The Second Wager

It had been fine. I had to remind myself what a convincing job Sally had done on me. Just because I was in jeans and a T-shirt this time rather than a long summer dress didn't make me any less easy on the eye, but I still found it hard to think of myself in those terms. She was right though -- I was for all intents and purposes, a pretty girl. But rather than dare the outside again, what I really wanted was to go and look at myself in the mirror, then maybe put my fingers into my panties and see if I could make that tingle grow into anything stronger, because I was getting desperate for some kind of relief. "I think we should stay in."

"Well, it's a good thing I invited Jenny and Simon over then." Sally grinned.

"You did what?" I rounded on her, aghast.

"Invited my cousin and her fiancé over," she said.

"What? Why? When?" How could she have done that after what happened?

"To stop us getting bored." She gave a naughty smile. "They should be here soon. We'll have lunch. Jenny was talking about going clubbing tonight."

"Well, I'm taking all this off for starters!" My hands went to my wig, fingers hunting the edge through all those blonde curls.

"Fine," she said. "But you have to girl-dress for seven days straight, so the clock will restart. And..." She stepped in close and put her hands around my waist. "Are you absolutely sure you want to meet Simon as a boy?"

"Just tell them not to come!" I snapped.

"I'm pretty sure they're already on their way." She shrugged in fake apology.

Sally was right though. As mortifying as seeing Simon again would be after what had happened -- especially with Jenny there, knowing everything, it would be ten times worse if I was 'myself', trying to be all manly in front of them. Somehow it would be easier playing a role, pretending. Even if that role was as the jezebel who had slept with Cousin Jenny's fiancé.

"Or!" I said triumphantly. "I can change and go out." Yes! That was it. I'd spend my Saturday in a coffeeshop. I had my phone, I could bounce around on social media or play games.

At that point the doorbell went.

"You won't be embarrassed pushing out past them?" Sally inquired. "Or do you want to climb out the window?"

If we hadn't been on the second floor I would have done exactly that. But in the end the idea of emerging from the bedroom back in my regular clothes and then hurrying away, muttering hellos and made-up excuses when all of us knew exactly what was going on ... it was just too much for me.

Instead, I sat myself in the lounge armchair and tried to look invisible.

Jenny led the way in, her red hair curling around her shoulders, a wide white smile framed by crimson lips a very similar shade to mine. She wore a classic little black dress, and it clung to a lithe figure, slightly narrower in the hips than Sally, less generously provided for in the chest, but still presenting a lovely outline to the world.

Simon followed, tall, dark and handsome, wearing a grey jacket tailored to his broad shoulders. He had a carrier bag in one hand. He smiled my way while Jenny and Sally embraced. "Hello again."

I flashed an embarrassed smile, not meeting his eyes, and feeling myself blush. Sally and Jenny hit the sofa together and Simon grabbed a chair from the kitchen, positioning it between the sofa and my armchair. He leaned over and set the carrier bag on the arm of my chair. "A present for you, Mary."

Flustered, I opened the bag, having no idea what to expect. It was of course the flowery summer dress I'd abandoned at his flat. I'd had to change out of it after having wet myself when he made me laugh, and then having Simon pour half a glass of wine into my lap in a gentlemanly, and largely successful, attempt to cover up my little accident, which was of course the chastity cage's fault. And his for making me laugh.

I will add, that it's very difficult to laugh girlishly when you're genuinely amused. I'd been pretty successful at softening my voice all that day, but I did wonder if it was the laughing that made him suspect I might not be all girl.

"Thank you," I said meekly. Suddenly I was very aware of the steel tube impaling my squashed little nub of cock, rendering it utterly useless. It made me think of how Simon had impaled me on his thick, rock-hard eight inches. I became conscious of the weight of the breasts on my chest, the cotton panties around my shaved and overfull balls. Completely against my will, my hips twitched. For a moment I felt so slutty that I didn't know what to do with myself. I shook my head to rid it of silly emotions, and put the bag down beside the chair.

Jenny looked up from her conversation with Sally. "You're looking great today, Mary. Did you get your hair cut?"

I raised an unconscious hand to my wig. "Thank you. And no. Sally didn't even tell me you were coming, or I'd have put on something nice." Jenny was toying with me. Two weeks ago, she and Sally had set me up as a gift for Simon because we'd both been bugging them to try anal sex. Whether she'd told Simon that she knew he'd fucked me I couldn't tell. Either he was a great actor or the answer was no.

Tea and coffee was made and drunk. Small talk flowed. Simon proved suave and funny as before, and showed no signs of awkwardness over our shared infidelity. I found I was all fingers and thumbs, too embarrassed or just plain shy to take a full role in the conversation. But that silence did give me time to sneak glances at the others as they talked.

Jenny was as vivacious as ever, all smiles, exchanging quick looks with Sally, though whether those were they were the kind that two girls who licked each other's pussies shared or whether they were over what they both knew about their boyfriends, I had no idea. Sally was also happy and talkative and brought me into the conversation, making up stories about going on holiday with me and how I was the one all the boys chased. All I could do when Simon looked speculatively at me was blush, bite my lip, and look down at my painted nails.

I watched Simon of course, his thick, neatly cut hair, the shape of his jaw, the intelligence of his startling blue eyes, his lips... I remember kissing those. How had it come to this so quickly? I'd been a regular guy with a banging hot, sex-loving girlfriend, and an idle comment while watching Mrs Doubtfire had got me kissing another man -- albeit it a large, handsome one -- within hours of putting on a pair of panties. It didn't make sense. But all I could think about now was how I'd gone on my hands and knees for him. And my tight little asshole was already twitching at the memory of his blunt cock bumping up against it that first time. "Oh god..." I shook myself, trying to pull it together. I was Mark, not Mary. Putting on some silicone breasts didn't change a lifetime.

"Sorry?" Simon turned attentively to me.

I made a smile. "Nothing."

Jenny and Simon stayed for an hour or two, and before leaving, made Sally promise we'd both come to the club with them that night.

"We'll meet you there at 11." Jenny beamed at our front door. "Don't be late."

"11pm, at The Basement. I'm excited for it already!" Sally hugged her and let her go.

I waited for her to close the door before voicing my objection.

"No way in hell I'm going to a nightclub like this!"

"Silly girl!" Sally grinned. "Of course not."

I relaxed fractionally. "Then why did you tell them we--"

"You can't go like that! You'll need a tight dress, and those heels. And..." She held a hand up to ward off my protest. "And you can wear those Victoria's Secret panties. How about that!"

"I'm not doing it!" I shouted. "I can't go to a club as a girl!"

Sally looked disappointed and shrugged. "I can't make you, it's true." She went into the kitchen carrying the dirty cups. "But I'm going," she called over her shoulder. "And if you come I'll let you out in six days instead of seven."

I watched her bum as she vanished through the doorway. One hand strayed between my legs and I pressed the metal dome of my chastity unconsciously. I stroked it with two fingers through the tight jeans and the cotton panties sporting the word 'PRETTY'. A small tingle rewarded my efforts. A day less to wait before I could fuck Sally again. And boy was I going to pound her after all this. I guessed it could be quite fun dancing as a girl. In the darkness of the club I was even less likely to be spotted for what I was. And Sally assured me I was convincing on a sunny day. Convincing enough for Simon to flirt with and kiss. And then later, even when he knew, to take to his bed.

"I'll do it."

Sally popped her head out of the kitchen. "Good girl."

For the club, as promised, Sally gave me the lacy red panties that looked like something a woman would wear to bed her lover, and let me exchange them for the cotton ones that had more of a teen girls' sleep-over vibe to them.

Sally regularly got dresses from her sister-in-law, Lucy, who worked at the evening dress department of Harvey Nichols in Knightsbridge. She picked out a wine-red, skin-tight little number for me, with a high neckline. I put it on and was dismayed to find how far above my knees it ended.

"Oh, shush. You've got lovely legs." Sally produced a pair of matching red high heels. "Let's see how you walk."

Not very well was the answer. So much of the rest of the day was spent learning to look elegant rather than drunk in the heels, and also how to dance in them.

"You're going to have to learn how to say no, too," Sally said. "If you don't want some strange man taking you home and broadening your horizons."

"I. Was. Drunk," I said.

"Uh huh." Sally smiled annoyingly. "Just try not to be a slut, Mary." She patted me on the bum. Then let her hand linger. "You really do look rather hot, girl."

The last few hours at home seemed to crawl by. I admired myself in the mirror a few times, and as the time to go approached, Sally touched up my makeup and applied lip gloss. With five minutes before the uber arrived, Sally dabbed me with her perfume, Calvin Klein's Obsession, which I'd bought for her the previous Christmas and always associated with an early girlfriend of mine. Sally wore the same fragrance, and looked as gorgeous as I'd ever seen her in a short white dress with a plunging neckline, her mascara and eyeliner making an enticing wonder of her eyes, her lips a scarlet promise.

The driver eyed both of us up as we crossed from the main door to the car. On the journey over I found myself getting more nervous by the minute. I was actually glad of my chastity for once. It made detection of anything unusual down there virtually impossible despite the body-hugging dress. If my four-inch erection had been given free rein inside the red lace of my panties it wouldn't have escaped, but would probably have made a tell-tale bulge through the dress.

Sally led me from the uber to the club doors. I was practically shaking in my heels, all the while making sure I didn't stumble or trip. The bouncers waved us through, and within moments we were approaching the boom-boom-boom of the dancefloor.

The place was packed. Warm, dimly lit, smelling of alcohol and perfume, the lights overhead sweeping colours over scores of young men and women moving to the beat.

"I'll get a couple of drinks." And just like that Sally left me there, feeling unsteady in my heels and practically naked, my body revealed by the dress I wore rather than hidden by it. I became conscious that my nipples made visible bumps through both bra and dress.

It took less than twenty seconds for a young man to break away from a group of his friends and approach me. He wasn't bad looking, a cheeky grin, well-muscled in a tight T-shirt.

"You here alone?" A warm smile softened the bluntness of the inquiry. He had a working man's accent, maybe a plumber, builder, something like that.

Even in my heels he was still slightly taller than me. Instantly I felt panicked. My voice dried up. I didn't know how to send him on his way.

"No, I'm waiting for friends," I managed to squeak out.

"I'm friendly." His smile broadened, and he held his hand out as if inviting me to the dancefloor.

"I..."

"Mary! You made it." Simon emerged from the rhythm of the crowd, larger and better looking than my confident young suitor.

"I did!" I smiled at my would-be partner, now lowering his hand. "Thank you for asking. Have a great evening."

"We're over here." Simon turned away, leading me towards the bar.

Sally and Jenny were sitting on stools, both looking gorgeous. Sally handed me a drink as I arrived. I sipped it, vodka and tonic. I drank most of it in one go, in full knowledge of how expensive nightclub drinks are. I needed the courage.

The girls didn't give me long before they were pulling me out to dance. And like with the sea it turned out to be lovely once you were in. Within minutes I was part of the throng, dancing, having a great time. Simon and Jenny stayed with Sally and me, an alpha male protecting his little hareem. Jenny and Sally enjoyed a lot of attention, and it seemed that I was getting just as much. Guys kept drifting over, dancing close by, trying to attract our attention.

When a slow number came up, Sally drew me to her and we danced holding each other close, breasts pressed together. And that only seemed to draw more male attention. As soon as the song changed we had men crowding us from all angles.

I leaned in to mention it to Sally and she laughed. "If we kissed, half of them would come in their pants right here."

The next time a slow dance came on, Simon gallantly partnered with Sally and Jenny unexpectedly took my hand. She wrapped her arms around me, leaned the slender length of her body against mine, and put her head on my shoulder. It was nice. We rocked slowly back and forth to a song I didn't know.

"We've got something new in common since the picnic," she murmured, turning her head so her mouth was close to my ear.

I stiffened a little. "I..."

"It's OK, I understand," she said softly. "He is very handsome. And he's got quite a way with him."

"I didn't mean to..."

"Shush." Jenny slipped her hands down over my bottom and danced tight against me.

The night continued and I danced until my feet grew sore. Sally provided me with several more vodka tonics, and those combined with the beat to make an intoxicating mix. There's something very primal about moving to a drumbeat. The sexual tempo of thrusting hips, all acted out on the dancefloor to entice a partner.

I grew drunk on the lust in the eyes of pretty much every man who came near me. The power my tits, hips, and arse held over them was remarkable. Though I felt that balance shift when a large hand groped my bottom on my way to the ladies. I hurried away from that into the sanctuary of a stall, and pulled down my red panties to sprinkle into the toilet.

Sally was touching up her makeup in the mirror when I emerged, and she did mine too.

"Seen anyone you like?" she asked.

I knew a trick question when I heard one. "Only you, baby."

My answer drew some side-eye from the brunette to our left, though whether she disapproved or wanted a piece of me, I couldn't tell.

When we returned to the dance floor the DJ was starting a slow section to herald the end of the night. Simon turned away from Jenny with a smile and reached for my hand.

"Will you do me the honour of this dance?"

My heart fluttered like a schoolgirl's. It was silly, but with his hand warm around mine I felt like a princess. I blame the chastity that had squashed my manhood to nothing and skewered it through the core, but as Simon drew me to his chest, I felt all girl from the ends of my toes to the tip of my tongue.

"Don't kiss. Don't kiss," I muttered silently to myself. I couldn't see either Jenny or Sally but I was sure both of them were keep a close eye on proceedings.

The first song was an oldie, Lady In Red. And I was in red. Red dress, red panties, red shoes. We danced very close. I could feel Simon's huge erection against my thigh and had absolutely no doubt that he was thinking about when he'd eased its girth into my ass and ended up thrusting into me until he spat his seed deep into my guts. I squeezed his hand and put my head against his chest. No kissing -- I reminded myself. His other hand slid down over my bottom and clasped one cheek, pulling me to him even more tightly. My poor little cocklette tingled all the more in its tiny steel prison.

I glimpsed other couples as we turned, and part of me, on seeing those other girls with their men, felt proud of the one I had. Even if he was on lone for just one song. I held onto his hard body and enjoyed the sensation of his cock pressing against me, knowing I'd made that happen just by looking hot.

The dance ended and we stepped apart reluctantly, looking for Sally and Jenny. Simon saw them first, and I followed his gaze. The two girls had their arms tight about each other, breasts squashed together, and their tongues down each other's throats.

"Well, that hardly seems fair," Simon muttered, he sounded as if he were trying to conceal a real anger. He looked away and reached an arm to pull me back to him, bending as if to kiss me, a question in his eye. I felt the same on both levels. It didn't feel fair, and despite all my protestations over the last two weeks, I really did want him to kiss me again. But all of this, the whole situation, was punishment for my own infidelity. I would hardly be making it better if when Sally broke from snogging her cousin it was to see me doing the same with her cousin's fiancé.

Reluctantly, even despite the alcohol in my bloodstream and the lust trembling through me, I set a hand to his chest and held him back. I shook my head and pulled free, then walked back towards the girls. The main lights went on, telling everyone the time had come to leave. Sally and Jenny broke their kiss, smiling at each other with such affection that a pang of jealously ran through me.

Simon overtook me and took Jenny's arm as she stepped back from Sally. Neither he nor Jenny looked particularly happy about the situation. Jenny shook free and stalked off, following the general direction of motion as people started to head for the exits. Sally stayed put and I looked at her questioningly.

"She's thinking of dumping him," Sally said, shrugging.

"Because of ... because of what we did?" I said, both dismayed and outraged at the same time. "But you two engineered that! You set us up! I thought that was what you wanted to happen?"

"You didn't think that, Mary." Sally sounded stern now. "You just gave yourself up to him because you're a little slut when it comes down to it."

"But--"

"Yes, we set it up -- but you didn't have to do it! Jenny thought the whole thing was a joke and that neither of you would ever go for it. If I leave a hundred pounds on the table, it doesn't mean you have to steal it. Same thing here." She walked off after Simon and Jenny, and rather shame-faced I followed, suddenly a little unsteady in my heels.

It was a warm night outside and Simon and I stood in the square watching the crowds clear. Jenny and Sally had gone to have a heart to heart, and I could see them standing together at the nearest corner.

Simon looked my way, grim-faced. "She knows about us."

I looked down at my feet. "Sorry. I didn't tell her. But Sally knew. She said she just had to look at us when we came back that day to know."

After a few minutes that felt like an hour, Sally came over and led me away from Simon.

"Jenny's staying with me for a while," she said.

"But..." I wanted to object that it was obvious they'd be fucking each other as soon as they were through Sally's front door. "She's talking about dumping Simon. And to be honest, I'm still not sure about you. That's part of the reason you're still locked up!"