When I was 17 I had a part time job in a man’s and woman’s clothes shop, it was an old established business run by an elderly bachelor and his spinster sister Mr and Miss Gibe. The customers who frequented the shop were unusually mature people, the styles and apparel reflected that. After some time my probation period elapsed and Mr Gibe offered me regular Saturday work and perhaps some evening work, guessing my nature Mr Gibe said it was my cute little bottom that persuaded him to offer me the job. My Gibe loved me working with him, it was not a busy shop but when the Gibe’s customers patronised the shop they certainly purchased a lot of clothing items.
I think Mr Gibe was a closeted Gay man who’d never had a sexual relationship with either sex, by his gentle nature and excellent manors indicated his sensitively leaned to feminism. Miss Gibe was a real spinster no man would ever get into her knickers or would want to I guess. One afternoon Mr Gibe asked me to open a box of his latest delivery of Y fonts underpants, while I was busy in sorting the y fronts Mr Gibe asked me what underwear I usually wore. As we’d became very good friends, I confided in him of my fetish for wearing skimpy briefs just lime girls panties. This admission didn’t seem to shock Mr Gibe he took delight in hearing me telling him about all my panty boyfriends, as our chat about my undies carried on I asked him if he’d like to see my knickers, “That would be nice Jay” Mr Gibe answered, with know one in the shop I quickly undid by trouser belt and dropped my trousers to my ankles then lifted up my shirt and tie, to display my lilac lace panties, Mr Gibe was gob smacked but I’d really impressed him. I quickly pulled my trousers up due to customer had just entered the shop.
When Miss Gibe was away on holiday or she was ill I was allowed to serve in the woman’s section, which I loved, especially having access to rummage through the panty slip, and knicker drawers. Most of the styles of the knickers Miss Gibe sold were the fuller types. Mr Gibe caught me a number of times trying a different panties but never once objected he didn’t seem to mind my actions. I use to visit the public toilets on my dinner break looking for cock, while cursing the public toilet I met a number of men who liked seeing a boy in girls undies. After our cock sessions in the toilet cubicle the men usually asked me to meet up with them again, during conservation with these men I told them where I worked. To my surprise a couple of the men at different times visited the shop and asked to speak to me, their excuse to visit the shop was to buy knickers for their wives. Mr Gibe was delighted with panty sales and news soon spread to other panty men, in one week I sold over 250 pairs of knickers and panties, mainly to men who want them for themselves. One or two men suggested to me why don’t Mr Gibe let you have a special panty night only for panty loving men so you model bras with matching panties for us. With Miss Gibe being away and Mr Gibe having little sexual excitement so when I broached the subject he became intrigued and readily agreed, Mr Gibe did stipulate it was to be only 4 men at a time.
On the night in question I wore a slip red slip with black lace edging and a matching midi style panty a bit bigger that I’d normally wore, plus red suspender belt and black stockings. I must say I looked like a real slut just want a man liked a woman to be before he has sex. At 21.00 the 4 men arrived, one after another, one worked on an open cast mine he was dressed in overalls, another was truck driver had his company dust coat, another was dressed in jeans and tie shirt he was a clerk, the last guy was very effeminate he was dressed immaculate in a suit shirt and tie. Once I was seen in bra and panties, cocks started to rise, as a young horny sissy panty boy, needless to say all four men fucked me in turn. I was fucked on the shop counter, in the changing room, on the floor, and in front of the mirror. I sucked one man’s cock while the another fucked me The first two were a bit rough they only wanted to quickly fill my pussy hole with cum, I sucked one while the other fucked me. I enjoyed it but the fuck was to quick and over in 10mins.When the two guys were dressing the effeminate guy took the opportunity to bend me over so he could kneel down and lick my cunt clean. The third guy was far better fuck he made sure my cunt was going to be used and abused, his cock fucked me for about 25 mins, again the effeminate guy licked my fuckhole clean, he pulled my panties up over my button and turned me around knelt down in front of pantied cock an sucked me until ejaculated my cum. Mr Gibe only watched but was delighted the 4 men bought 12 pairs of the most expensive satin knickers either for themselves or their wives. Mr Gibe allowed me to order briefer panties for myself from one of their catalogue at cost price. Mr Gibe was certainly impressed by my oral and anal activity.
Another time Mr Gibe asked me to lock the shop up after closing time one late Saturday afternoon, before closing time a man called, he was the son one of one of the farmers who patronised the Gibe’s shop. The man was about 32 years very old fashioned in dress. He asked for Mr Gibe but he was explained he was absence. I offered my assistance, he said his mother had sent him to buy some new underpants. One of my suggestions to Mr Gibe was for him to stock classic style briefs there were similar to Y fronts but looked better. I suggested to the man would he like to but some classic white briefs, he answered he didn’t know because his mother had always bought Y fronts, so I being a little persuasive and said why didn’t he try a pair on. To my complete surprise he said I’m a bit shy but if you strip down to your underwear I won’t feel do awkward. Fair comment I thought so I stripped down to my panties thank goodness they weren’t the frilly satin type on this occasion but a feminine style cotton type, the man was overcome you look better in those knickers than any girl I’ve been able to see though I’ve hardly seen any girls in the flesh or undies. The man stripped off naked boy was his cock big and wide with plenty of lovely loose foreskin. He put on the classic white briefs looked at him self in the mirror I liked the look of them. He pleaded with me to strip off down in to my undies, which I did we stood there only in panties and pants, he grabbed me ands kissed me, and said he’s not been a girl before, please can get into your knickers, I was not shocked but surprised how this situation had developed. Please can I fuck you the man uttered it will be the first fuck I’ve ever had, as long as you treat me like a girl I said. I always carry lubrication so I pulled my panties down and jellied my cunt with lubrication. Then I bent forward and held the cheeks of my ass apart, the man placed his cock at the entry of my boy cunt, because of his sexual frustration his cock had risen to an erect state. I was prepared mentally and physically for his prick, like most men or boys who’ve never fucked hole he rammed it inside me with no concern for my anus, I was in pain for a few minutes until my cunt got use to the size. Such was libido within 10 minutes he shot the biggest cum load inside my asshole is ran down my legs and made a pool on the carpet. Fuck, you’re the best fuck in world he said my anus was totally sore and felt raw, but the feeling of me being treated like a slut was great. The man said I was a better fuck than any of his sheep, I didn’t know if he was joking or not. That liaison continued for a few weeks every Tuesday and Friday, until the man mother’s finally let him marry a busty farm girl, he told me I was a far better fuck and prettier sight in panties than his girlfriend.
Shortly after my liaison with farmer’s son Miss Gibe died, Mr Gibe decided to sell the shop and retired to Bournemouth. But we still kept in touch at least twice a year by letter I use to tell him all about my new panties and my sex life. On my birthday he’d send me a pair of frilly panties and at Christmas he’d send me a pair really quality designer cotton knickers. He used to send from the same mail order company panty catalogue he knew that sold the undies I liked. When he died I was left £200 and the letters I’d written to him, plus a letter from his solicitor thanking me for my support