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Thread: My ladyboy Affair

  1. #1

    My ladyboy Affair

    As I walked out of the divorce court I was one pissed off individual, I got to keep the house and car but lost everything else including $800 a month in spousal support. I didn’t want to go home to an empty house so I decided to visit the Mall and see a movie hoping that would take the anger away.

    I selected “Toy Story 3” entered and took seat at the back of the theater. As I sat there watching and laughing at what was going on a young lady sat down a couple of seats down the aisle, I looked at her and noticed that she was about 4’7” tall and slim but very nice looking. After a few minutes she got up and moved beside me and sat back down. She leaned over and said her name was Kay and how was I enjoying the movie. I told her that it was alright and that my name was Mike, then I felt her hand on my leg which caused me to start getting an erection, as she rubbed my leg her hand brushed my crotch, I knew she felt my hard-on.

    She once again leaned over and told me that I had a nice one, would I mind if she took it out and held it for awhile, I unzipped my pants and her hand disappeared inside gripping my cock and pulling it free. As she began running her hand up and down she asked how big I was, I told her it measured 8” would she like some. There was no reply but instead she leaned over and took my cock in her mouth and a very talented mouth it was, and began sucking, I heard her gag as she attempted to deep throat him, but when she found out she was unable to take all of my cock, she concentrated on just the head and the part of the shaft she was able to suck.

    I will say one thing she, was good, she had me humping her mouth enjoying the pleasure she was giving. I told her that I was ready to cum and that’s when she really began sucking; she was after the juice that would be flowing from my cock. When the first shot left my cock I held her head in place making her swallow as fast as she could. She kept sucking even as he was going soft making sure she had every drop of cum that was still in the shaft in her mouth and down her throat.

    She rose up but still held my dick in her small hand moving it back and forth. I reached around her shoulders and slipped my hand down her blouse and started playing with her nipples and breasts. She snuggled closer to me and leaned her head on my chest still hoping to get me to rise up once more. We both noticed that the credits were rolling on the screen so she placed my dick back in my pants and I removed my hand from her tits. I asked her if she would like to join me for dinner, and she said she would very much enjoy doing that.

    As we exited the theater and headed for the car I got a real good look at her in the light, she was absolutely stunning, she was wearing a skirt, blouse, and 3” heels which made her look taller. We went to my favorite restaurant and had an enjoyable meal while telling each other our woes. She lived alone and worked in an office as a secretary taking calls and answering questions while her boss was away. I looked at her and said that this being Friday night and you don’t have any work tomorrow how would you like to come home with me, and we will spend tomorrow traveling around. She looked me in the eyes and told me she would love to, but I needed to know that she is not like other girls and based on that if I still wanted her to come with me then its OK.

    I asked her what she meant. She came right out and told me that I could fuck her in the ass and she would suck my dick as long as I wanted but that’s all I could do. I paid the bill and grabbed her hand and we left, once we were in the car I leaned over and gave her a kiss which she returned and I drove home; as I was driving she was playing with my cock through my pants so I reached down and unzipped and let her take him out for some fresh air. That didn’t last long; she leaned over and started sucking on the head getting him harder and harder, just as I was about to lose my load she stopped and said, to be continued.

    When we arrived at the house I parked the car got out with my dick waving in the wind and went inside; once inside I pulled her to me and waged war with my tongue in her mouth as we kissed. I was unbuttoning her blouse so I could get at her tits, once there I was massaging both of them and pinching the nipples, this brought a moan from her, so I started down south when she called a halt and reminded me of what she had said earlier in the evening, fuck her in the ass or she would suck me off, but no straight fucking.

    Kay saying this put a damper on my desire for the moment so I told her that my daughter is about her size, why don’t she go back there and see if she can find something to wear and get out of your clothes. I showed her the room and left to mix us a couple of drinks, when she came back out she was wearing a silk dressing gown and her heels. Seeing her dressed the way she was only excited me again and she came over and undid my belt and trousers letting them fall to the floor then went after my shorts pulling them off too. Here I stood naked when she made me sit down on the couch spread my legs and then she squatted between them and took my dick in her hands.

    As she was jacking my cock she opened her dressing gown and placed my dick between her tits and began jacking him off by rubbing him between those perfectly beautiful tits; she would dip her head and lick the head of my cock as it was on the up stroke, she knew that what she was doing was driving me up the wall, so after a few minutes of this she stopped got up and said where is the bedroom. I got up and with my arm around her and with her hand on my cock escorted her to my room. I turned on the night light and she said no lights as we lay on the bed, then things really got heated.

    I was lying on my back and she was slobbering all over my cock, then stood removed her panties and straddled me guiding my dick to the entrance of her ass. I was surprised at how easily I moved smoothly inside; every inch she took she would moan and tell me how I was filling her up. It was hard for me to understand how such a small girl could take all 8” up her butt, but she did.

    As she began wiggling around and bouncing up and down she would moan and telling me to fill her up with cum, I want every drop up my ass, OH God you feel so good!!! Fuck me, damn it Fuck me!! I held her hips and started fucking and pounding my dick in her ass and she would scream: Harder!! God Damn it harder!!! As we fucked she would squeeze her ass cheeks together adding that much more pleasure to the act. I told her to get ready I was going to flood her ass with more cum then she could fathom, and then I unloaded, when cum hit the walls of her ass channel she would moan that much louder; OH God!!! Your cum is so hot, don’t stop now, keep it coming.

    When I finished she would not release my cock but held on as it soften, then she rose up enough to let it fall out and remained in that position till all the cum was expelled from her asshole and on my cock and balls. She swung around and proceeded to lick every morsel of cum off my cock and balls then lay down beside me. We lay there cuddling till we fell asleep.

    The next morning I awoke to the smell of coffee and got up heading for the kitchen, once there Kay poured a cup and asked what I wanted for breakfast. I said I wanted her and picked her up and carried her back to the bedroom, I threw her on the bed and tore her panties off, she started crying and when I looked I understood why, she had a dick. It was cute and small like she was, I picked it up in my hand and felt how smooth it was, then surprise, surprise I took it in my mouth and sucked on it till it got hard, well as hard as it was going to get, and I moved up beside her and proceeded to jack her off.

    I kissed away the tears and asked her why she never told me before I had to find out the way I did; she told me that when ever she went on a date and told the guy she was with that she was a “Ladyboy” he would beat her up while calling her all kind of nasty names, so she decided that she would not tell the person she was with that she had a cock.

    I rose up and got between her legs lifting them and placing them on my shoulders, this opened her up and I sank my dick in as deep as I could go; then I began fucking her just like she were a real girl, I reached and grabbed her dick and began jacking her off while I fucked her ass. This brought more moans and groans from her each time I moved in and out of her ass; that’s when she told me to rub the head of her dick which I did and that brought out greater moans when she yelled: God Damn it Mike I’m Cumming!!! That’s when I really began pounding her ass because I too was Cumming and I unloaded in her ass with hot cum and listened to her yell what a bastard I was.

    When I had drained my cock in Kay’s ass I noticed that she had shot her load up on her stomach and tits; I let her legs drop and bent forward and tasted her juices as my dick softened in her ass. As I removed my dick I lay beside her and damn if she wasn’t crying again, I asked what was wrong? She looked at me and said; Mike when you bent down and licked cum from my stomach I never felt so happy in my life as I did watching you licking up my juices; Mike if you don’t watch it I could fall head over heels in love with you, and I’m sure you don’t want that, or do you?

    I kissed her and said, what makes you think I couldn’t change my life style for a girl like you, that’s correct I called you a girl, I will consider your little dick as your “little man in the boat”, which you will find on any real girl. We hugged and sucked face while I reach south and began playing again, except this time I included her balls and asshole in my play time. When I stuck my finger up her ass and hit her prostrate gland she arched her back and came all over her stomach and yelled: You are a Bastard Mike!!! When she relaxed and her breathing returned to normal she looked at me and said; God Damn that was good, no it was great, now let me take care of you.

    I held her down preventing her from getting up and going south on me, I just wanted to lay next to her and cuddle, she accepted this and we lay in each others arms until it was time to fix lunch. After lunch I told her to get dressed, we were going to go retrieve her belongings and she was moving in with me. After getting her things I decided to visit the Mall and do some shopping, we visited one shop that had nothing but exotic clothing so I told her to shop till she dropped. The things she bought would make a dead mans dick rise to the occasion. We had dinner at the Mall then drove straight home where we made mad passionate love up into the wee hours of the morning.

    The next morning as I sat at the kitchen table and as I watched Kay prepare breakfast I thought I might be the luckiest guy on the planet, here was a young Lady Boy wanting to enjoy life and here I was sitting here with a raging hard-on wanting to bend her over the table and feed her the meat at 6 AM. I called her over and took her in my arms and began playing with her asshole and hitting her prostrate gland which was getting hotter and hotter, even her little cock was raising up, so I turned her around bent over the table and drove my dick as far up her love canal as I could go.

    I started fucking her so hard that I was knocking dishes off on the floor and all she did was hold on and scream; “Daddy!! Fuck me harder!!” As we fucked she took her little hand and was jacking off while moaning her head off, I told her to get ready here it comes and I unloaded deep in her bowels, and she yelled; I’m Cumming too…………. When I pulled out and sat down she remained lying on the table top and panting till her breath returned to normal; after she got up she turned and kissed me while making a grab for my cock; then she bent over and got down so the head was level with her mouth and she planted a kiss and licked the last drop of cum lingering at the hole and said; “you, young fellow, are a very nasty boy, but I love you all the same”. Got up, cleaned up the mess we made and returned to fixing breakfast.

    I thought while I watched her run around the kitchen, that maybe this was my true calling, a lover of “Lady Boys”.

  2. #2
    Administrator April's Avatar
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    Thanks for the new story :)
    Don't worry... it only seems kinky the first time ;)

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  4. #4
    Awesome! I'm sorry I didn't read this one sooner. Really a hot one that got me stiff.

    Thanks for the contribution. :icon095:

  5. #5

  6. #6

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    I got a job in Vietnam after college working for a company made up mostly of men that were always grabbing my tits as they walked past me. I never like men trying to take advantage of me and my body. One Friday night at a club I noticed a group of girls together and while many men trying to push there way into the young girls. I walked over to them and asked if I could join them which several in broken English said yes. Upon sitting down I noticed that some of them had their breasts on display much like I did. It started to become a drag with all the men trying to get free feels of our bodies so I asked them if they wanted to leave and come over to my place which they all agreed. At the time I had not noticed how many there were mainly because several got on their phones and called others to come. Upon entering several noticed a sign in my living room that said no clothes allowed. At first they all got together with me and told me that they were different then me and said that I did not understand and they that they were called lady boys and they all had cocks. I said so what and as I started to my clothes off so they also followed. They were very correct in that their chest were flat to huge breasts and their cocks went from a few inches to well over ten inches. Upon seeing them I had an orgasm just standing there with several getting down on there knees and licking me out They hit the kitchen and started cooking while five huge cocked ones filled my hands and my three holes. While three shot their loads deep into my holes the other two came all over my huge breasts. As we ate they were talking with me and wondering if I was unhappy with the way they fucked and I told them that they could stay with me and fuck me as they all wanted. Several told me that they had boyfriends and girlfriends and I told them that all were welcome because I loved sucking cocks as much as I loved eating out juicy cunts. Needless to say I got pregnant many times by who I do not know along with their girlfriends and possibly not by their boyfriends.

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