Lady's underwear and other intimate items have always been around me. Mom's, my older sister's, girlfriends and the three wives I've had. I don't think it was unusual for a boy to try on a pair of someone's panties, or a training bra, or maybe some pantyhose. It's not unusual, is it?
I think everyone has done it. But for me, beginning with just touching the first pair of some dirty silk panties, my little dick would twitch and I'd be ready to jerk off right away. It didn't take long until I'd find myself in the laundry room searching for something interesting to put on, rub in my face, or wrap around my cock when I was alone and ready to make myself cum.
Pantyhose always held a special place in my heart. Smooth, silky, tight and snug all around my smooth little legs, my tight little butt and my hard little cock. They felt like they were pulling and grabbing me everywhere at the same time. I'd try on different pairs to see which fit me the best. Blowing a big load inside them did make it difficult to replace them in the hamper, though. So I would throw them away. Women in my life were always having to purchase more pairs, strangely.
Enjoying the feeling the tight wrapping of the pantyhose led me to wearing another pair over my arms and around my body. Upside down. The crotch area would be around my head and over my face. I felt sort of bound up. I'd press the cotton crotch area into my face and into my mouth. I'd hold it there. Then I decided to use another stocking to tie the crotch panel into my mouth, like a gag. I'd stuffed panties in my mouth before. Enjoying that. So, I loved the feeling of the wet, slippery, silky nylons, and the smell and taste of the cotton crotch. I'd get even harder, blow even bigger loads, and my orgasm would feel so much deeper.
Tying my ankles together like I was tied by a bad man made this even more erotic, for some strange, unexplainable reason.
A bad man? Somewhere between my innocent jerking off in the privacy of my own room, and where I had evolved to, my imagination had brought a bad man into the room. A man with a big, angry cock.
Why wasn't my mind thinking about some cute girl in these sexy undies? Why wasn't I thinking of some naughty woman being my mistress? I've heard of women who like to control and abuse their men in all sorts of ways. Stern ladies wearing black vinyl outfits and swinging a whip and holding a collar for her unfortunate man slave to wear. A sexy mistress would be erotic. A cute girl, too. But, no. I keep having a man's face and body in my dreams and fantasies. Put on some pantyhose, stuff my mouth with some panties or a cotton crotch panel, tie my ankles and my wrists like I'm a kidnap victim, and there it is. A big, hard, ready to blow it's load down my throat, cock.
I wanna suck one.
I tried not wearing the girly underwear for a while. But I'm weak, and horny. I love wearing them. I can't help myself. So, after several attempts to be a regular guy, I decided it was time to follow my kinky desire to be some hairy man's cock sucking, submissive, butt boy. Yes, when you dream of sucking a man's cock, you also can't help but want him to hold you down, shove his dirty shorts in your mouth, call you a whore and a faggot, then fuck you like a pig. Who knew?
Most of the men in chat rooms are more like me. Submissive and trying to find a real man to 'date'. On top of that, very few, if any of the men who described themselves as Dom, were into a guy who likes to wear ladies underwear.
I didn't give up. I searched and searched through several local sites until I finally met Harvey. He says he is a Dom and he likes sissy crossdressers very much. He is patient and enjoys meeting inexperienced guys to train like they are his pets. I'd need to take orders, do as he tells me, and expect to be a submissive, crossdressing, obedient, cock sucking play toy. I'd be a sissy gay faggot for him.
That sounds a bit rough. But after several more months of searching, he was the best Dom man I could find locally. I agreed to be his slave for a weekend. He picked me up in front of my house, and that's when it all began.
Harvey
His long Cadillac SUV was black with dark tinted window. When I approached, he rolled down the window and told me to get in the back seat. I didn't get a good look at him. I opened the door and slowly, carefully climbed in.
"Put the mask on." He calmly requested. I looked at the seat where a mask was placed. It's almost Halloween so I didn't really think much of it. I actually thought it was kind of silly. I looked up seeing he was wearing a mask as well. His was a black leather looking thing that covered most of his face, with is eyes and mouth showing. It looked a bit like the mask the Texas Chainsaw guy would be wearing. Again, it was almost Halloween, so I didn't panic.
Yet.
My mask was one that you would wear if you wanted to look like a showgirl. It was very soft and rubbery. It was a woman's face with just two small eye holes. There were a couple of straps hanging from it that were designed to go around my head and neck, to strap it securely on. As I slowly lifted it up to my face, I noticed that inside, where the mouth was located, was a large rubber ball. I quickly realized was going to be in my mouth. The eye holes were taped over inside. I wouldn't be able to see anything, or speak, when this was strapped and buckled on my head.
"Put the mask on." He repeated. This time a it more sternly. I obeyed.
The ball was soft but really big. It took me a bit of time to finally get it into my mouth. My mouth was sore and drooling almost immediately. I was fumbling with the strap and taking much to long as far as he concerned. I felt his hands take the straps and buckle them for me. He pulled the one holding the ball in my mouth extra tight. I let out a little squeal. He didn't say anything at all. Except one comment after my mask was tight and secure.
"Bitch."
I rode in the back seat for a long time. We were going out of town. We were on the freeway. I tried to speak but of course, I couldn't say anything except make some stupid muffled moans and squeals.
After a while I began to get restless and very nervous. What the fuck was I thinking? I started pulling at the back of the mask, looking for a buckle to release the horrible ball in my mouth. I was ready to call this off. I was in a bit of a panic.
The Escalade stopped. Doors opened and closed. I felt him climbing in the back seat with me.
"Let's get you settled down, by little bitch."
I was pushed back sitting with the door behind me. He had my wrists pinned together. I heard tape being ripped off a big roll. My wrists and arms were taped together with several wrappings. He pulled my arms up over my head, binding my wrists to the headrest up behind me. He pulled my shirt all the way up. The cute little bralette and corset he had requested I wear was exposed. He roughly opened my pants and pulled them all the way off. Under my pants I was wearing the cute pink panties and thigh high stockings he had picked out for me. He was looking me over. He held my head from behind by a hunk of my hair. His other hand was on the middle of my chest, gently touching the soft bra cups. Side to side. One bra cup, then the other. I wiggled. I tried to push the ball out of my mouth one more time.
"Mummph...fuck!"
He squeezed one of my 'tits'.
"Mmmmm... Nice, bitch." I could feel his eyes on me. My cock was hard. What the fuck?
His breath was hot. He was close.
"I'm going to take part of this mask off, and remove that nasty gag, then you're going to suck my cock like a whore. Right now. OK?"
I wanted the ball gone. Very much. I guess that was part of his plan. He could tell I was responding. This was it. My dream come true? Or his? I guess we would see.
I nodded.
Cock for me
He was hung like a horse. I learned over the next few days how he liked it sucked and stroked and played with. He let me wear all sorts of sexy outfits while I was learning to be his cock slut. After the first day he told me it was fucking time. He took his time and made sure I was prepared to be a fuck toy. Lots of training toys, dildos, butt plugs, beads and lube. Finally he pushed his huge one inside me, sliding in and out gently at first. But by the end f the weekend, he was pounding me like a puppet.
We didn't stay in touch after that. I haven't heard from him again. Until yesterday. He says he has a few days free next week, and he misses me. He said he would like me to dress like a bride. He was going to dress like a priest. Some kinky sex and roleplay. I've been shopping wedding lingerie. He said he's been shopping bondage and BDSM gear. Might be a great weekend.
Billy
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