The Training of a Sissy Whore

I met Bill and Jane through an advert they placed in a contact magazine.

The ad read "Dominate professional couple, early forties, seek submissive bi male / TV to train as their sex slave and party toy. Must be clean, discreet, obedient and very broadminded."

I answered their ad and we entered in a series of correspondence via, letter, email and eventually the telephone. They explained that they had considerable experience and had been involved in the fetish scene for some years. They also explained they were members of a local fetish group and were looking for a sub TV to train as their sex toy and plaything. The successful candidate had to be completely subservient to them and obey their every instruction without hesitation never mind how humiliating or degrading it was. Their slave would serve them both sexually and also entertain and serve their friends and any one else they decided.

Once the slave had been sufficiently trained they would be expected to serve and perform as instructed at gatherings of the fetish group. They were financial secure and could provide accommodation and equipment to act out various scenarios and where also prepared to invest in clothing and toys for their slave.

I explained that I was a 28 white male new to the scene and although inexperienced I had long fantasised about serving a dominant man or woman and acting as their plaything. I also explained that I had often experimented in dressing in my sisters clothing, before I moved out to a place of my own, but I has never had the courage to do it front of anyone else. After further discussions and the agreement of initial limits and safe words we arranged a meeting.

My stomach was full of butterflies when I got off the train at the instructed station. I left the station and proceeded to the car park where we had arranged to meet. I recognised Jane straight away from the pictures we had exchanged on line. She was standing next to a large range rover parked against the rear wall of the car park and was even more stunning in real life than in her picture. She had long blonde hair and an excellent figure for her age. She was wearing a full-length leather coat over a tight black sweater, black jodhpurs and knee length black leather boots.

I walked over to her and quietly said "Hi are you Jane" "You will call me Mistress Jane at all times you little slut" she replied at the top of her voice causing people passing back to look. I went bright red and quietly said in reply "Yes Miss sorry Miss" "I can’t hear you she said "Yes Miss" I replied again louder this time causing more people to look and my face to go redder. "Good she said now get in the car". I went to get in the passenger door but she stopped me and said, "no, slaves go in the boot" and pointed to the back door of the range rover.

I walked to the back and she opened the door, but before I could get in she asked me if I was dressed in accordance with their instructions, which they had given me previously in our last telephone conversation. I said yes and she then asked me to prove it I looked at her somewhat shocked. I had been instructed to purchase a black suspender belt, a pair of fishnet stockings and a pair of black thong panties and to put them on under my normal clothes. "Take off your pants" she said "and show me your underwear slut" I didn’t know what to do or say. It had been embarrassing enough having to buy the underwear in the first place in front of a giggling young girl who obviously knew by my embarrassment and lack of knowledge of sizes that they were for me, but to drop my pants here in a car park and show the world what a sissy I was, dressed in sexy underwear I just froze.

"Right slut you have a choice" she said "you can do as I say immediately or you can turn around get back on the next train and never contact us again, we don’t want timewasters we expect obedience this request is nothing compared to what we expect you to do so its your choice start as we mean to go on or leave"

My hands shaking a reached for me belt and began to remove my pants.

Mistress Jane just stood their smiling as I began to lower them "right off" she said and so I slipped of my shoes and began to pull them down revealing my black suspender belt and panties. When my pants were fully off she made me stand straight and then spin around so she could look at me. She then told to stand still while she went to get something from inside the car. As I stood there I looked around and although the open rear door of the range rover and the wall behind it offered some protection there were at least three or four people mostly women looking on. I could see them talking amongst themselves and shaking their heads and tutting.

Finally after what seemed like an age Mistress Jane returned with a pair of high heels "these should fit you like a glove" she said "as long as the sizes you gave me over the phone are correct". I took the black high heels from her and slipped them on. When I stood up Mistress Jane looked at me and said "not bad slut you have potential", just then a couple of builders walked passed and one of them mockingly wolf whistled at me, much to Mistress Jane’s amusement. She then made me curtsey to them as a thank you, which put them both into fits of hysterics. Finally she allowed me to get in the boot of the car and we were off.

After about twenty minutes we arrived at a large house set back from the road. Mistress Jane let me out and ordered me into the house, still dressed in my stockings and suspenders and high heels, she then led me upstairs and into a small bedroom. It looked ordinary enough with two large wardrobes on either side of a large cast iron style bed with metal railing type headboards at both ends. The room had an on suite bathroom and I was instructed to strip naked and wait while Mistress Jane prepared my bath.

She made me get in and then applied a hair removal cream all over my body from the neck down leaving only a small triangular patch of hair over my genitals. She then rinsed me down and ordered out of the bath and onto my hands and knees on the floor, she then left for a short while and returned with an enema kit which she then proceeded to use to clean me fully out.

I was then led back into the bedroom where Mistress Jane had laid some clothes out for me. The first item she picked up off the bed was a pair of false breast forms, which she attached to my chest with some type of glue, next came a black corset. Once on she had me lie face down on the bed while she got on top of me and put her knee into my back to enable her to tighten the corset at tightly as possible. When she had finished I could hardly breathe but it had had its desired effect as my waist was pulled tight and my false breast forced together and up to form quite an impressive cleavage. Then came a pair of stockings, which once on, where attached to the straps hanging from the corset. Then came a pair of black thong panties. Once these where on she had me sit on a small stool in front of a dressing table, she then went about applying false finger nails and then painting them bright red. She then spent some time painfully plucking my eyebrows and then she applied foundation, mascara, blusher, eyeliner and finally a blood red lipstick to finish.

She seemed very happy with her handiwork and told me I looked like a real slut, she then went over to one of the wardrobes and produced a long blonde wig which she fixed into position, she then had me stand up and walk over to a full length mirror fixed to the far wall. When I looked in the mirror I couldn’t believe it was me I was looking at.

I looked like a very sexy, very sluttish woman. Mistress Jane stood behind me admiring her handiwork "Oh baby she said you look hot just wait till Bill gets home he is going to give you such a fucking, I cant wait to see his big fat cock going in and out of your sexy red mouth, oh you are going to look great splattered in his cum". While she was talking I could see out of the corner of my eye that she had her hand down her pants and was playing with herself. She then said "Oh you naughty little slut you are turning me on come over here and kneel by the side of the bed."

I did as I was told and she lay back on the bed in front of me she then told me to take of her boots, then pull down her jodhpurs, as I did I could she was aroused as her white knickers were wet and she smelled of sex. She reached down and pulled her knickers to one side and said "lick my pussy bitch and you better be good" I quickly dived my head into her crotch and began to give her the best cunnilingus I could. After a while she began to pant and ordered me to take her knickers off she then lifted her legs up and told me to lick and tongue her ass "that’s it she cried stick your tongue right up my ass". After a while she lowered her legs and told me to lick her clit until she suddenly let out a cry, shuddered and came.

I lifted my head from her lap I was covered with her juices and when she saw the state I was in her eyes lit with anger, "look what you have done you little slut you have ruined your makeup you will be punished for this, up and over my knee" she then shuffled to the end of the bed and sat up. I got up and laid over her knees she then lowered my knickers to my ankles and began to spank me. Blows rained down over both my cheeks which were soon stinging and glowing red. Tears began to form in my eyes as the assault continued. Suddenly she stopped and said "you are making my hand hurt with this spanking now I am really going to have to teach you a lesson, you little slut" she then ordered me to stand up and go to the end of the bed.

She then had me bend over the metal bed end while she went over to one of the wardrobes.

Inside it was an impressive array of whips, canes dildos and all sorts of other weird and wonderful sex aids. She pulled out a pair of handcuffs and proceeded to handcuff my arms to the bed end. She then when back to the wardrobe and returned with a leg spreader, she roughly pulled my knickers completely off and then forced my legs apart and attached the leg spreader between them. She then returned to the wardrobe and spent some time examining the canes and paddles hanging there.

All the while I was standing there bent over the bed end, my bum completely exposed and vulnerable, still smarting from the spanking. She finally settled on a long wooden cane, which she removed from the wardrobe and began to viscously swing in practice, I could hear the swish as it passed through the air and I felt my arse cheeks involuntarily clenching in anticipation of what was to come

"Right you little slut I am going to teach you a lesson you wont forget. I will start with eight stroked after which you will say thank you Miss can I have another, do you understand", "Yes" I said, "yes what bitch" screamed, "Sorry Miss I mean Miss"

"Well you have earned yourself another two stroked for that," she said.

She then walked behind me and I could hear and feel her measuring the distance, aiming her strokes and then suddenly there was a swish and I felt a shot of pain right across the cheeks of my ass. The sting of the pain took me completely by surprise and I cried out, then remembering what I had to say I said "thank you Miss can I have another"

"Of course slut" she said and then there was another swish followed by the same unbelievable pain "thank you Miss can I have another" I cried.

Suddenly the next stroke hit, I was beginning to sob now my bum felt like it was on fire tears were in my eyes "thank you miss can I have another" I said between my sobs. The strokes continued to rain down until at last I felt the tenth stroke sting across my bum. I was properly crying now and I was almost to choked to speak but I managed to say, "thank you Miss can I have another"

"No, you cant have any more" she said, "but I am pleased you took your punishment well" she then removed the spreader bar and unhancuffed me. I collapsed to the floor and Mistress Jane left me there from some time as I sobbed and tried to rub the soreness away. Eventually she ordered me back into the bathroom to clean my self up after which she reapplied my makeup and made me put my knickers back on. She then had me straighten my stockings while she tidied my wig. She then produced from one of the cupboards a black leather mini skirt which she instructed me to put on. It fitted me perfectly, but it was so tight and short that it barley covered my stocking tops. I knew if I had to bend over at all or sit down it would give someone an eyeful of the bare thighs above the tops of my stockings.

She then produced a tight white blouse with the three top buttons missing, which meant I couldn’t hide my impressive cleavage. She then had me put on the same high heels I had worn on the way there. I was then made to practice walking and told what was expected of me when Bill came home and how I was to act. I was able to get a look at myself in the mirror while I was walking up and down. I looked like a real slut. You would have thought I was a prostitute going out to work the streets from the way I was dressed and made up and I knew if I had I would have got a lot of business. I sure would have wanted to fuck this little tramp.

Mistress Jane then led me downstairs to the living room and instructed me to get us both a gin and tonic from the drinks cabinet. I did as instructed and returned with the drinks as I bent down to put Mistress Jane’s drink on the coffee table she said "no little sluts don’t bend their knees they keep their legs straight when they bend over, now pick up the drink and do it again properly"

I picked up the drink and then put it back down again this time keeping my legs straight, as I bent over I could feel my skirt rise and I knew Mistress Jane had a clear view of not just my stocking tops and bear thighs but also my still red bum cheeks and thong panties.

"That’s better she said no finish your drink quickly and get yourself another it will help put you in the mood for Bills arrival".

I did as instructed and poured myself another large gin and tonic I then went and sat on the couch opposite Mistress Jane and waited.

Just as I was finishing my drink I heard the door open "oh good Bill’s home" Mistress Jane said "remember what to say slut"

"Yes Miss" I replied

I could hear Bill closing the door and taking his coat off and then I heard voices. Voices oh god he was not alone there was someone else with him and I could tell from the voice it was another man.

Mistress Jane obviously saw the look of concern on my face and a smile spread across her face "oh this is going to be fun" she said.

I stood up and turned to face the doorway and saw Bill walk in. I recognised him from his photographs, he was a tall, handsome well-built man with black greying hair. He walked in and after pecking his wife on the cheek, he looked over at me and smiled. The other man followed him in he must have been around forty, he was shorter than Bill and quite fat, he had a greying beard and was already sweating he was in all honestly quite repulsive. He too was staring at me his eyes on stalks and filled with lust. "Well, well, well what do we have her then" Bill said.

Remembering my "lines" I said "Hello Sir my name is SissySlutSue and I am a sissywhore I love to suck cock, swallow cum and get fucked up the ass, how may I serve you". Bill smiled and said well you can start by getting me and Jim here a drink "scotch Jim". "Yeah" said Jim still looking at me with hungry eyes.

I quickly went to the drinks cabinet and got them both their drinks and then brought them back to the couch where they had sat down. As I bent to put their drinks on the table I could feel my skirt rise and then two pairs of hands roughly grope me, my immediate reaction was to straighten up, but a quick glance at the stern face of Mistress Jane was enough for me to realise that I should let them carry on and enjoy it like a slut would. When I straightened up Bill said "I see you have already been a naughty girl I can still see the cane marks on your ass", "Yes Sir" I said.

I was then told to put some music on. I went over and turned the stereo on. Mistress Jane then said "Sue why don’t you entertain our guest, do a little dance for him a nice sexy dance". I did as she said and began to gyrate my hips and shake my body causing my false breasts to jiggle and my skirt to ride up to show my stocking tops and panties. I felt so humiliated but new I had to please my Master and Mistress.

Mistress Jane then said "Sue, lets turn this into a little bit of a striptease, remove your blouse and skirt". I did as Mistress Jane instructed still trying to act as sexy as possible soon I was down to only my underwear and I could tell from our guests heavy breathing he was enjoying it.

"Now Sue I think its time you entertained Bill and Jim and in a more personnel way, on your knees in from of the couch". I did as I was instructed and knelt in front of Bill and Jim. "Now get their cocks out" Mistress instructed. This was it I thought I am going to please these two men like a woman would, like a slut. I reached out my hand shaking slightly and began to undo Bills belt then his pants. I could feel the bulge of his cock as I undid his fly and reached into his boxers, my hand found his cock and closed around it. It was warm and I felt it twitch and grow as I began to move my hand up and down it. I let go of it for a moment and grabbed the waistband of his pants and boxers and pulled then down to his ankles.

Raising my head I came to face with his now exposed and fully erect cock.

It must have been a good seven inches long and quite fat I reached out and grabbed it again and began to wank him up and down. I was mesmerised by the site of my feminine looking hand with its bright red nails playing with another man cock. I was snapped out of my daydream by Jim grabbing my free hand and placing it on his crotch area. Turning my attention to Jim I undid his pants and pulled them down. He was wearing briefs underneath and they were being stretched by what appeared to be a very big cock. I reached under the waistband of his briefs and pulled them down to his ankles. His cock sprung out and pointed skyward, it was huge at least ten inches long and as thick as a wrist. I gulped when I saw it "impressive hey I thought you would like it you slut" said Bill "that’s why I invited Jim I thought if you were going to be broken in tonight it may as well be done properly".

"Now get sucking and wanking I want see those cocks rock hard slut" said Mistress Jane "and do a good job not every slut gets suck lovely big cocks to suck, so you better do a good job and look like your enjoying it"

I turned to look at Mistress Jane and saw her sitting in the armchair opposite, naked now herself, with her legs spread. She had got hold of a large double ended dildo from somewhere and was playing with herself as she watched.

I used one hand to wank Bill’s cock and with the other I guided Jims monster to my mouth. I gingerly stuck my tongue out and began to lick the end of his cock, a large drop of pre cum had formed at the slit and I ran my tongue over it and licked it up. It tasted salty but quite sweet. I then ran my tongue from his balls to the top of his cock and then over the sensitive glans, I knew how much I had liked this when I had my cock sucked and from the moans Jim was making he liked it to. I then began to lick and suck his balls, "further round bitch lick my ass" said Jim. I was appalled at the thought of licking this fat sweaty mans ass but my rock hard cock stuffed in my panties was evidence enough that it was really turning me on being a slut for this man.

I started to lick between his legs and then started rimming his asshole, I then made my way back round to his cock licking all the way. I then lifted my head and opened my mouth as wide as I could and then lowered my head and took his cock fully into my mouth. It was a struggle to fit it in and I could only get about a third of its length in.

"That’s it bitch suck it suck it good" said Jim as I began to bob my head up and down on his cock. As I did I began to use my tongue to lick all over his shaft. "Open your mouth and straighten your head and neck, then you will be able to get him right down your throat" said Mistress Jane.

I did as I was told and slowly but surely I managed to get his entire length in my mouth. Even thought it was humiliating I felt pride when Jim said "oh baby not women can take it all and your doing a mighty fine job for your first time, just wait till you meet some of the brothers down at the fetish club, they really have big cocks and will just love a little white hoe like you to play with"

"My turn now" said Bill and I raised my head from Jims lap, leaving a trail of red lipstick and my saliva all over his cock. I began to lick Bills cock and then took him fully into my mouth, sucking and licking his cock as my head bobbed up and down. I was really getting into sucking his cock and Bill was telling how he wanted it sucking, or if he wanted me to lick his balls or his ass. After I had sucked him for a while they got up and led to me to back of the sofa. Jim came behind me and bent me over the back of the sofa while Bill went round the front. Bill guided my head back down onto his cock and I began to suck on him again.

Meanwhile I felt Jim squirt something cold and slimy on my bum, oh god he was lubing me up he was going to fuck my virgin arse with that monster. Jim began to slowly stick a finger up my bum, then another, then another till he had three fingers inside me he then began to move them in and out. Although a little painful I found Jims actions quite pleasurable and began to move my hips to meet the thrusts of his fingers "this slut is a natural she loves it" said Jim.

Jim then removed his fingers and I then felt the tip of his cock against my ass. He rubbed his fat cock over my ass and then he slowly began to work it in. The pain as the fat head of his cock slipped into my ass was unbelievable and I screamed out, causing Bills cock to fall out of my mouth, Jim started to pull his cock out and then drive it in again. His fingers had been nothing compared to this and I thought I was going to be split in two as he drove into me again. "All in" he shouted and I could feel his heavy balls against the back of my legs. There where tears running down my cheeks and my legs were like jelly but Jim started to set up a rhythm in and out, I could hardly believe it I was getting fucked in the ass by another a man a very big man.

Jim was properly fucking me now pulling his cock nearly out of mass only to ram it home again. Bill grabbed me face again and forced his cock back in to it. I began bobbing up and down on Bills cock in time to Jims fucking, sucking as hard as I could and licking his shaft as it slipped between my lips. Jim kept on pounding my ass. I felt like I was a human kebab skewed on these two big cocks. I could see Mistress Jane fucking herself with the dildo as these two men gave me the fucking of a lifetime at both ends. All the while they were calling me names like slut and bitch and telling me to suck better or how I was gonna swallow their cum. This just turned me on even more, I was loving being used like a slut by these two men and it was making my own cock rock hard.

After a little while Bill starting moaning and then placed his hands on the back of head pulling it forward further onto his cock and then suddenly his cock began to twitch and then he let out an almighty groan as he began to cum in my mouth. My mouth was soon flooded with hot salty tasting spunk.

Bill held my head firmly and I had no choice but to swallow as wave after wave of spunk hit the back of my throat. I was swallowing as quickly as I could but still some spunk began to dribble from the corners of my mouth and down my chin. Slowly Bill slipped his cock out of mouth "clean it slut" he said and I began to lick and suck the last traces of cum from his cock.

All in all the taste wasn’t as bad I had expected and I felt quite pleased that I had been able to swallow nearly all his load without choking.

Jim was now really pounding into me and I could feel every inch of his cock as it went into me, he started to groan and call me names like slut, whore and bitch, his pace was getting quicker and quicker and then suddenly he pulled out of me. The sudden sensation of his cock being pulled out left me feeling empty as I had just started to overcome the pain and was actually beginning to enjoy it. "Turn round, kneel down and open your mouth slut" Jim instructed. I did as I was told and was once again face to face with his monster. "Now put your head back and stick your tongue out, I gonna cum in your mouth and your gonna catch it all and then keep it till I tell you, now get wanking me"

I knelt with my mouth open and began to toss Jim off into my mouth. After only a few strokes his cock twitched in my hand and then cum started to fly out, it went everywhere, on my face in my hair but mostly in my mouth. He must not have cum for a week judging by the amount that he shot over me.

Soon my mouth was swimming in his cum, it was so full some was dribbling out. "Not a bad load" said Bill to Jim. "Yeah I know" said Jim "now swallow it bitch slowly". I did I was told and forced myself to swallow the thick sticky salty liquid. It was thick and stringy but I managed to swallow it all, then Jim had me lick him clean.

Jim and Bill then went and sat down on the sofa and I managed to get to my feet my mouth and ass still sore from the treatment I had received. "Over her slut" said Mistress Jane and beckoned my over to her chair. "Lie down of the floor" she said and pointed to the middle of the room. I did as I was told and laid on my back, Mistress Jane then came over to me and sat my face rubbing her pussy into my mouth. "Lick me bitch" she said "lick me". I did as I was told and began to lick her clit to another orgasm after a while she turned round on my face and made me lick her arse while she got one end of the dildo she had been playing with earlier and began to shove it up my still sore ass.

After Jim’s big cock the dildo slipped in easy and she began to fuck me with it I actually found I was enjoying it. She then stood up and moved herself down my body, then turned to face me. She grabbed the other end of the dildo and slipped it into her pussy, then using her other hand she began to fuck us both with the dildo alternatively sliding into her pussy and then my ass. With her other hand she pulled down the front of my panties and began to play with my rock hard cock. As her breathing increased as she approached orgasm she speeded up her hand on my cock, with a grunt she came and so did I. I came so violently that cum shot right up my body some of it landing on my own face. Jane then scooped up the blobs of spunk off my body and fed them to me making me lick her fingers clean. Finally she stood up and pulled the dildo from my ass. I lay there sore, the taste of spunk still in my mouth as Bill walked over to me. "Not bad slut, you have potential, you have passed your initiation we will take you on as our slave. Now kiss my feet slut". I got onto my hands and knees and began to kiss his feet pleased that I has passed their test and knowing that this was only the first night of many.