This is my entry into the
Valentine's Day Story Contest 2023
. 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 add some twists & embellishments to keep them interesting for the readers. Names are always changed
Please remember, authors & our stories thrive on ratings. We get better with feedback, so PLEASE leave your comments on our stories and rate them when you are done!
Everyone in the story is 18 years of age or older.
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To say that my girlfriend of nearly two years, Tara, and I were not getting along would be an understatement. We were in the last part of graduate school together with the end in sight. We spent the Summer apart but fell right back into our relationship through the late summer and fall. Things started to change a bit as we approached the holidays and we started to have more little arguments and disagreements. We had just spent the holidays with my family and on a cold December night, we sat at a local bar and talked about "the future" with each other. We agreed that we loved each other and wanted to stay together but wouldn't let the relationship deter us from our individual career goals. Looking back, we had basically set a countdown timer to the end of our relationship, without actually ending it, putting us in a weird state of limbo.
After the break, we returned to campus and because we were on different tracks within our majors, we saw less and less of each other until we would converge at one of our apartments late in the night. By the time February rolled around, we started spending more time at our OWN apartments without the other one staying over. We would go out with friends, go on dates and still have sex, but most of the excitement and passion had faded.
When we were together, I found myself being tentative with my actions and words, as I didn't want to start any sort of conflict or make a downward trending situation any worse. Tara was also unusually quiet and reserved in and out of bed. There wasn't much fighting, more of just an apathetic co-existence. While Tara historically had a temper that would flare up, I'm not much of a yeller. When I'm angry or upset, I tend to get quiet unless I'm really pushed. But neither of us were arguing, just awkward quiet interactions.
More awkwardness existed because we were still a couple, and DID want to make the relationship work, yet we weren't connecting on any level. Worst of all was when we attempted to be intimate. We went from a couple that used toys, watched porn and tied each other up, to a vanilla pair that was going through the motions when in bed together. Tara seemed disinterested when I would try to talk her into bed. Then, once we got there, I was slow and tentative, constantly wondering what was so off between us.
This went on for close to a month and in an effort to hit a bit of a "reset button", we planned a quick getaway for Valentine's weekend to a nearby city. We booked a hotel room for Friday and Saturday and planned a fun, romantic weekend for just the two of us, hoping to reconnect. Friday afternoon, we packed up my car and made the 90 minute drive to the hotel. Leading up to the trip, there wasn't the usual excitement or flirting that we would normally experience for a getaway. No teases from Tara about special outfits she was bringing and no flirty, dirty comments from me. For the first time, we were awkward and reserved as we departed.
We did make SOME effort, however, to have a fun Valentine's weekend. On Friday night, we found a restaurant/club that was doing a Valentine's themed party, so we made reservations. We left Saturday (Valentine's Day) open to walk around and shop for the day and we planned a dinner at a romantic restaurant near the hotel for Valentine's night. While we didn't overtly discuss it, both of us were hoping to make use of the hotel room during the weekend to light a bit of a spark.
Arriving at the hotel, we checked to find that it was a classic hotel in the heart of downtown. The room was older and refined with fancy furniture, billowing curtains and a huge four-poster bed with sheer netting tied on the corners. It wasn't my normal style, but it fit the romantic feel for the weekend. We both explored a bit, checking out the bathroom with the oversized shower and opening the curtains that overlooked a large park below.
As we unpacked, the hotel delivered a bottle of champagne, chocolates, and strawberries as part of our "Valentine's Package". I wondered if we should open it and get the weekend started off with drinks, so I asked Tara, "Do you want to open this up and crawl into bed for a bit?"
She looked up and considered it briefly before answering, "It's going to be a late night and I'm tired from the week. Let's save it for later. Would you mind if I grabbed a nap for a few hours before we head out?"
I knew she could hear the disappointment in my voice when I answered with an abrupt, "Nope. That's fine." But if my disappointment did register, she didn't seem to care and she crawled into bed. 15 minutes later, she was sound asleep, and I was working on a project on my laptop, angrily banging away on the keyboard with sexual and emotional frustration.
As promised, Tara woke up a few hours later and seemed more relaxed. She took a shower (again declining my invitation to join her) and we got ready to head out. I wore a pair of black jeans with a red button-down shirt to stay in the spirit of the holiday. I waited on the bed until Tara emerged from the bathroom, ready for our night out.
Tara had high cheekbones, silken brown hair and brown eyes that were expressive and sultry. She was the type of woman who could get you instantly hard with a smile and sparkle from those eyes. Her body was great, too. Perfect tear-drop C-cup breasts, toned stomach and an ass that was just full enough to fill out the best pair of jeans. To head out that night, she was wearing a black pleated skirt that ended just above her knees. She had on a red, sequined tank top that was just low-cut enough to give a solid view of her cleavage. Her legs were covered in black patterned stockings that had lacy hearts sewn in. Finally, she was perched on a pair of low, red sling-back heels.
"Wow" I started, "You look amazing."
Tara was looking in the mirror, applying some deep red lipstick and answered, "Thank you. I really do want this weekend to be fun, so I thought I would get in the spirit a bit!"
We pulled on our coats (it was winter in the Midwest, after all) and got a cab to the club. When we got there, we found it to be perfect for the night. It was a dark gastropub with small, romantic booths around the edges. In one section, there was a live band playing music and a huge bar at the other end. We were seated and ordered a bottle of wine and dinner.
As we sat close together and the music played, we started to loosen up with each other for the first time in weeks. We flirted, we kissed, we toasted, we ate and we drank. We watched different people on the dance floor and at the bar while we enjoyed a romantic-themed meal. We got up a few times to dance and during one set, we found ourselves grinding against each other on the dance floor before sloppily kissing in full view of the bar patrons. We went back to the table for some more drinks, hand in hand. When we sat back down, I had one arm around Tara and the other resting on her skirt-covered thigh. She shifted slightly, letting my hand slide up and under her skirt where I felt her stockings end and her bare skin above the lacy tops.
"Are you wearing thigh-highs, babe?" I asked.
"Yup. I told you, I wanted to get in the spirit this weekend. I've been trying to get you to notice them all night."
While she was still being flirty, I detected a slight chill in the last part of her statement. Regardless, I didn't want the moment to end. I ran my hand further up, feeling more of her bare skin under her skirt. I was able to grip and grope her bare ass before bringing my hand back around the front. Tara was nuzzling my neck as she shifted again, and my fingers ran over the lacy panties covering her sex.
"Dammit" I joked. "I was hoping you had left the panties behind."
While I was attempting to be flirty and sexy, I felt Tara's head pop up and her hips twist away from me, losing contact with my hand. I looked at her face to see that her eyes were angry and directed at me.
"Seriously?" she snapped. "I try to be sexy and wear fucking stockings for you, but you have to make a comment me wearing underwear?"
"Babe" I replied. "I was just jok..."
"Yes. I wore underwear. Because we're in a club and I didn't want to be flashing my pussy to everyone. Sorry I wasn't sexy enough for you." Tara stood up and stormed off to the rest room.
Once she returned, I spent the next 30 minutes trying to explain I didn't mean anything by the comment, but it was no use. We ended up asking for our check, left the club and went back to the hotel. In the cab, I fumed about Tara's reaction. This was the girl who, over the course of our relationship had let me bang her in an elevator, impersonated her sister in bed, let me fuck her ass on the roof of my building, convinced her friend to join us in a threesome and now, suddenly, she was offended that I made a comment about not wearing panties.
The chill between us remained when we got back to the room and when Tara emerged from the bathroom in a pair of gym shorts and t-shirt, I knew any chance of romance was gone for the night. The night ended as it started, with Tara asleep in the bed and me on my laptop. This time, however, I wasn't working. Instead, I was blindly staring at screen, doing nothing for nearly an hour before I decided to crawl into bed myself.
The next morning, I woke up to find that during the night Tara and I had ended up in a spooning position. Her ass was pressed against my morning wood and my hand was around her waist. As I gained consciousness, I pressed my erect cock against Tara's ass. Feeling her gyrate back in response, I lifted my hand up under her shirt and cupped one of her breasts. Tara was still feigning sleep, but I knew she was awake enough to feel what I was doing. I nipped and kissed at the back of her neck, moving her long hair to the side. I pressed my cock harder into her ass as I rubbed and pinched her nipple under her shirt.
Tara was definitely awake at that point. She was pressing and grinding her ass against my cock and her breaths picked up in tempo. I continued to caress her breast until I moved my hand a bit and gave her stiffening nipple a sharp pinch. For the first time, I heard a moan from her, so I knew I was on the right track. I brought my hand back down and slid it into the waistband of her shorts. I was able to get a firm grip on her ass cheek and then her hip which allowed me to press against her harder. With one hand pinned under her, I was limited in my options, so I moved my hand back up her stomach to her tit and started to fondle it more. The feeling of her tit in my hand and her ass press against me had me rock hard and it felt like we were back on track for the first time. All of a sudden, I heard a frustrated groan from Tara.
"Fuck, Jay, are you ever going to go inside my panties?" Her tone wasn't making a sexy request, she was clearly upset.
"Uhh...I was getting there, T" I stuttered. "I just hadn't...."
"Ugggghhhh. You are so fucking timid, lately. For once, just touch my fucking pussy, would you?"
Instead of complying, I pulled my hand from under her shirt and wrestled my other arm out from under her, allowing me to sit up in the bed.
"What the fuck is your problem?" I snapped back. "Trust me, I was getting to your pussy."
