Ladyboy Mai


I was invited to a party in Naic, Cavite, Philippines where I met Mai, she was shy and reserved unlike a lot of the young ladies that I had met in the past. When I finally got her to open up and talk to me we became, you could say, good friends. Mai stood less than 5’, had a sculpted body, nice breast, nice ass, and was 26 years old. As the party progressed we made plans to slip out early and get a cup of coffee at one of the restaurants close by. When we left the party we walked to the Three Sisters restaurant, upon entering I noticed that everybody was looking at me and Mai, she was a very beautiful young lady.
After spending a couple of hours having coffee I told Mai that I would like to see her again, would that be possible? She smiled but said nothing. She mentioned that she had to get home so I offered to take her, on the way back to the car I stopped and took her face in my hands and kissed her, when she kissed back I knew that I would be able to see her again. She directed me to her house where she lived with her brother and older sister, her parents were deceased, we exchanged cell numbers and before I left;we sat in the car making out when her little hand came to rest on my thigh. I reached down and drug her hand up so she could feel how excited she made me. She massaged my cock and told me to move the seat back, where she unzipped my pants and reached inside pulling my cock out. She bent her head down and took my dick into her mouth and stated sucking, I started rubbing my hand up and down her back trying to reach inside her pants so I could play with her pussy.

She was having none of that and moved my hand away from her ass. I laid my hand on her head and whispered that I was Cumming, she never bothered to lift her head off my cock but took it deeper in her mouth and let each load enter and slid down her throat. When I finished and she had finished getting all my nectar I pulled her face close to mine and kissed her deeply. She put my dick back in my pants and zipped me up. She told me that she would call me later and got out of the car and walked towards the front door of the house. I waited till I saw that she entered the house and that she had looked back before shutting the door.
When I got back to my apartment my cell went off showing that I had a txt msg. I noticed that the sender was Mai so I opened it and read where she had enjoyed herself tonight and most especially when she sucked my cock. I txt’d back that I really wanted to see her again and if she wanted I would bring her to my apartment and cook dinner tomorrow evening. She txt’d back and instructed me to pick her up at the Three Sisters Restaurant at 6PM. I txt’d back that I would be there, good night.
I arrived at the Three Sisters Restaurant and standing outside was Mai, she was dressed in heels, skirt, blouse, and her long black hair soft and shinny. She got into the car and I leaned over and gave her kiss and we were on our way to my place. When we arrived I escorted her to the apartment and once inside poured us a glass of wine. We had dinner and she offered to clean up so I let her, and watched her every movement with an erection that wouldn’t quit. When she had finisher I grabbed her and pulled her onto my lap so she could once again feel how she excited me. As we kissed I picked her up and carried her into the bedroom where I laid her on the bed and began too unbutton her blouse and help her out of her bra.
As she laid back down I immediately made contact with her nipples sucking and licking each one in turn, I decided that I would continue my kissing and licking down her stomach, skipping the main course, I licked up and down each leg. As I worked my way back up her legs I pushed her skirt up as I went and was about to attack her pussy when she placed her hand over where I wanted to go and with the other pulled my face up to hers. That’s when she told me that her real name was Mike. I looked at her and reached for her groin, she tried to stop me but I got her panties pushed aside anyway, and low and behold she really did have a cock. She said I’m sorry, I should have told you last night but I didn’t, I’m really sorry, if you want to take me home, if not I can always catch a Tricycle, but, before I go I could give you another blowjob if you so desire.

I made Mai get up and stand before me and remove the remainder of her clothes, as she straightened back up I looked her over and noticed that she did not have a hair anywhere on her body. I reached for her little cock and her nut sack placing both in the palm of my hand and started massaging them just to see how big she would get. Nothing was really happening until I took my other hand and sucked on one of my fingers and stuck it up her ass, this brought about a change in the size of her cock, it reached about 4 ½” long. It reminded me of a very, very young boy who had not yet reached puberty. I made her lie back on the bed and went back to kissing my way down her body, but, this time I stopped at her little cock and before I took it in my mouth I removed my dentures and put her cock and ball sack in my mouth and started sucking. Each time I ran my tongue around the head of her little cock she would raise the lower half of her body and moan that much louder. I let her ball sack drop from my mouth and concentrated on just her small cock. She really started moaning and withering as I stimulated her cock and called to me that she was Cumming!!. The amount of juice that came out would not fill a sewing thimble, but, it did taste sweet and was some what milky which made it flow easier down my throat.

Mai said; “Daddy please stop! I’m way too sensitive”, Please!! Instead of stopping I inserted two fingers in her ass and began moving them in and out as I sucked her little cock. As my fingers stimulated her ass she was fighting hard to make me stop because of the sensations she was experiencing, but, when she was finally able to push my head away and pull my fingers out of her ass she laid there; her breathing was ragged at first, but as her breathing returned to normal she looked at me as I was replacing my dentures and pulled my face down so she could kiss me and tell me; “its been a long time since she had received that much pleasure”. She had me stand and helped me remove my clothes taking extra time removing my shorts, it was almost like a strip tease; she was kissing her way down as my shorts reveled skin. When she reached the part she wanted she licked up and down both sides and then took the head into her mouth, running her tongue around and around the head as I had done to her. She tried to take all of me into her mouth but only managed about 5”, she still had 2 additional inches to go.
She looked up at me and told me that she wanted me to fuck her boy-pussy, but, I had to take it slow as she had never had a cock my size in there. I told her that I was going to provide her with additional pleasure, that which she has never experienced before, we moved to the CR (bathroom) where I had her lie on the floor in the fetal position as I prepared the solution of warm soapy water and greased the butt plug. I inserted the enema nozzle in her ass and opened the flow control telling her to breathe normal and enjoy the feeling, when I had emptied the bag I inserted the butt plug and had her stand, once up I took her little cock in my mouth and began sucking, I would reach and rotate the plug in her ass. Having her ass full of warm liquid and a warm mouth on her cock was driving her up the wall; I told her to tell me when she was ready to expel her load of juice. I had just repositioned her over the commode when she yelled; here it comes!!! I reached and jerked the butt plug out and pushed her down on the toilet and finished her with my hand, she grabbed my neck and was holding on for life; the sensations she was experiencing were such that they caused her to faint. I held her until she returned to the land of the living. Once back among the living, I carried her back to the bed.
She laid there hugging me while regaining her strength and told me that she had never experienced anything like that before. I asked her to tell me about herself. She began by telling me that at very early age she was displaying female mannerisms and would sneak a pair of her sister’s panties and wear them. She went on to tell me that she would climb into bed with her brother and while he slept she would look and handle his dick watching it get hard, she even kissed the head on one occasion and tasted the pre-cum. One night, while watching and playing, I took the head of his cock in my mouth and licked around the head. I kept this up for a few minutes, but, when I began to remove my mouth I felt his hand on the back of my head and he whispered don’t stop. I continued sucking and I felt his cock expand a little and then begin to spurt fluid out.

He told me to swallow which I did and I fell in love with and wanted more cum so I sucked him again and got another load of juice. As I grew older I went to a doctor and explained that I wanted to be a girl. We discussed what would be required of me and that I would have to start taking female hormone pills in order to develop breasts. He provided me with a prescription for the meds that I would have to take and then he said he wanted to exam me. He had me get undressed and lie on the exam table and he started by lifting my cock and ball sack and stated that it was a shame that I would loose my lovely cock, then he bent over and took it in his mouth, as he sucked he inserted a finger in my ass; and that really felt good. It did not take him long to suck the juice from me.
He had me move down to the edge of the table and lift my legs then he stuck his dick in my ass and started fucking me, he must have pushed a button on his desk because the door opened and his male nurse entered, seeing what was going on he took his cock out and stuck it in my mouth, I was getting double penetration, mouth and ass.

Doc unloaded a huge load in my ass and his nurse unloaded in my mouth, which I swallowed with joy. Doc told me that he wanted to see me every week so he could check my progress but most of all fuck me as I had the tightest ass he has ever fucked. It took me three years to grow my breast and loose my body hair and I visited Doc every week for my loving injection of cum from his cock. My sister helped me with my dress; we would go to the market and purchase sexy under clothes and very sexy outer garments for me to wear. She would get so excited with my makeover that she would make me play with her and she even taught me how to eat pussy and satisfy a woman without fucking her. I did not like licking her pussy I only wanted to suck on a nice juicy cock.
As she was relating her story she was massaging and playing with my dick. Mai continued her story telling me that she went to Manila and went wild, sucking and fucking every thing that would let her. One morning she awoke and discovered that she, in her drunken stupor had taken on 15 guys the night before, this was the final straw that broke the camels back; she snuck out of the hotel room and came back to Naic. She told me that she has since led a quite life and was only fucking and sucking her brother; her sister tried to fix her up with a few of her friends but I would have nothing to do with them. Daddy…. You are the first date I’ve had in two months and I’m willing to do what ever you ask if I can be your girlfriend.

I hugged her and she laid her head on my chest, I placed my hand on the top of her head and pushed it towards my cock. Her head was now lying just above my groin area and she bent my dick so she could lie there and suck me slowly till I came. I started playing with her ass and I told her that I wanted to fuck her; she reminded me that I was to take it slow so she could adjust to my size. I reached in the bedside table drawer and got the tube of KY Jelly and let her apply it to my cock, then she rose up and straddled me so she could control the depth that I would be achieving as I fucked her. She placed the head at the entrance of her rosebud and wiggled around until the head slipped in, then she stopped. I noticed her rolling her eyes and a pained look on her face but she just stayed in the position she was in, with only the head of my dick in her ass.

As she became accustom to me she would accept a few inches more, stop and adjust, then more inches till she reached the bottom. Once she had consumed all 7” she started moving up and down, but, this time when she rolled her eyes it was in pleasure. I roll us over so she was on the bottom and lifted her legs up to my shoulders and I took over moving in and out of her ass. Mai looked up at me and started squeezing her ass cheeks together making her ass as tight as she could so I would enjoy the greatest pleasure from fucking her. She reached for her little cock and was massaging it so she could cum at the same time I did. I told her to get ready I was fast approaching a climax and if she wanted to be there she had better hurry. I screamed at her…here it comes!! As the first shot left my cock her cock let loose with her little bit of cum and that’s when I told her to milk my dick. She was squeezing and letting go, then squeezing again as each shot left my cock and was deposited in her ass.

We continued to see each other and enjoyed each others bodies, sucking and fucking till we could not fuck or suck anymore. A month after we had started seeing each other she txt’d that she was on her way over and 5 seconds later the doorbell rang. When I answered she was standing there dressed in a very sheik black strapless dress, with 3” high heels and her face made up with just enough makeup to enhance her beauty. As she entered and I shut the door and said; “baby…this is bull shit, why don’t you just move in with me”. She came running to me and jumped up wrapping her legs around my waist and her arms around my neck, saying yes…yes. I sat her ass on the table, pushed her dress up, removed her panties, and began sucking her cock to seal the deal of her moving in.