Straight Male / 45
Becoming A Sissy
After having issues when I was younger, I left for California, at the age of 18 I thought I knew everything, I only had 1parent that really didn’t care. I quickly found myself homeless, and not knowing much.
Hanging out with other homeless people, this older guy, we will call him Jeff, he took me under his wing, showing me where to find food, where to bathe, Jeff and I was hanging out one day and this old man drove by, in a red truck with a matching topper, Jeff told me never go to work for that guy.
I asked him why but he just said don’t do it. As the days, weeks go by, life got harder and harder, I was by myself and the guy in the red truck rolled up, this time he stopped, motion for me to come over so I did.
He asked me if I would be interested in working for him for a few days, maybe a few weeks, he said he has a place in the country, very private, and he needs some help, he told me I could drink beer, I could have hot showers and good food. He said he would even buy me some new clothes.
I was at the end of my rope. I just couldn’t stand the way my life was. I just couldn’t take it anymore, so I agreed, he told me to jump in the back, he said there’s some beer back there in the cooler and to help myself.
I jumped in, he started driving, I also started drinking that ice cold beer. We drove for what seemed like an hour or more, he stopped and told me to get out and open the gate, then close it after he drives through. As I jumped back in we drove on the dirt road that lead to his house.
His house had a circular drive with a fire burning in the middle, he parked and we got out. We walked to to the porch where 3 chairs and two door stools were, we sat there, as he sat down the cooler he had in the front of his truck. He told me to grab a beer from it and hand him one. We drank a little then he told me there’s an outdoor shower on the side and for me to go shower he said he would get me a towel.
I went to shower, and I found all the soap and shampoo, in the shower. God that warm shower felt good. When I got finished I pulled the plastic covering back to see a towel but my clothes were missing, I dryer off then returned to the porch where he was. I asked him about my clothes and he said I’ll get you some new. Those were ruined. Get me another beer, I didn’t question him I just did as told.
We sat there talking and drinking for hours, from time to time he would stand up pull his dick out and piss off the porch. I did too.
It started getting late, and we went inside, he sat in his chair, I sat on the couch, I was tired and drunk, so I layed down and passed out. I don’t know how long I was sleeping, but I was awaken to his dick in my mouth, when I woke, he said good your awake, he said sit up right so you can get it good.
I sat up on the couch as we went to work on me. He was holding my head pushing it futher on his cock as he let out moans of pleasure, he was telling me how good I was, and how he appreciated it. He told me real men like having there balls played with. I brought my hand up grabbed his balls and played with them. He pumped and pulled my head in. I just let him have his way with me.
Finley he pulled his cock out. Grabbed a fist full of my hair held me with in inches and he started jacking it. He let out a loud groan as he shot his lad all over my face, just covering me, it was dripping off my chin, it was everywhere.
After it was over, he told me to go clean up then come to bed. I followed him down the hall , I went into the rest room washed up, then went to his bedroom. I got into bed, and was told I have to sleep with my back to him. So I did. I wax awaken a few time during the night with him playing with my ass.
The next morning I was awaken up to him pushing on my back, he said ok I’m ready for my morning blowjob. I didn’t say a word, I just rolled over and started sucking him off. I sucked and sucked. Playing with his huge sagging balls. It seemed like 20 minutes, he Finley he’d my head down and shot his load in my mouth. He held me down and I had no choice, I swallowed his load, he released my head and told me to lick all of his cum. I did as told.
Me still not having any clothes, he told me to go make breakfast. I did. He came into the kitchen as i served him, he was nude, he say and ate. Then I was allowed to eat the leftovers. He got up and told me to follow, he sat in his chair, and he made me sat n a foot stool. To pull it up right between his legs. He started telling me all the rules of the house. He said I’m the cocksucker, and I would be treated as such, and helps the sir. I answered him with yes sir. He was humiliating me. Telling me he gets his cocked sucked off any time he wants it. My cock was super rock hard.
He noticed my cock, and he started laughing, and he said your just living this aren’t you cocksucker? I said yes sir. Then I asked if I could jack off. He laughed some more and said no. He told me, tonight he’s having a couple of friends over and for me to get the house in order, as I started cleaning, he told me to go into the spare bedroom, and pick myself some clothes. He went with me.
When I opened the door. I was shocked. There were all sorts of womens clothes everywhere in that room. There were French maid uniforms, plaid skirts, panties, stockings, high heels, bras, fake boobs, wigs. He told me to go shave my legs, then come back and start trying on these items, he said for me to model them so he could pick out the ones that looked the best.
I must admit, trying on these items was a huge turn on. My dick was dripping. I would model several different items, told to make different poses, as he took pictures of me. We rather, he decided I looked best in some pink panties, pink stockings with black pumps, and a matching black bra, with these huge fake tits.
I asked him again if I could jack off. He Finley agreed to let me. But I had to suck him off again but this time he wanted a video of me doing it dressed up as I was.
I swear you guys, with those nylon panties, tight stockings, and my huge fake tits getting in the way, I would have agreed to anything, he remembered lipstick, so he gave me some pink lipgloss, he started videotaping, as I got to my knees right in front of his cock. I licked it, then looked up begging for permission to suck it. I kissed it, calling him mr.sir, may I please suck your cock. I was haming it up for the video. I started begging for his cock. During this process he asked me if I wanted to be a total woman, then f corse I said yes. And begged for him to make me one.
I started sucking his cock like a mad person. He was filming from this side then that side. I’m not sure who was having the most fun. He Finley shot his load some in my mouth some on my face. I licked it up with my tongue, again for the camera.
When it was over he allowed me to jack off. He filmed me doing that too. I ate my own cum for the camera….
He informed me of the rules for tonight when his friends come over. I was to wear the French maids uniform, always call all men mr.sir, bend at the waist, not the knees, push my arms togather to squeeze my boobs, and never say no to anything..
His friends were these two overweight older guys. Slobs is what they were, I served them beer all night, I took a few slaps on my ass, they watched my video. And humiliate me all night. I loved it. The attention was such a turn on. Being called a cocksucker, bitch, and ever other name you can think of. I had to put ice on my cock several times during this time to keep it down, they liked it better that way. I would up sucking them off 3 and 4 times that night. There was so much video taken of me that night. They were treating me like the whore cocksucker I have become. When we Finley went to bed, I was asked if I wanted to be a total woman? I didn’t know what this ment, but I knew to answer yes sir.
He made me get some lube, grease up his cock until it was hard then he fucked me like a girl. He wasn’t rough, he took his time slipping it in. He worked his cock all the way up my man pussy, when it was all in. He just held it there for a while. He started pumping very slowly, I must admit, it really didn’t hurt. In fact when he was all in. He would hit this one place that felt GREAT. I guess he fucked me for about 45 minutes to an hour, he finished it off by making me get on all fours. I lubbed up his cock again then he really cut loose. He was fucking me like there was no tomorrow, he stopped and ordered me to turn around hurry hurry, I turned just in time to get his blast covering my face….
I learned what was expected of me, and I conform very quickly, I became his sissy slave, and I loved the humiliation, and the attention. I was introduced to 5 of his friends, he started loaning me out to a fire of them. Once I was loaned out for a week, and when I returned. He had another homeless young man he was training. We all three got along very well. He made several videos of me and the new slave making love, these he sold. For him it was heaven, for his friends it was a type of superior, to me it was heaven. I loved my new life and wanted more. I just loved watching men watch my videos and lusting to me.
Hanging out with other homeless people, this older guy, we will call him Jeff, he took me under his wing, showing me where to find food, where to bathe, Jeff and I was hanging out one day and this old man drove by, in a red truck with a matching topper, Jeff told me never go to work for that guy.
I asked him why but he just said don’t do it. As the days, weeks go by, life got harder and harder, I was by myself and the guy in the red truck rolled up, this time he stopped, motion for me to come over so I did.
He asked me if I would be interested in working for him for a few days, maybe a few weeks, he said he has a place in the country, very private, and he needs some help, he told me I could drink beer, I could have hot showers and good food. He said he would even buy me some new clothes.
I was at the end of my rope. I just couldn’t stand the way my life was. I just couldn’t take it anymore, so I agreed, he told me to jump in the back, he said there’s some beer back there in the cooler and to help myself.
I jumped in, he started driving, I also started drinking that ice cold beer. We drove for what seemed like an hour or more, he stopped and told me to get out and open the gate, then close it after he drives through. As I jumped back in we drove on the dirt road that lead to his house.
His house had a circular drive with a fire burning in the middle, he parked and we got out. We walked to to the porch where 3 chairs and two door stools were, we sat there, as he sat down the cooler he had in the front of his truck. He told me to grab a beer from it and hand him one. We drank a little then he told me there’s an outdoor shower on the side and for me to go shower he said he would get me a towel.
I went to shower, and I found all the soap and shampoo, in the shower. God that warm shower felt good. When I got finished I pulled the plastic covering back to see a towel but my clothes were missing, I dryer off then returned to the porch where he was. I asked him about my clothes and he said I’ll get you some new. Those were ruined. Get me another beer, I didn’t question him I just did as told.
We sat there talking and drinking for hours, from time to time he would stand up pull his dick out and piss off the porch. I did too.
It started getting late, and we went inside, he sat in his chair, I sat on the couch, I was tired and drunk, so I layed down and passed out. I don’t know how long I was sleeping, but I was awaken to his dick in my mouth, when I woke, he said good your awake, he said sit up right so you can get it good.
I sat up on the couch as we went to work on me. He was holding my head pushing it futher on his cock as he let out moans of pleasure, he was telling me how good I was, and how he appreciated it. He told me real men like having there balls played with. I brought my hand up grabbed his balls and played with them. He pumped and pulled my head in. I just let him have his way with me.
Finley he pulled his cock out. Grabbed a fist full of my hair held me with in inches and he started jacking it. He let out a loud groan as he shot his lad all over my face, just covering me, it was dripping off my chin, it was everywhere.
After it was over, he told me to go clean up then come to bed. I followed him down the hall , I went into the rest room washed up, then went to his bedroom. I got into bed, and was told I have to sleep with my back to him. So I did. I wax awaken a few time during the night with him playing with my ass.
The next morning I was awaken up to him pushing on my back, he said ok I’m ready for my morning blowjob. I didn’t say a word, I just rolled over and started sucking him off. I sucked and sucked. Playing with his huge sagging balls. It seemed like 20 minutes, he Finley he’d my head down and shot his load in my mouth. He held me down and I had no choice, I swallowed his load, he released my head and told me to lick all of his cum. I did as told.
Me still not having any clothes, he told me to go make breakfast. I did. He came into the kitchen as i served him, he was nude, he say and ate. Then I was allowed to eat the leftovers. He got up and told me to follow, he sat in his chair, and he made me sat n a foot stool. To pull it up right between his legs. He started telling me all the rules of the house. He said I’m the cocksucker, and I would be treated as such, and helps the sir. I answered him with yes sir. He was humiliating me. Telling me he gets his cocked sucked off any time he wants it. My cock was super rock hard.
He noticed my cock, and he started laughing, and he said your just living this aren’t you cocksucker? I said yes sir. Then I asked if I could jack off. He laughed some more and said no. He told me, tonight he’s having a couple of friends over and for me to get the house in order, as I started cleaning, he told me to go into the spare bedroom, and pick myself some clothes. He went with me.
When I opened the door. I was shocked. There were all sorts of womens clothes everywhere in that room. There were French maid uniforms, plaid skirts, panties, stockings, high heels, bras, fake boobs, wigs. He told me to go shave my legs, then come back and start trying on these items, he said for me to model them so he could pick out the ones that looked the best.
I must admit, trying on these items was a huge turn on. My dick was dripping. I would model several different items, told to make different poses, as he took pictures of me. We rather, he decided I looked best in some pink panties, pink stockings with black pumps, and a matching black bra, with these huge fake tits.
I asked him again if I could jack off. He Finley agreed to let me. But I had to suck him off again but this time he wanted a video of me doing it dressed up as I was.
I swear you guys, with those nylon panties, tight stockings, and my huge fake tits getting in the way, I would have agreed to anything, he remembered lipstick, so he gave me some pink lipgloss, he started videotaping, as I got to my knees right in front of his cock. I licked it, then looked up begging for permission to suck it. I kissed it, calling him mr.sir, may I please suck your cock. I was haming it up for the video. I started begging for his cock. During this process he asked me if I wanted to be a total woman, then f corse I said yes. And begged for him to make me one.
I started sucking his cock like a mad person. He was filming from this side then that side. I’m not sure who was having the most fun. He Finley shot his load some in my mouth some on my face. I licked it up with my tongue, again for the camera.
When it was over he allowed me to jack off. He filmed me doing that too. I ate my own cum for the camera….
He informed me of the rules for tonight when his friends come over. I was to wear the French maids uniform, always call all men mr.sir, bend at the waist, not the knees, push my arms togather to squeeze my boobs, and never say no to anything..
His friends were these two overweight older guys. Slobs is what they were, I served them beer all night, I took a few slaps on my ass, they watched my video. And humiliate me all night. I loved it. The attention was such a turn on. Being called a cocksucker, bitch, and ever other name you can think of. I had to put ice on my cock several times during this time to keep it down, they liked it better that way. I would up sucking them off 3 and 4 times that night. There was so much video taken of me that night. They were treating me like the whore cocksucker I have become. When we Finley went to bed, I was asked if I wanted to be a total woman? I didn’t know what this ment, but I knew to answer yes sir.
He made me get some lube, grease up his cock until it was hard then he fucked me like a girl. He wasn’t rough, he took his time slipping it in. He worked his cock all the way up my man pussy, when it was all in. He just held it there for a while. He started pumping very slowly, I must admit, it really didn’t hurt. In fact when he was all in. He would hit this one place that felt GREAT. I guess he fucked me for about 45 minutes to an hour, he finished it off by making me get on all fours. I lubbed up his cock again then he really cut loose. He was fucking me like there was no tomorrow, he stopped and ordered me to turn around hurry hurry, I turned just in time to get his blast covering my face….
I learned what was expected of me, and I conform very quickly, I became his sissy slave, and I loved the humiliation, and the attention. I was introduced to 5 of his friends, he started loaning me out to a fire of them. Once I was loaned out for a week, and when I returned. He had another homeless young man he was training. We all three got along very well. He made several videos of me and the new slave making love, these he sold. For him it was heaven, for his friends it was a type of superior, to me it was heaven. I loved my new life and wanted more. I just loved watching men watch my videos and lusting to me.
- That's Juicy! 15
- Remove It! 5
