The Wager

He pushed gently, then a little harder. I gasped and tried to press back. It felt a million miles from being able to fit. Despite myself I clenched against him and it was soon clear we weren't getting anywhere.

"I know what to do," Simon murmured in my ear. He reached two fingers to my mouth, and obediently I sucked them. They tasted buttery.

I rolled forward at his direction, spreading my legs. Moments later a wet fingertip found my anus, and I had to surrender to its gentle but irresistible pressure. His finger felt as big as his cock, filling me while I squeezed it very tightly. Slowly, while I moaned softly into the pillow, Simon fingerfucked me. First with one finger, then with two.

When he said Sally was probably doing the same thing to Jenny, I groaned and lifted my ass to him, rocking back until I'd taken both fingers as deep as they could go. "Simon..." I whispered his name.

I lifted onto my hands and knees, head down, shuffling back to the edge of the bed. Simon stood behind me and returned the head of his cock to my asshole. The stretching had worked wonders but still I cried out in pain as the pressure built and the tip of his cock started to make an ever-bigger 'o' of my poor little anus.

Immediately, Simon pulled back. "Mary..."

"No, I want you." I looked back over my shoulder at him, handsome, caring, his broad chest exposed through a half-unbuttoned shirt. "Fuck me. Please."

And so, gently, slowly, accompanied by my groans and suppressed cries, he entered me, inch by inch. With half of him in my tight ass he began to move his buttery cock fractionally back and forth. I bumped softly back against him, taking him a little deeper each time. Until, at last, he stood there, hilt deep in me, my bum cheeks pressed to his groin, his hands on my hips.

"God Mary... You look so fucking sexy like that." He pressed, trying to get even deeper. "You're so warm and tight and ... yummy."

My asshole felt like a ring of fire around the base of his thick cock, and I felt so full of him, so stretched, that I might burst. But on the other hand, the feeling of that penetration spread a deep, wonderful sensation through my insides, and there on my hands and knees I felt at once both deeply slutty but also that it was a strangely loving thing: even though I'd only known Simon a few hours I felt cared for and knew that I wouldn't have wanted to give my virginity to anyone else. I wanted to be his girl. I wanted him to fuck me. Hard. I wanted him to come inside me.

Slowly and deliberately, I began to rock back and forth, sliding on his cock, letting the glistening length of it escape from inside me before impaling myself on it once again. After a while, Simon held my hips and began to move too. I could hear him starting to feel it. His breath came faster. He started to thrust. His grip tightened on me. He lasted longer than I would have, but no man can hold out forever when their cock is being repeatedly buried to the base in something warm and wet and tight and sexy. Especially if it's new.

At the end he lost his gentleness and just fucked me with abandon. I knew I'd pay for it later with a sore ass, but right then I didn't care, just gasped and begged him to do it faster while my breasts jolted in my bra. He came hard, spasming against my bum, emptying his come deep inside me while he ground up against me. I fell forward onto the bed, and he followed, staying inside me, still pumping.

Pinned under his weight I let my hips move against the mattress. In my panties my chastity felt hot and damp. Simon lay on top of me, panting, pausing now and then to kiss my ear or the back of my head.

"That was so good," he breathed.

"Mmmmm...." I lay helpless beneath him, full of his come, squeezing his softening cock with my ass. I thought about the fact that I was in his girlfriend's dress and my girlfriend's panties, and I wriggled deliciously.

We arrived at Sally's flat about an hour later. I'd straightened out my dress, and done what I could about my makeup -- which honestly wasn't a lot. I rang the bell and Simon stood behind me with the hamper. I was still a little drunk and nothing felt quite real.

Sally opened the door, appraising us both with a smile before inviting us in. Jenny was in the kitchen drinking a coffee. The first topic of conversation was of course the fact I was wearing a different dress. The girls accepted our story of spilled wine, and Jenny said I could keep her dress. She said it looked better on me anyway. We sat and talked about nothing for a while before Jenny reminded Simon that they were supposed to be watching a play that evening. A few minutes later they were leaving to get ready for the theatre. Both of them gave me a goodbye hug and a kiss on the cheek.

"Well." Sally sat back in a kitchen chair and watched me over her coffee. "Did you have a nice day?"

"I won our bet," I said, still wondering what Sally and Jenny had been up to. There was nothing to show any mischief had taken place.

"Did you?" She raised an eyebrow.

"I did." I nodded. "You're not going to tell me that Jenny suspected?"

"No." She held her phone out to me. A series of text messages were on the screen.

Simon: Is Mary trans?

Sally: She is. Be nice to her.

Simon: Will do.

"Oh," I said, suddenly feeling crushed. The timestamps indicated the exchange must have happened while I was showering.

Sally smiled encouragingly. "I think you did a pretty good job."

"You do?" I still felt terrible. Simon knew?

"Well," Sally said. "You got him to fuck you. So, you got to have anal sex even without winning the bet."

"How did--"

"It was written all over both of you." She rolled her eyes. "I could see it right there on the doorstep." She shook her head. "It was kind of cute, really."

"You're..." I hadn't wanted to admit it. Still didn't. But I'd rather blurted it out already, so it was too late for denials. I blushed furiously. "You're not angry?"

"Angry?" Sally grinned. "Not at all. I mean. It's my fault really. Mine and Jenny's. We realised that both of us had boyfriends pestering us for anal sex. So, we put you together to see what would happen."

I stood up sharply. In a heartbeat I'd gone from worrying how angry she was going to be to being angry myself. "That's a terrible thing to do!"

"Nonsense!" Sally ignored me. "Nobody made you pull your panties down for him. You did that all by your slutty little self ... Mary."

Confused and upset I turned away. "I'm going to get dressed and then I'm going home."

"About that..." Sally said behind me. "I did win the bet."

I spun back round, half enraged, half amused. "Seriously? You're going to make me keep wearing your panties?" That had been the bet: if I lost, she could choose one item that I had to wear as often and for as long as she said.

"My panties? No, I want those back. If you want to be a girly-boy you'll have to buy your own lingerie, Mary."

I frowned. Confused. "What then?"

"The chastity, of course, silly girl." Sally leaned back in her chair and smiled. "You'll be keeping that on for quite a while."

And in that moment, I knew then that I'd lost a lot more than a bet that day. More than my virginity too. But also, that I wasn't at all sure any of it was a bad thing.