This is my entry into the 2025 Valentine's Day contest. I always like to reinforce that like my author's name says, all of the stories I tell here have a basis in truth and are based on actual events from my life. I've found that writing true(ish) stories from my experiences translate better to the page. That being said, I do add some twists & embellishments to keep them interesting for the readers. Names are always changed.
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Everyone in the story is 18 years of age or older.
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"That's it Jay! Fuck me! I want to feel you come inside me!"
My girlfriend Jessica was on top of me, riding my dick hard. I watched as the dark triangle of her pubic hair bounced up and down my shaft. My hands were gripping and squeezing her full tits and I felt the first burst of cum shoot into her pussy.
"Unnnnggghhh", she groaned as she knocked my hands away and fell on top of me. My arms fell to my sides as we both gasped for breath, our sweaty skin pressed against each other. We lay there for a few quiet minutes as Roxy Music played from the bedside CD player. When my deflating dick slipped out of her, she slid off me to the side, a trail of our mixed fluids dripping out of her on to my thigh. Rather than running to the bathroom, she snuggled in next to me and wrapped an arm and a leg over me. I could feel the juices from her cunt pressed up against my leg and saw the glint of sweat on her skin in the dim light.
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, thanks to years as a professional dancer and instructor. She wasn't skinny, as her boobs and ass were full and gave her a great set of curves, yet she remained incredibly flexible.
She was a girl who was sweet and innocent during the day, someone you could be bring home to grandma. But at night, she was willing (and often able) to try anything in bed. During my time with her, I probably tried more creative sexual positions than with anyone else. Jess' ability to move her legs in virtually every direction made sex possible in a multitude of ways. She also had the libido of a rabbit in heat which made for our very active sex life.
"Hey", I said breaking the silence, "Have you thought about what you want to do for Valentine's Day this Thursday?"
"I don't really know. What are you thinking?"
"I mean, I can have Helen call around and get us a reservation somewhere if that's what you want to do."
"Sure. That works." Her response was less than enthusiastic.
"I'll do whatever you want." I added. "I feel like Valentine's Day is more for women than guys anyways."
"You're not wrong. As long we wear something sexy and red, you guys are pretty much fine, right?" she added a little poke in the ribs to match the verbal jab.
"Seems like a fair trade for overpriced roses and cheap, heart-shaped chocolates." I joked back.
"The thing is" she continued. "Restaurants are packed with 'special' menus and terrible service. Plus, everything is so cheesy that night with every couple in the world going out."
"I would say we could get a hotel room for the night but it's sort of the same thing. Plus, I have meetings on Friday, so I can't even sleep in and enjoy the morning. We could wait and celebrate next weekend, though?"
"I can't. I have my cousin's baby shower on Saturday and I'm planning on going to the outlets with my mother and sister on Sunday."
"Well," I considered. "We are absolutely nowhere, then."
Jessica shifted a bit and leaned her head up on her elbow saying, "What about this? How about if we do a romantic night here? Act as if we're at a hotel with room service, but we don't have to deal with all the craziness. I'll make dinner, you make drinks, we both dress up. That kind of thing.'
"I could set up a little cocktail table by the windows, light candles" I added, thinking out loud. "I mean this place has the best view in the city."
Jess' mind was running at that point, "I love this. You take care of drinks, music, set-up. I'll take care of dinner and the bedroom! We can even order an adult movie on demand like we would in a hotel!"
"I'm totally on board. Are you sure you don't mind cooking? That's not really fair to you."
"Let me think about it. I bet I can call around and do some sort of take-out dinner from somewhere. Like they do all the components, and we just heat them up."
"Let's do it! A homemade Valentine's Day!" I agreed.
"But now," she said sliding toward the end of the bed, "I need to use the restroom. Your cum is still leaking out of me and starting to get sticky on my thighs."
I grabbed her waist and pulled her back toward me. "Or, you can get me hard again and I can add a fresh load into that pussy."
She slid back and wrapped her hand around my cock, giving it a few strokes. For the second time that night, we agreed on a plan.
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On Thursday, Valentine's Day, I picked up a bouquet of roses and a heart-shaped box of chocolates for Jess. I also got her a bottle of her favorite perfume. She found a restaurant that provided us a 4 course "meal to go" and all we had to do was heat it all up. She went to my place early to start getting things ready and I left work to meet her there. I had set-up the table the night before with a red tablecloth, candles and all the plates, silverware, and glasses.
When I got to my door of my condo, I was juggling flowers, chocolates, a gift bag, and my laptop case. I was able to hit my own doorbell with my elbow, hoping Jess was there to let me in. I heard the 'click-clack' of heels on my floor and the locks slide open. When she opened the door, I could see that she had already dressed for the occasion.
She had on a tight red sleeveless dress with thin shoulder straps that clung to her body. The scoop of the neckline dipped low and showed off her impressive breasts that were clearly being supported by a push-up bra. She must have dusted her cleavage with some glittered powered as her full, perky, globes shimmered in the light. The dress ended halfway up her thighs, leaving her muscular, stocking-clad legs exposed down to the red heels she was perched on. Her hair was teased out in big loose ringlets, and she had done up her makeup with ruby red lipstick and smoky eyes.