I have been a secret cross dresser since being a small child. It all started with my fascination with my mothers plastic mac and satin ball gown in the 1950s. When I used to dress up when left alone in the house. In those early days I did not understand why I had these wonderful feelings when dressed up but knew I enjoyed it.The dressing up continued right through my teenage years & into adulthood, and expanded into a fascination for PVC and rubber.
In my mid 20's I got married to a wonderful woman called Sarah. Sarah is a fuller figure lady & had a number of very sexy satin nightgowns and a couple of long Taffeta ballgowns, which I used to play with when left alone in the house. This continued for about 12 months and during this time I encouraged Sarah to wear her satin night gowns as often as I could. Often this would lead to me getting very aroused when cuddling up to her in bed. She used to joke that if I did not behave myself she would stop wearing them, but would always let me have my wicked way I think she enjoyed the attention and liked to tease me.
During one of our sex sessions I had tied Sarah up using satin head scarves which she enjoyed, & was caressing Sarah's nipples through the satin nightgown whilst whispering in her ear telling her what I was going to do to her. I also confessed as to how much I liked her satin nightgowns & how much they turned me on. Sarah told me she knew how much I enjoyed her satin and asked if I would like to wear one whist making love to her. My penis which was already hard almost exploded at the thought of this. I untied Sarah and she slipped of her nightgown and slipped it over my head pulling it down over my quivering body.
Sarah now took charge and before I knew what had happened I was tied spread eagle to the bed, & gagged with a rubber glove and Satin scarf, Sarah used another satin scarf to blindfold me. Sarah then whispered in my ear just what she had in mind for me and confessed how much it turned her on to dress me up in her satin as she had always fantasized about being bound and gagged by a beautiful lesbian and being forced to make love to her.
Sarah stated to rub my nipples through the satin whilst gently rubbing my throbbing manhood with a pair of her satin knickers. It did not take long for me to explode into the knickers, and the feeling of my wet cum flowing around my still erect penis was wonderful as I stained at the satin scarves and moaned through the rubber gag my body writhing in ecstasy as Sarah brought me to the most intense climax I had ever experienced. Sarah united me and allowed me to get cleaned up before I took charge. I quickly tied Sarah spread eagle to the bed gagging and blindfolding her. Still wearing the satin nightgown, I slipped on some rubber hairdressing gloves and began to play with her. whilst whispering in her ear telling her what a naughty lesbian I was going to be. We enjoyed the most fantastic sex which went on late into the night before we both fell asleep.
These play sessions continued although it was always me who initiated the games and would dress up in a nightgown stockings and suspenders surprising her when she came into the bedroom. This always lead to fantastic sex with me firstly tying her up, gagging her and blindfolding her, then being a very naughty sissy with her. After which she would take on the roll as a very naughty mistress tying me up, gagging and blindfolding me with a silk scarf.
However I still had my fantasy and longed for her to sissify me, dressing me up in a sissy satin bra, stockings and suspenders, a corset, satin knickers, a nice sissy satin blouse zipped up at the rear and padlocked, and a sissy satin long skirt finishing me off with high heals and a wig. Then fitting me with a vibrating butt plug. Sarah was aware of my fantasy, whilst always promising to fulfil my fantasy for me never seemed get round to doing anything about it. Years came and went and our games continued, with us introducing some more toys and continuing to have fun and fantastic sex. Whilst not forgetting about my fantasy, I accepted that it was never going to happen.
My birthday was looming and we discussed what to do for my birthday. We decided that we would go away for a long weekend to some nice secluded hotel in the country or perhaps a spa where we could relax and perhaps enjoy some of our sissy games in the privacy of our room whilst there. Sarah decided she would make the arrangements and the venue would be a surprise for me but did promise that she would ensure I enjoyed my birthday and that she would arrange some special surprise for me. My mind raced as I immagined what Sarah had planned. Not knowing what exactly she had planned just added to the excitement. The plan was to travel Thursday morning and to arrive at the venue by mid afternoon the same day. I booked the time off work Thursday – Tuesday giving us plenty of time for our trip.
The day finally arrived. Sarah had taken care of all the packing so I had know idea what we were taking with us or what toys she had packed for our naughty weekend. Sarah drove, the journey taking a couple of hours. We were deep in the county side with nothing for miles around. We tuned of the main road down a long track that lead to a most imposing building with large high gates and a high wall. At the gate there was an intercom, Sarah pressed the button and spoke to the reception and the gates slowly opened. The building was set in beautiful grounds and was very secluded, we drove up the gravel drive to the main entrance entering the building through the large entrance doors. The foyer looked like the entrance to a stately home with a large beautiful reception desk to one side.
The receptionist was dressed in a white uniform dress with wide black belt, similar to those worn by dental nurses. We were welcomed by the receptionist who hopped that we would fully enjoy or stay in the Secret Spa and Clinic. After signing what seemed to be the usual hotel/spa forms, we were shown through to a lounge where we relaxed with a welcome drink, whist our luggage was taken to our room.I have to say this was all very nice and the anticipation of what was in store for me was making me quite excited. After finishing our drinks we were shown to our room, when I say room it was more like a suite and were left to settle in. Sarah, went through to the on suite bathroom to freshen up leaving me flicking through the TV channels and exploring the suite. On one side of the room there was a locked door, which I assumed lead through to the adjoining rooms which would be used when families stayed giving access from one suite to another.
After a few minuets Sarah returned having freshened up,and told me to check out the bathroom which had a double walk in shower & and a very large Jacuzzi spa bath. Sarah followed me into the bathroom standing behind me and stroking my penis suggesting to me that I relaxed and took a long hot bath while she would unpack and then perhaps join me for some fun in the bath. I did not need telling twice and started to fill the bath, I was also getting a little aroused at the thought of having fun in the bath with Sarah. Once the bath was filled I got undressed with a little help from Sarah who could not resist having a stroke of my now stiff manhood.
Sarah nibbled my ear and told me to be good and she would be in shortly to deal with me. Deal with me I thought !! I was not sure what this remark meant but was sure it would be fun. The thought of being dealt with by Sarah invoked all sorts of images and just served to excite me more, making me stiffer and I was now having great difficulty in keeping my hands off myself. Sarah disappeared into the bedroom leaving my with all sorts of thoughts. After about 10 minuets the bathroom door opened and Sarah stood there wearing a white nurses uniform with a wide black belt just like the receptionist, stockings and High heels. She was also wearing a rubber apron and rubber gloves.
Now I really could not control my manhood which was now standing at attention. Sarah came over to the bath and looked at my manhood took it in her hand and gently started to stroke it, bringing me almost to a climax & then skilfully stopping leaving me squirming in ecstasy. Sarah washed my down then instructed me to stand up and get out of the bath & was holding a large white towel out for me. After carefully drying me which involved some carful stroking of my very stiff manhood with her rubber gloved hand. Once again skilfully stopping just before I reached a climax. Once dried she disregarded the towel and produced a large tube of cream which she carefully applied all over my body. The cream had a strong smell and a slight burning sensation. When I asked what it was she told me that it was a hair removal cream and that I was to give it a few minuets to do its work and I was then to shower it off using a very feminine shower gel that she gave me. As I stood in the shower the plug hole started to fill with my body hair leaving a very smooth feeling skin. Sarah told me that she would be back shortly and that I was to stay in the shower until she returned.
Sarah returned a few minuets later carrying what looked like a satin hairdressing gown. After Sarah made sure that I was fully showered I was instructed to get out of the shower and was dried by Sarah using a large white fluffy towel. All this attention again made me stiff something that did not go unnoticed by Sarah. Sarah then held out the satin gown and I slipped my arms into the long sleeves, the cool silky satin felt so good against my now smooth hairless skin. Sarah tied the gown at the back and then placed a large plastic cape around my shoulders which covered my shoulders and hung about half way between the top of my shoulders and my elbow. Both the gown and the cape were a very feminine pink. Sarah then lead me into the bedroom and sat me down at the dressing table which had its mirror covered and Sarah gave me a full makeover, Stopping occasionally to stroke my very erect nipples through the satin gown with her rubber gloved hands. This was getting too much for me and a pre cum wet patch appeared on the satin gown. Sarah finished my makeup & then applied a long blond wig to me. Sarah uncovered the mirror to show her handy work. Sarah had taken her time and had turned me into a very beautiful sissy complete with bright red glossy lipstick.
Sarah stood me up and immediately noticed the wet patch, mmm I think we had best deal with that she said. I don't want you to stain your satin underwear. Sarah reached into a draw and pulled out a large rubber penis gag which she stuffed in to my mouth pulling the leather straps tight behind my head, the penis gag filling my mouth making it impossible to make a noise. Standing behind me Sarah pulled my hands behind my back and quickly tied them, she then lifted my gown and took my manhood in her rubber gloved hand wrapping it in a satin scarf and gently stoked up and down its stiff shaft milking me to a climax. It didn't take long for my already excited manhood to explode, the warm sperm unable to escape the satin scarf that was enveloping my penis started flooding around my throbbing penis. I almost passed out with pleasure trying to scream out but the penis gag filling my mouth prevented that.
Sarah cleaned me up and lead me to the dressing room where my sissy outfit was hanging up. Sarah untied me and removed my satin gown and plastic cape placing them on a hook. Next Sarah placed a sissy satin training bra around my chest fastening it at the back and carefully adjusting the straps. She then leaned round me and gave my nipples a stoke through the satin bra it felt so good it almost made me come again. Sarah realizing how excited I was getting decided to slip a condom on my erect penis so as to avoid any accidents.
She then placed a satin suspender belt around my waist fastening it at the back. eight suspenders hung from it just waiting for the black seemed stockings to be attached. Sarah lifted one foot then the other carefully rolling the black stockings up each leg and clipping the stocking tops into the suspenders adjusting the suspenders so that they tugged slightly at the stockings. The feeling against my now silky smooth legs felt wonderful and sent shock waves running through my body. My penis still erect and throbbing despite having been milked only minuets before started to drip with pre come into the condom. Next Sarah placed a satin corset around my waist pulling the laces tight and drawing in my waist a good 3 or 4 inches and pushing my breasts up slightly. My body was now taking on a more feminine shape. Next came a beautiful Pink Taffeta mistress blouse which she slipped over my head carefully guiding my arms into the long sleeves pulling it down my body covering my satin corset. Sarah then pulled up the rear zip and secured it using a small padlock and buttoned up the long sleeves. Again taking time to rub her hands down my chest rubbing my nipple through the Satin & Taffeta, it was haven and I gave out a muffled moan whilst sucking on the rubber penis gag filling my mouth.
Next came a pair of pink Satin knickers Sarah placing each of my legs in them and pulling them up to encase my throbbing manhood, this all felt sooo good. Sarah selected a black satin skirt, Sarah held the skirt whilst I stepped into it. She then worked it up my Stocking clad legs and zipped up the rear zipper attaching another padlock. The skirt came just below my knees and was quite full. Sarah then placed a pair of 5 inch black high heels on me with locking ankle straps again adding padlocks to each ankle strap. I really was a sissy trapped in Satin & Taffeta.
I was then lead tottering on my high heels across the bedroom to a full length mirror to see my transformation. My manhood could be clearly seen standing to attention forming a tent in my dress. The taffeta blouse making a wonderful rustling noise every time I moved. This was a birthday to remember, Sarah standing behind me rubbing her hands up and down my body, whispered in my ear asking if I was enjoying being turned into a satin sissy, and was I willing to trust her no matter what. All I could do was moan through my penis filled mouth and nod my head in agreement. Sarah then removed my gag telling me not to speak unless spoken to first.
Sarah took my hand and lead me towards the door linking our room with next door. To my surprise the door was now unlocked and Sarah lead me through it. To my surprise waiting at the other side was a nurse wearing the same uniform as Sarah and holding out the satin gown which was quickly placed over my arms and fastened at the back next the plastic cape was placed on me followed by a large rubber bib. I was then taken through another door where I was lead immediately to what looked like a leather dental chair. I was placed in the chair and my wrist were immediately strapped down to the arms quickly followed by straps around my waist and chest. Sarah told me not to worry and that it was all part of the game. I felt venerable not knowing what was coming next, whilst being very very aroused at the same time
Both Sarah and the other nurse then left the room leaving me trapped and feeling helpless. My penis straining in my satin knickers and dripping more pre come in to the condom. A few minuets later Sarah and the nurse returned but were now wearing surgical gowns and hats. Face masks hung around their necks. Sarah again told me not to worry and that all would be explained to me shortly. The nurse then started to recline the chair taking me to almost flat with my head slightly raised. Next Sarah attached two stirrups to the chair and secured each of my legs to the stirrups. My legs were then adjusted so that my legs were in the air exposing my penis and bottom. Sarah and the nurse then tied their face masks in place and pulled on long rubber surgical gloves snapping them over their cuffs.
The nurse then wheeled a stainless steel trolley over which was covered with a green cloth. Sarah then explained that they would be shaving my genitals and that I was to be brave & keep as still as possible. Not that I could move much being strapped down as I was. The nurse lifted my gown and skirt and proceeded to cut my satin knickers off releasing my very stiff throbbing manhood. She then fitted a frame over my waste and placed green sheet over the frame so that I could not see what was happening.
The nurse then began to lather up my genitals and proceed to shave me. The feeling of her rubber gloves holding my penis was fantastic and I almost came in the condom. When the nurse had finished shaving me she cleaned all around my manhood and bottom carefully drying me off. By this time I was having real difficulty in controlling myself and was enjoying every moment.
Sarah then wheeled another trolley over from behind me and placed it just to one side of my head. The trolley was also covered with a large cloth which almost touched the floor. Sarah then proceeded to attach something to the dental chair behind my head which was just out of my vision line. Sarah then explained just what was going to happen to me. I was going to be fitted with a large vibrating butt plug which the nurse then showed me. The butt plug was very big and I began to plead with Sarah that enough was enough & I did not want her to hurt me. Sarah then pointed out that I had willingly signed an agreement to have this treatment. I protested but the forms that I signed earlier when checking in were produced, which I had not read and had assumed were the normal checking in forms. How wrong could I be, I had signed agreeing to become a sissy maid to Sarah agreeing to be kept permanently in Satin and to be put on hormones to slowly change me into a sissy.
Sarah continued to explain that they would lubricate me fully so as to cause as little discomfort as possible, and that I would be given something to help relax me. I continued to plead but to no avail. Sarah told me that as this was my fantasy & she was going to make it come true and there was nothing I could do. I would become her lesbian sissy maid.
The first part of the treatment involved me having an enema. I started to struggle at the same time pleading for this not to happen. Sarah nodded to the nurse who placed the enema tube into my bottom and switching on the pump it quickly flooded my bowls with a warm liquid. The enema tube had a rubber bung which prevented me from discharging myself. Sarah told me that I must learn to control the enema as I would be having them on a regular basis as part of my sissification.
After what seemed like hours the nurse placed a bowl under me and removed the rubber bung. The feeling of relief was immense and the bowl quickly filled as I lost control. They cleaned me up mopping my sweating brow, with Sarah still trying to reassure me. I was still straining at the straps holding me down in the chair and again pleading to be released. Sarah now uncovered the trolley that she had placed next to me. Revealing a anaesthetic machine with two gas bottles a rubber face mask hanging on the side and rubber re-breathing bag.
I moved my head from side to side violently shouting and pleading. Sarah told me that I was to be given gas to put me to sleep whilst they instated the butt as I had not had a butt plug fitted previously and she wanted me to be pain free as promised. I continued to struggle to no avail. Sarah stood behind me and placed her rubber gloved hand under my chin pulling my head back into the head rest. She quickly turned on the machine and forced the hissing rubber gas mask over my mouth and noise. Sarah then attached a head harness to the mask which she had fitted to the chair earlier which kept the mask firmly in place . Sarah continued holding me under the chin and pulling me firmly back into the head rest and telling me not to struggle and to take deep breaths. The sweet smelling gas quickly filled my lungs as the re-breather bag went in and out with each breath I took.
I soon felt this warm feeling flood my body, my legs started to tingle and I drifted off to sleep. I came round with the mask still firmly placed over my mouth and noise and was now breathing gas and air, which kept me in a dazed state unable to fully understand what was happening to me. Sarah and the nurse had inserted the large vibrating but plug placing a strap around my waste to keep it firmly in place. I moaned with pleasure as Sarah switched on the vibrating butt plug. They had also fitted a penis milking device on me and I was quickly brought to a dazed climax. Cleaned up and this was repeated several times over the next hour or so milking me almost dry whist the butt plug buzzed away massaging my g spot and giving me gas induced climax after climax whilst dressed as a sissy.
I was kept strapped in the chair on gas and air and in a semi dazed state for 24 hours being milked every hour by the nursing staff. After 24 hours Sarah returned and increased the gas I drifted off into a gas induced deep sleep. When I woke up I was strapped to a bed in a private room and had been undressed and placed in a very sissy satin nightgown. As I came round I noticed Sarah was sat next to me still in her nursing uniform, and was stroking my head telling me what a brave little sissy I had been even if I had made a bit of a fuss I could still feel the butt plug firmly inserted in my anus. Sarah told me that today I was to start my daily hormone treatment and I would soon begin to feel like the sissy I wanted to be. As I started to protest Sarah inserted a penis gag into my mouth securing it with the leather straps. That should keep you quite she said. A few minuets later the nurse returned to inject my hormones. The nurses continued to carryout the hourly milking switching on the butt plug to ensure a quick climax. My sissy life had begun and all because of a fantasy I thought would never happen.
Part 2 to follow soon: