“Stop flirting with me or kiss me.” So I did.
The summer after high school, my older brother’s friend got me a job barbacking at a small club – normal, relatively quiet, bar five nights a week, packed hip-hop club on the weekends. It was a great gig – cash under the table, minimal hours for enough money to have fun, a sharp increase in alcohol tolerance…
I was young and enjoyed the job, so I worked hard and quickly became the owner’s personal barback in the DJ room on weekends. She could count on me to keep everything stocked and glassware clean, which earned me a number of free shots and lessons in bartending.
We had a rapport but I didn’t think much of it – Alyssa was in her mid 30s, married, a couple of kids, not smoking hot but very cute. I had dated but nothing serious and I was pretty self-conscious about being a virgin. As a young, six-foot tall white guy with red hair to my shoulders I got a lot of attention from the mostly black female clientele but I had no game and never could figure out how to proceed. All summer the best I could do was an occasional makeout session.
As summer turned to fall, I started at a local university and began stopping at the bar after classes every now and then to sit around and chat with whomever was in that day – I was starting to feel more in common with day drinkers and bartenders than my actual peer group. Better stories to be heard, by far.
A few weeks before my 19th birthday, I stopped in and the bar was completely empty except for Alyssa covering someone’s day shift. She was on a stool at the edge of the bar, smoking a Parliament and watching something to fill the time. I grabbed a water and sat with her, we started talking about classes, life, dating situation (nonexistent), whatever was on the TV, her college experience. A while in, she asked me if I wanted a drink and I said sure. She made a strong Jameson on the rocks for me and poured herself a vodka cranberry.
The talking continued and the drinks needed refilling, then refilling again. We’re laughing about a girl fight from the weekend before when she stopped and looked me in the eye.
“Stop flirting with me or kiss me.”
Time stopped – what the hell? She’s married. Is this a joke? Is she fucking with me? We were flirting? After a moment’s hesitation I decided there wasn’t much to lose so I went with it. I kissed her. I pulled her close and we started awkwardly making out like drunk college kids (which I was).
My right hand went to her chest, cupping her 34Cs through the Patron t-shirt she had worn to work, her hand squeezing my thigh and working it’s way to my crotch. She broke the kiss and I momentarily froze, thinking it was over – instead she ran to the front door and locked it.
She walked back to me, smiling coyly, kissed me tenderly again and started to explain. After ten years of marriage, her husband wanted to spice things up so he had started pushing threesomes – two guys, two girls, whatever. Alyssa was uninterested but he kept pushing and then suggested an open marriage. Tired of hearing about all of it, so she agreed. She had no intention of taking part but after he fucked one of her friends (not a stranger, a woman that even I knew) that changed.
So here I was, the lucky guy who she had chosen for her first extramarital fuck. She had been trying to get me alone (and ply herself with a little alcohol for courage) and through dumb luck had succeeded.
“Are you interested? I know I’m old and your boss, so if you say no I won’t be offended.” Clearly Alyssa didn’t understand the mind of a teenage boy – older woman AND my boss? That made it twice as hot.
I hesitated, though, “I… I’ve never had sex.” Her smile grew a little more mischievous – “Have you ever had a blowjob?” I shook my head and she took my hand, leading me out of view of the windows at the front.
I sat in rolling wingback chair pushed into the corner where we were safe from anyone looking in and Alyssa knelt in front of me, kissing my already hard cock through my shorts. She undressed me, pulling my shorts down around my ankle and nuzzling me through my boxers, enjoying the tease. My heart was racing
Grabbing my boxers in both hands she looked up at me – “The only rule is that you warn me before you cum, okay?” I would have agreed to sell my soul at that moment. “Mhmm.”
She pulled by boxers and shorts completely off and started by licking my balls lightly, with the just the tip of her tongue, moving in tighter so my erection rested against her cheek. It felt amazing.
She moved from my balls to the underside of my shaft, the tip of her tongue tracing a line to the head of my cock, then her mouth taking the head. It was so incredibly warm, a sensation that I’ve ever tired of. Her lips sliding past the head, her tongue started working me.
She kept going, making sure to thoroughly coat my dick with saliva then moved back up, starting to stroke me while she sucked my cock and swirled her tongue around the head.
I was already starting to feel my balls tightening, getting ready to explode and she could sense the tension in my legs. She withdrew momentarily and asked me how it felt, lazily stroking my cock with her right hand, squeezing my leg with her right.
“Fucking amazing.”
“Good. Now touch me, stop grabbing the chair.”
I quickly did as I was told and started running my hands everywhere i could reach, squeezing her shoulders and playing with her hair as she returned her attention to my cock.
Again she started descending, working me with her hand, slowly getting deeper and deeper, until her nose was buried in my pubic hair. I moaned, feeling my dick against the back of her throat. Then I felt her tongue start to play with my balls where it could reach – later, I would learn she was incredibly proud of this trick, for now I just enjoyed it. Withdrawing momentarily for air, she started to speed the process up – faster strokes, sliding her mouth up and down my cock. I started to tense again as her speed increased, I felt my world narrow down into a single point of light – almost like my field of vision went black and the only thing I was aware of was her mouth on my cock.
Everything exploded. Sound and vision rushed back to my world and I felt surge after surge of cum pouring into her mouth. Swallowing every drop, she held me for a moment and then let my softening cock slip out of her mouth.
“Oh shit, I’m sorry, I couldn’t say anything,” I quickly started to apologize, hoping I hadn’t destroyed all future chances with her.
She laughed, “Don’t worry, I knew. I’ve never had someone moan like that – but then, I’ve never had a virgin before.”
Alyssa climbed up on my lap and put her head on my shoulder, sighing lightly. I turned my head to kiss her again and her breath was different – not quite tasting myself but definitely what I’ve learned to associate with post-blowjob breath.
A few minutes of contentment passed, the occasional kiss, mostly just holding each other. I started to desperately want to return the favor and the arm not wrapped around her began once more to explore her body. I undid the buttons on her shorts and slid my hand inside her panties, sliding past a thick bush and finding her absolutely soaked slit. My fingers traced up and down, lazily exploring her pussy, earning a deep sigh from Alyssa but she stopped me.
“While I’d love to continue this, it’s almost six and someone is bound to come in for a drink. I think we’ll have to wait until later.”
We straightened up, she went behind the bar and rinsed her mouth with vodka, I unlocked the door and we sat back on the two stools from whence we started. This time I took one of her Parliaments – it only seemed appropriate.
To my delight, it wasn’t that long before I got my chance to return the favor but as this is already quite long I suspect it will have to wait for part two.
Source: reddit.com/r/gonewildstories/comments/4utk32/in_the_corner_losing_part_of_my_virginity_mf