My sissy boy pick up 1
I was away on business a few years ago undertaking work and staying the week away in a hotel in a big city in England, away from the wife and family, free to be my other self. I had been there a few times before and I knew a few bars, those that, well catered for those looking for some fun. I wasn't sure what I wanted but I put on some casual clothes, but underneath there were some black fishnet open crotch tights and black lacey panties. So you can probably guess I was looking for some like minded person. When I got there those that were around were not really my type, too young, so I sat in a corner and had a beer, watching those coming and going.
I then saw a young guy come in, he looked young, around 20, and of Indian descent, he looked nervous, which I suppose considering what his peers would think of him here looking for a man, is understandable. When he went up to the bar, I got up walked over and asked him if he wanted a drink? He said yes could he have a strawberry daiquiri, he said I have heard others ask for that is it nice? I got us both a drink and invited him to my table. As we sat down I thought he is nothing like what I would usually go for, usually sticking to those similar to me an older, mid to late 50's, rather chubby crossdresser who likes a bit of cock.
When we sat down and chatted he slowly opened up and explained to me that his family didn't know about his preferences and had tried to hook him up with some cousin younger than him, after all he said I am 26 and should be settling down with a wife at least that is what they want, my parents and family. Wow I said I thought you were younger. I am a lot older than you, I am married and have k**s but I swing both ways. Yes everyone says I look younger and some say feminine. I don't feel right with woman but I have never been with a man before either. All I have had is some fumbles with other boys at school and an old uncle who touched me and rubbed his cock on me and cum on my back. You just need someone to be nice and gentle to you, you really should go out and find that girl and try that side before you decide on looking for a man. No he said I have looked at woman, you know nude and in videos but feel nothing. But if I look at a man and a cock I get hard, I also love to wear my sisters pink cotton panties and feel my tiny uncut cock rub in them. OMG you could have knocked me over, I love tiny uncut cocks, but a virgin, I would have to be gentle. He sat beside me and talked about how he felt and rested his hand on my crotch and said I feel you hard please take me somewhere private. He took my hand and laid it on his crotch feel I want you, please, I want to be with you and experience being with a man, you look nice and I think you would treat me nice. We agreed and I took him back to my hotel.
When we were in my room I slowly stripped him off of his outer clothes and laid him down on the bed face down all he was wearing were a pair of his sisters pink fullback panties. He lay there with his hands at his side and his legs together. watching me taking off my clothes, he gasped as he saw what I was wearing, my black open crotch fishnets with skimpy black lacey panties. I like your underwear he said. I straddled his legs and he said I can feel your fishnets against my bare flesh. I leaned forward so he could feel my small tiny cut cock through the lace rubbing his calves. Oh that is so nice he said. I slowly rubbed my cock back and forth as it slowly got hard meanwhile my hands were rubbing from the back of his knees to his panty covered ass cheeks just on the backs and the sides where when my hands reached his panties they slid under just a little teasing him. I hear him gasp Oh Yes Yes. Do you like that pantyboy I say, Oh Yes uncle please more.
Meanwhile, I took some oil from the bedside table on my hands and then back to his legs. They were now slowly sliding to the inside of his thighs just my fingers my palms are still on the back of his thighs but my fingers are now sliding up the inside of his thighs as I reach higher I hear my little pantyboy groan and start to wiggle. Slowly up and down mmmmmmm nice so so soft and smooth, I notice he has no hairs on his legs or back. My cock is still rubbing between his calves as my fingers slide slowly up and down but never quite reaching, my pantyboy is enjoying, he is groaning and asking for more. No keep stopping short, teasing, edging him slowly. Teasing tempting the groaning from pantyboy is louder I lift up and spread his legs kneeling between them my fingers now brush ever so lightly across his panty covered balls he flinches down and up down and up, then I cup his ball sack and roll his balls then off, No more please he cries, but I have taken my hands away. No I say wait I lay forward and my little hard cock fits nicely into the groove of my pantboys ass crack I start to rub it up and down the moans get louder, More More please he says. I grind my cock in the groove of his panty ass and my pantyboy groans and groans I have to imagine what my pantyboys cock looks like as I havn't see it yet, I sit up off him and kneel between his legs again I can see a damp patch on the panties down at the bed mmmmmmm must be precum I put my hands up the outside to the panties and start to edge them down and slip the panties off Yes there it is a tiny smooth cock with a big foreskin poking out under his smooth tight ball sack and I can see it is wet with precum. I so want to suck that cock but first I insert a finger in the skin and roll around the head teasing his glans he is squirming and groaning and twitching as I wiggle my finger inside his skin and rub his balls but I can see something else when I am here, his rosebud asshole.
I take my finger out his skin and my hand away from his balls he cries whimpers no no more more I give his ass cheek a gentle smack and I say quiet just lie still and do as you are told I take the palms of my hands on his ass cheeks and gently pull apart this opens his ass crack and puckers up his asshole I lean forward and gently blow on his rosebud it flinches I do it again he is groaning again it looks like it is winking at me then down with my head my tongue gently flicks at it the groans are getting stronger my tongue now circles around his hole across the grooves that allow his asshole to open and close his sphincter he is wiggling my palms push him down and hold him steady round and round my tongue goes sometimes flicking his asshole he seems to like it from his groans, I can taste him mmmmmmmm tasteeeeeeee. My tongue is getting his asshole wet but we need more it needs more than just the outside wet so the tip of my tongue slips into his hole not far just the tip and i wiggle it around in there he gasps and I can feel it slowly widening and I push my tongue in deeper his hips come up to meet my tongue and it slips deeper still I pull out my tongue and slap his ass again then push his ass into the bed and again say just lie still no moving and I return my tongue to his ass flicking rolling and probing deep then I lift of and drop a big bit of saliva right on the not so much a rosebud now. I return my tongue to his asshole and work my saliva into his ass then taking my left hand off his ass cheek I suck it's index finger and slip it gently in his ass the saliva allows it to slip in so I slowly work it in and out still with my tongue flicking and wetting I continue with my finger but now when it is in pantboys ass it circles round his asshole slowly pushing outwards stretching him I can see him widening I can almost get my tongue in beside my finger he is ready for next step fully out with the finger lick his ass, he groans more more. My finger goes in my mouth and I taste his juices mmmm nice making me horny and hard I rub my panty covered cock against his leg then I insert my middle finger in my mouth and wet both fingers fully then another drop of saliva on his ass as my tongue works it in then off and the two fingers slide in now deeper but they also can now stretch his anus and as I move my tongue away I can see it is wide enough that I can see a gap between my fingers he is stretching well for his first time his virginal ass is a natural let's get him really groaning.
I bring my fingers together in his ass and turn my palm down to his balls and with my fingers now curved towards his balls I slowly slide them up the inner wall of his ass looking for that spot, slowly gently then his whole body goes rigid Ah Haa we are there his prostate gently and slowly I have the tips of my two fingers around his bud and I am moving them in circles around he is now moaning and groaning I keep going and he is getting louder and faster shouting Yes oh Yes what are you doing its amazing I feel like I am going to cum I said just enjoy feel the sensations and let it flow I continue and his moans are getting stronger he is starting to pant I look down between his legs and cum is slowly seeping out of his foreskin I continue to watch his skin as my fingers slowly and gently rub his prostate more and more cum is oozing out Well that seems to have pleased you I said he could only whimper as I had been doing this the base of my fingers had still been moving around his anus so it was still wide open now for next part.
My fingers slipped slowly away from his prostate and back to his anus spreading them apart and stretching his anus wide he is ready oh he is ready my other hand slides down and moves my black Lacey panties off my cock it's not big but it's hard and the head is swollen fit to burst I take a big amount of saliva and cover my cockhead so it is wet and then stretch my fingers wide as they roll round as they slip out they are wet with his ass juices good that will help I put them in my mouth and suck them mmmmmmm tasteeeeeeee and before his asshole can start to close I position my cockhead at the gaping hole and slide the head in. It goes in easy so I push forward and all my little cock is in pantyboys little ass. As I say my cock is small so it only makes this opening and when all the way in just pushes on the next opening Oh I so wanted this and by his groans so did he I slowly pull out to just the tip and in all the way slow out quicker in slow out quicker in he is groaning and moaning. Do you like that pantyboy I ask, Ohh yes uncle.. I love this
My cock is now freely slipping in and out of my pantyboys asshole what we need is a bit more pressure so as I thrust in and out I move first one of my legs outside pantyboys leg and push it in and then the other this means the top of his thighs are closed tight and squeezing his balls and cock in his cum but also squeezing his ass cheeks together on my cock making it tighter oh gawd this is good I command him to cross his legs he does so and it is even tighter in out in out thrusting harder into his now tight ass he is groaning and shouts cum in my ass uncle and with that I thrust really deep and explode within his ass in out deeper deeper it just keeps cumming he is squeezing oh yes oh yes I feel you filling me give me more fill my dirty little ass and with one final deep thrust I am spent but there is one last thing to do to pantyboy if he wants well even if he doesnt
So I turn pantyboy over onto his back and raise his legs up and say now use your arms and hold those legs up at your chest yes uncle he says and i look down at his limp cock and balls covered in his cum and then to his asshole snapped shut holding in my cum I lower my head and take a bit of his cum from his balls mmmmm nice then I move to his asshole where there is a little bit of my cum and his juices mixed I lick this up flicking his hole as I do he flinches and squirms stay still I shout do as you are told giving his balls a gentle smack now when I say I want you to push my cum and your juices out of your ass slowly ok he says and I position my mouth under his asshole now I said and he pushes my cum and his juices start to ooze out my tongue catches them and takes them into my mouth, oh I love the taste of my cum mixed with ass juice when I have enough I say stop and lick the last away I move up to pantyboys head and he looks at me I just nod and he opens his mouth I dribble half of what is in my mouth into his and as I swallow the rest I say to him now taste and swallow he nods Do you like? He nods. More? i ask. He nodsagain. Let's see if there is more I return to his ass and flick it with my tongue to let him know I am there and say now he pushes and more comes out I again take it in then less then air and bubbles as he farts the last out I lick the last up and return to his head. Pantyboy has his mouth wide eagerly wanting some but I just swallow it all and say the best is the last that comes out and that is mine, but I will get you something else and I drop to his cock and balls and suck up his spunk still there and take that up to him and say taste your spunk now and I kiss him.
He says thanks thanks uncle for being my first, then he curls up on his side and I curl up behind him and we sleep spooned together.
Don't forget to save and share but please leave comments let me know if you want to hear more on this and my other adventures. Feel free to save any of my videos, galleries and posts to your own page favourites let others see perhaps they will like. Till next time keep cumming.
I then saw a young guy come in, he looked young, around 20, and of Indian descent, he looked nervous, which I suppose considering what his peers would think of him here looking for a man, is understandable. When he went up to the bar, I got up walked over and asked him if he wanted a drink? He said yes could he have a strawberry daiquiri, he said I have heard others ask for that is it nice? I got us both a drink and invited him to my table. As we sat down I thought he is nothing like what I would usually go for, usually sticking to those similar to me an older, mid to late 50's, rather chubby crossdresser who likes a bit of cock.
When we sat down and chatted he slowly opened up and explained to me that his family didn't know about his preferences and had tried to hook him up with some cousin younger than him, after all he said I am 26 and should be settling down with a wife at least that is what they want, my parents and family. Wow I said I thought you were younger. I am a lot older than you, I am married and have k**s but I swing both ways. Yes everyone says I look younger and some say feminine. I don't feel right with woman but I have never been with a man before either. All I have had is some fumbles with other boys at school and an old uncle who touched me and rubbed his cock on me and cum on my back. You just need someone to be nice and gentle to you, you really should go out and find that girl and try that side before you decide on looking for a man. No he said I have looked at woman, you know nude and in videos but feel nothing. But if I look at a man and a cock I get hard, I also love to wear my sisters pink cotton panties and feel my tiny uncut cock rub in them. OMG you could have knocked me over, I love tiny uncut cocks, but a virgin, I would have to be gentle. He sat beside me and talked about how he felt and rested his hand on my crotch and said I feel you hard please take me somewhere private. He took my hand and laid it on his crotch feel I want you, please, I want to be with you and experience being with a man, you look nice and I think you would treat me nice. We agreed and I took him back to my hotel.
When we were in my room I slowly stripped him off of his outer clothes and laid him down on the bed face down all he was wearing were a pair of his sisters pink fullback panties. He lay there with his hands at his side and his legs together. watching me taking off my clothes, he gasped as he saw what I was wearing, my black open crotch fishnets with skimpy black lacey panties. I like your underwear he said. I straddled his legs and he said I can feel your fishnets against my bare flesh. I leaned forward so he could feel my small tiny cut cock through the lace rubbing his calves. Oh that is so nice he said. I slowly rubbed my cock back and forth as it slowly got hard meanwhile my hands were rubbing from the back of his knees to his panty covered ass cheeks just on the backs and the sides where when my hands reached his panties they slid under just a little teasing him. I hear him gasp Oh Yes Yes. Do you like that pantyboy I say, Oh Yes uncle please more.
Meanwhile, I took some oil from the bedside table on my hands and then back to his legs. They were now slowly sliding to the inside of his thighs just my fingers my palms are still on the back of his thighs but my fingers are now sliding up the inside of his thighs as I reach higher I hear my little pantyboy groan and start to wiggle. Slowly up and down mmmmmmm nice so so soft and smooth, I notice he has no hairs on his legs or back. My cock is still rubbing between his calves as my fingers slide slowly up and down but never quite reaching, my pantyboy is enjoying, he is groaning and asking for more. No keep stopping short, teasing, edging him slowly. Teasing tempting the groaning from pantyboy is louder I lift up and spread his legs kneeling between them my fingers now brush ever so lightly across his panty covered balls he flinches down and up down and up, then I cup his ball sack and roll his balls then off, No more please he cries, but I have taken my hands away. No I say wait I lay forward and my little hard cock fits nicely into the groove of my pantboys ass crack I start to rub it up and down the moans get louder, More More please he says. I grind my cock in the groove of his panty ass and my pantyboy groans and groans I have to imagine what my pantyboys cock looks like as I havn't see it yet, I sit up off him and kneel between his legs again I can see a damp patch on the panties down at the bed mmmmmmm must be precum I put my hands up the outside to the panties and start to edge them down and slip the panties off Yes there it is a tiny smooth cock with a big foreskin poking out under his smooth tight ball sack and I can see it is wet with precum. I so want to suck that cock but first I insert a finger in the skin and roll around the head teasing his glans he is squirming and groaning and twitching as I wiggle my finger inside his skin and rub his balls but I can see something else when I am here, his rosebud asshole.
I take my finger out his skin and my hand away from his balls he cries whimpers no no more more I give his ass cheek a gentle smack and I say quiet just lie still and do as you are told I take the palms of my hands on his ass cheeks and gently pull apart this opens his ass crack and puckers up his asshole I lean forward and gently blow on his rosebud it flinches I do it again he is groaning again it looks like it is winking at me then down with my head my tongue gently flicks at it the groans are getting stronger my tongue now circles around his hole across the grooves that allow his asshole to open and close his sphincter he is wiggling my palms push him down and hold him steady round and round my tongue goes sometimes flicking his asshole he seems to like it from his groans, I can taste him mmmmmmmm tasteeeeeeee. My tongue is getting his asshole wet but we need more it needs more than just the outside wet so the tip of my tongue slips into his hole not far just the tip and i wiggle it around in there he gasps and I can feel it slowly widening and I push my tongue in deeper his hips come up to meet my tongue and it slips deeper still I pull out my tongue and slap his ass again then push his ass into the bed and again say just lie still no moving and I return my tongue to his ass flicking rolling and probing deep then I lift of and drop a big bit of saliva right on the not so much a rosebud now. I return my tongue to his asshole and work my saliva into his ass then taking my left hand off his ass cheek I suck it's index finger and slip it gently in his ass the saliva allows it to slip in so I slowly work it in and out still with my tongue flicking and wetting I continue with my finger but now when it is in pantboys ass it circles round his asshole slowly pushing outwards stretching him I can see him widening I can almost get my tongue in beside my finger he is ready for next step fully out with the finger lick his ass, he groans more more. My finger goes in my mouth and I taste his juices mmmm nice making me horny and hard I rub my panty covered cock against his leg then I insert my middle finger in my mouth and wet both fingers fully then another drop of saliva on his ass as my tongue works it in then off and the two fingers slide in now deeper but they also can now stretch his anus and as I move my tongue away I can see it is wide enough that I can see a gap between my fingers he is stretching well for his first time his virginal ass is a natural let's get him really groaning.
I bring my fingers together in his ass and turn my palm down to his balls and with my fingers now curved towards his balls I slowly slide them up the inner wall of his ass looking for that spot, slowly gently then his whole body goes rigid Ah Haa we are there his prostate gently and slowly I have the tips of my two fingers around his bud and I am moving them in circles around he is now moaning and groaning I keep going and he is getting louder and faster shouting Yes oh Yes what are you doing its amazing I feel like I am going to cum I said just enjoy feel the sensations and let it flow I continue and his moans are getting stronger he is starting to pant I look down between his legs and cum is slowly seeping out of his foreskin I continue to watch his skin as my fingers slowly and gently rub his prostate more and more cum is oozing out Well that seems to have pleased you I said he could only whimper as I had been doing this the base of my fingers had still been moving around his anus so it was still wide open now for next part.
My fingers slipped slowly away from his prostate and back to his anus spreading them apart and stretching his anus wide he is ready oh he is ready my other hand slides down and moves my black Lacey panties off my cock it's not big but it's hard and the head is swollen fit to burst I take a big amount of saliva and cover my cockhead so it is wet and then stretch my fingers wide as they roll round as they slip out they are wet with his ass juices good that will help I put them in my mouth and suck them mmmmmmm tasteeeeeeee and before his asshole can start to close I position my cockhead at the gaping hole and slide the head in. It goes in easy so I push forward and all my little cock is in pantyboys little ass. As I say my cock is small so it only makes this opening and when all the way in just pushes on the next opening Oh I so wanted this and by his groans so did he I slowly pull out to just the tip and in all the way slow out quicker in slow out quicker in he is groaning and moaning. Do you like that pantyboy I ask, Ohh yes uncle.. I love this
My cock is now freely slipping in and out of my pantyboys asshole what we need is a bit more pressure so as I thrust in and out I move first one of my legs outside pantyboys leg and push it in and then the other this means the top of his thighs are closed tight and squeezing his balls and cock in his cum but also squeezing his ass cheeks together on my cock making it tighter oh gawd this is good I command him to cross his legs he does so and it is even tighter in out in out thrusting harder into his now tight ass he is groaning and shouts cum in my ass uncle and with that I thrust really deep and explode within his ass in out deeper deeper it just keeps cumming he is squeezing oh yes oh yes I feel you filling me give me more fill my dirty little ass and with one final deep thrust I am spent but there is one last thing to do to pantyboy if he wants well even if he doesnt
So I turn pantyboy over onto his back and raise his legs up and say now use your arms and hold those legs up at your chest yes uncle he says and i look down at his limp cock and balls covered in his cum and then to his asshole snapped shut holding in my cum I lower my head and take a bit of his cum from his balls mmmmm nice then I move to his asshole where there is a little bit of my cum and his juices mixed I lick this up flicking his hole as I do he flinches and squirms stay still I shout do as you are told giving his balls a gentle smack now when I say I want you to push my cum and your juices out of your ass slowly ok he says and I position my mouth under his asshole now I said and he pushes my cum and his juices start to ooze out my tongue catches them and takes them into my mouth, oh I love the taste of my cum mixed with ass juice when I have enough I say stop and lick the last away I move up to pantyboys head and he looks at me I just nod and he opens his mouth I dribble half of what is in my mouth into his and as I swallow the rest I say to him now taste and swallow he nods Do you like? He nods. More? i ask. He nodsagain. Let's see if there is more I return to his ass and flick it with my tongue to let him know I am there and say now he pushes and more comes out I again take it in then less then air and bubbles as he farts the last out I lick the last up and return to his head. Pantyboy has his mouth wide eagerly wanting some but I just swallow it all and say the best is the last that comes out and that is mine, but I will get you something else and I drop to his cock and balls and suck up his spunk still there and take that up to him and say taste your spunk now and I kiss him.
He says thanks thanks uncle for being my first, then he curls up on his side and I curl up behind him and we sleep spooned together.
Don't forget to save and share but please leave comments let me know if you want to hear more on this and my other adventures. Feel free to save any of my videos, galleries and posts to your own page favourites let others see perhaps they will like. Till next time keep cumming.
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