Caught Ch. 06

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 is now Lianne. She is fully onboard, compliant and starts to participate in her own sissification. Suzanna starts to explore her dominant side. How will Allan react to that?

Tags : transgender, BDSM, fetish, gay, femdom, sissification, feminisation.

***

Allan woke early in the morning needing to have a piss. Lianne in her nightie was lying next to him without her wig or lipstick. it was a bit cramped in the bed with the two of them. When he came back to the bed he spooned with Lianne, both on their sides. She murmured and pushed back into him.

They were both woken by Lianne's alarm. It was barely light outside.

"Sir, we have to get up early if I'm going to shave you for Suzanna." Lianne was anxious that Sir wouldn't cooperate.

Allan stretched and lay back looking at the ceiling. He pulled Lianne over across his chest and kissed her. "I suppose we will have to get up then. How do you want to do it?"

Lianne was relieved. "Have a shower first and I'll shave you all over. Can you help me put on the waist trainer?"

"Of course. I like the way it narrows your stomach. I'll write up your training program. Meet me at the gym in the sports centre at 12:30 and I'll go through it with you. You won't need the waist trainer or butt plug at gym. Short's, t-shirt, runners and a drink bottle. I still want you to wear panties though."

"Yes Sir."

As Allan got out of the shower, Lianne had a glass of water for each of them and their six tablets. Allan took note of the labels and would see what they contained.

Lianne was meticulous with trimming and shaving Allan, making sure she got every hair. It took over thirty minutes. Allan enjoyed the grooming process. He pulled in Lianne for several kisses during the hair removal. He pulled off her nightie a few minutes into it so he had access to her whole body.

Examining his sissy objectively, while she tended to him, he thought that she needed to lean out. He would give her a muscle building program for her hips, glutes and thighs. She had a small belly and losing that would help her waist look better.

"Have you ever been in a gym before or done any exercise?"

"Never in a gym Sir and I only did the minimum at school for PE. Probably swimming was my favourite thing."

"Ever play team sport, AFL, football, basketball, tennis?"

"No Sir, I was always playing computer games."

"We will have to start easy then. I want you to workout three times a week. Mon, Wed and Fri with a rest day in between."

Lianne finished removing all of Allan's hair including under his arms and rubbed moisturiser all over. Lingering over his nipples, ass and groin.

She stepped back to admire his body. Tall, well muscled and lean. Narrow hips and broad shoulders. A handsome, masculine face with very short brown hair. His body glistened with the moisturiser, making him look like a body builder ready for competition. His cock, even limp, was long and thick..

"Sir, may I take a photo of you to send to Mistress. I'm sure she will appreciate it. You look magnificent."

Allan grinned, he was proud of his physique and appreciated the praise. "Sure. Get my phone."

***

Lianne as Liam, met Allan in the gym. In boys leisure wear but with panties on underneath. In chastity too.

He put Liam on the exerbike for 5 minutes to warmup, dialing it to easy.

He knew several of the people training in the gym from the sports science program. One of his mates came over to him and asked why he was working with Liam.

"Hey Al, how come you are working with the nerd?"

"He's a project I'm taking on. He wants to get fit. I'm supportive of him to improve himself and he's keen." Allan spoke casually but there was some steel in his reply.

"No problem, just didn't think it was your style."

"He is actually a fun guy once you get to know him. Very intelligent too."

"Liam? Fun? Whatever dude. Glad it's you, not me." He walked away, leaving Allan to his new "project".

Liam had heard the conversation. He was surprised that Allan was so protective. How things change, now they were in a relationship. He was starting to like Allan. A lot. He smiled, feeling better about life than he had in a long time.

***

"I can hardly walk. My legs are so sore!" Liam complained as they left the gym. If it were possible to limp with both legs, Liam was doing it.

Allan laughed, "You only did a few body weight lower body exercises for less than thirty minutes. You'll be sore for a few days because you haven't exercised before. I'll give you a two day break before the next session. You will be stronger soon. Won't know yourself in four weeks."

"I'm dying, carry me home Sir." Liam had looked around. There was no one close so he felt able to call his lover Sir.

"You worked hard, I was surprised. And pleased. Probably a bit too much for your first time. I'll add some protein powder and creatine to your supplements. Suzanna wants to selectively target your booty and hips. And did I tell you, no fast foods or soft drinks. It's water for you for a month or two and we start to see some results."

"Now I'm really dying. You are trying to kill me." Liam groaned theatrically and leaned against Allan for support. Allan quickly gave him a hug.

"That's enough, stop complaining or I will spank you tonight after I get back from Suzanna. You can bet I spank harder than Mistress too. It's for a good cause, making you a better looking sissy."

Liam sighed and stood up. He was slightly exaggerating his exercise tiredness, but at the moment he never wanted to see the inside of a gym again.

"The good news keeps on coming sissy. To lean you down, I only want you to eat in a six hour window daily. So if you have breakfast at 8am then you can only eat between then and 4pm. The other eighteen hours you are only allowed to have water. Definitely no snacking. Monday will be your fasting day. No food at all. I'll review your diet & exercise program in four weeks."

"But dinner is at 6pm! Food is one of the great pleasures in life. I'll starve!" Liam was genuinely shocked, Allan's diet sounded like a starvation plan.

"Nonsense, I do this every six months to stay cut. I'll print out your nutrition guidelines so you can't make a mistake. Five spanks cumulative for every error and demerit accumulated. To be dispensed by Suzanna at the end of every session. She just sent me your updated daily sissy schedule."

Liam was walking slowly. They both had lectures this afternoon.

"I'll see you at 6:30pm after dinner for some fun. I expect you to be in full sissy regalia ready to serve me before I leave to see Suzanna."

Liam sighed. Allan was serious with consequences if he disobeyed or stuffed up anything. Diet and exercise. Things he had avoided his whole life.

***

Allan researched the supplements Suzanna had given to him and Lianne. They were all foods and herbs with the highest concentrations of naturally occurring phytoestrogens and oestrogen's. Not as potent as real hormones and anti-androgens that a transwoman would take if they were really transitioning. Which required seeing an endocrinologist or specialist doctor for a prescription.

Research was mixed as to the efficacy of taking such a cocktail of natural herbs and foods. Anecdotal evidence was that they worked but there was little real research on the topic. Especially for men wishing to feminise themselves. One of the herbs he had never heard of before, pueraria-mirifica had some good evidence that it promoted feminine breast growth in males.

Suzanna had been more dominant lately. In every previous relationship he had been in, he was the dominant. The take charge guy. The alpha and bull. She was the only woman he had met who freely admitted to being a slut and took complete ownership of her sexuality. She would try anything in bed and their sex life was amazing. He knew she was trying things on to see how far she could go with him.

He was enjoying it. Her being more in charge. Perhaps he was somewhat submissive himself. It was hard to admit to himself as he had always been the alpha male previously. But he hadn't pushed back on anything yet. She hadn't fully disclosed what the herbs were, which made him feel somewhat uneasy. Something he would raise with her tonight. What else did she have planned? Lianne was into her own feminisation and was already a beautiful sissy.

They needed to sort this out immediately. What they were doing together required good communication between all parties if it was going to work. They had certainly talked about things in between sessions, but not enough, it seemed. He needed to be able to trust her 100% if they were to proceed. If she was going to be dominant over him. If he was going to let her.

***

Allan was looking forward to evenings with Lianne. She was pretty, submissive and eager to please. Quite a seductive sight in her lingerie. She was naturally taking on feminine mannerisms, whether from research or not. She looked and acted like a girl. A sexy girl that gave the best blow jobs he had ever had. Sleeping with her and their increasingly familiarity with each other was evolving naturally.

Lianne was anticipating how to make Allan feel good. Flirting very effectively. They were making a good pair. He realised that they were close to, if not already in love.

He walked into their room at 6:45pm. Lianne was standing in the middle of the room between their beds in her kitten heels. She was demurely looking down and had her hands behind her back. As he had requested - "ordered" - she was in full sissy regalia. Full set of lingerie except panties, exposing her tiny chastity cage. She had stuffed her bra with something to give her the appearance of real if only small breasts. She had done something to her eyes as well. Coloured her eyelids and they had darker outlines. She was painting her fingernails bright red every afternoon and removing it before breakfast the next day. Which must be annoying and time consuming. Allan was impressed with her commitment regarding her feminisation.

"Are you ready to serve me?"

"Yes Sir, nothing I would love more."

"Undress me slowly, make it a spectacle." He setup his phone on his desk and set it to record.

Lianne stalked him and circled before undoing his shirt, one slow button at a time. Before she removed it she looked up and Allan kissed her. Their lips pressed hard and their tongues danced together. They were both breathing hard. She was already moving well in her heels. Being careful in placing her feet.

She pushed back and Allan aided in removing his shirt. Lianne threw it onto his chair. She ran her hands all over Allan's smooth chest, kissing, licking and biting gently on his nipples. She cupped his cock in his pants and then backed into his groin with her ass, grinding on him. She teased him by undoing the button on his pants, then raising and lowering his zip several times before she relented and pulled his pants down. He stepped out of them and she threw them on top of his shirt.

Allan nuzzled at her neck licking and sucking while she lightly touched traced the outline of his cock in his underwear.

She pushed them down and his cock sprung up erect.

She grasped it, her fingers not big enough to circle it completely and massaged its length, thumbing the head.

"May I suck you Sir."

"Are you worthy, have you been obedient?"

"Yes Sir, I'm devoted to pleasing you and being the best sissy I can."

"I agree, you show excellent prospects." He gently pushed her down to kneel before him.

She smelt his essence, breathing deep before licking and then sucking the head of his cock into her eager mouth.

"Make me cum, give me your best."

She went to work his cock with her mouth, humming, sucking and licking. One hand lovingly fondled his balls and a pre-lubricated finger of her other hand pushed into his ass.

Allan came in seconds, his quickest ever. "Lianne, you are the best cocksucker."

Trying to speak around her mouthful of sperm, "You say the nicest things Sir."

He pulled her from her knees and kissed her so they shared his cum. They savoured it, unwilling to swallow.

"I love your sperm Sir."

"I love kissing you, Lianne."

"I think I love you Sir." She hugged him as tight as she could.

"I know, I've noticed. I think I feel the same."

Lianne felt warm and fuzzy inside with Allan's reply.

"I have to go and see Suze."

"Come back as soon as you can, I'll be waiting for you Sir"

"Watch the movie we just took. I'll send it to your phone. You were magnificent tonight. But get some study in and complete Suzanna's tasks."

They kissed and hugged for several minutes with wandering hands before Allan reluctantly pulled away, dressed and left.

***

Allan undressed completely in Suzanna's bedroom. Posing for her.

"That was a great photo of you after Lianne removed all your hair. You have a great body, babe. Almost as good as your cock."

He grinned and moved in to kiss her.

"I taste sperm, did Lianne share your cum with you?"

"I came, seconds after she started. Her finger up my ass did it." Suzanna digested that. "Watch this." They spent several minutes watching the movie of Lianne undressing him and making love to his cock earlier this evening.

"Fuck me, she's good!"

Allan held her at arms length. "We have some things to talk about babe."

"That sounds serious, what's going on?"

"You know I love you."

"Of course, I love you back."

"I can't believe I'm saying this, but I think I'm falling in love with Lianne. Can you love two people?"

"I'm not surprised, I see you together and how you have been the last few sessions. Culminating in her performance tonight."

"That's not all."

She raised her eyebrows.

"I checked on the tablets you gave us. Herbs and extracts with the most oestrogen content. Don't you think that's something you should have told me about beforehand?"

Her eyes turned away from his.

"I want to be able to trust you, I tell you everything."

Still nothing from her.

"I know you have been trying to be dominant over me too. Not as much or as obviously as with Lianne. But it's a thing."

Another long moment before she said quietly. "Yeah, guilty."

"What did your sister say?"

"What do you mean?"

"I think you told me she said CNC : consensual non consent. You can pretend it's non consensual role-play but it's really with the consent of the participants. I don't know if I explained that correctly, but you know what I mean."

Now she flushed very red and looked embarrassed and nervous..

"Guess what?" Allan asked.

She looked up at him again. She felt small and vulnerable in his arms.

"I let you do it because I liked it. I would like to explore it more. With you. But no more trying to secretly enact any non consensual aspects or not checking in with me first. Like trying to feminise me. Lianne wants it, but I don't or at least not currently. And you need to be up front with her too, she might be fine being a sissy but not want to go as far as transitioning. Not a lot of research on those herbs individually, let alone in the cocktail you concocted."

Suzanna had tears running from her eyes. "Allan, you are the most amazing man. I am so sorry. I almost ruined us."

"I think of it as more like getting you back on track. This is all new to us. It's easy to get caught up in it. I'm having strong romantic feelings for another guy. Never thought that would happen. Ever."

"Sorry." She repeated.

"Yeah you said that. Let's move on. I love you. And I think Lianne too. I'm not sure how far you can try to be dominant with me. Definitely not as far as with Lianne. You in charge, then me. I would like to stay above Lianne in the hierarchy. How about you do things like we did in session 9, using me to encourage Lianne to submit further. Think about it. I would like to explore it more on nights we are alone, without Lianne. Speak to your sister, she is more experienced than you."

"How did you suddenly become so relationship wise? I'm so turned on right now. This is amazing. You are amazing. I so much want to do this with you. With us together."

"Stop repeating yourself. Mistress." He knelt at her feet naked, looking up at her.

She paused for several long moments. She pushed him onto his back. Gently.

She whispered, "Thank you. Keep me on track lover."

Suzanna took her panties down off her hips, slid them down her legs and kicked them up to grab them as they flew in the air. She knelt down next to her new submissive's midsection. She wrapped them around Allan's groin close to his body and tied them off, circling his cook and testes. His cock was erect.

"This cock is now mine." She stroked him several times before she released her grip. "But I get off first. Always."

She straddled his head and gripped it tilting, pulling his mouth into her soaking wet pussy. "Lick," she ordered but Allan had already started.

He gripped her butt and caressed the soft globes as he sucked on her clit just as she liked it. She was grinding her hips on his face and he licked up and down her slit while trying to focus on her clit as much as possible.

"Finger my ass." He groped between her legs to feel for her nether hole. He stopped licking her for a second to spit on his fingers and then to resume feeling for her ass hole. Poking one finger in her, he sucked harder on her protruding bud. She needed constant pressure from oral for several minutes to come unless she was using a vibrator.

"Keep sucking. Focus on my clit. Suck it in and lick it." She was taking command and telling him exactly what she wanted. "Press hard with your tongue and rub it up and down while you suck."

Allan did exactly as directed. He was rewarded for his efforts as she came on his face, pressing even harder until she backed off to relieve the pressure.

"That was the first of many. Keep going til your tongue can't continue."

Allan had a lot of practice giving oral to Suzanna but after three orgasms, even his jaw and tongue were exhausted and cramping.

"Well done. You definitely deserve to come tonight as a reward for such good service to your Mistress." She slid down his body until she reached his groin, untying her panties and sucking his cock into her mouth. She couldn't deep throat him and even getting his cock fully into her mouth was challenging. His head was sensitive and she focused on that. He had been erect now for over thirty minutes while they had focused on her pleasure.

It didn't take long until he came in her mouth as she was expert in getting him off by now and knew what he liked. Not that any guy was very different. She retained his come and kissed him, dribbling it all into his mouth. He didn't need to be told to swallow.

She relaxed and lay next to him on the floor, her head close to his and they kissed in the afterglow of their sex. Both of them flushed and sweating.

"You know I am going to take this seriously."

"Consensuously serious." He expanded.

"I don't think they make chastity cages that would possibly fit you. Might have to get a custom cage made."

"Remember I'm bigger than you." He pinched her ass.

"But more submissive." She was glad they were having some fun with it.

"I want to fuck your ass with a strap-on and you will need training with butt plugs before I do that."

"I think I'm regretting this already." A delay and then, "Mistress." Laughing, indicating he was ready to submit.

"Remember I own your cock. No masturbating. Either Lianne sucks you or you get a release from me only."

He pulled her on top and they kissed.

"I will have to make a copy of your cock and fuck your ass with it with it. So you can see what everyone else has to stretch for."

"It's going to be fun. I'm already enjoying it" He volunteered.

"Love you, babe." Suzanna was so happy that the man she loved was giving her the freedom to explore her dominance. "Can you stay the night?"

"Of course. Lianne will be disappointed as we were going to sleep together tonight. Not have sex but just be in the same bed. But of course Mistress takes priority. I'd better message her."

"Hmm, yeah, I need to consider her too. It's so hot thinking of you and her together. A sissy sucking your cock and you loving it. Spend an hour with me cuddling and being close then go home to our sissy."

"Mistress needs to get naked."

"I can see it's going to be a problem with you topping from the bottom."

Allan grabbed her, picking her up, squealing in mock protest and slinging her over his shoulders. He carried her over to her bed and threw her down on it. "Remember I'm bigger than you. This submissive wants to be with his naked Mistress. Now."

She rapidly stripped off and held her arms out to embrace him.

"We won't always be mistress and sub." Allan told her.

"I can see that. A reversion to normal might be good every now and then. You've unleashed a monster though. Being dominant is a major turn on. I'm already enjoying it. A lot."

"Remember, CNC. I'm letting you do it to me. Because I want to explore it with you."

"I won't forget and I'm sure you will keep me on track."

***

Allan made it back to Lianne before midnight. She was lying in his bed under the covers and pulled them aside to display her dressed in her transparent nightie and cage.

"Move over, I need some sleep but I've been looking forward to cuddling my sissy."

He stripped off and lay next to Lianne. They kissed for several minutes before he spooned her.

"Do you want me to suck you Sir? I'd love it to help you sleep better."

"No, it's fine. Save it for tomorrow night."

Lianne pouted, "I was so looking forward to it Sir. I love your cock."

"Get some sleep. Big day tomorrow."

"You know something I don't?"

"Mistress always progresses you in something every session. I have no idea what she has planned but I'm sure you will like it."

Lianne snuggled her ass up against Allan's cock. "I love feeling your hard, masculine body Sir."

Allan ignored her efforts to seduce him. With difficulty. "Are you feeling better from gym?"

"I'm still sore."

"It might be a couple of days. You really didn't do much, just that you aren't conditioned. It won't take long to get you into shape."

"Thanks for sticking up for me today in gym too. No one has ever done that for me. It really meant a lot."

"Nobody messes with my sissy."

"Good night Sir."

"Good night Lianne."

Part 7 soon.