As I walked towards the modern house it wasn't quite what I had expected. Joe had worked in an old Victorian house which was rather run down; paint peeling on the outside, weeds in the frontage and a wild hedge that blocked the view of its large bay windows from the street.
I was extremely uneasy about doing this. Scared. Joe was my only experience with a prostitute and she had been more like a girlfriend.
I had met her in a London Hotel. "A hundred quid darling is my starting fee and that's for an hour", she said, dismissing my invitation as a time wasting. She had quite a lot of make-up on and smelt over- powering with perfume, but her face was sweet and her black dress was clingy but not tarty.
I was surprised how calm I felt. Her childish look and smallish features helped. "That's my fee darling. Staying here?", she enquired.
"Yep. Fifth floor, number 538". I wasn't sure what to say, I was just keen to get moving, there were plenty of people around who possibly knew me.
"I'll give you thirty minutes, but I want the money on entry", she demanded.
The session turned out to be much better than I thought. She stayed for well over two hours at my request and I really hadn't had sex like it before. She gave me her working address and I eventually went to see on a number of occasions and we even met for lunch occasionally.
About four months later I asked her a question that I was really nervous about. I had put it off last time but I considered if this relationship was to serve me then my full fantasy demanded more than just sex. I had long fantasized about being feminised by another women, but apart from reading about it could never imagine actually going through with it. My wife and previous girlfriends would have surely thought I was some kind of gay wimp and left me on the spot. The effect it could have had on my career would have been immeasurable.
"What do you think about men who like dressing up as women?", I asked, gritting my teeth in case she laughed. I was close enough to her now, to care about her thoughts. She replied quickly and without flinching
"I've tried a few times darling, but I've got to admit I'm not much good at it." I was instantly deflated as I was hoping she would give me more encouragement and at least suggest we attempt something. "Don't get me wrong. We can have a go, I'm sure it will be a bit of fun, but I've got none of the stuff you need, I'm sure you'll be disappointed".
I was disappointed. I only wanted to try a bit of make-up and somehow, after the big build-up, I had felt let down. My face must have shown my feelings. "Hey I just don't want you to waste your time, but I've got an answer. I know a place that is really excellent for kinky stuff, if you want that sort of stuff they'll do you a treat."
I still felt I wanted to end our relationship immediately. I couldn't see how we could operate now we had had the conversation, but she at least looked unaffected. "What sort of thing do you fantasize?", she went on.
"It doesn't matter, forget I ever asked", I whined.
"Oh come on, Donna I've heard is brilliant, please, you will love it", she enthused as she discussed her idea.
I explained how I wanted to be forced to be dress up as a women, but in particular, the make-up would have to forcefully applied and I quite liked the idea of then screwing a lesbian (or at least a women who found a bloke dressed up as a women a turn-on). I gave her more details and she told me she would sort it.
Donna apparently was a professional. At £500 for the afternoon she had better be an expert I thought. She was meant to be a bit tough and the whole fantasy would be acted on arrival, so I wasn't to start any chatty conversations on arrival. From the moment I entered the door I would be treated as a slave who had been caught and was going to be used for their pleasure.
I was scared. I didn't know how to indicate that I had had enough during the fantasy. What if it went too far, or I wasn't enjoying it. I would have turned away, but Joe had gone to a lot of trouble.
I knocked on the door. I heard the sound of feet echoing along a wooden floor and the door opening. An attractive tall blond hair women open the door. She was wearing a red dress and high-heeled red shoes. Long red fingernails and dark red lipstick. She stared through me and pointed up the hall.
"Into the room", she snapped. I walked past her; my heart was racing, almost wanting to run away. Another smaller girl was in the room. Dressed very formally in a doctors outfit with white coat and professional glasses which defied her age. She would have passed as the real thing apart from her liberally applied make-up. She had a blond bob and was rather busty.
"Right you will be converted into a women for use by our customer. Any disobedience will be punished with this instrument". At which point she plunged the metal prod (which was connected to a power point) against my hand and shocked me. It was very uncomfortable and made my hand numb and then feel like I had pins and needles.
"Hey steady, nobody said about a bloody prod", I shouted. I couldn't believe the cheek of the women, I had told Joe I wasn't into massive dominance although play-acting would be fine; this was far too serious.
She prod me on the other hand and said, "shut-up and get your clothes off".
I did it. I wasn't going to turn into one of those sissies who start begging. I told Joe to make sure she told them I didn't want any hair removed or dildos up arses etc. If they tried to push that one I was out.
I took my clothes off and I put on suspenders, stockings, shoes; I was amazed how well they fitted. I immediately felt weak. It was psychological and I tried to fight the feeling. The high heel shoes stretched out my muscles and made my legs feel quite feminine. I was fitted with false tits and bra and then had tight corset applied. It took several minutes to get the effect they were after. At the end, the reduced waist and the false tits looked realistic and then with the short red dress I looked unbelievely sexy (if not a bit too tall). They then spent a long time whilst a blond wig with shoulder length hair was attached to my head.
The plan seemed to be fitting back into place as the women went about transforming me. I looked in the mirror and I could not believe how well the clothes fitted me and the hair looked unbelievably realistic. The face though, was of a bloke and the changing of that was what I was excited about. To the women's credit they also were doing a convincing job of going about their business, although I still failed to understand why one was dressed up as a doctor.
Donna grabbed me from behind and pushed me. I felt strange on the shoes I had been provided and had to bend my knees slightly and push my ass out to keep balance. "Come this way", the doctor said.
We went to another room that looked a lot more like a dentist's theatre. A large black chair was at the centre of the room with all kinds of gadgets attached to it. There we steel bars at head height and other locks for arms and legs. This was a professional set-up and was very intimidating. If I was going to be forced, I guess this was what I had paid for.
I sat down and I felt my arm and legs get locked to the chair. My first unnerving shock though was the bars I had to squeeze my head between to lay back in the chair. A metal, leather padded concave plated supported my head. Two thin metal clamps were pulled out and then screwed tight against the sides of my head. In the mirror across from me I could hardly make them out as my blond hair flowed over them, but they restricted my head movement from side to side. I felt my cock get hard immediately.
I tried to move my head but it would only move backwards and forwards on two runners. I realised the clamps we connected to two wheels that were connected to two metal runners. As I pushed my head back again I came in contact with the leather plate at the back of my head.
A metal plate, with beige soft material was then place under my chin and the end was extended so two small metal claws just lipped over the bottom of my chin to gain a firm grip. With the clamps holding my head, the chin plate forced my mouth completely shut. I still had freedom to move back and forth although this seemed to be denied when the doctor tightened a screw above my head. My head was completely locked. I looked directly in the mirror and apart from the claws petruding about half an inch up from the bottom of chins, it was hard to see how my head was being held so firmly in place. My hands, legs and torso were firmly held and I felt completely rigid and exposed.
The doctor left the room for a couple of minutes and came back with what appeared to be an array of make-up. 'Here-goes', I thought. I stared again in the mirror and started to admire my hair. Although I felt very strange being so tightly held in place, I was very excited about the experience about to unfold.
They spent a while shaving my beard close (despite the fact I had already done this). They applied foundation liberally and spent a long time trying to get an even colour. The doctor eventually moved away and I must admit it was hard to recognise me from the mirror, I looked more like a ghost.
The doctor then drew some lines on my brows and put on blusher. The loose power flicked into my eyes and the inability not to move a muscle suddenly shocked me. I tried to tell the doctor but it came out as a muffled grunt. By my rapid blinking, she knew the problem and blew into my eyes as some kind of consolation.
The blusher made me look human again, and changed my face in to something more rounded and feminine.
They then went work on my eyes. I decided to blink to make it hard for them. Donna just stretched over and held my lid as several colour were applied. The eyeliner was then carefully applied and Donna held my eyes wide open while the doctor carefully painted. She smudged the effect. They both regularly looked intensely at me to ensure they had achieved the perfection they were looking for. It surprised me how studious they were given that the mirror was at least six feet way and the detail would be hard to pick up from where I sat.
Mascara was applied and then combed through. Again my eyes were forced open to allow my lashes to be stroked. My eyes were beginning to feel slightly heavier with all of the tugging and the newly applied make-up. They went to work on my lips. I found I could squeeze them tight stopping them applying the lipstick properly. The doctor turned a screw that pulled my jaw down forcing my lips apart. Whilst I struggled it was quite painful against my chin. I soon relaxed leaving my mouth ajar to their satisfaction.
They then put on lip pencil and lipstick and then gloss and sealer. The doctor blew on my lips to encourage them to dry. She then applied more mascara and a little more pencil. All the time she treated me like a painter's picture, just finishing the final touches. The doctor moved away and I was astonished by my looks. I was really sexy and the lips and eyes were not my own. I was very turned-on just by looking at myself. I tried closing and opening my eyes slowly and noted the swishing of my highlighted eyes and large lashes.
They put on long earrings and put hair spray on my hair making it stand out slightly. I look quite attractive.
The doctor loosened another screw and I was again free to open and close my mouth. She also loosen the bolt on top of my head allowing me to move my head backwards and forwards. I wasn't sure why I wasn't being taken out of the contraption at that moment, but the new freedom was gladly received.
The women both left the room.
A few minutes passed and I heard some talk outside. A mans voice, I was sure. My heart started beating again. What the fucks a man doing in here, I was told that this would be completely private.
"She is beautify and you have got twenty minutes. You've used it before and no funny stuff just the head okay". I could hear Donna say. I didn't understand what was going on.
The man walked in. He was a stocky middle-aged man in underpants and a tee shirt. He had a large neck and big hands and firm face. He must have been about 45ish and looked very confident (as if he had seen somebody like me before).
"What's going on here?", I shouted "what do you want?"
He smiled in a cool, curious way and came close to me to look at my face. He looked approvingly and felt my hair.
"Shut the fuck up, I've paid good money for you so I don't want you fucking moaning all the way through this session", he said coldly with a scowl.
"I'm a client, I don't want .. ahh". He'd plunged the prod against my hand and took my breath away. I was quite stunned. I started to feel mildly faint as I realised that this was going badly wrong and I was trapped.
"Make anymore noise and you get this in the bollocks" he said. I couldn't speak as I was in shock anyway.
He pulled around a purpose-designed seat that was linked by a swivel arm to the back of my chair head level. The seat rested next to the two runners that allowed my fixed head to move backwards and forwards. He got up on to the chair and was sitting right in front of me. His feet were on my arm rests and his black pants were staring me in the face. He sat above me looking at my face turning himself on.
I suddenly worked out the deal, but somehow I was just too frightened to do anything. Every part of my body was trapped. He start turning screws by my jaw and the claws opened my month wider, he then fixed them in place. My mouth was quite uncomfortably wide open but I tried to relax to ease the pain. He pulled down his pants and then I saw the erect penis. The male smell entered my nostrals as he pulled his foreskin back and forth to achieve a larger erection. I tried to move my head away and was slightly relieved as it slid back from the smell along the runners to the leather plate at the back of the chair.
He did not bother about me at first as he worked on his cock, although his intense staring at me was very unsettling. He then stretched over to get a squeezy bottle with a protruding spout and sprayed some of the contents into my open mouth. It was a bittery sour taste but immediately made me salivate uncontrollably. I then felt my head move forward as he held his positioned cock. It entered my open mouth but it touched my tongue and went back out again. He readjusted the screws and forced my mouth around his cock but just far apart from stopping my teeth rubbing on it. I tried to move my tongue away from his cock but my head was pushed from behind forcing it to rub against the tip. My lips sealed midway down his shaft. The taste was strong as his cock mixed with my saliva. As he withdrew saliva ran out of my mouth lubricating his cock. He moved my head slowly back and forth and I could feel him getting bigger. He looked at me intensely as he moved my head.
"Move your eye lash up and down you bitch", he said. I didn't know why but I did. It seemed to make him move my head slightly quicker.
For a while I got used to the movement although I noticed as he was getting bigger and the tip was getting nearer the back of my throat that meant I had to regulate my breathing with his rhythm. I tried to relax my neck muscles to ensure they didn't ache. For a while I started to concentrate on the experience as the initial shock slightly subsided. His cock was surprisingly hot and the throbbing was noticeable within it. A kind of moan and sharp in-take of breath occasionally joined the rhythm. He moved his cock around regularly to rub different parts of my mouth but seemed keener to push along my tongue towards the back of my throat.
He then without warning changed his pace and started to push harder and more frequently against me. This unbelievebly made him harder again and I could feel the force of his erection push towards the roof of my throat .He started to moan and breath in time with his rhythm. Occasionally he would shout.
"Look at me you bitch". The force of the pushing was now becoming very unpleasant. I felt like I was going to be sick each push and struggled to find breath. The deep blowing and sucking I was doing seem to be adding to his excitement. The speed of my head was over two beats a second for some minutes. I was nearly blanking out when he suddenly stopped.
"Stop fucking breathing, don't move", he ordered as the rhythm stopped. I was so out of breath that I had to breath-in strongly. He quickly pushed my head away and removed his throbbing cock.
"Fucking stop I said", he scream and he took deep breaths as I realised he was trying sustain his orgasm. He then moved my head slow towards him again and I felt the burning hot cock enter my sore month. This time he moved it very slowly. I could feel it throbbing hard. He stopped and then moved it again. Then he got faster and stopped again. I barely breathed and tried to keep my tongue out of the way.
"When I rub your ear I want you to lick the end, but stop as soon as I stop do you understand?" he asked.
I wasn't quite sure what he meant at first, but I complied. He rubbed my ear and I moved my tongue against his cock. He soon took his thumb away shouting, "stop!". He waited and continued again. He repeated and groaned each time taking breath in sharply each time.
For a while I hadn't looked at him, as he seemed to concentrate on his orgasm. I suddenly looked up at his face and he looked at my face and then started pumping slowly and then faster and quite hard but deep again. The rhythm was jerky and I felt him push very hard against me. His cock went deep inside my mouth and held it in. I tried to pull back to breathe but was held tight forcing me to suck hard and gag strongly against his cock. The effect was immediate has he let out a huge moan. I felt the rush of spunk go up his shaft. He pushed hard as the stuff spurted down my throat. The reaction caused me to suck harder, which in turn caused him to sigh loudly again. More was provided until he withdrew my head slightly and pumped more into my mouth. He tried to completely unload the contents for some time. Eventually the penis start to shrink and he withdrew and got off the chair completely satisfied.