I was headed for sex reassignment, but changed my mind. It was to be in three separate procedures to create a vulva. In the breast department hormones had given me two beautiful boobs that spilled out of a D cup. It was always exciting to see the way men eyed them. I certainly didn’t need implants. My mother was huge in the tit department, and they say that those genes can carry over even to a son.
My mother caught me more than once dressed up in her clothes. It started with just lipstick and went to heels, hose, and mini skirts. One day just after I’d plucked my eyebrows into two thin graceful curves, and had my makeup on just right, she came home unexpectedly. With my begging she gave in to the idea I wanted to be her daughter.
I was very feminine in my mannerisms which caused me misery at school. Let me say to you I’m sure it’s genetic. The female Y chromosome got mixed up with my male X chromosomes. I got used to them saying, “I bet he squats when he pees.”
At school there was name calling like fairy, fag, cock sucker, and queer. I had a terrible crush on a boy named Frank. He was everything I was not. Broad shoulders, husky, deep voice. Thick curly black hair that touched his collar. At sixteen even though he was clean shaven I could tell he had a heavy beard. I got that exciting little tingle in my crotch getting just getting glimpse of his hairy chest.
One day he invited me over to his house and play pool in the basement. I was flirting with him like mad, and trying to get through to him with my body language. I always wore panties under my jeans and they were getting soaked just seeing him lean over the table to make shots. He had a beautiful compact ass. His whole body exuded power.
I discovered soon after puberty how to really pleasure myself. One thing was beating off, but the best was getting to my prostrate with what ever I could find: candles, bananas, even my hair brush handle. It was the real thing that I wanted that day.
We finished playing and Frank returned with two cans of beer. My chest area since puberty has been swelling. My breasts were just big enough to have to give up going swimming in public. Later after I started taking hormones they really bloomed.
After our game Frank sat down next to me on the couch. As if my hand had a mind of its own it ended up resting on his leg. I turned to him and said, “I guess you know I’ve had a terrible crush on you.”
When he didn’t answer I figured I really blew it, but I followed up with, “I’d do anything for you Frank.”
He pushed my hand away. “Please, Chris, don’t misunderstand me, I like you but I’m not gay.”
“I’m sorry, Frank. Sometimes I can’t help myself.” I felt so small and helpless sitting this close to him, and I started to cry.
He put his arm gently on my shoulder. “Don’t feel bad. It’s okay. Do you really want to touch me there?”
“Oh yes,”
He took my hand and placed it on his crotch. One things was for sure I was turning him on. My fingers felt something I’d never touched before except my own. It was huge, probably twice as big as mine. I was wild to get it out of his pants.
“Go ahead,” unzip my pants.
I did and folded it out. It was uncut, about nine inches long, thick and leaking pre-cum.
“Frank, darling, just pretend that I’m your girl friend,” I said.
That really wasn’t too much of a stretch because I was wearing pink nail polish, and my thick blonde hair was shoulder length.
“Do you want to kiss it?”
“Oh yes.” I got down on my knees in front of him. My small hand could only go part of the way around it. The first thing I did was kiss the bulbous head and give it quick little sucks.
He reached under my blouse and found one of my small breasts. What I was tasting was heady, manish, seminal, what ever—I loved it. I could feel his hand on the back of my head. I wanted more of him but it was so big. I pressed down on it to take more. His hand fond the back of my head and he forced me down. I could feel it slide slowly over my lips. The next thing I knew he thrust his hips up and penetrated me to where my lips were pressed against his nest of public hair. I was choking and scared.
This must not have been the first time he was serviced. He released the pressure on the back of head and I came up for air. I’d had enough of cock sucking but he pushed me back down. This time I took in a breath of air and was deliciously aware of his monster sliding over my lips. We got into a rhythm, and I had no problem with my breathing. He was fucking my face so hard that it hurt, but I loved it.
It must have been my estrogen driving me to feel so female. What I wanted was his creamy load. I knew after that I would never be quite the same, and I wasn’t. His first spasm shot down my throat. He pulled out enough to flood my mouth with the second, and third creamy load. I swallowed as fast as I could. This pushed me over the edge and I came all over the rug and side of the couch.
The next thing that happened I couldn’t believe. With his strong arms he picked me off the floor, sat me down next to him, and kissed me. There was cum running down my cheeks. I was still trying to swallow it all. We sat there on the couch French kissing.
You might say from that afternoon on I became Frank’s mistress. He was the first to stick his precious cock into my male pussy, in other words he fucked the hell out of me and I loved it. Our relationship must have turned him around because after several weeks we ended up in a 69.
I much prefer playing the female part but he begged me to take him from behind. I’m afraid our relationship might have changed his sexual orientation. Several months after our affair ended I saw him with another person, This person had that androgynous look, so I couldn’t be sure if I was seeing a guy or a girl. . They were holding and hands.
I already knew I wanted to live as a woman before that afternoon. This was reinforced with Frank wanting to share me with some of his close friends.
A number of years have gone by. I’m living completely as a woman now, working as a real estate broker. I still see Frank now and then and some of his friends, but I’m living alone. When it came to the sex change operation I decided against it. I was having too much fun the way I am. Yes I’m still on estrogen, and I will be for the rest of my life. I did go through the long expensive, painful electrolysis for facial hair.
You might meet me some time in a singles bar. The guys tell me I’m good looking. I wish I was a little shorter so that I would always be looking up to a man, but standing 5’ 7″ in heels, it’s not too bad. My measurements are 38 w28 x 42—okay, so I have a big fanny. All the better for a girl like me with a male pussy. I forgot to mention that Frank, even though he’s married with kids, still comes back for a little of that.
By the time I was eighteen my mother was divorced and dating a lot of different guys. One in particular seemed to notice me even more than my mother. One night he dropped by when I was alone. It was one of the nights my mother was working late.
“I’m sorry Kathy,” he said. I should have called first.”
I lied saying, “She should be home any time Johnny, let me get you something to drink.”
I was wearing white tennis shorts, and a halter top. When I’m at home I hate wearing a bra, and I’m sure watching the look I got that this didn’t go unnoticed. John has a outdoor, cowboy look about him. Broad shoulders, thin, and a nice firm ass. He always looked like he needed a shave, but on him it looked good. I’d often imagined what it would be like if he kissed me.
I brought him a gin and tonic and took a beer for my self. Before I came out I ducked into the bathroom and renewed my makeup. I don’t wear that much just a little mascara, and lipstick. The electrolysis I’d been going through for the last year took care of any facial hair.
I leaned over to hand him his drink and my boobs about fell out of my halter. He was saying something about maybe he should go, but did not quite finish his sentence.
When you want something I’d found out you better go for it so I took a chance. “John,” I said sitting down next to him. “I lied to you.”
He gave me that boyish smile of his, “What do you mean by that, Rosemary?.”
“Mom’s not going to be home for at least two hours.”
He sipped his drink and gave me a puzzled look. “Now, why did you do that?”
When I didn’t answer he put his hand on my leg, and I think my look told him what I had in mind.
The End
