The Second Wager

"It was a one-time thing!" I protested "That. You. Set. Up."

"So, you want another chance?" she asked.

"Of course I do."

"You'll have to prove to me--"

"Anything!" I cut across her. "Don't do this."

She looked me over, eyes glinting in the streetlights. "You've got six more days of girl dressing--"

"Still?" I gasped, amazed.

"A bet's a bet," she said.

"So, you want me to go back to my flat and wear this dress for a week?"

"No, that would be silly."

I was about to say I was glad she'd seen sense. But she glanced over to where Jenny had just turned her back on Simon and was stalking back towards us.

"Six more days," Sally said. "And you stay at Simon's."

"That's what caused all this in the first place!" I shouted.

"I'll come over each morning to teach you to do your own makeup and check you're following the rules. I'll bring you fresh clothes."

"I don't think Simon will even want me there," I said.

"He will if Jenny tells him to," Sally replied. "And! If at the end of the week you can look me in the eye and tell me that the whole time you were staying with him you didn't let him fuck you again ... then we'll both have you back. Plus, as a one-time thing" -- she echoed my words -- "I'll let you have my bum. And if I like it, we can make it a regular thing. But! If you can't stop from being a slut, then we're through. I'll give Simon your chastity key and he can decide what to do with you. Deal?"

I shook my head. This was crazy. These wagers were just getting me deeper into trouble, further from sanity. I'd had a wonderful girlfriend, and now I was practically being given to her cousin's fiancé, in heels and chastity. None of it made sense.

"Or we can just say it's over now," Sally said.

"Deal."

And that's how I found myself walking back to a dejected-looking Simon, a little drunk, a little unsteady in my heels, and in a fairly similar place to where he was. Both of us on notice and under probation.

"Hey," I said.

"Hey."

"Give a girl a lift?"

He looked at me, eyes still lingering on my body. With a forced smile he said, "Well, if you're spending a week with me I probably shouldn't make you walk to my place."

"So, Jenny told you the deal," I said.

He nodded. "Part of my punishment." He met my eyes with a real smile this time, albeit a weak one. "She said you were going to stay with me as a test of my faithfulness. And that if we couldn't share the same roof for a week without repeating our ... mistake, then that was that, we were through. But now that I think about it, that makes no sense. I mean, why would you agree to it?"

"Maybe I want to test you too?" I said, suddenly bold. I returned his look with a frank one of my own. I needed to stay with him to repair my own relationship after all, so I had to play along. "I don't want to break you and Jenny up. But maybe if you can't behave yourself it will mean we were meant to be together. Besides, Sally asked me to, and it's the only way to keep her as my friend, and I really like her."

"All the girls do." Simon grinned ruefully.

"Let's just both try to be good and hope at the end of the week she believes me. The only thing you have to know is that I'm not going to lie about this. I'm a terrible liar anyway -- Sally will know straight away if I try. So, we really do need to not ... do that again, if you want Jenny back. For real."

Simon looked surprised but nodded slowly. "It's going to be tough, Mary, but I have to tell you now, I mean to pass this test. I do want Jenny back."

I nodded. This was going well. "So, where are you parked?"

Simon's BMW was parked in a backstreet a couple of blocks off. The walk through the warm night cleared my head a little. After the first corner he took my hand and we walked side by side.

At the car he opened the passenger door for me. I moved to pass him and get in.

"This is going to be tough," he said, as I came close. "I really wanted you tonight ... when we were slow dancing."

I looked up at him, daunted by his size again, feeling so girly. "I wanted you to kiss me," I admitted.

"And now?"

"We should behave."

"But you do?"

I looked up at him. The moon hung huge in the sky, wisps of high cloud across it. "More than ever."

He bent to me and his warm lips met mine. I opened my mouth to his tongue. The tingle in my panties made my hips twitch. I pulled back, "We shouldn't."

"Kissing's allowed. She didn't say we couldn't kiss."

"You know where it will lead." And with great self-control I got into the car, closing the door behind me.

He drove back, reaching the road that skirts The Fields where we had our picnic. The whole time I sat there I was feeling his kiss, his lips on mine, his tongue invading. Images of him lying in bed that last time returned to me. I felt drunk again and I wanted him. But I also very much wanted to win the wager with Sally. I wanted her back. I wanted the chastity off, and the promised reward -- that I could do to her what Simon had done to me. Anal sex after all she'd put me through would be sweet. I did not plan to be gentle. Or maybe I would be, in the hope we could do it regularly. But either way -- I wanted it!

Simon rested his left hand on my thigh. Suddenly I knew that there was no way we weren't going to end up fucking. Not after that kiss, that dance, those drinks. I was doomed before I'd even started. Sally must have seen it.

My mind raced.

"Turn down there," I pointed to the road that led to our picnic site.

"I live on the left," he said. "That's just the Fields."

"Jenny said if we couldn't share the same roof without repeating what we did, then she wouldn't have you back?"

"She did." He slowed the car.

"Well, we're not sharing the same roof ... yet," I said. "So, anything that happens before we do -- I don't have to lie about."

Simon made a hard right having almost missed the turn.

Within a minute his headlights illuminated the deserted carpark where we'd first met. The long grass of the Fields rippled on all sides.

"If we get this out of our system once and for all then we can survive the week," I said.

"We can." He nodded. "We can do it."

We got out of the car. With the lights off we were in darkness. Even so close to the town I could see stars overhead. The breeze was warm. He took my hand and I let him lead me towards our picnic ground, following the trail by moonlight. I took my heels off early on and carried them in one hand. They kept sinking into the ground even though it was dry.

After just twenty yards Simon turned me towards him and kissed me again, deep and passionate. My body ached for him. I pressed my fake breasts against him, wondering what it would be like to have real ones. I was going to let him have me again and the prospect thrilled me. I'd found a loophole and I was going to use it. Hard.

Before long we were alone at the dark picnic site, standing in the warm breeze amid the waving grass, wrapped in each other's arms, kissing passionately. Simon's hands roamed my bum, cupping my cheeks and pulling me tight against him until his erection pressed hard into my groin and my little chastity squashed against him.

While his tongue explored mine, his fingers rucked up my dress until at the front it was so high on my thighs I could feel the night air through my underwear, and at the back he had my bottom fully exposed. He slid both hands into my panties then, stroking, squeezing, separating my butts, touching a fingertip to my little pucker, rubbing in a gentle circular motion that made me sigh and told me exactly what he wanted.

Simon had had the foresight to brink a blanket from his car and spread it on the longer grass at the edge of the site, pulling me down to join him. For a while we lay side by side, kissing, not speaking. His hands returned to my ass and to touch my eager asshole time and again. I wanted him so much that my hips moved against him. He stroked and squeezed my breasts too, moving lower to kiss them through the thin material of my dress. I couldn't feel it of course, but it turned me on knowing he had his mouth on those stiff nipples.

He returned to kiss my neck, my mouth, my cheek.

"Mary..." he whispered so close to my ear that it sent shivers through me. "Sweetheart."

With that he rolled me onto my front. I was expecting him to take me then, but instead he moved down my body and started to kiss the base of my spine and the tops of my butt cheeks, stroking and squeezing both gently with his large hands.

With the lightest of movements he encouraged me to lift my ass to him, and, feeling very slutty, I did just that. He hooked two fingers under the crotch of the red lace panties Sally had dressed me in, and pulled them to the side. The first touch of his tongue against my asshole was a revelation.

"Oh God... that's so good!" I lifted even more, presenting myself to him, shameless.

He licked the full length of my ass crack, swirling his tongue across my little hole. On the second pass he paused longer, and the tip of his tongue probed me, trying to dig in.

"Oh God, yes." I gasped. "I want that." My hands were off the edge of the blanket and my fingers knotted in the grass, painted nails scoring the ground.

I lay with my bum in the air, knees drawn up to lift it, chest to the blanket, face too, turned to one side, eyes closed, mouth open. I discovered in the next few minutes a whole new world of unexpected pleasure. Simon's tongue owning my almost virgin asshole felt so divine it left me panting with lust. And when he relaxed the necessary muscle sufficiently and French kissed me down there, managing to penetrate a little way with his tongue, I shuddered with the desire for more.

When at last he rolled me onto my back I was totally ready to be fucked and rather surprised to find myself facing the stars instead of on all fours like our first time. Simon reached for my panties and started to ease them down. I tried to stop him, suddenly realising that I would be exposed.

"It's OK, baby. I already know what kind of girl you are." And he pulled them down. "...or maybe I didn't..." His fingers touched the little steel dome, and I writhed in shame. "That is so ... sweet," he said. He reached between my thighs and cupped my balls, rolled them gently, the rubbed his palm slowly over my chastity. The tingling throb came immediately, and my hips twitched. "How long have you been locked up?"

"I was in it when we met. Sally put it on. She has the key." Since Simon was being so nice I felt much better about it. "I've been in since then."

"But that's weeks..." He stroked me. "And you can't get out, even if you wanted to?"

"I do want to," I said. "I want to come. But no, I can't get out."

"Oh darling." He laughed, delighted. "That's perfect. I love it."

"You do?" I asked.

"I do." He undid his belt and moved on to his trouser button. In a smooth motion he skinned them down along with his boxer shorts, and I was staring at his throbbing erection, once more amazed at just how big it was compared to what I had when I wasn't squashed into a nub.

"Mmmm..." I reached for his gleaming member, marvelling at the girth of it in my hand. He was going to put the whole thing inside me again. I wanted him to. But I was a little scared as well.

"Baby girl..." He bent to kiss me, pressing me down to the blanket.

"Oh..." As he spread my thighs I realised he was going to have me like this, face to face.

Simon settled his weight on me, and once more I felt his erection against my thigh, only this time it was my inner thigh, and it was skin to skin.

I looked up at his face, the moonlight offered only the angles of his jaw and cheekbones. It glimmered in his eyes, and painted his dark hair black in the night. "I adore you." It was true, and locked away, wearing a dress and fake breasts I felt completely comfortable saying it. I ran my hand along the side of his face, and he kissed my fingers.

Simon lifted up on his arms. An adjustment of his hips brought the head of his cock questing between my bum cheeks. My asshole was well lubricated thanks to Simon's dutiful attentions, but in self-preservation I spat gently into my palm and reached down to guide him to his destination whilst at the same time working my saliva along his shaft.

His cock found my asshole and I shivered with anticipation. All the dressing up, the dancing, the whole night, it had all been leading to this moment in the warmth of a summer night out on the deserted heath.

"Mary," he breathed, pushing softly, "my angel."

I put my head back, lust making my breath come faster and harder.

Simon bumped his thick cock against my hole, pushed more firmly, and with a gasp I began to surrender to him.

"Do it," I moaned. "I want to be your girl, your sweetheart, your angel, your little whore..."

As the word 'whore' left my lips he entered me, one slippery inch following after the next. "Baby girl..."

"Gently." I put both hands to his hips. I wanted him inside me but it felt as if I were tearing open. It had been the same the first time. I knew it would get better as he broke me in.

I could tell that Simon just wanted to thrust into me and fuck me hard until he came. But he restrained himself, the moonlight catching his smile as he eased himself in, then nearly out, halfway in, then so far out that my poor little asshole barely had hold of the head of his cock, back in a little further, out almost as far, in again, deeper each time, opening me, owning me.

I spread my legs wider, wanting all of him. My cocklette tingled in its prison but the mix of pain and pleasure from my ass overwhelmed those sensations. This was all about my guts as Simon's long, thick shaft explored new depths of me.

I moaned gently and took my hands from his hips. Sally had made me into a pretty girl, and Simon was making me into a woman. The chastity had taken away my manhood, and the dresses, panties, makeup, all the rest had feminised me. As soon as men had started looking at me lustfully, something inside me had responded, wanting them back, wanting Simon. I'd let him kiss me, explore me, and now fuck me, with my little prison gleaming between us, a source of excitement for him.

"Oh gosh..." I was starting to really feel it now.

Simon sunk himself to the hilt, his heavy balls coming to rest against the cheeks of my ass. I reached up and pulled him down, and we lay kissing, with him filling me, his hips bumping gently to see if an extra millimetre might gain entry. My insides clutched at his thick cock, and as his tongue invaded my mouth I pictured the head of his penis, eight inches deep in me, twitching with lust, waiting to spurt his seed.

"Darling..." I loved that we were outside. Someone could happen upon us at any time, and it didn't matter, I was his girl again.

Slowly he lifted back up and began to thrust faster, slapping up against the insides of my spread thighs. I could see my Victoria's Secret panties hanging from my left ankle and something about the image made me pant.

Simon fucked me with long slow thrusts mixed with periods of fast short ones, sometimes just bucking against me, buried entirely inside the whole time. When he first came all the way out of me, only to slip right back inside a moment later, my asshole welcomed him without protest, fully up to its new role as Mary's pussy. I moaned and told him to do that more. I loved the feeling of him re-entering me. I felt so slutty, making demands about how I was fucked, and the slutty feeling made the throb in my chastity grow. My cock still couldn't get hard, and was still skewered by the urethral tube, but somehow managed to feel delicious even so.

Finally, Simon's breathing grew ragged and he started thrusting faster and harder than ever before, really pounding at me, so powerfully that I was a little scared. The sensation that wrapped its tendrils around my churned guts was so strange and wonderful that I cried out, not caring if anyone might be out late walking their dog nearby.

With a gasp and a grunt of his own, Simon orgasmed, his cock twitching as it spurted inside me. Four or five more strong thrusts and he was collapsing onto me, panting hard. I put my arms around him and took his weight, my breasts crushed between us. This was my time, when I was in charge, and he was my baby. His sperm was mine, his cock slowly softening, his balls drained, and his strength spent. I held him close, stroking his thick hair and kissing his forehead.

We lay like that for an age. At last, he pulled his limp penis from me and rolled clear with a sigh.

"Mmmmm...." I sat up and pulled my panties back on.

"That was wonderful," he murmured, looking up at me.

We walked back to the car, hand in hand. I could feel the wetness between the cheeks of my bum, and my asshole burned with the abuse it had taken, but I felt great, even though I hadn't come. My chastity did felt sticky, and my balls didn't ache. I thought that perhaps Simon had succeeded in milking some of the sperm out of me, drop by drop during his most powerful thrusts. Either way, I felt ready for bed.

At the door to his flat I stopped him. We stood close together by the porch, and I looked up at him, even back in my heels he was significantly taller than me. "That was our free-ticket. Once I'm through that door I'm living with you, even if we go back out to the Fields. So, this can't happen again. Because if it does, Sally will know about it, and then Jenny will know about it." I went on tiptoes and kissed his lips. "It's good that we got it out of our system, yes?"

Simon nodded, frowning.

"But for the next week we have to be good. Then you can have your lovely fiancé back." And, though I didn't say it, I could have my life back. I could get my chastity off. And as an added bonus, I could have the thing that started this whole madness in the first place: Sally's ass.