PranksGoneWrong: The Bachelor Party

Content Advisory: This story contains elements of incest, group sex, and nonconsentual sex. All characters are over 18 years old and all events are fictional...

Pranks Gone Wrong is a series of unconnected short stories about pranks backfiring in a humorous and or sexual ways. This is the first installment and my longest story to date. Please feel free to comment.

*****

My friend John was getting married in a couple weeks and he'd asked me to be his best man. He was my best friend, so of course I'd agreed. But as I was planning his bachelor party something occurred to me.

About a year and a half ago, John and I had been engaged in one of our all out prank wars. It had started out small and stupid, as these things do. But it escalated over time to large and idiotic. It ended up lasting for months, and the pranks just got bigger and dumber.

It only ended when John, in a monumental bout of stupidity, super glued my hands to my car steering wheel. I almost wrecked my car and I wound up in the hospital for two days. Someone could have been killed. John was horrified at what happened, and what could have happened. He apologized for weeks afterward.

The shock of what had happened shook us both up so much we agreed to end the whole thing then and there. For good.

I knew that was the right thing to do... but it always kinda rankled me that John got in the last prank like that. That idiot almost gets me killed and I never even got to get him back. Sure it was the mature thing to do, giving the whole thing up. But I never said I was all that mature.

So here I found myself planning my friends bachelor party. And this idea comes to me. It was a messed up idea, I admit. Crazy, and almost certain to fail before it even began. But once it occurred to me, I couldn't get it out of my head. If it worked it would be hilarious, and I could invite all our friends to watch. And if it didn't work, at least no one would get killed from MY prank.

There was just one problem. There was one person who's help I needed. And almost no way they would agree to this insane idea. But the whole concept hinged on the cooperation of Mrs. Lockley, John's 38 year old mother.

*****

I rang the doorbell at Johns mothers house. She'd been married for 12 years, until Johns father was killed in a car accident. She had never remarried after that. And she'd only dated a little in the last few years after John moved out.

When she answered the door I took a good look at her, while trying to seem like I wasn't checking her out. Mrs. Lockley had John when she was only 18. So even though her 20 year old son was getting married, she still looked as hot as ever. She had brown hair with blond streaks, a cute button nose, and bright blue eyes. She did have a few more freckles then most people, but the shape of her body distracted from any minor imperfections. Her hips and ass had gotten a little wide over the years, but in a very good way. The kind that made you wont to grab on and go for a ride. And her breasts must have been a solid D cup at least, and still holding firm. She was dressed a little conservatively, but the thought of what I was going to ask her to do made me hot around the collar anyway. I'd always had kind of a crush on Mrs. Lockley.

"Hi Jeffrey. I certainly wasn't expecting you. Please come in and sit down."

I followed her inside, growing a little more nervous about bringing up what I was there for. She sat me down on the couch, sitting across from me and we proceeded to make small talk for about 15 minutes before I worked up the nerve to try mentioning why I had come. After a few false starts I managed to bring up the reason for my visit.

"Mrs. Lockley, the reason I came over was... Well, you remember a while back when John and I were pulling all those pranks on each other?"

She nodded yes, looking curious, and I continued, sounding more nervous as I went. "You know that last prank John pulled on me that almost got me into a car accident. Well we both agreed to stop after that. But I always thought it was a little unfair that John got to pull the last prank, almost get me killed in the process, and I never got to get him back at all. So I came up with this idea... that I think will... be...uh. Well... it's a prank you see... and I kinda need you to help me.

I waited a full minute in silence, but she still didn't respond. I looked up at her, and she had a little smile on her face and there was a kind of twinkle in her eyes. Seeing it brought back something john had told me once. He told me he thought he must have gotten his love of practical jokes from his mother, because she had always been pulling stuff, before his dad died. I had never really taken that that seriously cause what kind of mom goes around pulling pranks. But looking at her face I finally started to understand what he meant.

"You know, I've been thinking about some things myself." She finally said. "John sees this girl for almost a year before telling me, and now they're engaged all of the sudden. I think he could use a little lesson. I'm in, I think. What did you want me to do?"

So I began laying out my plan. When she heard what I wanted her to do her eyes got wide and she started blushing furiously. But the only time she interrupted me was to suggest ways to make it work even better. It took an hour hashing out the details until we had a plan we both thought might work. Then we went our separate ways to handle our own sides of the job. As I was leaving Mrs Lockley called to me. "Oh, and Jeremy, please call me Megan from now on."

*****

It was a week later that the bachelor party took place. It began innocently enough. Me, John, and six of our friends went out to dinner at a steakhouse. We all had a few beers with dinner. Then we left the restaurant and went to a nice little hotel room I had rented. I had stocked it up with liquor beforehand, so once there we started drinking in earnest. I kept it light myself though, cause I wanted to make sure that I remembered every moment of what came next. But I made sure John was well on his way to getting trashed.

Then it was time for the entertainment. I had texted Megan an hour earlier, so she was all ready. I sent one more text that read simply 'GO' and waited. When there was a knock on the hotel room door I made a big show of wondering who it was and went to answer it.

When I opened the door, in walks a sexy older woman, with long black hair in a frilly black lingerie top and a tiny little thong. A trench coat fell off her shoulders as she passed through the doorway. She had something like a Mardi Grass mask covering the top half of her face and a small music player in one hand she set down. Her top was ridiculously low cut, and pushed her tits ups so they seemed ready to pop out. Aside from the bustier and the ity bity thong all she wore were knee high leather boots. She struck a sexy pose and said in a sultry voice "Who's ready to have some fun!"

She pushed her music player into the corner and put on some hot dance music. Laughing and catcalling the guys all grabbed chairs and made a circle in the middle of the room.

The stripper set to dancing for us, shaking her ass and thrusting out her tits. She'd run her hands sensually up her bare legs, while gyrating brazenly in the direction of one or another of the guys. Her tits shook and her ass jiggled hypnotically. For fifteen minutes this went on, until the music wound down and she left off to take a short break.

I followed her into the little kitchenette, making sure none of the other guys could hear us. "Megan?" I quietly asked, not really sure it was even her. She looked incredibly hot. She giggled looking up at me and slipped close to give me a quick hug.

"That was incredible. I've never felt so sexy." She said breathlessly. "Do you have anything to drink?"

I apologized, explaining that all we had was hard alcohol. She didn't seem to mind, downing a couple swallows of vodka.

"It's just as well. If I'm going to keep this up I'll need a little liquid courage." She said taking a third swallow.

"You look amazing. I never would have recognized you if I didn't know it was you. And your so hot dressed like that."

"Thank you, Jeremey. You know a woman does like to hear that kind of thing, once in a while." She said, looking at me coyly out of the corner of her eye. "So, at what point should I remove my mask.

It's no fun if I don't get to see the look on Johns face when I do." She asked me.

"I'd say not until after you've taken your top off. That way it will be really shocking." She just gave me a level look when I said that.

"You don't think that would be carrying this just a little too far?"

She responded after a moment.

"No! of course not... I mean, it's not like I just want you to take off your top because I've fantasized about seeing you boobs for years. It's totally for pranking purposes only." I said with a huge grin on my face to give me the lie.

She didn't look entirely convinced, but she didn't look entirely displeased either. She did two more shots to work up her courage and headed out to get back into the ring of horny guys. One of whom was her only child.

She danced erotically around the circle, paying close attention to John whenever she drew near to him. After a few passes, she stopped in the middle, shaking her ass, and started undoing her top. It was just three quick buttons in the back and the whole thing started to come away at once. She caught it with her arms and holding it in place she continued to dance. She let it start to slip several times, but stopped it each time before the best stuff could show. Then stopping where both me and John had a good view, she dropped her arms.

Dropping the garment to the ground she stood there a moment panting. She seemed to waver for a second, but the roar of enthusiasm from the guys seemed to spurr her on and she started up again, tits swaying freely to the music now. She seemed to get a charge out of the excitement she was generating in the guys.

After a few songs, a call went up for a lap dance. Not missing a beat, she dropped unto the lap of the nearest guy and started grinding away. Facing outward, she ground her ass against him for the length of a song, gyrating seductively. Moving on to the next guy with the next song she turned around, and sat on his lap facing him. She thrust her tits into his face and put her hands on the back of his chair, moving in slow circles on his lap.

When she moved on to the next guy, Freddy, she turned around again, to back up into him. But while her back was turned, he undid his jeans and whipped out a six inch cock. Seeing that, I almost said something. Almost. But after seeing the way Megan had opened up after taking her top off, I'm ashamed to admit that my desire to see how far she'd go out weighed my desire to protect my friends mom.

She was wearing just a g-string, knee high leather boots and a mask by now, so as she back up, the erect cock nestled perfectly between her large ass cheeks. From my angle I couldn't see her face anymore, but it was clear when she noticed the feeling and recognized what it must be, because she froze. Freddy, however, didn't. He put his hands on her generous hips and pulled her hard against him. With his cock buried between her cheeks, the head just poking out of the top, he began to move her up and down manually.

She never said anything, or reacted at all. She just stood frozen, bent over at the waist with her globular tits hanging down, while Freddy basically jerked himself off with her ass. After a few minutes, Freddy grunted, spraying cum up Megans back to run down her ass crack. When he released her hips, falling back in his chair with a satisfied look on his face, she finally moved, springing up and racing around the counter into the kitchenette. Even with her mask on, I could still see the tears in her eyes.

Now I really did feel bad. I headed toward the kitchenette, smacking Freddy in the back of the head on the way. I found Megan huddled in the corner with a bottle of whiskey in her hand.

"I'm sorry about that. Freddy's a fucking asshole. We should probably just stop this thing now." I said, putting a hand on her shoulder.

"Could you just... give me a minute. I just... just need to collect myself." She said, giving me a little half smile to show she was OK. The tremble in her voice made me think it was just show though.

"OK. But this whole thing is over. I'll tell the guys your leaving and we'll pretend the whole thing never happened. OK?" She gave me a tentative nod and I left.

When I told the guys the stripper was leaving there was a chorus of disappointed groans. And more then a few punches to Freddy's arms. After a good round of being cursed out Freddy said he'd go apologize to the stripper. He went into the kitchenette and didn't come out for about 10 minutes. The rest of the guys were drinking and joking, so I went to check on them. I met Freddy on his way out, and he winked at me. I didn't know what that was about, but I continued on to check on Megan.

She was standing up now. And looking quite a bit better, though I worried the nearly empty bottle in her hands might have something to do with that. I asked her how she was feeling and she told me she felt much better. Freddy apologized for what he did.

"He said I was so sexy he couldn't control himself. I didn't think I could still have such a strong affect on you young men. When I agreed to this I almost didn't think it would work. I thought I would walk through the door and see disappointed faces. Instead they're disappointed because I'm stopping so soon. I might start doing this for real." She said with a laugh.

Her voice didn't sound slurred, and she certainly sounded better. But I still just wanted to get her out of here as soon as possible. "let me walk you to your car." But before I could turn around she put her hand on my chest, leaned in, and kissed me. I felt her tongue brush my lips for a moment, and then she pulled back. "You know, I think I might keep going after all." She started walking past me back into the main room. "Those aspirin Freddy gave me are really kicking in."

Aspirin? I heard the music kick back on, and when I looked into the room, Megan was straddling Micky. I just stood there, feeling like something was off.

About halfway through the song, Megan took Micky's hand and placed one on each of her breasts. She then shoved her tongue down his throat. The deep make out session lasted until the end of the song, and then she moved on to the next guy. She plopped down on his lap and drew his head down to her tits, where he took a nipple into his mouth and started sucking.

I was trying to think what it was that was bothering me, but the show Megan was putting on kept distracting me. Then it hit me. Freddy carried hits of ecstasy around with him. And when her wanted to screw with someone, he offered them some 'aspirin'. Realizing what had happened, I stormed out into the middle of the circle to get Megan. First I'd get her out of here then I'd kick Freddy's ass.

But when I grabbed her arm and pulled her up, she just threw herself around me and started kissing me again. Nice as it was, I was too pissed to be that easily distracted. I started pushing her away, but before I'd made much progress I felt something new. Her hand sliding into my pants.

Before I knew it she had ahold of... Me. And I was a hand full in my current condition. "Wait!" I managed to get out, but stopped short as it became apparent that while she grasped me with one hand, her other had been hard at work undoing my belt and fly.

She was down on her knees and had my pants and boxers around my ankles in one motion. Before I had regained enough cognitive function to say or do anything, I felt her mouth engulf my cock and all hope of rational thought went out the window.

My eyed closed as she sucked me. her lips sealed around my shaft and she started taking long slow strokes. I don't know how long this went on for, but I sure noticed when it stopped.

Megan was still in front of me, but now Freddy was lying underneath her. His pants were around his ankles and her thong had been pushed to one side. His dick was inside her and his hands were fondling her round ass.

The reason she stopped blowing me was she had to sit back to get Freddy all the way in.

A part of me knew I should be angry or alarmed, but seeing the blissful look on her face, I just stepped forward and shoved my dick back into her mouth. She welcomed me with a moan and started leaning forward to take my cock, then leaning back to impale herself on Freddy's dick. Looking down at her I couldn't last long and I grabbed the back of her head, starring into her eyes, and rammed down her throat, cuming hard.

I stumbled back, only to be replaced by one of the other guys. She started blowing him enthusiastically. Then a guy came in from each side with their dicks out and she started stroking them while they fondled her tits. I just sat down in a daze, watching what had become of my prank while not being able to process any of it.

Freddy grunted, and I saw cum running down out of Megans pussy. The guy in front followed soon after, with the other two just behind. Megan was left with cum running down her shoulders onto her tits, down one side of her mouth, and dripping out of her pussy. She stood up, looking as dazed as I felt.

Then a call went up for the bachelor to take his turn and John stepped up in front of his mother, nude. Her gently pushed her back down to her knees and guided her head to his cock. My mind started screaming at me to do something but I felt too numb to move. When the head touched her lips she seemed to regain a little focus. She tenderly kissed the tip, then ran her tongue along the shaft. She sucked first one ball into her mouth then the other. Then her tongue trailed back up the shaft to kiss the head again.

John seemed to lose Patience with the slow and steady approach, grabbing the back of her head and shoving all seven inches of his cock down her throat. He held her there for a few seconds, listening to her gag, then released her just to thrust back in twice as hard.

I watched John brutally fuck his moms face for several minutes before I noticed that her right hand was busy vigorously fingering her cunt. It was shortly after that that John stopped, pulling out. He told her to lie belly down across the narrow coffee table, her ass in the air. She complied, and he got into position on his knees behind her. He lined his cock up, not with her pussy but with her asshole.

"God I've wanted this ass since the moment you walked in the door!" He announced to the room, thrusting the first few inches into her ass. Grabbing her hips for leverage, he forced a few more inches in before drawing out again and thrusting back in. He repeated this processes a few more times. Once she loosened up a little he started to get a rhythm going. Pretty soon he was fucking his mothers ass thoroughly, grabbing her tits and going to town.

Megan began making low grunting sounds with each thrust, and I could see from where I sat she had a string of drool hanging down from her chin.

Micky didn't let her mouth go to waste for long, kneeling down in front of her and inserting his dick into her mouth. Pinching and pulling her nipples, he thrust in time with John, crushing her between them. After a few minutes he pulled out, jerked his cock a few times. Right before he came all over her face, he yanked off her mask.

I felt a moment of panic. But Micky was quickly replaced by someone else, and with the cum running down her face and her cheeks distorted from the cock thrusting into her mouth I doubt anyone could have recognized her.

John continued fucking her ass, slowing down occasionally to keep from cuming too soon. It took about twenty minutes before John came inside his moms ass, during which every other guy there but me took a turn at her head, cuming on her face and hanging tits afterward.