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 physique 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 loner 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 bothering me, she tried selling me on the idea she was just goofing 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 over to 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 smirk, 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 sweating 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 of place being in a girl's home for the first time.
"What's your poison of choice?" She gestures 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 way to 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 discomfort now.
I remain 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 the screen.
"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 shoulder 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 knew about it." As she speaks, she turns my face toward hers. "But I actually 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 others eyes, before she says anything.
"You ok?"
I nod. "Thank you," I softly say.
She nods and a smirk 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 smirks 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, exposing 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 shaft 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 circling 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 begins bobbing her head while her saliva drips 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 wrench 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.
