I was in the kitchen when my coworker, and close friend, Macy came in. She informed me that she was having a couple friends over this weekend to watch the Super Bowl, and she wanted to invite me as well. I said that sounded like fun! I know, at this point, that any time I go out to Macy's, she's gonna pick on me in some way, and it had been a while since she had given me a wedgie, so I had high hopes for that too.
The weekend finally came and I drove out to Macy's. She lives pretty far out in the country, and her house and driveway are surrounded by trees on all sides. With it being early February, there was a chill in the air, and some snow was still on the ground. But it was a little warmer today, and the sun was shining. There was plenty of snow left over, but there was now plenty of mud, which made getting up their driveway a little difficult.
Once I got up to their house, Macy saw my car with some mud and asked if I had trouble getting in. "Nothin I couldn't handle" I said. She ushered me into her house.
When I first got in, Macy introduced me to a couple people who were there to watch as well. Macy also introduced me to her much younger, but taller, sister, Katy. Macy explained that Katy was going to be living there with them for a while. Katy smiled when she was introduced to me. Something about her smile almost seemed worrying to me a bit, like she had a dangerous ability to cause trouble. I couldn't explain it, but I couldn't stop looking at Katy. Katy's blonde hair and blue eyes were, honestly, so beautiful and alluring to me. She was significantly younger than Macy, and looked every bit of it. Fitter and more petite, but also looked to have some more muscle on her. But I didn't come here to think about that, I was there for football.
Throughout the game, we all had a good time and ate plenty of food. I had a couple drinks during the game, so Macy told me she wanted me to stay the night and not drive. Works for me, better safe than sorry, I guess.
The game ended, and everyone started saying their goodbyes. As they filtered out, all that was left was Macy, Katy and I. I started helping clean up for and things.
I notice Katy and Macy share a look and smile at each other. Then, Katy says it out of the blue. "So, (me), Macy tells me you like wedgies." I almost choked on my drink and coughed out most of the soda that was in my mouth. I turned beet red and had to hold back embarrassment. I could hardly look her in the face. They both started laughing.
Katy said, "Look, it's nothing to be embarrassed about, Macy and I used to give each other enough wedgies that they didn't ALL hurt so much. We had plenty of fun with them, too."
Macy chimed in, "we were horrible to each other, but always had some fun with it."
I could only reply with one word answers, trying to hide the embarrassment I was feeling with Katy knowing my biggest secret.
Katy says, "I hear you can give a pretty mean wedgie yourself, and that's hard to get Macy to admit to, after all the hell I put her through." I chuckled and smirked a little, shyly. I replied, "yeah, I guess I can."
"I also hear you can take a pretty good wedgie too." I didn't realize they had both made their way behind me, close enough for them to act before I could respond or react to Katy's teasing.
Before I had time to react, they each lifted up my shirt, exposing my big orange briefs. Four small hands gripped the waistband of my underwear and, with years of combined wedgie experience, yanked my underwear directly up my back together. I immediately squealed and shot up to my toes, gasping loudly. They both laughed at my shriek, not letting their grip loose for even a second. In a synchronized jerking motion, they kept hoisting my underwear up every couple of seconds, until Katy yells "ahh there they are!"
Apparently she was referring to the leg holes of my underwear, because, again, almost in perfect form, they each stopped and lowered their hands to my leg holes. I only felt slight relief for a brief moment as they both readjusted their grip to each grab a leg hole and lift up with all of their combined strength. I gasped and tried to yelp, but I couldn't get any words to come out. Immediately, I felt my feet leave the comfort and safety of the ground. My legs were trembling and the pressure on my ass crack and thighs was unimaginable. I was now at the mercy of these women.
I knew I could make it stop at any point, they'd let me opt out, but for some reason, I didn't want any of it to end. The pain and humiliation, while immense, was euphoric to me. The only thing I could think of was begging to know what they could do next.
Katy seemed to pick up on this and says "Oh Macy, I think he might be enjoying this."
Macy replied with, "I think so too. Wanna help me change that?" They both laughed and started to carry me towards the front door. My heart was racing as I wondered what was waiting for me outside in the cold air? Luckily I had already put on my sweatshirt, but it would still be more than chilly outside. I dreaded, but also yearned, for what they might be plotting.
Once outside, they started to carry me, still held by my underwear, to a tree across the driveway. Once closer, I saw this tree had two branches that had been cut off about 5 feet off of the ground, almost creating two perfect hooks on the tree. My heart sank. "Surely they're not thinking of hanging me up, are they?" I thought.
They got to the tree and set me down. Macy maintained her grip on my underwear, holding the stretched out fabric by the leg holes about halfway up my back, but Katy let go. "I've got the perfect idea, Macy. Hold our TOY here for a minute" Katy told Macy.
Katy walked away and Macy says, "Having fun yet, you dork?" I didn't answer, but I was breathing heavily, anticipating what on earth they could be thinking of. My mind was racing and I could feel the excitement building. Macy, seeing me focused on the door and not her, takes her grip off of my underwear and pulled my jeans down around my ankles, exposing my butt and legs to the cold air. I gasped as the air hit my body.
I suddenly see Katy come out of the house, and she was holding a paper plate. On the plate, Katy had a HUGE slice of the frosted cake she brought for the Super Bowl party. I couldn't figure out what she was thinking.
Katy said "open wide." I obeyed and opened my mouth wide. At the same time, Macy pulled my underwear back away from my body, opening up my underwear wide. Katy, then, plopped the entire huge piece of cake into my underwear. I gasped and shut my mouth and said "eughh ew!" They laughed and Katy returned her grip to my underwear. In sync, they yanked the waistband and I immediately felt cake smooshing its way in between my butt cheeks. I felt the red frosting dripping down my legs and cake smooshing out of the side of my briefs. They laughed at me as I readjusted my legs to the new, uncomfortable feeling. Katy said to Macy, "aw I think the loser thought the cake was for him. I hate to see someone not get some cake." With that, she released my underwear and grabbed a handful of cake that had squeezed out of my underwear and down my thigh and brought it up to my mouth. "Open up, big boy!" I shook my head no, and held my mouth shut. She said, "oh no, are you not gonna obey?" With her other free hand, she then grabs a giant hand full of snow, and shoves it into the front of my underwear.
Instantly, my balls are freezing, one from the exposure to the cold air, but now from the icy snow that's been packed against them. I yelped a high pitched squeal, opening my mouth, and Katy shoves the giant glob of cake into my mouth. Katy's hand brushes my groin as she shoves the snow in with her free hand, and I immediately become harder than I've been during this entire scenario. Katy giggles. "That's a good boy" she says as I struggle to close my mouth with all the cake in it.
My balls and ass are now freezing and covered in cake as Katy returns to being behind me. Katy and Macy return their grip to my waistband. Macy says "I told you he always wore stretchy undies!" Katy replies, "you weren't kidding, they are DEFINITELY going over his head!" With that, each took one of their hands and pulled my head back, maintaining their grip on my briefs with their other hand. Now that my head was facing the sky, they gave one more solid yank on the waistband and I felt their fingers on the back of my head. I closed my eyes as they moved their fingers forward, and I felt them cross my scalp, over my forehead, and finally opened my eyes to see everything turn orange as my wedgied underwear moved over them. But they weren't finished. They weren't yet satisfied, and Katy put her palm on my chin and shoved my head further back with one hand, and with the other, pulled my waistband down past my chin. I had never had an atomic wedgie go so far down my head. My arms were forced up in front of me and my neck was all crooked back. With the cake still in my mouth, I was forced to breath out of my nose, and it sounded strained from the angle, like a struggling pig, and from my nose being covered by my atomic wedgie. Macy was hysterically laughing at me and Katy seemed to be enjoying every second of this.
Suddenly, Katy and Macy look at each other, and begin counting down from 3. My eyes grew as I couldn't imagine how this could get worse for me. Stupid me.
"3...2...1!" With all their strength, they both grabbed my leg holes and hoisted me up in the air, and each lifted the leg holes of my underwear up onto the cut branches. They lowered me down until I stopped mid air. My feet dangled, high off of the ground.
Katy laughed and said "this isn't right." I had a brief moment of relief because I thought for an instant that they'd get me down. Again, how stupid of me.
Katy grabbed the jeans that sat around my ankles and pulled them down off of my feet. She threw them in a snow pile about 5 feet away.
"That's more like it" Katy says.
They stepped back to admire their work. My back was now arched with my underwear pulled completely over my chin, cake and frosting was dripping completely down my thighs, and ice was melting on my balls. My feet were suspended many inches off the ground, and I had more cake than I could chew in my mouth.
Macy said to Katy with a laugh, "damn, even though you're the youngest, you've always been the most evil one." Katy saw my throbbing erection and said "I don't think he's having too bad of a time, don't feel too sorry for him."
With my underwear over my head, I heard the snow crunching as Katy walked up to me. She lifted my shirt and gave me a massive titty twister, tightly gripping my nipples and holding them in a twist while I kicked and whimpered. As I used my hands to rub and relieve my nipples, Katy and Macy both stuck their fingers into their mouth and swirled them around. While I was distracted with the pain on my nipples, In perfect unison, they pulled my underwear back a little over my face and stuck their fingers into my ear at the same time, giving me a double wet Willy. It felt gross and I could feel their saliva coating both of my ears and dripping out.
"Alright, I think we've tortured the loser enough for today, Macy." Katy finally decided she was satisfied, as I hung there in agony from my punishment. "We'll be in the house, come get us when your panties rip, dork," Katy yelled behind her as they walked back into the house.
I worked on chewing on the cake that remained in my mouth, and the only thought I could muster was, "I need to get over to Macy's house more often."
YOU ARE READING
Game Day Blues
Short StoryAnother story involving my close family friend, this time she's got some help. They have an absolute blast torturing their wedgie nerd in all the creative ways they can think of.
