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.
"We're here" Zack said, from up front. "Get ready to bounce around."
I was excited. Stimulated from the sexual attention and anxious to see how this trail riding would be. Sean stepped on the gas and we took off fast and hit the first bump of the trail. I bounced pretty well in the seat and let out a little chirping scream. I placed my hand out to the side to brace myself while coming back down to the seat and became embarrassed when it landed in Scott's lap. "I'm so sorry" I said, but Scott just looked at me and smiled ensuring it was okay. I didn't move my hand and I felt his cock growing beneath my hand and I looked at him. He didn't look back and I just gave it a squeeze. I continued to pulse my grip on his stiffening member as we sped through the trails.
"Oh my god" Scott released, and we hit another bump. My grip did not let go of his raging hard-on, and I felt that I may have gave it a painful tug as I bounced around. Scott released a "OOHHH" with a grimace on his face and I apologized again. He still grimaced but a smile broke on his face and he began to laugh. I am sure it was a little painful but it wasn't that bad and the circumstances made the event funny. We both broke out laughing and Ron and Darren did too, obviously noticing what had just happened.
We hit a clearing and I released my hand from Scott's aching cock; probably aching in more than one way. He switched spots with Ron again and Darren took my hand and placed it between his legs. I could feel his erection beginning so I looked at him wide eyed. Ron grasped my right tit and gave it a squeeze. I turned my head to him and he planted a deep French kiss, making me squeeze Darren's cock. I broke this kiss and Ron moved his hand from my boob down to my thigh and glided his hand up to my pussy. He gave it a quick rub and moved his hand higher and unbuttoned my shorts. Darren was caressing the shape of my other tit and I just closed my eyes.
"Oh shit, here comes a big one" Zack and Sean screamed from up front. We all braced ourselves and prepared for the impact. The force set me bouncing up off of the seat sideways and I landed on Darren. When I landed, he let out an "umph" but he was okay. I could tell because I felt his hard cock pressed between my ass cheeks. He held me tight as we continued through the trail. His hard cock beneath me aroused me even more and his removing my tank top almost set off an orgasm from inside me. He cupped both my breasts as we hit another bump. We bounced together and when we landed I heard and muffled groan of pain come from behind the bench seat.
"What was that" I asked. I got off of Darren's lap and looked behind the bench seat. And there he was. I felt so bad for him. It was my next door neighbor, my eventual husband, hands and feet tied, and gagged.
"Okay, Sean it is time to stop. She found him" Scott said. I was so shocked to see Kenny there. No wonder he wasn't home today to hang out with. We got out of the vehicle and opened the back of the suburban. Kenny just lay there still, almost lifeless.
"Why do you have Kenny tied up like that" I asked.
"Rebecca it is a long story, but first off, Kenny has a huge crush on you and he has for a long time" Darren said. "This is the only way we could get him to finally ask you out, but there is a lot more to the situation."
"Then why are you guys putting moves on me? Rubbing my pussy, kissing my neck, fondling my tits?
"You see, Kenny hasn't had a lot of girlfriends and the main reason is because of his particular sexual desires. By doing what we did, we were testing you to see if you were the right one for him."
"I don't understand" I said.
The guys all replied to me telling me stories of Kenny's sexual fantasies. They revealed his secrets of wanting a girlfriend, who would be willing to be watched, take on multiple guys, double penetration, and many other kinky sexual desires.
"Kenny is a pornoholic and if he's seen it, he wants to live it" Scott said.
I just stood there topless, my nipples still erect and my pussy was still yearning for pleasure. "Untie him at least" I demanded.
They untied and ungagged him. "Is this true Kenny?"
Kenny sat up and rubbed his wrists where they were tied up and looked me in the eyes and confided his feelings. "I am in love with you Rebecca, and I just couldn't bring myself to express these things to you. That's why the guys pulled this off.
I thought about what was going on and before I could say anything, Sean, Zack, Scott, Ron, and Darren were approaching me. They surrounded me. They had there shirts off and cocks out of their pants. I looked over to Kenny and he stared back at me. They guys started rubbing my tits and were removing my shorts and panties. I stood there naked surrounded by these five guys who were sucking my nipples, kissing my neck, and squeezing my ass and rubbing my pussy. I looked again at Kenny and he stilled stared at the sight of me being taken by his five friends. I gazed my eyes downward from his face and noticed he was forming a bulge in his shorts that he needed to adjust. I said to myself "What the hell" and just let things happen.
It wasn't long before I was on my knees with a circle of hard cocks around me. One by one I went around the circle sucking each cock. The guys were moaning, some were holding me by my head and shoving their cocks deep into my throat. They ravaged my face with their stems and drool was falling from the corners of my mouth onto my tits.
I stood up and Scott picked me up and placed me into Kenny's lap. Kenny held me close and I could feel his hard-on pressing against my tailbone. Scott moved in close and inserted his cock deep into my wet pussy. He plowed in and out, while all the while Kenny whispered into my ear how hot I was, asking me if I enjoyed this, telling me he loved me. He kept saying dirty things in such a kind way and I felt so comfortable in his arms. The experience was pushing me over the edge as each guy took their turn ramming in and out of me. All I could do was make agreeable moaning noises. I was in pure ecstasy. My dirtiest fantasy was happening and I felt loved.
At sometime, I think when Zack (who had the biggest cock, maybe 8 or 9 inches) was sliding in and out of my dripping pussy I shuddered into a massive orgasm. I leaned my head back and whispered to Kenny that I was going to cum. He encouraged me to release my juices all over Zack's cock and I let out a mild scream as my pussy pulsated around Zack's cock.
After they had all taken their turns on me, I was positioned on top of Ron, who was lying next to Kenny in the back of the truck. I positioned his cock into my twat and slowly raised and lowered myself onto him. I looked to Kenny who was now stroking his nicely sized cock as he watched me fuck his friend. He looked at me and told me I was beautiful and that he loved me. Just then I felt someone climb up into the back and put his hands on each of my as cheeks. I then began to feel a cock resting at my virgin ass.
"OH, no, no. Not in my ass. I'm not comfortable with that just yet. I don't want it to be messy. Both of you should just take my pussy instead" I said.
That was all it took. There was no hesitation and I felt a second cock enter my hole. I was so full and the stretching feeling made me shriek and whimper. It must have been Zack's huge cock that entered me along with Ron. Their motions countered each others and the feeling was intense. As I finally became comfortable with such a stuffing, Zack pull out and another moved in. I was definitely losing my mind now and was caught up in the experience I was hoping for earlier.
"Oh my god Kenny, I'm fucking your friends and I love it! I love watching you stroke your cock while you watch me fuck your friends. Does this make you happy?"
Kenny looked at me in pure lust and shook his head to say yes while furiously fisting his cock. Everyone had double fucked my loosening hole and I had another orgasm. I was spent as I crawled off of Ron and wanted to lie down.
No rest for the wicked I guess as they told me to get on all fours and suck Kenny's cock. I did not hesitate despite how exhausted I was. I sucked him the best I could and noticed the five guys standing around stroking themselves. One by one as I sucked off Kenny, the placed the tips of their cocks into my hot juicy hole and stroked themselves to completion. The first one was the most alarming. As I felt the first seed which seemed to spiral its way deep into my womb, all I could think was I was going to get pregnant. I wasn't, nor have I ever been on birth control. I was scared and my cock sucking slowed down. I never released Kenny's cock from my mouth but continued by stroking him. My thoughts kept raging on as another seed was implanted deep into my pussy. I let out a humming moan onto Kenny's cock and another seed was deposited deep into me and Kenny began to spurt stream after stream of his semen into my mouth. I moaned more and swallowed while the guys finished depositing all of their loads into me.
I collapsed into Kenny's arms. Cum was leaking slowly out of my hole and I was struggling to catch my breath.
"Sit on his face Rebecca and make him eat the cream out of your pussy. Maybe it will help prevent you from getting pregnant" Sean said.
I looked to Kenny, thinking no way. This has got to be the grossest thing I've ever heard.
"Just do it Becky, I'm sure he will love it."
I looked to Kenny again and he looked back with an embarrassed smile. "I will do anything for you Rebecca. If it helps I will do it without any regrets."
I squatted over top of him and lowered my messy hole onto his lips. His mouth open and I stared down at my cunt dripping a strand of fresh cum from his friends aimed towards the back of his throat. I squeezed my pussy muscles to see an enormous amount of cum flood his mouth. It all dropped in and he swallowed and feverishly began lapping at my raw pussy.
"Oh man, look you guys, Kenny's getting hard again" Scott said. I turned my head and sure enough, he was ready for another round. I squeezed again and another gob of goo dropped into his mouth. He moaned as he swallowed another pile of semen deposited into his mouth. He cleaned me for nearly twenty minutes and until my pussy was no longer leaking any fluid. When he was finished I moved back and lowered my pussy onto his cock. I kissed his cum covered lips and inserted my tongue into his mouth as the length of his shaft buried into me. I could taste the remnants of semen on his tongue and rode him continuously until he deposited his load into me this time. I didn't make him clean me out though. I rose up off of him and we watched together as his spent cock juice drained from my now dilated opening.
The seven of us stayed together for the evening. The guys had a case of beer and we built a fire pit back in the trails. We spent the rest of the night hanging out and reminiscing about our pasts. Yes we did reflect on the days events but that was over now. We were like best friends spending time together before moving away.
Kenny and I were inseparable from that day on and he finally asked me to be his girlfriend which I could not refuse. I knew him well, felt his love, and most of all, I was sure to be sexually satisfied. Three weeks passed and I missed my period. I told Kenny and he offered money to abort the pregnancy, but I couldn't be positive it wasn't his. I told him it was too tough of a decision and said I was going to have the baby. He said to me whether it was his or not he would care for the baby like it was his. He proposed to me three days later and today we have been married for over six years and we are raising a six year old girl. She looks a lot like me, but I can't see any resemblance of him. He doesn't see himself in her either but he has kept to his word and is a great father. We both think we see Zack in our little girl.