Play Beginnings

by: Majcardinal 
View Story Details
Rating: XXX Add Review    Added: 05/16/2007
Complete: yes 
Synopsis:How I learned to have sex from the schools play.
Categories: Crossdressing / TV 
Keywords: Petticoats and Crinolines 


My first sexual experience was interesting. I was in ninth grade at a military school for boys. We wore uniforms, did physical training, the whole lot. We also did plays, musicals, and the hitch was that boys did the girls parts. I was young, had lean limbs, and could pass for a girl if I wanted too. I tried out for a new musical called Hair Spray. I did really well. I got a part called Tracy. My counter-part was a guy named Steve. His part was a part called Michael. Steve was built, very muscular. His hair was jet black, and eyes brown. His abs were just starting to show as well. His legs were nice and thick.

After our parts had been announced, we where handed scripts. I flipped through it and noticed some kissing scenes. I was shocked and didn't know how to react. But I took it in stride. Rehearsals went well until the night before we where supposed to do our kissing scene. We where also in costumes at this point. I was wearing a pink poodle skirt, a white blouse, and unfortunately a bra with some silicone breast forms. Steve was wearing jeans, black boots, and a white t-shirt.

After that evenings rehearsal Steve asked if we could go over some lines that evening. I agreed and he wondered if we could meet in costume. I said yes, and we walked over to his room. He was lucky enough to have a room of his own. We sat down on the bed, and whipped out our scripts.

We both turned to the next scene. It told us to embrace so we did. Our arms came around each other our and so did our scripts. We read each other our lines, and we both paused when we where supposed to kiss. I dropped my script to the bed and so did Steve. Steve took my head in his hands and brought his lips to mine.

The feeling was electric all over my body. I pulled back and looked at Steve. He had a glazed look over his eyes. I leaned into him again and put my lips on his. Once again electric was all over my body. I ran my hands over his arms. They felt so nice underneath his t-shirt. I was shocked to feel my penis get hard underneath my skirt.

Steve pulled back and slid his shirt off in one motion. I finally saw his chest. It was nice and smooth. The muscles felt nice when my finger tips traced over them. I pulled away and took off my shirt. He smiled when he saw my feminine chest. He leaned me back to the bed and kissed down my neck. His lips barely brushed my fake bra, and tickled my stomach. I erupted in giggles and he laughed along with me.

I grew quite and my breathing got quick as his hands felt my legs encased in tights. He spread them apart slowly and moved ever closer to my groin. He pulled down the tights, my underwear and started to caress my hard penis. It wasn't that big, and his hand nearly covered it as it went up and down.

My hands went to the back of his head when his tongue reached out and touched the tip. I had never felt anything so warm and wet as his tongue. I pushed down on it and he took the entire thing into his mouth. He sucked on it, caressed it, and rubbed it all at the same time. I had no idea what he was doing to me. But I felt something come out of my slit. He licked it up and continued to suck and lick. The feelings were soo nice and I started to shoot stuff into his mouth. Steve opened his mouth and showed me what I did. Inside was a little puddle of white stuff on his tongue. I felt glad that I did it for him. He made a big show and swallowed it all.

My hands crept up and down his body until they encountered his jeans. I unbuttoned them and slid them inside. His ass was nice and muscular. It felt great in my hands. Steve groaned loudly, and I continued to remove his pants. His hard cock came into view. It was about 8" long, and about 1" thick. I snaked my tongue out and touched his head. It started to leak a clear fluid. I took some of the fluid and rubbed it around the head. He smiled down at me and got off of the bed. I stood up with him and hugged him. His cock bumped into mine and once again I felt electricity. I turned him around and sat him on the bed.

I knelt at his feet and grasped his hardness in my hand. It was soft and hard at the same time. I loved how it pulsed when my hand made contact. I bent down and took the head in my mouth. Steve's hand came to the back of my head and encouraged me to take more of the monster into my mouth. I slowly took more of it, and pressed against it with my tongue. He gasped at this and my mouth continued to swallow him.

His cock was nice and warm. It felt like it was continuing to grow. The veins pulsed and I pulled back. Steve smiled at me and I looked up at him. He pulled me up onto the bed and reached for his night stand. He pulled out some vaseline and he opened it. His hands felt firm on my hips as he turned me over on to my stomach. I rose up on my knees to give him some better access.

The next thing I know is that his greasy finger is sliding into my anus. I quickly tried to squeeze him out, but his persistence paid off. Soon he was in me too his knuckle. It was a strange but good feeling emanated from my ass. It felt really great as he stretched me out with another finger. I bucked against his fingers and he must have taken that as a sign.

I felt empty as his fingers were pulled from my body. A new sensation came over me as he placed the head of his cock against my ass. My breath was coming in short gasps and I squeaked in pain as the head tried to enter me. Yet again Steve was patient and slowly pushed into my body.

My anus gave a last gasp of resistance as his cock head entered my virgin body. I loved the exquisiteness of his large penis in my body. I eased back onto him and I heard a soft groan from above my head. I keep moving back and soon I feel his thighs against mine. I contract around him and my ass is just humming in pleasure. I pulled off of him and shoved my hips backwards. If that wasn't great, then I don't know what was. My hips repeated the fucking and Steve's hands wrap around my hips. They urged me to go faster.

While I was fucking Steve, he laid on my back. He kissed my neck, felt my fake boobs, and wrapped his arms around my waist. It was quite a shock as to how easily he rolled us over. I stood up and pulled off my skirt. He grinned when he saw my legs come into view. I turned around to face his feet and the head was placed against my ass. My mouth formed an O and a loud groan came as his hard, long dick entered my body. When he was all the way in, I ground my hips and I felt a nice special place that I just wanted to have stroked. I looked down and my penis started to get hard again. I bounced up and down on it and Steve was trying to shove himself up further inside of me by moving his hips up while I was barely off his cock. I sunk down on it and gripped him again, and I was rewarded with more white stuff shooting from my body. Steve almost screamed and I felt him shoot probably the same thing into me.

Pretty soon he was softening, and I turned around and kissed him. I felt his tongue snake into my mouth and I briefly let mine play with his. I got off of him and he helped me dress. It didn't take long to make me look like a proper young lady, and he escorted me back to my room. I appreciated what he did for me, and when the coast was clear I gave him a good night kiss on the cheek. He turned and walked away, and I went to bed a happy girl.