A brief intro. Let’s say my name is Derek. I’m 5’8”, 122 lbs. I’m very skinny but I look toned. I’m a sophomore in High School and I live in California. This story is partly true but the actual seduction never occurred. This story involves cross-dressing and underage boys. If this is not your type of story please do not read it. If the responses are positive I will post part 2.
I’m 18 years old and for the last two years of my life I have had sexual urges toward my two best friends. It may sound weird however that I don’t consider myself gay or even bisexual. The only two men I have ever thought about sexually have been my two friends, Tristan and Chris. I have known both of them for my entire life and I never could act on any of the urges had.
Chris is the athletic one of our group of friends. He’s 5’10 175lbs. He is a safety on the school football team and also runs track. He has a very muscular tanned body, six pack and all. He is very attractive, blond hair blue eyes. The girls used to be all over him but a rumor was spread by his ex-girlfriend that he was a porn addict. He hasn’t recovered from that yet and hasn’t had a girlfriend since.
Tristan is the idiot of our group. He’s 6’0” 195lbs. He plays baseball but isn’t very athletic and plays 3rd base. He is kind of chubby and has a body that a lot of people wouldn’t fantasize about. But he is not fat. Every year since 8th grade he has had a 2.0 GPA or worse. He is shy and has never had a girlfriend but has hooked up with girls at various parties.
We still have sleepovers and a sleepover 6 months ago is why I’m writing this story. It was the summer and Chris had invited me over to spend the night. We watched the Padres lose another one and played some Xbox. It was around midnight and I fell asleep. Chris continued to watch T.V. and fell asleep sometime after. I woke up in the middle of the night and went to the bathroom. When I walked back into the playroom I saw Chris naked on the couch. His blanket had fallen off and his muscular body was completely exposed. I had fantasized about having sex with him before that but seeing his naked body was too much. I wanted to strip and have sex with him right there. But he has always been a light sleeper and I didn’t want to risk getting caught. Instead I stood in the doorway and masturbated to the sight of his soft, smooth cock. It wasn’t hard and it looked to be 3 inches. I finished and cleaned up and went back to bed.
For the next two months I couldn’t get the image of his strong masculine body out of my head. But I was sure he wasn’t gay and I didn’t know how to address the situation. I was sitting at home watching T.V. and stumbled on the movie The Animal with Rob Schneider. It was a pretty bad movie but it did give me a brilliant idea.
The main characters brother is constantly dressing up in her clothing. He wears dresses, shoes, and lipstick. I realized my way to have sex with Chris was to dress like a women. Chris isn’t gay but he is a horny kid. It wouldn’t be too hard to seduce him I thought.
I called him up and asked him what he was doing and he said he had to go to a movie with his parents latter that night. I realized that would be the perfect time to seduce him. My parents and brother weren’t home so I had the house to myself. I ran up to my mom’s closet and began to look at everything. I knew I would have to dress conservatively but I also wanted to be sexy enough to attract Dan.
It took me about an hour but I managed to transform into a somewhat attractive girl. I wanted to feel like a girl so I picked out a white thong and a matching bra. I stuffed the bra with toilet paper but I made sure that I didn’t use too much. Looked in the mirror and was pleased that they looked even and perky. I had some hair on my legs and didn’t want to shave them since I have P.E. at school. So I grabbed my mom’s pair of Spandex and put it on. I was satisfied to see that I had a nice round ass that Chris would find attractive. Over the spandex I put on a skirt that went down half of my thigh. For the top I picked out a tube top. My arms aren’t hairy yet and are small and skinny like a girl’s. But the tube top gave away my fake breasts and I had to put on a scarf to cover up my cleavage. The scarf also covered my Adam’s apple and gave me a conservative look. My hair s normally short but my brother had been a prostitute fro Halloween and had a nice wig. My hair was now brunette and went a little past my shoulders. It was fairly realistic but if Chris looked at it to long I was sure he would notice it was fake. I didn’t want to apply make-up and give myself away since I had never applied it before but I did decide to apply lip-stick. I looked in the mirror and would’ve given myself a 7 out of 10. I put on a pair of my mom’s tennis shoes and decided to get to the theater sooner rather than later.
I drove to the theater and sat in my car for 20 minutes to scared to move. I was about to leave when the image of Chris’s naked body flashed into my mind. My cock twitched and I got out of the car. I walked up to the ticket counter and tried to sway my hips slowly. My heart froze when I saw that the teenage guy behind the counter was an acquaintance at school. I walked forward and looked right into his eyes. I saw him look up at me and eye my body. I sighed in relief that he hadn’t noticed me but my hands were still shaking.
“Hello. What can I do for you today?” He asked.
“Um. Can I get two for Friday the 13th please?” I asked with a smile. I picked a horror movie that had been out for a few months for a specific reason.
I had one of my moms purses strapped to my shoulder with only cash inside. I reached in and grabbed a twenty. I was trying to hand him the money but I fumbled it and it fell to the ground. I reached down to grab it and could feel his eyes undressing me. I turned my head and caught him eyeing me. He glanced away quickly and I couldn’t help but smile.
I got up and paid for the tickets. The boy behind the counter kept looking away sheepishly. I went into the theater and waited for Chris and his parents to come in. I was extremely nervous but the glances I got from teenage guys reassured me.
It was about 30 minutes later when Chris and his parents entered the theater lobby. They walked up to the popcorn stand and it was time for me to act. Chris was glancing around the room and his eyes meet my body. I stared at him and his eye’s eventually reached my eyes. I put my finger up and motioned for him to come over. He just stood there staring at me and I did my best to entice him. He finally worked up the courage to come speak with me and I nearly ran I was so afraid.
“Hey there.” Chris said. He had a lot of confidence in his voice but I knew he was nervous.
“Hi.” I said softly.
“Are you here all alone?” He asked trying to sound sincere.
“Yes. My friend couldn’t make it to our movie and it’s a horror movie.” My voice said full of fear.
“Do you need a friend?” He asked.
“If you don’t mind.”
“No problem, what’s your name?”
“Marissa.” I blurted out.
“Alright Marissa, I’ll be right back.” He ran over to his parents and talked to them for a minute. They looked disappointed but I could tell by the look on Chris’s face that they said he could go.
He walked back over with a smile on his face and he escorted me to the theater. We walked into the black room and he started walking to the front row. I asked if we could sit in the back and he didn’t object. We walked to the very back row and sat down to watch the previews. I glanced around the theater and was pleased to see only one other couple in the front of the theater. The lights went black and the movie started.
The opening scene was a couple in a house making-out when they heard a noise. The boy walks around looking for the source of the crash when from behind him the masked killer strikes. It was painfully obvious what was about to happen but I had to play my act. When the killer struck I quickly reached out my hand and put it on Chris’s thigh. He looked over at me but I made sure I didn’t look back. The killer then attacks the girl that was hiding under the bed. I was still as calm as possible but I used the scene as an excuse to move my hand farther down his thigh. I could hear him breathing heavily and I knew his cock was starting to get huge.
He kept looking at me and finally mustered to courage to kiss me. His lips latched to mine and our tongues passionately intertwined. It was the best kiss of my life but it was interrupted when he started to move his hand up my thigh and skirt.
“Wait.” I whispered.
“Why?” He asked disappointed.
“Not down there. Or up here.” I said while mentioned my crotch and breasts.
“Alright.” He kissed me again and my own cock was standing at attention. I moved my hand down on his thigh and could feel the bulge in his jeans. I fumbled around on the zipper while massaging his tongue with mine.
I pulled the zipper down and put my hand inside. I found his cock and pulled it through the hole. I started to rub up and down the shaft and was shocked to find it was 7 inches. He moaned as I rubbed up and down the shaft. I broke of the kiss and moved down to kiss his huge cock. He grabbed the back of my head and pulled me towards him. I gladly went along with it but was nervous about my wig.
I opened my mouth and used my tongue to lick the head. He was anxious and excited and pulled me down farther. My mouth had 4 inches inside and I made sure my tongue gave attention to all 4 of them. The taste wasn’t as good as everyone makes t out to be but the fact that I had Chris’s cock inside my mouth made up for that. I had only been blowing him for a few minutes when he pulled my head back and told me he was close to cumming. I hadn’t wanted his load in my mouth but I had another idea in mind. I Got out of my seat and straddled him. I looked down at him and I gave him another fierce kiss. He returned it and I started to grind my hips on his hard cock. I reached under my skirt and pulled the spandex down to reveal my smooth round ass. I moved the thong to the side and grabbed his wet hard cock. I placed the head at my asshole and I let it sit there as we continued our kiss. I let my salvia lube my ass and I gained the strength to sit down. His cock penetrated me and the first inch felt like it was going to rip me apart. I pushed down farther and nearly screamed as it continued to slide into me.
I nearly orgasmed as his entire member was thrust into on one final push. Our tongues continued their fiery dance and Chris’s hands were holding my ass cheeks as he rhythmically thrust his cock into me. I met his thrusts with my hips and I couldn’t help but moan in pleasure. This continued for only a minute before I felt his cock twitch. I knew he was about to cum and I kissed him harder then any other time. He broke of our kiss and groaned in absolute bliss.
“I’m cumming.” He tried to whisper.
I put my mouth by his ear and whispered back. “Cum in me. I want you’re cum in me.” That did it and my ass was filled with load after load of his jizz.
We sat there panting, I didn’t dare get off of his cock, I wanted t n me for as long as possible. I leaned back but Chris wasn’t done. HE leaned toward me to kiss me again. While he leaned forward he brushed up against my rock hard cock. He started to speak but I leaned forward and met his kiss. He seemed to forgot for a moment or two but frantically broke off the kiss.
“What the fuck?” He asked nervously.
“Don’t worry about it.” I said trying to sound calm. I leaned forward again and kissed him. He returned the kiss and I could feel his cock starting to grow again.
“No, wait. What was that?” He asked more calm this time.
“Do you want to do this again?” I asked ignoring his question.
“Yes, that was amazing. But what was that?”
“I’ll show you.” I grabbed his hand and guided him up my skirt. His hand grazed my cock and he withdrew it immediately. However his cock was fully erect inside of me once more.
“You’re a fucking dude.” He whispered.
“Yes. But why does that matter?”
“It matters because I’m straight.” He replied.
“But you seemed to enjoy that.”
“I thought you were a chick.” He said angrily.
“It was still amazing though wasn’t it?”
“Get the fuck off of me.” He said louder this time.
“No.” I started to move my hips back and forth and got an immediate reaction from his cock. He met my movements instinctively. “I won’t tell if you don’t.”
He didn’t respond but started to pound my ass harder then I wanted. He slammed my hole as hard as he could but I was yelling in pleasure.
“I won’t tell, but your going to be my little slut from now on Marissa.” Chris said.
I could feel his cock twitch again and I knew I would be filled again. “My name isn’t Marissa, it’s Derek.” I replied.
Hs face was that of pure shock. He didn’t know what to do. He was just sitting there staring at his best friend while load after load of his cum filled me up.