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Part 5

It is hard to recount every occasion when I have embraced the female persona that is Stephanie or to recount the number of times I have sat in the bath scrubbing at my skin uttering promises to god that if he forgive me for the sins of dressing as a woman and pleasing myself then I would never do it again. Sadly there are too many. Just as there are too many occasions where I have driven up to clothes bank and deposited my slightly used skirts, bras, knickers and blouses. I often wander whose job is to sort through these banks and if they ever realise what they are looking at, whether they realise that they are looking at the aftermath of a man struggling to accept who they are. I wonder if they think what strange woman has deposited these clothes, or if they think that some freak has a misguided idea of what clothes charity shops want.

I remember one occasion I had stayed with a friend in Cardiff. We had drunk way too much and when I woke the next day I was hung over. After breakfast I was feeling better and was desperate to leave. My partner at the time was visiting with family so I knew I had an empty house to get back to. On top of this I also become horny as hell when hung over and so I was faced with the opportunity to going home to an empty house whilst feeling horny. This meant a chance to get into some sexy clothes and be me for a few hours. I made my excuses to leave and although I was hung over jumped in the car and started to make my way home. I realised on the drive that I passed the outlet shopping centre and this could be the opportunity to buy some new sexy clothes. I stopped, found a shop that looked like it would sell my kind of clothes, quickly dived in the shop and started to browse the rails. As I passed every woman I could feel my face flush. I was convinced the children with their parents would ask “why is that man looking at skirts”, to  my knowledge none did but by this time I was convinced the whole store was going to stop, point and laugh. I held my nerve and spotted a tiger print short skirt (one of my favourite styles). I grabbed it and a couple of rails over there was a white blouse that I thought would match. I grabbed that as well. I was so convinced that people were staring I barely noticed their sizes. I got to the till and paid for my purchase. It was whilst standing at the till being served by the young sales assistant that I had the clear thought of what the hell do you look like, unshaven, smelling of stale booze and no female anywhere to be seen. I could barely look at the woman. She had to have known or she must have thought that my partner was the unluckiest woman alive to have a man like me. I darted out of the store with my purchase wrapped up in its bag. I struggled to make eye contact with anybody convinced that they would all be able to read my inner most thoughts and know that in my bag was my sordid purchase that I planned on wearing and pleasing myself in. I threw the bag into the car. Drove home. I was stripping as I entered the house. I showered, shaved. Found some knickers that I liked and held everything in a nice neat bulge, tights next and a bra. Knickers and bra did not match but I did not care. As I was on my own for the night bra marks did not matter either. A stuffed a pair of socks into each bra cup, as I was going for the full “realistic” look. I then raided the make up drawer for lipstick. Found a nice red and applied it as best I could. I was starting to feel good, hangover gone and the endorphins were flowing. I got my bag with my new purchase in and I had a flash back to how I must have looked when purchasing the clothes, guilt written all over my face but now I did not care, now I was a sexy female and I welcomed the sales assistant stare, now I welcomed the people in the shop looking at me, now I wished that they had asked me what I was doing because now I would have told them that I was beautiful person who looked sexy in a skirt. I pulled the labels off the blouse first and put one arm in to the sleeve followed by the other. I buttoned it up and it hung like a sack. I wanted it to be tight showing off my imaginary curves, instead it showed me as a blob. Not deterred I grabbed for the skirt. stepped into it, pulled it up to my waist, buttoned it, zipped it and let it go, it fell to halfway down my bum. My heart plummeted, the endorphins decided to leave my brain and I stood looking at myself in the mirror and thinking what in the hell am I doing? What the hell do I think I look like? How on earth is this normal? Dejected, I removed the skirt and blouse. Bagged them up. I removed the rest of the items and sat naked for a few minutes, dejected and disheartened. I looked at the skirt again, tried it on again, had a light bulb moment and found a safety pin. Made a fold, used the pin and suddenly had a skirt that kind of fitted. With my new found enthusiasm I set about dressing again. I felt amazing and I did not last long dressed in my tights, skirt and baggy blouse which I had tied in a knot.

After the enjoyment the guilt flooded in, the disgust in what I had done, who I was, the lie I was living, the betrayal of my partner. I swore to myself that I could be better than this, that I was not a bad person, that I was confused. I placed my new purchases in a bag, drove to the nearest clothes bank, deposited them. As the bin closed I felt relief wash over me. I had removed  the evil from my life, temptation was gone, I was going to be a better person. The clothes had not last a day. I went home and continued my life as “normal” (or vanilla as I now like to think of it).

A few weeks later I was shopping in the local city centre and I passed a charity shop selling clothes. There in the window was a mannequin wearing a short tiger print skirt. I cannot swear that it was mine but I am pretty sure it was and I know I wanted it back.

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A Fantasy

I wake as usual at 6 am and can feel the silk nightie against my skin which excites me but the excitement just serves to remind me of the chastity device that keeps me in a state of frustrated excitement. I climb out of bed quietly making sure that I do not disturb my sleeping beauty. I slip on my silk robe, loving the feel against my bare arms. I step into my slippers. They have a slight heel and are open toe with fur across the bridge of the toes. When I walk the fur tickles my toes and I can see my painted nails. The heels make little clicking sounds that reminds me (as if I need to be reminded) that I am sexy sissy. I go downstairs and make my breakfast. I am allowed 30 minutes of me time before I need to shower, shave and dress. It is Saturday so full make up is expected with no leg, arm, face or chest hair. The clothes are the usual for Saturday. It is the maid outfit. It was placed on the door hook last night to ensure that I saw it when I woke.

After breakfast and dressing (contoured face, red lipstick, false nails, chunky necklace, bracelets and inserting my plug) I totter to the kitchen and make my mistress her cup of tea and then go to wake her. She thanks me for my tea making and inspects my appearance. She ensures that I am plugged and caged. All the time I can see her nipples through her top and her cleavage. She knows this tease of her body excites me and she makes sure that I see that her nightie has risen up just enough that it makes me want to touch her and lick her. She lets me gaze for a few moments and then hands me the list. Dusting, hoovering, breakfast for her, beds to be changed and the food shopping will be delivered at 12.00. She pulls her nightie down and sends me on my way with a dismissive flick of her hand.

I start to work on my chores. The plug reminds me constantly of her ownership and my clicking heels exciting to the ears remind me of my desired sexiness. At 10.30 she comes down for her breakfast, it is laid out ready on the table with a flower. She is pleased with my efforts and promises me that I will be uncaged later if this good work continues. She goes to shower and and I move on to the ironing.

At 12.00 a van pulls up outside. The food has arrived. I am still in my black heels with the little bows, tights, a satin effect maids outfit, full face of make up and wig. He knocks on the door and she tells me to open it. I nervously approach the door. Knowing that he will see me for who I am but also knowing that this is what my mistress wants. I open the door and he looks at me. He is amused and smiles. He calls me a pretty lady and hands me the shopping bags, one at a time. My wife comes to the door in a summer dress sitting just above the knee and clearly showing her cleavage. She invites him in for a cup of tea and he accepts. I now have to make him tea and serve him. They sit and chat at the kitchen table whilst I stand and wait for the next instruction. I can see him looking at me and I can tell my mistress is enjoying the power she has. I stand and wait.

As I stand in the corner waiting to be told to take the dirty cups away I notice how the delivery man continues to look over at me. At one point I swear he licks his lips, as if his mouth has gone dry. Could it be that he is excited, that he finds me attractive, that he is turned on by this maid. I can feel my cock trying to stiffen in its cage and losing the battle, my mind is swirling and I can barely stay focused, my heart is thumping. Still my mistress talks and laughs, she touches his leg in a friendly gesture and I see his response small as it is but still that little flinch that says he is excited by her touch. She looks at me and smiles and then asks him outright “what do you think of my maid?” He blushes, stutters but mumbles “she looks good, how obedient is she?”. “O, very, would you like to see?”. “Yes”, he stutters. My heart is racing and I realise how excited I am by the whole thing and how scared I am. “Stephanie, here, how”. I totter over. “Lift up you dress”. I obey without thinking and show this man my cage cock that is leaking. “Look” she says. He is excited to see you. “Put your dress down” I obey, again without thought. She looked at the man who was touching himself. “Why don’t you show the sissy how excited you are?” Without hesitation he undid his trousers and drops them to the floor. His cock his hard, throbbing and pointed at me. She looks at me and orders me to my knees and tells me to open my mouth and say hi to the man as only a sissy maid can. I act without thought and find myself on my knees with his throbbing cock in my mouth. I move my lips up and down just like she has had me practice on her dildo. I take my mouth off his cock and run my tongue over the tip and around the shaft, I wrap my lips back around it and work my mouth vigoursly up and down I can hear him groaning and I can feel him twitching. My mistress holds my hair back and encourages me by calling my a good sissy whore. My mind is a blur all I want is to taste him and then she says “stop” . It takes all my will power to stop I so want him. I hear him say “what? No not yet”. She laughs. I turn to look at her and I realise that she has been pleasing herself with the one hand that was not holding my hair. She takes her hand out from between her legs. I can see her fingers glistening with her juices and she places them in my mouth so I can taste her. She looks at the man and says. “IF YOU WANT HER TO FINISH THEN YOU HAVE TO OBEY MY RULES”. He looks shocked at how this sweet attractive woman has just turned into a domainant lady. “Ok” he says. His cock erect and throbbing. “Upstairs in the bedroom, I have left you a present, you want him to finish, you will know what to do”. He goes upstairs, leaving me kneeling and sucking her fingers. She takes them from my mouth, lifts her dress and sits down. “Sniff but no touching she says”. I can see her wet knickers and I place my nose against them. I can feel their wetness and smell her juices. I want to lick but I know she will not be happy.

We stay like this for what seems like an eternity and then I hear a clicking noise, a stumble and some more clicking. “Good” she says. My head is still between her legs but I sense somebody beside me. She directs me to look at the delivery driver, he is standing there in a pair of my heels and tights. His cock is still erect and is trapped behind his nylons, mine is desperate to break free but is still gaged. She directs me to his cock and I eagerly take him again desperate to get his juices. His groaning starts again and I can feel he is close. I so want to taste him. “Stop”. Instantly I withdraw my head and I stare longingly at what was going to be mine. This time he does not moan and I notice his look of surprise. I turn and see her wearing her strap on. “Now ladies it is my turn”. I turn and present myself to her, just as i have been trained, dress up tights down. He stands there surprised “o honey” she says mockingly “this is not for you” “You have to be a special girl to get this” she continues as she applies lube all over the dildo. She approaches me from the rear and I feel her fingers close around the butt plug and pull it out in one quick movement that makes me wince and then I feel the head of her dildo against my ass. Gently at first it pushes against me and I can feel myself open and give myself to her as I feel myself opening and her entering me slowly at first I hear her saying “what are you waiting for , he has another hole”. With that she thrusts quickly I feel as if I am going to split I give a little yell and then his cock is in my mouth

I feel myself push back against her as she thrusts into me, back and forth to a rhythm that reminds me of a jack hammer. I can feel myself getting aroused and although trapped I know I will explode like only a caged cock can with dribbles but at the same time I don’t care because I have his hard throbbing flesh in my mouth and I am working it like I have been taught, my lips are sliding up and down the shaft and then I use my tongue around the top, I can hear him groaning and know he is not far off and then it happens I feel my caged cock give up its juices as she pounds away at my ass. My cock is screaming to be erect but knows it cannot manage so just releases its juices in a long dribble, my heart is hammering and just as the relief washes through me the cock in my mouth explodes in two big jerks. His hot cum hits the back of my throat and I swallow it all enjoying the warm feeling as it moves down my throat. I continue to work his cock until he has given me every last drop. I am not too sure at what point my mistress had pulled out of me but I hear her say “clean that mess up” I look at the what was my clean floor and can see my cum and I move to a point wear I can lick it up. The delivery man is catching his breath I can hear him panting as I lick at the floor. “I am sure you have other deliveries to make today” I sneak a glance up and feel sorry for him as he realises that it is over and he will not be getting any of her. He looks at himself and I can see the light bulb moment when he realises he is standing in some womans kitchen in tights and heels whilst her husband, who is dressed as a maid is licking cum from the floor and she is standing there in a light blue dress with cleavage bursting out of the top and heaving back and forth with a strap on tied to her waist. ” I best change” he says and totteres out of the kitchen. Next I hear the buckles being undone and then a thud noise as the strap on is placed on the table. “Now me”. I turn to see her sitting at on the chair, legs apart and her wet pussy looking straight at me. I feel my cock attempt to stiffen again at the thought of those juices and I move my head between her legs. The smell of her juices are enough to send my mind spinning again and I startto lick the sides of her thighs and move close to her clit ensuring I get ever drop of her. My tongue is working away when I hear him come back into the kitchen. “you need to sign” he says. She laughs and I hear her sign as her breath becomes short “now get out”. He shuffles of and I barely hear the door close as I continue to work my tongue all round her clit, she puts her hand on my head and pushes it hard so that I can barely breath as my nose and mouth are in her, “faster” she shouts and I work as fast as I can licking , then flicking with my tongue. Her grip tightens and she lets go with a waterfall of juices I lap them up ensuring that no mess is made except for my fresh puddle from my limp caged cock. “You have been a good sissy so far today, if you continue this good work, I might unlock you later”. She stands up and goes to leave the kitchen but stops and returns to me. “You thought I forgot didn’t you?”. I do not reply I have learnt not to. “Turn around” I do as I am told. “Present yourself”. I comply without think and I feel my plug being reinserted. “Clean up the mess and complete your chores”. She walks out. I lick up my mess like I have been taught. Stand up and straighten my dress. I walk over to wear my list lays. I take out a pen and cross off number four – give delivery man a blow job. I pick up my box of cleaning product and head upstairs to clean the bathroom. I only have an hour until our neighbour comes around for a cup of tea.

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Part 4

Throughout my teenage years the journey continued as you would expect. I spent hours going through the catelogue looking at the women clothes and fantasising about wearing, especially the lingerie. I would delve into my mothers underwear drawer when I could. Every now and then I plucked up the confidence to buy my own tights due to be scared that my mother would notice hers were stretched. I would wear them and throw them out. I noticed that the girls I dated all had big breasts and I loved to touch them and please the girls. Sex was not a big driving factor but being with a girl and pleasing her was. Outwardly I was a standard typical boy but internally my desire to dress was growing.

I lived like this through my teenage years and through my early 20’s. I still debated the whole concept of if I dressed as a woman did that make me gay but I still did not find men attractive and I loved being with a woman and so my confusion continued. When I was in Uni my chances to dress disappeared. When I was home my sister had moved out and by now I was bigger than her anyway. I survived by sticking to wearing tights every now and then. My girlfriend at the time discovered  a porno mag I had and she went nuts. If she had looked a bit harder in the bag she would have found the tights I wore when looking at the mag. Now that would have been an interesting conversation. Over those years I had many near misses. My step father coming home earlier than expected when I had just slipped my sisters skirt on, was one of those. Luckily I heard the car door and I was able to strip and pretend I was going for a shower. My heart was racing and I must have been flushed. Another time was when I tried on my mothers lipstick. I looked stunning (in my opinion) and I felt great. Then came the time to take it off. It was not so easy. I scrubbed and scrubbed. I was convinced everybody knew when they came home and I kept rubbing my lips to make sure there was none on there.

It was not until I moved in with girlfriend after Uni that I started to embrace the cross dressing. At first I dabbled with her clothes but none seemed to fit and her underwear sadly was not sexy. It was at this time that I started to purchase my own clothes. The first shop I went to was Asda. I bought knickers, a bra, a skirt and a blouse. everything was on sale. I had no idea on sizes and I was scared that the shop assisted was going to point and laugh at me, whilst calling me a dirty pervert. My hands were shaking at the till and I had guilt written all over my face. My heart was pounding and I was sweating. Bizarrely I have none of these feeling when buying my wife clothes but on this occasion I was convinced the woman knew they were for me. I rushed out of the shop as quick as I could. I drove home, locked the door stripped naked and started to put the clothes on. Pink knickers, barely fit. Pink bra, too small and left marks. Plaid skirt. stunning. Blouse, too big, looked like a sack. My heart sank. I removed the clothes that did not fit and noticed the bra marks. Panic set in. all the clothes were removed, bagged and hidden in the attic. I then set about what can only be described as beating myself to try and remove the bra strap marks. I did everything I could. By the time my girlfriend came home I was stressed and unsatisfied. It was a disappointing night and my spirits were low. I promised not to waste money again and give up this cross dressing for good. Fast forward two weeks and my girlfriend was visiting her parents for the night. I had bought her a little Miss Naughty silk nightie and there I was laying in bed in cased in silk and feeling beautiful.

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Part 3

I was lucky when I was growing up to have a sister four years older than me. Our size was pretty similar and I was able to use her clothes. Thats is not to say that I was in her wardrobe all the time but she had one outfit that caught my attention. It was a black velvet skirt and jacket. You have to remember this was the 80’s and she was a fan of Madonna and the Breakfast Club movie. This outfit fitted that style and I loved the look of it. This outfit marked my journey from knicker wearer to cross dresser. At the time I did not realise this and again just thought of myself as experimenting (how naive was I).

By the time I plucked up the courage to raid my sisters wardrobe for this velvet desire I was now regularly wearing tights for my sexual release but I had also discovered a body suit. It was black and snapped together between my legs. It was so tight fitting. I can remember the excitement I felt putting this on and how sexy my body felt to touch. The feeling of being sexy was earth shattering and I remember pressing myself up against a mirror to imagine what it would feel like to have another person on me. I loved that body suit and to this day I prefer them to basques.

On this particular occasion I remember pulling on the tights and then the body suit. I snapped the poppers shut and felt my body becoming enclosed. I then entered my sisters room. I carefully opened her wardrobe and after making a mental not of how everything looked I pulled out the hanger with the skirt and jacket. I pulled the skirt on and then the jacket. I was hooked. It felt as wonderful as what I had hoped. It made a crinkly noise when I moved and the feeling of the netting touching my nylon legs was electric. I felt so light headed but not dizzy. The feeling was excitement mixed with sexy. I felt beautiful but needless to say it did not last long the emotions were too much and it was all I could do to strip before I climaxed.

I remember that feeling so fondly. For the first time in my young life I had truly felt free. Unfortunately whilst I laid on the floor breathing heavy after my climax the thoughts of disgust returned but now they brought a friend. This time the penny dropped. It was not normal what I was doing and therefore I must be gay. That was horrifying. Here I and was barely 13, I had just climaxed after dressing in my mothers tights and body suit and topping it off with my sisters skirt and jacket and now I had to contend with the belief that I may be gay. I hated myself. I cleaned up, I scrubbed at myself, I cried a little and then I put it all in a box in the side of my head and denied it. I promised myself I would not do it again. I promised myself that I was not gay because thats not what people were in my friendship group. I settled on being confused and weak.

Needless to say. I could not keep my promise to myself of not doing it again and my fears of being gay grew every time. I must say at this point I have no issue with people being gay. My fear was based on my age, location and how I perceived the world at that time. It was scary and I had nobody to talk to. The internet did not exist and the battle I started to face then is  a battle I have faced up to a few years ago when I realised crossdresser does not mean gay. There were lots of other things that made me think I was not gay the main one being I did not find men attractive. The problem with this was I did not find men attractive but I like to dress as a woman to climax so surely that meant I was a woman in a mans body and at my age that meant gay.

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Part 2

When I think about cross dressing the woman from the story in my first blog is never far from my thoughts. I remember the story describing her slender body in jeans that hugged her figure and the blouse that was billowy but showed enough shape and definition that the firm breasts were obvious. I remember how the woman was confident about who she was and that it was her, that noticed the man, it was her that called him into the shop, it was her that challenged him on staring at her and it was her that instigated sex by taking control of the matter.

It was the confidence of this woman that appealed to me and still does. I recognised in this woman a level of confidence and authority that I lacked when I wore my jean and t-shirt. I found the confidence she had in herself intoxicating. At the timeI did not realise these feeling and I just found her confidence a turn on and for years I craved this type of woman. Somebody who will take control and put me in my place. I have since discovered that this level of control manifests itself in my desire to have a woman strip back my masculinity by dressing me as a female and taking on the stereotypical role of a female.

The woman in the story awakened my sexual urges but I found that those urges were never truly reproduced until I slipped on the first pair of silk knickers. The actual thought process from looking at the lingerie pages of a catalogue, to looking in the knicker drawer of my mother to touching them and then wearing them escapes me. I can only assume that I was suitably curious enough to make each of those steps and in the heat of the moment saw nothing wrong with the actions but just assumed thats what all boys do. However, what I do know is that when I stepped into those knickers the first time I felt a level of sexual confidence that I had never felt before and it to was intoxicating. I did not know it at the time but I had started to feel how I imagined the woman in the story had felt (it took me a long time to make that connection and by the time I got there I was well on my journey of crossdressing and self realisation). At first I was happy to just use knickers to satisfy my craving for this sexual feeling but soon I discovered nylons. It was when I plucked up the confidence to put a pair of tights on for the first time that the sexual brain cells exploded. I have never felt something as empowering as tights. To this day they are still the my favourite item to wear and they instantly transform me from feeling like a weird man in knickers to a confident human who has sex appeal. This is heightened by the addition of heels (but we will get to them later).

The downside to these initial footsteps into crossdressing was the guilt, the hatred and the disgust I felt towards myself as I took the clothes off. This was of course coupled with my worries of being caught. Would my mother discover her tights had been worn?, would I put the clothes back in the wrong place?, would somebody come home and see me in knickers and tights with a “hard on”. I hated myself but I was constantly drawn back to repeating the actions over and over again. I am not a religious person but I found myself believing I was going to hell. over the years I have even prayed to god and asked for help in moving away from the feelings. I have since realised that these feelings are wrong and that it is ok to crossdress but for a long time I viewed myself a degenerate. It is hard to truly explain the roller coaster of emotions that I felt but if you can imagine a 13 year old boy sitting in the bath scrubbing at his skin and praying to a god, asking for forgiveness and help in not repeating the actions you will start to understand how the elation of feeling empowered was easily replaced after I had released my sexual energy.

crossdressing

My Crossdressing Journey

Placeholder ImageI cannot remember the first time I wore female clothes. I know I was young, a teenager going through the mind field of puberty. I remember reading a story in an adult magazine (yes i read the stories) and it talked about a woman working in a shop window and a man noticing her pubic hair sticking through a rip in her jeans. One thing led to another and they had sex. I remember being turned on by the thought of this woman’s body and pubic hair. At the time I thought it was the normal way to feel but when I came to explore myself i did not picture the woman I tried to imitate her. I put on some knickers and a dress. I was lucky that I had an older sister and I raided her skirts but it was my mothers knickers that I went for as they were nicer, more like what I imagined the woman in the story would have worn. I put the clothes on and I remember feeling excited as the crush black velvet skirt touched my bare legs. The excitement was amazing and I became very aroused. I loved the feeling right up until I came and then I found myself disgusted but what I was wearing. I assumed this was normal. I took the clothes off making sure that I had not stained them and returned them to their place. I told myself thats what all boys do but somewhere deep down inside of me I knew that was not true. I made sure that I did not tell anybody and that was how my journey started. It was a journey that has lasted until now and will continue. I hope to use this blog to write about my experiences and to express the journey that I have been on. A journey that has resulted in self loathing and finally acceptance.