Made to Obey Ch. 07

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). Ruth, as a part of my punishment, was setting me tasks until Esther (who'd taken my laptop and mobile phone) could verify I'd never visited such sites before. I'd been forced into a chastity cage and made to wear panties all the time. She'd been advised by the partner (Geri) of her assistant at work (Penny) to let me have sex, to see if I was still a "man" and capable of heterosexual sex, or was I really becoming a sissy?

The door opened and at first, I couldn't see who'd opened it as Ruth blocked my view, then, as I moved forward, I said probably the worst thing it was possible to say in the circumstances.

"You've got to be bloody joking!"

Ruth turned around at me in anger and the look Geraldine gave me, in just a fraction of a second conveyed not just anger, or fury but contempt. In that one, six-word outburst, I'd confirmed to her - a "big" woman - all that she hated most in men. How most men thought they were above having sex with someone her size, how they'd be ashamed if all they could pull was a "porker", that their friends would look down on them if they knew.

"Put the bag down and go and sit in that chair at the far end of the room, in front of the bay window. Now," Geri ordered me.

I obeyed, sensing what I thought was going to be a great morning was now turning into a nightmare.

Things were to get worse though. As I walked from the short hall past Geri and into the large living room, Penny appeared. She too had a look of sneering contempt when our eyes met, as she made her way to meet Ruth at the door.

I took my place on the seat, too far away to hear what was being said, but, given the stern faces that occasionally looked around at me, I was not in anyone's good books.

Geri was dressed in a red dress that (in my humble opinion), was just a little too short for her. A thin belt at the waist emphasised the large bust at the front and the large buttocks to the rear. Her tall, strong legs were bare and, they were perhaps -- from a distance -- her best feature, tapering down from wide thighs to calves that showed no signs of being swollen. From the quick look I got of her face, she had done a good job on her make-up. Her shoes were black, open-toed and slipper-like with a small, fluffy pom-pom on them.

Penny looked as though she hadn't bothered to dress for the day yet. A plain white with thin, light-blue hoops, cotton nightshirt managed to just about hang over her thin bottom. It was possible, just, to make out that she had white briefs on too, doubtless ones that no half-respectable pervert would ever steal from a washing line.

I was trembling a little as the ladies still chatted away, Ruth reaching into the gym bag I'd brought in and showing them various items within, all no doubt meant for me to wear. As they did, I scanned the apartment to get any clues as to what the two lovers were planning for me. The large living room had a wood laminate floor and was well-furnished, looking clean and tidy, certainly not cluttered. As I looked down the room towards the women, to the left there was a raised step of about one foot in height that led to the open-plan bedroom which featured a large double-bed and dressing table. At the bedroom wall nearest to where I was sitting, there was large, white canvas or cardboard panel. Around this panel sat an array of lighting equipment and various cameras. Maybe this was here all the time and not just for today; Ruth and Penny sometimes went to photo-shoots for work; maybe Penny even helped set-them up. I hoped that was the reason for their presence anyway.

The wall to my right had two doors, leading to, I assumed by some configuration, the kitchen, the bathroom and other bedrooms.

There were two large settees in the living-room and another chair, like the one I was on, nestling at the end of a settee. Over this chair, I could make out a pair of white, fully fashioned stockings. I didn't need to be Sherlock Holmes to know they were Geri's. They were too large at the top to be Penny's; she could have fit her whole body into just one of them I reckoned. At the foot of that chair was a large box. I couldn't make out what was in it, but it did look a little out of fashion in the well-kept room. Perhaps it contained stuff needed for the day ahead.

In a bookcase - about four-feet high - I could just about make out a number of books by authors who seemed familiar, perhaps I'd seen the same authors in the bookcase at Esther's house -- Bechdel, DeGeneres, Naomi Wolf. The pictures and posters that dotted the apartment all seemed to have symbols or slogans that suggested the women didn't have too high an opinion of the male gender.

The women stopped talking for a moment and Ruth stepped forward towards me until I was within hearing distance, with Penny and Geri not far behind.

"Now Carla, after your outrageous comment when we arrived, I hope you're going to be a good girl and do everything these kindly ladies want. Without question, understand?"

I nodded, almost in tears at the thought of being left alone with them.

"Remember, prove you're a "man", at least one capable of "getting it up" (the others chuckled at this), and who knows, if Esther can't show you've a dressing-up, shemale fetish history, I might let you into my knickers too! Misbehave though and who knows? I've got your brother's email address remember!"

"Oh, and just one more thing, I've cut your credit cards up and closed our joint bank-account. I've locked away your business account cheque book and cards and I wouldn't recommend you calling in at a branch to try and get cash. If you do need to write a cheque for the business, ask me, understand?"

I nodded.

"I'll give you a little spending money, say £5 later next week, but you'll obviously need more cash to get by - petrol, and suchlike. So, I've come to an arrangement with Penny and Geri. They'll pay you £60 for every orgasm you give them today, providing you don't come first. Is that clear? You've got to fuck for your cash. If that makes you feel like a whore, then so be it."

Ruth turned and gave the smirking Geri and Penny a farewell peck on the cheek before reaching into her handbag and extracting a key; she gave it to Penny.

"Oops, nearly forgot something," she laughed, looking over Penny to me and winking.

She strode towards the door, Geri following, leaving Penny, dangling the key in front of me.

I heard Ruth saying she'd be back around 4 p.m. and then the door shut and Geri returned to her lover's side, both eyeing me with a glint of wickedness.

With Ruth gone, I sat in trepidation, feeling like a frightened, abandoned puppy. Soon, the two women were standing in front of me, both with a look of simmering fury and contempt.

Penny was still dangling the key to my cage, Geri I noticed, had reached a hand down to Penny's backside and was moving it inside her lover's briefs. I got the faintest whiff of aroused vaginas above the scent of the candles and joss sticks which, a moment ago, were the predominant smells.

"Right pantie-boy, take your clothes off here and leave them on the seat, then go and sit on that dressing-table stool. Now."

"Yes Miss Penny," I thought it best to address her like that in the circumstances.

Penny walked away and went to set up the lighting and check various gadgets, leaving me alone with Geri, as I, with trembling hands, took off my clothes as ordered, but left my black, lacy briefs on. As I was stripping, Geri was telling me what she thought of me.

"So, sissy princess thinks she's too good to have sex with me, is she? You can do better than a fat, 40-plus year-old. Is that it?"

I didn't reply.

"Look at you, you big Nancy in your black panties. Not a big-shot now are you? You arrogant whore. You've got to fuck for your money now."

As I was about to walk towards the dressing-table, I averted Geri's sneering gaze, but became filled with a thought so dreadful, I nearly fainted. Ruth had said I could have some "pussy" today. But what if the pussy belonged to only one of them? Perhaps the other one had a cock? These days, that seemed just the sort of trick Ruth would pull.

As I sat at the dressing-table, I tried to work out which of the two might be the shemale. Whose dick would I have to suck or, worse still, have to take up my virgin ass?

I could see in the mirror Penny standing on tip-toes, stretching to secure a light high-up a pole. She looked too slim to have a cock and besides, the swift peek I'd had of her so far, suggested her panties had no lumps. So -- if there was a cock -- it must be Geri. I gave an anxious gulp, perhaps the first of many, and awaited my fate.

Geri was behind me now and had turned to Penny.

"Nail varnish first I think, don't you? Give it time to dry before we do her hair."

Penny agreed. I tried to see from the reflection in the mirror, if Geri looked to be a little loaded in the crotch department, but her red dress gave nothing away.

Penny had finished her lighting checks and came over to me and lifted my hand, whilst Geri selected a light-pink nail varnish.

"So Carla, too good for fat and too good for plain eh? Wouldn't look twice at drab Penny eh? She's just there to make your tea and post your letters. Huh, typical man -- well, sort of man. Oh, I've seen how men ignore the likes of me; thinking they'd have to be desperate; they're all handsome sex-gods of course. But most men are crap at sex anyway, aren't they Geri?"

Geri nodded. She had now started to paint the nails on my left hand.

"Bloody useless. Think they're good in bed, know how to satisfy women, yet if they knew the truth! Most of the troubles my students have are caused by men."

"There now, don't smudge that Carla. Now give me your other hand. And by the way, you must address me as Auntie Geraldine okay? And ask me or Penny for permission to speak, okay?"

I nodded.

Fingers and toe-nails painted, I was then marched to the bathroom, where Geri rinsed my hair before being led back to the dressing table to have it dried and shaped in a more feminine style. My hair was not that long, but long enough to be clipped a little and manipulated into a more feminine look, before it was heavily sprayed. (Earrings would have completed the look I thought.) Geri also applied my make-up, a little foundation, eyebrows shaped and highlighted, false-eyelashes applied and a bright red lipstick. I had still to work out which -- if either -- had a dick. Geri was still the more likely I figured.

"Now, stand up and let's see our little pansy bitch," Penny ordered, "and take your panties off, let's see if you need a shave."

"Yes, Miss Penny." I wriggled out of my panties and stood there like the wimp I was as they sniggered at the sight of my caged cock, not, it must be said, a most impressive sight. Fortunately, they decided I didn't need a shave down there. I usually kept it very trim, Ruth had always demanded I kept it tidy.

"Now, turn around and put these on sissy". It was Geri now; she'd been rooting in the gym bag Ruth had made me bring and fished out a pair of purple silk panties with a large white lace trim. As I put them on, I could see they were a crotchless.

"How do they feel whore? Nice?"

"Yes, very nice Auntie Geraldine." Even though I was still anxious about possibly having to take cock, the feel of the new panties and guessing they'd once been worn by Donna started to stir my dick a little.

Geri knelt down and manipulated my chastity cage so that my balls and dick were fully hanging out of the crotch opening. She then stepped back to allow Penny a clear look at my equipment.

"Look," laughed Penny who'd been watching all this, "her little pigeon-dick is getting stiff."

"Time for action then I think," said Geri. "You just double check the lights and the cameras, and I'll get her stockings and gloves out before we begin."

Geri fished around again in the bag, retrieving long, black, lacy fingerless gloves that came up to just below my elbows, and black silky stockings that had a large, elaborate darker-patterned top. The suspender belt was black too with a frilly trim about the front. I was very shaky putting these on and by the time I'd eventually succeeded, Penny had finished checking all her equipment, and was anxious for things to start. She had the key to my chastity cage and I was expecting her to uncage me at this point, but no release was forthcoming.

"Now," she ordered me, "have a good look at yourself in the mirror. Make sure you've fastened those suspenders and stockings properly."

I twisted to double-check the straps fastened to my stockings at the rear and could feel my dick becoming restless at the feel of the elastic pulling on the tops of my stockings.

"Now Pansy, those panties were your mother-in-law's I believe. Doesn't that make you a very, very inadequate sissy?"

"Yes, Auntie Geraldine."

"What does it make you? Tell me what it makes you?" Geri asked again.

"A very inadequate sissy Auntie Geraldine."

"Good girl. Now, undo my belt and unzip my dress you whore and then Miss Penny will tell you exactly what to do."

With trembling hands, I managed to undo the belt and then as she turned her back to me, undid the zip that went down to just below the waist. Now for the moment of truth.

Holding on to Penny to begin with, she wriggled out of her dress and stepped out of it. Penny noticed my cock stirring and whispered into Geri's ear something to that effect.

Geri wore a purple silk corselet featuring a half-cup bra. It was quite a feat of engineering I thought, the metal hooks at the back managing, just, to constrain the giant mounds that wobbled at the front. Her nipples were proud, large, clearly aroused and invited suckling. I may have dribbled a little on seeing them (I don't think it was noticed). Her panties though were not quite in keeping with the sexy corselet. They were more what you might call large drawers or bloomers, light-blue and of see-through nylon, elasticated at the legs. Certainly not from "Eve's Temptations". As Geri was led to the double bed, Penny positioned her for the ensuing action as I stood gawping but tremulous by the dressing table.

Geri was now face down on the bed, propped up on all fours, her big fat arse staring right at me. I couldn't look away if I'd tried. It was a great relief, believe you me, to see through the flimsy gusset, not a big cock, but a dark, moist patch of excited fanny drizzle. My still encaged dick was squirming and turning like a hen in a bucket.

"Okay pansy. I want you to go to Geri, pull her panties down and give her butt a good tonguing; deep mind you, not just a lick. Got that bitch?"

"Yes Miss Penny."

I walked towards the giant blue knickers now staring out at me, dreading having to perform on such a big bottom, imagining how my mates at the sports club would mock me if they knew what I was doing, yet -- beginning to dribble a little from my knob.

"Come on whore, jump to it, lick a real woman, lick a real woman deep," Geri ordered, "I'm waiting, don't be shy."

I climbed on to the bed and steadied myself, head lowered, ready to make its journey into the unknown. I reached up and lightly took a hold of the top of her knickers and gently yanked them down towards her knees, struggling to get them over her large behind but grateful that the nylon never gave me a static-electricity shock.

Penny stood close by with her mobile phone capturing a close-up of my descent into her lover's back-passage.

"Go on princess, lick that butt, get that tongue in and working like a good little whore," she urged.

Geri lifted one leg up slightly and reached down to hook her knickers off that leg so that her spread-eagled legs didn't rip them. Once off, her legs spread a little wider, I had to go in.

As ordered, I first licked her crease, tasting a mixture of new sweat with a slight hint of soap or similar; thankfully it became clear I wasn't the only one who'd douched that morning. My straining tongue, like a goldfish swimming up the mouth of the Amazon, moved downwards, taking in small amounts of moisture before reaching the point of no return. As soon as Geri felt the tip of my tongue at the entrance to her anus, she pushed her arse up a little, encouraging me to take the plunge. By now, her fat cheeks blocked out almost all peripheral vision and Penny had one hand on the back of my head, pushing it further in to the cave opening, my sensitive tongue now pressing on someone else's sensitive inner skin.

"In Princess, deeper sissy. You can do better than that," Geri goaded.

I strained my tongue and forced it further into the cavern, hoping desperately that her anal-nerve endings were now feeling its' moist caress. The thing was, I realised as I strained the poor thing deeper, if I could make Geri orgasm by giving her anal nerves a good, vigorous tonguing, I'd collect a pay-out and, although it seemed totally ridiculous to have such a thought crossing my mind at this time, I'd calculated that I was going to need maybe two qualifying acts to get comfortably through next week without my credit cards. I wriggled my tongue and desperately tried to exert downward pressure as well as twisting it around to excite as yet un-licked anal nerves. Truth be told, I wasn't an experienced butt-licker, Ruth would only allow a little oral invasion there, preferring my tongue to get working on her clit. The thought of licking Ruth's fanny helped me focus again on the job in hand. Geri kept wriggling her not inconsiderable arse to try and get me further into her hole; my tongue was beginning to ache and my jaw too. After one vigorous circular wriggling of her bum, she moved it away from my face and moved aside.

"She's not as good as you Penny love, see what you think."

Geri got off the bed, taking her knickers with her. I tried to give my jaw a quick, soothing rub as I watched Penny take off her little briefs, these too now showing darker, moist patches of arousal.

"Can I have a quick drink of water please?" I asked. Both ignored my plea.

"Auntie Geraldine, may I have a drink of water please?" I asked again.

"That's better." And she went down to the box of tricks by the chair in the living room and brought back a small bottle of water.

Penny, now panty-less (unlike me) had now got on to the bed and was knelt on all fours. Her nightie had slid down her back revealing her tight little bum, quite a contrast to Geri's.

"I hope you work a bit harder on mine whore. Now get down and lick my arse and don't you ever forget I'm your superior. Understand?"

I took a long, soothing swig of water before attending to my task.

Penny's arsehole was easily more tempting than Geri's. Although it had doubtless been "invaded" before, I wondered if this was the first time a man had trespassed there. Her hole looked quite small -- in proportion to her neat bum - and seemed to have a little pucker of skin at the opening. It actually looked quite inviting and I sensed my dick once again straining for release. Although the water had eased my aching tongue and jaw a little, I hoped my mouth, not having to bridge such a wide surface as Geri's butt, might actually give me a chance to go some way in; maybe even earn my £60 fee which I'd clearly failed to do with Geri.

My gloved hands gently held Penny's up-thrusting thighs and I lowered my tongue in the direction of its' hole, licking slowly downwards along her crease in the hope that she'd get stimulated a little before I pushed and nuzzled my revived tongue into her opening. Geri stood nearby, filming all this. I hoped she wouldn't take offence if I showed more enthusiasm licking Penny's bum-hole than hers. Women can be so fickle; so easy to take offence.