Lizzie & Mike Pt. 04

Lizzie & Mike Pt. 04

Set in the near future... A young married couple exploring their sexuality get caught up in events beyond their control.

Synopsis :

Married for one year, Lizzie and Mike, (now Michelle), have started to further explore elements of a female led relationship. Lizzie takes charge with Michelle delving deep into the feminised sissy rabbit hole. Lizzie cucks him for the first time with another woman. Is Raven who she appears?

Tags : transgender, romance, sci-fi, femdom, feminisation, sissification, hormones, anal, watersports, lesbian, toys, BDSM, mind control

Thanks to lpacphantom who has taken on editing this story. Any errors are mine alone.

Events are seriously ramping up. If you thought this was going to be your standard Mistress wife & her submissive sissy husband story, then think again. Skipping chapters wont be useful, so reading sequentially from chapter 1 is recommended.

There are no STD's in this future fantasy world.

===

9 Sat - Onwards without Blinking - Day 7 Part 2 (continued)

They both slept for a few hours and it was just getting dark when Lizzie woke as Michelle started to stir. Michelle rolled out of bed to go to the toilet and came back into the bedroom to see Lizzie's eyes following her. She lay down as the front spoon and Lizzie wrapped her arms around her sissy and cuddled up close.

Lizzie spoke first. "Michelle, I'm sorry, it's my job to look after you and I didn't do a very good job yesterday. I should have streamed the video live to make you more a part of the scene but I got caught up in the moment with Raven and she took charge and it just didn't happen. Sorry."

She continued, "That was our first reclaiming sex and I don't know about you but that was the hottest fucking thing ever." She was pinching and rubbing Michelle's hairless nipples. Michelle still hadn't spoken.

"Do you want to watch the video with me and Raven?" One hand moved to cup Michelle's balls and the cage while the other pinched a bit harder on the nipples.

"I do but want to talk about earlier first. I virtually raped you and I'm, so, so, so sorry. I couldn't control myself." Michelle was weeping quietly in Lizzie's arms.

"My love, I was completely willing and while I wasn't ready for you, I absolutely endorse what happened and take complete blame.

"It.. was.. not.. your.. fault," Lizzie emphasised each word.

"I said I would video and let you know what was happening. I teased you and kept you in the dark. I had no idea of the extreme emotions cucking you with Raven would cause and plead ignorance and inexperience. It's me who should be sorry."

Michelle turned, faced Lizzie and kissed her. "I know that I say it all the time, but I love you so much. You are the best partner and Mistress I could have."

"I love you too Michelle. Aaannnndd, now that we have that off our chests let's watch the video and I will tell you all about my day."

They sat back up on the bed and Lizzie got her phone and linked it to the TV so she could stream it. She started and then paused the video.

"Can't neglect the important stuff sissy," and she handed Michelle her pill and they both washed one down with a mouthful of water.

Then she began her story ...

I met with Raven at a cafe near the sex mart and we sat in a secluded spot at the back. She was dressed in a latex LBD with a very short hem, her big tits almost spilling out the top. Very kinky and I was surprised she wore it out in public. I thought the maitre'd was going to refuse us entry. We gossiped for ages and she told me lots more funny stories of her experiences. She has seen it all! As we talked she moved close and put her hand on my leg and started rubbing up and down on it. As I wasn't objecting she went closer to my already wet sex, feeling my vag through the g-string. I leaned into her and she moved my panties aside and teasingly ran her fingers up and down my wet slit.

She asked about you. I told her we had been married a year and literally just started exploring this new dynamic this week but had been hiding in your case and submerging in mine our kinks. You are my sissy in training and have been locked up all this week.

She has a live in female slave at home that helps her in the dungeon. She prefers women but most of her clients are submissive men. She is all about female empowerment and trying to spread FLR and femdom. She is so naturally dominant, I was helplessly submissive immediately. Soon she was fingering me deeply and rubbing two fingers hard into my g-spot while fingering my clit with her thumb. I would have come but the waitress, a cute girl around 18 hung around when she came to pickup our empty plates. She was obviously intrigued and couldn't keep her eyes off us. Raven told her if she wanted to see more to call and gave her one of her cards. She slapped her bum as she left and she almost dropped our plates.

We got up to leave and she left me close to an orgasm. That's when we took the first selfie of us arm in arm hugging in the cafe. She took it further with the setup of the second selfie at our cars. She arranged us as you saw in the selfie and then made me take off my panties. I drove to her house while she teased me the whole way but wouldn't let me come. She pulled the top of my dress down and pinched and pulled my nipples. I was soooo hot and dripping wet and have a better idea of how you feel in chastity.

When we arrived at her place, a two story unit at the edge of an industrial estate, she led me inside.

Raven said, "You are so fucking hot, you could be a supermodel. I love your look and can't wait to fuck you." She kissed me just inside the door and rubbed her hands over my ass.

Her slave welcomed us at the entrance way. She got down on her knees and bowed to Raven. She was covered in tattoos and piercings with half her head shaved (think Leigh Raven) and dyed green. I was a bit shocked but everything she did was next level compared to us. Penny was her slave slut she explained. Penny's tattooed red eyeballs were disconcerting. She told Penny that we were all going upstairs.

She led me up holding my hand and told me to get undressed.

She's very serious about hydration and kinky sex. I drank 3 glasses of water while I was there. She was ordering me around and telling me what to do and how to feel.

Penny was already naked. She had a complete dungeon setup taking up the whole floor except for two rooms at the back which she said were a toilet and shower. Rubber flooring in most area, the walls were light grey not black like the floor and it was well lit, but she said the lighting could be dimmed.

It was full of all sorts of BDSM apparatus and furniture. Whips, floggers, canes, paddles hanging on a wall and shelves full of every sex toy you could think of : cuffs, gags, ropes, handcuffs and much more. Chains and mounts on the ceiling and walls. A gym type of square frame with fastening spots all up the supports and rim with a small hoist set into the centre above. A large wooden cross on one wall and a padded bench, one horse, a set of stocks, couch and chairs. Two cages against the wall, just large enough to fit a person it. A few mirrors.

I was trying to take it all in, it must have cost a fortune. She even had a video setup for streaming with a large TV in one corner and cameras up in every corner and along the wall. A series of large framed photos where you couldn't identify the faces of naked men and women being tied up and dominated in a variety of positions.

She asked me if I wanted a video of the session. I said yes as I told my sissy I would video it for her. She went to her corner streaming and computer setup and fiddled with stuff on the screen.

"Just yell and shake your head if you find anything too intense," she warned me. "But I'll go easy on you tonight." I nodded to her and she grinned.

She took my unlocked phone and set it up on a tripod facing the horse so I would have my own video. She would send an edited movie from her own setup later.

--

Lizzie said, "I'll start the video now and keep talking. Watching it will explain more." Lizzie unpaused the phone video and she sat back again to cuddle Michelle and watch the 4K movie on the TV. Raven had set it up at a perfect distance and angle to catch everything. Even though it was from a stationary camera all the action was caught.

--

Once I was naked she moved me into position bent over the horse with Penny on the other side. My butt was facing my phone at an angle. She attached a ball gag that I shared with Penny with a strap going around the backs of our heads. I hadn't noticed until Penny opened her mouth to receive the gag that her tongue was black and the end of her tongue was forked. Penny was playing with her tongue around the gag. She also had a stud near the end of each fork tip.

Penny and I were staring eye to eye, our lips almost touching, fastened together. Raven cuffed our hands together and tied a rope under the horse. Next was a spreader rod between our legs keeping them wide apart. I'm not sure why I was letting her do all of this, she just took charge and did it. I could have objected at any stage which was tacit approval. I did nod at the beginning which I suppose was acceptance.

She got some lube and squirted it into her slave's outthrust butt and pushed in a massive 12" long 2" wide dildo and twisted it slowly all the way into Penny's ass. She told her that if it comes out that's 20 canes on her feet. She put some greased fingers up my bum, I was petrified I would get the same dildo as Penny, but she put in a 1.5" butt plug that felt good. She put some sharp, teethed nipple clamps on Penny's nipples and some normal clamps on mine. She hung some heavy weights on Penny and some lighter ones on me. Penny was licking around the bottom of the gag over my lips. I was very wet and could smell a strong dose of female arousal.

She fingered me and bent over to suck on my clit to get me revved up even more. She arranged a fucking machine into my slit and started it to slowly fuck me, keeping me on edge.

Raven told us to bite into the gag. She selected a paddle with holes in it and started to whack Penny's butt extremely hard. With every hit Penny grunted and jolted forward which pushed me back. The dildo thrusting me was going at a slow steady pace and the weights hanging from the nipple clamps were swinging. As well as the butt plug in my ass everything was keeping me aroused. She must have given 40 paddles to Penny and I'm sure her butt must have been bruised and red. Then it was my turn. I got 20 much lighter hits and she caressed my ass every few hits which was very soothing and felt great.

As you could see it was impossible for me to video and Raven will send us her footage. She then took a flogger and striped three sets of twenty on Penny's back, legs and butt. She flicked up another twenty on her hanging tits. She did another ten into her sex swinging up between her legs. Penny was getting a major workout and was sweating and squealed with the ones into her sex. I felt every hit as I was attached to her. Raven left me alone and I didn't get any hits from the flogger. She finally picked one of her canes and asked me if I remembered her telling me they were intense. She walked around us several times, lightly swinging the cane into her palm.

She stopped behind me and gave me four fast hits, two on each side. I jumped and squealed into the gag, trying to wriggle my hips away from the pain. The stripes of the cane were exactly as she said intense! I had never felt such sharp pain before except when I broke my arm from a fall once. I moved around so much that the fucking machine's dildo slipped out and Raven had to arrange it back in my hot, wet, soaking pussy. As the pain slowly settled from the initial searing strikes, she walked around behind Penny with the cane. She swished once intentionally missing and Penny jolted with the expected impact. Penny got 14, 10 on her butt and 1 each in the crease between butt and leg and on the back of her knees, each harder than mine, one second apart. Probably planned by Raven but the 12" dildo was ejected out of Penny's ass early in her caning.

Once the caning was finished, she left us tied up but removed the ankles rods, nipple clamps and fucking machine. She rubbed a soothing cream over both of us where she had struck, starting with me. She made it as sensual as possible and spent some time caressing my pussy but never letting me get close enough to orgasm. I was trying to push my hips into her but every time I did she removed her hands. She untied me and my side of the gag strap and pulled me in for a kiss and a hug. She told me to have a glass of water while she tended to Penny.

I stopped the recording from my phone. Almost 40 minutes of footage! My pussy felt stretched from the dildo pumping into me for that long.

I rubbed my nipples and butt as they were still both sore. Looking over my shoulder at a mirror, I could see the four raised welts from the cane and the red flush from the paddles. The cool drink of water was totally refreshing after the session. Raven was tending thoroughly to Penny after untying her. Penny was shaking and I could see the importance of aftercare as Raven caressed and whispered to her. They were hugging and kissing. Raven led her to the couch and lay her down with a doona over her. Penny was red all over her front & tits, back, butt and legs. Her ass which had taken the 10 stripes from the cane was bleeding in several spots where the lines crossed. I never wanted to get such an intense whipping as that. But watching Raven at work was very informative.

Once Raven was sure that Penny was fine, we went downstairs to her bed and made love. Penny came down at some stage and watched but didn't join in. We kissed, caressed, fingered, 69'd which was where Raven took the photo she sent from my phone. I gave her three orgasms and I had two from her. I was totally involved in the moment and sorry that I didn't video that part with Raven other than the one photo.

--

Michelle was riveted watching the BDSM scene upstairs and was frequently looking at Lizzie to see her face as they watched.

"How do you feel about Raven?" Michelle asked.

"She is fascinating and I do like her. She is teaching me so much, but she's not you. I'm not married to her but to you. She could turn into a friend with benefits or maybe I'll be a sub when I'm with her. It was actually good to be submissive and it taught me about how you must feel. I definitely want to see her again and you are coming next time. If she doesn't want you as part of the bundle then I simply won't see her anymore. We didn't swear undying love between us but she obviously liked me. Probably more than I do her."

"One of the best things out the two of us is that we are at the same stage of our sissy & Mistress relationship which is built on top of the layers of our existing vanilla relationship. I love what is going to happen in the future and how we both evolve. After the session with Raven I couldn't wait to get back to you."

This was all reassuring to Michelle.

"Now we missed out on your surprise today and you are going to locked up for two weeks from tonight. We can go out tomorrow for the surprise and I think I owe you ten too. But we can delay that for tomorrow. You may sleep with me tonight, but you still have to do cleanup from coming in me today. I want two of your best orgasms. Be careful with my butt, it's still sore."

Michelle knew that she never forgot anything and lay back as Lizzie straddled her face and got to work licking her out.

===

10 Sun - Reinforcing - Day 8

Michelle woke early at 6am just as it was getting light as they had both overslept. A lot had happened yesterday but she thought they were in a good place. Lizzie was still asleep. She got up carefully as she wanted to look good for her Mistress in the morning when she first saw her sissy. Into the guest bedroom and a shower with enema. The new hair removal device had worked well with no regrowth at all. Being smooth was so sexy. The cage was back on which was starting to feel like her natural state of affairs. Moisturiser all over and a dab or two of perfume. Lipstick was easy and she left it at that until she had done some makeup tutorials. She put in the 1.75" plug and got dressed into her lingerie. She could squeeze in an hour of sissy hypno's and wanted to watch some daily. She had a series lined up to keep her busy for weeks. Still no sign of breast growth. Maybe her nipples were the slightest bit tender but nothing she could actually see.

Today she wanted to go shopping for clip on earrings, some high heels, possibly a maid costume and a waist trainer. She was very tempted to pluck her eyebrows some more and would check with Mistress if she thought it was appropriate.

Her tummy was rumbling as the only food she had yesterday all afternoon and evening was licking her own sperm out of Lizzie.

At 8am she was at Mistress's closed bedroom door. She could hear her in the shower. A post-it note was on the door telling her to come in. She went into the ensuite and waited patiently in a sexy pose until Mistress saw her. She couldn't get in to wash Mistress as she was in lingerie so just stood there posing. Lizzie quickly noticed her sissy and smiled at her.

"We will do gym first, lots of glute work today to build that sissy ass. I'll make breakfast while you change the sheets"

Her legs were almost recovered. The easy ride yesterday was no problem. She worked hard and pushed for the burn today in gym. She made it through all three sets - just. Lizzie was a machine and pumped through five again easily.

After changing the sheets in both bedrooms and having a quick shower again, she walked sexily into the kitchen where Lizzie was waiting with their herb milk shakes, a poached egg and some mixed, unsalted, fresh nuts. Lizzie had already started and nodded for Michelle to eat too. Her favourite part was always the shake.

"Looking good sissy!"

Lizzie loved to watch Michelle dressed up as a sissy. Every day she was looking better, trying to walk and act in a more feminine manner, getting better at lipstick and makeup. Michelle was all hers and couldn't wait to see what she looked like after three months of taking the pueraria-mirifica. Although she had been against feminising her husband into a sissy, it now gave her a massive erotic charge and she loved that Michelle wanted it even more than her.

"I have your surprise today, my lovely sissy slut and we can spend the day working towards feminising you more. I want you to wear a pair of my girly coloured spandex training pants and a pink tight top from my wardrobe without your bra. Are you daring enough to wear sandals and show off your red toenails?

Michelle shivered. She was going to look pretty feminine as it was, bright red toenails would be too far. "Maybe next week Mistress."

"Parade what you think works for me and I'll approve it if it's feminine enough. We must build up your own sissy wardrobe as I don't want you wearing all of my stuff."

Sissy tried a pair of tight yellow and pink spandex with a pink t-shirt she found in Lizzie's drawers. She modelled it for her Mistress and got her approval. A white pair of runners and they were ready to go. Lizzie was dressed similarly to Michelle, highlighting the feminine nature of Michelle's clothing. They could almost have been girlfriends if it weren't for Michelle's hair and lack of breasts, although her man boobs did protrude marginally. Michell had wiped off the lipstick but had applied more perfume.

Lizzie had an itinerary planned for the day already. "Sis, I'll drive."

Michelle jumped into the passenger side and Lizzie headed off with no explanation of her planned surprises.

Her first stop was at an up market lingerie shop where she planned to buy five sets of differing colours of styled and matching lingerie sets for Michelle. All lacy, frilly and completely feminine. Each set was composed of stockings, panties, garters and a bra. They purchased A and B cup versions of each bra in expectation of her tits growing. Michelle was very excited and tried on everything in the changing rooms and modelled each set for Lizzie. Their shop assistant was very helpful and this obviously wasn't the first time she had helped to fit out a man / sissy / crossdresser. Shop staff didn't blink an eye and had been there before it seemed. Lizzie queried the female shop assistant and she said usually the guy comes in by himself and says he is buying it for his wife or girlfriend. She says they are easy to pick especially if they are doing it for the first time.

The next purchase was for some sleepwear and perusing through the store they settled on a babydoll, negligee and a cami set. All skimpy, see through and feminine.

The store also sold shape wear and they enquired about waist trainers and corsets. Lizzie got Michell to try on an underbust white waist trainer with three adjustments that she could wear to work under her shirt and during the day except for exercising. The first adjustment was tight and would likely last her a month, depending on how fast she lost her belly fat. She bought another looser one that could be worn while sleeping. Corsets needed to be custom made and fitted for men as their hips are different from women so they decided to leave that and just go with the waist trainers. Lizzie was pleased how it pulled in sissy's waist and gave her a more feminine and curvy body shape. The staff member advised that best results were obtained with a combination of diet, exercise and wearing the trainer as much as possible.

"Sissy, that wasn't really your surprise as we needed to expand your wardrobe anyway," Mistress advised when they were walking out the store, bags in hand.

"Mistress can we buy some shoes and clip-on earrings please?" Michelle pleaded. "And can we pluck my eyebrows some more?"

"Sissy how can I ignore such a heartfelt plea, of course we can. Follow me. I'll do your brows when we get back home."

They ended up buying some women's flats, pink joggers and three pairs of high heels in 2", 3" and 4" for sissy to progress through and for her own personal use. Lizzie observed that Michelle was showing remarkably little embarrassment or humiliation from obviously being a male trying on women's clothing and shoes.

At a jewellery store, Lizzie would only let her buy a single pair. A large hoop clip on earring. "Cant we get more Mistress?"

"No sissy one will do for the moment. Your surprise will take a while and we need to move on."

A message came through to Lizzie's phone from Raven as they were leaving the shopping centre.

"Hope you enjoyed yesterday, I did, and would love you to come over again for more fun and discipline. The link is to the unedited movie from my cameras, I'll send a better edit when I get the chance. This is a private movie and not shared with anyone. Can we catch up again for a date, one evening this week and have a session on the weekend?" The message included a few high resolution images of Lizzie being spanked, showing the spreader bar and butt plug with the hanging nipple clamps and weights. One caught her being caned at the moment of impact with her butt dimpling in along the line of the cane strike and a ripple of flesh spreading out. It included a cloud link to download the movie.

"Sissy, look at the image Raven sent me," she called Michell over to have a look at one of the images.

"Wow Mistress, she captured the moment perfectly. I love seeing you caned!"

"Well it was a break from dominating you and to be honest I did enjoy it."

She texted back, "Dinner sure, 1 night st8 after work, Wed good for me. Weekend session will have to be with my sissy as well."

The reply came back almost immediately, "Done, see you Wed, sort details later. Sissy welcome, understand you are a couple, no problem."

Lizzie was relieved that Raven would allow Michelle to come as she definitely wanted to explore further with Raven.

"We are both visiting Raven next weekend and I'm having dinner with her on Wednesday."

"Dinner alone Mistress?"

"Yes but it won't be for sex, just getting to know her better, and I'll send photos."

Michelle was quiet, at least she was going with Lizzie on the weekend.

"Come on sissy, time for your surprise."

At the next stop Lizzie pulled up outside a tattoo and piercing shop. Moderately sized and modern.

Lizzie didn't get out of the car and turned to Michelle to talk. She used whatever title was best appropriate for the moment, in this case Mike's feminine alter-ego, Michelle.

"Michelle, I'm amazed at how quickly and thoroughly you have bought into being a submissive sissy and in the process feminising yourself. There is of course a long way still to go and currently we could stop or even go back and you could resume as a man. I'm noticing that you are more submissive as a sissy than as a man. You seem happier, sexier, more obedient and willing to work towards my goals for you. I want to make you a feminised sissy with real tits with the changes permanent so there is no going back."

Michelle paused and slowly said, "Mistress, I'm finding that whatever you want, I want. Our sex life has never been better. I completely accept that you are the leader in our relationship and working towards what is best for both of us. Being a sissy, submissive and feminine is taboo in mainstream vanilla society. I love it though."

"I'm deliberately trying to push your boundaries, hence this next step today. I want you to get some temporary tattoos and some piercings. The tattoos will be a large colourful butterfly tramp stamp on your lower back, Property of Lizzie above your groin and an interlocking flowering pink vine around your ankle. The piercings will be in both ears, studs for the moment and an ornate belly piercing with short dangling chains. All obviously feminine and something unlikely any man would have. The speed at which you are going femme is crazy. In one week you are trying to grow breasts, narrow your waist, dressing, acting and wanting to be as feminine as possible, with a locked sissy clit and wearing a butt plug most of the day.. We need to think how this may impact your work. I believe it would be ok at your job to turn up dressed as a woman or gradually doing so. Talk to HR and the transition would hopefully be seamless. Sure some people might have issues but it will be unlikely to affect your job. Parents and family are a bigger issue. I think next week you will be ready to appear in public dressed as a woman and I encourage you to do it."

Another pause as Michelle framed her reply carefully. "I agree with everything you are saying and want the process to go as fast as possible. There was a guy who transitioned or at least presented as a woman at work last year and there were no issues except two guys who gave him a hard time. HR had to sort them out. My mother is very liberal, my father not so sure, it's one of those things that you never know until you do it and come out. You are probably better off judging your parents. Friends - if they can't handle it then they aren't great friends. But the important thing is us and what we have with each other works."

Lizzie reached over and held hands tightly with Michelle. It was an emotional moment for both.

Michelle continued, "If you told me two weeks ago this would be happening then I would have said no way in hell. I've never been a fan of tattoos or piercings but simply because you want it, so do I. I love it when you push my boundaries, I want to be femme. It's liberating and also at the same time completely terrifying. I'm finding that being and acting as a male is boring and I can't wait to be dressed in lingerie, makeup and being your submissive sissy."

"Let's do it, come inside with me and we can both pick the details for the tattoo designs and the piercings."

"Make it so, Mistress!"

--

Michelle walked out several hours later with everything complete as they had discussed. With advice how to clean and look after her piercings and tattoos.

- -

At home, Michelle undressed immediately, had a shower and enema and the changed into one of her new lingerie sets, with a garter belt over the top and her shortest heels. Mistress wanted the waist trainer left off until her piercing & tattoos healed so she could take some pressure and rubbing.

Lizzie made some grilled chicken fillets with fresh veggies. A smaller serve for sissy. The herb was mixed in with their drinks.

Lizzie cut up her sissy's meal, handcuffed her hands behind her back and made her eat from the floor. She made her take her drink standing first. Lizzie found controlling every aspect of Michelle's life in what, where and how she ate, what she wore, charged her up physically and mentally. She finished her meal quickly and sat back to watch her restrained sissy struggle to eat kneeling and bent over without being able to use her hands. The feminine figure in front of her didn't look anything like her husband of the previous week.

Once Michelle was finished Lizzie cleaned up the dishes.

"Into my bedroom and stand in front of the bed. I'll be there soon."

Lizzie sat down to watch the news for thirty minutes and then went to the bedroom. Sissy was standing patiently waiting for Mistress. She fastened the ball gag and the blindfold to sissy's face and pushed her face down onto the bed.

"Up on your knees slut and hold your bum up." Sissy had to turn her head to be in a semi comfortable position while she rested her shoulders on the bed. Lizzie was in a particularly dominating mood and pulled her slut's panties down to her knees to see her chastity and butt plug.

She paddled her cheeks with twenty each side from the paddle until the skin was bright red. She massaged her butt gently to ease the soreness. Then she did twenty hard strikes on each side with the flogger covering the tops of her legs too. Again she massaged the sore and now very red skin. Finally she finished with 10 each side striping her legs and butt with the cane, not overlapping any hit. Sissy was crying soon after the cane started but didn't use her safe word or gesture.

She knew sissy had just had an enema and would have greased up her butt plug. She pulled it out and eased in progressively four fingers and pushed them in hard. She tried to fit in the 2" butt plug and it got very close but sissy's ass was still too tight. Squeals as she tried to push it in fully were arousing.

She left the plug out and attached the strap on dildo harness with the 8" long and 1.75" dildo. She lubed it with her hands covering it all over. Sissy was still writhing her raised ass to try to relieve her very sore cheeks. Lizzie slowly rubbed in some cool moisturiser covering all the areas of skin she had struck. She reached under and massaged her nipples pulling and twisting.

Moving behind sissy she pulled her legs onto the floor with her knees against the bed. She gripped her hips and lined up the dildo with her hole and in two thrusts was fully in, groin to butt inside her sissy. She then fucked her for 20 minutes continuously to full depth but varying the pace. She loved the large femme looking butterfly tramp stamp tattoo on sissy's back, she had the perfect view of it from where she was fucking her. It went full width across her back. She imagined sissy in a bikini at the beach.

Michelle's locked cock was leaking drips of pre-cum onto the towel as she was being fucked in doggy by her Mistress. She was trying to have a sissygasm but still couldn't manage it. Lizzie pulled out and flipped Michelle over onto her back, knees bent, her arms under her. She took her blindfold off so she could see her Mistress. She relubed the dildo and squirted some into sissy's ass hole. She went back to fucking her ass again for another 15 minutes in missionary. The 8" dildo pumping all the way out and in. Her anal rim stretched almost to her limit.

"Hey sissy cuck, imagine it's your best mate, Paul fucking you and making you clean his cock after coming in your sexy, little ass."

She pulled out and manouevered sissy around so her head was hanging off the edge of the bed, took the ball gag out and pushed the strap on dildo to the back of sissy's throat, making her gag and choke.

"Take it all sissy, your mate is going to come down your throat after fucking your ass. Then he is going to fuck me and you are going to clean my pussy to get out all his cum."

She pulled out and grabbed the 6" dildo and told sissy to deep throat it. She pushed itin to the back of her throat and then slowly deeper into her throat. "Relax sissy and take it all." With her head hanging over the edge of the bed she had a straight run into her mouth and down her throat. Drool was dripping down sissy's face into her eyes and over her forehead.

She could see sissy's throat bulge as the dildo went all the way in. "Hold it as long as you can. Paul is coming now, you're a cocksucker, sissy."

She pulled the dildo out and kissed her and licked her drool off her face and fed it back to her as they kissed again.

"Organise yourself, sissy cuck and lick me to two orgasm's while you lick out Paul's fertile semen from my hot wet cunt."

Lizzy lay back on the bed while she was pleasured. Michelle was struggling as her hands were still behind her back, but Lizzie wasn't going to make it easy for her tonight.

After 15 minutes she came twice and they cuddled for a few moments after the handcuffs were released.

"Sissy, I want your ass to be looser. Sleep with the 7" dildo in you tonight. Off to bed."

==

11 Mon-Fri - The Weekly Schedule - Days 9-13.

Lizzie wanted to get Michelle into a routine, to normalise always dressing as a sissy, day and night except when at work. And when at work push the boundaries with plugs, chastity, painted toenails, panties & garter, pantyhose, shape wear and bras. Michelle was a willing accomplice and was always thinking of ideas to assist Mistress when she was at work or in public - adding clear varnish to nails, clear lip gloss to lips, wearing women's flats to work. She still wore earring studs to work but wore overtly sexier earrings and makeup at home.

They found it was easier if Lizzie did the meals as that freed up Michelle to get changed into lingerie, flush with enema's, practice makeup and do chores, feminine and submissive tasks. Breakfast was more casual as they were on a tighter schedule before work and just needed to get things done to get out the door. Exercising, runs and gym in the mornings didn't give them any time to play. Lunch was either at work or again casual when they could talk more as partners rather than domme and sub / Mistress and sissy. Dinner and evenings were strictly power play times with sissy eating on the floor without hands or being fed by hand by Mistress.

Lizzie was practising bondage positions for Michelle to be restrained in for increasingly longer times. She particularly liked strappado as it was a punishing position that placed sissy's ass perfectly for paddling or fucking with her strap on. With a spreader bar, bent over with her hands behind her raised up above her body she was completely helpless. She needed to keep still to minimise the pain of the position. Gagged, blindfolded, caged and plugged she was completely in Lizzie's control. This Sunday she planned to put the dildo gag in and grab sissy's head while in strappado and use her as a living dildo to fuck herself.

Evenings after work and particularly the 9pm play time was now established as their primary sex, bondage and impact play time. Lizzie had multiple daily releases either by dildo, vibrator, sissy licking her or all three. Michelle found she was becoming more submissive as the time extended between releases. She wanted to get off and her arousal was high. Mistress was going to be her only release when she was finally allowed. She found that pleasing her Mistress and anticipating her needs and pleasuring her gave her great satisfaction. The comparison of their situations was not lost on her. She knew she was complicit in her own compliance and submission and loved every moment.

Sex Schedule

Mon Fucking Mistress with strap on then lick

Tue Paddling and then pegging sissy's ass & lick Mistress

Wed Massage, pamper & lick Mistress

Thu Caning across legs, ass & back & lick Mistress, dildo in ass overnight

Fri Sex toys for Mistress

Sat Dressed femme in public & sissy anal stretching session working towards fisting

Sun Bondage in various positions, clean cock and chastity and tease & lick Mistress

They had found that two heavy anal or punishment days in a row were impractical as she needed a rest day (or two in between). Caning in particular had Michelle sitting down carefully for a day and the bruising needed time to fade. Combining arousal, anal sex and pain was linking the sensations in Michelle's mind and she was finding she wanted bondage, anal sex and punishment together during sessions when she was being used by Mistress. Lizzie varied the details to keep her sub guessing.

Because Michelle fucked Lizzie over the weekend after she arrived home from Raven's, she was now in chastity for two weeks. She had her twice weekly cage and cock inspection and cleaning sessions but her hands were always restrained during these. Lizzie had complete ownership and control of Michelle's cock. The anti-pullout mechanism on her chastity really worked and there was no way short of using tools to get out of the cage.

She published a weekly sex schedule that she stuck to the fridge and in Michelle's bathroom and bedroom. Other than externally at work, Michelle was now always dressed in lingerie and in a sexy nightie when sleeping. She wore shapewear twenty hours a day, only removing it when working out, showering and for a brief rest period after dinner until 9pm. The looser version she wore at night, which helped her to breathe easier. Her waist was pulled in 3" when she was wearing it and they both loved the curvier shape it gave her, making her hips look wider. Some women, typically more observant than men, were giving Michelle unobtrusive glances and stares at work as they were likely noticing the glossy nails, flats, studs in ears, bra & shapewear outlines under her male shirts, studs in ears.

Michelle was working on her female mannerisms, posture and speaking in a higher voice when at home. Some of this may be carrying over to work. Michelle wanted to be feminine and didn't particularly care if anyone at work noticed now - even if she was only into her second week of being a sissy.

Almost every moment of her day was taken up with chores, sissification, feminisation, sissy hypnos every night, makeup videos, voice training, deep throating practice and sex with Lizzie. She was always gagged, in lingerie and heels when doing chores. When Lizzie met Raven on Wednesday after work, she had picked up two maid costumes for sissy to wear exclusively when doing chores.

Michelle loved staring at her hairless body after showers or when changing. Her navel piercing, "Property of Lizzie" sissy tattoo above her cage, her large butterfly tramp stamp and ankle vine tattoo turned her on and had her cock trying to get hard inside her cage. She was rubbing, twisting and pulling on her nipples and breasts every day. She was applying the pueraria-mirifica cream on her breasts and nipples nightly. She wished she could suck on them.

She was slowly getting used to her exercise routine and could now do three sets in gym but still without weights and was extending her jogging portions between walking on her runs. She was still sore and glad for the recovery day on Wednesday. Dietwise she was still hungry all the time and limited to water, tea or coffee for drinking without sugar. Processed foods or drinks were banned and she was only eating small servings of whole foods. The herb was religiously added twice a day to their meals or drinks. By the end of the second week she could detect a slight swelling and the beginning of breasts buds. Her nipples were definitely more tender.

--

Lizzie was messaging Raven daily and they were becoming good friends. Lizzie really liked Raven. She was the only non-vanilla friend she had and they could talk about the many sexual things going on in their lives. Sure, Lizzie had some female friends but they were mostly standard hetero in vanilla relationships with no kink. Lizzie had moved on from that space. Talking with Raven gave Lizzie a chance to act as more of a sub or at least less of a domme and take a break from being a Mistress all the time at home with Michelle. Lizzie sent Michelle several photos of their dinner. Raven had teased her during most of the meal. When they arrived Lizzie had shown Raven her panties in her hand and Raven in turn gave Lizzie a 2" wide butt plug to put into her ass before she came back to the table. Raven spat on the panties and put them into Lizzie's mouth.

Lizzie had to use liquid hand soap as a lube and it took several painful minutes for her to insert the plug. She definitely felt very full and stretched as she was only up to the 1.5" plug at home.

Raven held her hand out when she got back to their table and Lizzie took her panties out of her mouth. Raven spat on them again and ordered Lizzie to put them into her pussy immediately. Lizzie was soaking wet by this stage and she stuffed them into her pussy after they kissed and sat down.

Lizzie briefed Raven on her progress with Michelle. She said that Lizzie was the most organised domme she had ever met - timetables, structures and lists. She was impressed. She asked her how she expected their 3 month dom/sub trial to go. Lizzie said she expected them to make it permanent at the first monthly review. It had come to completely take over almost every aspect of their lives and she couldn't see either of them able to go back. It was still evolving rapidly.

Raven laughed and understood as alt lifestyles were much more interesting and vibrant. Lizzie talked about cucking Michelle as from her reading of the book about insatiable wives she was aware of how the progression of their lifestyle and involvement with people outside marriage would go. Lizzie still liked real men with real big dicks but had partitioned off that part of her life when she married Mike. Raven agreed and many cucks and sissies wanted their Mistress, slut or hot wife to fuck other men. She expected Michelle to raise it herself and want Lizzie to open up their marriage to others. Lizzie smiled and said it already had with her and Raven.

Lizzie asked about Raven's slave. Apparently she was an IT consultant and worked remotely for her clients. Raven had collared her 2 years ago and ever since she had lived with Raven. She had her wages paid into Raven's account's and owned nothing of her own. She had no responsibilities except for work and to obey Raven, who ran her life. She was paid well and it enabled Raven to live a much better lifestyle and to help build her full time Mistress and domme business. She also had an Always Fans account as a pain slave slut and did daily scenes by herself and twice a week scenes with Raven. Income from that was also building. She assisted Raven in the dungeon as required. Her family had disowned her but Raven was her life and she had completely submitted to Raven as her owner and Mistress.

She asked if they had considered putting Michelle on hormones to further feminise her as they both seemed so keen to advance that aspect of their relationship. Raven urged her to do sos as she would be so much more femme. Lizzie looked unsure and said that they wanted to have kids in a few years. Raven laughed and told Lizzie that looking like she did, she could get into cucking her sissy and have a choice of bulls or studs queued up to impregnate her. She was rubbing her pussy hard now trying to get Lizzie off.

Raven fantasised for Lizzie, "Just imagine you being railed by one of your bulls, a real stud with a massive cock in your own bed. Your sissy on fluffing duty to get him started and then cleaning his cream pie from your dripping wet, overflowing cunt while the bull fucks Michelle in her little sissy ass. She's been on hormones and has real tits, a sexy bubble butt and is your full time live in sissy maid in permanent chastity.

Raven pressed hard on Lizzie's clit and she came hard gripping the edge of the table while her orgasm ripped through her. The same waitress as last Saturday was watching their sexy antics.

Lizzie said after she eased down from her climax, "Yes that's a sexy fantasy but I want to have kids with Michelle."

"You really want a femme cuck sissy to be the father of your children? Ok, it's your choice," she said derisively, "Surely you can do better than that. Hey she's a great looking sissy and only going to get better over time."

Lizzie was getting a bit annoyed with Raven pushing so hard, especially when she was putting Michelle down and was about to retort when Raven changed the subject. "I've got some great fun planned for Saturday with you and your sissy. She has to come dressed as her most feminine self and all four of us will have such a great time."

"I've got to go as I left Penny tied up and we have an Always Fans session scheduled for tonight. It's so great to catch up. See you at 1pm at my place on Saturday. Wear the plug on Saturday."

They hugged and kissed and Raven had some words with the waitress as she walked out.

--

When Raven arrived home she untied Penny from the cross. A wand was taped around her waist with the vibrating head on low pressed against her clit. Penny was pressing her hips hard against it.

"How many orgasms?"

"Twelve, Mistress."

"Not a record, do better next time. Our online pain session is due in 40 minutes. Needles and fisting tonight."

"Can't wait Mistress."

"Get everything set up, I have some calls to make."

-

"Lizzie and her sissy are coming on Saturday as well as a new young couple, Jessica and her boyfriend Ryan.

"You are spiking everyone's drinks except mine with a strong dose of the aphrodisiac, hypnotic and relaxant cocktail."

"I'm going to play with Lizzie and I want you to paddle and then cane the sissy's butt hard. Ryan plays with boys and girls and I want to get the sissy to suck him off and take it in the ass from him. I've got a hardcore feminising hormone cocktail from my endocrinologist slave and you're going to inject it into the sissy to speed up his feminisation big time. Supposedly it's got the latest new tech with stem cells, nanotechnology and other stuff that reprograms the liver and bone marrow to produce feminising hormones. The effects last up to three years. I want you to cane him, inject the sissy in her butt as the doc showed you. Understood?"

"Yes Mistress, it's going to fuck up his masculinity permanently. I'm horny just thinking about it."

"Yeah all the stuff it does is crazy, trannies who want to go full femme love it. Cuts off all testosterone production, ramps up oestrogen, penis & testicle shrinking, massive breast, areolae and nipple enlargement, voice box tightening, female fat distribution, muscle loss, permanent arousal. I forgot half the things he told me it does. Things that couldn't be done even two years ago and needed surgery. Set and forget. He tried to mansplain it to me but it was way over my head."

"No fuckups with this. Lizzie is important to me and the feminised sissy might be useful to me, she has some potential but Lizzie is my main target."

"I've got it Mistress. Boy to girl as you wish."

"Do you want me to feminise Ryan also?"

"Whatever you like and I'm sure you do. Have some fun with him."

Raven had spiked Lizzie's drinks at every one of their meetings. She was running short on the mind control drug so she could only use small doses and had to take her alterations slowly.

==

12 Sat - Changes Every Which Way - Day 14

Michelle presented at Lizzie's bedroom door an hour earlier than usual at 7am this morning. She had already flushed with an enema and plugged herself with the 2" butt plug which she had moved up to on Tuesday after her pegging session.

Lizzie was already up. She announced immediately when Sissy presented at the door, "It's a big day of firsts today sissy, your first time in public dressed as a girl, getting your makeup and hair done professionally. We have a lot to do, I'll see you in gym for a quick HIIT circuit. We aren't going outside for a run or ride this morning. Pink lingerie set today."

"Ok my lovely sissy, photo and measurement time, then breakfast." They stripped off and took photos and measurements for their records. Michelle now inked with her temporary tattoos.

Lizzie prepared porridge with berries, banana, bran flakes, protein and pueraria-mirifica powder while Michelle cleaned up after gym and filed their photos and logged their measurements.

They were sweating profusely after their twenty minutes of high intensity exercise with Michelle in particular breathing hard. They exercised naked which both enjoyed.

"The hard work is paying off sissy, another 3 kg down in weight, hips the same, waist 2" down and chest 1/2" up. I can't see your boobs getting bigger but I think your nipples look swollen and puffy. But given you lost 3kg overall this week, for your chest to be getting bigger without doing upper body exercises it must be the herb working. That's 6kg overall since you started two weeks ago."

Michelle grinned, it couldn't happen quick enough, but progress was in the right direction, even if small. Given any noticeable changes were always going to take months, to expect anything in two weeks was unrealistic. Lizzie told her that weight loss could be rapid but feminisation takes much longer.

"You'll be fit sooner than grow your tits. Of course we want both. Be patient sissy."

"Shower and enema again with your 2" plug in. I left out a sexy pink wrap floral dress for you. 2" heels. Large circle earrings, no makeup. I'm getting impatient for your tits to grow out and I might get some breast forms for you, but not today."

"Yes, please, Mistress!"

Lizzie thought Michelle looked leaner overall and her waist definitely had lost belly fat. Gains would come increasingly slower but she was very pleased with Michelle's improvements and commitment to exercise, diet, submission and feminisation.

Michelle flushed twice more and had as clean a colon as she'd ever had. She lubed the 2" plug and pushed in and seated it. She had grown to love the feeling of her ass being plugged. The long conical shaped plug would press on her prostate keeping her edged and aroused.

Lizzie also had Raven's 2" plug in. It was a different shape as the others they had purchased and not as long. Harder to get in and extract. Lizzie was dressing up with a shimmering bodycon blue dress and 3" heels. The dress hugged her figure and accentuated her athletic curves. Without a bra, her nipples tented the front of the dress but the shimmering material disguised them somewhat.

They were ready before 9am. Two very attractive looking blondes ready for a morning outing. Lizzie had given Michelle a small handbag. Her sissy was confident in heels as she had been wearing them to do chores and move around the house for a week. Her mannerisms were also coming along well. Voice still needed a lot of work.

They were due at Raven's at 2pm. Their first stop was at the beauticians and hairdressers. They were both having manipedi's, in Michelle's case vibrant red. Lizzie had organised hair extensions and a full makeover for Michelle. Sissy had been well overdue for a haircut when they started their new lifestyle two weeks ago. Lizzie was in and out within the hour and went shopping while the staff worked on Michelle.

Michelle was amazed at the extent and fuss of her visit. Her new bright red fingernails extended only 10mm longer than her natural nails and looked beautiful. The hair extensions took the longest as they had to be threaded close to her scalp. Lizzie had sent a photo of her hair so they could match her hair colour closely.

Michelle knew that she was going to be talking to HR at work on Monday as she would be unable to hide her transition in her current state. She wanted to stay in female mode all the time now. This was the point of no return. Once her hair was done, the beautician started on her makeup, explaining every step of the way. Michelle saw she would need weeks of practice to even get close to what the professional was doing. She selected colours that matched her style and face well. Working from scratch she realised was much harder. Having a known working palette and a sequence was a perfect start. Today wasn't going to be cheap but seeing the results she thought it was worth every cent.

Staring at herself in the mirror at the end result, she was in awe. Looking back at her was a completely feminine young woman with perfect makeup, big hoop earrings, slightly wavy long blonde hair below her shoulders, lovely eyes with extended lashes and deep red lipstick matching her nails. She almost matched Lizzie in looks. The hairdressers staff were very happy at the result too and had taken before and after photos that they were going to use for promotional purposes. Michelle's androgynous face now looked completely feminine and sexy.

When Lizzie arrived back, she too was stunned at Michelle's transformed appearance. They were about to kiss when they realised it would smudge her lipstick so they hugged and laughed at arm's length.

"Girlfriend, you look wonderful. This is truly your natural state."

The whole studio was clapping and cheering, staff and clients as they too had all seen Michelle's transformation from a semi-obvious sissy to a beautiful, completely passable woman.

"Ms Lizzie, this is the best day of my life, I can't thank you enough for organising this."

Michele looked totally feminine. They paid and left arm in arm to the car and headed off to Raven's.

--

There were three cars at Raven's as they parked in the driveway. Michelle was still on a high and Lizzie was ecstatic that she had blossomed from her overweight husband into an amazingly beautiful woman.

Penny greeted them at the door, dressed in a latex hood with a gag and her hair in a high ponytail cascading out a hole in the top. Tight bands constricted each of her tits which were a dark red, contrasting sharply with her otherwise white skin. A butt plug with an extended tail hung between her legs. A short chain hobbled her ankles. Her arms were up behind her back in a reverse prayer tie. Otherwise she was naked and her body was covered in tattoos and piercings. Her eyeball whites were vampire red and Lizzie knew that her tongue had been tattooed black, pierced, split and forked.

They glanced at each other and both wondered how she could even open the door. As she turned and walked away, they followed.

Raven asked as they walked into her living room, "Have you had lunch?"

There was another young couple present also.

She took a second look at Michelle, standing next to Lizzie, "Did you bring a friend and leave your sissy home?"

Lizzie and Michelle grinned and Lizzie presented, "My newly transformed sissy - the lovely Michelle."

"Stunning, she is the most passable sissy I've ever seen. She looks all girl and if I didn't know she had a penis I would have thought she was a woman. You've done a wonderful job with her."

"Well, it's not only me, Michelle is fully on board and doing most of the work actually. And as to your original question, no we haven't eaten yet."

Michelle hadn't noticed but she had naturally deferred to let Lizzie take the lead in social situations and even more so now they were domme & sub.

Raven turned to the other couple and introduced them. "This is Jessica, who you met at the restaurant and her boyfriend Ryan. They wanted to be introduced to the scene and I didn't have another free spot this weekend, I hope you don't mind."

Lizzie answered, "No, of course not."

"Just a light meal and you must have a glass of water. Bondage and discipline is thirsty work."

Raven and Penny(?) had served up a plate of cold cut meats and a garden salad. A jug of ice water with lemon and lime slices and 4 already poured glasses were on the table. Everyone took a glass and sipped the pleasantly cool citrus flavoured water. The two couples didn't notice that Raven's glass was already in her hand, but looked identical to theirs.

Michelle looked at Penny. Her banded breasts looked to be getting even redder, towards purple. The bands constricted her tits close to her body were very tight making her tits bulge out.

Raven gestured for her slave to kneel next to her. Somewhat awkwardly, she lowered herself adjacent to Raven as she sat down. She reached across and viciously twisted Penny's nipples digging in her fingernails and then slapped her breasts.

She turned to the others, "She is such a pain slut."

"Eat and drink up, I want you to be well hydrated for the rest of the afternoon."

By the time they finished their meal, everyone had drunk at least one glass. Lizzie and Michelle had two as their last meal was at breakfast.

"All done?" Raven queried, "Bring your glass and let's head upstairs."

Penny struggled to stand but made it without falling and followed her Mistress and the others upstairs.

Raven was dressed in a bondage corset leaving her pussy and breasts free with 4" platform heels and her black hair pulled back in a tight ponytail as usual.

"Everyone please strip off completely but I want Lizzie and Jessica to remove each other's clothes and Sissy and Ryan to pair up."

Raven untied her slave's arms and removed her gag and breast bands. Penny showed no obvious pain. Her breasts were now a deep purple and the arm bondage had looked extreme too. Her elbows had been tied together behind her back with her fingertips high up level with her neck.

Lizzie and Jess had stripped each other quickly, hanging their clothes on chairs next to the wall. Michelle and Ryan were a bit slower but soon they were all naked. Other than Penny, Michelle was the only one tattooed and of course had her cage on. Ryan was very well endowed at almost 8" and thick. He was erect already. Michelle's cock looked tiny in comparison locked up in her tiny curved down cage. Sissy blushed in shame and was glad she had the excuse of being locked up to hide her small dick away.

Ryan was well muscled and lean with a handsome clean shaven boyish face. His large hanging balls matched his dick. His girlfriend, Jess, was slim and attractive with round B cup tits.

Lizzie was by far the best looking and surprisingly, Michelle was the next most attractive. Raven was statuesque and looking very domme in her black corset, long laced boots and severe hair.

"First up a game to get everyone introduced. Penny will put blindfolds on you four and you are all to kiss each other in turn for a minute."

Penny arranged them in a small square and Raven spoke in a calm measured tone.

"Welcome to my dungeon, we are here to enjoy ourselves and leave our inhibitions behind. Listen to my voice and relax, we are here to have fun. Listen and obey, I am your Mistress today." She went on for several minutes, relaxing everyone. It had been twenty minutes since they had all drunk the drugged water and were all receptive.

"When I slowly count down from 10 you are more receptive and relaxed, listening to my voice."

"10 and you are completely relaxed, waiting to enjoy yourself."

"9 and you are listening to my every word, going deeper and relaxed."

"8. You are relaxed and aroused, you trust me, you want to obey me."

"7 and you are very relaxed, listening to your Mistress' voice."

And so it went. All were in a trance even Penny, who had also drunk the same water.

"2 Relax even deeper, you want to come back here, trust me

"1 Listen, relax, obey, trust, enjoy, be aroused, love everyone, no inhibitions."

Penny who wasn't blindfolded was told by Raven to pair up Lizzie with Jess and Michelle with Ryan.

"Embrace your partner and kiss them. Passionately and with desire. Two naked bodies pressed against each other. Kiss deeper and with passion."

Michelle deeply in her feminine persona, enjoyed kissing Ryan, the first male she had ever kissed. Their naked bodies pressed against each other with his erect penis against her was arousing.

Raven let them kiss for two minutes and they reluctantly parted and moved to the next pairings - Lizzie with Ryan, Jess with Michelle.

Both couples were kissing passionately again and obviously enjoying themselves, hands roaming over the other's body. The aphrodisiac had kicked in. They were in a trance, highly aroused, listening and obeying Raven.

They had paired with each other but Raven announced one more rotation. They swapped again and she told them to hold their partners genitals and finger or stroke their partner. Michelle had no hesitation and pumped Ryan's cock while Ryan caressed Michelle's scrotum. "Caress your partner's butt, rub your hands around and fondle their body with love and affection while kissing. You love kissing and touching your partner, the sexy feel and closeness of their body."

"Have another glass of water to stay hydrated."

"Lizzie and sissy, remove your butt plugs."

"Penny, make sure that everyone's ass is well lubed."

"Lizzie, are you and your sissy clean? Do you need enemas?"

"We are clean, Mistress."

"Penny, clean out Jessica and Ryan."

"Yes, Mistress."

Jessica and Ryan meekly followed Penny to the bathroom where enema hoses were setup in the toilet and shower.

Even naked, Michelle looked very feminine, having much longer hair, earrings, makeup and tattoos all helped her appearance. She had leaned off slightly but her man boobs hadn't reduced in size at all and as measured had increased by 1/2". They were probably A cup although shaped differently to a woman's breast. The nipples were still small and man sized although a bit puffy. The makeup and hair extensions in particular had transformed her look.

Raven cuffed their hands to a rail along the wall in front of a large mirror. Raven seemed to like spreader bars as she attached a 1m bar to their ankles and a short chain to the middle of the bar to a low rail forcing them to bend over with their legs spread. She ran her hands over Lizzie's lovely ass and fingered her pussy. Lizzie wriggled her butt to increase the contact and depth of the fingering.

Penny came back after ten minutes. "I've cleaned them Mistress, shown them how to do it and to come prepared next time. Ideally they would do more flushes but they are as clean as can be given the circumstances."

"Slave, lube them all. 2" dildo for Lizzie, 2.25" for Michelle and 1" for Jess and Ryan, they are anal virgins."

Penny went to fetch all the dildo's while Raven attached Jess and Ryan to the wall as Lizzie and Michelle. She played with Ryan's cock and fingered Jess as she had Lizzie.

Penny lubed everyone's ass thoroughly and inserted all the dildos as specified.

Raven told Penny to get between Lizzie's legs and lick her pussy and fuck her ass with the dildo while she started to paddle her butt. The 2" dildo was really stretching Lizzie's hole and was on the verge of being painful, but having her clit licked kept her arousal high. The aphrodisiac they had all taken had them all wanting a release. Raven gave her 20 moderate spanks with the paddle and regularly caressed her butt between paddles. She left the dildo in her butt, turned the vibrator on and moved to Michelle. Penny continued to lick Lizzie until she had her first orgasm.

She put some Ben Wa balls into Lizzie's pussy and told her to hold them in.

Raven was paddling Michelle much harder than Lizzie and Penny, who had moved between the sissy's legs, was punching in the bigger dildo full length and faster too. Raven gave her 30 harder spanks and pushed the dildo all the way in before moving to Ryan. Again the vibrator was turned on. Michelle was leaking pre-cum drips continuously but still couldn't manage a sissygasm.

Penny was sucking on Ryan's dick slowly so as to delay his orgasm, Raven wanted to save his cum for Michelle. Raven gave him 20 moderate paddles similar to Lizzie. Raven had a real fetish to feminise men and Ryan was her next target. She wasn't sure if Jess was a dominant enough personality to take charge of Ryan so she might have them both be her subs. They weren't rich or well off like most of her older male clients but they would always be useful as subs in her business. There was a growing and lucrative market for online fem sissies and prostitutes. If she dosed them three times she could have them tranced and hypnotised to obey her completely. Neither seemed very bright and she knew they would be easy to corrupt in whatever way she wanted.

She moved onto Jess and didn't turn on the vibrator in Ryan's dildo. Jess also got 20 strokes and an orgasm from Penny.

Raven and Penny detached everyone from the rail and gave them a quick break with more drugged water. They were all drugged strongly by now after several glasses each. Their arousal would be very high as would their trance level.

Raven put an arm sleeve binding both arms on Michelle and tied her up in strappado with the large vibrating dildo still in.

She went over to Lizzie and while she was still very suggestible, said how good it would be for Michelle to have her first experience with a man. "She would love it and you would love watching her. Sissy's love to take it in the ass. After, you can have a real cock again. You know you would enjoy that so much." She repeated it several times reinforcing the command while rubbing Lizzie's clit as she orgasmed again.

She led her over to Michelle and told her to tell her that she wanted her to suck off Ryan and then to be fucked in the ass for the first time by a man. Lizzie complied and Raven knew that Michelle was going to get it tonight.

Raven tied her arms down on the horse facing Michelle with her legs over the end and spread.

Penny had a double dildo strap on and was fucking Jess in doggy with one in each hole. Raven told her to fuck Jess to several orgasms and then get her to go to sleep.

Raven led Ryan, whose dick was very erect in front of Michelle. "Sissy, your Mistress wants you to suck off your first man, are you going to obey?" Michelle nodded. "Ryan, she is all yours."

Lizzie was watching as Ryan teased her sissy's lips as she sucked in the head of his cock. She was licking around the head and obviously enjoying herself. Ryan started to push in further, gradually until she reached Michelle's throat. She had been practising deep throating and once the 8" was pushing into her throat, she relaxed and started to swallow to get it in. Ryan was able to go full depth and then pulled almost all the way out and back in.

Lizzie was watching her sissy with Ryan. Raven was talking to her, telling how much she loved watching her sissy suck off a real dick. Raven arranged the fucking machine with a 8" long and 1.5" thick dildo to start fucking Lizzie slowly but full depth in her cunt. Lizzie's pussy was soaking wet and dripping down her legs. She had another orgasm after two strokes into her sex. Raven had a wand vibrator in one hand and a cane in the other. Lizzie was about to have the best sex of her life. A 2" thick vibrating dildo in her ass, another fucking her pussy, Raven lightly caning her and holding the wand against her clit was giving her almost constant forced orgasms.

Ryan had cum in Michelle's mouth. She had swallowed it all and cleaned up Ryan's cock afterwards, savouring the taste. Her first cock. She hoped Mistress was proud of her.

Raven paused with Lizzie for a moment and moved Ryan around behind to Michelle's rear and pulled out the massive dildo stretching her ass. "Sissy, your Mistress wants you to get fucked in the ass by a man for the first time and you are going to have your first sissygasm."

Ryan's cock didn't wilt for a moment. He grabbed her hips and pushed into Michelle's ass straight away. As she was well stretched he went full depth on the first stroke. He started to pump away into Michelle's ass and was going for twenty minutes until he could manage a second orgasm as Michelle's ass slowly tightened up. He pulled out after depositing deep inside her and moved around the front so Michelle could clean his cock up again. Near the end of Ryan's fucking her butt she had her first sissygasm with any direct stimulation to her cock enclosed in chastity. A stream of semen came out of the end of her cock as she orgasmed.

"Lizzie, your sissy slut just had her first sissygasm and with a man fucking her ass. What a slut she is. She loved it."

Raven gestured to Penny to lay out Ryan next to Jess so they could sleep together. She made him get into panties, a bra and lipstick first, which he did obediently. She told him he looked great as a feminised man and needed to do it again.

Penny got out an even larger dildo for Michelle. 2.5" now and with some force and a lot of lube pushed and twisted it all the way into Michelle's ass. Her rim was as stretched as it had ever been but dosed up as she was she was feeling only some minor discomfort.

Raven gestured for Penny to cane the sissy hard and inject her with the feminising hormones.

Raven untied Lizzie, removed the dildos and took her downstairs to her bed to make love, whispering on the way, "You love me, your Mistress unconditionally. You love your Mistress taking care of and controlling you. You are totally submissive and obey Mistress at all times. You love and are aroused by being disciplined and punished by Mistress. You get aroused when with your Mistress. You want to be with Mistress all the time. You want to have a passionate affair and a relationship with Mistress. You want to feminise your sissy and dominate her completely. You want your sissy to have sex with men. You want to make your sissy a pain and piss slut. You want to degrade and humiliate your sissy. You will lose all respect and love for your sissy. You want to treat your sissy like a slave. You want to keep her in chastity permanently. You love sex with Mistress, it's the best sex, no one else is better."

They had gentle, loving sex for another 30 minutes and several more orgasms before falling asleep in each other's arms. Raven had initially programmed Lizzie during every meeting and with this final reinforcement it would be impossible for her to break control. She was now in complete control. And of course she could reprogram her any way she wanted with further applications of the drug.

Penny, in line with what her Mistress had told her how to program Michelle, told her that she wanted to be punished hard tonight and every night and that she loved being spanked, paddled, whipped and caned. She was a pain slut and being hurt aroused her. She was a piss slut, being pissed on and drinking piss aroused her. She wanted to be degraded, insulted and humiliated. She loved being in chastity, plugged and fucked in the ass. She was an exhibitionist and loved showing her self off and exposing her body. She loved and was aroused by men, their bodies and their cocks. The only way she could orgasm was by sissygasm and being fucked in the ass by dildos and real cocks. She loved sucking and being fucked by real cocks and drinking their semen. She loved the taste. She loved licking and rimming her Mistress. She wanted to expand her ass so she could be fisted. She wanted her Mistress to have an affair and fall in with Raven. She loved and wanted to be a woman and a sissy slut full time. She hated her male side. She was completely submissive to Raven and Lizzie. Michelle in a suggestive trance nodded repeatedly to everything.

She was still totally aroused. Penny then put an internal dildo gag hood with a blindfold on Michelle and noise cancelling headphones playing feminising sissy hypnos repeating much of what she had told her before into her ears. She left the 2.5" vibrating dildo on high in her ass and started to cane her. She gave her 40 overlapping strokes from each side and back. Her butt was red and purple and bleeding in several spots where the cane stripes crossed. Having the blindfold and headphones on made the unpredictability of each strike a tension building wait. Her cries were muffled and she was in a trance from the drugs, the pain and the hypnos. At the end Penny with great pleasure injected the special hormone cocktail from the endocrinologist deep into her ass. She was now fucked physically and mentally.

She left her tied up on the horse face down over the edge with the blindfold and the headphones on all night while she was still suggestible to reinforce her programming. Penny went down to sleep on the floor at the base of her Mistresses bed. The doped water's effects would wear off overnight and everyone would remember every part of the day. There was a strong residual hypnotic effect on the commands that Raven and Penny had given and wouldn't fade over time. They would be reinforced even more upon repeat application.

Raven had gotten the drug cocktail from a drug boss who used it to train women as prostitutes or punish captured rivals. Supposedly it had originally been developed by spy agencies and had eventually leaked to criminal organisations. It kept recipients aroused, submissive and under hypnotic control after several days of repeated applications. It was banned worldwide and very illegal. It was also tasteless, odourless and very effective.

Raven had drugged Penny many times and she had zero resistance to her Mistress. She had perfected her hypno techniques on her and changed her personality and sexual preferences several times. She had moulded her into the creature she now was. She was originally a mild kinky lesbian, but was now Raven's tattooed and pierced slave and there was nothing she wouldn't do if commanded.

Raven kept away from the criminals even though she was very good at training and breaking men and women and in high demand. She only did special jobs for them and took the drug as payment. The risk in getting involved at any level with them was very high and she really just wanted to build her sex empire and indulge herself.

She initially wanted to make Lizzie into a hot wife and have some fun with her but she found she liked her so much. She was so beautiful she had changed her mind to keep her as a submissive girlfriend permanently. She would degrade and corrupt the sissy and see how she felt about her later. Regardless she was going to make Lizzie lose her attachment and love for the sissy. She was a very attractive sissy and might make a perfect online porn star or trans prostitute to make money from. She was set on her feminising path regardless now after her injection yesterday.

She had drugged several of her wealthy male clients into findom arrangements who paid her regularly. She dominated and feminised them for fun. She cared little for men and the patriarchy. She could have quit her job at the sex store now but she had fun meeting kinky people. She was slowly expanding her femdom empire with the training and corrupting women in her Mistress' clinics that she had just started up.

Part 5, the conclusion is written, being edited and will be uploaded soon.