Becoming a sissy crossdresser for him

The set up.

Mom had big tits. So she attracted lots of new boyfriends. Jay was around the most. But none of them ever moved in. 

All her bras were DD cups with very wide straps. The backs had 4 and sometimes 6 clasps. Longline bras they call them. Most were those old-style things. Those are the ones I fell in love with. Going through puberty and being hard all time was very confusing. Anything girly. Those secret hidden garments like bras and panties, girdles, and stockings made me feel like I was closer to a girl. I wanted to be close. Why do girls wear those sexy underclothes but hide them? Just giving us a glimpse of when a bra strap would slip out over her shoulder. Or maybe you might get a peek up under a girl's skirt and see a flash of what color panties she was wearing. I couldn't get those naughty undies out of my head. I just wanted to roll in them, rub them in my face, wrap them around my cock, and cum all over the place. And I did. 

Wearing the clothes made me feel even closer to the girls. I didn't have a girlfriend, so this was the best I could do. I wouldn't know what to do with a girl anyway. Even if I did find one who liked me. I felt myself up and jerked off. She had some girdles with garter straps hanging from the leg openings. There were lots of tan-colored stockings too. The girdles and stockings felt so nice against my smooth, young skin. Tight and stretchy. I came all over them too. 

All the foundations smelled really nice. Maybe it was the Playtex rubbery fabrics, or her perfume lingering on them. But I liked them. I smelled them close. I rubbed them in my face. I put them in my mouth and sucked them. I'd rub and suck on anything she wore under her clothes. I started rubbing her worn panties on my face. The laundry room was my new favorite place to search for fun items. I stuffed a few pairs in my mouth. I felt like I was being gagged by some mysterious dominant person. I can't cry out! I can't scream! Maybe they were violating me. Why did I want something up my ass? I remember the first time I gagged myself with her panties and touched my butt hole. I came like crazy. 

By now I'm out of school. I've got a large assortment of her old undies in a box hidden deep in my closet. But now my younger sister is finally wearing training bras and cute little panties. Out of the silly cotton ones she wore her whole life. Her stuff is even more erotic for me. Not that I ever think of her as a sexy girl, she is my stupid sister, but her underwear sure trips my trigger. Every time I'm alone in the house, on weekends usually, she has carelessly left some of her cute underwear out on her bed or hanging in the laundry room for me to discover and try on. I fit in her stuff much better than Mom's. And there is plenty of it! She must buy new stuff all the time. I was in heaven!

When I was 19 I was thinking about moving out. One of my buddies had a place I could move into. I got a call from Jay, my mom's sometime boyfriend. He said he needed to talk to me. Something important. We met at my new place. He said he wanted to see it. I thought her was pretty creepy, actually. One of those manly men with a beard and hairy arms. He had a tablet with him when he stopped by. 

There were hundreds of videos of me in mom's and my sister's underwear. I only watched a moment of the first one. He put his hand on my knee and told me he had been watching me for years. He said he had purchased most of the underwear, leaving it out for me when he knew only I could find it. He looked me in the eyes and told me he wanted me to dress for him for real. He said he wants us to hang out all day. He said he wants me to be his girl. He squeezed my knee and moved his hand up my leg.  I was so fucking nervous. Confused and ... well, I was grateful. Was he the first person to understand me? Or is he a dangerous pervert I should avoid?

My mind spun around and ended up here. What a sweet man he was. Buying me cute underwear. Watching me, saving those personal videos for me, and telling me he likes me. I was all warm and shaking. His hand felt nice on my bare skin. He kissed my cheek. I looked at him. He kissed my lips. I kissed him back. What the fuck? Is this where I am? Is this who I am?

I took a few extra minutes getting dressed. He had brought a new bra and panties set. He said he liked the longline stuff a lot. The bra was stiff and wide. It had 4 clasps in the back. Even though it was a heavy longline Victoria's Secret bra, the bra cups were AA. Barely there at all. It looked so cute on me! The panties were full coverage and fit me just right. There was a pair of knee-high socks like a cheerleader would wear. He had brought a sexy little pink leather choker too. I've never seen one of those before. But it looked so cute on me! He said he wanted to take some photos of me posing in the cute pink and white panties and bra. When I came out of the bathroom he was on the bed, naked. He was holding his phone in one hand, pointing it at me talking a video. His cock was in his other hand. It was hard, poking straight up like a flagpole. He said it was for me. He had brought me a gift, and this was it.

I posed for a moment, trying to look sexy. Then I walked up to the bed and climbed on. I looked up into the camera and asked what I was supposed to do. He asked me if I loved him. I told him I did. With that, he took my head and pulled me down into his lap. His cock tasted like sweat. Salty and sweet at the same time. I loved it. The light from his phone was in my face. He was recording it all. He was hairy. I did my best to love his cock. I licked and sucked his big manly shaft. I rubbed his balls as I'd seen in porn videos. He loved it too. His hands were all over me. Rubbing and pulling at the sexy bra and panties. He told me if I can make him cum, he has another gift for me. 

I know I was supposed to swallow. But this was my first time. And I did a very bad job. He said it was ok. After I cleaned up, using a towel on myself, he showed me the gift I had earned. 

He produced a ball gag. It's a bondage and discipline item. Used to keep a victim quiet and submissive. It works. Once you've got that thing strapped in your mouth, you realize quickly how vulnerable you are. This one had a very soft rubber ball. But it was extra big. It felt like a huge marshmallow in my mouth. Filling it completely. Strapped in deep and tight. He took a lot of pictures of me gagged with it. He was hard again almost immediately after buckling it. 

He was on me for hours. Grabbing me and kissing me everywhere. Lot's of places he shouldn't have. He worked my butt hole with a finger. Then 2. He licked my ass for a while too. Then more fingers. Lube and spit made me slippery and able to take 3 fingers all the way in. He took a detour around noon. He tit fucked me, coming all over the pretty bra and in my surprised, gagged face. He said he has always wanted to do that to me. He said he wanted to do that before he poked his cock up my ass. 

I tried to remove the gag several times but he liked it in my mouth. Until he wanted me to suck him off, of course. But after I blew him he put it back. I was grunting and trying to scream when he was fucking me. Some of it because it did hurt, but mostly because I knew he wanted me to. The more I squirmed and tried to cry out, the harder he squeezed me and the deeper he tied pushing his cock in my ass. It was magical!

Moving in with the pervy man. 

Jay had a big house. He was a contractor who built commercial buildings. There were building plans all around the house. In the basement was my room. A simple queen size bed and a white dresser. There were some girly clothes there. He had purchased some but told me we would be shopping for more now that I was there. When the day came to go out shopping, I expected to go to a lingerie store for some pretty things, but we stopped somewhere else. Have you ever been in a Castle store?

Out front there are plastic lingerie models in skimpy outfits. Inside there are more all around. The models are in the middle of each different section so you know how to find what you are looking for. The store is HUGE! We ended up in the back part of the store. There was a model in white and red lingerie also wearing a full body leather harness and leather face mask. he was looking it over when a pretty girl asked if we needed any help. She was tall and dressed like a Victoria's Secret model. She was wearing traditional lingerie. Black and lace. She was very nice it seemed. I liked her. But Jay looked at her and simply said: "Do you have this exact outfit in this little cunt's size?"

The clerk immediately blushed and laughed. Jay didn't laugh at all. I was so fucking embarrassed. I just wanted to leave. Why would he do this to me in front of this nice girl. The clerk pointed to a wall of hanging outfits and leather goods. I was leaning back toward the front door. Jay took my arm and held me close. He was looking at me sternly. "Stay here, bitch!"

I was frozen in place. I watched the clerk hold up outfits and look at me to decide if they were my size. After a long tome I was summoned back to the dressing room area. While we walked back, he was talking to the sweet clerk. "He has a fetish and I'm going to help him with it. he is kind of a pussy, isn't he?"

She just smiled, nodding as she covered her face, laughing at me. She waited outside as she requested, holding more stuff for me to try on. In the closed dressing room, Jay ordered me to strip and get on it. I quickly obeyed even though I was flushed and just about ready to cry. I was SOOOO embarrassed. 

He put me in the same red and white lingerie the model was wearing. it was tight, just the way he likes it , he said. After we were decided on the out, Jay invited the girl into the room, leaving the door open. She was surprised when she saw me, again covering her face as she laughed at me. Jay asked her opinion. "What do you think? A little bitch, right?"

She could barely speak she was laughing so much. "Yes! Oh my God! He is a little bitch, isn't he?"

She was holding the leather gear out for Jay to put on me. "No, you should strap that stuff on him. You are the professional. Is that ok?"

"Ha! Yes, of course. I help dress little sissy guys like him all the time."

Jay sat back and took pictures of her leathering and chaining me up. Most of the gear was pretty standard. Black leather wrist and ankle cuffs, a black leather collar and silver chain leash. The harness was a little trickier. It took a couple of tries to get it around my chest and waist just right. The chest straps went around around my chest with two straps, one just above and one just below my 'tits' in the lace bra. A little ring pulled them together between my 'tits'.  On the front, back and sides of the waist strap were rings to attach the wrist cuffs to. A crotch strap dropped down in front of me with a small slit for my little package to fit into. Then there was a then a long strap to be pulled up under me, and attached to a buckle in the back of the waist strap. She looked at Jay as if to say she wasn't quite comfortable being that close to my genitals. Even though they were completely wrapped up and docile in the pretty silk panties. I was so fucking nervous and embarrassed It felt like my dick and balls were nearly sucked all the way up inside me.

"Go ahead, if you want to. But pull it tight for him. Real tight."

"Oh fuck!" I whispered to her. The cock strap tightened around my little package of dick and balls and the under strap spread my cheeks and pressed firmly against my little butt hole. It was plenty tight already, I thought to myself. 

"Give it one more pull."

The clerk laughed and pulled the strap up one more hole and finished buckling it. And then she said: "Yep, that's just the way it should fit him. I like it!"

I winced and let out a gasp. I could tell my face was beat red in the changing room mirror. I looked so stupid! How humiliating! My eyes were watering, dripping tears down my cheeks. The strap was to tight around my dick and balls. The rest of it was pulling my ass cheeks apart so roughly, I knew I'd have a rash or leather marks back there for a long time. They both laughed. "I'll bet that hurts", she said. 

All that was left now was the leather hood. It was a thin, stretchy leather hood with a long collar that almost covered the dog collar I already had on.  When the zipper on the back of it was pulled down, I could feel the leather pressing against every part of my face, head and around my neck. I had eye and mouth holes, and there were two little holes so I could breath out my nose. I asked if it was a bit tight, because it felt that way. 

"Hmmm... No, I think it fits just the way it should." The clerk answered. Jay laughed. 

Jay thanked the clerk for her assistance and asked for the fetish kit he had picked out earlier. I didn't know what that was. I was even more nervous and embarrassed. She left to retrieve it. Jay used some little paddle locks to attach my wrists to the back of the waist strap. He locked a short silver chain to my ankle cuffs, leaving it hanging between them. It was maybe 6 or 8 inches long. I'd never be able to walk with that being so short, I thought. Standing up besides me, Jay leaned in close, took one of my perky 'tits' in his hand, and squeezed it. He kissed me on my leather clad cheek. With the hood over my head, I was having a little trouble hearing everything that was being said. but I heard this.

"When I get you home, I'm going to fuck the shit out of you so hard you'll never make it back."

I wasn't sure what that meant exactly. But it sounded bad to me. I struggle a little bit against the cuffs. "Keep struggling, bitch. I like it when I make you nervous. And today, in this outfit, you should be very nervous."

The clerk returned with more kinky stuff in her hands. I've never seen an inflatable cock gag before. This one had a big black rubber dildo about 5 inches long and was very, very big around. Bigger than any dildo or cock I'd ever seen. And that was before it was pumped up! Once the straps were carefully positioned and tightened around the back of my head, Jay gave it a little squeeze. My mouth puffed opened wide and I couldn't relax it again. The cock spread my cheeks like blowing up a balloon, stuffing my mouth completely full. My eyes popped wide open. It was a really big 'What the fuck? moment. I barely could hear my little squeal and cry for it to stop. "Mummph!"

"Oh, that looks great!" The clerk exclaimed. "That will keep the little bitch quiet!"

They both laughed.

The last item I would wear was a horse bridle. You know the kind that has blinders in the sides by your eyes? They worked together to buckle it in place. Suddenly, all I could see was straight ahead. There were tight straps up under my chin with a rein that linked to the silver leash hanging from my dog collar.  The straps were tight around my head too. More shit to fuck with me? I assumed.

"I think you did a good job, Melanie."  The clerk nodded and smiled, trying to hold back a loud laugh. "Let's settle up and we'll be on our way. Oh, by the way, I can have him wear this out, can't I?"  

I almost fainted. I could feel myself sweating in the silky underwear even though it was chilly in the dressing room. 

"Oh my God! YES!" The clerk answered with enthusiasm. "Will you let me video you leading him out?"

Jay smiled and nodded. 

I was drooling, shaking and crying.

Sure as shit, she and a collection of pervy customers all had their phones going, pointed at me as we walked out. Jay had a bag of some of his other favorite items under his arm, and the lead coming from my bridle and collar in the other. I stumbled like a retard trying to keep up with the short chain between my ankles. I almost fell a couple of times. It was so fucking rude. Someone I couldn't see pinched me on my ass and another on slapped it. Jay didn't seem to care. He just pulled me along until we were out in the open parking lot. He took plenty of time getting us back to his car, making sure lots of people got a good look at me. Some people stopped, stared, and took pictures of their own. I was happy no one could see my face, covered with the hood. But that was all I was happy about.

Back at the ranch

coming soon.

Bill