scary trying to be yourself

Introduction.

Jerking off in her stuff was always the best. Just thinking about sneaking into her room, looking through her drawers for naughty little bras and panties, got me hard. As we both got older she would be buying more sexy stuff. No more training bras for me. She had a boyfriend and a Victoria's Secret credit card now!

I tried playing in panties and her bra with my first girlfriend. It didn't go well at all. A few girlfriends later I tried it again. More disappointment. I was afraid she might tell my friends I wanted to wear her stuff when we had sex. I didn't want any embarrassment or trouble, so I shelved the idea for a while. But I still enjoyed jerking off, wearing some of their stolen underwear, for years. I even began to steal other women's panties and bras whenever I had the opportunity. it's so much better wearing someone's actual stuff than just buying random things at the store. One of my neighbor's girlfriends would leave her sexy undies in their laundry basket in their bathroom. When I would visit I'd always find something sexy to take home. 

Sex was always a bit of a disappointment for me. I wasn't the passionate, aggressive guy the girls all seemed to want. And if I'd ever suggested trading underwear or anything like that, it would end poorly. I was drifting from girl to girl, unhappy and unsatisfied. Unless I was alone wearing some sexy lace and satin girly underwear. 

The internet sure changed a lot of things. I've been cruising the chat rooms for years. I do find myself searching for a lady or woman or anyone who might like a boy in a girl's underwear. Not too many hits. I thought I'd try some photos next time. The dating sites say it helps a lot to have photos. 

I posted a few pictures of me. I used a recent face picture one of my old girlfriends had taken of me. I looked cute and nice. I decided to go all out and show my little harmless fetish. I took several of me posing in a sexy black lace pushup bra and matching panties. I'd stolen them from my 50-year-old Aunt a few months ago. The main part of the bra around the body was extra wide. The style was with 6 clasps to hook the back together. A longline style. Very old-school looking. The shoulder straps were wide with little lacey frills along the sides. Vintage looking. Very sexy. It was a B cup with padding. It looked great on me, especially since it was a little tight. 

I deleted the first set of photos. My body hair looked horrible. So I shaved real close and tried it again. Much better. The panty was a full-coverage style, all lace except for a wide waistband. It was shiny satin and came almost all the way up to my naval. They felt, and looked great on me too. I had a pretty noticeable bulge in the front as I couldn't help but get hard, wearing her underwear. I did my best to hide it, but there it was. I also took several pictures of my ass, bent over, to include in my posting. 

Well, there weren't any ladies who replied to my post. I got pretty much nothing from the usual dating sites. I guess it was silly to expect to catch any normal woman's attention, or even most not-so-normal women, with pictures like that. But, I did get a few replies.

A few of the men surfing the profiles noticed me. I deleted their messages right away. A couple of them kept it up. They were begging for more pictures of me. One even offered to buy and send me some lingerie to wear in photos for him. He told me he would love to treat me like his girlfriend. If I wanted to act like his girlfriend for him. I figured that out pretty quickly. I don't want to be any man's girlfriend. 

Do I?

Chapter 1

Our first meeting.

Big Jim, he called himself, sent me a full set of maid's outfit and lingerie. Like a sexy girl would wear to a Halloween party. He included a short black wig and some red lipstick. Requesting I wear them all when I photograph myself. I took a few pictures and sent them. I didn't reveal I'd jerked off several times before, during, and after I dressed in the outfit. It was soooo fucking hot on me. 

He begged to meet me. I was really nervous. I'd only agree if we meet somewhere public where I felt safe. He didn't care where we met. He just wanted to 'get a friendship started', he told me. He sent me a waist-up photo of him. He was an OK-looking guy in his mid 40's or so. He had a nice smile. I felt better.

Outback Steak House was close to both of us. I found a long coat, like a cape, at a costume shop in town. It was dark gray and went almost all the way down to the floor. I put on the maids' outfit, wig and lipstick, just like I'd worn in the photos. The bar was dark enough to hide the fact I wasn't a girl. The restaurant was much too well lit. I waited at the end of the bar, in the darkest area, drinking wine. Big Jim sat right next to me. He took my hand and thanked me for 'coming out'. 

"I'm not really 'coming out," I said. "I'm not even really sure this meeting will last much longer." 

"I promise I'll be a total gentleman. I just wanted to meet you and see if we might hit it off."

I was getting warm with nerves. I could tell I was nervous and I wasn't sure I'd make any good decisions under the stress. "I'm going to use the restroom. And then I think I'll go home. You've been nice. Maybe we can try this again later."

I waited until the restroom was vacant. I slipped into the men's room. But realized I couldn't lock the door. Big Jim pushed walked in behind me. I moved back until I hit the wall. He slowly moved up in front of me. 

"I'm not really comfortable with this. Can you back off a little, please?"

Jim backed off. He just stood there looking me up and down. "You're in the maid's outfit, aren't you? At least you could let me see it before you leave."

I felt like he would be cool and let me leave once he got a look. I looked down, then carefully lifted my hands up to the large buttons holding the coat closed. Jim took out his phone and pointed it at me. I slowly unbuttoned each one, from the top down to the last one by my knees. I shyly opened the coat for him. 

"Oh fuck me!" He exclaimed. The flash of his camera went off several times.  "Are you sure we can't go somewhere else and talk about this?"

"I'm not sure I'm ready for anything, Jim. This was a big step for me, you know?" I closed the coat and buttoned up the first few buttons. "I'd appreciate you letting me get out of here, and going home."

I stood outside my car for a minute. He had been very polite. This went well, I suppose. I'd gone further and done more than I ever thought I would. I was sort of proud of myself. I was daydreaming, recounting what had just happened. How crazy it was I'd dressed up for a stranger and actually met him. I was in a bit of a daze. Then a big SUV pulled up right next to me. Jim rolled down his window. He just looked at me standing there. He didn't say anything. I heard the door locks of his SUV pop up. He glanced over to the passenger door, then back at me. "Come on. I think you want to get in. Don't you?"

The Escalade was really nice. Warm, soft leather. A Huge digital center screen with all sorts of fancy stuff going on. A big switch from my 10-year-old Honda. "Is it OK if we just go to my house for a drink? I'll bring you back to your car whenever you like."

I didn't answer. I just looked forward out the window. He dropped the gearshift into drive and off we went. My thoughts began to race and collide with each other in my head. What the fuck am I doing? 

His house was really nice. We drove into a huge 3 car garage. There was a Corvette or something really cool under a car cover in the other stall. He waited for me to get out, then took my hand and led me inside. 

"I'm so glad you decided to come along. I've been hoping we would have a chance to do this."

I thought to myself, "What exactly does he think we are going to do?"

He opened a bottle of red and poured us a glass. When he handed a glass to me, he took my arm and pulled me close. We were chest to chest. His face in mine. Before I knew it he was kissing me. I'd never kissed another man before. But the feeling of the tight lace undergarments and sexy skirt and blouse were doing a number on me. Did I feel ... feminine? Or submissive like a shy young girl? Or was I being seductive, like a slutty woman would be to get a man's attention? I was confused. But I knew I liked his lips on mine. And his warm wet tongue pushing deep into my mouth. I felt my closed eyes sort of roll back in my head. My knees got weak. His arm was around me, holding me close. I looked for a place to put the wine down. He took it for me, and off we went. 

I was sprawled out on the bed. He was shirtless, taking pictures of me posing for him. I did whatever he asked. I rolled over so he could get some nice ass shots of me. It started with the coat still on. Then it progressed to me with not much more on than the corset, garter and stockings, and panties. He took a lot of pictures. "These are what we might want to call, before pictures."

Once he was on me, there wasn't much I could do. He had me pinned on my back, kissing me passionately, hands all over me. Nowhere was off-limits. I've been groped a few times by drunk women. But this guy was really into me. The sexy underwear was a focal point as well. He pulled and pinched and fondled and kissed all the remaining lingerie I was wearing, and everything under and inside it. When I tried to move away from him grabbing my ass, He pushed my arms up,  back down on the bed, and continued. 

He had my dick in his hands and pushed my hands into his crotch to hold his. 

"Be a good girl and help me cum, please."

I liked that he called me a good girl. So the next thing I know I've got both my hands in his crotch with my fingers wrapped around his cock. I'm jerking him off while he is kissing me and fondling my panty-covered balls. 

"It might be better if you'd have it in your mouth. Will you do that for me, please?"

He is so polite. I'm up on my hands and knees, with him on his back. My head is bobbing up and down trying to get him to blow a nice load in my mouth. Every time I move, the tight sexy corset, garter, panties, and stockings are pulling, pinching and caressing my skin. They, and Jim calling me a good girl, remind me without question that I'm in the female role here tonight.

Just before he finally unloads in my mouth, I notice his phone clicking away, flashing in my face. I look up as a flash goes off. My eyes looking right at him, with my mouth full of his hard, fat cock. I decide I don't care. I put on the lady's slutty clothes. What was I expecting? I knew it could end up just like this. I knew it would end up like this. And I proceeded anyway. 

I choked and gagged and spit and drooled it everywhere. He took a big handful of it off my chin and slipped his dripping fingers into my mouth. "Get used to it, baby. There is a lot more of it coming before you get out of here tonight."

It was pretty disgusting. But I took his advice. I began to swallow what was left in my mouth. I licked some off my lips. I loosened the corset pulling it up to my face. I licked and sucked the dripping off of it.  He just watched, smiling, taking videos and pictures. 

Chapter 2, Our second meeting.

coming soon