My First Crossdressing Experience in Public – Part 1

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

I was idly browsing online on day not really looking for anything in particular and a new website was prompting me to check it out. It was a transformation shop, wondered what was all that about so I opened the link. It had a pretty lady with a stunning pair of legs and a cute smile, what’s not to like about that.

When I opened it up and had a good look I was very, pleasantly intrigued and so wanted to look at least half decent as the lady on the web site. It wasn’t a woman, which at first glance I thought was, it was a guy, wow. Amazing makeup and fantastic body and beautiful clothes, wig and heels.

I wanted some of that, lol, so I took a brave step and called the phone number of the shop to speak to a member of staff. Gulp! I said, “Hello I’m Sam” and the person on the other end of the phone said, “Hi what’s your femme name?”

That threw me and I was slightly embarrassed, but it told my thought process that they wanted to make me feel relaxed as my female side, which was very special. My real name is Sam, which is a male/ female name, but I prefer Samantha. So I nervously said, “Samantha.” I must have not said it clear enough because they said, “Pardon Dear”, so I said in a clear and confident manner again, “Samantha,” and they replied “That’s a lovely name how may I we help you today?”

I was on my own outside a public inn in the morning sun, chilling in my running leggings and top, trainers with a cuppa, my local haunt on my days off. So I asked if I needed to make an appointment to come and see them in the near future. They said don’t have to, just turn up early or in the afternoon and let’s get started. What a super cool place, amazing.

The week after I phoned it was all I would think about becoming a woman for a few hours or the whole day, it all depends on how much I had to spend on this new experience. As this was my first time going I would only spend £200 for now as I had to get there by train and find a hotel to stay at for a few days.

I was off work for the week so I decided to just take myself and my small back pack and essentials and catch a train early next morning. I worked in a male oriented environment, so no one there knew about me and what next step of my journey I had started to go on.

I had dressed up years before but this was different. It was in private and never went out or interacted with anyone. Now 8 years later I wanted to take things further but I had to go somewhere far away from work and the town I stayed at.

I wanted to know how I looked honestly as a woman fully transformed, if I didn’t like what I seen in the mirror then I would totally stop and not take that next step of going out in public as a man dressed as a woman.

Anyway as I was in the train travelling the 90 minute trip, I was starting to get more anxious before I got there, to me this was a massive step forward on my ultimate journey to my happiness. I took some deep breathes when the train stopped and walked the short distance to the shop as it was only a few minutes walk from the station. Shame it closed down a few years ago, as it was a nice relaxing place. I got there but walked past super nervous but quickly glanced into the window display, amazing. I kept waking for about 5 minutes to try and calm down and said to myself, look you have come this far so you might as well pluck up the courage and go in for a look and introduce yourself.

So as my pulse was racing and my heart thumping I walked back and stood outside the lovely place, it was like Aladdin’s cave for people like us. I stood there for what felt like eternity and then held my breath and opened the door and walked in.

Once in, I was proud that no one approached me or bothered me, which I didn’t want to happen. I felt a little at ease and started to look around, but things were there that I never seen before or new existed. Fake breasts and full vaginas, which are also on sale at roanyer, they are miles better now than when I was young years ago and off excellent quality.

I didn’t want to touch anything I just looked never said anything or bothered anyone, I was still shy and nervous even though I had dressed before, but this was totally different and I was out of my comfort zone.

I looked around and seen some lovely crossdressing books which I so wanted to buy and read and look at the pictures. So I picked up two and took them to the female staff, who were so lovely. The woman said to me if it was my first time dressing up and I told her no I do it in private since I was young. It was my first time there and she knew that from how I acted really quiet and shaky nervous. Then she asked me my name and. I said I’m Sam I phoned here last week and someone lovely spoke to me so I had to come and visit. Then she asked me would I prefer to be called my Femme name and I said yes it’s Samantha with a nervous smile, the lady smiled back and said that’s a lovely name and it made me feel super welcome.

After paying for the books I put them into my back pack and felt at ease to ask for some help from the all female staff. They were so caring and lovely. I asked what do you wear to make your waist smaller and how small can my waist go to. I had a 26 inch waist at the time normally and they said there are waist clinchers and corsets that take up to 8 inches off your waist, wow. I was hooked with that idea and I said can I see on me how it looks please with a big smile.

I took off my male tee shirt, I was wearing boxers, jeans socks and trainers the only set of male clothes for the next 3 days. I wanted to just wear them from my work place to the shop then back to train in 3 days time from a hotel that would accept me being dressed as a woman in public for the first time ever in my life.

Standing there in front of a full length mirror with my top off and a lady putting and slowly pulling thick strings to shrink my waist and me watching before my own eyes my waist line getting much smaller than normal. Well honestly I felt my little man clitty becoming hard, more than normal. Maybe it was because my breathing was become constricted, as it was difficult to breath, I was told to breathe short controlled breaths and try to relax. The lady stopped pulling with all her night and tied the loose strings around my waist and ticked the excess away. Then she measured my waist. My waist was normally 26 inches then. It’s 29 now getting older lol, The tape measure was 21inches!! My upper body looked a wee bit more towards becoming like a woman’s and I could have had the waist clincher which was on me down to 18 inches, which is 8 inches off my waist as it said on the sign on the wall beside all the corsets. I just had to shorten my breath and stand up stomach in with my shoulders back and chest out and relax.

It was lovely to look at myself in the full length mirror and I had it on for a few minutes. Then something came into my mind out of nowhere not even without thinking , a great idea and put my plan into action.

I kindly asked the lady to take it off me and said thank you for your lovely assistance with a big smile. I put my tee shirt back on and my back pack. I said I will see you later and went back to the lady I spoke to first at the cash desk. “Do you know any hotels close by that accept people like me, because I want to stay in the area for the next 3 days dressed as a woman with you and your lovely staffs help?”

“She smiled again and said yes I will give them a phone and let them know that you are coming soon. Such a lovely person and so helpful and kind, not many people like that in the world nowadays. Especially with this awful Covid-19.

The hotel was only £99 for 3 nights but it was a private place and more like a b&b. I like breakfast gets me going for a good day on my nice walks dressed as a woman in public, minding my own business.

I thanked her and asked when is your place open to as it was 10am. It was open to 8pm but I wanted the full 4 hour experience first so would make sure that I was back before 4pm but 2 pm would be much better incase there were people coming in after me later.

I got the b&b details and it was only 5 minutes walk the way I walked right past the transformation shop just before going in. I was so happy and not nervous anymore of being there or going back in later for dress up fun like a wee girl in s sweet shop, yeah I love sucking on lollipops hehe.

I got to the b&b and said I was Sam and they did a double take and said that they were excepting a woman to come in called Samantha and I felt my face get red with embarrassment. But then I slowed my breathing down, pretending that I was in a waist clincher and said, “ Oh Yes Of Course Later On in the evening of that is Alright?” “Of Course Miss Samantha how are you paying for your room and board cash or charge?”

I gave them cash from my back pack and given a key and said thank you and I will be in the dining room for my supper at 9am, would like some nice sandwiches and a cup of coffee for starters.

I was going to enjoy the next 3 days with no one knowing me or judging me but if they did that’s their choice just keep your opinions to yourself, if not then later and if you don’t like then please jog on, bye.

I got to my room it was nice and big for what I paid and had it for 3 days. I put my back pack on the bed taking some money out of it and my room key and went down to the reception, making sure I locked my room, well I had about £500 in notes in my back pack.

I bought a nice bottle of red wine 14% and asked for a wine glass. Heading back to my room I was so happy but still a bit nervous at the same time. My mind was buzzing with what was about to happen in 4 -5 hours time.

Back in my room, door locked, do not disturb sign hanging outside on the handle. Time to prepare for my transformation to womanhood. I poured out full glass of the nice wine and put it on a side table by the bed to let it breath. Then I took off all my male clothes and laid them on the bed trainers on the floor next to the side table.

Fully naked I didn’t like what I saw which was male hair everywhere. Not loads because I have fair hair but enough that It needs to be removed. Trim, shave pluck etc. All gone and half of the bottle of wine drank. Nice wine need some more. Rubbed some baby lotion all over my smooth body and went back to mirror, a wee bit better getting there, it’s a start and I can wear nude glossy stockings.

I have always had nice toned legs and cute bum so I’m half way there to femininity. I started to day dream looking into the full length mirror and I noticed that I was getting slightly aroused again. Wake up ! My alarm is beeping, omg it’s 3pm. How did the time go so fast already!! I need to get dressed quickly and get around to the transformation shop or I will miss my 4 hour slot as it’s not booked so it’s first come first served.

I necked the other half of the bottle of wine whilst pulling my boring drab male clothes on, it will give me some dutch courage in the new dressing place. I had some mints in my back pack so had a few then left my room locked up and dashed to the transformation place.

Flustered I got there with red cheeks at 3.20pm. No one was getting dressed so I shot over to the lady I met first and asked what could I get dressed in and how much it cost. I wanted to be dressed in a casual look like any woman you see in public to try and blend in. £120 for 4 hours bargain. That was the basic one there were a lot of different styles, like full lingerie and thigh high heeled boots, sexy as hell.

I paid the amount in cash at the desk and then a lady came out and took me with her to a another place in the building, it was behind a sliding set of black laced curtains, a whole unique place where some of the transformation happened. Just before we went through there were loads of gorgeous wigs and hair pieces and she asked me which one I would like to wear, which one would Samantha suit do you think. I looked at them all at once and was drawn to a shoulder length strawberry blonde going onto light brunette straight cut wig, it was gorgeous and my little clitty moved around twitching so therefore that was the one for Samantha. Even the lady with me said with such glee that I picked the right one.

Next we both went through the curtains to a whole other world and I was the only one there for now. We went to a side room that had corsets, lingerie, tights, stockings and underwear, “What colour of lingerie do you like white or black?” I said black but later on I should have said white but that would be for the next day or the day afterwards. “And type of underwear, tights or stockings.”

I let her pick my underwear but I should have wear a nice thong or very high waisted tanga brief and black stockings. Most of her customers had to wear thick tights but I told her that I had shaved my legs, and she was so happy saying that I could wear thinner sexier ones, good girl we will have so much fun. I was getting more and more relaxed with every passing second and loving every minute of this new experience. She also pulled out what was called a cache sex, a strange contraption that tucks your man clitty and testes back high and tight. Showing me where to put them and how to pull it up and back, I said ok thank you miss . “Take the cache sex, nice sexy black lacy panties and the black sheer tights and go through there,” pointing straight ahead to another set of black laced curtains. I asked if I could have a quick shower first and she said of course Samantha. I said thank you and said before going that she could call me Sammy if she wanted it was entirely up to her. She said thanks Sammy and smiled and I said see you in a bit.

Let’s get that nice shower Sammy and get the stuff on, and get out ready to get dressed and makeup etc. I stripped off my man clothes and put them into my back pack and hang that up on the rack in the shower with a nice fluffy pink towel that was there on the rack and used some feminine body wash all over my smooth body. It was just as well I had the shower because after washing my legs I seen a wee bit must have missed in my room at the b&b, so I took care of that with a spare razor blade in my back pack, I came prepared for any eventuality.

There was no one around and I wanted to get out of the shower naked and walk to the other cubicle along that said the dressing room, but far too nervous for that, so with towel wrapped around me smelling rather feminine and girly I put my back pack over one shoulder and had the three lingerie items in my other hand nervously walking to the dressing room.

I got there and hung up the towel where I was told by the information in the cubicle and put my back pack down beside me. I was just about to get dressed when I heard a female voice the other side of the curtain in my cubicle. “Are you ready yet?” “No!!” I thought I only had got out of the shower and this woman wants me to rush around in her time and be ready, no chance, this was my time and it was only 10 minutes into my 4 hour experience. I wanted to totally enjoy every minute and take my time, after all I paid for it and £120 was a lot of money in the nineties. That was one week’s wage and I worked hard to earn it. So I wasn’t ready, she asked it when I was trying to get my leg into the tights that it scared me and I nearly fell out of the bloody curtain and she would have seen everything lol.

“Give me 10 minutes to put this contraption on please!” “ Do you need a hand sweetie?” I said no thanks but maybe I should have opened the curtain and let her fully dress me up. Not today, maybe tomorrow or the next day, as I’m still nervous and shaking all over the place but trying to enjoy the experience and calm down at the same time. What a rushing feeling is going over my whole body, intense pleasure and such a sexual release of tension and stress becoming the woman of my dreams for the next 4 hours, well 3 hours and 50 minutes left. Wish time would stop and just stay in the place forever without a care in the whole world.

I took off the tights when I noticed that there was a big hole in the bottom and folded them up next to me in the cubicle. I took off the lacy panties because I didn’t like them at all, she picked the wrong ones, I should have seen what was there to choose from, after all I’m the one wearing them not her. So I folded them up and put them on top of the ripped tights. I took off the cache sex and re did it and took my time this time. You put your man clitty and testes in a front pocket and it clips to a bra clasp on the back of your bottom then the top strap clips around your waist once you pul back and high as comfortable as you feel like. Got it right this time around and it’s smooth at my front, amazing and under control. I stood there and said to myself that it’s going to be a very long 4 hours in this contraption, next something inside me told me to take it off and wrap that towel around you take your stuff to the shower and relieve ones self. That was lovely, sorry everyone does it, everyone it’s natural and nothing to me ashamed about. I headed back to the cubicle once I sorted myself out with another quick shower, after getting rid of all my man stuff for a wee while.

Putting the cache sex back on, it was white, I quietly sat there and thought, hmm, a lacy white thong with very sheer white seamed stockings with a sexy suspender belt, compete with a waspie, which chinches your waist up to 8 inches maximum. Yeah go for the full experience, no pain no gain. Going for a 18 inch waist today, bring it on. I sat there in this white cache sex with my legs crossed one over the other, it felt super natural, that is how I’m sitting now I’m my leggings writing this right now. It’s super comfortable and I need to tell my story to the world. 

To be continued...