When I was in my mid-20s, I got a job as a checkout guy at a well-known health foods supermarket chain, in an upper-middle class suburban area. For the most part I enjoyed the job and getting to chill with my coworkers. The clientele was a wild card – you had your health food nuts, your chill regulars, your crazy regulars, middle-aged stay at home moms who had an above-average grocery budget, and more. Overall not that different from your average retail/food service gig, but one thing I realized early on was that this chain tended to attract a certain kind of girl – usually of the artsy, hippie or hipster-type persuasion. Another thing I realized was that if you were decent looking and charming, a checkout guy could pull mad tail among the store’s customers, if you were so inclined. A little about me – I am (and was) 6’4” tall, white, a little on the lanky and thin side, but I wear it well. Very long hair, stubble, a couple of visible tattoos, play in a band. Honestly, if you imagine a typical “health food checkout guy” I’m probably not that far off. I’ve never been a player or your typical jacked “hot” guy, but I’m definitely a certain kind of girls’ “type”, as I would find out. I have a few fun stories of my time working here to share.
One of the first girls I had my eye on was a regular we’d see a couple times a week – let’s call her Jessica. This girl checked so many boxes for me; taller, around 5’8” or 9, pale skin with lots of freckles, cute round glasses and blue eyes, this auburn-red hair that went down her back. She had a lovely figure, but curvy in all the perfect ways. Jess didn’t have your typical supermodel look, but she was just stunning with her own unique style, and she was a few years older than me, which is also a plus in my book. She also looked like she was dressed for the occasion every time she went grocery shopping, like she was hitting some chic club or gallery with her friends right after. My favorite outfit of hers was this orange top that left her midriff and arms bare, paired with this short black skirt. The first time she came through my line, I had to stop my eyes from popping out of my head. I tried to be extra friendly and courteous, and before long I started to noice that she always made a beeline straight to me to check out, past everyone else. Over time I got to learn a little about her – she was a professional interior designer, she enjoyed checking out local art galleries and spaces, she was Jewish, and her taste in things like movies and music was stuff I had close to ZERO familiarity with. Think a lot of classical music and old foreign movies. The fact that she was so sophisticated and self-assured just drove me even crazier. Once, she showed me a picture of her Halloween costume from the previous year, some kind of ballerina from a movie, and it took everything I had to play it cool after seeing her in that outfit.
I was anxious about making a move at first, at least partially because I didn’t want to get written up for skeeving on customers, but eventually I decided that I need to shoot my shot. So I finally asked her one Thursday if she had any weekend plans. She told me she was planning to hit a gallery opening with some friends in the city’s arts district. I nonchalantly said I’d be down there too and we might run into each other. She was excited to hear this and told me we should meet up. I got her number and felt excited by her response.
This is already getting long so I’ll try to cut to the chase. Come Saturday night, I met up with Jessica and some of her friends, and she looked beautiful as always. Her friends seemed a lot like her and were nice but kind of gave me a wide berth. Jessica was really happy to see me though, and after the gallery we ditched her friends and headed to a wine bar, just to talk (and flirt). Everything about this night seemed unreal – it’s like what you expect going out with a high-class rich girl in the city to be like. Jess wasn’t snobby or pretentious at all though, and I managed to be a good conversationalist and keep her laughing. As we talked, we snuck little touches here and there – a graze of the arm, a touch on the small of her back, a quick brush. Finally after a while of talking, I asked about the movie she had taken the aforementioned Halloween costume from. I said I’d never seen it, and she just smiled and said, “Well, why don’t you come by my place and we can watch it?”
One Uber later, and we were at her loft apartment, which was exactly as chic as I expected. We grabbed a couple more drinks, plopped down on her couch and started the movie. I honestly don’t remember much about it, I was just a bundle of nerves, but I figured if I’d made it this far then things looked pretty good for me. We did that thing where we tried to nonchalantly nudge closer to each other on the couch until we were practically right on top of each other. She caught me looking at her, and after a moment of just watching each other, we finally started making out. It was ravenous, we had our hands all over each other, it was like a big balloon of tension just popped. I kissed her neck and she gave this deep moan; I filed this information away for later. I started trying to undress her and that finally made her come up for air; all she said was “Bedroom”, and she took my hand and led me.
When we got there, she turned around to face me, and instead of continuing our kissing, she started undressing. There’s just something so hot about seeing someone you’ve fantasized about for months taking her clothes off in front of you. Her breasts were like these perfect globes, and she often wore clothes that accentuated that lovely rack. Finally getting to watch her remove her bra and set the girls free was an image I’ll keep in my brain forever. When she was done, she just gave me this sexy smile, and I couldn’t take anymore. I tore off my shirt and pounced on her, taking her to the bed, exploring every inch of her body. I love playing with and sucking on a girl’s breasts, and I had the time of my life, while she moaned with pleasure. After a few minutes I made my way down to her pussy. No joke, one of the most beautiful vaginas I’ve ever seen, and with a short landing strip, and I dove right in, teasing her clit and licking voraciously, inserting a finger when I knew she was on the edge. Her cries and moans were so damn sexy, and I couldn’t help but think about how crazy it was that I was having my way with the gorgeous supermarket shopper. Finally, after a couple minutes, she pushed me away and said “I need to suck your cock.”
Well, I’m not gonna say no to that! I quickly ripped off my pants and boxers (my enthusiasm earned me a giggle), and sat on the end of the bed. Jess knelt down in front of me and started gently touching my rock hard dick, teasing me the way I did her only minutes before. Finally she took it in her hand and slowly slid my cock into her mouth. I don’t usually come from oral, just always been this way, but there was no denying how enjoyable it was getting head from this sexy bespectacled redhead – her enthusiasm and the lovely view made me feel like I’d died and gone to heaven. After a few minutes I whispered an idea into her ear, and she moaned in the affirmative, which is awesome when it’s your dick in her mouth. I pulled her up and lay back on the bed, and she climbed up and turned around on top of me until we were in a 69 position. I lapped at her wet pussy eagerly for a few minutes while she licked my cock until she finally came up for air. I knew what she was gonna say and said it first – “I need to fuck you right now.”
I ran back to my pants to grab a condom and lay back down on the bed. Jess held out her hand and said, “Allow me.” I handed her the condom, and she opened the wrapper, put the condom on her lips, and applied it using her mouth. Fellas, if you’ve never had a girl do this to you…it’s truly an S-tier move. It drove me wild that this chick I had been talking to about Ingmar Bergman movies a couple hours before had so many dirty tricks up her sleeve. After making sure it was rolled on properly, she saddled me and began rubbing my dick against her wet opening. She knew how to tease, and it’s like she read my mind – I love it when a girl takes me for a ride. Finally, I put my hands on Jessica’s hips, and she knew it was time. She guided me in with a moan, and after she got used to me – I’m pretty average, but I don’t think I’ve ever been harder – she started rocking back and forth on my cock, which soon moved up to full-fledged bouncing. I thrust my dick with plenty of enthusiasm, both for the tight sensation of her pussy and for the glorious view of watching this gorgeous girl ride me, her face contorted with pleasure, biting her lip and moaning. I reached up and grabbed those amazing breasts again, at first pinching her nipples, and then I sat up so I could properly suck on them again. I love driving a girl crazy with pleasure, and Jess was very accommodating. I pulled her back down with me after a minute and performed my coup de grace – kisses on the neck and a nibble on her ear. This sent her into overdrive, and before long she was whimpering “Oh my god, oh my god, I’m gonna cum” into my ear. This just convinced me to thrust harder and deeper, and soon she had her orgasm, throwing her head back with this super sexy guttural moan as she came.
I barely gave her time to catch her breath before I flipped Jess over and started pounding her in missionary, which usually makes me finish pretty quickly. Sure enough, after a couple of minutes I was at my limit, and I flooded my condom with my cum. We just lay there for a minute, exhausted, before I finally rolled off, and we lay in the afterglow in her dimly-lit bedroom. After we cracked a couple “checkout” jokes and caught our breath, Jess got up and moved to the bathroom door. The door frame captured her silhouette perfectly as she hit the light switch, and said, “I’m going to take a shower. Care to join?”
Uh, yes. I hopped up and joined Jessica in the bathroom. It took a couple seconds for my eyes to adjust from the dark, and to dispose the condom, but getting to see her incredible body in the light more than made up for it. We got in the shower and both initially started scrubbing, but we couldn’t keep our hands off one another. I love grabbing a girl from behind, playing with her sensitive areas and kissing her, and gladly did so while she soaped up my cock, which was quickly becoming primed for round 2. I took the chance to kiss her neck once again, and that sent her over the edge. In a night full of incredible views, this was the best one yet – the tall, pale, freckled, sexy redhead with a perfectly curvy ass, leaning forward in the shower, presenting her holes to me. She looked back over her shoulder, and I saw her face, without glasses for the first time, makeup running off from a mixture of water, sweat and tears. She said nothing, but nothing needed to be said.
No condom. I went for it anyway (dumb move, kids). I had to. Properly feeling her pussy was everything I’d dreamt and more. I didn’t waste time and got to work hitting her nice and deep. There’s nothing I love more than a girl who wants you so bad she can’t hold it in, and her moaning made me feel like the king of the world in that shower. I couldn’t help but notice her asshole as I fucked her from behind, and I decided it couldn’t hurt to try my luck. I rubbed a cursory thumb over it, and it elicited yet another deep moan from Jess. I continued to tease and toy with her back door while I slid in and out of her sopping wet pussy. Finally, I couldn’t take anymore. Fortunately, my pull out game was pretty strong, and I removed myself just in time to shoot my hot cum all over Jess’ back and ass. She turned around and kissed me again, and after we cooled down and finished our shower, we crashed in her bed and I left for work the next morning.
Jess and I hooked up a couple more times before she across the country. But that first experience was so hot and gave me a lot of confidence, and remains a wonderful memory.
Sorry about the length, lmk if you want to read more stories!
Source: reddit.com/r/gonewildstories/comments/jxtq0x/heckout_confessions_part_1_the_sophisticated
Great story!!
More please!?
When have you last contacted her?