I had my first real girlfriend when I turned 19. When I say "real girlfriend", I mean one that would let me have sex with her. I was a late bloomer. Girls made me nervous as I had no confidence in actually engaging with them successfully. Not that I didn't have fantasies about the prettiest ones, the cheerleaders or the sexiest ones. I definitely had fantasies about having them as my girlfriend and having sex with them, but my fear of being rejected or laughed at, made me too shy to even take a chance talking to them.
I wasn't really ugly or anything, but I wasn't into sports and never developed the body that girls seemed to be attracted to. I was kind of tall, almost 6 foot, but both bony and skinny. I was a shy homebody kid that hung out with my loser friends that didn't have girlfriends either. I was into cars, motorcycles, hard rock music and smoking weed, trying my best to be cool. My best asset was my cock, which nobody would ever get to see cause I too scared to even talk to a girl. Even with nothing to compare to, I was pretty sure I had a bigger than average cock, a fraction over 7"s and cut. Playing with my cock was my favorite activity. Still living at home, I spent many hours locked in the bathroom jacking off to porn on my phone.
My first real girlfriend was Sherry. She was 18 years old, one grade behind me and was a sister of one of my loser friends. I was around his house a lot and she always wanted to hang out with us guys. Eventually me and her got on friendly speaking terms and it finally turned into a date. q Sherry was really built, nice firm titties, a flat athletic tummy and a big round butt. We started dating and it eventually turned hot and heavy. It might have been the happiest time of my life once we started having sex. I was insatiable for her hot athletic body and she seemed to love my cock, never refusing me sex, giving my cock all the attention I could hope for.
I was always at her house and her father kind of freaked me out. His name was Albert Carpenter, but of course I never called him that. I referred to him as Mr. Carpenter when I addressed him, which was rare in itself. He really never even spoke to me at all, mostly just seeming to tolerating my presence. I avoided him as much as possible when I went to her house and he was there. He actually scared me as I felt he knew what I was doing with his daughter. I'm sure he didn't really like the idea of me fucking his daughter, but of course he never said anything really insinuating about that to me. He just gave me these creepy looks like he wanted to kick my ass, so I avoided him as much as possible.
One reason he was so intimidating was that he was really into weight lifting and body building. While I was about the same height as him, he could physically crush me if he wanted to. Mr. Carpenter was all muscles, as all he ever did was go into the downstairs garage and lift weights. He was almost bald but really fit and muscular. He would wear these muscle shirts when he worked out that would show off his huge arms and chest. I guess he was about 40 or 45 years old, but his muscular body belied that, making him look much younger.
I remember Sherry told me once that her parents were fighting about something. She had eavesdropped and discovered her mother had found a pair of women's underwear in the glove box of his truck. I found out later that this wasn't the first time he denied his infidelities to Mrs. Carpenter. Apparently he screwed around on her a lot.
The Carpenters were not wealthy, in fact, to look at their house and furnishing, they appeared to be barely getting by. Mr. Carpenter worked as a mechanic in a garage. Mrs. Carpenter was sometimes was a substitute teacher, did some baby sitting on the side and took some odd jobs for neighbors when available. Conversely, my parents were very well off. My dad was a bank president and my mom was a doctor. We had a really beautiful home compared to theirs. I actually think Mrs. Carpenter actually liked me as a possible future candidate of a husband to her daughter. Maybe that I could provide a better life for her daughter than her marriage offered. I think I was in love with Sherry, but now thinking back on it, perhaps "in lust" with her, was a better definition of my heart's feelings.
