My dad and mom dead, my stepmom only kept me around for the money benefits. She caught me crossdressing and then taught me a lesson.
My mom died, my dad remarried, and then he died when I was 14. My stepmom was really hot looking and I’d sneak into her room when she wasn’t around and look at her naked and being fucked pictures she kept, and started wearing her clothes. Mostly bra, matching panties, thigh high stockings, even garter belts. I was getting really good at it and looking good. I have a thin body, sort of feminine actually with indented waist and almost no body hair. I made up an excuse about swimming to shave my legs. I was starting to wear some of her short mini skirts and dresses but it was in her undies that she caught me. She accused me of being a sex pervert, then being gay. I denied it and she made me keep the undies on the rest of the day and night. I wasn’t allowed to wear any jeans or shirts. She got me a pair of her old high heels and gave me lessons (ones I didn’t want) on how to walk through the house with them. At night I tried to take off the clothes and go to my room but she was having none of it, still berating me and calling me a good gay little girly boy. She kept showing me pictures of real girls my age and a little younger and to tell the truth even though I was 14 I did look like a 12 year old girl. I was told to take off the bra, and the rest. I thought I was escaping my very embarrassing punishment but no. She made me stand around naked, and she’d “accidentally” touch my cock or my ass. Then she overtly sucked on both my nipples and gave me to chance to suck on hers.
“Well since we’re both girls anyway it doesn’t matter” she said as she took off her clothes. I was so damn hard it was actually hurting. “Oh, look your gay cock likes pussy huh?” With that she gave me 5 swats on my ass with her hand, then hit my cock and balls so bad I bent over and went immediately soft. She picked out a nightie for me to wear and one for her. “We girls can sleep in my bed” she added and with that we got in bed and lights out. It took forever to go to sleep but she woke me up early by taking my hand and putting it between her pussy lips and humping my hand till she came.
“Get up baby, we have a lot on our plate today, we have to change you over, then teach you not to be such a sneaky little piece of ass” She put make up on me, styled my hair so I really looked like a girl. She put what she called “cutlets” in my bra and dressed from the inside out, and tucked my cock between my balls, shoved them up inside me and glued my skin around my cock. I could pee sitting down but it looked like I had a pussy. We went shopping and out to lunch. A couple of girls from my school sat near us at the restaurant but I don’t think they knew it was me, though they did recognize my step mom. Stepmom would make comments about guys we saw and how big their cocks must be and how a young thing like me must be excited too, knowing the boys all want to fuck me. I kept denying and wanted to stop but I knew that was useless. Then at night, she told me we were going out, and she’d make sure by the end of the night, I wouldn’t want to be a faggot at all. I again, tried to explain that it just excited me because it was her underwear not because I was gay. “Well don’t worry, in case you’re wrong and I’m right . . . and I KNOW I’m right, you’ll be straight after tonight”.
I was taken to a Trans swing party. She made me strip to my undies, taking off the panties she told me to keep on the stockings, garter and bra, and of course my high heels. With that two big hulky guys took me and bent me over this contraption in front of everyone. They tightened the fasteners and made sure I couldn’t move. One of them was the first. The first to fuck me in my ass, and the other was the first to fuck my mouth. I got cum at both ends. I was begging my stepmom the whole time to please get me out of there. Her answer was “As soon as you have had enough to admit what you are, then mean it when you tell me you’ve changed” I tried to say that then but she wasn’t taking it. She watched as 8 more men used my ass and other 4 used my mouth. I was crying and begging telling her I wasn’t gay and didn’t want this. Then she told me “Say what I want to hear”.
I told her while the last guy was cumming in my ass “I have had enough, I am gay and I have had enough of being a gay girly boi, I want to be straight, I want to fuck women, not be fucked by men” that did it, I was let go, but not allowed to clean up. I could only pull on my panties so the cum didn’t leak all over the car on the ride home. I kept telling her I had to poop so bad after what I’d been through. “You’d better not shit in my car, you hold it and don’t throw up either, that sperm inside you should remind you how it really feels to be a gay sissy”. My only response as I was trying to clamp down on my ass muscles “Yes maam.”
We got home and I got the toilet. I shit out so much cum, and shit but I knew I wasn’t cleaned out totally, and then I threw up. She was waiting with mouthwash, toothbrush and toothpaste. I brushed my teeth and she told me to strip as she did at the same time. She undid the glue as it was hurting so bad with me getting hard seeing her black haired bush on her pussy and her tanned big tits flopping around. “LIke what you see baby? ” she asked and I told her I did, she asked if I was a faggot anymore and I told her absolutely not. “What are you baby?” I’m a man, and I want to fuck a woman.
With that she took me to her bed, laid me down, sucked me off, taking it in her mouth and swallowing. “See, to a woman that taste good, do you like the taste of men cumming in your mouth?” “No maam”
Holding onto my balls and moving her hand around I never went totally soft, then when hard again, she mounted me pushing my cock into her pussy. I lasted enough time for her to cum twice. After I shot inside her, she responded that she did that as it was my first time after that we’d have to use a condom as she wasn’t on any birth control after my dad died. The next morning, I learned how to eat a pussy, and after three orgasms she took me in her ass. “See now, you know what all those men were feeling when they were fucking your asshole. Tell me baby which do you like better?”
“Fucking your ass” i said
“Not fucking any old ass? Like another faggots ass?”
“No maam, fucking your woman ass”
“Good, I think you’ve learned your lesson. Cum quick and get it over with, I have other things to do.”
That was the only times we were sexual. I did please my girlfriends in high school, and the ones that didn’t put out, I got to do it, as I’d been taught well. I still remember the pain and humiliation of having to dress, to go out in public then at being forced into that contraption and sucking men and getting fucked. Worse I remember the feeling of trying to hold whatever was still inside me in the car. My stepmom was at my wedding to my wife 7 years ago, we gave her 3 grandkids.
Caught, turned out, turned around and never again.
