Who Wears the Trousers

by Lauran Travis

 

A few months later I received a letter from Trudy. We had kept in touch and it was nice to have someone who was in a similar situation to talk to, what was special about this letter was the invite to go over to her home and help her with a job she had been asked to do. She described it as being waitressing, like we had done at the hotel, and that the clothes would be provided, all I had to do was turn up and be prepared to enjoy myself.

With an invitation like that how could I refuse? So once I had got Sue to let me go I rang to say yes. A week of excited anticipation followed, until I finally stepped out of the taxi at Trudy's front door. I had tried to look unnoticeable in a trouser suit, but when she opened the door in a dressing gown that did not conceal the stockings at all well, I dared not turn to see if the driver was looking. It was still the morning and Trudy obviously had the day planned, first we had to pick up the outfits, then she had an appointment at a salon. Which she reckoned would leave us enough time to eat and get ready for the evening.

Soon I was holding onto my nerves as Trudy took me into the costume hire shop, where we picked up the waitress outfits, then we had to buy new stocking, and I did not have any stiletto sandals so Trudy said the job would pay for them so I ended up doing my first clothes shopping with out the aid of a catalogue. Next we had the salon to visit, Trudy had an appointment, and planned on a trim, blonde streaks and styling, but when we got there it was empty and instead of sitting watching and reading magazines, I was persuaded to have the same, which as a first I found tremendously soothing and stimulating at the same time. The hair was then styled so it fanned out on the back of my head, as though an explosion had occurred there. I was sure I could not repeat it, but loved the sight of my hair properly done. I made a mental note to approach Sue about having my hair done at home.

Once back at Trudy's we ate, then set about getting ready. The evening was a corporate dinner, where the organiser tries to do something different each year. Last year it had been medieval, the year before Caribbean, and so on. This year it was drag, there were drag acts for entertainment, the menu was full of camp food names, and they wanted drag waitresses, which was us. The dress was stereotyped, French maid short skirt, frilly underskirts, stockings, stilettos, and tight waisted with bare shoulders. We used bright red nail polish to match our lips, and deep eye shadow colours. At seven we said good night to Trudy's partner, put long coats on and went out to the waiting taxi.

I was on a high, not since the training had I been dressed so provocatively, and I could tell Trudy was enjoying it as well.

We arrived; the organiser inspected us, then complimented us and introduced us to the maitre-de, who was another trannie Trudy knew, but was dressed in the most stunning evening gown. She explained what our duties would be and told us to sort ourselves out, and be ready for eight with trays of wine, when the guests arrived. The evening went brilliantly, we flounced and strutted our way around, serving drinks, and then helping the regular staff with the meal. There were between 130 and 140 there so it was busy, but we still managed to have fun with the diners. When the cabaret started it got easier, as it was just serving drinks. The drag acts were the usual innuendo humour, some of which was aimed at us, and encouraged the more adventurous men to let their hands wander where they should not, but a comment to the women on the table always put a stop to that, if we wanted it stopping. When they had the dance we all but finished, they got their own drinks and we just collected empties now and again. I had a nice chat with Trudy's friend in the gown who had got us the job, she suggested we could do it again knowing I was enjoying myself, she also asked if I had accepted any chat ups, I blushed because I did not know how to respond, 'Trudy said you were a virgin, you flirt well, we have got rooms here if you want, how's about it?' I ummed and arred, then said it was all new and flirting is one thing, sex is different. To which they replied, if I did not have the extra bit that I had tucked neatly away most of these men would have wet dreams about me. I changed the subject and asked about the gown she was wearing, oh just work clothes she said, some work clothes I thought it looked expensively luxurious.

After a good nights sleep at Trudy's we had the day to ourselves, I was not expected back for anything other than housekeeping, and Trudy was a kept partner as well, her man having a good city job and lots of money. So we were set for a girly time.

We did nothing of consequence, just drifted around shops and drank coffee, but Trudy was texting her mate and giggling, then announced we were done and were getting back. Fine by me I thought, but felt something was being planned, and I was right.

Once back Trudy explains how Dave (her partner) would meet them after work in town. This usually means he has a business colleague to entertain, so it was our job to be the pretty escorts for them.

So as we dressed Trudy is giving me clothes to borrow, silk underwear, sheer stockings, a red Chinese dress, my trouser suit would apparently not do. Soon I was admiring her stunning fuchsia tube dress, and pulling a wrap around my shoulders.

The taxi dropped us at the door of this smart restaurant, feeling over awed I lent on Trudy for support 'don't worry, you look great and they will pay for everything' and we entered linking arms as friends do.

We were first so started the tab with cocktails, with my back to the door I was trying to be unnoticed, but Trudy was keeping an eye out for Dave. He appeared after the second drink with his colleague, a man called John, both smart in their suits and looking handsome. Dave gave Trudy a greeting kiss, and then we were introduced and had a round of cheek kisses. The meal went fine, I was obviously John's 'date' and he was charming friendly and not to forward. For me I tried to be the same, but on a toilet visit Trudy hugged me, telling me how great I was doing but if I did not start flirting with him she was going to have a try for him. My shocked expression said everything, could I should I would I.

On our return I started to lean closer, and look only at John, and basically flirt. The meal was really nice, but the wine was lovely. So no surprise when I needed support to leave the place, which came easily from John. I held onto him as we strolled along the streets watching the other nightlife pass by. At his hotel John invited us in for a drink at the bar, where we found ourselves sharing a settee. The closeness of our bodies was new and nice to me, but when Trudy and Dave said it was late, I made to get up but Trudy lent over pushing me back down, and as she kissed my cheek whispered 'He knows we are not real girls, remember what they taught you at the training hotel' Dave kissed me good night, and they left. Dave poured out the last of the wine, and as the bar was getting empty suggested we take it to his room to finish it.

My dilemma, do I tell him he is the first, or try to act like an experienced escort and be brazen? I need not have worried, he lead me gently to his room after closing the door coming up behind me as I looked around. He kissed my neck and squeezed my waist, I could feel his erection pressing on the small of my back., I had never knowingly done this to a man before, and I felt myself getting more excited.

After some more cuddling and groping he starts to undo my dress, but it is not the easiest to remove, so I make my excuses and use the bathroom. Coming back without the dress, a bulge obvious in my panties from my straining taped back penis, John underdressed and is waiting in bed with the lights on low, 'you look beautiful' he complimented me, I slid a hand over my groin, but he just took the hand, stroked my panty, and whispered 'that is beautiful also'. Before I could stop him I was under the covers with him and exploring each other's skin, the size of his cock shocked me; well it was the first I had handled besides mine. Before long his cock was between my arse cheeks, and being considerate he slid a condom on, then massaged cream into my arse. Slowly he entered and then moved in and out gently, my legs in the air and arse wide open. I was getting over the stretching pain and starting to enjoy it, when he pushes deeper in, and touches something inside me that makes me tingle, now it is my turn to move as I try to get him on the prostrate again, as I do I get more tingles and I can tell he is getting closer to his climax. Once he has cum, I finger him hard again; I want that tingle back and ride above him as he tries to stay hard. In the end I thank him for his efforts by sliding the condom off and sucking him off, to my surprise he sucks me as well at the same time.

That was exhausting and I was thinking about leaving, but he holds me close and asks me to stay.

Come the morning I woke up as he was leaving, there is a note by the bedside.

'Thank you for last night. Could we meet this evening? I have left some money for you to get something nice. XXX

I had to ring Trudy, what was I to do; I had been paid for sex. And had no easy way to get out of the hotel, besides looking like a dishevelled hussy. Trudy came as quickly as she could, with make up, coat and advice. She explained she got paid for sex; it is just called housekeeping in their relationship. That did not make me feel much better, but the make up and a coat to cover up the crumpled look was well received.

I was still uncertain as we left the hotel, but Trudy had it planned. She had listened to my telling of the nighttime activities, and would take charge.

First we went round a few shops to get ideas, and then we found a salon with a slot for me to get my hair restyled. Next was to get a dress, Trudy's only concern was that it came off easily. Soon I had a big floaty dress which only a few ties to keep it from coming open, then some sandals to match it, and a bag, and best of all satin undies. With one last purchase, a nightie. Then it was back to the hotel to get ready.

I had already texted John to confirm he was genuine, then to find out what the plans were. The meal and the film were unimportant, we were like kids holding hands and kissing. Until John just leads us back to the hotel and finds out how easy my clothes came off, then I had the fun of undressing him, then pushing him against a wall as I knelt before him, he was about to collapse when I stopped and took him to bed, still hard I rode him, then turned over for him to ride me. I was really getting into this when he came.

Next morning there was a similar note to before, this time I did feel cheated and sent a text to say so. The return was very apologetic promising not to do it again.

So I went to see Trudy, take her clothes back, and pick up mine. Then have a debriefing on events. John had told Dave how much he liked me, but was going at the end of the week. Trudy then made me describe the sex, and she tried to give me advice until in the end she suggested it would be easier to demonstrate. So stripped off and her playing the man, she showed me several positions and how to get the most from his cock.

That night I wore the trouser suit and had a sedate evening in a bar watching the world and playing under the table, until I could stand it no more and insisted we go back to the hotel. I had made sure he was hard early on, and now went out for as much pleasure as possible. I had what I guess was an orgasm except it felt different to cuming. Instead of falling asleep we talked about the fact that we would split at the end of the week, and how much he did not want it to end there, I made it clear I was not to be a handy mistress when he was in town, then cuddled up and slept.

Thursday morning and he left the usual gift, except it asked me to get a mini skirt. Odd I thought but did as asked, it was his money, and got a crop top as well. We meet at the hotel and changed, saying we were going to a club that evening, so it was full on sexy look. Make sure he is looking at me, and possibly getting him jealous as others look at me. It worked he was very protective which was lovely. The more casual clothes meant we had more fun while we were out as well. We both sneaked into a cubicle so I could give him a blowjob, and by the time we were back at the hotel I was sore from his touching, and he was hard again. The beauty of a mini is it doesn't get in the way as he found my pleasure spot again and again.

The morning came to quick, we had to be packed and out, but not before John had given me his address and told me how to find it and when he would be there, serious I thought, not just an escort or I would not be seen again.

Well I went to see Trudy before deciding I really should go home, the job, and the break had been wonderful, but I had best get back to see the boss and sort out the house.

Well she was not pleased; the house was a mess and wanted to know where I had been, just with Trudy I lied. I soon had the house looking nice again, and her clothes all sorted. After a couple of days I hoped she would have forgiven me for being away and not being the wife to her, but she didn't and all I longed for was some sex with John. I tried to get her excited but she just turned away. 'What is up with you?' I asked. She then confessed to enjoying her work enormously, which left her too tired to be interested in a relationship with a wimp who wears dresses. 'But it is what you wanted' I replied' maybe it was but she now had a life apart from home and loved it, and I was not special enough to make her want me now. By this time I was crying and went to get a drink and sit alone. While sitting I came up with a plan to borrow the car and drive up to John's.

On Monday I packed everything I wanted, left a note saying bye, then went to wait for John. He has a very nice house but not a private drive so I could not park and wait outside. I returned early evening to find him home and shocked that I was there on his step and wearing his mini skirt, which only meant one thing, sex.

After I had seen every position on the couch, he then in the afterglow got me to explain why I was there. His answer was the one I wanted. 'You can stop here as long as you want, just look like a wife daytime, and randy tranny at night' I agreed and settled into being Ms John.

 

So I went to see Trudy, take her clothes back, and pick up mine. Then have a debriefing on events. John had told Dave how much he liked me, but was going at the end of the week. Trudy then made me describe the sex, and she tried to give me advice until in the end she suggested it would be easier to demonstrate. So stripped off with her playing the man, she showed me several positions and how to get the most from his cock. By mid afternoon we were sore and tired, but when John's text asking if I could do dinner later how could I refuse, I wanted to try out what Trudy had taught me.

We met later; I had my trouser suit on, but with satin underwear, which kept me in the mood. We made it back to the hotel early and as I stripped for him, then undressed him I knew it was going to be a good night. We were not disappointed, he was able to stay hard and give me wonderful time ending in a rush as I came.

We had one evening left and I drifted off to sleep I wandered how it would be spent, the week had been so great I did not want it to end, but it had to, so hoped it would be a great finish.

As usual John had crept out without disturbing me and left a note for me. This time it read, 'You once thought I was treating you like a hooker, now you know better I hope.' Then on the back 'Here is payment for last night, see you on the corner of Sorrel St tonight'

I knew he was poking fun at me, but as I dressed I had a thought develop around the prostitute comments. I of course had to ring Trudy for moral support and suggestions as to where to shop, and she loved it.

So come the evening I was stood on the corner of Sorrel St. What I had not really thought through was the response I would get from other people. Let me explain what I was wearing, red stiletto sandals, ankle chain, red mini dress with lacing up both sides from hem to arm pit, which meant no underwear, I had had my hair highlighted and done up big, and lots of big bangle jewellery. Hardly surprising I was attracting attention, on old dear told me I should be ashamed, but two men asked how much, I told them I was already booked.

I saw John as he walked towards me, then as he got closer he saw me, the closer he got the dawning realisation that it was me stood on the corner appearing to be looking for trade, was a wonderful thing to see. He first said hello in an embarrassed sort of way, then took his jacket off and suggested I might be cold, then said please, then suggested the police might not think it funny. I slipped the jacket over my shoulders, which only helped a little, as it was longer than the dress.

We went into a bar and found a quiet corner, which allowed him time to take in the female image he was now sat near. I noticed he had a few winks and nods from men who let on to him, his ego could have been boosted but I was not sure after his first words. 'Sorry about earlier, this is such a shock, never imagined you dressing like this.' A pause 'You are stunning, quite stunning.' I gave him his jacket back, 'Not so bad yourself.' Then lent over kissed him and felt for his upper leg to see what reaction I was getting there, I was not disappointed. Sliding up close so I could stroke more discretely, he smiled as he got stiffer, then put a hand on mine 'stop, you shall get me there if you are not careful' 'who mentioned careful?' then took his hand 'go to the toilet, I shall follow you' and have him a knowing wink. Luckily the bar was quiet, and I went into the gents unnoticed, I found John just stood there, so lead him into a cubicle where I released his erection and gave him a long slow blow. I left him there to go and repair my face half forgetting I was in the gents when a bloke walks in, says opps sorry, nearly leaves but then sees John looking dishevelled but happy, and smiles at him then turned to me, he nearly said something but bottled out. We would have a great time imagining what he was going to say later.

'Hungry?' 'I could be, what did you have in mind' 'Food really, where do you fancy taking me. Where do you think you could take me?' I said with a big grin. 'Back street or posh?'

We wandered down a few streets, and came to the place he had chosen, a nice looking Chinese, when we got in I immediately saw why we were there, Trudy and Dave were waiting for us. Trudy got up to give a greeting kiss, Dave was too stunned to move, my outfit had caught him unawares, which was brilliant, just what I wanted. We chatted and ordered, and then Trudy winked at me and said 'ladies' which meant she wanted a private chat. But once in the toilet she gave me such an embrace I was left wondering what next, 'You are so sexy, I hope John has reacted well?' 'Oh yes very well' and I thought of my previous time in a toilet. Then she led me into a cubicle and pulled up my dress, 'no knickers, does John know?' 'I don't think he has worked it out yet. Then she starts to massage me, 'I would love to have you to myself' I went all serious and suggested we might be missing the duck starter, 'Maybe later' we agreed and after a long kiss and make up repair we returned. Trudy then steers the conversation to what me and John had been up to earlier, which ended up trying to put words into the mouth of the man who found us in the toilet

The meal went well, plenty of banter, and a bit of footsie, but not sure who with. We drifted from there back to the hotel bar were John and Dave started talking work seriously, so Trudy quietly asks if she can use our toilet, I went to give her the key, but she took my hand as well. It was not long before I realised she would not need the loo, as soon as we were in the room she was on me, not that I objected. The dress hem was up and I was over the back of a chair letting Trudy enjoy herself, so I did not notice the door open, Trudy did and paused in her actions, I guess she was encouraged as she continued with renewed vigour, cuming in a big way.

Still spread over the back of the chair I heard voices and clapping, I was horrified; John and Dave are stood watching, applauding our show. I started to apologise to John, Trudy is trying to sooth me. When John explains how things were, I was dressed like a whore, and behaved like one, him in the toilets, Trudy just now. Then looks at Dave as asks him if he feels left out, he squirms about, making no eye contact, then when Trudy catches his eye she obviously lets him know she does not mind, and whispers how good he is in my ear. Things are moving to fast for me, but it is settled when John gives me a big kiss and quietly 'just go and play the slut with him, it will be fun' and I did fancy some more sex. So I stepped over to Dave and kissed him while undressing him, I tried not to think of the others watching, at some point Dave took over, his inhibitions gone and laid me on the bed pushing until I was exhausted. Dave's cum soaking me completely.

As we finished Dave rolled off me to let me go to the toilet, but Trudy coughed and said 'Got another here if you want it?' she was massaging John's dick, how long for I had no idea, but it was enormous. Dave and Trudy then coupled us together and made sure I was getting the full benefit of another dick, before they left us to make love on their own.

It was early hours when I fell asleep, waking to find Trudy in bed with me. John and Dave had crept out and gone to work, leaving us to clear up and leave.

Trudy wanted to know how I felt, how sore I was, what would I do when John went back that day. The answers were, quite sore, confused as I had never behaved like that before, and I would go home and see what live was like with my wife.

But before we got up properly, we had another tumble on the bed, I was still securely taped back, so Trudy had to take the male role, and I had to just lie back and enjoy myself.

Later that day I arrived at my home to find it a tip, she had done nothing, obviously it was being left for me. When she got home quite late, there was no 'Nice to see you, had a good time?' she just threw a folder down, got a drink and asked what was for dinner.

I had spent all afternoon cleaning, and then cooking, I swallowed and tried to be as nice as possible, tried an affectionate cuddle but got shrugged off. Over our meal I tried to ask what was up, she just said work was tiring, so do less I suggested, no way I enjoy it too much she countered. The conversation went downhill, I accused her of loving the job more than me, she accused me of being a poor excuse for a man, I asked when was the last time she had sex, unexpectedly she went a bit misty eyed, then asked 'With you?' what did that mean, was she thinking of someone else more recently. 'With me or anyone else?' It did not take long to give up the bickering, it was late and we headed for bed, when she saw my new nightie, she asked a similar question to mine about sex, I hesitated in my reply, which made her look up. 'So when was your last time?' should I say this morning, best not I thought, but asked again 'You never said when your last time was' 'If you must know, just before I came home, happy now?' she paused to let that sink in, 'So come on when was yours?' 'This morning' I admitted sheepishly, 'Was it good?' 'yes, and you, was he good?' 'I don't think that would help' 'So a yes then, and better than me' ' well a big hairy male you are not, maybe not as affectionate, but he certainly takes charge and makes sure I have good time. Was it good for you?' 'Different if I am honest' 'Male or female?' 'Trudy' I answered 'male lesbians, how different indeed' We were being very sensible in our talk, open and frank, the bickering gone, so when I asked if she would ever fancy sex with me again, she thought then said she doubted it. 'But you made me look like this, and now you don't like it, where do we go now?' 'I did prompt you into doing the housework, but I have not had any complaints since you went to the training hotel, so I took it you liked appearing as a woman. Maybe sex as well?' I paused then asked 'Would you like see this man again?' 'I have no choice, we work together, he thinks we are girlfriends, and yes if he invites me I shall go out again.'

It seemed our marriage was over, she loved work, and had a new man, I was just the maid. That night she slept in the spare bed, got up and went out before I was up. In the night I kept remembering Johns invitation to join him more permanently, by the morning I had decided to leave and give it a try, I dressed up in one of his dresses, then packed all my stuff into the car. I dithered over leaving a note, but she came back as I was about to go, saw the new dress and the loaded car. We had a few civil words, I told her where I was going, she told me to keep in touch, and I left, with a cloud over me.

As I drove the sadness at splitting up was replaced with the thought of seeing John again. So by the time I had found his house I was excited. After the shock of surprise at seeing me, he invited me in, asked what I was doing there, when I told him I fancied more than a few hotel nights, he told me how I had been on his mind constantly, pulled me to him and gave me a welcoming embrace, which soon turned into sex with me over the back of the settee.

Was I ever going to stop wanting this, would he ever stop, could I keep him happy? All these thoughts faded as I felt him stroking that sensitive spot that makes me tingle. I was here and enjoying it, that was enough.

  

  

  

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