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This is my entry into the April Fools 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!
This story has some long buildup, but then some great sex toward the end
Everyone in the story is 18 years of age or older.
I had known Kimberly since high school. Back then we were friends, but never dated. She was a cool chick who wore cool clothes and hung out with cool kids. I was somewhat less cool. She was a cheerleader and dated hockey players. I played varsity tennis and dated theater girls. She smoked, drank and went to parties. I watched movies with friends. And yet, we were really good friends for all four years. When we had classes together, we’d partner up for assignments. When we were in social clubs, we’d work together on projects. And on the rare occasions when we would be at the same party or dance, we would end up laughing together and hanging out, even if it caused a problem with our respective dates. Did I have a crush on Kim? 100%. But back then, my instincts and abilities were lacking at best, and we remained friends until graduation. We partied with our classmates that summer, but as John Mellencamp sings, “Life goes on….”. Kim and I went in separate directions for college and then grad schools.
It was pure serendipity that we both ended up back in Minneapolis where we grew up for our first post-graduate jobs. Despite growing up in the area, I was at the stage of life where I had to make new friends, so after receiving an email to a “mini-reunion” at a local bar I decided to go. Upon arriving, I quickly realized I didn’t know many people and worked my way to a corner of the bar. I ordered a beer and was trying to connect with a few of the other grads there when I heard a long-familiar voice ring out.
“Holy fuck! Look what the winds blew in!” I turned around and saw Kim striding toward me with a huge smile on her face. Her formerly bleached blonde hair was now a curly, shoulder-length brown. She was older, obviously, but had kept her petite figure. It looked like she had come from the office because she had on a skirt to below her knees with a professional blouse. I did notice that the top of the skirt was hugging her hips as she jumped up and wrapped her arms around me, giving me a huge kiss on the cheek. She was on her tip toes, stretching up against me and I could feel a slight arousal toward my long-standing crush.
Before I could say anything, a second, deeper voice called out, “Damn. I brought her here, but you get the hug and kiss?” It was Greg, one of our classmates and good friend of mine back in the day. Greg had always had an even bigger crush on Kim than I did, and I knew they had kept in touch over the years. For the next hour or two, the three of us commandeered the corner of the bar where we drank and caught up. The more Kim and I drank, the more we flirted. I mentioned I was in a fading long-distance relationship, she said she was single. Each time we started to cozy up in the corner, Greg would jump back in, effectively cock blocking any potential connection.
Fortunately, something in the back of my buzzed mind realized that Kim and Greg had obviously arrived together and even though she didn’t seem to be interested in him, he had designs on her. Not wanting to screw over my high school friend, I backed off my flirting with Kim and started to talk İstanbul Escort to some of the others in the room. As the night wound down, I found myself talking to a girl named Andrea who had graduated a few years behind us. She had long, straight black hair and a body that showed that she kept in shape. Her ass filled out her tight jeans and although not huge, she was displaying some decent cleavage. The longer we talked, the more she was rubbing up against me and laughing at my stupid jokes. We stole a few kisses, and I was able to grab a few handfuls of her tight ass. Andrea and I started to feel each other out about continuing the night back at one of our apartments, when one of her friends came over and pulled her away to the rest room. As I awaited her return, Kim was at my side again with the same big smile on her face.
“Did you tell the little hussy about your long-distance girlfriend?” she asked.
Before I could finish, Kim gave me a punch in the chest, continuing, “Don’t worry. I’m not going to blow up your spot. At least one of us should get laid tonight.” Despite our mutual attraction, Kim and I were still buddies and our old rapport had returned instantly. When Andrea returned, the look on her face changed when she saw me laughing with Kim, though.
Through gritted teeth, she walked up to us and said, “Alright. Well, my friends are leaving, so I guess I will too….”
Kim immediately piped up, “Why? It’s still early! Hang out with us for a while longer. You and Jay should come over and have a last round with me and Greg!” The tension in Andrea’s face released a bit, partially because of the realization that Kim and I weren’t together and because of Kim’s general likeability.
“I mean, I could definitely stay” Andrea said hesitantly.
“Well, let’s go over to Greg, then!” Kim took Andrea’s arm and continued. “Wait. It’s Andrea Greenwell, right? Weren’t you on the field hockey team when Amanda was captain? She was my co-captain my senior year when she was a junior….”
Thanks to Kim, the four of us went back to the bar and closed the place at last call. As Andrea and I prepared to catch a cab back to my place, Kim handed me a napkin with her phone number on it.
“Hey, let’s not lose touch. Give me a call and let’s grab lunch or something soon.”
An hour later, I was back at my place with a naked Andrea sprawled out on my bed. I was right about her being fit as she had her legs spread wide with her ankles on my shoulders. My cock was sliding in and out of her and I was watching her tits bounce with every thrust. The sounds of our flesh slapping against each other were only interrupted by her moans and our groaning as she worked toward an orgasm. I fell forward a bit and felt her legs spread even wider, opening her pussy wide for me. As I felt the cum begin to build up in my balls, I closed my eyes and found myself thinking of Kim’s smiling face as I exploded into the condom enveloped by Andrea’s pussy.
As a result of that night, three things happened. First, I started to date Andrea for short while. Next, Kim and I started to hang out more as friends, catching a movie or a sporting event when they popped up, and we established a tradition of a monthly drunken Sunday brunch. The last thing that night put in motion was that it started a pattern of Kim and I NEVER being single at the same time. While I dated Andrea, Kim was single, despite Greg’s best efforts.
After Andrea and I broke up, Kim started dating a guy at work. I started dating a co-worker, myself, and then Kim’s relationship ended. This went on for close to two years, but our brunches never changed. Once a month, we would show up, eat, drink and gossip about our respective relationships. Right around Kadıköy Escort the two-year mark, I started to travel more, and Kim and I weren’t able to get together as often. We kept in touch by phone and by email but hadn’t seen in each other in a couple of months.
Ironically, it was late-February when we saw each other again, at our old pal Greg’s wedding. Kim and I were both invited – she was bringing her boyfriend, Mitchell, and I was going solo. Thanks to work and travel, I was on a bit of a dating dry spell. Of course, that was like saying the Sahara Desert was in a bit of a “dry spell.” I was on a terrible run. I hadn’t dated or met anyone in a few months. I had a few disastrous blind dates. I was hoping that a wedding with single women and bridesmaids might break my streak.
I was dressed in my suit, standing at the bar of the reception. I hadn’t seen Kim at the ceremony, but knew we were sitting together for dinner. Across the room, I heard her voice and looked up to see her hugging some friends. Her back was to me but at her side was a large guy who I assumed was her date. He had slicked-back black hair, long sideburns, and a single earring. Maybe it was a pang of jealousy, but I didn’t like him already. The bigger surprise was when Kim pulled away from the hug and turned toward me. She had her curly hair styled and her bangs had grown out. She had highlights of blonde back, which brought back immediate memories of her younger self. Her bright green eyes were highlighted by her makeup, and she wore an appropriately tight blue dress. She looked like the same Kimberly whom I had been crushing on for years…except now her boobs were considerably bigger.
As I said, Kim was always petite and had tiny breasts. I had seen her in tank tops and bathing suits and knew that she wasn’t well endowed, naturally. But Kim now had a set of fleshy globes stretching the top of her dress. She had a deep cut of cleavage that hadn’t been there a few months before. I moved toward the group and Kim lit up, moving toward me, as well. We hugged and I could feel her new tits pressing against my chest as we gripped each other. One person who wasn’t enjoying our hug was Mitch. Although we had never met, he was glaring at me. I separated from Kim, and she introduced us. I’m a big guy at 6’1″, but Mitch was bigger than me and he gave my hand an overly-aggressive squeeze.
We all moved to the table for the usual wedding festivities. We all laughed, ate, celebrated, and drank. I was being pleasant but not overly familiar with Kim mostly because I didn’t want to get my ass kicked at a wedding by Mitch. Everyone at the table was stealing glances at Kim’s new features and would look away when she made eye contact. Even Greg, the groom, mentioned her new cannons to me when we were alone for a minute, “Shit. Did she have to wait for my wedding day to bust those out?”
When the dance floor opened, we all did our best to dance to the beat without embarrassing ourselves. My streak was continuing as it seemed like the only single females at the wedding were either the bride’s teenage nieces or various widowed aunts. I was standing at the bar when I heard that familiar voice say, “Hey sailor, buy a girl a drink?”
I looked over to see that Kim had just come off the dance floor. Her bangs were matted to her forehead, and I could see the perspiration shimmering on her inflated bosom. I shifted my gaze higher to see that Kim had smirk on her face, having caught me staring again.
I got us some drinks and we sipped as we watched the party in front of us. We made some small talk about work. I lied and said that Mitch seemed nice. I asked about her family, she asked about mine. We said we had to have brunch again. Finally, I couldn’t resist any more. I leaned Ataşehir Escort over and said in my best British accent, “Fuckin’ hell. When’d you get the new tits, luv?”
Kim threw her head back and burst out in laughter, “Finally! It’s about time you said something you dick! I paid a ton for these a few months ago and nobody wants to say anything about them?!?”
We were instantly back in synch with each other as I returned the laughter and banter, “What did you want me to do with Mitch right there? Reach out and give them a good ‘honk’ to see how they feel? The guy already wants to punch me in the face after the hug you gave me before.”
“Yeah. He can be a little jealous. But he’s a good guy.”
“Who gives a shit about him? I was focused on those funbags pressed against me. In all our calls and emails, you didn’t think to mention them?”
“Really? And how, exactly, did you expect me to bring them up? ‘Hey Jay…how’s work. By the way, I got new tits and don’t look like a middle school boy anymore.'”
There was a flash of hurt on Kim’s face with her last words. Despite our friendship, I hadn’t realized just how insecure she must have felt. Given the time and place, I opted for a quick joke, saving the serious questions for later.
“No, but I mean, a picture or two would have been appropriate.”
“A picture? And ruin the surprise? At least you got a quick feel when we hugged.”
“Well, thanks for that. Definitely the high point of my night, so far. I mean, fuck, that’s the most action I’ve had in months.”
A look of realization crossed Kim’s face. “Oh….the curse! That’s right! I’m dating someone so you must be single!”
“Kim, I’m not just single. I’m in the middle of a dry spell that would compete with the priest who performed the ceremony, today.” As Kim finished talking, Mitch walked over, put his arm around her waist and signaled the bartender for another round.
“Babe! You snuck off the dance floor!” he bellowed. “What are you two talking about over here, all secretive?”
“Nothing, really, just helping Jay scope out potential women.” Mitch looked around the room and replied, “Yeah. Not much talent here, they’re either too young or too old, pal.”
We then spent some more time at the bar before returning to the table. For the rest of the evening, I found Mitch to be … a decent guy. As much as I wanted to dislike him, he was kind of funny, personable, and not as much of dick as I thought originally. In his defense, he was probably just as conflicted with my presence as I was with his. We spent the rest of the night talking, drinking, joking, and dancing with the rest of the guests.
As the night wrapped up, Kim and Mitch had the look of a couple who were eager to get up to their hotel room together. Their kisses were getting longer and deeper, they were touching more and whispering into each other’s ears. As they left, Kim gave me a big hug and said, “Sorry, but we’re gonna head up” quietly in my ear.
“Don’t worry about it. Have fun. No need for everyone to suffer for me right now.” I said back.
Mitch then approached me and shook my hand with much less strength and aggression than earlier in the night. “Nice to meet you, Jay. We should all hang out again soon.” I returned the platitudes, and we all went our separate ways.
A few days later, I opened my email at work to see an email from Kim.
>> Hey Jay –
Was awesome seeing you again. I was talking to Mitch, and he mentioned that if you’re up for it, I have a friend you might like. Her name is Marcy. We work together, she’s really fun, and pretty. What do you think? We could double date so it wouldn’t be totally awkward.
K > K-
Wonderful. April 1st is a Saturday night. Whelp, why the hell not? My dating life has been a complete joke so the irony is perfect.
Let’s keep in touch. Safe Travels.
Sorry. Things have been crazy since I got back. Still on for Saturday. Let’s meet at Rumblefish at 7:00. I’ll make the reservation. See you then.
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