It All Started... Ch. 01

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. I could definitely feel Cheri's firm tit digging into my arm as she went on about Chas and Jennifer's history. I wasn't really paying much attention, I had wild thoughts of my own.... Mitch, maybe feeling a bit left out, since he wasn't groping anyone, suggested we go to their place soon. Chas said he wasn't drinking tonight, and had a big van, so he'd drive.

I was in one of the back rows, between Kim and Cheri, who was getting into stroking my thighs. Loud music stalled most talk, and we came to a run down looking house, parked, and went in behind Chas.

It was a bohemian style place, older furniture, big rooms, lots of pillows and cushions, but apparently clean. Chas went to the kitchen to get drinks, and Kim sat down with Gina and Mitch in a big papasan chair. I wondered if she'd been here before, and the thought of my prudish sister in law having group sex would have been way too much, if she hadn't just introduced me to a bunch of orgy goers.

Chas handed out beers, and Cheri, still glued to my side, led me off to the powder room. She pulled a joint from her purse and lit it up as I explained how Kim caught me jerking off earlier, what I'd been wearing, and our deal of secrecy. She said that, like me, she'd always loved wearing bras, lace, and women's clothes. Charley had been a bartender, till he'd saved enough for C cup implants, and come fully out of the closet just after that to become Cheri, working the same job, but having so much more fun as a woman. Buzzed further from the joint, we touched up our lipstick, and went back to the big room.

Chas was nude, his muscular body impressive, sitting with Gina, her massive creamy breasts packed into a white sheer bra. White corset, stockings, and heels made her tanned, curvy figure gorgeous, and quite a contrast to Chas' black skin as she stroked his thigh. Mitch was nude, and Jennifer, whose breasts were hormonally achieved (smaller and softer than either Cheri's implanted cones, or my water balloon jugs, was in a red crotchless fishnet body suit, her uncircumcised cock in Mitch's grasp. Gina watched her husband warm up with Jennifer. Kim sat, smoking, dressed in her jeans and tight sweater, her hand cupping Gina's left tit. Cheri pulled me down to a cushion on the floor and kissed me, her hand cupping my boob, moaning softly as I kissed back, and our tongues touched. The buzz, the warm shemale starting his/her foreplay, and the way everyone was so relaxed combined to really let me go with the flow when Jennifer unsnapped my garters to pull off my gaff. My cock sprang free, and Cheri was on it, licking it slowly as my garters were redone. I was getting so hard, it hurt. Jennifer left the room, to get some toys, she said, and Mitch moved over to Chas and took over stroking that black cock, now so big I wondered how much more there could be.

Gina was kissing Kim, and had a hand up her sweater. I wasn't sure if stodgy Kim was planning on this, but she wasn't fighting it. Cheri stopped licking me as Jennifer returned with a big box of toys, I was told to get into the doggie position. Cheri selected a long slim vibrator, lubed a finger, and teased my ass with it, then slowly eased the tool into me. I'd had several toys up my ass before, and always dreaming of being taken by a man, or better, a real cock on a 'woman', and tonight, I was definitely going to get my wish.

Cheri pulled off her tight panty, and asked, "Can I take him first? I want this virgin ass. If he's gonna get fucked, let's make it a good memory. You guys know I'll be a lot more gentle than you will." (well, I was all for that, I was all heated up, wanted to get buttfucked, but the less it hurt was fine with me). Mitch and Chas just nodded, and Jennifer moved around me, her small, soft cock hanging just before my made up face. "Just lick it, hon. Have you ever sucked cock before? Just the fact that you're still here, and down on your knees, tells me you're gonna like it a lot."

I admitted I hadn't, but that I almost always fantasized about getting one hard in my mouth and tasting the hot cum while I was dressed.

"I know how you feel, but trust me, a cock in your mouth will just make you feel so girly you won't believe it. You know what you like down there. Just lick it slow till I get harder, and whenever you're ready, take it between your lips and suck. Get it nice and wet, and then bob on it. Fast or slow, just keep up a steady rhythm. Mmmm, yes, that's it, honey." The head of her cock was pushing out of its foreskin, and it was gaining some size. I sucked deeper, feeling it grow in my mouth. This was great! I relaxed to a steady, slow stroke up and down that slim cockshaft, and was taking a bit more down my neck with each gentle push of her hips. Cheri was spreading my ass, and whatever was pushing slowly into me was a surely a lot warmer than the toy had been. Gentle pressure got it past the first ring of my ass, and, as I sucked Jennifer's cock, suddenly I wasn't a virgin anymore, a hard cock slid slowly up my 'cunt'. Cheri just rested there inside me, letting me get used to it. Jennifer, though, was slowly fucking my mouth, now fully hard. Maybe 4 inches, but very hard. I sucked and met her strokes, and began pushing my hips back to get all of Cheri's cock in me that would go. I wanted every bit of it. She matched the timing of Jennifer, and I was getting plunged into from both ends slowly. A cock in my ass and mouth, deep for a second, then nearly out of me, the back in. It was beautiful, I needed cock. The rhythm changed, and I was getting sawed back and forth, in and out, on hard cocks at both ends. We were a mass of grunting, groaning, horny cocks and tits. Jennifer had me by the hair, pulling me onto his cock, and Cheri had a firm grip on my hips, fucking me deeper with every stroke.

I looked over, saw Mitch sucking greedily on Chas' huge boner, looked the other way, and Kim was putting on a strap on cock, (?), her jeans and sweater gone. I'd seen her in a swimsuit before, she had a hot body, but in a lacy bra, sporting a black 7 inch strap on cock standing over the voluptuous Gina, she looked magnificent. Gina was sucking on Kim's 'cock', getting it wet, and fingering herself.

I was getting the fucking of my life, the sex I'd dreamed of only by my lonely self, so many times. It felt so good to have both holes filled, I was a bit surprised and half disappointed when Jennifer shot off in my mouth. She stiffened, and poured spurt after spurt between my sucking cheeks. I tried swallowing as much as I could, but she pulled out and shot several squirts on my face and tits. The first real thought I had was 'not yet, don't stop! I want more!' Cheri, too, couldn't hold it in, and oozed her thick hot cum deep in my virgin asspussy in several slow, pulsing spasms. Several more slow strokes drained her balls, and I could feel the hot gobs running down my thighs. Gina, spread wide open on the couch, applauded Jennifer's facial work on me, as she took Kim's strap on cock all the way into her shaved cunt.

Cheri pulled out of my ass, and we collapsed on the floor with Jennifer between us, watching as Mitch worshipped Chas' dick. Cheri was kissing Jennifer's cum off my face, neck and chest. I needed more cock, more cum, and went over to the men. Tapping Mitch on the shoulder, I asked if I could cut in. He moved over to play with his wife's heaving tits as she bucked to get all she could between her legs.

I bent over Chas, on my knees like the whore I now was, and tried to get it in my mouth. It was huge, wet and glistening, about two and a half inches thick, and at least 10 inches long. I licked at the big purple head, and got a few inches of his shaft past my lips, bobbing up and down on it slowly. My tits jiggling, my earrings swaying, my cum streaked face showing my determination to get all the cum out of those big black balls. Chas helped out, lubing up his big hand and stroking most of the shaft I just couldn't get to, and I just kept up the bobbing suction. Gina came loudly, several times, as Kim pounded her twat with the thick strap on. Mitch shoved his cock in her mouth to quiet her down, and she just whimpered, sucking on it as she took the multiple orgasms Kim was dishing out. I could see the TVs cuddling on the floor, and Cheri was stroking her cock lazily.

Chas' cock was getting even thicker, it too, pulsed spasmodically, and when he came, it was a flood. So hot, thick, sticky, and so MUCH. No way could I swallow that much. He pulled out and shot stream after hot sticky stream of cum in my eyes, hair, bra, and open, begging mouth. When finally, he was done, I took the head of his dick and sucked out the last drops. Cum was covering the front of me, I felt like I'd been varnished.

Kim pulled slowly out of Gina, and Mitch took over fucking his insatiable wife. Kim moved behind Cheri, and stuck her 'cock', slick with Gina's juices, deep in her asshole. I hadn't cum yet, and went over to Cheri, who greedily sucked my cock as she took her fucking from Kim.

Chas went off to get more beers, and brought one back for Jennifer and me. He lit a cigarette, stuck it in my cum smeared face, and sat back to watch Mitch pull out and shoot his load all over Gina's huge titties. I drank my beer and smoked, as Cheri, her ass getting plowed, took my cock all the way down her throat till she tasted my first squirt, then backed off so I could coat her face with my pressurized load.

Jennifer was underneath Cheri, sucking her cock as Kim slowed down her fucking. Cheri came all over Jennifer, and we all stopped to look around. Kim was the only woman not covered in cum, and she slowly undid the strap on harness. I could see that it had a 6 inch dildo on her side of the harness, too, it'd been filling her divorced cunt while she'd fucked everyone. No wonder she'd been so vigorous and thorough about having a cock for the night.