Made to Obey Ch. 12

Reprise: I'd been caught wearing my Sister-in-law's underwear and jerking off to shemale porn by wife (Ruth), Sister-in-law (Esther) and their mother (Donna). I'd been forced into a chastity cage and made to wear panties all the time. Furthermore, a curious email I'd sent to "Bowser" before I was married led to my past fraudulent activity being uncovered. I'd been sent on a six-week training course to prepare for my future as a transsexual at the beck and call of my wife and Esther and Donna.

Self-confidence, self-assurance, call it what you will, can be a pretty fragile thing. Months ago, Carl Henley-Gifford was a self-confident, assured man, now confidence in that man had all but gone. Instead, as I stood in my underwear looking at my reflection in the mirror, I had more confidence and assurance in the Carla Gifford that stood there. My, I was pretty.

Long, stocking-clad legs and tight, bum-hugging skimpy cotton briefs that emphasised how peachy my pert behind had become gave me a body most women my age would be jealous of. The hormones I was taking had seemed to narrow my waist as well as endow me with two small, pert bosoms. The fabric of my little bra could not hide the fact that my cute, upturned breasts housed two strong, pert nipples. One other positive from the hormone treatment was that I no longer had to shave.

It was the Saturday after I'd completed my training with Mrs Johnson and Young Mistress Jasmine. Ruth was taking me to a nearby shopping centre to buy some new clothes to compliment my new more feminine figure, so I was spared having to don my bell-ringing anklet and choker. I'd lost a little weight over the previous weeks and Ruth did even wonder if I might now be able to fit into some of her clothes.

She insisted I wore a skimpy white blouse under a smart black jacket and a skirt that came down to just above my knees. There was little chance that my stocking-tops would be exposed if I comported myself as I'd been trained to by Mrs Johnson. Black high-heels made me stand a good few inches above Ruth and I was allowed to wear a gold-chain necklace and matching bracelet. My nails were varnished a bright pink and my make-up and hair were done to a high enough standard to add to my glamorous appearance.

I was still a little apprehensive about appearing in public as Carla and even more apprehensive about the job Ruth had told me she'd arranged for me, most of the earnings from which would go to a fund which, on reaching £140,000, would be given to a charity to atone for my fraudulent deception of Enid Mercer all those years back.

After my initial wariness, I began to feel more confident in public and in the shops as Carla. No one looked at me oddly or thought my rather husky voice odd. We went into quite a few ladies' clothes shops and, if I'm honest, I quite enjoyed holding the dresses and skirts up against me for us both to see if they suited me. I tried a few on in changing rooms and ended up buying quite a lot of stuff. Needless to say, I had to buy some bras and (although I blush when thinking about it), a couple of rather sexy basques.

During our shopping, we paused to have lunch in the cafeteria of one of the department stores we visited. After getting our food and drink, I noticed one or two men staring at me after I removed my jacket and placed it over the back of my chair. I was concerned that they'd sussed-out I wasn't really a woman, but Ruth assured me that the only reason they were staring was because my prominent nipples were evident under my blouse.

"You see now what we ladies have to put up with Carla.? Dirty men always trying to look down your cleavage or up your skirt."

"Pathetic aren't they," I agreed (not having to add "ma'am" as we were in public).

After we'd finished our food, Ruth pulled out a glossy folder from the large bag she'd brought with her.

"Here Carla, have a look at this, it's Mrs Johnson's final report on your training."

My look of surprise at being allowed to read this prompted Ruth to elaborate.

"You may as well read it. I've always been open and honest with you and I won't change now, even though you're not the straight man I thought I married."

The front of the folder was labelled "Mrs Ruth Gifford - Private & Confidential", and on Page 1 - "Carla Gifford. Sissy No.134".

Most of the following pages rather reminded me of a school report with marks given out of ten for such things as "make-up skills", "voice training", "housework skills", "dress sense" "hairdressing skills" and suchlike. I was pleased to see high marks for all of these categories. Ruth hurried me along to the last few pages where Mrs Johnson had given her conclusions and recommendations.

"Carla has the makings of an attractive and convincing woman. She should be encouraged to mix in public to gain confidence in her new female persona. I understand you require her to earn money to repay a debt and working outside of her domestic, sissy duties, perhaps part-time in an office environment, should help add to the commission you are earning from her internet-site subscribers whilst simultaneously building her womanly confidence.

Carla has shown a reluctance to accept her deep seated, true feminine nature and her sexual attraction to submissive situations. However, she did, eventually, masturbate with some enthusiasm to scenes of ladies such as her being used and penetrated, both in chastity and uncaged. I enclose a DVD of just such scenes and would encourage you to allow Carla to continue to masturbate whilst watching this DVD in the hope she will come to accept her innermost sexual desires.

Carla has a rather narcissistic streak and believes - not without justification - that whether dressed as a male or female, others find her attractive, yet she suffers from cognitive-dissonance in refusing to accept her femininity and submissive nature.

You state you enjoy your control over her male sexual desires and wish to continue down that route as a means of dominating her. I would therefore strongly recommend Carla has her breasts enlarged (special discount available from Mrs Johnson approved surgeon - see brochure), so that her oestrogen intake can be reduced; this would help maintain her capacity and desire to achieve an erection and ejaculate - and thus your control over her - without risking her losing her feminine shape or growing body hair.

Many thanks for referring Carla to me. I hope I have helped her accept her new role by showing her how convincing a female she really is and to have the confidence to exist as such. If I can be of any further help, please do not hesitate to contact me." Signed Mrs Johnson.

It was quite a lot to take in; I had to read some of it over again to make sure I understood what had been said.

"But I don't want plastic surgery on my breasts; I don't want breast enlargement and, besides, we've just spent quite a bit of cash today on bras and..."

"Whoa, hold on a minute," Ruth interrupted. "It's entirely up to you, I'm not going to make you have them enlarged. What kind of a wife do you think I am?"

I calmed down a little.

"But you'll have to keep on with the same dose of female hormones to keep them the size they are and to avoid growing facial hair and having to shave. That may, over time - as Mrs Johnson alluded to - mean your ability to get an erection diminishes; maybe it won't though. Like I said, it's entirely up to you."

I calmed down a little and took a sip of tea, trying not to leave a lipstick smear on the rim of the cup. What else had I read that required enlargement? Oh yes...

"And I absolutely refute that I have cognitive-dissonance."

I looked again at the summary to remind myself of other issues I had with Mrs Johnson.

"The, you know, bit about me..." I looked around to make sure no one was eavesdropping, "jerking-off to sissy porn. I only did that because I, like, you know - needed release. I was pent-up. I'd have jerked off to film of the inside of an empty cardboard box. It wasn't because it turned me on or anything."

"No," Ruth chuckled in amused disbelief, "of course it wasn't. After all, you're clearly an alpha-male aren't you?"

I blushed at her put-down. Although I couldn't think of a retort to her barb, deep-down, I knew there was a residue of manliness in me; that in the right circumstances, I was as masculine as any of my peers and it was just because of one, simple mistake to have tried on my sister-in-law's underwear that I found myself in the position I now was.

"And Mrs Johnson's recommendation that I find work outside of my role at home?" I asked.

"What about it?"

"Well, you're not going to follow her up on that are you? I mean..."

Again, Ruth cut me off.

"Look lady, you've got to earn a lot of money to make good what you stole. You can't use what's in your business account, that's needed to meet your loan repayments, so you need to work to earn it. Get that through that pretty little head of yours. I've got you a job, you start on Monday and I don't want any arguing from you or I'll put you over my knee and spank you, understand?"

I nodded and blushed and squirmed uneasily in my seat, the crotch of my panties now nestling too tightly between the cheeks of my soft, peachy bum. I'd have to go to the ladies soon (another thing I was having to get used to) and ease the fabric out a little.

The thought of going to work as Carla, in an office full of other people was quite daunting. Ruth could sense it frightened me.

"Look Carla, you won't get exposed as a man; Mrs Johnson's right, you'll easily pass as a woman, no one will question you about that, why, even your Adam's Apple is unusually small for someone born a male."

"So, where's this job you've found me then?" I asked in a rather sulky tone.

"It's at the local college, where Geri works. She helped me get it for you. Secretarial work for three days a week to begin with. It's only temporary though, six months at most, but it will help you get used to being, well, you, Carla - a woman. And I'll take a percentage of your earnings to add to the money we'll give to charity. The rest of the week you can resume domestic duties and assist mother on the project if she needs it."

"But it'll take years to accumulate, what was it? £140k. That's not fair."

Ruth shook her head at my grumble. "You should have thought about that when you contrived to steal that poor woman's money. Anyway, I'm not going to argue. Do as I say or I won't let you "relieve" yourself - I was thinking of once a week, Friday evenings perhaps, watching your new DVD of course. I might just make love to you every now and again if you behave yourself. Got it?"

Gratefully, I nodded. Once again, the thought of making love to her had put all my inclinations to stand up for myself on the back-burner. The threat to spank me if I was disobedient or reduce my opportunities to wank was bad enough, as was the knowledge that she could easily send pictures of me to my brother if I really got stroppy was sufficient to restrain me, but the chance to make love to her, even if only occasionally, if I behaved and did as I was told, somehow made my obedience worthwhile.

Over the next few weeks, I suppose I could say that things became "normal"; that I'd got into a routine of being Carla the secretary for three days a week and Carla the obedient sissy for the other days.

Ruth had told Marsha at her workplace that I was now working full time with Donna. In reality, Donna seldom had to ask for my assistance. I'd spoken to Max a few times on the phone, remembering to try and sound a little less feminine when doing so. He was becoming more housebound and Donna reckoned that when and if I next met him in person, his eyesight would have deteriorated to such an extent that he wouldn't know if I was wearing a bikini or a deep-sea diving suit.

Geri had been most helpful in getting me settled-in at the college and introducing me to the other girls in the office., and never asked me to refer to her as auntie. I think she rather fancied me but the feeling was not reciprocated. It still seemed strange walking past the gents toilet to go to use the ladies, but eventually I just accepted that this was how it was. The work was pretty straightforward and a lot of the time was spent gossiping about nothing in particular and filing my nails. The pay was not exactly generous but, after Ruth's deductions to pay for my fraud, I was left with enough to buy the odd nice item of clothing or make-up.

One interesting fact came to light during my time at the college. Although it hadn't been confirmed or publicised, I found out that the University nearest to where our project was sited had plans to expand and were going to build new lecture-theatres and laboratories very near our development. This was great news as it made it much more likely that we'd find buyers and renters for the residential and commercial properties we were building. The news came as no surprise to Donna, Max it seems had sussed out the likelihood of this happening long ago.

Each Friday evening, Ruth allowed me to take off my chastity device and "relieve" myself. She would make sure I always did this whilst watching the DVD Mrs Johnson supplied. Did this kind of porn turn me on I hear you ask? Well, alright, I admit it did - sometimes; just a little. Deep down though I knew I was a real male as, even though Ruth had yet to let me have sex with her, the knowledge that she would at some unspecified time in the future, turned me on more than the DVD.

With just a month or so of my college contract left, Ruth surprised me one morning by saying that we could make love at the end of the week. It was her way of rewarding me for sticking with the job and doing as I was told. I was of course jubilant at the thought; all my trials and tribulations of hiding my masculinity and behaving as a woman were to be rewarded. I did wonder though if there wasn't some other reason why Ruth, at this particular time had decided to reward me, she was a somewhat calculating madam.

The sex was such a great relief, I felt a real man again. I'll spare you all the intimate details, except to say that, once again, Ruth took the dominant role and I wore my sexiest lingerie as well. I made sure Ruth enjoyed the experience and the restraint I'd now become used to certainly helped me push her to a climax before I came too.

There was though, one downside. I'd expected to be able to come at least three times so lustful and full of pent-up spunk was I, yet, I couldn't really get hard enough for even a second mounting. Ruth kindly let me try and jerk-off before I was caged again; I felt dreadful about having to do this, lying on the bed in my panties and stockings, especially as I wanted to prove Mrs Johnson's assessment of me totally wrong.

"Maybe it is the current dose of hormones that you're taking that make you limp after one shot," Ruth suggested. "Have you noticed any facial hair growing again?"

I hadn't but quickly ran my hand over my chin and cheeks to make sure.

"It's probably just me being over-anxious, you know," I suggested. I'm not sure that Ruth, or me come to that, really believed that though.

The next morning, I'd dressed in my usual underwear and plain cotton dress plus bell-ringing choker and ankle chain, and prepared Ruth's breakfast. After her granting me sex with her the night before, I'd decided to take her breakfast up to her in bed, and, putting my best frilly pinafore on, hoped my efforts would meet with her approval.

She sat up in bed to greet me and ushered me to sit alongside her as she took the tray from me.

"Look Carla, I've got some news for you. Next week will be your last at the college; I've told Geri. I've got you a new job from the following week."

Somehow, I guessed I wouldn't be too enamoured by what I was about to hear and wondered if last night's sex wasn't just to make me more accepting of the news.

"Your friend, Bowser, Henry whatsisname..."

"Hutchinson ma'am," I reminded her.

"Yes, Henry Hutchinson. Well, his secretary Joyce retires next week and guess who is going to replace her?"

My stony silence prompted Ruth to carry on.

"Why you silly. Isn't that wonderful?"

"Do you mean ma'am that I'm to revert to men's clothes again and to work for him as Carl and not Carla?"

"Well, no. You'll still be Carla. I spoke to him a fortnight or so ago and told him that as part of your punishment you'd be transformed into Carla and that he was to make sure you were given Joyce's job or else. He was stunned at first, but I showed him a recent photo of you and told him no one at his firm would ever suspect you of - well, I won't say being a "man" - of having a penis, and that you'd blended in without a problem as Carla at the college."

"And what did he say ma'am?"

"Oh, he made some nasty remark apart poor Carl, crossing swords with the Gifford women and that we had "form" in that department, but he's taking you on as his secretary and you'll both enjoy it; Monday to Thursday, nine 'til five. The hourly rate is higher too, so you'll be earning a little more which will help to repay your debt now won't it."

This was dreadful news; devastating. I dreaded the thought of turning up for work at Bowser's workplace and even though it might mean my debt was repaid sooner than if I'd remained at the college, it was an appalling thought that Bowser knew of my predicament.

"Look, Carla, let me finish breakfast and when I've changed, I'll come down and show you something else that might lift your spirits a little."

This turned out to be a spreadsheet on Ruth's laptop that showed how much money I'd banked so far towards my £140k debt. It was over £60k, mainly due to internet subscribers to the website featuring my "journey" plus a few thousand from my earnings at the college. Ruth was also confident that sometime in the next twelve months, we'd start earning income from our development as rental from the first of the retail premises came onstream and the completed houses were sold. My share of the profits would, at first, go towards my fraud debt.

I noticed a few deductions on the spreadsheet though, most for quite small sums but one of over £6,000. Ruth explained this was for my training with Mrs. Johnson.

"And when it's all paid off ma'am, what then?"

"Well Carla, I've given some thought to that. If you want, if it's what you truly want - and providing Donna and Esther agree that it can be done in a way that won't jeopardise the success of our business - you can leave me."

I looked at her in shock and amazement.

"I hope that's not what you decide of course; you clearly belong in a subservient, female role, you can't deny that, and you might as well be that submissive with someone you love. And I deserve to have an attentive sissy and enjoy it enormously. Also, remain with me and I'd still let you have occasional sex with me, assuming you were still able to get an erection."

"So, I can leave and return to being Carl you're saying ma'am? Without my chastity-cage?"

"If that's what you really want. If you want to go back to wearing underpants and trousers and socks and ties, yes. You'd only have to contact me and the family over business matters, otherwise you'd be independent. You could of course leave and still live as a woman if you wanted."

"And ma'am, you wouldn't threaten to expose my cross-dressing to my brother or anyone else?"

"No Carla., not under any circumstances that I can foresee. I reckon you'd have served your punishment. In fact, had we not found out about your crime against Enid Mercer, you could have been making this decision now. Now, put that news behind you, it'll be a while before you've raised the extra, what, eighty thousand. Until then you remain Carla; my Carla. Understand?"

This news placed me in something of a dilemma. Deep down, I still knew I was a man yet I couldn't deny the thrill of dressing as an attractive, sexy woman. The thought of wearing socks and underpants again did not compare with that of silky, frilly panties and stockings. I also took a fair amount of pride in just how good-looking I was as Carla, how attractive my long, sexy legs looked in stockings and how nicely my panties sat on my cute bum.