crossdressing was a hobby

Part 1

I played for a long time in her clothes. I even took some pictures of me dressed up pretty. Now I have men calling me all the time. What should I do? Does dressing make me gay? I do dream of sucking a big fat cock a lot. Maybe I'll answer one of the guys.

She is long gone. She has been for years. But I kept a lot of her underclothes and a few dresses hidden before she moved out. She even asked for some of them as she was packing. "Have you seen my red party dress? And I seem to be missing a lot of my Victoria's Secret bras and panties."

Dressing in her underwear and trying on her dresses and shoes has been a hobby of mine for years. But I never really liked the way I looked fully dressed. Something always seemed to be missing. So, I secretly bought a long blonde wig in a costume store. Holy shit! The wig changes everything! I had it tucked away out of sight until she was gone. Now I wear it, and all sorts of pretty underwear and clothes almost all the time when I'm home alone.

After looking at myself in the mirrors all over the house I couldn't help but pose and take some selfies. I got a little carried away one afternoon shoving a big pink dildo into my mouth for some of the pictures. I opened my eyes wide like I was surprised and barely able to take it. The pictures turned out pretty good. I looked like an innocent girl getting a cock shoved down her throat for the first time. It was fun!

I took some extra time and posed in different stages of dressed and undressed. Wearing the sexy clothes and stripping them off in front of the camera got me pretty horny. Which of course was the whole point. But I was getting bored posing and taking photos for just myself. I started joining some crossdressing and sissy websites. I posted some pictures and chatted with like minder people. It was reassuring and fun.

The men who hang in the chatroom are kind of creepy. They say rude and disgusting things to me and the other crossdressers. Some of them try to be polite hoping you'll show them more pictures of you, or even skype live with you. They want you to take off your girly clothes for them and show off your butt. Sometimes they get pretty rude and I turn off skype. But I always seem to come back for more. One afternoon a guy had me sticking a vibrator up my ass while I sucked on my pink dildo. He was on the video call jerking off until he came all over himself. Those sorts of video calls became more and more frequent. What was happening to me? This is pretty weird. But I love it!

Local guys are rare. But all of a sudden I have 3 different fellows who live close by calling me all the time. I can't turn on skype without at least one of them calling in on me. I've seen all of them undressed and hard. Jerking off while they chat and tell me about the different ways they want to molest, manhandle and rape me. 

The other night I had a dream with one of them being my groom and I was his bride. I'd been crying because I didn't want to marry him, but he was forcing me to go through with it. I didn't remember the ceremony but I vividly remember it right after. He had me pinned face down on a big round honeymoon bed, me still in all my wedding clothes. I could see myself in my white wedding dress and sexy white bride's lingerie. My ass was propped up with pillows, as he was pounding me. I'd never dreamed of being fucked before. The dream made me really nervous. It was so real!

The man in the dream was George. He lives just a couple of miles away. He has been the most verbal and rudest of all the men I've chatted with. I often shut his skype chats off. Especially when he starts warning me he will break into my house and kidnap me. He knows what part of town I live in. But I don't think he knows exactly where. I hope not, anyway. He showed me some bondage gear he recently bought with me in mind. Some kinky leather cuffs and a dog collar with the words 'Cock slut' printed on it. He has a nasty vinyl discipline hood with no openings except a tiny nose vent and a mouth hole in it.  It has a wide strap going around the neck. And another one hanging under the chin with a red rubber ball on it. A naughty, mouth-filling, speech-stopping, begging for mercy muffling ball gag. When he starts showing me how they all fit on a mannequin's head he has, I tell him to 'fuck off' and I disconnect. 

But sometimes I sit there and take it. He tells me how hard he is going to ram his huge cock up my tight little virgin ass. How he is going to grab me and fondle my sweet, pretty body for hours. He tells me how long he will kiss me, and then how deep he will slide his cock down my throat. He tells me he will turn me into a real sissy cock craving whore. He says he can do it. He says I'll never be able to go back to being an innocent closet sissy. He says he will own me forever.

Then I shut down my laptop. But I dream about him grabbing and fucking me, night after night. I can't get him out of my head. Now when I dress up, I feel like I'm doing it just for him. I remember what he told me he prefers. His favorite underwear is the white lace bride's outfit. His favorite dress is the purple prom dress I borrowed from my sister when she wasn't looking. He said he likes an open bottom girdle with lots of garters hanging from it and lace top nylon thigh-high stockings. And I dressed just like that. Then I pray he is online when I log in. But I tell him I'm not interested. He tells me that he knows different. He is changing me. 

One day while I was completely dressed for him with my wig and make-up and everything, I gave in. I told him I'd have a coffee with him. I told him I'd show up in drag and he could check me out first hand. The Starbucks down the street would be perfect. He told me to be there in 10 minutes. 

I was really embarrassed when I walked into the place. I hoped no one would notice me. The teen at the counter didn't even give me a second look. I took a seat in the back and waited. And waited. The fucker. A half-hour later I walked back out to my car. Embarrassed and humiliated. I felt like such an idiot. I unlocked the door. But he was there parked next to me. I glanced at him and gave him a look like 'I didn't care anymore.' 

"I'm sorry I'm late. Do you want to get in my truck?"

The door lock popped up. I was in a strange, do-or-die predicament. Do I get in? Or do I go home? It was my choice. I drove here on my own. No one put a gun to my head. I suppose this is something I want? He looked the same as in the skype chats. He is tall and looks like he works construction or something. He is wearing a flannel shirt and jeans. His hair could use s trim and his beard could use a little attention as well. But he is a handsome guy. Everything seems ok so far.

I closed my car door and locked it. The door handle on his truck was big and heavy. I had to pull it twice to get it to open. I slowly slid in. He was watching my every move. I pulled the door closed. I didn't know what to say. So he spoke first.

"You look pretty good in person. Better than on that stupid skype shit. If I take you back to my place, we can have a coffee there. Are you good with that?"

Gee. He was being so polite. Maybe the rough tough-guy image was all bullshit? I reached over and put my hand on his arm. He gently took my hand in his. He looked e in the eyes. I was staring back.

"Sure. Having coffee at your place would be great."

And off we drove. He lived just a few blocks away. He showed me the way through the garage and into the kitchen.

The coffee was a day old. But it wasn't really about the coffee, was it? He was looking me over and smiling like the cat that ate the canary. I was feeling very vulnerable and fragile. 

"I'd like to photograph you. You look so great! I do some professional photography sometimes. I've got a little studio in the back. I can't believe you are here. I'm really happy you agreed to meet me."

I didn't say yes. And I didn't say no. Not yet anyway. 

"I'd also like to put you in the leather stuff I bought. I showed you some of it this week. Would you be Ok letting me do that, and posing for some pictures in that stuff too?"

I liked the idea of him photographing me. I take a lot of time getting dressed up properly and looking as feminine and sexy as possible. And that is not so easy. So I take his offer as a compliment. 

But, I figured once I let him get me back to the studio, and certainly, once I let him handcuff me, all bets are off. I'd be at his mercy and wouldn't be able to stop him from doing whatever he has in mind. I noticed my clothes were a little ruffled from getting in and out of his big truck. I was stalling. I pressed my hands over the front of my dress, pulling it down into its proper place. I was smoothing the wrinkles away, and adjusting the top over the perky silicone-filled bra cups underneath. I pulled and twisted the tight dress into place the best I could. He liked the way the dress fit me. I was trying to distract him. I wasn't ready to answer.

He put down his coffee and moved next to me. He took my arm and pulled me close. His lips kissed my smooth, warm cheek. 

"I'll be a gentleman, I promise."

I turned toward him. He kissed my lips. We both leaned back, gazing into each other's eyes. Another kiss. This time he slipped his wet tongue into my mouth. He pulled me closer. His arm slipped around my back, hugging me gently. My hands moved up to him. My arms resting on his shoulders. Then for some unknown reason, I wrapped them around his neck. I heard myself let out a nearly silent sigh. How were we suddenly here together, in this romantic moment? He didn't stop kissing me. His warm wet tongue rolled around in my sweet, cherry flavored lipstick-lined mouth. It was a magical moment. I stopped him for a moment. 

"I'd love you to photograph me. You can pose me any way you like."

He smiled and gave me a little peck on the lips. 

"This is going to be really fun! I'm so excited this worked out! Thank you so much for being here!"

He took my hand and led me through the kitchen, back down the hall, into a rear wing of the house. 

Part 2

I walked into the studio and immediately tried to turn around and get out. But he was right behind me with a pair of police handcuffs. 

"Oh fuck! I didn't sign up for this!"

In front of the large greenscreen backdrop was a large, rough wooden framework going up to the ceiling with lots of chains hanging from it. There was a post in the middle with chains and handcuffs attached all over it. Around the center 'stage' were several workboxes with drawers. On them were an assortment of leather gear, ball gags, face masks, dildos, and bottles of lotions and lubes. Leather straps and spanking paddles were hanging on every wall. After he cuffed me he forced my mouth open filling it with a big fat leather ball, mouth gag covered with a wide leather panel and straps to hold it in. He held a small towel under my nose. It smelled of alcohol. 

"It's OK, baby. I'm going to make you famous. You're going to be on every pervert's 'favorites list'."

I woke up kneeling on the floor, back against the post in the middle of the studio. My arms and hands were wrapped in leather, tied tightly around the post behind me. A wide leather strap, or collar, was around my neck holding my head up and back to the post. My ankles were cuffed back to the post too. I was still in my girly clothes. I was fucked.