First Contact

This is actually based on real events, strange but true.

At a time before the internet, I know I don't look that old. A time when my spots had gone and I was a bright, eager, and thoroughly inexperienced twenty year old. I was at an age where, a well known TV personality who always jokingly misquoted things said, "The world is your lobster!"

I was a strange guy. Allegedly I was handsome, but for a couple of years I had been ever so slightly interested in wearing ladies clothes. I have no idea when it started, but at twenty I realised I looked at what women wore rather than how attractive they were or how big their bust was. I never tried anything on, but just started to imagine what it would feel like. Wearing a dress or skirt in a breeze for example. In those days, there was the memory of the glamrock 70s and people wearing almost anything they wanted, but at this time, LGBTQ+ was not even in the twinkle of anyone's eye.

One Saturday, I was doing my usual of wandering around town. As I say, this was before the internet, so ALL shopping was done person to person. We did have catalogues, but sometimes you had to wait weeks for that to be delivered and things were never as nice as in the book.

As entertainment goes back then town centres were boring places. Apart from hunting for Christmas or birthday presents, the only relief was a cafe, with its plastic seats and formica wipe clean tables. There was a chain of burger bars in the UK, but they were a poor copy of the American brands. It was all fun, fun, fun in the UK back then....not.

As I wandered around town I walked past a charity shop. Without Facebook or Twitter telling us everything that was going on, we would only know of new shops by word of mouth or literally walking past. Charity shops were a fairly new thing in our town, so I guess the thought of cheap clothes interested me. That is the only reason I went in, I guess.

It had a funny smell of old lady about it, lavender and mothballs. There were two rooms, the front shop room had row upon row of rails, all in a disorganised fashion. Men's and women's clothes were all mixed together. Looking through into the back room, it had more "stuff" there and had a pair of red velvet curtains that could be closed to shut it off from the front.

I wandered around and it was almost impossible to find anything either male or in my size, but I persevered. As I scanned the rails, I noticed two retired ladies behind the counter watching me and a third lady in her 50s, busying herself sorting a display. The way they watched me, I wondered if they thought I would steal something, but with all I had seen so far, no one would want to steal. This was the age of drainpipe trousers and before me were rows of massive flares. All the men's shirts on the rails had collars big enough to fly and big bold colours and patterns. A long way from my Fred Perry button down collar shirt.

I was about to leave when I stumbled on something that caught my eye. Whenever I look at women's clothes, it is the design, the cut and the feel of the material that matters. Here was a 70s blouse in a plain white, simple but very smart design. The collars and cuffs were not a crazy size and the overall cut was really elegant. It felt like silk or could have been satin and had a lovely feel to it. It was a woman's blouse, but I was just transfixed by it. Yes, it was white, but men's shirts are never that white. How are women's clothes that much whiter than men's?

The ladies must have still been watching me, as the lady in her 50s suddenly appeared next to me. She asked me if I was ok and only then did I jolt from my fixation. Sure I blurted, but she was quite insistent or maybe intrigued in me.

She then described the garment as Italian silk. The conversation carried on all very matter of fact. We never broached the subject that it was a woman's blouse and I was a young man. What suddenly made the event real, was she suggested I try it on. I had a look of shock on my face, but she smiled at me saying she could tell I liked it a lot.

My heart was racing. I could just put the item back, leave and that would be it. Another boring Saturday in a boring town ending in a boring way.

Looking at her, she had a twinkle in her eye and a relaxed smile about her. Without getting an answer from me, she took my hand and the blouse and directed me towards the back of the shop.

Going into the back room, I was almost hyperventilating as she drew the curtains behind us. In the corner was a bench seat as well as many items that were going to be put out in the front once there was space.

She carried on talking about the blouse and how it was a well known designer, and she commended me on spotting it. I literally had no idea where this was going.

Her hands started to unbutton my shirt. I stood there like a rabbit caught in headlights. After placing my shirt on the bench, she slipped the blouse on me. "Slipped" was the right word, as the lovely light material caressed my skin giving me goose bumps. Being young I didn't have much body hair, but the material slid over my body hair and tingled.

While enjoying the feel, she buttoned up the blouse and it was possibly a perfect fit with a bit of room in the chest area. She twirled me round to check at the way it fitted. Her hands nipped at places and straightened where she thought it needed.

I looked in the mirror and the feeling was amazing. It felt very weird but just right. The lady though had a sad face. She piped up that the blouse was great on me, but it didn't go with everything else I was wearing.

Before she had been calm and careful but now she was quick and sharp. Within a couple of minutes, she had removed my shoes socks, trousers and underpants. She picked up my shirt from the bench as well and took everything to the front of the shop. I just stood there naked, apart from the blouse, frozen still.

From the other side of the curtain the lady asked me my sizes. Waist, then inside leg, and finally shoe size.

Very quickly the situation made my cock go rock hard. I could feel a breeze under the curtain and somehow it found its way to the hairs on my balls. It made me feel really exposed. The lady returned, not with my clothes but with a few other things that she had found.

The breeze had made my cock half subside, so only stuck out a little. She looked down and smiled at my semi erect penis. She grabbed something from her pile and soon was slipping a pair of pink floral knickers up my legs. They were a couple of sizes too small I thought, but she got them up. Once in place she got me to push my penis back between my legs and once there, she lifted the waistband up a little more. There was no bulge of my cock any more.

She then was putting on me a pair of dark grey trousers. I only noticed something different about them when she was doing them up. The zip and button were to the side and the waistband had a little elastication. They didn't have any pockets to spoil the lines and cut. Tucking the blouse in, looking at my behind in the mirror, the trousers fitted over my bum perfectly. The lady then picked up a matching jacket. It was just a nice tailored dark grey suit jacket.

I now had a good look in the mirror and although all I was wearing were women's clothes, people would have to really look to notice. Any casual glance and nobody would notice anything odd.

To finish the lady got me to sit on the bench. She slipped on me a pair of black patent shoes. They had a bit of a heel, but it was a block style so very late 70s. The hem of the trousers covered over much of the design to hide that they were ladies shoes.

Looking in the mirror again, I just looked incredibly smart in a well cut suit. I didn't even really notice that the silk blouse and jacket were buttoned the other way, and wondered if anyone else would notice?

Before I properly thought that one through, the lady took my arm and we were through the curtains and showing off my new outfit to the older ladies. They were very impressed, saying that I look a very smart young man.

I was pretty calm now and comfortable with the very soft, lightweight materials of the blouse and suit. In shock though, the lady told her colleagues she wanted a break and was heading to the cafe round the corner. Before I understood, she had taken my hand and we were walking down the busy shop lined road.

This was a really strange feeling. I had been curious about wearing women's clothes, but would never have done anything about it possibly for years. Yet this lady read my mind and made all the decisions for me.

My confidence grew as we walked. I very quickly learnt to walk with the raised heel, after all they were only about one inch. We got to the cafe and sat at a table half way down the side. It was the usual bench seating and wipe down table tops. On the table was a red bound menu, one of those sugar dispensers and tomato ketchup in a tomato shaped bottle. A lady in one of those check gingham polyester overalls served us.

We both asked for a cup of tea and were quickly given glass cups and saucers with steaming hot tea in them. Sipping away at the tea, we didn't talk much but our eyes looked around the room at other patrons and at each other. It was as if we were having a full blown chat, just with our eyes.

What was intriguing was that I was sure the lady pretty much knew everything that I was thinking. Including wondering how those gingham overalls felt on the skin.

Finishing our teas, the lady paid, then we headed back to the shop. Inside there were a few customers, but it wasn't busy. The lady suggested I buy the outfit and wear it home and that is exactly what I did.

The door to a new world had been opened. I visited the lady in the shop quite regularly and she kept back certain things she found that may be of interest to me. Over a couple of years, I built up quite a wardrobe.

A few times she joked about dressing me fully feminine and taking me out, but I felt it would be years before I plucked up the courage to do that. Or so I thought.

Once she insisted I try on a mini dress from the 60s. It was heavily patterned with greens and oranges. The dress was so short it barely covered my backside. She added knee length boots and a bob wig. Even without removing my blond arm and leg hair, I was shocked at how girlie I looked. She tried to take me out into the main part of the shop to show her friends but I wouldn't let her. She did though manage to take my photo with one of those instant Kodaks. That was to become a regular thing and she built up quite a portfolio of photos of me dressed up.

Back then there was no discussion about being TV or TS, or whatever was the appropriate pronoun like today. There was no sexual tension or anything implied. The lady and I just had an understanding of mutual enjoyment. Her dressing me for fun and me being her mannequin. Sometimes we would go out to the cafe as a form of dare, but maybe that could be for another day to be told.