Kiss My Ass

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Man realizes he enjoys playing the part of a woman.
1.5k words
4.45
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It all started when my friend and I went to the bar. His wife and my girlfriend were both out of town so we decided to have a boy's night out. We were having a good time and both of us were pretty drunk. There was this beautiful woman with the nicest ass I ever seen. Tom and I both noticed and had a hard time not staring at her. Tom made a comment about how he loved licking ass and that he would go crazy to taste hers. I made a comment how my girlfriend sometimes licked mine and how much I enjoyed her doing it. He told me I had a nice ass and he would like to eat mine. Being drunk, horny, and half joking I said sure.

As we drove back to his house, he said again how much he enjoys licking and eating ass. He described in great detail the things he licks to do. He described an erotic detail how he likes to cup an ass in his hands and slowly feel up the cheeks. He sometimes would slowly squeeze with both hands and move one hand to slide down between the cheeks to let his one finger slide inside. Sometimes in his slow tease he would let his finger touch the opening and lightly tease it by rubbing his finger in circles around it. He also said how he enjoys kissing an ass, alternating side to side slowly. He liked to take his time and savor the moment. He would wet his lips and gently suck, almost like a sucker bite. We got to his house and he said how he never licked a man's ass and he doesn't intend to start now. But, he said if I would shave off all my hair and moan like a woman that he would do it. I told him I was not sure. He said all I had to do was pretend I was a girl while he licked my ass and we both would enjoy ourselves.

I told him yes, so we went to the bathroom and proceeded to shave my ass. He made this a fun time and put me at ease by saying how turned he was watching me shave. When I was completely shaved, he made comments about my ass and said it looked so sexy. He felt my ass and commented on how sensuous it felt. He said it felt so nice and that he is looking at it as if it were a woman's ass. He asked me to help him pretend I was a woman. He told to pretend and play act like I was girl. He told me to giggle like a girl and act all sinfully innocent. He said, girls know when they are naughty and love acting like they are all innocent. I was starting to get into it when he pulled out lipstick and a sexy pair of feminine panties. He said to put this on and it would help me that much more sexy and sensuous.

I put on the lipstick and panties and he was right. I felt very sexy and was ready to feel his tongue lick my ass. I told him so and he lay on his back and told me to sit on his face. I did what he asked and straddled his face, my knees on the bed on either side of his face, with my head facing towards his cock. He brought his hands up and cupped my cheeks. He lightly felt my ass and moved them so gently across my ass. Sometimes he would cup me and squeeze. Once in a while I would feel his lips kiss my ass and it was very slowly. He was really getting into this. This went on for sometime and he told me how sexy I felt and what a turn on this was to him. I saw his cock was getting very hard and knew he was enjoying it. He told me to continue playing the part of girl enjoying her ass being felt and kissed. I started to feel his tongue as he kissed me. He would cup my ass, place his lips close to his hands, squeeze me, and then I would feel a warm lightly moist trail as his tongue moved from one side of my ass to the other.

His kisses would sometimes get harder and his squeezes would sometimes be hard. They would at times be forceful but gentle and always sensuous. He started rubbing his one hand up the middle of my ass and toyed with my opening. He put his hands around my hips and forced me to lean so my face was only inches from his cock. This allowed him to cup my ass better and for him to lick my opening. He licked all around my opening, making me very wet and then he pulled me closer with hands and moved his tongue into my ass. I heard him moan and could not believe the sensation. It felt so good. He moved his tongue in and out of my ass, stopping sometimes to kiss around my cheeks and to give my ass a nice squeeze with his hands. He told me my ass was so sexy and better than any girl he ate before. He told me to start playing with my clit. I hesitated not knowing what he meant and he moved one of my hands to my cock and told me to play with it. I started to do this and was coming close to cumming.

He then told me, what a good little girl I have been by allowing him to eat my ass. He said how excited he was and that I made him so excited by offering my ass to his pleasure. He said he was ready to cum and wanted me to pretend to be a girl that also enjoyed sucking cock. He told me he was going to place his hands on my head and that I was to open my lips and allow his cock fuck my mouth. He said he would control my head movements with his hands. He then went back to eating my ass. I then felt his hands on both sides of my head. He gently but forcibly moved my head down and said open my mouth. His cock was by my lips. I never sucked cock before and hesitated. I was not sure about this. He said I was acting so good being like a girl that he wanted me to go a little further.

He said my ass made him so horny. He then told me being a little kinky and pretending to be a girl and pleasing a man sexually does not make me gay. He said that this would be very kinky and fun both of us. I opened my lips and tasted my first cock. It felt so different. I never expected it to feel the way it did. It was hard but soft. It was rubbery but the texture was pleasant. I felt so erotic having his cock in my mouth. Here I was, being told I was a sexy girl, lipstick on my lips, a pair of sexy feminine panties on, my ass completely shaven, being in a sorta 69 position with me on top, being bent over with my mouth open and a cock inside it, his mouth kissing my ass, his tongue up my ass, his hands on my head using and fucking my mouth. I felt very sexy. He told me how good I was and how kinky his girl was being. I started to really enjoy sucking his cock. He then held my head tight so I could not move and he told me he was going cum and I was to swallow. I did not have anytime to object. With his hands holding my head down on his cock I was pretty helpless as he came in my mouth. I was forced to swallow so I could breathe. After he came he continued to eat my ass until I came. The feeling of a warm wet tongue up my ass as I came was incredible.

The next weekend I went to his house and his wife Becky was there. She answered the door and welcomed me in as Tom was getting ready. She was beautiful, very feminine, and had a killer body. She said to sit on the couch while we waited. She told me Tom discussed in every juicy detail what happened the week before. She said how turned in that made her. She continued and said that Ton is allowed to be sexual with anyone he wants to as long as it is not with another woman. She said they enjoy turning a man temporarily into a woman and enjoy having fun that way. She said she likes to watch Tom having fun and especially likes to help make a man look like woman and then watch her creation being sexual with Tom. She said she knows what Tom likes in a girl and would make me very sexually appealing to him. Tom came joined us during the later part of Becky's talk. She said she would like to place makeup on me and dress me up. She wanted to see Tom take my virgin ass and would help me girl-to-girl to take his whole length in.

To be continued...

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AnonymousAnonymousalmost 3 years ago

hope to see part 2

AnonymousAnonymousover 4 years ago

Ohhh I want to hear about Becky dressIng you up . How exciting that would be!

AnonymousAnonymousover 6 years ago
hot

Was a very good story.I can relate as I was once a friend of mines other woman and his wife use to help me look sexy for him

AnonymousAnonymousalmost 9 years ago
Fantatic!!!

Loved your story. I hope to cum back as a woman in my next life.

AnonymousAnonymousover 9 years ago
can't wait for the next chapter

Please continue this story, it's so hot. I would love it if my best friend's wife dressed me up as a sexy sissy slut and then her husband (my best friend) would feed me his juicy cock to suck and then he would fuck me deep and hard while she watched. That's my fantasy (I'm already a CD, so I just need to get my friend & his wife to agree). I can't wait to read the next chapter of your story.

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