Made to Obey Ch. 13

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LAST CHAPTER. Out of the frying pan?
10.1k words
4.57
17.7k
16

Part 13 of the 13 part series

Updated 06/09/2023
Created 06/14/2019
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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 start wearing 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, Esther and Donna My gain from my past fraud had to be repaid to Ruth (who'd give it to charity), only then would she consider releasing me from my submissive life – if I actually wanted to be freed. Meanwhile, forced to work as a secretary at a firm of solicitors, I'd fallen in love with my new boss – Pamela - and told her all (well, nearly all) about my real self and my being forced into femininity because of my crossdressing misadventure. To my surprise, my affection was reciprocated.

At first, when we awoke on the Saturday morning, I was afraid Pam would regret our previous night's lustful activities. Seeing me with my make-up and lipstick smudged, my hair dishevelled and my dick encased in the cage with the small pink padlock, might make her feel repulsed that she'd ever contemplated taking things with me further. But on waking and seeing my anxious look, she reached out a hand and placed it on my shoulder.

"Last night was good Carla. You're so much better at foreplay than Keith, he just wanted to fuck, he never thought about bringing things to the boil slowly. If I can ever get you out of that cage-thing of yours, our sex could be amazing don't you reckon?"

A big smile lit up my face on hearing this.

"Thanks Pam. I was really worried in case, you know, you wished we hadn't gone so far; that maybe you only did so because we'd both had a bit to drink."

"Don't be daft. Besides, I didn't have that much did I?"

She sat up in bed, her breasts now daring me to suck them again; my nipples too were proud and aroused. They'd needed a good sucking and fingering and Pam ensured they got it - in fact they were still a little sore. My tongue too felt like it had been in a marathon, I wasn't sure I could perform quite as well as I did the night before. So rather than go at it again and - conscious of the fact that Ruth might ring me at any time and ask for a quick talk - I decided to get dressed.

"I'd better get changed and get a bus back to town. I need to get home in case, you know, Ruth wants to check up on me. Did I tell you how she does that?"

"Yes. No worries. I'll get changed too, we can share a taxi to work and pick up our cars together. Hey, if Ruth's away for the weekend, why don't I follow you home and you can cook me breakfast? You said you'd like to cook for me didn't you."

I slid my long legs out of her bed and looked around for my pink panties whilst deciding whether Pam's suggestion was viable. As I slid them up my legs, I could see her admiring my girlish frame, my petite breasts and trim waist. It would seem a shame to pass up the opportunity to indulge myself and show that I was still a man, capable of making my own decisions in my own home.

"Yes, great idea," I said as I fastened my bra. "Just let's have a quick wash and tidy up a bit and then the day is ours."

It felt good to be acting more like a man again. I'd laddered my tights somehow so left them there, then waited for her to change. She dressed in a tight pair of blue jeans and a crisp white blouse. She hardly needed any make-up to look her usual attractive self, I on the other hand, lacking her confidence, asked to borrow some of her mascara and lipstick. We then took a taxi into town to pick up our cars and then Pam followed me as I drove home.

Once indoors, I became more Carla the submissive creature of my familiar environment than the new Carla of the previous evening. I feared Ruth calling me now and asking why my make-up was so shoddy, why wasn't I wearing stockings? In a panic, I asked Pam to take a seat and give me 10 minutes just to get ready in case my demanding wife rang. She agreed of course, aware of the hold that Ruth had on me from our recent conversation. She took a seat in the living-room and, to my horror, I noticed that the glossy folder Mrs Johnson had prepared on me was lying on the coffee table there. I hastily went over to retrieve the folder and to hide it from her; I didn't want her reading such stuff, especially nonsense like my being a narcissist!

It was a good call to redo my make-up and get changed. Ruth rang just as I was leaving my bedroom, now looking my glamorous self and suitably dressed in short dress, white hold-up stockings and cheeky white lacy cotton briefs. I just had time to fix my choker and anklet on.

I'm sure Pamela could hear my talking to my wife; heard my apologetic and submissive tone, I just hoped this didn't diminish me in her eyes.

When the call was over, I entered the kitchen, choker and anklet bells announcing my approach, and started on our breakfast. Pam came out to see me and put her hand playfully up my skirt and tugged teasingly on my briefs.

"Let's see if your cookery skills are as good as you say," she smiled. I smiled back at her.

"They're almost as good as my foreplay skills," I boasted.

"Mmm. Yummy. I'm in for a feast then."

As I made sure my fried-bread, poached eggs, bacon, sausages, fried tomatoes and mushrooms were cooked to an exacting standard, I couldn't believe my luck. Here was a woman – an attractive woman at that – who wanted the best bits of Carla and the best bit of Carl!

I certainly deserved a change of luck after all I'd been through but this was better than I could have dreamed of. Only two thoughts kept my happiness under control. One, how long would it be before I'd raised all the money I needed to allow me to leave Ruth and two, could I satisfy Pamela's sexual desires when uncaged – as a man? It seemed the answer to the latter problem was the counter-intuitive one of having my breasts enlarged!

Pam really enjoyed her breakfast and, after we'd eaten, I showed her around the house and the gardens. She told me to keep my bell-ringing accoutrements on, saying they both made me even more divinely feminine, which is what she wanted if she was to have another 'woman' in her life.

When we climbed the stairs to check out the bedrooms and the bathrooms, I went ahead, knowing Pam could see up my skirt and see my panties hugging my beautiful cheeks. This time, the sound of the bells ringing actually excited me rather than annoyed me. I let her look through my wardrobe and cupboards.

"Wow, how many panties do you own? You must have a whole shop's worth here," she exclaimed, pulling out the more luxurious and frilly ones and stretching the out between her hands and holding them up to me.

"Here, try this on and attach it to some sexier stockings, now," she demanded as she pulled out a recently purchased black basque. Needless to say, I was only too happy to oblige, the fully-fashioned seamed stockings I sought out and attached to the basque straps were made for legs as well-turned as mine. I could hear Pam breathing quicker than before and see her eyes widening slightly and unconsciously licking her lips as she watched my long legs now adorned in the silky hosiery. Once done, I turned to her full on and stretched my arms up in the air and swivelled my hips.

"Does madame approve?" I asked.

"She sure does."

We had a most enjoyable day caressing and fondling. I concentrated more than ever on ensuring my foreplay satisfied Pam's demands and my tongue worked harder than it had ever had to do before, even when going down on Auntie Geraldine and Miss Penny that time.

To top things off, Pam asked if there was a dildo in the house. I blushed and showed her where they were kept. She eagerly went over to the cupboard and then ordered me to kneel down on all fours and, after applying some lubrication to my anus, pleasured me to ejaculation with it. Of course, my cage meant it wasn't how I'd want to shoot my load, but it was a relief of sorts and for that, I was grateful.

The next few days involved much the same kind of mutual pleasure, but once Ruth returned, I would have to face and overcome the barriers to my becoming Pam's lover. I never mentioned a word to Ruth about Pam, there'd be time enough for that later. Ruth had had a lovely time with Maggy and I told her that my time without her had been boring. She'd bought me a red-tartan kilt as a present which, when I tried it on did look rather fetching although I wasn't sure what knickers I should wear under it.

Pam and I shared our frustration at the lack of opportunities for us to get together again in private but she understood how things were with me and Ruth. Sure, we sneaked a few kisses and fondles at work when no one else was around and I was still in a bit of a daze at how one so good-looking as Pam could want me and, be prepared to wait to have me.

It was some weeks after Ruth's return before she allowed me to be "ridden" by her. True to form, after I came from my first stiffy, I wasn't able to quite rise to the occasion again. This was not altogether something I minded as it would give me the perfect reason to suggest to Ruth that, perhaps I needed to have my breasts enlarged in order to reduce my female-hormone intake and thus improve my virility.

Ruth looked absolutely delighted when I asked about having the boob job. It was as though this meant I'd concluded that staying with her as her sub for ever was my intention. She sent a few emails back and forth and, a few hours later told me that Mrs Johnson had arranged for me to go for surgery with her approved plastic-surgeon in London three weeks later. The only downside Ruth informed me was that, even though I was getting a huge discount as a Mrs Johnson trained-sissy, the cost of the surgery - £5,000 – would have to be taken from my "fraud" fund. I agreed to this.

"How much do I have in the fund now ma'am?" I asked.

Ruth got her laptop out and went to the spreadsheet where she would find the figures.

"Just over £92,000. The subscription earnings from the sissy web-site have slowed down quite a lot recently Mrs Johnson says, but, after your boob job, she recommends you do another photo-shoot. That might even cover the cost of the surgery with new or renewed subscribers buying in."

When next in work, I booked two weeks holiday so that I could have my new boobs done. Pamela asked what I was doing in those weeks but I just told her to wait and see, and that I was doing it for her, to show her how much I loved her.

Ruth accompanied me down to London where the operation was to be performed. The surgeon never even asked me to show any letters from my GP approving my need for the implants, as a Mrs Johnson trained sissy, he accepted it was natural for me to want the operation.

Ruth and I had looked through a sort of catalogue of breasts and nipples before the operation and selected the size and shape we thought best. Not great swinging mammaries that apparently were very popular with Mrs Johnson sissies, but 36-inch B-cups. No change was required to my nipples, they both pointed slightly upwards – which I liked- and my cupola-like areolas were divine too.

The operation was carried out without my chastity cage being removed – the Surgeon knew all about such things on people like me he said. It was a complete success and, even though I was both drowsy to begin with and sore for a while afterwards, I was delighted with my new tits and was sure Pamela would be too. I had to carry on with the same dose of female hormones for a little while after but would soon be taking just enough to stop body hair growth. Whilst down in London, Ruth took me shopping to buy a whole new set of bras and basques and corsets to fit my new, fuller figure (the cost deductible from my fraud fund of course).

Although it was Pamela I wanted to fuck, I was still keen to see if my plan would result in my being able to successfully get more than one "rideable" erection when next allowed to have sex. In the meantime, I had my usual Friday evening wank to footage of sissies sucking and getting ridden by dicks. I reckoned the new, alpha-man with renewed dick that was me, was at least as pretty as some of those sissies I watched on screen.

I couldn't wait to get back to work and show Pamela my new, enhanced breasts, I was sure she'd approve. I wore a half-cup bra under my blouse that first day and had to go to some lengths to avoid giving some of the men who saw me an eyeful. I wore a cardigan when in company and it seemed to take ages before I was alone with my new would-be lover long enough to unbutton my blouse and thrust out my proud, inviting breasts.

"Wow, they're tremendous," she gasped, almost frightened to touch them; to suck on those gorgeous nipples in case the reality turned out to be all a dream. "And you did all this for me?"

"Yes love. I want you to want me, to ravish me as Carla as well as Carl, when I eventually get free of Ruth."

The photo-session with Mrs Johnson and Young Mistress Jasmine took place on a Saturday afternoon. Ruth had not let me wank for a fortnight and I was heavy-laden with spunk-filled balls. I'd been made to douche that morning (nothing unusual there). Norman picked me up and drove me to Mrs. Johnson's place.

At first, I had to undress and let the two women look at and feel my enlarged tits.

"Yes Carla, they're lovely. Our Surgeon did a good job," Mrs Johnson nodded as she lifted up each breast one by one and allowed Young Mistress Jasmine to inspect them too. Norman stared at me as they moved my breasts and nipples about in their fingers.

My cage was unlocked and the next hour or so involved my dressing up in various sexy panties, bras, stockings, suspenders and foundation garments. Sometimes my dick would be filmed stiff and poking through my panties, my boobs always in shot. I wanted desperately to jerk-off but Mrs Johnson made clear that would not be allowed.

When all the filming had been done, I was told to put a pair of pink cotton panties with white frills and bow and sit down. Mrs Johnson had a proposition to put to me.

"Look Carla, I gather you're having to work to get enough money to pay off some debt to your owner, is that right?

"Yes Mrs Johnson. That's right."

"Well, I've asked Ruth -Mrs Gifford, if I should put this proposition to you and she said it was fine, but it's entirely up to you. You don't have to agree, understand?"

"Yes Mrs Johnson, what is it?"

"Well, although this new breast-job shoot will get us a few more subscribers which will help you, you can earn a lot more - £15,000 is on offer if you agree to do one thing. We can do it today, in the next hour or so if you wish."

"But what is it I'd have to do Mrs Johnson?"

"You see Carla, this business, my business, is partly owned by a man who likes sissies like you. Ordinarily my clients like their sissies to submit to this man, to have them perform oral on him, maybe even get fucked by him, but Ruth, your owner, specifically asked that you didn't do this. This man has watched over you ever since you first came here and he's very taken by you and very frustrated that he hasn't had the pleasure of performing with you. So frustrated is he that he's willing to pay you £15,000 to lose your oral and anal virginity with him. Not only will you get £15k, but your takings from the increased subscribers that are sure to follow would increase too. How does that sound? That will help you pay off your debt that much sooner won't it."

The idea appalled me, I was now really, underneath the breasts and the panties, a man renewed, a man with a woman who wanted to be fucked by him. I didn't want cock!

Yet by agreeing to this offer, I'd be able to free myself from Ruth and the Giffords and be able to fuck Pamela like the alpha-male I really was so much sooner. I was still an anal virgin and, as far as anyone else knew, an oral virgin too. I could see why I was so appealing to a man who liked this kind of sex. I looked around at Norman, at his big muscular frame and strong powerful limbs. He seemed to be grinning in expectation, like a dog waiting to be given a juicy bone. He was nearly always present, watching over me whenever I was here, he'd clearly seen so much of me that he just had to have me.

I gulped; my throat dry. I wanted to say no, but then pound signs appeared in my head and the thought of screwing Pamela and freedom from Ruth came to the forefront of my thinking again. I'd survived my blow-job with the supermarket delivery driver without any adverse effect. Would it be the same if I now took anal?

My dick began to wriggle and push out the fabric of my frilly briefs. Was it trying to tell me something? I hadn't had a wank for a while now and maybe, if I closed my eyes and thought of England, I could get the deed done and forget all about it.

"Well Carla? It'll just be a one off, over within an hour or so. He's very experienced and will give you lots of lubrication. He's disease free too, I insist on him having regular checks. Think of the money."

I was about to shake my head and reject the offer but wavered. I was itching to screw Pamela. I wanted that to happen as soon as possible; the thought of my now (I hoped) re-invigorated dick pleasing her time and time again, of her rushing home from work to make love with me was just so exciting. I gave a reluctant nod of the head, half believing I'd made the wrong decision even as I did it.

"That's a good girl Carla. Now, follow Young Mistress Jasmine and she'll lead you to the room and we can get this over with. You really should be flattered; he's never had to pay for this before."

I was taken to a room with a large bed and cameras situated about it. A large mirrored ceiling meant I'd see everything that was going on. Well, I would have done if I hadn't been blindfolded after being dressed in the usual seamed hold-up stockings, high-heels, silky red panties and long, lacy gloves. A white silk ribbon with two small bells on was tied in a pretty bow around my neck by the Young Mistress.

I was told to lie face down on the bed, whereupon Young Mistress Jasmine attached my wrists to some leather straps.

"Now Carla, put your butt up in the air. Don't be afraid, it'll all be over soon and think of all the times you've wanked off here to sissies being screwed, you'll probably love it," she whispered to me.

I heard a door open and the footsteps of two people entering and approaching, me – Mrs Johnson and Norman I presumed. Mrs Johnson started to give instructions to Young Mistress Jasmine about lighting and angles and suchlike and then, to my horror, I heard and felt the movements of Norman mounting the bed and placing his hands on my lovely buttocks. I squeezed my eyes tight shut, even though they were blindfolded and prayed that what happened next didn't hurt too much (Norman was probably well-built in the dick department) and that it would all be over quickly. I had to endure it and take it like a man.

My panties were pulled down over my stocking tops and I felt hot breath on my bare cheeks and then the wet tip of a tongue seeking out and pushing in to my butt-hole. His hands rubbed over my bum and thighs and his tongue would leave my hole and lick along the length of my bum crease, before diving in again and taunting the nerve endings in my anus.

Young Miss Jasmine comforted me. "See, I told you it would be fine, it looks like you're enjoying it too. Now relax, you're in the hands of a master."

In spite of having no intentions of enjoying it, my dick was now fully extended and aroused, that this was so was very embarrassing to me.

After a long period of tonguing, my left leg was lifted and my panties pulled down over it, letting them fall down to my right knee. Next, I felt fingers smearing cold gel over my butt-hole, a finger pushing some of it an inch or two inside my virgin cavern. My heart was pounding in fear as, under orders from Mrs Johnson, I pushed my butt higher up in to the air and waited.