The Wager

"Jenny!" Sally squealed and hugged her cousin. "This is my friend, Mary," she introduced me. I smiled back, speechless.

"Lovely to meet you, Mary." Jenny grinned. "And this is my boyfriend, Simon."

I smiled back, somewhat frozen and still unwilling to speak.

"Come on then," Sally encouraged, then paused. "Oh, Simon, a nice strong man like you could carry the hamper for us?"

Simon obliged. Well over six foot he dwarfed me at 5'8" and Sally at 5'7", easily lifting the heavy basket out of the car.

The four of us walked off into the Fields in search of an isolated spot to have our meal. Jenny and Sally led the way gossiping about family and old friends. Simon and I followed. I kept my head down, not having to pretend to be shy, though probably not for any reason Jenny or Simon would suspect.

Rather gallantly, Simon tried to make conversation with me, opening by asking how I knew Sally.

"She's my g--" I bit off the word 'girlfriend' before it escaped. I'd been too focused on speaking softly and at a more female pitch than on lying. "Good friend. Old friend, I mean. From school." I felt myself blushing under my makeup. I could have said girlfriend. Simon probably knew Sally was bisexual. I even suspected, from things she'd let slip, that she and Jenny might have experimented together as teenagers on shared family holidays.

"High school?"

"Primary," I lied unnecessarily, getting flustered.

"That's nice," Simon said. "Little girls together. I don't know any of the kids I was at primary school with anymore."

We carried on walking, following small tracks and talking about nothing in particular. I focused on keeping my voice soft and asking questions so that I wouldn't have to answer any. Simon, it turned out, had recently moved to the city and worked in banking. He didn't strike me as a typical banker though. He had a sense of humour for one thing and managed to make me laugh twice before Sally declared that we'd found our spot.

The tablecloth went down, and blankets were put out to sit on. Sally played mother, taking the goodies out of the hamper, and the rest of us watched. I sat with my skirts pooled around my thighs, and my legs on display, being careful not to part them in an unladylike fashion. The sun was warm, the sky blue, a gentle breeze stirred the air, and even though the wine remained corked as yet, I felt slightly drunk. Liberated maybe. The air on my legs, the pretty dress, the cotton panties -- it all felt delicious and exciting at the same time. My poor little cock tingled in its tiny prison, and I smiled encouragingly at Simon as he told us all about a trip he'd made to Tanzania and how he'd ended up being chased by a herd of goats.

We started our picnic and passed around the wine, the first of two bottles, a nice dry white. I picked at the bread sparingly, not wanting to spoil my lip gloss. Jenny and Sally did most of the talking, but Jenny made an effort to draw me into the conversation. The whole thing was going really well and despite my impending victory I really wasn't thinking about claiming Sally's ass that evening. I was just focused on how nice the experience was.

A K-Pop ringtone startled me as I was about to answer a question Simon had just asked me. Jenny handed me her wine and fished her phone out of her little white handbag. She frowned as she answered it. I couldn't hear the other person, but Jenny looked increasingly serious.

"I'll be there." She put the phone away.

"Problem?" Sally asked.

"My mother's had a fall. I don't think it's too bad but I need to go check. That was her cleaner and the woman's English isn't good."

Simon stood up. "We'd better go then."

Jenny shook her head crossly, red curls bouncing. "You know she's still angry about Christmas. If she's broken her leg, you're the last person she'll want there."

"I'll drive you." Sally reached out and touched Jenny's arm. "Aunty Gladys likes me. I can help you with her."

Everyone was standing now except me, so I drank both the glasses I was holding, set them down, and got to my feet too.

"No, Mary. You and Simon should stay and finish the picnic. This doesn't have to spoil everything. Knowing my aunt, it's probably nothing and we'll be back in half an hour."

"Yes," Jenny said, already walking back toward the cars. "That's a great idea. You two stay. Have fun. It'll be fine. I'll call." Her voice dwindled as she headed away.

Sally squeezed my hands, grinned, and set off in pursuit, almost running to catch up.

Simon frowned, shrugged, and sat back down. "So, Mary, just you and me then on this fine summer's day." He reached for the nearly empty first bottle of Chardonnay. "More wine?"

I settled on the blanket, arranging my skirt around me. "Thank you." I held my glass out. I was going to need another drink. It was one thing playing a girl on the periphery of a conversation between four people. Now I was a lone man's sole focus.

I needn't have worried. Simon was attentive but did most of the talking. I realised with a little thrill that he was actually flirting with me. Gently -- he wasn't coming on heavy -- but definitely flirting. I felt his eyes on me, occasionally falling to my breasts and thighs. I'd never had a seriously gay thought in my life, but dressed as Mary an undeniable tingle was running beneath my panties, making me wriggle my hips to try to stop it.

We finished the bottle and opened the other one. I realised, as I sipped and listened, that I was more than a little drunk. Simon held my hand to steady the glass while he refreshed it, and met my eyes, both of us acutely aware of warm skin on warm skin. I pulled away gently, surprised at my own reluctance. I knew I was being silly but part of me couldn't help imagine Sally's face if I told her later that not only had I fooled Simon, I'd even got a kiss from him.

We settled back on our blankets and talked. I admitted I didn't have a boyfriend.

Simon frowned. "You and Sally..."

"Oh, no, we're not like that," I said. Well, we weren't. Not lesbians.

He smiled. "Then I'm amazed you're single, Mary. Entirely by choice, I'm sure."

I returned his smile and let him spin out one of his travel stories. At one point his impression of an argumentative taxis driver had me snorting wine out of my nose. I was still coughing and spluttering when I realised with horror that I'd wet myself. The urethral tube must have loosened my control somehow, and when I laughed and then nearly choked... A wet patch was spreading on the front of my skirt, my panties were sodden, and warm pee was running down my thighs.

Simon saw my look of horror and, alarmed, came gallantly to my rescue, thinking perhaps that I was still choking.

I pushed him away weakly, mortified by my accident and still hoping he might fail to notice it, or at the very least, pretend not to.

"Hey." Simon put his hands on my shoulders. "It's OK. It happens to everyone sometime. I pissed myself laughing at a Jimmy Carr show once. My friends never let me live it down."

Rather drunk and still horrified that I'd wet myself I found myself further embarrassed at having tears in my eyes.

"Oh gosh." I tried to stay in character. "How awful..."

And just like that, Simon tipped the remains of his wine into my lap. "Never happened, sweetheart. I spilled my drink on you. That's all."

Our eyes met and I mouthed a 'thank you'.

He reached for my hand and began to get to his feet. "Come on."

"Where to?" I resisted. "I think I should stay sitting, don't you?"

"Well, you could sun-dry." He smiled. "But we could also get a quick uber to mine, and you could clean up. Jenny's suitcase is there. She won't mind you borrowing something."

And so, ten minutes later I was sitting with him -- on a blanket -- in the back seat of an uber, smelling of wine, and wriggling uncomfortably in warm wet panties.

Simon lived even closer to the Fields than Sally did, and it wasn't long before he put his hand on my knee. "This is us."

His apartment was a sunken basement at the front, though still with good light, and it opened onto the building's garden at the back. The place was large, airy, and well decorated with white walls and modern fittings in greys and browns. I couldn't tell if the art on the walls was cheap or expensive, but I liked it well enough.

I stood nervously in the hallway while Simon hunted for Jenny's suitcase. He emerged from the bedroom after a short while, his hands full of dresses, skirts, tops, and panties.

"I didn't know what you'd want," he said apologetically. "The bedroom's yours to change in."

"Thank you," I said, still shy despite the wine. "I think I should take them into the shower, don't you?"

"Ah." His turn to blush. "Yes. It's right here."

I took the bundle of clothes from him -- our fingers touching just a few beats too long once again -- and backed into the bathroom.

My first order of business was to finish the wee that had started this whole thing. I sat on the toilet like a girl and sprinkled through my chastity, feeling so much more comfortable as my bladder emptied.

A knock on the door startled me. "Yes?" My voice came out a little deep. I softened it. "Yes?"

"It's just me. I got a text from Jenny. Her mother's fine. She's at Sally's now. Says it's too late for the picnic. I said we'd finish up and meet them there in a while."

"Ok. That's fine." I wasn't really listening, too worried he'd come in and catch me peeing.

I finished, dabbed myself dry, and belatedly locked the door. Next, a hurried shower, taking care not to wet my wig. I dried myself on Simon's thick, white towels and patted at the silver nub imprisoning my cock, and at the pink balls beneath, which somehow looked smaller than usual. I realised that I was quite drunk and that the tingle of excitement in my shaved groin was only growing.

I put on the lacy black panties from Sally's handbag, and wriggled into one of Jenny's little black dresses. The thing was pretty tight, especially over my Sally-sized breasts, which were a couple of cup sizes larger than Jenny's boobs. The black material clung to me like a second skin, making me feel more exposed than I had been when wearing nothing at all.

Looking down, I couldn't see even the slightest bulge over my chastity. As an afterthought, I rucked up the leg-hugging skirts and slid one of Sally's sanitary pads over the steel dome in my panties. It wouldn't have stopped the earlier flood, but it could take care of a small accident. Even so, I resolved not to let Simon make me laugh again.

Slipping my shoes back on I unlocked the door and went out, leaving the rest of Jenny's clothes on top of the laundry basket, and my wet stuff in the shower.

"Wow!" Simon was just coming out of the kitchen, holding two steaming coffees. "Mary! You look like a million dollars!" He put the cups down on a sideboard and reached for my hand.

"Thank you." Surprised, I let him twirl me for inspection. We ended up closer than we had been, me looking up into his startlingly blue eyes. "And thank you for being so understanding."

"And for tipping wine onto you?" He smiled, holding his gaze on mine.

"That too," I murmured.

"And my reward?" He raised his brows suggestively.

I blame the wine for what happened next. And the moment. I went on tiptoes and kissed his cheek softly before slipping back onto my heels.

At the same time, he put his hands on my waist, one further round, almost on my bottom. "Well, that was lovely. Is there any more?"

I tried to back away. "We really shouldn't. Jenny--"

He kept me there. "I'm pretty sure that Sally has three fingers knuckle-deep in Jenny right now."

"What?" I asked, shocked and shaking my head.

"It's okay." Another smile, voice soft. "Before she agreed to get engaged Jenny said I had to agree to her occasional girl-flings. Her and her cousin have been doing each other since school. I thought you'd know that. Weren't you in their class?"

"Primary school," I murmured. Sally was fucking Jenny as we spoke? I didn't want to believe it.

"Ah." He pulled me softly to him. "So?"

The size of him, the sheer physical presence, made me weak at the knees. My mind whirled with confusion and alcohol. I was intensely aware of the hand he had on my ass, of his body pressed against the length of mine. The breasts compressed between us. Suddenly, I realised that the firmness pressed against my groin wasn't my own cock but Simon's erection felt through his trousers. And running through it all was the thought that Sally had abandoned me at the picnic to fuck her cousin. Had Jenny's mother even hurt her leg? Had that even been a call from her?

When Simon bent to kiss me I didn't fight him off. When he put his large, gentle hand on my neck I opened my mouth and his tongue filled it. After that I was lost. We stood kissing in his hallway, hands roaming each other's bodies. And although my cock stayed soft, tiny, imprisoned, and impaled the whole time, I'd never in my whole life felt so turned on.

It wasn't until we broke from kissing and he took my hand to lead me into his bedroom that I realised what a situation I'd gotten myself into. I followed helplessly into a fresh-smelling room dominated by a double bed with black sheets. Sunlight streamed in through net curtains over the garden window. Birds were singing outside. Time seemed to slow as the expanse of the bed drew closer. I'd no idea what to do. I'd no idea how to stop Simon discovering my secret, or what he'd do when he found out.

Simon closed the door behind us and positioned himself half on, half off the bed, still holding my hand and inviting me to join him. My mouth still burned with his kisses. Want trembled through me.

"I ... I'm on my period." Genius! I was even wearing a sanitary pad.

A frown briefly marred his brow. "Good thing I like cuddling and kissing so much then." He grinned, and pulled me to him.

We fell, semi-drunkenly, onto the bed, laughing. He found my mouth with his and for what seemed like an age we were kissing, stroking each other, pressing against each other. I found myself on my back with Simon on top of me, kissing my neck, his erection hard against my thigh. If Jenny's dress hadn't been so tight I would have opened my legs for him then and there. I felt very aroused and very slutty. I thought of Sally and Jenny, and moved my hips under Simon's, thrusting against him.

I realised that one of his hands had moved to my breasts. Disaster threatened. I caught his wrist and locked my fingers in his. "There are other things we can do," I said, moving my other hand under him to take hold of the bulge between his legs.

Simon seemed to like that suggestion and rolled off me, starting to unbutton his shirt.

"Clothes on is nice," I said as I fiddled with his fly. "And if anyone comes, we can just zip up -- nothing happening here."

"I thought you were single?" He didn't sound too bothered, his head back on the pillow. It's hard to complain when you're about to have your cock sucked.

"I'm thinking about you, silly." I tugged his trousers down past his hips. He lifted up to help. "Jenny might come."

"I'm sure Jenny's coming," he said. "But not here."

The image of Sally and that red-headed tart making out on the bed she'd sucked me off on just that morning flashed through my mind, filling me with jealous anger. The jealously was what gave me the courage to take Simon's underpants down, and saved me from wetting myself again -- in fear this time -- as his huge cock sprang free.

"It's so big..." I gasped.

"I've had no complaints."

I set my fingers tentatively against its thick, veiny length. The pink nail varnish that Sally had painted on that morning renewed my sense of outrage at her duplicity and strengthened my resolve. I took a firm hold, marvelling at how hard he was, and steered what had to be a good eight inches, towards my open lips.

"Mmmmm...." Simon gave a deep, happy groan as the head of his cock filled my mouth. I'd always enjoyed sucking on Sally's nipples, but this was somehow so much better. There was a faint, musky taste, to it, but mostly it was just warm meat of just the right shape to satisfy my mouth.

I took his shaft in both hands and wanked him gently, my lips just past the glans. In a moment of clarity, I realised that I was in a strange man's bedroom sucking his cock while wearing his girlfriend's dress. It was a million miles from how I'd imagined my Saturday would go, but somehow I was far more into it than I would ever had admitted or even imagined in my most secret fantasy.

I rested my head on Simon's groin and sucked on his dick like it was a popsicle and I wanted all the juice out of it. He reached down and stroked my neck, and for quite a while we stayed like that, a gentle, loving thing.

Of course, as his excitement grew he started to make small thrusting movements with his hips, trying to get more of his shaft into my mouth. I knew I should be taking more of him in. I should let him get right to the back of my throat. Down my throat even. Certainly, if I wanted to get all of him in, like Sally took all of mine, then I'd need him halfway down my throat.

The problem was my gag reflex. It's always been pretty strong. I can't even spend long cleaning my back teeth without starting to feel a little nauseous. Simon thrust, just a little, and the extra half inch had me gagging and spluttering.

"Sorry, baby," he murmured.

I carried on, but my jaw was getting tired and I knew from personal experience that it's hard to come if just the top of your cock is getting sucked. I stroked my hand up and down his shaft but that wasn't really doing the job. How long, I wondered, before he gets bored? How long before he pulls away and is back to exploring my tits, or I found fingers hunting around my pussy, wondering if maybe we can just do it anyway?

If he hadn't been such a big boy I might have done a better job, but my jaw really was starting to hurt. I realised that I'd got myself in even deeper and that there might be only one good way out.

I pulled away, planting a gentle kiss on the top of his huge, troubling penis.

"We could ... try another way?" I moved up to lie beside him. I met his blue eyes. "Only, I've never done it before..."

Simon's face lit with soft delight. He kissed my mouth tenderly and reached a hand around to clutch my ass through the tight black material of Jenny's dress. "Little Mary's a virgin?"

I bit my lip and nodded. "You'd have to be gentle."

"Oh, I will."

"I mean, like super gentle. Like a brain surgeon. And if it's too painful--"

"If it's too painful I'll stop immediately, baby." He kissed me again. Then again. Then three more times. Long, tender, kisses that melted me inside and had my hips bouncing me against him.

I could have kept kissing like that for hours, but reluctantly, I let myself be rolled away until my bum presented itself for his attention. I hiked the dress up to expose my cheeks and reached down to tug my panties aside. Looking back at him over my shoulder I suddenly felt like a very very naughty girl indeed.

"You might need something to help..." I didn't think my saliva would be enough lubricant, and besides, I hadn't got it over much more than the tip of what he wanted to put inside me.

Simon rolled to the side of the bed where he'd left the picnic hamper when he came in to find clothes for me. He rummaged for a second and held up one of the little pats of butter that Sally had put in that morning. "Good enough?"

"Mmmm..." I batted my lashes at him. I was scared but at the same time I wanted him so much. We were way past the point of turning back. I wanted his cock in me. I wanted to be his girl.

Deftly, Simon rubbed the butter over the considerable length of his cock and moved up close behind me. He held my shoulder with one hand, his mouth close enough my ear that his breath tickled me deliciously. He used his other hand to steer himself between my ass cheeks. I reached back for the final guidance and was soon rewarded with blunt pressure of his cock up against the tight virgin pucker of my asshole.