Sissy trainer Parts 1 and 2

Hello. I am Ian Roberts, and I am a professional sissy trainer. Women hire me to train their husbands/boyfriends to be the perfect sissies and cuckolds. Sometimes a woman might have a partner that is mean and disrespectful towards them, and maybe even violent, that's when they call me to change that behavior and attitude. For those women I do what I do for free. Once their man is properly trained, I then start charging them for my service. My service does require me to have sex with men, but only as a dominant top. I love women and have more than my share of pussy. I am single but I do have a regular GILF who I have sex with everyday, she used to be a client.
I am a black male, 48, 6' tall, 235 pounds of pure black toned muscle, shaved head and better than average looks. I have a 9x6" black dick with huge low hanging balls. My GILF (Paula) was the one who got me into this one of a kind business. She was in an abusive and demeaning marriage. I was at a local bar alone, having a few drinks before I went to my hotel room for the night. The place had seating everywhere to include a row booth along one wall. In the last booth, towards the back, was a couple. My GILF and her husband. Paula is 60, 5'3, 115 pounds, 34-26-36, with big round DD tits and nice round ass. She has short black hair, with ice blue eyes. She could get a dead man horny. Her loser husband, Mario, 63, 5'9", 200 pounds of blubber, a bad comb-over brown hair and what I still think was a spray on tan. He was wearing a lot of oversized gold jewelry. It was obvious that they had lots of money.
It didn't take much to see that Mario was a dominating punk, has no respect for any women, let alone his wife. He was loud and obnoxious, ordered her, not asking her to go get his drink. As Paula got close to the bar, to place her order, her head was down. When she looked up and made eye contact with me, I could see the stress and fear in her eyes. I was raised to never treat a woman that way. Women should have to fear any man let alone her own husband. She gave me a weak smile, and a soft hi, I felt badly for her. She went back to her booth with her drinks. Right away, that ass hat of a husband starts yelling at her, because the drink was not the way he asked for.
I know it was none of my business, but, my mother would haunt me from her grave if I just sat there and let him treat her like this. I decided to go and try to put an end to this abuse, at least for as long as they were in this bar. It wasn't busy, but other patrons looked up, and then looked away like there was nothing happening. As I approached them, Paula was facing me. She saw me coming and her eyes got big as saucers. Mario, noticed her shocked look, as said to her, what the fuck is wrong with you, the turned to see me just as I go to the booth. He looked at me and said, what the fuck do you want. Keeping my composure, I asked Paula if she was ok. Before she could answer, he says she's fine, mind your own business and walk away while you can, boy! Not missing a beat, gave Mario a quick jab to his throat. He grabbed his throat, gagged, and when his head bent down, I slammed it into the table. Paula gasped loudly in shock, but I am sure I saw a faint smile. I forced Mario to slide over to the inside of the booth. With difficulty, he asked who I was and why I attacked him for no reason. Calmly, I said I am a person who can't stand a man who thinks it's ok to abuse a woman like I saw you do. Mario tells me, she's my wife, I can treat her any way I want, I am the man, I am the boss. Again, I slammed his face into the table, this time, causing his nose to start bleeding. When he recovered, I said you are going to apologize to the lady. I look at her and she smiled again. Mario says, fuck you, you black bastard, bang, another table face plant. I get real close to his face and tell him, I can do this all night and not break a sweat. He starts to say something smart ass again, so I reached under the table and grabbed his balls and squeezed them really tight. It hurt so bad he couldn't scream. His eyes bugged out of his head, she turned three different shades of red. Then to make it worse, while still with a death grip on his balls, I leaned over and kissed Paula. Even though she was shocked, she responded and kissed back. After the kiss, i leaned back towards Mario and said, I am going to let go of your pathetic little balls, and then you and your little lady are going to follow me to my hotel room and figure out a way to change your attitude towards this lady. Then I told Paula she can trust me, and she will be safe, this is all about this piece of shit. Still not sure, she shook her head ok. Giving Mario a death stare, are we going to have any trouble. He shook his head no. We got up from the booth, and with him leading the way, bloody nose and all. People in the bar started cheering and laughing at him, and Paula and I arm in arm following close behind.
When we got into my suite, I told Paula to make herself comfortable on the sofa. Mario started to follow her when I stopped him and said, not your bitch, move that table and sit on the floor. He started to complain, but my gut punched him, causing him to double over on the floor. I got down on his level and said, the only reason I don't beat the living shit out of you right now is because of that lady sitting over there. Don't make me forget she was here. Paula was gleaming at seeing him cowl. I left the room to go get some ice. It took me a couple of minutes, when I got back, Paula was on the floor about a foot away from him and yelling at him for treating her so badly for all of these years. I asked is every? She said yes, as soon as you left, he started calling me names and threatening me. Then he started in on you with racial slurs, and how disgusting it was to see you kiss me. I told him I like it a lot. I looked at him and said, you didn't like me kissing your wife, well then you're going to hate this. I stood him up, punched him in the jaw knocking him out.
Later he woke up tied to a chair in the corner of the room. Mario realized that he was nude and not far from him on the sofa, was me in my underwear, and Paula in a very sexy bra and thong. He said, why am I naked, and where did you get those underwear? I answered, We went out and bought them for her, after I knocked you out, and you are being nude is part of your training. Training he asked. I said yep, I am going to teach you to be kinder and obedient towards the sexy beautiful woman, then I grabbed her huge tits causing her to moan and smile. Mario got mad and said, don't touch my wife like that. I then informed him that she was no longer his wife, but his mistress and he will now be her sissy slave and do as she orders. Paula got up, walked over to him smiling big. She got on her knees between his legs and repeated what I just said. He started to object, but she grabbed his balls and squeezed as hard as she could with her small hand. Mario screamed out in pain, Paula laughed at him and said that sexy black man over there is my new daddy, and I am going to go back to him and let him fuck me and use my body as he pleases. Then she got close and whispered in his ear, I am even going to let him shove that big black dick in my ass and fuck me as long and as hard as he wants, and you get to watch it all.
She let go of his balls, and crawled back to me and started sucking my cock over my underwear, while playing with my nipples at the same time. She stood up, faced her slave/husband and was given a sexy striptease of what little she had left on, never taking her eyes off of him. Even though he was still in lots of pain, you could see the fury in is face. After she was naked, she sat back on my lap, grinding her bare shaved pussy on my covered dick. I reached around her and got two handfuls of her big tits, making her moan loud. Then she focused on Mario again. While grinding on me, she used one hand to open her wet pussy lips, and her other to play with her hard clit. She says to him, do you like my shaved cunt, he shaved it for me while you passed out, and it feels so good. MMMM you're going to love watching his hard meat sliding into me, aren't you my bitch? Paula stood up bringing me with her. Then she dropped to her knees, pulled my underwear with her, helping out of them. She turned me enough so that Mario had a good view, and started licking and sucking my dick. After a few minutes, smiling at Mario, she says to him, MMMM tastes so good. Feels good to have a real mans dick in my mouth instead of that tiny thing you have. Wait till you get to watch me lick my new black daddy's ass.
Paula guided me back to sitting on the sofa, lifted my legs high and started sucking on my balls and licking my tight ass, and I have to admit, it felt great. She had me so fucking horny, my dick was as hard as it could get. Without warning, she stopped, looked up at me and said baby, I need to do something else before we fuck. She walked back over to her husband, Bend down, took his head in her hand and forced her tongue in his mouth, right after having it buried in my ass and licking my balls. Because he was tied up, he couldn't stop her. I was thinking about how much she has changed in just a few hours, and we aren't even halfway done with our plan for him.
As she came back to me, looking at her fucking amazing body, I couldn't help but think what a fool her hubby was. If she was my wife, I would have been treating her like a queen and fucking her like a slut everyday. She was built for fucking. She had me lay on the carpeted floor with a pillow under my head, she straddled my lap, made sure he was watching and then lowered her wet pussy down onto my thick cock balls deep. She looked right into Mario's eyes and fuck, he so big, he is splitting me open and I love every inch of it. Mario wasn't able to turn away, so he tried to close his eyes, but Paula was so loud and fucking so hard the slapping of our body could be heard all over the suite, plus she was taunting him. This lady has one of the wettest, tightest pussy's I have ever been in. Then through her moans she tells Mario to watch this. She rises off my dick that is really wet from her constant orgasm. Then she lines my cock up with her virgin ass, and forces it slowly in her. Even though she is in pain, she keeps a forced smile on her face while sliding down on me, then makes sure to tell him how good black cock feels in his wife's ass. When she gets used to me in her, she starts fucking me hard and deep, moaning a groaning the whole time. I started getting that feeling in my balls, letting me know I am close to cuming, and I tell her so. Paula stops riding, gets off of me and faces me. She tells me, baby, I want as much of your cum as you want to give me, but I think I should share it. Because of pre-planning I knew what she meant, but Mario didn't. I told her ok, I understand, she kissed me deeply and said thank you daddy.
We both looked at a confused Mario. Paula points with a huge smile, look, daddy, his little prick is hard, he like watching a black man fuck his wife. We both laughed out loud at him. He was really pissed at us for laughing at him, and at him for his dick betraying him. Paula and I stood on either side of him. She bent over with her huge tits brushing against his shoulder, she spoke softly to him. She says, for years you have treated me like a piece of shit and made me feel that I was ugly and less than human, but in the last 6 hours my new black daddy has let me see that I am a hot and sexy woman, and way more than you deserve. But, I am not going to leave you Mario. I am going to take charge of this marriage. By the time we are through with you tonight, you will be my slave and do whatever I order. Also, your tiny dick will never touch my body again, and I will fuck my new daddy as much as we want, and in front of you, and you will willingly watch. Mario, says loudly, you're my wife and you will do what I say. Paula nibbles his ear, and says nope, you be my sissy bitch.
I lifted his face so he was looking at me, and then I knocked him out again. When he woke up, he was bent over the coffee table with his ass in the air. I was kneeling in front of him with my hard cock inches from his mouth. It took him a minute to realize that his face was covered in my cum. He said, WTF. Smiling, I said, while you were out I fucked your face, throat and gave you a nice hot facial. I bet you are a better cocksucker when you're awake. Just as he starts to say something, he screams out in pain. Paula was behind him with a big black strap-on and shoved it balls deep in his ass in one thrust with only spit as lube. Paula and I start laughing out loud at his pain. Paula says take my black dick bitch. I am going to fuck the living hell out of you. She gabs his hip and starts fucking him hard and as deep as she can, poor little Mario grunting and begging her to stop, but it's only making her fuck harder. I was so into watching Paula, fuck her husband, I forgot to play. I grabbed him by the hair trying to force his mouth open. I said open up sissy and suck my cock, it's time to get spit roasted. He refused. I reminded him that I will hurt him badly if he doesn't open up. He did the right thing and I tried to shove all 9 thick inches down his throat. Paula and I were really doing a number on him. Paula tells me she wants to have a turn fucking his throat, she wants to see his face while she is punishing him, I have created a sexy ass monster.
I guess Mario didn't hear her say she wanted to fuck his face. He was relieved, we both stopped our assault on him, giving him a very quick break. Being tied to the table, he couldn't move much. Standing over him at both ends with my balls rubbing at his forehead and Paula's fake dick in between his ass cheeks, we were in a deep wet kiss, humiliating and angering Mario even more. Paula tells me how much fun she is having. I say clear enough for Mario to hear, this is only the beginning baby. We both sat on the sofa, less than a foot from where he was tied up, making out like teenagers, with our hands all over each other Paula notices and say look daddy, he's still hard, he must like getting fucked and treated like a sissy slut. His dick was rock hard and had a small of pre-cum under him on the floor. Paula tells me, breaks over. We got up, changed places. I got to fuck his tight racist ass, and Paula fucked his face with her big fake black cock. I shot a big load into his ass and when I was done, I forced him to clean my cock in his mouth. Then Paula and I fuck the rest of the night. I fucked her hot tight ass on the sofa, right in front of him. Then we went into the bedroom and fuck some more leaving him tied up all night. Hours later, I woke up alone in bed. I heard moaning coming from the other room. I found Paula on her hands and knees, forcing her ass into Mario's face. She had the strap on buried in her cunt fucking herself. She saw me standing there watching with morning wood. She waved me over, had me sit in front of her, and gave me a world class blowjob swallowing my load.
Paula told me that she woke up an hour ago very horny, but she didn't want to wake me, so went out and fucked Mario's ass again. Then she pointed under the table in a pool of cum. She said while she was fucking him, he had an orgasm from being fucked in the ass. I looked at him and said, good boy, you're a true sissy now. Paula had climbed up in my lap and buried my dick balls deep in her cunt and fucked me slowly, while we taunted him. Just as I was about to cum, Paula pulled my cock out of her pussy and aimed it at Mario's face just in time to shoot all over his face.

CHAPTER 2

You will refer to Paula as Mistress Paula. You will do whatever she tells you and when and where ever she tell you. You will go to work everyday and come right home after you're done. You will strip naked as soon as the door closes behind you and you will put on whatever you are told to, if anything at all. Your sex life will be only what your mistress allows if anything at all. For some stupid reason, Mario forgot everything he just went through, because he tried to be a tough guy again. Paula went behind him and grabbed his balls and squeezed and pulled them hard. At the same time she shoved the big strap-on dildo that was on the floor deep in his ass. The scream that came out of him made me cringe. He started babbling that he was sorry. Paula said, try again bitch. I am sorry for speaking out of turn Mistress, I will be good. To make sure, I point to the 3 different video cameras that Paula and I had got and set up while he was u*********s. I promised him that if he ever tries to cause any problem for either of us, in any way, the hours and hours of video will be sent to his friends, family, co-workers and uploaded to the internet. Also the first part of the video has already been made to look like you are a willing participant in the taping, so crying **** or anything would be useless. Paula satisfied that he will behave, let go of his balls and pulled the toy out of his man cunt. She straddled her hot naked body across his and spoke softly in his ears, I own you bitch, and for all the years you treated me like shit, I am going to pay you back. I hope you enjoyed all the times you forced me to fuck you, and all the sluts you cheated on me with, because it is over, this worthless dick is owned by me and it will never get inside of my cunt or ass again, maybe nobody else. But you face ass and throat are going to be stretched wide.
We untied him and made him sit in the corner and watch me bend her over a chair and fuck her hot tight ass. When I pumped another load in her, she sat on his face and made him suck the load out of her ass. They got dressed to leave. I told her I would talk to her, and made plans to see her tomorrow, and check on the training. They left with him walking behind her with his head hanging low.
That was about two months ago. Paula is still in charge. Mario is the learning more and more to be a good sissy. I have lost count as to how many times I have fucked Paula, at least 10 times a week, sometimes we have double teamed or tag teamed Mario. When he is at home, he is now known as Mary. He is always collared, and mostly naked except for being made to wear ugly granny panties. He has a Bluetooth controlled butt plug he wears to work, and his cock and balls are always caged. She only allows him to shoot his load when he is getting fucked, and it is in a cup, so he can drink it afterwards. We are planning to take him to a cruising spot and let him get gang banged.
Paula's new found freedom has become very profitable for me. She has had other women that were in similar situations as her contact me, and for a fee, I would meet them, break him down to a sissy bitch and fuck her all I want and get paid for my time. Tonight, I will be meeting Paula and three of her friends who are attached to losers, and think they are gods gift to women. Tonight that changes, all of these men (for now) have made open passes at Paula and commented about her tits, and hot ass. They think that they are meeting at Paula and Mario's house for a small dinner party. The women are all going to slip something into their partners drink, causing them to pass out, also I took a special pill, because I am going to be doing a lot of fucking and cuming tonight, way more than normal. When they wake up, they will all be tied over the back of a chair, wearing ugly granny panties with the ass cut out. Except for Mario (Mary), he would be wearing a too small French maid outfit, remote controlled butt plug that had a horse tail attached to it and a cock cage that had a remote that sent a shock to his balls. He is the ugliest French maid alive.
After about 2 hours, the sissies in training, starting to wake up. So we didn't have to listen to them whine, they all had ball gags in their mouths. The first things they see, is me naked except for a bright red jockstrap with the word master on it sitting there surrounded by their naked partners stroking and rubbing my body. When they are all awake. One of the women, Alice is the spokeswoman for the group. Alice is 55, 5'2, 155 pounds shoulder length brown hair, dark brown eyes, Full D cup tits with small but hard nipples. Even though she is a little heavy and round, she is pretty and has a sexy fat ass. She sat on the floor about a foot in front of her boyfriend and spread her legs wide, so all of them had a great view of her fat pink pussy. Paula ordered Mario to sit behind her so she had something to lean against. As Alice told the men what was going to happen tonight, she was playing with her pussy, and pulling on her big tits. She went into perfect detail as to what is going to happen, to them. You could see the look of anger in their face when she told that that I will be fucking all of the women, in all of their holes. But, the look that came over their faces when she told that before the night was over, they will all have their faces and ass filled with hot black cum, and that all the ladies are going to fuck them with big black strap-ons. She says, we have had enough of your mean and abusive ways, we are taking charge. By the end of the night, you are going to be as much a sissy, and cock loving whore as Mario. Hope you like his cute little dress, because we have one for all of you. So my sluts, while we are using you as we please, one of us will be getting fucked in our cunts, mouth and ass by that gorgeous black man over there. When she pointed towards me, one of the other women, Jackie had my cock out and in her throat. Jackie is 60, but looks like she is in her 40's. She is 5'6", 110 pounds perky B cup tits with long nipples small semi flat ass and a baby smooth shaved pussy. she is a very pretty lady. The other lady, Franny. She is the only black woman in the group, and she is married to Randy. He is a big Irish fuck, and the most abusive of them all, but that is going to change real soon. She is 5'5, 145 pounds, huge EE tits, and big nipples. Despite her weight, she is thicker than fat, except for her big ass that is built for a big dick to be buried in. She was sucking on my very hard and sensitive nipples.
The ladies, decided that Randy ( who is now Roberta) would be the first to start the training on. Paula (the leader), had Franny and Jackie switch. Jackie stood up and put her pussy in my mouth and Franny turned, facing her husband, and slid down balls deep on my big black cock. She moaned out loud, fuck, I forgot how good a big black cock feels in my cunt. She looked straight at Randy and said, MMM Randy, his black cock is filling me up so much more than you do. She waste any time, and start fucking me like it was going to be her last time. Jackie had sat her bald pussy just right to get a good licking and tongue fucking, while reaching around and Playing with Franny's big tits. Alice made Mario (Mary) lay on his back and hold his legs up and open. She was fucking him with the butt plug and slapping his caged cock and balls at the same.
The other three sissies in training were so in shock watching what was going on in front of them that they didn't notice that Paula had put on the same big black strap-on that she used to break Mario in with, has moved behind Randy. She had put just enough lube on it to help slide in his man cunt. The lube she was using was one that gets hot when it is inserted into something tight (an ass). Then she winks at Franny as in a signal. Franny raised up, aimed my fat wet dick towards her tight ass. As soon as she started lowering her tight ass onto my cock, Paula slammed her fake dick into Randy's tight ass. I am not sure who screamed out louder, Franny or Randy, and he had a ball gag in his mouth muffling most of it. Paula wasted no time in fucking the hell out of Randy, the other two sissies had a look of horror on them and were squirming around trying to get free before they got fucked. While she was bouncing on the first dick in her fat ass, and moaning loudly, her gaze was on Paula fucking her husband hard, and deep in his ass and trying to scream out around the ball gag, she couldn't believe it was happening, yet it excited her, so much, she had an anal orgasm.
After a while of banging Randy in the ass, Paula stopped moving and she saw that he was moving back and forth on the fake dick. Paula says look, he must like it, he's fucking me and his dick is hard. The ladies stopped what they were doing to watch Randy, u*********sly fucking himself, and he dick betrayed him by getting hard and leaking. When he realized what he was doing he stopped, but he could hide his erection. Franny was even more excited than before. She got off of my dick, put on one of the other strap-ons and took paula's place. She rammed that toy deep and hard in his man cunt so hard, the chair almost tipped over. His eyes bulged out and a loud muffled grunt came out from deep in his gut. Franny said loud enough for all of us to hear, MMM bitch I am so proud of you, for taking this dick like a real slut, get used to it, because you are going to get lots more of it, Then she started fucking him harder than Paula was.
My dick didn't get a chance to rest, as soon as Franny got off of me, Jackie dropped her tiny ass all the way down to my nuts in one move. She moaned out, fuck daddy you are so fucking big, it feels like you are splitting me in half. She looks at her husband Victor (soon to become Vicki). This is why I never let you fuck my ass, it wouldn't feel like this. That was Paula's que to ram her dick into his ass and started fucking him deep right next to Franny fucking Randy. I looked over to see that Alice had Mario on his back, she was sitting her fat ass on his face making him eat her ass, at the same time abusing his dick and balls. A while later it was Alice's, husband Billy to start his training. Paula move over to him, Jackie started fucking Victor. It's Alice's turn to ride my cock with her fat ass, but I was ready to cum, so before we started, I got up and went over and stroked out a big loud on all three sissies faces, returned to the couch and let Alce have her ride on me, then take her place behind her partner and fuck him too. Because his shot a load while Alice was riding his face, Mario had to be punished. Paula got a towel, wiped off my dick from the other ladies juices. Then she made him sit his ass on my hard prick dry. You could tell it hurt his so much he wanted to pass out, but he knew better. The only problem was, it was painful for me also. Paula says, I am so sorry daddy, it was the best way to punish my bitch. Paula pushed him off of me, shoved the butt plug with the horsetail back into him and made him stand in the corner.
Paula took my cock in her mouth and gave me a nice blow job until I filled her mouth with hot cum. Then it was time for the next phase of sissy training. All the ladies stopped fucking their partners, took off the strap-on's and then sat in front of the and played with their cunts. Paula says to the sissies, now you're going to be tested, by our daddy to see if your training is working. If not we start all over again. I took up a spot behind Billy (now Bella), shoved my dick in his pussy and fucked him until he blasted out a nice load. I repeated the same treatment with the other two, only with Randy being last, and the biggest ass of them all, I saved the best for him. I had Paula take his ball gag out. She warned him that if any sound came out of him other than a moan, he would be punished. She then holds up a big dido in his face and says she will shove it down his throat. I hate fucked that bitch. Grabbed his hips hard and tried to fuck my dick out of his mouth. Then I gave him one more hard stroke, left myself buried in his gut, and filled his man's pussy with a big load of my hot cum, My orgasm triggered his. Paula said the view was perfect. My cum dripping out of his gaping ass and his dripping from his.
I went back to my seat on the sofa with the ladies sitting around me rubbing and stroking my body. Paula spoke for the group. Since you are no longer men, you are sissie to your partners and you will refer to them as Mistress. You follow all of her rules and orders. your useless penises will never penetrate any part of their body, and your only sex relief will be what she allows. Then she says look around the room, there are several cameras that are recorded every second of tonight. The tape will be edited to look like you were willing participants. So if you forget your new role in life, we will make sure that the recording is released to everyone you know. The ladies untied their partners and re-tired them in the chairs the normal way, and put their ball gags back in place. For the rest of the night They were forced to watch me fuck their women in all of their holes over and over. More than once they got my cum shot all over them.
After two days of serious sissy training they were allowed to get dressed and go home. The only one who decided to revert back to being an asshole was Randy. So we kept our promise and released the video of his training. He was forced to quit his job, Franny divorced him and got almost everything he owned. Last we heard, he was homeless living under a bridge. His family won't have anything to do with him. Since that group, Paula and I have trained about two dozen more sissies, and still find time to fuck each other as much as we want.
Published by bruce1425
2 years ago
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