Uncle Jim & Jenny's Secret

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.

I got along pretty well with my cousins because we were close in age, I was a tomboy so I wasn't like other "soft" girls and they treated me like one of the guys too. Every summer we'd sneak some of our parent's beers and go off into the woods to drink. I think our parents knew but they never said anything.

Things changed dramatically the summer after I graduated. When we got to the lake house, I was wearing a pair of tight short shorts and a tank top which immediately drew stares from Uncle Jim.

"My, my, look who's all grown up. Wow, Jenny, you look great."

I could feel Uncle Jim's eyes scanning my young teen body. It felt a little weird but it also made me feel a bit sexy by getting the attention of an older man. My cousins looked at me differently too. It was weird but deep down I kind of liked it.

During that week, my uncle seemed to be around me more than usual. I remember bending over in my bikini, looking in the fridge for a soda when Uncle Jim came up behind me. He scared me half to death but I felt him rubbing his crotch up against my ass. I could feel his manhood pressing against me as I stood up. He put one arm around my waist as he grabbed the soda for me. He stood there staring at my breasts as I thanked him. I didn't realize it but my nipples got hard from the air conditioning in the lake house and the cold air from the fridge.

Uncle Jim made a crude comment, "Umm, are you cold or just happy to see me?"

I didn't understand what he was talking about but I followed his eyes down to my chest and saw my nipples pushing out through the fabric of my bikini top and I began to blush. I didn't say anything as I walked away totally embarrassed but I could feel his eyes watching my ass. Before I walked out the door, I turned to see if he was watching and he gave me a wicked grin. It's hard to describe it in words but it was obvious he was looking at me in a sexual manner.

I remember playing volleyball on the beach in my bikini with my cousins and other young people vacationing at the lake. Uncle Jim sat in his lounge chair with a beer watching us. Every time I looked over at him, our eyes would lock onto each other and he'd give me a little smile. I'm not saying I wanted him to look at me but maybe sometimes I wouldn't pull the bottom of my bikini out of the crack of my butt so I'd give him and the other boys a look at my cheeks. When we'd score a point, I made sure to jump up and down to make my tits bounce. Sure enough, Uncle Jim was watching closely.

When we played Marco Polo in the lake, it's like a game of tag with your eyes closed, Uncle Jim made sure he would touch my thighs or ass when tagging me. I'm sure he was cheating by keeping his eyes partially open. One time, I let out an audible gasp when I felt his hand slither up between my legs, touching my young pussy through my bikini. Even my cousins began to touch me in some private places. I may have unintentionally kept my chest below the water when Uncle Jim was "it" knowing he would try to touch my chest. I swallowed hard when I felt both his hands groping my tits underwater for a brief moment.

Being a tomboy, I never liked wearing a bra and I would go without one as often as possible depending on what I was wearing. In the evening, I would relax and play video games with my cousins wearing a nightshirt and I know they and their father were checking me out. As I moved around on the floor, it was almost impossible to keep them from getting a peek at my panties and I know they were trying to see down the top to see as much of my breasts as they could. I may have left a couple of buttons undone to show off some cleavage. In bed at night, my hands would drift down between my legs and I'd rub my clit reliving the ways Uncle Jim looked at or touched me.

One time when I was wearing a pair of yellow booty shorts and a white sports bra, my cousins thought they'd be funny and they pummeled me with water balloons. I got drenched and I ran around trying to get revenge not knowing that my top had become transparent leaving my breasts and nipples visible for all to see. My shorts clung to my body and I didn't realize until later that I had a visible camel toe and it was obvious I was wearing a thong. I might as well have been naked. My Uncle Jim watched it all unfold and finally told Jake and Junior that was enough. My cousins, of course, thought it was funny to embarrass me like that

As I was going into the house to dry off and change, Uncle Jim stopped me and said, "You are a lovely young lady, Jenny," his eyes scanning my body again.

I didn't realize how much of my body was exposed until I got to my room and looked in the mirror. I got mad at my cousins but a rush of excitement shot through my body at the thought of being exposed like that. Thank goodness my parents and aunt had gone grocery shopping and didn't witness my near-nakedness. I got my cousins back later in the day when I pulled their swim trunks down to their knees and I started calling Jake "pee wee" and his brother, "pee wee junior." That really pissed them off which made me feel better.

The whole week wasn't filled with my uncle and cousins perving on me. We also had fun swimming, boating, jet skiing, and campfires at night under the star-filled skies. Junior and I talked about going away to college to get away from our parents and Jake gave us some advice on what to expect.

My eyes were opened to how much of a perv my uncle was primarily by the way he would say sexual innuendos to my mother and aunt and the way he would sneak a feel of my mom's butt or tits too. She even warned me to be careful around him. I'm sure she didn't want to cause any problems between her and her sister-in-law so she kept quiet about his wandering hands.

As the week wore on, Uncle Jim never missed an opportunity to rub my shoulders, touch my waist as he was walking by, or brush up against my tits or ass. In hindsight, I should have said something to him but I was like my mom. I was too introverted to stick up for myself and didn't want to cause any problems. I don't like confrontations and it was easier to keep quiet. It's not like it was a horrible experience either. I was having a little fun too. It was naughty and risky.

One night, my cousins and I snuck off into the woods with some beers. When we were younger we would pretend they were haunted and sometimes the adults would follow us and scare us. We found a secluded spot with some logs to sit on. I was wearing a long sleeve white t-shirt without a bra and a jean mini skirt. We set our flashlights on the ground simulating a small campfire and started drinking. We talked about school, our parents, and our futures. But after a couple of beers, Junior suggested we play truth or dare.

This game always starts off innocent but I could tell by the way the boys were looking at me that it was probably going to get interesting, to say the least. We asked if the others were virgins and to tell us about our first time having sex. They asked my bra size and I told them I'm a 36b. They asked me if I swallowed, which I had done. After several truth questions, I asked for a dare.

Jake said, "I dare you to show us your panties."

I was feeling no pain and a little horny from all the sex talk so I stood up and lifted my skirt to show them my pink bikini panties. Junior picked up a flashlight and put it on me like a spotlight. I turned around to show them my satin-covered ass then sat down again. I had them show me their underwear too. When it came to my turn, Junior gave me another dare.

"I dare you to show us your tits."

I pretended to be thinking it over and began to lift my shirt, then pretended to change my mind. They begged me to go further under the threat of losing the game and I ever so slowly lifted my shirt. Both boys grabbed their flashlights and shined the light on my chest. I stood there in their spotlights letting them gaze and my perky breasts.

I was about to pull my shirt down when I heard a voice asking, "What's going on here?"

It was Uncle Jim who came looking for us. I was shocked and quickly covered up. He told his sons to go back to the house. I was so embarrassed, that I could feel my whole face turning red. He waited a few moments until Jake and Junior were gone. I thought I was in big trouble.

"I'm sorry Uncle Jim, I don't know what got over me. We were playing a game. It will never happen again. I promise."

"Don't worry, Jenny. I won't tell anyone. Can I tell you something between us though?"

"What's that, Uncle Jim?"

"You've got nice tits, Jenny," and he reached out, lifted my shirt, and cupped my breasts, gently groping me for a few seconds before he said, "let's go back to the house. This will be our little secret."

As we were walking back to the house, the only words spoken were when he said, "You know, pink is my favorite color."

Holy fuck, he was watching the whole time. I was doubly embarrassed. I went straight to bed when we got back to the house. I masturbated before I fell asleep, thinking about showing off my panties and tits to my cousins with my Uncle watching and having him touch my bare breasts.

The next morning at breakfast, my cousins and I were pretty quiet and no one mentioned what happened the night before for the rest of the vacation. We only had a couple of days left before we'd go our separate ways anyway. My uncle continued to give me knowing glances and touched me a few more times, like when he grabbed my ass helping me onto the jetski, or touching my leg when I was sitting next to him at dinner. He first put his hand on my knee and then gradually moved it up my thigh. I didn't stop him until he got close to my pussy.

At dinner we were talking about the college I was going to and he said he does a lot of business in that city and that we should get together for dinner when he's in town. He mentioned he gets lonely being out on the road and that I would probably appreciate a nice meal because the food on campus sucked. I politely told him that would be nice. My parents thought that was a good idea too. It would be their way of checking up on me indirectly.

When the vacation ended, I was happy to get back together with Oliver. I was so fucking horny after what happened to me on vacation and I hadn't had sex in almost two weeks. Oliver was just as horny and we had sex twice in the backseat of his car the night I got back.

Just before I was going to leave home to go away to college, my mom announced at dinner that my aunt was divorcing my uncle. She was tired of his cheating around on her and waited until Junior was going to be out of the house before leaving my uncle. I wasn't surprised after seeing how he flirted with my mom and me. Who knows what he was doing when he was out of town all the time? Granted, he was pretty wealthy but he also paid a price for all the hours he worked and his cheating ways.

I lost contact with my uncle but we were still friends on various social media sites. He didn't post that often and didn't comment on any of my posts. I was able to reset my social life or should I say, I started to have one in college. It was a fresh beginning and I became friends with my roommate, Ally. I started to socialize and date a few guys, something I never did in high school. I was still introverted and had deep-rooted body image issues but I wasn't as neurotic about it as I was when I was younger. I liked being away from home and being on my own. I had a partial scholarship and got a part-time job to help with my expenses but I was still a poor college student.

During my second semester, I got a surprise private message from my uncle saying he'd be in town the following week and wanted to keep his promise of buying me a nice dinner. I told him I was pretty busy with school and work but I was intrigued when he said he had a business proposal for me. I reluctantly agreed to meet him for dinner the following week and he mentioned to dress nicely seeing it was a fancy restaurant.

My options for dressing for dinner were limited, after all, I was a poor college student. I chose a simple black dress and black heels. It wasn't sexy at all but I figured it would be fine. When I met my uncle at what turned out to be a five-star restaurant, he bought me a drink at the bar while we waited for our table. Thankfully, I had a fake I.D. Uncle Jim told me how beautiful I looked and thanked me for joining him for dinner. We talked briefly about his divorce and admitted he slept with other women but that wasn't any big secret.