I’m 28 now, thinking back on my first sexual experiences and where they went right (and pretty wrong, at a couple of points).
I was an awkward, fat kid, I never even kissed someone in high school. The tide began to turn spring semester of senior year, I’d hit my last growth spurt to 6’1″ and wasn’t so much fat as just awkward.
In college I got in better shape, grew my hair long, grew a beard and learned to dress (after a fashion – peak workwear era, Red Wings, raw denim and flannels/workshirts – I looked like a fucking lumberjack) – I wound up being reasonably good looking, but I still saw myself as that fat nerdy kid (also: untreated depression).
Looking back, I realize I was missing signs of interest from women but c’est la vie. At my first job waiting tables, a cute server named Amanda took me back to her apartment two nights in a row after we got drunk… and I just talked at her.
Just after turning 21 I took a job at a dive bar doing everything but bartending – I worked the door and “security” (threatening frat boys who got handsy), I barbacked, I DJed here and there, I helped out with some of the bookkeeping, I developed a mildly serious drinking habit.
The owner was Emma – mid to late 30s, regularly changing hair colors, prone to maximizing her cleavage for the shifts she took as bartender, mother of two. I wasn’t running to my sad studio apartment to jerk off to her (which I was doing 4 times a day) but I definitely found her attractive. Which was irrelevant because I was a loser destined to die a virgin and she was married anyway.
Emma took me under her wing, teaching me to bartend when she wasn’t in the DJ booth with me picking out danceable goth music for ’80s nights and making fun of the failure of my classic hip-hop night (the audience did not go crazy for Boogie Down Productions and Kool G Rap).
It was four months in, just the two of us sitting at the bar after close when she dropped a bomb on me: “Stop flirting with me or kiss me.”
My mind went to her being handsy, us brushing against each other, our rapport – oh, shit, I had been flirting with her. I was at a loss for words but finally got out “you’re married.”
“We’re an open marriage.”
I spilled the whole story of my non-experience and ignorance that I had been flirting with her – barely even any over the shirt action in your history will do that.
“You’re an idiot.”
Emma then took it upon herself to kiss me. She was surprised that I was pretty decent – not too hesitant but not too much tongue, not too sloppy. She told me about one guy who had licked her face from chin to forehead – he became known as “cow tongue” to her friends.
She lead me to the office where there was a couch in much better (and more sanitary) condition than the ones spread around the bar and straddled me as we started making out. Shirts came off and I explored her, finding the erogenous zones on her neck and shoulders, figuring out the right amount of pressure and pull to make her moan when she lead my mouth to her breasts.
She took off her pants and underwear and sat on my lap, back to my chest. As I kissed her neck, she sucked on two of fingers before guiding my right hand to her pussy, my left hand zeroed in on her breasts and nipples. She guided me as I fingered her, soft yesses and moans, “right there” as I found the right pressure and motion for her clit, she shuddered when I held pressure on it with my thumb and slowly worked those two fingers in her. Breathing a bit heavier, she stood and I got my
Emma had what I’d call an excellent mom-bod – stretch marks and no perfectly taut stomach, she complained that her breasts weren’t as perky as they had been once upon a time – but she was sexy. She had strong, toned thighs (later she tried to get me to go to Crossfit with her – I declined, I like my shoulders undamaged).
“No sex tonight, but you’ve really never gotten a blowjob, you’re not saying that just to seduce me?” Emma’s right eyebrow was arched, teasing me.
I assured her that my dick had never been touched by anything but my own hands. She leaned over to kiss me again and got down on the floor between my legs, pulling my boots and jeans off, feeling and kissing my erection through my briefs.
I do not by any means have a porn dick, but it’s longer and a bit thicker than average from what I’ve been told – one FWB’s sex blog reviewed it as “feels amazing when thrusting” – I’m also a grower, but that was far from an issue here.
When she removed my briefs, my cock sprang out and bounced against her cheek. Those safely tossed in the corner, she turned her full attention to me, maintaining eye contact as she took hold of my shaft and licked the precum from my head. I moaned deeply and my eyes rolled back for a second – but I didn’t want to miss a second of this.
She took my head in her mouth, lazily moving her tongue around it as she began to slide her mouth down, agonizingly slow, enjoying herself. I started to thrust involuntarily and she stopped to giggle. “Calm down, you don’t want this to be over too soon, trust me. Touch me.”
The process began anew and I reached down her breast, feeling and gently rolling a nipple between my thumb and forefinger. My other hand went to her head, just resting and playing with her hair, caressing her neck. “Mhmm” she hummed on my dick.
She took me down in dips and releases until I reached her throat, one hand around still making sure that I didn’t accidentally start to thrust too deep while the other started to play with my balls.
She released me from her mouth, a line of saliva from the tip of my dick to her lips and began to lick and suck my balls, gently stroking me. The involuntary thrusts were getting harder to control and she took me in her mouth again, all the way to her throat again and began bobbing at a steady rhythm, kneading my balls in concert.
I began to feel a familiar sensation and gasped that I was going to cum and she picked up the pace, no stopping the thrusting now and with a final moan I came in her mouth, she swallowed and swallowed, not a drop missed. She kept me in her mouth until she was sure I was done and let me slide out, resting her head against my thigh.
I pulled her up to kiss her, which took her by surprise – she said most guys she’d been with wouldn’t kiss after a blowjob. I’m not looking for a snowball but I’d find it weird if a woman wouldn’t kiss me after I went down on her.
She curled up against me on the couch, I was still processing and basking. “I just started doing that, you’re lucky.” “What?” “Swallowing.” (Yes, I was lucky.)
She laughed after a couple of minutes, noticing I was getting hard again just from proximity to her naked body.
We got up and got dressed, kissed again, and then headed for the front door. She told me keep some condoms on hand and take her somewhere classier next time, like my apartment.
Source: reddit.com/r/gonewildstories/comments/rguh8f/had_most_of_my_first_sexual_experiences_with_a
Great story, hope you write more x