderful vibe from her, and her responses and statements and way of talking and expressing herself and her own humor and friendliness would excited me, and she would likely often give me an erection without even really trying! I couldn't believe how fully developed her breasts were for a high-school girl! She was always studying advanced classes, she did much better academically than I ever did. I could never care about schoolwork or homework or want to do homework the way other students did. It was all a bunch of bullshit and headaches to me. I made the best of the situation in my own ways. As flirtatious as I was with many, many girls in high school, I was always awkward with asking a girl out, and whenever I did, the girl always said "no," either because she didn't share an interest in me, or she already had a boyfriend. I didn't ask a ton out, just the ones who I had crushes on, the ones who were very special to me at the time. Stephanie was dating some guy when we were in high school, so I couldn't ask her out then. She once told me during one of our conversations that she had had a dream in which I was trying to seduce her. I once had a dream around that time that she embraced me while she was naked! I didn't tell her about that dream, though. She graduated a year before I did, and then we rekindled a year after I graduated. She was no longer seeing her old boyfriend. It had been two years since she and I had gone to school together and bonded in the hallways. She lived far enough away from me. I had to take a railroad to meet up with her at a station where she picked me up in her car! She was more of an adult than I was at that time, it would still be years before I would drive. She looked as beautiful and as dream-like as ever. It was the summer, and she was wearing a short-sleeve blouse/shirt, a black skirt, and flip-flops. I've always had something of an attraction to women's feet, and it was exciting for me getting to be with an essentially barefoot Stephanie! She took me to a mall that was local to her, and we spent several hours together. My eccentric humor was in full swing. I made a lot of witty statements and tried to entertain her and charm her. I tried to bring the magic of my high school persona back. I just wanted her to like me. I wanted so badly to get romantic with her, but I had never kissed a girl in my life up to that point! I was very awkward at the idea of dating a girl. It was something I didn't have practice in, something I didn't know how to do. This was one of my first times spending time with a girl one-on-one outside of the walls of my high school. I was nineteen, and I felt behind my peers in many ways, as if I didn't know how to socialize normally and be like the rest of people my age. I just knew how to put on a showy act, how to be a clown, how to be an entertainer. Having a deep relationship with a woman, a romantic, or intimate, or sexual relationship was something I wasn't able to confidently pull off at nineteen. After she went shopping with me and we hung out in the mall, she took us to a restaurant for dinner. Hours were passing by since we first met that day and I didn't know how to make a move on her! I didn't know how to hold her hand or try to make things go in a romantic direction. I didn't know how to go from friend to potential love interest. I had to use the bathroom after dinner, and she drove me to her house where I used her toilet to pee. It felt interesting pulling my dick out in the house of a girl I was excited about. She waited in the other room where I could hear her playing notes on a piano. She drove me back to a train station and it was dark out by that time. We were in her car, and when it was time to say goodbye, I think she went in for a hug. I don't remember if I gave her a hug back or not. I'd like to think I did. I definitely remember I put out my hand for a handshake. I could tell she was upset. I think she wanted more from me. She wanted me to make a move. I wonder to this day if she wanted me to make out with her in the car. Secretly, I wanted nothing more than to play with her big beautiful breasts! I wanted it so badly! Up to that age, I had never touched a pair. I was so nervous. I didn't know what I was doing. I didn't know how to get from Point A to Point B with a woman. I was hoping she would lead the way. I guess it didn't work like that. I think she lost interest in me that day. I had admired her for years. When we spoke on the phone afterwards, she sounded depressed. I don't know if she really was, or if she just was not happy to talk to me. I believe she stopped answering my calls after a while. I reached out to her online about a year and half later and told her how she was one of my favorite people from high school and I sense she was disappointed with our get-together. She told me in response how she saw admirable things about me, and sensed a depth and intelligence behind my artificial presentation, but that I had made her uncomfortable during our get-together and that I was too quirky for her taste. She said could only handle small doses of that intense quirkiness. I never heard from her again. I wouldn't kiss a girl or feel a pair of breasts for the first time until I was twenty. I'm not much of a clown anymore. I keep to myself these days. I don't joke around with people unless I know them extremely well. I'm a quieter person. This past night I looked at a picture of Stephanie and her beautiful cleavage, popping out of her top, ever so teasing. I wonder what her breasts feel like. I wonder what her nipples look like. I wish I could've felt them in the car that day, almost six years ago. I wish by some miracle it could've led to that, that night. As I looked at the picture, the passion from my teenage years flooded back. I always liked that girl. A lot. My penis tingled. I got excited. I stripped off what little clothes I had on. I masturbated to Stephanie. I wished she liked me back. I wish I could've fondled her breasts. If she knew I masturbated to her this past night, I don't think she would like that. Maybe she would think it was creepy. It's funny how things fall apart. It's funny how the people I care don't about don't care as much about me. Sometimes I wish a woman out there could read this and want to meet up with me and masturbate and let me play with her breasts. There's so many great, exciting, sexy masturbation stories on here. I wish I had better mutual masturbation stories and experiences to tell. I wish I could catch a woman sunbathing topless and then tell you how she shows an interest in me and we end up masturbating! There's often a sense of longing in my masturbation. I sometimes wonder - What do we really accomplish with the sharing of our stories?

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