Losing Bet

"I think it's time for your rosebud to become jewelled now, don't you?"

"Mmmmm yes, fill me with it."

I wiped my fingers on the damp cloth I'd thought to bring from the kitchen and picked up the metal plug. Instead of smothering it in lube and inserting it straight away, I teased her further. I stroked the cool tip of the toy along her folds, slickening it with her juices, pushing deeper inside each time, then withdrawing and exciting her swollen clit with the tip.

"Fuck me with it. I want it inside me."

"Really? Ok then, you asked."

I pulled it out, still dripping in her juices, and pushed it into the tip of her tight opening. I pushed it deeper, opening her up as far as I had before pulling back and repeating the move. Each time, the resistance I felt pushing back lessened, and I went a little deeper each time. Eventually, I found myself just shy of pushing the toy past its widest.

"Nearly there, next time you'll take the whole thing, you kinky little girl. I want you to stroke your clit as I slide it home. Enjoy the moment of losing your toy cheery."

Immediately her hand shot back to her nubbin, flicking across its surface. Bringing herself to the edge of an orgasm as I held her open with the scarlet metal plug. It slid in and out, twisting the toy slightly to further stimulate the sensitive nerves at her opening.

"Do it, do it now; I'm about to cum."

I pushed harder, and the moment it went past the widest girth, the plug was pulled from my grasp as her sphincter took hold. Moments later, Jen collapsed in a shuddering orgasm as the waves of pleasure crested over her.

"Nnnnggggghhhhh fuuuuuuuck me, baby. That was great!!!"

She collapsed on me in a beautiful heap. She was shuddering through the spasms of her orgasm eventually. Finally, however, she picked herself up and pulled her knickers back into place, wiggling her bum at me to show off her new jewellery and turning this way and that to see it in the mirrored pillar off to one side of the sofa.

"What do you think? Is it cute? Do I fit the title of classy and kinky?" she asked, still a little unsteady on her feet. Then, before I could answer, her eyes fell on the pronounced tent in my shorts. "Oh, dear. Did I do that? It looks uncomfortable. Perhaps I could help you ease that swelling I can see."

She helped me to my feet and kissed me fully and hungrily. Our tongues met and snaked across each other in the passion of the moment. Her hand slid down inside the waistband of my chino shorts and grasped my rocklike manhood wanking me slowly as we kissed. I groaned into her mouth as she did so, the pleasure pulling the sounds unbidden from me. Then, she broke our kiss with a slight laugh and looked down.

"Yes, I think I really ought to fix this, don't you?"

Jen dropped to her haunches with her legs spread and her face in line with the apparent bulge in my crotch. Then, never taking her eyes from mine, she pulled down my clothes, freeing my tool, glistening with precum.

She licked the surface, sampling the lubrication with a smile.

"Hmm, yes, an excellent vintage. I'll take the whole bottle."

With that, she swallowed me near whole. She alternated between bobbing along the length of the entire shaft and then licking from balls to tip. Between the events of this afternoon and her admissions, I knew I wasn't going to last long, no matter how much I wanted it to last.

"Oh god, I so want to fuck you, but I can't last like this. I'm gonna cum in your beautiful mouth."

For a moment, she stopped, only to say, "Good. I want your cum. I want to taste you."

And back she went sucking my head, flicking her tongue along the underside of my glands.

I could hold on no longer, and rope after rope shot from my tool into her waiting mouth. She sucked and swallowed until finally, my orgasm subsided, and she released me with a smile.

"Oh god, that was good. I'm just sorry I couldn't fuck you."

"Oh, we have some time yet. Perhaps if we watched a little television, you could recover."

Jen went over to the laptop on the counter.

"Hmmm, decisions, decisions what to choose. This one? No. Maybe this one. Ah, I know."

I quickly stripped naked while she was deliberating and returned to the sofa.

"Be a darling, find the remote and turn on the tv, will you? I think I've found one we'll both enjoy."

I flicked the enormous on and watched as Jen used the Chromecast to mirror what she was seeing on her laptop. I expected to see the website, but Jen said that the streaming ruined the quality. She had the original file. I guessed then that this was something from Sam personally, and I wasn't wrong.

Jen clicked on the video file in the folder she was reviewing and put it to Fullscreen, filling my view. Sam was walking towards two women, stockings and high heels like her. Unlike Sam, though, the older redhead was already sporting a strapless dildo, and her younger friend was lifting her leg on a chair to insert her own. While there was no audience, no one wore a mask or were blurred to obscure identities. This was for private consumption.

My friend took her place beside me on the cream leather and before long had one foot up on the table and her hand in her pants, slipping her fingers between her drenched folds. On-screen, the two unknown women, were taking turns fucking Sam on a wide bed in various positions, slowly building in pace and roughness.

Before becoming too rigid, I thought it best to make a quick detour to the toilet to relieve my bladder. When I returned moments later, Jen had repositioned herself, so she was standing legs spread behind the sofa, her knickers draped across a cushion in front of her. She was leaning across the back with one arm, and I could also hear a wetness that implied I was not the only one enjoying the film.

"Fuck me, darling. Come here and fuck me. I want you inside me. Shove your meat inside me while we watch Sam get fucked like a slut by these two women."

I didn't have to be asked twice, so I quickly positioned my now fully hard cock at her opening, coating myself in her juices.

"Don't tease me; you did that enough today. Fuck me!"

With that, she pushed back against me until I bottomed out against the jewel of her plug with a grunt.

"Fuck yes, this feels great. I love the feel of your plug against the head of my manhood."

"Oh yes. I'm never taking this out. I feel so full."

We started to fuck slowly while watching the homemade porn. With every thrust, I could see the neck of the plug move as my cock pushed past the thin wall.

"So will you show everything tonight then? Will you fuck yourself for your friend and all those strangers online?"

"If I do, will you wank to it?

"I'll do more than that. I'll fuck you watching it."

"Then I'll have to be extra sexy. Maybe not for strangers just yet. They can get photos, but I think you and Sam deserve a video of me fucking myself."

The talk was turning me on, making me even harder, my pace picked up. On-screen, Sam's cries of pleasure grew louder as the women D.P.'d her.

"You'd like that, wouldn't you? Sams rubber cock in your pussy and my cock in your arse."

"I've never been fucked in the arse before."

I grunted as I fucked her deeper.

"That's not an answer."

"Oh god, I'm cumming."

I could feel the walls of her cunt contract around me, and I carried on fucking her. It felt delicious. I didn't stop, but I did at least slow down long enough for her to catch her breath.

"Was that an answer then?" I said, grinning as I thrust away

Jens juices were now dripping down my thighs and soaking the tops of her stockings. A wonderfully erotic sight as I worked away at her pussy, pushing her closer to another orgasm with every thrust of my member. With every slap of my balls against her engorged clit.

"If you don't let me know, I'll stop."

I, of course, had no intention of doing anything but shooting my load deep inside her, and I'm sure she knew that, but it drew a response from her.

"You wouldn't."

"I'm sure Sam would love to. I can video call her now and ask if you'd like."

"Don't!" she panicked.

"Well then. Do you want me to fuck your tight little virgin arse?"

"Hoooooonngggghhhh," was the breathy reply as another orgasm building. "Yes. Yes, I want you to take my cherry and fuck me up the bum."

"And Sam. Do you want her to fuck you?"

"Hoh god, oh god, oh god." She was getting closer, and so was I. "Yes, I woke myself up dreaming about it last night."

"And what did you do?"

"I buried my dildo in my cunt like a little bi slut until I came."

"Good girl. Now tell me. Do you want us both? Both of us to fuck you at the same time?"

Jenny's breathing became more ragged as she got closer to what I thought would be a monster orgasm. I wasn't sure if she could even hear me now or if she was lost in the moment and the pleasure we both found in each other.

"Fuck yes. I want to be fucked. Use me. Cum in me, Cum on me. I want to watch you fuck her, and I'll fill myself with the biggest dildo I can fit in me. I don't care. Just make me cum and cum again. I want it all."

This was absolutely the sexiest thing I'd ever heard, let alone while I was fucking a girl. Finally, it was too much, and I exploded into her. My orgasm pushed Jen over the edge, too, and she collapsed over the back of the sofa, a quivering mess while I pumped my seed into her.

Jen went to clean herself and change her cum soaked stockings. When she returned, makeup touched up, and lingerie tidied she was still every inch the sex bomb was greeted with an hour or so ago. I had to leave. It was Sam's turn to enjoy the view.

"Do you think she'll know?" Jen asked as she saw me to the door.

"For sure, the place positively reeks of sex. I'm sure she'll think it's perfect for the evening's fun. You never know; maybe you'll get laid again."

"I hope so."

I left in a cab and returned to my unfinished flat in south London. No redecorating got done that night.

The next morning though, I had an email from Sam with a download link for a folder containing the evenings' photoshoot and several video files. The message read:

Mark,

Thanks for helping Jenny's shopping yesterday. I hope you will be available to help again next week, not with the shopping but to warm her up again as you did before my arrival.

Unfortunately, I could not fuck Jenny tonight as I did not think to bring the right toys with me. So instead, I had to satisfy myself by lapping at her cunt as she did the same to me. I have enclosed the evidence of our evening, and I hope you enjoy it as much as I will, thinking of you wanking.

P.S. Stick around next time. I'm sure you'd make a wonderful subject of a film or two.

It looked like the following Wednesday would be more fun than I'd imagined.