Four Days of Giving Thanks

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.

Jess took me in deep a few more times before releasing my cock with a slurp. She wiped some saliva from her chin as she stood up saying, "I want you in me, now."

Jess led me over to the couch, where she bent over the back bracing herself on her arms. She spread her legs and showed me her dripping snatch was ready and waiting. I took my cock in my hand and lined it up with her wet slit. I was immediately aware that Jess was just as ready as I was, as my cock slipped into her with no resistance. Her warm, moist folds enveloped my shaft and we both moaned at the sensation. From my angle, I had a great view of my cock splitting open her lips and her asshole pulsing with every stroke. Her sweater had fallen forward, up to her shoulder blades showing more of her muscular back. I had a firm grip on Jess' hips as I kept thrusting into her. The room filled with the sounds of our flesh smacking against each other as I picked up the tempo and began fucking her with a solid rhythm. Even though her face was buried in her arms and the sofa cushion, I could hear Jess grunting every time my cock filled her up to the hilt. The booze was helping me a bit because as amazing as Jess felt, I was just numb enough to hold off from coming too soon.

We were deep into a steady rhythm when Jess lifted her head and said, "Hold on, let me adjust."

I pulled out and Jess pushed herself back up vertically from the couch. I mentioned earlier that Jess had been a dancer for years and was not only muscular but incredibly flexible. Jess kept her left foot planted firmly on the floor and lifted her right leg up, placing it on the back of the couch so it was now parallel to the floor. With her legs at a vertical right angle, she shifted her hips back slightly and planted her hands on the couch by her crotch.

"Hold on to my tits for support" she ordered.

I did as I was told and grabbed her boobs. They were just larger than a handful and I could feel her nipples pressing against my palms. Jess reached under herself and guided my cock back into her dripping tunnel. Then, moving just her hips and pelvis she started pumping against me. Because of the position of her outstretched leg, I had an amazing view of my dick sliding in and out of Jess' pussy. Her lips were split wide and the muscles in her ass flexed with each movement she made. She was soaking wet and I was leaking precum, so there was a ridge of fluids building up where my cock met her pussy. I had a strong grip on her tits and I was squeezing them hard, as I tried to pull her deeper on to me.

As we continued the pace, I could feel a sheen of sweat starting to build on Jess' chest. She was panting and moaning as we both got closer to our climaxes. Jess' hands had a death grip on the couch cushion and I could see it bending and wrinkling in her clutches.

"I'm so close" she finally groaned. "Your dick feels so good." Jess released her grip and flopped forward onto the couch. Her flexibility was amazing as her body seemed to be at an impossible angle. One leg on the floor, one outstretched along the back, all while her torso was folded forward over the couch. After a few more thrusts, she spoke up again.

"My ass. Play with my ass."

Jess and I had done some anal play before, from me fingering her to full penetration with my cock. Her position still had her spread wide for me and I could see her puckered opening clearly. I took my thumb and gathered some of the combined juices flowing out of Jess' pussy and coated my digit. Then, using both hands to fully spread her cheeks, I slid my lubricated thumb past her tight ring and into her ass.

I could feel my own cock through the thin membrane separating her pussy and ass but barely had time to enjoy it as Jess exploded. A string of expletives poured out of her.

"Oh...fuck....shit.....fuck my pussy. I'm fucking coming. Fucking grab my ass. Fuck. Oh....Fuuuuuck."

As Jess' pussy clenched around my dick, I felt her ass gripping my thumb. As she moaned and yelled into the couch, I felt my cock start to explode inside her. Wave after wave of cum shot deep into her pussy as we both kept thrusting against each other. When I stopped spurting, we were both gasping for breath.

"My leg," I heard Jess whimper.

Realizing she was still in her pretzeled position, I took my thumb out of her anal passage and slid my cock out of her pussy. I immediately felt a flow of our juices come out of her pussy as I pulled out. Helping her up, she shifted and pulled her leg down from the back of the couch. She was a bit unsteady as I got her fully upright and turned her back toward me. We kissed and enjoyed the post-orgasm moment.

"Mmmmm..." she said giggling. "Kitty is very happy right now." She gave me a quick kiss and bounced off to the bathroom to clean up. I stood there with a deflating cock, covered in fluids thinking, "Really? Kitty? Again?"

----Thursday, Thanksgiving ----

Thanksgiving morning was rough -- I'm not going to lie. We were both hungover from the booze and the sex the night before. Our goal was to be on the road to her parents' place by 9am, but it was almost 10 by the time we were driving. Plus, I knew I had to leave by 3:00 in order to get back for my shift. I dressed in slacks, shirt and sweater and brought my work suit with me figuring I could change either before I left or at work later.

Jess looked amazing. She was wearing a dark brown skirt that was loose, pleated and ended just above her knees, showing off her amazing legs. Those toned legs were covered in black tights that led to a pair of low heels. She was also wearing a form-fitting beige turtleneck that hugged her curves and showed off her full rack. Her outfit was totally appropriate for a family Thanksgiving but attractive and sexy at the same time.

We had been on the road for about an hour when we hit some traffic. We flipped on the radio and heard there was an accident that would slow us down by about 45 minutes. As we crawled on the interstate, Jess and I made some idle chatter about not being together for the weekend but looking forward to staying at the hotel after the reunion on Saturday night.

"You know who's gonna miss you this weekend?" the girly voice was back.

"You?" I replied.

"And my kitty" Jess said. "It felt so good having you inside her last night. I don't know what I'm gonna do without you."

As she spoke, Jess adjusted in her seat, took my hand that was resting on her thigh, and moved it up closer to her crotch.

"I don't know if kitty will be able to make until Saturday night." She now had her left leg up on the seat and was spreading herself open. As she moved my hand further up, I felt her tights come to an end at the top of her thighs and I could feel her wet pussy lips. Jess moaned as I started running two of my fingers up and down her slit, spreading the moisture along its length.

"Mmmm....that feels good." She uttered. Her head was now back against the headrest and her eyes were closed. "But I don't want to get my skirt wet."

Jess opened her eyes and lifted her hips slightly, just enough to pull her loose skirt up to her waist. For the first time I could see how I had access to her pussy. Jess had taken some scissors and cut out the panel on her tights that covered her crotch. So, while her conservative winter tights were fully intact, her pussy was completely exposed.

Jess reclined her seat a bit and spread her legs wider for me. She guided my fingers to her clit while she took her own and began slowly moving two of them in and out of herself. Traffic was still at a crawl and we were surrounded by other slow moving cars. For most people, it probably looked like Jess was just sleeping but anyone in an SUV or truck would probably be able to see what was happening in the passenger seat.

Because of the angle, I was only able to use two fingers on Jess' clit, but I went back and forth between flicking her little button and sometimes pinching and squeezing it between my digits. Jess, meanwhile, was fully thrusting two of her own fingers in and out of her cunt. Her hips were bouncing in the seat and her tits were heaving under her tight sweater. I kept switching my view between the traffic, Jess' pussy and the cars around us.

As Jess approached her climax, there was a pickup truck next to us riding a big higher than my sedan. The guy who was driving was blatantly looking down as Jess and I worked over her pussy with our hands. His passenger was leaning all the way across him trying to get a view for herself. I wondered if she was rubbing his cock while they both watched Jess start to thrust and moan with her orgasm.

Jess' fingers suddenly thrust fully into herself, her hips rose and she grabbed my wrist with her other hand. She was moaning and gasping for breath as her orgasm washed over her. I could feel her squirt just a bit of fluid as she peaked and rode her orgasmic wave.

"HOOOOOOOOOOOOOOOOOOONK"

The sound of a loud horn behind me made me realize that we were passing the accident and traffic was starting to move again. Both my car and the pickup truck next to me were blocking the only two moving lanes. I think we both had the same "Oh shit" moment as we pressed our gas pedals and started moving forward again.

Jess, meanwhile, had brought her wet finger up to her lips and was licking them clean of her own juices. Rolling her head over toward me, she said, "Too bad traffic started moving. I wanted this to be you in my mouth, but I guess you'll have to wait until Saturday."

The rest of the ride was uneventful, except for my raging hard-on and a growing case of blue balls that I tried to get under control before arriving at her family's house. When we did arrive, it was a typical family setting. Everyone hugged and greeted each other. Jess helped her mother in the kitchen, while I caught up with the different family members who were there. Everyone was disappointed that I would be leaving early and wouldn't be there for some of the traditional holiday decorating and tree trimming over the weekend.