My senior prom was the most memorable night of my life. My date, Caitlyn, was stunning. She is nearly 6’ tall, with flowing auburn hair, all natural. Looking at the freckles dotting her body was enough to be certain, but the little red bush was confirmation. She kept it mostly shaved because of her swimming, but left just enough curls on top to emphasize the match. She swam varsity and all that training gave her an athletic, lean frame along with a small firm ass. She had a fairly flat chest, barely an A-cup, topped with tiny little nipples.
Despite being one of the more attractive girls in school, Caitlyn was nearly as shy as I was. Her shyness was often taken as being conceited, but having talked to her during class at times I thought I knew better. I think that her tall, athletic build intimidated plenty of guys. It only made her sexier in my eyes.
I’d had a crush on Caitlyn since our sophomore year. Two months before Prom, I finally got the nerve up to ask her out. I had never known her to go on a date. The only dances she attended she was with a group of girls.
She was from a strict Catholic family, so before we ever went out, I had to meet her parents to get their approval. The first couple of dates were movies at her house, I guess to demonstrate that I was serious about getting to know her. Even after that, she could only go out once per week, and had to be home by 11pm. So we didn’t have a great deal of time alone together. In seven weeks of “dating” we had kissed a few times and engaged in some light petting over our clothes.
The week before Prom we both lost our virginity in the backseat of my Mustang. I was not expecting it. As it turned out, it was more awkward than memorable; I never did get positioned to go more than half way inside of her. But we had done the deed. She even bled, so it was “official”. I was so nervous about being caught that I didn’t even cum, and it was clear she didn’t enjoy it that much either. But we assured one another that Prom night would be better. Both our parents thought we would be at an all-night lock-in event. We had a picnic shelter area at a nearby park picked out. I planned to bring a soft blanket and some candles.
Prom night came and Caitlyn looked smoking hot. The long, backless, black dress emphasized her lean body. It was slit high up one leg, where, if she moved just right, I could see her creamy thigh above her black stockings. At dinner she slid my hand under her dress to show me that she wasn’t wearing any underwear. After a quick brush across her bare pussy, she moved my hand back to the table. My dick nearly tore through my tux pants. We did the bump and grind all evening, or at least when a chaperone wasn’t telling us to cool it. My balls ached like they were in a vise by the time we left the dance.
We drove straight to the park. I knew about a service road that led into the park because of my part-time job with a landscaping company that had the contract for the parks district. The service road has a gate, but I copied the key one day at work, figuring it would come in handy. I figured we would be safe from police or curious park rangers as long as we stayed away from the main entrance area.
I chose a small, secluded shelter that would be well away from the main areas even in the daytime. If a ranger opened the main gate and drove through the parking lot, it would still be hard to notice us, or my car parked behind the shelter. I was also certain we would notice any car lights with plenty of time to avoid any compromising position.
I spread the blanket over the table and risked using a few candles so I could better enjoy my beautiful date. As anxious as I was to start, I wanted to take my time and make this a special memory for both of us. I stroked her hair gently as we kissed. I ran my fingers lightly down her bare back, savoring every inch. I moved to kissing her neck lightly as I tried to gently slide the dress off her shoulder to expose her breast. I say tried because I was more clumsy than it sounds. I wasn’t exactly the smooth, experienced lover that I wanted to image myself. My kisses flowed the dress off her shoulder and down her arm. My hand slid to her breast and began a gentle caress, trying to avoid the nipple for later.
Everything was going exactly how I had fantasized since before I asked her out. Soon my mouth would be on her breasts and after that, working my way down to taste her pussy. Although we had sex once before, I had never nibbled on a nipple or tasted a twat. I had kissed my way back up to her shoulder and was working my way down her chest. Just before my mouth reached the top edge of her breast we were interrupted.
“That’s one fine piece of ass, isn’t it”
I was too shocked to answer, but before I looked up I heard several voices agree. The voices were unmistakably black and rough. Seems that my ideal make-out shelter was also an ideal drug transaction location. Nor was I the only one with access to gate keys.
They lifted me off Caitlyn and the one who spoke first took over. Except he wasn’t interested in foreplay; he immediately pulled her dress up and exposed her pussy.
“This party needs some light”
One of the boys pulled a car around and positioned the lights to shine directly into the shelter. I could see how scared Caitlyn was, but I was helpless against 5 muscular black teens. Particularly since they all looked like they had some experience with fights and I was a white boy from suburbia.
It was a good thing that Caitlyn was as excited from our evening long foreplay at the dance as I was. I could see in the light that her bald lips were moist. Once I had more experience with women, I could look back and realize that those lips were swollen a great deal too. The gang leader had unzipped his pants and was in the process of pulling out a baseball bat. Or at least that is how big his dick looked. I couldn’t tear my eyes away as that monster dick moved closer to Caitlyn. It was shiny black against her creamy skin and I couldn’t imagine something that large fitting inside her tiny body. When he placed the head against her pussy, it seemed to run the entire length of her lips. Forcing that into her tiny hole would rip her wide open. She might need to go to the hospital and be sewn back together, but I couldn’t take my eyes off of what was about to happen.
He was much more gentle than he could have been, although you might never convince Caitlyn of that. He slowly pressed forward and used his hand to move his dick slowly back and forth. Soon the tip was starting to align with the growing hole. He continued pressing forward and the hole stretched more. Slowly the invader pressed onward until finally her pussy swallowed the last inch of the head almost instantly. He was inside her and her started thrusting slowly back and forth.
“Are you a virgin?”, he asked my date
Her eyes were closed and she just nodded no.
“Well you sure feel like one. I’ll bet your boyfriend over there has a pencil dick.”
His friends all looked at me and laughed. His dick was probably a foot long and a thick as Caitlyn’s forearm. He was halfway inside her now and she was begging him to stop. This only turned him and his friends on more. He steadily, but persistently, continued to work himself deeper and deeper into her cunt until he was balls deep. Once she was opened up, his pace quickened.