by Alice Lloyd
Then I wanted my first piece of blackmail evidence.
I got him to take down his trousers and underpants and to start playing with himself whilst sitting in his desk chair, looking at the computer screen. When he was about to cum he should stop and tell me.
Standing behind him and leaning over his shoulders I typed some searches into google. My first search was ‘granny porn videos’ and I selected a clip of the fattest, ugliest, oldest woman I could find. Richard was clearly hard, dick in hand and the lovely lady was clearly in shot when I took the first picture. I told him to look around at me in horror as if I’d just caught him in the act. It looked very realistic.
The second search was for adult baby porn – guys dressed in baby gear and getting bottle-fed by their nanny mistress. Richard started to moan and told me he was about to cum – so soon? Did he secretly like this? Did he want me to dress him as a little girl? An ickle sissy girl? Would he like that, because we might just have to do it. He really did look like he would cum at any moment, so I told him strictly to stop before he came – we weren’t done yet - and I took another picture for the album with him looking down at his very erect penis, a sissy girl in a pink dress in shot just behind him.
My final search was for ‘sissyslut fuck’ and I think he knew exactly what I was doing when I deliberately pretended to be indecisive about whether the video should be one where the sissy is dominated by women or by men. I chose men.
There was a video of a sissy transvestite being spit-roasted by two well-hung guys. I told Richard this would be the clip he would spunk to and I would want to capture it on video on my phone. Just before he came he would turn to the camera and say ‘my name is sissy Rachael and I want to be fucked by two big hard cocks.’ He would then make sure to spray his spunk all over the screen and then he would lick it off. Enthusiastically. Saying he loved the taste of spunk."
"Bloody hell, Holly, you don’t do things by half," I said.
"Did he do it?" asked Sarah, clearly interested in how she might progress with Nicola’s submissive training.
"Not only did he do it, he loved it. I think at that point it was probably the most erotic moment of his life."
"And how did he feel the next day?" asked Sarah, "Did he regret it and ask you to stop?"
"Well, I had my doubts. We were lying, cuddling in bed together the next morning, when I told Richard that that I’d give him two chances to change his mind. One would be right now and the second would be exactly one month from now. His hardening cock against my bum as we cuddled told me the answer to the first option. I wriggled my bum against his cock and said I’d take that as a ‘No, mistress, I wouldn’t like to stop just yet.’
Then, still wriggling my arse against his erection and secretly toying with my clit – I was getting very horny playing this dirty game - I told him to describe what a blackmailed humiliation slut ought to wear under his suit to work today. I agreed that ‘my used panties’ was a reasonable first answer, but I said I knew he could come up with an even better suggestion than that.
After a moment’s reflection he then said the big out of town supermarkets sold lingerie and they would be open from seven this morning. A real slut would buy their own set of lingerie and put it on before work.
I turned over, pecked him on the forehead and said that was such a good suggestion that he deserved a reward. I reached over to the bedside table and got a condom..... he was pretty hard by then and I rolled it on him. I got him to lie on his back so I could climb on top of him and guide his cock into my pussy. I was wet and he slid in easily. I lay there on top of him, my legs straddling his, my torso slightly raised on my forearms and elbows so I could adopt a dominant, controlling position with his cock inside me. I remember looking at him like a praying mantis about to devour her lover.
I didn’t do anything more than squeeze a little gently up and down with my hips, all the time staring into his eyes, and he kept getting harder and harder inside me. ‘Tell me exactly what you will buy to please me. A slut like you needs to wear more than just a pair of women’s panties under your suit.’
He told me he would get a full set of the silkiest, laciest, most feminine panties, suspenders, stockings he could find... and also a matching bra.. even though that would mean having to wear his jacket all day to hide it... I rewarded him with another little controlled squeeze of the hips up and down his straining erection with my warm, tight pussy muscles.
His lack of performance in our relationship to date had meant he’d never actually been able to cum inside me before then, but there was very little doubt in my mind that it was about to happen right now. I was still looking directly into his eyes when I said;
“So to recap, you’re going to buy the underwear this morning. You are going to put it on in the toilet at the supermarket immediately after you buy it and arrive at work wearing all of it under your suit. You will be wearing it all day, sending me photographs on demand if and when I text you, and finally, this condom of spunk that you’re about to produce? You’re going to take that to work and put in an empty take-away coffee cup and the second you see Claire, your rather attractive boss that we both fancy, you will drink it. All of it. Promise me, sissy Rachael, promise me you will do it. I want you in panties and drinking spunk at work. Don’t disappoint me, understood?”
He nodded, trying hard to hold back his orgasm.
“Now I’m going to make you cum. Look at me and say thank you Mistress Holly…... Again……... Say it again....
[ my hips and pussy muscles were tightening and thrusting rhythmically now, rocking up and down ]
Whose bitch are you? – I slapped him across the face - Yes, that’s right, keep saying it.... I’m Mistress Holly’s bitch....My name is little sissy Rachael, Mistress Holly’s little blackmail bitch......say it...... say it again, louder.....- I swapped hands and slapped him again, harder this time, whilst milking him with my pussy and hips….
....and then he came, closing his eyes and arching his back as I kept slapping his face again and again…….the orgasm shook his entire body.
When he open his eyes I was staring back into them and admiring his face reddened by his shame and by my slapping - I sniggered, dismounted, carefully unrolled and tied off the end of the condom in a knot without spilling a drop, and placed it in his jacket pocket.
He looked at me as if to say, “Shit, she meant it. I’m actually going to have to do it.”
Of course I meant it – he wanted blackmail, humiliation and control, so that’s what I gave him.
He never doubted what I was capable of after that. He learned to expect the worst.
I made him drink a lot of spunk in those six months or so when we dated. It always seemed like a good way to reinforce his humiliation. I think he got quite a taste for it in the end.
He licked spunk off my hand, off my boots and off the floor.
I made him drink it out of coffee cups in public when a pretty girl walked past.
I also made him iced cum cubes which I put up his bum before inserting a butt plug.
And the best bit?
Not all of it was his own.
Chapter 7. [ Sarah speaking ]
I was excited by Holly’s account of her relationship with Richard Thornberry and couldn’t help thinking of how things might turn out eventually between me and Nick. I wanted to know how the relationship had developed and how and why it had ended. Holly was clearly no longer with this man. Would the same happen to me and Nick? Despite everything I still wanted Nick (and Nicola) to be in my life.
Holly was only too happy to tell us more.
"Well, yes, of course we went our separate ways in the end – as I said, I discovered soon after that guys were not really my thing, but if I was going to be married to a man I could have done a lot worse than Richard Thornberry. He was a lot of fun.
Sarah, I think Nick is pretty much an identical type of man. Our relationship was basically this: All he really wanted from me was to control and play
with him sexually and he would love me for it. In return I got a nice guy – he was very sweet natured – to look after me and I also got to do whatever I wanted. I got to spend his money (he was pretty well-paid) and also sleep around with anyone I fancied. He wanted that. It turned him on. Can you imagine? On a Friday or Saturday night he loved it when I made him stay at home in his chastity device, dressed as a French Maid and clean my flat, wash and iron my clothes, while I went out and chatted up other guys (and later on, girls) and brought them back home with me. If my one night stand was up for it we would fuck right in front of him."
"You did that?" I asked, "and he didn’t flip out?"
Holly laughed. "Sarah, he loved it. It frustrated the hell out of him and it made him red-faced with shame and humiliation, but that was exactly what he wanted.
"And that’s when you first got into girls?" Jane asked.
"Well, thinking back I’d probably always been into girls, but it was the first time I’d slept with one.
It was a real mind-fuck for Richard when I brought a guy home for the first time and he had to listen to me being fucked while he hid in the cupboard. It was much worse when I tied him to a chair and made him watch me with another guy and then we laughed at him and made him clean us up afterwards –
I’d started going to clubs, taking a photo of him dressed up as a maid and asking guys if they wouldn’t mind coming back with me so I could make him suck them off. It would help me to humiliate him. I got him to do that twice."
"Bloody hell, Holly," Jane said.
"Well he hated it, but also loved it, if you know what I mean – but the worst, by far the worst for him, was when I had sex in front of him with a woman."
"Why?" I asked, trying not to betray how excited I was by her whole bizarre story.
"Because I knew it was a massive turn on for Richard and I told him I would make it memorable. Excruciatingly memorable."
"Oh my God, Holly, what did you do to him?" asked Jane, anticipating how creative and cruel Holly would be in a situation like this.
"Well, all I did was to swap his chastity device.... for a spiked one."
I looked at Jane as she covered her mouth as she gasped.
"The spikes weren’t razor sharp or anything. Not quite so sharp that they drew blood, but we both knew when we tested it that they hurt like hell if he got an erection, digging in painfully to his cock, and almost, but not quite, puncturing his foreskin. It certainly left a very pretty red polka-dot pattern when I inspected him afterwards."
"Sometimes, Holly, you can be a real bitch, can’t you? I’m going to need to watch out for you in future," said Jane.
"Oh, don’t kid yourselves. I got a dozen red roses the next day – one for each mark on his cock - and, no, I hadn’t told him to buy them...."
"What was it like..? - you know, sleeping with a girl for the first time?" I asked, "I mean, it’s a big step, isn’t it?"
I could see Jane look at Holly as she raised an eyebrow. I’m sure they knew it was more than academic interest on my part. I think by then I wanted them to know I was interested and available for a threesome.
"Well, I’ll assume you’ve yet to have that pleasure?" Holly asked.
"No,.... not yet..." I replied coyly.
"Well, you really don’t know what you’re missing. Once you’ve tried sex with a woman, at least to my mind, there’s no going back. Women’s bodies are just so..... beautiful....so sexy....... and you know, at the end of the day it was a girl, and girls know from experience what another girl needs to get her off, she certainly knows that much better than a man... and anyway, I was with a pro. She really knew what she was doing."
"You mean an escort? A prostitute?" I asked.
"Yes. I got Richard to pick her for me. I wanted him to choose someone he really fancied and someone he would love to be allowed to fuck himself, but I would deny him. The safest and easiest way to make it happen was to pick a really expensive escort who did both guys and girls. He would know that he could have paid this woman to sleep with him, but instead he’d be paying her to be in his bed having sex with me.
So with my full blessing he picked a leggy, curvy, strawberry-blonde with milky white skin, who called herself Amber. He said she looked like a glamorous old-fashioned pin-up poster-girl. Not really my type, Jane honey, so please don’t be jealous, but she was undeniably beautiful and I could see what Richard meant about the 50s screen goddess – all curves, big green eyes, long strawberry-blonde hair and bright red lipstick. She said she was genuinely bi-sexual and whilst she was happy to provide all the normal services she also did a side-line in domination. I made Richard pay her for the whole night. It was a good thing he earned good money. It cost him a small fortune."
"And what was he doing the whole time while you were having sex?" I asked.
"Amber and I had already gone to the bedroom to dress up in fantasy schoolgirl outfits when we called him to come up. Then we dressed him up to match our outfits – we put him in a little pleated skirt, white blouse, stockings and heels and so on, topped off by a wig with pigtails, and then we tied him standing up at the foot of the bed with a spreader bar between his ankles and his hands handcuffed behind his back, big ball-gag in his mouth, the spiked chastity device already digging in, and we told him he wasn’t allowed to look away from us for a second.
Amber had brought various whips and strap-ons with her and made sure Richard had seen how big and vicious some of them looked, telling him we would punish him severely if he as much as blinked.
I remember the agony and ecstasy in his eyes when Amber and I, dressed as schoolgirls – something I also knew he loved - started slowly making out on his bed - kissing and undressing each other down to matching stockings, suspenders and heels, and then we kissed some more, our hands and fingers exploring each other, our breasts and nipples brushing together. I’d never been that wet before. Amber gently spread my legs and then went down on me, licking me slowly to orgasm and then I returned the favour. She then covered the bed in a large rubber sheet, we both stripped naked and we poured generous amounts of baby-oil all over each other, slipping and sliding our oily hands and bodies against each other, directly in front of where Richard stood, until we both came again. Amber had stupendous tits and I made sure to oil them up when she was facing Richard so he could get a direct view of the show.
We decided he’d not been concentrating to our satisfaction and on several occasions we’d seen him close his eyes in frustration and pain, so we had every excuse to whip and paddle his arse and turn it pink with red stripes before pulling his panties back up and returning to our fuck fest.
This time I took the lead, donning a large, smooth, pink strap-on and taking Amber from behind as she held on to the iron bed-frame in front of where Richard was bound, dressed as a schoolgirl and wearing his spiked chastity device. She pulled down his panties again and put his cruel cock-cage in her mouth and to his immense frustration she started to lick and suck it. I was warning Richard all the time that he would be next in line to be fucked with my strap-on.
Amber came soon after – genuinely came, no faking, as she told me in the shower - and then we removed the oily sheet from the bed.
Richard must have thought his ordeal was over when we released him from the foot of the bed, but we quickly re-tied him, this time face down and spread-eagled on the bed, his wrists and hands attached to the four corners of the bed posts, stretched tightly. I had meant it when I warned him he would be next and we both grinned as Amber and I explained what we’d discussed in the shower and what would happen next to sissy Rachael.
Amber said she enjoyed this next little game a lot – it was one of her favourite activities when she saw couples. I was to fuck Rachael, the schoolgirl, who was tied face down on the bed, and Amber would fuck me with a vibrating strap-on from behind. I would take my cue from her, taking it slowly and gently to begin with, but then harder and deeper, until both Amber and I came. I’d make Rachael feel what I felt, fuck he
r like I was being fucked. Amber would control the pace and the vibrator in her strap-on would allow her to cum at exactly the same time as me, all I had to do was give her some warning.
It was absolutely amazing. I could see us all in the mirrored wardrobes when I looked to my right. Me ordering Rachael up onto her knees, holding on to her hips so I could fuck her more deeply and Amber’s hands running all over my tits as she fucked me, keeping herself at the point of orgasm throughout and clearly loving it. I knew then that I’d be shopping for a vibrating strap-on the next day.
That whole night felt like we were starring in our very own porn movie. I came long and hard and many, many times."
I looked at Jane and I could see that she was as excited as I was by Holly’s story. Oblivious to where she was (I assumed) Holly had been absent-mindedly thrusting her hips and running her hands over her black-rubber catsuit reliving the memories of that night. Jane and I had just looked on, speechless at the little show she was putting on.
Through the material of her tight riding mistress blouse I could see that Jane’s nipples had gone hard. Jane looked my way and recognised instantly what I was thinking and what I was staring at.
She smiled.
"Holly, look at you, you bad, bad girl, " Jane said, "you’ve got the two of us here all hot and bothered. I can’t speak for Sarah, but I’m absolutely gagging for it right now."
I nodded in agreement and went to retrieve from my office the two strap-on harnesses with internal vibrating dildos.
Holding them up by the strap in each hand in front of me, I said as calmly as possible:
"Would either of you object if we continued our staff training this afternoon with a little demonstration? You only have to take part if you like, no pressure....."
My heart was racing again when they both, very enthusiastically, said they would love that.
Chapter 8. [ Sarah speaking ]
Not long after that the office door opened and a rather flush-faced Nicola came in carrying a bag of sandwiches.
