A boy poses in girl’s panties, stockings and nude for old Roy to enjoy.
I’d moved to the big city for work straight after university as a young man aged twenty two and I was renting a dingy room. I was very lonely having left all my mates and contacts behind, and I was sexually frustrated too. I got friendly with Roy (name changed), the man living in the flat below. I think he sensed I was lonely and took me under his wing. I guess he was in his fifties. He was dark haired, always neatly dressed, quiet and kept himself to himself. He was some kind of civil servant and he was unmarried.
He would invite me in for a cup of tea and a chat. I soon discovered he had a huge collection of girly porn magazines. We would browse through them discussing the women in the pictures.
I soon noticed how there were a few gay porn magazines full of pictures of naked men in his collection. I also noticed how his hand would often brush against my thigh or my backside and occasionally linger. I realised he was sexually interested in me. I’m not gay but unexpectedly I found I was getting excited by his touches.
Perhaps I was excited because I’d gotten into boy-on-boy sex when I’d started at university. I’d been nineteen and I’d hoped to get a girl straightaway. But I was unsuccessful and I got very sexually frustrated. I’d soon found I there were lots of boys my age there as sexually frustrated as me and as ready as me for anything our hungry young penises could get. Soon I was masturbating together, hand-jobbing, sucking off and frotting with other boys my age.
I was with Roy one evening browsing his magazines. I couldn’t resist looking through a gay porn magazine. I was looking at a picture of two naked boys looking not much older than nineteen, the age the magazine assured its readers was the minimum age of all its models. They were in missionary position one on top of the other rubbing their erect penises together just like I’d done at university. Roy put his hand on my thigh.
“Do you like seeing boys like that?” he said excitedly. “Go on, strip off for me and show me what you’ve got! You want to don’t you?”
At that moment the memories of the pleasures I’d had with boys flooded back to me. I stood and stripped to my underwear. I was in a light blue male thong, very brief, bulging in a huge ridge over my erection and barely covering my hard up penis. I stood there nudging my bulge toward Roy. He had a good long feel of my penis and balls through the thin cloth then pulled my thong down.
My six or so inches of hard muscle bounced out bending up from my hairy balls to its big round purple-grey circumcised head. I let my thong drop, kicked it aside and stood spread legged thrusting my hips forward. Roy’s hand was instantly all over my naked genitals and buttocks.
After months of just solo masturbation the feel of Roy’s hand excitedly caressing my bum cheeks, cuddling my balls, ruffling my cock fur, playing with my cock shaft and reaching under me to finger my taint and anus was exquisite. His adventurous hands told me he knew just what a boy wanted.
That first evening we just hand-jobbed each other. Roy got naked too and I wasn’t surprised by then to see he was wearing women’s panties, a red see through red lace pair with a decorative red bow at the front. His uncut cock was longer than mine with a big mushroom head and stuck out erect just above horizontal. His bush was neatly trimmed round his balls while mine was natural and unkempt.
His well-lubed hand stroked me methodically full length from my bush to sliding over my cock head. His fingers caught my frenulum, the centre of my penis pleasure, just the way I like. As he wanked me standing next to me his own hard up penis poked and brushed my naked thigh. He fondled my bum cheeks and stroked his fingertips along my bum crack and I played with his stiff cock and his balls. I came with a big spurt of semen arching from my cock to splash onto his rug.
I wanked Roy too. Some of the boys at university had been so excited they shot their load the moment my fingers, lips or tongue first touched their straining penises. Roy took ages of my rhythmic tugging and stroking of his foreskin. My freshly wanked cock smeared his thigh with residual semen and he fondled my bum the whole time.
Just like those boys back at university his penis suddenly hardened in my hand and he gripped my bum hard to pull me against him squeezing my cock and balls against his bare thigh. I love that moment when I’m wanking another boy. When his cock finally jerked in my hand he shot as much cum as those boys and his cum mingled with mine on his rug.
After that first evening I was down at Roy’s most evenings of the week. It wasn’t long before I discovered his secret fetish. We were browsing his porn magazines one evening when Roy put his hand on my thigh.
“Will you do something for me?” he asked.
From the box where he kept his magazines he produced some tiny white lace-edged cotton panties, just like teen schoolgirls wear, a pair of sheer seamed black nylon stockings and a pair of black high heels.
“Will you put these on for me and pose like these boys?”
He opened one of his gay magazines at a set of pictures of a young man looking my age doing an erotic striptease from a pink baby doll negligee, sheer tan stockings and pink satin panties. The set ended with a big centrefold of him laid back naked on a bed wide legged with his erection arching over his belly and with his hand round his cock, obviously wanking. The camera had caught his jet of semen spurting from his cock to land on his belly and chest. Roy flicked through the pages. The other pictures were all of men posing erotically in women’s underwear, in stockings and of course nude.
I couldn’t resist the kink. I stripped naked, slipped on the panties and pulled on the stockings. Roy must have got the high heels from a sex shop as they were big enough for a man’s feet. The feel of the soft panties taut over my straining hard erection was delicious. My cock pushed them out in a huge cone over the rounded apex of my cock head. The outline of my hard up cock showed through the thin cotton and my balls and pubes peeped out where my cock pushed the panties out at the sides. The back was just a thin thong gusset nestling deep between my bum cheeks. I ran my hands down my stocking-clad legs. They felt as sexy as a girl’s legs. As I did a slow twirl for him my erect penis slipped out. The panties were so brief half of it stuck out above the top hem.
Roy got naked too. He wasn’t wearing any underwear that time. He told me how he wanted me to pose for his voyeur pleasure.
I stood wide legged thrusting my hips forward. I squatted wide legged on my high heels. I got on all fours on his rug with my legs wide. I bent over one of his upright chairs thrusting my bum toward him. I stepped a high heeled foot up onto a chair getting my legs really wide, and lots more. After I’d posed in panties stockings and heels he asked me to take the panties off and pose nude but for the stockings and high heels.
He didn’t just enjoy me with his eyes. He felt my straining hard penis and caressed my balls through the thin cotton of the panties. He ran his fingers down the thin gusset between my bum cheeks from behind and between my legs to stroke my anus, taint and balls. He stroked my stocking clad legs and bare thigh above and slipped his hands down inside my stockings. He pulled my panties aside at the front so my erect cock sprang out for his exploring hand and he pulled the thin gusset aside at the back to finger my anus.
When I was nude, as well as his excited hands on my naked body, he ran his by then fully erect stiff penis along my bum crack, poked my anus with its head, ruffled my cock bush with its head and rubbed it against my own stiff penis.
He fingered his own penis steadily as he watched me and played with me and it steadily rose up hard. As he moved around me his penis swung erotically and poked and brushed against my body. When it swung near my face I leaned forward to kiss and lick it and take just its head into my mouth to massage with my lips and tongue. Roy liked that!
I think he enjoyed seeing me in panties and stockings and feeling me through them even more than my fully naked body. I found the kinkier the poses got the more excited I got and the more desperate I was to shoot a cum.
Then he asked me to let him watch me masturbate. I’d already realised he had a thing about watching men masturbate, both in porn pictures and me for real. I was certainly ready. My straining cock felt ready to snap.
So just in the stockings and high heels I knelt wide legged on his big round coffee table with my penis bending up in front of me. That’s one of my favourite masturbation positions. I love the heavy feel of my erection sticking out in front of me and the feel of my hanging balls. Spreading my legs pulls my muscles tight and if I’m with someone he or she can get their hand down between my spread legs to pleasure me. I wiggled my hips to swing my penis at Roy.
Roy obviously approved of the pose too. His hand was instantly down between my legs for a play. Being on his coffee table got my penis just the right height for him to rub his cock against mine, something else he liked.
He picked up those little white cotton panties and hung them on my penis. He got me to rub them over my balls and penis and run them back and forth under me between my spread legs. I wetted them with my pre-cum. Then he stepped back to watch me masturbate.
At university, wanking with boys and wild student parties with girls squealing for us boys to show them some wanking had taught me how to put on a good show. I fingered my balls and lightly stroked my penis to the peak of erection stiffness and pleasure sensitivity. I thrust my penis forward, wrapped my thumb and forefinger round my cock and began the full length stroking and tugging. I grunted, squirmed and thrust my hips with the sexual pleasure. As I hand-pleasured my cock Roy reached down under me from behind to lightly finger my balls. I edged, holding my nearly exploding penis on the exquisite brink of orgasm with the veins standing out on my shaft and its erection-swollen head almost glowing purple.
“Cum over my knickers!” Roy said excitedly when he sensed I was about to cum.
He held the little cotton panties right in front of my penis brushing my cock head. When I came I rammed my cock into them. I grunted loudly as I came, with my whole body juddering in my explosion of pleasure. I also farted noisily. The panties quivered as my semen splashed into the white cotton.
As I knelt there afterwards with my still half erect penis swinging in front of me Roy used the panties to wipe off the strand of semen dangling from my cock head and where it had dripped onto his coffee table. Then it was Roy’s turn.
“Bend over for me and show me your bum.”
The coffee table was big enough for me to get on all fours with my legs slightly parted and to stick my bottom up. Roy’s hand was all over my buttocks, my stocking tops and bare thigh above and of course between my legs from behind. I could feel his fingertip in my anus and his stiff penis poking and brushing against my bottom as he moved in close. He was grunting with excitement.
I felt his lubed penis sliding up and down along my bum crack. Then it slid between my thigh tops above my stockings and its head pushed upward with its erection stiffness against my anus and taint. I knew he wasn’t into anal and wasn’t going to enter me. I squeezed his shaft between my thigh tops. Roy liked that.
His cock withdrew from between my thighs then I felt its head poking between my buttocks. Roy took hold of my stocking clad thigh with one hand. A moment later I heard him grunt then felt his hand pat-patting my buttocks as it slid over his cock head as he masturbated into my crack. As always he took ages. As he wanked his spare hand slid over my thigh, my stocking tops and between my spread legs. He called me things like a slutty little twink and his whore bitch. I liked that.
Finally he grunted loudly, he gripped my thigh hard, his hand round his cock patting my bottom suddenly went faster and his cock head pushed really hard into my crack. Moments later with another grunt his warm semen spurted into my crack and over my buttocks and thigh tops. After he’d shot his load Roy staggered back from me panting. I stayed on all fours feeling his semen trickle down my bum crack and thigh tops to catch on my stocking tops. Roy used the semen-soaked panties to wipe his semen off me.
“You lovely boy!” Roy said when he’d finished cleaning my bottom, and he gave my buttocks an affectionate pat.
So that’s how it all started between me and Roy. It was many years ago now. We had a very kinky and very satisfying few months together. Then I found somewhere better to live nearer to work, I finally got a girl, and sadly that was the last I saw of Roy. But I still think of Roy every time I play with my seventeen year old daughter’s schoolgirl panties.
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