Extreme Stories » Andy and the Team
First off, let me tell you about myself. My name is Andy, and I am fourteen years old. I am four-foot-eleven and only weight eighty-five pounds. I have blonde hair and blue eyes.
After my mom divorced my dad, he decided we needed a change, so he got a new job, and we moved to a small town. I played soccer at my old school and was good at it, so I decided to try out. Thanks to playing soccer growing up, I had strong legs and proved to be good enough to make the team.
In my first week of practice, I met six-foot-ten, two-hundred-ninety pounds of muscle named Brian. He is a senior who is being recruited by several colleges. As it turns out, Brian and I live on the same road. There is one house between us. He was kind enough, but since I was the new kid and a freshman, we did not become good friends at first.
The first week of school was miserable, with no friends, learning a new school, and meeting all new teachers. That Friday, we had our first game. It was a hard-fought, close game. I made the final goal, and we won. After that, things improved. Students were nicer to me, and I was really part of the team. Brian invited me to ride to school and then home from practice with him. He even asked me inside to play video games with him. He was smart, funny and I enjoyed hanging out with him.
Then I met his sister Shannon. She was gorgeous. Long blonde hair, big breasts, and the cutest ass you have ever seen. I was barely fourteen and had not yet kissed a girl. However, I masturbated, and let me tell you, she was the center of my fantasies. She was a college freshman who lived on campus.
I was happy, and everything was going good until homecoming week arrived. It seems it was a tradition for the homecoming pep rally for the seniors to pick six new players, and they had to dress up like a cheerleader. As you would expect, I was chosen to be one of the six.
Usually, it is just guys dressing like girls for laughs and receive good-natured ribbing. I was telling Brian I could not do it. He told me to relax. His sister had been a cheerleader in high school, and I could probably fit into her stuff.
Since the Pep rally was the last period on Friday afternoon, Brian talked to Shannon, and she agreed to come home on Thursday and help me out. Since their dad worked second shift, he never got home before midnight, so after practice on Thursday, I rode home with Brian.
“Are you nervous, Andy?”
When we got to Brian’s house, he told me Shannon would be home in about a half-hour or so. He offered me a beer. It was the first beer I had ever tasted. While we waited, I drank a second beer, and I was feeling the effects of the alcohol. Finally, Shannon showed up, and she told Brian to amuse himself while we went to her old bedroom, which she still used when she was home.
I was so embarrassed that I just stood there.
“If you want my help, you’d better strip. Now!”
Still, I could not do it. Finally, Shannon slapped me hard across the face.
I was in shock as I followed her directions. When I was down to my underwear, I stopped.
“Your underwear, too. Take ‘em off!”
Afraid of getting hit again, I slid my underwear down and stood there naked.
She handed me a pair of red panties
“Put ‘em on.”
I slid them up my leg, she handed me a pair of tan-colored tights and showed me how to put them on. She pointed and laughed. Oh, god, I was getting hard.
“You must really be enjoying this! Maybe you want to be a girl.”
I am sure that I flushed several shades of red. Finally, Shannon handed me a white skirt to put on.
“You’re looking good so far. It’s a good thing you have no body hair.”
Shannon handed me a white bra.
“It’s only a 32B, but don’t worry, a lot of guys like girls with small boobs.”
She laughed again. Finally, I put the sweater on. I looked in the mirror, and as you would expect, I looked like a guy in girls’ clothing.
“You need some makeup.”
“I don’t need makeup. I’m not supposed to look like a girl. I’m just supposed to wear the outfit.”
She slapped me hard and set me down at her makeup table. She showed me how to put on makeup and how to take it off. I put it on and took it off four times before she said I was good enough. Then she tied my hair into a ponytail with a red ribbon. She led me to a full-length mirror, and the girl looking back at me was really cute.
She made me put on a pair of white socks and a pair of pink tennis shoes she had in the closet. Then she looked at me and said it was time for my debut. She led me from the bedroom to the family room where Brian was still drinking beer and watching TV.
“Close your eyes, Bri.”
She then pushed me into the room to stand in front of Brian.
When Brian opened his eyes, the look on his face was odd and scary.
“Wow, Shannon! You did a good job. If I didn’t know who it was, I’d want to hit on her.”
While she was gone, Brian just stared at me. It made me nervous. Shannon returned, and I saw a flash. She was taking pictures, and she started telling me how to pose.
“Turn around. Shake your ass.”
She came over and flipped up my skirt.
She took several more.
“I need to get back to my dorm room,” Shannon said.
She handed the camera to Brian
“Make sure you download the pictures and email them to me.
“Andy, you’ll be the most popular cheerleader tomorrow.”
As I heard Shannon drive away, I started back up the stairs to change.
“Wait, Andy. Let’s go to my room first to see how the photos turned out,” Brian requested.
When we entered his room, he sat down at his computer.
“Sit on the bed, Andy.”
Instead of hooking the camera to the computer, he started taking more pictures.
“Brian, I don’t like this. Please, let me change.”
I started to get up. Brian stood and pushed me back down.
“Please, Brian, let me go get changed,” I begged.
That’s when he slapped me. The look on his face scared me. I tried to make a run for it, but he was faster and, of course, stronger. He punched me in the stomach knocking the wind out of me. I doubled over, and he grabbed my ear and tugged me back to the bed.
“Listen, sissy boy, you will do whatever I say, or I will beat the crap out of you, and then you’ll do whatever I want anyway.”
“I don’t like this, Brian. Why are you doing this?”
“Because, Andy, I can!”
He then told me different poses he wanted me in and even made me take off my shoes and socks. He took several pictures of me sliding my pantyhose off, and then he told me to take off the skirt and sweater while snapping photos the whole time. Finally, after he took several of me in bra and panties before he put the camera down.
“I broke up with my girlfriend right before school started, and I’m tired of jacking off. Kneel beside the bed, fag.”
I was scared and thought about trying to run for it again but figured he would just beat me up, and I did not like that idea. All of this was going through my mind as Brian took his t-shirt off, and then he slid his shorts and boxers off. Oh. My. God. His cock was huge—seven inches, at least. He sat down on the bed and spread his legs.
“Kiss my cock, queer boy!”
“Please, Brian, don’t make me do that. Please don’t.”
He just laughed and slapped me again, knocking me backward. Finally, I got back on my knees and crawled around until I was between his legs.
“Do it!” he ordered.
I took a deep breath, leaned in, and kissed the head of his cock.
He was taking more pictures. I kissed his cock several times.
“Lick the shaft!
Oh, God, I can’t believe I was doing this. I am not gay. I like girls. He moaned as I licked the shaft.
“It’s been too long since I got my cock sucked. Get the head in your mouth.”
I took another deep breath and let the tip slide past my lips. I started sucking on the head.
“That feels good.”
“Start working your mouth up and down my cock—and watch the teeth.”
I was crying by this point but trying my best to get it over with.
He put the camera down, grabbed my head, and started forcing his cock deeper into my mouth. I was not sucking his cock—he was fucking my mouth and throat. I was getting light-headed because I could not breathe. Finally, he forced his cock into my throat.
“Here it comes!” he screamed.
I felt shot after shot hitting the back of my throat until he let go of my head, and I pulled off, trying to catch my breath. He patted my head as if I was his pet dog.
“That was okay, but you’ll get better.”
“I will never, ever do that again! It will never happen!” I shouted at him.
He laughed at my histrionics.
“You’ll do what I say when I say it, or the pictures of you with a cock in your mouth will be sent to everyone at school.”
He laughed when he saw the defeat in my eyes.
“Clean my cock up, cocksucker.”
I leaned in and started licking his cock to clean all the cum off of it.
“Get the fuck out of here. You tell anyone what happened tonight, and I’ll beat the shit out of you. Oh yeah, and don’t forget to wear your uniform tomorrow.”
I heard him laughing as I got dressed and ran out of the house. Thank god, Mom was not home. I ran to my bedroom, stripped off all my clothes, and entered the shower, and while crying, I tried to wash off what happened to me.
I tossed and turned all night, visions of what Brian had made me do going through my mind. I had a headache and felt terrible when I was getting ready for school. I thought about not going, but if I missed school, I could not play in that night’s game, and that would definitely make my teammates mad at me, so when Brian pulled in my driveway, I reluctantly went to meet him.
All he said was, “Do you have your cheerleading uniform with you?”
After that, we drove to school in silence. Brian kept looking at me funny and was glad when we finally pull into the parking lot. I grabbed my bag and headed inside. Most of the day went by in a daze. At lunch, Brian pulled me aside and told me not to change after the pep rally but to wear the cheerleading uniform home. Finally, it was last period and time for the pep rally. I joined my other five teammates dressing up like cheerleaders in the locker room.
I heard Jim say, “Wow, Andy, you’re really getting into this. You must dress up a lot.”
The other guys laughed at his comment. I decided not to wear makeup, as I did not want to look “too good.” We finished getting ready and waited behind the stage in the dark, waiting to be called on stage. As we were waiting, I jumped when I felt a hand groping my ass, followed by laughter. Soon we were called out. The six of us did our little routine, and the students laughed and applauded wildly. Instead of waiting for the end of the rally, I decided to slip back into the locker room, get my stuff, and wait by Brian’s car. As I was getting my stuff together, I was pushed against a locker from behind and held in place.
“So, I lost my spot to a fucking faggot.”
Right away, I knew it was Jason, the senior whose position I had taken. I tried to move, but he was holding me in place.
“I should kick your ass right now, but the coach will throw us both off the team for fighting.”
I felt his crotch press against my panty-covered ass and his hand rubbing my thighs.
“What the hell is going on in here?”
It was Brian. I felt relieved because I knew he would stop it. Jason let me go as he jumped back and gave a nervous laugh.
“I was just teasing the faggot,” he replied.
I received a big shock when Brian said, “I know you want to beat the crap out of him for taking your position, but you can’t do it here. Come back to my house with us, and I promise you can have your revenge and, maybe, have some fun in the process.”
Jason replied, “Are you shitting me, cuz?”
That’s when I remembered Brian telling me that he and Jason were cousins.
“I promise you it will be more fun than when we used to jack off together.”
Jason smiled and said, lead the way. We pulled out of the parking lot of the school with Jason following behind in his car.
“Brian, what are you going to do to me?”
“Just shut up, faggot. You’ll find out soon enough.”
As we entered Brian’s house, he told me to go get them a couple of beers. When I returned with their beers, Jason was on the couch, and Brian was coming down the stairs with a couple of DVDs. He inserted the first DVD, and there I was on the big screen TV in my cheerleading outfit. He flipped through the pictures of me in various poses. I had hoped that he would stop before he got to the ones of me undressing, but he did not. Jason was making all sorts of rude comments. Then Brian told Jason to watch this. He began showing Jason the pictures of me sucking his cock. Jason was laughing and said I looked like I was enjoying myself. After Brian had shown Jason all the pictures, he put the second DVD in, titled World’s Best Blowjobs.
“Watch carefully, cocksucker. Maybe you’ll learn something,” Brian said.
“Why don’t you sit beside me?” Jason requested.
I sat down beside Jason, and Brian sat down on the other side of me. Here I was still dressed as a cheerleader sitting between two boys from the team. As Jason and Brian drank their beers and watched a cute blonde girl sucking a big cock, I noticed them rubbing their crotches and adjusting their cocks. Brian and Jason talked about how much fun it was when they were younger and watched porn and jacked off together. I watched in horror as both Brian and Jason unzipped their jeans and took out their hard cocks.
It did not take long until Brian told me to get on my knees. I pleaded with him not to make me do this. That is when he slapped me hard across the face. Jason laughed and said that he wanted to do that for a long time. Brian told him to go ahead. Jason slapped me hard across my right cheek, and then he hit me again as I started to cry. Brian laughed.
“I have an idea, why don’t we paddle his ass?”
“Excellent idea, Brian,” Jason agreed.
Jason pulled me across his lap, and his hard cock pushed against my stomach. He started slapping my ass over and over. After about ten whacks, I noticed that after each one, Jason would cup and grope my ass cheeks. His cock just seemed to get harder if that was possible. Finally, Jason tired of spanking me and pushed me off his lap. I landed on the floor on my still stinging ass, looking up at his hard dick. He gave me a look that was cruel and lust-filled at the same time, and then he told me to suck his cock as I did Brian’s last night.
At this point, I knew it would do no good to beg, so I resigned myself to getting this over with as quickly as possible. I crawled back to Jason and took just the head into my mouth. I heard Jason moan. I started working my mouth up and down his cock. He told me I was doing well but to lick and suck on his balls. I hesitated before I could bring myself to lick his sweaty balls and then suck on them.
Damn it! There was Brian with that camera again.
He took another picture as I went back to sucking on Jason’s cock. Besides taking more pictures, Brian was also jacking off watching me suck Jason. Again, I started working my mouth up and down, up and down, taking the cock deeper and deeper into my mouth. Jason really did start moaning then. I felt him stiffen even more and knew from last night with Brian that he was about to cum. That is when he surprised me by pulling out and shooting strand after strand of cum all over my face. When Brian saw Jason cumming, he gave a big groan and started shooting on my face mixing his cum with Jason’s cum.
Brian took several pictures on my face covered in cum. He told Jason that he would add them with the others of me he took last night. Jason told me to scoop up all the cum and be sure to swallow it.
Great, now he has pictures of me eating cum. As I was finishing wiping the cum off my face and licking my fingers, he was zipping up and said he had to go, and he would see us at tonight’s game.
After Jason left, Brian told me that he did not have a date for the homecoming dance after the game and that I was to tell my Mom that I would be spending the night at his house. It was getting late, and I had to go home and change. As I left, Brian said he would pick me up in about thirty minutes. I went home, changed out of the cheerleading outfit, took a quick shower, brushed my teeth, and gargled several times.
After the homecoming game, Brian and I rode back to his house in silence. Brian was mad because we had lost the game. I was dreading what was going to happen tonight. In the last two days, I had given blowjobs to two different guys, and I knew tonight I would probably be forced to do it again.
As we pulled into the driveway, Brian told me to get his bags and bring them in. I grabbed his stuff and followed him into the house. As I entered, he was listening to phone messages. One was from Shannon, asking how I looked and did at the pep rally. The other one was from his dad, informing Brian that he had to work a double shift and that he would not be home until the next morning.
Brain led me up the stairs.
“I’m going to shower. You can use Shannon’s shower. I’ll lay out your outfit on the bed for you.”
I assumed I would be wearing the cheerleading uniform again.
“Make sure you apply to apply lipstick and some perfume. After you dress, come down to the family room.”
After my shower, I tried to take my time to put off what was going to happen, but I knew I could not put it off forever. After I dried myself off, I went into Shannon’s bedroom to see what I was supposed to wear. Oh God, it was not the cheerleading outfit. It was a purple lace teddy with a snap crotch and garters attached. He had laid out the matching stockings and a pair of black three-inch high heels. After I put on the teddy, I sat on the bed and rolled the stockings up my legs. I stood and attached them to the garters. I applied the lipstick and sprayed myself with Obsession. I put on the heels. They were a little tight but not too bad. The first time I tried to stand, I lost my balance and fell to the floor on my ass. The second time I held onto the bedpost and regained my balance. I tried to walk and realized that if I took small steps and kept the weight on the balls of my feet, I was still wobbly, but could manage to walk.
I knew Brian would be getting impatient, so I made it to the door and down the hall. I had to maintain a good grip on the banister to make it down the stairs without falling. As I made my way into the room, I saw Brian sitting on the couch, drinking yet another beer watching porn on the big screen. A redhead was on all fours having a cock forced up her ass and another one being feed to her painted lips. He looked at me and said that I did not look too bad, and he made me walk back and forth in front of him. Of course, the camera came out, and he took several pictures of me.
“Damn, those small steps sure do make your sexy ass wiggle.”
After he took pictures of me in various poses, he told me to get him another beer. When I returned, he was naked sitting on the couch, stroking his cock. I handed him his beer, and he told me to walk back across the room. As I got to the door, he told me to turn around.
“Get on your knees and crawl back to me.”
Knowing I had no choice but to obey, I got down on all fours and crawled back across the floor. Brain gave me a malevolent smile.
“I want you to beg to suck my cock, and I want you to be believable.”
I looked up at him. Turning red from humiliation, I heard myself saying, “Brian, may I suck your cock?”
“You’re not asking me for a favor. I said, ‘Beg me, bitch.’ ”
“Brian, may I please suck your cock?”
“You’re a sorry fucking faggot. I said, beg!”
“Please, Brian! Please let me suck your big cock!”
“Now that’s better, and since you seemed sincere, you may give me a blowjob, and it better be a good one.”
I swallowed hard then crawled closer to Brian. I started by licking the head, then sucking and licking his balls and then licking the shaft. I took the head in my mouth and sucked, as I played with his balls, I started working my mouth up and down his cock. I must have been doing well because I heard Brian moaning, and he began to breathe harder and harder. I felt his hand on the back of my head.
I heard him mutter, “Here it comes, fucking cumdump.”
He stiffened up and started shooting his cum into my mouth. He held my head in place.
“Swallow it all, cocksucker!”
I had no choice but to do as I was told. Finally, Brian relaxed, and his cock started to soften. He released my head, and I let his cock slip out of my mouth.
“Please, Brain, can I get dressed and go home? Please, I want to go.”
“We’re just getting started, faggot. Go get yourself something to drink if you want.”
I came back from the kitchen with a Coke and saw that Brian had restarted the porn movie. He was watching the redhead sucking on monster cock while another guy was spanking her ass hard with a paddle.
“Sit down, cocksucker, and watch the movie.”
As we sat there, I felt his hand rubbing the inside of my thigh.
“You like watching porn?”
“I guess so.”
“Take your little clitty out and play with it.”
He took that damn camera and started taking more pictures. He laughed at me when he saw how small my prick was. Even rock hard, it was just four inches. He told me he had seen porn stars whose clit was bigger than that.
Brian ordered me to play with my “clitty” until I came. I was so embarrassed, but it did not take long before I shot what little cum I could into the palm of my hand. Brian got some close-ups of me swallowing my own cum. Oh, great, more to add to the blackmail file.
“Tuck your sissy clitty back in your panties.”
As he turned off the TV and DVD player, he told me, “It’s time for bed.”
Brian told me to go up the stairs first. As I started up, I felt his eyes on my ass. I was wearing a purple lace teddy with garters and stockings, and the three-inch black heels that I was getting better at walking in as long as I took small steps.
As we entered Brian’s bedroom, he turned and shut the door, locking it. He walked to the bed and flopped down on it. I was not sure what he wanted, so I just stood there watching him. He told me to get on the bed and kneel at his feet. I had no idea what he was going to do to me. He started by telling me to kiss his feet. I leaned down and kissed each foot, and he laughed and told me I could do better than that.
I was to lick the soles of his feet and then to kiss each toe individually. God, it was humiliating doing this, at least he was not taking pictures of me as I licked the bottom of his feet the kissed each toe until he was satisfied. He was laid back, his head resting on a pillow as he told me to plant kisses on his calves up to his knees and his thighs all the way up to his cock. I proceeded to work my way up his muscular legs kissing here and there.
As I was kissing his thighs, I hesitated, and he said, “go ahead, I know you want to kiss and suck it some more.”
Unlike previous times where he had a raging hardon, this time he was still semi-limp. I kissed the tip and then took the whole cock into my mouth. As I started sucking, I felt it begin to grow hard again. I was sucking on the head while working my hand up and down the shaft. I heard Brian start to moan as his cock became fully erect. He said enough and pushed me away. I looked at him, confused, and he laughed at my expression.
“I know you like sucking my cock, and you’ll do it a lot in the future, but tonight, I’m going to fuck that tight ass.”
My mouth dropped open, and I started begging him.
“No, please, Brian, just let me suck it some more. I can make you feel so good.”
I was still pleading with him not to make me do this when he got off the bed and started looking in his desk drawer. He found what he was looking for and walked back to the bed. He had retrieved a tube of Vaseline.
“Please, Brian, don’t do this. I’m not gay.”
He slapped my face.
“I’m not gay either. Now get on the bed face down and push that ass up in the air.”
I looked at him one last time, hoping he would change his mind, but seeing that it was a lost cause, I climbed back on the bed and got on all fours. By this time, I was crying, knowing what was going to happen to me. I felt his hand caressing my ass. Then he was unsnapping the crotch of my teddy. Brian told me to spread my knees farther apart, causing my ass to open more. Brian grabbed some pillows and placed them under my stomach. Then I felt it, Brian’s finger working into my ass. I felt the cold lube as he spread it around my anal opening. I felt him working a second finger into me, trying to stretch me out. Brian removed his fingers, then leaned in and whispered in my ear what he learned from watching porn videos.
“Unless you want it to be incredibly painful, you’d better push out as I start to fuck you.”
By now, the tears were really running down my cheeks. I felt the tip of Brian’s cock pushing against my ass.
“No, I screamed. “No, Brian, it’s too big.”
He laughed and slapped my ass.
“Shut the fuck up and take it, faggot.”
Oh, God, it hurt so much. The pain is incredible. He continued to push, and then the head of his cock passed through my anal ring. I wailed as he impaled me.
“Oh, man, you’re so tight,” he says as he starts to push farther into me.
“Please stop! It hurts too much!” I am whimpering by this point.
“Sorry, bitch, but you can’t believe how tight you are and how good it feels.”
Finally, I feel his pubic hair against my ass cheeks. He is finally all the way in. We stay this way, as he lets me get used to having him in me.
“I’ve never fucked a virgin before. You’re my first.”
He starts pulling back slowly. When I feel he is almost all the way out, he slams back into me. He repeats this several times. My ass is on fire. I can’t believe I am being fucked by another guy. In and out, he works his cock, starting to increase the pace. The pain has decreased, but it still hurts really badly.
“Oh man, this is so fucking hot, you are tighter than any girl I have ever fucked.”
I had my head resting on my forearms, eyes closed, trying to block out the pain. By now, he was driving his cock hard and deep into my ass.
“Oh, man, oh, man,” he kept repeating. “Oh, shit, here it comes.”
Brian slams his cock deep and holds it there. I feel his cum shooting into ass.
“You’re one great fuck, you dirty sissy cock whore,” he whispers as he leans over me.
Finally, as his cock starts to go soft, he pulls out of my ass. He takes the time to slap my ass a few times just for fun.
“Ewww, you have cum running out of your ass. Go clean up, but don’t take too long.”
I crawled off the bed and went to the bathroom. I held the hem of my teddy up as I sit on the toilet. I push and feel the cum pouring from my ass and splashing the water. I clean up, redo the snaps on the crotch of my teddy and go back into the bedroom.
Brian was lying on his back, so relaxed he is all but asleep. He sees me and motions me onto the bed. He turns on his side, pulls me into his arms with my back to him. As we lay there, he has one hand around my waist as he presses his cock against my ass. Soon I hear him snoring. I cry myself to sleep, dreading what I will have to do in the future as I lay there thinking about what all that has happened to me.
I feel Brian shaking me, waking me up, sunlight is coming through the window. It is seven-thirty in the morning. He tells me I need to get dressed and leave before his Dad comes home. I do not even shower. I put my male clothes on and start out the door. He follows me down the stairs
“Thanks for a great fuck.”
I lower my head and keep walking. I get home and head to my room. I throw myself on my bed and start to cry. After what seems like hours, I pull myself together and get into the shower. I smell of sweat and dried cum.
The rest of the weekend was uneventful as I stayed in my room and tried to rest. Every time I closed my eyes, I see visions of what I had been forced to do with Brian—the blowjobs and the fucking. My ass was sore Saturday and Sunday, but I was starting to feel better by Monday morning.
Brian was busy with a project all week and never mentioned what had happened, which was fine with me. Jason, on the other hand, every time he would see me, would laugh at me and yell “faggot” loud enough for everyone to hear. I started hanging out in the library during the lunch period just to avoid running into Jason and his friends.
After practice on Thursday, Jason called me aside. He said I had to do what he said, or he would get the pictures from Brian, and everyone would see what a cocksucker I was. Jason’s goal was to humiliate me.
He told me I had to go up to Tony and Jerome (both were seniors, really muscular black guys, and friends of Jason) and ask them if it was true what they said about black guys. The locker room was full of players getting dressed to go home after practice. Jerome and Tony were standing by their locker wearing only a towel after getting out of the shower. I took a deep breath and walked over to them. I figured if they started beating the crap out of me, the other players or Coach would eventually make them stop. I walked up to them.
“Hi, guys, can I ask you something?”
Tony laughed and said, “Sure, man, what do you want?”
“Uh...well....ah...” I stammered.
“Spit it out. We ain’t got all day,” Jerome told me.
“Well, is it true what they say about black guys?”
“Man, what are you talking about?” Tony said as he was looking at me with a disgusted look on his face.
“Uh…about your cocks being bigger than white guys.”
My face was red from embarrassment.
“Jason said you were a sissy. Now you’re asking us about our cocks, you’re a real faggot, aren’t you?” said Tony.
“Now, Tony, you can’t blame the faggot for being interested in black cock,” Jerome retorted. “Here, see for yourself.”
Jerome took his towel off. I was thinking to myself that it is no bigger than Brian’s cock when Tony said, “Check this one out.”
Oh. My. God. Tony was limp, and it was still eight inches. When hard, it had to be ten to eleven inches long. I could not help but stare.
Jerome said, “Look, Tony, you’re making the sissy drool.”
Tony replied, “I bet you want to suck it, don’t you? Well, not today, faggot, but I may let you some time if you ask nicely.”
I turn to go back to my locker when I heard a snap and felt the sting of a towel. Everyone was laughing at my embarrassment. Jason was laughing so hard it was all he could do to stand up.
“I know Brian is busy again today, so you are coming home with me.”
I followed Jason to his car, and we drove to his house. He went into his parents’ bedroom and came back with a blue and white bikini and a tube of dark red lipstick. He handed them to me and told me I knew what to do. I went into the bathroom and undressed. It dawned on me that I was not even putting up a fight anymore.
I slipped on the bikini bottoms and tied the top in place. It was a little loose, but not too bad. I then applied a thick coat of lipstick and then returned to the living room. Jason said to follow him, and he was heading to the sliding doors. I froze. He was headed outside. When I did not follow, Jason turned.
“What’s the problem, bitch?”
“I can’t go outside dressed like this.”
“Oh, come on, we have a privacy fence. No one can see, and I have always wanted a blowjob while sitting by the pool, so get your sissy ass out here!”
I lowered my head and went outside. Jason had changed into a Speedo and was sitting in a lounge chair.
“Come stand here.” He pointed to the ground in front of him. “Now, turn. Nice ass. Now, kneel before your god and master!”
I slowly got on my knees and looked up at Jason sitting there. You could see his hard-on growing in his Speedo. He told me to lick his cock through the suit. I started licking him. The Speedo felt smooth against my tongue, and you could feel the heat of his growing cock. After licking his cock and balls for what seemed like forever, he told me to remove his Speedo. I reached for the waistband, and he slapped my hands away.
“I want you to remove it using just your teeth.”
I grasped the waistband with my teeth and worked it down a few inches, and then repeated the motion on the other side of his waist. Working back and forth, I got the Speedo worked down to his knees. Finally, I got them down to his ankles, and he stepped out of them. He stood up and turned around.
“Kiss my ass, faggot.”
I leaned in and quickly kissed his right butt cheek. He laughed and told me I had better do better than that, or he was going to beat the snot out of me. Scared, I started planting wet kisses all over his ass.
“Damn, faggot, you’ll do any sick and perverted act, won’t you?” As he sat back down, he told me, “Now, suck my cock and make me cum.”
I remembered what he wanted last time, so I started licking his shaft, and I kissed and sucked on his balls as well. I took the head into my mouth while working my hand up and down the shaft. I must be doing well because he was moaning.
“You’re getting better at this, you fucking little cocksucker. You must really like sucking my dick.”
I could feel my cheeks burning from embarrassment, but continued to suck. I started working my mouth up and down Brian’s cock leaving red lipstick rings. I would deep throat him, then gently suck on just the cock head, and then back, taking the whole thing into my mouth. He was really moaning now, and I could hear his breathing getting faster and faster.
I felt his cock start pulsing in my mouth, and then my mouth was filling up with cum. I started swallowing on instinct, but he was cumming so fast and so hard that I could not swallow it all. I felt cum running out the corners of my mouth and down my chin.
When he was drained of cum, and his cock was going limp, I let it slip from my mouth and started licking around his dick, cleaning his cock and crotch area. I then realized I was doing it without being told to do so. God, I really am becoming a sissy faggot. When I was through, Jason said I did a good job but should leave. I went in and got dressed and washed off the lipstick. I asked him if he was going to give me a ride home because it was at least three miles to my house. He laughed at me.
“You can walk or hitchhike. Someone should give you a ride, but who knows what you would have to do for them.”
I started walking. It would be dark soon. It seemed to take forever, and when I reach the house, I was exhausted from all the walking. Mom was home when I arrived.
“Where’ve you been, Andy? You’re supposed to come directly home after school unless you tell me otherwise.”
“I’m sorry, Mom, I was at a friend’s house and should’ve texted you.”
I went to my room and cried myself to sleep once again.
It had been a few weeks since I had to give Jason a blowjob while dressed in a bikini and even longer since Brian had fucked me after the homecoming game. Jason had made up with his girlfriend, and Brian had found one. I was starting to believe that maybe, just maybe, I could put all that behind me. Sure, Jason still called me faggot, sissy, or cocksucker whenever he saw me, but other than that, they had pretty much left me alone. Football season has ended, and Brian was working out with the wrestling team. So after school, it was either ride the bus or walk home. During lunch period, I had started hanging out in the library to avoid Jason and his friends. My grades had begun to improve since I was actually spending time studying.
One day, I was studying for a history test when I heard someone ask if I had an extra pencil. I looked up to find a skinny black-headed boy with a friendly smile. As I was fishing a pencil out of my book bag, he introduced himself as Jamie. I said hi and told him my name was Andy. He said he had seen me in some of his classes, we compared notes, and it seemed we had chemistry and English together.
He said he was shy and sat at the back of the class while I usually sat somewhere in the middle. We talked until it was time to go to our next class. He said he would see me tomorrow, and I found myself looking forward to it. Over the next several days, Jamie and I talked all through lunch. We seemed to share a lot of the same interests, and we seemed to hit it off and become fast friends. Things seem to be going right for me for a change.
One day, I had stayed over to look something up in the library and missed my bus. I did not think much about it because really it was not that far of a walk home. As I was walking home, I heard a car pull up beside me.
“Hey, sissy, need a ride?”
It was Jerome and Tony. Two very muscular black guys who were friends with Jason. I told them thanks, but I would just walk. Jerome jumped out.
“Get into the car.”
I thought about running, but Jerome grabbed me by the arm and pushed me into the back seat. As Tony pulled away from the curb, Jerome asked me where I lived. I told them, and he asked if anyone was at home. I guess I probably should have lied, but these guys made me nervous, and I blurted out that I lived with just my mom and that she was at work.
“Is it true, what Jason says? That you like to dress like a girl and suck cock?”
I just hung my head and did not answer. I heard Jerome laughing.
“Man, I just thought Jason was picking on you. You really are a sissy faggot, after all.”
We pulled into my driveway, and as Jerome got out, he held the seat up for me. They followed me to the front door, where I was so nervous that I was fumbling with the keys. Jerome took them from me and unlocked the door, pushing me into the house. They asked if we had anything to drink, and I told them there was no alcohol in the house.
Tony said it was okay and for me to show them around. I led them from the living room, through the kitchen, and down the hall to my bedroom. Tony said I had missed a room and started back toward my mom’s bedroom. They started looking around and going through drawers. I heard Jerome say, “Look at this,” holding up a twelve-inch vibrator.
“You still have the cheerleading outfit?” Jerome asked.
“No, it belongs to Brian’s sister, and I had to return it.”
“Well, that’s okay, maybe we can find something of your mom’s for you to wear,” Tony said.
I pleaded with them not to make me do this. That’s when Jerome punched me in the stomach, doubling me over. He said either I could do this, or they would just wait and use my mom for their pleasure.
As I was gasping for breath, Tony started looking through the closet and came up with a dress I had only see my Mom wear a few times. It was a dark blue halter dress that came to mid-thigh. Jerome spoke up and said that I might as well forget the bra and panties, but he wanted me to put on a pair of pantyhose.
I looked in her lingerie drawer and found a pair of tan pantyhose. I took them and the dress into my mom’s bathroom. As I was undressing, I had a flashback to the time in the locker room where I had seen Tony’s cock. Limp, it was still bigger than anyone I had seen before. My hands were shaking as I slide the pantyhose up my legs. I smoothed them over my thighs and hips, worked the dress down over my head. I tied the halter in place and looked at myself in the mirror.
I had not had a haircut, and it had grown a lot in the last month. I grabbed a rubber band and put it back into a ponytail. Even though Tony or Jerome had not told me to, I put on a little makeup and did my lips in a cherry red lipstick that my mom used on occasion. Again, I looked in the mirror and realized I looked cute. I figured I had stalled as long as I could and returned to the bedroom.
Tony was talking on the phone, and Jerome was lying on the bed watching television. As I walked into the room, Tony told whomever he was talking to that he had to go and hung up. I felt so weak and scared when I noticed the look of lust in their eyes.
Jerome turned the TV to a music channel and told me to dance for them. I have no rhythm, but I was trying my best to sway my hips to the music. After a while, Jerome pulled me onto his lap and told me to wiggle my ass. I tried my best to imitate the strippers I saw in movies when they were giving lap dances. Oh shit, I could feel his cock against my ass, and it felt rock hard already. Tony was watching us closely as he took off his jeans and t-shirt.
I felt Jerome reach around and start rubbing my nipples under the halter-top. He whispered in my ear that he preferred girls with big tits, but my nipples must be sensitive because they were getting hard. He started pinching my nipples and pulling at them. He viciously twisted and pulled one, then the other sending severe pain through my body.
A slow song came on the TV. Tony pulled me off of Jerome’s lap and pulled me close. Without thinking about it, my hands went up around his neck. I soon felt Tony’s cock pressing into my stomach, and his hands were mauling my ass.
By this time, Jerome had taken his clothes off and was standing there in his boxers. I felt Tony kiss the top of my head as we danced. I felt so small and frail as Tony held me in his arms. To my surprise, I think I liked being held by a strong man.
As Tony held me tight, Jerome had taken off his boxers and came up behind me. I felt his cock grinding against my ass. Tony let me go, as Jerome continued to dry hump my pantyhose clad ass. I watch Tony as he slid his underwear down, exposing his huge cock.
Jerome pushes me forward, and I fell, my forehead hitting Tony’s knee. I felt a little dazed as I felt Jerome’s foot on my ass, pushing me into Tony’s crotch. His massive cock is hitting me in the face. Tony lifted my head up by my chin and guided my mouth to his cock. The head was so big I had trouble getting my lips around it. I was trying to work my mouth up and down Tony’s cock. It was so big that I could only get a small part of it in my mouth.
As I was trying to work my mouth further down the shaft, I felt the hem of my dress being pushed up, and then I felt Jerome rip the pantyhose I was wearing. I heard him spit and felt his wet fingers start working into my ass. Tony was being kind, letting me work at my own pace, and not forcing his monster cock down my throat. Jerome, on the other hand, was brutally fingering my ass.
I felt the head of Jerome’s cock pushing against my ass. I remembered what Brian had said about pushing out and was doing it when Jerome pushed hard, driving his cock into my asshole. I had lifted off of Tony’s cock as I felt the pain of Jerome entering me. I closed my eyes and tried to block out the pain as Jerome worked inch after inch into my ass. Finally, I felt hair against my ass cheeks and realized that Jerome was inside me completely. He held it there for a few seconds. Jerome started working his cock in and out slowly. After a few minutes, I took a deep breath and took the head of Tony’s cock back into my mouth.
“Goddamn! This sissy is tight!”
As Jerome kept a steady pace fucking my ass, I started working my mouth up and down Tony’s cock as my hand stroked the shaft as I sucked. I tried to swirl my tongue around the head, but it was challenging since the head was so big. I realized that my ass did not hurt as bad as it did when Brian took my virginity. It still did not feel good, but it was bearable. Jerome was picking up the pace and breathing heavy. I noticed that Tony’s cock had started to throb in my mouth, and I knew he was close to cumming. Tony had his eyes closed and was moaning as I sucked.
“Oh…fuck…ugh…here it comes, faggot.”
Tony started shooting massive amounts of cum. There was no way I could swallow it all, and I pulled off of his cock to keep from gagging, I held my mouth open, and he continued to shoot cum into it for what seemed to be forever.
Jerome grabbed me by the ponytail and pulled my head back as he was ramming his cock hard, fast, and deep into me. My neck was hurting from the strain as he let out a growl and came in my ass. As Jerome pulled out of me, I felt cum running down my thighs. I looked up at Tony, who was smiling at me when he patted my head.
I leaned down and start licking the cum out of his pubic hair and off his shaft. I licked his muscular thighs where his cum had ran down his legs. I licked his flat stomach, making sure to get every speck of cum. It dawned on me that I was acting like a cum whore doing all this without being told. As I finished cleaning Tony, I felt Jerome wiping his cock off on my pantyhose.
“Fuck, Jerome, we got to get going.”
I stood up and observed Tony as he started dressing. He was a handsome guy. Did I really just think that?
They both finished dressing, and I walked them to the door, just to make sure they were really leaving. That’s when Jerome slapped me hard and told me not to say anything to anybody, not even Jason and Brian.
Jerome was getting into the car when Tony came back. He was bringing my book bag to me that I had left in the back seat. As he got close, he winked.
“Sorry about Jerome,” and then he leaned in and whispered, “Thanks for the good time.”
I stood there and watched them drive away. I ran back to my Mom’s bedroom and tried to straighten up. I hope I had put everything back into place as I hung up her dress. I scrutinized the dress to make sure there were no tears or stains on it. I realized I would have to get rid of the pantyhose because they were torn and sticky with dried cum. I went to the bathroom and took off my makeup and lipstick. As I was cleaning myself up, I heard Mom pulling in the driveway. I rushed into my room and put on a polo shirt and shorts. I met my Mom in the kitchen, and she looked at me funny.
“Your hair looks nice,” she said.
It dawned on me that it was still up in a ponytail. Embarrassed, I stammered a thank you and went to my room.
I was confused. I had hated everything that Brian and Jason had done to me, and I was repulsed by Jerome, but every time I saw Tony, I caught myself smiling and thinking about the day we danced. He held me in his strong arms, my arms around his neck. Every time I thought about it I got a warm feeling and felt my cock started to stir. What was wrong with me? I was sitting in the library thinking about things when Jamie sat down. He looked at and asked what I was thinking about. He was the closest thing I had to a friend at school, but of course, I could not tell him the truth.
“Lack of a love life.”
“Tell me about it.”
I know he had a crush on this cute little brunette girl, and while Jamie was a really nice guy, he was shy, skinny, and kind of a nerd. Chances were that if he ever got the courage up to ask her out, she would say no.
It was Friday, Jamie asked me what I had planned for the weekend, and I said probably just stay home and play on the computer or play video games. He said it sounded like fun, but before I could ask him if he wanted to come over, he said he was going out of town with his family, so here I was on a Saturday night sitting in my room watching some boring movie when I heard the doorbell. I figured my mom would answer it. A few minutes later, I heard Mom call for me. As I walked into the living room, I saw Brain standing there. I froze. I had no idea why he would be at my house this time of night.
“Andy, your friend Brian is here. He wants to know if you want to go to his house and play a new video game he has.”
“Sorry, Brian, maybe some other time.”
“I’m thirsty. May I have a glass of water?” Brian asked.
“Sure. Andy, take Brian into the kitchen and get him a glass,” my mom replied.
As I was getting Brian his glass of water, he pushed me up against the counter.
“Look here, faggot. I’ve had a fucking bad night, and I’m pissed so you’d better do as I want, or I’ll show your mom some photos.”
After Brian has finished his water, we went back to the living room.
“Mom, Brian talked me into it. I’ll be home tomorrow morning.”
I started out with Brian.
“Andy, shouldn’t you take your pajamas?” my mother asked.
“He probably won’t get much sleep.”
I went to my room and stuffed some clothes in my book bag. I was dreading this but had no choice. As we walked to Brian’s house, he told me about his night so far. He had a date with Karen, his new girlfriend. They were making out, and she was driving him wild, then all of a sudden she stopped him, said it was that time of the month and she wanted to go home.
We went in and headed upstairs. I dropped my book bag inside the door. I had a feeling I would not need any of my male clothes tonight. I followed Brian into Shannon’s room. He was already going through the closet. He handed me a short black skirt and a white sleeveless mesh shirt. He looked in Shannon’s lingerie drawer and came up with one of her old black bras and the matching panties. He gave me an evil grin.
He left, and I started undressing. After I was naked, I pulled the panties up my leg. I hooked the bra and turned it around. I realized something was not right. Then it dawned on me. Shannon was an attractive 34C. I rummaged around until I found some old pantyhose and stuffed and molded the cups to look like I had a nice size chest.
I pulled the skirt up and zipped it into place. Then I pulled the shirt over my head. I found a brush and fixed my hair, and then added some blush and red lipstick. I found the same pair of two-inch black heels that I had worn before and slipped my feet into them.
I looked in the mirror and noticed that with breasts, I looked pretty good. I went looking for Brian. He was not in his bedroom, so I figured he was downstairs. I went down the stairs. I was getting decent at walking in heels. I found him sitting on the couch, naked, and drinking a beer. I was starting to wonder if he had a drinking problem.
He saw me enter the room and stood up. He said it was about time and started toward me. He grabbed me by the arm and led me to the couch. Instead of sitting down, he threw me over the arm of the sofa and ripped the panties off of me. I could tell he was all worked up and in a hurry, as I felt his rock hard cock start to jab at my ass.
“Oh…god…Brian, use some lube…Brian, please…use…oh, god…don’t fuck me dry…please.”
“Shut the fuck up and take it, bitch.”
His cock finally found my anal ring, and I felt him pushing against it. Oh. My. God. It hurt so much.
“No, Brian! Stop! It hurts!”
The head popped through, you would not believe how much it burned; my ass was on fire. I was begging him to slow down, but I think that at this point, he was so overcome with lust that he did not even hear me. By now, I was crying because it hurt so much, Brian did not care he was too busy raping my ass. In and out. In and out. He was breathing heavy and pounding my tender ass.
“Oh, Karen, you fucking slut, I knew you wanted to get fucked tonight.”
Was he calling me Karen?
Jerome was rough when he fucked me, but even he was nothing like this. The pain was so intense it felt like he was tearing me up inside. I may never walk right again.
“Oh, fuck, Karen, you’re so fucking tight, here it comes.”
He drove his cock deep and held it there as he emptied his balls deep into my ass. The cum hitting my raw ass caused the pain to intensify until I thought I was going to pass out.
He laid there on top of me panting, his cock still in my ass. I figured he would eventually go limp and slip out of my ass. I was wrong. After several minutes, I felt him start to move again. Instead of pulling out, he started working his cock in and out of me once more.
At least his cum had lubricated me, and it did not hurt quite as bad as when he fucked me the first time, but it was still excruciating. I felt him getting harder inside my ass. He was taking long slow strokes this time. He was in no hurry to cum again. He was slapping my ass occasionally as he fucked me.
“I will teach you to tease me, then turn me down, you fucking whore.”
He thought I was Karen, or he was pretending to fuck Karen. After twenty to twenty-five minutes, he started picking up the pace. My knees were starting to get sore along with my ass. He was starting to moan again. I felt him stiffen, and then he was shooting his cum into my ass once again. This time after he came, he pulled out and collapsed on the couch. I just lay across the arm, too sore to move as cum flowed down my legs. My eyes were closed with tears running down my cheeks.
“That was one hot fuck. I need another beer. Maybe you should bring two I really worked up a thirst.”
My legs were weak, and I was not sure they would support me as I wobbled toward the kitchen. While I was there, I took the time to use a paper towel and tried to clean the cum off of my legs. When I returned, I handed Brian his beers.
“Can I go clean-up?”
“Sure, why don’t you take a shower and clean your sissy cunt. When you’re done, put on that purple teddy that you know I like.”
I stripped off the skirt and blouse, took off the bra, and got into the shower. I let the warm water wash over my sore body. After several minutes I dried off and went to Shannon’s room to find the teddy. I got dressed, attached the stockings, put my heels back on, and fixed my makeup. I walked into Brian’s bedroom, and he was lying on the bed. As I walked in, I was not sure what he wanted me to do, so I just stood there awaiting his next demand.
“I thought you were going to take all night. While I recover, why don’t you make yourself useful and clean up my room?”
I started picking up his dirty clothes. They were spread all over his floor. I took them and put them in the hamper in the bathroom. Then I picked up the trash. He told me to take that downstairs and put it in the trashcan outside the door.
When I came back, Brian told me that all I had to do was to vacuum the carpet, and I would be done. He told me where the vacuum cleaner was, and I went and got it. By now, my feet were starting to hurt as much as my ass was. All this walking in heels was getting to me.
I finished the cleaning and put the vacuum away. It was almost two-thirty in the morning. Brian said it was time to have his cock sucked. I crawled on the bed and got between his knees. I started kissing and licking his cock. I figured this was better than what he had done to me earlier.
As I started to suck Brian’s cock, I almost gagged. He had not washed it since he had fucked my ass. I tasted sweat, dried cum, and my shit. I did not want to think about that. Once he was hard again, he pushed me away and scooted over.
“Lie down on your back.”
I was wondering what he had in mind when he grabbed my legs, forced them up and over my head, and slid my panties to the side. I watched him line his cock up and start pushing into me yet again. God, my ass was sore, but he slipped in easily. I closed my eyes, trying to block out what was happening. That is when I felt Brian slap me hard across the face. My eyes flew open in surprise.
“I want to see the look on your face while I fuck you, you little cumdump. Tell the truth. You love being fucked like a little girl.”
He was taunting me.
“No, Brian, I don’t like it,” I replied. “I hate it.”
“Don’t lie to me! Why else would you let me, Jason, and who knows who else fuck you?”
I was crying again. I seemed to be doing that a lot lately. He was holding my legs high and spread wide. He was pumping in and out of me, calling me names like bitch, whore, fuckhole, sissy, cumdump, faggot.
“I told you to keep your eyes open and to look at me while I fuck you.”
Tears were running down my checks from the sting of the slaps and the humiliation of his verbal abuse. As he was fucking me, my little cock was trapped in between our bodies. It had to be the friction of my satin panties rubbing against my cock head because I was hard. Sure, it was small, but my cock was rock hard. I tried to stop it. I really did, but I could not hold back anymore. I moaned.
I started to cum, coating my panties with cum. With every strand of cum I shot, my ass spasms, along with the stimulation he got from humiliating me, his cock twitched, and then for the third time that night, he was shooting his load of cum into my ass. The whole time he was staring at my face and forcing me to look into his eyes. When he pulled out, he saw that I had cum also.
“See, little faggot, it turned you on, and you loved it.”
I did not answer him because there was nothing I could say.
He let my legs go and got off the bed. He told me to take off my sticky panties. Then he took them from me.
“These need to be cleaned before your cum dries.”
That’s when he shoved them into my mouth.
“Suck all the cum out of them, you little cumdump.”
After sucking the cum out of my panties, I put them back on. I was sitting on the bed when Brian came out of the bathroom.
“You can sleep on the floor at the end of the bed.”
He turned out the lights and crawled into bed. As I lay there on the cold floor, I heard him start to snore lightly. I must have been exhausted because it was not long until I was in a deep sleep.
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