Chapter 2: Sean making his way to the tailor

  • Facebook
  • Twitter
  • Reddit
  • Pinterest
  • Invite

Status: In Progress  |  Genre: General Erotica  |  House: Stripping and Humiliation

Reads: 438

I am so excited about going to the tailor’s shop.  I have never had clothes made specially for me.  I am lucky to get new clothes at all as opposed to hand me downs from my brother.  The t shirt (a too small, worn, hand me down) and thin tight shorts (again hand me down) is way more what I typically wear.  And for here, these clothes are enough.  I very much fit in with the style here.  My choice of wearing briefs may not fit the style, but I like them, they are comfortable, they are cheap, and thus I wear them.  You can’t get between me and my white briefs.  I may not look like Boomer Esiason did in his but I am still OK.

The walk from my house to the tailor’s is about a couple of miles but I am a fairly fast walker so it is about 15 to 20 minutes.  I left an hour since I figured I could go to other places downtown while I was there and I wanted to show respect by arriving early.  As I was on my way my heart sank as I saw several members of our football team playing in the local park.  I tried to creep by unnoticed but no such luck.  Scott and Tim (the two big guys who humiliated me at school) called me over.  I was too far from the store to chance running for it so I, head down, made my way over to the field.  They were having some fun, or at least I am sure that is what they would call it, with a cute little guy named Ned.  Ned has red hair, fairly large ears, is thin, blushes easily, and was sadly given pretty good reason to blush.  He was functionally naked, his briefs, all the remaining clothes he had, were down to his knees and he was bent over Tom’s (Tim’s younger brother) legs getting what seemed like a fairly painful hand spanking.  Ned’s butt was getting quite red as was his face.  They matched his hair quite nicely.  It had to be pretty horrible.  Ned was very much a favorite target of the team during that initiation week.  He and I both got the unwanted attention of the team.  Ned and I even got a swirly tour of the locker room after gym class one of the days.  There are ten toilets in the locker room and we each got a swirly from all of them.  So I had been through it with him so to speak.

I could see that the team had rechargeable clippers and a set of black shapries and my heart sank.  Clearly they were fixing to utterly destroy poor Ned.  I couldn’t bear to watch this happen to poor Ned.  I would rather be humiliated myself than watch a good friend take it.  And this was going to be so bad.  Poor Ned would never live this down with school starting in just a week.  While I was lost in the nightmare of what was about to happen to poor Ned, Tim was clearly trying to get my attention.  Since calling my name wasn’t working, he reached down my shorts and pulled my underwear about 2/3 of the way up my back.  The pain was very intense and it was a bit humiliating.  But it also got me to focus on what Tim was saying.  I was being offered a deal.  I had to entertain them for next twenty minutes or else Ned was going to get the treatment.  I had their word if I went along no one would have their hair cut and no one would be sharpied.  I figured what the hell, let them have their fun, I wasn’t going to see them again.  How bad could it be.  Tim was several inches taller and many pounds heavier than me.  He had curly black hair, a well built chest, tan skin and some amazing legs.  I love a good set of thighs.  His younger brother could have been his twin.  They were a big contrast to me, my dirty blond hair, short stature, slim wiry body, and skinny legs.  But the one place we had some similarity was in our rear ends.  We both had big butts which on Tim fit but on me stuck out.  Because of that, my shorts and pants were always tight.  On him, the tight pants and shorts looked fantastic.  Today he was wearing a hot pair of spandex shorts with a looser pair over them.  That and a very tight t shirt which showed off his very good body.  I found myself getting hot to despite myself. 

I agreed to entertain them for the 20 minutes.  He set his stop watch and played a bump and grind song on his phone.  There were 10 members of the team there along with Ned and I.  I was expected to strip down for them as they hooted and hollered at me.  It took me 3 minutes but it seemed more like 3 years.  I started by taking off my shoes and socks.  I was wearing a pair of sneakers with hard sturdy soles which I was about to find out just how sturdy they were.  Then it was my shirt.  It was so tight it was hard to remove and keep the beat.  The boys were jeering and catcalling.  I turned completely red.  You could see my pulled out briefs way up my back, my tight shorts.  The kids were laughing and fighting over my clothes.  Then I had to take off my shorts and dance for them in nothing but wedgied briefs.  It was all I could do to keep from crying.  Then it was time for the briefs and for me to dance naked in front of the jeering, catcalling crowd.  I was so humiliated.  They talked about how exited I was getting, how red I was getting, then they felt me up.  Hands on my arms, my legs, my stomach, and my genitals.  It was both humiliating and oddly exciting.  Then it was time for the main event.  Each one was going to get to use the shoe on me five times as I stood up with my hands locked behind my head.  So it was one dose humiliation as I was naked in front of all of them and one dose pain as I got hit hard with that sneaker.  The first couple of guys hit hard and fast straight on my ass which was now on fire.  I tried to stand still but it was impossible so kids got to see my willy go hither and yon.  I was starting to tear up but it was only going to get worse.  They seemed to go in an increasing order of pain.  I took shot after shot after shot to my now flaming ass.  I know it was going to be well and truly bruised after 40 brutal hits.  I gave up any pretense of bravery and was balling my eyes out.  Finally I was down to just Tim and Tom and for a second as Tim said my ass looked to bad to take another hit, thought it might be over, but oh no.  Each one gave me five solid shots on my thighs.  I only thought the ass was painful.  Finally the beating was over.  It hurt so badly but they weren’t done yet.  For the five remaining minutes they took turns pushing my face into their clothed crotches and dry humping my naked ass.  It was total humiliation but at least the pain was over.  They were good as their word, in that I got my clothes back, as did Ned, and we got to leave.  As we were walking out, Ned turned and called to me and as I turned my face toward him he pulled me in toward him and kissed me for what seemed like an eternity.  It frankly felt really good.  I always wanted to do that to you, and this is probably my last chance for at least several months.  You saved me back there, I know that had to be awful, thanks.  I will miss you so much.  I kissed him back and left to make my way to the tailor’s.


Submitted: November 28, 2020

© Copyright 2021 dsc999. All rights reserved.

Chapters

  • Facebook
  • Twitter
  • Reddit
  • Pinterest
  • Invite

Add Your Comments:

Boosted Content from Premium Members

Short Story / Literary Erotica

Short Story / Sci-Fi and Fantasy Erotica

Other Content by dsc999

Book / General Erotica

Book / General Erotica