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5-STAR POSTS!!     |
13/11/2011
It started when a friend of mine invited me to join one of those social networking sites. She said that everyone was using them. You know the ones, Twitter, My Space, Facebook, etc. She said that she was on nearly all of them! She pointed out, that I might make a friend or two!
So I joined one of them. I thought about what I wanted to say on my “site” now that I had registered. It had been two years since I had a relationship with a woman, but every relationship I have ever had with a woman, had failed since college. Truth is, two relationships stood out in my mind. Back in college I dated a T-Girl. She started out as my college roommate. Little did I know, that Kevin really wanted to be Stephanie! It took about six months of rooming together, before she revealed herself to me. After that we started dating. Kevin would go to classes as a male by day and be my female lover at night. This lasted until I graduated.
My second relationship that stood out was with Brenda. Brenda was a female who loved to be humiliated and dominated! She taught me how to be a Dominant to her Submissive. We explored the world of BDSM and had a Master-Slave relationship. It was a good relationship until I refused to let he have sex with my male friends. Then she decided that I wasn’t the Master for her and left.
Now, I decided that I would look to recapture what I have in college with a special girl. They say that you can’t go back again, but maybe you can capture the magic that once existed between a man and a special woman. So I set up my page as a Master looking for his Submissive T-girl. To my surprise, the page drew a quite a lot of attention. Not all of it welcome. I tended to get a lot of men interested from 20 -60 from all over the world. (If that was what they truly were! For all I know they were 40 year old guys from Nigeria!) I turned those down.
I did strike up a friendship with some nice people. I had a mixture of men and women. Some were local to where I lived. Others lived in the surrounding states. I chatted with all of them as often as I could. I really liked two people. One lived in the next state and was a cross dressing male a little younger and the other one was a cross dressing male that lived in the same city.
I struck up a friendship with Jerry/Jennifer. He was married, but loved to dress in women’s clothes and wanted to live his life as a female as much as he had time. Jerry was 35 years old and a out of work bank executive. As a result of the economy and bank mergers, 1 out of 10 out of work people in town were from the banking industry. Jerry’s wife, Diane, still was an executive for a mega bank here in town. Jerry would dress in his girlie clothes during the day while he took care of their home. Because of his wife’s disapproval of his cross dressing, he always changed into his men clothes before she got home.
I thought that we should meet first so that Jerry/Jennifer and I could see if we were compatible. Jerry told me, he really wanted to be dominated. We hit it off and he followed me back to my apartment. Jerry had brought everything he needed to transform himself into Jennifer. So I left him alone in the bathroom. After almost 45 minutes, Jerry appeared in the Living Room as Jennifer!
Jennifer had long silky brown hair, long slender legs, stood about 5’-10” tall, without heels. Jennifer had silicone “falsies” to fill out her bra. She wore plain blue dress that did little to show off her long legs. Bottom line, Jerry/Jennifer needed a lot of work. He looked like a guy in drag. If I was going to turn him into my sissy slut/maid, I would have to get him some different outfits. I had cleared out space in my closet and dresser so that she could keep clothes over at my place.
Jennifer had the potential to be pretty. She was a natural when it came to kissing, but I led her back into the bedroom. Jennifer had only been with 2 other men in her life and was awkward at sucking a man’s cock. I could work with her on that. She knew the mechanics, but was in too much of a hurry to get results. I had to make sure she would pace herself when it came to sucking.
We got to the point that Jerry would come over to my apartment during the day and then change into Jennifer so that we could have an afternoon of play time. I also started her on a regimen of female hormones. They would soften her skin, help with formation of breasts, and soften her male features. Jerry was scared that his wife would notice the change. Since she was against his cross dressing, he was having to sneak around. I reassured him that it would be gradual and that she would barely notice.
I also invited many of my friends over to help me with training. Women who taught Jennifer the art of make up and oral sex. Men who taught her the art of sucking cock! When she hesitated, I punished her with a mixture of bondage and pain. I was always careful not to leave marks that would arouse suspicion from his wife. Jennifer’s transformation into womanhood was faster than I had imagined. What I thought would take at least six months was happening in a little over two!
When Jennifer didn’t do something right, or hesitated at doing what I or my friends ordered, she would get punished. It could be something as light as a spanking with a riding crop, whipped with a leather paddle. For more serious correction, she might have her balls tied up and the rope ran behind her like a thong to her “D” ring in her dog collar. This served to keep her posture nice and straight. If she bent over, she would pull hard at her balls.
Besides having the formation of breasts and the fact that they were always tender, Jerry was having a problem with getting hard when his wife wanted to have sex. He could only get semi-rigid at best. Diane would chastise him for not getting hard enough to penetrate her. This made Jerry break down and cry. Which in turn, would make Diane go off even more on him. I had to constantly reassure him that everything would turn out alright.
With all the hormones it was getting tougher and tougher for Jennifer to get hard at all. The only way that she could, was to either have me give it to her up her ass, or use a large dildo/vibrator up there. The hormones also were causing Jennifer’s breasts to lactate. I knew it was a matter of time before Diane would confront Jerry about all the changes. Jennifer had turned out to be a good sissy girl though.
She would dress in in her school girl or maid outfits when she was over at my house. She would drop to her knees anytime myself, or one of my friends wanted her to please them. Occasionally, we would go out and I would have her dress in short skirt and sheer blouse. People could see her black g-string panties, black bra and black stockings. With all the hormones, it was doubtful that anyone who knew her would realize that it was Jerry.
Guys would stare at us as we shopped. Once, there were 2 teenage boys following us around to get a better peek at Jennifer under her short skirt. We were in Sears and I dropped my wallet on the floor, I asked Jennifer to bend over an pick it up. The boys almost fainted when she did. I figured that it would give them jack-off material for days to come. I also ordered Jennifer not to get a hair cut. I wanted her hair to grow out naturally.
Another time, we were in a shop that catered to people who wanted to buy dildos, vibrators and various outfits. I had her try on a skirt that flew up as she would twirl about. I told her that when she went into try it on, that she would leave her g-string off when she came out to show it off. She came out and twirled for everyone in the store. As the did, her penis came into clear view of everyone. The young women who worked in the stored burst out with laughter.
The owner, was a big woman, who I had met several times from being in the store. I asked her if it would be alright with her, if Jennifer would go into the back room and service any of the stores sales girls. She said that it was fine with her, as long as she was first. I ordered Jennifer to removed the skirt and get down on her hands and knees and to follow her. Little did I know that they had a giant supply of toys in the back room that they kept for pleasuring each other.
Marjorie, the owner, removed her dress to reveal a corset and stockings. She ordered Jennifer to stand up and bend over a chair. Marjorie put on a giant strap on dildo and lubed it up. She bumped up the huge dildo against Jennifer’s man-pussy hole and started to slide it in. She saw was how easy it was going in, Marjorie then pushed with all her weight! Jennifer almost lost control leaning against the chair, but recovered. After thoroughly assaulting Jennifer’s ass with the strap-on Marjorie unfastened the giant dildo and ordered her to kneel on it on the floor. Jennifer did as she was ordered. Marjorie brought the chair over and propped up one leg on it and ordered Jennifer to eat her pussy. Marjorie’s pussy was already dripping at the anticipation and it didn’t take long before she, very loudly, had a orgasm.
Marjorie ordered Jennifer to stay seated on the dildo, put her corset and dress back on, came out and announced, “Next!” Lisa, a young girl of maybe 20, had more tattoos than one could count. She walked back into the room. Jennifer was still kneeling on the floor with the giant dildo up her ass. Lisa pulled down her leather pants to reveal her many time pierced labia and clit. She ordered Jennifer to lick her to orgasm. Jennifer was all to happy to obey. She lapped at the girl’s pussy like a dog drinking water. Jennifer stopped occasionally to suck on the ring that ran through Lisa’s clit. Lisa didn’t wait too long before she had her orgasm! When Lisa recovered from her orgasm, she pulled her pants back on and walked out of the back room.
She looked at the youngest member of the sales force, a girl who looked maybe 18! “Have fun,” is all she said. The young girl walked back and ordered Jennifer to strip off her bra and blouse. Terri, the young girl, sat on the same chair and ordered Jennifer to start to eat her pussy. After almost 10 minutes, Terry told Jennifer to stop and open her mouth side. Terri, proceeded to rub her pussy and squirt a torrent of liquid right into Jennifer’s waiting mouth. She told Jennifer to swallow, and she did what she was ordered. Terri kept on squirting and Jennifer tried her best to catch it all. There was so much liquid that it ran down her chest and right down her erect cock. Terri order her to clean her up with her tongue.
Terri came out and all of them complimented me on how well trained my sissy slave was. That they wished they had one of their own. I told them that maybe some time in the future, that could be arranged. Terri said that Jennifer was back there on the giant dildo with a raging hard on! There were no customers in the store so I asked if we all cold go back and watch her jerk off. All four of us went back and I ordered Jennifer to sit the chair and jerk off for our amusement. Marjorie gave her a Styrofoam cup to jerk off into.
Jennifer was so horny by now, it didn’t take her long to explode into the cup. I ordered her to drink every last drop out of it. Just to top things off, I ordered her to suck me off as well! I thanked the ladies and told them that we would be back again. Marjorie suggested that we do it close to closing time, that was we would have more time to play. We had just made some new friends. Eventually we would visit the women at the store and they would have parties at our home.
Now was the time I put my other plan in motion. I had Jerry start to give Diane Viagra every other day for 2 weeks in a row. That Friday, I told Jennifer that I was going to come over to their home on Saturday afternoon. Jennifer begged me not to, but I reassured her that everything was going to turn out alright. That this was the last time he would ever see Jerry. She left my apartment that Friday afternoon after having turned back into Jerry.
I pulled up in the drive way of a very spacious 2 story house. Diane came to the door and greeted me. Diane was good looking. She was 5’-6” tall, 35 years old with little extra padding. Some men would say “slightly plump”. Medium brown hair, with blonde highlights. She wore a baggy t-shirt and jeans. She was barefoot and I could see that she went for a manicure and pedicure once a week. Even without makeup, Diane was a beautiful woman.
My plan was to make her a sex slave, through bondage and discipline and drugs. I would have her fucking anything and everything! That was my plan at least. Until she opened the door. Whether I felt sorry for her, or Karma, I felt an instant chemistry between us. Time to change plans!
The front door opened and I introduced myself. “Hello Diane. Please allow me to introduce myself. I am Master B.”
She had a totally confused look on her face. She looked back at Jerry who stood in the hallway, looking as if he was going to pee his pants.
“What’s this all about?” She asked.
“If you allow me to come in, I can explain.”
She motioned me to come in. I pointed at the sofa and told her that she might want to sit down. I looked at Jerry and told him to go get dressed. Jerry, scampered down the hall to put on his maid outfit.
“I know this is going to come as a shock to you Diane. For the last several months, Jerry has been coming to my place for sex and to be turned into Jennifer. I thought it was time we all met.”
“That son-of-a-bitch! I knew something was going on. He couldn’t get it up with a crane! The breasts, the soft skin, the nails, letting his hair grow longer! I should have seen it coming. He said, no he promised me, that he was done with his dressing as a woman!” Diane shouted at the top of her lungs! “You fucking homo! You can’t get it up for a real woman, so you have to become one!”
“Everything is going to be alright.” I reassured her.
I started to explain to her everything that Jerry/Jennifer had been doing. The fact that Jennifer had become adapt at both pleasing both men and women. The more detail I went into the more turned on Diane was getting. I could see by the way she was shifting on the couch that she was trying to give some pleasure to her aching pussy. It had been months since she had a good fucking and two weeks of Viagra, was making her hardly able to stand it. Listening to all the sex her husband was getting and giving, proved more than she could take. Diane kept squirming on the couch trying to relieve the yearning coming from her pussy! I placed my hand on her knee and offered no resistance.
Just then, Jennifer came in wearing her maid’s outfit. Diane’s mouth dropped open. There before her was the man she married, and yet he was dressed as a sissy maid! I moved my hand between Diane’s legs and rubbed her pussy through her jeans. She spread her legs for me. She broke down and started crying. I wrapped my right arm around her and pulled her close to me. She was crying into my chest. I started to massage her breasts through her t-shirt, and whispering that it was okay, that she had a new man in her life now.
I reached up under her t-shirt and she continued to cry. I pulled her bra loose from her breasts and started to massage them and roll her nipples between my thumb and fore finger. She looked into me eyes. I told her not to worry, that Jennifer was going to be our new sissy maid and that she now had a new man and master! She couldn’t get out of her clothes fast enough. I stripped off my clothes and ordered Jennifer to come over and kneel on the floor where she could watch us. She kneeled down on her hands as she had been trained.
I was already hard and proceeded to enter Diane with no resistance. She was wet and so horny that it didn’t take her anytime to have her first orgasm! She kept looking at Jennifer while I kept pounding into her on their sofa. We finally relocated to the bedroom, where I made love to Diane several more times that day and night. All while Jennifer watched us. At times when we took a break, Diane would go over to Jennifer and, she would grind her foot into her limp dick! This seemed to bring Diane great pleasure.
That weekend, I gave her a taste of wearing a strap-on to butt fuck Jennifer. Diane and I wore each other out! Jennifer did all the cooking, and cleaning, including changing the cum stained sheets. We allowed her to sleep in the spare bedroom as long as she didn’t play with herself. Jennifer was made to watch as we showered together. Diane was surprised at well trained her, once Husband, was.
Within a week I moved in. I moved right into the Master Bedroom with Diane. Jennifer became our sissy slut/maid. Diane takes great pleasure from placing her in endless humiliating situations. It’s really is surprising how little you know about your neighbors and vice-versa. If anyone asks, we tell them that Jerry moved out and left town. That I had met Diane and it was love at first site. That Jennifer was our live-in maid. I think our neighbors are jealous that we have a live-in maid. Diane still has Jennifer watch as we make love. Often times, she orders Jennifer to clean up both up afterwards.
Diane accepted her roll as Mistress to Jennifer and Slave to me. I have her dress in more revealing attire when she isn’t at work. In the Summer, when she isn’t at work, I have Diane wear a bikini around the house with just a wrap around her waste. We have monthly sissy parties with Marjorie, Terri and Lisa. It turned out that Diane likes Marjorie so much, that they are like Mother and Daughter! My friends, who helped train Jennifer, are now helping me train a new sissy for Marjorie! Marjorie in turn, has friends who would like one of their own.
Diane takes great pleasure in disciplining the new sissy slut with the riding crop! Diane’s new found confidence has also helped her at work. She has had two promotions within the last 18 months. She has accepted my dominance over her with ease. Everything outside of her work, she leaves up to me. Diane does like occasionally, strapping on a dildo and butt fucking Jennifer until Jennifer has a raging hard on. Then she stops and won’t allow Jennifer to pleasure herself. She has also taught Jennifer to be on her elbows and knees when she comes home from work and kiss and lick her shoes.
We put in a pool with a 10 feet tall privacy fence in the backyard for pool parties. Jennifer services the pool cleaner whenever he comes over. As soon as he arrives, she lubes up her man-pussy. She runs out to greet him and has him sit down in a chair so she can get him hard with her mouth. Jennifer has turned out to be a great cock sucker! When the pool guy’s nice and hard, she then turns around and lets him slam into her man-pussy. This gets her so hard, that she has to jerk off as well!
We got Jennifer breasts implants to further accentuate her bust line. Diane likes her to dress in tight tops when ever she goes out. It looks like the buttons will burst any moment. Men and even some women, young and old, go crazy when they see her. Jennifer has been hit on by every guy in the neighborhood! They have no idea what’s she’s hiding between her legs! Diane loves to take her former husband to Marjorie’s store. Marjorie had a Glory Hole (A hole in the bathroom stall) where certain clients can stick the cock through. Diane makes sure that when a cock comes through the hole, Jennifer is eager to suck it dry! She even has had Jennifer suck some of her bosses off during a Christmas party we held at our home!
I’m retired and Diane doesn’t mind. After all, we have sissy’s to train!
FUCK MY WIFE!
CLICK BELOW TO FIND A BULL
So I joined one of them. I thought about what I wanted to say on my “site” now that I had registered. It had been two years since I had a relationship with a woman, but every relationship I have ever had with a woman, had failed since college. Truth is, two relationships stood out in my mind. Back in college I dated a T-Girl. She started out as my college roommate. Little did I know, that Kevin really wanted to be Stephanie! It took about six months of rooming together, before she revealed herself to me. After that we started dating. Kevin would go to classes as a male by day and be my female lover at night. This lasted until I graduated.
My second relationship that stood out was with Brenda. Brenda was a female who loved to be humiliated and dominated! She taught me how to be a Dominant to her Submissive. We explored the world of BDSM and had a Master-Slave relationship. It was a good relationship until I refused to let he have sex with my male friends. Then she decided that I wasn’t the Master for her and left.
Now, I decided that I would look to recapture what I have in college with a special girl. They say that you can’t go back again, but maybe you can capture the magic that once existed between a man and a special woman. So I set up my page as a Master looking for his Submissive T-girl. To my surprise, the page drew a quite a lot of attention. Not all of it welcome. I tended to get a lot of men interested from 20 -60 from all over the world. (If that was what they truly were! For all I know they were 40 year old guys from Nigeria!) I turned those down.
I did strike up a friendship with some nice people. I had a mixture of men and women. Some were local to where I lived. Others lived in the surrounding states. I chatted with all of them as often as I could. I really liked two people. One lived in the next state and was a cross dressing male a little younger and the other one was a cross dressing male that lived in the same city.
I struck up a friendship with Jerry/Jennifer. He was married, but loved to dress in women’s clothes and wanted to live his life as a female as much as he had time. Jerry was 35 years old and a out of work bank executive. As a result of the economy and bank mergers, 1 out of 10 out of work people in town were from the banking industry. Jerry’s wife, Diane, still was an executive for a mega bank here in town. Jerry would dress in his girlie clothes during the day while he took care of their home. Because of his wife’s disapproval of his cross dressing, he always changed into his men clothes before she got home.
I thought that we should meet first so that Jerry/Jennifer and I could see if we were compatible. Jerry told me, he really wanted to be dominated. We hit it off and he followed me back to my apartment. Jerry had brought everything he needed to transform himself into Jennifer. So I left him alone in the bathroom. After almost 45 minutes, Jerry appeared in the Living Room as Jennifer!
Jennifer had long silky brown hair, long slender legs, stood about 5’-10” tall, without heels. Jennifer had silicone “falsies” to fill out her bra. She wore plain blue dress that did little to show off her long legs. Bottom line, Jerry/Jennifer needed a lot of work. He looked like a guy in drag. If I was going to turn him into my sissy slut/maid, I would have to get him some different outfits. I had cleared out space in my closet and dresser so that she could keep clothes over at my place.
Jennifer had the potential to be pretty. She was a natural when it came to kissing, but I led her back into the bedroom. Jennifer had only been with 2 other men in her life and was awkward at sucking a man’s cock. I could work with her on that. She knew the mechanics, but was in too much of a hurry to get results. I had to make sure she would pace herself when it came to sucking.
We got to the point that Jerry would come over to my apartment during the day and then change into Jennifer so that we could have an afternoon of play time. I also started her on a regimen of female hormones. They would soften her skin, help with formation of breasts, and soften her male features. Jerry was scared that his wife would notice the change. Since she was against his cross dressing, he was having to sneak around. I reassured him that it would be gradual and that she would barely notice.
I also invited many of my friends over to help me with training. Women who taught Jennifer the art of make up and oral sex. Men who taught her the art of sucking cock! When she hesitated, I punished her with a mixture of bondage and pain. I was always careful not to leave marks that would arouse suspicion from his wife. Jennifer’s transformation into womanhood was faster than I had imagined. What I thought would take at least six months was happening in a little over two!
When Jennifer didn’t do something right, or hesitated at doing what I or my friends ordered, she would get punished. It could be something as light as a spanking with a riding crop, whipped with a leather paddle. For more serious correction, she might have her balls tied up and the rope ran behind her like a thong to her “D” ring in her dog collar. This served to keep her posture nice and straight. If she bent over, she would pull hard at her balls.
Besides having the formation of breasts and the fact that they were always tender, Jerry was having a problem with getting hard when his wife wanted to have sex. He could only get semi-rigid at best. Diane would chastise him for not getting hard enough to penetrate her. This made Jerry break down and cry. Which in turn, would make Diane go off even more on him. I had to constantly reassure him that everything would turn out alright.
With all the hormones it was getting tougher and tougher for Jennifer to get hard at all. The only way that she could, was to either have me give it to her up her ass, or use a large dildo/vibrator up there. The hormones also were causing Jennifer’s breasts to lactate. I knew it was a matter of time before Diane would confront Jerry about all the changes. Jennifer had turned out to be a good sissy girl though.
She would dress in in her school girl or maid outfits when she was over at my house. She would drop to her knees anytime myself, or one of my friends wanted her to please them. Occasionally, we would go out and I would have her dress in short skirt and sheer blouse. People could see her black g-string panties, black bra and black stockings. With all the hormones, it was doubtful that anyone who knew her would realize that it was Jerry.
Guys would stare at us as we shopped. Once, there were 2 teenage boys following us around to get a better peek at Jennifer under her short skirt. We were in Sears and I dropped my wallet on the floor, I asked Jennifer to bend over an pick it up. The boys almost fainted when she did. I figured that it would give them jack-off material for days to come. I also ordered Jennifer not to get a hair cut. I wanted her hair to grow out naturally.
Another time, we were in a shop that catered to people who wanted to buy dildos, vibrators and various outfits. I had her try on a skirt that flew up as she would twirl about. I told her that when she went into try it on, that she would leave her g-string off when she came out to show it off. She came out and twirled for everyone in the store. As the did, her penis came into clear view of everyone. The young women who worked in the stored burst out with laughter.
The owner, was a big woman, who I had met several times from being in the store. I asked her if it would be alright with her, if Jennifer would go into the back room and service any of the stores sales girls. She said that it was fine with her, as long as she was first. I ordered Jennifer to removed the skirt and get down on her hands and knees and to follow her. Little did I know that they had a giant supply of toys in the back room that they kept for pleasuring each other.
Marjorie, the owner, removed her dress to reveal a corset and stockings. She ordered Jennifer to stand up and bend over a chair. Marjorie put on a giant strap on dildo and lubed it up. She bumped up the huge dildo against Jennifer’s man-pussy hole and started to slide it in. She saw was how easy it was going in, Marjorie then pushed with all her weight! Jennifer almost lost control leaning against the chair, but recovered. After thoroughly assaulting Jennifer’s ass with the strap-on Marjorie unfastened the giant dildo and ordered her to kneel on it on the floor. Jennifer did as she was ordered. Marjorie brought the chair over and propped up one leg on it and ordered Jennifer to eat her pussy. Marjorie’s pussy was already dripping at the anticipation and it didn’t take long before she, very loudly, had a orgasm.
Marjorie ordered Jennifer to stay seated on the dildo, put her corset and dress back on, came out and announced, “Next!” Lisa, a young girl of maybe 20, had more tattoos than one could count. She walked back into the room. Jennifer was still kneeling on the floor with the giant dildo up her ass. Lisa pulled down her leather pants to reveal her many time pierced labia and clit. She ordered Jennifer to lick her to orgasm. Jennifer was all to happy to obey. She lapped at the girl’s pussy like a dog drinking water. Jennifer stopped occasionally to suck on the ring that ran through Lisa’s clit. Lisa didn’t wait too long before she had her orgasm! When Lisa recovered from her orgasm, she pulled her pants back on and walked out of the back room.
She looked at the youngest member of the sales force, a girl who looked maybe 18! “Have fun,” is all she said. The young girl walked back and ordered Jennifer to strip off her bra and blouse. Terri, the young girl, sat on the same chair and ordered Jennifer to start to eat her pussy. After almost 10 minutes, Terry told Jennifer to stop and open her mouth side. Terri, proceeded to rub her pussy and squirt a torrent of liquid right into Jennifer’s waiting mouth. She told Jennifer to swallow, and she did what she was ordered. Terri kept on squirting and Jennifer tried her best to catch it all. There was so much liquid that it ran down her chest and right down her erect cock. Terri order her to clean her up with her tongue.
Terri came out and all of them complimented me on how well trained my sissy slave was. That they wished they had one of their own. I told them that maybe some time in the future, that could be arranged. Terri said that Jennifer was back there on the giant dildo with a raging hard on! There were no customers in the store so I asked if we all cold go back and watch her jerk off. All four of us went back and I ordered Jennifer to sit the chair and jerk off for our amusement. Marjorie gave her a Styrofoam cup to jerk off into.
Jennifer was so horny by now, it didn’t take her long to explode into the cup. I ordered her to drink every last drop out of it. Just to top things off, I ordered her to suck me off as well! I thanked the ladies and told them that we would be back again. Marjorie suggested that we do it close to closing time, that was we would have more time to play. We had just made some new friends. Eventually we would visit the women at the store and they would have parties at our home.
Now was the time I put my other plan in motion. I had Jerry start to give Diane Viagra every other day for 2 weeks in a row. That Friday, I told Jennifer that I was going to come over to their home on Saturday afternoon. Jennifer begged me not to, but I reassured her that everything was going to turn out alright. That this was the last time he would ever see Jerry. She left my apartment that Friday afternoon after having turned back into Jerry.
I pulled up in the drive way of a very spacious 2 story house. Diane came to the door and greeted me. Diane was good looking. She was 5’-6” tall, 35 years old with little extra padding. Some men would say “slightly plump”. Medium brown hair, with blonde highlights. She wore a baggy t-shirt and jeans. She was barefoot and I could see that she went for a manicure and pedicure once a week. Even without makeup, Diane was a beautiful woman.
My plan was to make her a sex slave, through bondage and discipline and drugs. I would have her fucking anything and everything! That was my plan at least. Until she opened the door. Whether I felt sorry for her, or Karma, I felt an instant chemistry between us. Time to change plans!
The front door opened and I introduced myself. “Hello Diane. Please allow me to introduce myself. I am Master B.”
She had a totally confused look on her face. She looked back at Jerry who stood in the hallway, looking as if he was going to pee his pants.
“What’s this all about?” She asked.
“If you allow me to come in, I can explain.”
She motioned me to come in. I pointed at the sofa and told her that she might want to sit down. I looked at Jerry and told him to go get dressed. Jerry, scampered down the hall to put on his maid outfit.
“I know this is going to come as a shock to you Diane. For the last several months, Jerry has been coming to my place for sex and to be turned into Jennifer. I thought it was time we all met.”
“That son-of-a-bitch! I knew something was going on. He couldn’t get it up with a crane! The breasts, the soft skin, the nails, letting his hair grow longer! I should have seen it coming. He said, no he promised me, that he was done with his dressing as a woman!” Diane shouted at the top of her lungs! “You fucking homo! You can’t get it up for a real woman, so you have to become one!”
“Everything is going to be alright.” I reassured her.
I started to explain to her everything that Jerry/Jennifer had been doing. The fact that Jennifer had become adapt at both pleasing both men and women. The more detail I went into the more turned on Diane was getting. I could see by the way she was shifting on the couch that she was trying to give some pleasure to her aching pussy. It had been months since she had a good fucking and two weeks of Viagra, was making her hardly able to stand it. Listening to all the sex her husband was getting and giving, proved more than she could take. Diane kept squirming on the couch trying to relieve the yearning coming from her pussy! I placed my hand on her knee and offered no resistance.
Just then, Jennifer came in wearing her maid’s outfit. Diane’s mouth dropped open. There before her was the man she married, and yet he was dressed as a sissy maid! I moved my hand between Diane’s legs and rubbed her pussy through her jeans. She spread her legs for me. She broke down and started crying. I wrapped my right arm around her and pulled her close to me. She was crying into my chest. I started to massage her breasts through her t-shirt, and whispering that it was okay, that she had a new man in her life now.
I reached up under her t-shirt and she continued to cry. I pulled her bra loose from her breasts and started to massage them and roll her nipples between my thumb and fore finger. She looked into me eyes. I told her not to worry, that Jennifer was going to be our new sissy maid and that she now had a new man and master! She couldn’t get out of her clothes fast enough. I stripped off my clothes and ordered Jennifer to come over and kneel on the floor where she could watch us. She kneeled down on her hands as she had been trained.
I was already hard and proceeded to enter Diane with no resistance. She was wet and so horny that it didn’t take her anytime to have her first orgasm! She kept looking at Jennifer while I kept pounding into her on their sofa. We finally relocated to the bedroom, where I made love to Diane several more times that day and night. All while Jennifer watched us. At times when we took a break, Diane would go over to Jennifer and, she would grind her foot into her limp dick! This seemed to bring Diane great pleasure.
That weekend, I gave her a taste of wearing a strap-on to butt fuck Jennifer. Diane and I wore each other out! Jennifer did all the cooking, and cleaning, including changing the cum stained sheets. We allowed her to sleep in the spare bedroom as long as she didn’t play with herself. Jennifer was made to watch as we showered together. Diane was surprised at well trained her, once Husband, was.
Within a week I moved in. I moved right into the Master Bedroom with Diane. Jennifer became our sissy slut/maid. Diane takes great pleasure from placing her in endless humiliating situations. It’s really is surprising how little you know about your neighbors and vice-versa. If anyone asks, we tell them that Jerry moved out and left town. That I had met Diane and it was love at first site. That Jennifer was our live-in maid. I think our neighbors are jealous that we have a live-in maid. Diane still has Jennifer watch as we make love. Often times, she orders Jennifer to clean up both up afterwards.
Diane accepted her roll as Mistress to Jennifer and Slave to me. I have her dress in more revealing attire when she isn’t at work. In the Summer, when she isn’t at work, I have Diane wear a bikini around the house with just a wrap around her waste. We have monthly sissy parties with Marjorie, Terri and Lisa. It turned out that Diane likes Marjorie so much, that they are like Mother and Daughter! My friends, who helped train Jennifer, are now helping me train a new sissy for Marjorie! Marjorie in turn, has friends who would like one of their own.
Diane takes great pleasure in disciplining the new sissy slut with the riding crop! Diane’s new found confidence has also helped her at work. She has had two promotions within the last 18 months. She has accepted my dominance over her with ease. Everything outside of her work, she leaves up to me. Diane does like occasionally, strapping on a dildo and butt fucking Jennifer until Jennifer has a raging hard on. Then she stops and won’t allow Jennifer to pleasure herself. She has also taught Jennifer to be on her elbows and knees when she comes home from work and kiss and lick her shoes.
We put in a pool with a 10 feet tall privacy fence in the backyard for pool parties. Jennifer services the pool cleaner whenever he comes over. As soon as he arrives, she lubes up her man-pussy. She runs out to greet him and has him sit down in a chair so she can get him hard with her mouth. Jennifer has turned out to be a great cock sucker! When the pool guy’s nice and hard, she then turns around and lets him slam into her man-pussy. This gets her so hard, that she has to jerk off as well!
We got Jennifer breasts implants to further accentuate her bust line. Diane likes her to dress in tight tops when ever she goes out. It looks like the buttons will burst any moment. Men and even some women, young and old, go crazy when they see her. Jennifer has been hit on by every guy in the neighborhood! They have no idea what’s she’s hiding between her legs! Diane loves to take her former husband to Marjorie’s store. Marjorie had a Glory Hole (A hole in the bathroom stall) where certain clients can stick the cock through. Diane makes sure that when a cock comes through the hole, Jennifer is eager to suck it dry! She even has had Jennifer suck some of her bosses off during a Christmas party we held at our home!
I’m retired and Diane doesn’t mind. After all, we have sissy’s to train!
 TAKE MY WIFE |
 FUCK ME |
Poster:
Bimaster