tagTranssexuals & CrossdressersShemale Shock Continues

Shemale Shock Continues

bystandingstones©

I met Cheryl at a party thrown by my sister. I asked Cheryl to come to my place afterwards and she agreed. That was where I discovered Cheryl was a shemale. I did something I had never done before. I sucked on Cheryl's cock and I took her load down my throat. After that I ended up fucking Cheryl's tight ass and giving her my own load of cum.

We had now been seeing each other for a few weeks. One Friday evening when Cheryl was over she made a request.

"Can we try something new Tom," she asked me.

I asked her what she had in mind. She told me to get on all fours on top of my bed. I knew what was coming and it was something I had never tried before. I reluctantly got on my hands and knees. Cheryl placed a pillow at my head and she told me to lift my bottom up. I then felt Cheryl's hands on my hips and her cockhead was pressing on my opening.

Cheryl pushed her cock into my hole slowly. Damn, did it hurt. Cheryl wasn't all that big cock wise and her dick was sort of thin, but it hurt nonetheless. Cheryl told me not to tense up. I tried to stay calm as she pushed deeper into my hole. I soon felt Cheryl stop as she had filled me completely with her female dick.

Cheryl started to stroke me slowly at first. That womanly cock was stretching me, preparing me to take a good fucking. That is exactly what happened. Cheryl was now slamming that dick of hers deep into my ass. God help me, I was starting to get used to her cock being in my bottom. I grunted as she laid across my back and fed me her erect pole.

"I wanted to fuck you so badly Tom," Cheryl let me know.

"Oh fuck yes," I screamed out loud.

Thank God, Cheryl wasn't any bigger than she was. It felt like a log pole was buried in my shitter. I lost track of how long Cheryl took my virgin hole. I could tell she was getting close to cumming as she was making these whimpering noises. She pounded me a few more time and then she let go. I felt her warm seed hitting deep in my belly. I did what came naturally and I squeezed her shemale cock with my ass muscles. This made Cheryl cum even more.

She poured her hot cum into me for a long time it seemed. Eventually she started to slow down and I felt her getting soft in my ass. Cheryl pulled her dripping dick from my hole and I collapsed onto the bed. Cheryl told me to turn over and then she was on top of me kissing my mouth. I could also feel her spent dick rubbing against my pecker.

As a man I hated to admit it to myself, but that was some of the best sex I had ever experienced.

"Did you enjoy that Tom?" Cheryl was looking deep into my eyes.

I told her yes and Cheryl got a big smile on her face.

"I had been wanting to do that for a long time, but I was afraid to ask you," Cheryl told me.

Now it was my turn, I figured. I flipped Cheryl over onto her back. Her eyes looked wild as if she knew it were her turn now. My cock was so hard by now. I lifted Cheryl's legs up by her ankles and I rested my mushroom at her opening.

"You are mine now, I am going to fuck you until you beg me to stop," I told her.

I quickly drove my prick past her rim. Cheryl let out this scream like she was being fucked by a wild animal. I pulled out and then pushed in all the way. Over and over, I gave Cheryl the longest strokes I could.

"Please Tom, harder!" Cheryl was pleading now with me.

I pushed in hard, my nut sacs were slamming against her cheeks. I knew I had a big load saved up and I wanted Cheryl to have every drop of me. I took Cheryl like she took me. It was a hot, passionate ass fucking I gave her. The time finally arrived. I couldn't hold back another minute. I felt my balls tense up and I erupted inside my shemale lover.

I sent hot geysers of cream into Cheryl's belly. She screamed when she felt it enter her stomach. That made me cum even more. I kept fucking my shemale lover until she had milked my cock dry of my love offering. I left my dick in Cheryl as we tried to calm down some.

"That is the kind of lovemaking I want to have with you Tom," Cheryl explained to me. "I want us to share cocks," she went on to say.

I never thought I would like to take a cock up my ass, but with my shemale lover Cheryl doing it, it felt so hot. I know this is just the start of some intense lovemaking with my new lover.

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by Anonymous

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by davefoley196206/20/14

Good reading

It is always a pleasure to read a story in this category that is about sex with a "shemale" rather than a crossdressing man caught by his wife.
Well written, to the point yet still well detailed.

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