Winter break. Part 1.
Fiction by Johnny Cumlately
I was due a few days holiday to be taken before the end of the year. It was already mid November and the nights had closed in. I did not want to fly off to foreign parts and the papers were full of adverts for short winter breaks. A city rather than a remote rural hotel made more sense and I chose Newcastle because I had never been there and it seemed to offer plenty to do and see even if the weather was wet and cold. I booked a good city centre hotel and decided to travel up by train.
I had always had a problem with excessive masturbation and choose to wear a chastity belt. It is a beautiful SheMale belt which nicely hides my male bits and cost me a bomb! I did not have a keyholder and usually left the keys in some fairly inaccessible place at home or took them with me if I was away. There are two identical keys and I have always kept them together. On this occasion, however, I decided to tempt providence and leave them both at home. The prospect of being locked up for nearly a week with no possibility of relief was exciting.
Another quirk of mine is that I always wear women’s trousers with no flies when I am belted. After all, I have no use for fly openings and have to sit to pee anyway. Worn with sweaters or jackets, the difference is not noticeable except on close inspection and they are a pleasant reminder of my situation.
I wore a sweater and pull-on cords for comfortable travel, arriving late afternoon. The hotel came fully up to my expectations. I had a leisurely bath and changed into an open neck shirt, jacket and a pair of smart “classic” pull-on slacks which I had bought from a well known multiple store. The restaurant was not yet open so I sauntered down to the large bar, which at that early time was empty. I sat on one of the high bar stools and ordered a drink.
A few minutes later, an attractive lady came in and sat on an adjoining stool. I noticed that she wore an identical pair of slacks to my own. They were a pleasant grey/blue check with the usual small ornament on the front of the waistband. I had not done up the button on my jacket so that the front of my trousers was clearly visible and girls are quick to notice such things!
After ordering her drink, she looked across to me and said “I see we have a similar choice in clothes. But I didn’t know they made gents slacks in the same material.”
I blushed and only managed to say “They don’t.”
“In that case we really do have the same taste.” Fortunately, she went on to talk about how nice the hotel was and we made small talk for some time until a waiter arrived to say that the dining room was now open and we found ourselves sitting at single tables at opposite ends of the large room.
The next day was fine and dry so I spent the time sightseeing in and around the centre of the city, admiring the Tyne bridges and crossing the river to see the new Sage Centre in Gateshead and was back in the hotel in plenty of time to change and have a pre-dinner drink.
The same lady was in the bar before me but we both did a double take when we realised that once again we were again wearing the same trousers from the same “classic” range, only this time in a green/brown mix.
I took the lead. “Well, this proves we have the same taste, so maybe we should get together. Why don’t we share a table tonight instead of being treated like lepers?”
“Thank you. I should like that.”
It turned out that her name was Sheila. She looked about five years older than me and told me she was a divorcee living in Scotland although she did not have a Scots accent. “My husband was Scottish and we lived up there. I stayed after the divorce.”
Sheila was good company and there was no shortage of conversation but it was only when we had retired to the lounge for coffee that the trousers were mentioned again.
“Why do you wear women’s trousers?”
I decided there was no point in trying to duck the question. “Because I have no need of access to my male equipment.” We were sitting together on a settee and I guided her hand down the front of my slacks so that she could feel the hard smooth front of my belt.
“Wow! A chastity belt. Do you choose to wear that, or does someone else control it?”
“It’s my choice.”
“So you’ve got the key and can take it off whenever you want.”
“Not exactly. I’ve left them at home this week.”
“So you can’t take it off now, even if you want to?”
I shook my head.
“You and I have a lot in common as well as our choice of trousers.”
“You mean you wear a belt?”
“No, but I know someone who did. He was my husband. I caught him fucking my young 18 year old niece who was half his age. A prostitute would have been bad enough but not my own family. I’d read something about chastity belts for erring husbands and told him he could choose to wear one or get out. He chose the belt so we bought the most secure one we could find on the internet and I kept the keys. I didn’t allow him out for three years except when I tied him up for a quick hand job and a clean up once a month. In the end, he whined continually and was so frustrated he chose to leave but I ensured I got a good deal and wouldn’t give him the keys until all the documents were signed and sealed.”
“I guess the difference is that I wear mine by choice and he didn’t.”
“You know, I’m very curious to see your belt. Why don’t we go up to my room and then I’ll tell you what else happened?”
I followed Sheila upstairs wondering what I was going to hear or see next. She shut the door of her room and dropped the latch.
“Stand up straight!” She stood in front of me and, as there were no buttons or zips to undo, easily slid my trousers down to my feet. I was wearing black opaque tights and a tight long legged panty girdle. They also finished up around my ankles revealing the plain front of my chastity belt. I explained that I had chosen the shemale belt because it looks almost identical to a female belt from the same German manufacturer.
“Oh! My! You do do the job properly! Judging by the steps you take to make sure your male bits are hidden away and inaccessible, I suspect you would actually prefer to be girl. Your belt is beautiful, lovely shiny stainless steel, and I know its very secure because I did some research before I ordered my husband’s belt. Now I’ll tell you the rest of my story....
“After a time, it wasn’t just my husband who was frustrated by being locked up. I was equally frustrated by not having my usual amount of sex. There was a lovely Canadian girl renting the house next door while she was in Scotland and I had a passionate affair with her. She was openly lesbian and taught me a lot about my own sexuality. And one of the things we used was this...” She crossed the room to her suitcase which was open and produced a strap-on dildo which she proceeded to put on me.
“I love it because it never goes soft.” She dropped her own trousers and panties and pulled me onto the bed. She played expertly with my nipples so that my penis was straining in its narrow prison before she guided the dildo into her cunt. In spite of the constraint of my belt, I found myself hugely enjoying fucking her. Half an hour later, she had had several orgasms and finally became exhausted. “Thank you. I haven’t had a session like that since Helen went back to Canada.”
For the next two days, Sheila and I did more sightseeing together and each evening after dinner had sessions with the dildo.
“Would you like to come to Scotland for Hogmanay? I could do with some company and I want to take you to a fancy dress party.”
I had no other plans and readily accepted.
“There is just two conditions. You must wear exactly what I tell you. And bring the keys.”
We parted with a long kiss in the station next morning when she caught her train north and I caught mine south. I was again wearing my cord pull-ons and secretly admired the front seam and lack of a fly opening all the way home. I wondered what lay in store for me in Scotland.
It seemed a long time to Christmas and the New Year. As soon as I had finished work on Christmas eve I put on my belt and resolved to stay locked until I returned from Scotland in the New Year. I’ve always spent Christmas day with an old Aunt and Uncle who are my only remaining relatives. They never seem to notice what I wear and probably would not comment even if I turned up in a skirt but I had on a nice pair of side-zip black slacks.
Three days later I was on the train to Edinburgh. Fortunately I had booked a seat as the train was very crowded. Having had problems on a previous occasion, I was concerned about using the toilet on the five hour journey in view of the need to sit and then mop up carefully but all was well.
Sheila met me at Waverley station. After a quick kiss, I realised that she was running her hand down the front of my usual pull-on slacks and feeling the hard shield of my belt. “Good Girl! Properly dressed and all locked up for me.” Girl? I decided not to comment there and then!
She drove me straight to her large terraced house in the southern suburbs of the city where I was shown up to my room and was surprised to see a selection of girls clothes laid out and that the bed had not been made up. “You remember when I invited you, I laid down two conditions, one of which was that you would wear exactly what I tell you? That condition starts now. We’re eating in tonight so I suggest you have a wash and brush up and change into something comfortable. I think you’ll like all these things which should fit quite well once I’ve fixed you up with some false boobs and a bra. And I’ll give you a hand with makeup until you get the hang of it. I can’t have the neighbours thinking I am entertaining a gentleman friend. It wouldn’t be proper, would it? ... And please hand over your keys for safe keeping. Don’t expect them back any time soon.”
I had half expected that the fancy dress party might involve some cross dressing but Sheila obviously intended that I should be en femme throughout my visit. I was a bit dismayed but also excited as I had never cross dressed before. Nor had I ever given the keys to anyone else.
An hour later, we were downstairs enjoying a cup of tea. I was wearing a white jumper over a long denim skirt and strappy sandals with manageable one inch heels. I had a wig with shoulder length brown hair and modest makeup and a pendant on a narrow gold chain. The jumper emphasised the shape of my new boobs.
“How do you feel now?”
“Much better, thank you. I was really ready for a cuppa.”
“No. No. I meant how do you feel in yourself?”
I paused for a moment. “Comfortable. I just feel right and relaxed. This the first time I have ever worn a skirt, but its lovely. You said we are going to a fancy dress party tomorrow and if you told me to go upstairs now and put my male clothes back on, they would already feel like fancy dress.”
“That’s just what I thought you would feel. Right from the first moment we met in Newcastle I felt sure you were more female than male.”
We chatted on about what we had been doing since Newcastle and over Christmas and then Sheila said “By the way, the neighbours have invited us to a pre-lunch drinks party tomorrow. Its not a formal affair but I think a dress would be more appropriate than trousers. There is a nice black cocktail dress on the bed for you. Short sleeves, about knee length. There’s a stole as well which will look good with it. Its nearly the same colour as your hair. You’ll need to wear tights and there’s a pair of patent leather shoes. They have two inch heels which you should be able to manage. Oh! And you’ll need to shave your legs before you can wear sheer tights.”
“So they are expecting me to be female.”
“Of course. I’ve told them your name is Joanne, or Jo for short.
When I went up later for a long soak and a shave in the bath, Sheila asked if it mattered if my belt got wet. “Its fine as long as I use a hair dryer to make sure its absolutely dry.” I went down afterwards in just a negligee over bra and panties feeling delightfully smooth and fresh and we soon retired to Sheila’s large bed for a dildo session before falling asleep. I woke next morning with the large artificial cock still attached. It felt strange.
I loved dressing for the drinks party. I had often worn thick opaque tights, but sheer tights over shaved legs were something else! The dress and shoes fitted perfectly and with Sheila’s help, I was confident of my appearance and enjoyed socialising with her neighbours, managing to soften my voice to a sort of husky alto. The only problem was that, standing a lot and not being used to wearing heels, my legs ached badly by the time we got home. I guessed I would get used to that.
In the evening we dressed up to go to the party. Sheila had a super Robin Hood outfit. Her green tights nicely complimented her long legs, the very model of a pantomime “principal boy”. She dressed me as Maid Marion in a full length white dress and changed my wig for one with long blond hair which came right down to my waist. Sheila was careful with my makeup so that I looked and felt genuinely feminine. A taxi took us to a club in the city centre where security was tight. Bouncers carefully inspected our invitations. There were about 40 guests in every conceivable sort of costume, many obviously cross-dressed. We had an excellent meal and Hogmanay was duly observed in true Scottish manner. There was a lot of merriment and a lot of alcohol was consumed but no one appeared unduly the worse for wear.
Well after midnight, I was approached by a man dressed as Dracula, obviously male, and after a few minutes chat realised that he had succeeded in getting his hand under my long dress, eventually reaching the hard front of my chastity belt. “Wow, young lady, I see you came prepared for every eventuality and are definitely not available. Does Robin keep you locked up against mediaeval knights?” Little did he know how close he was to the truth.
We got home at around 3 o’clock and both fell asleep as soon as we got into bed.
On New Year’s Day we got up late and then Sheila took me to join the crowds in the sales, so that I could buy some more clothes. I had decided that I would not be leaving Joanne in Scotland so I wanted some simple cheap things to wear around my flat when I got home. A couple of bras, a sweater and tops and more slacks. I would order another pair of breast forms on line.
I was due back in London the following day and when I was about to leave to catch the train home, I asked Sheila for my keys.
“Oh no, Jo. Its not as easy as that. If I hold them, I can be sure that my new girl friend comes back to see me before long.”
“But Scotland is a long way from London. What happens if I need them in emergency?”
“I’ve thought of that. I have a friend living in London. We’re two of a kind! I am going to mail one of the keys to her with instructions not to hand it over unless I agree. I will give her your name and address but I’m not giving you hers, so you can’t pester her for it.”
So that was that. I’d had a super time with Sheila but I was going home still locked up for what might be a long time.
Winter break. Part 2.
Except for being locked into my chastity belt with no access to the key, life returned to normal. I was back at work in the new year and just had to remember that I couldn’t use the urinals in the gents. I don’t think any of my colleagues noticed.
About ten days later, there was a letter waiting for me when I got back from work. The writing was unfamiliar but obviously female.
I’m Sheila’s friend and can’t wait to meet you. She has told me all about your visit to Scotland and how you much prefer being a girl. I’m sure I can help you a little further along that road. Please give me a ring and we will arrange to get together. Love Alice.”
There was a phone number, but no address. Was this something that Sheila had set up, or had Alice decided she could use the key as an opportunity for some fun? Either way, I didn’t need any encouragement. A meeting with Alice might even get me unlocked. I dialled the number and the phone was answered “Nurse Williams.”
I paused, “Hello. Is that Alice?”
“Oh, Hello! That must be Jo! So glad you’ve called. Are you going to come and see me?”
“Yes, please. I think you have something of mine of a rather intimate nature.”
“Yes, Jo. And I have strict instructions from Sheila on what to do with it – or rather what not to do with it, so don’t get excited about it. Saturday afternoon 3 o’clock Okay? 5B, Trafalgar Gardens. I’ll look forward to meeting you, Jo. See you then. ‘Bye.”
She had emphasised the name Jo, so I had no doubt that I was to go en femme but tried to be androgynous by choosing my usual pull-on cords and a thick sweater which would partly hide my artificial boobs. It was the middle of winter, after all. Just a smear of lipstick. It would be the first time I had ventured out on the streets of London as Jo but I need not have worried. People out shopping on a Saturday afternoon were not likely to notice me anyway.
5B turned out to be a first floor spacious flat. My ring was answered by a buzz and a voice on the intercom. “Hi Jo! Door’s unlocked. Come on up.”
The girl at the top of the stairs was obviously Nurse Williams.
“Hello, I’m Alice. I’ve just come off shift at the hospital and haven’t had time to change so we might as well do the business first and then I can get to know you later. Come with me.”
I was taken into the bathroom. “Strip off! I’ll be back in a moment.”
By the time I had taken off my cords and panties she had returned carrying a small black bag from which she took a familiar key. She put on some rubber gloves and examined my belt carefully. Very professional!
“I like that. Better than some I’ve seen. You'd be surprised what we see in the accident department. But at least I won’t have to call the fire brigade to cut it off you. Stand in the shower and put your hands above your head.”
I had not noticed a length of cord hanging over the shower rail which had slip knots at each end and quickly found my wrists had been secured. Alice unlocked the belt and as it fell away my cock immediately came to attention. “Been over three weeks, has it? I’m not surprised.”
She reached into the bag for something else, which I couldn’t see in spite of there being a mirror above the wash basin immediately opposite the shower. I felt something pushed up my back passage which started to vibrate. Alice held a plastic cup in front of me with one hand while she manoeuvred the probe with the other and I soon saw cum dripping from my cock. There was no sense of climax but two or three spoonfuls of cum had been collected in a couple of minutes and by then I had gone completely limp. I was literally drained.
Alice washed the belt, sponged my groin area and quickly refitted and locked the belt.
“Good Girl! That should keep you safe for another month. Don’t bother to dress yet. I’ll go and change into something more comfortable.”
She reappeared a few moments later dressed only in a see-through negligee which left nothing to the imagination. She took me into her bedroom and strapped a dildo on me which was very similar to Sheila’s.
“Sheila’s told me all about your romps in Newcastle and in Scotland and has told me I can have some too!”
I thought Sheila had been good at keeping me turned on but Alice had an intimate knowledge of erogenous zones and despite being re-locked, I loved fucking her until she squealed so loudly that I was concerned about her neighbours.
Afterwards, we chatted for a long time. Alice asked much the same questions as Sheila had about my belt and my gender. As a nurse, nothing surprised her and I found it good to talk frankly to someone who was so sympathetic and understanding. And she offered to help me with dress, fashion and makeup.
It was quite late when I returned home and I found a message from Sheila on the answerphone. “Please ring me as soon as you get home, no matter how late. I want to know all about it.”
It was already nearly midnight, but I knew Sheila was unlikely to be in bed.
“Hello. Its Jo. I’ve only just got home but you said to call you.”
“I know. I’ve already had a long chat with Alice but I want to hear your story.”
I described everything that had happened since leaving home earlier. “I think you had better plan another visit to Scotland. Make it a long weekend. Maybe you should wear a skirt on the train next time. You must have worn those cords out by now. Anyway, neither Alice nor I are going to unlock you until you’ve learnt to be a good girl all the time.”
“I’d love to come up to Scotland again. And with a bit of encouragement from Alice, I might even summon up the courage to travel as Jo.”
I managed to arrange a Friday off three weeks later, so that I could travel up on Friday and back on Sunday. In the meantime, I paid several more visits to Alice who spent time teaching me more about makeup and all things girlie and took me on a shopping trip to buy some girl’s tight patterned jeans ( I got used to them having a short zip which did up the “wrong” way) and I splashed out on a lovely pair of brown leather knee length boots. It was the middle of winter, after all! The boots had two inch heels which I could manage because they supported my ankles and made me feel a million dollars.
Talking to Alice one day, she asked “Did you always want to be a girl?”
“Yes, I think I did. But I knew I was a boy and never had any doubt about my gender. It was just that I never liked my male appendages and envied the girls their figures and nice clothes.”
“Is that why you took to wearing a chastity belt, to cover them up?”
“Yes - and to stop me masturbating.”
“So Sheila was right about dressing you as Jo. With a bit more experience you’ll be a lovely girl and never want to go back.”
My time with Alice always ended on her bed with the dildo. She seemed to have an inexhaustible desire for sex - but not with real men. Just like Sheila.
The journey to Scotland was uneventful. I wore a sweater with a long denim skirt and woolly tights and the boots as snow was expected in Edinburgh and settled into a corner seat on the train. Sheila met me at the station with rather more than a sisterly kiss and eyed me up and down with obvious approval. “Well done, Jo. I can see that Alice is doing you a lot of good.” She took me home where we cuddled up in front of a bright fire before adjourning to Sheila’s bed.
Fortunately, it had not snowed on Saturday and the weather was sunny but cold. Sheila took me sightseeing. I wore my new jeans and boots and we walked the whole length of the Royal Mile from the Castle to Holyrood House.
We had both been invited out in the evening by two gentleman friends of Sheila’s for a meal. I was a bit intrigued by the idea that Sheila was being entertained by men, in view of her being openly lesbian. She insisted that we dress up for the occasion. I wore the same black dress as I had for the drinks party on New Years Eve. She said, jokingly, “You’ll be quite safe. They can’t rape you while you’re all locked up, and I think I can look after myself.” David and Peter turned out to be very good company. It was a new experience for me to be flirted with and I’m sure Sheila enjoyed the attention she received. I felt sure they were a gay couple. They must have known Sheila’s sexual orientation and probably guessed my true gender but played up to it. Either way, it was a good night out.
Back at Sheila’s home, we had a long chat. “I just knew from our first meeting in Newcastle that you were not a proper guy and you’ve taken to being Jo like a duck to water. Have you given any thought to the future?”
“Not really. I definitely prefer being Jo to Johnny but I suppose Johnny has to earn a living and I can’t quite see myself turning up at the office in a skirt. Not at present anyway.”
“You mean there might be a time when you would? If you really mean that, you should start planning now. I might have a word with Alice, because she could help you on your way.”
Sheila’s comments set me thinking. We arranged that she would come down to London soon and stay with Alice. I suspected that they would both try to encourage me to change.
Back home in London, I continued to visit Alice regularly and Sheila joined us for a weekend a few weeks later. I soon found my self enjoying a lesbian “threesome”. They returned to the question of my future and by now I had made a decision. “Who are you going to be, then, Jo or Johnny?”
“I’m spending more and more time as Jo, except for work, and feel really comfortable about it. I feel confident when I’m out and about. I don’t have any close relations to worry about and I’ve told my old Aunt and Uncle who I spent Christmas with that I might visit them wearing a skirt one day and they just said “That’s all right, so long as you’re happy.”
Sheila and Alice looked at each other and Sheila said “You’re due a monthly milking. Alice will get a strong transdermal hormone patch and fix it under your belt where you can’t touch it. So that will be final. She will need to replace the patch once a month and in six months you should have a pair of budding breasts. Agreed?”
I nodded my consent, knowing that I was making a life changing decision.
Next day, when Alice came home from work at the hospital, Sheila asked her if she had everything they needed. They turned to me. Alice asked “OK? Not changed your mind?” I nodded again. “This time I’ll give you a jab. It’ll put you out for an hour or so while we do the necessary.”
I was actually quite pleased that I would not have to witness both girls milking me. I hadn’t minded Nurse Williams’ professional touch, but wasn’t so sure about Sheila. Anyway, Alice’s jab knocked me out pretty quickly.
I woke up lying on Alice’s spare bed and discovered I had been asleep for four hours. I felt decidedly odd and a bit sore in my groin. My belt had been locked on again. By then Sheila had left to go back to Scotland.
Alice appeared with a welcome cup of tea. “All right now? You’re another step along your journey. No regrets? - its too late now to change your mind. The patch may make you feel a bit queasy for a day or two and the soreness under the belt should go quickly. I’ll be keeping an eye on you. Come over one night during the week so that I can do a quick check.”
As I was still a bit shaky after the anaesthetic, I got a taxi back home and felt fine the following morning going to work as usual in male mode. I did still feel a bit sore and wondered why, but it soon wore off and on Wednesday night made a short visit to Alice. She told me to go in the shower and again roped my wrists while she undid the belt and after a brief inspection announced that all was well and re-locked it. “Everything’s fine. The hormone patch is quite strong and without a supply of testosterone you should soon find some changes, particularly around your nipples.”
I kept up my weekly visits to Alice and went to see Sheila a couple of times during the spring. In early summer, Sheila paid a visit to London. By then, there were very definite signs, not only physically but psychologically. I was aware that my attitude to work had changed. I no longer felt so competitive and seemed to identify more easily with the female staff. My breasts had developed so that I wore a training bra and had to make sure it was not visible under my shirt at work. I had put on weight around my hips and no longer got the usual early morning attempted erections. I let my hair grow and tied it in a pigtail when in male mode. I would soon have to decide when and how to “come out” at work.
It was Sheila who provided the solution. “Come and live with me. I’d love that. Your company has an office in Edinburgh, doesn’t it? Why not ask for a transfer? Tell the personnel people in confidence what’s happening to you and ask them to take you on in Edinburgh as Jo, instead of Johnny.”
“Thank you. I’ll see if they can do that.”
It was time for my regular milking. When Alice took my belt off, I could see that my penis had shrunk a bit and no longer sprang to attention when freed from its narrow tube. Also, the result of Alice’s efforts with the vibrator produced nothing more than a trickle of colourless liquid. When she cleaned round between my legs, I realised that no balls were visible. She noticed my concern.
“You’re well past the point of no return now. We removed your testicles when we first put the patch on, so that you would stop producing male hormones.”
“You mean you castrated me?”
“Technically, yes. But think of it as just another step along the way.” She turned to Sheila. “There doesn’t seem much point in keeping her in the belt any longer, does there?” Sheila agreed and the belt was put aside on a table, together with Sheila’s key which she always carried with her and which had been used to unlock me this time. Putting my panties on without it seemed odd at first after so long but my limp penis nestled down between my legs so that it was scarcely visible.
Sheila had always been fascinated by the belt. She picked it up and could not resist pulling her panties down, removing the penis tube and stepping into it. To our surprise, it fitted her almost exactly and in a moment she had snapped the lock closed. Alice and I looked on and exchanged glances as we both reached the same idea. I quickly grabbed the key off the table before Sheila could reach it.
“You look really sexy in that. Its almost the same as a real female belt, except you might be able to get a finger under the front. But there’s no way you could enjoy a dildo. I think its my turn to keep you locked up.”
Sheila looked as though she didn’t know quite what to make of her predicament. “You can’t keep me locked up! I’m wet already just thinking about it.”
“Oh! Yes, we can.” Alice and I said together.
It was by then time for Sheila to leave to get her train home, and we flatly refused to release her. “You’ll bring the key when you come to see me in Scotland, won’t you?”
“I’ll think about it.”
Winter break. Part 3.
On Monday morning, I plucked up courage to see the personnel manager. Ms Smith was a pleasant and understanding lady - about 55. Married, or spinster? Nobody knew.
“I have something to tell you in complete confidence and then I want to ask a favour.”
“Go on, then.”
I opened the front of my jacket to reveal my budding breasts and said “I am undergoing a sex change.”
“My dear, that’s wonderful! I see you are well on the way to joining the better half of society.”
“That’s why I have come to see you. I have reached the point at which I can no longer keep it a secret. I’ve been Joanne for some time now everywhere except here at work and I don’t know how the staff will react if I suddenly appear in a skirt. ”
“And the favour?”
“I wonder whether it would be possible for me to transfer to our office in Edinburgh? I have a close friend there who had offered me a home and I think I might find it easier to start in a new job as Joanne. People are bound to find out sooner or later, but I’d rather it was later.”
“Well, I don’t know whether it will be possible because all our branches a trying to reduce costs and staff numbers but I’ll have a word with my opposite number up there. Don’t expect an answer for some days. Thank you for confiding in me. I will respect that.”
That night I had a call from Sheila. “Have you asked about moving to Edinburgh? When are you coming to see me?”
“I have asked but I shall not know just yet. Anyway, I only saw you yesterday.”
“But you’ve got the key to the belt and I’m already going crazy not being able to even touch my self properly.”
“Ah! So that’s what the hurry is. I’m afraid you’re just going to have to wait. You’ll get used to it and then find you like wearing it. I’m rather missing it, myself.”
It was nearly two weeks on Friday afternoon before Ms Smith called me into her office. “I’m afraid Edinburgh is no go. But I’ve a suggestion to make. We don’t want to lose a good employee. I can give you a month’s sick leave and in the meantime break the news to your colleagues. They may be curious but I’m sure they will be very supportive and will have had time to get used to the idea that you will be wearing skirt in future.”
“Okay. I’ll try it, but if they won’t treat me as a normal colleague, I’ll have to hand in my notice and try to get another job.”
“I’m sure you won’t need to do that. Is there any particular work you must finish?”
“No. I’m pretty much up to date.”
“Good then I’ll see you four weeks on Monday. Good luck!”
As soon as I got home, I rang Sheila with the news and also spoke to Alice whose main comment was “Don’t give her the key just yet!” I arranged to catch the train north the next morning.
As before, Sheila met me at the station with a hug and a smacking kiss. “Have you brought it?”
“Brought what?” I teased.
“The KEY! .”
“I think so. I threw a lot of things into the bottom of my case. It may have been among them”
“I’ve made a decision. I’ll tell you tonight.”
As we snuggled up in bed together, Sheila told me. “You were right, I like the feeling of being locked up and protected. I’ve ordered a proper female belt for myself. With any luck, it will arrive while you’re here.”
I spent some chaste but happy weeks with Sheila. She did not pester me for the key but I now knew that I would have to use it when her belt arrived. In the meantime, she took me on a tour of Scotland. We stayed mostly in Bed and Breakfasts and I was pleased that not once was an eyebrow raised at the idea of two girls sharing a room, often with a double bed. Even in these more enlightened times, I doubt if two men would have had the same experience.
The day before I was due to return to London, a parcel from Germany arrived for Sheila. I watched her excitement growing as she opened it A beautiful shiny steel edged with soft rubber. It looked almost exactly like mine except that the front shield was rather wider and obviously intended to prevent even a single finger of access. I got the key of my belt and unlocked Sheila. As it fell away, she instinctively moved her fingers to her pussy. “God, how I’ve waited for that!”
She disappeared into the shower and I guessed from the noises that she was making the best of her freedom. When she had dried and powdered down, she asked me to put the new belt on her. It was a perfect fit but I suggested she should wear it for a few hours to get used to it until bedtime. I would finally lock it on before I went home. She insisted that I wear my belt immediately, however. I loved the feel of it after so long even though my cock was no longer truly functional and I knew that she would be keeping the key in Scotland.
That night, we used the dildo for what may be the last time. As soon as Sheila had reached an enormous climax, she said “Lock me up. NOW! Don’t wait until tomorrow.”
We had a tearful parting at the station next day and I promised to be back soon, but did not promise to bring her key.
As soon as the train pulled out of the station, I discretely fingered the pair of keys hanging down my cleavage, one of which I looked forward to giving to Alice. Then I booted up my laptop. I had five hours to finish this autobiography and to consider my future.
By the time the train reached the outer suburbs of London, I was up to date and actually looking forward to Monday morning with confidence. My colleagues will be expecting me to arrive in a skirt and I will not disappoint them. I shall get up in plenty of time and put on a black pencil skirt - just above knee length - black tights and simple court shoes with modest two inch heels which I can now cope with quite well. I will wear a purple blouse over a black bra which will reveal a small amount of cleavage and show the shape of my budding breasts. From a silver pendant will hang a small key. My hair will have been done by Alice’s hairdresser and I will use only a small amount of makeup.
Everything else is in the future.
Fiction by Johnny Cumlately
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