It All Started... Ch. 01
Keywords: 01, All, It, Ch., Started...,
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It all started when my sister in-law, Kim, came over after work one day to tell me my wife was just called out of town for her job. I had planned on her being gone, anyway, and so I'd left work early to get my other wardrobe out of the attic, thinking I'd have the place to myself for a few days.
I just happened to be wearing a pointy cup black 36D bra, black garter, corset, stockings, heels, jewelry, makeup, and a wig, as she walked through the house. I was also sitting on a big dildo, and it was buried in my ass as I jerked my cock furiously, as she edged toward the bedroom door with the strange grunting noises.
I didn't know she was watching me, wide eyed and speechless, until I'd come all over my lace and hand. I groaned, lay back on the bed, and began licking the sticky goo from my fingers as I slowly worked the big vibrating dildo in and out of my butt. She knocked on the door she was peeking through, and quickly walked fully into the room, with a big grin on her face.
She asked me if I was having fun, and if I really liked having things up my ass. Having just cum a geyser of jizz all over myself, it was hard to deny.
So I just breathlessly and resignedly said "yes", and by the evil looking grin on her face, I began to wonder what she was thinking, besides that that I was a pervert. "What else have you got for clothes? Show me," she said.
So I got off the bed, pulled my panty girdle up to hold my still-bulging cock, and led her to the attic, where she was a bit amazed at my feminine wardrobe. She selected a red, knee length jersey dress, saw my big shoulder bag full of toys, makeup, jewelry, etc., and told me to meet her in the bathroom.
I could hear her on the phone with someone as I went in the bathroom, stripped off my undies, and got a quick shower. She came in to watch as I dried off, and selected my new outfit. She said, "I'll do your makeup and hair, we can't have you going out looking like you were."
Stunned, scared, and excited, I asked, I'm going out dressed as a woman?"
"No, you're going out with me, dressed like a whore", she said with a grin. "I always thought of you as a sort of manly guy, but tonight, we're going to find out how much woman you can be. I called Gina and Mitch, they're going to meet us later. We've got about an hour to get you all dressed up for a slut night on the town."
I groaned, but began to get hard again, and she went right to work on my face, heavy beige base makeup, lip liner, eyeliner, heavy shadow, blush, and my darkest wine lipstick. Then came my other wig, long wavy auburn, and my underwear again, with tight gaff-panty, open bottom girdle with garter straps, opaque black hose, 3 inch heels, and the tight fitting dress, that showed off my big 36D water balloon 'tits'.
"You're ready, let's go. I have to admit, you make a pretty hot slut," she said, gathering up some stuff she thought I'd need. She drove, and I felt very self-conscious riding around in public. At least it was dark outside.
I asked where we were going, and she said, with a sideways grin, "to meet a couple of friends of mine from work. You'll love them, trust me." She drove us downtown, to the more gay strip of bars, and parked the car in front of a joint called 'The Queen of Clubs'. It was early, about 8:00, and the place was nearly empty. We sat at the bar, ordered drinks, and waited for her friends. She wouldn't stop grinning, staring at me, running her eyes up and down my body. "You know, I always kind of thought you were kind of studly," she said, sipping her drink. "does Dina know you like to crossdress and have anal sex?"
God, I hope not, I thought. I said, "no, and I'd really rather she didn't find out. I've been dressing for years, and I think I'm pretty good looking, too, when I have time to do it right." Kim really had me by the balls, and we both knew it. I couldn't believe I was sitting in a gay bar, leaving lipstick on my glass and cigarette, with big jutting tits, tight dress, lacy underwear like a Frederick's model, with my sister in law. I was nervous, excited, scared, and having a blast waiting to see what would happen next. I knew she was not a mean person, but I had no idea what her plan was. She watched me closely, and I finally asked, "What?"
She thought a minute, and said, "You're so....feminine. the way you sit, smoke, drink, and look. You must really be into this. I had no idea, like I said, but I want to find out how feminine you can be. That's my price for not telling Dina. You do everything I ask until midnight, Sunday. Everything. I won't try to get you hurt, but I want to push your limits. It'll be fun to watch. I'll pay for cabs, because I want to drink while I watch, you just be the girl that I'll bet you've always wanted to be. Agreed?"
I nodded, and thought, this is what I've always wanted, but was too afraid to go out and find it on my own. I'm screwed anyway, if she tells my wife, friends, or anyone in the family. Give it a try. I said, "Agreed. But can we keep as low a profile as possible? I don't want everyone to know."
She knew she had me, and ordered another round, then turned to me and said. "I wouldn't say 'low profile' is what I have in mind, but I'll try to keep you away from anyplace you usually go. It'll just stay our little secret, as long as you keep up your end of the bargain. You look pretty good, your posture and movements are great, and your voice is passable, if you speak softly. Relax, you'll be fine, let's have some fun. You are enjoying this, so far, aren't you"
"Yes, I am," I agreed, "I have to admit, I'm scared, thrilled, edgy, and excited, all at the same time. I've only been out in public once before, a few years ago, and had a long coat and boots on for a walk in the dark. I guess I have to trust you, just please don't let this turn into a disaster? I'd really like to know what you have planned, or part of it, I think that would allow me to relax some."
Kim said, "ok, I called my friends, told them I had a hot crossdresser that wanted some fun and games, if they felt like partying. So I think we'll end up with 5 or maybe as many as 8 people going to a house for a little party later on. You'd better feel up to it, because I just know you want to play with a real cock instead of being frustrated with your dildoes. I know exactly how THAT feels...artificial. I want to watch you become a woman, instead of just dressing up like one and pretending"
Before I could reply to that, a guy and two gorgeous women walked in, and seeing Kim, walked over, said hi, suggested a table away from the bar, ordered, and we moved to a corner of the dim place. I was dressed like a whore, and felt a bit self-conscious around the other three more conservatively dressed women. I was thinking feverishly about what Kim had just said. She wanted just about the same thing I'd fantasized about for years. Was this the night? I felt a little lucky that someone I knew was going to be with me. Not the way I'd always planned it, but probably safer, if I could trust her. I was getting pushed into something I'd always wanted anyway.
We all sat, and Kim introduced Gina, a curvy, long black haired beauty with huge breasts, her husband Mitch, and Cheri, a tall redhead with a trim figure, nice jutting boobs, and long fishnet legs. Kim and I hadn't given me a female name, and since I didn't look much like a Tony, I said my name was Trixie.
They were all very good looking people, and I began to relax, as Kim was doing most of the talking. I just mellowed out, and thought about having sex with any of them, let alone all of them. The only thing taking my eyes off Gina's endless cleavage was the pointy, jutting cones of Cheri. Mitch was whispering something to Kim, and Gina, who could hear, giggled, and passed whatever it was on to Cheri. Her eyes widened, and they both broke out laughing, suddenly giving me a knowing look. I guess I looked more passable than even I had thought, because Cheri told me I made into a very pretty guy. Then she asked if I'd guessed she was a man, too. I was just floored, trying to believe this hottie had a cock in her panties, too.
Kim explained that Mitch and Gina were both very bisexual and sometimes got together with Cheri and some of her friends. They'd been planning to get together tonight, anyway, so when she called to tell them about me, they were ready to include us. Or me. It turned out Cheri broke up with her 'other' a few months before, and was getting very horny. Kim insisted she just wanted to watch my feminine initiation. Gina said she wanted some pussy tonight. Mitch gave me a wink, and I began to get hard again. (not NOW...I'm a woman, I should be getting wet.)
So, they decided to walk down the block to another bar, to see if we could find someone named Jennifer. Feeling a buzz from the drinks, I tagged along, getting a little more comfortable in the role of a party girl. At least these strangers had accepted me, as a woman, crossdresser, TV, it didn't seem to matter. We found Jennifer, a big boned transvestite with a very muscular black guy named Chas. After more introductions, Cheri, who seemed to have taken me under her wing, said, "Jennifer has been living as a woman for three years now. She lives with Chas, a football player at the U. He's a lot more gay than he likes to admit, but at least he's open minded enough to know he likes Jennifer's cock better than his high school sweetie's pussy.
Chas was looking me up and down, and although I'd been thinking that I'd be getting Mitch's cock, (from his bulging jeans, and I was already excited), but Chas had a huge bulge going in his tight jeans, too. Right then I knew I wanted one in my mouth while the other fucked my 'virgin ass'. I was glad I had a very tight panty girdle on to keep my boner down. The conversation was getting a lot more racy, and Gina seemed to be moving closer to Kim, yes, she was deliberately rubbing her huge breast against Kim's as they chatted and traded hand touches.
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Keywords: 01, All, It, Ch., Started...,