New Challenges
by Lauran

We were going to do it, we had discussed what was needed, and how we were going to do it, all we needed to do, was to actually do it.

Running marathons like a lot of things needs planning and preparation.

It started off with one of those idle chats about what if we could do anything, and he suggested that as a serious shopper and general couch potato I would never consider doing a marathon, I liked my heels too much he told me.

Then it was my turn, and his comment about heels made me think down a rather perverse route, he liked put across this manly image he would never go out as a woman, in heels, the full works in fact.

We both laughed and took another drink of our wine. But then as we were getting ready for bed I glanced at myself in the mirror, I was getting a little out of condition and maybe some exercise would be good for me, and told him that maybe I should do a marathon as I pulled my tummy in. the look in his face was priceless, he went pale, started telling me how hard it would be, how people die doing it, how I had no kit, but what I think was at the back of this was that if I did this then maybe I would want him to do the challenge I set him. And that seemed like fun.

The next day I had done my research, a marathon was do-able, six months proper training and the right shoes should see me get to the finish line. I choose a big city race with lots of fun runners so I could go slowly and not stand out, then ordered my shoes and some kit, then waited for the look on his face.

Three days later the packages arrived, I left them out deliberately so he would ask about them, which he did, and as I opened them he wilted a little, asking if I was teasing him, or was I serious, so I showed him my receipt for the entry to the race and he laughed but only weakly, he knew if I got an idea I would see it through.

I had my training schedule written up with how far I should run each day, or do some cross training, everything just getting gradually longer or harder each week over the next six months, alongside it I made out a schedule for Mike so he could train for his challenge, which would take him from a man to being a woman. While I would go from couch potato to athlete.

My first run was to make sure everything fitted and was comfortable, while doing a couple of miles running and walking. Mike was to look through magazines and a few stylebooks I had so he could get an idea of what lay ahead and as I put it to visualise how he will look in six months, rather like me visualising the finish line. My run I think was easier than his experience, he looked worried and confused when I got back. He had convinced himself he would never look like a woman, and it was ridiculous to try. Maybe I had given him the wrong information first, those models do look great, and Mike would never be a model, so I showed him some cross dressing websites to show him how a man can be transformed into a reasonable looking woman. When he had been reading for a couple of hours I asked him what he thought, he was a little more positive but still doubted he could do it. I used the running metaphor, I did not know if I could do the marathon, but I have to start with trying out easy stuff until I get better, maybe I would fail, and suggested he take the same attitude, small easy steps first and see how they go. This went down better as there was the option of failure, though I don’t like it, I will accept certain things just cant be done, but I knew both our challenges were possible even if Mike did not.

One thing I was going to be insisting on with Mike’s challenge was that he was going to be a feminine woman, not a butch half way woman. His training plan got more detail, but whereas mine was a daily schedule, his was more of a weekly plan

Week 1. Buy knickers, camisole, pop socks and low heeled shoes.

Week 2. Wear the socks and shoes around the house, underwear when ever possible.

And so on until

Week 29. Go out fully dressed, be a woman and do something Michelle has never done before.

The highlights were for Mike and possibly me.

Week 3.

Running for 30 minutes without stopping.

For Mike wearing knickers to work, he described it as slightly wrong, stimulating thinking it was wrong, and stimulating as the satin caressed his man tackle.

Week 4. Proper noticeable heel

We went out and bought higher heels, 40cm block but it was getting there.

Week 5. Wig

This week I ran my first 6 miler.

Mike now has a long brunette wig that flips out around the bottom and brushes across his eyes. He looks very cute.

I tried and succeeded to get an extra experience into the schedule, when I am on I persuaded him to also wear a tampon, so he can empathise with my monthly routine. On the Wednesday we were having sex and I found the cotton thread there, so nice to know he is taking this so well. He is only using light, but I think by the end I shall be giving him extra heavy.

Week 7. Wear a bra with filling

I went online and found a runners website called fetch, lots of people on there doing the same race, lots of support. Also joined a running group that makes the longer runs easier with the company.

We ordered false tits for him, and two 34C bras, without any comment from me he has included them into his evening dress change programme.

Week 9. Tampon.

I managed 10 miles, without stopping.

Week 10. Blouse or female top

His first blouse, a soft white cotton, very nice. The bra was pulling his shirts and he admitted they were uncomfortable with his shirts. It looks a little incongruous but with time he will get there

Week 11. Female cut trousers

This I thought might have been harder, but we bought black cords, the flat front, side zip fastening did raise a few murmurs of why a side zip, but it is small steps leading towards the goal. They are nice and long as well to go with heels.

Week 12. Wear trousers all weekend, and bra when at home evenings.

I did buy him a short leg pair of trousers, so he could wear them with his male flat shoes, made sure there was a side zip though, which was hard. Now he can go out at the weekend without changing.

Week 13, Tampon, (large)

I read an article about how running increases libido, I realise we are doing it more, but I had put it down to Mike turning me on with his dressing.

Week 14. Skirt and tights

His first skirt, flared calf length denim. He is wearing it around the house with dark opaque tights. I don’t know if he is just copying me, but he quite naturally wears a skirt, tucking it under as he sits, being careful when crouching so as not to stand on the hem, little things like that. Also bought more tops for variety, a vest, a pink T and thin cardigan set, and a thicker knitted cardigan.

Week 15. Full shave

This one he did not like, it is a more permanent change, and he could foresee problems if anyone saw him in shorts. But when does he wear shorts? Only on a holiday. He gave in and I showed him how to use imaac and a lady shave. Rubbing in the moisturiser got him in the mood for an early night. When he wore his tights the next time he told me how nice they were on hairless skin. I took that as a yes to there being no more trouble keeping him hair free.

Week 16. Make up. First try.

I did this on the Sunday, and I knew it would be good, his features are not heavy set so when I had given him the works he looked really good. With his wig on even he accepted I was right and he looks good and would pass as a woman, visually anyway. During the week he practised with the make up, coming for tips when he got stuck.

Week 17. Full make over. Tampon

I have done the first of my 20 mile ‘long’ runs, this is really tough.

Make over done at the weekend, by himself while I was on my run, make up, wig, full underwear, skirt, blouse and heels. He did not go out, just pottered about the house. I did though and bought him some satin pyjamas, a treat for getting this far. I am not sure who enjoyed them the most, but the satin and smooth skin turned us both on.

Week 18. Go out in trousers wig, and make up.

A week after his first complete cross dressing we toned down the make up to mascara, lip gloss and light blusher, and chose clothes so he could go out totally in female attire. At a glance you would not notice anything. We did feel the bulge at the front of the trousers needed some attention, Mike has been told to experiment on hiding his man bits for a flat front.

Week 19. As above, but with breasts.

My second 20 mile run.

He has now gone out as a woman, the full works, bra, wig, full make up and heels. We added a pale pink nail polish this time, will use more obvious colours in coming weeks. It was only a walk down a road at night, but it has been done.

Flat front sorted, he has bought a gaff, does not look to appealing when in panties, but does the job, and he will try to think of something better.

Week 20. Deportment lessons.

He is quite good already but it is on the schedule, so I had him walking with a book on his head, and telling him off if he clenched his hands or did not sway his hips.

His toenails are painted fulltime now, and today they are baby pink.

Week 21. Evening’s, full change. Piercings? Tampon

The full change he just did without prompting, I came home Monday to find him as Michelle and cooking the meal. After much deliberation he agreed to have studs in his ears, I explained how they needed time to heel, and it needed to be done now. Good job his work does not have a smart dress code.

Week 22. Go out in a skirt.

For him to go out after dark for a walk with me was easier than either of us expected, he was nervous as he always is when he worries who might see him, but he has been out a few times in trousers so to add the skirt was not as big an issue as it might have been. His female routine is getting more involved, with changing when he gets home, shaving, and now cleaning his piercings he is realising how much goes into being a good looking woman.

Week 23. Last long run.

Evening out with me as Michelle.

With a few evening walks under his belt as it were, we went out to a more public place. There is a gay area in the city that we knew would be safe, so after a Saturday spent going over all his preparations we went out for a drink and a meal on Canal St. He looked so cute and I could tell he was getting a buzz from it, as for me walking down a street holding a females hand was an unexpected delight.

I found out when he undressed that he was not using the gaff, looked great undressed, but sex was hard, as he had taped his bits between his legs.

Week 24. Start tapering.

Go out solo. Tampon (super)

Entered a half marathon, felt good at the end, pleased with the time.

He had already done a few walks alone, but this had to be more public. First off he did a late night shopping at Trafford centre, just window-shopping, but he came back with a new top and a neat flared mini skirt, said he wanted to know how it felt and if he liked showing so much leg. Next, at the weekend we went to Canal St separately so I could watch from a distance and save him if he got into trouble with men, he did look the part, possibly to well. He glued his breasts on for the first time on Thursday and kept them on until Monday, it is quite odd sleeping with him with his breasts under the nightdress, but odd in a nice sort of way. Another event of note this week was the super heavy tampons I gave him, he never questioned it, just used them.

Week 25. Long nails, and tanning moisturiser.

He was spending all his non-working time as Michelle, even did the weekly shop on Friday in trousers and heels. While out, he picked up the essentials for this weeks session. Saturday saw him with long nails fixed to his fingers, and his pale skin getting a little bit of colour. This would take time but I felt it would be worth it.

Week 26. 75cm narrow heels. Stiletto sandals?

Last long run, I start tapering.

The nails only lasted till Sunday evening, but he kept on with the tanning every evening, by the end of the week his skin was looking quite good. So we went shopping and bought him the stiletto sandals that he could wear without tights, but also bought stockings and suspenders, because we could and so he could enjoy the sensation of wearing sexy underwear. Now I felt he was getting close to the challenges final stages as we went out that evening with him in a skirt and proper high-heeled sandals.

Week 27. Decide on final event

We have two weeks left and over a drink in a bar we decided that he really had to do something totally girlie, something only a woman would experience, as far removed from Mike’s experience as possible. I did not like to say but he had already done lots of girlie things Mike would never have done, but I was looking for an extreme situation now. We considered a salon trip, but what extra would he do that was new? Then I noticed a couple kissing, and remembered the odd occasion when Mike had got chatting with men in bars when he was out on his solo runs. So I suggested that Michelle as a girlie girl should have a boyfriend, Mike paled under his make up, but I told him to hear me out, Mike was not gay, but with me we looked like lesbians, a couple of women being affectionate, to look proper female Michelle needed to partner a man. This raised questions about who and where to find such a man, but I said he should leave it to me I was sure I could find someone nice to partner him as Michelle.

Week 28. En femme as much as poss. Tampon (extra super)

Michelle is around fulltime it seems, the house is very tidy and the washing is always done now. I found a partner by going online in some of the cross dressing sites, explained what I was looking for in the classified ads and was amazed how many replies it got. Most were weird but three I followed up, then I got one to ring Mike and ask for Michelle, who was not in on this at the time. Pete was great, he rang asked for Michelle, Mike stuttered a little, then said yes in his best voice, Pete chatted and explained about how he would like a partner for the weekend as he was going to watch a marathon, but wanted to make the most of the time as he could not run, and spend the weekend with Michelle. Mike knew it was a set up but quickly fell into the charade, and went online to get a look a Pete’s blog. I came in behind him as he read. Pete was a good looking guy who liked his women different, he was a fit and active man who should have done this marathon but was injured so with the travel booked he was going to go anyway. When I said he was a nice bloke, Mike or maybe Michelle replied with a rather unexpected ‘umm, yes he is isn’t he’

This triggered a sequence of events not in the plan. On Wednesday Michelle had been on the phone to Pete again and made firm plans, Michelle would travel with me to the race, but I would go off with new found running friends I had meet on a runners website for a meal, then apart from sleeping we would spend the weekend with our new friends. This meant Michelle had to get ready and had soon found a salon that would accept a man called Mike for an appointment later that day for several treatments.

His hair was not long enough, but they weaved his wig into his own hair, he had proper false nails fixed and painted on his fingers and quite to my surprise had let them thin his eyebrows far more than I had ever dared.

Thursday he declared that he would need a new outfit, and went shopping alone, coming back with a gossamer thin red dress that lay over a red satin slip, a pair of strappy spike heels and a neat red clutch bag. His only defence was if it is worth doing, it is worth doing well.

Friday he spent primping and preening himself in the morning, and then about midday we loaded the car and set off. If he had not been driving I am sure he would have been texting Pete all afternoon, I was beginning to think I had maybe been too persuasive. We were only spending two nights away but he was acting like a woman, he had enough stuff for a week, as Mike he took a hold all, now a suitcase was bulging, as well as some clothes on hangers in the back.

He had travelled in his low heels to drive and some tight trousers, but once unpacked he went and showered then went through his make up routine finally dressing in his satin cream blouse and brown disc skirt, tan stockings and the stilettos. He was certainly doing his challenge to the full.

I had dressed in a nice comfortable running top and jeans and was ready to meet my new friends for a pasta meal, but before we parted we had a little chat about how well he had done, he knew everything he needed to know, and he could go through with it, he would be Pete’s woman, Michelle, and he was to enjoy it now all the hard work was over. Funnily enough he almost gave the same speech back about my marathon the day after. We parted at the hotel door, and I watched a very sure woman stride away from me making the skirt swish and the heels click. What a transformation, he had certainly achieved the goal, now could I?

Week 29. The race. Success is assured if the training has been done well.

We both claimed success.

Jenny asked me to write down my experience, so here it is.

She has covered much of the ‘training’, I was not keen at the beginning but there were three events that kept me going.

First was the sensation of female knickers, we had bought the silky ones and they were just fantastic to wear, even the camisoles which I felt a little more conspicuous, were very nice on my skin. When I started wearing them fulltime it gave me a sense of doing something I shouldn’t be doing, not quite wrong, just not quite right a bit like a naughty secret that harms no one.

Second was the body hair, again I was resistant, but once I did it my skin felt so different, especially when I wore tights or stockings.

Third was the thrill of going out dressed in female clothes, even the starter trousers and a white blouse that looked like a shirt, but that I knew were women’s clothes gave me a buzz, like the knickers but better, I was doing something way out of my normal and I was not caring how people reacted I was enjoying being different. This only got better with the introduction of skirts and heels when going outdoors, that feeling of ‘I should not be doing this’ was just great.

I think what Jenny really wants me to note down is my time with Pete. As I say the skirt wearing was brilliant, I had been out to Canal St and shopping many times in the weeks before, the last few days being fulltime. So I should have been confident of myself but I was going to meet someone I had only spoken to and e-mailed, what would it be like in the flesh, would I be any good at keeping up the pretence of being a woman?

We had arranged to meet at a coffee shop near the hotel, and having exchanged pictures it was easy to recognise each other. He looked every bit as fit and handsome as his pictures, I was even his height when in heels, but then I am on the small side. The coffee went well, we chatted about running and his other interests, then about work. After a while we moved onto the marathon expo, a large show with lots of stalls selling running stuff really, I felt very conspicuous in my heels, as everyone else seemed to be in trainers. Pete meet a few people he knew and promised to give them a cheer in the race, I bumped into Jenny as she moved between the vendors, she had bought another running top and had a smile on her face. She had contacted some of her group, they had a meal booked and she intended on an early night, so told me to come in quietly and make sure I get in the right bed. The hotel only had twin rooms left. With a quick peck on the check she told me Pete looked gorgeous, I smiled back and told her I knew.

Anyway Pete was not running so we could drink and eat whatever we fancied. As the evening moved on we tried a couple of bars, then a pizza restaurant with more wine, we even did the sharing sweet. I was really getting into this girlie thing, so much so that as we ate I would touch his leg with my foot, then when we left I linked his arm. We found ourselves near our hotels in another bar and I was on the gin, I asked about his liking for us special women, and about his exploits, which he was candid about, he was gay but did not like being intimate with a full on man, whereas with someone like me he gets the best of both worlds. Sex he said was better than with a real woman and told me about some of the trannies he had been out with, one he even lived with as a couple for two years until she decided she no longer wanted any male bits, and had SRS which Pete was not happy with. By this time we are well cuddled up together and I am thinking if he invites me to have some sort of sex what would I do, it sounded quite exciting to my female immersed body and alcohol dulled mind.

It was getting late when we decided we should head for our hotels. He offered to see me to the door, I pointed out it was only across the road and as we turned for a good night kiss I opened my mouth a little wider than I intended and within seconds our tongues were meeting for the first time. When suggested he show me his room I just threaded my fingers into his and followed, this was just so much fun pretending to be the girl.

His room was nice; he had got a double room and what I expect is a nice view in the day, much better than ours. He brings out some cups and offers me a coffee while I made myself comfortable on the side of the bed. Before the kettle boiled we were kissing again and getting into it, his hands caressing most of my body, undoing buttons and exploring the tops of my legs, I was not so forward, until he said I could do whatever I wanted, as he took off his jumper, his muscles looked excellent, so toned. I ran my fingers over his chest and for some reason noticed his trousers bulging at the front, I must have stared because he confirmed that I had done that to him, then stroked it through the material, I felt it twitch, wow that was me doing this, he slowly undid the fly zip and I got my first close look at another man’s penis. Completely lost for what to do, I never considered this situation, but I was being girlie and asked him what he would like me to do. Stroke it he suggested, this made his breathing get a little heavier. Then he asked if I would kiss it or stroke it with my tongue. By now I knew he would cum soon, I had been there myself, and I was just taken up with the whole experience, so as he lay back I leaned over and kissed the tip, the licked it, feeling it pulsing, then for no better reason than I always wanted Jenny to do this, I swallowed his dick and started bobbing up and down on it. About four strokes and he came straight into my mouth. He pulled me to him and kissed my still cummy mouth asking if I liked it, I had nothing to compare it too, but honestly said it was not the most revolting thing I had had in my mouth. We lay for a while until the energy returned and told him I should be going, which I did after a quick tidy up of my appearance, and left to spend the rest of the night in my single bed.

Next morning Jenny was up and anxious about how she could complete her challenge. She was dressed and ready early so she could eat early with time for it to go down. I was being girlie so I took my time dressing and doing my face. We then went to the start where I had to leave her and wish her good luck, then for me it was off to find Pete.

I had not mentioned anything of the night before, but seeing Jenny made me feel as though I was cheating on her in some way, but I was not going with another woman as in an affair, I rationalised it as two men mucking about in a role-play situation. So when we meet up a bit later I happily greeted him with a full kiss and took his hand as we walked to the point he said would be a good place to watch from. I had come prepared in my denim skirt and a warm jacket, I was not sure about a full day on my feet in heels but you only get to do some things once. We behaved like teenagers really; he would cuddle me from behind letting me feel his erection in my back. Then we spent ages cheering on people we had never meet just shouting out names we read on their vests. Pete’s friends went past, then a good while later Jenny jogged past I called her and she waved back, then she was gone. A coffee and make our way to the finish Pete suggested. His friends finished two hours before Jenny, so I did a lot of standing around while he went off chatting with mates. I was beginning to think something terrible had happened when at five hours she jogged over the finish looking quite fresh and beaming a fantastic smile. We hugged, she told me it was great, what a brilliant experience, then saw Pete behind me, gave me a kiss and told me that there was man waiting for me to be his woman. She had made lots of friends and they were meeting up for a celebration later and I should do whatever I wanted she would see me in the morning. Had I heard right, she virtually told me to go and let this man make a woman of me, and not to rush back.

We had most of the afternoon to kill, so I suggested a walk around the shops and get a bite to eat, this was done like a young couple, I spent ages looking in dress shops windows asking what he liked, and wondering what I liked. We ended up in the hotel bar, and watching some runners arriving looking worn out but happy. But this was getting boring so I asked if I could use his toilet as a pretence for going to his room. And after I had relieved myself I made it obvious I wanted to repeat the previous evenings action when I undid his pants and knelt before him. It was just so far from my usual Mike behaviour I was able to do anything I thought Michelle would like. So when he had pumped his load into my mouth, and I had given him a cummy kiss. I told him I was going to get changed for the evening and I was not going to accept McDonalds as a restaurant.

I left for my hotel room, and a shower, then a moisturise, next a careful night time make up, then my new outfit, red strapless bra, red thong, bare legs, the red dress, chandelier ear rings, some necklace and bangles I borrowed of Jenny and my spike heels, I checked I had everything in my clutch bag, then waited for his call to tell me he was in the lobby.

After a decent pause, I went down to meet him, I felt almost naked in such a thin dress and skimpy underwear, but his expression as I wafted towards him was best described as open mouthed. So I went up to him kissed it and told him to close it. He did not look too bad either in a smart suit.

We had a lovely meal, I enjoyed the walking around in the dress it was so sensual as it brushed my legs and hands I thought I could easily get used to this. But all nice meals do end, and as we had our brandy to finish with, the conversation turned once again to how good I looked, and how much Pete would like to spend more time with me, I insisted he only had that night, so he insisted we make the most of it. He then told me we were going back to his hotel because one thing he had been asked to do was to make me feel like a woman. I told him he had already done that and I knew I looked like one and was enjoying it. No he insisted in his hotel he could make me feel like a woman.

I took a while to get there because I wanted to walk and enjoy the dress, but once he had the door shut I started to kiss him, then went for his cock, but he pulled me back, undid my dress so it fell to the floor, ‘just as gorgeous without it’ he told me then started kissing me, ‘tonight is about your pleasure’ this would be hard I thought my equipment is securely trapped in between my legs, but he continued to arouse me, then with a move I did not expect slipped a finger into my arse. I tensed but I soon relaxed as I realised what he had in mind, could he make me feel like a woman by inserting his dick in my hole in a similar way that any man might fuck a woman? I relaxed and let him get on with it, trying to respond as best I could. Soon I was on my back, legs in the air with my hole lubricated and his erection finding it’s way inside, I flinched as the muscles stretched but I guess the tampons had been helping me down there, then he explained about a g spot he hoped to find, he was gentle as he slowly pumped into me, then he hit something that sent tingles through me, and a wow out of my mouth, good he asked, all I could say was wow between the ouches, he was getting more vigorous until I was pulling his buttocks into me and telling him to keep going, then I exploded inside, I am sure he came as well, but I did not care as I lay there exhausted my arse full of cum and the muscles feeling shredded. That had been one very different experience that Mike would never have done, and one Michelle had not done before.

Ramifications

For me the result of getting fit and succeeding at the marathon left me wanting to stay fit and continue running, it had been such a fantastic experience, Paula Radcliffe need not fear me but I had achieved my goal and wanted to do another race, but for the first week I was told to rest, and I was knackered so that was easy, then I rejoined my local running group and started training again.

I felt so knackered and so good at first I did not realise that the challenge Mike had done had left a legacy with him as well. First thing I noticed was a week or so later when sorting the washing, there were no boxers in there, when I challenged him over it he just simply told me that he had learnt much from his experience, and the knickers felt much nicer than his regular male pants so why not. I did not disagree; I would not choose boxers either.

About a month later I realised that his skin was still tanned and hairless, I did expect the body hair to be returning but maybe it was slower growing than mine.

Maybe I was going out more and had not been taking particular notice of Mike’s appearance but one weekend we were shopping for our food and I recognised that he was wearing his ladies cords and a top that though much like a T shirt was not a loose man’s style. Rather than come out with it directly I took a detour into the clothes section of the supermarket and picked a few items, then picked up some flat sandals that were Mike’s size, ‘Do you like them?’ he pointed out they were not my size, so I pointed out they were not for me.

‘In that case I prefer these’ and picked up a black flip-flop. I just put them in the trolley and carried on as if it was quite normal for my husband to choose delicate shoes.

But then when we got back to the car he took them out and tried them on, ‘Do you like them?’ he asked

‘Well I am a little surprised, but they do go with your outfit well. I think we need a talk’ there was a pause,

‘About shoes?’ he asked

‘No about you, your clothes in particular’

‘Why do you not like them, they are not my favourite but they are good enough for shopping’

He had never been scruffy, clean and tidy more than smart, but I had sensed he was more aware of his looks since the marathon, I was at a lose as to how I should react, ‘We never talked about how you felt after our challenges’

‘You talked about your running but I was never sure how to explain how it felt, even how I feel now’

‘Do you want to talk, the clothes have stayed with you, and they look good on you’ ‘Thanks I wore them today to see how I would feel being out in women’s clothes, not as a training exercise, just to see how I felt’

‘And?’ I asked

‘I like it, men’s jeans and a T are so predictable, I had to think what to wear, and I feel different, I am not just a bloke in jeans I am me, do you like it?’

‘Why can’t you do this with regular men’s stuff?’

‘Don’t know, I like the fact I am dressing differently I suppose, there is a part of me wanting to express differently, anyway answer me, do you like it?’

‘Yes you look very sweet, but I would like to hear about your challenge’

That was when he wrote out his piece. To say I was shocked would be an understatement, I did not think I had encouraged him to have sex with Pete, but he obviously did, and I had to think what that act meant to our relationship, was it 2 blokes mucking about, did I want him to experience a woman’s position, was he overtaken by the whole being girlie thing and lost it for a while. I was not sure, but once he wrote it, he gave it to me and took a very long walk leaving me plenty of time to mull things over, he knew what he had written could have deep implications, but honesty is one of things I love about him. For me I did not know how to take the news and when he returned just acted as though nothing had happened, made our evening meal, watched TV, went to bed, made love. Well it was Saturday.

When a week later I asked why he had not worn his new sandals, he said he was unsure how I know felt about such things, I asked if he liked them, he said yes, I said well why not wear them. This relaxed him and over the following weeks wore his less manly but not overtly womanly clothes, that is until the weekend when he wore a lemon blouse, at first glance it was just a soft yellow, but if you cared to look it had small buttons and was to short, that plus the sandals made him look quite camp, and I told him so, ‘Do you mind’ he asked.

‘Or would you rather I went for a more extreme look?’ I was on the spot, I had opened up this Pandora’s box, he had never been uber male but he was not looking particularly male as I looked at him.

‘Are you wanting to wear a skirt do you think?’

‘Not at the moment, I am happy just wearing nice fabrics and these clothes fit the style I want’ I conceded I did not mind and we went out for our shopping.

I suspect it was that moment that lead to his more flamboyant style developing, he bought tops with no cuffs so the sleeves opened out to a bell shape, linen trousers that looked so cool in the summer and more flimsy sandals that he said were so comfortable.

It must have been months since he had had his hair cut and while watching a TV programme asked if he would suit a style like a certain presenter who had his hair gelled so it swept forward and across his eyes the neck falling comfortably past his collar. ‘Why don’t you go to my hair dresser and ask to look through his magazines, you might see something else you like better’ next evening I find out he had an appointment and wants me to go along to make sure he does nothing daft. I was uncertain as to how to react but agreed to accompany him.

John spent a while chatting trying to understand what Mike wanted to do and how much trouble he was prepared for, both in care and looks. Mike said he was not bothered if the style was a bit unusual, and he was happy to maintain a style if it needed it. John was persuasive and both of us accepted he could do whatever he wanted. I had other things to do and left Mike in John’s hands. Three hours later I went to pick up my restyled man, who was a bit poorer in the pocket but definitely richer in style. His hair was now lighter with highlights around the edges, his longish hair had not lost much length but seemed to have more volume, it was standing up and pushing forward, imagine the wind blowing from behind, with a feathered edge. I was not sure if it was the colour or the shape that struck me most, but together it was striking when compared to his previous boy style.

He had gone dressed quite conservatively for Mike now, but once home changed into his cream mohair jumper, brown linen trousers and sandals. Coming out of the bedroom to ask what I thought. ‘Very nice, you are unmistakably camp you know’ ‘That’s fine with me, is it with you?’

‘Of course, should we go out tonight, no point wasting the hair style on the TV’?

He changed again before we went out, choosing a loose lime green blouse with a wide satin ribbon around the waist tied in a bow to create a belt, tight black trousers and of course sandals, he even had jewellery on if you class a short bead band round his neck and wrist as such. What was most interesting was his keenness to get out and see how he looked to others, we did a few bars and people did notice, a couple of strangers even said hello in a friendly way, and when one couple started chatting we found ourselves invited to another bar we knew nothing about, but soon realised it was for the more interestingly dressed folk. Mike even looked normal compared to some in their fetish gear.

All the while my running is continuing, and I came to realise that while I was out Mike was experimenting with his look, always careful to tidy up before I got back but things did get missed.

He was good at looking after his new hair style, washing and gelling it to keep it looking good, at times gelling it into a different style, the side parting and across his eyes being the most common.

Changes started to become common place, one time he came to bed in a new set of nightwear, he had stayed with the satin pyjamas mostly, but these were not the usual button up blouse type, they had an over the head camisole top with trouser bottoms, all in cerise. It might have been feminine but it did not stop his manhood working, if anything it improved with my being able to caress his smooth skin under the satin fabric.

Another hint as to my changing man was that I was getting through tampons far quicker than I used too, especially the larger sizes that I rarely had a need for, but he was always discreet and never let me find a cotton string hanging between his legs.

Then one day I could not find my tweezers, turned out he had been using them, and when I took a looked at his eyes I knew exactly where they had been used.

Another time he had a sore face, and admitted he was having his beard removed, bit drastic I said, he just pointed out how I never liked a man with a beard, and he would soon be able to stop shaving.

His work has always meant that every now and then he was away for a few days, but when I found out his red dress was missing on one of these trips, I suspected his dressing was going beyond camp.

On his return I offered to help him unpack, which lead us into why he did not want any help and then into why had he taken the dress, which lead to, do you want to wear skirts again, which lead to would you like to be Michelle more often, which lead to do you fancy a night out this weekend, which became not just a night, but a whole weekend of Michelle.

To be fair he did not wear anything he had not worn before through the day, trousers were still most practical for shopping and housework, but it was the make up and nail polish which defined him as beyond camp and into feminine looks, then in the evening we both dressed up, heels, skirts and full make up and for Mike some new pendant ear rings. Then it was off to visit some bars we had been introduced to before to see if our new image would fit in. At first we were taken for lesbians, but then we meet up with the couple who had first invited us and were full of praise for Mike’s transformation. We had a great night pretending to be a gay couple before going home and proving to ourselves that we were not.

That evening opened us up to a whole new life. Mike became more relaxed about being Michelle and if he was working from home would often do it in a skirt, but doing the whole thing so if anyone came to the door they meet a woman, not a man in a skirt. He was getting back to the stage before his big girlie weekend where he would quite happily go out dressed in a dress and heels without really thinking he should look like the man his body was telling him he was.

Then we meet an interesting couple; he was a very dominant man while his partner was a sexy woman who seemed to like our company. We chatted about lots of things but she kept coming back to Michelle’s great looks, and how fantastic we both looked. Later on we ate in a curry house where I sat next to Suzie and Mike next to Paul, I nearly choked on my wine when I felt Suzie’s hand brush my leg, I apologised and said there was nothing wrong as I regained my composure. Suzie then invited me to go with her to the ladies, where she apologised for being so insensitive but told me I was gorgeous and she fancied me, I asked about Paul the big man, but was told not to worry about him he was not so good when it came to pleasing women, but as for her she was quite good at pleasing women, then stroked my arse as I made my way back to our table. Mike and Paul were quite happily chatting away when we returned, when asked why we had been so long, we just told them we had been getting to know each other a little better, which got a very sly smile of Paul and a confused look on Mike’s face. I did not flinch the next time she let her fingers touch my leg, which progressed as the meal passed to a hand remaining on my thigh. Paul was being equally attentive to Mike, I could not tell what was happening under the table, but he was always offering too do things for him, I remembered what Mike had written about his weekend with Pete and wondered how much he wanted to have that experience again. It was getting late when we paid the bill and we promised to keep in touch, exchanging mobile numbers, then it was home to let Mike finish off my already wet pussy.

We did keep in touch, and next Friday Mike was getting into full Michelle style because Paul had told him he should, while I knew Suzie would be flirting with me again. I had discussed what Suzie had said about Paul not being interested in women and Mike seemed to think she was right, but would not explain how he had come to that conclusion. Mike was in his highest heels, the red dress and looking great, I did my best but went for trousers in an attempt at modesty in the face of Suzie’s flirty texts. I was confused by being chased by a woman and completely lost as to how I should handle the situation, but oddly one thing I did not want to do was cry off even though Mike as well as myself were entering a totally new experience.

We meet at a plush bar, Suzie gave us both a greeting kiss, mine on the lips, Mike’s on the cheek, Paul only gave Mike a kiss, I got a hello, the evening went well and pretty much as expected, they successfully paired us off between themselves, Suzie letting her hands touch me as often as possible, while Paul was giving Mike equal attention and making it appear they were a straight couple. The whole evening was completely strange to me, I was used to playing a lesbian with Michelle, but with Suzie it was for real and exciting, no woman had been so sexually attracted to me and she was very sensual and I was aroused by the situation. I was unsure how Mike was taking the experience, but later when we parted promising to do it again I found Mike was just as aroused only he could do nothing about it, in preparation for the evening he had taped his bits up between his legs, but after my initial disappointment he brought out a vibrator that he used to satisfy my urges, it was while he was pleasuring me it struck me why he should have such a thing, then thought that he may have been using it himself, which made sense if he was using my tampons. So when I had recovered I offered to return the favour, and was surprised how much he enjoyed being fucked. It was then I realised how much the challenge had affected Mike, I knew we could have great sex, but to find out he enjoyed it both ways was a revelation.

As we lay in the afterglow I asked if he was bi sexual, he might be he replied, but then went on to ask if I would give in to Suzie, I said I doubted it, he said I should try it, it is only sex and it will not be like ours. So I came back by asking if he would consider sex with Paul, he admitted to being asked already, well not quite asked, Paul had told Mike that he was going to have him next time if he gets half a chance. Both of us fell asleep not sure what we wanted or what the other wanted either. I knew though when I was given breakfast by a particularly sexy Michelle in the morning that somehow we would find out which way we would go pretty soon.

We ended up chatting about what we thought was being proposed by our new friends, Mike had admitted to sex with Pete and we knew he had enjoyed it the night before, but now he was wanting to know if I minded, I knew that if I said yes he would give in to Paul, I also wanted Mike’s approval for anything I did with Suzie, I knew her attentions had excited me, and I was sure Mike realised this. Our uncertain positions were pushed further when our mobiles sounded to let us know we had texts.

Of Suzie ‘we are having a BBQ, forecast is good, fetch a bottle and sun cream’

Before I could really tell Mike of the invite his went off.

‘Paul here, you will come, you are so hot I cant wait to see your sexy body’

Then Suzie sent another ‘please come and be sure Michelle is with you; Paul is on heat here for her. I wouldn’t mind seeing you either, xxx’

We were sat together and as we read the messages Mike’s first comment was ‘I haven’t got a sun dress or shorts’

‘I don’t think either will be that worried what we are wearing to be honest’ I replied ‘Suppose not really, should we say yes, or do you not fancy it?’ from that I guessed Mike fancied going,

‘You just want an excuse to shop before we go’ he then told me of these denim shorts and a black and white dress cut top he had seen that he fancied.

Then suggested ‘try it once, or even just see how you feel, we can always leave’

Our day was planned, dress, shop, get ready after lunch, go over to Paul’s, and see what happens.

Mike was all taped and glued for a woman’s weekend from the night before, so was ready about as quickly as myself. First we shopped for clothes, I got a nice long floaty summer dress, spaghetti straps and sheer. Michelle found some tight shorts and a top that nearly covered the shorts and was cut so it supported his bust meaning he could go braless. He also bought white spike heel mules; 2” drop earrings with a matching necklace.

We arrived about four, it was still hot and we sat outside and drank the wine we had brought, Paul after a while began to get the coals hot and start cooking, BBQ is such a male thing Suzie just sat and offered advise, I sat watching as Paul had Michelle running around doing his errands. I know it was while they were cooking that Suzie got me alone and told me how Paul had plans on getting into Michelle’s knickers, I said I thought as much, but then added that I thought she had plans for my pants as well, to which she blushed and laughed, ‘off course, you are so sexy, every time we have meet I have been so wet I have had to force Paul to satisfy me’ I felt myself stimulated and knew this would be a day a learnt if lesbian sex was for me.

While I was being flirted with, Mike was not going short. Paul often touching him in normally out of bounds areas between men, and when I went to the toilet I caught them being more intimate than needs be when getting a bottle of wine from a fridge.

We ate chatted and drank, then as the evening cooled we moved indoors. I sat on a sofa and not unexpectedly Suzie came and sat beside me, Paul and Mike followed a few minutes later hand in hand, and when Paul sat in a chair pulled Mike onto his knee deliberately placing a hand on Mike’s thigh. I know it was not our house but Mike was the one who made sure our wine was topped up and going to the kitchen if any of us wanted anything. It was while Mike was out that Paul came out with a shock statement ‘Jenny, I don’t know if Suzie has told you but I have been forced to have sex with her because of you, I have done it twice, I will not do it a third time, you have enjoyed our hospitality now it is your turn to finish what you start’ I was a little stunned.

‘Ignore him, he likes to bully people’ Suzie said, but followed it up with a deep kiss. At this moment Mike walked back in with whatever he had gone out for,

‘And as for you my beautiful young lady, even if they cant get it on, I promise you I intend to have that lovely arse of yours, now get over here I need some attention’ Mike just submitted to this bully and went to sit on his lap then responded to his kisses.

Suzie whispered in my ear ‘our turn now’ and pulled me up of the seat and lead me by the hand to a bedroom. Where I found out it does not always need to be a man filling a wet pussy to get me to enjoy an orgasm. And from the noises coming from the sitting room a man can enjoy being filled also.

Suzie wore me out that evening, it was coming light when I thought I ought to be stopping and making some effort to go home and see how Mike is. I found him in the kitchen in Paul’s enormous dressing gown.

‘You ready to go home?’

‘Let me get my clothes, are you sober enough to drive?’

That Sunday we did not really come round till the afternoon, then it was only to eat, shower and zonk out in front of the TV.

Monday work kicked us back into reality, Mike was a man again, well nearly, we had both had texts asking how we were and thanking us. Over a pizza I asked Mike how he felt, he said sore but wanted to know if I would consider seeing Suzie again. I hesitated and he put in with the observation that I had spent enough time finding out if I liked it, so I agreed it had been a different experience, but was not going to go rushing off as I had Mike already. I got from Mike that he only really thought of men when as Michelle, and though he liked dressing, that somehow being treated as a woman by a man made the cross dressing thing complete.

I am not sure what Paul was saying to Mike, but Suzie was sending me lots of texts suggesting what she would like to do. By Thursday I gave in and told her to meet me after work, Mike was away. Once again she got my juices going and later enjoyed some intimate moments, but I was feeling guilty about Mike.

When he got home on the Friday I suggested he have some Michelle time, he seemed unsure that I should be so encouraging, but told him no taping tonight, he wore a flared skirt and no tape, then when we got home I had full range of his pleasures and rode him before fucking him with the vibrator. He was knackered. And I was torn between Suzie and my unmanly man.

By Saturday afternoon he was looking ultra feminine in a tight skirt and I knew his dick was lost for the day, when I asked what he had in mind, he replied that he thought I would be out with Suzie so he would not be needing it. Then it came out Paul knew about Thursday and the information had got to Mike, how naive to think they did not talk. And Suzie had asked me out to a lesbian bar, so without the men, who she assured me had plans of their own.

I was later to see Michelle teetering along on her spike heels and showing a lot of leg while hanging onto Paul’s arm, but I was no better having my arm around Suzie’s back.

Over the following months I really got to liking Suzie and wanting to be in her company, Mike was also spending a lot of time with Paul who had got him wearing corsets, size D bras and padded pants, so he had a great figure, if not entirely his own. We did go out as a foursome at times, it was at these moments I saw how Mike allowed himself to be dominated, he would do anything Paul told him to do, from what to wear, to where to sit, to when to talk, we had always been equals, now he was submissive beyond belief.

A big surprise was being invited for a meal at Paul and Suzie’s, but they were not the host it was Michelle who cooked and served, sorted out drinks and made sure everyone was happy, I even suggested he should get a maids outfit, to which Paul said it had been discussed, but Michelle had wanted to eat with us and a maid would not be allowed to do that.

Gradually our relationship changed, our sex diminished while our new partners became more important, I could end up at Suzie’s three nights a week especially when Mike worked away, but none of us were very good at the housework so increasingly Michelle would spend her weekend with Paul and clean their house. Then when he spent several weeks working away only coming home at weekends he changed at ours, then went out with Paul, stopped over and ended up staying till Sunday when had had to revert to Mike for work.

I am sure our lives would have turned out differently if I had not decided to run that marathon, but I was still fit and in better shape than at any time in my life, Mike had found something in himself that surprised us both, but disappointingly we were drifting apart, we had become good friends, enjoying each others company and sharing a house. It should not have surprised when Suzie made her suggestion.

Mike was away and recently when that happened Suzie would stop over some nights. We were relaxing after a nice meal, cuddling up watching a soap.

‘We could do this all the time you know’ Suzie said softly

‘That would be nice, but I have think of Mike, he still lives here, well sometimes’

‘Have you seen some of the gifts Paul has got him recently?’

‘You mean the corsets, stilettos and revealing outfits?’ I suggested

‘Obviously not’

I asked her what she meant and she told me about a side of Mike/Michelle I was largely unaware of. He had some thongs with ‘Paul’s’ written on them, he has a classic maids outfit which Paul likes him to wear on a Saturday when he is cleaning the house, and she had turned up unexpected one evening to find Michelle in some of the sexiest underwear she had ever seen, tied to the kitchen table with a vibrator running inside her arse, and Paul nowhere to be seen. Apparently Michelle had made it obvious from the way she was dressed she wanted sex, Paul needed to go out, so just tied Michelle to the table who did not resist, then left her to get on with it by herself.

I felt a bit more distant from Mike after that, I did not really want to ask about his sex life, but did ask how things were, ok he said, and sex, that’s good as well he confirmed, and the maid’s outfit, a bit of fun he said, who for I asked, Paul likes it, I was told. Then I noticed his navel had been pierced, well his blouse was only buttoned around his breasts, I said how nice it looked and took a closer look, from the stud hung a tiny disc which read ‘mine’, whose I asked, Paul’s he replied, so I’ve heard I told him.

The next day I meet Suzie and told her about the stud.

‘Come on face it Paul can get Michelle to do anything he wants’ she paused ‘I am not sure if I should say this, or if you are ready’ another pause ‘I want to move out of Paul’s’

‘That sounds like a good idea’ I ventured

‘And live with you’ Suzie completed her sentence

I was a little dumb struck, ‘What about Mike?’

Suzie stated the obvious, he was hardly ever at home, and then as if to confirm Mike’s transformation I asked Suzie Mike and Paul for a meal and brought up the idea of Suzie moving in with me, when I asked Michelle (she was in something quite sluttish, so Mike seemed wrong) she turned to Paul, who answered for her.

Apparently Michelle would be happy to live with him if Suzie was leaving it would leave extra wardrobe space and Michelle would be free to be herself all the time. Michelle never said a word, and when Paul got up to leave he told Michelle to get whatever was in my house so she did not need to come back to collect things. Then they left.

Suzie moved all her things in that weekend and from then on we hardly ever saw each other. I heard Mike was working from home a lot that meant Michelle would be fulltime, but it was a year later I got my biggest shock, we meet at a bar and she was in a very skimpy top showing a lot of cleavage. We did the pleasantries of how well each other was looking, and then I commented on his figure.

‘Do you like them double D, they feel smashing’ she boasted

‘They fill your top’

‘Paul had my bum filled as well’ she turned and gave it a wiggle, most girls don’t like their arse being big, Michelle loved it, a hollow back and round hips looked good on her.

‘Lovely, you are never Mike anymore?’

‘Never, changed my name to Paul’s and I am always Michelle’

‘And work?’

‘Cool about it, they need my skills, and cant sack me for being transgendered, so I should say thank you, it was your challenge that got me going, how’s the running and Suzie?’

So that was it Mike had disappeared, he loved being Paul’s woman, and there seemed to be no regrets from him. I had none either, earlier in the day Suzie and myself had bought matching diamond rings and were out celebrating our intention to be a legal couple.