Surprise Hanging

Story Info
My best friend and I surprise you with a wedgie.
1.4k words
4
46k
5
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

Before I met you I'd never heard of a wedgie fetish, the thought of it when you finally mentioned it, not only made me curious, but also very nervous. I didn't know what you mean by that, as far as I knew wedgies were for embarrassment or to hurt someone, something bullies did to people to make them feel small. Which now makes sense to me, during sex you love to be bullied, as well as bully whoever it is you're with. Now that I know that's it, wedgies turn me on to no end. I've got the biggest fetish for them now because of you. Now anytime I see a picture I instantly get wet, and when you talk about doing it to me, I squirm. I look for panties when I go out so I can find good ones that stretch nicely, because I like it when you rip a nice big pair of panties up my ass, and make me scream.

I was out one day with my best friend Jas, just looking around a new store that came open not too long ago. We both really enjoyed the panty section when we came up on it, I almost squirted everywhere thinking of all the wedgies you were going to give me and I was going to give you. I picked a pair up, feeling their stretch, and heard Jas come up behind me and comment on them. "They'd be perfect for a wedgie" and I just blushed, because I knew she was right. I started looking more now, because that meant she would join me when I found the perfect pair. She knows I love to give you wedgies, and she loves to join in. She enjoys the look on your face when we both get to pull on the panties and they crush your dick and balls while we just laugh and you beg us to stop. We pick out a nice pair, big ones that are lacy and super stretchy, and we find a pair of suspenders to help them last us longer, and we head out the door. We went back to her house, grabbed her over the door hanger that her dad uses to lift himself up, and we decide to try and use that to hang you, and we head back to our house to surprise you with what we had...

Since it was just an impromptu trip to the store, you didn't know what he had planned when we got back. We checked to make sure you were in the living room playing games like before, and snuck off to the bedroom to get ready. We put up the door hanger making sure it was secure, and we both undressed down to our panties, we know you like them so it's all we wear, especially when Jas comes over. We can hear you in the next room but we want you to be surprised so we start playing loudly by ourselves first. Kat gets up on a chair, and I begin to loop her panties around the door hanger, and attach the suspenders to the panties for extra support so they don't rip right away, and before she's ready I quickly move the chair so she can't stand anymore, and she falls a short distance feeling the panties ride up her ass, and she moans loudly, we know you hear that from the other room because we hear the game pause, so we keep going.

I start swinging her back and forth on the frame, digging the panties into her ass and she's moaning, begging for more, as we hear you begin to sneak around the corner. Your panties are ready for you on the floor outside, with a note that says put me on before you enter. Along with my vibrating anal plug, and the suspenders. You take off all of your clothes, take the plug and slowly start moving it up your ass, I want you to feel it vibrate during the wedgie, and you get excited when it finally pushes all the way in. Next you put the panties, on, and are confused about the suspenders but you do it anyways, they'll help me later though, and you slowly slip into the room.

"There's my little boy" I say as you walk into the room, you've got your hands behind your back, trying to make sure the plug doesn't fall out, but it won't. You see Jas hanging and your dick begins to get hard into your pants, and I tell you to watch for a few minutes as I pull hard on her legs yanking her further down, and she winces. I see your dick jump in your pants, I know you enjoyed that, so I pull hard again and you bite your lip. "Don't worry" I say "It's your turn now". I grab the chair so Jas can stand, and you can see the relief in her face when she finally does stand, then she looks up ready for you. I unloop her, and now it's your turn to stand on the chair.

You hurry up there, I know you're excited for this. The panties we got you are beginning to fall a little, so I begin fast, and start looping you in, "I hope you're ready for this," I say, "because we're not letting you down for a while"... You didn't really know what that meant yet. I get you fastened with the suspenders and everything, and I kick the chair hard from under you, and you fall with a thud into the panties, almost screaming. The panties are cradling you just right, and you can feel the vibrations start to intensify as the plug is pushed further up your ass. I turn the speed to the highest, and we begin throwing you back and forth between us like a ball on a playground, and you can feel the underwear pushing further and further up, your dick just getting hard as hell in your pants, and we are just giggling and laughing as we push you around like nothing.

You want to cum just from the vibrations and the panties, and can feel it welling up, and you almost cum hard in your pants. We stop suddenly, and she and I leave you hanging and move over to the bed. "You just stay put" I say with a smile, and i bend over, getting ready for Jas, and she yanks hard on my panties, making me moan, but I just look up at you. I can tell you want to help her but you can't, you can only watch. You squirm, but nothing works, and you stare as Jas puts my big strap-on on and gets ready to fuck me hard with it. "Let me down" you say, begging us at this point. But we just shake our heads no and keep going.

She gets the head ready behind me, and then pushes hard causing my back to arch, and starts fucking me hard. We're really into it, both moaning hard, and I'm getting ready to cum everywhere, while you just swing yourself back and forth on the door frame. You start taking the suspenders off, you figure that's what's keeping it from ripping, and you're trying so hard to get down from the door, and when you finally get them loose, you fall further down, ripping the panties hard and putting you on all fours. You surprised us both, but Jas's into what she's doing, so instead of stopping we let you join like you wanted to. You come over and smack me hard on my ass, leaving a red hand print behind, and start whooping me hard as Jas fucks me. I'm squirming and trying to get away, but you're focused on what you're doing and you keep going, you're not going to let me get away.

Tears are streaming down my face, and my ass is so red at this point, but you like it when I cry. You get behind Jas as she's fucking me, and you slip your now throbbing dick into her, and as she's fucking me she comes back hard against you, and it feels so fucking good. You're slamming hard into her at this point and she's barely moving now, the vibrating can be felt by her too so she's about to cum everywhere as you do, and as you push into her she just pushes harder into me so now we're all just about to cum at this point. Finally, you start to feel it come and the vibrating in your ass is too much and you finally cum hard pounding into us, and the both of us cum with you. We all fall on the bed in an exhausted heap, and look at the mess we made everywhere.

Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
1 Comments
AnonymousAnonymousover 6 years ago
Great Job!

i love the f/m and m/f wedgies! this is amazing!

Share this Story

Similar Stories

The Contract - Sexy CEO Pt. 01 Fantasy CEO making up for a mistake.in Exhibitionist & Voyeur
Katie's Wedgie Humiliation Pt. 01 A new graduate student is humiliated by her roommate.in NonConsent/Reluctance
House-Sitting Panty Lover Pt. 01 Sissydream come true housesitting for his two neighbours.in Transgender & Crossdressers
Chastity Resort Pt. 01 My wife agrees to a nudist resort, but on her terms.in Exhibitionist & Voyeur
Lick It Clean -- The Black Version She gets down 'n dirty with two ghetto sistahs.in Lesbian Sex
More Stories