Who's the Fool?

This is my entry into the

Literotica 2022 April Fools Day Story Contest

. 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.

Last year's April Fools story "Weekend Trip Home" was one of my most highly rated ones. Hopefully this one is equally well-received.

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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I met Monica in my mid-20s when I had started a new job in the Twin Cities. We were in different departments but would interact now and again. After about 6 months of working together, she left for a new opportunity and at her going away party, I got her number to ask her out. We went on a few dates over the next month and I started hanging out with her and her group of friends since I still didn't know a whole lot of people in the area socially. Eventually, we started officially "dating" and spent more and more time together.

Monica was thin and fit with a sandy brown "Rachel" haircut that was popular at the time. Her chest was on the smaller side and her ass and legs were tight and athletic. She did yoga and pilates so she was uber-flexible when we would make out or roll around in bed.

She was living with three other people, two guys and a girl, but nobody was involved romantically with each other. In fact, most weekends there would be a myriad of boyfriends, girlfriends, friends and friends with benefits hanging out at their place. The guys, Chris and Ray, were normal twenty-somethings who drank, watched sports and were pretty easy going.

Her female roommate, Carol, had short, curly blonde hair that would bounce around as she bopped around the house. She had a huge, bright smile and bore a striking resemblance to Kate Hudson in the movie Almost Famous. Carol favored wearing leggings and shorts around the house, often with a cropped t-shirt or loose top. That meant that her perky tits and ass would also bounce around the house. Carol flirted with everyone: her male roommates, Monica, me, waiters, bouncers, taxi drivers and any of the various people she would meet. Whenever we all would go out, Carol would be the one leading the fun for the night.

The whole group would always have fun going out together, drinking and partying. But, for me, the fun ended there. See, after a month of dating, Monica & I would only make out or feel each other up - no sex. There was some touching below the waist, but never too much. We had both stayed over each other's places for the night, but still there was no sex. Oh, I tried. But as soon as my hands would wander under her panties, she would giggle and move them away. Weirdly, I knew she wasn't a virgin, either. We had talked about past partners and sex, so she seemed to open to it, but just kept pushing off whenever we got close.

That's not to say we didn't have some fun. After one night of drinking, she took me in her mouth and blew me, swallowing my entire load. When I tried to return the favor, she pushed me off and rubbed herself through her panties until she came. She once made herself come when we both fully clothed on the sofa watching a movie, just by grinding her denim-covered pussy against me. We had even showered together a few times after spending the night, so I knew that her pussy was covered with a well-trimmed patch of hair that matched her sandy-brown hair. Our hands would wander and I she would let me play with her soapy tits, but never her pussy.

The closest we ever came to actually having sex was after a wedding for one of her friends. She was in the wedding party and we both had a lot to drink at the reception. I had already determined that there would be no action that night because we were sharing the room with Carol who 'needed to save money'. At the reception, Carol ended up leaving with some guy, so we were going to have the room all to ourselves. We got back and were all over each other. We tumbled through the door planting sloppy kisses all over each other's mouths and necks. With our hands getting active, clothes started coming off. I was down to my boxers, while Monica was in a burgundy, lacy shelf bra and matching lace thong. She was panting and breathing heavily as I pressed my rigid cock against the cleft of her ass while gripping her small tits through her bra. I was planting kisses on her neck and started to bend her over the bed. For her part, Monica had one elbow down on the bed while the other hand was reaching back to grab my dick. As I snaked out of the fly in my boxers, I could just feel the heat and moisture of her pussy on the tip of my dick when Monica pulled away with a jump.

"Jay! We can't do this right now."

"Mon...why not? We have the room to ourselves, I can tell you're hot right now. I have condoms in my bag if that's what you're worried about."

"No...it's just that....uh...Carol may come back and interrupt us."

I was now laying next to her on the bed, running my hand over her breast trying to get her back in the mood.

"So, let's tie something on the door...she'll get the message." Monica then grabbed my hands, pushed them away and stood up.

"Not tonight. Let's just get ready for bed." Not for the first time, I went to bed with an insane case of blue balls that I was able to somewhat relieve the next morning in the shower. The pisser of the story? We didn't see Carol until 20 minutes before brunch the next day when she came back to the room. By the look of her, at least someone had been well and duly fucked the night before.

That wasn't the only time I got to practice abstinence while Carol ... didn't. I would sometimes stay over their joint apartment and on some nights, Carol would bring home a friend or conquest for the night. As I would lay in bed with either a case of blue balls or slight relief from a handjob or blowjob, Monica snoozing by my side, I could hear Carol's nighttime activities through the walls of the house. There was more than one morning where we would all see a red-faced guy (and one time a red-faced girl) emerge from Carol's room knowing that we had heard all the details of their escapades through the walls.

So, it was an early-spring Sunday and we were all lounging in various degrees of our hangovers, watching a movie in their living room. As we were chatting, Ray mentioned that a bar downtown was having an "80s April Fools party" the following weekend. It really wasn't much of a theme: they were promoting crazy drink shots, 'bad song' karaoke, and encouraging people to dress in crazy, bright colors. After some banter, we all decided it would be something fun and different to do the following weekend.

On April 1

st

, we all met at their apartment to pre-game and then went over to the bar together. Monica & Carol had chosen to embrace an 80's vibe for the party. Monica was in shimmery pink leggings under a silver leotard. She had on legwarmers and sneakers and her hair teased up with lots of hairspray. The outfit showed off her tight athletic body perfectly. Carol went more the techno-Madonna look. She was wearing a short pink miniskirt and high heeled ankle boots. Her tights were yellow and she was wearing a neon purple crop top that was stretched over her tits. Rob, Chris, their girlfriends and I all wore a mix of crazy shirts and colors to keep the spirit of April Fools. Right before we left, Monica & Carol produced a big bag of light up necklaces and bracelets (like the ones kids wear on Halloween to be seen in the dark). We all wrapped them around various limbs and went out the door.

For a bar party that wasn't one of the big ones -- Halloween or St. Paddy's Day -- the bar did this one right. They had Karaoke -- but also an "80s cover band" which was a string quartet playing 80s tunes on violins and a cello. Even with the booze, it was an awful mashup of music. Speaking of the booze, they had girls going around with test tubes full of "mystery shots". I give credit to the owner on this one. He had us all paying $10 for shots of whatever expired booze he had in the back room that they were putting in those test tubes.

When we arrived, they were stamping our hands with different stamps -- smiley faces, clovers, hearts, etc., and said it would be explained as the night went on. After we had been there for a bit, the sound system starting blaring "Kissing a Fool" the old standard. A DJ got on and announced that every time the song played, we had to find someone with the same stamp on their hand and kiss them. There was a mad scramble in our group as nobody could find a matching stamp. Finally, Carol matched up with Chris' girlfriend and gave her a quick kiss on the lips. I turned to a girl on my right and we both saw a star on our hand. We gave each other a quick kiss on the cheek and turned back to our groups.

As the night went on, all the games got more fun. The Karaoke got worse, the shots stayed the same and the kissing game got more active. Some people had tired of the game, while others had obviously found a "mate" and were getting more amorous. Monica and I were having a fun night, dancing and drinking with the gang. A few times on the dance floor she would grind her spandex covered ass against me as we danced. By the sixth time "Kissing a Fool" played, we had all abandoned the game until I heard Ray's voice, "We both have a star!!!!"

He spun me around and planted a kiss on my lips. The entire group erupted in laughter as I pulled away and grabbed the nearest shot girl to rinse my mouth out. With that, we all started to make our way toward the door as it was nearing 1am. I asked Monica where we wanted to crash that night and she asked if we could go to my place since it was closer. We told the group we were leaving when Carol came up to us.

"Hey...can I crash at Jay's place?" she asked gesturing to her male housemates. "Those two are going to be hooking up with their girlfriends and I don't feel like dealing with that noise. I can crash on a couch if you don't care."

At that point, my usual disappointment emerged since I realized a few things. First, I wasn't getting laid that night. Second, even Carol knew I wasn't getting laid. Third, it felt like everyone else in the bar was getting laid. Wishing it was some sort of April Fool's prank, I realized it wasn't.

"Sure. No worries. Plenty of room at Casa de Jason." I wasn't even hiding my displeasure at this point.

Carol, Monica and I walked back to my place. The doorman, Artie, gave me wink as I walked through the lobby with two tipsy girls dressed like they were. We took the elevator up and got into my condo. While the girls used the restroom, I grabbed a pillow and blanket for Carol so she would be comfortable on the couch in my living room. I got each of the girls one of my t-shirts that would basically function as a nightshirt for them. I offered Carol a pair of boxers or shorts to wear as pj bottoms, but she declined saying that she would be, "perfectly comfortable in just the t-shirt."

I stripped down to my boxers and climbed into bed with Mon who was still wearing her panties under her borrowed t-shirt. Once it sounded like we had all settled in, I wrapped my arms around Monica in bed and began to grind my dick against her. She returned the attention by starting to make circles with her ass against me. I licked and kissed the back of her neck while my hands worked their way under her shirt.

Monica started to quietly moan as I played with her tits, squeezing, rubbing and gently pinching her nipples. For her part, she had her hands behind her, holding my hips against her while she pumped her ass against me. When a slightly louder moan escaped Monica's lips, I whispered, "Shhh...we need to be quiet so we don't wake Carol."

"Mmmmm....don't worry. Once she's asleep, she doesn't hear anything."

Feeling how Mon was rubbing against me and how quickly her moans and breath were coming from her, I worked one hand lower, snaking across her tight abdomen and into the top of her panties. I felt her lightly trimmed patch of hair and then my middle finger make contact with her hooded clit, swollen and wet.

Then, after that moment of contact, she pulled away from me completely. Before I could say anything, she had turned over and loudly whispered,

"Jay! You know not to do that until I'm ready. We were having a great time but you had to push further, didn't you? You really wanted to pick tonight to fuck for the first time?" she sounded legitimately angry now. "We're both drunk and Carol is right outside. Is that 'special' to you? Doing it this way and right when Carol would hear us?"

"Mon, calm down," I replied. "I'm not going to apologize for wanting to fuck my girlfriend.."

"Forget it" she interrupted. "I'm not getting into this tonight. I'll go sleep in the living room with Carol." Monica jumped out of bed and grabbed her pillow to take with her. I heard voices in the living room and the sounds of her getting settled in on the other sofa.

In theory, I should have followed her out there, but I was done. I looked at the clock to see it was almost 2am and I was, once again, laying in bed with a raging hard on and no way to release it. I was pissed that I was left like that again, especially with two hot girls only a wall away. As I willed myself to relax, I decided that it was time to end whatever it was with Monica. No sex I could deal with, but the constant teasing and lack of communication wasn't worth the effort anymore.

I eventually fell asleep, only to be awakened by Monica crawling back into bed after what seemed like only minutes later. I could see my blurry clock saying it was 4:15am so I figured that the couch got uncomfortable and she assumed it was "safe" to come back since I would be asleep. I kept my back to her as I felt her get settled in close to me. Just as I started to drift back to sleep, I felt her hand wrap around me and start stroking my cock through my boxers.

While my dick responded as it always would, I was still pissed and whispered, "Monica, enough with the little pranks and teasing. We're not going to go through with anything, so just let me get some sleep."

It was another voice that whispered back, "Well, I'm not Monica, this isn't an April Fools prank, and we are DEFINITELY going to do something." Carol slithered down the bed and gripping my hips, rolled me over on to my back. When she lifted slightly, I bridged my hips enough for her to remove my boxers. Before I could say another word, she took my entire length in her mouth. My hips instinctively lifted pushing my dick further into her mouth as she swirled her tongue around my head and shaft.

Carol started bobbing her head wetting my entire cock. She paused at the head, keeping her lips wrapped around me, while licking and sucking on the sensitive crown. I'm not sure if it was the surprise awakening, the slight buzz, or the complete lack of sex for months, but I remember that Carol's skills were among the best I had experienced. Carol was using one hand to massage my balls while still working her mouth up and down my dick. I could feel my cum starting to boil in me and I let out an involuntary moan.

Carol immediately stopped sucking and popped her mouth off my dick as we both froze, listening to hear if Monica had heard anything from the other room.

Desperate to get myself back in Carol's mouth, I whispered, "Did you shut the door? I think we're ok. But this is still really bad, Carol."

"Yes, the door is shut, but we are WAY beyond 'bad' sweetie." Carol continued, "But just in case, we better try to keep it down a bit more." With that, she lifted up the bottom of her t-shirt to reveal a completely shaved snatch. She swung one leg over my head and straddled me in a perfect 69 as she dropped her mouth back on to my cock.

Her bare pussy was soaked as she pressed it against my face. I grabbed her thighs and pulled them apart to give me better access to her slit. The pungent scent of her pussy filled my nose as I began to lick up and down her pussy lips. She tasted sweet with a slight acidity to her pussy juices as I began to work my tongue and lips over her. Focusing on her pussy was actually helping me keep my own focus away from the way she was expertly sucking my cock. The more I licked, the harder she worked my cock in and out of her mouth.

Her juices were flowing even more, so I started working my tongue in and out of her, which made her grind herself against me harder. Without warning, I locked my lips around her clit and formed a strong suction around it. At the same time, I used the tip of my tongue to rapidly make a flicking motion on her exposed button. That was enough to send her over the edge. I felt her thigh and ass muscles seize in my hands as a flow of sweet liquid came out of her. Her cunt was pressed hard against my face as I kept up the suction and action on her clit. Carol's entire body trembled and she took my entire cock into her mouth and throat.

I moaned loudly into her pussy as jets of my own cum began to shoot into her mouth. Carol stayed where she was, her mouth and throat swallowing my load while her body began to relax from the final throes of her orgasm. It had been so long since I had come with anything other than my hand that it felt like I had enough to fill a water bottle shooting out of me. Even with that exaggeration, Carol never spilled a drop swallowing the entire load. As we both came down from our orgasms, Carol swung her leg back over me and snuggled up against me.

"I'm going to use the bathroom, then check on Monica" she whispered. "If she's still out, I'll come back in and see if I get you up for another round." Carol gave my earlobe a lick and went back into the main part of the condo. I heard her use the bathroom and then go into the living room where, hopefully, Monica was still asleep.

Meanwhile, I was still in a state of buzzed, sleepy shock. Part of me still thought this was some sort of weird April Fools' joke. But it wasn't because just moments before, my kinda-girlfriend's bisexual roommate just snuck into my room and sucked me off while said-girlfriend was sleeping in the other room.

As I lay there wondering if Carol was going to come back, I heard what sounded like whispering and then the sound of Carol re-entering the bedroom.

"She's still asleep" she said as she pulled her t-shirt completely off and over her head. For the first time I got to see Carol's naked body. She was athletic but had some curves in her thighs, ass and tits. If I had to guess, her boobs were probably a C-cup that sat on her chest perfectly. In the darkness, I could see the two silver barbell piercings that went through each nipple.

"I thought I heard voices? Are you sure she's not going to wake up?" I asked as Carol got back into the bed.

"That was me. I got close to her and tried whispering to see if she would wake up. She drank quite a bit tonight, so she's not waking up. I mean, we should still be quiet, though, right? I mean if you are up for more."

Carol had thrown one leg over me and was moving it over my crotch, gently massaging my dick and balls. Her tits were pressed against my side and she was kissing and licking at my chest and neck. Even though I had just come, I could feel my cock slowly stirring again. Carol shifted up and we both rolled to our sides so we were facing each other. I cupped her face and pulled her face to me. Our tongues started to explore each other's mouths and our free hands kept exploring each other's bodies.