When I pictured losing my virginity, I always thought it would be with a boyfriend that I cared for. There would be rose petals sprinkled on the bed; candles lit around the room; and romantic music playing in the background. The sexual tension would be so palpable that my stuffed elephant, Mr. Fluffypants, would’ve ran for the closet as soon as we entered my room.
The lights would be dim; not too dark and not too bright. We’d be so busy making out that getting undressed would be more of a hassle than anything else. There would be passion; and fireworks; and breathing so heavy the windows would fog up.
But here I am, a twenty-three year old virgin about to have sex with a man I just met from the internet. Tinder, to be exact. After two months of swiping left; swiping right; and cringing at the amount of dick pics I received, I finally decided on one man, Gabriel.
He’s twenty-eight; a stock broker; and was born in Arizona. That’s all I know about him; and it’s all I need to know. Because I’ve seen enough train wrecks first hand, to know that becoming friends with benefits – or fuck buddies, with someone, is skating on very thin ice.
One lingering look; one misinterpreted text message; could be the difference between enjoying our casual encounters and falling hopelessly in love.
“You good?” Gabriel asks when I come out of his bathroom. I’d been in there for a few minutes too long – not taking a shit. But analyzing myself in the mirror; wondering if I’ll look any different after. Wondering if when I walk into Starbucks tomorrow for my regular Vanilla Cream Cold Brew, my favorite barista, Kaitlyn, will be able to tell.
“Yeah. Just freshening up.” I lie, not even knowing what freshening up means. It sounds sexier than freaking the fuck out in your bathroom, while wondering why it smells like a giant bag of potpourri. Potpourri isn’t really something that a single bachelor would keep laying around his place; more like his pregnant girlfriend who’s really nice and has no fucking clue he’s cheating on her.
In my search for casual sex, I’ve encountered a lot of taken men with a wandering eye. One dating app in particular – no, not Ashley Madison; was notoriously bad for it. Pregnant girlfriend; married, looking for something discreet; trying to get back at my girlfriend for flirting with other guys. Those were some of the more memorable bios, which practically made me give up my hunt all-together.
If I was carrying the child of someone and that fucker had the nerve to go on a dating app looking for someone to spoil in bed, I would literally lose my shit. My reaction would be somewhere between throwing all their stuff out the window; and jumping on a plane, with the only communication being done between us through my lawyer.
“We don’t have to do anything; if you’re having second thoughts.” Gabriel assures me, leaning against the wall outside his bedroom. His place is fairly small; a one-bedroom, one bathroom, with a tiny joint living room/dining room. The two takeout containers from our Chinese food, are still sitting on the coffee table. Mine remains mostly untouched; I can never eat on a nervous stomach.
The only way I was even able to convince myself into doing this, was by shutting down my emotions and looking at it from a purely educational standpoint. I want to gain experience; confidence in the bedroom; and learn how to give amazing head.
I’d always thought it would be with a kind and patient boyfriend, but my search for a romantic relationship has been seriously cock-blocked by my dad. Who yes, I still do live with. Rent in New York is astronomical and given that I just quit my call center job a few months ago, I don’t really have any other choice.
“Can you teach me how to give head?” I ask, timidly looking over at him. Despite discussing my numerous goals in extensive detail over text, saying it out loud is a foreign concept.
“Cutting right to it, eh?” He half-jokes, biting his lip. Joking around seems to be something he enjoys doing, which works for me, because I laugh when I’m nervous. Instead of dropping his pants and thrusting his Johnson in my face, he moves towards me. Not stopping until my back hits the wall and his chest is almost touching mine.
He’s only a few inches taller than me; and we’re naturally at eye-level with each other. His breath tastes like he just swallowed a pack of Tic Tacs – winter mint flavored. “You wanna do the kissing thing tonight; or another time?” He inquires, his thumb tracing over my bottom lip.
“Probably another time.” I answer, trying to calculate how much we can fit into the two hours before I have to take the subway back home. My dad gets off work from the NYPD at exactly 01:30. And if my ass isn’t in my room by the time he gets home, there’s guaranteed to be a missing person’s poster with my face on it, before dawn.
“Okay.” He nods, taking my hand into his and leading us into the bedroom. It’s pretty bland; with only a queen sized bed and two night stands. No pictures from Spring Break; no clothes on the floor; and no TV. “You prefer me laying down or standing up?” He asks, pulling his t-shirt over his head and revealing his chiseled body. Unlike me, he doesn’t appear to dawn a single ounce of body fat on it. Which is both alluring and intimidating.
“I don’t know.” I admit, after picking my jaw back up from the floor. “Like I mentioned, I’ve never done it before.” I remind him, tying my long blonde hair back. Maybe it’s less hot than having it down; but I’d rather not have to worry about it while having the very first dick in my mouth.
He licks his lips, watching me. “I’ll lay down.” He decides, unbuckling his belt, unbuttoning his jeans, then dropping them to the floor. Good god. Is he smuggling a python in there? Even through his boxer briefs, I can see the unmistakable shape of what appears to be a Bratwurst sausage. “You wanna feel it?” He asks, his eyes glazing over when he notices me looking at it.
“Sure.” I say it without even thinking. My brain appears to be running on pure horniness right now. Whoever said man have two heads; didn’t realize that women do, as well.
Sitting back on the bed, he shrugs off his jeans, motioning for me to come over. “Can I take this off?” He asks, his fingers playing with the hem of my t-shirt dress.
“Yeah.” I nod; and he stands up, pulling it over my head in one foul swoop. I bought matching black lace underwear for this specific occasion. Mostly because my normal undergarments consist of sports bras and multi-colored bikinis. And something about them just doesn’t scream I’m hot, fuck me.
“Mhmm.” His hands roam over my sides, easily reaching into my bra and cupping my boobs. “Can this come off?” He asks, toying with the back of it already. I nod, and he easily unclasps it, dropping my brand new bra to the ground. Only a man who’s been around the block would be able to pull off a move like that. I would be annoyed, but then he starts playing with my nipples and my annoyance washes over. “I’m gonna have a lot of fun with these.” He says, his eyes beaming like a kid in a candy store.
After a few moments, he sits back down, bringing my hand onto his manhood. It’s hard as a rock and throbs underneath my touch. “You got me all nice and hard, baby.” He says, his fingers running down my arm.
“You’re really big.” I comment, part of me filling with excitement; the other part of me wondering how the hell he’s supposed to fit in my mouth – let alone inside of me.
Taking it as a compliment, a smug smirk plays on his lips. “You ready to put it in your mouth?” He asks, giving my ass a squeeze.
“If it’ll fit.” I retort, letting out a nervous laugh.
He chuckles and scoots back, resting against a mountain of pillows. Nonchalantly, he pulls off his boxer briefs; allowing his member to slap against his stomach. “You like it?” He asks, grinning when he sees the expression on my face. It’s safe to say that no matter how light he may pack; he always has a carry-on at the airport.
A part of me feels relieved, because I was worried, I’d be so traumatized by seeing a dick for the first time that I’d flee the country and never come back. My biggest concern was man-scaping; if a guy had a hairy dick, there’s no way I could put it in my mouth.
With no connection to the owner of it; and maintaining my own nether-regions quite well, I just wouldn’t do it. I’m not saying it has to be hairless, but if it looks like an Amazon forest; I’m out.
If I, as a woman, am expected by societal norms to be as hairless as a Sphinx cat; the least you can do is run a razor over your junk.
“It’s nice.” I finally respond, not really sure how else to describe it. It looks like a piece of Polish sausage that’s about to be shoved down my throat.
He chuckles. “Come here.” His hands grip my hips, guiding me in-between his legs. His dick looks at me, like it’s trying to wave hello. Leaning forward, his hand cups the back of my head; and I have a horror movie moment where I think he’s going to try and face-fuck me. Instead, he gives me a small smile, before pressing his mouth against mine.
I’ve kissed men before; I’ve made out with men before. But I’ve never really known what I’m supposed to do. Do I follow their lead? Shove my tongue in their mouth? Bite their lip? Cosmo is about as helpful as an audio book to a deaf man.
The kiss is slow, and erotic, like a sensual dance. Thankfully he already knows that I can’t kiss for shit; so, he takes the reins. With one hand cupping the back of my head and the other underneath my chin; he molds and moves our mouths together until we’re both breathing heavy. I try to do my part; trying to follow his lead like a person getting dressed in the dark.
“You ready to take my cock in your mouth, baby girl?” He asks, pulling away to rest his forehead against mine.
Maybe it’s the lack of blood going to my brain, or his fingers toying with my nipples; but I bite my lip at the thought. “Just tell me what to do.”