tagTransgender & CrossdressersFrom Her Ex-Boss to her Bitch

From Her Ex-Boss to her Bitch


A past employee seduces her straight married ex-boss and turns him into her bitch.

He was straight married family guy away on a conference. A lot of work to be done but also some fun to be had on the nights out, at the very least a few drinks with friends.

The conference was going well, he'd got the wines ready for tasting as he looked up he saw her. Tousled long brown hair, piercing green eyes and that smile and laugh.

She'd worked for him in a retail setting, always on time, full of energy and strangely attractive, Pete had always been taken with her.

One of those attractions where he would inwardly gasp as she bent over to pick something up. She was 24 and he 49 so she'd never be interested in him. Especially as he was married with kids.

She'd certainly put weight on, the jeans well filled out, with what had always been a fine ass, now much more a serious booty. She looked somehow stronger and more alluring with the extra weight.

He had a dark side, he'd dabbled in BDSM since his twenties and had visited a fair few Pro Femdommes before he was married and since. For him it was an itch he scratched once in a while when he travelled.

He didn't completely see it as cheating, his wife was absolutely vanilla and their sex life was non-existent, as with so many 40 somethings. But he always felt guilty after, then the yearnings to be dominated would grow until he had to scratch the itch once more.

Today though as he saw her, BDSM was the very last thing on his mind.

He was just happy to see Rachel, and it seemed she was to see him, she strode across and gave him a big firm hug, her small breasts pressing into his chest, her perfume pricking his sense of smell. Her face lit up as she told him that she was so pleased to see him. They chatted about her new job and said they'd catch up over a drink later in the evening.

The day raced by just focussed on work. A fleeting look across the room at her a few times always seemed to end in her catching his eyes too and smiling. He hoped she didn't this he was being creepy. Then he saw Rachel coming across with another stunner from another winery who had similarly long tousled hair.

Rachel introduced him to Claire said that they'd both catch up with him later at the dinner and then look to go for a drink or two. He knew the chances were they'd probably not catch up, but secretly hoped that they might, it would be lovely to spend the evening with two hot twenty year olds.

The evening went by quickly, some great music, excellent food and lots of networking, Pete hadn't seen the two girls until they were all leaving the place as the bar closed.

Rachel and Claire raced over to him and each one took one of his arms, as Rachel announced it was time for Havana bar. All slightly drunk and swaying as they walked, they chatted, sang and walked in step.

The night was a bit of a blur, drinking the bar out of tonics after round after round of G&T's, finally the bar began to thin out, Pete was sitting on a bar stool each girl either side of him and somehow his arms lightly around their waists, neither of them seemed to find that strange.

Finally Claire declared she had to go as she was getting up for work early, they kissed on both cheeks and Rachel walked her too the door, the two of them giggling at something Rachel said.

She tottered back over to him on her lovely nude patent high heels, her ass swaying suggestively as she walked, he was looking far too intently, but beyond caring about what others thought.

"Let's got through into the back room, it's a little more intimate there."

Her suggestion took him by surprise especially the use of the word intimate, but it was a good surprise.

The sat alone in one corner of the bar, low lighting, intimate as she'd said and Rachel sat very close to Pete. Their thighs touching, in fact almost rubbing against one another.

"Claire's a really cool girl." Pete said with a hint of trepidation.

"She is, and very sexy don't you think."

"I hadn't noticed to be honest."

"You bloody liar, your eyes were all over her, but I can't blame you I have a thing for her too."

"You do, my Gaydar must be off, I didn't realize." He hadn't expected this turn of events.

"No it's not your Gaydar, it's your Bidar." She smiled as she looked directly into his eyes as she said this.

"Ahh I see, you swing both ways, I didn't know." Pete was still fishing and somehow pleased at the revelation

"Why would you, I don't tell many people, I just happen to like pussy as much as I like cock. I reckon most people do if only they would try." Now she had a mischievous look in her eyes.

"Who knows, you might be right, I guess somehow it's still more acceptable for women to be bi, than for guys, somehow the whole gay thing rears its head."

"Maybe for your generation, but I have lots of outwardly straight male mates who love nothing more cock in their holes, I'm completely relaxed with it. In fact for many women it's a massive turn on."

Shit was getting real for Pete now, not that comfortable discussing being with guys, the closest he'd come to that was having a session with a TV Mistress one time. Well that and a lot of experience of strap-ons and butt plugs.

"Good for you, not for everyone though I guess." He tried to change the subject slightly wanting to know more about Rachel's bi tendencies.

"So what about you, you a giver or a receiver when you're with a woman." As the words came out of his mouth he thought "Shit did I just go too far."

She looked on and moved her face even closer to his. "Well aren't you a dark horse, first your staring at both of us all day long, looking like you're undressing us with your eyes and thinking of how you'd fuck us both. Then you have your arms around both of our waists and now you want to know if I wield a big strap-on or open my legs wide for it, you horny little man."

He smiled back at her, worried he really had stepped over the line, then the comment about wielding a big strap on or opening her legs wide , had him reeling. She was so much more suggestive than him, but now here he was getting horny and hard in his jeans just thinking and also focussing on the words big and wide apart. The final thought was her use of the word little, he was a pretty big guy, what was she alluding to. Rachel was obviously a bit naughty, he ought to be careful.

"God sorry Rachel, I didn't mean to offend, I was just curious."

"Hell you didn't offend me, I'm not easily shocked, in fact I'm never shocked and for the record I'm a wielder of big strap-ons." "and not just with women, I'm a top with guys too..."

She left the two statements hanging in the air, truly amused at what his response would be,.

He blushed "Wow more information than I needed, but good for you."

"Now we both know that's not true, don't lie, it doesn't suit you. Your longing to ask me more, look how turned on you are." She looked down at his small bulge and put her hand on his thigh."

He almost jumped with the electricity of the touch, fuck what was happening.

"Ok busted, I am fascinated, I confess."

"Ok then your turn, confess something to me that others don't know. Any bi thoughts, any bottom thoughts?"

It was a trap he should have walked around but his small prick was rock hard now, he longed to be able to rearrange it.

Almost as though she could read his mind, she said "You might want to rearrange that hard cock of yours, it must be uncomfortable." As she said it she brushed her hand lightly up his thigh and fleetingly over his cock. He let out a small gasp.

He knew he shouldn't, fuck what was he doing, but this conversation was too far gone now.

He leant back in the chair and reached down into his jeans rearranging his tackle so he was more comfortable.

"So now you're more comfortable, answer my naughty questions."

"Ok I admit it I have had bottom fantasies."

"I knew it, I can always tell a real sub, one who's not just playing at it, but feels the need in their very soul. That's you isn't it?"

"I guess it is Rachel, fuck you cannot tell anyone this."

"Jesus Pete, of course I won't, I just told you I fuck women and men with strap-ons, I think you have a bit on me too."

"Ok I guess so, well I have had quite a lot of experience of strap-ons, I've visited a lot of Pro Fem Dommes over the years."

"Ok so you're a true bottom, what about men?"

"No not so much, just one visit to a TV Mistress."

He could see her hand gently rubbing between her legs, she was enjoying this "Fucking perfect, so did you suck a real cock and take a real one in your man pussy."

"Well I've never called it that, but yes I did try both and can't say I'd race back."

"I'm not sure I believe that or why would you have sucked and fucked in the same session and not simply have backed out after sucking one? You carried on for a reason."

"OK maybe it wasn't so bad, but I prefer women,"

"No you prefer the idea of women so you don't have to feel guilt, is that closer to the truth."

"Shit, what are you a psychologist, fuck you seem to know what I think."

"I know what big guys, with small cocks and a submissive bent think, that's all."

He was offended "What do you mean small cocks."

"Well" she said stroking the outline of his cock upwards from his balls as he moaned slightly.

"In my experience guys with more than 6 inches pack it down their leg not up their stomach. And what's more I can feel it's not big. Although the balls feel good and large."

"Don't be ashamed I love small cocked men, all the more fun from my point of view."

"Fucking hell what point of view is that Rachel."

She looked deadly seriously at him, still stroking his cock through his jeans. "From the point of view of a Domme, I love to dominate men and women and I love to make men as submissive to me as possible."

"Jesus Rachel this is getting heavy, are you coming onto me or what?"

"Well ever since I met you I was sure you were submissive, but I only hoped that you were Bi, that makes it so much more fun for me. Now tell me was the TV Mistress bareback or wearing a condom"

"But I'm not Bi it was one session. But yes she was bareback."

"I thought so, and you chose her bareback, you chose to explore the fantasy. I know what it takes for guys like you to do that, you have to have fantasised lots of times to get to that point, isn't that the truth. Accept it you sucked a cock and got fucked by one. And I'm pretty sure you loved it."

He knew when he was defeated, "I did yes."

"I did yes Mistress."

"Are you fucking serious, we're in a bar, we know people here."

"Oh shut up, you love this, you and I both know it, it's time to have some fun... Say it."

"I did yes Mistress."

"That's better slut." Again the words changing as she took him deeper, he'd gone from little man, with a little cock, to slut in five minutes. She knew what she was doing which was frightening in one so young.

"So let's summarize what we know, I am a strong young hot Domme who loves to dominate submissive older men, well any age, truth be known and also to use submissive women as my playthings. I love to use strap-ons with abandon and you are an older submissive male with a small cock and bi sexual tendencies, who loves things in his ass pussy. Does that sum it up slut."

He hesitated only for a second, the thought of being dominated was like cocaine to him "Yes Mistress that does sum it up."

"Good then let's begin, it's only 1 am and we have some fun to have, don't you agree slut. I think it might be more fun back at my place."

"Yes Mistress I do agree." He was almost panting with anticipation. Although he'd fantasized about licking her pussy and fucking her from behind, this reality was way more exciting to him. In a different league.

She reached into her handbag and passed his a pair of black lace trimmed panties and a decent sized black butt plug. The gave him two silver foil packets containing what he knew to be Ducolax suppositories to clear his bowels.

I take it you need no instruction in these matters slut?"

"I need no instruction Mistress."

"Then go and come back prepared in 5 minutes, do not make me wait slut."

He'd been dressed by a number of fem dommes over the years, all part of the fun, but the humiliation was always bitter sweet for him as he knew as a heavy set guy he'd never even be close to passable and the whole sissy hypno scene truly excited him.

He jumped up and went into the small bathroom, quickly taking off his shoes and trousers then his briefs. He opened both silver packets and took out the small white waxy torpedoes and as he had no lube he licked his index finger and sat on the toilet reaching under and pushing the first one in as deep as he could, then the second. He knew from this point he had the maximum of an hour before he would be desperate to empty his bowels.

He picked up the black butt plug and licked the tip, trying to coat it in as much saliva as possible in lieu of lube. Again he reached under and began to tease his ass hole with the tip of the plug, he looked at his watch and realized time was slipping away, he had to go faster.

He rested the base of the plug on his three middle fingers and began to rock the butt plug up and down, going a little deeper every 10 strokes, widening his hole bit by bit until the last set of ten when he managed with a big push and by bearing down on the plug to lodge it in all the way.

He breathed out, picked up the panties and saw that they were used from the slight staining on the crotch, he had to smell them, the aroma was intoxicating, pussy and piss and he loved it. He looped his feet into them, stood up and pulled on the panties, actually loving the feel of them as he had done in the past. They sat snugly against the base of the plug and he pulled them up high. Then on with his jeans and shoes and socks, just out in five minutes.

What he wasn't aware of was that during those 5 minutes of preparations Rachel had not sat idly by, she rang Claire straight away "Hey there, we were both right, but the best bit is he's more experienced than I first thought so we can take him much, much further and really let you get some good dirty experience. Make sure you stay well hydrated and I mean fit to bursting, get dressed in the clothes I put out for you, the full outfit, then hide in the guest bedroom until I call. Have you got all the equipment ready Claire."

"Yes Mistress Rachel everything is ready, I've got the biggest sizes of all the clothes, not sure the shoes will fit him, I was looking at his feet earlier and they look quite large."

"Don't worry, I think the size 13's, 5 inch heels will fit this bitch perfectly."

"Mistress I'm so excited my first slave."

"Well not quite Claire, he'll be my slave but he will be sub to you and as you live close by I'm sure that I'll allow you to have a lot of fun with him whilst training him for me."

"Yes Miss Rachel."

Ok, make sure the drinks are made, I'll want him drunker than he is at the moment, just make mine with water, get the poppers out too and all the toys."

"They are all out on the side table Miss, they look bloody impressive if I do say so myself."

"Don't even think about using them now you tart, I want you as horny as possible for the training and don't forget stay hydrated."

"Yes Miss Rachel, I will."

As Rachel put the phone down, her latest conquest came out of the bathroom walking rather bow legged.

Perfect she thought, absolutely perfect.

"How did you like the aroma of the panties slut."

"How did you know Mistress."

"Because you are a submissive slut and the smell of a new Dommes pussy and piss are like drugs to you."

"You have me there Mistress."

"Then just remember. I'm your superior and I'll generally know what you're thinking before your simplistic slutty sub mind has formed the ideas. Once you were my Boss, now you'll be my bitch, how does that sound slut.?"

"It sounds wonderful thanks Mistress."

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