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

An Older Billionaire Took My Virginity on Valentine’s Day

He bought it fair & square at an auction. But thanks to his experienced hands/cock, I’m getting the best end of this deal!

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Content warning: This story features some elements of consensual dubcon, rough/degrading sex, BDSM and dominant/submissive power play that some readers might object to… and others might really enjoy!

Blake

I can’t believe I finally found my dream girl at Club Hot Commodities. It’s an auction club where billionaires buy virgins. But for me, it’s Heaven right now, as I slowly admire and pleasure my prize. I’d been determined to be the highest bidder, and I was.

I wasn’t intending to start off this way. I’m taking things a bit more slowly than I usually do. I look down at Tessa’s exposed, vulnerable pussy and her confused yet trusting eyes.

I can’t believe I’m going so easy on her. I should be furious and demanding a refund from Adella. Clearly Tessa didn’t sign up for this and she’s not the pliant submissive I thought she would be.

And yet I feel differently about her than I do other girls I’ve taken to this room. The way that I feel different is in the fact that I feel anything at all. That’s rare, and this feeling is actually quite overpowering.

I shouldn’t continue this session. It’s obvious that she’s in over her head, as am I. Both of us are being stupid.

But I can’t stop looking at her beautiful pussy. I need to make it mine. But first I need to find out who this unique creature who just walked into this room — and my life — really is.

I rub the head of my cock up against her pussy. She squirms but I can tell it’s out of delight instead of fear. I can feel that she’s dripping wet for me.

“Do you like this?” I ask, pinching her nipple. “Do you like when I play with your body while playing with my cock at the same time?”

“Yes,” she nods, still shy but opening up a little bit.

Usually by now I’d have her tied up to the fucking ceiling. I should be pissed that she’s such a novice, but I did want a virgin.

About that. I’d better confirm. As far as I know, it’s only based on a rumor.

I hold up the vibrator.

“Has there ever been a cock inside you?” I ask her.

She shakes her head.

“No?” I ask, needing to hear her say it out loud.

“No,” she says. “I mean, that’s correct. There’s never been a… cock inside me.”

That’s the right answer, so I place the vibrator up against her clit and let it work its magic.

“Oh, my God,” she breathes out, her whole body quivering along with her pussy. “That feels good.”

“You’re cumming for me already, aren’t you?” I say, as she leans her head back and moans along with the humming vibrator.

“Yes,” she says. “Yes, yes.”

Juices run out of her, making a nice natural lube. I run my hands along the opening of her little pussy hole. Then I stick two fingers inside her.

“Ouch,” she calls out, struggling to sit up, but she’s unable to do so because of the ropes I’ve tied her up with.

“Good,” I tell her, as I feel along her tight, perfect pussy. “It should hurt.”

Yes, she’s a virgin all right. And I can’t wait to change that fact. But first, I have to find out a little more about her.

I kneel down on the floor and take my cock back in my hand. Stroking myself, I run my tongue along her beautiful clit. Then I suck on it a little bit.

“Mmmmm,” she moans, her clit still engorged and sensitive from the way I made her come with the vibrator.

“Why did you come to this club tonight?” I ask her.

She tenses, obviously wanting my tongue back on her pussy.

“Because my friend Brianna couldn’t,” she answers.

“Was that the only reason?”

“No. I saw you here last time and I couldn’t stop thinking about you.”

Now that’s more like it.

My cock hardens even more now that she’s admitted this. I’m so glad she’s been wanting me as much as I’ve been wanting her. She came here to see me, even though she had to have been afraid.

“Were you afraid?” I ask her.

“Yes.”

I put my tongue back on her clit and I can feel it throbbing as I taste her delicious juices. I run it in and out of her pussy hole, tasting her sweetness.

It’s clear she’s telling the truth. She’s a virgin, she was scared, and yet here she is letting me take her, because she wanted to see me. But if all she wanted to do was see me, that begs another obvious question.

“So why the pink bracelet?” I ask her.

I would have thought she’d ease her way up to sex, with something less scary.

“Sally told me it meant I just want to have dinner,” she says.

I shake my head.

That bitch Sally. She clearly set Tessa up for this. Just to get my money. I’m going to demand a partial refund for procuring it under false pretenses. And then I’m going to give that to Tessa, in addition to a hefty tip.

“Tessa,” I tell her. “I’m sorry. That’s not how this club is supposed to work. You don’t have to do anything with me that you don’t want to do.”

She nods, but she doesn’t say anything.

“So, do you want to have sex with me?” I ask her, raising my head so that I can look into her eyes.

What the fuck has come over me?

This isn’t like me at all. I’m a take charge kind of guy. I should have her over my knee, spanking her for saying she only wanted me to take her to dinner instead of letting me tie her up right away.

But there’s something about her that just does it for me. Fulfills a deep, aching longing I didn’t even know was there. And makes me want to protect her. After I defile her, of course.

“Yes,” she says, and I can tell that she’s sincere.

I return to licking her pussy, which isn’t something I usually do except if I wanted to bring her close to climax and leave her hanging, begging me for more.

But right now, I want her to feel pleasure. I want to taste her cum in my mouth again, but this time I want it pouring out as my tongue does all the work instead of the vibrator.

I almost feel like I don’t even need to use any special tools or equipment on her. I just want it to be her and me and our naked bodies mixing and melding.

I must be losing my fucking mind.

“How come you haven’t had sex before?” I ask her, although not sure I want to know the answer. “Have there never been any boys your own age you’ve been into?”

I’m getting jealous now, and I never get jealous. It’s like I’m torturing myself emotionally in the same way that I had planned to torture her physically. I’m sure there had to have been some close calls — with her beautiful body, her perfect pussy — and I don’t really want to hear about them.

And yet I want her to tell me in drawn-out detail about how she’s never been with anyone like she’s about to be with me. It’s a sick need I don’t even know how to explain to myself.

“It almost happened on Prom night,” she tells me, tensing up with pleasure as I lick her up and down. “But it didn’t.”

“Why not?” I ask her, sensing that for some reason she’s embarrassed.

I like that she’s vulnerable with me, both emotionally and physically. I can tell she hasn’t told many people what she’s about to tell me, and I love that. I want to take her, own her, claim her, make her mine in every possible way.

“I thought it was going well, and I returned his advances. Maybe I even made a few of my own in return,” she says, as I continue licking her pussy.

But now I stop because she has.

“So, what happened?” I press.

She shrugs, which is difficult to do in the ropes I’ve tied her up with.

“He didn’t really reciprocate… didn’t do anything much from there, and I felt really stupid.” She sighs. “We went to the same church; we’re both from religious families. I guess he wasn’t expecting the same thing out of Prom night as I was.”

“Or else he felt too ashamed by his expectations,” I offer.

I look up at her again and she’s gazing down on me as if she hadn’t ever thought of that. She nods.

“Or that,” she says. “But he told people I was too ‘forward.’ I felt like a real slut. I never really pursued it with anyone after that.”

I flick her clit with my tongue, playfully, to lighten the mood.

“Well, I sure am glad it didn’t work out,” I tell her. “And any guy who says you’re forward for wanting to have sex on Prom night sounds like he’s got real issues.”

She laughs, and then she moans as I suck on her clit.

“I’m glad too,” she says, “now that I found you.”

There’s a pause, and I can tell she thinks she’s said too much. I take a break from teasing her clit to tell her, “I’m glad I found you too. Up there on stage wearing your pink bracelet not even knowing what it meant.”

We both laugh.

“I was wondering why you paid so much,” she says, with a giggle so cute I wish I could bottle it up and keep it forever.

I hate this feeling that’s come over me, of being powerless and out of control for her. But I also love it. I’m beginning to think I love her, as crazy as that might sound.

That’s not possible, I tell myself. I just met her. Yes, I’ve been thinking about her non-stop but I don’t even know her. Plus, I don’t fall in love. With anyone.

“Apparently it was so that I could make you feel good,” I tell her, as I lightly bite her clit and then suck on it while her back arches up off the table.

I think it’s the most beautiful sight I’ve ever seen.

“That does feel good,” she tells me, as I feel and taste her juices gushing into my mouth. “Oh, God. Blake. I’m cumming.”

I grip her ass cheeks and bring them closer to my mouth while I continue sucking her clit.

“I’m cumming, I’m cumming, I’m cumming,” she says, until her breath slows and the orgasm ends.

“That’s not really all that I paid all that money for,” I tell her once she’s done with her long orgasm, and we laugh again.

But what I say next is no laughing matter.

It’s what I’ve been wanting to do since the first time I set eyes on her.

“Now I’m going to take your virginity.”

Tessa

I never thought I’d be so quick to agree that a stranger should take my virginity, but somehow Blake doesn’t really feel like much of a stranger. I’ve just told him my most embarrassing secret and I’ve been completely intimate with him.

He slides on a condom, reluctantly so, as if he doesn’t really want to. Then he climbs on top of me, and I can feel the head of his cock up against my pussy.

This is it.

This is how I’m going to lose my virginity.

It feels amazing for me, but I hope it’s not going to be a letdown for Blake. I’m sure he’s used to things being a lot kinkier.

“Don’t you want to, like, spank me with a whip and put a ball gag in my mouth or something?” I ask, just before he enters me.

“Yes,” he tells me. “But not right now. There’s always another day. Right now, I just want to take you the old-fashioned way.”

I look at the ropes tying me to hooks on the wall and he gets my gist.

“Well,” he says, “as close to the old-fashioned way as I know how to be, anyway.”

He pushes his cock into me, and it slides in quite easily.

“Wow,” I tell him, as he grips my shoulders and pumps harder into me. “I thought it would hurt more.”

“You’re very well lubricated,” he says, which is true.

“You did a good job of getting me that way.”

“And I had fun doing it.”

He pushes in and out of me, each time spreading my pussy hole open wider to make room for his huge cock. He’s nearly all the way inside me and it’s driving me crazy. I’m so sensitive I feel like I’m going to cum again.

“Mmmm,” I moan, embarrassed that it’s about to happen yet again.

But Blake doesn’t seem to mind at all.

“Cum for me,” he says, whispering into my ear as he thrusts himself further in me.

I do, squeezing my thighs and my pussy tight up against his cock, which makes him moan too.

“You’re my dirty little slut and I just popped your cherry,” he says, which makes me want to cum all over again before I’ve even had time to recover. “I want you to beg me to keep fucking you.”

“Please keep fucking me, Blake,” I cry out, as his long and hard cock pumps in and out of me. “You make my pussy feel so good.”

“Your wet, tight little pussy likes to cum for me,” he says. “It’s only ever had my big fat cock inside it.”

“It only wants your big fat cock, Blake,” I tell him, as he fills up my entire pussy. I can feel him all the way deep inside me. “Just fuck me forever, Blake.”

“It’s all I want to do,” he says, twisting my nipples.

It hurts but I don’t say anything.

I remember how he said I could tell him to stop at any time, but I don’t want him to. It feels good when he makes it hurt some. My pussy is sore and aching for him, and now my nipples are too.

“I just want to fuck my little virgin slut forever,” he says, pounding me hard with his cock.

I can tell he didn’t mean to say that because he immediately falls quiet. He keeps stretching out my pussy hole with his big cock that he’s thrusting in and out of it, but he isn’t talking anymore.

Suddenly he starts grunting and slapping my ass.

“You’re so bad, Tessa. You make me want you so much. You make me love fucking you. You’re such a little slut for me.”

I love how he’s spanking me, and I don’t want him to stop, even though I know he could. He starts yanking on my clit, twisting it and pinching it while his cock is pulverizing my pussy hole.

All of it starts to feel so good that I’m cumming over and over as he uses and abuses me — just the way I like it.

“Oh, Blake,” I moan. “I love being your slut. You make me feel so good.”

He spanks my breasts and my ass, putting red welts all over me.

“Don’t make me stop,” he says. “I need to cum in your pussy. I need to spank you for being such a dirty slut for me.”

“Don’t stop,” I tell him. “I don’t want you to.”

His slaps are stinging me, but I like the feeling of his big, strong hand on me. He’s punishing me for being bad for him, just like I need. I want him to be in charge of me, in control of me always.

I’m having the best orgasm yet when I start to feel his cock throb and pulse inside me as he says, “Fuck, Tessa. You’re going to make me cum in you.”

“Cum for me, Blake.”

“I wish I was cumming in your pussy without any condom on,” he says. “I wish I was filling you up with my load.”

“I wish that, too,” I tell him, surprised that we both want that, and confused about what it means.

Did he just imply that he wants to knock me up?

And did I just agree that I’d like that?

I don’t have time to think anymore because I feel myself getting ready again too. We cum together, as he continues to slam his cock into me, grunting and yelling, “I love your fucking pussy so much.”

“I love your cock so much; I love when you give it to me.”

“I love your virgin pussy.”

“I love your filthy mouth. I love this so much.”

“I love this so much, too,” he grunts out.

As he cums in me, he holds me tightly in his strong, muscular arms while we both pant and come down off the high we were just on together.

I can’t believe how amazing this was. I’m so glad I subbed for Brianna and I’m even glad for the bracelet mix-up. Sally had clearly tricked me, but it had turned out to be for the best.

I can’t believe my mysterious billionaire turned out to be such an amazing lover for my very first time.

It hadn’t even been nearly as kinky as I thought it would be, and I was both happy and sad about that. I’d liked that Blake had treated me tenderly. But I’d also enjoyed the kinky stuff he’d started to do, and I was intrigued by it, wanting him to do even more of it.

Blake himself had mentioned something about there being other days he could do other things to me.

Does he mean at another auction? Or would he want to see me again separate from this whole crazy club scenario? Would that be against house rules?

I forget what Brianna was saying about that. My mind feels so muddled that it’s hard to think straight.

Was it okay that we’d told each other we love doing things together?

That seemed to be awfully close to saying we loved each other.

But that’s okay, right?

We were just getting into things and expressing how much we liked it?

I have so many thoughts running around my head!

I honestly don’t know what to make of it all or what to think.

All I know for sure is that I’m really glad I finally got to lose my virginity to my handsome, mysterious billionaire, and I’m hoping we can see each other again, no matter what kind of issues it’s sure to cause with my parents.

I know I’ll already be in enough trouble with them for staying out so late tonight, but I’ll soon have money to get a place of my own, and finally live life the way I want it, having been bought and freed by a rich, older, experienced man who showed me it’s okay to go after the things I really want in life.

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

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