"What To Do About Charlie"
Charlie moved next door to me when he was just a little boy. His parents became friends with me and my wife and over the years I watched him grow up. He was a polite almost shy boy. He was not interested in things like little league baseball or boy scouts. Charlie was a loner.
I never mentioned that I noticed this to Charlieās father until he brought up the subject with me. Charlie was in high school by then. Bill , his father had told me he was really worried because Charlie had no interest and dating girls and was so closed off at making friends in school.
Bill and I had a few strong scotch whisky when he broke down with tears in his eyes. He told me that he had found girls bras and panties hidden in Charlieās bedroom. Bill told me at first he took this as a sign Charlie had been messing around with some young girl after school.
Then he found Charlieās diary. He showed me the diary and the panties he had found . He read out loud what was written in the diary . It explained the desire to be treated as a female and some graphic fantasies. Charlie wrote about wanting to be dressed as female and having men āmake him suck and fuck themā. Bill was in tears as he told this to me. I didn't know what to say to him. At the time I didn't know what to think or feel either. I didnāt have c***dren, so I'm in no position to give him any advice. Bill and I are friends and I felt bad for him.
Over the next several weeks, each time I saw Charlie, I could not help but think about the diary. The panties and I also began to notice his slim girlish figure. I tried to ignore it or any thoughts about the situation. Most people didnāt approve of transsexuals, gays, crossdressers, They considered it to be deviant behavior. I personally don't have a problem with it, LGBTs are okay with me.
A few days later, Bill told me the Charlie situation was causing problems in his marriage and he and his wife had decided to take a short vacation. Just the two of them. Their hopes were to sort out the problem and decided what to do about Charlie.
They planned to spend a week on a Caribbean cruise. He asked me to check in from time to time on Charlie while they were gone. I told him that I would look in on him to make sure everything was okay while they were gone.
I had been divorced for several years and was quite used to living alone and doing tasks like cooking for myself. I had done some dating lately but I had always been highly sexually charged . My ex-wife was a real freak in the bedroom. I had not found anyone to satisfy me like she could. My ex-wife was awesome at oral, anal sex and we both were into role playing. I have been horny since we split up.
The day after Bill and Janet left for their cruise, I needed some things from the store for my morning breakfast. I decided to see if Charlie needed anything from the store. I waited for several minutes and he finally answered the door wearing a long t-shirt. It was obvious that I had woke him up. Charlie asked to come with me if I could wait a minute for him to put on some shoes and shorts. I said that I would wait.
I stepped inside as he ran up the stairs, I could not help notice the thong panties he was wearing underneath the T-shirt. I remember shaking my head and thinking āwhat a silly, freaky boy he was.
In the car on the way to the store I tried not to pay any attention to the smooth shape of his legs and kept my eyes on the road. Charlie had his ear buds in and was listening to music so I didnāt feel any need for conversation.
Inside the grocery store, the way he walked was feminine, shaking his ass.The magazine he bought was something a teenage girl would buy. I ignored it and was glad when got back home. I remember shaking my head as Charlie wagged your his butt inside and closed the door to his house.
Later that morning I was outside doing yard work and could hear noises coming from the patio next door. I started to trim this tall hedges and needed a short ladder to do so. As I stepped up on the ladder and started to trim the hedges, I was shocked to see Charlie laying naked on a lawn chair at their swimming pool.
Quietly I stood on the ladder and watched as he caressed his body and started to stroke his dick while rubbing and pinching his nipples. What I had heard earlier was his moaning.
I don't remember how long I stood on the ladder watching but I do remember that my big fat 50 year old cock was rock hard when I climbed down. I felt ashamed of myself at first then I felt angry. Angry at myself and angry at Charlie. I thought about the anguish Bill was going through. My anger and curiosity still didn't stop me from stepping back up on the ladder and watching as Charlie finger fuck his ass.
The next few minutes are unclear to me as to what exactly happened but the next thing I remember was opening the gate and standing over him. Charlieās eyes were closed and he stroked his shaved cock with one hand and fingered himself with the other.
Suddenly his eyes popped open and I thought he would scream or jump up and run in the house. Then I realized why he didn't. Charlieās eyes were fixed on the huge bulge in my shorts.
It was lust in his eyes that made me forget my anger as he continued to stare at my hard cock. I had forgotten what I intended to say and didn't really care. I do remember saying this.
"So you want to be treated like a girl?... You pathetic little boy!...Do you have any idea the pain you're causing your mother and father?...You really piss me off!!!
The next thing Charlie said, I'll never forgetā¦āLooks like you're more turned on than you are pissed off at me...Wow it really big isn't it? " He pulled the ear buds out of his ears, looked at meā¦ āI saw you watching me when you were on the ladder. ā He eyes went to my crotchā¦āNow your dick is about to rip your shorts. āā¦Charlie said. He had a smirk on his face. Then he nonchalantly lay back on the lounge chair. His just started stroking his cock again.
I was so shocked and caught off guard by what he said. His reaction to me seeing him masturbate and the fact that he was still stroking his it blew me away. I noticed then, Charlie was right, my cock was so fucking hard!... I was lost for words...I didnāt know what to say or do...I just stood there watching himā¦Charlie had made me so horny!
Then Charlie looked up at me and saidā¦ā Mmmmā¦ Mr. Austin take yours out and stroke itā¦ come onā¦I know you wanna do it. ā I felt hypnotized . My shorts hit the pool deck and my cock sprang out throbbing.
I heard Charlie gaspā¦ āJesusā¦ I knew it was gonna be bigā¦ but Mr. A you got a monster cockā¦ Wow! ā
Deleted
I sat down in a chair next to him my cock standing up. I stared right at him, Charlie watching me. He just whisperedā¦ āItās so bigā¦ so long and thickā¦Itās beautiful. ā
I smiled and began to stroke it. I got harder and longer, as I watched Charlie admire my cock. I realized showing off for him aroused me to a new level. I had not felt like this in a long time. Now I was the one in control of the situation and I loved it!
āNow let me see you stroke yourself Charlie, more your chair closer to me. ā I reached out and pulled his chair to me until our knees touched. I watched him watching me as we started jerking off together. I think it was turning him on as much as it was me. Charlieās cock was pretty and looked bigger now because of his petite body and small hands on it. I noticed that Charlieās had polished his fingernails and toenails a light pink color. His shaved balls bounced and that smooth, soft body was so sexy.
ā You like this donāt you Charlieā¦us doing this togetherā¦ donāt you?ā Charlie just nodded his head.
āOhā¦ yeahā¦ Mr. Aā¦ I love watching youā¦ itās so bigā¦so beautiful. ā
āYou too Charlieā¦youāre so sexyā¦ so cute. āā¦Charlieās eyes shined with lust. I took each of his ankles and placed his legs on top of my thighs then scooted his chair as closely as possible. Then I pulled his body even closer so that his cock and mine weāre only inches away from each other.
I let go of my cock and it stood straight up. Then my hands rub each of his legs from foot two inner thighs feeling his soft skin. I could feel Charlieās tremble to my touch.
āYou like this donāt you Charlie?...The way I touch youā¦Donāt ya?...It feels so good to me too. ā I kept massaging his legs.
ā Iāve never done thisā¦ With anyone beforeā¦ It feels so good Mister A. ā
I could see the first drop of clear precum leak out of Charlieās dick. I pushed the head of my rock hard cock against Charlieās cock. Then I took both are cocks in my hand and stroked them together. It felt so good but I didnāt want to cause him to cum yet... I had more plans for me and Charlie. So I stopped. When I pulled away there was a string of precum connecting our cocks.
Charlie let out a breathy moan and saidā¦ āLet me touch it Mr. Aā¦ I want to so much. ā
āGo aheadā¦ Charlie do it! āā¦ he started to stroke meā¦ his small hand wouldnāt fit all the way around my cock and his pink fingernails looked so good as he stroked me from base to tip.
āThatās right stroke it squeeze itā¦ stroke it Charlieāā¦ā I love how your big cock feels Mister Aā¦.so longā¦ so hard. ā
I started to kiss and lick up and down the sole of his small sexy foot. Then I began to suck and lick his toes. āIām gonna teach you how to suck my cock like this Charlieā¦you are going to learn how to suck my cock so good. ā
He stopped stroking me and looked upā¦āOh please Mr. Aā¦ I want that so badā¦I love your big cock. ā
ā Then letās go inside the house Charlie letās go get on the bed and Iāll show you.ā
I caressed Charlieās back a cute little ass as walked inside. My cock was standing straight out as we entered his bedroom.
Charlieās bedroom reminded me of a girlās room in the way it was decorated. I pushed stuffed a****ls off the bed and lay down pulling Charlie on top of me. His skin felt so soft and my cock was so hard. I had never been with a man before so I decided it was best to role play with Charlie. That would make things a lot easier. I think thatās what he wanted anyway. It turns out I was right.
āDo you want to be my sweet sissy slut Charlie?āā¦I said.
He hugged me and saidā¦āYesā¦ I want you to teach meā¦Show me everything about sexā¦Show me how to make love to your big cock. ā
āIāll show you sweet baby. ā I hugged him back and kissed him on the top of the head and pushed him by the shoulders down between my legs. It turns out I didnāt have to show him very much at all because Charlie had been watching internet porn and had a good idea what to do already.
His hand gripped my cock and started stroking it and I watched his warm pink tongue lick up and down the shaft. He would lick up and down to the head of my cock and back down to my balls.
Deleted
God... it felt so good it been a long time for me.
āDoes that feel good Daddy? āā¦This was the first time he called me Daddy. It turned me on. I liked it.
āOhā¦ yes babyā¦ lick itā¦ suck Daddyās cockā¦ it feels so nice. ā
Charlie licked and sucked me passionatelyā¦ So much better than I could have wished for. Despite my girth...Charlie could take over half of my cock in his hot little mouth. I just laid back and watched him work on me. It felt so damn good. I couldnāt remember ever getting better head. I showed him how to bring me so close to orgasm then stop squeeze the base of my big cock and then start sucking again.
Charlie licked and sucked on my cock, moaning and talking dirty to me. I have never sucked a cock in my life but was overcome with desire for Charlie. I positioned him on top of me in a 69 and use my tongue to lick up and down Charlieās cock from his balls to the head of his cock back to his balls over and over. Then I started licking his ass and rimming and thrusting my tongue into his tight hole.
āOhā¦ Daddyā¦ oh itās so good daddy. ā
I was on fire with burning desire for him as we pleased each other. I took Charlieās cock into my mouth, and use my hands on his ass to coax him to fuck my mouth with his cock. It didnāt take long before Charlie moaned ,trembled and cried outā¦ āOhā¦Oh Daddyā¦ Iām gonna cumā¦ Ohā¦Iām cumming! ā
I wrapped my arms around his waist pulling him to me and taking his cock to the balls. I felt his body spasm and he cried out as hot cum filled my mouth. It tasted delicious to me. I licked and sucked on him until his moaning subsided.
I couldnāt hold back any longer so I repositioned Charlie and started stroking my cock placing the head of it in his mouth. Charlie licked and sucked on the head of my cock as I stroked it until I exploded a huge load of cum into his mouth. It felt so damn good I almost passed out.
Deleted
We both laid on the bed caressing each other afterwards. It felt natural and completely normal to do this with him. We didnāt talk for several minutes.
ā I love the way you made me feelā¦Mr. A. I want to play Daddy and be your Sissy slut a lotā¦ I hope you do too. ā
I hugged Charlie tight for a minute and saidā¦ā I Like It to Charlieā¦I have a planā¦āWould you like some sexy lingerie, a make up kit and a cute little wig? ā
Charlie turned around and smiledā¦ āOh yes!... You do wanna be my Daddy! ā
We just laid there quietly after that for a few minutes. Then Charlie whispered in my earā¦ āI want you to teach me how to fuckā¦ I want your big cock in me Daddyā¦ I want to ride it and to feel you fucking meā¦ fucking me so good Daddy.ā
Just the thought of it caused another erection and Charlie learning more about how to suck my cock. He was an A student.
Later that afternoon, I floated in the swimming pool sipping a cold beer, watching Charlie lay in the sun. We made plans to go to a local āadult storeā called āSeductionsā to get things for Charlie.
The sun, the pool and everything else felt great. I realized that I knewā¦āWhat To Do About Charlieā
Part 2 Cumming Soon
I never mentioned that I noticed this to Charlieās father until he brought up the subject with me. Charlie was in high school by then. Bill , his father had told me he was really worried because Charlie had no interest and dating girls and was so closed off at making friends in school.
Bill and I had a few strong scotch whisky when he broke down with tears in his eyes. He told me that he had found girls bras and panties hidden in Charlieās bedroom. Bill told me at first he took this as a sign Charlie had been messing around with some young girl after school.
Then he found Charlieās diary. He showed me the diary and the panties he had found . He read out loud what was written in the diary . It explained the desire to be treated as a female and some graphic fantasies. Charlie wrote about wanting to be dressed as female and having men āmake him suck and fuck themā. Bill was in tears as he told this to me. I didn't know what to say to him. At the time I didn't know what to think or feel either. I didnāt have c***dren, so I'm in no position to give him any advice. Bill and I are friends and I felt bad for him.
Over the next several weeks, each time I saw Charlie, I could not help but think about the diary. The panties and I also began to notice his slim girlish figure. I tried to ignore it or any thoughts about the situation. Most people didnāt approve of transsexuals, gays, crossdressers, They considered it to be deviant behavior. I personally don't have a problem with it, LGBTs are okay with me.
A few days later, Bill told me the Charlie situation was causing problems in his marriage and he and his wife had decided to take a short vacation. Just the two of them. Their hopes were to sort out the problem and decided what to do about Charlie.
They planned to spend a week on a Caribbean cruise. He asked me to check in from time to time on Charlie while they were gone. I told him that I would look in on him to make sure everything was okay while they were gone.
I had been divorced for several years and was quite used to living alone and doing tasks like cooking for myself. I had done some dating lately but I had always been highly sexually charged . My ex-wife was a real freak in the bedroom. I had not found anyone to satisfy me like she could. My ex-wife was awesome at oral, anal sex and we both were into role playing. I have been horny since we split up.
The day after Bill and Janet left for their cruise, I needed some things from the store for my morning breakfast. I decided to see if Charlie needed anything from the store. I waited for several minutes and he finally answered the door wearing a long t-shirt. It was obvious that I had woke him up. Charlie asked to come with me if I could wait a minute for him to put on some shoes and shorts. I said that I would wait.
I stepped inside as he ran up the stairs, I could not help notice the thong panties he was wearing underneath the T-shirt. I remember shaking my head and thinking āwhat a silly, freaky boy he was.
In the car on the way to the store I tried not to pay any attention to the smooth shape of his legs and kept my eyes on the road. Charlie had his ear buds in and was listening to music so I didnāt feel any need for conversation.
Inside the grocery store, the way he walked was feminine, shaking his ass.The magazine he bought was something a teenage girl would buy. I ignored it and was glad when got back home. I remember shaking my head as Charlie wagged your his butt inside and closed the door to his house.
Later that morning I was outside doing yard work and could hear noises coming from the patio next door. I started to trim this tall hedges and needed a short ladder to do so. As I stepped up on the ladder and started to trim the hedges, I was shocked to see Charlie laying naked on a lawn chair at their swimming pool.
Quietly I stood on the ladder and watched as he caressed his body and started to stroke his dick while rubbing and pinching his nipples. What I had heard earlier was his moaning.
I don't remember how long I stood on the ladder watching but I do remember that my big fat 50 year old cock was rock hard when I climbed down. I felt ashamed of myself at first then I felt angry. Angry at myself and angry at Charlie. I thought about the anguish Bill was going through. My anger and curiosity still didn't stop me from stepping back up on the ladder and watching as Charlie finger fuck his ass.
The next few minutes are unclear to me as to what exactly happened but the next thing I remember was opening the gate and standing over him. Charlieās eyes were closed and he stroked his shaved cock with one hand and fingered himself with the other.
Suddenly his eyes popped open and I thought he would scream or jump up and run in the house. Then I realized why he didn't. Charlieās eyes were fixed on the huge bulge in my shorts.
It was lust in his eyes that made me forget my anger as he continued to stare at my hard cock. I had forgotten what I intended to say and didn't really care. I do remember saying this.
"So you want to be treated like a girl?... You pathetic little boy!...Do you have any idea the pain you're causing your mother and father?...You really piss me off!!!
The next thing Charlie said, I'll never forgetā¦āLooks like you're more turned on than you are pissed off at me...Wow it really big isn't it? " He pulled the ear buds out of his ears, looked at meā¦ āI saw you watching me when you were on the ladder. ā He eyes went to my crotchā¦āNow your dick is about to rip your shorts. āā¦Charlie said. He had a smirk on his face. Then he nonchalantly lay back on the lounge chair. His just started stroking his cock again.
I was so shocked and caught off guard by what he said. His reaction to me seeing him masturbate and the fact that he was still stroking his it blew me away. I noticed then, Charlie was right, my cock was so fucking hard!... I was lost for words...I didnāt know what to say or do...I just stood there watching himā¦Charlie had made me so horny!
Then Charlie looked up at me and saidā¦ā Mmmmā¦ Mr. Austin take yours out and stroke itā¦ come onā¦I know you wanna do it. ā I felt hypnotized . My shorts hit the pool deck and my cock sprang out throbbing.
I heard Charlie gaspā¦ āJesusā¦ I knew it was gonna be bigā¦ but Mr. A you got a monster cockā¦ Wow! ā
Deleted
I sat down in a chair next to him my cock standing up. I stared right at him, Charlie watching me. He just whisperedā¦ āItās so bigā¦ so long and thickā¦Itās beautiful. ā
I smiled and began to stroke it. I got harder and longer, as I watched Charlie admire my cock. I realized showing off for him aroused me to a new level. I had not felt like this in a long time. Now I was the one in control of the situation and I loved it!
āNow let me see you stroke yourself Charlie, more your chair closer to me. ā I reached out and pulled his chair to me until our knees touched. I watched him watching me as we started jerking off together. I think it was turning him on as much as it was me. Charlieās cock was pretty and looked bigger now because of his petite body and small hands on it. I noticed that Charlieās had polished his fingernails and toenails a light pink color. His shaved balls bounced and that smooth, soft body was so sexy.
ā You like this donāt you Charlieā¦us doing this togetherā¦ donāt you?ā Charlie just nodded his head.
āOhā¦ yeahā¦ Mr. Aā¦ I love watching youā¦ itās so bigā¦so beautiful. ā
āYou too Charlieā¦youāre so sexyā¦ so cute. āā¦Charlieās eyes shined with lust. I took each of his ankles and placed his legs on top of my thighs then scooted his chair as closely as possible. Then I pulled his body even closer so that his cock and mine weāre only inches away from each other.
I let go of my cock and it stood straight up. Then my hands rub each of his legs from foot two inner thighs feeling his soft skin. I could feel Charlieās tremble to my touch.
āYou like this donāt you Charlie?...The way I touch youā¦Donāt ya?...It feels so good to me too. ā I kept massaging his legs.
ā Iāve never done thisā¦ With anyone beforeā¦ It feels so good Mister A. ā
I could see the first drop of clear precum leak out of Charlieās dick. I pushed the head of my rock hard cock against Charlieās cock. Then I took both are cocks in my hand and stroked them together. It felt so good but I didnāt want to cause him to cum yet... I had more plans for me and Charlie. So I stopped. When I pulled away there was a string of precum connecting our cocks.
Charlie let out a breathy moan and saidā¦ āLet me touch it Mr. Aā¦ I want to so much. ā
āGo aheadā¦ Charlie do it! āā¦ he started to stroke meā¦ his small hand wouldnāt fit all the way around my cock and his pink fingernails looked so good as he stroked me from base to tip.
āThatās right stroke it squeeze itā¦ stroke it Charlieāā¦ā I love how your big cock feels Mister Aā¦.so longā¦ so hard. ā
I started to kiss and lick up and down the sole of his small sexy foot. Then I began to suck and lick his toes. āIām gonna teach you how to suck my cock like this Charlieā¦you are going to learn how to suck my cock so good. ā
He stopped stroking me and looked upā¦āOh please Mr. Aā¦ I want that so badā¦I love your big cock. ā
ā Then letās go inside the house Charlie letās go get on the bed and Iāll show you.ā
I caressed Charlieās back a cute little ass as walked inside. My cock was standing straight out as we entered his bedroom.
Charlieās bedroom reminded me of a girlās room in the way it was decorated. I pushed stuffed a****ls off the bed and lay down pulling Charlie on top of me. His skin felt so soft and my cock was so hard. I had never been with a man before so I decided it was best to role play with Charlie. That would make things a lot easier. I think thatās what he wanted anyway. It turns out I was right.
āDo you want to be my sweet sissy slut Charlie?āā¦I said.
He hugged me and saidā¦āYesā¦ I want you to teach meā¦Show me everything about sexā¦Show me how to make love to your big cock. ā
āIāll show you sweet baby. ā I hugged him back and kissed him on the top of the head and pushed him by the shoulders down between my legs. It turns out I didnāt have to show him very much at all because Charlie had been watching internet porn and had a good idea what to do already.
His hand gripped my cock and started stroking it and I watched his warm pink tongue lick up and down the shaft. He would lick up and down to the head of my cock and back down to my balls.
Deleted
God... it felt so good it been a long time for me.
āDoes that feel good Daddy? āā¦This was the first time he called me Daddy. It turned me on. I liked it.
āOhā¦ yes babyā¦ lick itā¦ suck Daddyās cockā¦ it feels so nice. ā
Charlie licked and sucked me passionatelyā¦ So much better than I could have wished for. Despite my girth...Charlie could take over half of my cock in his hot little mouth. I just laid back and watched him work on me. It felt so damn good. I couldnāt remember ever getting better head. I showed him how to bring me so close to orgasm then stop squeeze the base of my big cock and then start sucking again.
Charlie licked and sucked on my cock, moaning and talking dirty to me. I have never sucked a cock in my life but was overcome with desire for Charlie. I positioned him on top of me in a 69 and use my tongue to lick up and down Charlieās cock from his balls to the head of his cock back to his balls over and over. Then I started licking his ass and rimming and thrusting my tongue into his tight hole.
āOhā¦ Daddyā¦ oh itās so good daddy. ā
I was on fire with burning desire for him as we pleased each other. I took Charlieās cock into my mouth, and use my hands on his ass to coax him to fuck my mouth with his cock. It didnāt take long before Charlie moaned ,trembled and cried outā¦ āOhā¦Oh Daddyā¦ Iām gonna cumā¦ Ohā¦Iām cumming! ā
I wrapped my arms around his waist pulling him to me and taking his cock to the balls. I felt his body spasm and he cried out as hot cum filled my mouth. It tasted delicious to me. I licked and sucked on him until his moaning subsided.
I couldnāt hold back any longer so I repositioned Charlie and started stroking my cock placing the head of it in his mouth. Charlie licked and sucked on the head of my cock as I stroked it until I exploded a huge load of cum into his mouth. It felt so damn good I almost passed out.
Deleted
We both laid on the bed caressing each other afterwards. It felt natural and completely normal to do this with him. We didnāt talk for several minutes.
ā I love the way you made me feelā¦Mr. A. I want to play Daddy and be your Sissy slut a lotā¦ I hope you do too. ā
I hugged Charlie tight for a minute and saidā¦ā I Like It to Charlieā¦I have a planā¦āWould you like some sexy lingerie, a make up kit and a cute little wig? ā
Charlie turned around and smiledā¦ āOh yes!... You do wanna be my Daddy! ā
We just laid there quietly after that for a few minutes. Then Charlie whispered in my earā¦ āI want you to teach me how to fuckā¦ I want your big cock in me Daddyā¦ I want to ride it and to feel you fucking meā¦ fucking me so good Daddy.ā
Just the thought of it caused another erection and Charlie learning more about how to suck my cock. He was an A student.
Later that afternoon, I floated in the swimming pool sipping a cold beer, watching Charlie lay in the sun. We made plans to go to a local āadult storeā called āSeductionsā to get things for Charlie.
The sun, the pool and everything else felt great. I realized that I knewā¦āWhat To Do About Charlieā
Part 2 Cumming Soon
7 years ago