Sign up!

My First Crossdressing Experience in Public – Part 3

Author: Miss Samantha Pink, own 40 years’ experience of crossdressing

I was told to stand up in the middle of the room and raise my arms out to my side and hold them there and not move, my mind was racing and thinking loads, what’s going to happen next. It was only to measure my chest size, then I was asked what cup size I preferred. “Do you mean breasts?” I replied and the lady giggled and ask me again and I said I want to know that I have breasts under my clothes but I don’t want them getting in the way. I stood there with my arms on my hips waiting for the lady who was dressing me up to come back from wherever she went to. A few minutes had past, that felt a life time, she then returned and showed me what she was going to put over my chest. They were fake 36C silicone breasts, lovely, but Roanyer do a very generous selection in different sizes and at reasonable prices. Check out their web site, beautiful stuff and professional staff and brilliant customer service, first class. 

Once she put on the fake breasts and a white, padded push up bra, I really liked from my neck downwards what was in the mirror looking at me. The girl inside me was coming out finally. I was told to walk around to get used to all the foundation garments on me and the other heels. I was even offered a nice cuppa, which I accepted and walked around the room checking myself out in the mirror, and tried my best to walk like a woman, shorter steps, one foot in front of the other and held my head up high with my hand on one hip. 

When the tea was given to me and I sat down, the lady asked me a few things about what style of clothes and makeup I wanted next. Interesting, but I first asked her for some hip and butt pads to fill me out more, so she got up and came back in a jiffy. She knew what size to get so she must have worked out my body measurements from using her eye with her knowledge of the trade she was in. Amazing. 

The hip and butt pads are also available from at great prices. When I put them on under a pair of thin, shaper, ladies briefs, my bottom half was even more curvier like a real woman’s and with the 18 inch waist, I had an hourglass figure, feeling super sexy like a real woman, getting there just the top half to go and then get dressed. 

I was so happy that I had calmed down my breathing and the pain inside my belly was dying down as well as the pain of my feet inside the size 6 high heels. Now the next thing was to choose an outfit of my liking, full makeup, false nails and eye lashes. There was so many outfits to choose from I could choose 2 outfits and wear them for my last hour after my face makeup is put on. I picked a nice cute, above the knee length, white and black tartan design skirt with a nice white, short sleeved blouse, my arms were fully shaved as well. I also wore a matching thin jacket the same design as the skirt. 

The lady told me that I could go braless with the blouse on, which I loved the thought of doing. So she took off the bra and the fake silicon breasts attached to fake silicon skin. Then went away for a wee while to get some nice fake breasts and something else that I didn’t know about or ever try on. I’m writing this part of my experience whilst wear a nice tee shirt and thick grey cotton tights on. This is my heaven on earth. I checked my watch and there were 180 minutes left or 3 hours, so the faster they put my makeup on, the longer I can be fully dressed as a woman . 

Coming back after a short while the lady told me that I will be asked to go way out of my comfort zone, now I am really worried and getting nervous again. She said to calm down best I can and do what she asks and do be embarrassed as she has seen things that would make most women blush. What’s she wanting me to do, take everything off when I only have 3 hours left with this beautiful experience. Anyway I just calmed down and breathed shallow because that waspie pain was coming back and it was getting more intense. There is a fine line between pleasure and pain and I was pushing on the verge of unbearable pain, so calm down Samantha Sweet. 

“Arms stretched out wide reaching for the sky and hold your chest out and stomach in Samantha” I couldn’t pull my belly in any further but I pushed out my chest, which is small for a guy. The lady sprayed around my nipples and chest area this stuff with a fine mist, it felt sticky on my skin, just as well I shaved my chest hair which is fine anyway, so not much there. Then fake silicon breasts were gently pushed on my chest and massaged in so there was a smooth finish and they stayed in place. I was told to slowly bring down my raised arms and put them on my hips, standing square on informing of the long mirror. After a short while I was asked to lightly jump up on and down in my heels, kinda hard but I did little jumps whilst looking at myself in the looking glass. The new breasts looked real and the jiggled up, down and around like the real thing, lovely. Now I was to relax and calm right down for the next part, big gulp. 

Please take off the shaper pants, hips and bum pads, leaving them on the little coffee table in the room, neatly. Once that was done I wondered what would be next. She said with a cheeky glint in her eyes, take off that thong but keep it separate on the coffee table, and take off the white cache sex!!

If I did that I would be naked in front of a total stranger and be very ashamed with my man clitty and testes on show. I was convinced that it was for the best to get the full realistic women effect. So I looked at my watch thinking that the longer I don’t do what is asked off me the less time I will have in this beautiful place unless I pay more but it was only open to 8pm. Right I said to myself just go for it and don’t worry I am sure she has seen worse things than a naked slim smooth guy. So off they came, with my man clitty showing its racing rock hard helmet, how was I gonna calm this down now. 

“Looks like I will have to help you there Samantha!” By the way I am called Stephanie, I was born a male but now I’m fully female with all the surgery. She had pretty good surgery especially when I thought she was a woman, there was no trace of a man in her at al. Amazing surgery very immaculate dresser. So I totally trusted everything she told me about fully dressing as a woman, making my inner confidence become more stronger, which then made me feel happier as my true self. So glad doing this and I’m having a lovely experience. I wasn’t yet comfortable calling the lady by her first name. So after checking her fingers for a wedding band, then seeing she never had one, I decided to just call her Miss since she was nice to me and never judged me, on what I was, a slim awkward crossdressing guy. “Follow me Samantha”, she said as I was led by my hand to a different room. It had a red lacy curtain, the rest of the previous curtains in front of rooms or areas were black lacy material. I asked about the colour of the curtains, wondering why they were all black, except this one which was red lace. Miss informed me that all the curtains in the building were black lace except the red one and another one, somewhere else which was white and gold. These were the special rooms and I couldn’t wait to find out later on, what the very last room with the white and gold curtains had inside. I was intrigued to what was behind both of these curtains, I was going to find out soon enough with the red lacy one. 

Miss slowly opened the red lacy curtain as I was standing there, my little clitty totally erect with my tiny testes taunt and up high just from where they came down from when I was a teenager. All there was there was a table with a pink fluffy towel covering it right in the middle of the room, the walls had a marble effect the floor was warm like it was heated and in the left corner a small table with baby wipes and some oils and feminine spray. 

I was told to lie on the table face up which was waist height, well it was to the lady’s waist height. Then I had to close my eyes and relax and enjoy the experience. So I lay on this comfortable table on my back and closed my eyes, with anticipation of what would happen next. I felt something soft touch my man clitty and testes massaging it slowly up and down whilst other soft feeling touching my testes all over, then something wet and moist was licking me all over down there. I couldn’t keep my eyes closed and when I opened them this lady was arousing me with her soft little hand, with her wet tongue and cute, kissable lips licking my man clitty and testes, She noticed that I seen her and suddenly stopped and scolded me. “Turn over on your belly you disobedient little girl!!” I did was she told me squashing me down below and in pain and saying sorry Miss. “For opening your eyes when Miss was being so nice to you, you will get a good, hard slap and like it!!”  With that she held me down pressing hard on my back and slapped my part bum cheeks so hard and so much that I started to scream and cry like a real girl. “When I tell you to do something, you will obey my every wishes no matter what, ok my girl!!” “Yes Miss I’m Sorry!!!” She said again, “I Never Heard You Girl!!” “ I’m Sorry, I won’t do it again Miss!!!! Every word she said the slaps on my bum were getting harder and more severe. I just cried and screamed loudly into the fluffy towel and she then stopped. “ Get off the table, now girl and stop crying!!!!” With hearing that I jumped up and held my breath to make myself stop crying and try to calm down. I still had an erect man clitty and didn’t know how to make it become soft and flaccid. 

“Listen to Miss, play with that man thing and make it go down now, and hurry up about it!!” I was under her power and did what I was told, even though it was very embarrassing playing with myself but I felt I had to do what she said to totally and fully enjoy this ultimate experience. She must have known by the way I was standing that I was about t release, because she got on her knees and sucked on my man clitty and I felt fully drained whilst she stuck her ruby red finger nails into my peer bum cheeks. I closed my eyes and had the most vivid thoughts of living as a woman in public all the time under this lady’s spell. It was amazing then after I was spent I came back to reality. 

“Open your eyes Samantha, you only have 2 and a half hours with me, so let’s get started” “ Yes Miss Thank You for helping me” She smiled and called me a good girl and that I was much better and she was happier. I wanted to please her and do whatever she asked me to do and enjoy this crossdressing experience. There were wipes that I was given in the room to clean myself up and I was told to sit on the bed and wait for Miss to return soon. My bum cheeks were sore but I sat down without complaining as Miss asked me to, you don’t get the pleasure without some pain in life. 

When she came back I stood up and I’m ready Miss to be dressed up as your little girl. She smiled and came over and told me to stand in centre of room, which I did, and step into this silicon fake vagina. Never seen one before and she explained how to hide my man clitty and testes inside and pull it on tight so it looked like I had a real vagina and smooth down below. I was not allowed to look into any mirrors yet. Then she told me to stand up with my legs shoulder width apart and my hands relaxed by my sides. Spraying some sticky glue with a fine mist on my chest, Miss glued on size D fake silicon breasts, saying that I suit much bigger breasts because of my tiny waist. Then she put on and very, very tightly tied a stronger, boned structured under the bust corset on my body. She told me to breathe in as much as possible and to hold my breath, then pulled with all her might, even putting on off her sheer stocking little feet on my lower back for leverage. All the time I had to stand there whilst I was getting the breath sucked out of me, it felt like an eternity. You can breath now my girl!” I tried to breath out and it was very difficult, it felt like a massive weight was on my body. I was fighting for a good breath but all I could get was a small rasp and I started to panic. Miss noticed this and helped calm me down by talking softly to me and reassuring me that it will get easier, just slow breathing down and concentrate on your pulse rate. It worked I calmed down and even though it was extremely difficult to get a good breath I still had enough that I managed not to pass out. “ 17 inches good girl”. I thought to myself wow and extra inch less makes all the difference. Miss got me some foam and bum pads to make me more curvier and feminine. I had yet to see myself in a mirror as there was not one in this current room. Roanyer sell silicon hip and butt pads and they are fantastic price and very realistic too, please check out their web site and it has pictures of all the items with full descriptions. 

I was taken by the hand back to the room full of lingerie. Walking back in my jet black 4 inch heels, which I still never took off, Miss suggested that I should be wearing 6 inch high. I just agreed and said whatever makes you happy I will do it. So off my heels came and was told to sit down in a fancy feminine chair but upright with my legs crossed over each other like a lady. Didn’t take long for Muss to come back with 6 inch high heels of the same colour and style, my bum cheeks were still tender but I sat on the chair and never said a word until Miss spoke me. “ Do you like these ones Samantha?” Miss said with a nice smile. “ Yes Miss Thank You “. I then was told to put them on whilst sitting in the chair, they were size 6 ½ and they fit like a glove. Then I had to stand up slowly, which I did wobbling a bit but I focused on my balance and concentrated. The sheer pain in my body also kept me totally focused and helped me concentrate much more. Once I got my balance I stood there waiting for Miss to tell me what to do next. She told me to sit back down as there will be plenty of time to walk in the heels later and told me to take them off and leave them by my side. 

Miss left and I looked at my watch timer there was 2 hours left to go. Wonder what would happen to me next I was a bit anxious but excited at the same time. Whatever it would be I would have to do it or I would get another severe spanking and waste my dressing time, which would make it an awful experience. Miss came back with some sweet tea and nice biscuits and a clothes rack with lingerie skirts dresses tops and a little cute pink box. Wonder what is in the box. I would find out in the next hour. Miss spoke to me in a soft voice whilst we were both sipping our sweet tea, I never took a biscuit because I didn’t think I would have any room for it in the corset. I was sitting in just the corset with my fake breasts on show and my bottom half on show so I needed to be dressed decent before I could go anywhere next. 

Miss was asking me what I liked to wear and what’s my style. I said I would like a nice lady thong with a matching pretty bra, sheer seamed stockings, suspender belt. All the underwear white lace. A short tartan skirt with a nice white blouse, a matching jacket same design as the skirt and some nice jewellery simple handbag with fierce makeup and finally the wig of my choice. Also smelling like a woman with a sweet perfume. 

Every word I was saying Miss was paying attention to it and she was looking at me closely and felt like she was trying to get into my mind and soul. “ Finish your tea then stand up my lovely”. I did what I was told straight away. The next hour Miss transformed me right in front of my eyes into the woman of my dreams and I looked stunning and like a real woman. 

I was then took to the last curtain, the white and gold one, I had a walk very small steps because of the 6 inch high heels but I had to get used to them and not let Miss down or get upset. Once there I stood in anticipation, what could be behind this curtain, Miss opened it and there was a camera on a stand in the middle of a room with white walls and a white fluffy long rug in the back centre of the room opposite the camera next to one of the walls. 

“Pose for me Samantha, stand on the rug please” said Miss to me. I did what she told me and did different poses in my skirt and top with full makeup and long strawberry blond wig on. It was so lovely and then the last pose was lying down on the fluffy rug with my legs on top of each other showing them of in the sheer nude stockings to the lacy stockings tops and all the time smiling and loving it. Miss showed me the pics and I said I was a beautiful girl in the photos and I was allowed to pick one and it would be printed and put in a pretty frame and sent to a address of my choice out of privacy. I picked the one lying on the rug as it showed of my best assets my legs. That was my experience over and I had to get all the makeup and things off and back to boring male mode. I did come back the next two days before going back to my work place but that is another story that I will tell you some other time. I’m sitting here with my black pantyhose and long top on in my comfy couch writing this experience and I hope you like what I told you.

  • Prev:My First Crossdressing Experience in Public – Part 2
  • Next:How to pick a flattering wig for your face shape?
  • ×