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Caught Ch. 05

A dominant young woman and her boyfriend blackmail and sissify a fellow student at university after he was caught secretly recorded them having sex. Liam becomes more compliant and starts to participate in his own sissification.

Tags : transgender, BDSM, fetish, blackmail, gay, femdom, non consensual, sissification, feminisation.

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"Suzanna just sent me some video links for you to watch on makeup tutorials. She said she will get you a makeup kit for the next session tomorrow." Allan was lying naked on his bed, checking his phone. He was the intermediary for any orders to Lianne between sessions. He forwarded the message to Lianne's phone.

Lianne was kneeling between Allan's legs stroking his cock. She was totally focused on the task. She was in her usual lingerie excluding panties with chastity locked on and butt plug inserted. Allan took several photos and a short movie of Lianne masturbating him.

"Suck the head in while you pump the shaft. After I come, you can shave my groin. Suzanna wants us all hairless."

"Yes Sir." She bent down further and licked around the head of his cock, teasing him while she gripped and held his shaft firmly. She pressed the tip of her tongue into his urethra alternating between swirling it around his mushroom head and sucking on it. She had read that humming also worked well and provided extra stimulation. Between humming, sucking and her hands rubbing along his shaft, Allan soon ejaculated into her willing mouth.Caught Ch. 05 фото

"Sissy, you get better every day, you get me off so fast. Gargle my cum and then swallow it down."

Lianne tilted her head back and gargled Allan's load as directed. She finished by blowing sperm bubbles out of her mouth while gargling. She showed Allan the pool of cum in her mouth before she swallowed it down, licking her lips to indicate her pleasure in the task. She sucked his cock as far down as she could go only partway into her mouth and clamping her lips around it, pulled up any remaining spend into her mouth, sucking on the tip to get everything out and gulped that down too.

"Sir, I love your come. Did I do a good job?"

'Lianne, you have only been a cock sucking sissy for a few days and already you are the best cocksucker I've ever had. The porn tutorials you have been watching are really working well." Lianne revelled in Sir's praise. "Come and kiss me."

Allan loved the taboo eroticism and sexual play with Lianne. She slid up Allan's naked body, licking from his groin, into his navel and pausing for a moment to latch onto each nipple before pressing her lips against Sir's. They both enjoyed the intimacy of kissing. The wet slipperiness and sensitivity of lips and tongues sharing a kiss.

"Sissy, you are a great kisser too. I can't believe how much you have changed." Lianne loved the new relationship she was enjoying with Sir and Mistress. She was getting more sexy every day and Allan was ramping up their time together with kissing, hand and blow jobs. Allan was on the receiving end only as Lianne was locked in chastity and currently on a six day schedule between releases.

"Sir, are you seeing Suzanna tonight?" Lianne asked.

"Yeah but you have to shave my groin before I go." He slapped her butt and pushed her to the edge of the bed.

Lianne sat up and rose tempting Allan by swaying her ass all the way to the bathroom to get the shaving gear. She came back in a few minutes with bowl of hot water, a face washer, shaving cream, rmoisturiser, azors and their battery operated shaver. She lovingly washed and caressed Allan's groin with the face washer soaked in hot water.

"Lianne, keep doing that and I'll cum again. Stick to the job as I need to get to Suzanna's. I need to save a load or two for her."

"Yes Sir," she grinned and stopped her caresses.

She used the battery shaver to trim all the excess hair, holding Sir's cock out of the way as necessary. Between the trimmer on the shaver, the foil head and finally the razor blade, she cleaned Sir's groin as close as she could. Allan bent his knees and spread his legs apart so she could also clean up between his legs and around his ass hole. She wiped the shaven area with the face washer and examined her work carefully, touching up some areas.

"Do you want me to shave your ass cheeks too Sir?"

Allan looked at the irregular semi-circular shaven area around his cock and balls. It looked a bit strange with hairy legs and torso surrounding the hairless region.

"Lianne, why not. I love fondling Suzanna's smooth, hairless ass, so let's do that too." He rolled over and Lianne quickly shaved his ass as well.

"Sir, I might try the depilatory cream next time." She rubbed moisturiser into his ass and over his cock and balls. She lingered with her hands, turning it into an erotic massage and Allan's semi limp member was getting more erect.

Allan was enjoying Lianne's manipulations. "Definitely feels better being hairless, you'll have to keep both of us hairless now."

"Looking forward to it Sir." Lianne's smugly agreed. She was learning to love feeling aroused in her chastity and having her erection filling the tube but unable to get fully erect. Being plugged and in lingerie added to the sensations she was feeling. Every time she saw herself in the mirror, multiple times every afternoon and evening made her feel very feminine. She was totally embedded in her feminisation process and loving it more every day. She had moved up to the 30mm butt plug herself as she knew that the eventual goal was to be fucked by Allan's considerably thicker member.

Stripping off her boy clothes and dressing up as a girl every afternoon was arousing on many levels. It was as if she changed personality, stripping away her masculinity as she changed. Her chastity was ever present, reminding her of her locked cock. She loved the process of pulling on her stockings, attaching the garter and bra. As she looked in the bathroom mirror putting on lipstick and her wig, she invariably posed for several minutes, staring at her femininised self, embracing the look and feel of her clothing. Even the regular shaving and use of the depilatory were tantalising in the maintenance of her female self.

She found herself staring at Allan's naked body and particularly his cock all the time. Sir kept her busy cleaning and tidying. Their unit had never been cleaner or better kept. Performing the submissive tasks for Sir reminded her of her status. She loved being ordered around too. Allan regularly fondled her and lightly slapped her ass as they moved around the room. Randomly he would pull her in and kiss her, fondling her ass and hugging her. Feeling Allan's naked body against hers kept her totally aroused and having him control every caress added to his submissive control and dominance of her. She wasn't allowed to initiate anything.

"Ok, sissy, I'll be back later. Send a picture of yourself posing sexily to me and I'll show it to Suzanna tonight." Allan was changed and headed towards the door.

Lianne opened her laptop and started to watch the first link Suzanna had forwarded to Allan. She was disappointed she didn't have any makeup to practice with yet. After finishing the thirty minute makeup tutorial and taking notes, she watched a sissy porn tutorial on cock sucking. Most of the dicks in porn weren't as thick as Sir's cock. She took Sir's requested image lying on her back exposing her plug and chastity. She spent several minutes taking several shots before deciding on a sultry pose with lidded eyes highlighting her toys and lingerie.

"To Sir, with Love." She messaged with the best image and spent the rest of the evening studying. Sir was usually back late from being with Suzanna.

***

"Hey babe, things are going really well with Lianne. She is happy and submissive. She sucks a mean blow job and really gets into it." He was stripping off before Suzanna who was still in her clothes.

She pulled her panties off but left everything else on. "Did she suck you off tonight?"

"Certainly did, I came in just a few minutes, she was gripping my cock, sucking on the end and humming. Best blow job ever."

"Better than me," she pouted.

"Lianne has been watching cock sucking porn tutorials and practising on me. She is completely embracing her sissy self. And yes, sorry to say babe, better than you. You'll have to lift your game," he joked.

"Did she shave your groin? Let me see." Allan removed his pants and underwear. "It looks good. Turn around, did she do your ass too?" She lay back on her bed exposing her hairless pussy, while she peered at Allan's hairless midsection. Her lips flowering open as she became more aroused.

"I like the feel of it. I told her it's another job she will do for me every few days."

"Come and lick me. I want to have an orgasm before we fuck." He removed the rest of his clothing first.

Allan got down between her legs and pulled her forward so her hips were over the edge of the bed. He fingered her slowly with one and then two fingers while starting to lick up and down her increasingly wet cleft. She liked him to warm her up before going down on her clit.

She had a vibrating dildo ready too. "Ok, clit time." Allan was working her g-spot with two fingers inside her pussy as he moved his mouth up to her clit and sucked it, sealing his lips around it and rubbing the flat of his tongue up and down over the exposed organ. She liked him to gradually increase the pressure and suck her hard as she approached her orgasm. She rubbed her nipples to increase her pleasure and lay back with her eyes closed.

She reached for the back of his head to pull him in tight. The signal to suck hard and fast. As she got close she closed her legs on his head too and curled her toes down. She quivered as she came and gasped.

"Ahhh, ahhh, lick me. Fuck, I'm coming!" She squealed as she spasmed with her lover between her legs. As she came down from her peak, she pushed his head away.

"That was a great one babe, well done." She praised Allan. She grabbed the dildo and inserted it on low vibe to keep her simmering.

Allan wanted to see his lover naked too. "Take your clothes off babe, I want to feast on your body."

He lifted her to sit on the bed, the dildo, obscenely protruding between her legs. He pulled it out, soaking wet and raised her off the bed to stand in front of him. He started to remove all her clothing until she was naked. Her blond hair cascading behind her shoulders, down her back. Her sexy curves and naked, lean body pressed against his and they kissed while they hugged and caressed each other.

He looked down between them, her breasts with erect nipples brushing against his torso.

"I like your smooth ass, it feels much better." She rubbed it with one hand as she held his erect cock in the other. She ran her hand around his shaved groin. "I like this too. Can't wait until we fuck."

"Doggy first." She moved away and knelt on the bed. Wriggling her ass to tempt and torment him. She was totally wet after her orgasm and using the dildo.

He gripped her hips and lined his cock up with her pussy. He always started slowly as his girth was massive. She was ready for him but it usually took a few increasingly deep thrusts to warm her up. She loved the feeling of being stretched by his cock. Allan was the largest she had ever had and the combination of his 8" and very thick cock always got her off. Allan started to thrust faster and full depth. She held the wand on her clit and had two rapid fire orgasms while he fucked her.

Allan had excellent staying power and had already come from Lianne sucking him earlier. He loved watching his cock move in and out of Suzanna, pulling her pussy out and then gripping him tight as he slapped his hips into her ass. Suzanna had been fucked by cocks as long as Allan's but none were as thick as his. The stretching made sex with him the best she had ever experienced. She didn't think she was a size queen but now having had regular sex with Allan, she never wanted to go back to smaller dicks. Unlike with many past lovers, she orgasmed with him every time.

He pulled out and flipped her onto her back into missionary. She pulled him in with her legs hooked behind his ass and wrapped her arms around his neck pulling him down to her. Her nipples were still tingling and erect from her previous orgasms as they rubbed against his chest as he pumped into her. They kissed sensuously as her stroked into her.

"Yes, babe, fuck me. So good, so thick." She murmured around his lips.

He set up a steady pace and she had another orgasm before he came deep in her. He slowed down dramatically staying deep in her and raised up on his elbows so her didn't press on her too hard, She tilted her hips up and down to match his slow pace, coming down slowly as his member shrunk slowly. He pulled her over so she was on top with his cock still inside.

"I love your big, fat cock. It gets me off every time. Can't wait until you fuck Lianne with it."

"She went up to the 30mm plug today. I didn't even tell her to upsize. She posed for a photo after I left. She is looking great. Very femme."

Suzanna whispered, laying on top of Allan, "Tomorrow's session will be great. I love how she is turning out."

Allan's cock completely limp by now, slipped out as she ground her hips over Allan's. She could feel her plugged pussy release his cum down his balls onto the bed.

She rotated so they could 69. Neither had any issues licking the other's sex and secretions after they had orgasmed. She sucked his limp dick into her mouth and slowly sucked on it, enjoying the taste of them both. Allan licked deep into her cunt. She pushed out his sperm which he cleaned up.

They lay back on the bed after their 69, Suzanna's head cradled in Allan's arm, resting her head on his chest. He showed her the photo Lianne had sent him. Legs spread wide with her ass hole exposed and plugged. Her tiny cock encased in her cage. Wearing her stockings, garters and her training bra. The black wig made all the difference in making her look femme. She was very passable and looked, apart from her cage, completely feminine. The added effect of her hairless body, red nails and lipstick completed the picture of a femme sissy. She would look even better with makeup. Wearing a choker or collar to minimise her adam's apple, which was barely noticeable anyway.

Suzanna observed. "As a man, he was ok looking. Sort of skinny, cute androgynous. But dressed as she is here, with wig, lipstick and lingerie, she is actually beautiful."

"Yeah she is really starting to own it. You should see her cleaning and prancing around the room. She deliberately teases me. I can't keep my hands off her. She is always staring at me and my cock. I don't let her initiate anything though. She melts in my arms when I touch her. She is so submissive." Allan smiled thinking about Lianne earlier tonight.

Suzanna snuggled against Allan. "Excellent. Makeup and heels tomorrow. Her waist could do with some narrowing to make her curvier. Plenty of places we can take her. Fake breasts, corset. She does look a bit flabby. Hips are a bit narrow for a real girl too. Her face is exceptional though, which makes a great launching place for further feminisation."

Allan offered. "I can do an exercise program for her. Limit her food so she leans out. Give her a heavy leg and butt workout, leaving her arms untouched. She is totally obedient and seems happy now. She's into it completely."

"What do you think about everything so far? Want to keep going? Suzanna asked.

"Absolutely, Lianne adds so much to our relationship. Another dimension. I'm really enjoying it. To think I am bunking with a submissive femme sissy at my beck and call is just crazy. But I love it. Watching you lead her into further feminisation turns me on."

"I'm still researching stuff. And thanks for the funds. The makeup kit was expensive. Haven't bought her any clothes yet but I'm loving the semi naked lingerie look. Almost a shame to cover her up. My sister has some very kinky ideas for Lianne. She has opened up more after I told her we dropped the blackmail and Lianne is on board voluntarily. I have a couple of surprises for her next session too."

"Anything that makes her more femme gets my vote."

Suzanna continued. "Once she can walk in heels, I want to take her out in public dressed as a girl. Go shopping for jewellery and earrings. Try on some clothes at a lingerie store. Really embed her in the feminisation process."

Allan agreed. "I reckon she will be totally into it. Drip feed her with sex, which she loves. She's such a submissive slut. The naked male, clothed female dynamic was a great idea. Even I enjoy that."

She changed the topic. "What did you think of shaved sex tonight? I preferred it. Skin to skin was an amazing feeling."

"Yes, Lianne now has a permanent ongoing job to add to her routine to keep me shaved. Sex feels better and so does wearing clothes while shaved. I might do even more."

"That doesn't bother you? What if anyone notices?" She queried.

"No problem, lots of athletes shave down, cyclists, swimmers, etc. I'm a sports major and an athlete. It's easy to explain. And all my mates know I'm a horn dog. All I have to say is that sex with you is better and they won't blink an eye."

Suzanna laughed. "Hairless horn dog with a fat cock! I love it."

***

Session 9

Lianne was kneeling on the floor with her hands behind her head. Suzanna had ordered her into the submissive position immediately she entered the room.

"Lianne, I'm just checking in with you. How are you enjoying your time with us?" Suzanna examined Lianne carefully. Her presentation was immaculate, she had obviously spent some time carefully getting ready for the session.

"Mistress, I'm not sure what to say. I've never felt this way about anyone, both of you. I've never dressed as a girl, never watched sissy porn, anything fetish at all really." Lianne was speaking slowly as if she was unsure of her feelings or at least how to express them.

Suzanna prompted, "Go on, I want to know."

A slight pause. "My whole life now revolves around you and Sir, Mistress. I can't stop thinking about the things we do. I can't wait to get back here after lectures every day." Gushed Lianne.

Suzanna smiled, "So that sounds like you are having fun. And dressing up? Being our sissy? Does that excite you?"

"I find it hard to believe, I, we have come so far in such a short time. It's as if my sexuality is being rewritten Mistress. And in a good way. Dressing as a girl and being submissive resonates deeply with me."

Allan and Suzanna looked at each other. She was surprised. Suzanna knew that Lianne was intelligent, she was acing her assignments and exams and Central U was one of Australia's top universities. They had never really talked to her as Liam and had discounted him as a nerd with limited emotional intelligence and poor social skills.

"I have to admit Lianne, we both like the femme you a lot more than Liam. I think Allan would also feel the same way that we are very much enjoying our three way relationship." Allan nodded agreeing.

"You know that Lianne is doing everything voluntarily and that blackmailing was a mistake?"

"Mistress. Sir. I want this. To feel this way about myself. I never thought that dressing as a girl would be so exciting. I used to wank off to porn and your videos daily, sometimes two or three times a day. Now I'm in chastity with you in charge of my cock. The way I feel about it is crazy. I'm so aroused and charged sexually. Thinking back on the past, I always avoided any conflict and wanted to please people. I want to please both of you. If that means I'm submissive, then fine with me. I want what we are doing to continue." Lianne looked at Suzanna and Allan in turn then down at the floor.

Suzanna lifted up Lianne's chin and they gazed at each other. Suzanna the blond statuesque goddess and the very attractive sissy kneeling at her feet. "It's sad that you were such a nerd and a social outcast. It took discovering your feminine side to be able to communicate your true feelings. But I'm glad you have. I'm finding that I love being in charge."

 

"Allan, anything to say?" She turned to Allan sitting naked on the bed.

"Sissy Lianne turns me on. She is such a cheeky thing too. She flirts with me all the time. I can't believe that Liam and Lianne are the same person. In fact they seem to be two different people. I don't think of Lianne as a boy."

"Sounds like we are all in! From what you have said you are happy to be our submissive sissy and to continue in our throuple and to be feminised further?"

No hesitation from Lianne, still looking up at her Mistress. "I'm yours completely, Mistress."

"Allan stand in front of Lianne and let her suck your balls." Suzanna was fully clothed as per the session routine every second day with Lianne and Allan in their room.

Allan moved into position spreading his legs to give Lianne better access. She bent over and sucked one of his oversized balls into her mouth. Suzanna knelt down behind Lianne and ran her hands over her body, caressing and tweaking her nipples, reaching under her bra. Lianne was swapping between Allan's testes, licking and sucking on them carefully.

"Ok, lick the head of his cock now. Savour the taste and flavour and fondle his balls while you suck on him." Suzanna had found that she could control both of them during their sessions. Even Allan was compliant with whatever she ordered. She enjoyed being clothed when they were naked.

She stroked down Lianne's back, caressing the smooth skin, tracing the crack between her ass. Continuing down between her cheeks, she felt for Lianne's butt plug and pulled it out until the widest part was just inside her ass. She kept it there and pushed it in and out slightly, stretching the entrance.

Leanne was humming on Allan's cock. The shaft was too big to fit into her mouth much past the head so she usually focused on that. Allan's hands held her head but let Lianne control how she sucked him.

Lianne had a 7" dildo around 30mm in diameter, the same as Lianne's current plug but much longer. She pulled the plug out and swapped it for the lubed dildo. She slowly pressed it in past the head and then kept twisting and applying pressure with it going deep inside Lianne's ass in one smooth push. She felt her sissy's ass and hips move forward as the dildo went deep.

"That's a 7" dildo, sissy. Still smaller than Sir's cock but we are working you up to it. You don't get a release tonight but just think of Allan's fat 8" cock driving into your ass. Taking your ass and making you his slut." Lianne was moaning and humming around the tip of Allan's cock, her tongue wetly caressing it.

"Make Sir come in your hot little sissy mouth, then kiss him, sharing his come, between you."

Allan didn't consider himself gay but neither did he consider Lianne a guy. She was a sissy and he never had a problem eating his own cream pie after fucking Suzanna either. The taboo nature of sex between the three of them and with Lianne between sessions was very arousing.

Suzanna moved to the side so she could see Lianne in profile. The majority of Allan's massive member protruded from their sissy's mouth as she sucked on the head. She was caressing his balls simultaneously. She had left the dildo fully inserted in sissy's ass. She reached around and pushed her lubricated middle finger into Allan's ass, feeling for his prostate.

Without warning, Allan ejaculated into Lianne's mouth and she clamped her lips around the base of the head so she could retain it all. Lianne could feel his balls lifting as the load filled her mouth. Suzanna encouraged her to stand and kiss Allan. She replaced Lianne and cleaned off Allan's cock, getting the remainder of his cum as the two kissed. She moved up for a three way kiss hugging them tight together.

After they shared and swallowed Allan's large load between them, she lay back on the bed, dragging Allan between her legs. "Get me off babe, my turn to cum."

"Sissy, lay on the bed next to me and fuck yourself with the dildo. Add more lube if you need it. Pull it almost all the way out and push it all the way in with full thrusts. Imagine it's Sir's cock. Which it will be soon."

Suzanna and Lianne lay side by side on their backs, their arms touching. Allan going down on her and sissy plunging the dildo into her ass. Both their legs were pulled up, touching also. Suzanna was fully clothed except for her panties, Allan's head was under her skirt. She loved Allan being naked. Naked and hairless would be even better. She was limiting Lianne's sexual contact with her. She was the dominant and seeing or touching Suzanna sexually or naked was going to be a very rare privilege. She was pushing Lianne and Allan together sexually, which her sister had suggested she try.

Allan seemed to enjoy being in charge of Lianne and getting off daily either with Lianne or her. Typical male, anything to get their rocks off. Sissy Lianne was revelling being in a sexual relationship albeit in chastity the majority of the time. Compared to her previous history of zero sex with other people, anything was an improvement. Now she was constantly engaged in a highly charged sexual environment.

"That's it Allan, lick me. Great job stud." Her boyfriend was close to giving her an orgasm. "Sissy keep using that dildo, I want to see it all the way in." Exhorting Lianne also.

"Allan, I really like you smooth, it feels sooo much better. Can you get Lianne to keep you hairless all over? I think she would love to be your body servant. Wouldn't you sissy?"

"Yes Mistress, I love taking care of Sir. I'd like to see him hairless too."

"Well your opinion doesn't really count, does it. You do what we tell you."

"Of course, sorry Mistress."

"Babe, almost there, suck hard on my clit." Allan wouldn't get to fuck her tonight as Lianne had already given him an orgasm.

She came, a good but not a great orgasm. She sighed, "Well done babe, I love your mouth." She pulled him up for a kiss.

"Keep fucking yourself sissy, no one told you to stop." Lianne was slowing down and sped up again.

"Babe I love you naked and you would be even better shaved and hairless. You would fell so good when we make love."

"Suze, no problem, LIanne will take care of it won't you?"

"Yes Sir, I'll keep you well groomed."

Suzanna propped herself up on her elbows to watch her sissy use her dildo on herself. Allan lay on his side watching also. The faint wet sounds of the dildo sliding into her ass was the only noise in the room.

"That's enough, sissy. Can't have too much of a good thing. I'll have to get you a series of bigger dildos and plugs. Your ass has to be a lot looser to take Sir's cock. You need to practice with it for 15 minutes every day. Five minutes deep throating and ten minutes in your ass."

Lianne's ass was getting a bit sore even though she had added more lube twice.

"Sissy, pull the dildo out and put your plug back in for the rest of the session. Go and wash it and I'll show you the makeup kit."

Suzanna had several items for Lianne tonight, the dildo was just the first.

By the time Lianne came back, Suzanna had the makeup kit out and went through explaining all the components. "Did you watch the on line tutorials I sent?"

"Yes Mistress, but I'll need practice. Lipstick is pretty easy."

"I want you to focus on your eyes next, that's the easiest transition and can really transform a girls face. Eyeshadow, eyeliner and mascara are what you will be focusing on. Watch the tutorials on those aspects next and work at it an hour every night. I want your eyes to be made up for our next session."

"Yes Mistress."

"You are very lucky, your skin and complexion are almost perfect, you won't need much makeup. But eyes first. I've got some heels for you tonight. Two pairs, 2" and 3". Try wearing the 2" first and then the 3" once you get confident. Walking around the room is fine. Wear them and walk in them for two hours every night. Be careful, we don't want you to sprain an ankle."

Lianne was excited, her sissification was proceeding rapidly under Suzanna's guidance. She took the two pairs of shoes, a red leather 2" kitten heel and a white 3" stiletto. She would get her some 4" & 5" platform pumps next. They would go out shopping soon enough and Lianne could pay for expanding her own collection. Ballerina flats, Mary Janes and pink joggers would give her a range of feminine footwear options for a variety of situations. Nothing the least bit masculine.

"Put them away. I want you to start organising your wardrobe and closet into separate male and sissy sections. Throw out all but 2 pairs of your male underwear as you will only be wearing panties from now on. I'll get you some girly socks suitable for sissies too."

"Your waist needs slimming down. Nowhere near as feminine as I want to see it. Until we can go shopping for a corset, I got you an elasticised waist trainer. They pull your waist in and give you some curves. Wear it during the day when you are out of the room. Garters when you are with us. Fake curves of course but better than nothing."

"Stand up and take your garters off." She ordered. Lianne rapidly unclipped them from her stockings and pulled them down. Suzanna had purchased a flesh coloured waist trainer with velcro fasteners which were contoured and wrapped around her waist.

She told Lianne to exhale, suck her tummy in and wrapped the trainer around her waist and progressively pulled it tight.

"A definite improvement." Allan complimented.

Suzanna stepped back and agreed. "Looking good sissy. But still a long way to go."

"Have you noticed how fit and toned your Mistress is?"

"Umm, not really. I mean you always look fantastic of course Mistress."

"Nice save sissy. A lot of work goes into making the complete feminine package. Exercise, diet, good posture, no slouching. If a girl, or in your case, a sissy is to look her best you need to work hard at it. Sir has graciously consented to give you an exercise program to work on your thighs, butt and tummy. And to loose weight."

"There are some natural herbs and foods that will work well in your diet. Soy, flax seeds, red clover, fenugreek and some other herbs will work wonders for your complexion and skin. I've put together a range of supplements for you to take daily."

"These aren't hormones are they?"Lianne was concerned that this might induce permanent changes.

"Of course not silly, you need to see a doctor to get a prescription for hormones. These are completely safe and natural supplements you can buy in any health store."

Lianne was relieved. Being a sissy was fun but transitioning was another step entirely.

"Allan is going to take them too."

"I am?" he queried, suddenly unsure of where Suzanna was going with this.

"Of course, your skin can do with some improvement too. And it will reassure Lianne". She snuggled up to Allan. "You'll do it for me won't you babe?"

"Yeah sure." Not quite convinced.

She handed over a bag with six vitamin like bottles in it to Lianne. "One from each bottle for each of you. Great for heart and bone health too."

"Ok, that's the boring bit over with. Lianne, have you ever been spanked?"

Lianne clarified. "Spanked as in hit?"

"MIstress." She corrected.

"Mistress, ahh no, never."

"It's really fun. Sir and I do it regularly. It adds another dimension to our sex play. Since you are in chastity you will find it especially fun and sexy."

"I'm allergic to pain Mistress." Lianne objected.

Suzanna chuckled, "Nonsense you silly little sissy. You'll love it. Watch, I'll spank Allan first to show you how it works."

Allan turned to Suzanna and raised his eyebrows. They had played with bondage and some spanking, but he wouldn't have called it regularly. In fact usually he had spanked Suzanna. She winked at him. Well they had gone this far.

"Babe, hands on the desk and bend over. I'll turn those shaved cheeks a nice shade of red. Take it like a man and show Lianne how tough you are."

Allan was now determined to demonstrate to Lianne how easy it was. Lianne was looking forward to see Suzanna spank her boyfriend. Something she had never explored or even thought much about.

Out of her bag of seemingly unlimited items, she pulled out a paddle and swished it through the air.

"Ready stud?"

She struck him lightly, slowly ramping up the intensity. Each impact made a loud slap. The paddle was not completely stiff and it wrapped around Allan's ass with each swing. Lianne watched fascinated - likely she would be next!

Allan took 40 spanks with the paddle, half on each cheek. It was starting to really hurt by the end and he wanted to squirm and rub his butt but he pretended to be stoic. Suzanna was very aroused inflicting punishment on her boyfriend. She was inexperienced and for safety had only progressed the severity very slowly. After she finished she slowly rubbed Allan's by now deep red cheeks. Caressing them lovingly.

She murmured softly to Allan. "You were very brave babe. You took it like man. Perfect example for Lianne."

He knew it would be very difficult for Lianne to back out now. He could see the logic in Suzanna's strategy. Her soft hands rubbing over his sore butt felt very nice. The soreness rapidly faded while the red remained.

"Your turn Lianne. Take it like a sissy for me, your Mistress," she announced. She manoeuvred her to bend over the desk, replacing Allan. She kissed Allan as he moved away, whispering in his ear, "Thanks babe that was perfect to help to get Lianne into it."

He wasn't sure about that, but the aftercare felt very nice indeed.

"If you remove your hands off the desk, that's five more added to the total. Allan took 40, surely you can take 20?"

Lianne thought it was hard to tell if she was hitting with the same intensity as she did with Allan but the slaps sounded very similar. She did five a side and then swapped. After every swap she relieved the pain by rubbing his butt.

Allan watching Suzanna spank her sissy, he felt irrationally proud he had taken more than Lianne.

Suzanna stared at Lianne's increasingly red ass cheeks. He was wriggling after each impact, resisting the temptation to rub his ass after every hit. Suzanna did a much harder hit and Lianne's hands immediately went to rub her ass.

"That was 16 and you only had 4 to go. I'm a bit disappointed. That's another five to the total. Hands back on the desk."

She finished the five making twenty for ten each side. "Only five more." She rubbed his ass softly and sensuously all over the red areas she had been striking. Lianne felt her cock expand out and press against the inside of her chastity cage. Yes the spanking had hurt, but it was sexy, especially the caresses after every fifth hit.

She reached under his torso and squeezed Lianne's nipples under her bra but above the waist trainer. For the last five she hit a little bit harder and sideways across both cheeks at once. Lianne was in an endorphin haze and had lost count.

"That's it, sissy. Only one weak moment. Well done. Such a brave gurl." She pulled Lianne up and helped to steady her as she was a bit wobbly on her feet. She gently kissed her and hugged her tight.

Allan was a bit jealous as Lianne was getting better treatment than he had received.

"Lie face down on the bed sissy. Allan will rub some moisturiser into your ass and then you will do the same for him."

She poured some into Allan's hands and told him to rub his hands together to warm the cream. Lianne was shivering slightly but relaxed as Allan rubbed the cream into her sore butt. The aftercare was worth the punishment for sure.

"Time for you to look after Sir." They swapped positions on Allan's bed and Lianne did her best to provide aftercare for him. Rubbing her hands gently in circles all over the raised red areas on Allan's ass. Massaging as best as she could.

"Sissy, time for me to go. Please repeat all your new tasks for me." Allan was almost asleep from Lianne's gentle ministrations.

Lianne focused and tried to remember everything. "Organise my wardrobe and throw away all but two of my jocks. Watch makeup tutorials working on my eyes. Take my pills daily." He paused trying to remember everything. "Shave Allan all over and keep both of us smooth. Practice with my new dildo, mouth and ass to enlarge my ass to be able to take Sir's cock. Wear my new heels, starting with the 2" ones. Try on my shape wear during the day. I think that's all Mistress."

"Exercise too and don't forget everything else you have been doing. Keep working on enlarging your ass. Lingerie, nails, lipstick, perfume, wig, etc. I'll send a list to Sir as he will supervise you. Don't forget to suck him every day, your job is to keep him satisfied as his submissive sissy. Learn to love the taste of his spunk. The more practice you get with real cocks the better. There are no better cocks than Sir's."

"Yes Mistress."

"You are to keep up with your studies. Must not neglect those either. You are going to be a busy little sissy, no more computer games or time wasting for you. Come and kiss me and I'll see you in two days. I want to see Sir hairless when he visits me tomorrow."

Lianne rose from the bed and Suzanna gave her the very best of passionate kisses.

"Lie down and cuddle Sir. Sleep with him tonight after you have cleaned up and put your nightie on."

"Thank you, Mistress."

End Part 5

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