This is my entry into the
Literotica 2021 Winter Holidays Story Contest
. I always like to reinforce that, like my author name says, all of the stories I tell here have a basis in truth and are always based on actual events from my life. That being said, I do like to add some twists & embellishments to keep them interesting for the readers. This one has less embellishment and I actually found myself chuckling when I thought back about this weekend.
This story has waves of exposition, story and sex, so be prepared for some repeated build-ups between sex scenes. I appreciate comments and always welcome guesses as to which parts are totally true and what I added for twists.
Hope you enjoy -- please leave feedback.
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---Prologue---
Of all the women I write about in my stories, Jess is the one who gets mentioned the least and undeservedly so. Jess was probably the nicest woman I ever dated. She was a professional dancer (jazz & tap, not pole you perverts!) who had toured with a few big names during her career. By the time I met her, we were both in our late-twenties, and she had transitioned to teaching kids at a local dance school.
Jess was of Greek heritage and had raven black hair that was cut at her shoulders and beautiful olive skin. She was solidly built with broad shoulders, a full set of breasts and a dancer's muscular ass and legs. Like I said, Jess was probably the nicest, most caring girl I ever dated. The problem is that she was the "rebound" between my college girlfriend, Kat, and my next girlfriend, Tara. My time with Jess was fairly short and truth be told, I kind of screwed her over by meeting, dating, and sleeping with Tara all behind her back.
But even though our time together was brief, Jess and I still had some fun times and one or two that are worthy stories to be told here.
---Thanksgiving Weekend, 1990-something---
For the holidays, Jess & I agreed that we would split up for Thanksgiving and then travel to see my parents (who lived in warm Florida) for Christmas. She was going to visit her family and I was going to stay home and work. Things got a bit more complicated when her High School class announced that their 10-year reunion would be on the Saturday of Thanksgiving weekend at a country club/resort that was shut down for the winter near their town. I was working as a manager of a hotel and managed to trade some shifts so that I worked the overnight on Thanksgiving, Friday afternoon and Saturday morning.
Her family lived about an hour and a half away from where we were, and we made the decision to go out with friends on Wednesday night and drive to her family's place early Thursday morning. I would stay for a little while, then head back to work for the weekend and meet her for the reunion on Saturday. My relaxing holiday weekend suddenly looked like I would be spending as much time driving as I would eating turkey.
----Wednesday Night----
After work on Wednesday, Jess came to my place and we went to a local bar where we met up with some friends who were also there to officially launch the holiday season. Jess was dressed in a typical Midwest autumn outfit. Skinny jeans that showed off her toned legs and ass, an oversized sweater to stay warm and a pair of camel-colored riding boots that went up to her knees. The night started off tame with all of us catching up and drinking various beers on tap. Then came the witching hour when the whiskey started flowing. Like any group of 20-somethings clustered in a bar as we all got tipsy, we all got more public with our displays of affection. Around the bar, you could see different couples standing closer to each other while others seemed to have their hands wandering under the tables or just out of sight of others. Singles were pairing off and kissing in corners or in plain sight. Jess and I were no exception. I was standing at the bar talking to friends with Jess in front of me. The longer we stood, the more I noticed that she was grinding her denim-covered ass against my crotch. I had one hand on my beer and wrapped the other one around her waist, quietly pulling her tighter against me so she could feel my increasingly hardening dick. At the time, we thought we were being perfectly sneaky when in fact everyone around us could probably tell exactly what was going on.
As the clock passed midnight, Jess turned to me and wrapped her arms around my neck.
"Gimme a kiss" was her only request.
I obliged and leaned down to kiss her, wrapping my arms around her. Our quick kiss quickly turned into our tongues exploring each other's mouths as we forgot our public surroundings.
"Harrrumph! Get a room! Harrumph!"
I broke the kiss to see one of my friends, Barry, faking a cough with his eyes rolling back as he called out our PDA. Jess, however, was unfazed and pulled me back for one more quick open-mouthed kiss.
"For once" she said with a smirk, "I agree with Barry. Let's get out of here."
Even though we were both eager to get out of the bar and back to my place, it still took us nearly half an hour to say our goodbyes and work our way out the door. The air was typically chilly and windy as we walked with our arms around each other toward my building. Jess was huddled as close to me as possible as the wind cut through our garments, sobering us both up as we walked.
"You sure were anxious to get out of there" I joked as we picked up our pace to get out of the cold wind.
"Well" she said, "I wanted to get you home so we could play!"
"Play" was always Jess' code for sex. She would always say it in an almost juvenile girly voice. It was strange, she would never say "sex" or "fuck" or anything else. It was always "play" in a girly voice. Sometimes she would combine it with other words and phrases like "my kitty" and "bum bum". Truth be told, it was kind of annoying and disconcerting. Maybe it's me, but I'm not really turned by someone who talks like a juvenile. It's just kind of creepy. I remember thinking she should just say something like an adult when she wanted to fool around. But it was always "let's play". Then, when we would start "playing"... her tone would change into something out of a porn movie. But more on that as I continue....
"You know I'm always on board" I replied, "Especially when you spend half the night rubbing that ass against me in public."
Jess giggled in that girlish tone again and said, "Well, you're probably not going to get to play with my bum or anything else while we're at my parents place or while we're apart, so we better take advantage of tonight."
Jess had warned me that her family wasn't as "progressive" as some others we knew. I got along with everyone I had met to that point, including her father who looked like a blue collar Tom Selleck when he was on Magnum PI. I am a solid six feet tall with some muscle, but he still had a few inches on me and was even broader. Her mother was a small rotund Greek woman who gave big hugs. I had met her younger brother once and he seemed fine, as well as some of her extended family.
All that being said, there was still an aspect of "don't ask, don't tell" when it came to the fact that Jess spent a lot of time at my place and not her own. It was made clear that during our visit, PDAs would be kept to a minimum and sex of any kind wouldn't be an option.
After about 15 minutes, we made it to my building, keyed in and walked up the 3 flights to my apartment. As soon as the door was open, Jess pushed me aside dropped her coat in my arms and declared, "I have to pee!" as she ran to the bathroom closing the door behind her.
While she took care of her business, I hung up both of our coats and started turning on the lights and the heat in the apartment. I had just kicked off my own boots when I heard the toilet flush, the water run, and bathroom door open.
Jess emerged, still wearing her oversized, cranberry-colored sweater and apparently nothing else. Her feet and legs were bare, and the sweater came down to barely cover her ass and crotch. With every step, the sweater would ride up a bit and I could see Jess' trimmed pussy hair. Unlike some women, Jess liked to leave her pussy well-trimmed in a neat triangle but not completely bare. Her full breasts seemed to be bouncing unencumbered under the sweater as her bare feet padded across the hardwood floor toward me.
With a big smile on her face, Jess pushed me against the wall and started fumbling with my belt buckle. "Okayyyyyy! It's Playtime."
For a split-second, my cock softened at sound of those words and that voice, but it rebounded when she got my pants undone and placed her hand on my cock. Jess sunk to her knees taking my jeans and boxers with her as my cock sprang free. Jess' sweater rode up as she sat back on her heels, revealing her naked ass.
Without a word, Jess took my cock into her mouth and wrapped her hands around to my ass cheeks, pulling me further into her mouth. After bobbing her mouth up and down my shaft, she pulled back until only the head of my cock remained in her mouth. Looking up at me she swirled her tongue around my head, flicking it repeatedly on the sensitive underside. Without losing eye contact, she plunged her mouth back down my cock until she was pressed against my pelvis. She repeated this a few more times until she allowed my cock to pop completely out of her mouth dripping with precum and saliva. Jess wasn't done yet, though. She adjusted her head slightly and from the side began licking and kissing up one side of my cock and back down the other. At this point, the wall was the only thing holding me up as my own neck and head lolled back against the wall with my eyes closed, focused on the feeling of Jess' mouth on me.
