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.
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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 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.
“Uh….well….I….”
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 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 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.
I went on my trip and didn’t think much about any of it until I returned. As the date got closer, I knew Kim was back from her trip, so I sent an email confirming our double date for the following Saturday. When I didn’t hear back right away, I thought I had her return day wrong, so I didn’t panic. I sent a follow-up on Wednesday and still didn’t get a response. On Friday, I called Kim and got her voicemail. I left her a message and tried to be lighthearted but still directly asking if we were still on. I made a quick joke about not standing me up on April Fool’s Day and hung up. Later that day, I got an email from Kim that calmed my worries.
On Saturday, I caught a cab to the restaurant and got there right at 7:00. The restaurant was crowded as I made my way to the hostess stand and asked her if a party of four under “Kim” had checked in yet. I tried “Mitch” and then my name. When she still couldn’t find the reservation, I asked if I could take a walk around and look. I circled the restaurant and didn’t see Kim or Mitch. I checked the bar and lounge before checking my cellphone for any messages. I wondered if my blind date was there already and realized that had only seen the one picture on my screen and might not recognize her. I walked around again to see if I could recognize her to no avail. I tried calling Kim to see if they were running late, but her phone went right to voicemail.
Like any normal person, I was mentally flipping from aggravated to concerned to pissed to confused. I sat on a bench in the lobby/waiting area with my phone in my hand in case Kim called me. A burst of cold air from the door made me look up to see a windblown Kim walk in. I stood up and saw that nobody seemed to be with her. Kim read the questioning look on my face and gave me a sort of sad, sweet, half-smile.
“April Fools! It’s just us tonight. Let’s grab a table and I’ll bring you up to speed.”
I followed her to the hostess stand a second time where we were led to our table. Kim politely asked for something off to the side and we went to a small table in a corner of the restaurant. I sat down and watched as Kim took off her winter coat. Her cheeks were still flushed from the cold and her curly hair was unruly from the wind. She was wearing a tight royal blue turtleneck that showcased her enhanced breasts. Her black pleated skirt ended at her knees and a pair of black boots went up her calves. She was the perfect image of a midwestern girl out for a chilly night on the town.
Kim sat down and before she could say anything I had to ask, “So? Is this the big April Fools joke? Marcy no-showing? And Mitch bailed?”
“No. Marcy didn’t cancel. I told her there was a change in plans. And Mitch…” Kim’s voice trailed off and I saw her eyes well up with tears. She hunched over to hide her face a bit and I watched as her shoulders moved slightly with quiet sobs.
“Kim. I’m sorry. What happened?” Before she could answer, the waitress approached and came to a sudden stop when she saw Kim crying.
“Uh… can I get you a …. Uh…. Cocktail?” she stammered.
“Definitely” I replied. “I’ll take a cosmo and she’ll have a Bombay Sapphire martini, up. Thanks so much.” The waitress got away from our table with astounding speed, and I spoke to Kim again. “Thanks. Now she thinks I dumped you at the start of dinner. Probably gonna spit in my food.”
Kim chuckled at the realization of our appearance, lifted her head and started to dry her eyes a bit.
“Sorry” she sniffled. “I guess the jokes on you keep coming, huh?”
“It’s the spirit of the night. Want to tell me what happened?”
“Remember we were going back and forth with emails because as soon as you came back from your work trip, I left on mine? Well, last Thursday, I was able to get on an early flight home. I didn’t tell Mitch, but I ran to my place and put on a sexy little outfit to surprise him. I threw on my big coat and went over to his place. We talked that morning, and I knew he was working from home and would be there. I got to the building and the doorman knew me, plus I gave him a little flash and wink and asked him not to ring up to Mitch so I could surprise him.”
“Oh no” I interrupted.
“Yup. I took the elevator up to his apartment and rang the buzzer. I waited a few seconds and nothing. So I rang it again. I heard someone moving around and then I saw the peephole kinda darken, so I knew he was looking through it. I opened my coat and gave him a little show.
“I heard the locks being moved and then he opened the door about halfway. He was standing in just his boxers, and he looked like he had just woken up and kind of flushed. My stupid first thought was that he was sick, and I was about to ask him if he was ok when I saw some movement in the place behind him.”
“Fuck” I interjected.
“Yup. He knew I had seen something and started stuttering, ‘Kim, babe, why didn’t you tell me you were coming over?’ I didn’t even answer, I just pushed past him and into the apartment.”
At this point, the waitress came back by the table with our cocktails. She had heard the last parts of Kim’s story and simply said, “I’ll give you some time with your drinks and come back and get your order in a few.”
“Wow” Kim said taking a sip. “We’re going to be legendary with her, huh?”
“Yup. She’s gonna start a ton of stories with ‘So, it was April Fools Night and this couple comes in…”
“So” Kim continued after taking a large sip of her drink. “At that point, I’m in the apartment and I can see into his bedroom where there is another girl in his bed, with the covers pulled up to her chin. When I tell you the room smelled of sex, I’m not exaggerating. They must have been fucking for hours the way the place smelled. Mitch moved over and closed the bedroom door and sort of led me into the living room.”
“What did he say?”
“Y’know? I thought it would be like a movie where he tried to make excuses or something. But nope. He basically banged out with ‘Sorry, babe. I didn’t know you were going to come by early.’ I went a bit nuts, yelling and screaming at him but he pretty much just stared at me. I was crying and getting hysterical, but he just did nothing. No explanations, no excuses, no apologies. Just let me rant. When I finally calmed down, I made the mistake of asking a simple question, ‘Why?’ Clearly it was the one question I shouldn’t have asked.”
“Why? What did he say?” I said in shock over the story she was telling.
“He said, ‘I just wanted someone hotter.'”
“What an asshole.”
“Yep. He said that when we first started dating, he didn’t mind that I had quote, ‘tiny tits’ and that it was kind of new and fun. Then, when I got my ‘fakes’ he thought he’d be into them, but he thought they just felt ‘weird’.”
“Again, I say, he’s an asshole.”
Kim was getting emotional again as she continued her story. Her eyes were welling up and her chest was starting move as she took deeper breaths to maintain some composure in the restaurant.
“I confronted him and questioned that the reason he cheated on me was because of my tits. Jay, that bastard stayed perfectly calm, looked right at me and said, ‘No. She’s just willing to do more, too.’ I asked who she was and apparently, she’s someone he works with. This went on for a while and it’s so weird. He wasn’t even trying to be mean, but he told me what she would do for him that I wouldn’t. Things like blowing him in a cab, giving him a ‘tit job’, and other stuff he never even brought up to me when we were together. Meanwhile, this other chick is still hiding in the bedroom 10 feet away from where I was sitting, half naked, under a coat.”
The waitress had returned, and we paused for a moment to order some food after quickly looking at the menu. I also noticed that a few of the tables around us where slyly trying to listen to our conversation, without looking like they were listening. We ordered food and a bottle of wine and Kim continued.
“So, I left and did a walk of shame. When the doorman didn’t make eye contact, I figured that he must have seen both of us coming and going with Mitch and knew this was going to happen. I went home, called in on Friday and cried through the weekend. When you started calling and emailing, I didn’t know what to say or how to answer. I did tell Marcy at work and asked if she would mind postponing. I was going to just cancel with you, too, but then I saw the date on the calendar and figured, ‘What the hell’ and surprise you tonight.”
“Well” I said, lifting my glass again. “Unless you want to keep talking about him, let’s toast to him being the biggest fucking asshole April fool, forget he ever existed, and pretend tonight is a much-delayed brunch for us!”
Kim laughed, raised her glass and toasted with me. We spend the next hour or so eating, drinking, laughing and generally trying to avoid the emotional subject that started the night. As dinner wrapped up and sipped on one last drink, I could tell Kim was getting melancholy again.
“Kim. Let me say it again, he’s an asshole. I always thought he was an asshole and turns out I was right. You can’t give a guy like him another thought. You’re funny, you’re hot, you have amazing tits, and you are generally an awesome person. You have to know that me and half of the guys in our class have had a crush on you since high school.”
“I know, Jay. But it’s not him. It’s what he said.”
“What are you talking about?”
“Jay. I’ve been in therapy for years about my body image and as I got older, my sexuality. In high school I basically had an eating disorder that lasted into college. I hated my body and felt awful that I didn’t develop the way other girls did. As I’ve gotten older, I’ve hated that I couldn’t wear certain clothes or outfits like other women. That’s why I got the enhancement surgery. I purposely didn’t get giant D-cups. I got a set of C’s that would fit my body and make me feel…well…normal for the first time ever.”
“Fuck, Kim. I’m sorry. I had no idea. And I was an asshole, too, for making jokes to you.”
“No! That was fine! I wanted people to treat me like normal and even notice me. But that day I showed up at Mitch’s? It was the first time I wore something that I truly felt sexy in. Under that coat, for the first time, I felt like a powerful, slutty vixen that would be a man’s fantasy. And then to be shut down and told I wasn’t enough. It’s soul crushing.”
For the first time, I realized just how self-conscious Kim had been for years. I always saw her as the cool, fun, pretty, and popular girl. Now, I was finding out she was just as confused, scared and frustrated as the rest of us.
“Kim, I can only say I’m sorry, again. I had no idea what you’ve gone through. I totally would have understood if you wanted to cancel tonight. Seriously, thank you for even coming out.”
“Jay, there was another reason I wanted to meet up with you tonight. As much as that dick has hurt me and insulted me, he did one thing right.”
“What’s that?” I asked.
“He broke the curse.”
“Curse? What curse?”
“THE curse. The whole point of tonight was to find you a date. Thanks to dickwad, I’m officially single. For the first time in history, we are both single, available, and together.”
A smile creased my face as the realization of her words hit me. She was right, we were both single with no attachments or commitments.
“So, Kim, are you saying you want to go on a date … after all these years? Like officially?”
“No, you idiot. We just had our date. Now, I want to go back to my place and do what couples do after a date.”
I felt myself stiffen slightly at her words, but I was still worried if she was forcing this or rushing into things after all the time that had passed between us. Or even a terrible April Fools joke being played out.
“Kim. I’ve had a crush on you since high school – I’ve told you a million times. But are you sure this is the right time?”
“Jay, ever since the reunion, I’ve regretted letting what’s-her-name…”
“Andrea”
“Sure. Andrea. What fucking ever. I regret letting you leave with her that night. I have no idea where you or I or any of us are going to be down the road, but I’m not regretting this again. Now, pay the bill while I run to the ladies’ room and then we can continue our April Foolishness celebration at my place.”
Kim got up and left me reeling. Every physical fiber of mine thought this was a great idea – finally getting to bang my high school crush. But some stupid moral beacon in the back of my brain was flashing with warning lights:
‘She’s on a bad breakup and rebound!”
“She’s your friend – don’t ruin it!”
“Maybe it’s a big prank still!”
As my mind raced and I whipped through all the different scenarios, I paid the bill as Kim returned to the table. She remained standing and simply said, “You ready?”
“Kim..I just want to make sure…”
“Oh, for fuck’s sake. Here. I got you a little gift.” Kim grabbed my wrist and pressed something into my hand. I opened my fist to see a pair of lacy black panties that she must have removed in the restroom.
“Now, let’s go. Thanks to the asshole’s comments. You are going to see exactly what I’m willing to do with someone.”
Kim’s aggressiveness shut down the last of my reservations and we walked quickly out of the restaurant. I stuffed her panties into my coat pocket as we grabbed a cab at the curb and piled in.
“You ok with going to my place?” Kim asked. “I have another surprise you’ll like.”
I agreed and we gave the address to the driver who pulled into the light traffic. As soon as the cab was in motion, Kim turned to me and gestured for me to lean in. I wrapped a hand around her waist and pulled her closer as our lips met for the first time. We were both tentative at first, as we gently kissed and licked, exploring the new sensations with each other. Before long, our tongues started to explore more, and we were soon kissing passionately in the back of the cab. My other hand had moved to the back of her neck as I pulled her mouth tighter and deeper against my own. Kim was adjusting her position and moved one of her legs up higher, causing her pleated skirt to ride up her thigh, exposing more of her flesh. I allowed my own hand to drift down and rub first her thigh, then move up higher to her bare ass cheek. Our limbs were now entwined as we made out and groped each other in the back of the cab. I cupped and grabbed one of her tits through her top and she leaned into my hand. I felt her hand snake its way down to my crotch to feel my erect dick. She was moving it up and down the length of my shaft getting me harder by the second. She paused and pulled away from my mouth for a second readjusting her position in the seat.
Kim grabbed my wrist and directed my hand under her skirt between her legs. For the first time, I felt her pussy that was covered in a short layer of soft hair. In the darkness of the cab, I kept catching glimpses of Kim with a sexy smile on her face as it was illuminated for brief seconds as we passed under lights or the headlights of another car. Kim held my hand firmly and I could feel the dampness of her arousal on my palm. I applied some pressure and rubbed my palm on the front of her pussy, feeling her lips slightly parting and the bud of her clit at the top of her slit. She leaned back in the seat of the cab and I watched her ample chest rise and fall with faster, deepening breaths. I looked forward and saw the driver glancing into his mirror, sneaking peeks at the action taking place just a few feet behind him.
Kim moved her hand and adjusted mine on her pussy. I felt her move my hand, so it pointed downward. My thumb was on her clit and my fingers on her wet lips. I strummed my thumb on her clit and she started to rotate and thrust against me. Two fingers slipped into her wet tunnel, and she let out a quiet moan. The scent of her arousal began to fill the car as I coordinated the movement of my thumb with the thrusting of my fingers. Kim was speaking with a hushed voice, one hand on top of mine, the other trying to grip the vinyl seat of the cab.
“Oh…..unghh….feels so good….please don’t stop….I’m gonna cum….”
I had read somewhere that when a woman is giving you positive vibes, keep doing what you’re doing – so I didn’t change anything. I kept lightly flicking her clit while driving my fingers in and out of her pussy. Kim was biting down on her thin bottom lip and thrusting harder against my hand trying to reach a climax. A slight sheen of sweat started to appear on her brow, and I watched her clench her eyes shut tight as her pelvis and legs locked up for a moment. She took a bunch of short, gasping breaths and let loose a high whine as she came on my hand. I felt her entire body shudder as I slowed my motions.
After a full minute, her eyes fluttered open and a huge smile appeared on her face as she said, “Wow. That was fucking amazing.” She straightened her skirt and looked out the window, wondering aloud, “Where are we?” Once she got her bearings, she added, “Good, we have just enough time for this.”
Taking a quick glance toward our driver, she bent forward in the seat, unzipped my fly and wrangled my dick out of its enclosure. She used her hand to give me two quick strokes before taking me in her mouth. I felt the heat and moisture of her mouth slide down, making me pulse against her tongue. Because of my pants and boxers, only part of my shaft was protruding, so Kim was able to take my exposed length into her mouth easily. She swirled her tongue around my sensitive head and sucked and licked my shaft. I made eye contact with the driver in the mirror who clearly knew what was happening behind him. It didn’t last long, as my head slumped back against the head rest and I closed my eyes enjoying the oral ministrations of my long-time crush. Kim used her hand to release more of my shaft and plunged deeper, taking me toward the back of her throat.
I felt my balls begin to tighten and my cock spasm as I neared a climax of my own. Kim was still expertly licking, swirling and sucking creating a myriad of sensations on me. I opened my eyes and looked down to see the curly ringlets of her hair bouncing and moving as she bobbed on my cock. That image, of a girl I had wanted for over a decade, my dream girl, bobbing up and down with her cute hair bouncing sent me over the edge. I uttered a quick warning, then felt my cock and balls release into her mouth. Kim locked her lips around my shaft and I felt her tongue shift as I exploded into her mouth. The cum pulsed and filled her mouth and when I finally stopped, Kim swirled her tongue one more time before swallowing my load. She slowly pulled off my dick, taking as many fluids with her as she could. I watched her lick her lips and then gently wipe them with the back of her hand.
With a smile again on her face, she said, “Fucking April Fools joke is on him. I just needed the right person to blow in a cab.” I zipped up and we both put ourselves together as we pulled up to Kim’s building. I tipped the driver who was making no secret that he knew what we had just done.
Kim and I walked into her building with our arms around each other, through the lobby, up the elevator to her place. She opened the door, and we threw our coats on a nearby rack. She led me to the kitchen where she grabbed a bottle of wine, some glasses, and a corkscrew. We were both a bit giddy and giggly about what had just happened as we sipped on the chilled wine. There was still a ton of sexual tension between us as we both readied for the next round.
“So, I feel like I’m being used.” I said to her.
“Oh really? Used do you?” she chuckled.
“Yup. Are you just using me to prove the asshole wrong about things he said you won’t do?”
“Do you care?”
“Nope. But if that’s the case, can I call him and give a list of other things to accuse you of not doing?”
Kim gave me a punch to the chest and then a kiss on the lips.
“No. You may not call him. But there is something else I want to do. Follow me.”
Kim had me pick up the wine and I followed her to her bedroom. She told me to get undressed and that she would be back in a few minutes. I watched her rummage through a bureau drawer, then her closet, before she disappeared into the bathroom. I stripped down to my boxers and waited for her return.
Close to ten minutes later, the room was lit by the light from the opening bathroom door. Kim stepped into the shaft of light and I felt my breath catch in my chest. She was wearing a lacy piece of lingerie that had less fabric than two hankerchiefs. The black stretchy lace started behind her neck, then criss-crossed at her throat, stretched over her tits before coming together to cover her stomach and crotch. The entire outfit was see-through lace making her nipples and pussy visible. Her thigh high black stockings were attached to some small straps on the bottom of the garment, and she was perched on a set of black high heels. When she shifted her legs slightly, I could see that the crotch was split in the middle giving easy access to her sex.
Kim sauntered over to the bed and pulled on the waistband of my boxers, working them down my legs and off me.
“So,” she said. “This was my surprise outfit I wore to the asshole’s place that day. You and the doorman are the only two who have seen any of it. So, I guess the April Fool is on the asshole, after all.”
I loved that Kim was now refusing to say his name and would only refer to Mitch as “the asshole”. But what I loved even more was when she climbed up on the bed, threw one leg over me, gripped my erection in her hand and guided it into her wet opening. I felt her pussy lips open slightly as the head of my cock split them open. Her warmth and moisture enveloped just the tip of my cock as she moved her hips slightly to line up properly. Incredibly slowly, she rocked back and forth and allowed my cock to slide into her tunnel. With every inch, I could feel her inner muscles gripping and releasing my shaft as I penetrated deeper and deeper.
Kim had her hands on my chest, her eyes closed, and head tilted forward when I felt the fabric on her crotch meet the skin of mine, signifying that she was fully impaled on my dick. She was still gently shifting and moving as we both got used to the sensation. When she finally opened her eyes, she looked down into mine and said, “You feel incredible in me, Jay.”
I couldn’t control my words and spilled out like teenage schoolboy, “Kim, I’ve literally waited close to fifteen years to feel this. You were my high school crush, you’ve been a best friend, you’ve been the one that got away. Now, finally, I’m inside you. Fuck……that sounds corny.”
We both laughed at ourselves, and the movement made me twitch inside her. She took the cue and began to ride me harder. She pressed her pelvis into me, grinding her pussy and clit against me. I could feel the tip of my cock rubbing against the fleshy walls of her pussy and she would moan and shudder when I would hit her g-spot. Unable to resist any more, I reached up and pulled down the crisscrossed pieces of lace and got my first look at her naked breasts. They stood out from her chest like perfect globes, bouncing with her movements, her erect nipples stiff and protruding. I took them each in one hand and squeezed them. They were more solid than natural breasts but felt better than I thought they would. I ran my thumbs over her nipples and Kim let out a long moan.
“That’s it, Jay. Play with my tits. Squeeze them, pinch them. I’ve caught you sneaking looks at them, now they’re all yours!”
I followed her instructions and played more aggressively with her tits, grabbing them hard enough that I was supporting more of her weight with my hands. This let Kim ride me harder. She was no longer grinding against me, instead she was bucking her hips up and down the length of my cock. I had waited so long to be inside her; I swear it felt like I could feel her lips gripping and dragging up and down with every thrust. I could feel her fluids flowing off my cock and down to my balls as her arousal grew.
I wanted to change things up, so I took my hands and batted her arms to the side, making her torso fall forward on to my chest. With her tits now pressed against me, she was moving only her pelvis to ride me with short, fast strokes. I reached around and grabbed her ass cheeks, forcing her to slam against me even harder. The sound of our flesh slapping filled the room and it felt like we were both getting closer to coming. I could feel the sweat on our skin making our bodies slick and when I tried to adjust my grip on her ass, my hand slipped and I brushed against her asshole.
When I regained my grip, my middle finger landed squarely on her rosebud and while it didn’t penetrate her ass, it caused it to open slightly. Kim immediately froze and a loud scream erupted from her. She bucked hard against me a few times and I felt a rush of juices flood from her pussy. She gasped for breath as she slammed her pussy into me again and again as she orgasmed for the second time that night. She was moaning incoherently into the pillow by my head as she rode a wave of mini-orgasms until her body finally came to rest.
“Holy shit. That was fucking amazing.” I finally heard her say. “I felt that orgasm in my fucking toes. Why the fuck did we wait so long to do this?”
“Well, you were too busy dating assholes, and I was too busy dating bimbos. But at least it was worth the wait.”
“Definitely. But I want to make you come. How do you want me?”
“I fucking want you any and every way. But, even though it’s a little late, do I need a condom?”
“No. I’m on the pill and like you said, too late now. Want me to ride you more so you can play with my tits? Want me bent over? Tell me, Jay.” She was almost pleading.
“Roll over on your back.” I replied.
Kim rolled over on her back and settled her head into the bed’s pillows. She spread her legs with her knees bent, her high heels digging into the mattress. I settled between her legs, lined up and slid back into her. Her pussy was tighter than moments before, thanks to her recent orgasm. With every thrust of my hips, I could feel the tender, muscular walls of her tunnel grip by turgid unit. She adjusted her legs slightly, lifting them so I could hook them with my arms as I moved forward and back in a rocking motion.
Kim was breathing heavily with the activity and smiling up at me. I watched her tits bounce with every thrust and was transfixed by their motion.
“I have to say” she uttered. “I’m glad you like them.” Kim reached up and cupped both of her tits in her hands and made a show of squeezing them and playing with them. My cock stiffened even more and throbbed inside her. “Oh…you like watching me play with my tits, too? That turning you on even more?”
Kim began to pinch and play with her nipples making moaning at the dual stimulation. Watching her play with her own tits had me ready to come and I could feel my climax approaching. Kim felt the impending explosion and put her hands on my hips, pushing me away.
“Stop for a minute. Before you come.” She ordered. She had stopped me just in time as I was so close to orgasming inside her. Still, as I pulled out, a trail of pre-cum spread and connect the tip of my cock to her wet opening. Once I had shifted away, she reached into the nightstand and produced a bottle of baby oil. She poured it over and between her tits, then spread it all around with her hands. Her fleshy globes were now shining and glistening in the minimal light of the room.
“We need to break this curse and finish this the right way. I want you fuck my tits and come on them, Jay.”
It took us a few seconds to arrange our bodies properly. I straddled her body higher up, sitting on the bottom of her ribcage, being careful not to put too much weight on her. She shifted on the pillows so that the cavern between her tits lined up with my cock. Using her hands, she pressed her tits together and created a tunnel for my cock. I began to rock back and forth, coating myself with the oil she had spread on her flesh.
I had never tit fucked a girl with breasts as large as Kim’s before and it felt amazing. When the tip of my cock would emerge at the top of her breasts, it would send a shock through me every time. I continued the rocking motion and Kim encouraged me with moans, groans and encouragement.
“That’s it Jay. I want to feel your hot cum all over my tits, baby.”
I let out a deep groan and felt my balls release. The first burst of cum was trapped between Kim’s tits, but as I shifted forward, the second hit her on her torso and chin. She released her hands and I sat up slightly, spraying the remainder of the load over her tits and nipples. My hips and cock spasmed a few more times before I flopped over on my side next to her.
When I got my breath back, I muttered, “That was incredible.” I looked up to see Kim spreading the cum and mixing it with the oil on her tits. We both just lay there as we basked in the afterglow of our activities. A few minutes later, I felt Kim shift and move out of the bed.
“I’m gonna clean off and take this thing off. I feel like I’m all tangled in a wet fishing net at this point.
“Cool.” I replied. “Uh…do you want me to stay or uh….”
“Jason. We waited this long, you’re not going anywhere tonight.”
“Ok. I don’t have anything to sleep in.”
“That’s ok, I think sleeping naked is a better idea tonight anyway.”
Shortly after, a naked Kim climbed back into bed, and we fell asleep with me spooning her from behind. Sometime in the night, we both stirred, and she spread her legs enough for me to slip inside her from our spooning position. We had a quiet, slow fuck that time, that had me reaching around and holding on to her tits while we sensually moved with each other. When she gasped, moaned, and came I followed by sending a load into her pussy. We didn’t bother cleaning off, but simply drifted back to sleep.
I woke up the next morning with the sun lighting up the apartment. Kim and I had drifted apart in the bed and had both managed to get under some covers. I got up to use the restroom and splash some water on my face and when I walked back in, she was stirring.
“Go under the sink” she said. “I have brand new toothbrushes and some travel size stuff if you want.”
I brushed my teeth, and we switched places. While Kim was in the bathroom, I found my discarded boxers on the floor and put them back on, propping myself up in the bed. She emerged from the bathroom with an oversized t-shirt on, but I could still see her nipples through the fabric.
“What would you say to some coffee?” she asked.
We moved to the kitchen, and I sat at the counter while she made us two cups of coffee. There was a bit of an awkward silence that I decided to break.
“So, curse is broken. April Fools Day is over. The asshole is gone. Uh…..what now?”
“Now?” she said. “I have no idea. We know we’re good friends. We’ve proven we’re great in bed. So, I think we should continue with those two. As for everything else…. I’m not sure.”
“Well, I have an idea. It is Sunday. We’re together. Which means….”
“Brunch!” she chirped!
Epilogue:
After that brunch, we went back to my place where we spent that afternoon and night in bed again. We continued that pattern for a few months, not really dating, more than friends. We both started traveling for work again and saw each other less and less.
Every now and again, we would meet up, but post-brunch sex dwindled. There were a few times, though (after too many tequila shots, a late night booty call after a bachelorette party, another friend’s wedding, a weekend trip to the Dells) that we would hook up.
It was fall when I saw Kim calling my cell phone. I answered and we chatted for a few minutes when she finally said, “I have news.”
“Are you pregnant? Because I haven’t seen you in a few weeks.”
“Fuck off. No, I’m not pregnant. But, I met someone.”
Kim went on to tell me about a guy she met through a friend. His name was James and they really hit it off. I ended up meeting James and Kim for brunch one day and son of a bitch…he was an awesome guy. Ironically, the next month, we met for brunch again, this time with my new girlfriend and future wife, Sherri. When James got up to go to the bathroom I looked seriously at Kim.
“Tell me the truth.” I said.
“What?”
“You picked a guy whose name was close to mine so if you yell out my name in bed, you can cover, right?”
Kim laughed out loud and gave me a familiar punch in the chest as Sherri squealed, “Jason! Don’t be an asshole!”
I lifted a glass and said, “No, I’m not the asshole. But here’s to the asshole who broke the curse on April Fools Day and got us all here today!”
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Thanks for reading. Hope you enjoyed this year’s entry to the April Fools Day Story Contest 2023! Let me know what you liked and what you didn’t. What you think was truth and what was added to the story. Remember, VOTE, COMMENT and SUPPORT all your favorite authors!