As I arrived at work that Monday, I knew that it would not be a normal day. My throbbing head was a distinct reminder of how my weekend had been.
Saturday night was a blinder. It was my friend Kevin's 30th birthday, and as such, we decided to make it a bit of a blinder. It started out with paintball, went on to karting, dinner, and a strip club. Prague's strip-clubs are something truly special. The girls are beautiful to say the very least, and there's always something for everyone.
We bought Kevin a special treat for his birthday; two strippers took him on stage, stripped him (almost) naked and danced on him. He was totally humiliated, and determined to get us back. The others placed the blame on me, after all, it was my idea, so Kevin decided that I needed to suffer the most.
And suffer I did. As I was sat at the table, a gorgeous latex, corset clad brunette came over to me, fastened a collar and chain to me, and pulled me into a back room. The room looked like some sort of dungeon, with a wooden cross and a leather coated with a hole at one end. The girl seemed young, maybe twenty one, twenty two. She was tall and could've been a model.
"Get over to the table and strip." She ordered. "Lie down, put your face in the hole."
I did as told.
She told me to put my arms under the table. When I did, she clipped my wrists into some cuffs. She then proceeded to whip my ass with a crop. Then she lit a cigarette, blew the smoke in my face, and ran the tip on my skin.
She looked at her watch.
"Your friends only booked 15 minutes with me." She explained. "So, I'll have to be quick." She went over to the wall and lifted a strap-on cock and put it on. Then she put on a condom. She led me over to a leather coated gym horse. She bent me over it and tied me in place.
"Please don't." I begged her.
She laughed. "Don't be a baby." She rubbed lube in my ass, then slowly pushed the cock in me. To save time, she pushed all the way in first time, then began pumping fast and hard. The initial brutal pain subsided, and in its place was a tickling pleasure running up my spine from the prostate. I knew I would never live this down. Eventually, she reached around, grabbed my cock and wanked me off quickly. I came in her gloved hand which she then put to my mouth. "Lick it up."
I did as she asked, then she pulled the latex cock out of me. I felt ashamed, dirty. She had a smug grin.
"If you're worried about your mate, then realise one thing;" she leaned close to my ear and whispered; "I did exactly as he requested."
I groaned as she smiled, walking away.
My mates were in stitches when I walked out. "How's your ass?" The laughed.
"If you mention this to anyone, you're all dead!" I told them, before going on to get seriously drunk.
So, as I sat there, at my desk, I knew this day would not be normal, because in my free time, I found myself looking up stuff about what happened to me, on the net. I found myself reading stories about it, and looking at pictures. I then realised I was disgusted in myself and closed it.
No sooner had I shut explorer down, did our HR manager enter my office. "Mike, I'd like to introduce your new part-time assistant. This is Martina, she's a student." My jaw dropped when I saw her walk in. When she saw me, she smiled, as if recognising an old friend, then she realised where she knew me from and the smile disappeared. She was worried that she'd lost her job even before she started.
I felt sorry for her. "Hi Martina, good to meet you." I told her.
"You too Mr…"
She smiled. "Mike."
The HR manager, Anita, smiled and pointed out Martina's desk, which was opposite mine. Martina thanked Anita, and took her place at the PC. Anita walked out of the room. Martina stood and shut the door.
"Go on then." She said, sitting back down. "Ask away."
I rubbed my temples, preying my headache would disappear.
"There's nothing to ask." I told her. "It's pretty obvious. You're a student, who needs money. But surely the job at the strip-club makes enough?"
She nodded. "More than enough, but I can't put it on my CV can I?"
I laughed out loud. "True enough."
We sat in silence for a bit, then, when I found the time, I delegated some work to her.
"Did you enjoy it?" She asked.
After a moment of silence, I said; "yes I did. Very much, but I don't know why."
"Good. I'm proud of my work."
"Did you enjoy it?"
"Very, very much so. I just play myself. I do what makes me happy."
"So you're a sadist?" She nodded. "Why?"
She shrugged. "I don't know why exactly, I just love to see men, and women, cowering below me. I love torturing them, seeing them cry, seeing them fighting their conflicting emotions. I love every second of it."
"Right. What do you like most?"
"Causing physical pain is great, but emotional pain is best. Humiliation, forcing men to do things they don't like, just so they can please me."
"Hmmm… Forcing what?"
She licked her lips. "Feminisation, homosexuality, public exposure."
I burst out laughing. "You force people to do that? Force them how?"
"I can get any man to do what I want."
"I fucked your ass without too much persuasion."
"Okay, okay, keep that to yourself."
"And what will you do if I won't?"
"Aha, I see how this works."
She smiled. "Don't worry." She got up and walked up behind me. "Still got a headache?"
"Yeah, terrible." She put her hands on my temples. They felt so soft and warm. She rubbed me gently. "Oh God, you're amazing."
"Hmmm…" Her voice was soft. "Close your eyes, and relax." I did. "Do you have a wife?"
"Good. I want you to serve me."
"Excuse me?" I said, jumping up. She pulled me back and continued rubbing my head.
"Sit still. Would it be so bad?"
"Public humiliation? Forced homosexuality? Yes, it would be so bad."
"Relax. I won't do anything you truly don't want to do."
"Can't we start it with a date?"
"Sure. What sort of date?"
"A date, date. Dinner, a movie."
"Great. Then maybe you can come back to mine."
I gulped. "Maybe."
Dinner was nice, the movie was crap, but it allowed us a chance kiss and cuddle. I then took her home and followed her up for a cup of tea.
There was no tea. We kissed the moment we entered the door, and seconds later, we were naked on the bed, with her on top of me, riding me like a cowgirl. She reached down and picked up her pink satin bra, then she started to thread it onto me.
"What're you doing?" I asked her, panting as she bounced on me.
"Indulge me. How's it going to hurt you?"
I nodded, and she fastened the bra behind my back. She kept her hands on my chest and used her thumbs rub my nipples through the thin satin. I had to admit it felt good. She had her first orgasm seconds later, I still hadn't; this was a first for me, usually the sign of an orgasm brought on my own.
She continued to bounce on me. "Can I put more on you?" She asked, gasping for air. I nodded.
She reached into a bedside drawer and pulled out a long pink satin and lace nightie. She lipped it over my head and down to my cock. She rubbed the satin all over my body; it felt amazing.
"Oh God!" She cried out, another orgasm; yet still I hadn't cum. "Do you want to cum now?"
I nodded, confused at how she could induce an orgasm. But she did. I felt her pussy muscles clench down and ripple up and down my cock. I stared at her in shock as I came hard. She pulled off me and knelt over my face. I didn't know what she was doing until I felt the first drop of cum land on my face. I tried to pull away, but she held my face in place and let the rest of the cum fall on my face, then she pissed on me.
"Open your mouth." She ordered. "Do it!" I opened my mouth and swallowed her golden stream. It wasn't so bad, once I got over the initial fight in my head. "Mmmm." She lowered her pussy onto my mouth, then whispered. "Lick up." I did. "Good girl, very good girl." She whispered.
She got up and opened her cupboard. It was full of sex toys and torture implements. She pulled out a cane and flipped it a little.
"Turn over." I did, knowing what was coming. I turned my head to look at her, and watched as she slipped on a strap-on cock. I couldn't help but find the look of a sexy six foot thin woman wearing a 9inch rubber cock sexy. As I was thinking about this, I felt the first lash of the cane on my body. I screamed out. "Yeah!!" She called out. "Cry for me baby girl, cry." She brought the whip down fifteen more times in quick succession. I jumped around the bed trying to get away, but she kept getting me, hard. Tears ran down my face.
She grabbed me by the hair and pulled me to the bed, onto my knees, and then pulled my mouth to her cock. She rammed it down my throat and fucked my mouth hard. "Get it wet bitch, c'mon, get it wet baby girl." She said between clenched teeth.
I did my best, then she got behind me and plunged in, buggering me hard without remorse or mercy.
"You love it bitch. Don't you girl?" She called out.
"Yeah! I love it!"
"Yeah! Tell me baby girl, tell me how much you love it!"
"I really love it. Mnnngghhh…." I moaned as we bucked about on the bed. "God I love it!"
"Me too. Can you imagine doing this every night? Go on, say it, say you'll be my bitch."
"I'll be your bitch."
"I'm your bitch!"
"I'm your bitch!"
"Say you'll serve me forever!"
"I'll serve you forever!"
"Say you'll do whatever I want!"
"I'll do whatever you want! Mnnnnghhh, oh God, this is sooo nice."
"I know. Say you'll do all the things we talked about today!"
"I'll do everything we discussed today! Everything! I promise!"
"You'll let my other slaves fuck you?"
I was silent, as if in a vain hope she might drop the idea.
"Yes, I'll let your slaves fuck me!"
"Good!" As she fucked me, she bent around and gently rubbed my cock, but this time, she wasn't masturbating me, she was milking me. I came, but I had little or no orgasm. I felt unfulfilled, but that's what she wanted. "I need you to stay focused. I need you to really do the things you promised."
"I told you I would."
"But if you orgasm, then your head will tell you otherwise. Get dressed."
"Where am I going?"
"Home. Unless you plan to wear the same clothes two days in a row?"
As I was about to leave, she threw some long pink satin bloomers to me; they had thick white lace around the edges.
"Wait here." She ordered. I stood holding the panties. When she came back, she had two men, both dressed as women, on their hands and knees and on a leash, crawling by her side. "Kiss them both goodbye."
I was shocked by the scene in front of me and didn't move.
"I said, to kiss them both goodbye."
"Who are they?" I asked.
"Two of my slaves. I told you I had slaves."
"Live in? Four. Kiss them."
I got down on my hands and knees and kissed them on the cheek.
"No. Kiss them! Like lovers."
I frowned, tilted my head, and kissed each of them for a good few seconds; our tongues intertwining. It didn't hurt me, and it didn't turn me on that I was doing it, but what did turn me on was that I was being pushed into it. She was right all along. I looked up at her, and she knew what she had to do. "Kiss them again." She ordered. "NOW!" I did. "Feel the satin on them." I rubbed them all over. "Hold their cocks. Their panty covered cocks. Feel the satin and lace." My cock was rock hard. "Rub them." I did. "I was going to save this for another night, start you off slowly, but obviously, I'm too horny. Sissy Jamie, fuck his ass. Sissy Kelly, fuck his mouth." The sissies pulled my pants down, and one of them fed his cock into my mouth, whilst another fucked me. Martina picked up a digital camera and photographed me in all different positions. "That's it, fuck him like the whore he is." She whispered. She bent down to my ear and whispered. "Soon I'll make you look like them. Would you like that?" I nodded with the cock in my mouth, enjoying the sweet humiliation.
The sissies didn't last long, and soon enough I was tasting cum straight from the source, and feeling it fill my ass. I loved every second, for some strange reason. For some strange reason, I felt these men dressed in puffy, frilly, bright satin dresses were somehow extremely sexy, but I just didn't know why.
Of course, Martina pointed out to me just how right she was. "I told you I can get men to do whatever I want, even gay sex."
I frowned at this comment.
She passed the bloomers I dropped back to me. "Wear those under your work clothes tomorrow. And remember, I will check."
I knew this was the start of something very important in my life, but I couldn't think what. If I really did get involved with Martina, full time, then how would I do it? I still had family, I had a high-powered job, and then there was the question of what would I be for her? I asked her that the next day.
She shrugged. "I don't understand."
"Well, you've got these four live-in slaves, yeah?"
"Well, if I was to start seeing you, regularly, what would I eventually be for you?"
She looked at me as if I was some sort of idiot. "You want to know if I would treat you as some sort of lover, or something, don't you?"
"Look, if you were to move in with me, then you would have to become completely enslaved to me. If, or maybe when, that happens, you will be in the same position as the rest of my slaves. You will not spend the night in my bed, you will spend it tied up, gagged, and locked in a cage in my basement. Eventually, I aim to move to a bigger place outside Prague, where I will have about 10 or so slaves who will serve me."
I frowned, disappointed. "So I'll just be another slave to you?"
"Yes. Why is it that every man at the beginning wants to be the one. I don't work like that. You all receive the same amount of attention, the same amount of care, the same amount of everything. In the end, you will have the freedom between each other."
"What does that mean?"
"It means that you will not be free from me, but you will have the freedom to play with the other sissies, in your spare time, which you will have very little of."
"So you plan to turn me into a sissy?"
She sighed. "I really have the urge to spank you right here and now, but I'm worried I'll lose the job. We discussed this last night. I told you, you will look like them. You agreed."
"But that was…"
"In the heat of the moment? Yes. Tough. Anyway, you're already my sissy."
"Drop your pants." It clicked. I knew what she meant. Reluctantly, I dropped my pants to reveal the knee-length pink satin bloomers. Then I pulled the pants back up quickly. The rule was that people were meant to knock on my door before entering, but no-one ever did. In fact, company rule was that all office doors were to stay open unless in a meeting, but Martina had started closing mine. Then again, corporate rules, from the US, stated that I was not to be alone with a woman at any point, but everyone ignored that in the Czech office. Either way, I was worried people would walk in. "Pull them back down and bend over the table."
I sighed, double checked the door, and did as she asked. She picked up a wooden ruler I had lying on my desk, strolled over in her black high heeled patent leather shoes, and pulled down the bloomers to reveal my arse. She then gave me twenty hard whacks on my already sore ass.
"Get dressed." She ordered, and we got back to work. "I'm ordering some sandwiches in for lunch, so don't make any plans."
"Why?" I asked her.
"We're going to eat here, whilst the office is empty."
She made a definite corporate no-no at lunch and locked the office door and closed the blinds. She then told me to bend over the desk with my pants and panties down.
I watched as she dug around her bag and pulled out a latex glove and a tub of Vaseline.
"This is going to hurt, a lot, but you'll like it." She told me, as she also pulled out a ball gag. She put the gag on me, and zip-tied my hands behind my back. She then put the glove on and then rubbed Vaseline all over it. I wasn't stupid, I knew what was coming. She inserted two fingers into me, and pumped them in and out. Then she introduced a third and fourth, making sure to widen me as much as possible. I moaned into the gag as she began trying to add her thumb and get her hand in past her knuckles. Tears ran down my face as I thought I'd be split in two. "God this is one of my favourite things." She moaned. She was using her left hand to rub her clit.
She pushed her hand in hard. I screamed into the gag. With a sudden slip, the hand went in me. I felt my sphincter close around her wrist, and she let out a satisfied sigh. Then she closed her hand into a fist and pushed in as far as possible up her arm. Then she pulled out right to the tips of her fingers and pushed in again. After doing this nine or ten times, she kept her hand a fist and pulled that all the way out, then pushed back in again. She did that faster and faster until I could see her arm was a blur with the speed of her fisting. She milked my cock until I came on the desk, then she rubbed my face in it. She unfastened the gag. "Lick it up." I did.
She then had me get between her legs and lick her pussy.
We cleaned ourselves up, ate our sandwiches, and went back to work.
"After work, go home, get enough clean shirts and socks to last you 'till Friday. Then come to my place. I'll be waiting for you, so hurry." She tells me.
"I prefer, Yes Madam."
It occurred to me that she said until Friday because she worked in the club Friday and Saturday nights. Of course, I was wrong.
"You will be spending the rest of the week with me." She tells me later. "You won't need your own clothes this weekend."
"Don't you need to work this Friday and Saturday night?" I ask her.
"I do, but that doesn't mean you can't wait for me. What do you think the rest of my slaves do whilst I work?"
"I never really thought of it."
"They work during the day, a couple are students, but on Friday and Saturday nights, they spend the night chained up in their cages."
"And they don't mind?"
She shrugged. She doesn't care.
It was a strange feeling. Not something I wouldn't like, just a strange feeling. It was if my body was in a strange battle with itself, but I didn't know which side I wanted to win. I decided that since I had done the things I had done in the past few days, then this should not matter so much, but for some reason it did.
I stood there, in front of Martina and her four slaves, each one dressed the same way I was, feeling embarrassed. The puffed up satin party dress was not meant to be sexy, in its original form, but was in its current form; at least I think it was.
Martina was proud of herself. She hadn't done my make-up, her slaves had; which made her all the more proud because it meant she had trained them well.
"Tonight, I want you to do some things you would normally never consider doing." She explained. I was slightly confused. "By that, I mean work things. For example, my personal toilet is next door. I expect you to clean the rim and seat with your tongue."
My stomach jumped when I heard that. "But that's unhygienic." I told her.
She slapped my face hard. "Don't be stupid, I'm not going to make you do anything which will make you ill. I don't shit on my seat or rim. Now, the next thing I'm going to expect you to do is to hand wash all my lingerie. I expect you to be the toilet tonight, for me and my slaves. The rotation changes on a nightly basis."