With renewed apologies for having to censor my last chapter, for the truths revealed were too recognizable, I continue! “Wishing for what might have been”…. So it is for me. What happened with the Agency had an effect on many things in my life. There’s more pure sex in this chapter — no apologies — but my dressing will return!

Chapter 24

The love-making after the party was great for both myself and my “Wife-y”. It would lead to much more experimentation between us but, ultimately, to a severe ultimatum (from her to me).

Our role reversal for the party, as I tried to indicate before, released a different attitude in Christine, my wife. She had looked really good in her male gear, just as I had looked at least passable as a bloke in a dress. She was very assertive that night when we got home from the party. She took the lead in ways that I had never known her to do. Ways that I enjoyed hugely.

I found that this took away all of the pressure “to perform” — a term I absolutely HATE with a vengeance (mainly because I failed to “perform” on many occasions around that time. My late 30s were a time of falling confidence in a lot of ways. To find us romping away playing with few inhibitions was a joy.

Christine found that I would respond when she pinned me to the bed with a vice-like grip on my wrists, sufficient for her to have a really rampant ‘ride’ on an unusually stiff cock. She also enjoyed riding me with her pussy over my face and having me delve deeply into the beautiful folds of her lips down there. She chose, for the first time, to give me a long and luscious oral until I could cum with such force I had nearly lost consciousness. Wow! Was this a direct result of a night’s crossdressing?!

I thought so, maybe even believing that Christine was getting to enjoy that side of me. She had always guessed, I’m sure, but hadn’t been sure. She also hadn’t revealed anything about her more dominant side.

(Please don’t be concerned, dear Reader, this is real life and it’s not going to go off up some bizarre S&M fantasy. The activities that follow were real and may not have lasted too long — I mentioned an ultimatum, remember?)

Over the weeks that followed, I contained my delight about the way things were going by imagining my own part in this to be of a female — perhaps a little submissive female. My love life had rarely been better. I wasn’t dressing for any of these encounters. My mind took me to places where I enjoyed myself more than enough.

Christine didn’t mention my dressing again after the night of the party, nor did she suggest that she dress in a male fashion either. We had simply been ‘released’ by the party.

My birthday that year — 1988 — brought me a surprise package. Along with several boring, everyday gifts (you know the sort of thing!), I found one small extra gift, wrapped in shiny red paper with a crimson ribbon and bow tied around.

Christine had a sly smile on her face when she gave it to me saying “These are for quiet nights in at home….” Her hands were unusually tipped with wonderful bright red nails — I couldn’t resist pausing to admire them.

But then I couldn’t wait to find out what she meant but carefully un-picked the bow and opened the parcel. To my surprise, a black velvet pocket-bag revealed a pair of cuffs. Something I had heard that people enjoyed but had never explored myself.

“These are for me?....” I asked, also smiling. “They are indeed, honey…… but….” was her reply.

“But? But what??....” I asked. “But I may ask for them sometimes, if you’d agree.”

I would rather have had a lovely nightie or a bra, panties and suspenders… but….. beggars can’t be choosers! I responded urgently, saying “Whenever you like my darling…..!”

“Then just do as I say, and do it now…… Go shower and wash very carefully. You have seven minutes and I’m counting. I want you back here on the bed before 7.43! I shall be ready for you. Be prepared to give yourself up to me… you are MINE!” I got up from the bed.

Oh, if only I were wearing some beautiful undies…… For the first time I WANTED to be discovered! But I had none to be found in. If only I were wearing make-up! But I had none to wear. I just had to do as I was told.. and fast. I left pieces of clothing all along the passageway to the bathroom where I arrived stark bollock naked. The shower was hot and left me gasping. The towels were warm and fluffy and luxurious. I towel-dried my hair and briefly gave thought to its (then) lack of style. I HAD to do something about that.

I went back to the bedroom having, also briefly, thought about putting on Christine’s sexiest, white satin, dressing gown which hung on the bathroom door. But I thought better of that — just the thought gave me a nice stiff cock to go back to the bedroom with. All of this was too good to have dreamed of — on my birthday!

Back on the bed, I found Christine with just her bra and panties on. Lovely, lovely…… She had brushed her white blonde hair and it was now piled high on her head in a chignon. Her lipstick was full and fresh.

She rose to stand face-to-face. She took hold of my cock, her eyes not blinking, as she said “Pleased to see me?” Which naturally, I was. “Not half as pleased as I am to see you.”

She very deliberately reached for my right wrist with her left hand, leaving my cock in her right hand which was now gripping me hard, her fingernails causing discomfort. There was more of that to come, as she said “Pick up one of the cuffs… NOW!” Her eyes stayed fixed on my own.

I did so. The cuffs were within easy reach. She released her grip on my cock. For a minute. Within seconds, the cuff was in her ‘free’ hand. It proved to have a quick-snap lock, engaged by her closing the cuff over the wrist that had delivered it. Immediately, her hand was back on my cock. The second cuff dangled.

“Do the other one yourself”. Her instruction was clear. “No, wait a minute…. You hold this… “(she said, handing me my own cock)….. “and put your arms behind your back. NOW!” So I did so. The lock of the second cuff snapped shut and I was again face-to-face with this woman who was now in control.

“You enjoy what’s to come, and then you can return the favour…”

So, I was on a promise!

--oo00oo–

An hour or more later, I was satiated, exhausted, and knew that the compliment was to be returned. Christine was, by now, as horny as hell. She had cum a couple of times when her pussy was riding my face, oh, and another when she felt me cum inside her. “Double-top” we called that.

(I’ll spare you the details of how that came about, dear Reader).

She gently removed the cuffs from my wrists as I lay there on the bed. It was clear that she would want to be seduced as expertly as I had been by her. I didn’t have the wrapping of the gift to offer, so I needed surprise somehow else. I stood up and put on my own short dressing gown. Sadly, not a sexy item at all really.

My mind ran wild but came up with nothing……. I decided to do the reverse of what she might be expecting… and, at the same time indulge a little fantasy of my own. Before I got started, my cock rose again, a bit embarrassingly….. First, I would dress her and do her make-up and her hair, as if we were going out on the town.

“Stand up, my wife!” I commanded — in a most unusual way for me; I don’t ‘command’ anything much. And she did. We stood face-to-face. Now, go to your vanity unit and sit down….. Take your cuffs with you. I stressed the word “your” as the cuffs were now no longer “mine”….. (They became “ours”).

As she sat, I looked her in the eyes in the mirror and my hands took her by the wrists behind her back. I slipped the cuffs on to her slender arms and admired them, along with those wonderful crimson nails. I knelt down behind her and kissed the backs of her hands. My tongue traced the lines on the cuffs above the hands. Then, I licked the fingers and sucked the fingernails, allowing Christine to study her own reactions in the mirror.

I have already said she was as horny as hell. Well, I was right in doing what I was doing. She let out a very quiet moan as she squeezed her thighs together, raising the tempo towards a climax. Already aroused, she was ready to cum. So I spun the stool on which she was sitting and, with her now facing me and away from the mirror, I pushed her thighs apart and went down into the glorious pleasure park that opened for visitors that minute.

All I have ever learnt about tongue-fucking a woman came into play and I was soon lost in my own dreamworld. How long I was in there, I have no idea. She still had her lovely panties on so I pushed them aside with my tongue and held them aside with a finger. My other hand took care of her clitoris that was all pink and wet by now. How many times I heard her cum, I cannot recall….. maybe not at all, maybe ten times. Whatever, we were both overjoyed…. But I was not yet finished.

Turning her stool to face the mirror again, I took the pins that held her hair out and laid them on the vanity. Her hair fell to her shoulders and the brush I took in my hands was easy to run through it. Avoiding vigorous brushing, the clean waves of hair tumbled just as I hoped they would. Parting the hair centrally, I pinned the hair from her temples back to the crown…. Gwyneth Paltrow style.

Her selection of cosmetics beckoned. The foundation was light and easy to apply with a finger or two. The eyeshadow was also light to apply. Less is more — I remembered. She wouldn’t want to look like the tart I usually ended up being. Then I dared to put on some liquid eyeliner. My hands weren’t steady enough and I gave that up as a recipe for disaster. Likewise the mascara. So I turned to the lipstick that we had so many times put upon eachother’s lips whilst preparing to fuck. Easy. I leant back and admired my handiwork. Her eyes still needed defining. An eyepencil would be less risky, so that was what I used.

She was allowed to look at herself. “Stand, now.” I whispered. She stood there in her bra and panties — which I so was jealous of! “Find some stockings. And a suspender belt.” I was insistent — she would now fetch and carry, and I would put the clothes on her. The belt was first.

As she did so, I told her to sit again at the vanity. I knelt at her feet and rolled the first jet black stocking into a roll which then went over her toes and ankles…..

Within minutes, I had dressed a woman entirely myself. We paused only to release the cuffs while a beautiful sexy blouse was laid upon her shoulders and her arms threaded into the sleeves. The cuffs then went back on. She was dressed when she finally stood after I put on the highest stiletto-heeled shoes that she owned on her dainty feet.

My words then to her will not be repeated here but she was left knowing how much I loved her, how sexy she was that night, and what a wonderful lover she was.

I then pushed her back onto the bed, parted her panties and got back in with her pussy… I was tongue-fucking a beautiful woman, just in the way another beautiful woman would do. The more I did this, the more I felt like the male lesbian I knew I had become.

I didn’t want to fuck other women besides Christine. I certainly didn’t want to fuck with any men. This was the Promised Land!

--oo00oo–

As our lives extend, there are fewer “first times” to report, it’s natural. Keeping on doing what gives pleasure means repetition not new frontiers all the time. Increasingly, the experiences we find anew are further spaced apart. So it was in the months after “that” party.

Having my own eyelashes dyed. Yes, that was one. I had always wished my eyes were more distinctive and could never manage with false lashes myself. So having my own lashes dyed was an alternative worth trying. I did make it clear, when booking an appointment “for the local theatre”, that I wanted only a very light change of colour. And that was what I got. It was the most bizarre experience of my life, having this done to me (and I have had some bizarre experiences, as you know!). Talk about “up close and personal” with the beauty assistant, Chloe by name. I was pleased with the result and, if Christine noticed, she didn’t say anything.

Then there was the time when I found myself buying a pair of silicone false tits (and having nowhere to hide them). That was another visit to ‘Transformation’ in London. I had been given a bonus from work and fancied indulging myself.

So I went to my favourite high street store, bought a new bra and proceeded to strut my stuff with what felt like genuine tits! I loved myself a little more. That’s something I had rarely done before…… and not much since either. Such is the lot of a dedicated Crossdresser.

That same event led to my shaving my nipples and underarms. After all, a girl can’t have nasty hairy armpit, can she?! I kinda liked the way it was all flushed away in the shower. Again no comment from Wife-y, Christine…… but then when did she ever look at my armpits??

At this time, aged 39, I was tempted again to buy some more clothes and to risk keeping them hidden. I was tempted also to go on some ‘fieldwork’ visits where I could stay away from home and maybe indulge some dressing which I had denied myself for several years now. The sex at home was much better than it had been for years. I was enjoying my inner-self fantasies… but I felt ready to try a little more.

This led me to a visit to Manchester and to a budget hotel room by the M6 motorway that is the main north-south artery around the city. I knew that the ‘Transformation’ business had its first shop in this area and that it was far far away from my being discovered if I went there.

Booking a room in a hotel, I knew a ‘chain’ where there were few services like Reception 24/7, Night Porter, Restaurant and such. It was literally, a room for the night. After 8pm, the doors were controlled by access keys that were the room keys.

I stopped on the drive north from London and went shopping. I bought a white cotton blouse with a lady’s business suit in a pale lilac, stockings and suspenders, bra and panties. All from a local Marks & Spencer store and a nearby Bon Marche store in Macclesfield, near the M6. I would rely on ‘Transformation’ to provide shoes for my size 9’s (which are tough to find shoes for ANY where!)

Having checked-in, I drove the remaining seven miles to the shop in a north Manchester suburb, went in immediately after parking the car, allowing myself no time to have second thoughts or ‘chicken out’. I walked in and said that I wanted a “Make-up & Change” service and showed my bag with its contents.

The shoes were going to cost me, big-time. So, too, would the wig. My own hair was nowhere near long enough for the look I was hoping to create. “Certainly, love!” was the reply from the (quite) mature lady assistant who served me. (There were three of them on duty serving. One was younger but obviously new to the business, the other two were older and quite used to people like me and their wishes).

We spent time choosing the wig (which I loved and prolonged, trying on at least four!) and the shoes, of which there were only three pairs to suit my needs. The wig was a fall of auburn curls, with feathery bangs, the length reaching my low neck, and with highlights framing the face.

Within an hour, I was changed, served with tea, made-up and be-wigged. In my business suit, I looked better than I could have dreamed or hoped. In the many mirrors surrounding the dressing room, I looked, if a little tall, ready for the world. I was so glad that I had bought and brought my own clothes. My previous ‘Transformation’ Awaydays had offered a charity shop selection of clothes to wear.

Several photographs were included in the cost of the service, so I posed as any girl would. However, none were close-ups of my upper body and face and hair which I would have liked. They did show, remarkably, that my legs looked good in stockings. I was right proud!

And I left the store, having paid and said my thanks. I left the store! I went out into the street — not in a party costume like before, but in a woman’s outfit, with a woman’s hair, shoes and attitude!!

It was now 5.15pm and getting dark. Walking to my car, I took deep breaths and enjoyed the feel of the clothes. Catching my reflection in a shop front, it was easy to stop and admire the image. Reaching the car, and pausing, I got in and drove away, unaware of and uncaring of the thoughts of any passer-by who might have seen me. I didn’t want to go and meet other people. I didn’t want to get mixed up with shopping crowds or travelling commuters.

I spotted a nearby public park which appeared to be quiet and yet still open. So, risking being mugged I now realize, I went in and sat quietly enjoying the approach of the evening sky.

Content with life. But what would my wife say. Was this betraying her?

Chapter 25 will show that it was.