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.
Looking at my expression, she made a small twirl and asked, "You like?"
"You look amazing, babe!"
She moved to the side to let me in and grabbed the flowers and chocolates from my arms.
"Thank you! I love that you got me 'overpriced roses and cheap chocolates', was it?"
"Cheap 'heart-shaped chocolates'" I corrected. "I have a little something else for you, too." I laughed.
"Why don't you get settled, then we can have drinks and exchange presents before dinner" she suggested.
I went to the bedroom and cleaned up a bit. Stripping off my work clothes, I took a quick shower and changed into a pair of black slacks with a black button-down shirt. I pulled on a pair of bright red dress socks to stay in the spirit and tied on my dress shoes. Underneath it all, I wore a pair of red satin boxers, knowing I wouldn't be able to match Jess' underthings, but wanting to make an attempt at being romantic.
Peeking into the kitchen, I saw a bunch of foil-lined containers all set-up on the counter. When I got to the living room, Jess had dimmed the lights and lit some candles around the room. As I've mentioned in other stories, my condo complex consisted of three different buildings, all 40 stories tall. They bordered a common area with a pool, small lawn area and benches that all the buildings shared. My condo was on the 34
th
floor and looked out over the sparkling lights of the city. The condo had huge windows that ran from about waist-high to the ceiling, giving us incredible views.
She was flipping through a magazine on the sofa but looked up when I walked in and said, "Honey, you look amazing! I love that we're dressed up for a night in!"
"Thanks. This is awesome. Let me just take care of a few more things."
I went to the 5-CD changer and started the mix of romantic music for the night. I took a few minutes and made two martinis, one with olives, one with a twist and carefully walked them over to the couch. We clinked our glasses in a toast, gave each other a peck on the lips and took a sip of our cocktails.
The mood was more romantic than any restaurant we could have chosen. Music was playing, candles were flickering, and the city skyline shone in the night outside the windows. My eyes kept drifting from Jess' legs to her protruding tits. Her hand was lazily rubbing my leg and I felt myself swelling in my pants. She moved her hand, placed her drink down and grabbed two wrapped packages on the coffee table.
"Let's do gifts!" she announced, handing me the wrapped packages. I reached over and handed her the card and envelope I had waiting.
"Sounds good" I replied. "You go first."