The Wager

[[ Before the story starts, I want to give a heads up about the contents so that hopefully nobody will be disappointed or end up reading a story that wasn't the kind they wanted.

These will of course be somewhat spoilery -- so if you're feeling brave and adventurous, then just jump in. It's a self-contained story in the same setting as my previous work. At 8,700 words it's a longish short story. I hope you enjoy it!

So this story contains: boyfriend and girlfriend action -- a girlfriend dressing a boyfriend as a girl -- male chastity devices -- a picnic where the boyfriend poses as a girl for a bet -- panty wetting -- cross-dresser on male oral sex -- male on cross-dresser anal sex -- a small degree of trickery. ]]

*

"Anal."

"You're saying if I win, I get to have anal sex?" I tried to sound only mildly interested.

Sally gave me that wicked little grin of hers, the one that had first attracted me to her, before I'd even seen all the other treasures god had blessed her with. "Isn't that what all the boys want these days?"

"Say it." I didn't trust her unless she said it out loud.

"If you win you can have anal sex." Again, the grin. "It's not like I don't notice your fingers exploring down there." She managed to look prim about it, arching an eyebrow at me, and tossing her long blonde hair over her shoulder.

"Wait, I know this one!" I shook my head. "You're going to whip out a strap-on and try to peg me."

"Nuh uh!" She looked offended. "Proper anal sex, baby." She bit her bottom lip and looked at me under her lashes, sexy as hell.

I frowned. As tempting as the offer was, I still didn't want to take the bet. We'd been watching Mrs Doubtfire and I'd remarked how easy it was to pass as a woman if you weren't too tall. A wig, some makeup, and nobody's going to question what's presented to them. It wasn't as if Robin Williams was trying to be an attractive woman, just some old biddy.

Sally shrugged. "So maybe it's not so easy after all. It's not just lipstick and a pair of these." She lifted the sizable breasts straining her T-shirt then let them fall. "It's how you act. There's more to being a woman than being the same shape as one!"

"I do want your bottom though..." I tilted my head to peer at it. Sally pursed her lips and continued to sit on the object of my desire, which wasn't helping me view the prize on offer. "How would we even judge? I mean, I'm going to dress up and you're going to laugh at me and tell me I'm not doing it right and I've lost the bet."

Sally shook her head. "I told you. It's not about how you look. I'll get you dressed and do your makeup. I'll agree that you look the part before we even start."

"What then?"

"My cousin Jenny's coming up to visit her mother this weekend. I said we'd picnic on the Fields if the weatherman's right and it's sunny. You come too. I'll introduce you as Mary instead of Mark. If you don't get called out or Jenny doesn't say something to me before we get home. You win." She stood up and patted her tight little bum. "You won't fool her though."

"Not if you don't do a good job on me," I said.

"I'll dress you and do your makeup," Sally replied. "We're almost the same size, my clothes should fit you. And if you don't think I've done a good enough job, then don't come. What have you got to lose?"

"Apart from my dignity?" I snorted. "Nothing." But the truth was that as Sally walked off to the kitchen, her sweet behind twitching in those skinny jeans ... I was thinking more about what I had to gain. It wasn't that I didn't enjoy her pussy, but the tight little hole that winked at me whenever I had her doggystyle was very inviting. There was something so tempting in the naughtiness of it all. Sodomising her. Taking her virginity. "Deal," I called after her."

She turned round and looked back at me. "Of course, I'll want something if I win."

I frowned. I'd thought that the humiliation of being caught out would be punishment enough for me, without having to give up something else. "What?" I asked reluctantly.

"If I win you have to keep wearing part of the outfit for as often as I say and as long as I say."

"Nope. I'm out." I shook my head. "You could have me in a skirt for a month!"

"I promise it wouldn't be anything that showed." She batted her eyelids at me, suddenly seductive.

"Hmmm." I didn't particularly relish having to wear her panties any time she pleased. But ... set against the promise of having her sweet little asshole when I won... "Deal."

The weekend came along faster than expected. I spent most of my Friday at work daydreaming about all the nice little moans and groans Sally was going to make as I inched into her butt for the first time. She'd always steered me firmly away when I got too interested in the rosebud pucker of her anus. A few touches and that was enough. No kissing. No licking. And absolutely no penetration. Maybe, once I'd broken her in, we'd talk about moving in together. We'd been dating six months. It felt like time.

Sally had agreed to source a wig and anything else I'd need. If I wasn't happy with the ensemble, I didn't have to go through with it. It felt like a win-win. I still imagined I'd end up saying no, but Sally would have her fun dolling me up and would probably turn herself on doing it, and a turned-on Sally was always a party.

I arrived bright and early on Saturday morning, low key anxious about the whole dressing up thing, but keeping my eyes on the prize. Even if I didn't pull it off, Sally would have still put anal on the table, so's to speak. If I played my part and showed willing we'd definitely get there. Everyone said she wore the trousers in our relationship, and it seemed to me that not only would claiming her ass be exciting and delicious, but it would also establish who was boss, at least in the bedroom. Sally had had mainly girlfriends before we started dating and whilst I found that exciting, I also found it intimidating. Claiming her ass felt like it could be something that was just ours and that she wouldn't be comparing with prior experience.

I'd be the boss in the bedroom. She could still have her way everywhere else. When we moved in together, she could choose the curtains -- it didn't matter to me, certainly not if I got to shoot my load in the tight, warm depths of her behind.

Sally had her entire wardrobe laid out on her bed, on the armchair next to it, on the dresser, and even dangling from hangers along the picture rail. It was all organised, she was a very organised girl. Panties, suspenders, and stockings down one side of the bed, bras and blouses down the other. Skirts, summer dresses, and more blouses on the rail. She had lots of dresses. Her older sister, Lucy, lived in London and was the manager of the Evening And After Six department in the Knightsbridge branch of Harvey Nichols. Little sis was forever getting huge discounts on 'damaged' items.

Sally led me in and turned as I entered behind her. She reached out a hand and pressed her palm to my groin. Through my jeans she squeezed the hardness of the erection I hadn't been aware I had.

"This," she said, "is going to be a problem."

"It is?" I hadn't realised I was so turned on until she took hold of me, but it didn't feel like a problem with her hand around it.

"Jenny's not going to take long to notice this thing trying to signal her through one of my skirts!"

"We can ... tuck it away," I said.

"Not like this we can't. And tucked between your legs it's going to be uncomfortable every time it tries to get hard again. Which will show when you walk." She shook her head and released me. "We're going to have to put it back to sleep then..." She rummaged in her lingerie draw and pulled out two objects. "...use one of these." The first was a pink plastic chastity cage no bigger than my thumb, complete with a tiny black padlock. The other was a stainless-steel device with an integral lock and a tiny, perforated dome not much bigger than both my thumbnails put together. A slightly curved steel urethral tube reached down about an inch from the dome.

"Where the hell'd you get those?" I yelped.

"Amazon."

"Well, I doubt I'd fit in the plastic one," I said. "And there's no fucking way I'm trying the other one. It looks like a medieval torture device. Plus, you'd need an inch long cock to have a hope of getting it on."

Sally smiled. "You'd be surprised." She shrugged. "Either way, you're going to need to wear one of them if you want to stand any chance of winning the bet." She turned her ass towards me and bent over slowly as she put the chastity cages on the bed next to one of her black thongs. "First things first. We need to tame that bad boy." She directed a look at my groin.

"Time for a quicky." I grinned and started to unbutton my jeans.

"Ice cube," Sally said. "We're on a clock here."

"Let's meet in the middle." I made a counteroffer. "Blowjob."

Sally took the baby oil off the dresser and cleared some space in the middle of the double bed. "Ice cube if you're going to tuck. Hand job if you wear the pink cage. Or blowjob and you wear the steel one."

"Hand job." That was easy. No blowjob was worth having a steel tube inserted into your urethra for! And losing my erection to an ice cube didn't sound like any fun at all.

Sally smiled and lay back on the bed. "Come on then, Mister Scaredy Cat." She started to unbutton her blouse. "But if you come in my mouth, it's the tiny cage."

I pulled down my trousers and underpants, releasing five hard inches for her immediate attention. She unhooked her front-loading bra, exposing full, D-cup breasts, large-nippled, full of creamy goodness, my target zone for today. She knew that if it was to be a quick hand job I'd come much faster with her tits to spurt across.

I moved over her on all fours, straddling her, then rose to my knees, holding the headboard with both hands. Sally took an oily grip of my cock, slim fingers wrapping its length, angling it towards the fullness of her breasts. She began to masturbate me expertly, smooth firm pulls interspersed with tugs and squeezes aimed at coaxing the sperm out of me as fast as possible. I imagined how tight her ass would be squeezing me when I claimed it that evening, and my hips started to move without instruction.

I looked down at her large, pale breasts and pink nipples, excitement mounting, picturing them dripping with the warm come I was imminently going to spurt over them. Sally looked up at me, knowingly, continuing to wank me, certain that she was going to get what she wanted out of me. She opened her pretty mouth and slid her tongue over her bottom lip, holding my gaze all the time, and I just couldn't help myself. There was something so sexy, so invitingly slutty in the way she just opened her mouth for me that I had to fuck it. A moment later my cock was deep inside her, red lips circling it as I slid in and out and in and ... I lost my load down her throat, jolting my groin against her face as she held me back with both hands.

"Oh god..." I let her suck me dry. "Mmmmm...."

She released my wilting penis from her mouth. "Good boy."

I sat back on her knees as she shuffled up into a sitting position, licking her lips. "The steel cage it is then."

Not gonna lie. Getting that cold metal tube into my pee hole hurt. Sally did it while I lay back and swore. On the plus side. Well, maybe not the plus side... Anyway, in its efforts to retreat from the process my cock shrank to the point where the whole of it would fit under the dome that was hardly bigger than a thimble. Sally locked it in place. By the time I stopped tensing and sat up to look, the key was nowhere to be seen.

"All done," she said brightly.

"That really hurt," I complained.

"More than virgin anal sex?" she asked.

I shut up and tapped the shiny little dome tentatively. "How does it all fit under there?" It seemed impossible.

"Magic!" She reached out and tugged at my T-shirt. "Clothes off! We've got some shaving to do."

I frowned. I don't have a lot of body hair but it wasn't as if Jenny was going to be examining me that closely.

"We've got to do your armpits and your legs," Sally said patiently. "May as well tidy up here and there as we go."

I pulled off my socks, took my T-shirt off and followed her into the bathroom. When Sally was on a mission it was best to let her have her way, and the armpits did make sense. It was promising to be a warm day so I wouldn't be able to cover up. "I hope this thing doesn't hurt as much when it comes off." My imprisoned cock was still stinging where the tube impaled it. I guessed it was there to make taking the thing off totally impossible without the key. The plastic cage might be slipped off with some twisting and a careless disregard for the wellbeing of your balls, but not this thing.

Sally led me out of the bathroom twenty minutes later, smelling of flowers. I was more closely shaved than I'd ever been before and in many more places. My pubic hair was a thing of the past, my testicles an alarming shade of pink. I reminded myself of the prize at the end of it all and followed her back into the bedroom.

"Which panties do you want?" With a dramatic sweep of her hand Sally indicated the array she'd laid out.

"These are nice." I picked up a pair of lacy black ones that I'd enjoyed kissing her pussy through on several occasions.

"Tart!" She smacked my hand and passed me a sensible pair of white cotton panties with small blue blossoms embroidered on them. "You're going on a picnic, not a hot date."

Chastened, I put them on, tucking my balls in. The chastity was invisible under the cotton and I made hardly any bulge at all.

"So ... no suspenders then?" I asked.

"So keen!" That wicked smile again. "Maybe next time."

"This is to win my bet, girl. There's not going to be a next time."

Sally didn't argue. She picked up a simple white bra to match the panties and helped me into it. The empty cups sat unconvincingly on my chest. Sally vanished and reappeared with cottonwool.

"It's going to take more than that," I said, looking significantly at her boobs, each of them a significant handful. Just cramming cottonwool into the cups wasn't going to improve the illusion that much.

"You really need the sort of girlfriend who plans ahead." She looked down.

"It's fine," I said. "I doubt Jenny's going to squeeze them--"

As I said it, Sally grinned and brought her other hand out from behind her back, holding a box. The glossy pair of tits on the front left me confused. "Silicone breast forms," she explained.

"Jesus! How much did you spend on all this?"

"Relax. They were twenty-five pounds." She met my gaze. "And you're paying for them."

"Fine." I rolled my eyes and let her fill the bra. They felt good and heavy, capable of the right sort of sway and jiggle when I moved.

"And now the dress," she said.

My eyes found one of the two little black dresses she always looked so good in.

"Picnic!" She steered my head towards a selection of summer dresses. "We're not going clubbing. It's a picnic!"

"That one." I pointed at the middle one, a strappy red dress densely covered in hundreds of small white flowers. The skirt came to just above the knees on Sally and I recalled it flaring out whenever she turned. Shaving my legs had been worthwhile!

"Good choice, baby." She went to get it.

I wriggled into the largest piece of my ensemble and Sally arranged it to her satisfaction. It was a little tight over my new breasts but perhaps no tighter than it had been over Sally's last time she wore it.

"Does my bum look big in this?" I craned my neck, pretending to try and look over my shoulder to see.

Sally smacked me, snorting at my imitation of her in every dress ever. "It looks pretty good, actually."

"So, we're done?" I wanted to see myself in the mirror.

"Idiot." She shook her head. "We're only just started. Hair and makeup next."

And she wasn't kidding. That took an age.

I sat back and let Sally have my way with me. She brought out a nice enough wig, mid-length, sandy hair. Fixing it to my head proved to be a fiddly business involving lots of teasing and tucking and a certain amount of adhesive tape. After that the brushes, blushes, powders, and paints came out.

As the hour and more crawled by I became more and more excited to see the results. Sitting there in my summer dress, cotton panties and well-filled bra I felt surprisingly feminine, a situation only enhanced by my complete inability to get an erection or become even vaguely hard. Reduced to a nub inside its steel prison my poor impaled cocklette could only tingle. It didn't stop me feeling very aroused though, and I was glad that Sally was all business, because if she'd started kissing me or even talking dirty, I don't know what I'd have done with myself.

Finally, with the last eyelash curled, the final foundation touch up, and the last application of lip gloss, it was time for the big reveal. Sally brought out the full-length mirror, covered in a sheet, and positioned me in front of it, still fussing like I was her favourite dolly.

"Ready, to see Mary?" she asked.

"Ready."

With a flourish she removed the sheet. And there stood Mary, pretty as a picture in her summer dress, slim at the waist, full at the chest, a face I didn't recognise framed by bangs of luxurious sandy hair. I looked younger, wide-eyed, innocent rather than tarty.

"Wow," I said. Then spoiled it with, "I'd do her."

"Me too," said Sally. "I'd fingerbang you right here, sweetie, if you had a pussy." She kissed my ear and sent shivers through me.

I turned, slowly, keeping my eyes on my reflection.

"So," she said. "Are you coming to the picnic?"

I pursed my glossy pink lips. I didn't know if I could fool Jenny once I started speaking, but nobody was going to be pointing and laughing in the street. If anything, I'd turn men's heads for the right reasons. "Sure. Let's do it." And suddenly, although it was still mostly about claiming Sally's butt ... it wasn't all about that!

The Fields weren't fields as in 'farmers' fields', it was an area of meadows and small copses on the edge of town before it broadened out into a heath that swept up to the Malan Hills. It was a popular area to picnic, but never crowded since it covered such a large area. Sally packed a wicker basket with baguettes, cheese, and wine. The set included china plates, wine glasses, knives and forks, all very civilised.

There had been a moment of panic as I realised I was bare foot and Sally was two sizes smaller than I was. Fortunately, big sister -- Lucy -- had left a pair of flat slip-ons last time she visited, and they fit me fine.

Sally drove us, and I spent the ten-minute journey checking out the contents of the handbag she'd hung over my shoulder. No real woman would leave home without a bag, she assured me. It appeared to be one of her older ones, full of the sorts of things she always carried but which I never really paid attention to. Though there were some surprises too. A money purse with spare change, a pack of condoms, tissues, cheap lipstick and eyeliner, a pack of three sanitary pads, a clean pair of lacy black panties, three old keys, half a pack of polo mints, and a rape alarm. "Spare panties?" I asked.

"You never know," she said innocently, and turned left from the main road. We followed a track up into a gravel carpark surrounded by tallish grass and distant trees. "Now, best behaviour, Mary, that's Jenny's car." She indicated the yellow mini with the tinted windows that she'd pulled alongside of. "The bet is on. One false move ... and you've lost."

We emerged from the car together. I'd closed my door and was watching Jenny get out of her mini, all curling red hair, wide smiles, and white teeth, when I realised that someone else was climbing out of the other side. A tall, dark-haired man, classically handsome in that TV anchor sort of way.