How I Became a Transvestite

This story is mostly fiction, I will leave you to guess which parts are autobiographical.

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I'm now in my seventies, happily married to Denise. These events happened a long time ago now, but document the start of our less than usual relationship.

- - - o 0 o - - -

I admired Denise's pert bum as she got out of bed and headed to the bathroom for a shower, before we went out for the evening.

As I lay there listening to the shower, I looked at our clothes discarded around the room.

Spying her panties, I couldn't resist, getting out of bed, I picked them up and sniffed them. Hmm, heaven they smelt of her and they were even still slightly damp from her earlier arousal. I couldn't resist putting them on, knowing her wet patch was up against my genitals had me hard again in seconds.

I picked up her bra and held it against my chest. As I admired myself in the mirror, I thought back to my childhood and how even then I'd been wanting to try on girls knickers. I was always trying to look up girls skirts, wanting to catch a glimpse of their pretty knickers, how well and how smoothly they fitted, compared to boy pants.

I was sent to a minor all boys public school. Sex education was very vague, even the boys who had sisters couldn't really answer our questions, so it was 'dirty' magazines we learnt from. In those days female genitals were airbrushed out, but we didn't know that.

I can't remember what the other boys thought, but I assumed that girls must pee out of their bottom, after all they had nothing else to pee out of, or did they? I needed to get a better look.

About halfway home from school there was a public toilet just off the High Street. I checked around to see if the entrance to the Ladies was overlooked, it wasn't. After a few days I finally plucked up courage, nipped in, shut myself in one of the cubicles and waited. It wasn't long before I heard women using the toilet, I'd sit there quietly listening to them pee. It still didn't answer my question. When nobody was about I looked under the partition, no good they might see me looking up at them. I looked over the partition, if I moved far enough back they'd have their back to me. I would try again another day. I tried at irregular intervals, sometimes nothing, sometimes I'd see them lift their skirt pull down their panties, see their bottom as they hovered over the seat, pee and then wipe themselves. I still wasn't seeing, what I so desperately wanted to see. I wanted to know the SECRET. I was hooked I kept going back, then one day I got a fright. I nipped in as usual and there was a woman doing her makeup, we made eye contact via the mirror, I fled, never to try that again.

Not long after, I think money must have been tight because, I started at a state school. In my mind this was wonderful, there were GIRLS!

I soon discovered that after gym class when we were supposed to be changing, if I went back into the gym, I could look through the keyhole into the girls changing room. There were girls in various states of dress. There were girls going into or out of the showers. There were breasts, some were just developing, but best of all I saw the prize, the slit, some with a bit of pubic hair, they weren't smooth with nothing there.

I thought I knew about sex. A man put his 'dick' in a woman's 'cunt' and she got pregnant. Oh how ignorant I was, I hadn't a clue what a woman's 'cunt' looked like. I just knew it was somewhere between her legs.

What I did know was I wanted to go and pinch some of their underwear, so halfway through a lesson, I asked if I could go to the toilet. I went and checked the boys changing room, there were clothes hanging on pegs and I could hear activity in the gym. Back out in the corridor I checked there was nobody about and quickly entered the girls changing room. Once inside I stood still, quiet, listening and looking. There was nobody in the changing room. I grabbed panties from one peg and bra and panties from another, before escaping to the boys toilets.

I shut myself in one of the cubicles, my heart was pounding. I don't know why, but I started sniffing the crotch of the panties. Oh the aroma was like nothing I'd ever experienced, it was heavenly, I wanted it next to my skin. Taking off my trousers and underpants, I pull on a pair of the panties and put my trousers back on. I needed to get back to class. First I stopped at my locker and hid the extra underwear in my sports bag.

Back in class "Smith you've been a long time?"

"Sorry miss, I had a really bad tummy ache."

I'd got away with it. I heard nothing more. I let some time pass before mounting another couple of raids, each time taking two panties. Girls were gathering and whispering, I assumed they were talking about the disappearing panties. Then there was an announcement in school assembly about theft of underwear, so I stopped my raids.

I now had six pairs of knickers and one bra, I never did find out who they belonged to. I gave up on the bra after finding it difficult to put on, but I often wore the knickers to school. I would never wash them, I didn't want that heavenly girl smell to go, but eventually I had to bin them. They had become stiff and encrusted with cum and pre-cum. I never had another opportunity to pinch any used panties, new or washed ones were not what I wanted.

I'd forgotten about my girlfriend in the shower, as I held her bra up to my chest with one hand and my other hand rubbing my erection through her panties.

"WHAT THE FUCK ARE YOU DOING?" Denise yelled.

I couldn't answer, she'd caught me red handed.

"How long have you been dressing in women's clothes?"

"I...I...I've never dressed in women's clothes." I stammered.

There was a long silence as she as she circled me.

"Go get a shower," she ordered, "then I'm going to dress you, before we go out."

I understood she was pissed off with me, but in my shock, I didn't cotton on to the meaning of her statement.

As I was showering, she came into the bathroom and told me to shave my armpits and my legs. She wasn't going to dress me as a woman, was she?

"Why?" I said fearing the answer.

"Just do as your told! I've put out some clothes for you to try."

Once showered and shaved, I went back to the bedroom. On the bed was a matching set of bra, panties and suspenders, some stockings, an under-slip and a beautiful green dress.

"I can't go out dressed like that." I mumbled.

"You can and you will Danielle!"

"I'm called Daniel." I said, trying to put my foot down. Resistance was futile.

She watched over me as I dressed, helping me with the bra and stuffing it with some rolled up socks. I pulled on the panties. She put the suspender belt on me pulling the dangly bits under the panties and instructed me on how to put stockings on. I then stepped into the under-slip and pulled it up.

Both now in our underwear she made me sit, while she combed, brushed, trimmed and styled my hair. When she was satisfied with the style, she sprayed it. Then she started on the makeup, cleanser, foundation, eye liner, eye shadow and lipstick. I sat through it all too shocked and afraid to put up a fight. The green dress went on and she zipped it up at the back.

I still didn't know what I looked like as she wouldn't let me see myself in the mirror. I had to sit in the corner while she finished her makeup and got dressed. We were both wearing sheath style dresses.

When she was dressed, she selected some jewellery for us, clip on earrings for me, a necklace and a couple of bracelets. She then handed me one of her small clutch bags, told me to put my phone, some money and my credit/debit card in, we were going out to eat. Opening the bag there were some tissues, some makeup and some feminine items I would never need to use.

Now she let me look in the mirror. I was shocked at the transformation. My hair was in a short feminine style, how she'd achieved that I'll never know. When she was doing my makeup, I thought she was plastering it on, but no. It looked as if there was barely any, just my cheek bones highlighted, my eyes looked amazing and pale pink lip gloss. The dress fitted perfectly, despite the rolled up socks for breasts. In fact I looked a very presentable and classy woman.

Handing me a pair of shoes with three inch blocky heels, she said, "You are taking me to that French restaurant near the church on the High Street."

I knew exactly the one she was talking about. It had a reputation for being very posh and serving top quality food at eye-watering prices. I was in no position to object.

As we walked to the restaurant, I tried to hold her hand, partly for help walking in heels for the first time, but mostly to try and calm her anger and reassure her of my love. She brushed me off.

Part way there she asked, "How often have you worn my panties, do you or have you ever wanted to dress up in women's clothes?"

I started to explain about my childhood and the things I had done. Soon we were seated in the restaurant, and I carried on. No I'd never dressed in women's clothes. Yes I had thought about it. I went on to explain that in my teens, along with a group of friends, one of us would pick a pub or bar to visit. It might be to watch football on the TV, play darts, snooker, cards or whatever. One week a lad called Ian, the homo in the group, took us down some steps round the side of a cinema. There was a dimly lit bar in the basement. There were 'women' sat on men's laps, they were kissing, the men had their hands up the 'women's' skirts. The only real woman in that place was a young, very bored looking barmaid.

This story seemed to excite Denise. For the first time she seemed to relax, she moved in close, her hand on my thigh, moving up under my skirt. I looked down, I had a tent in my dress, her hand rubbed my erection. Just then a waitress appeared and asked if we were ready to order.

"Not yet, I think we need to go to the Ladies Room first." said Denise.

"I can't go to the Ladies!" I mouthed.

"What, you think you can go to the Gents, dressed like that? Hold the clutch bag in front of you, nobody will notice."

In the Ladies, she pushed me into a cubicle.

"Lift your skirts." She ordered.

I did as I was told, still unsure of her mood and intentions. She yanked my panties down.

"Sit."

As I sat, she lifted her skirts and pushing my legs apart, squatted in front of me. She grabbed my cock and swallowed it. Never had she taken it in that far, I groaned in surprise and pleasure. Her head was bobbing up and down, my prick going down her throat, that had never happened before. I watched her rubbing her pussy through her panties. The door to the Ladies opened, we froze.

There were only two cubicles, so she was just the other side of the partition. We heard her peeing, then she farted and burped. We were both biting the backs of our hands trying not to giggle. We heard the spinning toilet roll as she pulled off the paper, we listened to her wipe herself. Denise licked the tip of my cock, I bit harder on the back of my hand to stop myself from making any sound. Her cubicle door opened, she washed her hands, the hand dryer burst into life, then there was a few minutes silence till at last, the door to the Ladies opened and closed.

We finished what we'd started, she swallowed every last drop of my cum, I got a good feel of her sopping panties as she came. Denise was going to put her sopping panties in her bag and go commando, but I begged her to swap panties. After all I loved panties that somebody had cum in next to my genitals.

Once we'd cleaned ourselves up, tidied our hair and makeup and sat back at our table, our waitress returned.

With a big smile on her face she asked, "Are you ready to order now, ladies?"

When she went off with our order, I said, "Do you think she knows?"

"What, that we had sex? Yes but she thinks we're a couple of lesbians."

I wondered if any of the other diners had noticed our long absence, did they think we'd been having lesbian sex in the toilets? Strangely I rather hoped they did.

During the very enjoyable meal, we talked and relaxed more into the new dynamics of our relationship. We seemed to become closer more intimate on a personal level. Walking home hand in hand, we occasionally stopped and kissed.

Arriving back at our flat and closing the door we grabbed each other passionately, fighting to undress each other and scattering clothes as we went. We didn't make it as far as the bedroom. Denise pushed me to the floor, I pulled her panties down, she straddled me, flung her bra away, pulled my panties to the side and guided my erection into her very wet vagina. The sex was raw, rough, needy and passionate all rolled into one.

Later in bed when things had calmed down, she admitted that although she had been shocked and pissed off with me. She'd wanted to humiliate me by dressing me as a woman, but as she was doing my hair and makeup, she became intrigued at the possibilities and wanted to see how I would cope. Just being dressed as a woman I'd, started to act like one, my voice became more feminine, I checked out other women, not the way a man would, but like a woman, I was checking their hair, their makeup, the way they dressed, moved and interacted with other people. If other people thought we were lesbian, she didn't care, it even excited her.

Nothing more was said for a couple of weeks, then in bed one night.

"I miss Danielle" she said.

I turned to her, held her in my arms, and with a lump in my throat I sobbed, "I do too."

The next morning was a Saturday. When we got up, over breakfast, I asked what did she have in mind for Danielle and Denise's next outing.

She said, "Well I've been thinking about that bar you and your mates went to, and I thought we could try a lesbian club."

"I didn't know you had lesbian thoughts? Whatever we decide, I want some stilettos and I don't want to rely on a sock stuffed bra."

"Of course I've thought about lesbians, doesn't every girl? It doesn't mean I am one, it doesn't mean I'll never experiment, but I'll be happy if they think you and I are."

So we fired up the computer and looked for some breast forms. Not wanting to look ridiculously large we ordered a pair of size 34D breasts. You could also buy a suitable bra to go with them. Great I wouldn't need to worry about a bra fitting. Delivery would be within the week. I then started fretting about stilettos, I wanted them soon so I could practice walking, before we went to this club. Oh I would need a dress as well, I didn't have anything to wear.

"Calm down. First lets shower and pamper ourselves, this afternoon we'll go for stilettos and a dress."

"But I haven't anything to wear to go shopping in!"

I was beginning to sound like a spoilt little girl.

"I have a whole wardrobe of clothes that we can look through. Stop stressing."

We both showered, shaved our armpits, legs and Denise trimmed my pubic hair, shaped it into a little triangle, like hers. We moisturised. She shaped my finger and toenails, before painting them. Once dressed and made up, we went shopping.

By the following weekend, everything was in place and I was more confident. I was in full Danielle mode.

We had a great time at the lesbian club, people assumed we were an item. That didn't stop the kissing or the hand lingering just that little bit longer. If anybody suspected that I wasn't what I appeared to be, they never said anything, I was treated like any other woman there. We both danced and chatted with other women.

Arriving home in the early hours, we were undressing each other as soon as the door closed. We got to the bed this time, by now I was down to my bra, suspenders and stockings, Denise was just down to her suspenders and stockings. She pushed me onto the bed, lent over to reach in her bedside draw.

"Tonight your going to be my woman," she said taking strap-on and lube from the draw.

"My god," I gulped, "I didn't know you had one of those."

"I ordered it, when you ordered your breasts. I can fantasise too, you know."

She was right, of course she could have fantasies, but I was afraid. It was about the same size as me when I'm aroused, but it looked too big for where she intended to insert it. She put it on.

"Now suck my cock," she said.

'Really,' I thought, I didn't fancy sucking silicone, but as she straddled my face, I didn't have much choice. While I sucked, she started to lube and loosen me up, sticking one, two, then three fingers in me. When she judged me ready, she spun round, spread my legs and started pushing into me.

After some initial resistance and discomfort, she was suddenly in me and pumping away. This was better than I expected, I was beginning to enjoy this, pleasant sensations were building deep inside me. It was unexpected, but I felt an orgasm building. I couldn't hold back, I didn't want her to stop. I wrapped my nylon clad legs around her, encouraging her to pump harder and faster. Suddenly I was screaming, my insides were turned to jelly. I lay there exhausted, floating on a cloud, warm, safe and contented.

As I came back down to Earth, I realised that Denise had also cum. How did that work? Only when she removed the strap-on, did I see the cleverly sculpted rear of it, that would have been rubbing her clit.

Over the weeks and months, I dressed more and more frequently. If people thought we were lesbians, when we were out and I was dressed, we'd reinforce their perception. We still visit lesbian clubs on occasion, but under my clothes I'm still male.

I still love to watch women peeing, made so much easier now we have the internet. Over the years I've filmed Denise peeing in the woods, down alleyways, between parked cars, in abandoned buildings and using urinals in the Gents.

At home in private we became a married couple, but we would mix up our gender roles. Sometimes we played the opposite of our true gender, sometimes we'd both pretend we were the same gender.