Crossdressing

Part 1. The Beginnings

I'm older now. I've actually had a few experiences with guys. Some were ok, others were not all that great. But I'm still looking for Mr. Goodbar!

When I was young I was always envious of the girls. They get to wear those mysterious cute little bras and panties. We only get a glimpse of a bra strap showing over the shoulder. And the outlines of the rest of the bra and panties under their tight shirts and leggings. So selfish of them to keep their pretty undies covered up and so secret from us. The little bitches.

But mom leaves her underwear out on her bed. I can find it most anytime. I can never venture into my sister's rooms. Those places are off-limits. So a bone-white Playtex closed bottom girdle was my first love. It felt so soft and rubbery. It would slip on over my young, smooth skin. I would pull the stretchy fabric until it was all the way on. Tight and very snug on me. I didn't know what to do with the sexy little garters hanging from the bottom of it. I couldn't figure out how the clasps worked. But I would pull on some of her thigh highs. Those felt so nice wrapped around my legs. I remember getting hard almost immediately, feeling my little hard-on under the rubber fabric, and cumming. I suppose that is why I still have a fetish for similar foundations. 

After a while I found myself digging through her drawers looking for more. Mom was a slender lady, with B cup boobs. The style of the day was longline, wide strap, padded white braziers. The kind with 4 or even 6 clasps in the back of the bra. One of my favorites had even more clasps. It was more like a corset. Still in conservative white. But the bottom part wrapped around my body almost to my naval. With a girdle, I was nearly covered from my bottom, to the top of my chest. It felt GREAT! More instant hard-ons. More wonderful masturbation.

I remember one day being in a full assortment of her undergarments, just looking at myself in the full-length wall mirror. I would pose like I thought a girl would pose for her boyfriend. Looking fuckable. I pulled my hair back and put on a little bit of mom's red lipstick. Gee, I almost didn't recognize myself. 

All of her stuff was a little tight on me. I liked that. Oddly, it gave me a secure feeling. The more of her underwear I'd put on, the better I felt. I wanted more. I tried on one of her dresses one day. But it was much too long on me. It hung too far down from my shoulders, too. I'm not as tall as her. I needed something else. 

One Saturday morning the house was completely empty. I decided to break all the rules and take a peek into my sister's room. She was a couple of years older than me. She was home from college for the summer. But out of the house for the weekend. I carefully wandered around her perfectly organized bedroom. I knew if I moved even the smallest item, she would know it. Well, I hit the motherload. Her bras and panties were all the sort that you'd see in the sexy ladies' magazines. I wanted to bury my face in them and jerk off. But I didn't dare. I was in the secret places no boy or man is ever invited to see. It was in the forbidden city. My sister and her friends were all so sexy. Posting naughty pictures on their Instagram pages where they know mom will not see them.  Teasing the boys. Lifting and pulling aside their shirts just enough to show off their fancy undies. I was so horny!

I couldn't touch any of her stuff. But what a great tour I was having! I plunged face-first into her closet. Felling her soft, sexy shirts and blouses hanging there. And then I found them! Her old prom and party dresses from high school. She had them all pushed in the back in a special corner. There were slips and padded bras and cute little ruffled shirts. There was dust on the tops of some of them. She hadn't looked at them in years. I might get away with this!

Hanging inside one of her prom dresses was a full body stocking. The kind you'd wear under a dress in case it was a little too see-through. It was light tan in color. It almost matched my skin tone. It had cute spaghetti straps over the shoulders and fit under the crotch with a snap bottom. One of those things that have 4 clasps, like on the back of a bra. But it's under your crotch. I'd never seen one before. But it was love at first sight. 

I undressed and tried it on right there. It was a perfect fit! My little cock and balls needed to be secured before I could clasp the bottom. I took a chance and borrowed a pair of her panties. I wanted a regular full coverage type. I didn't think any of her skinny little thong-backs would do the job. There was some right there in the hamper. After pulling them up, I clasped the bottom and looked at myself in the mirror wearing her awesome body stocking. It fits and looks pretty hot! But, I need tits. 

I picked through the dozens of training bras. Some must have been from back in Jr High. I chose an innocent-looking white cotton 'A' cup bra with little blue flowers on it. It was tight. Just the way I like it. I rolled up a few pairs of panties from the hamper, stuffing the tiny bra cups. Slicking my hair back and using her pink lipstick, I looked myself over in the closet mirror. The stuffed bra looks perfect under the tight body stocking. Ther lipstick changes who I am. It's funny how just the right accent can make such a big difference. I'm pretty hot!

I fucking look just like her!

Part 2. The dressing up

I spent the next few months wearing her party dresses and old underwear. The tighter the better. I'd rummage through the hamper every day now. I'd find all sorts of fun and naughty underclothes. I'd dress up, get hard, and wank off two or three times a day. But the next chapter in my dressing adventures happened when she went back to college. 

Everything she left in the closet was fair game now! I found a garment bag full of her old Halloween costumes. Oh My God! It's the mother of all mother loads! I was a sexy maid, a naughty nurse, and a witch with a pointy hat and everything. This was when I started wearing wigs. There were several in with the Halloween costumes. I started taking pictures of myself too. It seemed silly not to keep some photos of me after taking all the time to dress up. Then, of course, I'd fall on the bed, roll around in the sexy clothes and jerk off. 

This is where it gets kinky. After a few weeks, I got to the bottom of the Halloween costume garment bag. What was this? A black shiny bodysuit. Very stretchy. It feels like thin vinyl or leather. It's a onesie! Before I stepped into it, I put on a cute little padded bra and a black thong back panty. I slowly pulled it up as it stuck to my warm skin. There are feet at the bottoms of the legs and glove things at the ends of the arms. It zips up the back, and it's a little small for me, so I had some trouble with that. At the top, above my shoulders, there was more of it. It's like a hoody. But it's tighter. I pulled it up over my head. There was more. I pulled it around my face. There's a zipper down the front of it. There are only small eye and mouth holes. I slowly pulled the zipper down. It closes, going all the way from under my chin to below my neck. It's covering my entire face. It's tight. I can barely see out the holes. Mostly just straight out. I slowly turn toward the mirror. "This is going to be good," I thought. And it was. 

Fuck yes!  : )

I noticed some buckles hanging at the wrists and ankles. There are straps built-in around those places. Buckling the straps makes them into bindings or cuffs or something. They are wide straps with two buckles for each. They felt naughty wrapped tight around me. Like I'm some sort of captive or a kidnap victim. I liked it. Humm? I really liked it!

The bottom of the suit had a zipper. I could feel myself up, open my crotch area, and jerk off like crazy all I wanted. And I did. 

After a few naughty episodes in the bodysuit, I found its packing bag. It turns out this is some kind of fetish Halloween costume. Whatever that is. There is a picture of a girl wearing it. I think I looked just as good as she did. Haha! On the other side of the label were two more pictures. One, the girl's hands were cuffed behind her back and she was blindfolded. The other one was a close-up of her face with a red rubber ball strapped into her mouth. What the fuck was my sister into? And more importantly, where were the blindfold and the ball gag? 

Being in that tight rubbery catsuit with buckles securing bondage straps around my wrists and ankles got me harder than I've ever been. The hood covering my face and the thought of being blinded and gagged were even more than I thought I could ever handle. But I wanted to try! I dug through the bag. No blindfold. No gag. But then, in a pocket inside the garment bag, success!

A purse sort of thing was full of stuff. Two ball gags, (One red one and another with a bigger blue rubber ball), a pair of metal handcuffs, the blindfold, some clothespins, and a long, white plastic vibrator. I jumped and dropped the vibrator when I twisted the end to see if it was working. It was. Gees! Humming and bouncing away like crazy!

I took a load of pictures of me in the mirror. Then I was ready to have some fun. Did I want to go down to my room, or jerk off in here? I've used her bed many times, now that she is gone for months. But it feels more private in my room. Should I try walking through the whole house in this getup? What if someone comes home early? That would be bad. Today I decided to pop in one of the gags and finish right here, in her bed. I've never worn a ball gag before. They kind of suck. But nothing looks naughtier or nastier than a ball stuffed in and strapped deep inside your mouth. It's so worth it!

I was gasping for breath and gaging on the ball. It was very uncomfortable. But that added to the excitement that I was a victim of some hostile kidnapping and rape. 

Part 3. The violation

Humm? Rape? Was I being raped? Do want to be? Maybe that's what I can use that vibrator for? I've never had anything up my ass. Do I want something up my ass? The first time I tried it I couldn't believe I'd overlooked this all my life!

I used some belts to strap up my ankles and wrists. I was bound on the floor in one of her matching pink ruffled panties and a training bra. I was in pink tights. They were warm and silky. I used two of the clothespins pinching my nipples. I wanted to take them off right away, but I 'bit the bullet' and left them on under the bra. I pilled the belts tighter. Only leaving one hand halfway free. I struggled, wiggled, and reached around, shoving the vibrator in. "Oh Fuck!" I worked it in then managed to turn the vibration part on. That made it even crazier! I pointed it straight up and pushed it in as far as It would go, then sat down over it. "Oh, my fuck!"

The panties were pulling against the skin around my ass. The bra was tight, tugging at the clothespins, pulling and pinching my nipples every time I'd move. The vibrator wouldn't stop humming and touching me inside. I was feeling so many different things and in new places. I loved the feeling of being helpless. I liked all the soft, silky girly underclothes rubbing against my bare skin. I liked being strapped up and struggling against the bindings. I was so fucking hard!

I caught myself moaning and crying out like a little bitch. I couldn't reach the bag with the gags in it. I wasn't getting out of this position easily anyway. I used my free hand to grab three pairs of dirty panties, stuffing them in my mouth. I always have plenty of her old panties and bras lying about. I found this sort of gag felt much better than the hard rubber balls. But as soon as I leaned back on the vibrator, I let out a loud "Oh fuck me!" and my mouth spit them right out. "I'll work on that next time." I moved again, making the vibrator twist inside me. The bra pulled at the clothespins. "Ouch! Fuck!" This was nuts!

After a few minutes, with only being able to barely touch the tip of my dick, I shot the longest load I'd ever felt or seen all over the floor. I let out such a squeal I was afraid the neighbors may have heard me. Next time I'll use a gag for sure. I'm struggling to get the vibrator out of my ass. That's when I felt the 'violation factor', I call it. I was done. I wanted to relax and enjoy the thrill. But something wasn't letting me. I was still being violated. I wasn't in control anymore. I was still that captive. That victim. A rape victim? Or that rape slut. Slut? Am I a slut?

The feeling of not being in control was new to me. I liked it. I pretended I'd been forced to dress like an innocent little girl. Someone was pushing that vibrator inside me whether I wanted it there or not. What would that be like? I was getting the feeling of being a real captive. Dressed up girly and used for a sex slave. Humm? Would I like that? What would that look like? I looked at the pictures of the girl in the catsuit. Blindfolded and gagged. I wondered how that would be. Then I came again.

Part 4.  Am I gay? Coming soon.