Sissy-life

J, D, JQ, M, MM, A, and MS have witnessed some part of my proclivity for dressing up like a woman. The last one (MS) divorced me for it, the first one (J) got me into it. 

Well, not true, D, was really the first. I was renting a room from her and her husband. I used to go through her panty drawer and when the house was empty I'd try on her sexy teddies and chemises. She had this totally slutty teddy with garter straps that I loved to wear, she was a big woman so even her hose fit me nicely. 

I came home drunk one night and stumbled into the living room because the TV was still on. D and her husband B smoked weed so I was going to see if they wanted to smoke, but it was only D, and she was passed out on the couch wearing the slutty teddy outfit I was telling you about. 

I backed up out of view just in case she'd woken up, but after making sure she was asleep and that B wasn't home (he worked nights), I crouched down on all fours and knelt beside her. I stared at her every curve and line. Her thighs, her smooth calves and ankles drove me insane. It was like a dream come true. She was clearly drunk and was passed out.

I took off my clothes. I told myself this is what she intended. She knew B wouldn't be home until morning and that I would be the person who would find her like this watching TV late at night. I told myself that she wouldn't wake up, I was only looking, and if she did wake I'd scramble behind the couch and down the stairs before she could see me. 

I knelt on my knees and stared at her body. Her breasts had fallen out of the scooped V-line teddy and one of her legs had fallen off the seat cushion opening her legs. I could see through the gossamer material that she was shaved smooth.

I knelt before her and masturbated until I came. I secretly wished she'd wake up. I wanted her to wake up right at the point where it would be too late to stop. I wanted her to see me naked and jacking off my hard shaved cock for her, to her. 

She didn't. But after that night, she would leave her lingerie out on top of the clothes baskets in the laundry room. Every time I did my laundry I had a nice surprise waiting for me. I am certain she wasn't asleep that night.

Anyway D was technically the first. I was really young, hadn't even had proper sex. I'd never even had a real girlfriend before. I don't think D knew I liked wearing women's panties, I think she just thought I liked smelling them and playing with them while i masturbated. But it's possible that she knew, so that's why I include her on the list of people who know I enjoy cross-dressing. 

The first person was J. She got me started. Up until I met J, I'd play with panties. I had a few pairs from stealing them from my sister and mom or stealing a pair or two from JC Penny's. I liked Vanity Fair because that's what my mom wore. White, silky, gossamer-smooth full-cut Vanity Fair panties. 

When I started dating J I hid them away as if I was hiding Aladdin's Lamp, buried deep in the confines of the air conditioning ducts. It was my horror that she would find out. 

It was an amazing stroke of luck then, one night during our sex games, she asked me to put on her panties. I tried to appear shocked. She must have seen right through it because before the night was over we were both in a pair of sheer-to-waist nude pantyhose, we'd painted each other's toes and nails, and she even painted my mouth with red lipstick. We scissored like a couple of drunken lesbians that night.

Over the years J and I have kept in contact. She knows just about all of my story. She's seen almost every pic and vid I've ever made. She's married and still looks spectacular. She sent me a couple samples from a professional shoot she did for her husband. She is still a goddess.

When J left me, I was distraught, certain I'd never find anyone like her. I started buying panties and lingerie online. I gave up hope of finding a woman and bought a couple vibrators. I think I decided that my imagination was better than going through the pain and suffering of finding a mate.

So when I met MM I wasn't even trying to engage her or go after her. We were just friends. I was good with that. And we stayed friends until today. We catch up on SM or email and that's it. She knew about me because she found my stash one day. I didn't hide it, just kept them in the top drawer of my dresser, but I never imagined a friend, woman or otherwise ,would go rifling through my clothes closet. 

I came out of the kitchen one day and she's holding a handful of panties and a vibrator. She wanted me to model them for her. I did. I tried on every pair and showed her my bottomless panty-girdle with Wolford thigh-highs. That was a one-time event. But over the years, I'd send her photos of me whenever I got the itch to share. She's never given me any indication that she likes it, I think she tolerates it because we are friends.

MM and I were only ever friends. It was strange modeling the outfits for her. I never got hard. It wasn't a sexual thing, it was a mental thing. That day still ranks in my top-10 moments though.

I was getting braver and going to high-end department stores now to buy lingerie. I was shaving my crotch and ass. I was taking long baths by candlelight. I was using a vibrator nightly, and on weekends I would penetrate myself. I was dating myself.

That's when I met M. 

M looked like a teenage boy. But she was a woman. A pan-sexual woman. I fell in love with her right away. She found my stash. I tried to hide it from her, but it had become a pretty big collection so I didn't try to hide it so deeply. 

I came home from work and she was lying on a pile of my panties, hosiery, and chemises. We fucked and dressed up all night. 

M used a strap-on on me. M wrote me stories. M loved hotel rooms. M gave my best friend a blow job while I watched. M did a porno. Then M broke my heart and left me.

We've kept in touch over the years, even had a couple affairs, and I've also shared some of my photos with her, but not a lot. She wasn't really into the CD thing.

After M, I gave up on women. I moved to Florida and started a panty buying frenzy. I started going online and camming. I'd go online and show anyone who wanted to see. 

I was dating around but nothing serious. I was going on craigslist a lot. I'd chat with some guy, send him pics, he'd send me pics, we'd set up a time and place and I'd never show. 

Until one day, I was high on vicodin, weed, and bourbon, I invited the first guy who replied to my CL post over to my condo. I told him to meet me at the pool. I lived in a snowbird condo complex, so during the summer the place is empty and I felt confident I'd be the only one at the pool. 

I draped a beach towel around my waist to cover my pale blue VF panties, and walked over to the pool with a drink in hand. I was terrified. I threw my towel on a deck chair and slid into the pool. 

I waited. I thought of running, but forced myself to wait.

Then a man came into the pool and smiled. I walked him silently back to my condo and as soon as I closed the door, got on my knees and opened his jeans. I knelt before him in my wet panties and took my first cock into my mouth.

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