Made to Obey Ch. 10

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. Humiliation was now a frequent event. Esther, who had investigated my internet usage on my laptop to see if I'd visited shemale porn (or similar sites) before, had found no evidence of that. Yet she did want to know about "Bowser" and a curious email I'd sent to him some years back. Donna was looking in to my finances prior to my marrying Ruth.

Of course, being allowed to have sex again with my wife was something I should have been delighted about; don't get me wrong, I did enjoy it, very much so. But the knowledge that on both occasions I'd been "ridden" by Ruth, that she took the dominant role was something that, the more I thought about it, upset me.

Over the next few days after my birthday, I wondered why, even though I found Ruth looking so sexy in her underwear, I couldn't get stiff enough to penetrate her. It wasn't as though I had some kind of erectile dysfunction, I could get firm but it seemed I now needed to be wearing lingerie in order to achieve the level of stiffness needed. This, more than wearing panties and a chastity cage, depressed me most. Why had my masculinity so diminished?

I concluded it was because I was being made to spend so much time in ladies' underwear; that if I was allowed to dress like a man, a proper man, a few days before we next had sex, I wouldn't have the need to wear panties and stockings in order to become sufficiently erect. This seemed a reasonable diagnosis, so I decided to make this point to Ruth when the right opportunity came along.

My workload at the office had increased somewhat over the next few weeks. Documents and costings from numerous businesses and officials regarding Max's new big project (well, our big project really, seeing as how me and Ruth were partners in it) were being addressed to me to handle and this, plus the dregs of my own property business, never allowed me to have the quiet word with Ruth about my "erection" issue. She too was nearly always working with Miss Penny, making opportunities to bring the subject up non-existent.

At home, always being dressed in women's clothes and underwear, meant I didn't feel able to plead my case to be allowed to be the man I really was prior to sex. Ruth had given me no hint as to when she'd next allow me to be fucked by her, but she'd not said it wasn't going to happen again and, in a way, not knowing when I might next be unlocked by her to perform was somehow erotic. Even so, I needed to let her know that I must be given some time to be dressed as a man before we next had sex; that I would then be able to satisfy her in a manly way that befitted my true masculine nature.

Eventually, as good an opportunity presented itself as I could expect. Driving to work one morning, Ruth informed me that Penny was on holiday that week and so she'd be based in the office for most of the days ahead. I couldn't really bring it up right away, I had to concentrate on my driving, and anyway, I wanted to rehearse in my mind just how I was going to broach the matter. Unlike at home, at work I was dressed as a man, a quite handsome and fit man I feel I ought to point out again. True enough, I was wearing a chastity cage and, this day, pink cotton briefs with a red bow and lace trim, but I could still present myself to Ruth looking, ostensibly, like one fit hunk.

I did a bit of work for a couple of hours, mulling over just what I would say to Ruth as I did, until I decided to man-up and grasp the nettle; to be decisive. Marsha gave me an odd look as she saw me knock on Ruth's office door and wait for permission to enter but I didn't let that unnerve me. Ruth, as convention demanded in Marsha's earshot, said "Hi, come in Carl." I shut the door behind me so that Marsha couldn't hear what was said.

"Sit down Carla, you look a little on edge. What did you want to see me about?"

"Thank you, ma'am." I took my seat and shuffled uneasily, trying to recall the words I'd decided to start with but hopelessly forgetting.

"Er, it's like this Ruth, er ma'am. You know the last time we -- on my birthday, you know when I couldn't..." I was about to continue but Ruth tried to help me out.

"Get a hard-on?" she suggested. I nodded.

"Yes, you know. Not at first, not until you, I, er, you know..."

Again, Ruth interjected. "Until you got to wear lingerie? Yes. I remember. What about it?" Her tone was one of understanding, although I well knew that it could change rapidly if I wasn't careful.

"Well ma'am, it's just that I think that, maybe, perhaps, if I hadn't been made to dress up so much before then, that it might not have been a problem, you know, getting a hard-on without having to wear, you know -- stuff."

She smiled and her eyes showed a look of both amusement and sympathy. "So what are you proposing Carla?"

"Well ma'am, maybe if before the next time we, that is you, decide I can have sex with you, I'm allowed to dress fully as man for a week or so, then maybe I might not need to er, you know like, dress up and I could maybe, if ma'am agreed, go on top, perhaps."

She laughed, not an outright mocking laugh, more one of amusement; amusement that what to her was a trivial issue had seemingly been playing on my mind to such an extent that I could hardly ask her about it.

"But when we had sex downstairs before your birthday; when I was watching Penny's video of you with her and Geri, you enjoyed our sex then didn't you? You didn't ask to go on top or take your dress and knickers off before we went any further did you?"

"Well no, that was great and yes..." I was fumbling for an answer but Ruth cut me off.

"So you've got nothing really to complain about. Besides, I think we've established now what you are; what turns you on. Don't try and kid yourself you're something you're not. Have you ever thought that maybe, you've got some sort of 'cognitive dissonance' regarding your sexuality? If we have sex in the future, and I might let you every now and again, you might surprise us both and get sufficiently aroused without the need to wear anything but don't fight it. Besides I've spent quite a bit on getting you some lovely things to wear, I don't want all that to be wasted, you make a lovely sissy Carla, take a pride in it. Now, no more silly suggestions, go and get me and Marsha a drink and we'll talk no more about it, run along. "

"Yes ma'am. Thank you, ma'am."

Crestfallen, I turned to leave and make the drinks.

These thoughts about my -- dare I call it - "impotence" unless clad in lingerie had pre-occupied me and, in the absence of any word from Esther or Donna on the Bowser Gmail, I'd largely forgotten about that issue. Until that is, that afternoon after my talk with Ruth. Donna had called Ruth and asked her to get me to join them in a video conversation. Ruth called me in to her office and I shut the door behind me to sit next to Ruth as we both looked at Donna on the computer.

"Ah, Carla, good. There you are. I've just got a couple of questions I want you to answer, about your old bank statements. I haven't had time to go through them all yet though."

I gulped, clearly of those she'd studied, she wasn't entirely happy. I hoped they'd be minor issues that I could just pretend to have forgotten about over the years.

"First off, in May, the year after you got divorced, you paid in exactly £9,228 in cash into your bank account. Where did that money come from?"

I let out a silent sigh of relief. Bowser had given me an alibi for just this matter.

"Oh, let me see now, "£9k+ was it?"

Donna nodded.

"In May you say. Oh, I remember that. I won that at the races. I went as a guest of somebody, some local business. I'm sure any number of the other guests can vouch for it. I did get rather drunk and celebrated my win quite loudly I recall."

I felt confident that that should put an end to any further doubts about the provenance of this money. But I was wrong, Donna hadn't finished.

"So, you won exactly £9,228, did you? What was the name of the horse? What price was it? How much did you have on it? What racecourse was it at?"

"Hold on, hold on, it was all some time ago and, like I said, I did get rather drunk." I didn't have prepared answers for these questions, the only real answer I could give was about the racetrack I was at, the rest I'd have to conjure up on the fly, so to speak.

"It was at York races; they have a big meeting there in May."

"Okay. Got that, York in May. Now, what about my other questions?"

"Er, let's see now," I started, trying to think of an answer which sounded plausible. All the time Ruth was watching me and, I think, hoping that I could come up with a believable answer.

"Well I must have won £10,000 and spent a few hundred before banking it. Maybe I bought a round of drinks at the track and spent a few pounds paying bills in the days after; I can't be sure. It was a few years ago now."

Donna came back at me. "So, what was the price of the horse? 9/1, 2/1, Evens? Surely you can remember that?"

This threw me a little, I wasn't really a horse racing fan and knew little about betting. I just tried to give a realistic answer in the hope that she would leave it at that.

"Er, I think it was 9/1. Yes, that's it 9/1."

"So Carla, you're telling me that you, who'd just gone through an expensive divorce and was just about scraping a living, managed to find £1,000 to bet on a horse because that's how much you'd have needed to have on it at 9/1 to get £10,000; £9,000 winnings plus your stake back. "

Damn this woman I thought. Sure, she was one well stacked, glamorous even, older woman but damn, she wasn't half making my life awkward. I was just a little pleased that her screen image didn't give me a sight of her cleavage, that might have got me even more unsettled than I already was.

"Well, I guess I must have been winning from various bets in other races and, being a bit drunk, foolishly placed a big bet on this horse at 9/1 with my earlier winnings. Yes, now I think about it, that's what happened. I was probably trying to impress some of the other guests that I was, you know, a big punter."

Wow, I thought. Where did that come from and under so much pressure? I could almost sense Donna's deflation at my giving such a credible answer.

"So, Carla, this horse that did you such a big favour, won you so much money. What was it called?"

"Mmm. Let me think now," I scratched my chin a bit to give me time and to look as though I genuinely might have a chance of remembering a name.

"No. Sorry. It's gone. I know I was drunk though and, to be honest I'm not sure if I didn't just back the horse by race card number rather than name."

Donna raised her eyebrows, defeated. She knew she'd not caught me out on this one.

"Okay then. From the June of your year of divorce and over the next year or so, you made nearly 125 deposits of less than a thousand pounds but all over £500. Where did this money come from?"

"Well Donna, I guess it must have been cash-in-hand payments, you know, for various work I'd been doing. I'd got quite handy at DIY by then and knew plenty of tradesmen who needed a hand and preferred paying their helpers off the books."

"But Carla, all above £500? That's what's so odd. That's what made me think of Bemford's Law, remember? And anyway, if you were only helping people out, they were paying you much too much if the smallest payment was, let me see, £513. Tradesmen themselves, skilled tradesmen, wouldn't have earned that in a week in those days, and I know about such things as Max and I use building tradesmen too."

Ruth shot me a glance suggesting her mother had clearly caught me out.

To my credit, considering this was not a question I had a clue was coming, I thought I batted it away rather well.

"Okay Donna, look, the money wasn't all for me. A number of other guys working for cash in hand, you know, immigrants, people in temporary accommodation who couldn't get bank accounts, they asked me to bank their wages for them. It's really that simple. Okay, the Inland Revenue might have frowned upon it, but it hardly makes me Al Capone. Besides, I was helping out these guys; it was more an act of kindness than an act of fraud."

That, I thought, was game, set and match to me. Bowser would have been proud of how I had handled myself with so little preparation; in his cricketing terminology, I'd hit Donna for six.

"Is that so Saint Carla?" Donna retorted in a tone that suggested she still had another ball to deliver.

"Tell me this then, how come all these cash deposits, when added up, come to an exact figure that ends in three zeroes?"

I looked baffled, I knew what she was getting at; why she was asking this question, but was stumped for a logical explanation that I could give. The best I could do was shrug my shoulders and say that I didn't know why this should be so; perhaps it was just a coincidence.

"Just a coincidence!" Donna mocked. "Well Ruth, I've finished with Carla. Perhaps we could have a word in private now."

Ruth nodded for me to leave the room and I got up to leave but Ruth called me back.

"Aren't you forgetting your manners Carla?"

"Sorry ma'am. Thank you, ma'am."

Ruth smiled and waved me away, I could hear Donna in the background sniggering at my servility and discomfort.

What the two of them discussed, I don't know, but Ruth never raised the subject of the bets again or my numerous bank deposits all adding up to a nice, round number. I guess she found Bemford's Law as boring as most people would and didn't understand the significance of Donna's point.

Days turned into weeks and, with no further word on the subject from Donna (although I had 'phone and internet communication with her), I allowed myself to conclude that she'd been unable to find any reason to suggest I'd been up to no good. One day, I managed to sneak into Bowser's office and left a note with the receptionist for him to meet me at around 1p.m. at a nearby café. He managed to turn up and I mentioned Donna's series of questions to me and how I'd managed to stifle any further suspicions (or so I thought).

"Good fellow, good fellow. You batted away a couple of tricky questions there. I told you though that she was nobody's fool that Donna; Bemford's Law eh? Never heard of it. Look, from now on, just play everything with a straight bat (a cricketing term meaning to be ultra-defensive; play it simple, give as little away as possible). Just say you don't remember or were drunk and, for heaven's sake -- although I know I don't need to tell you this -- my name must be kept out of this at all costs."

On the sex front, I'd had no relief since my birthday and was now beginning to think I might just, accidentally, ejaculate -- a nocturnal emission perhaps, like some teenager who'd just reached puberty.

Ruth had insisted that, most nights and weekends I practised applying lipstick and make-up and, at the weekend, always painted my nails and toes. At home, I also wore the ankle-chain with bells and one of the chokers with bells that Esther had bought for me. Of course, my attempts to suggest all this was unnecessary (she did, after all, have me totally under her control), was easily batted away by her. "You want sex with me again don't you?" she'd ask, which of course I did. She then made it clear that my total compliance to all her demands was necessary or else further sex with her was out of the question. But I was so pent up now, most days my dick oozed a little pre-come and it was very hard indeed not to think about how I might get relief. I knew Ruth had now hidden the key(s) to my chastity device in places I wouldn't stand a chance of locating, so that path was a non-starter. I concluded that the only recourse I had to relief, was, when next at home on my own for any length, to root out one of Ruth's dildos and ride that! That's how desperate I was becoming.

It was a Tuesday at the end of another frustrating day at work, that things changed. Ruth seemed in a particularly cheerful mood that afternoon and, on our journey home, informed me that she'd received a call from Maggy, an American businesswoman she'd met when down in Birmingham recently with Penny. Maggy had invited her down to a hotel in London this coming weekend.

"She's a really beautiful, smart woman Carla. We took to one another within minutes of chatting. It's been a little while now since I've had a fling with another woman so I think I deserve my fling, don't you?"

"Yes, ma'am," I replied, not too convincingly.

Ruth laughed at my churlish, jealous response.

"Look Carla, you used to love hearing me tell you about what I'd got up to on my lesbian flings didn't you? So, when I get back, we can have sex and I'll tell you what me and Maggy got up to; it might help you get hard without having to dress-up."

Although not too happy at being reminded about my inability to "rise to the occasion" recently, the prospect of having sex again, of draining all the spunk that was stored up in my balls, was enough to bring a smile to my face and to change my demeanour to one of the happiest man in the world.

"I've booked the train tickets and am leaving early on Friday afternoon, returning Monday evening. I'm so excited. Maggy's husband has, well, how can I put it? - "disappointed" her. When I told her, what had happened to you and how I'd handled it, she just couldn't wait to hear more. Your ears sure are going to be burning this weekend!"

I should have been annoyed that she'd told a complete stranger about my situation and, in all probability, shown her pictures of me in panties but, I was so delighted at the thought of sexual release, I didn't really mind too much. I could feel my dick straining once again against the cage, a slight moisture oozing out on to the fabric of the yellow lacy panties I was wearing that day.

"It's a bit unfortunate though," Ruth went on, "but it's this weekend that I'd arranged for Esther and mum to come round and stop at ours , just for us to have a girly weekend and for them to let me know what, if anything, they'd concluded from searching into your past behaviour."

"Can't you cancel it ma'am?" I asked, now a little rattled at the thought of being cross-examined again on a subject I'd hoped had been dropped, bearing in mind the time that had elapsed since they'd first heard about the Bowser Gmail.

"Well, ordinarily I would, but mum's booked dad into a luxury private health care place for a few days and she can't cancel that. He's looking forward to it and mum will be glad of the break. She's really looking forward to seeing Esther again too and they can kill two birds with one stone; they can get together again -- albeit without me -- and they can put an end to all this -- what's his name again stuff?"

"Bowser ma'am."

"Yes, Bowser, that's right. Esther says she's not quite finished her searches but both she and mum said I must go and see Maggy. So that's it. I've booked my tickets, mum and Esther are going to be your guests over the weekend and you're going to do exactly as I say, understand? Otherwise, you can forget about me letting you anywhere near me for sex, got that?"

"Yes ma'am. I understand, I'll obey your instructions." (Why wouldn't I? I desperately wanted to fill Ruth's sumptuous pussy with my dick; her mum and sister knew all about my cross-dressing lifestyle so it wasn't as though I'd be facing humiliation afresh with a stranger.)

And, (and this was the bonus), it sounded from what Ruth had said as though Donna and Esther's investigations into me were kind of "winding down".

"Now Carla, while I remember, you must now refer to them as Miss Donna and Miss Esther when in their company or ma'am, when it's clear who you're addressing. I've agreed this with them and they'll tell me if you don't comply, understand?"