M/F ~ Virginity Auction ~ BDSM ~ Age Gap ~ Older Man/ Younger

Selling My V-Card On V-Day

An older, handsome, mysterious billionaire wants to bid on my virginity at an auction. And I just might let him.

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Mirror, mirror on the wall, who looks the most elegant but is actually the sluttiest of them all?

I stare at myself a little too long in my best friend Brianna’s full-length mirror, repeating this silly phrase I’ve just made up in my head and trying to remind myself that it’s really me in here.

Plain Jane Tessa Davenport. Tomboy, nerd, misfit.

Except that right now I look like a knockout. Brianna’s been telling me that for the past hour, and it’s starting to sink in a bit, even though I don’t even recognize the girl staring back at me in the mirror.

From the looks of what I’m wearing, you’d think I was going to a fancy party. All the details are in place.

Except I’m going to an auction club where rich billionaires can bid on my virignity. And I’m doing it so that Brianna — the one who usually works there — can have the night off and go to dinner with Billy, the guy she’s been dating.

The things I do for my best friend!

Although, at least I’m going to look spectacular while doing her this favor.

I’ve donned a shiny black and silver evening gown accentuated with a tiny diamond necklace, which was a gift from Brianna the night before Prom.

She’d been excited that a guy named Tom was taking me. But the next morning she cooked me breakfast and hugged me while I cried about what a jerk Tom had been.

I’d thought I’d never be interested in anything related to sex again after that but here I am, about to go to Club Hot Commodities after having way too many fantasies about the sexy stranger I’d seen there.

And I sure am all dolled up for the occasion. My red fingernails feature dainty pink hearts that the nail stylist painstakingly painted on earlier today.

The same stylist also did my hair, adding volume to my normally flat, thin red strands and piling them all up on top of my head with tightly rolled curls spiraling down in a style reminiscent of my high school Prom.

Where I almost lost my virginity but didn’t.

That’s still intact, although my pride was wounded if not completely broken that night. And now that I’m going to a dinner club where I’ll be auctioned off like cattle, there’s not much of my pride left of which to speak.

Brianna keeps insisting that only my companionship is being auctioned off. Not my body and not my virginity. But it still feels wrong. And I’m starting to think I shouldn’t have agreed to do this.

She continues re-explaining the whole sordid situation to me even though I think I’ve had about enough explanation and am ready to just experience it myself.

Usually, I’m the one who’s the over-analyzer and the over-explainer. But now that she’s falling in love, she’s become worried that it won’t work out. She’s been freaking out a lot, but I still love her.

“So, I can’t ditch Club Hot Commodities on the busiest night of the year — their special Valentine’s Day auction. But I also can’t skip out on Valentine’s Day dinner with Billy and miss out on finding out whether he wants us to be in an official relationship. So, that’s where you come in, and I’m very grateful to you for helping me out.”

“But is it really that easy to just substitute you for me?” I ask her, feeling skeptical. “Aren’t there, like, regular customers of yours — ”

“Clients,” she interjects, as if I’d just called her a prostitute.

“Fine, clients of yours that will be upset if they show up intending to bid on you and instead see me up there on the… stage?”

I squish my nose up in disgust.

“And how does it feel to be up there on the stage?” I ask, as one of many follow-up questions that I have. “Like a cattle auction? Seriously?”

“Tessa, you’re sounding judgmental again,” Brianna growls.

“Sorry. Just wondering. Since I’m going to be the one up there and all. I have so many questions and issues about this. Maybe a lot of it is stemming from insecurity. I’m not nearly as confident as you are. Not to mention as pretty. Won’t they be disappointed if they’re expecting to see you and instead, they see me?”

Now that I’m the one who is going to have to be doing this, I definitely feel worse about the whole thing than I already did when it was just my best friend having to do it. And I also wish I would have had more notice, so that I could have lost some weight in advance.

I feel insecure about being pudgy, and having my body judged like it’s a piece of meat.

“Look, you know you’re the only person I could ask to step in for me,” she begs. “You’re the only person in the world who even knows that I do this.

“I understand where your judgment is coming from and maybe I deserve it in return for the favor you’re doing for me but it’s not like I’m cattle. They want me across the table from them at dinner. They want my conversation. Not just my looks but also my personality. My amazing wit.”

I laugh.

“Well, you do have all those things,” I tell her.

And she does.

“But yes, initially it’s based on looks. Isn’t that how human biology works? Sure, we stand up there, so they’ll see what they’re bidding on. And no, they won’t be disappointed when they see you instead of me. Trust me.”

“What do you mean?” I ask her, my interest piqued.

Now she’s appealing to my ego.

Brianna’s good.

“Well, just look at you,” she says, waving her hand up and down to indicate my entire figure in the full-length mirror hanging on her bedroom door. “You’re every guy’s wet dream.”

“I am not,” I insist. “I’ve gained my freshman fifteen and then some, and I don’t even know how, because I don’t live on a campus with a cafeteria or anything like that.”

“That doesn’t matter,” Brianna insists. “The weight gain has only enhanced your curves, your boobs. It’s given you a healthy glow. You needed to gain some weight. You look healthy now. Vibrant.”

“Thanks, Dr. Brianna,” I tell her sarcastically.

Secretly, though, I’m pleased that she thinks the guys will like me…. the guys who will be at this human auction I would never go to if it weren’t for her… because that means that if the mystery man’s there, he might still like me.

I know he was definitely into me when I went with Brianna to check out the Club, but a whole month has passed, and I’m worried he’s forgotten all about me.

I’m probably just one of many women he stares at there, and he’s likely moved on to find himself a steady date, or whatever it’s called at this Club.

“And they like new girls. Believe it or not,” Brianna says sarcastically, “due to the stigma of this kind of work, there aren’t a ton of attractive, intelligent young women willing to do this, even though it pays very well, and you get free filet mignon and unlimited drinks out of the deal as well.”

“You drink with them?” I ask, aghast. “We’re not even old enough to drink.”

“Oh, honey,” she says, as if I have a lot to learn.

And I guess she’s right. I do.

“Money talks. No one cards these guys or their dates.”

That’s good, because I could certainly use some liquid courage.

“They’ll be thrilled to see a new face and they’ll thank me later,” she insists. “It’s a tight-knit club and the whole goal is to please the clients. I’ll get extra brownie points and maybe even a bonus when I go back tomorrow. If I go back tomorrow.”

She pauses, staring off into the distance as if daydreaming.

“If Billy doesn’t ask me to be his girlfriend, which I really hope he does,” she concludes.

I take her hand again and squeeze it.

“He will definitely ask you to be his girlfriend,” I tell her. “And you can quit working at the cattle auction and live happily ever after with your handsome sugar daddy.”

Billy is in finance and makes a lot of money. Brianna’s not with him because he’s filthy rich, but it sure doesn’t hurt.

I really do want her to continue to find love, stability and wealth with the guy of her dreams. So much so that I’m willing to stand in her place as human cattle.

“And you might just actually surprise yourself and have fun tonight as well,” she responds.

I raise an eyebrow at her, incredulous. Even though I was already kind of thinking that myself. I’m not going to admit it to her, though.

“Oh, come on,” she says. “Just think of what happened with you and Tom.”

“I don’t want to,” I quickly say.

Why does she have to bring that up?

It’s definitely not the way to stay in my good graces. If Brianna wants me to keep agreeing to do her this big favor, she shouldn’t get on my bad side by mentioning things I don’t even want to think about.

“I’m just saying,” she continues. “These men are experienced. Older — but not too old. They know what they’re doing. You might actually find that you like the power dynamic. You might be able to loosen up and let yourself go for once.”

“I thought you only have dinner with them,” I tell her.

She blushes, just the slightest bit, and I realize there is way more to her secret life at this club than she’s revealed to anyone, even me.

She probably usually only has dinner with them, but I bet there have been one or two men that she’s let do more, for the right price.

As far as I know, she’s a virgin, like me, but she’s been willing to experiment more without going all the way. Guys have always flocked to her, and she’s been curious.

It’s not that I judge her for that. In fact, I’m jealous of her openness compared to my shyness.

“I’m just saying,” she says. “You never know what might happen.”

She’s right. I don’t know.

I hope my mysterious billionaire is there and that he’ll bid on me. But if so, what would happen after that? How exactly will things go down if I decide to let him buy my virginity?

Maybe he’ll want to take it the old-fashioned way. He could lay me down missionary style and get on top of me, pushing his big cock into me and kissing me gently so that it doesn’t hurt too much.

Perhaps he’ll be so big that his cock won’t be able to fit all the way inside me at first.

At that point, his lips will trace themselves up and down my body as he kisses me all over. He’ll gently kiss my clit and then suck on it as I beg him to keep making me feel good.

My juices will flood his mouth as his tongue laps them up, and then he’ll be more easily able to slide himself inside my opening and fuck me for my very first time.

No.

I don’t think it would go down like that.

He seems to have particular tastes and be very demanding.

He might want to make me pleasure him, and I’d be happy to. I’d open my mouth up wide so he could put his cock in it, and I’d try hard not to choke as he pushed his long, wide shaft all the way in.

I’d do my best to deep throat him but I haven’t had experience so he might get frustrated and have to face-fuck me some.

“Come on,” he’d urge me. “Open up your mouth wider and take my whole cock inside of it like my good little slut.”

Yeah, that’s more like it, I think.

He’d probably be into rough sex, and, with him, I’d be into it too. I’d let him fuck my mouth and pull my hair so that he could stick his dick even further inside it. He could cum all over my face and then let it dribble down to my breasts.

He could slap my breasts with his cock and then fuck my tits.

And then he could turn me around doggie style and put his cock inside me. I’d let him put it in my ass if he wants, but at first, he would want to start with my pussy.

His dick would already be hard again, and he’d use it to spread my pussy hole wide open.

I’d start to cry because it would hurt some, but not enough to ask him to stop.

He’d check with me by saying, “Does this hurt too much or are you going to let me have my way with you like the little slut I know you want to be for me?”

“Do whatever you want to me,” I’d tell him. “Keep going.”

“That’s it,” he’d say, as he’d force himself inside me until his cock was stretching my pussy hole open so wide, I thought it might split into two. “Let me into that little virgin pussy of yours. My big cock needs to defile it.”

“Mmm,” I’d moan, half in pain, half in pleasure as he thrust his big dick in and out of me.

He’d slap my ass so hard I’d jump, but then he’d pull me back towards him by my ass cheeks and make me ride his cock as he fucked me even harder.

“Do you think you can get away from me?” he’d ask me. “You said to do what I want with you. And I want to fuck you, and to discipline you for trying to get away from me.”

“Discipline me,” I’d beg him, as his hand would strike my ass again and again.

One of his hands would be holding my ass cheek in place so his cock could keep fucking me, while his other hand would be striking my ass until there were red welts all over it.

“There you go,” he’d say. “Good girl. Take my cock in that little pussy of yours even if it hurts. Let me fuck you nice and rough and hard.”

“Oh, yeah,” I’d moan, as I came all over his cock.

“Yeah, cum on my cock while I fuck you. I’m going to cum in you now. I’m going to shoot my seed in you and put my baby in you.”

Woah, I think, not sure where the pregnancy fantasy had come from. But I guess it just makes sense that I’d want someone with genes as good as my mystery man to knock me up.

Obviously I don’t want that in real life — I don’t think? — but in fantasy, it’s pretty hot!

“Are you okay?” Brianna asks me, and I realize my face must be flushed as red as my ass cheeks had been in my fantasy.

“Yes,” I tell her, not wanting to admit what I was thinking about because it’s just so plain crazy, and also because she doesn’t even know about this obsession of mine. “I’m fine.”

“Okay, well as I was saying,” she continues, and I’m glad she’s babbling on instead of realizing that I’m sitting here thinking of a man I don’t even know knocking me up!

“Well, good luck with Billy. I think you’ll be in an official relationship after tonight and I want to hear all about it.”

“Not until tomorrow,” she says, shaking her head. “No cell phones are permitted at Club Hot Commodities. It’s a very strict rule.”

“What?” I ask, thinking that this is probably just one big thing on a long list of many things she should have told me before I agreed to work her shift tonight.

“Never mind,” I add, as I peer down the hallway of her small apartment and look at the devil-tailed cat clock hanging above her kitchen stove.

We both have to go, or she’ll miss her Valentine’s Day dinner date and I’ll miss the craziest thing I’ve ever agreed to do in my life.

“Do you have any quick words of wisdom for me before I embark on my descent into debauchery?” I ask her.

I know she’ll think that’s a judgmental comment, but I’m getting her back for bringing up Tom — my most dreaded and embarrassing subject.

“Yeah,” she says. “Just make sure you choose the right colored bracelet. I know I’ve gone over this a million times but that’s a make it or break it thing.”

Shit.

I hadn’t been listening well enough and now it’s going to show.

“The yellow bracelet is the good or bad one? It just means dinner? What do the other colors mean? What are all the bracelets for? Why do there even have to be bracelets?”

But she’s already left the bathroom while I’ve been asking my million questions. Now she’s gathering her coat and purse from the living room, and she must have seen a missed call from Billy because she’s hurrying to text him.

“I’ll be right there,” she says, reading her text to him out loud to me. “Just putting the final touches on becoming beautiful for you!”

Then, turning to me with an excited smile on her face, she says, “Okay. It’s go time for both of us.”

It sure is.

And I guess the significance of the different-colored bracelets is just one of the many things I’m going to have to find out for myself tonight.

I’m sure they’ll explain it all to me when I get there.

Or maybe I’ll have to let my sexy stranger do that, after he places his winning bid.

Thanks for reading! This was part 5 of my erotica serial called Selling my V-Card on V-Day. To continue on to the next part, called Craving Her Curves, click here.

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If you missed the first story in this serial and want to start at the beginning catch up, click here to read Part 1.

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