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Caught Ch. 07

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, now Lianne, becomes more compliant and starts to consensually participate, enjoying his/her sissification and feminisation.

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

***

Allan woke up with Lianne slowly sucking on him. His cock 3/4 hard. She was licking up the shaft and gently sucking on the head under the covers. Once he was awake he rapidly rose to full length.

"That's one way to get your protein supplement." He encouraged his early to rise sissy to continue.

She pulled her head away to speak, "My favourite flavour Sir." Muffled from under the doona. She went back to work, sucking harder and humming now he was awake.

Lianne made it an event every time she sucked his cock. Pumping his shaft, sucking and licking the head, humming, trying different variations. Massaging his prostate - which she wasn't doing this morning.

He needed to piss badly he realised now he was awake, which likely woke him up as much as Lianne's very gentle and slow sucking.Caught Ch. 07 фото

"I need to piss, I'll come back."

Lianne stopped again. "Stay Sir, I'll take it."

"What? Are you sure?" Allan was surprised at Lianne's request.

She didn't answer but he felt her lips seal around the head of his cock as indication of her wanting to proceed.

If Lianne was fine with it, then ok.

"Don't spill a drop." Allan warned.

Allan relaxed his cock to release a small amount. He felt the warm urine fill her mouth and bathe his cock head. Lianne gulped loudly and swallowed. She stayed locked on the tip of his cock. It was a strange feeling to piss with an erection. Harder to get the flow started.

He tried to control the urine, to let it slowly come out. His submissive lover sucked it all in and drank it down in successive swallows. Once he was finished, she licked and sucked him until she got every last drop. Then she resumed fellating his cock again.

The taboo nature of her actions had Allan ready to go very quickly as was becoming the norm with Lianne. Lying on his back, he could see the bed covers rise and fall with the movement of Lianne's head. He could feel her hands on his shaft. She was using everything she had to get him off. One hand was rubbing his taint between his ass and balls, the other around the base of his cock while her mouth was around the tip and licking and sucking hard.

It didn't take long until he came in her mouth. He could hear her moaning in pleasure just from receiving his load. She rose from up under the doona until their heads were close. She moved her head next to his and paused.

Allan thought, why not? He pulled her in close and kissed her softly, their lips just touching. He could taste his sperm with an overlay of urine. It turned him on to think about the kinky nature of kissing another guy, who was dressed as a sissy that had just drunk his piss and sucked him off. His cock was fully erect again as he kissed her hard, taking in a portion of his own cum, retaining its warmth from his body while in Lianne's Lianne's mouth.

"How was that Sir?"

Allan answered truthfully. "Very erotic Lianne. But don't think you have to drink my piss to please me. You are already doing a great job."

"I wanted to try it at least once. I really do want to please you. Being a submissive sissy to you and Mistress has been a turning point in my life. I never knew what I was missing being in a relationship." Lianne's voice oozed sincerity and restrained excitement.

"It's been a milestone for me too. I like it. A lot. The best of both worlds - having a girlfriend and a sissyfriend. Thanks for the wake up suck this morning."

"Sir, always a pleasure to receive your cum."

"How are your legs feeling today? You were moving around like an old woman yesterday."

"Don't remind me! Even worse today. Not looking forward to gym again." She complained.

"It's called DOMS. Your muscles can feel sore for a few days after exercise. It gets better after every session. The first few sessions will be the worst. Lay down and I'll massage your legs."

Allan threw off the covers as Lianne lay face down. Lianne had noticing that Allan's interactions with her had changed over the last week. Caring and sharing to say the least. She was starting to understand and appreciate the benefits of being in a real relationship with another person. They cared for each other. Small things like communicating, touching, caressing, kissing and more.

Allan gently massaged Lianne's legs from knees to hip after she pulled her nightie off. Lianne groaned. "That's a feel good pain."

The redness from her spanking had faded completely. Allan didn't go deep or press hard as he rubbed her legs. "Turn over and I'll do your front."

He wasn't trying to make it sensual. "The front hurts worse Sir."

"Yeah bigger muscles. Massage will help a bit but nothing you can do except put up with the pain for a short while. I'll do less with you next time we are in gym. Stay active and walking around will help a bit." He could see her chastity push out slightly from her groin as her sissy cock tried to get erect. The tip of her cock was pressed tight to the end of the tube.

"I could stay here all day with Sir taking care of me like this. Loving our new relationship dynamic."

Allan stopped massaging and licked Lianne's nipples before kissing her again. "That's it for this morning. I've got an early lab I need to prepare for and a biomechanics tute. My hardest subject, I'm struggling with it." Allan had previously never shared much with her in the past.

Lianne immediately piped up, excited at the chance to reciprocate for gym training. "Sir, I'm good at maths, I've seen your biomechanics material and I can help you with it. I'd love to in fact." She had worded it carefully not putting Allan down.

Allan smiled, appreciating the offer. "Lianne, that's great, I'll take you up on that. Exercise from me and maths from you."

"Sir, ask me for anything. I'm yours to command. Seriously." Lianne sat up and hugged her lover, the two naked bodies affectionately embracing.

"Lianne, as much as I'd love to stay here, we will both have plenty of fun tonight. Mistress is really embracing her dominant nature. Expect her to push you a bit more every session."

"Sir, every day is amazing, whether with just you or Mistress as well."

Allan agreed. "As it should be! Don't forget, no fast foods and the limit of a six hour eating window. Take your herbs and tablets this morning. I like the shapewear. It gives you a much more feminine shape. I wouldn't leave the checklist that Mistress sent me for you lying around. Keep it secure on your phone and laptop." Forgetting that Lianne was an IT major.

"Sir, the routine of getting ready each afternoon for you is one of my favourite parts of the day. I feel my feminine persona blossoming each day as I prepare. I get better at it every day."

"Lianne, you are a treasure. Come here and kiss me goodbye."

***

Suzanna was relieved that everything had gone so well with Allan last night. She didn't realise she had got it so wrong. He was totally on point with everything he had said. Thinking about it after he left, she realised that he had taken the opportunity to educate her and bring things back into alignment. And to confirm how he wanted her to proceed. With his consent. She was naive to think that she could have proceeded as she had planned and that everything would magically fall into place. Her sister had laughed at her when told what had happened and said she still had a lot to learn. That she was lucky to have such a mature, understanding and seemingly submissive boyfriend and with a big cock. She loved Allan more than ever after last night. She didn't know exactly how things would precede with their fetish relationship adding Lianne into the mix now they had embarked on it. But she couldn't wait to find out.

She had previously ordered several items in anticipation for session 10 with her boys tonight. She was planning at least a session or two ahead. She was picking up some gel inserts today to give Lianne more realistic looking breasts. Just like real women had to deal with. B cup sized. Hopefully her strap-on had arrived too and more dildos in a variety of shapes and sizes.

She already had a range of butt plugs at their unit and she wanted to start Allan using them as well, progressing and enlarging his ass too. Lianne was up to 30mm unless he had gone up in size again since their last session. She estimated that she needed to stretch her up to taking a 50mm plug before she could take Allan's cock.

She planned for 35mm tonight for Lianne. The stem at the base of the plug was thin and she thought that it didn't stretch her ass much, dildos were better. Opinions varied on-line on how best to stretch ass holes but everyone pretty much agreed that slower was better than faster. Tearing Lianne's (or Allan's) ass would be a major setback and delay things considerably. It looked like large conical dildos and anal speculums were best for gradual stretching with 2-3 days rest between sessions depending on how hard you went.

She had ordered both the conical dildo and speculum for pickup before session 11 which would be a release session for Lianne. She had reviewed some extreme online content which totally amazed her how far an ass could be stretched. Sisbet and Argenbana were two online anal athletes who must have worked for years to get their asses to take such large objects. 2 litre plastic bottles, arms up to the shoulder, footing, triple fisting, prolapsing, extreme dildos and more - all quite shocking. And they were far from being the only ones. It seemed to be an active contest to see who could make the most extreme content. She would be happy to get her boys up to taking her fist eventually. Even that was a long term goal. While she didn't know how she would feel in months or a year away, those sorts of extreme weren't where she planned to go. Just the power play and dominance was what excited her. Having obedient submissives following her commands was hitting all her kink buttons.

She had done several searches and read through forums for large chastity cages for Allan. There was nothing readily available as a stock item that could take his girth. The best option appeared to be Kinkcages, who had an excellent reputation for comfort, security and custom fitting. Based in the US, they had established fitting shops worldwide. They had numerous components in a wide variety of shapes and sizes for each section of their cages. Men could come in and try them on to on to get the perfect fit. They said there was no cock they couldn't lock. She was planning to take him for a fitting this weekend. Even thinking about having both of them locked was very arousing.

Lianne would hopefully be ready for an excursion out of their unit this weekend. She had several things planned for Lianne while outside. She would have to handle it carefully to get her to agree to cross dress outside for the first time. Hello world, here I come!

She already had possession of all the other items she needed for tonight. As much as she enjoyed dominating and feminising Lianne, she was even more excited and motivated to have Allan as her submissive. She was on the phone with her sister daily to ask for advice. Her sister had given her links to numerous resources to digest and read. Quality BDSM & transgender fiction. Podcasts, erotic literature, blogs, forums and fetish sites. She was on a crash course for all things kink. She was even considering interning with a local BDSM Mistress. Her sister had suggested several likely prospects.

Session 10

"Position." Suzanna ordered as she entered the room.

She had given Allan a list of Lianne's routines : clothing, sissy practice, protocols, diet, exercise, etc. Which he had added to and passed onto Lianne.

The latest protocol from Mistress was for Lianne to drop to the floor and kneel with her hands behind her back and her head down whenever Suzanna entered the room.

Lianne had been practising walking in her heels while cleaning the room. She immediately dropped at the designated position upon hearing her Mistress. In anticipation of the arrival of her Mistress, she was already dressed and made up with blue eye shadow and black eye liner. Her eyelashes were darker too. Every little addition to her routine was making her look more feminine.

"Let me look at you." Suzanna examined Lianne kneeling as directed. Circling and appraising her appearance.

Allan was naked and sitting on the bed watching. Being naked with Suzanne clothed was exciting. His cock was almost fully erect.

"I must admit, you are looking good Lianne. Very feminine. Certainly obedient. Allan, has she accumulated any demerits?"

"She has been perfectly behaved. She is trying very hard. I'm sure she will make a mistake eventually but nothing since the last session."

"Very good my sexy sissy. Checking in now, Lianne. How has everything been? Give me a detailed report."

"Mistress, I have started Sir's exercise program and diet. Walking in the heels has been progressing. I'm going to try the stilettos tomorrow. Getting better with eye makeup."

"Yes I can see, needs to improve but acceptable given your inexperience. I think you should wear the shapewear in the evenings too. I like seeing you with a narrowed waist, so skip the garters for the moment. They look sexier but a curvy shape is good too."

"Of course Mistress."

"I hear you are enjoying your time with Sir. Catching some feelings for him?"

"Mistress, no reflection on you but I think I love Allan, his body, cock, kissing and cuddling, serving him, sleeping with him every night."

Allan agreed. "Suzanna, the feeling is mutual. Lianne is compliant, loves to serve me in every way and has been the perfect submissive companion, servant and sissy." Allan was sincere in opening up about his own feelings.

"Allan and Lianne, I never imagined the trajectory of our three way relationship heading this way. But I'm finding it the best and most satisfying time of my life ever. It has been and is so good. I love my man and sissy."

Allan stood and pressed up behind Suzanna, his arms wrapping around her front.

"Lianne, I need to further clarify about the herbs and tablets you are taking. They are all high in naturally occurring oestrogens and phytoestrogens. They are not hormones but might have a minor feminising effect on you over time. Allan can explain more."

Allan took over the explanation. "Not a lot of research on this, particularly with respect to feminising men but Mistress's initial comments when she gave them to us to take was correct but not the full story. So with full disclosure, we don't know how potent the cocktail will be. Very likely more than taking only one. Any changes, if they occur, will take months and years."

"Sir, what sort of changes?"

"I'm not really sure but things like : female fat distribution, softer skin, maybe less facial and body hair, maybe minor breast growth. I'm still researching it but if you stop taking them, I believe the changes are reversible. But don't quote me. Trans women take real hormones, which have a dramatically bigger and quicker effect. They get a prescription from doctors. But you really need to get expert advice. Which is not me."

Suzanna's face was flushed red and she looked embarrassed. Allan wasn't blaming her, but her neglecting the details initially which he had just clarified was important to be explained.

Silence for a minute.

"So nothing short term and reversible if I stop taking them?" Lianne looked up at both of them as she spoke.

Suzzana elaborated. "Completely up to you if you want to continue to take them or stop. No orders or compulsion from us."

"I understand there is a difference between a cross dresser and a transwoman. I've been reading up on it myself. A sissy could be either it seems." She paused. "I feel very feminine whether dressed as a sissy or not. I definitely prefer being dressed as a girl and am really enjoying it. I want to continue being submissive to both of you, cross dressing and to be feminised more."

"We love the feminine Lianne." Allan, spoke for both of them.

"Given there is no immediate effect and it's reversible, I want to continue. Is Sir going to take them too?"

Allan had seriously thought about it since doing his research and talking to Suzanna yesterday. He made a spur of the moment decision. "Yes."

Suzanna was startled. Allan had reversed his stance overnight. She turned to look at him. "Really?"

"Yes, I want to take them too. We can talk more about it later."

"It seems I might have two sissy's on my hands then."

Lianne smiled and facetiously asked, "Should I still call you Sir?"

Allan looked at Suzanna. "We will let you know. Sir for tonight."

Allan hadn't yet taken the tablets today. He dispensed the full complement into his hand and swallowed them with some water..

"We got a bit sidetracked there. I was checking in with you Lianne. Everything good to continue with our throuple and fetish play?"

'"Definitely. I want to be feminised further, dress and act as a sissy and be submissive to you both." She stated it definitively again.

"Allan or perhaps Alana, do you want to put on some panties for me? I'd really like it if you did."

Allan looked indecisive. This was a big step for him. He looked at Lianne's hips, she wasn't wearing any but she was a lot smaller than him. He had substantially more muscle and was much taller. A manly man, her boyfriend and lover.

Suzanna was quick to make some decisions for him and could see the practical issue at hand. She wanted to run with the vibe of the situation and push him further. "Lianne, go get your biggest, stretchiest pair of panties and Alana can try them on." She realised that her own hips were much wider than Lianne's and that Allan/Alana might be better suited wearing hers.

"Actually, Alana, try on mine, they will be a better fit." Lianne who had started to sort through her panties, stopped and came back. Suzanna was wearing skirts almost all the time lately so Allan could lick and fuck her more easily. She was able to remove them quickly.

"Alana, these will fit you perfectly. Your Mistress wants you to try them on." She dangled them in front of him. Lianne was watching intently.

Allan looked at them. Pastel yellow. Lace trim. Subtle floral pattern. Completely feminine. Slightly damp at the front. He blinked... and took them. Almost in a daze, he oriented and slowly stepped into them.

Lianne asked if she could help and moved close to Allan. "May I assist Sir?"

She took the panties and slowly raised them up Allan's legs. She caressed his shaven, hairless cheeks and lifted them all the way up. Not a perfect fit but certainly good enough.

"Alana, you look lovely. I love how they are on you." Complemented Suzanna. Allan was motionless.

Lianne untangled Allan's cock and it stuck out above the front of his panties. Very erect. As she was handling it, Allan spontaneously ejaculated. She quickly took the tip into her mouth and sucked to get his load. Several ropes of cum dripped down her face.

Suzanna was amazed at how events had progressed this evening. It was beyond her wildest fantasies. "Kiss your fellow sissy, Lianne. Alana wants to taste and share her cum with you." She was taking every opportunity to reinforce feminine terminology with Allan as Alana. Allan hadn't objected to anything yet. Having released, he might have a mental drop and second thoughts. Important to get a chastity cage for him as soon as possible to maintain his arousal and reinforce her dominance.

Allan and Lianne were kissing and Allan was licking up the sperm on her face. Suzanna wouldn't try any further feminisation on Allan tonight except for a butt plug. They would discuss everything their first time alone.

 

"I love to see my girls kissing. Such a lovely sight. Lianne, I have some special plans for you tonight. The evening is just getting started."

She went to her ubiquitous bag of tricks. Which looked full as usual. She pulled out two realistic looking B cup fake pink breasts with protruding and slightly darker nipples with large areolae. They could be slipped into bra cups or glued on. They were semi sticky and adhered to smooth skin so they wouldn't slip even if not glued. She had purchased several larger cup bras to match.

"Sit down Alana." She guided Allan back to his bed. His cock had shrunk after his release and she tucked it back into the panties.

"Sissy, take off your bra and put one of these on." Lianne took her training bra off and Suzanna quickly helped her to put the new one on, placing a fake breast into each cup. Much better looking than stuffing her training bra's with socks.

"Now that should feel much better. Just like real ones. What do you think Alana?"

Allan was watching. "Lianne, you look fantastic with those."

Lianne could feel increased pressure from the bra shoulder straps as the inserts weighted down her bra cups. The nipples tented out the thin bra material, looking very natural as she had planned. She cupped them in her hands feeling the heft.

"I love them. Thank you Mistress."

"Remove your butt plug, I'm going to put the 35mm one in tonight. Get it and go down on all fours on the bed. Alana, I want you to help. Get the lube please."

Suzanna pulled out a prostate vibrator and an 8" dildo out. The dildo was still a lot thinner than Allan's member but a bit wider than the 7" she had used on Lianne in session 9. She wanted to see if she could get Lianne to have a sissygasm tonight. Unlikely, but another goal for her sissy to work towards.

"Lube her ass Alana and play with the 35mm plug inside her for a few minutes. Stretch and work the hole."

Lianne was on all fours on her bed. Allan had already inserted the plug all the way in and was cycling it in and out. Twisting as well.

"Relax your ass sissy. How does that feel?"

Lianne was feeling good. "Not too tight, I'm really loving the feel of my ass being penetrated."


"More where that came from tonight. You're going to love it. Keep going Alana." Suzanna encouraged.

After a few minutes of playing with the plug, Suzanna wanted to move on. "Ok Alana, take it out and try the 8" dildo next."

Allan placed the plug on a towel on the bed and lubed the 8" dildo. It was about the diameter of the plug that had just been in her ass.

"Wait a moment Alana, I think you need to join your fellow sissy in plugged ass solidarity. Time for a butt plug for your cute shaven butt too. Do you want to start with the 20mm or 25mm plug?"

Allan was acting very submissively tonight. Being a sissy suited him it seemed, even after he had ejaculated. "The 25mm plug please Mistress."

"Done. Get it and I'll insert it for you. I'll have you upsized in no time." She was enthusiastic at the progress of the evening, juggling the domination of her two sissies.

Suzanna squirted some lube onto the plug. "Alana, is your ass clean?"

Allan hesitated and said in a low voice after a moment, "No Mistress."

"A demerit for each of you then. Lianne you can't neglect getting your fellow sissy prepared for a session. The plug is going in regardless."

She was loving this. Both of them were so submissive tonight.

"Alana, I want you next to Lianne on the bed. The plug is going into you first and then the 8" dildo into Lianne."

She pulled his panties down clear of his butt and poured lube down the crack of Allan's ass. Without much preliminary warmup, she pushed the plug into his hole, twisting to assist the penetration. It popped straight in and seated in his crack. Then she placed the 8" dildo at the entrance to Lianne's puckered hole. She was already warmed up and she pushed it in and out several times before it was all the way in, the realistic shaped testes at the base of the dildo. It had a flanged socket in the base where an attachment could be fitted for connection to a strap-on harness.

With a hand on each, she simultaneously moved the plug and dildo in and out of their asses for a few minutes.

"Wait a moment, perfect time for a photo." Lianne had her garter and stockings on. Allan's panties were pulled down halfway down to his knees. The plug and dildo sticking out of their respective ass holes. She took several photos at various angles and distances.

"Alana you had better remove your plug in the toilet and wash it. Lianne fuck yourself with the dildo for a few minutes, but lay on your back with legs spread, I want to take some more photos'."

She sat back on Allan's bed to take a video of Lianne at play. Her ass stretched by the long, black dildo.

"Lots of stuff planned for the next session on the weekend sissy. And how many days since your last release?"

"It will be 6 days Mistress."

Allan came back into the main room holding the cleaned butt plug. His cock jutting up well above the pantie line. Otherwise he was naked.

"That's a sad look for a sissy Alana. I will have to do something about it as soon as possible. And Lianne, that's enough for you. Dildo out. Paddle time now. 20 each plus 5 extra for your dual demerit point."

She picked up the paddle and swished it through the air. "Ok, each of you kneeling on the ground and bent over your own bed."

As they moved into position she put a set of padded cuffs on Lianne, restraining her hands behind her back. She hadn't come prepared for Allan tonight so she used one of his ties to bind his hands in the same position. She took some more photos of their currently pristine bottoms. She nudged their knees apart so she had access to their groins.

"Every noise either of you makes will be an extra smack for both. Understand my sissy's?

In tandem they replied. "Yes Mistress."

Like in the last session, she started light and gradually increased the intensity of the blows. Five paddles each on one cheek then swap to the other sissy. She was glad the rooms had thick and soundproof walls as the paddling was noisy with each strike giving off a resounding smack. Their ass cheeks becoming increasingly red. She went a bit harder on Allan. She paused several times to record their "redness" on her phone. Neither made a sound as she had warned.

The same number of paddles as the last session but she went harder on both, starting with Lianne. She caressed their skin after every five. They obviously appreciated the rubbing and pushed back into her hands. Lianne was in chastity, so she only stroked Allan's cock at the same time as she caressed his ass cheek's before resuming the beating. His cock hanging down erect. Dripping pre-cum.

After finishing Lianne's 25 paddles and some aftercare with her, rubbing and caressing her red ass, she told her to get between Allan's legs, the cuffs still on, lay on her back and suck on his cock while he received his last five paddles.

"Alana, tell me when you are close. I want you to come on the last paddle. Count them down and thank your Mistress with every strike."

Lianne had moved awkwardly into position as she was still cuffed with her hands behind her back, with Allan's cock head in her mouth. Suzanna set up her phone at an angle to record a movie of the last few hits.

Whack! "5. Thank you Mistress." That was harder than every previous hit. On his left cheek. His ass was much redder than Lianne's.

Whack! "4. Thank you Mistress." Slightly harder again on his right cheek.

Whack! "3. Thank you Mistress." Incrementally harder on his left cheek. Splotches of purple amongst the red now.

Whack! "2. Thank you Mistress." Matching strike on the right. Allan was squirming now, wanting to avoid the strikes.

"Lianne suck hard. I want you to get Alana off. Tell me when you are about to come Alana." She paused until Allan said he was about to come. She picked up the 30mm butt plug in her left hand and quickly lubed it.

"Now Mistress. I'm coming now."

Suzanna hit twice, the hardest two paddles yet, once on each side as Allan started to cum in Lianne's mouth. She could see Lianne's cheeks puffing out as Allan filled her mouth with cum. She pushed the 30mm plug into Allan's hole quickly while he was still pulsing his sperm out. A slight barrier and pause but she barged through his tight sphincter and seated the plug.

Allan groaned as he came, harder when Suzanna hit him hard twice and the pitch of his voice raised as the plug stretched him as she rammed it home.

"Ahh, fuck, 1. Thank you Mistress."

"Lianne, move up and kiss Alana while I moisturise her ass." Lianne crawled awkwardly out from between Allan's legs with her mouthful of sperm and lay on the bed next to Allan. Suzanna could see them kiss as she tenderly caressed his butt. It was very red and she soothed it by rubbing the cream in lightly for several minutes. Allan's hairless ass felt good under her hands. It was tight and muscular without her added layer of fat. Eventually she tapered off with her aftercare and pulled her yellow panties up Allan's legs to seat them on his hips.

"How are you feeling Alana?" Allan was still bent over his bed face down, head turned, kissing Lianne. He pulled back from Lianne and twisted around, his hands fastened behind his back also, to lay on his back between Suzanna and Lianne. Gingerly easing his back down.

"You really laid into me today. Especially the last five. But... I can't say I didn't like it. I'm making some very submissive choices and it's actually turning me on immensely."

Lianne was just laying back listening, pressed again Allan's side, one raised knee bent over his stomach. Suzanna turned to Allan. "No rush with anything, I pushed a bit hard. Just take things as you feel ok about them. But I'm feeling great about the both of you. Dominating my two girls is such a buzz." She had noticed that Allan wasn't correcting her about calling him a girl or Alana.

"Lianne, the session isn't over for you yet. Are you ready for more?" Given how the evening had gone so far she wanted to solidly establish her mastery of both of her new girls.

Lianne had been looking at Allan and looked up to gaze at her. "Of course Mistress."

"Bend over your bed again, same as before, kneeling on the floor. I want to see that cute little red ass on display." She got the strap-on harness she had picked up today and fastened the 8" dildo at the front. She pulled down her skirt and stepped into the harness, tightening the straps.

"Alana kneel next to me and watch me peg Lianne but the far side, away from the phone." Allan slid off the bed and manoeuvred into position, hands behind his back. Suzanna checked and her phone was still recording.

More lube on the dildo, jutting out from the front of her harness, drooping down, unlike a real cock. She grasped it to lift and point it at Lianne's puckered hole.

"Here it comes sissy, your first pegging from your Mistress. Tell me how much you want this."

"Mistress, please fuck my sissy ass."

"Not anywhere good enough. Beg for it." She slapped Lianne's ass twice over the red patches on each cheek.

Allan was grinning at the two of them in action. Wishing it was him. He loved the way Suzanna was taking charge.

"Mistress, I beg you to take charge of your slutty sissy. I want your cock so much, buried it all the way in my cute sissy hole. Take me hard."

"Better, but you still need to work on it." She pressed forward and the tip slowly opened up her hole. "Whose ass is this?"

"All yours Mistress. All of me is yours."

"Don't forget it." She pushed in and out until she was fully buried. Her hips pushing on Lianne's butt. She wished she had a real cock so she could feel it. She gripped Lianne's hips and started to thrust harder. The end of the dildo almost exiting and thrusting hard to slap her hips into Lianne's red ass. She added a few slaps. It took her a few goes to get the angle and depth right.

Allan was swaying, pushing his hips forward, wishing he could get some contact with his cock. Watching Lianne get pegged hard.

"Push back onto my cock, sissy. Fuck yourself on my 8". Don't just kneel there." She wanted to make Lianne complicit in her own pegging. "I bet that little clitty is straining inside your chastity."

Now with every thrust, Lianne was timing pushing back as Suzanna lunged forward. She kept going for ten minutes, varying the depth and cadence, forcing Lianne to adjust. She finished with ten hard and fast, full depth pumps, then pulled out. Unstrapping the harness, she undid the tie keeping Allan's hands behind his back and passed the harness to him. "Clean this Alana, then come straight back."

She ran her hands down Lianne's ass, her ass still gaping slightly from being pegged. She pushed two and then three fingers in, twisting. She added a fourth but couldn't get in very far, not even close to her knuckles. "Your sissy ass needs a lot more stretching before you can take Alana's cock. I want you to work on it. I'll leave the 8" dildo with you. Progress to the 40mm butt plug soonest."

Allan walked out of the bathroom holding the harness. "Remove the dildo and suck it while I stimulate Lianne's prostate."

Allan examined the harness and detached the dildo, immediately sucking on it. Trying to get it to the back of his throat where he immediately gagged. "Keep going, relax your throat," Suzanna advised.

Suzanna pulled out the last item for the night a curved and fairly short prostate dildo and vibrator. More lube. She had charged it up before she came.

"Lianne, I want to try to give you a prostate orgasm, a sissygasm while you are still in chastity. You are allowed to come if you can. I'll press it in and tell me when it's in the best position." It was smaller and thinner than the 7" dildo but had several bulges along its length.

"Yes Mistress."

She turned the vibrator on low and pressed its curved, bulging length into Lianne's loose ass. She pushed it in slightly. Then further in and out a bit more with every thrust.

"Just there Mistress, that feels good. Keep moving it back and forwards slowly." Suzanna turned the vibrator to medium.

"Ahh, never felt anything like this before." Lianne's moaning overlayed with Allan's gagging, saliva drooling down his chin.

Suzanna hope she could get Lianne to come from anal and prostate stimulation while still in chastity. "Are you going to come Lianne?"

"It feels amazing, better than the 8" dildo Mistress but the sensation plateaus and I'm not sure if I can come."

She turned the vibrator to high. "How about now?".

Liane was pushing back and grinding her hips to maximise the stimulation. Suzanna continued for another ten minutes but Lianne couldn't orgasm from the prostate vibrator. She pulled it out slowly, tantalising Lianne and turned it off.

"That's enough. Alana, clean this vibrator too."

She undid the padded cuffs from Lianne's wrists. She would have to purchase another set for Allan. She picked up her phone and stopped the video. Over thirty minutes of recording.

She laid out all the toys on a towel. Lianne and now Allan were building quite a collection.

"Alana, see if Lianne's gaff fits you. Until I can get a cage that fits you, a gaff will have to do." Lianne searched in her drawers for a moment to find her gaff. It was a tight fit on her. Allan couldn't even get it half way up his thighs.

"Oh well, more shopping then. Big weekend planned my sweet, loveable sissies. Now incorporating Alana. Expect some femme underwear coming your way tomorrow."

They were both listening attentively, Lianne in lingerie, her new B-cup inserts making her look more feminine than ever. The wig was partially askew and Suzanna adjusted it for her. Allan was standing next to Lianne wearing Suzanna's panties. Looking very butch. Lianne could very likely pass in public dressed as a girl, but Allan never. She would have to talk to him alone when he came over next and see how he felt about tonight and where they wanted to go with his submission and feminisation to her. She wanted to take him further but likely not in public. Liane was going all the way.

"It's been an amazing session, my sweet things. The best ever. And welcome Alana to the mix. I couldn't be more pleased."

Lianne and Allan glanced at each other. Smiling, blushing.

"Give each a big passionate kiss and then come and say goodbye to me. It's getting late."

Lianne spoke up. "Mistress, can I wear nail polish outside the unit. I would like to go with black and the same for my toes."

"That's a big step, are you sure?" Suzanna didn't want to out her. Any decision to go outside with any externally visible feminine accoutrements, clothing or makeup would be her choice to make.

She explained, "I think I can go goth and do my eyes too. There are a few guys in my course with earrings, studs and painted nails. No sissy's or trans women... or at least none that I know of. I want to slowly push the envelope and get more comfortable outside. Hard core sissy only alone with you and... Alana of course."

"I'm proud of you Lianne. How far you have come. Alana, give her a big fat kiss & hug for being so brave."

They turned to each other, Allan standing much taller than Liane. They were obviously comfortable in each other's arms. Kissing and hugging, they were pressed against each other in a sexual embrace for minutes, lost in their own passion.

Suzanna was soaking wet watching them and would need a session with her vibe tonight.

'Break it up girls, I'm going and you need to say farewell to your Mistress. You can have more fun tonight after I'm gone. Alana, I want the second key for Lianne's chastity back. I'll pick it up tomorrow. You're both going to be locked up and I will make other arrangements for emergency access to a key when I'm not here."

Reluctantly, they both pulled away from their embrace and came to kiss Suzanna's extended hands, one on each side.

"Lovely work tonight girls. Session 11 for Lianne will be tomorrow, Saturday. Alana, I will call today's session #1 for you. #2 will be tomorrow. Alana, keep my panties overnight but I will want them back, cleaned and folded. We will all be going shopping tomorrow. Girl's day out, big day for everyone. I'll be here at 8am to help you get ready."

She turned away and left. At the door, she glanced back, Lianne and Alana were already embracing & kissing again. She would have to add Alana to her planned activities for tomorrow and update her plans.

She texted Allan on the way home : I love Alana, so looking forward to getting to know her better.

Part 8 soon.

Rate the story «Caught Ch. 07»

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