Chapter 28: Brief CD Master fun
This was a potentially great CD introduction that I messed up badly.
I used Craigslist again in search of other local men that liked to dress up. I wanted to go further than panties, garters and stockings. Received many replies, but mostly it was from men wanting pictures of me in panties etc. I was getting discouraged until I received a reply from a man that said he wanted to be my CD master if I passed his list of requirements.
After many emails and phone calls he accepted me as his CD "student". I was instructed to search out and purchase a list of fem attire that he would like to see on me. It wasn't easy searching and finding the sizes and styles that might fit me...… I eventually just stuck to the outlet and second hand stores like Ross for example.
Some trial and error with the fit of the cloths....lots of return trips.... not to return items(I took the stuff that didn't fit or look right to Good Will) but to try and find the proper fit.
Eventually had a shiny black dress, black teddy for underneath the dress, elbow length black satin gloves, cheep necklace and clip on earrings, mid length black wig, lipstick(my wife's slut red:), and black 3" heels(needed size 12 at least, but could only find an 11...bit to small). I already had garters, stockings and panties:). He had instructed me to arrive locked in chastity with panties that displayed the cage.
Once I informed him that I had the fem gear he invited me to his house that was east of me by about 1 hour drive. I was nervous, excited, and apprehensive because I had dressed at home to check the fit etc. and thought I looked awful....so I was very worried that I would be a disappointment for him.
He lived in a very upscale gated community surrounding a golf course. He answered the door dressed casually in a dress shirt and slacks and greeted me warmly. He was trim and a couple inches shorter that me and was making a good effort in making me feel at home.
Once the small talk subsided, he showed me to a room where I could exchange from my manly attire into my fem gear. I took my time in an attempt to look fem and sexy( a total failure I thought). I really felt slutty and sexy though, but in all honest I looked silly.
Once I was dressed and had my tight 3" pumps on I returned to the main room. He told me that he liked what he saw, and that I might make a very good sissy for him. He had me stand while he circled around inspecting me. He lifted the hem of the skirt up to check on my locked cock and my crotch less panties....he gently felt me up all around my caged sissy cock and ass.
Next instruction was for me to bend over at the waist....this I did. He was holding up the skirt with one hand and then gave me a good spank on my ass with the other. Totally surprised by that(ouch:). He said that he was sure that I was a bad "girl"....a slut probably.
Whack....another stinging spank....whack, one check then the other..... all the time telling me what a cheep slut I was etc. etc. I didn't like it much at first, but got used to the stinging and loved the verbal humiliation. He maybe spanked me about 8 times each cheek, then lowered my skirt and gently rubbed my ass.
I had expected him to undress thinking he would have panties and stockings on at least, but he never undressed the whole time that I was in his house. I was soon instructed to walk around the room as much like a girl as possible. He had me lift my skirt exposing my sissy cock as I walked by his big picture windows that overlooked the golf course. I could see a few golfers out on the fairway, but he didn't seem concerned about them spotting me(would have really thrown their game off if they had).
He asked me how far I wanted to take my CD play. I told him of my fantasy of being an oral CD cum dump for a half dozen alpha men. He said that could be arranged once I had "developed" further. I was then told to stand by the high backed leather chair, bend over again, this time leaning on the chair for some support. I noted then that he had a towel covering up something on the side stand beside the chair.
He then would walk slowly around me, all the time touching and caressing my ass and caged cock, plus verbally humiliating me. I was getting aroused and made an attempt to feel his cock through his slacks. My hand was briskly pushed aside and I was told to keep my hands to myself.....got two goods whacks on my ass as well!
It wasn't long until his finger(the fingers) started to probe my ass. He lubed his fingers and started working them in and around. I have tried plugs and a small thin dildo back there, but never have found any sexual highs coming my way with toys in my ass. His manipulations though started to have a nice effect on me...……… soon fingers got replaced by a some kind of dildo or prostate massager(I never got a look at the toys). Along with copious amounts of lube he eventually had my sissy cock dribbling a bit of pre cum.
I was now pushing my ass back to accept his probing. Some pain, but the ass manipulation was getting me hot, and I thought that if he this kept this up I might just cum(I doubt it now, but the feeling was there for sure). When I started to push back in time with the dildo insertions, he would spank my ass in time as well.....call me a slut....tell me that I wasn't man enough to fuck my wife, and that she is fucking others while I am with him etc.
This talk just made it all the more intense and exciting for me. I really wanted to cum, but he had other plans:(.
He got me to the edge and told me that "that's enough for now"!
As far as I could tell he never once stroked his own cock, and never took one piece of clothing off. He showed me to a washroom where I could clean up my lubed ass, and said that I should get dressed.
I had expected and was hoping that I would be sucking his cock before I left....not so. I was somewhat disappointed but I did leave feeling very slutty and satisfied with my first real taste of CD company. He assured me that he would be in touch for another CD lesson:). He told me that he had a couple of friends that might like to "use me" once I had become more comfortable in my new lifestyle direction..... I wanted to ask many questions then, but I sensed that the visit was over.
We met up again about a month later at my house. It was difficult arranging safe visit dates because he was also married and in the closet. Our second meeting was very similar, but we got into the play faster this time. He was more verbal and aggressive now. I had also followed his instructions regarding the use of butt plugs to open up my tight sissy ass pussy in between visits.
I'm not sure that I was any more open back there. He brought his toys and lube with him, and seemed to really enjoy messing with my ass again. I was dolled up as before, but tried to do a better job with the makeup. Still had the tight 3" heels, and was relieved when I took them off to climb up and kneel on the bed.
Locked cock like before, but hiding it behind a pair of pink panties. He worked me up to a similar edge like before.....got to feel like I was going to shoot, but didn't:(. Also, like before no cock sucking action for me!
I did like to hear that he thought his friends would surely love to meet me soon. He didn't elaborate when I asked about his friends, and what they might have planned etc. Just left my mind to think of all kinds of cool nasty kinky scenarios....lol.
A good CD visit again, but like before he kept his cloths on and didn't let me touch his dick. He told me that he would plan another visit for next month if our schedules connected well...….BUT
I fucked it all up about two weeks later when I found another CD man via Craigslist. I think his name was Tim and he was local. Tim came to my house, put on his fem dress and panties. No wigs, shoes or makeup on either of us. I had garters, stockings and panties on, but no other true fem stuff.
We had fun...Got him up on the bed.....sucked him and rimmed his ass, went back to his cock(average cut) and sucked him dry. As we had arranged there was no reciprocation from him required or desired.
I had some fem stuff that didn't fit me well, and I gave what I had to Tim. He seemed very pleased, and we talked about getting together again.
MY BIG MISTAKE....was telling my CD master about Tim's visit...sent him pictures as well. I thought he would be pleased to hear of my CD adventure, but instead he was pissed because I didn't get his permission to have Tim over & have that fun! So I fucked up what might have turned into some great CD fun. The CD master dropped me like a rock!
Live and learn I guess. Plus be loyal to your master or mistress(or be sure to ask permission:)
FYI, I do have a couple of pictures saved from my meeting with Tim. Not the greatest pics, but I will forward them if anyone wants to check them out. Any pictures of me in full CD fem gear got deleted....no real loss because I did look like an ugly slag & although I loved how I felt when dressed, I hated how I looked!
Thanks for reading.
I used Craigslist again in search of other local men that liked to dress up. I wanted to go further than panties, garters and stockings. Received many replies, but mostly it was from men wanting pictures of me in panties etc. I was getting discouraged until I received a reply from a man that said he wanted to be my CD master if I passed his list of requirements.
After many emails and phone calls he accepted me as his CD "student". I was instructed to search out and purchase a list of fem attire that he would like to see on me. It wasn't easy searching and finding the sizes and styles that might fit me...… I eventually just stuck to the outlet and second hand stores like Ross for example.
Some trial and error with the fit of the cloths....lots of return trips.... not to return items(I took the stuff that didn't fit or look right to Good Will) but to try and find the proper fit.
Eventually had a shiny black dress, black teddy for underneath the dress, elbow length black satin gloves, cheep necklace and clip on earrings, mid length black wig, lipstick(my wife's slut red:), and black 3" heels(needed size 12 at least, but could only find an 11...bit to small). I already had garters, stockings and panties:). He had instructed me to arrive locked in chastity with panties that displayed the cage.
Once I informed him that I had the fem gear he invited me to his house that was east of me by about 1 hour drive. I was nervous, excited, and apprehensive because I had dressed at home to check the fit etc. and thought I looked awful....so I was very worried that I would be a disappointment for him.
He lived in a very upscale gated community surrounding a golf course. He answered the door dressed casually in a dress shirt and slacks and greeted me warmly. He was trim and a couple inches shorter that me and was making a good effort in making me feel at home.
Once the small talk subsided, he showed me to a room where I could exchange from my manly attire into my fem gear. I took my time in an attempt to look fem and sexy( a total failure I thought). I really felt slutty and sexy though, but in all honest I looked silly.
Once I was dressed and had my tight 3" pumps on I returned to the main room. He told me that he liked what he saw, and that I might make a very good sissy for him. He had me stand while he circled around inspecting me. He lifted the hem of the skirt up to check on my locked cock and my crotch less panties....he gently felt me up all around my caged sissy cock and ass.
Next instruction was for me to bend over at the waist....this I did. He was holding up the skirt with one hand and then gave me a good spank on my ass with the other. Totally surprised by that(ouch:). He said that he was sure that I was a bad "girl"....a slut probably.
Whack....another stinging spank....whack, one check then the other..... all the time telling me what a cheep slut I was etc. etc. I didn't like it much at first, but got used to the stinging and loved the verbal humiliation. He maybe spanked me about 8 times each cheek, then lowered my skirt and gently rubbed my ass.
I had expected him to undress thinking he would have panties and stockings on at least, but he never undressed the whole time that I was in his house. I was soon instructed to walk around the room as much like a girl as possible. He had me lift my skirt exposing my sissy cock as I walked by his big picture windows that overlooked the golf course. I could see a few golfers out on the fairway, but he didn't seem concerned about them spotting me(would have really thrown their game off if they had).
He asked me how far I wanted to take my CD play. I told him of my fantasy of being an oral CD cum dump for a half dozen alpha men. He said that could be arranged once I had "developed" further. I was then told to stand by the high backed leather chair, bend over again, this time leaning on the chair for some support. I noted then that he had a towel covering up something on the side stand beside the chair.
He then would walk slowly around me, all the time touching and caressing my ass and caged cock, plus verbally humiliating me. I was getting aroused and made an attempt to feel his cock through his slacks. My hand was briskly pushed aside and I was told to keep my hands to myself.....got two goods whacks on my ass as well!
It wasn't long until his finger(the fingers) started to probe my ass. He lubed his fingers and started working them in and around. I have tried plugs and a small thin dildo back there, but never have found any sexual highs coming my way with toys in my ass. His manipulations though started to have a nice effect on me...……… soon fingers got replaced by a some kind of dildo or prostate massager(I never got a look at the toys). Along with copious amounts of lube he eventually had my sissy cock dribbling a bit of pre cum.
I was now pushing my ass back to accept his probing. Some pain, but the ass manipulation was getting me hot, and I thought that if he this kept this up I might just cum(I doubt it now, but the feeling was there for sure). When I started to push back in time with the dildo insertions, he would spank my ass in time as well.....call me a slut....tell me that I wasn't man enough to fuck my wife, and that she is fucking others while I am with him etc.
This talk just made it all the more intense and exciting for me. I really wanted to cum, but he had other plans:(.
He got me to the edge and told me that "that's enough for now"!
As far as I could tell he never once stroked his own cock, and never took one piece of clothing off. He showed me to a washroom where I could clean up my lubed ass, and said that I should get dressed.
I had expected and was hoping that I would be sucking his cock before I left....not so. I was somewhat disappointed but I did leave feeling very slutty and satisfied with my first real taste of CD company. He assured me that he would be in touch for another CD lesson:). He told me that he had a couple of friends that might like to "use me" once I had become more comfortable in my new lifestyle direction..... I wanted to ask many questions then, but I sensed that the visit was over.
We met up again about a month later at my house. It was difficult arranging safe visit dates because he was also married and in the closet. Our second meeting was very similar, but we got into the play faster this time. He was more verbal and aggressive now. I had also followed his instructions regarding the use of butt plugs to open up my tight sissy ass pussy in between visits.
I'm not sure that I was any more open back there. He brought his toys and lube with him, and seemed to really enjoy messing with my ass again. I was dolled up as before, but tried to do a better job with the makeup. Still had the tight 3" heels, and was relieved when I took them off to climb up and kneel on the bed.
Locked cock like before, but hiding it behind a pair of pink panties. He worked me up to a similar edge like before.....got to feel like I was going to shoot, but didn't:(. Also, like before no cock sucking action for me!
I did like to hear that he thought his friends would surely love to meet me soon. He didn't elaborate when I asked about his friends, and what they might have planned etc. Just left my mind to think of all kinds of cool nasty kinky scenarios....lol.
A good CD visit again, but like before he kept his cloths on and didn't let me touch his dick. He told me that he would plan another visit for next month if our schedules connected well...….BUT
I fucked it all up about two weeks later when I found another CD man via Craigslist. I think his name was Tim and he was local. Tim came to my house, put on his fem dress and panties. No wigs, shoes or makeup on either of us. I had garters, stockings and panties on, but no other true fem stuff.
We had fun...Got him up on the bed.....sucked him and rimmed his ass, went back to his cock(average cut) and sucked him dry. As we had arranged there was no reciprocation from him required or desired.
I had some fem stuff that didn't fit me well, and I gave what I had to Tim. He seemed very pleased, and we talked about getting together again.
MY BIG MISTAKE....was telling my CD master about Tim's visit...sent him pictures as well. I thought he would be pleased to hear of my CD adventure, but instead he was pissed because I didn't get his permission to have Tim over & have that fun! So I fucked up what might have turned into some great CD fun. The CD master dropped me like a rock!
Live and learn I guess. Plus be loyal to your master or mistress(or be sure to ask permission:)
FYI, I do have a couple of pictures saved from my meeting with Tim. Not the greatest pics, but I will forward them if anyone wants to check them out. Any pictures of me in full CD fem gear got deleted....no real loss because I did look like an ugly slag & although I loved how I felt when dressed, I hated how I looked!
Thanks for reading.
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