My Pranks

By WedgieBoy6969

28.2K 60 4

Series of true short stories of pranks I've done. Mostly includes wedgies. More

4th of July, 2005

Weekend Trip November 2015

9.8K 24 2
By WedgieBoy6969

This happened last weekend and I gotta say, it was funny as hell.

Mary and I haven't pranked each other for about 3 years now. We kinda stopped after she got married. Now she's like 5-6 months pregnant with her first kid, so clearly she grew up. Her husband was on a business trip, so she felt a little lonely. She decided to call up her sisters for a weekend trip (I'm not going to say where).

In the previous part, I told you that Mary was the third of five kids. Well, she has two brothers and two sisters. Her sisters are Nicole and Felicia. Nicole is a year older than Mary and Felicia is two years younger than Mary. They all have the same hair, but Nicole's eyes are blue. Our families are kinda close, which is why Mary had more opportunities to bully me. My mom used to tutor Nicole when she was in high school and coincidentally, Felicia tutors my younger sister, Kate. However, my only connection with them is that they're the cousins of my friend Jake.

As it turns out, I had a fall break that weekend and my mom decided to take a family weekend getaway (which she's been doing a lot of since Dad died). When she heard the sisters were also thinking about a weekend trip, she decided to make one big trip. At the time, I thought it was going to be troublesome, especially considering I was the only guy there. Let me say, I was wrong.

So, we got to the hotel and we had three rooms. My mom and Kate would share one room, the sisters would share the other and I had a room to myself. Now my mom could be really cheap sometimes, but I'm glad she had the sense of letting me have my own room. I remember this one family vacation where she had reserved only one hotel room and the three of us (me, Mom, Kate) had to share it. Trust me when I say that sharing a room with your mom and sister is super annoying and weird. To make matters worse, Kate had her period and I saw it happen. Seeing that is weird enough, but when it's your own sister...ugh. Anyway, I was glad that I had my own room.

The first day went pretty well. Around 7:30, my mom and Nicole went to go rent a movie or something and Mary was taking a nap. Felicia, Kate and I hung out by this awesome fireplace. We talked a lot about what's going on and what's new. Then we kinda started reminiscing about the past.

Felicia said, "Those were some good times"

I replied, "Are you kidding? Mary practically terrorized me with wedgies"

Kate said, "Hey, it's not like you were the only one that got a wedgie from her"

"Yeah, but I was her favorite target because I got stuck with her most of the time"

Felicia said, "Yup, you kept us safe and our underwear in our pants. You're kind of a hero"

I sarcastically said, "Gee, glad to be a big help"

They both giggled. Then Felicia said, "Well, she'll be spending more time with the baby now"

I sighed, "Yeah. Makes me feel sorry for the little guy"

They both looked confused for a sec. Once they understood, Kate said, "Oh, come on. No mom would ever give her kid a wedgie"

I answered, "You never know when it comes to Mary"

Felicia asked, "Hey, when was the last time either of you gave the other a wedgie?"

I thought for a minute and said, "About three years ago, I think. Mary gave me a wedgie the night before her wedding"

Felicia suddenly grinned, "Well...I think she's long overdue for some payback. With interest"

I looked at Kate and could tell that we were all thinking the same thing. We went to the sisters' room. We opened the door carefully and peeked inside. Mary was still sleeping. We removed the blanket. The only problem was that she was sleeping on her back, so we had to roll her over. She's a pretty heavy sleeper, so we weren't too worried.

We finally got on her stomach and slowly pulled up her night gown. I got a good look at her pregnancy panties. For those who don't know, imagine a really stretchy pair of granny panties. They were pink with black polka dots.

We were all anxious to go, but decided that I deserved to start. I slowly grasped the panties then gave a hard jerk forward.

Mary instantly woke in pain and confusion. "Ow ow ow OW OW OW! STOP!!"

I laughed. "Nope!"

I was barely putting any effort and her undies were almost at her neck.

I heard Felicia say, "Ok, I want some of this!"

She ran to the other side of the bed and pulled on the waistband with me. If Mary wasn't pregnant, she could have easily got out of this situation. But since she could barely move, all she did was wiggle around and complain. We gave her a few smacks on the ass for good measure.

After a couple minutes, Kate got on to the bed and sat on Mary's knees. She grabbed the leg holes of the panties and pulled.

Mary screamed. "AAAAARRRRRGGGHHH!!!!! Please stop guys! They're too far up my ass!"

Kate said something clever, "I don't think so. We'll go so far up, the baby will get a wedgie!"

We all pulled as hard and it almost went over her head. But then the door opened and Mom and Nicole walked in. At first, they were really stunned. Then Nicole instantly started cracking up. Mom, however, did not see the humor in it all and stopped us. It was short, but very sweet.

After Mary picked her wedgie, Mom helped her lie back down. As Felicia, Kate and I were leaving, Mary told us to stop.

I asked, "What?"

She had this familiar scary look in her eyes. "After the baby is born, watch your asses. Cause I'm coming for them"

So we have a few months to prepare ourselves for the storm that's coming. But for now, we're just enjoying our sweet revenge.

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