This isn’t about me being raped but more a follow up to what happened after I was raped by two boys in the woods.
After I was raped I did a lot of thinking and exploring my sexuality. When the two boys that did it made me suck their dicks, I pretended not to like it but I actually liked it quite a bit. I had never sucked a cock before that but I had been cross dressing in my mom’s and sisters clothes for 2 years behind closed doors. When they took it a step further and raped my asshole, I hated it.
Most of my thinking was centered on whether or not I was gay. It always ended quickly when I realized that I did like girls. In fact, I preferred girls. It didn’t explain why I liked dressing in women’s clothing or having those two boys put their cocks in my mouth though.
While I laid in the woods with my pants around my knees, tears streaming down my face and cum trickling from my sore anus, I thought that if they had been gentler, I might have enjoyed that. So when I discovered my mom’s vibrator I had to try it out. It was just a silver wand looking thing and it slid inside my hole fantastically and the intense orgasm’s were second to none!
About a month after, I went into my moms bedroom looking for her vibrator and it wasn’t in her drawer. I tore the room apart for a half hour but never found it. I would never see it again.
My mom always had a very strong sex drive and my sister and I would regularly listen to our parents fucking. Even sneaking a peek every now and then but by the time I hit high school, dad had left for good and maybe moms sex drive left with him. She never brought a guy home and as far as I know got rid of her vibrator and never had another one.
For the next three years of high school I chased girls and struck out every time. My first girlfriend didn’t come until I was 17. Most of my exploration came in the form of my cross dressing, and a boy next door.
Joe, was my neighbor and a year younger than me and we eventually started fooling around when I was 15 and he 14. However, all we ever did was kiss, and rub against each other until we came. Joe was not nearly as bisexual as I wanted him to be. So I spent 3 years trying to find a way to satisfy this other urge I had. I would still wear my mom’s clothes and I would masturbate while wearing them. I liked to put on my sister’s outfits and pretend I was Joe’s girlfriend.
I never quite got what I was looking for from him and I was too young to go to a sex shop and buy my own vibrator or dildo. This was the mid to late 90’s and the internet wasn’t nearly what it is now so finding something around the house to put in my ass was the best I could do. I tried the plunger handle, a shampoo bottle, a baseball bat and a broomstick but nothing worked. The baseball bat didn’t even come close to going inside me.
Three years had gone by, I was 17 and beginning my senior year of high school. I was desperately searching for a girlfriend and getting better but still no success. The cross dressing was still a huge thing and the anal sex was on the back burner, that is until it finally happened.
I was staying after school to run some laps. I was on the wrestling team and in order for us to get our cardio in, we had to run the hallways since it was winter and much too cold to go outside. I stayed a little later than the rest of the team cleaning up some mats and stuff. When I entered the locker room I heard a voice. There was a caged room in back where the school kept some equipment locked up. I approached the room and could tell that the voice was coming from the caged room. When I peeked around the corner I saw one of the freshman wrestlers on his knees giving Mr. Kennedy, my English teacher, a blow job.
They must’ve thought they were all alone because they both had their pants completely off. They also must’ve really been enjoying it because they had no clue I was just outside the cage less than 10 feet away watching.
I found myself staring at Mr. Kennedy the entire time. He was in fairly good shape and had a full head of gray hair. He had a thick dark brown mustache and a stubble beard. He had his shirt pulled up and I could see that he had a dark patch of chest and stomach hair. But what stood out the most was how entranced I was by his cock. I couldn’t take my eyes off of it!
It was just a minute or two of watching from behind this cage but it felt like an eternity. Mr. Kennedy’s head fell back and he looked straight up at the ceiling and I could tell he was cumming in this kids mouth. As soon as he stopped I tried to sneak away unseen but I failed. Mr. Kennedy saw me out of the corner of his eye and quickly pulled his pants up to chase me but I was gone before he could ever get close. I ran home scared shitless but also with a raging hard on. I had no idea if he had identified me or not.
The next day he seemed completely normal in class and I got no impression that he knew it was me spying on him and his boy lover. Over the course of the next few weeks I found myself getting rock hard erections in his class. Day dreaming of his cock. I couldn’t believe what was happening in my head.
I quickly found out that even the shyest of boys will do the boldest things if their libido demands it. After 3 weeks of fantasizing about my English teacher, I decided to try and get some one on one time with him.
I asked Mr. Kennedy if I could stay after class and he could help me with my homework. He agreed. As the bell rang ending class, I stayed seated and my legs were shaking so much that the desk was rattling. I couldn’t hear myself thinking because my chest was pounding so hard.
“It was me.” I mumbled
“What? Who were you?” Mr. Kennedy replied confused.
“I was the one spying on you in the locker room.” I said putting my head down
Mr. Kennedy ran over and closed the door as quick as possible and placed his hands on his hips.
“I don’t know what you’re talking about.” He said sternly “…I think maybe you should go now.”
I stood up and approached him and handed him a note that I spent hours working on the night before. It was your basic high school note but I explained that I saw him but I didn’t want to snitch on him but instead I wanted to be with him. It said how I had been fantasizing about him constantly and I just wanted to make my fantasy come to life. He escorted me out of his class before he could read it though.
The following day he said nothing to me the entire class until about 2 minutes before the bell.
“I’ll need to speak with you after class.” He said
After the standard “oooh, you’re in trouble” from the class, the bell rand and every one left. Mr. Kennedy handed me my note back and told me he shouldn’t have this in his possession. Then he followed it up by placing his hand on my shoulder and saying he was flattered but he couldn’t possibly have a relationship with a student.
As I left the classroom, I opened my note that he gave me back and there was a message from him at the bottom.
“I’ll be in the cage at 5:30”
My heart skipped a beat and then began racing like crazy! I couldn’t catch my breath! I spent all of 7th period Math thinking about Mr. Kennedy and what we might do. I had to sit very awkwardly to cover up my hard on!
After school ended I went to wrestling practice and again couldn’t concentrate on anything. My coaches were yelling at me for the entire practice.
When practice was finally over I again offered to sweep and clean the mats. I had to almost beg one of my teammates to let me do it alone.
Finally, all my teammates were gone and the last of our coaches had locked his office.
“Finish up, I wanna get outta here!” Coach yelled to me.
“I’m going to run some laps when I’m done so you can take off, Coach.” I explained
“Way to go the extra mile.” Coach said as he pay me on the back and left.
I quickly finished up sweeping the mats and raced towards the locker room. It was shortly after 5:30 and I don’t recall ever seeing or hearing the school so quiet and empty. As I entered the locker room I made sure to lock the door behind me just in case. I nervously made my way around the corner to the caged room and saw Mr. Kennedy standing there.
“Hey you.. you look nice and sweaty.” He said extending his hand and pulling me into the room.
Mr. Kennedy pressed himself against me and pushed my back up against the cage in the process. He held me in place by my hips and I could feel his hard cock pressed against my equally hard cock. Without saying a word, he leaned in and kissed me with his tongue. The tickle of his mustache on my nose was strangely erotic. I absolutely loved pretending I was Joe’s girlfriend and now I was finally kissing a real man.
We kissed for about 30 seconds before he reached his hands down the back of my gym shorts and squeezed my ass cheeks. I returned the gesture by sliding my hands up his shirt and running my fingers through his chest hair. A little push of his wrists and my gym shorts and jock strap had fallen to the floor. Before I could finish kicking them off my ankles, Mr. Kennedy had a firm grip on the shaft of my cock and began stroking it. I felt a shockwave of pleasure and my eyes rolled back in my head as he squeezed and thumbed the tip of my dick rolling the small drop of pre cum I had already made between his fingers. Mr. Kennedy spit in his hand kneeled down and began vigorously jacking me off. Within 15 seconds I was going to cum. He opened is mouth and put the top of my dick between his lips and I shot my load in his mouth! He kept squeezing and stroking my cock getting every drop of cum he could.
“Your turn.” He said as he stood up and unbuttoned his khakis.
As his pants fell to the floor, his cock pointed straight up at me. It was magnificent! Average girth but at least 8” long. I quickly put my hand around it. I loved how warm it felt in my cold hand. My hand was shaking so much I was actually worried I’d make him cum from being so nervous!
I kneeled down and opened my mouth. This was the first time I voluntarily put a dick in my mouth. I was terrified! My lower teeth hit the extremely sensitive part as I put it in. I was embarrassed and apologized before trying again. The second try was much better. His cock smelled really good and tasted great. I had no idea that dicks were all so different!
“Are you gonna fuck me?” I asked looking up at him
“Do you want me to?” He asked running his fingers through my hair
I nodded and smiled but on the inside I thought my heart stopped. I’m so unbelievably shy and all of this happening the way it was wasn’t like me at all!
Mr. Kennedy helped me up to my feet and walked me over to a table inside the room. We kissed a few more times before he put his hands on my shoulders and turned me around. I felt his rock hard erection against my ass cheeks. He placed his hand firmly on the upper center of my back and bent me over the table.
“Spit in my hand.” He whispered placing his hand in front of my face
I did as he asked and gave him as much spit as I could. I watched him run it all over his cock and then he bent down and spit on my asshole. Mr. Kennedy then took a step forward in between my legs and pressed his cock against my hole. I felt a hard push and then the tip of his dick slid inside my ass.
“Oh god!” I moaned out
Mr. Kennedy grabbed firmly to my hip with his right hand and held me down with his left by pressing down on my upper back. After about 5 soft gentle thrusts in and out I thought I was going to pass out. To be honest it felt like I was taking a huge shit over and over again.
As my asshole began to stretch and I became more relaxed I realized I absolutely love the feeling of his cock sliding in and out of my hole. So much so, that I started to moan and yell pretty loud. Mr. Kennedy reached around and covered my mouth which just made me want more!
So I guess I officially identify as a bisexual cross dresser. When I am with a woman, I love being in control. I love having a woman ride me for 15 minutes and cum 4 or 5 times so that when it’s my turn I can get behind her and just fuck her and pull her hair as hard as I want. I love it when you’ve satisfied her so much that she’s powerless and lets you do what you need to do as a man.
On the other hand, when I’m with a man I’m the other way around. I love to be controlled and dominated. I love when his cock is throbbing inside me, his hands are on my hips and he’s just pounding my ass harder and faster. I love when he pulls my hair, chokes me and even an occasional slap!
With one hand covering my mouth and the other pressing me down against the table, Mr. Kennedy let out a loud grunt and shoved his cock as far up my ass as he could! I could feel it pulsing and pumping. I felt his cum squirting into my ass! His legs were shaking and we were rattling the table quite loudly. Some explicit words escaped his mouth and he quickly pulled his cock out of my ass. I immediately felt cum pouring out of my stretched out hole and drip down my inner thigh.
“Fuck that was good!” He grunted
I began to turn towards him but he shoved me back down on the table. My first thought was, oh my god, is he going to fuck me again? I absolutely would’ve let him!
“We shouldn’t be seen leaving together.” He said pulling up his pants. “…stay here for a few minutes before you leave.. that was fun.” He added as he smacked my bare ass and turned and left.
I stayed bent over the table for at least 2 minutes just basking in the awesome feeling I had. I felt used and satisfied! I had gotten exactly what I wanted. I absolutely loved it! And I definitely needed more of it!
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