Paul has not worn men's underwear in months now. He wears my panties to work every day, or wears the silky things I make him pick out and try on at the Victoria's Secret at the mall. This humiliation ritual is just one of the many things I do to him to keep his male-ness in check and turn him into the perfect lesbian slave for me.
Paul stands before me in a long latex hobble skirt.
He looks delicious as usual, this time he’s put even more off balance by a pair of black patent leather pumps with 6 inch heels. Tonight he will be the center of attention as the slut toy of my 3 best friends. My girlfriends are to arrive shortly and he is preparing my place for their arrival, struggling so beautifully as he does.
Paul has not worn men’s underwear in months now. He wears my panties to work every day, or wears the silky things I make him pick out and try on at the Victoria’s Secret at the mall. This humiliation ritual is just one of the many things I do to him to keep his male-ness in check and turn him into the perfect lesbian slave for me.
He’s nervous tonight for two reasons. One is that tomorrow we start his hormone therapy (months of using a breast enlargement machine on his tits has done no good) and tonight he is going to be the hole for one of my girlfriends who has never used a strapon before.
Both things terrify him.
The inflatable, vibrating plug in his ass makes it even harder for him to walk. I have a remote control that I keep in my pocket and can cause him all kinds of humiliation at a moment’s notice. Sometimes I turn it up on high just to watch him shudder, and I walk over to him and look at the way his whole body trembles as if he is in an electric chair.
I stroke his cheek. “Aww…poor paulina, is that uncomfortable?”
But Paul cannot speak. Panties are in his mouth, the panties I masturbated in while he watched just an hour ago. A harness is over the lower part of his face to keep them intact. The harness also has a buckle in front so I can attach a large, protruding dildo. This is so he can service my girlfriends later that night, face – to – pussy, while I take him from behind.
This is going to be a long night for Paul.
But he has come a long way.
**
When I met Paul he was a typical wisecracking, arrogant salesman for a large medical supply company. I met him on a road trip when he tried to hit on me (and cheat on his girlfriend at the time).
“So wanna come up to my room?” he had asked, leaning over to me. I could smell the beer on his breath.
“I thought you said you had a girlfriend?” I reminded him, pushing him back a little.
He smiled. That sleazy, salesman smile. “What she won’t know won’t hurt her,” he had said.
Little did he know how much it would hurt him.
**
I let Paul up into my room that night. And when I tied him up, he had the typical, lecherous man-toy response, something like, “Oh baby, kinky, I like that. I like kinky.”
“Oh yeah?” I asked, taking out a huge dildo, a tube of K-Y and a long leather whip. His eyes got a little wider.
“Shit, what the hell are you into?”
I straddled his face. Don’t get me wrong; Paul was a good looking guy. He was quite gorgeous actually. Which is why breaking him was even more appealing.
“You like to eat pussy?” I asked him.
His eyes were focused on my panties; my skirt was hiked up a little and I was teasingly rubbing two fingers on the crotch of my silkiest pinks. “Oh yes,” he said predictably.
“You won’t be getting any pussy tonight, Paul,” I said to him.
I dismounted and he moaned, trying to get loose. But I had tied his wrists securely to the headboard with stockings, and he wasn’t going anywhere.
This is the part I enjoy the most, I think. When a man who has never seen a woman like me watches me step into a strap on harness. Because at first he thinks it is some contraption I will use to fuck myself; oh no, not at all.
Then he sees that the big, 8 inch dick sticking out is for him. Oh, you should see the look in his eyes. Panic. Begging. Sometimes laughing in disbelief.
But Paul was a sharp one. He knew he’d screwed up. He knew it, even as I pulled his legs over his head and chained them to the bed frame. He knew when I pulled down his designer briefs, slapped his ass and told him he was going to be re-trained and learn to treat women right.
And damn, was his hole tight. He howled so loud I had to bring out my biggest cock gag, which took some work to get into his mouth thanks to his homophobia.
“Later you’ll be sucking THIS dick,” I told him as he fought and howled.
It shut him up sufficiently, and I enjoyed riding him for a good long time before his ass loosened up and his dick started to stiffen under my expert grip. In that position I could smile down at him and taunt him with his growing erection.
“I think you like it up the ass,” I told him. “Your dick is so hard. It’s harder now than it was when my pussy was in your face.”
He looked so humiliated. But his dick was dripping pre-cum already. Drip, drip drip. I pointed it into his face. It got into his eye. He tried to get away but couldn’t.
I fucked him and pumped him until he came all over his face, then I released his legs and let him lay there until the cum had dried completely.
Then I took a polaroid, only after slipping my panties on him.
And I told him I’d send copies of the picture to his office unless he followed my directions.
**
Needless to say, Paul did as told. I was at his apartment the next week, taking all the men’s underwear from his dresser and shoving it into a big bag.
He watched me despondently.
“I am altering your wardrobe,” I told him. “And I am taking over your dick. You don’t cum without permission, and you can forget about sticking your cock into every woman you meet on the road.”
I could tell what he was thinking – I could tell, because he didn’t see all that worried. Because he figured he’d go out and buy new underwear when I left, and he’d stick his dick into whoever he pleased when he was out of town in a few days.
Until I took his wallet. I took away his credit cards, checkbook and money. I took everything but ten dollars.
Then I had him bring up my luggage – I informed him I would be staying a few days, to ensure the start of his training went well.
Then I locked the steel chastity pump onto his dick. It was a specially made steel harness that crushed his balls together (to make him more compliant) and prevented him from getting hard. He could piss out of the top, barely. And it was secured with a lock at the base and two more locks on the side.
“This is temporary, until I get a piercing on your dick,” I told him.
His eyes widened.
I smiled and patted his ass.
Then we started his training.
**
Paul, or “paulie” as I started to call him, had to first learn to eat pussy for hours, to worship the female body and to get no pleasure for himself. This is my favorite part of a man’s training.
First, I made him meditate in the corner with my wet panties over his face, taped in place. I would command him to lick the crotch, but only on my order. This would start and stop over the period of an hour or so until the panties were licked clean. They would then be inspected, and I would bring over the next pair.
Eventually I put my panties on him, and they were too tight. The steel device made them pretty much impossible to get on (as I am pretty petite), so we went out shopping for his own panties. I made him try them on in the store. Already his cocky attitude was fading. After all, he was waddling around in a steel trap around his dick and he had a small training plug in his ass.
Nightly I would mount his face and pump up and down on his tongue, and he had to hold positions that I explained to him. Sometimes I would just crouch down on him and smear my wetness all over, then dismount him and masturbate on his chest, making him wail in pain because his erection throbbed so hard in the device.
One night he cried to me. He was on his hands and knees doing anything I told him, begging for release from the device. He said his balls were crushed and his dick felt like it was on fire. Big tears streamed down his face. He said he was suffering from an infection. He demanded to be taken to a doctor.
I handed him the phone. “Go ahead and call 911” I told him.
Because I knew it was all bullshit. He was just horny. And the more horny a man got, the more desperate he was.
**
By the second weekend I had him dusting and vacuuming nightly. He would wear a short maid skirt and put a big bow in his hair. He was used to the tight cock harness by now and he could accommodate a medium sized plug with ease.
Our nightly pussy worship sessions were peaking at 90 to 120 minutes without a break for him, and I started to make him do my friends, too. They always look forward to this part of the training because they get free orgasms and are not required to do anything in return. Not even look at the guy or talk to him.
It’s like a girls’ slumber party, we eat ice cream and wear lingerie, and talk as if he is not even there. But we switch off mounting his face and one of us enjoys the licking, nibbling and sucking.
My friends know the codes, too. And we just bark them out like he is an automated pussy worship machine. “Tongue,” means deep penetration, “SUCK,” means alternating deep sucking and soft sucking. You get the picture. There are fourteen commands in total, and Paul knew them all.
By the end of the night his face was chaffed and he looked like shit. His hair was stuck to his face, stuck with pussy juices, sweat and spit. He was led into his puppy cage and put down for the night.
Then the three of us sat up drinking champagne and talking about the real men in our lives.
**
So, let’s see. Around week three I started toilet training him and he was doing complete house chores. He was also dressing only in women’s clothes when he got home from work, and he was allowed one orgasm every two days but he had to drink it all from a glass, and it was only for that week only; then he would return to one orgasm every 4th month. This was just a break to start his cum-eating training, so that I could eventually use him as a service whore at fetish parties.
The best thing about Paulie, though, was his change in attitude. He would assume position at my feet each night, he was compliant and sweet to all women he came in contact with .
The true test was when he brought me to a work function one night. He was in his work mode, in a nice suit and looking very handsome. The women in the office all giggled and pointed to him.
I was sipping wine when one of them came up to me to compliment me. “I don’t know what you did to Paul, but ever since you two started dating he has been such a nice guy. You probably don’t know this..but before, he had the worst reputation in the office for being a pussy hound…no offense. He just was such a skirt chaser.”
I smiled and introduced myself to her. She was cute, a little younger than me. In fact, I sensed she might like to know more about how complete Paul’s change was. “Well, it’s taken some work, but I think he’s on his way to being a perfect gentleman. You should come over some time, I ‘ll let you in on my little secret.”
She laughed. “Yeah, I’d like to know how you did it. I know of a few guys that could use a similar treatment!”
Yes, I thought. This was a girl I wanted to get to know.
**
That night, after the part, Paul removed my shoes and rubbed my feet. He looked up at me adoringly as I fingered his hair. “You are so much more likable now,” I told him.
“Thank you,” he said, and he beamed. He had long since learned that the only pleasure he sought in life was my pleasure. When I was happy, he was happy. Nothing else mattered.
“Take me to bed,” I ordered. “I want you in garters, stockings and bra. Put on a lace nightie for me. Then, service my ass for a half hour. If you do a good job, I will let you sleep at the foot of the bed.”
He looked genuinely thrilled.
And the rest of the night was perfect.
**
So now, some three weeks later, I sit waiting for Paulina (her new name now) to finish party preparations.
My new strap-on trainee is none other than the secretary in his office that I met at the party; he has no idea, and when he sees her buckled into my brand new 9-incher he will die of embarrassment, especially since he will be on all fours with a big cock in his mouth (mine).
The skirt looks lovely on him, though, I must say. And he moves as gracefully as he can. In a moment the guests will start to arrive, but not before I take him back and practice a few slave positions with him.
Then I am giving him away, sadly. Tonight is my last night with him; I plan to offer him to my friend Cindy.
There is another man that needs training. The arrogant, mindless guy I see at the gym all the time. He’s 210 pounds of solid muscle, at least. He hit on me for the last time the other night.
Tomorrow, I will start on him. In a month he’ll be wearing women’s leotards at the gym and working out with a big plug in his ass.
He just doesn’t know it yet.
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