Awkward moments at tailors

[deleted2553771]

Have any other big show-ers here had interesting moments when getting fitted for a suit. The other day I got fitted by a tailor and basically told me I had a big package and he needed to adjust it haha. He also seemed shocked by my size lol

 

[Tony56]

Sadly, that never happened to me. But recently I was being fit for a custom suit and the guy marking me up for the tailor said that I have big calves. Which is true. I used to bike ride a lot and my calves got large. Now that I am old the rest of my body has gone to hell but my calves still are big.

 

[Rippedspeedo]

Fitted for pants last week spilled coffee on my white shorts and polo shirt.He said he would get the stains out. He told me to take them off.This was early in morning and I was only customer.I took them off leaving me in Calvins and socks.Off he went with my clothes.I was flexing and my dick got hard in three way mirror.Two ladies entered and I went behind a dressing screen.The tailor came back out and saw me hiding behind screen.He waited on the ladies.Then he came behind screen and laughed as I asked for my clothes back.Later ,he laughed and started pulling my Calvin's down my tanned legs.I struggled but he had them off and then my socks.I was stranded in my tanline and the women were headed my way.

 

[ericbear]

It wasn't a tailor, but a custom bootmaker. I was getting measured for a pair of custom crotch-high motorcycle boots, wearing the jeans I intended to wear with the boots. They were close-fitting (but not stretch), since baggy jeans legs would get all bunched up in such boots. After measuring my feet in the usual way (size 15), he had to take a series of measurements of the girth of my legs at regular intervals, starting at the ankle and working all the way up, so the boots could be cut to fit properly on my calves and thighs. He completes the right leg first, bottom to top, then starts over at the bottom of the left leg. As he gets to the second-to-last measurement, he looks slightly concerned, but then he really didn't know what to do for the final, topmost measurement. I hang my cock and balls down the left leg, making a large and quite obvious bulge in that sort of jeans, made even more prominent by the fact that I'm seated, and he's kneeling next to it. (You know what they say about men with big feet...) He starts to approach with his tape measure, then quickly backs away. He starts to approach again, hesitates, then gives up and writes down the same number he measured for the right leg. By the way, the boots fit fine. They droop down a bit when standing, so my cock doesn't actually tuck into them.

 

[HotBulge]

In 2019, I was at a suit shop in downtown Boston. The young sales associate was taking my inseam, and he kept taking glances at my crotch while trying to be discreet . After the session, I returned to the dressing room to change back into my street clothing. I was wearing a black undershirt and probably some pouch bikini briefs when the sales associate came to the dressing cubicle with the receipt for me to look over. I wasn’t shy, invited him into the cubicle while reviewing the receipt, knowing he would be looking at my crotch again. Half way through the receipt, I saw the alteration note “crotch out 15” (I presume centimeters or about 5 inches) and told him thank you. He smiled and quickly pointed at my crotch and said that I needed the room .

here’s the receipt

 

[NudePreston]

A few years back I was in Hong Kong and decided to get a Custom Suit made. Plus--I'm a 24/7/365 freeballer. I've not owned any underwear since the day after my high school graduation ceremony! Needless to say, that I was hanging free at the Tailors!

The old tailor really was a bit nervous measuring my inseam. But he did. When I came back a few hours later for the preliminary fitting, he avoided my thick cock hanging down my left leg...

I had a 6am departure from the hotel to get up to Guangzhou for a week-long set of meetings, and so they delivered the suit to my hotel concierge. I packed it and jumped in the taxi to the train without trying it on.

When I finally tried it on... the crotch hung half-way down my thigh! The old man was so afraid of my dick, that he just made it a baggy crotch! The Jacket was beautifully made. Truly! As were the three dress shirts i had made. C'est la vie!

 

[Steve6M]

Fitted for pants last week spilled coffee on my white shorts and polo shirt.He said he would get the stains out. He told me to take them off.This was early in morning and I was only customer.I took them off leaving me in Calvins and socks.Off he went with my clothes.I was flexing and my dick got hard in three way mirror.Two ladies entered and I went behind a dressing screen.The tailor came back out and saw me hiding behind screen.He waited on the ladies.Then he came behind screen and laughed as I asked for my clothes back.Later ,he laughed and started pulling my Calvin's down my tanned legs.I struggled but he had them off and then my socks.I was stranded in my tanline and the women were headed my way.

0/10

 

[bulgingpkg]

I've written about this previously, but I enjoy tailor stories myself, so i'll repeat it.

Decades ago, back in suit and tie days for me, I was a regular shopper at a mens store I could walk to from my office.

I got to know the salesmen there and they finally offered to call me when they got something in, in my unusual size (41L).

On one occasion I responded during my lunch hour and bought a blazer and trousers to go with it. They required some simple alterations and a hem.

I thought at the time the tailor, a handsome young Asian man, took extra time and care with me. When they were ready, I returned and they were waiting for me. I tried everything on and the tailor took a careful look, while his colleague, a very fit young white man with trim reddish beard, watched with interest. The tailor's fingers glided quickly over the fabric with an expert touch, tugging at certain seams, smoothing out minor wrinkles, making sure everything fit just right. (A lost art, I think, unless you're paying super high prices, which I wasn't.)

I had noticed the trousers fit snugly, emphasizing my prominent bulge in my left leg -- I wore loose silk boxers with my suits in those days.

He got to the bulge and instinctively tried to"smoothe" it and it wasn't going anywhere. He looked at it and then with the flat palm of him hand, PUSHED my bulge, and it persistently sprang back into position. I looked up at his salesman colleague and he smiled slightly and winked.

After this, my bulge was abandoned as hopeless.

My clothing was pronounced ready and I left the store, a happy customer with my cock hardening down my leg during the short walk back to my office.

I was a loyal customer there for years.

 

[Caseywiththeaveragebat]

Fitted for pants last week spilled coffee on my white shorts and polo shirt.He said he would get the stains out. He told me to take them off.This was early in morning and I was only customer.I took them off leaving me in Calvins and socks.Off he went with my clothes.I was flexing and my dick got hard in three way mirror.Two ladies entered and I went behind a dressing screen.The tailor came back out and saw me hiding behind screen.He waited on the ladies.Then he came behind screen and laughed as I asked for my clothes back.Later ,he laughed and started pulling my Calvin's down my tanned legs.I struggled but he had them off and then my socks.I was stranded in my tanline and the women were headed my way.

And....and? so he pulled down your Calvin's and did what exactly?

 

[hungstoner80]

I got fitted for a suit for a wedding. So I had to select the one the bride chose. When I weny yo get fitted the guy had me stand on the stool and measure the pant leg length. While staging there I asked if he could do anything about this (pointing me my crotch). I thought maybe they could find a different pair? They had to let out the crotch. I’m not sure how they do that. But afterwards I’m glad they did. They fit much better.

 

[Rippedspeedo]

And....and? so he pulled down your Calvin's and did what exactly?

I now get free tailoring.

 

[Steve6M]

I now get free tailoring.

Sure Jan.

 

[Rippedspeedo]

Who is Jan?

 

[deleted3155011]

 

[Rippedspeedo]

Now I see.Calling me a liar.

 

[ericbear]

This was far from awkward, but did involve a tailor and crotch. When I was relocating from the New York area to California 20-some years ago, I decided to take a memento of NY, so I went to Leather Man NYC and had a custom pair of leather chaps made to measure. I don't remember anything in particular about the measurement process, but when I returned to pick them up I was sent downstairs to the workshop area. There I met the tailor, this hot latin guy who checked the fit and made a few final adjustments (hem to length, etc.). After that, he puts them back on me, and we had a great time as he is showing me exactly how to position them for maximum effect. He says something like "Turn them to the side a bit to get more flower." I never heard it called "flower" before, but by the time he was done, my cock and balls, which normally hang down the left leg, were in a huge bulge protruding and hanging over the top of the chap left leg. He sent me on my way with a big grin.

PS: Since it was one of my last nights in NYC before moving, I wore the new chaps out of the store, and made a walking tour of my usual bars (sadly many gone today): Boots and Saddle, Hangar, Ty's, LURE, Eagle (original on 21st street), and Spike. My goal was to get the new chaps broken in, by collecting at least one cum load on them per bar. The bar patrons were quite happy to help me out, and by the end of the night I was more than completely successful...My new black chaps were milky white and dripping all over!