Hello, my name is Michelle and I am an out the closest transvestite. Below is a complete fantasy story of how I was forced into becoming nothing more than a sissy fuck toy and also to be feminine practically all the time. Would I like this in real life? Well, it's fantasy and some things are best to be kept as as fantasy.
If you have any feedback, comments or anything you want to talk about my story then my e-mail is michelle1983@live.co.uk
Michelle's the bitch
This is a rather long story of how I went from your regular out the closet transvestite to a completely owned sissy slut bitch all done by my wife and my fuck buddy. Yes I did my fuck buddy; it's a weird relationship, but I've now got used to it, and to be honest, I really enjoy it. So hold onto your seats (just as I am doing while the fucking machine I'm sitting on pounds my ass as I write this) as it's going to be a thrilling ride.
Chapter 1
I'd describe myself as 50% male and 50% female. To the every day person I act and look male, though when in my own time I dress and act in a feminine manner. For as long as I can remember I've always been interested in girly things. I don't know why, I've just been attracted to them. I remember playing with girl's toys of the girl my mum used to be babysit. When I 'check' women out not am I also admiring their beauty but also what they're wearing. Sometimes I'm only looking at women because I like their boots they're wearing or they way they have done their make up; it makes me want to wear the same boots and do my make up in the same way. I work in an office with many female co-workers and when they're having conversations about nails, dresses make up etc I feel jealous and I want to join in their conversation.
I'm quite lucky as I came out to my wife many years ago and as such I don't have to dress in secret. At first it was tough, but we got through it and over time it has improved our relationship - when we're out shopping my wife asks my feminine opinion on a new skirt or top etc. She also gets to wear my dresses too as we're the same size, another bonus for her.
In the past me and the wife have visited gay clubs with me dressed up. It was exciting but also a nervous time going out dressed to a public place, but I had no problems. I felt free when going out, as if my feminine side has been released instead of hiding locked away in the house etc.
One weekend there was a gay parade for the weekend up Manchester. I mentioned this to the wife and she suggested we go up and stop over night in a hotel. She said I could stay feminine the entire time while I was there, this was great as usually I only get to dress for about 5-8 hours. It appears I could be in 'fem-mode' for at least an entire day.
So we had been out that night to several gay bars in the Manchester gay village. We saw many different people going from ultra camp gays to super butch lesbians to dolled up drag queens. All stereotypes of the LGBT community had made an appearance that night. Now I'm just a casual tranny, I just like to dress like a normal one, so nothing outrageous for me. That night I wore a black short skater dress with black tights and black wedge ankle boots. I finished the look off with gold bracelets, watch, necklace and big hoop earings, oh and a mid section belt too. I like to blend in, well, try to blend in.
We had fantastic night down letting our hair room and went back to the hotel room. The room was nothing fabulous, but we wasn't slumming it either. The room was an upside down L shape with the bathroom en suite on the left when you come through the main door, then the double bed just around the corner. In front a long desk with a TV on. A comfy chair was positioned at the desk.
"I want to do something different night" explained wife. "I've bought you a treat. Here"
Wife handed my a large box. I opened it up and inside was a black maid's outfit with fishnet holdup stockings and a pair of black PVC 6" strappy platform heels.
"Go in the bathroom and get dressed and put your chasitity on too"
I had bought a chasitity device for myself about six months ago. It was the traditional CB6000 and see through plastic, nothing special. I don't know why I bought it really, I suppose it was just for a laugh and to play a 'game' with myself as I can't masturbate or do anything. Wife wasn't happy at first, but after she got into it and realised it did no harm. In fact she would sometimes have the key as a little game and keep me locked up for a few hours before we had sex.
I went into the bathroom and took off my dress and everything else. I was down to my black satin lace panties with matching bra and black waist clincher, hey a tgirl has got to get a figure some how!
I slipped the maid's outfit over my head, it felt very light, soft and was made from satin so very silky. I tightened the apron around me which helped show off my feminine figure. I then pulled the fishnets stockings over each leg, they settled at the top of my thigh. I've only wore fishnets once before and that was a long time ago, damn they look sexy and kinky. I slipped my feet into the heels and fastened the ankel straps, when I stood up damn did I feel tall (I'm average height at 5ft10). Lastly I slipped my cock out. As a transvestite I keep myself shaved and this includes my cock. Not only does it make my cock a bit bigger (not that it's big, it's only 3" when soft and 5" when hard), but I think it looks more feminine, that's if you can have a feminine penis. I put the ring of the chasitity around my balls, slipped the top bar over and then the tube over my penis and locked the chasitity in place. I had no idea what wife had planned, but damn it looks like it's going to be kinky.
I left the bathroom and gave her the key to the chasitity.
"I want you to look a little more slutty. Let's get you ready" ordered the wife.
I sat down on the edge of the bed where she painted my finger nails a bright red and also put matching bright red lipstick on me too. She finished it off with some gloss making my lips look ultra yummy.
"Let's get some pictures of you. Stand by the door and I'll get some good ones of you"
Like an obident puppy I went near the door and posed like a catalogue model, pouting my lips out, sticking my arse out, stretching my legs wide etc. Wife also got some pics of me in chasitity, in fact they were her idea.
Suddenly there was a knock at the door! I scrambled away like a scared rabbit and hid around the corner.
"I'll get it. You stay there" bossed the wife.
"Oh, hi, how are you?" said the wife. "I'm very good thank you. It is really nice to meet you at last" replied a deep man's voice. "You too. Come in; it's time to have some fun!"
What the fuck did my wife mean "have some fun"?
"Michelle come and out and say hello to Derek" ordered the wife.
I came around the corner from by the bed and standing by the main entrance to the room was a tall muscular black guy. I'd say this 'Derek' fella was about 6ft5" and was probably 20 stone of muscle. He was a guy you wouldn't want to mess with. His black hair was short and shaved and he had a light black beard. I'm not attracted to guys, but you know a good looking person when you see one; I'd say Derek was average attractiveness.
"Well, well you damn look mighty fine" said Derek to me. "Er, thanks" I said. "So, babe, this is Derek, I met him on Craigslist a few weeks ago" explained wife. "You see I accidently stumbled onto your fe-mail (I have an e-mail account for feminine releated e-mails and for ebay etc) and found out your tumblr account and also the ads you had put on Craiglist. I knew you liked acting feminine and looking feminine, but I had no idea you wanted to be with a man" explained wife.
I'll explain myself to you, the reader, I had a tumblr account and followed many tranny related accounts. Some of the images were just tranny porn and others were sissy captions. Some of these captions I had 'liked'. In moments of raging horny madness I had also put a few ads on Craiglist. I had never met anyone, so don't count me as a bad husband completely. I guess you can just label me as a time waster. It appears the wife had discovered all of this.
"Babe, I can explain. They were just things I had done in the spur of the moment so to speak. Nothing more than a fantasy"
The entire time me and the wife discussed me going's on Derek eyed me up like some piece of meat. I mean who could blame him, a pretty girl was standing in front of him in a short maid's outfit with high heels, fishnet stockings and bright red nails and lips.
"Don't 'babe' me! Lust is just like anger, when it takes control you show your true feelings and colours. I know deep down you want to be with a man. I know it will make you feel more feminine, after all been with a man is the most feminine experience you can have" explained wife. "At first I was upset and then I released that we're best friends and it doesn't matter it you want to look like a woman, act like a woman or have sex with men. You're my husband and as long as you stay with me and end up back in my bed at the end of the night I'm happy. See put an ad on Craiglists, I found some sexy photos of you and posted them. I've got to admit I had a lot of responses, but Derek was the diamond in the rough. See I figured it would be okay you having time with a man if I can control it and by putting an ad on Craiglist I can pick and choose who you see and who you have no strings relationships with"
I was completely speechless. Not only had the wife caught me red handed with my fantasies but also acted upon them for me and keeping them in control.
"So, tonight babe, you get to suck cock and get fucked by a man. Derek, do you want to check my sissy bitch out?" "I sure do!" replied Derek like an excited kid.
He stepped over to me and swooped his big thick arm around my waist and pulled me close into him. My fake double d breasts pushed against his big muscle chest. His other arm reached around my and he placed both hands on my ass and gave a squeeze while running his hands up the side of my waist feeling my figure.
"Wow! You sure feel great. I've been waiting to get my hands on you since I saw your pictures. I can't wait to fuck you hard tonight, smash that fuckable ass and fill your ass with my cum"
"Look, Derek I'm not sure about this. Babe, I don't think this is a good idea"
"Michelle, it's fine. I am perfectly happy with it" replied the wife. "In fact I strongly insist you act your fantasy. It's taken me a lot of effort to arrange this and I am also pretty sure Derek doesn't want to have his time wasted"
Derek nodded in agreement while staring into my eyes with his deep brown eyes.
"I'm not going to do it. I don't want to" "Okay. Well I didn't want to do this, but if you don't have Derek's cock in your mouth and let him fuck your ass I will send these pictures I took earlier to your work and you parents. I am sure you don't want that do you?" "You wouldn't dare! That's utter bullshit" "Try it and find out!"
I knew she wasn't bluffing. My wife is very stubborn and will stick to her guns when she wants. She will ensure she gets her own way and won't ever give in.
Derek put his hands on my shoulders and gentely guided me so I was sitting on the corner of the bed. He moved towards me so his crotch was a few inches from my face.
"See what I've got for you then, slut" he commanded. This was his hint for me to unzip his jeans.
I did as he suggested and unzipped his jeans. As I said this he took off his top revealing his super toned body with slab like pecks with a washboard stomach sporting six pack.
I reached inside his underwear and felt what I can only describe as a semi soft pipe in his pants. I pulled his cock out and watched it grow in front of my eyes. Just like the rest of his body his cock was a specimen. It was dark, cut with an even darker fat head. His cock was about 6" in width and about 8" long.
"Wrap those sexy red lips around my cock, baby. I want your red lipstick painted on my fat black cock" ordered Derek.
I opened my mouth and took my first ever taste of cock. It's a hard to describe taste, but it wasn't nasty. I guess I can describe cock tastes like a not so sour pussy. His cock in my mouth felt huge, it filled my mouth. I could just about get it in my mouth. I wrapped my hand around the base like my wife has done to me and like I had seen in porn films and bobbed my head up and down on his shaft taking his head in and out of my mouth. Even though I had my hand around the base of his cock there was still so much more to put in my mouth.
As I sucked my first cock I began to enjoy it. It was completely different to licking pussy, but regardless I enjoyed it. As I got into sucking Derek I noticed my wife recording the entire sex act on ehr mobile phone.
"That's it, babe, you suck that black cock. You enjoy it." commented the wife. "Do you like sucking my cock" asked Derek" I felt obliged to answer "yes, it's great!" I carried on sucking Derek, he was loving every moment of it, so was my wife, who was sitting in the only chair in the room with her legs spread rubbing her pussy with one hand and filming my entire blowjob with her phone in the other. Not only were they enjoying it, but I was too. "That's it, baby, I'm nearly there. You suck cock so good. I can't believe your a man as no man sucks cock this good!"
I bobbed my head faster and faster. I knew Derek was getting ready to blow his load. I wasn't sure if I was excited this entire forced ideal would be over or if I was enjoying getting him off and wanted him to squirt his load.
Then I felt Derek reach behind my head and pull be close into him. I felt his cock swell and then boom his cock erupted into my mouth, at this point Derek was now fucking my mouth while moaning making sure he squirts as much as possible and get off the best he can. Of course he had his cock in my mouth and there was no chance I could take it out if I wanted, so the only thing I could do was swallow his load and boy it was a big load!
"You're so good, tranny bitch. You've even been a good slut and swallowed my cum. You've got a right good slut here, you know!" "I know!" responded the wife "Slut, come over here and like my pussy"
I did as ordered by the wife and went over to her from the bed with the taste of cock and salty cum in my mouth. I knelt before her and pushed my head between her legs. Her clit was rock hard and her pussy was so wet. I licked my tongue up and down her, her pussy a more sour taste than Derek's cock. It took me about 5 minutes of licking her and her clit got wet and she squealed and came.
"Wow, babe, you're an even better pussy licker once you've had some cock down you. Now, you're the only one left to cum. Do you want to cum?" "Yes, babe, I do" "You need to cum properly then. You need to cum like a girl, okay?" "Okay" at this point I was ready to burst. This entire time my small cock has been swelling up the best it can in the chasitity. The chasisity put pressure on my cock and gave me a nice feeling, but that was it. With it on I had zero chance of getting off the normal male way" "I want you to ride Derek's cock, babe. You can cum like a girl that way" "Okay"
I know I had no chance of fucking my wife. I know I had no chance of getting my cock out the chasitity so I could whack one off. The only way I was going to cum was by having Derek's cock inside my ass. I've never cum by anal, but I was so hot at this point I would give anything a try so I could blow my load. I gave in without arguement as I know it was pointless. I looked over to Derek who at this point was already lying on the bed with his legs spread wide and his 8" thick black cock pointing to the ceiling ready for me to mount it.
"Come on then, sissy. I've been dying to fuck that sweet ass of yours" smiled Derek.
I couldn't believe that his cock was still hard waiting to fuck me. Usually once I've blown my load I'm ready to get to sleep. Though Derek was the complete opposite, he couldn't be more awake.
I climbed onto the bed ready to mount Derek traditional cow girl style.
"Go reverse, I want to see that sexy ass of yours grinding on my cock"
I did as he asked and squatted just in front of his cock, in fact I could feel his cock resting between my butt cheeks and touching my lower back. Damn this monster is going to hurt!
Once I had got myself comfy I raised myself up a bit and I reached behind and grabbed Derek's cock. His cock felt wet and slightly gooey, probably a mix of cum and my saliva. At least it would slide in easy! Derek grabbed my ass with his hands and spread my cheeks so his cock would slide in eaiser. What seemed like an age I slowerly lowered myself onto Derek's cock, I felt his head touch my asshole, my tight ass opened up and accepted his head. My ass felt stretched and tight as his cock head slowly slid into me followed by his thick shaft. His cock didn't hurt as much as I thought it would, it was a mild discomfort at best which soon disappeared once my ass was flat resting on his crotch with his balls touching my ass cheeks. I guess the buttplug I used on a regular basis helped along with my saliva on his cock, though my buttplug was no where near as his cock.
I then began to rock my hips. I rocked backwards and forwards feeling his huge cock taking up all the room inside my rectum. As I fucked his cock my wife was sitting in the same chair with her pussy on show while she filmed the entire lot with her mobile phone.
As I fucked Derek he squeezed my ass. My hands were holding his hips, I could feel even muscle there too! I moaned like a girl. I was starting to feel pleasure with his cock inside me, it was rubbin on my g-spot and it felt great.
"Wow, it looks like you're enjoying yourself, girl" said the wife. "I've got an idea, let's play a game. You like acting like a girl, looking like a girl and been a complete cock whore. Derek loves fucking you. I love him fucking you. In fact I enjoy our relationship more when you're feminine than when you're a man. So here's what's going to happen; if you cum first then this will be the first and last time you will fuck a man. You've had your fantasy and that's it. This will never happen again.
If Derek cums first then you will be our sissy bitch. You will dress and act feminine when you're in the house at all times. You will be Derek's sissy fuck whore and my sissy pussy licker. You will never have sex with me or in fact another woman again. You will only have sex with Derek. Also the chasitity will stay on permanently, after all you won't need your little cock any more for fucking as you'll be the one getting fucked.
Now luckily for you Derek has already cum, so it will probably take him sometime to cum again. You stand a good chance of this been a one time deal if you can get that little cock squirting with a cock up your ass.
Let the fucking begin!"
Oh my god. My wife has just pushed me into some kind of promise or deal which determines how our relationship will be moving forward. While I love been feminine I like to do it when I want to and not all the time. Playing with cock has been an experience, but I'm not attracted to men and I'm pretty sure I wouldn't want to just fuck cock for the rest of my life - I want to fuck sweet pussy to! I'm also in a lose/lose situation. If I cum first then I've just got off with a cock inside me. If Derek cums first then I'll be getting a lot more pleasure from his cock. Either way I'll be getting off from cock very, very soon or very, very often for the foreseeable future.
I began to ride. I began to ride fast and as hard as I could grinding my ass into Derek. His cock went deep into me. Dman it felt so good. I really wanted to get off, but I was really enjoying myself too. As I was riding my tiny cock locked in chasitity was flinging about. I could hear the lock bouncing off the plastic making a repeated cacking sound.
I ground my ass faster and faster on Derek's cock. I was moaning like a real whore and I wasn't faking it, I was doing it because I enjoying myself. I was also subconsciously cupping my fake tits and rubbing my nipples through my maid's outfit. The entire time my wife was filming this on her mobile phone.
I could feel Derek's cock in my ass putting more pressure on my g-spot. Whatever I was doing was really getting off. I could feel my cock ready to blow any second. I was about to have my first orgasm via anal. I couldn't wait to cum, not only was fucking cock really, really nice, but I was also desparate to blow my load before Derek.
"Ohhhh, I'm gonna cum" I slipped out in my sexual cock riding rampage.
The entire time I was edging myself closer and closer to getting off while moaning and I was right on the edge, I just needed tipping over, I needed that little more pleasure on the ride spot to get me to blow.
"I'm gonna fill you up, babe" said Derek in an erotic voice.
This whole time I was desparate to get off before Derek and I hadn't noticed he was ready to blow. I guess me grinding faster and faster with his fat cock inside me and really gotten him going quicker. I hadn't even noticed until he said those words. Then I felt his cock swell. I felt his cock pulse and pump my ass full of his black seed. I knew my future had been sealed. This was also what I needed to go, my tiny cock pulsed and squirted what it could, cum dribbled out the chasitity device really pathetically, like a baby drooling is the best way I could describe it. My load was nothing compared to Derek's, which continued to flood my ass. It's pretty poor that Derek had already came once and that my load is still smaller than his and it still took me longer to get off than him. It's also really ironic that I needed Derek's cock to cum inside me to make me go. It's even more ironic that me and Derek had a vicious orgasm circle, see his cock pulsing made my cum, in turn my ass spasms which then make his cock pulse again. We kept going like this until Derek's balls were completely drained. Until he had filled me up and made me his bitch. My cock on the other hand only squirted the first pathetic dribble and that was it, but, damn that was the best orgasm I've ever had! So much better than having an orgasm with my cock. Is it strange than at the moment I'm slightly looking forward to only fucking cock on the future?
The wife put the phone down and stopped recording. I was huffing and puffing in exhaustation. I had literally rode my ass off on cock and lost the cum race. I looked behind me and Derek had a massive smile on his face, he also winked at me. He knew he had his own personal sissy slut fuck toy whenever he wanted.
"Well, well, well, babe, it looks like you enjoy getting fucked by a big cock more than you like fucking my pussy. I mean you even came from fucking a cock too, though it is a shame you didn't cum first. As I said, if Derek came first you will be our sissy slut. You will dress like a woman and act like a woman whenever you're at home. You will never fuck me again. Your little cock will stay locked forever, and to be honest I'm glad it will as I never got anything from it anyway. I only got off from your tongue. Your cock has always been a let down, never good enough. Look at the tiny mess you've made, you've got a tea spoon of cum the best. Stand up by the side of the bed and let Derek's cum drip out of you" said the wife.
I dismounted from Derek's cock and stood at the side of the bed. The entire time Derek said nothing but eyed me like his possession. I slightly stood with my legs apart and felt Derek's massive load follow gravity inside me. A massive glob dripped out on the floor between my legs. I looked down and I could see just this blob of cum here was much more than mine and yet I still had loads of jizz inside me! About another 4 decent size blobs of cum dripped out, I'd say about two tablespoons if cum lay on the floor between my legs.
"Here you go, Derek, she's yours as well now" smiled the wife as she gave him a one of the two keys to my chasitity.
From this day forward I knew I was the bitch.