My name is Jenny and when I was growing up, I was a tomboy. I always hung out with the boys in the neighborhood and at school. I cut my brown hair short and never, ever wore a dress or a skirt. Well, my parents forced me to dress like a girl at times for family or religious functions but I hated it and changed into my blue jeans and t-shirts the first chance I got. I played football and baseball or whatever sport the boys were playing and they treated me like one of the guys. My two older sisters even tried to get me to be more feminine like them but they were unsuccessful in their efforts.
I was always taller than most of the boys and I could hold my own playing against them in sports but I had to earn their respect. Things changed when the boys started going through puberty when they got bigger and stronger than me. It was then that I started to get left behind. It wasn't cool to be hanging around playing with a girl anymore. Besides they started getting interested in other girls.
I was a late bloomer and through most of high school, I was the tall skinny girl who didn't wear any makeup. I wasn't as pretty as the other girls and I didn't fit in. I never hung around with other girls so I never developed any life-long friendships with any of them. I started hanging out with a couple of other outcasts after the boys ditched me.
All through high school, I wore jeans and baggy tops like sweatshirts to hide my ugly body. I didn't date because no one asked me out. Looking back, I didn't do anything to try to become more outgoing either. I didn't go to my junior prom because no one asked me and it was too late for me to fit in with classmates.
Things began to change in my senior year after I turned eighteen. All of a sudden, my body seemed to change. My boobs got bigger and my ass began to take shape. I let my hair grow longer but I still had body image issues. I thought my tits were too small, my ass too big and I felt all the other girls in school were prettier than me. All I wanted was to finish high school and get the hell out of town so I could go away to college where I could start a new life.
Some of the boys noticed the change in my body and would make comments on my ass or tits as I walked down the hall. I even got invited to the senior prom by one of the nerds in school. I wasn't going to go but my mother kind of forced me to. She must have noticed my loner status in school and was thrilled that I finally got asked out on a date. I think mom wanted to help me get all dressed up in a gown and finally put on some makeup. Deep down, I think she thought I was a lesbian and was thrilled that I was going out with a boy. I also think she wanted to relive her teen years through me and I was finally cooperating.
Mom and I did all the girly things in preparation for my big prom date. We went dress shopping where I tried on more dressed than I had ever worn in my entire life, went to lunch, and continued shopping where she helped me choose my dress, high heels, and jewelry to go with my outfit. Mom convinced me to get a long slinky gown that followed every curve of my body and it had a slit up my thigh. It was so low cut, my boobs were practically falling out but, I hate to admit, it felt good to get dressed up like the other girls. I wasn't comfortable showing as much skin as this dress would but my mother liked it so much that I didn't want to disappoint her. I almost broke my ankle in the high heels we bought but I practiced walking in them when I was alone in my room. When we got home, I tried on the dress for my dad. I could tell he didn't like the fact that I was showing off my legs and boobs and the fact that I was now a grown woman.
He told me how pretty I looked after mom prodded him, "Doesn't she look lovely, dear."
After a long pause, Dad said, "Yes, you look very pretty, darling."
On the day of the prom, mom took me to get my nails and hair done as well as having a professional put on my makeup. I have to admit, I felt pretty for the first time in my life. I wasn't very comfortable being all dolled up but it helped build my confidence.
Mom helped me put on my dress and accessories before my date came to pick me up. She was in tears when we were done. She finally saw me dressed as a girly girl after eighteen years of seeing me in jeans and baggy tops. It was her dream come true. My dad almost choked when he saw me.
Before my date arrived, my dad even told me, "If your date wants you to do anything you don't want, just call and I'll pick you up, no questions asked."
I smiled and replied, "Okay, daddy."
He knew I looked pretty, even sexy, and was afraid someone would take advantage of his baby girl. When my date, Oliver arrived, his jaw dropped wide open. He even told me later that he almost didn't recognize me and couldn't believe someone as pretty as I would go to the prom with him. The other kids couldn't believe my transformation either. I went from my frumpy old clothes to looking elegant and sexy. As the evening wore on, I reveled in the looks and stares of the other boys. The more people complimented me the sexier I felt. I even let Oliver grab my ass during a slow dance at the end of the night. I could tell he was excited to touch my butt if you know what I mean.
Oliver and I were invited to a party after the prom where there wouldn't be any adult supervision. We danced and had a few drinks. It was during a slow dance that Oliver gave me my first kiss and felt my boob. By this time, I was feeling sexy and a tad drunk. We ended up in one of the bedrooms where I lost my virginity to a very nervous and awkward Oliver. We were both scared because this was our first time. It wasn't anything exciting but I finally lost my virginity. I heard all the other girls talking about sex and now I could relate.
Oliver and I continued to date and have sex until we both went away to college. It got better with more experience and he gave me my first orgasm in the back seat of his car while we were parked in a lover's lane.
My summer love was interrupted by our yearly family vacation at the lake with my uncle and cousins. I didn't want to go but my parents insisted. It was going to be our last vacation before I went off to college and it was sort of a tradition. My older sisters weren't going anymore because they lived out of town. My parents aren't wealthy and struggled financially my whole life and this was always a cheap vacation for us because my Aunt Sharon and Uncle Jim paid for just about everything. My mom was always close with her sister-in-law and it was a chance for them to get together also. They lived in a more exclusive part of town and we didn't get a chance to see each other very often. My uncle is a very successful businessman and travels a lot. He is my dad's younger brother and I think my dad was a little jealous of his success and had rejected several offers to work at Uncle Jim's company over the years. He said he didn't want any charity.
I heard family gossip over the years that it was suspected that my Uncle Jim had several girlfriends or slept around when he traveled but my aunt never said anything because he was a good provider for her and their two boys, Jake and Junior. Jake was a little older than me and Junior and I were the same age. I believed the stories about my uncle because whenever we saw him he always flirted with my mom and on a few occasions, I saw him grab her butt or get a quick feel of her boobs. Everyone wrote it off as good-natured fun and Uncle Jim being Uncle Jim. He was a very handsome man in his early 40s.
