Micheal Finds Jamie

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Straight guy finds his buddy all dolled up and gets some.
1.6k words
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Tonisshy
Tonisshy
62 Followers

I sat on the edge of the recliner looking at him in awe on the couch. My friend Jamie lay there sleeping soundly as I looked on. I always knew Jamie was different yet I would never had guessed this.

I couldn't stop looking at his legs, one long tan leg smooth and shapely crossed over the other. An anklet on that leg. His toenails painted red and a toe ring on the index toe. I was amazed at how beautiful his legs are.

Then his ass, in a word is perfect. A great upside down heart shaped ass with nice hips and a thin waist. He wore thin cotton pink pajama short shorts and I could see the pink thong, part of it disappeared between his cheeks.

The small of his back is curved as he snuggled the pillow. The white tank top barely holding in what I guessed to be prosthetic breasts. And his long dark brown hair spread out over his narrow shoulders and over the couch was so shiny, silky looking. I wanted to run my hand through it.

But the most amazing part of Jamie, his face. Even in sleep he was gorgeous. He has high cheekbones and a perky little nose with a nose ring. His lips are supple, pouty almost.

Why hadn't I ever seen him like this before now? Did Jamie set it up for me to find him like this?

No that was impossible he had no clue I'd be coming over like this.

It's 3am and I had no place else to go. Gina was fucking another man at our place when I got home. So I left and drove around for awhile before coming here. I did call and text and almost didn't come over but I drove by and saw his car so...

I knocked on his back door but no answer. I knew where he had a key on the back porch so I just let myself in.

Jamie rolled over and opened his eyes and saw me. Panic crossed his features but faded quickly. Then panic hit me!!

"Michael, what're you doing here?"

Even his voice was softer, more feminine than what I'm used to.

"My nights been full of surprises."

He smiled and I felt like a school boy talking to a pretty girl for the first time, "I'm sure. What else surprised you tonight besides the obvious?" He asked.

"Jamie, why didn't you ever tell me about...this?"

Jamie sat up and curled his legs under him like a girl would. He propped his arm up on the back of the couch and rested his head on his hand. "It's not the kind of thing you tell your straight friends about. But this is how I'm most comfortable. What other surprises did you have tonight?" He asked again.

"Gina-"

"Fucking around? Are you actually surprised?" He said cutting me off.

That kind of hurt my feelings. I nodded though.

Jamie reached over and touched my arm, "Hey, you can do better."

I didn't know what to say. I was so attracted to him at this point. We sat there in silence for too long. I wasn't sure if I was supposed to say something or do something. I wanted to but I didn't and wasn't sure.

He took my hand and pulled me to the couch. I didn't resist. He pulled me down on top of him and whispered in my ear, "don't think, just go with this. I won't ever disappoint you or cheat on you." And the he kissed me softly on my lips. His lips were so soft. I kissed him back passionately as my hands groped all over him.

"I'll be your girl..." Jamie whispered.

I'll let you be my girl I thought to myself. I saw Jamie as a girl. She smelled nice, felt so small under me and kissed me so sweetly. She moaned a little as we kissed causing me to kiss her more. Her legs wrapped around my waist as I dry humped her.

"Roll over Michael."

We switched places easily as she is so much smaller than myself. With her on top now I ran my hands down her small back and at last I could feel her beautiful ass with both hands. Again she let out a soft moan.

Jamie placed kisses on my neck and then helped me out of my shirt. Then she kissed my chest, my nipples and down over my stomach. Then, Jamie knelt up between my legs and undid my belt and pants helping me out of them too. Then she repositioned herself over my crotch pulling down my boxers just enough to let out a gasp.

"Oh my, Michael. Why in the world would that little bitch cheat on you?"

I watched her as she leaned over my cock and lift it up with her small hand, she licked her lips and opened her mouth taking the head into her sweet mouth. I moaned.

She swept her hair to the side so I could see her face as she took more of my cock into her mouth.

I ran my hand through her beautiful hair as she took a few more inches deeper into her mouth. I would be surprised if she managed to get all 8 plus inches.

Our eyes met and locked onto each other as she slowly went up and down my shaft.

Then to my surprise and delight Jamie went all the way down until her cute little nose was buried in my patch of pubic hairs. She moaned softly as her tongue licked my balls with my cock deep down her throat.

My cock had never been down anyone's throat before. The feeling was soft, moist and completely wrapped snug. I could cum easily but I wanted to enjoy this longer.

Jamie must've sensed this as she came back up slowly and then went back down. She continued this for a few moments as we kept eye contact.

She stopped, taking me out of her mouth while holding me with her tiny hand, "I want you to fuck me."

I smiled and nodded.

Then she went back down, slow and tantalizing her tongue working the underside of my meat. Such a lovely mouth. Then she released me and took me by the hand leading me through her apartment and down the hall to her bedroom. She pushed me back on the bed and we kissed again.

She worked her way back down and engulfed my cock once again. She seemed to purr as she slowly sucked on my shaft.

Then she stopped and reached into the night stand. She returned with a condom and some gel. She climbed back up on the bed and expertly rolled the condom down over my cock. Then she slid her pajama shorts off nice and sexily. She applied some gel to her ass and climbed on top of me.

She took my member in her little hand and guided the head to her hole. As she sat back I felt myself at her entrance and with a gentle push I felt a pop and I was inside her ass.

"Ohhhh!" Jamie moaned aloud. Then ever so slowly Jamie pushed herself down on my rock hard rod.

"Oh oh owww, ooooo!" She moaned louder.

"Are you okay?" I asked concerned.

"Mmmm, yes." Jamie said as she began to ride me. I still wasn't all the way in her but Jamie was working her tight little ass with what she had of me.

"Ooohhh gawd your so big!" She moaned and slid down taking even more of my fat cock.

Then Jamie had me, she had my entire cock inside her fine ass! And she was squeezing her anal cavity working me up into a frenzy as she rode me.

Looking at Jamie now I saw how sexy she really is. My hands were on her smooth thighs then on her hips. Her hands were on my chest then she leaned back and ran her hands through her long hair. She was really enjoying this. Moaning and wriggling and squeezing!

"Oh God Jamie I'm gonna explode!"

"Take me from behind!" She said with a sexy pout. How could I say no?

She slid off me with a soft 'pop' and got on her hands and knees.

"Oh no Jamie, you know how I like my girls, remember?"

She giggled and said, "face down ass up."

I watched as she lay her face on the bed, that beautiful hair draped around her, her slender arms above her head. I took her by the waist and positioned my cock at her hole and slowly pushed in.

"Ohhhhhhhh", Jamie moaned as I slid all the way inside her. I was so deep I felt the tip of my cock stop on something causing Jamie to moan louder, her mouth wide open and eyes closed.

I began to pull out and push back now holding onto her silky smooth hips.

"Ohhh gawd Michael fuck me harder!!" She cried.

I started pounding her tight ass so hard I was lifting her up off the bed. I knew I wouldn't be able to hold out much longer.

Jamie's back was arched, ass up high and her pretty face on the bed and I knew I was about to explode. I grabbed her hair and pulled as I shot my first load deep inside her.

"AHHHH YESSSSS!" She moaned.

I kept pumping her ass and kept filling her with my cum as load after load shot out of me.

A moment later I collapsed on top of her and she reached behind holding me inside her.

"Mmmmm, please stay inside me." Jamie whispered as I kissed and nibbled her ear and neck.

We fell asleep shortly after this.

Tonisshy
Tonisshy
62 Followers
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8 Comments
smoothed273smoothed273about 2 months ago

💖💖💖💖💖💖💋💋💋💋💋💋✌

cdCindy1cdCindy1over 4 years ago
I'm Jamie

I'm a sissy CD cocksucking faggot -- like Jamie -- and I would love for my male friends to feed me their cocks and fuck me. Please tell more stories like this one. It's so hot.

AnonymousAnonymousover 6 years ago
Fun story, hot too

I enjoyed the encounter. Hopefully it will turn into a long story! I have a friend that I think is like Jamie. I often daydream about finding him like this and starting a new relationship together.

AnonymousAnonymousover 6 years ago
Implausible

He has a girlfriend that cheats but won’t do oral.

Just too stereotypical with the key hidden on the porch and the

"Ooohhh gawd your so big!"

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