Whose trousers?

Fiction by Johnny Cumlately

“Do you always wear girl's trousers?”

The question came out of the blue. Bob turned to face the questioner and paused before answering “Not always. But quite often.”

….....................................................................

Bob's meeting had finished early and he had booked into the large modern city centre hotel. It could have been any hotel in any city in the world. They all look much the same, these days. He had spent an hour in his room writing up his notes and making a couple of phone calls before changing and going to have a drink in the bar. He was standing at the bar enjoying a nice cold pint of lager.

“Do you always wear girl's trousers?”

The girl who asked the question was standing quite close to him and had just ordered her drink. He guessed she was between 35 and 40. Long auburn hair flowed down over her shoulders. She was dressed in a grey pinstripe trouser suit and heels which made her legs look very long. A white blouse with a dark red scarf was tied loosely round her neck. It would probably be described as power dressing but actually the masculine look made her attractively feminine.

“Not always. But quite often.” Bob had no wish to elaborate but added “I like to get into something casual when I change out of my business suit.”

He waited for the obvious question but was relieved when she said “I had a boyfriend once who liked to wear my panties. Lots of blokes seem to enjoy that sort of thing.”

Bob had changed into a pair of pull-on beige slacks with a draw string waist and a brown turtle neck sweater. He was surprised that anyone would notice.

The girl then introduced herself as Liz and changed the subject by commenting on the hotel and her work. She said she represented a well known clothes manufacturer and had been visiting an important customer. Her work meant that she always took particular notice of what people were wearing.

They had been chatting for a few minutes when a waiter approached them with menus. “Will Madam be dining tonight? Sir?” He obviously assumed that they were together.

Bob hated dining alone and seized the opportunity to ask if Liz would like to join him.

“Yes, please. That will be a welcome change from being put at a single table in a corner where the staff seldom take much notice of you. And you can tell me more about my question, later” she said smiling.

Bob knew he would not be able to dodge more questions but in the meantime would at least have some pleasant female company. They talked about lots of things and discovered they had quite a lot in common. They both lived in the same town and neither was currently in a relationship. They enjoyed a leisurely meal and it was not until they had adjourned to the lounge for coffee that Liz said “Come on! Tell me more about your choice of trousers. Are you wearing panties under them?”

“Yes.”

“Are you a cross dresser, then?”

“Not completely, but I have experimented once or twice.”

“This is getting interesting! Tell me what else you are wearing right now, that I cannot see.”

“That would be telling!”

“Go on. We're strangers. You can trust me.”

“I like to make sure that my male bits are safely tucked away out of sight and out of touch, so I wear a chastity belt. Panties and girl's trousers without fly openings are a logical choice.”

“A chastity belt? Does that mean that you can't take it off? Does someone else keep the key? Or do you have a key yourself?”

“Unfortunately, I don't have anyone else to hold the key but I can't take it off right now, even if I wanted to, because I've left the key back home.”

“So there is no way you could rape me, even if you had a mind to. Oh! I get it! You can't even jack off! That must be very frustrating.”

“That's the way I like it.”

“Well, I said we're strangers. But we're getting to know one another and we've already discovered we live in the same town, so I guess we should see more of one another.”

Bob had begun to wonder where the conversation was going but now he guessed that Liz might be leading up the holding his key. The thought was exciting but frightening as well.

However, Liz stood up and said “I don't know about you, but I have work to do tomorrow so I'm going to call it a day.” She handed Bob her card. “Its my business card but its got my home phone and email on the back. I have a feeling I'll be hearing from you! Thanks for a fascinating evening. Good night!”

Bob had a feeling that Liz was right!

…..................................................................

Four days later, when Bob had been back home for two days, he picked up the phone and dialled Liz's number. “Hello!”

“Hi! Liz. Its Bob here. I was wondering whether we could meet up. I'd be happy to take you out for a meal, if that's what you’d like.”

“I was wondering when you would call. Yes. I'd love to do that.”

“Great! How about Arturo's Bistro?”

“OK. That's only two blocks from where I live. So that's fine.”

“Tomorrow. 7 o'clock?”

“Thank you. See you there. And come back to my place for coffee. Make sure you are suitably but casually dressed and bring the keys. 'Bye.”

Bob had a pair of women's pull-on draw cord denim jeans which he reckoned fitted the description of suitable and casual. The advert in the catalogue described them as “the most comfortable jeans you'll ever wear” and he agreed. He had had to find the most suitable size by trial and error and in this case 14 (GB) proved right even though he had a 36 waist. But pull-ons had to go over a girls hips anyway. They had prominent seams down the front of the legs which he had never seen on men's jeans.

The instruction to bring the keys slightly surprised him because the possibility of Liz acting as key holder had not been specifically mentioned. But of course he would comply.

So the following evening saw him wearing these jeans and a light weight pale blue sweater. He got to the bistro just before 7 and Liz arrived almost immediately afterwards wearing designer jeans, heels and a sweater which hugged her breasts. She looked super!

She looked Bob up and down and nodded approval. “Yes. They are obviously women's jeans but they suit you well in view of what I already know.”

They enjoyed the meal and then walked to Liz's spacious first floor flat where she had already put out a tray with coffee cups. She made the coffee and they had finished drinking it before Liz finally said “Now hand over the keys and let me inspect my goods!”

Bob had never actually asked her to be his key holder but Liz had clearly taken it as read.

He handed over the keys and Liz undid the draw cord and eased the jeans down until they rested round his ankles. The panties followed so that his chastity belt was exposed for inspection.

“Wow! That's awesome! And you have actually chosen to wear that?”

“Yes. I tried another type and then made one or two myself but this is what I always wanted. It's a shemale belt made by a company called Neosteel in Germany. It cost me an arm and a leg.”

“I don't know about an arm and a leg but now you've given me the keys, its going you cost you your cock and balls. I'm getting wet just thinking about having total control over you. Don't even think about when I might get around to unlocking it.”

She ran her fingers over the polished front of the belt, admiring its quality. Of course, Bob couldn't feel that but he felt his cock trying to respond.

“You know I work for a clothing manufacturer. I'm going to get you some more clothes which will be even more suitable for someone with no cock. And you'll come to wish you had real boobs to go with them. I need to take your measurements to ensure a proper fit.”

She got a tape measure and expertly measured his chest, waist, hips, inside leg and several more places while he stood in front of this gorgeous girl who he scarcely knew but to whom he had already given charge of his most intimate bits. “Right! I'll let you know when I'm ready. In the meantime, just remember that I'm in charge and its no good whining if you get frustrated. If you do that, I shall just throw away the keys and have nothing more to do with you. Thanks for the meal. Time you went home.”

Bob was a bit taken aback by this abrupt change in her attitude as she showed him out.

…........................................................

He had to wait more than a week before Liz contacted him. For the first time, he was locked into his belt with no means of escape. He found it exciting and, as a result, very frustrating.

Eventually, his phone rang. “Hi! Bob, its Liz. Listen carefully. Come to my flat tomorrow, Friday, at exactly 7 o'clock. Make sure you've shaved all your body hair. I've got some surprises for you.” Click! The line went dead.

Bob wasn't quite sure what to make of the instruction to shave. It wasn't something he usually did but the next afternoon he left work early and called at the chemist on his way home. He bought a tube of Nair hair remover which he thought would be better than risking cutting himself with a razor. He went in the shower and liberally coated himself with it. He didn't have much hair on his chest but he included that as well. He couldn't remove his pubic hair which was covered by the belt. After some minutes, he turned on the shower and watched all his body hair disappear down the plug hole. It made him feel delightfully clean and fresh.

At 7 o'clock prompt, he rang the door bell for Liz's flat.

She answered the door wearing a T shirt, jeans and flipflops. “Come on in. Glad to see you in those nice jeans again, but its time to give you a complete makeover. I promised you some new clothes and I think you may be surprised but pleased. However, I must remind you - although its probably not necessary - that I'm in charge. I expect you to obey my instructions implicitly. We have the whole weekend and by Sunday night you'll forget you were ever male.” She took him into what appeared to be her spare bedroom. “Now strip off — right down to your chastity belt.”

There were some obviously brand new clothes laid out on the bed. Bob immediately noticed that they were all girl's clothing and they confirmed his suspicions as to what was in store. He had in the past experimented briefly with cross dressing but without help his efforts had always fallen short and he had therefore never ventured out dressed.

Liz noted the lack of hairs and nodded approval. “First of all, I've bought you some breast forms which are adhesive backed so I'm going to attach those first. Then I'm going to paint your finger and toe nails.” The breasts were soon fixed and looked very realistic and permanent, particularly as Liz added some extra adhesive. And his nails were painted a pleasant shade of dark red. Not too garish but certainly not a natural nail colour.

Next, she selected a suspender belt which she fastened around his waist and then handed him a pair of “nude” sheer nylon stockings. She showed him how to put them on without laddering and attached them to the suspenders. His painted toe nails were clearly visible thought the sheer material and he was amazed at the feel of the stockings over his hairless legs and how the bare bit at the top of his legs made him feel very vulnerable.

A bra and pantie set followed. They were a very flimsy material and the panties scarcely covered his chastity belt. But the B cup bra seemed a welcome asset to support his new breasts.

By now, it was time to add a wig and make up. Liz was ready with a brunette wig with quite short hair which curled in at the neck and then set about using her make up kit. Bob lost track of which items she used and Liz said “Next time, I'm going to teach you how to do this yourself.” After she had added eye-liner and lipstick, she finally pronounced Bob ready to see his — or rather her — new self. He — She — saw an attractive woman dressed only in bra, panties and stockings. His belt ensured that there was no trace of a bulge amidships.

“You're my girl friend Bobby now, short for Roberta and we're going to have a lot of fun. Are you happy?” asked Liz.

“Yes. Its a strange feeling but it somehow feels right. It's something I've always had a secret longing to try.”

“That's good. One advantage of working for a clothing company is that I can borrow things on a sale or return basis. That large pile of clothes are for you to try on and see what works and what doesn't.”

They spent the next couple of hours trying on various garments. There were several dresses. Those with a plunge neckline didn't work because Bobby had no natural cleavage. But there was a pretty print dress with short sleeves and a round neck. It came just above her knees and looked super with two inch strappy sandals. Cropped jeans also looked good with a plain white T shirt. And Bobby loved a pair of black slacks which had a side zip and a smooth front which would have shown a bulge if she had had one. They looked good with a bright multi-coloured blouse. Lots more — good and not so good. Bobby enjoyed every minute of it.

“OK. That's enough for now. I'll get you a sandwich and coffee before bedtime. Incidentally, don't imagine that staying here overnight might lead to you getting unlocked. You're sleeping here in the spare room. Tomorrow, you've got to practice being female!”

….................................................

Bobby spent a rather restless night but eventually fell asleep until she was wakened by Liz with a cup of tea. “Come on, sleepy head! Time for my new girl friend to wake up and get moving. We're invited to Ros for coffee this morning. I'm hoping to have her approval of my new protégée.”

“You mean I'm going out already?”

“Yes. I've known Ros for a long time. She has an interesting history.”

They had a leisurely breakfast and it was soon time to go out. Liz helped Bobby choose some black leggings with some brown knee-length leather boots with two inch heels. “The boots should help to support your ankles and you'll soon get used to the heels.” She also wore a long loose top which at least partially covered the plain front of the leggings. Bobby loved the way the leggings fitted so tightly. Liz helped Bobby with her make up, which was just as well, because Bobby was going to need a lot of practice with it.

Bobby was glad that the walk to Ros's place was quite short as she tried to get used to wearing heels. She was a little surprised by the woman who greeted them. Ros was all of six feet tall in her stockinged feet. She had long flowing hair and a nice figure but Bobby thought her hands rather large. Her voice was a low contralto and was that an adam's apple?

All was explained when Ros told Bobby that she was transgendered and had come out about ten years previously. Liz thought that meeting her would give Bobby more confidence. Liz had known Ros way back when she was still known as Peter and Ros said how much she had appreciated Liz's help and support when she first came out as Ros. Bobby wondered whether Liz was now expecting her to follow the same path. Although Bob (Bobby) was quite certain that he was “merely” a transvestite who just loved wearing womens' clothes, he found meeting Ros fascinating and her comments were definitely helpful. He hoped they would meet again.

The rest of that day turned out wet and Liz suggested they stay in and watch a movie. She had quite a large library of DVDs and chose one which she described as a “weepy”. Girls need to let their emotions go sometimes and Bobby did indeed need a handkerchief at the end. But then Liz found another DVD called “Chaste Nuns!”. It was a blue movie which featured graphic descriptions of lesbian sex. “If you're going to be a woman, you'd better find out more about what turns us on.”

They were sitting beside one another on the sofa and Bobby could not help noticing that Liz had a hand down her own jeans. When it was over, Liz said “Come on. Let's see how much you've learned from that!” and led the way into her bedroom which featured a large double bed.

A few minutes later, Bobby found herself naked except for the belt and Liz strapping a large dildo on her. Liz got Bobby to undress her - jeans, top, bra, panties - until they both fell on the bed in each others' arms. They slowly explored each others' bodies, exchanging deep kisses. Liz fondled the dildo and cupped Bobby's breasts as if they were real before easing the dildo into her pussy. As Bobby gently worked the dildo and teased Liz's nipples, Liz continued to play with Bobby's “breasts”. Bobby was left in no doubt when Liz came, not once, but several times, with noisy screams. Then she turned over and was instantly fast asleep.

Bobby, however, was wide awake and quietly went to the bed in the spare room. As far as she was concerned, although she was very turned on, her “breasts” covered her real nipples and the belt prevented any erection, so that she had experienced little or no satisfaction. And as Bob, he now badly wanted to masturbate but couldn't.

Before she finally nodded off, it occurred to her that Liz might get her kicks from liaisons with trans-sexuals. Was that her relationship with Ros? Had Ros had surgery? Did she still have a cock? Did that make Liz a lesbian?

…..................................................

Once again, Liz woke Bobby with a welcome cup of tea. Neither of them made any reference to last night's activities but Liz said that Bobby needed more lessons in makeup. She also had to practise with heels and softening her voice. Ros had said she would come round and later they would go to a club.

This time, Bobby noted that there was clearly something between Liz and Ros, especially when Ros said something which suggested she knew what had been going on the previous night. By mid afternoon, it was time to dress up to go out. Bobby wore black stockings with the suspender belt but this time chose a “little black dress” with short sleeves with which she wore a red chiffon scarf, red belt and red shoes with three inch heels. With her dark wig and help with makeup she looked super — very feminine. Liz and Ros were both dressed up, Liz in back trousers with a sequined top and Ros in a powder blue trouser suit which, although very feminine in colour, seemed to over-emphasise her height. Ros ordered a taxi.

It was a fairly short ride to a large suburban house. There appeared to be about 20 girls there — except that some of them weren't girls. Liz explained that it was a select group of people who met once a month, mostly trannies or trans-gendered and some had wives or girl friends with them. Liz introduced Bobby, saying it was her first real outing.

Bobby was relieved to find that the meeting was fairly low-key — mostly just girly chit-chat. But she met several “girls” whose experiences were similar to her own and she hoped there would be opportunities to attend the club in future.

They returned to Liz's flat before midnight in time for Bobby to catch a bus home as Bob had to go to work the next morning. Liz refused to let Bobby change but fortunately it was a warm night. Waiting at the bus stop, she felt very vulnerable but made it home without incident.

However, when Bob came to undress, he realised that he didn't know what adhesive Liz had used for the false breasts which were very firmly attached. Standing naked in the bedroom, he saw that with boobs and his belt creating an apparently smooth crotch, he looked and still felt female. He couldn't even remove all the traces of make up. How was he going to dress for work tomorrow? He decided he couldn't and that he would call in sick and say he had a dose of gynecomastia. If he mumbled the word quickly, he doubted whether anyone would understand and know that it was the medical term for men having swelling breasts! He had a disturbed night, frustrated that he could not masturbate nor even play with his nipples. However, if pushed, he might admit that he found that frustation pleasurable.

......................................................................

Next morning, he tried to phone Liz but there was no answer on her home phone. She did answer her mobile, however. “Sorry, Bobby, can't talk now. I'm with a colleague and we're just about to board a plane to Milan. Should be home on Friday. See you then.” She rang off. No work for Bob that week!

Then he had an idea. He found Ros's number and rang her. After he had explained his problem, Ros agreed to come over on condition that she was visiting Bobby and not Bob. She would bring make up and some spare clothes. Later that day, she arrived carrying a suitcase.

“Hello, Bobby. I had a feeling I would be seeing you again soon. I don't know what adhesive Liz used either, so I guess you're going to have those nice boobs for the next few days. So you might as well make the best of it. I've brought some of my stuff which should fit you — just casual things — slacks, a skirt, tops, sweater and a cardigan.”

Ros helped Bobby with make up and Bobby chose some beige slacks and a sweater. The slacks had a “wrong side” front zip whereas all her own slacks were either pull ons or side zip. They were an excellent fit.

They spent the evening chatting and Bobby learned a lot about Ros. As Peter, she had never really thought she was any other than male, although as a teenager, she had tried to avoid the rough and tumble of boy's games and tended to identify with the girls. Later, when all his friends started dating, he realised that he was not attracted to girls sexually but loved the shape of their bodies and the clothes they wore. He wanted to be one! Gradually, this thought became an over-riding passion. He bought some girls' clothes and started to wear them in private.

And that's how he came to meet Liz. He answered a discretely worded advert on a contact page. “Female seeks male company with mutual interest in clothing and TV.” Peter had wondered whether there was a hidden meaning and was not disappointed. With Liz's help he learned a lot about clothes and make up and soon had the confidence to venture out dressed. He started to take hormones and had his balls removed by a surgeon abroad. It was not long before his breasts developed and he finally came out as Ros.

Bobby had held back about asking the inevitable question but Ros answered it anyway. “No. I've not had the operation so I've still got a small cock. But that doesn't worry me. I can live with it rather than undergo major surgery.”

Ros returned home after insisting that Bobby visited her next day. That would mean she would have to travel on the bus in broad daylight.

….....................................................

Bobby slept well and woke feeling confident and positive. After all, hadn't Bob dreamt about being dressed as a girl and going out feeling that she really looked like one? Now she had no choice — at least not until Liz returned from Italy and even then it would depend entirely on what Liz wanted Bobby to do. And in the meantime, she could enjoy Ros's company and advice.

She spent a long time on her make up. It was the first time she had had to do it alone and it had to be perfect. Then she put on her favourite pull-on jeans and teamed them with a white T shirt which emphasised her boobs, a loose jacket, a pair of ankle boots and a bead necklace. Admiring herself in the mirror, she left a fairly typical modern girl. The bus ride was uneventful and Ros expressed her approval when she opened the door. “Wow! You've done well! Come on in.”

Later, Ros said “You seem to be enjoying yourself. Have you given any thought to your future? I mean — are you happy just being a transvestite or is this leading to something more permanent?”

“I don't know. It's all happened rather quickly since I gave Liz the keys to my chastity belt. And I know that she has a thing about feminisation. Maybe that's one reason why she was so willing to help you. I think she'd get a kick out of turning me into a woman.”

“I know she would. But what about you? How do you feel?”

“Right now, I feel great. Liberated from conventional men's things. I don't think I'm trans-gendered, just a transvestite but I imagine spending more and more time dressed female.”

“I know just how you feel. I started like that but it gradually became a 24/7/365 thing, especially when I started on hormones. And now I've come out and transitioned, I wouldn't ever want to revert to my former self. But I warn you, its not an easy path to follow. Society isn't ready to accept people like me too readily.”

“I guess I'm not going to have a lot of choice when Liz gets back. After all, she literally holds the key to my future.”

Ros nodded. “Guess so!”

….........................................................

Liz returned on the Friday afternoon and invited Bobby round that evening. “Hello! I can see that Ros has been giving you good tuition.”

“Yes. I could hardly go to work with these -” she put her hands under her boobs “ - so I had to stay at home. Ros and I have spent quite a lot of time together this week and had several long chats. But I hope I can get back to normal as Bob next week. I have to earn my living.”

“Ah! Yes! You didn't have the right solvent, did you? We'll have to see about that! Anyway, you'll definitely be keeping those nice boobs for the weekend. And your chastity!” Bobby had expected that reaction and was not surprised. Neither was she disappointed but sincerely hoped that Liz would relent before Monday. Nevertheless, she was quite looking forward to the weekend with Liz.

That night, she was shown into Liz's bed who enjoyed the same dildo session as the previous week leaving Bobby once again without relief. And again, Liz just fell asleep leaving Bobby to spend the rest of the night in the spare bed.

Saturday night was different. Ros stayed with them and Liz had set up a three-some. Actually, it wasn't really a threesome as Bobby found herself more of a spectator as Liz and Ros enjoyed quite a steamy session. She discovered that Ros's small cock was still functional!

They had a lie in on Sunday morning and after lunch, Liz announced that it was time to check on Bobby's chastity belt. Before Bobby realised what was happening, Liz and Ros had stripped her down to bra and panties, tied her hands behind her and added a blindfold. They told her that they would start by milking her and she felt a probe going up her backside and was relieved to find it a pleasant sensation although well short of a full erection and ejaculation. Ros held a small glass under her belt and soon reported a stream of cum.

Liz then unlocked the belt and sponged her clean. Bobby felt something cold applied to her cock which was still limp when Liz slid it into it's tube before putting the belt back on and locking it. “You didn't think I was going to leave you unlocked, did you? And even if you weren't locked up, you won't be getting the tube off any time soon.”

“What have you done with it?”

“I've used some of the adhesive that's been holding your boobs in place.”

“I'm hoping that you can get my boobs off. I've really got to go to work in the morning and I can't go with these.” She held her hands under them and merely succeeded in looking as though she was proud of them.

“Maybe. Wait and see.”

Bobby had to wait until the evening before Liz said “You've been very patient. Now we'll see if this solvent stuff works. The adhesive has certainly proved good and held you for over a week.” She produced a tube of a colourless goo and applied it to the top of one of Bobby's breasts and tried to work it under the plastic with no success. “Nothing doing! It looks as though you're going to have to stay female a bit longer. I'll have to ring up the manufacturers for help and they won't be open until tomorrow.”

“Here, let me read the instructions. No. It says here put the solvent under the false breast and leave for an hour. OMG! What if it doesn't work?”

“That will be too bad. You'll have to tell your employers you're having a sex change.”

“But I'm not! OK. I love dressing up as a girl but that doesn't mean permanently!”

To Bobby's huge relief, an hour later the breasts came loose. But even then, Liz and Ros had not finished with her. Where the false breasts had been, her nipples were now extra tender and they made her endure having them teased so that Bobby's cock almost burst out of the chastity tube.

Finally, they relented and allowed Bobby to become Bob again. But he still wore his favourite jeans to go home and now found it odd not to have the weight of his breasts on his chest. And of course, he was still locked in his chastity tube.

….................................................

He arrived at work the next morning only to find the personnel manager wanting to know more about what had been wrong with him. It seemed that they had heard what he had said about having gynecomastia and had discovered what it was. Bob had a very red face as he assured them “it was just a minor swelling but the doctor had been concerned lest it might prove to be more permanent.”

“Like changing sex?”

Bob's hesitation suggested that the question might have been rather close to home. “No. Not really. I'm not taking hormones, if that's what you mean.”

Fortunately, the manager let it rest at that. “Anyway, we're glad to see you back at work. If there is any problem you want to talk about, don't hesitate to come and see me.” Bob wondered whether the manager suspected that Bob's “illness” was not all it seemed and kicked himself for mentioning gynecomastia in the first place. Perhaps he should just have said he had flu. But he thought it likely that with Liz in charge, there might be problems in future.

That night, he thought long and hard about where things were going. His long held wish to have a keyholder had come home with a vengance. And he knew that he would not be giving up the idea of cross dressing. He felt sure that it would not be long before he had breasts again and would enjoy wearing them. And as for girl's trousers, he had already changed into his favourite pull-ons when he got home from work.

Liz phoned. She wanted to know how Bob had got on in work and Bob told her about his interview with the manager. “It looks like he suspects that there is more to your absense than you've admitted and he's not far wrong. Just wait till I've finished with you. You'll have a lot more to explain. And are you wearing girl's trousers now?”

“Of course!”

Fiction by Johnny Cumlately.

[email protected]

November 2013.