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By *ampire69 OP Man
over a year ago
Birmingham West Midlands |
I had just taken my very first anal fucking at the hands of an elderly tailor in the back of his shop where I had taken some trousers to be altered and got much more than I was expecting, I had allowed him to pop my anal cherry even though that had not been my intention at the start of the day.
As he climbed off me and I felt him pull his cock out of my ass I knew this was going to be a pleasure I was going to want and need I knew I was going to be hooked, he turned and looked at me and said open your mouth which I did and he placed his semi hard cock in my mouth and told me to suck and lick his shaft which I did with no hesitation, I tasted the last drippings of his spunk in my mouth. When he was satisfied, he withdrew his cock and I was told to get dressed which I did, he came back into the changing room cubicle and said your trousers will be ready next week at the same time, be here at exactly one pm and don’t be late, he handed me a small brown paper carrier bag which felt heavy and said now go and I will see you next week, I departed as ordered and left the shop.
Walking down the road I was trying to recall what had just happened had I dreamed the event, I made my way to the bus sop and while waiting for the bus I looked in the carrier bag and found a quantity of hard-core gay magazines and some female underwear with a note saying make sure you’re wearing this next Wednesday. The wait for next Wednesday seemed to take for ever, I wore the items given to me and arrived at the shop at 12-55pm to the second, I entered the shop and I could see that he was talking to another male about 50-60 years of age, I pretended to be looking at some of the clothes on the rails even though there was no way I could have afforded them maybe a pair of socks and that was about all. I saw him depart from his customer and he came over to me and bid me good day and guided me in to the back changing rooms where I was told to get undressed, he asked are you dressed the way I asked I responded yes sir, what size shoes do you take he asked I told him and he returned with a pair of red high heel ladies shoes put these on I will be back, after about 15 minutes he returned, this time he too was wearing a selection of female garments, stockings suspender belt some French knickers and a camisole top, I was a little taken as to how well he walked wearing his high heel shoes.
He told me to turn around and bend over and I heard him walk towards me he began to stroke and caress my ass, I felt him rubbing my cock he told me to open my legs wide and I felt his finger probe my ass hole, a mild discomfort and I could feel his finger deep inside me. He worked my ass hole for a few minutes and I was aware of his cock being pushed against my anus stretching me while he began to insert himself in to me, a few seconds later I could feel the thrusting begin as his shaft rammed my hole long deep hard thrusts almost knocking me off my feet, suddenly I swathe lights switched off in the back room only one dim light in the corner illuminated the room, just enough light to show four other men semi naked all dressed in female lingerie coming towards me and taking their positions around me, the one that stood in front of me offered me his cock and I was ordered to take it , show it some respect and love and to suck it.
These four men took it in turns to put their cocks in my mouth and in turn I performed oral sex on their erections, I have to say I was enjoying the experience even though I knew I was out of my depth. I felt each one taking it in turns to fuck me, I craved the feeling of their cocks exploding there loads inside me, love the feeling of their knobs shooting their spunk, I was hooked on this pleasure. I used to go to the tailors every week for months and experience this Wednesday pleasure until one week when I arrived, there was a for sale sign outside and clearly the shop was closed I later found out the owner and I never did know his name had died and that was the end of my training, they were very informative sessions sadly missed.
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