My First Time Going Out As A Cross-Dresser free porn video

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MY FIRST TIME OUT AS A CROSS DRESSER
A true story

It was 14 years ago and I had been married to a beautiful petite woman she had long Cole black shiny hair with green eyes.. We had been married about a year and one night I came out playing around in a pair of her sexy blue panties and a sexy blue Teddy and started rubbing on her and having fun it made her so hot we both had the best sex we ever had in our lives..
The next Friday when I got home there was a bag on the table she told me to open it.. I open the bag and there was 2 pair of silky French cut Panties with matching bras, 1 pair light green and 1 pair a pinkish color With 2 real nice Teddy's the same colors, 2 pair of dark stockings with garters the same color as the outfits..She came over and helped me put everything on and had me model for her.. I felt real odd the first few times getting dressed up around her but from the first time I loved the feeling of the silky things on my skin and we always had great sex..
Overtime she bought me all kinds of stuff skirts, dresses, low-cut tops, stockings and pantyhose, all kinds of panties and bras to match the outfits, Nice heels, she taught me how to do makeup and what colors to use with different outfits.. how to walk in heels naturally and graceful with that little wiggle in my ass.. how to speak and carry myself like a proper lady.. she also made me a harness for my boobs to train them to be firm and round but we didn't know it would make them grow also now there 40DD she love to play with them and I enjoyed it too…
One day she came home with a big thick strap on; it took me 9 months but she taught me how to deepthroat it to the base and what I should eat and how long I needed to wait before throating it so I wouldn't choke or gag.. overtime I got really good at it and found out that I actually enjoyed being throat fucked...She taught me how to work and hold my ass to make it easier for her to drive it as deep as possible with no problems..Every night when I would shower I would clean myself out real good because I never knew when she would want to take me and she loved to eat my ass and if it did not taste right I would have to go clean it out again!!
It became natural for me to come home from work and slip into something sexy around the house at night or weekends if no friends or family we're coming over..it was pretty cool I could be a manly man to her or be her soft sexual bitch she had the best of both worlds and I liked it !! But she passed 4 years ago in a car crash a drunk driver ran a red light and slammed into her driver's door...

I still get dressed up all the time and have a wide assortment of dildos and plugs but it's not the same.. I had never been out in public before but I have mist being touched and held for so long I knew I had to do it.. one night I got up the courage to get dolled up and go outside..I went to the gas station and filled up my vehicle it was a cool night and the cool air blowing On my silky legs and up my skirt made my ass and legs tingle..
It was a feeling I had never experienced before and it made my puss juice up some...People were just going by not saying anything a couple of guys walked by staring real hard I think they were just looking at my big boobs like guys do and I did look pretty hot in my heels and sexy outfit..
I went to the drive-thru and the only thing anyone said about me was the girl who took my money she complimented me on my beautiful nails the next Saturday I spent 5 hours to get perfectly dolled up Because I had picked out an alternative nightclub.. When I got there I was so nervous Walking from the parking lot to the door I just stood there for a while before opening it.. I finally said this is it!!! and opened it the doorman was standing right there I paid him the $4 and he open the next door for me and told me to have fun.. When I walked in it was a whole new world there was girls hugging and kissing each other Guys with their arms around each other..But people were just having fun drinking and dancing I found a spot at the bar and ordered a drink the bartender was real friendly and I started to feel comfortable.. I was just another sexy Bitch having fun...
When the bartender came back and gave me a drink.. I reached in my purse to get him some money and he said no this drink is on the guy across the bar and he pointed at him.. the guy held up his drink so I held up mine and nodded my head..pretty soon I had 5 shot glasses in front of me Different guys were buying me drinks and coming over to talk to me.. A few of them would rub my ass as they said some nice things to me I didn't say a word I kind of liked it..
But I did notice they didn't look in my eyes... I see what girls mean they were talking to my boobs lololololololol except for one guy He was quite handsome with a slim muscular build he did rub my ass but he looked at me when he was talking..I felt real comfortable with him and we talked for a while and we laughed and joked like old friends.. After 3 or 4 drinks I was feeling pretty frisky And grabbed his arm and slid his hand under my skirt on my ass..He just smiled at me and started playing with it as we talked I like his hand gently gliding on my Silky ass.. I told him to hold my place because I needed to go to the bathroom..I tried not to wiggle my ass too hard as he watched me walk away..
When I got to the bathroom I wasn't sure which one to use but I felt like I couldn't use the men's room with my big boobs and in stockings and heels so I went to the ladies room and of course there was a small line and the girls were just staring at me till the one girl in front of me started talking to me.. Not knowing I was a guy I have a real natural feminine voice Also... You wouldn't believe what girls talk about as we move forward in line I told her I was a guy and she thought I was lying to her she said no way your boobs look so natural and I told her they were..I let her feel them which was a mistake because before I knew it there were 3 or 4 of them Checking them out.. and once we got in the bathroom they wanted me to show them my chubby clit so I did.. One of them wanted to take me home We went back to the bar where Jimmy was and I introduced her to him... we were having a lot of fun when Jimmy said let's go to his place...
I had been longing to be held for so long I jumped on the opportunity.. We all drove to his house Beth and I were as giddy as schoolgirls..When we got inside Beth whispered in my ear that she had not been with a guy in a long time!! I told her it was okay I knew what to do but I had never been with a guy before .. Beth and I sat on the couch and Jimmy when in the kitchen.. she started kissing me and rubbing my boobs I undid her pants and started rubbing her pussy through her panties when Mark came back in the room he just stood there and watched us making out then came over and joined us.. Jimmy just sat there while Beth and I undressed each other in front of him..
We got on our knees she undid his pants and I pulled them off.. I kissed her Then she held his cock playing with it and showing it to me waiting for me to suck it!! So I went down on him getting it hard..Then I did the same for her we were having fun and laughing sharing his cock .. Then Beth let me take over we were both on our knees in our panties and bras having fun.. She got behind me and started licking my ass I could feel her slide my panties to one side and started munching on my puss mmmmmmm It felt so good as I throated Jim’s cock.. She made me super juicy!!! Then we swapped I ate her ass and fingered her pussy and ass I was having so much fun with it.. Jim must have been real Hot because I could see he was going to Cum.. I moved up to Beth and tried to get her to stop but she just kept going till his cock was ready to blow she pulled it out and started jerking on it real fast pushing my head over it with the other it the first load went right in me eye and she started laughing I put my lips on the head and let the rest shoot in my mouth she told me not to swallow it as she jerked him off milking it all in my mouth when he was done I sat up..
Beth licked the Cum off my face and kissed me taking the Cum from me !! And motioned me to get on the couch I sat beside Jim and she crawled up on me putting her hands on my shoulders I put my head back and open my mouth and started to drip the Cum back in mine letting Jim watch us we swapped it back and forth kissing and playing with each other enjoying the tasty Cum..
Then I got on all 4’s and held my ass up for her she worked her tongue as deep as she could pushing the Cum in me and mixing it up in my ass.. Jim was rubbing his cock watching us not saying a word .. when Beth was done she got on her back between my legs and told me to push.. my ass was facing Jim so he could see the creampie but Beth was catching it in her mouth as it ran off my balls and swallowing it when it was all gone she licked my balls and puss clean and shared it with me giving me a taste of my juices mix with the Cum!!!

We took Jim by the hand and took him in the bedroom and got into bed we let Jim finish undressing us Beth and I took turns he took off Beth bra then mine I moved back and Beth moved up letting him slip off her panties then I moved up and he slipped mine off they were all wet from Beth working my ass he through them on the bed Beth jump over and got them sucking the juice from them as I just razed up my ass and laid my head on the bed waiting for Jim to take it!!! I felt him grab my hips real hard and move up behind me slipping his cock on my back.. Beth put her pussy right in my face with her knees up as she sucked on my panties so I started munching on it… I could feel the head of Jim’s hard cock opening my juicy puss I was in heaven as he worked it in.. I pushed Beth knees back and started eat her ass and working my fingers in
Jim short stoked me for a bit then drove it deep in me and started pounding my ass making me cry out AAAA AAAA BABY FUCK ME MMMM YES MMMMM FUCK ME MMMMMMM I put my face back between Beth legs and start going crazy on her ass and pussy making her cry out too.. OH YOU FUCKING BITCH EAT ME MMMM MAKE ME CUM MMMMMMM JAM YOUR TONGUE IN MY ASS AAA AA YES EAT IT MMMMM every time Jim slammed his cock to the base it dove my tongue Deeper into Beth .. She started Cumming She was crying out real loud I couldn't understand what she was saying it was like it was talking in Hebrew or something but her whole body was quivering Jim was pounding me so hard I was crying out in Beth's ass because I couldn't stop eating it.. Her pussy Cum tasted so good; I would suck it out of it and work it in her ass.. Beth pulled back a little bit and raised up some and started squirting all over us.. I could see her legs trembling as it squirted out then she just dropped to the bed and laid there quivering and crying out MY GOD MY GOD !!!!! Jim was pounding me so hard and fast it was going to make me Cum…
He fucking me faster driving my face in the bed I’M GOING TO CUM he stopped and pulled it out and grabbed my hard clit and folded it back pushing it in my ass making me Cum in my self he was fucking me with my clit I could feel my warm loads shooting making me Cum even more he milked all he could in me and jammed his cock back in working my Cum Deep in me I started fucking him back real hard crying out YOU FUCKING BASTARD AAAA FUCK ME WITH MY JUICY CUM OOOOOO WORK IT IN ME MMMMM FUCK ME FUCK ME HARD MMMMM GIVE ME YOUR CUM OOOOOO CUM IN MY ASS MMMM he started crying out as he drove it to the base and held it MMMM I CUMMING AAAAAAAA AAA AAA AAA AAA I could feel the load shoot deep in me .. I told him; Cum In My Ass Fill Me Up I Want It All..
Beth moved over and was rolling him balls in her hand as he unloaded in me .. I kept fucking his cock mixing our juices till he pulled it out.. I just stayed there with my ass in the air so Beth and Jim could eat me she would get a mouth fill and share it with me here and there but Jim kept it all.. I didn’t care he was having fun with me!!! When we were all done we just laid there on the bed naked and exhausted.. Jim was done for a while but Beth wanted more of my ass and I wanted more of hers.. She climbed on top of me and folded my legs way back and put her ass in my face and we started munching on each other like a couple of Lez’s …
Till Jim has ready again !!! and he took Beth (with her tilling him to fuck her ass too) I know it was ready for him I made it so juicy eating and fingering it … He push her to the bed on her Stomach and climbed on top of her on his knees I spread open her ass for him as he ran the the head up & down her crack letting me watch it as he drove it in and started fucking her real hard I moved up and put my chubby clit and puss in Beth's face and she started sucking and jerking on it while fingering my ass going in rhythm with Jim we were all being fucked at the same time… it took a while but I couldn’t wait to eat Beth Cum filled ass.. Jim was fucking her like a pro I could see she was real enjoying it her ass was moving around fucking him back..
I climbed on top of Beth a started kissing Jim as he fucked her he grabbed a handful of my tits twisting my nipples and kissing me.. Beth's back was getting all slippery from the juice licking out of me and I was sliding it all around on her in rhythm with them.. Jim and I were both up right on our knees on top of Beth kissing Jim was fucking her ass real good when he started to Cum I reach around and worked a finger in his ass to make him Cum more I could feel Beth razing her ass up to accept it and Jim was Kissing me Hard and passionately as he Cummed… When he was done I gave him to Beth to suck clean.. I just want her Cum filled ass I spread open her legs and went down on her ass it was so good all hot and juicy I could feel her inside pulsing when I would push my tongue real deep and it tasted so good with her ass juice and Jim’s Cum mixed together MMMM … I still fuck both from them here and there once in a while all 3 of us will get together... Beth bought a Big Strap On and has got real good with it.. I slipped Jim a Viagra one time and fucked him for 5 hours none stop… Well that was my first experience on going out as a cross-dresser I hope you have enjoyed it because I really did lolololololololololol Sextoy101

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Rebecca was slightly depressed because she had suffered some redness on her backside from the oversexed male scoutmasters who pestered her to drop her drawers for them because she was female and definitely not of jailbait age. Of course, her attitude and her appearance were misleading, and she reveled in the attention she received because she looked like one of the underage female scouts and not a scoutmaster in her own right. A couple of the good old boys got carried away by the sight of...

Property of Devils Outlaws Part 13

Less than 50 miles away from where Hannah was suffering, inside a tavern also owned by the Outlaws, another whore was having a miserable night of her own. Ellen Duffy, the incredibly hot redhead and Miss Washington contestant, was on her back with her legs spread while a fat, greasy Mexican fucked her pussy raw. He was the fourth Mexican in the past 20 minutes to fuck the young redhead, and he was in a state of euphoria as he pounded into Ellen like a savage. “So boys, we got a deal?”...

Crossover Chronicles of Outfall

Some are human & some are furry humanoids in this plot twist co-existant world. This is an alternate Chronicles sample of different pov per page as long as its pointed out. Similar in some aspects to the Passion Humiliation Club story, if need to see a humans only based, read that one as planned for it to be continuous also w/multiple endings. The city is Outfall. County is Canti, has a light rail for other destinations not shown. Canti Park has an indoor public gym for sports & the like,...

First Time for Everything A Jo Cross Story

"Kirsten?" Even though I was dressed in male clothes --- not even wearing panties --- I looked up instinctively from my booth in the diner. After all, in the great scheme of things, Kirsten was my preferred name. "I thought that was you." Jesus. Talk about a blast from the past. Jo Cross as I live and breathe. And still looking gorgeous with a warm, sweetheart smile. "Jo?" She grinned and bent to hug me. I felt her fingers exploring my shoulders. "You're not wearing a...

Cross Burning For Dummies

To “Hardcore” Hardaway’s way of thinking, the three snot-nosed young farts standing just inside the door to his cluttered work shed didn’t look good for much, most of all a Klan job.At first, they’d tried to act cocky, like this wasn’t no big deal. But none of ‘em said a word after seeing the cross he’d put together that afternoon. Now he was back out here trying to teach these whelps a thing or two while the half-finished can of beer he’d left inside went flat.Why in hell did Jack Tidwell, who...

Humor

Karl to Kayla Cross Your Heart

This is my first attempt at this so, please be kind with your reviews. Email your comments to me at '[email protected]' Karl to Kayla - "Cross Your Heart" By Kayla Eastcock Eatscock My name is, or should I say 'was' Karl Eastman and it all began one evening while I was at work. I am an average looking 26-year-old guy. Short, sandy-brown hair, blue eyes, 5'10", 145lbs. Okay, so I was a little thin, no big deal. Over the past few months, I had developed a bad habit...

Property of Devils Outlaws Part 6

Hannah was rudely awoken, like always, with a hard smack to her face. She yelped in pain and immediately began whining in terror. She could hardly remember getting pulled from the shower and tied to the bed last night. However, she did recall puking up a huge amount of sperm and piss into the tub. Her jaws and throat were still extremely sore from the dozens of blowjobs she’d been forced to give, and the burn mark on her back was still very raw and inflamed. “Get your ass up cunt, you...

Story Treatment TerriTerry and the Cross Time Pirates

"Satirizing reality, since time travel is impossible! and we needed to make a few bucks" Terry and the Cross Time Pirates is a twisted reality show. The plot line fills in what they are trying to do in bits and pieces that are made up situations involving advertisements that bookend the show all being for none existent products and events. A skewed sense of absurd paradoxes presents this crew of would-be crooks trying to run a scam and make lots of money off of it, but they are also...

The Priest Teaches His FlockChapter 10 Sally Rides the Cross

Father John hadn't even said hello to Sally. Pulling her along the corridor again, Sally knowing that they were going back into the basement again. She shuddered when she saw the cross. It was huge, standing over eight feet high, four feet wide, made out of heavy wood. It was a little strange for a cross, it looked like it was upside down, the cross piece lower down the upright, not near the top like a normal cross. At least the altar was gone, but she feared the cross, not sure what it...

De toutes sortes

It provides a list of the “in” places to go, but I’m not really an “in” place person. However at the end of the listings I came across a series of Petites Annonces – Personal Ads. I was just looking at it out of curiosity – yes curiosity I was not looking for the advert which ran “jolie fille sexy recherche rencontre hot sur Paris” and I did not answer that one (honest). Then I noticed a section headed Photos - Modeles which seemed to consist mainly of photographers looking for lady models...

Crossover

Crossover Janet L. Stickney [email protected] There was never any doubt that I was going to be a girl someday. I mean, from early on I would wear pale lipstick and eyeliner with my hair usually braided. Then came the Crossover week and I was able to dress like a girl from the skin out, complete with hips and boobs. My father was a drunk that never cared what I did, and my mom was long gone so how I dressed was never an issue. I work at a small shop that makes and repairs video...

How I started Cross Dressing and other first times

I love to cross-dress! I love everything about it!Like most of us cross dressers, I love everything about ladies undergarments. I like seeing lingerie in ads, in stores, on models, on TV, on women, on men and of course on me! I love the feel when I am dressed up. I love the taboo of wearing them. I love the thrill of being “underdressed”, which is wearing lots of lingerie under your manly clothes, when I go to work. I especially love the incredible horniness and lack of all boundaries...

Garys Golf Outing Chapter 14 Ladies Favorite Pasttime

Gary's Golf "Outing" Chapter 14 - Ladies' Favorite Activity I finished all of my work assignments and my home chores by Thursday. I had chatted with Kay a few times and was surprised when the phone rang on Thursday evening. "Hi Gabrielle, this is Kimberly. Are you all set for Saturday?" "Hi Kimberly, what's happening Saturday?" "Don't bull-shit me, you bastard. You know what's happening as well as I do and I'll bet you've been thinking about it all week." "I have...

Garys Golf Outing Chapter 1 Seven Hole Washout

Gary's Golf "Outing" Chapter One -- Seven Hole Washout My wife's mother called to tell her she wasn't feeling well and she wanted my wife, Kay, to come up to Chicago to be with her. She is a hypochondriac and it's not unusual for her to interrupt our vacation, or whatever we're doing, with her demands. I was hoping to play golf this day but it was getting cloudy as I drove my wife to the Fort Lauderdale Airport. As I kissed her goodbye, I told her to give my love to her mother....

Mortimer and Myrtle A Love Story

Note: This is not your usual Lush story. It is an experimental play in a theater of the absurd style. There is no sex but it is an entertaining comment on marriage. I encourage you to indulge in something different. I think it will make you laugh and maybe cry. Scene: A formal living room. Mortimer is seated on a sofa in the center of the room when Myrtle enters and sits on the sofa next to him. She is wearing a blue floral dress and a pearl necklace, her gray hair is tied in a bun. Mortimer is...

Young Cross Dressers Secrets

Young Cross Dressers Secrets *Sandy was busting at the seams to tell someone some very exciting secrets she was keeping. She couldnt tell anyone she knows. She decided to tell them here. __After reading My Bra and Panties are Missing, my own real story kept nagging at me to be told, but I wasnt sure how. I decided to change all the names and write a story all about this secret world I stumbled into. I started getting very horny just thinking about all that had happened&hellip,. __My story...

SouthboundChapter 10 Showtime

Things were happening quickly, almost in a blur. I interviewed Lucas Randall in late February for the controller position on the recommendation of Dave Charles. If he was okay in Dave's view, then it was guaranteed he had the qualifications and experience to manage the money at Tracy. It was really only a matter of whether he and I could get along. "You met with Dave, so you know my limitations," I began as we sat in my office. "I'm dependent on you to keep me up to speed and aware of...

The United Kingdom of Zoo A fake BBC documentary seriess6e21 The Portsmouth Womens Institute

Series 6, Episode 20 The Portsmouth Women’s Institute (ages 50-60), from Portsmouth We open with a very simple and idyllic establishing shot of the front of an unobtrusive building with a little square of grass around it. A sign reads, “PORTSMOUTH WOMEN’S INSTITUTE” A small car park is half filled with sensible middle-class cars a Volvo, an Audi, a nice VW, etc. Trees rustle as the wind blows through them. Very safe violin music plays on the soundtrack and then The needle on the record...

Confessions of a Sex Crazy Cross Dresser Part 4

Hi Everyone, I hope you like these chapters, please let me know if you want the next two. Chapter 7: Triangle of Fun I slept great that night with a full stomach of drink, food and Peter’s cum. I woke up on Friday and thought this is going to be a hell of a weekend. I played around with my cameras and had finally figured out how to use the self timer on the 35mm and how to use all the options on my movie camera. They were both relatively new as I bought them in Phoenix, just before moving...

Confessions of a Sex Crazy Cross Dresser Part 4

Hi Everyone, I hope you like these chapters, please let me know if you want the next two. Chapter 7: Triangle of Fun I slept great that night with a full stomach of drink, food and Peter’s cum. I woke up on Friday and thought this is going to be a hell of a weekend. I played around with my cameras and had finally figured out how to use the self timer on the 35mm and how to use all the options on my movie camera. They were both relatively new as I bought them in Phoenix, just before moving back...

Crossdressing

Crosstraining

Cross-training Belladonna "Are you ready, pet?" "Yes, mistress," George Bloom responded as Celene knocked upon the iron door. George heard the loud clink of the old fashion knocker upon the door as he pulled at the hem of his short skirt. He anxiously waited for the door to open, hopeful that he would not be noticed by those passing by on the street below the staircase leading to the porch he was standing upon. George had never been to a Dom-sub party like the one that his...

Cross Dressing Cock Slut Party

Sadly this wonderful story is just a fantasy, but who wants to make something similar a reality!?!The evening had taken a while to arrange, but had finally arrived. All 5 guests turned up within 15 minutes of each other and as they did, I fixed them a quick drink and showed them into the living room to get to know each other. Alan was a suited businessman in his mid thirties. Dave and Brian were dressed casually in jeans and Tshirts and both in their mid forties. Jeff and Keith were my age,...

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