Weedy Boys Have More Fun

by Lauran Travis

 

I had been gay for several years, and enjoyed a steady relationship with Dave. There came a point when we felt we wanted to progress and live together, which involved looking at flats together, but we felt uneasy about the reaction we got when people realised we wanted to share as a couple not as friends.

We did think of viewing separately, or just being friends, but as this discussion was done in a bar after several drinks an unexpected suggestion was put in by one of our friends.

'Look like a straight couple'

After a laugh he continued to explain how he knew a trannie who you would swear blind was female, so why should one of us not dress up and go along as a female partner.

Dave is built like a rugby player whereas I am a 5'6" weed, the whole conversation then turned to this idea, and before I really knew what was happening it had been arranged for me to meet this Geri person who would assess my potential. Our friend then left to sort something out for the next evening. We agreed to this arrangement, or rather Dave thought it would be a good laugh and I was interested to try anything once.

 

I got quite excited while I was at work the next day wondering what would happen that evening. I was to call at Geri's about seven so I worked late then stopped at for a burger, before catching the bus to Geri's.

It was a rather nice flat, but the surprise was being greeted by a person I was assured was a bloke, but looked a perfect woman.

I avoided any gender references and we had a coffee and a chat. She had got the gist of what we agreed the night before and at first she thought I was a time waster just wanting a quick thrill.

To prove if I was serious, she set down some challenges that if I were prepared to do then she would help. I had to shave the moustache off first, allow her to choose the clothes, and at the end I would have to call Dave who would have to call round and take me out. I would not get my trousers back until I had been somewhere public!!

I agreed and Geri rang Dave to tell him to call at nine. I was then shown the bathroom and told to have a close shave and strip off. I found a dressing gown on the door and shaved. Next I had put on a bra and knickers, then sit still while she applied make up.

She did not stick to the challenges strictly, as she gave me the choice of trousers if they fitted or a skirt, as it was my first time.

A pair of loose fit black trousers fitted well, and a cerise silk blouse ended up the choice. She found a pair of sandals that fitted me, then placed a shoulder length wig on my head.

On being shown the mirror I was shocked by the change. As a bloke I looked poor, but now I looked attractive.

Geri asked if I approved, I said very much so, that was until I tried walking in the heels. I was told it takes a little practise.

Before long Dave arrived, and he did not laugh he complimented me on how good I looked, but he was reserved.

With great fear of being mocked as a bloke in a dress, I left Geri's front door trying to stay close and hide behind Dave. He drove us to a gay bar we do not use, where he fulfilled his part of the night and made sure I was out in public, but after one drink we left and he took me back to Geri's. It was barely ten.

He said he would wait outside for me to change, and left me to go to the flat alone. Geri was surprised to see me so soon and alone.

I did feel a little upset at Dave's brusque attitude; after all he had encouraged me. Geri took me in her arms and held me gently and as I relaxed she took me in and gave me a drink. Then without telling me she went out to Dave and told him to go.

Geri restored my spirits and asked some probing questions about how I felt. After a few more drinks she declared how alike we were, both submissive, both prefer men, not to mention both being a size 12 with only one size different in shoes and both looking good in drag.

She offered, only if I wanted to that was, to take me out one evening and show me how she spent her time. I said I had better check with Dave first, which she acknowledged but described him as no better than a homophobe.

As I cleaned up she showed me some of her wardrobe, with comments like 'this would look good,' and 'feel this one.' I caught the last bus home, and spent the journey mulling over the events.

 

The next evening Dave was acting as though nothing had happened, until I raised the subject, then he went cold. He called Geri a freak and had a real go at her, and indirectly at me.

I was hurt because I had enjoyed myself, liked Geri and rather fancied meeting her again. There was just Dave stopping it. I did not wish to offend Dave so arranged to meet Geri that Saturday, and told Dave I was helping my mother.

 

I could not wait, Geri told me to call after lunch so I arrived just after one, she had meant later but said nothing.

I had to strip just inside the front door and put my clothes in a bag, then wrap myself in a dressing gown. I had eaten but Geri had not so I helped her make a light meal, and then had a drink with her.

She complimented me on the other evening, and said there were many more things I should try to do.

She showed me a list she had made, saying she thought I could manage all that day. The list was something like this.

1. Shave body hair.

2. Do own make up (with help).

3. Wear high heels. (Which I thought I had done)

4. Wear a dress or skirt.

5. Try long nails.

6. Go to Freddie's bar.

 

I was ages in the shower shaving, but was sure when I finished it had been worth it as I rubbed in the moisturiser.

Geri had left out a red set of underwear which I readily put on and inserted the breasts. For the afternoon I was given a denim dress and told to make my mind up as to how short or long I wanted the skirt for the evening.

Then I had a make up lesson. I never realised how much care was needed, or how many different products used.

Then with a shoulder length wig in place I pulled on some tights, much finer than last times opaque pair. Finally Geri gave me a pair of sandals with heels on. I was complete and felt good.

 

It was late afternoon, Geri needed to get a little shopping, I could have gone but felt nervous about going out in daylight, so stopped in and looked at a few trannie magazines. I could not believe the pictures, some were great, others horrid.

When Geri returned I said I would only go out if I were great, to look like the horrid ones would kill me.

We sat and talked for ages, we just seemed to get on so well.

Geri booked a taxi for eight so I could buy us a meal before we went to Freddie's.

Geri went to change and invited me to join her. She found herself a purple dress; it fitted everywhere and did not get much past the stocking tops.

I took off the denim dress and looked at the choice, Geri finally decided for me, a short dress in black. Now she observed how her crutch was flat and mine had a bump. I had a choice again, tight control pants or the silk. I chose the silk but did not realise until Geri asked me to get down on all fours and fastened tape to my penis that silk was not the easy option. But with the knickers pulled up I looked good.

Next I had to master stockings, which was not too hard and felt so sexy. I was asked if I felt OK in the heels I had on earlier. I thought I could manage them, so Geri said I should try some higher ones,

'they go with the outfit', she said.

So I fastened on a pair black sandals with a small platform and to me, enormous heels, but I coped and walked around a little.

'They will ache by the end of the evening but they look fantastic' Geri assured me as she zipped up a pair of stiletto boots.

'Now then to show you how evening make-up looks.'

I watched as she applied bolder colours to her face, complimenting the purple dress. Then it was my turn.

Geri had to keep on giving advice but I got there. My eyes seemed to have grown, and the lips and cheekbones had so much emphasis I knew it was me, I just had trouble realising it.

After sorting out a necklace, bracelet, earrings, ankle chain and a few rings, it was still only seven thirty.

'Time to do nails' Geri said ' I bought these specially for you' and opened a pack of long nails. 'Now read the instructions while I do mine, then I will paint yours.'

I was soon gluing the extensions on and filing them neat, I soon started to notice how awkward my fingers became, but once Geri applied the matching deep pink to the nails I could not help thinking how good they looked, long and elegant.

The taxi arrived and it was a warm evening so we picked up the handbags we had filled earlier, and I walked out into the evening full of confidence that I looked great.

 

We ate at a small restaurant and for the first time I noticed how people reacted differently to me dressed as a woman.

I did rather follow in Geri's wake, she was so cool and confident, whereas I suspected everyone who looked at me saying unkind things about men in skirts.

When we got to Freddie's it was still quiet, but Geri seemed to know lots of people and soon I was being included in the chat, and receiving lots of compliments.

I had a problem when I needed the toilet. First I nearly went into the gents!

Geri steered me out of that one, then I had my penis facing backwards so had to sit and relax before I got any relief.

The best flattery was when a bloke genuinely mistook my gender until I spoke and then the look on his face was priceless.

 

I made two phone calls that evening, one to tell my mother I would be stopping out the night, after Geri invited me to sleep on her settee. It would be easier to get changed at her flat than change in town before going home as I would have to carry the male stuff with me.

The other was to Dave. Geri set me up to this.

I rang Dave and told him that I had finished earlier than expected and was now in town. 'Did he want to meet up?'

He said yes and was just nearby. So with a few vodkas in me we walked round to where Dave was. We knew he was with our regular group, so we planned it to shock.

I walked up sat on Dave's knee gave him a peck and looked for the reaction.

Most of the friends did not realise what was happening as they took a while to recognise me. The friend who had introduced me to Geri saw it and reached out to congratulate me, then Dave pushed me away.

I stood up and brushed my dress down,

'So I guess you don't fancy me?' I asked.

'If I wanted a bird I would have a real one' he replied.

'Hang on, this was your idea last week' was my response.

'Well it's not mine now, get that stuff off'.

I had not quite expected such hostility, 'I suppose you don't want to go flat hunting together then, I'd make a good girlfriend'

Geri stepped in and told him he did not know what he was missing, took my arm, bent down to kiss her friend good bye, then lead me out of the bar. A very embarrassed Dave trying to justify his actions could be heard behind us as we left.

The whole episode saddened me, I had felt a real affection for Dave and now he had thrown our friendship away, though I expect he would say I had thrown it away by going against him. Whatever was between us died that evening.

Geri told me I was released to be the new me, the attractive, feminine, girly, sexy, stunning, beautiful woman that has for too long been hidden.

It made me feel quite special all those compliments. The evening lasted for ages, yet passed to quickly. I was soon back at Geri's getting undressed and making a bed up on the settee.

I slept eventually but I was so excited it took a while to calm down.

 

It was late morning when I awoke, Geri was making a drink and looking as good as she did the day before, except she was wearing a long nightie and looking very elegant.

I pulled a sheet around my self feeling self conscious about being in the buff.

Once we were properly awake Geri asked how I considered the previous night's events.

Did I enjoy it?

….Would I do it again?

….How uncomfortable was I? (I was still taped up)

….Had my feet recovered?

 

I in return asked ….if I had been any good?

….Did people genuinely find me attractive?

….Did she mind having me hanging around?

 

The overall feeling was that we both enjoyed each other's company, and if I wanted to go out again then Geri would help me.

We chatted for ages about allsorts of things, but eventually I left for home promising to ring and arrange another outing. I knew I would ring up but decided to leave it until mid week so I did not seem too pushy.

 

To my pleasure Geri rang on Tuesday for a chat, to see how I was and ask me around on the Saturday. Of course I said yes.

We spoke later in the week and she suggested I buy my own underwear before I arrived!!

This meant a nerve-racking lunch break in the women's shops.

I knew what size to get; it was terrible not blushing at times. I had a white set and a pair of stockings of my own which distracted me all afternoon, and could not wait to get home to try them on.

 

The Saturday was a long morning, but eventually I arrived at Geri's, prepared for an overnight this time.

I undressed at the door and put on my underwear, and wrapped myself in the dressing gown.

The welcome was as warm as I expected, and soon I found myself in front of the mirror playing with the various colours and textures, trying desperately to remember what each one did.

After several clean-offs I had something that looked near to how I looked last week, but Geri gently added a few touches that improved the results immensely.

With the wig on and brushed out, we sat and chatted.

Sometime during the afternoon I attached the long nails and painted them myself, along with my toes this time.

I looked at catalogues, imagining what I might look like in the clothes, or wondering if I should buy some things from the magazines. If I was to continue I would have to buy my own stuff, it was a bit much borrowing all the time, maybe next week I would buy something, I thought, and Geri agreed, I needed to be me not her copy.

I asked where we were going in the evening, all she would say was it would be smart, and we had been invited out to a party.

 

Geri started to get ready after tea, showering and preening herself, then making up with great care. Finally she stepped into a black trouser suit with a tight cerise top, the trousers falling just right when she fastened the sandals to her feet.

She had found me a long Chinese dress with slits up both sides, and flowers emphasising the bust. Not only did I have to reaccustom myself to the heels, but also now I had a hemline that came to my ankles, and split up to the mid thigh. Some care would be needed not to sit badly or put a foot on the hem.

Regardless of the troubles I was elated to be dressed again.

At eight thirty the bell rang, I was expecting a taxi, but Geri let in two men, one was Paul, the friend who had introduced me to Geri, and another called John.

They complimented Geri, then Geri introduced me as Georgina, I smiled and said "You can call me Gina, for short".

Then Paul paid me a big compliment saying he thought I was a real woman until he realised it had to be me. My confidence soared.

He treated me completely differently. He was an attentive gentleman, always opening doors, helping me with my jacket, things like that, which he would never have done if I was in trousers.

John was driving and soon had us at a very smart house. There were plenty of people there already.

Gina took my arm as we entered

'This is not a gay party, the host I know a little, more John's friend than mine, there will be plenty of straights, just be careful of men's hands. Don't let them have a nasty surprise, you look great a truly gorgeous woman'

All I could do was look dumbfounded at her,

'how could you drop me in it like this?'

'You'll be fine, remember what I've taught you, and there's always Paul, John and me to look after you, enjoy yourself'.

Paul heard our conversation and came to take my arm, 'We'll stick together if you want, I'm a bit lost as well' I thanked him and we walked into the party.

We ate from the barbeque and drank the wine. Paul asked me about the dress and how it felt.

I asked him how it felt to be with me.

Paul chatted with several people while I hung back playing the shy girlfriend. It worked well and I enjoyed myself in Paul's company.

One particularly amusing moment was meeting the host, who knew Paul and John and about their sexuality and made some comment about being out with girls. We all looked at one another, guessed he had not read us and started to laugh.

I certainly did not say anything as I was feeling out of my depth anyway, but sometime later a few people came up to Geri and myself asking if we were women or men. Geri told me to take it as a compliment.

A couple of women rather rudely told us they could tell us a mile of, to which Geri smiled then turned to bitchily say they were only jealous.

I certainly enjoyed myself that evening, but it did not end with the party.

John ran us back to Geri's, and then came in for a coffee. John said he needed the toilet and Geri said she would show him where it was, and could I put the kettle on.

I sat with Paul and chatted while we waited for Geri to return.

After an unexpectedly long time neither had returned, and I said something like….'She must be holding it for him'

….to which Paul replied 'something like that anyway'

I felt a little stupid. They were obviously enjoying an intimate moment and I never noticed the signs. I made a drink for the two of us, and we politely drank it.

After much prevaricating, Paul eventually asked me if I would like to go out again. I was flattered, saying yes but I did need to get some clothes of my own instead of borrowing Geri's.

He said he would ring in the week, and see what we could do together.

I said it sounded fine, and if he had an idea where to go I could buy something appropriate.

The evening ended with John returning from the 'toilet' saying a few words,

Paul then got up gave me a quick kiss and promised to ring. Geri appeared later in a nightie, to have a drink. I had sorted out the settee for myself and was ready for bed also but not in such nice attire, I had my George T shirt and shorts on.

'Next time you get yourself a nightie or I put you out, OK' Geri joked.

 

Things continued in a regular way. I was George through the week, but after work on Friday I would go to Geri's and be Gina for the weekend. My wardrobe grew eventually having part of the hanging rail and several boxes stuffed with assorted lovely feminine clothes.

Paul became a regular partner, not fixed but we would be there if the other wanted a companion. Occasionally I stopped over at his house. Sharing a bed was very nice, he liked me because he had the best of both worlds, he liked the way women look, but also fancied men, so I filled both roles which pleased him.

With Paul it was safe and friendly, but Geri's nights out tended towards the wild. She knew lots of people, was loud after a few drinks, and very good fun. Her appetite for sex shocked me at first, maybe I was reserved but she soon changed that.

Some nights we went out dressed with only one thing on our minds, and it would be obvious, usually it ended up a quick fumble in the dark, other times a very nice affectionate warm up followed by a pleasurable climax.

One night we both got drunk, and when we got back to the flat we undressed each other. Then with Geri's lead we touched, then petted and eventually we ended up in her bed, both dildoed, both spent, then we slept.

It happened on rare occasions, but was very nice and seemed to affirm the friendship as something special, a strong bond between us.

  

  

  

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