This is something I’ve always wanted to have happen to me, but I’m assuming it never will, so it looks like it’ll happen to me here.
I walk into the massage parlor to find almost all the lights off, ambient spa music playing. I walk up to the front desk to find a woman speaking in almost a whisper, asking me what I’d like done and what gender I’d prefer. I say male, and the type of massage is up to them on what they think I need. I sit down in the waiting room, before a large man walks into the lobby, calling my name. I stand up and walk with him into a private room. He tells me to strip to my comfort level, and leaves the room. Because this is my first time with him, I take my shirt, shoes and socks, but leave my pants and underwear on. I climb on to the table and assume the position, face down, ass up, like a typical massage.
He walks into the room and announces his name as Dave. Dave turns on music, at a bit of a loud volume, then gets the oil in his hands. He starts working my back, my shoulder blades, my arms. As he moves to my lower back, my body has been being bounced around by Dave, and my black waistband of my briefs becomes noticeable. All I hear him say is, “What are you wearing down here?” And my eyes shoot open wide, as I bite my bottom lip, hoping he investigates. I feel Dave’s hand on my lower back, then lifting my pants up slightly just to read the waistband of my underwear clearly - “Hanes”. Dave then says, “Hanes huh? What kind?” I’m a little confused at first, but I’m glad we are going this direction, and my dick begins to harden under the table. I say “Briefs!” Dave responds by saying “Oh, you like wearing briefs huh?” I respond, with a “Yeah they’re some of my favorite pairs.” He says “Yeah, me too, especially like Pump and Champion, and Calvin Klein, you heard of those?” We continue this conversation for a bit. He asks me what other underwear I have. I answer honestly, “Adidas sports briefs, Calvin Klein boxer briefs, Reebok boxer briefs, Nike trunks, Under Armour boxer briefs, and these Hanes briefs.” He tells me that he likes being a masseuse both for the massage, and to see what people are wearing. This is when I go in for the kill by saying, “Well, if you couldn’t see them very well, you can always grab them and look some more?”
He stops massaging me for a moment. I fear that I messed up. After a few seconds, he says, “You don’t say…” He walks up to my side, and shimmies my pants down, about an inch to better see what he’s working with. “Well given it’s a client request, I have to oblige.” Dave teases. He walks back up to my head and places his hands on my back as he slides them down to my lower back. He grips the black waistband, with the word Hanes bunched into his fists. It was at this moment that I realized how much this is going to hurt since his profession is largely based on how strong he is.
Without warning, he leans back and pulls my briefs with him. The black waistband and dark green fabric emerge from my pants with such intense ferocity, like this is not the first time someone has asked him. Enough that my legs come off the table for a moment. I moan and quiver at this response, in which he turns up the music with one hand so no one can hear me scream and moan for him. He recoils by leaning forward, up to my neck, and yanking back again, his two hands up to my shoulder blades with my undies. I groan and mutter, rocking my body back and forth in pleasure. “One more and I think I can get this atomic,” Dave says, which confirms to me that this is not his first wedgie to give before. First, he grabs the legholes and gives small wedgies there, to help the fabric and seams pop open a bit more. He then takes a wad of my briefs, his hand covering waistband to leghole and pulling back on that to hear the fabric sound like it’s ripping, cotton bursting at the seams, my hole being on fire as my hard cock is squished into the table. He goes back to my stretched out waistband, and heaves one final time, as I loudly moan and gasp. He gets the waistband up to my head, but rather than lifting up my head, he wraps my waistband over the pillow and snaps it to my forehead there, practically strapping me to the table by my underwear. Dave doesn’t skip a beat and continues to knead the skin of my lower back, as well as part of my ass now that this wedgie has made that possible. A massage happening to my ass while a wedgie is taking place would be incredible.
As I sit there immobilized because of my underwear, Dave continues the massage. Because of the pain, I don’t feel Dave taking my pants off and leaving me in just my green briefs strapped to the table. He massages the rest of my ass, followed by my thighs, calves, and feet. As I begin to question what’s happening, he reminds me by taking a fistful of my briefs that are roped into my ass and yanking until he hears me whimper. He ends this session by grabbing my phone near my stuff, taking pictures of what I look like, and putting the phone back. He says, “You ever want more requests done, here’s my business card.” And he places it on top of the pile of my stuff. He tells me to take as much time as I want, flipping the sign on the door to “Do not disturb” then leaves the room, as I sit there shocked to what just happened. Needless to say, I will be requesting for Dave next time!
I doubt this would ever happen, but here’s an exaggerated version of what I’m hoping to happen! Comment down below what brands of briefs or boxer briefs you’d like to see in stories!
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