tagTranssexuals & CrossdressersBecoming My Roomate's Wife

Becoming My Roomate's Wife

byAlberta_CD_Slave©

This story is true and is based on what has happened in my life in the last 6 months. Basic details have been changed for anonymity reasons.

I am a bi-sexual MtF crossdresser and have recently started being dominated by my best friend. As part of my submission to him he has ordered me to start writing up how our relationship started and what it has evolved to.




Him becoming my master started a year ago when we moved in as roommates – we are both in our mid 20's and had relationships break up at the same time (we were sharing apartments with our girl friends at the time). We have known each other for more than a decade and have no secrets from each other which included him knowing I like to dress up as a woman from time to time and knows that I am bi like him, including having given him a couple blow jobs over the years.It is actually his older sisters fault that I started cross dressing but that is another story.

When we moved in I brought along a small collection of woman's clothing with me that my ex had help me build up and would dress up about once every other week, usually on a night when he was out of town or spending a night at his current girlfriends place.

Just over 6 months ago he went out for a Saturday night of clubbing with friends and said he was going to crash at a friends house afterwords if he didn't pick up a girl and go to her place and since I wasn't feeling up to it decided to stay home and get into my female persona (we will call her Lindsay). Around 1 AM I was really getting into it had my self fully dressed up, little black dress, corset, heavy pattered tights, padded bra, long blonde wig and full make up – I was looking hot and enjoying it when I hear the front door opening. I didn't think this was going to be a big deal as my roommate had walked in on me a few times before and I just go to my room to finish playing for the night and nothing is said. However he bursts in making out with a little red headed bar tramp just as I am starting to masturbate to a porno I put on about 15 minute earlier.

The girl sees me and freaks out, running out the door (My buddy talked to her later and finds out that she thought I was his actual GF and that she was about to be forced into a threesome not realizing I was a guy in drag.) I stand up and try to apologize to Dan about what happened and he just shrugs. Being fairly drunk at this point he apologizes for not warning me he was coming home and it that it is ok.

I ask him if he wants me to leave or if I can stay out and finish the Porno, he tells me I can stay out as long as I get him a beer. As we are sitting finishing the movie he looks over at me and starts talking.

"you really have started improving your looks and skills with being a woman, I can hardly see the male anymore when you are like this."

"Thanks" I reply in a girlish voice trying to stay in persona "I have been practicing my makeup and voice during the day when I am at home working."

We watch about another half hour when he looks over at me and slowly places his hand my thigh and starts moving it up towards the hem of my dress. "Have you been practicing any other female skills I should know about?"

"Yeah" I respond in a smooth as voice as I can "I practice with a banana once a week like you showed me. Want me to prove it?"

"Maybe you should, given that you scared off my fuck toy for the night, she was interested in kinky stuff so I was going to show her my collection of handcuffs and toys and she how she liked it."

"Oh that sounded like fun, so sorry I really wish I hadn't scared her off, but let me try and at least make it up to you. Let me just go freshen up a bit and I will be back to show off that talent."

I go off to my bathroom for just a minute and make sure my hair is nice and set and touch-up the pink lipstick I a wearing as well as putting on a small spray of perfume. I also change from a pair of little wedge sandals I am wearing to a pair of 5 inch black stilettos.

I walk back into the living room and without a word drop down onto my knee's in front of him and start playing with the zipper on his jeans. Once I get it open I reach inside and start slowly fondling his nice thick cock. After a couple minutes of this he stands up and pulls off his pants completely and opens the buttons on his boxers. He then sits back down on the edge of the couch with his cock staring me straight in the face. Without thinking any more about it I bend in and start slowly sucking on his cock, taking nice long strokes to get as much of it as I can in and the sucking back off until I make a pop sound as I finish off on his nicely cut head. After a couple rounds like that I stop and run my tongue over his balls and back up the shaft. I do this routine for about 10 minutes before he is nice and hard and dripping lots of yummy pre-cum for me to start on.

"Stand up if you want a real treat" I tell him "I have been practicing something really good."

He looks down at me for a minute "Sure but go freshen up again I love that shade on your lips and want to see more of it, and touch up your eyes as well if I am going to be looking down at them I want them nice and standing out so I can see how well you have progressed."

Deciding that he wants a real show I go back to my room and do as he requests, as well as changing into a nice deep purple lace & silk gown and robe set I have. While I am doing this I can hear Dan get and go to his room but by the time I am back he is standing there in just his boxers with that amazing cock of his still rock hard.

"Wow I didn't know you had gotten clothes like that or I would have started suggesting you wear them around the Condo more often."

"Thanks I did a big online order for stuff like this about 4 month after we moved in but didn't want to show it off to much." With that I drop to my knees again and give him a couple quick sucks just to get his cock wet and make sure it is nice and hard. I then lean my head back to open up my throat as wide as possible and start taking his 2 inch wide cock into my mouth and down my throat, deep throating with a real cock for this first time. It took me a couple minutes to get past the gagging reflex but once I did it was the most amazing thing I had ever felt. I was able to keep the deep throating for more than 15 minutes before Dan pulled back and asked if I wanted it on the face or down my throat. At this point I was incredibly turned on and wanted my first facial more than I could imagine. "Shoot it all over my face, and if you are good enough to get past 3 shots I will take the rest in my mouth and swallow."

I reach forward and suck on him for a couple more seconds before he pulls back and starts gushing cum all over my face. The first 3 loads cover my eyes, cheeks and hairline and when I can see he isn't done I open my mouth wide and put it right in front. He ended up shooting at least another 4 loads into my mouth and some started dribbling down my chin. Once he is done he looks down at me "Well aren't you going to swallow that like a good little slut?" Getting even more turned on by his wording and attitude towards me I close my mouth and start swishing the cum around, not enjoying the taste but the feel in my mouth. I open my mouth again and then swallow, allowing him to see me taking his full load. I quickly wipe up the bit that spilled from my mouth onto my chin not wanting it to drip onto my gown with my fingers and suck it down as well.

After that we just kind of stayed still for a moment until Dan reached into a pile of stuff on the couch and pulled out a set of hand cuffs and a fairly large ball gag.

"I was going to use these on that little slut you scared away but since I don't have that option anymore maybe you should take her place." I just sat there on my knees, stunned at what he was suggesting. Part of me was horrified, not that it was my best friends as I had given him a couple BJ's before but because I had heard him with girls he had brought home over the last year and not all of them made happy and pleasant sounds when he was like this. The other part of me though was really getting into it. I hadn't masturbated to an orgasm in more than 2 days and was very very turned on by what had just happened. Also while with women when I was in my day to day male persona I was actually quiet dominant when I was en femme I tended to be highly submissive.

"What exactly are you thinking of doing to me tonight?" I ask him slowly while trying to keep my female voice on, which is actually easier when recovering from a massive dump of cum down your throat.

"Very simple, I am going to cuff you behind your back and strap the ball gag in, after that you are mine for the night, I won't do any real harm to you but there will be no safewords or any way of stopping till I say so."

I was kind of shaken at this point but my hornyness took precedent and I simply turned so my back was facing him, put my wrists together "Yes sir, please take me for the night." Even to this day I don't regret saying those words one bit.

He calmly put on the handcuffs and then fastens the gag into my mouth, it was a huge gag and completely covered my mouth making sure I could not make a sound.

He then led me into my room and bent me over the short side of the bed. "Stay here, I need to go get some stuff from my room."

I couldn't even tell how long I was alone but the standing bent over 90 degrees while wearing stilettos is not fun and was starting to think this was the punishment he wanted to give me.

When he finally comes back he stands outside the door and tells me to close my eyes. He then walks in and fastens a blindfold over me, a very good heavy leather one with separate eye patches I found out later on. "Go ahead and open your eyes tell me if you can see any thing."

Doing as he says I open my eyes and I can not tell the difference from when they are closed. I try mumbling something past the gag but it comes out a couple of grunts.

He then undoes the handcuffs but just for a minute as he pulls my arms forward and over my head so that they are reaching towards the other end of the bed. He re-secures the cuffs and explains that he is securing them with a rope to keep me stretched out that way. He then comes back and puts some lines cuffs on my ankles and starts forcing my legs apart. Once they are well spread he starts talking "The cuffs on your ankles are secure with small pad locks and in a minute I am going to put a spreader bar between them and lock it in place as well."

Once I am completely secured like that he lifts my robe up until it is bunched up on my upper back and pulls down my tights till the ankle cuffs stop them from coming all the way off.

He then starts with a nylon flogger over all of my exposed skin. I have no way of knowing how long this part lasted for but it felt like 20 minutes or more. I really didn't make much noise during this time as it barely stung. He then moved onto what felt like a leather strap flogger. This one hurt much more and once he built up a rhythm and started hitting same tender spots like the back of my legs more and more I started crying into the gag a bit. Once that was done he started using a full leather cat of 9 tails on knots on the stands. I stared crying from this from the first swing to my ass, it hurt more than I could have ever imagined. After a couple more test swings to my back and legs to get his targeting right he starts counting off the strokes and stops at 25. Once those are done he grabs an ice back and starts running it over the worst area's to try and help lessen the pain and heat that is building up. I start feeling relaxed about this thinking it is just about over, especially when he starts rubbing some sort of soothing cream into the worst areas.

After about 10 minutes of this care I feel him pull away and I start thinking that he is getting ready to untie me and have some more fun.

CRACK – without any sort of warning I feel a cane strike directly on my ass. At this point I can't stop my self and I start screaming and sobbing into the ball gag. I lose count after 20 strokes but he just kept on going lining my legs, ass and back like a railroad with that cane. By the end of that I can barely keep my breath as I am so worn out from the pain and screaming. He walks up the side of the bed and leans in towards my head, I can feel his breath on my ear. "Don't worry it is just about over I have only one more toy left to use on you and we will get back to the fun stuff. Just try and focus on the number 10 and it will go faster." This doesn't help me at all cause I have no idea what he is going to use on me next and the idea of 10 hits with anything makes me want to curl into a ball and cry for days.

I hear it a split second before it connects with my left ass cheek, the whistling sound of a full single tail whip being used. I start screaming into the gag again and focus on the number 1. He ends up doing 2 quick circuit hitting each ass cheek, then thighs and then one to my lower back twice. Once the whipping is done he leaves me there until he can tell I have stopped whimpering into my gag and starts using the ice pack and soothing cream again.

"Here is what is going to happen next I am going to untie your hands and release the cuffs and help walk you to the bathroom. Once in there I am going to undue your blind fold and leave you in there for 15 minutes so that you can fix up your make up. Given how much you were crying your eye makeup must me a mess. I only want you to fix it up, not the rest I want to see the cum stains on the rest of your face still. Don't waste to much time looking at your back as the real marks wont show up for a couple of days.

Once I am in the bathroom I do as I am told, I quickly take off my current eye make up and start applying new stuff but in the same colors as before. Knowing how much he likes slutty looking women and wanting to please him to make sure I don't get another beating like that tonight I focus on extra mascara and eyeliner and make sure that it looks perfect. While waiting for a coat of mascara to dry I take a look at the cuffs and bar on my ankles and realize that he wasn't lying each cuff is secured with a small brass padlock and they are attached to the spreader bar by a larger steel lock. I have to be very careful as I am trying to balance my self on 5 inch stilettos with my legs spread 3 feet apart. As I am putting on the finishing touches of makeup Dan yells to me "2 more minutes slut be ready."

Once I am done just stand with my back to the door with hands crossed at the wrist behind my back. The ball gag is huge, at least 1.75 inches diameter and dark blue. Dan knocks at the door and tells me to face away from the door and put my hands in front and close my eyes. I am already in the right position so I move my hands up front and close my eyes. I feel him walk up behind me and put the blindfold back on. "Ok I am going to guide you back to the bed again so do as I tell you to and you won't trip." I start trembling again worried that he is going to repeat the beating or something worse. He can tell I am scared. "Don't worry no more impact play tonight we are going to have some fun now."

When we get back to the bed he ties my hands up top like before with the cuffs and then comes back to the other end and removes the spreader bar and forces my legs apart wider bar, closer to 5 feet I would have to guess at the time.

"Ok you have already agreed to be my toy until I am done with you but I am going to need you to nod your head in agreement, I am recording this on my phone just for safety sake." I start nodding my head, I had said I would do this. "Also do you now agree that I can have protected anal intercourse with you in your current position?" I start nodding again hoping this would be the outcome of the night.

Over the next couple of minutes I hear him getting ready including putting some lube on my puckering ass hole. I was really glad at that moment that I had been playing with my dildo and butt plug earlier that day as it means I would be a bit more loosened up for when he decided to take me.

The only way I can describe what happened next would be consensual rape. While he had put a little bit of lube on my ass I had presumed he was lubing up his cock nice and well. Instead he had put on a pre-lubricated condom and nothing more. He walked up behind me, rubbed the little bit of lube he had left there around and sunk one of his finger to the second knuckle into my ass to get the lube in there, pulled it out and then just starting thrusting his monster cock into me. It took him 4 thrusts to bottom out on me and by the time he had started the third thrust I was crying and sobbing uncontrollably. This was my first sexual experience with a man and it was just brutal. He went on for more than 25 minutes I found out later, just pumping in and out of my while I sobbed into my gag wondering if he could actually split me open inside and occasionally being very glad I had used the plug for an hour just before he got home. I didn't even come during that time, it was just to painful and brutal for me to find any pleasure in it.

When he was finally done just pulled out and smacked my ass. "Thanks slut that was actually more fun then I likely could have had with that bar bimbo. Im going to let you recover for a few minutes and then I will help you get ready for bed.

About 10 minutes later he came back and untied me, and changed the spreader bar between my legs to a 1 foot bar with 9 inch chains coming off each end. Still hind of hobbled me but at least I could walk. He walked me to the bathroom and then cuffed my hands behind me again. "Ok here is what is going to happen, you are going to close your eyes and I am going to take off you handcuffs and put on some soft locking cuffs like on your legs, as you see the night is not done yet. After that I am to remove your blindfold and gag, you are to say nothing. I will then leave and close the door behind me and then I will tell you to open your eyes. You will have a few minutes to get ready for bed, use the toilet, brush your teeth ect. Under no circumstances are you to touch yourself or fix your makeup, you are to stay like this and I will come get you when it is time for the next bit of fun."

I close my eyes as he redoes my cuffs, allowing my arms to be free and then he quickly removed my gag and blindfold. I start moving my jaw around as much as I can to get feeling back into it after having it wedged open for so long. Once the door is closed he says I can open my eyes.

My makeup is a mess, my mascara and eyeliner have run everywhere. I have that fresh fucked whore look and find myself getting turned on by it. Not knowing how much time he is giving me I quickly start brushing my teeth and using the toilet.

When Dan finally comes back I have been able to get fully ready for bed or what ever he has in store for me next. He walks in to the bathroom with a small glass of water and some pills – Tylenol and Advil. "Here take these you are going to get really sore soon so take these to head them off." He is almost being nice to me which make me want to cry after the brutality of what he put me through.

"I changed my mind there is nothing else I want to do to you tonight, I think you should just go to bed now. However if you want the complete experience of what I normally do to total sluts like you I will put you to bed the way I would have that little red head." Since I had not come yet tonight his dirty talk got me really turned on again. "Oh yes please give me the full slut treatment like the whore I am."

He leads me back to my bed and has me sit cross legged on it right near the edge. He pulls out some fairly heavy chains and using more locks attaches it between my cuffs and then down to the bar / chain combination between my legs. "I always leave my sluts locked up for the night just to re-enforce how meaningless and useless they are, now look straight at me and don't flinch or I will redo the beating from earlier." I do as I a told and stare him straight in the face, not knowing what is coming next. Without any real warning or notice his hands come up and slaps me across the face on each side and then quickly spits on my face. "Very good you didn't flinch at all but I can see tears starting. Don't worry I didn't hit hard enough to leave bruises on your face, now lay down on your side whore and I will cover you up. Sweet dreams."

Report Story

byAlberta_CD_Slave© 2 comments/ 57442 views/ 23 favorites

Share the love

Report a Bug

Next
2 Pages:12

Forgot your password?

Please wait

Change picture

Your current user avatar, all sizes:

Default size User Picture  Medium size User Picture  Small size User Picture  Tiny size User Picture

You have a new user avatar waiting for moderation.

Select new user avatar:

   Cancel