A typical Friday evening. Sitting alone at the bar just a short walk from my apartment building, watching the Yankee game.
But today, there’s something else I’m watching.
I can’t take my eyes off girl sitting alone in the booth in the far corner. An absolutely stunning woman with brown eyes and blonde hair, sitting with her legs crossed wearing 3 inch heel ankle boots. Her black jeans show off her long, muscled legs. Her unzipped gray jacket reveals the black top she’s wearing underneath that doesn’t totally cover her stomach, revealing her impressive abs. Her physics is enough to make any guy’s mouth water.
She’s sitting alone, and while half of me wants to approach her, the other half of me is certain that doing so would end in total disaster. I’m not sure if it would be more of a disaster because There’s no chance that she doesn’t have a boyfriend coming to join her. Or if it would be a bigger disaster because she would see right through me.
I’m 22 and still a virgin. I’ve never even kissed a girl. It’s not that I’m some lonely who can’t get a date just, dating was not something I took seriously throughout school. But about 2 and a half years ago, when I started working full time, it became something I wanted more. I began wanting that sense of companionship as I moved into adulthood but I didn’t know where to start looking.
I have simply refused to try dating apps. I’ve gone on a single date with a few different girls from my gym but none of them went anywhere.
The last date was almost three months ago. She actually began mocking me for being a virgin. When I told her that her words were bothing me, she tried selling me on the idea she was just going off, but I couldn’t bring myself to see her again.
The waiter drops another drink on the girl’s table.
Is she *actually* not waiting for someone to join her?
Just do it. The worst she can say is ‘no’.
Before I know what’s happening, I’m walking overto her in the corner booth.
“Do you mind if I join you?” I ask trying to not fall over myself.
She glances up at me with a raised eyebrow. Her eyes narrow, as if she’s inspecting my face for a minute.
I swear the 18 seconds between pitches in the Yankee game lasts about 5 years.
I’m almost ready to turn and walk away, telling myself. “Well hey, I tried.”
“Sure.” I’m glad I sit down, because the smile she gives me would’ve made my knees buckle.
“Taylor,” she extends her hand
“John.” I nervously say shaking her hand, her pink manicured nails digging a little bit into my hand.
The next forty five minutes or so fly by as we talk about our jobs and gym habits.
She’s been working out since she was 10 years old, having been a gymnast throughout school. She’s now 25 and works as a car saleswoman.
I silently think to myself that this woman could probably sell me anything in the world right now.
—
We look at the TV across the bar, watching the final out of the Yankee game.
As the post game show intro starts, our eyes meet.
“You wanna come back to my place?”
What the hell do I do now.
I nod and she calls the waiter over, paying both of our tabs without saying anything.
I’m not a guy who would be bothered by that, but I’m honestly still shocked that this woman hasn’t told me to get lost yet.
“Just over there, Beef.” She points to the condo complex down the road.
“Sounds good Abs.”
We both smile, having used the nicknames we gave each other when we spoke about our gym habits. I almost melt when she takes my hand in hers.
We walk slowly, my palms smoking so much that her grip slips multiple times as we walk the few blocks to her home.
—
She slides the key into a door and opens the door, revealing her condo.
I follow her around, exploring the place for a few minutes until she opens a cabinet. My nerves return a bit, feeling a bit out ofplace being in a girl’s home for the first time.
“What’s your poison of choice?” She courtesys to her liquor cabinet which is fully stocked with whiskey, vodka, rum and tequila.
“Bourbon.” I answer.
“Excellent choice.” She pops open a bottle and pours out two old fashioned.
We cheers as we sit on the couch.
We continue to talk for a little bit, my nerves easing as time goes on.
—
“Alright.” She loudly says breaking a momentary silence as she loudly puts her glass on the table. “I’ve always wondered if these are fun.”
“What’s that?” I ask as she takes her phone out.
“A question generator,” she cheerily says. “It gives questions and we both have to answer… Interested?” She asks after a brief pause.
“Yeah why not.”
We answer a few basic questions. Most embarrassing memory, comfort show, favorite pastimes, etc.
But after a few minutes, a question pops up that I really hoped wouldn’t.
What is your favorite wayto be intimate?
She answers first.
“Physical touch, you know, kissing and cuddling.” She grins before tilting her head for my answer.
“Um,” I sit silent for a moment. “Confession time,” I almost inaudibly say. “I’ve never actually had a girlfriend.”
“Ok,” she softly says. “So ‘unsure’.” She taps the button to have the website generate a new question.
She begins reading the next question, but her voice trails off before she finishes reading it.
“You ok?” She asks noticing my obvious disappoint now.
I still still as she squeezes my shoulder.
“Something wrong?”
“I ju… I um.” I feel more embarrassed right now than I have in the entire rest of my life combined. I just confessed to the hottest girl I’ve ever talked to that I’m a virgin.
I look at her phone resting on the couch in between us, another question about intimacy showing on the screen.
“Oh.” She says sounding a bit surprised as she notices my eyes directed at thescreen.
“You’ve never had a girlfriend,” she softly says. “Are you a virgin?”
I nod looking at the floor, no part of me feeling brave enough to look at her.
“Is that what you’ve gone all quiet about?”
I nod again, her hand sliding from my supposed down to my wrist.
“It’s ok, don’t be embarrassed.” She softly says, taking my hand in hers.
I just barely manage enough courage to lift my head up, our eyes meeting as she squeezes my hand.
“Don’t be embarrassed. Please.” She closes the gap on the couch between us.
I nod, but I feel like she’s just trying to make this evening less difficult for me.
After another few minutes of me not really reacting, she seems to figure out that her words aren’t easing the embarrassment I feel.
“Look I get it.” She reaches out and cups my chin. “Being a virgin at 22 for a guy is basically a death sentence if people know about it.” As she speaks, she turns my face towards hers. “But I actually really really respect it.”
I slowly look up and meet her soft eyes.
“I really respect that you haven’t just given it away.”
We spend a few seconds in silence, looking into each other eyes, before she says anything.
“You ok?”
I nod. “Thank you,” I softly say.
She nods and a smile crosses her lips.
“Umm,” she chuckles. “Absolutely no pressure,” she holds her hands up. “But… if you’re interested enough and comfortable enough… I would like to change that for you.”
I nod. “I would like that… If you really want to.”
She smiles running her nails down my arm.
“Well, what do you wanna do first?” She innocently asks.
“Well…” I pause for a moment, nervously reaching up to cup her cheek. “My first kiss sounds like a good start.”
She chuckles and leans in. I feel electricity run through me as we kiss.
“How was that?” She asks as we break apart.
I chuckle and, completely forgetting my nerves from being here, lean in to kiss her again.
“Can you suck me off?” I ask as we break apart.
She nods. “I’d love to.”
She reaches for my belt, undoing it and feeling my noticeably hard cock through my jeans. Her face lights up as she lightly rubs her hand over my hard members.
“Holy shit you’re rock hard.”
I unzip my jeans and slide my underwear down, expposing my throbbing member.
“My oh my,” she gasps. “I really wanna suck that hard thing.” She gets on the floor in front of me, resting on her knees. “No pressure about lasting baby, just cum when you feel like it.”
I nod and she lowers her eyes, lightly running her tongue over the shake and head of my cock.
I take her hand in mine as she wraps her lips around the head of my cock, gently sucking for a moment before lifting her head up and just circled her tongue around my head.
I throw my head back, just enjoying the pleasure and squeezing her hand in mine.
She wraps her lips around my head again and beginsbobbing her head while her saliva drops down my cock.
After a few minutes, she lifts her head up and my whole body stiffens.
She chuckles at my body’s reaction. “Can you do something for me?” she asks.
I nod reaching out to stroke my cock, but she pushes my hand away.
“Oh no, I’m gonna wrong this orgasm out of you.” She gives my tip a soft kiss before looking back up at me. “So can you do something for me?”
I nod with my cock, oozing pre cum, throbbing in front of her pretty face.
“I want you to hold my head down while I suck you,” she licks her lips.
She takes my cock in her mouth again, releasing her grip on my hand.
I slide my hand into her hair, hearing her moan around me as I thrust into her face.
It’s not even two minutes before I start crying out in ecstasy, seeing stars as I cum in her mouth.
My eyesight returns, to see her still kneeing on the floor, smiling as she loudly swallows my load of cum.
She lets outa refreshed “Ah” sound and I reach down to cares her cheek.
“Thank you.”
“No.” She stands up. “Thank you.” She leans down to kiss me, her arms resting on either side of me. “Virgin cock is so tasty.”
We break apart, and I look up into her glistening eyes. “So did you…” I softly say reaching up to cares her cheek. “Still wanna have sex?”
“Oh yes.” She grins. “As long as you’re up for it.”
I nod and she grabs my hand with a smile, pulling me onto my feet.
“Why don’t we head to my bedroom?” She winks.
“Sounds scary,” I chuckle.
“Oh don’t worry.” She softly kisses me. “I don’t bite,” she takes my hand. “Unless you want me to.” She turns and leads me across her condo.
We enter her room and she turns towards me, wrapping her arms around me and kissing me.
“Would you like me to put on some lingerie for you?” She asks in between kisses.
I nod, feeling her nails scratch up my back.
“You don’t have to, but I’d like you to… But only if you want to.”
She chuckles. “You don’t have to worry about being a nice guy tonight.” She softly kisses me. “Pick a color.”
“Umm…” I pause for a moment. “Pink?” I more ask than answer.
“Sounds good.” She gives me another kiss before unwrapping her arms. “Turn around, no peaking.” I turn around and hear her closet door open, Then shut a few seconds later.
“Why don’t you take your clothes off and I’ll be right back.” She lightly smacks my butt and leaves the room, shutting the door behind her.
I strip, putting my clothes on the chair next to the bed, my cock hardening with anticipation at actually fucking this woman.
I accidentally drop my shirt, but reach down to pick it up and notice something under the bed. Some big, black box.
It’s not my proudest moment but I slide it out from under the bed, wondering what’s inside of it.
I try to open it, but it actually has a combination lock.
I play with the dials for a moent, but the trunk won’t open.
The door opens and I look at her, feeling like a deer caught in headlights.
“Snooping?” She smiles.
“I can explore… I’m so sorry… Please don’t kick…”
She remains calm, leaning against the doorway, and looking flawless in her pink lace bra and panties with matching stockings.
She approaches me, with a smile. “Do you wanna see what’s inside?”
I hesitantly nod.
“Alright,” she slides the first dial to 1. “Let’s just say,” she slides the second dial to 0. “I’m into some kindy stuff.” She slides the third dial to 3 and fourth dial to zero, the trunk popping open.
She lifts the top of the trunk up, revealing every kind of restraint imagineable a whip and paddle, and a smaller black box.
As someone whose read BDSM stories for years, I feel like I’ve just won the lottery.
Grinning, I look up at her to see her examining my reaction.
“Did that just turn you on even more?” She chuckles, leaning downto kiss me, and trailing a hand inside my tigh to my cock, twitching with anticipation.
I nod as we break apart, standing up to run my hands over her lingerie clad body.
“Would you like to introduce me to BDSM tonight too?” I softly ask feeling her breast through her top.
Her grin widens. “As long as you ask nicely.” Her nails dig into my arms a little bit as she smiles up at me.
“Please tie me up.” I softly say.
That seems to be enough for her, because she shoves me onto her bed and leans down pulling out a pair of handscuffs.
I let out a gentle moan as she cuffs my hands to the headboard.
She notices me trying to rub my cock against my leg and lightly slapse the head of my cock.
“Nuh uh,” she grins. “You have officially given up control of this.”
She picks up two more black cuffs from the trunk. She cuffs these two to my ankles, a little bit tighter than necessary, and ties them around the footboard.
She lies down on the bednext to me. One leg resting on top of my bound leg and one hand dancing around on my chest and abs as we kiss.
“You feel all better now?” She grins softly, kissing me again.
I nod, feeling my cock start to drip pre cum again.
“So if you’re a virgin.” She stops speaking for a moment, seemingly trying to gauge my reaction. “… I’m going to guess you’ve never licked a pussy before either.”
I nod, blushing a bit as I can feel her pussy dripping onto my leg.
“Would you like that to change?”
I nod and understand around for a second.
“Don’t worry.” She encouragedly says sliding up the bed and pulling her panties to the side.
My mouth waters as I look up at her sex, a small part of me even intimidated by it.
“This is my clip,” she holds her finger just above a small nub. “That’s very sensitive,” she explains. “So stick your tongue out.” She lowers herself a little bit, until there’s only a few inches between my lips and her dripping pussy. “Just let your tongue roam around sweetheart. Don’t worry about making me cum right now.”
She lowers herself the rest of the way and I began licking her all over, savoring her taste and using her moans as a guide for spots that she likes.
I know she said not to worry about it, but no part of me wanted her to lift herself up without having an orgasm.
As her moans soften, I tilt my head back and flick her clip repeatedly with my tongue until I feel her body begin rocking.
Suddenly, her juices exploit all over my face and I feel the weight on the bed shift as she moves around.
She scoops some of her juices off my face and sucks her fingers clean.
“Did you enjoy that?” She asks scooping up the rest of her juices.
I nod. “Wait,” I softly Say as she brings her juice covered fingers to her lips. “Can I suck your fingers clean?”
She smiles at me. “Of course you can.” She extends her arm towards me, her fingers sliding into my open mouth.
Sheslides her fingers out of my mouth.
“You might be the most adventurous virgin ever,” she chuckles as we kiss.
“I know,” I softly nod. “I just feel so safe with you.” I confess.
“Aw thank you,” she responds with a geneine smile and another soft kiss. “So I’m guessing you still want me to take your virginity tonight?”
I nod and her grin widens.
“I wanna tease you a bit,” she says caresing my cheek. “Are you ok with that?”
I nod and she lightly teas my frenulum with her fingers.
“Good.” She lifts herself over me, pressing my cock into my stromach, and tracing it with her dripping pussy.
She rubs her clip and then sticks her wet fingers in my mouth. With her fingers in my mouth, she spends what Feels like hours just rubbing herself against me like this as I helplessly wrong beneath her.
“Please.” I whimper as she takes her fingers out.
“Please what?” She taunts rubbing my head against her clip.
“Please fuck me.”
“Fine.” She smiles down at me. “I guess you’ve earned it.”
She lifts herself off of me, her hands on either side of my head.
“Baby?” she softly kisses me. “Remember this moment honey.” We kiss again. “You’ll never be the same after this.” She grins and lowers herself onto me.
The moan I let out when she takes me in is more of a squeal, as she begins grinding on me.
I just lie there as she grinds on me, lost in the incredible feeling of her tight wetness for the next few minutes.
“You feel me gripping you?” She softly asks as we kiss.
My eyes are closed as I moan into her lips.
“You feel fucking amazing.” I begin to match my hip movements with hers.
“I feel very full.” She chuckles, running her arms under me and digging her nails into my back.
We continue to kiss and grind into each other for another few minutes before she let’s out a growl.
“I’m gonna… cum on you… baby.” She weakly says. “I want you… to cum… deep inside me.”
She kisses me again and I feel her convulsing around me and her juices coating my cock.
I give her one last thrust before I feel myself exploit deep inside her.
I don’t have a rational thought for a few minutes, until I see her reaching up and releasing my wrists.
I wrap my arms around her, deeply kissing her.
“Was that a good first time?” She chuckles.
“That was amazing.” I kiss her forehead.
“Yeah that was pretty awesome.” We kiss again, and she grins as we break apart. “You realize don’t you baby?” She reaches out to cares my cheek. “You’re not a virgin anymore,” she clicks her tongue.
I nod. “Thank you baby.”
“Oh thank you.” She nestles herself into me. “That was incredible.”
We lie in silence for a few minutes before she looks up at me again.
“Can you stay the night?”
“Only if you promise to until my legs.” I chuckle.
“I can make that work.”
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