Sarah has a Crossdressing Friend

I love to dress-up as a girl and get naughty with someone who understands the love of dressing as a girl. So I advertised on Craig's List for a crossdressing buddy; someone to play with and get naughty. A guy emailed me and we started exchanging emails and then a couple of phone calls. We discussed what we each liked to do. I love to kiss and cuddle before exchanging oral fun. I love the taste of cum in my mouth before I swallow. We agreed to meet and play the next time my wife was at work.

I explained that I live in a really nice gated community and so I would have to meet him outside and take him in. My wife takes the car to work and so he could use my designated parking space. We planned to meet at a 7/11 car parking lot just outside my complex. Thinking about what might happen the next day made me horny all night. I resisted the desire to masturbate wanting to keep it for him.

To meet him, I put on a short denim skirt with a "frayed" hem. I love this skirt. The zipper at the front is only three inches long and I wear a white belt with it. I think it looks very girly. I added a black top with matching yellow bra and panties. I did full make-up and brushed my blond hair (95% genuine blond plus a little bottle) around my face. I wore "dangly" earrings. I love the way I can hear them tinkle when I shake my head.

I am comfortable in heels but I normally wear flat sandals. For one thing, they show off my red toe nail polish but also I am already 5ft 10in and I don't want to add to my height. I don't want to stand out more than I do anyway.

I got to 7/11 a little early and so I sat on a wall and waited for him. The anticipation over what would happen was so intoxicating. What would it be like to kiss him? How would his cum taste? He soon arrived and beckoned me over. I got in the passenger side and smiled at him. I put my hand in his lap and gave his cock a squeeze. There was an enticing bulge there already. I liked my lips and said "Nice, lets go and play".

We hadn't actually scripted what we were going to do but we had discussed what we each liked. As soon as I closed the front door, I put my arms around him and we french kissed. Then I did one of my favorite things.

I dropped to my knees and looked up into his eyes and licked my lips. I undid his belt and slowly pulled his zipper down making sure my fingers ran across his cock. He had said that he couldn't be dressed when he met me but I had asked him to at least wear girls' panties. Sure enough, he was wearing black satin panties. I leant forward and kissed his cock through them.

I had to see it and so I lowered his panties and gave the head of his cock a kiss. I didn't want him to cum just yet but I had to have a little taste. I I took it right into my mouth for a few moments. It was a lovely cock. It was just a nice size to suck. He put his hands on my head and pushed my head down. I pulled away a said "Later, lets go play".

He asked if he could take a quick shower before we started. I showed him to the bathroom but left the door open while I chatted to him. He stripped off with no embarrassment. He stood in front of me with his cock sticking out. I called him a tease when he made it jump but he said "Just wait and see what's next. "

He stepped into the shower and started the water. I was so horny I stripped off and climber in with him. I went to put my arms around him but he said "Soap-up first". We got all soapy and then we kissed while we rubbed our cocks together. At one point, I rapped my hand around both of our cocks and rubbed then together. I was so erotic cuddling each other all soapy wet. I put my hands on his butt and rubbed our cocks together. He loved it when I used the hand spray from the shower on his balls. At one point I got behind him, put my cock between his legs and took hold of his cock and pushed our bodies together. His cock jumped when I put my tongue in his ear.

We were getting to close to cumming but we wanted to play more first. So we got out and dried off. Then we started to dress. We helped each other do up our bras. I put my denim skirt and black top back on. She put on a white lace trimmed nightie with a pink bra and panty set. At one point, I came up behind her, cupped a boob and squeezed her pussy. I licked the back of her heck and she pressed back against my pussy.

Then we did our make-up standing side-by-side looking into the mirror. I was surprised that she did eye-liner on both her upper and lower lids. I normally only do my upper lid. I will have to try doing the lower lid too. She was quick and had clearly done it many times before.

I put my dangly earrings back on and I brushed my hair again

Then I lead her to my bed. We started by French kissing while we pressed our pussies together. Then I had to taste her again and so I went down on her. I started with just the head of her cock in my mouth and my hand holding the base. I cupped her balls with my other hand. I masturbated her for a bit and then took her cock right into my mouth. She put her hand on my head and pushed me down. I love it when a girl does this.

After a while, she pushed me away and said "My turn". I rolled over on to my back. She went down on me and did the same to me. I loved the way she masturbated my cock as I watched her mouth bobbing up-and-down on my cock. I put my hands on her head to go really deep.

Then I had an idea, it was something I had done in the past. Oral was making us too close to cumming but this would slow things down.

We had agreed to play at being naughty school girls in front of the head mistress. I called her a naughty slutty girl for letting the boys on the school bus feel up under her skirt. I had heard she even put her hand on the front of their jeans. First, I had her bend over the arm of the sofa. I lifted up her nightie and stroked her butt through her pink panties. I traced the hem and gently pinch her cheeks. I then pulled her panties down. I gave her a gentle spanking while I made her suck my cock. Finally, I put my hand between her legs and gave her pussy a squeeze. She didn't see it coming and so it made her jump. I loved holding her cock and licking the back of her neck. She loved it when I put my tongue in her ear.

She got the message and did the same to me. It was wonderful when she tried to lift up my denim skirt but it was too tight. So I had to stand up for her to pull it up. When she saw my panties she said "This is another violation of school rules; these and not regulation panties, another stroke for you". She had me bend over and open my mouth. I was so embarrassed when she spanked me and fed me her cock. I loved being called a slutty girl and accused of playing with boy's cocks and showing off my panties.

By now we were so horny we went back to the bed and she went down on me. I came almost as soon as her mouth surrounded my cock. I loved the way she wrapped her hand around my shaft. I pulled her up and we had a sloppy French kiss; cum and lipstick together. Then it was my turn to taste her cum. I tried to copy the way she had masturbated my cock. Sure enough; it worked. She filled my mouth with wonderful hot cum.

We went back to sloppy French kissing. Finally we fell back on the bed holding hands; our cocks completely drained and limp. She got up and changed back to being a guy but still wearing his satin panties. I asked if he needed me to walk him out but he declined and left.