sexstories.com

Introduction:

51 yr old crossdresser thinking back upon his introduction to sex

It all started when I was in third grade. That is when I started to crossdress. I would strip down and put on my mom's bra and panties. Even though they were too big for me it was exciting. I was thrilled. My heart beat faster, my breathing increased, and I reveled in the pure joy of dressing up. My little cock would jump at every movement of the silky fabric of the panties. I would walk around in front of the mirror and admire how I looked. I ran my hands up and down my body. Feeling my hard cock push against the fabric making a tent of the panties. I would also slip on a pair of heels. I liked how they forced my ass up in the air.

One day I was walking around dressed up when my older brother caught me. He told me in order to be a true girl I had to climb on top of him and get him off. He disrobed to his underwear. I was still dressed so I climbed on top of him and started grinding my hips into his body. I felt his cock getting hard. I continued to work my hips rubbing my cock on his through the panties. Suddenly he thrust his hips up in the air. He came in a big moan and shot his cum all over his underwear that also soaked into the panties that I was wearing. I had many emotions running through my mind. I was elated that I made him cum. I was scared. I felt dirty. I wanted more. I wanted to make other guys cum. I knew the power of being a woman.

I continued to dress up in bra and panties in the following years. I met a guy in middle school. His name was Wayne. I would have sleepovers at his house. We would listen to music and talk about the kids we went to school with. We would play with other kids in the neighborhood. I would wear bras and panties while we did these things. I would change in his bathroom when getting ready for bed. I played it off as my being modest. I didn't know how he would react to me wearing my special clothes.

On one particular sleepover we talked his parents into letting us sleep in their camping trailer. After dinner, Wayne and I went out to the trailer and made it ready for our evening. We filled it with snacks and drinks. Then we set up the beds. We got everything the way that we wanted.

It started out normally with conversation about fellow students and consuming our drinks and snacks. The conversation soon turned to sex. We talked about masturbation and girls that we fantasized about. I couldn't tell him about my dressing up. We started to get ready for bed. We undressed to our under clothes and continued to make conversation. I looked at him in his underwear and noticed that he had a hard on. I comented on his hard member. He laughed and took his underwear off freeing his hard cock. My jaw dropped and my mouth watered. It was pink, hard, and inviting. He was seven inches long. The head was shaped like a wedge. I wanted to suck on it. I had to have it. He came closer to me and reached out his hand to take my underwear down. He hooked his fingers in the waistband of my tighty whiteies and slid them down. I had butterflies in my stomach as my rapidly hardening cock sprang free. My six inch cock was at attention. We compared sizes and shapes. My head is shaped like a helmet. We were both about the same thickness. I nervously reached out and took his cock in my hand. It was warm to the touch. The skin was smooth and soft. The shaft was hard like a basball bat. I slowly started stroking him. His cock felt good in my hand. He was moaning softly. I noticed that his cock was leaking precum from the head. I ran my fingers over the tip and scooped up some of the precum. I brought my fingers to my mouth to taste it. I ran my fingers along my tounge to deposit the precum on it. I swirled his juice in my mouth. It was thick and sweet like nectar. I needed more. I wanted to swallow his load.

I pushed him down on the bed. I opened his legs and slowly crawled in between them. I worked my way up to his package. I lightly touched his balls and noticed how they tightened up against his body. A moan of pleasure escaped his lips. I leaned in closer. I slowly started stroking his cock again. This went on for a few minutes. I was admiring his cock. I noticed more precum leaking out. I leaned in and placed my mouth over the head of his cock. My tounge automatically started worshipping his cock. It circled the head lapping up the precum that was bubbling out. Eagerly I took his cock into my mouth. I bobbed my head up and down on his shaft. My saliva coating his cock. I slid my hands under his ass and grabbed it forcing his cock further into my mouth. I greedily swallowed that glorious cock. I couldn't get enough.

I kept working his cock with my mouth. He reached down between my legs and found mine. He switched between stroking me and playing with my balls. I wanted Wayne to shoot his load down my throat. But even more than than that, I wanted to ride him until he filled my ass with his cum. I stood up, turned around, and started to sit down on his cock. My virgin ass was resistant. His cock was slick from my saliva and his precum. I kept working my ass on his cock. He started to enter my ass. Then with a pop he entered me fully. I took a deep breath. My ass was screaming in pain but my head was swimming in exstasy. I sat motionless. My hole was throbbing. Finally I relaxed and began to slowly rock back a forth on his cock. I was in heaven. I increased the tempo. Soon I was bouncing up and down on his cock. I would squeeze his cock with my ass as I went up and relax on the way down. Suddenly I felt his cock swell. He let out a grunt and thrust his hips skyward. He began to empty his balls into my ass. I squealed in joy. I kept working my ass on his cock. Milking it. His cock softened and I slid off of it squeezing my ass to keep his cum inside me.

There was an awkward moment when we realized what had happened. We sat next to each other and I told him that it was ok. We talked a while longer about what happened and how we got there. We both accepted it. Meanwhile, we were both still naked. Our teenage hormones were taking over. He started getting hard again. I was semi hard. Wayne reached over and began playing with my cock. He would reach down and play with my balls also. He continued this noticing that I had a gob of precum on the head of my cock. He massaged it all over my shaft. My climax was building. I was going to explode. I kept going over the recent events. I remembered how good it felt to suck my first cock, how my ass felt with his hard cock in it, and how complete I felt having his cum inside me. These thoughts and his working on my cock sent me over the edge. I came hard in his hand. I lost my senses. When I came back I picked up his hand and licked it clean.

I then took his cock into my mouth again. Bobbing up and down. Working it with my tounge. I tasted his cum and my ass on his cock. The scents and taste was incredible. I licked up and down the shaft. Cleaning his cock with my tounge. I also sucked on his balls. I would take one into my mouth. Licking it and sliding it in and out of my mouth. I then switched to the other one giving it the same attention. Then both at the same time. What a thrill. I went back to sucking his cock. He told me that he was close. I took him as deep into my mouth as I could. He grabbed my head and held me on his cock while he exploded. His cum shot down my throat filling my stomach. He let go of my head. I kept his cock in my mouth. I gently sucked on it until he was hard again. Then I blew him again. This time I made sure to taste his cum and swish it around in my mouth. It was the best taste and feeling of my young life.

We laid next to one another. I told him about my dressing up. He was surprisingly accepting. He said that he kind of figured because of the way I acted. Nothing would ever be the same. We continued to have sleepovers. I continued to enjoy his cock. I gained nourishment from drinking his cum. He loved filling my ass with cum. We incorporated my crossdreesing into our sleepovers. I was complete. It wasn't to last past high school. But I was happy for as long as it did.

---