I had always been a shy girl growing up. I seemed so skinny compared to other girls: my breasts weren't as big, and my hair was so thick and hard to manage, I could barely keep it looking nice. Whether it was a lack of self-confidence or that I didn't really amount much to other girls, I never had many boyfriends. Revealing this, I never had many sexual encounters either. But through high school I did happen to have a couple of lousy boyfriends who pressed me to perform oral sex before leaving me in the need of wanting; after thirty second sessions of intercourse. Needless to say, I knew how to please myself and did it quite regularly; often thinking of guys I wished would acknowledge me. Sometimes I would even imagine multiple guys tending to my needs while I twisted my nipples and rubbed my pussy over the edge of excitement.
This all changed when I met who is now my husband the summer after graduation. Back then he was a taller guy with a nice body, but he needed a little filling out. Over the last six years he has filled out and has steadily worked out to keep in shape. That summer though was different. He was also a shy guy and was always the subject of ridicule from his friends who teased him about his lack of sexual encounters.
It was a Wednesday afternoon. I had just been to the salon for a cut and color and also had my eyebrows shaped. I had the stylist straight iron my hair too so my hair was sleek and shiny. Usually if I do not straighten it myself it has a little puff to it because of how thick it is. I was feeling good about how I looked. My skin was tanned and my boobs were perky and had grown through my senior year, but they were not huge. 34 B's but I was proud of them. I was still skinny, but nowhere near anorexic looking, so I saw myself as just a petite girl. I did my makeup, got dressed braless in a tight powder blue tank top and a snug fitting pair of short stretch denim shorts with a floral decorated white swatch with sea foam green and dark and powder blue flowers that I wrapped through the belt loops. I looked in the mirror and I was pretty. It slowly hit me how much I desired the love and attention of someone. I wanted to be in a solid relationship. These thoughts started to bug me so I decided I would go for a walk to the party store near my home.
While I was walking back from the corner party store less than two miles from my home, a 1984 suburban pulled up next to me and a classmate rolled down the window and asked how my summer was going. I replied that it was pretty boring so far and not much had been going on. My girlfriends all seemed to be on vacations and the only person to spend time with would be my next door neighbor. He wasn't home this day so time was apparently dragging on.
"Why don't you come for a ride with us, Rebecca? It's me (Zack), Sean, Ron, Darren, and Scott. I'm sure we could fit you in here too!"
I was a little hesitant, even more nervous. My heart rate increased and sensations sparked between my thighs. I'm sure the look on my face told the story to Zack. These were all guys I wished had acknowledged me before. The ones I had fantasized about while spinning my clit towards orgasms that my pathetic past boyfriends could never even possibly bring me to.
"Where are you guys going? What time will you bring me home?" The questions kept coming and I am sure Zack thought I was giving him the 20 questions run down. He gave me a look as if what did any of that matter. I had nothing going on so I stopped with the questions so they wouldn't just pass me up.
"Okay" I said, and entered the suburban. I took a seat in the back bench seat with Scott, Ron, and Darren. I nestled my way between Ron and Darren and crossed my legs. My short shorts rode up a little and I know Darren had a good look at my exposed thigh. Darren looked at me and smiled and I watched his eyes move down towards my thigh.
"Well, what are you guys up to today?"
"Oh, not too much, we are just thinking of going for a bumpy ride through the trails behind Zack's farm" Ron said, as he put his arm around my shoulder. "Sound like fun to you?"
"Sure that sounds fun, I have never done that before" I said, as I felt Darren's hand sneakily slide the length of my exposed thigh. I looked over at him shocked by the attention I was receiving to notice a calming grin on his face. At that moment I realized my nipples were hard, poking through my tank top and the burning passion between my legs made me clench my crossed legs.
"That's great, I hope we can make this a good experience for you Rebecca" Zack said, from the passenger seat. My mind took that statement in different ways. One in a literal sense and the other in a sense geared towards my most devilish fantasy.
"How far to the farm" I asked.
Zack said it would be at least fifteen minutes and then another ten minutes until we were deep enough into the trail for a good ride. There was plenty of time to kill so I asked the guys about their girlfriends. I found out that they all had been dumped the day after graduation because everyone was planning on going to different colleges and it seemed like the right thing to do. Zack was the only one who didn't get dumped but he decided if all the couples were not going to spend time together during the summer, then he should break it off with his girlfriend too. And he did.
The drive consisted of mostly small talk and Darren and Ron's hands touching me more daringly. I would slap their hands away as if I didn't approve, but behind that, my nipples were still rock hard and my barely used pussy was getting so damp. I uncrossed my legs and felt the juicy heat down there and rested my hands on my lap.
We pulled into Zack's driveway and headed for the trails in the deepest areas of his parent's property. Ron leaned over, placed his hand on my stomach and rubbed slightly up under my breasts, making me gasped for breath in excitement and whispered into my ear, "I hope you enjoy yourself."
He left it at that and switched spots with Scott. Scott nestled up close and asked if I was ready. I just grinned and said, "I guess so." At that moment both Scott and Darren took one of my hands and held them.
"Hold on tight, this part of the ride is a little bumpy." Their grips on my hands were firm and each snuggled up closer to me as we made are way back into the trails. Simultaneously they leaned in closer reaching with their free hands to place on my thighs. Scott leaned in and let a shot of warm breath and a gentle kiss on my neck. He opened one thigh and moved his hand up my thigh, while Darren nibbled on my ear and whispered into my ear that he thought I looked so hot as he opened the other thigh and slid his free hand up towards my steaming love box. All this made me release a deep breath and lean my head back. As I relaxed for that moment, I felt both of them use their index fingers to press against my aching clit. They continued the stimulation for a brief moment and stopped.
