Losing Bet

"And?" I asked.

"Hahaha, what do you think happened? I came. I swear, Mark, I barely touched my clit, and I just came there and then on the loo. I couldn't help but think about being on that site, all those men and women looking at me, not knowing who I was but getting so turned on by what I would be doing. It turned me on so much that I came harder than I have in years."

"Fucking hell! I would never have placed you as one of those women."

"Me either. Sure, I've fucked myself to the idea of it in the past but never like, seriously. I mean, after one of those erotic stories, maybe, but that's it... Anyway, when I came back, I could hear a noise from the living room, you know, like moaning?"

"I think I can guess the kind, yeah."

"Well, when I get there, Sam is sprawled out on the sofa with her hand down her bikini bottoms, fingering herself like mad. She'd put one of the videos from the site upon the telly. I swear on the big screen, large as life, was this beautiful woman with her head between another's legs, fucking her with this massive dildo. It was so big, Mark. She couldn't get her fingers to touch holding it; it was that big. But, still. it was going in and out of her like a fucking piston, you know?"

"I can imagine, yeah," I said, a little dry-mouthed.

"And Sam was just watching, open-mouthed, fucking herself. So I just watched her until she saw me and stopped. That's when she made a bet. Sam said we should both strip off and wank to a video, and whoever would cum first should pay a forefelt."

As you could imagine, this had come as a little of a shock. I mean, lingerie shopping with your mate was a bit of a stretch for our friendship. But, her admitting the reason we were is that she'd been wanking with her mate last night to porn on the big screen is something else. I couldn't help it; I was horny as hell and needed to know more.

"So?"

"So? I agreed, of course. I thought I'd just cum so I would be ok for a bit. So we sat there naked while she cued up the next clip, and... well mate, I was creaming myself already. This time it was one woman with three guys taking turns fucking her. She was sucking and fucking. Wasn't it even like she was all that hot, you know? She was just some housewife in her 50s but fuck man, she was going for it, and I'm going at my bean like I've never jilled before in my life. Sam's there next to me with three fingers inside herself and moaning away like I'm not in the room."

Jen looked around, making sure no one was eavesdropping on us.

"So I think I'm safe, right? She's about to cum there and then surely, but no, she just keeps finger fucking herself in time to the cock on the screen hammering away at this slut who's just loving it."

I swear I have never been so glad for a secluded table as I was now. I had a raging hardon, and it was all I could do not whip it out and start beating myself off there and then.

"Are you alright?" she said, looking at me right in the eye. Did she know what she was doing to me right now? "You've not touched your food."

I took a mouthful of the Bahn Mi I'd ordered half-heartedly. For some reason, I was less interested in eating than when I arrived. Jen hungrily wolfed down her noodle salad and continued as this was just a normal chat.

"When I looked back on the screen, one of the guys blew his load all over her tits." Jen said between mouthfuls, "I knew I was in trouble as I almost came there and then, but I kept it together somehow. The next thing I know, she sat on one guy fucking him, and the last one gets up behind her and sticks his cock in her arse! Oh god, two cocks at once, the lucky bitch and then...."

I paused with the sandwich half way to my mouth.

"Bam... I came. I came watching some housewife, some perfectly normal woman getting fucked by two old guys like a complete slut and I'm a quivering wreck because I wanted to be her with mu pussy and arse full of cock. Then, not ten seconds later, Sam lets out this massive groan and let rip her orgasm right there next to me."

I said nothing; what could I say? It took all my effort just to get the sandwich the rest of the way and take a bite. Jen looked at me expectantly.

"Well then. Say something."

I almost choked on the crust of the Bahn Mi.

"What the fuck do you want me to say? Despite never talking about sex at all with me before in the entire time we've known each other, you have just told me in explicit detail about how you had your friend wanked to porn last night and had multiple orgasms. I dunno Jen, it's a lot to take in in one go."

"I'm not finished, though. Do you want to know the end?"

I could make a good guess, I thought. I wanted to hear her tell it, though. I wasn't sure what was happening here, but I was too far along not to see it out to the end.

"Go on then, tell me."

Do you want to know? I'll only tell me if you want, really want to know."

I nodded.

"Say it then. Tell me you want to know more."

I looked at her. This was not the Jen of old. This was a new woman.

"Say it. Say it, or I won't tell you."

"Oh fuck yes. this is the sexiest thing I've ever heard from you, from anyone. Please, tell me what happened next."

Jen smiled, comfortable that she hadn't fucked things up between us.

"That's when Sam told me what she had in mind as punishment for losing, that it was to do me good; you now increase my confidence? She wanted me to do a solo photoshoot with her tonight, something sexy. I could remain anonymous, but I had to flash some skin, at least my boobs, but as much as I was comfortable with. I said I wasn't sure, and I'm not like her, you know? I've never even been naked in front of more than one person before. Sam explained I wouldn't be, and it would just be her.

Jen finished her bowl.

"That's when she suckered me for a second time. She said we could always go double or quits if I felt that way. So, I would shoot two sets for her, whatever I wanted, as hardcore as I wished, and Sam would have to do it if I won. If she won, though, well, I'd have to do two sets.

She didn't say I'd have to get my fufu out, but it was strongly implied."

"And you thought you could win this time?

"Honestly, I didn't know. Anyway, I was horny as hell and wanted to carry on, so I figured what the hell, in for a penny, right?"

The waiter arrived and asked us if we needed desert or anything else.

"I don't need anything to eat. Are you going to be ok to walk?" Jen said, looking at me before turning to the waiter and explaining, "Sorry he's got a bad leg, injured it playing football, you know? Can we get a couple of beers?"

The waiter hurried off to get our drinks and returned with a couple of pints. We thanked him for our drinks, and Jen continued with her story.

"Well, this time Sam wants to up the ante, right? So she goes off to her bag and gets a couple of vibrators. Don't ask me why she had two of them. I don't know, alright? Anyway, she did, and she gave the little buzzy bugger to me the lipstick size while she kept a life-size, cock shaped vibrator for herself. We drag to the coffee table over to put our feet up, and she sits down right next to me, close enough that we're touching.

We are not touching each other like, you know, down there, just really close like we're snuggling, but not. We both scooch down to the edge of the sofa, so our arses are hanging off the seat and our knees in the air as she put on the next clip. Apparently, this was one of her favorites."

She paused to take a sip or two of beer and carried on.

"This one had a bunch of guys all stood around a bed while this big black woman in white lingerie and stripper heels is fucking this white girl from behind who's in all-black lingerie and high heels. You know stockings, corset, the works. Now I think this is horny as hell, right? I'm fingering myself in my sodden cunt and buzzing the hell out of my clit with this bullet vibe, right. Sam's next to me doing the same with a bigger vibe that's she's alternating between her clit and slipping it inside. The white girl starts moaning and cumming on-screen, and the whole crowd is cheering her along, beating off as they go. Eventually, the black girl pulls out for a moment to reposition, and that's when I see it's not a strap on! This girl is trans. This beautiful trans girl is fucking this woman with her fat cock! Fucking hell, I thought that's fucking amazing. Instead of putting her cock back in the sluts pussy, she pokes it at her back door. The white girl just pushes back, impaling herself on this big black lady cock."

Jen is visibly turned on telling this story to me. Flushed and tiny beads of sweat on her brow even though the restaurant is air-conditioned.

"Fucking hell, that's so hot."

"I know, right? That's what I said when I watched it. I knew I was going to come soon and started moaning. Sam told me to hold on, that the best bit was just about to happen. She wasn't wrong either. The camera started moving again, and as it moved around so you could see the face of the white girl getting fucked in front of a crowd of wanking men! It was Sam all along. She was wearing a mask, but it was her getting fucked in the arse by a big black trans woman and cumming again and again. I couldn't help it. I blew my load there and then! I have no idea when Sam came. I was lost in the stars."

"You wanked to a porn flick featuring your mate? Fucking hell!"

"I know. I wasn't sure it happened until this morning. After that, I knew I had to tell someone too, or I wouldn't be able to go through with tonight."

"So you're doing it then?" I asked

"Of course I am. Besides, if I don't, what are you going to beat off to?"

She had a point. I'm not sure I realized she'd just said she would be making these pics for me specifically, but in the hindsight of telling, I see it now.

We drank the rest of our pints in quiet contemplation. I paid for lunch, the least I could do as Jen had provided the entertainment. On the way out, she slipped her arm through mine as we had done many times before, and I asked her what was next.

"I'm not sure." I wasn't sure that I'd be able to get everything this quickly, if I'm honest."

"It's amazing what you can do when you throw money at a problem, eh?"

"What? The rules said classy and classy don't come cheap."

"I think 'classy' came several times last night for free." I joked.

"True." She agreed. "Wait, you think I'm classy?"

"No, I've known you for too long, but I think you'll make a great impression."

"Hahaha." The laugh came easily. She was comfortable with me still, with the situation. I'm not sure I was, but I was getting there.

"I've got an idea," I said.

"I don't like that look you've got."

"What? You'll love it, I promise."

"So, where are we going?"

"Covent Garden," I said. "Seven Dials, to be precise."

So off we went. We were laughing, joking, taking the piss out of each other as if lunch had never happened. We strolled from one end of Oxford Street to the other. It was late on a Wednesday lunchtime, and while the worst covid restrictions were over by then, the crowds would not return for another week or so. Without the tourists and throngs of shoppers getting in the way, we made good time and soon wandered down Charring Cross Road and cut towards the clocktower.

"Where too now then?" Jen asked as we drew closer.

"A little shop I know. I need to buy you a little present. Something to really fit the brief of your briefs."

We walked a little further until we found Coco de Mer and took Jen inside. Coco's is technically a sex shop, but you could happily walk in and not immediately notice if you didn't know. It's a high-class boutique with polished wooden floors and artfully arranged merchandise. I knew it well, though, and acknowledging the sales assistant, I walked Jen straight over to the sex toys. Pointing at the jewelled metal butt plugs asked my friend to choose.

"I think you need a little accessory to finish your outfit. Something to up the kink levels, maybe."

Jen picked up the toys one by one, feeling the smooth cold metal, the bluntly pointed tip, the weight of them in her hand, admiring the sparkle of the jewel in the flared base.

"I've." She looked up at me. "I don't know; I've never put anything up there before."

"You've wanted to though, am I right? Besides don't worry about that, plenty of lube, and it will slide right in."

"Like you'd know."

"Ha-ha, yeah, about that. I've got quite a collection, but this isn't about me."

"No way!"

"Way. Nothing wrong with a little bum fun."

Jen paused, unsure in herself but given confidence by my admission to owning a collection of anal toys.

"Hmmm. If you really think so. What color should I get?"

"Well, the rest of your look for tonight is black, right?" I said, moving towards the black anodized aluminium plug.

"Except for the shoes. There's always that red sole."

"True." I thought for a moment, "Red it is then. Accessories should always match."

We left after paying and headed to the chemist. Jen bought the biggest bottle of lube on the shelf and took it to the counter. The girl behind the till was young and could barely contain a giggle as she bid us goodbye and told us to enjoy the rest of the day. When Jen held up the Coco de Mere bag and told her she would, the poor thing collapsed in a fit of laughter behind the counter.

We left laughing our arses off too.

"Well, what did she expect?" Jen asked once we were in a black cab heading north again. "Cheeky bitch, it's not like I was going to get all embarrassed."

"She probably thought I was going to fuck you senseless when you held up that bag." I joked.

Jen laughed, but I noted she didn't deny it being an option. We got back to her flat soon enough, and Jen let us both into the top-floor penthouse. As she headed off to the bedroom to deposit her bags, I was told to find some wine. I'd spent enough time there before that I knew where the glasses were and went to the fridge to pull out a fresh bottle of pinot.

Jen quickly returned, opened the sliding door to the terrace, and sat out on the balcony looking out over London. I joined her with a chilled glass of white, enjoying the sun and view of the city quietly enjoying her company. After 25 minutes I couldn't take it, I had to know.

"Are you really going through with this then? Are you going to do a sexy shoot with Sam?"

"I think so. I think that if it's just her and me, then I can go through with it."

I must have looked more disappointed than I thought. I have never been any good a poker.

"Hahaha. You poor thing, look at you all upset. So sorry, I don't think I could do a sexy shoot in front of you. Not for my first one anyhow."

I tried to laugh it off like I wasn't getting my hopes up, but it was too late.

"Look, not tonight. That's too much of an audience for a first go."

"Fair enough. I got the wrong end of the stick; that's not your fault. I just figured after lunch... But you're right. This is for you, not me."

I brightened up. She'd shared a lot with me already. It was clear that we wouldn't be the same kind of friends as we were ever again. I was happy with that, and I wanted to see what would happen, not pressure her. I finished my glass and headed back inside to leave.

"God, you're an idiot sometimes. You might not be here for the shoot tonight, but haven't you forgotten something? I made a deal with you, remember? I intend to pay up."

I didn't remember, but Jen stood up with her wine and walked past me into her room.

"Why don't you refill your glass and wait here for me to come back with the lingerie you chose for me."

I did as I was told, quickly topping up the glass and waiting in the living room, mind racing. I didn't have to wait long. Soon the tell-tale click-clack of stiletto heels on a polished marble floor meant I was to see my friend of something like 20 years in very sexy lingerie.

There she was, 5'11 in her stiletto heels, stockings, and stunning Bordello lingerie: all straps, sheer mesh and promises of something more. The bra was comprised entirely of black straps gold buckles. The nipples stood proud and struggling against their restraints, and an areola could be seen between strips of gloss satin. Through the mesh of her knickers, you could easily see her snatch had been waxed of all hair, and her puffy mound was hidden from view only by the lowest rising gusset I've ever seen. I could even make out the top fold of her sex through the gauzy nylon.

Jens legs were long and toned, elegantly encased in the sheerest of fully fashioned nylons riding high on her thighs. The seams ran perfectly down the backs of her legs and only served to highlight the curves of her legs in the most erotic way. Finally, her boots, 6-inch stiletto heels, the darkest of black suede leather with the most petite silver buckle on the side completed the look.

Fuck me. She was perfect. I would scarcely have believed it was her had I not had been there when she bought what she stood before me wearing. So much so that the ornate black lace mask that hid her face save for her blood-red lips was barely needed. No one who knew Jen in real life would say she was the sex goddess stood in the living room. They would be wrong, and the sex goddess was always there, I think. Now it had been let to the surface.

"Well, what do you think? Am I classy now? Could I be kinky enough?"

My mouth moved, but no sound came out. Then, I realized I was sitting on the very same sofa where this beautiful woman had fingered herself to orgasm after orgasm mere hours before. I realized that she was here for me as much as anything else. When I failed to speak, Jen let out a little laugh and held up the lube and butt plug.

"Shocked silence. Perfect. I still need a little help, though; perhaps you could accessorize me properly."

I beckoned her over, and she half stood, half knelt across my lap with her bum raised in the air.

"Are you sure about this? Telling a story is one thing, but this is something else entirely."

"I need your help. I'm not sure I can put this in on my own."

I slid the back of her sheer knickers down, allowing access to her tightest hole. Looking down, I could see just how puffy and wet her folds were. I wanted to slide my fingers inside her, but that's not what she had asked for, and I still didn't want to make the wrong step and ruin everything.

"This is going the be a little cold," I said as I squirted the sticky lube all over her ring. "Let me know if anything hurts, and I'll stop."

She nodded agreement, and I started stroking my middle finger around her anus, relaxing it and getting Jen ready for a new sensation. After a while, I warned her that I would begin to insert a finger inside. Again a nod from my friend, so I continued. I could feel the muscles tighten as I slid inside up to the first knuckle, holding it there for a moment, allowing her to relax.

"How's that? Should I go on?"

She just moaned gently and bit her lower lip. I took that as I should continue, so my finger slid deeper inside to the second knuckle and then all the way in. I withdrew slowly until just the tip remained inside, then quicker this time slid back in, slowly fucking her virgin hole with my finger.

"More?"

She nodded, but before I could continue, I felt her shift again, and my eyes were drawn down again to her pussy by the movement of her fingers here.

"Are you touching yourself?"

"For fucks sake," she gasped 'you've got two fingers in my arsehole, of course, I am!"

"Would you like me to help?"

I reached down and stroked my ring and little finger across her glistening labia, hearing a gasp from the woman in my lap.

"Oh god," She rasped, "That's so good."

I carried on stroking her lips with two fingers and fucking her tightest hole with the other two, teasing her. I noted she never took her hand away from her clitoris, still stroking across her sensitive button with her fingertips.