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!"
