Shemale Shock

My s****r Louise was always trying to set me up with women she knew. Somehow she felt as if she were responsible for my love life. Louise's latest scheme was to throw a party and invite me and all her women friends that she could.

I arrived at my s****r's party and to her credit there were other men there besides myself. Unfortunately most of the women there didn't interest me in the least. Some were real tarts, some were loud d***ks, but most of the women didn't know I existed. One woman there did interest me.

Her name was Cheryl. She worked in the same office as my s****r. My s****r barely knew who she was, but she made a blanket invitation to all her co-workers and Cheryl showed up. I was glad she did. Cheryl was average looking to be honest with medium long brown hair. You would probably not notice her walking down the street.

I disliked women who put on airs and Cheryl was not one of those. I struck up a conversation with her and it seemed like she was interested in me. It was hard to say really. Cheryl seemed shy, but I try to loosen her up with a few glasses of wine and it seemed to be working.

The party was winding down and I finally popped the question to Cheryl. Would she like to stop over to my apartment afterwards. To my surprise she said yes. Cheryl followed me in her car back to my place. Once inside I took Cheryl in my arms and we kissed. Cheryl seemed a bit reluctant at first.

"Tom, you need to know, I am different," she explained to me.

"Different how?" I asked Cheryl.

She didn't answer at first and we kept kissing and I was undoing the buttons of her top. The top came off and I got her bra off as well. Cheryl didn't seem to mind that I had my lips planted in the tips of her nipples. I was sucking both nipples into my mouth. After a few minutes of this Cheryl pushed me away.

I was a little confused. She seemed to be getting into the kissing and touching. Cheryl stood up and started to undo her pants. I sat there watching her every move.

"You need to know about me, Tom." she told me.

The pants dropped to the floor, but something was wrong. Cheryl had a bulge in her underwear. Then she stripped off the undies and I knew her secret. Out popped a cock hanging between Cheryl's legs. My face must have said it all. I was shocked. I didn't know what to say.

"Do you still want me now, Tom?"

My cock was stirring in my pants. I was a bit confused still. I somehow did want Cheryl despite her having a cock. I stood up and shed my clothing and took Cheryl in my arms. We stood there in my living room and were kissing each other passionately. Our cocks were rubbing against one another.

To be honest, Cheryl's cock was average size but on the thin side and her balls looked small. my cock wasn't gigantic by any means, but I was very thick. I managed to get Cheryl over to my couch and I fell on top of her. Our cocks were having a sword fight now. Then Cheryl whispered in my ear.

"Suck my cock please, Tom"

I was a little shocked to be honest. I had never taken a cock in my mouth before. If I didn't suck on Cheryl's dick, would the sex stop right there? I moved down between her thighs and lifted her dick in my hand. I lowered my lips around the tip of her shaft and began to suck on head.

Cheryl was moaning and running her fingers through my hair. Her moans were getting me worked up and I went down further on her dick until I was all the way to the root. Cheryl was now pushing her hips into my face. My head was bobbing up and down her totally erect pole. Cheryl's cock had grown to a good size from all the action from my mouth.

Cheryl was now holding down the back of my head with her hands. She was urging me to take her. Her hips came up from the couch and she was gagging me with her female pecker. Then Cheryl let out this cry and I felt my throat being flooded with her cum. I was going to pull off, but Cheryl held my head down on her hard root.

I ended up swallowing all her female seed down my throat. Cheryl kept pumping her dick and sending the last drops of her seed down to my stomach. She was growing soft now and she let me pull away from her cock.

Thank you Tom, God that was intense," Cheryl told me.

To be honest my jaw was hurting a little and I had the taste of Cheryl's cum in my mouth. But my cock was rock hard from all that wild sucking that had taken place. I was looking down at Cheryl. Her body was sweating and her cock had drops of cum leaking out from the tip. I wanted her so bad still.

I took Cheryl's legs up and spread them apart. Cheryl gave me a wild look. I think she knew what I had in mind. I then placed her legs over my shoulders and I moved the head of my cock to the entrance of her ass.

"Go easy please, Tom" Cheryl pleaded.

I slowly pushed forward. Cheryl had a pained look on her face, but I kept feeding her my shaft. After some minutes I was inside her tight hole completely. It felt like my cock was in a vice. I began to pull out then I slid all the way into Cheryl's shit hole.

Cheryl had her head thrown back as I pushed in and out of her. After a few minutes, Cheryl started to meet my thrusts with her own movements. We were getting into it now. I wanted to fuck her in the worst way and make her mine for good. Sweat was pouring from both of us. Each stroke produced the sound of my nuts slapping against her ass cheeks.

I was getting deep as was humanly possible and Cheryl was taking every hard inch I possessed. We must have fucked like that for close to a half hour. All that hard gripping of Cheryl's ass muscles had me nearly ready to cum.

I pounded her tight hole a few more strokes and then I couldn't hold it any longer.

"I'm cumming!" I cried out.

I began to blow a quart of cum deep into Cheryl's bowels. We both were thrashing upon the couch, fucking one another like two a****ls in heat. Cheryl gripping my dick with her ass and milking all my seed from me. Looking down at her face, she looked like she had to have my love offering. I squirted a few more ropes of cum and then my cock felt spent.

I left my dick in her hole until I finally softened and slipped out. We were both panting and I lowered my mouth and started to nibble on the tips of her breasts. This last little bit must have pushed Cheryl over the edge. Her hard cock twitched and then shot wads of cream all over my chest. After Cheryl came for the last time, we collapsed on top of each other.

"That was the best sex I ever had Tom," Cheryl told me.

I had to agree with her. After we cooled down some we took a shower. There was more groping and kissing and Cheryl knelt down and worked her mouth up and down my dick. I had thought I had died and went to heaven.

Cheryl stayed the rest of the weekend with me. Most of the time was spent in bed having sex. We have both decided that we want to be together and enjoy the unusual sex we have already tried out.
97% (59/2)
Categories: AnalGay Male
Posted by Acebottom
4 years ago    Views: 3,466
Comments (8)
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1 year ago
Pretty good
2 years ago
4 years ago
congrats my friend
4 years ago
mmmm hot story
4 years ago
4 years ago
O that was so hot had to jack off half way through thanks
4 years ago
fuckin great story wish i was that fly on the wall! better still wish i could join u both!
4 years ago
great story!