The Lad in the Lingerie Shop Ch. 10

The run up to Christmas was an extra busy time at "The Lingerie Emporium". As Edna had predicted there were even men coming in to buy Xmas presents for the women in their lives, a fair percentage of which would be returned by the women as being the wrong size or totally unsuitable or both.

I seldom crossed paths with Yvonne but when I did, her manner was slightly friendlier than before, but if anyone else was within earshot, she'd make it clear she was the one giving the orders. I blew hot and cold as to whether I should participate in a threesome with her and Mitch; still a little anxious about having Mitch take my anal virginity but still absolutely wild about the thought of getting anywhere near an undressed Yvonne.

By now Anita was home from University and back working with me. She'd made the odd passing reference to my cross-dressing (she new Joyce and her mum both knew about it and that they had put me in chastity), but I was reluctant to engage her in anything other than short responses, still feeling somewhat betrayed that she'd got a boyfriend.

One Friday afternoon, Joyce called me in to her office to ask me to do her a favour. She had been talking to Anita about the possibility of selling more lingerie to men via adverts in Men's porn magazines and the local papers. She wanted me to go and buy 5 or 6 of the top selling porn mags for her so that she could see if any other ladies' underwear businesses advertised in them and how they were worded. She'd give me the money from petty-cash but I'd need to provide receipts.

I agreed, with some reluctance as I didn't really fancy going in to a newsagents and gathering dollops of porn-mags from the top shelf and then having to ask the shopkeeper for a receipt! How many men ever asked for receipts? Also, I didn't like the idea of buying such stuff in the local shops which I might visit occasionally for other stuff.

Joyce could see my reluctance but said that, instead of working in the shop on the Saturday morning, I could take the works van to some other town and buy the magazines there, where I'd be unknown. I could bring the purchases and receipts in to work with me on the Monday.

That afternoon, when work was over, I went to see Mrs Ferguson to get her to give me the key to unlock my chastity device as was the norm. However, she refused to unlock me.

"Well Robert, as you'll have pornography with you over the weekend, Edna and I think you'd best stay caged, just to discourage you from self-abuse. I'm sure you understand."

I was about to object but she ushered me out of her office making it clear she would brook no argument: she was the boss; she had control over my chastity cage. She added that she'd told Yvonne not to give me the key either.

I bought the magazines in Leeds. On handing them over to Joyce together with the receipts and change, she called Anita in so that the three of us could discuss how best to advertise in a way that would tempt cross-dressers to buy. It was agreed the ads would have to make clear larger-sizes were available and items would be posted in packaging which gave no indication they were from a lingerie shop and that there would be no follow-up contact.

Purchases from these adverts would have to quote a code so that we'd know to send them out without franking or any other means of a third-party knowing where they were from. It was too late to get ads in the porn magazines before Christmas, but the ads in the two local papers resulted in a marked increase in postal purchases, especially of larger-size stockings and panties.

As we left the meeting, Anita suggested we went on our break together as she wanted to chat with me. I agreed.

"What's up Robert? You seem a little frosty with me since I came back from Uni. Don't tell me you're now embarrassed to talk to me following our little games. Is that it?"

"No, it's not that and anyway, I wasn't aware I was being frosty," I lied.

Anita shrugged her shoulders, clearly not believing me.

After a moment or two of silence I spoke.

"How are things with this Oliver I've been hearing about then?"

She laughed out loud at this. "Ah so that's it is it. Little Roberta is jealous is she?"

I blushed a little and looked down into my coffee to avoid her scrutiny which would have confirmed her suspicions.

"And who told you about 'Oliver' then? I bet it was that Angie wasn't it?"

Again, I refused to respond.

"Well, for your information, it's not 'Oliver', it's Olivia, got that, Olivia - another woman. Does that make you feel better?"

I lifted my head and let out a little smile. Deep down I was very relieved and pleased but didn't want Anita to see just how jealous - and childish - I'd been.

"Look Robert, mum knows all about Olivia and is fine with it, but she thought she'd better tell anyone who asked if I was seeing anyone that it was 'Oliver', you know how prudish people up here are. Besides, it's only a casual thing, a bit of lesbian fun. I'm bi-sexual and don't see why I should deprive myself of same-sex fun just to keep the puritans up here quiet."

"Sorry Anita," I managed to say. "I guess I was a bit jealous and you're right of course, what others think of your sexuality is none of their business. I know that as much as anyone don't you reckon?"

The air had now been cleared and, over that dinner-break, at Anita's request I told her all about how Joyce had come to find out I wore panties and how she and Edna had put me in chastity "for my own good" and also how I'd been attacked by rugby players from Mitch's team. She already knew most of this but she didn't know about my having to let Mrs Ferguson's frumpy neighbour suck me off as I wore a basque, stockings and panties. She laughed herself silly with this and that I'd got paid for it!

Then, making sure no one else was near enough to hear what I said next, I leant closer to Anita and told her about Yvonne's offer to use me as a sissy in a threesome with Mitch.

At first, she could barely believe me.

"What, Yvonne? Miss Frosty-knickers of 1973! You're kidding me."

But, after reassuring her that it was all true, she asked me the question I'd been asking myself since Yvonne's approach. "Did I really want to experience being 'taken' by Mitch and humiliated by him and Yvonne whilst dressed like a slut?"

When she put it like that - and considering she'd only just told me about how she wasn't going to let the prudery of others stop her indulging in her sexual fancies - I agreed that I did get turned on by Yvonne's suggestions.

"Good girl Roberta," she half mocked me. "Look, leave it with me. I'll check when the rugby team has a break in its fixture list and sort it all out with Yvonne: we get on okay really. I'll get you made-up and dressed before handing you over and make sure it isn't a set-up to get you duffed-up by his willy-waving players. Okay?"

"Okay," I agreed, pleased that Anita was now back in control of my sexual proclivities and making me come to terms with my submissive side without the need to feel shame or guilt.

"And you'll have to start stretching your anus in readiness for Mitch. I gather he's rather well hung."

"What do you mean by stretch?" I asked in all innocence.

"Just leave it to me. I'll get you the items and the lubrication and tell you what to do to be better prepared for Mitch, okay?"

I saw Anita and Yvonne in close conversation a few times over the following days and guessed what they were discussing.

Eventually Anita told me that they'd decided on a weekend in late February. Neither Yvonne nor I were working on that Saturday and Mitch's team had no fixture, having been knocked out of some cup competition that took place then.

My sense of anticipation, excitement and nerves had never been higher.

Once the date was agreed, Anita had sat me down and explained how I'd need to insert the butt plugs she'd bought for me, starting with one about four inches long and gradually progressing to the eight-incher.

She'd also bought me the lubrication and told me to wear briefs that had a bit of substance to the gusset, not thongs or similar, as it would help hold the plug in place as I went about my day-to-day business. Needless to say I complied, at first finding it painful but towards the big day I was getting eight-incher in my butt like an old-hand, well, in so far as it wasn't too painful after insertions. Even so, I was always aware of its intrusive presence.

I'd been shaving my legs maybe twice a week since that first occasion and now they were as smooth as a baby's bottom. My hair was long, as was the fashion in the early 70's but I'd completely removed my sideburns. Only my well developed biceps and not-too prominent Adam's apple would betray my masculinity if I had my hair fashioned and face made up as a female.

On the Friday before the big day, I went to see Edna to get her to unlock my chastity cage but she told me she'd agreed to a request from Anita to give her the key, adding that she didn't want to know what shenanigans she or we were planning.

I waited patiently in my flat on the Saturday for Anita to finish work and come round and prepare me for whatever lay ahead; a little miffed at still being locked-up in chastity but maybe grateful that I was as I would surely have had a quick wank or two just thinking about Yvonne slipping out of her dress and underwear.

Anita - who told me to practice douching a while before - had told me beforehand to eat little on the Friday and then nothing on Saturday and to douche my bottom that afternoon. Complying with this readily re-enforced my sense that I was really going to go through with this; the eight-inch plug reminding my anal nerves too.

Anita arrived, still wearing her "The Lingerie Shop" dress and bringing in her car all she deemed necessary to get me ready for my trip to the posh hotel where Mitch had booked a room.

I was itching to get things rolling; almost able to smell Yvonne's pussy nearing my face, but Anita insisted we took our time; everything had to be just right.

Nearly two hours later, I emerged from the flat to be taken by Anita to the hotel. She'd clipped and curled my longish hair and made my face up to look ever so feminine. I now had long false eyelashes on and dark-red lipstick. Anita had helped me dress in the underwear Yvonne had told her Mitch would most like. A white "A" cup long-line bra was put on first, followed by white, seamed fully fashioned stockings, held up by a white, 4-strap suspender belt.

After fastening the stockings, Anita helped me clamber in to a semi-sheer pair of white panties with a dark-blue piping and bow at the front. They were a kind of "V" cut design, being quite narrow at the sides but having a front and rear of slightly more material than a thong or g-string. My butt was still clamping the eight-inch plug I'd put in that morning.

A black mini-dress that just about covered my bum but not my stocking-tops and black open-toed high-heels plus a light, silk scarf completed the outfit. My toes and finger nails were both varnished dark red and Anita had given me a generous spraying with her perfume.

"When we get there Roberta, I'll just need a minute or two with them to sort things out and then - the night's all yours!"

"But what about my chastity cage, you are going to unlock me before we get there aren't you? My balls are aching to empty."

"I've got that all in hand. Don't worry. Just sit back and trust me."

Anita deliberately parked at the far end of the hotel car park so that I had to walk quite a way - past numerous people - to the Hotel entrance and then through the lobby to the room Yvonne and Mitch were in. I was acutely aware of my stocking tops being visible to all and sundry as I tried to walk as ladylike as I could in my heels and with a large object up my sissy anus. I waited nervously as Anita knocked on the door and when Yvonne answered, she looked me up and down and clearly liked what she saw.

"Come in. Robert - I mean Roberta - you stand there and don't move while Anita and I have a quick chat."

I stood just inside the well-appointed hotel suite as the two women walked off towards the other end of the room - too far away for me to hear what they were saying, but I did see them exchanging things from their handbags and assumed it was simply Anita handing over the key to my chastity-cage. This was a relief for me, my dick was now relentlessly trying to expand, failing and then trying again as it squirmed within the confines of the whalebone cage, a little bit of juice oozing from its poor, unsatisfied head, smearing the thin sensuous fabric of my panties.

Anita gave me a broad smile as she walked past me on her way out.

"Just do as you're told Roberta, they've paid me the fee up front. They'll ring me when they've done and I'll come and pick you up and take you back."

I'd no idea I was being whored out and that Anita was my pimp! Not that I objected, in fact it gave me a little bit of a kick.

Yvonne, who was dressed in a simple one-piece blue dress and tan tights or stockings - I couldn't be sure - called me over to her. She was now sitting on the end of the bed and had kicked her shoes off.

As I got close to her she said that Mitch was just finishing off having his shower and that I must do as she ordered until he appeared.

She then stood up and ordered me to take off my dress and scarf and then her dress too. She watched with mocking eyes and I stepped out of my little black number to reveal my panties and long-line bra. Then she turned her back to me and told me to unzip her. She pushed her bottom out a little to further tantalise me as my trembling fingers moved the zip down towards her bottom and the top of the back of her panties.

Once the zip was undone, she wriggled out of it and I could see her sumptuous legs were clad in hold-up stockings that had about 3 inches of denser, patterned material at the top. Her back was towards me, not allowing me a glance at her beautiful breasts.

"On your knees Roberta and gently take my stockings off; don't ladder them whatever you do."

Talk about the agony and the ecstasy! The feel of her skin as I gently pulled down her stockings was divine and I got a good glimpse of the little light-blue panties she wore tight against her sumptuous bottom. How I longed to bury my head in those mounds but no, I knew better than that and did as I was told.

Once the stockings were off, Yvonne ordered me to look at the floor and not to ogle her as she then sat down again on the bed and leant back a little.

"You may now lick and kiss all my toes, slowly now."

Kneeling, I leant forward a little to accept a big toe in to my mouth, enjoying the sensation of my suspenders tugging gently on my stockings and my panties tightening across my behind, the butt-plug moving slightly as I knelt, exciting a few nerve-endings that had been ignored when I was standing. As I licked each toe slowly, longingly, I glanced up a little to see Yvonne's pantie gusset getting a slightly darker shade, the odd ginger pubic hair peeking out from the sides, the smell of excited fanny-juice gently teasing my nose which was aching to immerse itself in her bush.

I was in a sort of heaven; I'd have given anything to have been in this position with her - and now I was and, was getting paid for it!

After those few minutes of bliss, I was instructed to stand up.

"Pull your panties out a little Roberta, I want to see if you've got your chastity cage on properly."

As I stood I glimpsed for the first time Yvonne's well-formed B cup breasts within the flimsy constraint of a bra that matched her panties. I couldn't take my eyes off them as I held the waist of my little panties out for her to inspect me, my dick now in exquisite torture, aching for release but held firmly within the confines of my employer's device. I could sense the dribble of a little pre-cum on the end of my poor knob.

"Yes, Anita's done a good job on you but I can see your getting a little too excited. I'll have to put a stop to that; we've a long evening ahead. Go and stand facing the table over there and put your hands on it and spread your legs and stick your bum out. I'm going to punish you before Mitch sees you."

I walked over to the table in as feminine a gait as I could in my high-heels, beginning to immerse myself in the role of whore, call-girl, prostitute, slut, call it what you will, that Anita had fashioned for me.

Yvonne then ordered me to lower my panties down past my bottom; I obeyed.

"Stick that bum out and don't you dare whimper. Understand?"

I nodded. "Yes Yvonne"

"It's Mistress Yvonne to you. Got that?"

"Yes Mistress Yvonne"

She then reached for a nearby hair brush but delayed spanking me until she had removed the butt-plug which had now become visible to her.

"Anita's trained you well I see," she noted. Then the smacks came, very hard smacks too, maybe twenty on each cheek. I clenched my teeth, determined not to howl or cry out in pain.

When she'd finished, I was instructed to pull up my panties which I did, but to leave the plug out.

"Now, what do you say?" I was asked.

"Thank you Mistress Yvonne," I instinctively responded.

"That's right.

It was then that I heard the door to the bathroom open and footsteps approaching. It was Mitch, about 6 feet tall, athletic and powerfully built, with short dark hair. He was wearing a white dressing-gown and I realised, nothing else.

He gave his wife a kiss and then started to run a hand over my sore, pantied bottom.

"So, this is the little pansy that felled my two players. Who'd have thought it possible? If only they could see you now. I don't know who'd blush more you or them."

They both laughed and Mitch's dressing grown opened a little at the front as they did. I gasped as I saw his manhood swinging underneath. Even in its still flaccid state, it must have been at least three inches longer than mine when erect and was certainly twice the diameter. Perhaps Anita should have furnished me with a 10 inch plug! Mitch noticed I was staring at his manhood.

"Like what you see bitch? That's a real man's dick not that little girly caged thing you've got. Now go and stand by the bed. I'll show you how a real man has sex.

I walked over to the bed, trying to wiggle my hips and bottom as Anita had suggested I did when dressed as a woman and stood as ordered; my face now almost as red as my recently spanked behind.

Yvonne came over to the bed and slowly took her bra off, waving her tits at me as she did so. Next, her wet, damp, scented panties were removed and these she stuffed in my mouth.

"That'll keep you silent while I let a real man own me," she smirked.

I then had to watch as Mitch fondled and teased Yvonne in as long a session of foreplay as I'd ever managed with Angie before I had to come. Yet Mitch had not yet penetrated her, his large dick extending up past his navel in arousal for me to get a good look at.

Eventually, Yvonne opened her long legs as wide as she could; I nearly fainted at the sight of her beautiful, sticky fanny. Mitch then approached with his large, magnificent, erect pole and squished it way into her ginger, bushy cave. She gasped in almost uncontrolled desire as he slowly, slowly, pummelled his meat into her; the sound of her juices mulching against his tool adding to my heightened sense of arousal.

I can't speak for Mitch, but by that time I was nearly ejaculating, how he managed to control himself amazed me. Then he withdrew his penis from his wife, the head of his knob wet and glistening from basting in her vaginal juices.

"Over here slut, take those panties out of your mouth and clean this now. It's the nearest you'll ever get to my wife's fanny and I know you fancy her. Lick it now, make the most of it."