Disclaimers: Everything you read in this story is my intellectual property and as such should be treated with utmost respect. This is a work of fiction based. The people described in the story do not exist as described but you can still find personalities like those presented. ANY RESEMBLANCE TO REAL PEOPLE IS ENTIRELY COINCIDENTAL ON MY PART.
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Biology-Final-Bet-10
Recap From -1 through 9: I am Paul, 16. I lost a bet to Jen, my grade rival in high school, which obligated me to eating her pussy and jacking off in front of her friends. My best friend Tom came with me just to make sure things did not get out of hand. When we got back to my house, Tom and I got off with each other for the first time.
Tom flipped back to put his head on the pillow next to mine. We looked at each other and laughed. The heat of the moment had taken us on a journey we did not expect. We believed we were straight at the beginning of the evening. Now, we knew we could also take care of each other without hesitation. Does that make us bi?
Before we could process our thoughts my phone let me know I had a text message. I got up and retrieved the cell phone from my jeans. Carol and Sue wanted to know if Tom and I would like to go to Carol's Saturday evening for a swim. Swimsuits would be optional since her parents would be gone for the weekend. Tom slapped my ass and said to count on him to be there.
Carol and Sue are both on the cheer squad with Jen. Carol is about 5'5" and 120 pounds. Sue is a little shorter, about 5' 3", and roughly 115 pounds. Both girls have great skin, beautiful legs and nice size tits. No horny guy would turn away from our opportunity to swim with them.
After two rings of the doorbell, Carol opened the door with Sue standing back behind her a little. Both girls were both fully dressed in shorts and nice tops, which accented their bodies. As we sat down, Carol sat with me on one section of the L shaped couch and Sue sat with Tom.
We played a strip game with lots of necking and groping. Each time the necking and groping increased and lasted longer. Carol smiled as she dealt the next hand. It was obvious that Tom and I lost. The girls helped us out of our underwear. I am not sure how long we were necking. The girls stripped naked and ran into the pool with Tom and I chasing behind. We were swimming and playing when Carol's older brother, Jake, showed up and turned on the yard spot light. He made a huge production of the situation and ended it by having Tom and I suck each other off and then Jake jacked on our faces. Carol promised us she would get him back.
Just before the 4th of July, Carol had Sue, Tom and me over for another swim party because her parents were gone for a long weekend. The four of us had mutual oral sex. Carol had found her brother was selling pills. She hid his supply and money as she implemented a blackmail plan as a payback for what he did to our first get together and to turn his life around. Her brother was humiliated, pissed and trapped into following Carol's directions.
Carol held a party for a dozen kids including her and Sue on the 4th of July. We played two games. One was strip polo the other was a variation of spin the bottle. Everybody had fun looking and touching the guests who were in a state of undress. At the end of the party, Jen and a boy named Nick gave me a blowjob for some unknown reason. As we cleaned up after the party, Carol's brother called to tell her he had to talk to her alone right away.
Tom and I sucked each other off as we got ready for the fireworks. Tom has really become extremely interested in my ass but I think any ass would do.
Carol's brother, Jake, got the shit kicked out of him by the guys providing him drugs to sell. They made him watch another young guy get raped over and over as a warning to return their stuff and all the money he owed or he would suffer the same fate.
It appears Tom made contact with Nick, the guy with Jen, when I got a BJ at Carol's party. His mom said he went over to Nick's house.
The important news came from going to a family barbeque. I lost my virginity to a college coed in a three way that included my 18 year old girl cousin.
Tom and I got together to talk about me losing my virginity and Tom fucking Nick. Tom seems more interested in trying to get with my cousin and her roommate then doing a repeat with Nick. Tom did not rule out fooling around with a guy, mainly me. Carol is waiting for my call.
Carol and her uncle saved Jake from the drug dealers. Jake, Carol, Sue and Linda are away at a cottage for a week. My cousin, Terry, and her college roommate, Fran, had us over to their place. Tom lost his virginity, while we all had sex. This was bisexual all the way, including a dildo and more.
Tom has been pushing me to let him fuck me. Things he said told me that Nick had fucked Tom. I don't want to be gay but Tom is not gay and he has been fucked. The police found the drug dealers Jake was in with, tied to tables where they had been raped multiple times. Jake was lucky. The girls will be back in a few days.
The Carol and Sue got back and we necked in the park. They told Tom and I about Carol, Sue and Linda using small pickle cucumbers to simulate sex with a guy. Tom took their idea and convinced me that the two of us should do the same thing to simulate anal sex. Once we had done that Tom decided we should seize the opportunity to do the real thing.
NOW CHAPTER 10
Tom put lube on the condom covering his dick. He picked up my legs and put them up his chest exposing my asshole. Tom leaned in and said, "Paul just take deep breaths and relax. I will take my time. I promise I will not hurt you. It will not change who you are."
He positioned his cock head against my hole and pushed. I could feel my sphincter give and the head of his dick get past the gate to my ass. There was burning but not intense. The feeling only reminded me that the burning related to the pickle gave way to a strange feeling and pleasure. Then Tom continued deeper. With my legs in on his shoulders I had no control as he hit my spot. I must have made a sound because I could tell by the look on his face he knew he was giving my prostate a workout. He started to pump in and out. He made sure he hit my spot over and over again. I could feel my orgasm building. I tried to stop it but Tom was in complete control. Then it happened; my wad boiled over and I shot volley after volley of cum onto my chest. My ass ring clenched tight on Tom's shaft sending his cum shooting into the condom. We stayed very still for a few moments before he slowly pulled his dick from my ass and let my legs drop to the bed. I had been fucked.
Tom smiled at me saying, "You sure got a lot of cum on your chest. You didn't even touch your cock." Then he went to flush the condom and get a wet wash cloth to clean me up.
My cock was quickly getting hard as I thought about fucking Tom. I got up on my knees on the bed and shook my cock at Tom as I said, "You are going to love this."
I tore the wrapper and unrolled the condom onto my dick. I put a generous amount of lube all over the condom. Tom looked at me as I lay on my back holding my stiff dick straight up. I let him know what I wanted, "Straddle my dick and start by fucking yourself. We will change positions in a couple of minutes."
Tom's cock was not yet stiff as he lowered his ass onto my dick. He grimaced as the head of my dick entered his hole. Slowly he lowered himself till he had my entire dick inside. The warmth around my cock was amazing. He sat very still for a minute. Then he leaned forward and started to rock. My dick moved in and out with every motion Tom made. Tom was not moving fast but very deliberately. He was watching himself in the mirror on his dresser. His dick was stiff and waving as he began to sit more upright and bounce on my cock.
The time had come to change positions. I told him to climb off my dick and lay on his back but position himself so he could watch in the mirror. I pulled his legs up across my chest and to my shoulders. When I looked down, I thought his asshole was winking at me. I leaned in to push his legs toward his chest and quietly said, "I have an advantage because I already got a load off. I will be able to hold off longer this time. You are going to be so well fucked by the time we are done."
I pushed my cock all the way in a single push. Tom gave a grunt as I bottomed out with my balls on his ass. My strokes were slow on the upstroke and hard on the push-in. As I picked up speed, I was drawn to Tom's eyes. Tom's eyes had a glazed gaze, like he was only focused on the dick working his ass like a piston. "Tom look at yourself in the mirror. You like being my fuck toy?" Tom turned his head towards the mirror and then back to my face. He smiled.
Tom reached down to his stiff dick, which was leaking pre-cum all over his abs. He held his balls out of the way of my body as I pushed. I started moving my dick in a circle on the upstrokes. Tom's dick twitched as I rubbed across his prostate. He was moaning with every stroke. I could sense my balls start to churn a pending release. Tom took both hands to my ass, pulling me as deep as I could go. Tom's dick exploded, shooting cum between our chests. I told him, "Time for your rabbit fuck." I worked my dick in and out of his hole as fast as I could move, till it unloaded in the condom.
I let Tom's legs go as I collapsed on his chest. We had ragged breaths and were sweating profusely. I moved my head and kissed Tom's forehead as I pulled my softening cock from his hole. Tom smiled as I rolled off to run to the bathroom to dispose of the condom. I also took the opportunity to take a piss.
As I flushed the toilet, the door to the bathroom opened. Tom came in the bathroom, grabbed two towels and turned on the shower. We quickly showered, dried and returned to the bedroom to pull-on our briefs. Tom took the bag with the condom wrapped pickles down to the trash in the attached garage. He hid the rest of the condoms and lube in his nightstand.
As we climbed into bed we heard the garage door opener signal Tom's mom and dad were home. We quietly whispered about the evening and our sexual experimentation. Of course we talked about the afternoon with the girls. We had never thought about girls playing with themselves or in groups like guys. "Paul, you really pounded my ass. I am not sure my asshole will ever fully close. When you told me to look in the mirror, I thought my balls would unload right then. Do you think this will change the way we feel about girls?"
I responded, "I can on only speak for myself but I still love tits and pussy. Helping the girls have orgasms was almost as good as the girls getting us off. I am not going out looking for a guy to put his dick in my ass. But, I now see why some guys like anal sex for the warmth, closeness and prostate massage."
"I want you to know, it was so much better with you than with Nick. Maybe it was because I care about our friendship and your feelings." Tom stated flatly. He reached over and patted my stomach. We fell asleep with one of my legs on top of one of his legs.
We woke to a tapping on Tom's bedroom door. Tom's dad told us breakfast would be in fifteen or twenty minutes. Tom and I yawned, stretched and kicked off the covers. Tom rolled over on his stomach and said, "My ass still hurts."
I quickly jumped across his legs and sat on his thighs. My hand grabbed his briefs and pulled them down in the back. Taking two hands, I pulled his ass cheeks apart to show his slightly red asshole. I took in a deep breath and blew my exhale, like a whistle, across his hole. "Well, it looks like you will live. May I suggest you avoid putting things up that ass for a while?" I laughed. We wrestled for a minute then ran to rinse in the shower and quickly get dressed.
When we sat down for breakfast, we found out Tom's mom was already out shopping. Tom's dad put down platters of scrambled eggs, hash brown potatoes, bacon and toast. As he sat down to join us, he placed the box of wine in the middle of the table. "Either of you boys going to tell me what went on last night?" We knew we were busted for drinking.
"Dad we each had a glass of wine. The twins had left and the kitchen was cleaned. We were playing video games and just wanted to try some wine. We stayed in and went to bed early. I am sure I can speak for Paul, we are very sorry for stealing your wine. How did you know?"
"I trust you boys. I also know kids want to grow-up too fast these days. Life is going to put a lot of temptations in front of you. At 16, underage drinking can lead to a lot of trouble for you and the adults around you. There are worse things like drugs but drinking can be a major problem. As a parent, I always want you to act mature and responsible. That also means your mother and I expect you to be honest and obey the rules even when we are not watching. You were honest about what you did so as a first offense I will let it pass. I weighed the box last night and again this morning, so I knew you had been in the wine." Tom's dad said in a lecture voice. Then he smiled as he asked for the bacon.
Terry called me later the next week to tell me she and Fran would be heading back to college. She wanted me to know that they both had fun and hoped we would keep our minds open in sexual matters. Before Terry hung-up she said she would be back at Thanksgiving and that maybe Fran would come with her.
Labor Day and the start of school were fast approaching. Carol and Sue seemed busy with shopping. Tom and I would just get a couple of pairs of jeans, a few tops and a couple of team logo sweat shirts. We started pushing our parents for our drivers' licenses. Of course we talked about all the freedom a license would give us. That freedom included the ability to date girls and get a little privacy with them. Family commitments kept Tom and I from having sleepovers. The standard start of school letter came to our homes, with administrative details and information on various clubs and sports teams. Some of those things actually start before the beginning of school.
Tom and I were at the park playing Frisbee and just hanging out. The topic of trying out for the Football team or the Swim team came up. Neither of us had ever played organized football and our size seemed to make being successful at that very iffy. The swim team on the other hand did not have extensive tryouts for the purpose of making cuts but used tryouts to determine where on the team you might fit and what strokes could be honed for competition. We both were excellent swimmers and had spent a lot of time in lessons when we were younger. The best part was that boys and girls practice together even though actual seasons and competitions were separate. Swim team studs we would be.
Tom and I went to the Swim team organizational meeting. We got the permission slips and information regarding parental involvement and practice times (6:30 - 8:30am and 4:00 -- 6:00pm Monday to Friday). The coaches had everyone suit up and start swimming laps. Most of the team- established kids had Speedos or last year's team swimsuit. Tom and I wore lose fitting suits. Seeing some of the girls by the pool started Tom and me to chub. There were girls, I had never considered as date material or fodder for jack-off sessions, who were absolutely stunning in a swim suit with high cut sides and breast lifting tops. The girls were "sizing up" the guys too. Tom and I dove into the pool and started doing laps. Every now and then one of the coaches would blow a whistle and tell us to change strokes. We went between free style (crawl), butterfly, breast stroke and back stroke (back crawl). By the end of the session, most of us were very tired. We were told to hit the showers and be back ready to swim at 6:30am the next morning with our signed permission slips.
The boys' locker room was filled with mostly very fit young men. Everybody went to the locker where they had stored their clothes. A coach came in and blew a whistle. "Gentleman everybody on this team takes a shower after every practice. Please pay attention to the sign at the entrance to the showers, No Swim Suits in the Shower Area. Take your suits off at your locker and get a shower. When you leave the shower take a clean towel from the rack outside the shower. Once you are dressed, please leave your wet towel in the roll around basket at the door to hall. Be sure the area around your locker is tidy as you leave. Be warned that forgetting to take care of your towel or leaving your area untidy will lead to individual or team punishments. Now move your butts through the showers." He turned and went into an office with a large window looking down the locker room main aisle and next to the shower area.
Tom and I stripped off our suits and walked to the showers. The steam was rolling out of the shower room. Inside were young guys from 14 to 18. The steam was so thick you could only see those immediately around you. There were no really fat guys and a few skinny guys. Cock sizes and shapes ran the complete spectrum. Most guys were circumcised but a few were not. Although I am sure we all glanced around, no one was focused on dicks. We did laugh and talk about some of the girls but we were careful not to go over the top with comments for fear of a boyfriend being in the room. As we walked out of the shower area, a guy was loading the racks with towels. When Tom and I each grabbed towels, our mouths dropped open when Nick stopped loading racks long enough to say, "Hi. It's great to see you." Tom and I got dressed and left the wet towels in the basket as we left.
Before we got out of the school, two girls came up to us and asked if we had a car. They were looking for a steady ride for swim practice. We told them that at the moment we were on foot. As we walked the mile home, Tom and I talked about Nick, the girls and some of the guys. Tom said his dad could drive us to morning practice but we would probably have to walk home. I told him I would see about afternoon practice rides.