The Tailor

by Roger

5 Jun 2018 9055 readers Score 8.3 (92 votes) PDF Mobi ePub Txt


My brother is only 18 and he is getting married. I suspect more for convenience than for love although I know he is really fond of his girlfriend.  Up until now my brother and I have had a very close bond, very close, but that's another story. We never had a very good upbringing as our parents never had much time for us, they preferred work to family.

I am Gary his younger brother by two years. I am going to be his best man and needed to get my first suit. Our parents were well off so they were footing the bill for the wedding.

My brother and I went for our first visit to the tailor and of course everything was made to measure, even down to our shirts.

When we arrived at the shop it was very busy and we were taken care of by one of the older tailors. He apologised for the shop being so busy and assured us that we would be seen by the manager on our future visits. We did the usual selecting of material and the initial measuring up process and then went on our way.

Because of other wedding appointments my brother could not come with for my second appointment to the tailor and I had to go alone. My appointment was for after hours so that I could be dealt with by the manager as promised.

I was greeted by this young guy, possibly in his 20's who said he was the manager which surprised me as I was expecting someone a lot older. We started on the fitting with the trousers. I say trousers, just bits of material held together with pins. I was only wearing a jock strap and was feeling very embarrassed at being touched so intimately.

He started to adjust the trousers, taking pins out and replacing them in different positions. A couple of times the backs of his hands brushed against the front of my jock which sent a thrill right through me. He also kept smoothing down the material with both hands one inside and one outside of my leg. I was praying my cock stayed soft as he stroked the inside of my leg.

As I said at the start, we were also getting made to measure shirts which was going to be the next job in hand. He told me to remove my t/shirt which alarmed me as I assumed he would measure me over the top of my existing clothes.

I must say I don't have the type of body that I like to show off. I am a bit full bodied, but not fat , what they used to call puppy fat. My boobs are a bit full on and I am desperate to firm them up at the gym. The worst part of my body are my nipples. They are big an puffy, almost like a girls. During the summer I always wore a t/shirt and never exposed my chest.

I felt my cheeks going red as I removed my top and I felt his eyes wandering over my tits. What made it worse was that he then took out a couple on pins on the trousers and the material fell to the floor.

I was now standing there in just my jock strap red faced and totally embarrassed. He placed the tape measure around my chest and slipping two fingers underneath the tape checked for tightness gliding his fingers forwards and backwards along the tape. Of course his fingers slid across my nipples causing the nubs to firm up. The feeling was very nice but unfortunately had an effect on my cock which started to thicken.

He turned me round to face the large full length mirror, walked round to the back of me and placed the tape around my neck and noted the size. I could feel his body close to mine, A little too close I thought as I felt him gently push up against me. Our eyes kept making contact in the mirror and |I had to keep looking the other way.

He measured my shoulders and the length of my arms still standing behind me. He placed the tape round his neck and smoothed his hands across my shoulders. Hi gripped my shoulders gently and pulled my back onto his chest. I could swear I could feel a bulge in his trousers pressing against my bum.

He lowered his head and placed the softest kiss on my shoulder looking at  me in the mirror. He then slipped his hands over my shoulders and cupped my tits. As he squeezed gently I gave out a little moan and laid my head back onto him. It was a wonderful          feeling as he massaged my chest rolling my ample nipples between his thumb and forefinger.

My cock was now at full mast which he saw in the mirror. He removed his hands and placed gentle kisses on the back of my neck. While doing this he started to undress and  within seconds was naked. He pulled me back towards him and an electric shock went through me as our hot bodies touched.

He kissed my neck with more passion as his hands roamed all over me going lower with each second. He took hold on the waist band of my jock pulling it down, my hard, dripping cock springing forward. He turned me round to face him and for the first time a got a look at his smooth, well toned body

He started to kiss me with more force as he rubbed his hard cock against mine. His hands were on my bum cheeks pulling my cock onto his. He was looking into my eyes as our cock ground together.

I could feel my orgasm building as we moved faster and faster against each other. I am close I moaned. Cum for me baby he said as I spunked all over his stomach and up to his chest. His own  orgasm hit almost at the same time as he came in torrents all over me. 

We stood there holding on to each other sharing gentle kisses. I can't wait for my next fitting. Who knows what may happen.

by Roger

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