The Second Wager

[[ I love talking about my stories and getting ideas & opinions from readers for future work, so do get in touch.

No real content warnings on this one, it contains pretty much exactly what the tags say -- it's a continuation of The Wager (see my story list) but can probably be enjoyed on its own. It's focused on the feminisation of the main character by his girlfriend for another man. A chastity device features heavily. There are sexual encounters between the feminised man and a woman, and later, a man. The feminisation is consensual, but our main character is certainly conflicted over the issue. ]]

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The Second Wager

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The first week of chastity had been hell. My girlfriend, Sally had sucked the sperm out of me to get me in the thing in the first place. It wasn't the standard little pink plastic cage, with a tiny padlock. This, my subsequent research had shown me, was hardcore chastity. A stainless-steel contraption in which the whole of my cock was contained beneath a small, perforated dome about the size of half a table tennis ball. Worse still, in addition to the steel ring clamped firmly under my balls, it had a urethral tube long enough to impale the scant inch of cock remaining to me.

The thing was impossible to take off without the key, and probably quite painful to remove even with it. Any form of erection was totally impossible, and it left me on the edge of incontinence, liable to wet myself if I didn't sit on the toilet and have a regular sprinkle, or if someone surprised me, or made me laugh too hard. The latter had been what happened with Simon and the event had taken me back to his flat to borrow one of his girlfriend's dresses, after which the wine had taken over entirely, and one thing had led to another...

The only good thing about chastity was that Sally had had me stay at hers ever since she put it on. She said it was to ensure my 'good behaviour'. Though whether that was to make sure I didn't somehow escape the thing, or if she thought I might sneak back to Simon for 'round 2', I didn't know.

For the first two days after Simon took my virginity, I couldn't sit down without a painful reminder of what he'd done to me. I'd alternated between shame and disgust at myself, interspersed with moments when I remembered the picnic, me in a summer dress, makeup and wig expertly applied by Sally. Trapped in chastity I'd felt strangely free rather than imprisoned, and had loved fooling Simon and Jenny into thinking I was a woman. I'd enjoyed feeling girly, the dress, the fake breasts, cotton panties, all of it. And catching Simon's eye as we all drank wine in the sunshine. At other times I remembered how he'd entered me and how at the end, after thrusting and pounding at my ass, he'd ejaculated inside me, collapsed panting on top of me, and slowly softened in my depths. At that moment I'd felt almost in charge. As if despite his strength and dominance, his easy charm and good looks, I'd got what I wanted. His seed deep inside me, and him sated and pliable in my arms. Albeit in the bed he so often shared with Jenny.

After more than two weeks in chastity my main opinion on the matter was that I was horny. I desperately wanted to come. My poor shaved balls felt full to bursting and had started to ache so that I was reminded of my state in every quiet moment.

In desperation I'd started fingerfucking myself, thinking of how Simon had done the same thing to me when I'd proved too tight the first time his cock came calling. I liked the feeling and the accompanying throb inside my chastity hinted that if I could just stimulate myself enough there might be some reward, some release, even in captivity as severe as the sort I was enduring.

To my shame I started eyeing up everything in Sally's apartment that was even vaguely phallic in shape, considering it as a possible sex toy. Sally didn't own any dildos, and the small vibrator that normally lived in her lingerie draw had vanished when I looked for it. So, I was reduced to considering the handles of kitchen implements. I even looked through her woefully small collection of tools and spent some time pushing the rounded grip of her largest screwdriver back and forth through my hand, imagining Simon's thick penis opening me up.

In the end I settled for the handle of her favourite hairbrush, which had more length and girth to it than my two fingers but wasn't so large that I might be in pain after a thorough 'stoking of my pot'.

The first time I used it was nice. I sat in the temporary privacy of the bathroom and determined to sort myself out. The pleasant sensation of the handle stretching my anus and sliding inside me combined with the tingling throb under my chastity. And when I touched my fingers to the steel dome and jiggled it, the pleasure was enough to make me gasp. I leaked a little precum, but sadly that was the limit of it. And afterwards my balls felt fuller and more achy, rather than relieved.

The second time was while Sally was out shopping. I decided to have a real go at it. To help things along I stripped down to my T-shirt and borrowed a pair of her panties, silk knickers, pale blue and frilly, from a camisole set. With these on, I lay on her bed, pulled the gusset to one side, and pressed the handle of her hairbrush to my little hole. My spit-lubricated anus surrendered to the pressure and I slid the whole length of the handle inside me. With my legs up and eyes closed I lay there on my back, jiggling my chastity and thinking of how Simon had fucked me.

It was very nice. I lay there for a long time. It made me sigh. It made me pant. It did not make me come.

"Mary!"

I opened my eyes and discovered with a mix of shock and horror that Sally had returned from her trip and let herself back in quietly enough to take me by surprise. I slammed my legs down and felt myself going crimson with shame. I would have sat up immediately, but the hairbrush made that impossible without considerable pain.

"Oh baby," Sally crossed the room with a mocking smile. "You have got it bad, little girl."

She reached between my legs and took hold of the brush end of her hairbrush. "What's this!" The tone of her voice implied she knew exactly what it was and had been watching me for some while.

With a firm hand she wriggled the handle deep inside me. The feeling was delicious and to my mortification I opened my thighs for her, biting my lip. "Poor baby." She covered my chastity with her palm, pressing gently.

Sally sat on the bed, working the handle gently in and out of me. "I suppose Simon is really quite handsome. Too alpha male for me though. Too tall. I like my men bite-sized." She pushed the handle in as deep as it would go and I moaned gently. "Jenny tells me that Simon has quite a big cock. I imagine it's much bigger than this brush?"

I didn't answer but the thought of it made me gasp as she wriggled the thing inside me again.

"I can get you a proper cock, Mary. A nice big silicone one, with balls, and a sucker to stick it to the toilet seat so you can sit on it. How about that? My treat!"

My asshole contracted around the handle and the throb in my chastity grew powerful.

"No," I said, clinging to the shreds of my manhood. "I don't want a dildo. I don't want Simon. I'm not gay. I just want to come. I want this damn thing off!" And I tugged at the chastity. The pain was immediate and killed any chance of an orgasm.

Sally pursed her lips, and pulled the brush out of me with a wet 'plop'. "If you say so, Mary. But you're the one wearing my frilly knickers and fucking herself with household items." She patted my chastity, making me wince. "Put them in the washing pile, please. You've leaked on them. And once you've cleaned my brush with hot water and detergent, DON'T use it again."

By Saturday I was desperate for release. I watched Sally move around our flat and savoured every angle of her, every bounce of her breasts, every sway of her ass. She knew it too and showed no mercy, straining in a tight T-shirt for stuff on the top shelf, bending over in front of me at each opportunity.

I was glad, in a secret kind of way, to have had an experience with another man. Everyone should try on gay for size at least once. That was certainly a philosophy that Sally subscribed to -- she'd had more girls than boys. Moreover, although she hadn't admitted it, Simon had convinced me that after Sally and Jenny had abandoned us at the picnic and we had had our ... encounter, Jenny and Sally were in fact fucking each other silly just as they had on many other occasions.

All that aside though, what I really wanted, I told myself, was for Sally to bring the whole bet thing to a close. The wager had been that if I lost the bet and was spotted as being male, I would have to keep wearing part of my outfit for that day for as long as she chose. I'd only been expecting to meet Jenny, but she'd brought her boyfriend to the picnic too.

In the end, in a scenario engineered by the treacherous Sally and Jenny, I'd been manoeuvred into taking Simon to bed and letting him have my virgin bottom. The anal sex had been to avoid the embarrassment of having let things go so far whilst not actually possessing the pussy that all signs pointed to me owning. It turned out I didn't have to worry about that as Simon had seen through what really was a very convincing transformation and had texted Sally before the act, whilst I was showering, to ask her if I was trans. She'd told him yes, and he'd still bedded me. So, I'd got fucked and still lost the bet! And rather than keep me in panties as I'd been expecting, Sally had decided to keep me in chastity.

Watching Sally get out of our bed in her negligee I could honestly say that all I wanted was to get the chastity off right there and then, to let my long-denied erection flourish, and to use it on her, at length, thereby reclaiming the manhood that between them she and Simon had managed to ... hide, subvert? I wouldn't say steal, since technically I was in this position of my own free will. I'd accepted the bet, and only my own sense of honour was keeping me to it. I was sure if I demanded that Sally produce the key and unlock me, she would do just that. Though how far her disappointment in me might go, I didn't know. She might tell me to start sleeping in my own flat. She might say we were over completely. Even if she didn't, I would be disappointed in myself. I liked to follow through, and Sally had always said it was one of the reasons she liked me so much. If I said I would do something -- I would do it.

"Baby?" My gaze roamed her body.

"Not today." She stripped off the negligee in a fluid motion and stood there, gorgeous, heavy breasted, slim hipped, a slight curl to her long honey blonde air. I guess her pubic bush would be dark, the stubble looked almost black, but she never let it grow long enough to tell for sure.

"But..."

"I said no, Mark."

"You don't even know what I was going to ask." I tried not to sound petulant.

"Surprise me?" She took a pair of white lace panties from the top draw and paused, looking at me, faintly amused.

I had of course been going to ask if the chastity could come off. I'd been asking more and more often over the past few days, even, to my shame, becoming rather sulky about her refusal. "I was going to suggest you came over here and let me kiss you." I offered my most suggestive smile. "But if you put those panties on first then you won't get the full effect."

"Tempting." She smiled, then pulled her panties on and reached for her bra. "But I don't want to get you all frustrated."

"WHAT--" I bit off the word and tried again in a softer, more reasonable voice. "What is it that you do want? You get me frustrated just by standing there. And I'm assuming you don't want a complete end to our sex life?" I was being unfair. She had straddled my face pretty much every other night since the chastity went on and had let me lick her to orgasm. And, since she knew I'd cheated on her, she had the moral high ground as well as the physical high ground when she lowered her pussy onto my mouth. Her own infidelity with Jenny was only alleged, on the basis of no evidence. She denied it and Simon's assurances could well have been purely motivated by his desire to get me to lift my ass for his cock. I definitely had let him fuck me, and some would say Sally would be perfectly justified if she threw me out.

Sally continued putting her bra on, fastened it, then moved back to stand beside the bed. She pulled the duvet off me, appraising my nude body. If I'm honest, there wasn't much to appraise. I wasn't muscly, or tall, but I did have a flat belly and -- so she said -- a nice bum. In bra and panties she moved over me and set a single finger to the little dome of my chastity, moving it slightly and making me bite my lip.

"Let me dress you up again," she said, suddenly all business. "And if you girl-dress for seven days I promise to hand over the key."

"I can't go to work like that!" I was prepared to do a lot to be released. Murder wasn't on the list but give it another month and it might be. But walking into my office in a skirt and make-up wasn't one of those things. The murder came first.

"At work you can just wear panties under your normal clothes," Sally conceded, still stern-faced. "But at home, if you go outside other than for work, you wear whatever I say. Dresses, skirts, stockings, a nighty or camisole at night, anything I say."

"Deal!" It was the best offer I was going to get. She could have me in chastity for a month otherwise, or a year, though I'd never last that long -- my sense of honour did have a time limit and I was pretty sure it lay somewhere between a month and a year. And after all, a bet was all that was keeping me locked up.

A week of girl-dressing was fine. Then we'd back to regular sex and our old ways. It was all good. Especially as I'd enjoyed wearing the dress. Might as well get some more in while I had no cock to use. If nothing else it would help pass the time, and I'd take some of my own private photos for any future lonely night when I wanted a little thrill.

"Well now, that's what I wanted to hear." Sally's business face melted into a warm smile. "Let's start now. Then we can see about that kissing." She put her hand between her legs. "The only lips that are allowed down here are going to be ones wearing lipstick."

An hour later I was back in full makeup again and wearing the sandy blonde wig. The stubble under my arms, on my legs, and around my groin had all been shaved back to smoothness, balls too, pink and fresh. Sally had secretly invested in a high-quality pair of strap-on breast forms which I wore like a bra except in place of cups there were realistic silicone breasts, flesh coloured with stiff, dark nipples. She'd chosen them to match her own D-cup handfuls so that I could borrow her bras. I definitely had no plans to be in a repeat of the awkward situation I'd found myself in with Simon, but if I ever was then the bra could come off without anything coming off with it, and there would be a juicy pair of boobs to play with underneath.

With the weight of the breasts sitting on my chest I immediately started to feel femme again. Sally put me in a pair of her panties and one of her T-shirts, a white one bearing the legend 'Girls On Top'. I found myself loving the way it stretched over my new tits. The panties were simple white cotton with the word 'PRETTY' stitched in small pink letters just over my chastity. I'd eyed up a red lacy pair she'd bought from Victoria's Secret but she'd seen me looking and had shaken her head as if sexy lingerie was something I had to earn somehow.

Satisfied at last, Sally pushed me down and moved up the bed, setting a knee to each side of my head. She reached down, tugging her own white panties aside, presenting me with a very close look at her shaved pussy. Its enticing scent reached me. It looked moist and tasty and very much something I wanted to push my tongue into.

Sally looked down at me. "What do you say?"

"Please?" I guessed.

She smiled. "I say no to Mark. I say yes to Mary." And with a happy sigh she settled herself onto my painted mouth.

For the next ten minutes, until my tongue ached and my lips felt bruised, I was kept busy between Sally's thighs. I lay there with my tongue exploring her vagina, sometimes thrusting as far into her as far as I could, sometimes chasing her slippery clit through the folds of her flesh. For some of the time my mind was empty of thought, in the moment, focused entirely on the task in hand ... or rather -- in mouth. Ten minutes is a long time though, and for some of the time I imagined Jenny doing to Sally what I was now doing to her as Mary. Simon had been pretty convincing when he said Sally and Jenny had been fucking since school. It seemed entirely plausible given how pretty Sally's cousin was, and how many girlfriends Sally had enjoyed before her long hiatus with me.

At the times when her bum pressed down on my breasts, and I imagined myself a lesbian, licking out my girlfriend just as Jenny had, I got a delicious little tingle in my poor, trapped cocklette. It wasn't much, but it had been so long since I'd felt anything down there without touching it, that I was excited to greater efforts and I made my tongue flicker back and forth, hoping I was doing at least as well as Jenny could.

Sally drew the process out, moaning softly the whole time, gasping now and then. She edged herself, lifting off when she came too close to orgasm, until finally pressing her weight upon me and letting me finish her off.

She wriggled comfortably, squeezing my head between her thighs, and them lifted off with a long, "mmmmmmm". Looking down at my wet face she added, "I'm going to need to redo your lips and foundation."

With my makeup fixed, Sally completed dressing me. I squeezed into a pair of skin-tight jeans she'd acquired for me, and slipped into the flat shoes I'd worn to the picnic almost two weeks earlier.

"We'll get you dolled up in a nice dress tomorrow," Sally promised. "Stockings, suspenders, heels, the whole nine yards."

"Heels," I asked?

"I ordered some your size." She grinned. "You're paying. And for these." She cupped my breasts.

"It almost seems like you were just waiting for stuff to arrive before you struck this chastity deal," I said, suspiciously. "You're really that into dressing me up?"

She reached out and touched my cheek. "We both are, Mary. You know that!"

I shook my head. "I'm not a cross-dresser. I mean, once for a bet, sure..."

Sally arched an eyebrow and continued to dress herself, jeans and a T-shirt just like mine, except hers was red and didn't boast 'Girls On Top' across her boobs. "It's a little more than cross-dressing, Mary. You let Simon fuck you."

"He did not--" I bit my lip. He had actually fucked me. I wanted to say we made love, but that would only be digging the hole deeper. Much deeper. "That was one time." I felt that tingle in my chastity again, slightly stronger than when I was licking Sally's clit. "An experiment. I was drunk! He made--" I swallowed that lie. Simon hadn't made me do anything. I could have stopped him when he moved to kiss me. I could have walked away at any point. Even got up off the bed and left the house. I should have.

"Awwww..." Sally came up behind me and patted my bum. "Mary's so cute when she gets flustered."

I ignored her. "So, what are we doing today?" Leaving the house was out of the question now.

"We could go to the shops. See if we can find you some nice outfits."

"I'm not going out. And I don't need outfits. This is for a week. I can borrow your stuff."

Sally stood behind me, hands resting on my hips. "We went out before, Mary. It was fine. Don't you want any more boys checking you out, pretty girl?"