Uncle Ray
I had met Ray whilst indulging in my favorite activity ......wanking inside public toilets with my stockings and suspenders on .....Ray had caught me 'dressed' and rubbing my cock as he had peered over the top of the cubicle...... within a few minutes I ended up on my knees sucking him off inside my cubicle....He had waited outside the toilets and when I came out he basically asked if I would like to go home with him and continue with our sex fun as he said he had a large collection of undies and outfits he wanted to see me in..As a young boy just starting out in this new world of 'Dressing' and sucking cock in toilets the idea of being able to wear sexy undies and have a mature male watch me turned me on big time.
Once at Ray's house he asked if I minded him taking a few pictures of me when I was 'Dressed' he said it was for his own personal use and no-one else would see them......being a very naive boy of 14 years I said ok and asked if he would let me see what he had for me to wear......taking me upstairs Ray took me to a bedroom and opened a wardrobe which was full of flouncy big dresses and skirts with loads of frills underskirts and petticoats hanging up in there.....he then opened some drawers and took a handful of underwear out placing them on the bed he smiled and asked me if I would like to try some on. Oh yes would I .....the feel of the silky soft undies made my cock twitch and I was so excited at this new turn of events .....I stripped off without any embarrassment and picked a pair of purple panties up they were so soft and feminine but Ray said ''Hold on a minute you need a suspender belt first'' bending down he opened another drawer which was full of suspender belts of all colors and designs some with 4 suspenders and some with six ......Ray produced a purple one to match the panties and asked me to turn around so he could fasten it around my waist ....he then produced a pair of black fully fashioned seamed nylons and told me to sit on the bed so he could slide them up my legs. He was sweating a little as he slowly placed my foot in the hose ....pulling it along my leg and up my thigh his knuckles touched my balls making me moan softly a my cock twitched and became erect .....the feeling of the nylon on my legs always produced this reaction and Ray noticed how hard I had become...''My my we seem to be excited don't we boy.....do you like wearing ladies nylon's'' he asked as he clipped the suspender tabs to the stocking and adjusted the seam down the back of my leg .....he stroked and caressed my leg moving his hand up and down the nylons asking me all the time '' Are you enjoying this boy.....do you like being a naughty stocking wearing boy'' he kept teasing me as he now slid the other stocking on my leg and fastened the suspenders to them. Ray had me face the wall as he adjusted the seams again making sure they were arrow straight and pulled taut by the suspenders .....he had me turn and face him so my throbbing cock was now inches from his face.....''Oh you poor boy'' he moaned ''How you must ache for some relief'' he added ...I thought he was going to suck me.....but no he got off the bed and went to the wardrobe again searching and then returning with a pair of high heel shoes......they were black and very shinny ..... he bent down and placed first one foot then the other into the shoes making me wobble a little as this was something new for me .....I gained my balance and had such a thrill surge through my body as I looked down at my slim stocking legs in high heels......Ray passed me the panties and I put them on sliding them up my thighs and over my cock trapping it to my body as I pulled the panties tight .......Ray kept saying nice things about how good I looked and what a natural I was at wearing ladies undies and nylons.......I felt hornier than ever and wanted to get down to some sex but Ray wanted to make this session last awhile as he was so excited at finding a boy willing to model for him.
The camera came out and I posed and preened for Ray teetering on the heels prancing around the bedroom ......I felt wonderful and loved the whole experience of letting a mature male see me in undies......Ray then sat on the bed and rubbed his crutch as he looked at me ......he asked ''How do you feel about making a man horny'' ........I just swayed and teetered across the bedroom towards him reaching out I cupped his balls through his trouser's and squeezed him lightly........''Why don't you get this out so I can show you'' I teased.......Ray moaned and unzipped his trousers sliding them down his thighs I could see his erection tenting inside his boxer shorts...they soon followed his trouser's and he sat there all exposed his cock standing erect and throbbing with anticipation.
He beckoned me over and I knew what he wanted so I slid down to my knees and dipped my head between his thighs opening my mouth I took his cock between my lips and sucked......flicking my tongue along his shaft I wanked him as I sucked pulling his uncut foreskin back I tasted his salty bell end and marvelled at the fact I was so relaxed in his company.I love to suck cock and had found that I was good at it .......many previous times at the toilets I had sucked 4 or 5 men off as word got around a 14 year old schoolboy in stockings was in there.......but here with Ray in his bedroom it was different .....more relaxed and unhurried not having to worry about being discovered ......I licked sucked and wanked his cock as he kept saying things like ''Oh good boy'' or ''Yeesss suck me .....suck me deeper'' I didn't need his encouragement as I was loving every minute of it and wanted to taste his 'cum'
Ray was in heaven being sucked and wanked by a schoolboy in stockings and heels ........a slim sissy schoolboy who actually liked doing it as well......he placed his hands on my head and applied pressure making me take all of cock length into my eager mouth he pushed my head down and held me for a few seconds then let me slid my mouth back up his shaft.......''Oh God your'e going to make me shoot my load'' he moaned ........''OOH yeeessss I'm cumming'' he almost cried out as I felt his cock swell and then erupt in my mouth as he shot his load of spunk into the back of my throat ......I swallowed quickly but such was his cum blast I couldn't help but gag and cough as he emptied his balls into my mouth.......I tried to remain calm and kept my mouth closed around his cock as he subsided and finally I got my breathing back under control ........my cock was fit to burst as it throbbed inside my panties leaking pre-cum........I let Ray withdraw from my mouth and looked up at him licking my spunk sodden lips as I did ......he smiled and reached out to pull me up to him and I thought he was going to wank me off........but no he suddenly pulled me across his knees and yanked my panties very tightly between my bum cheeks trapping my aching cock even more firmly he then pushed my head down and started to spank me.......slap slap slap slap his hand kept up a steady rhythm making me squeal and wriggle on his knees......my bottom became hot and started to burn as slap slap slap he kept spanking me.........''A good Sissy Boy needs discipline'' Ray quoted as he continued to spank me........''A good Sissy Boy should know his place'' he added ''A good Sissy Boy will not expect to be allowed to 'cum' but should wait for his reward'' slap slap slap he stopped spanking me. ''Now get up and show Uncle Ray your Sissy Cock'' he ordered ......I stood up on shaky legs and pulled my panties down to my knees exposing my hard on which even after the spanking had not subsided ........Ray got off the bed and went to the wardrobe and returned with a flouncy Black and White Maids uniform .......one that had obviously been altered at the skirt was shortened to a ridiculous length ........''Put this on Sissy'' he ordered handing me the uniform.......I quickly 'Dressed' and stood their feeling really silly as the flouncy skirt billowed out above my hips and my cock throbbed and bobbed under the hem all on view........Ray smiled and called me his 'Sissy Prissy Maid ' ''Now you may wank yourself if you need to'' he said in a matter of fact way.......my face must have shown my dissapointment at having to do it myself as being wanked by a mature male was much better.......I stood before Ray straight legged and took hold of my cock wanking it in one hand as I had been ordered to do ......the experience I had just gone through was a first for me and had turned me on big time .......but wanking myself now was a little bit of a let down ........but Ray obviously had been in this situation before and knew how to handle a Sissy Boy from experience as he sat down on the bed and opened his legs ''Come here'' he ordered and I wobbled up to him standing between his legs jacking my cock in front of him..........''Now your'e allowed to 'cum' Sissy ......but you have just one minute to do it'' he smirked as I pumped my hand along my shaft like a demon ......I felt his hands caressing my nylon legs from the back of my knees to the top of my stockings and then down again making me shudder as I wanked myself ''Tell Uncle Ray when you are going to 'cum' Sissy Boy'' he said and pushed a finger between my bum cheeks entering my arse hole........Oh God he was finger fucking my arse and I was going to spurt.........''Now Uncle '' I bleeted out ''Now ......I'm going to 'cum' '' and as the first spasm hit me and I let fly Ray plunged his mouth over my spouting cock taking all my spunk into his mouth he sucked and swallowed devouring my cock as his finger plunged inside my arse with practiced movements he milked me completely........I had to place my hands on his shoulders to steady myself as I was shaking and panting ........Ray withdrew his finger and let my cock slide from his mouth .......then he told me to pull my panties back up and straighten myself out ........''Tomorrow you will learn how to take a cock in your Sissy Boy Bottom'' he said adding ''Any problem with that Sissy Boy'' ........I was trembling and so excited at how things had turned out I couldn't wait for tomorrow and replied ''Oh Uncle Ray that would be so nice'' .................................and it was believe me he fucked me like a true Sissy Boy should be fucked and that was just the start of our relationship ....
Once at Ray's house he asked if I minded him taking a few pictures of me when I was 'Dressed' he said it was for his own personal use and no-one else would see them......being a very naive boy of 14 years I said ok and asked if he would let me see what he had for me to wear......taking me upstairs Ray took me to a bedroom and opened a wardrobe which was full of flouncy big dresses and skirts with loads of frills underskirts and petticoats hanging up in there.....he then opened some drawers and took a handful of underwear out placing them on the bed he smiled and asked me if I would like to try some on. Oh yes would I .....the feel of the silky soft undies made my cock twitch and I was so excited at this new turn of events .....I stripped off without any embarrassment and picked a pair of purple panties up they were so soft and feminine but Ray said ''Hold on a minute you need a suspender belt first'' bending down he opened another drawer which was full of suspender belts of all colors and designs some with 4 suspenders and some with six ......Ray produced a purple one to match the panties and asked me to turn around so he could fasten it around my waist ....he then produced a pair of black fully fashioned seamed nylons and told me to sit on the bed so he could slide them up my legs. He was sweating a little as he slowly placed my foot in the hose ....pulling it along my leg and up my thigh his knuckles touched my balls making me moan softly a my cock twitched and became erect .....the feeling of the nylon on my legs always produced this reaction and Ray noticed how hard I had become...''My my we seem to be excited don't we boy.....do you like wearing ladies nylon's'' he asked as he clipped the suspender tabs to the stocking and adjusted the seam down the back of my leg .....he stroked and caressed my leg moving his hand up and down the nylons asking me all the time '' Are you enjoying this boy.....do you like being a naughty stocking wearing boy'' he kept teasing me as he now slid the other stocking on my leg and fastened the suspenders to them. Ray had me face the wall as he adjusted the seams again making sure they were arrow straight and pulled taut by the suspenders .....he had me turn and face him so my throbbing cock was now inches from his face.....''Oh you poor boy'' he moaned ''How you must ache for some relief'' he added ...I thought he was going to suck me.....but no he got off the bed and went to the wardrobe again searching and then returning with a pair of high heel shoes......they were black and very shinny ..... he bent down and placed first one foot then the other into the shoes making me wobble a little as this was something new for me .....I gained my balance and had such a thrill surge through my body as I looked down at my slim stocking legs in high heels......Ray passed me the panties and I put them on sliding them up my thighs and over my cock trapping it to my body as I pulled the panties tight .......Ray kept saying nice things about how good I looked and what a natural I was at wearing ladies undies and nylons.......I felt hornier than ever and wanted to get down to some sex but Ray wanted to make this session last awhile as he was so excited at finding a boy willing to model for him.
The camera came out and I posed and preened for Ray teetering on the heels prancing around the bedroom ......I felt wonderful and loved the whole experience of letting a mature male see me in undies......Ray then sat on the bed and rubbed his crutch as he looked at me ......he asked ''How do you feel about making a man horny'' ........I just swayed and teetered across the bedroom towards him reaching out I cupped his balls through his trouser's and squeezed him lightly........''Why don't you get this out so I can show you'' I teased.......Ray moaned and unzipped his trousers sliding them down his thighs I could see his erection tenting inside his boxer shorts...they soon followed his trouser's and he sat there all exposed his cock standing erect and throbbing with anticipation.
He beckoned me over and I knew what he wanted so I slid down to my knees and dipped my head between his thighs opening my mouth I took his cock between my lips and sucked......flicking my tongue along his shaft I wanked him as I sucked pulling his uncut foreskin back I tasted his salty bell end and marvelled at the fact I was so relaxed in his company.I love to suck cock and had found that I was good at it .......many previous times at the toilets I had sucked 4 or 5 men off as word got around a 14 year old schoolboy in stockings was in there.......but here with Ray in his bedroom it was different .....more relaxed and unhurried not having to worry about being discovered ......I licked sucked and wanked his cock as he kept saying things like ''Oh good boy'' or ''Yeesss suck me .....suck me deeper'' I didn't need his encouragement as I was loving every minute of it and wanted to taste his 'cum'
Ray was in heaven being sucked and wanked by a schoolboy in stockings and heels ........a slim sissy schoolboy who actually liked doing it as well......he placed his hands on my head and applied pressure making me take all of cock length into my eager mouth he pushed my head down and held me for a few seconds then let me slid my mouth back up his shaft.......''Oh God your'e going to make me shoot my load'' he moaned ........''OOH yeeessss I'm cumming'' he almost cried out as I felt his cock swell and then erupt in my mouth as he shot his load of spunk into the back of my throat ......I swallowed quickly but such was his cum blast I couldn't help but gag and cough as he emptied his balls into my mouth.......I tried to remain calm and kept my mouth closed around his cock as he subsided and finally I got my breathing back under control ........my cock was fit to burst as it throbbed inside my panties leaking pre-cum........I let Ray withdraw from my mouth and looked up at him licking my spunk sodden lips as I did ......he smiled and reached out to pull me up to him and I thought he was going to wank me off........but no he suddenly pulled me across his knees and yanked my panties very tightly between my bum cheeks trapping my aching cock even more firmly he then pushed my head down and started to spank me.......slap slap slap slap his hand kept up a steady rhythm making me squeal and wriggle on his knees......my bottom became hot and started to burn as slap slap slap he kept spanking me.........''A good Sissy Boy needs discipline'' Ray quoted as he continued to spank me........''A good Sissy Boy should know his place'' he added ''A good Sissy Boy will not expect to be allowed to 'cum' but should wait for his reward'' slap slap slap he stopped spanking me. ''Now get up and show Uncle Ray your Sissy Cock'' he ordered ......I stood up on shaky legs and pulled my panties down to my knees exposing my hard on which even after the spanking had not subsided ........Ray got off the bed and went to the wardrobe and returned with a flouncy Black and White Maids uniform .......one that had obviously been altered at the skirt was shortened to a ridiculous length ........''Put this on Sissy'' he ordered handing me the uniform.......I quickly 'Dressed' and stood their feeling really silly as the flouncy skirt billowed out above my hips and my cock throbbed and bobbed under the hem all on view........Ray smiled and called me his 'Sissy Prissy Maid ' ''Now you may wank yourself if you need to'' he said in a matter of fact way.......my face must have shown my dissapointment at having to do it myself as being wanked by a mature male was much better.......I stood before Ray straight legged and took hold of my cock wanking it in one hand as I had been ordered to do ......the experience I had just gone through was a first for me and had turned me on big time .......but wanking myself now was a little bit of a let down ........but Ray obviously had been in this situation before and knew how to handle a Sissy Boy from experience as he sat down on the bed and opened his legs ''Come here'' he ordered and I wobbled up to him standing between his legs jacking my cock in front of him..........''Now your'e allowed to 'cum' Sissy ......but you have just one minute to do it'' he smirked as I pumped my hand along my shaft like a demon ......I felt his hands caressing my nylon legs from the back of my knees to the top of my stockings and then down again making me shudder as I wanked myself ''Tell Uncle Ray when you are going to 'cum' Sissy Boy'' he said and pushed a finger between my bum cheeks entering my arse hole........Oh God he was finger fucking my arse and I was going to spurt.........''Now Uncle '' I bleeted out ''Now ......I'm going to 'cum' '' and as the first spasm hit me and I let fly Ray plunged his mouth over my spouting cock taking all my spunk into his mouth he sucked and swallowed devouring my cock as his finger plunged inside my arse with practiced movements he milked me completely........I had to place my hands on his shoulders to steady myself as I was shaking and panting ........Ray withdrew his finger and let my cock slide from his mouth .......then he told me to pull my panties back up and straighten myself out ........''Tomorrow you will learn how to take a cock in your Sissy Boy Bottom'' he said adding ''Any problem with that Sissy Boy'' ........I was trembling and so excited at how things had turned out I couldn't wait for tomorrow and replied ''Oh Uncle Ray that would be so nice'' .................................and it was believe me he fucked me like a true Sissy Boy should be fucked and that was just the start of our relationship ....
9 years ago
