This is a print version of story Sissy For My Flatmate, Chapter 1 – Caught In by Yosho from

Sissy For My Flatmate, Chapter 1 – Caught In

My heart was racing as I gazed up at my flatmate, there was an something of an evil gleam in his eyes as he looked down at me and my mind kept jumping back to the events that lead to this moment.

I'm a closet crossdresser, yet now my flatmate (whom I managed to hide my “hobby” from for the past six months) had me on my knees, wearing what I can only describe as the sluttiest clothes I own, hands cuffed behind my back, waiting for the “surprise” he had planned.

The previous night:

Work can get pretty stressful, I'm not complaining – I enjoy my job and I have my own ways of dealing with the stresses of my life. When I get home I like to relax by indulging in my secret hobby. Crossdressing. Now this is something I've always been careful about, I wait until my flatmate (a friend from my University days) has left and lock my door. This way there's no suspicious noises and even if he gets back early, he doesn't have a key to the door of my bedroom.

I started to get changed in to one of my favorite sets. Black stockings, matching suspender belt, panties and six inch high heels. As part of the outfit I also wore a chastity belt. It's hard to explain, but dressing as a girl I felt like I needed to hide my cock away.

I donned my wig and started to lace up my corset. I've always loved the feeling of a tight corset and it gave me a jaw dropping figure (even if I do say so myself).

I put my hands on my hips and started to admire myself in the mirror. Growing up I always hated having a “girly” looking face. I hated wearing shorts, I always got comments about “shapely” legs. I always got my hair cut short, any longer and everyone would call me a girl. Make no mistake – I HATED the way I looked. But since I started dressing up, I had my private moments. In these moments I saw the things that I was picked on for, the things I hated, in these moments I saw them differently. Damn right I looked like a girl and I looked sexy.

I was pulled back to reality when I heard my door open. SHIT! I forgot to lock it!
My heart sank as I realized I'd been caught.

“So that's what you get up to in there!”
Shit! I'd probably go so far as to say that Ben (my flatmate) was my best friend, I'd never had particularly close friends but he was probably the closest friend I ever had. Even HE can't understand.

“Get out...” I whimpered. Trying to muster up a voice under these conditions proved to be soft, quiet and a few registers higher than I hoped for. I even sounded like a girl!

Walking over to me, he put his hands on my waist (no doubt he noticed the effect of the corset)
“Oh, I'm sorry to startle you...” He said in a mocking tone “there's no need to be shy”

“Look! Get out! You don't understand!” I replied, once again whimpering.

He drew his arm around my waist and pulled me closer. “Uh uh. I know your little secret now.” He whispered in my ear. “But I can keep a secret. I know it's your day off tomorrow, I want you wearing that lovely little outfit when I get back. I'll leave instructions for you. By the way...”

He reached in to my panties and grabbed my chastity belt. “Have the keys to that on the table for me”

With that, he left. When I heard the door close, I collapsed on the bed and started sobbing. Ben knew my dirty little secret and to make matters worse he was treating it all like some kind of game. I didn't want to go along with it but at the same time I knew it would ruin my life if my crossdressing became common knowledge. I felt worthless.

The following morning:

Normally I'd look forward to a day off. This time I had a knot in my stomach. Stepping in to the hall, I saw a note on the telephone stand. There were a pair of handcuffs on top of it. This did NOT look good.

I picked up the note and studied its contents:

Sissy, I will be home at 6:30. Make sure I receive a proper welcome. Today you will remove all your body hair. When I arrive, you are to be kneeling in the living room. You will be wearing the clothes I saw you wearing last night and the chastity belt. The keys to the belt will be presented on the floor, in front of you. Additionally, you will be wearing these handcuffs, behind your back. If you fail to follow these instructions or you fail to show me the proper respect, there will be consequences.

The floor seemed to drop away as I read the note. He was getting me ready to do something kinky. The last part terrified me, I had a good idea what the “consequences” would be. I knew I had no choice. I'd never shaved my body before, I'd tried shaving my legs a few times but stopped when I got scared of people noticing. This was going to be a long day.

Later that evening:

He was gazing down in to my eyes. I edged around on my knees, tugging at the handcuffs.

“Well done sissy!” He said, placing his hand on my thigh “So smooth, I'm impressed!”

Sissy – I hated that word! I was fuming, but I found myself getting excited. I'd often fantasized about being in this position. The more I dressed up, the more I started to wonder what it would be like not only to dress as a sexy woman, but to have sex like one.

He presented a key. “Listen, you're probably angry with me. But I assure you, I was never going to tell anyone. I wasn't going to threaten you, or blackmail you or anything like that”

I scowled at him “Then why did you make me do this? Do you have any idea how fucking humiliating this is!” I glared at him while struggling with the handcuffs. “TAKE THESE FUCKING THINGS OFF ME!”

Ben grinned at me. “you know you look cute when you're angry.”

“This isn't funny! Get these FUCKING handcuffs off me!”

I'm sure he did find this funny, I never swear and now I'm swearing like a trooper, while dressed in a way that even the town harlot would find slutty. All the while, looking like a cute, angry chick. What a joke!

“Okay, okay. But before I do I just want you to know that I suspected for a while. I've seen the way you looked at me, or rather the way you stared at my junk.”

He unzipped his fly and pulled out his cock, the same one I'd apparently been eyeing up for the past 6 months.

“You left a draft blog post that I saw, sorry. I know about your little fantasy and I just want you to know that it really turned me on. If you want to act it out, you can.” He now had his cock in his hand and was holding it in front of me.

I know the blog post he meant. I had a fantasy about giving a blowjob on my knees, hands cuffed behind my back while dressed up. My anger faded as I realized he shared my fantasy, it turned him on. Not only that, he found me sexy.

I opened my mouth, closed my eyes and leaned forward. I felt his warm cock fill my mouth, it was everything I dreamed of. I closed my mouth and started to suck, bobbing my head back and forth, feeling my lips rubbing along his erect shaft. I thought to myself, I'm sucking a cock. I'm sucking a cock and I love it!

I started moving faster as I heard him groan. I opened my eyes, looked straight in to his eyes and ran my tongue all the way along the length of his shaft. Something inside me started to take over. I pulled out “grab my head! Grab my head and fuck my slutty little mouth!” - Did I really just say that? I said something that dirty?

He put his hands behind my head. “You really are a little slut, aren't you?” He started thrusting in my mouth. I almost gagged and he pushed it in. “You like that? Don't you? You little sissy slut!”.

I heard him groan more “When I cum, swallow it all, every last drop!”

He stopped thrusting, I instinctively opened my mouth as he jacked off. I felt his warm cum fill my mouth. It tasted salty, strange but nice. He groaned more as he emptied his load in to my waiting mouth.

After the last drop I swallowed it.

He looked in to my eyes and asked “Do you want to be my sissy, my slave?”
Barely able to breathe, I managed “Yes”

“Good. Your next challenge awaits you tomorrow. All the rules will be explained to you, my sissy” He patted me on the head.

“Now, as my sissy slave, you will give me control of your orgasms.” He picked up the key from the floor. “Stand”

I started to raise myself to my feet. Not easy with my hands stuck behind my back, wearing heels struggling with the rush of excitement.

He pulled down my panties, removed the lock from my chastity and attached on of his own. I could now see he was wearing a key around his neck.

“Now, we just need a name for you”

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