Caught Ch. 03

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.

Session 6

"Lianne, I've been very pleased with your obedience and progress. Have you been enjoying our sessions?"

Liam was actually unconsciously starting to enjoy the sessions with Suzanna and Allan. He was even reluctantly starting to admit it to himself. Masturbating to porn and even to his secretly recorded videos of Allan and Suzanna was nothing compared to being involved with them in sex play, limited as it was and dressing up as a sissy. Suzanna masturbating him to an orgasm with her hand, even though he had only lasted 30 seconds was the highlight of his pitifully limited sex life. Even the taboo nature of dressing in lingerie as a woman was exciting.

He was currently dressed in a thong gaff, bra, garter and stockings while wearing lipstick standing in front of Suzanna fully clothed with Allan wearing only his underwear, sitting on Allan's bed. He had no breasts, so he was flat chested under his padded training bra. But Suzanna thought he looked quite feminine and was very pleased with his progress, incomplete as it was. With some makeup, fake breasts and a wig, he might even be passable. With his slim build and not particularly manly features, she could see his feminisation proceeding well. He seemed to be increasingly submissive every session. Things had improved with his compliance when she switched to praising him and his resentment for being blackmailed had disappeared.

He was even starting to participate with his sissification. She found being in charge of him and the whole process exciting and arousing. Every directive she had given him, he had been compliant with.

Liam said nothing, so she prompted him. "Lianne, I think you are starting to enjoy our sessions together. Admit it, please."

He finally, slowly whispered, "Yes."

"Thank you for admitting it. I have too." Suzanna smiled.

She pulled down the front of Allan's jocks and started to pump his flaccid cock with her hand. It rapidly stiffened in her hand. Liam watched it grow as Suzanna caressed and stroked it. She pulled his foreskin back as she moved her hand grasping his cock down and then back up. His 8" cock was covered in veins and the mushroom head expanded as he approached full stiffness.

"Doesn't his cock look wonderful, it's so big and stretches my pussy. I would need two hands to hold it. Allan can fuck me for ages and gives me several orgasms." She promoted Allan's manhood to them both.

Liam was getting off on the humiliation. He reached one hand inside his gaff to push it down to start to masturbate.

"Not yet Lianne, just watch."

He stopped. His cock was trying to get erect but bent back inside his gaff it limited his erection.

"I want you to try to hold back. I want you to last longer than 30 seconds. In fact I have something tonight to help. If you don't orgasm and don't masturbate, I promise you another big surprise in session 8." She purred her promise as her hand worked it's magic on Allan.

Liam thought about it. Suzanna had stroked him to an orgasm two days ago in session 5. "But that's another four days away," he protested. Two days of restraint had been difficult enough. Six would be impossible!

She counter argued convincingly, "Lianne, haven't our sessions been exciting for you? Have you ever felt as aroused over the last week? Cumming over my hand in 30 seconds, tells me that you were very excited."

"Six days, I couldn't do it." Less stridently than before.

"Lianne," she always referred to Liam as Lianne now to emphasise how she thought of him. "Get down on your knees, close to Allan's cock and watch me pump it."

He slowly dropped to his knees, close to her hand clenched around Allan's erect cock. Watching her movements. And Allan's cock. A glistening drop of pre-cum slowly emerged from Allan's urethra. It bulged out and eventually spilt over and dripped down onto Suzanna's hand.

"Wouldn't you love me to do this to you and maybe even more in a few days time. I will, but you have to refrain from cumming. For four more days. You can do it."

Liam groaned. The scene in front of him was so erotic, that he wanted to tear off his gaff and stroke his cock. He was so horny he felt like he would ejaculate in seconds. He had never felt so aroused in his life.

Suzanna stopped rubbing Allan's cock. Now Allan groaned, Suzanna's hand felt so good. "Lianne, take off your gaff but don't touch your 4" cock."

Liam stood up and pulled his gaff down his stockinged legs, freeing his cock. It immediately stuck up, unfolding from between his legs, as rigid and hard as it had ever been. Pulsing and purple. The hardest thing he had ever done was to not touch his cock at this moment.

Suzanna reached behind her for a package she had placed on the bed. She unwrapped it. A pink chastity cage. Already assembled.

"This is going to help you. It goes over your cocklet and stops you from getting erections. To stay chaste for me for four more days. So I can give you a big surprise in session 8. Isn't it worth it and to please me."

"What. Really! It looks too small. How does it work?" Liam didn't know what to say. This was a big surprise for him.

"It will be really comfortable, I promise. A ring goes around your cock and balls and the sleeve slides onto your cock. Then I lock you up and keep the key. I'll be your key holder."

"Four days?"

The fact that he said that, meant that she had him.

Liam looked at the cage. There was no way that his erect cock would fit in the sleeve. "It wont fit. It's far too small."

"You can't have an erection silly. You have to be limp." Suzanna had estimated the size of Lianne's soft cock and purchased what she hoped was the appropriate sized cage. It came with several sizes of cock rings and spacers. His soft cock was just a nub. So she had purchased "The Vice Micro" cage. The latest version now included the anti-pullout mechanism that had previously been limited to the bigger cages.

She wanted to get Allan involved too. "Allan, please get some ice from your freezer. And put it in a bowl with some water."

Suzanna was pulling apart the cage into its component parts. She had practiced with it before she came and watched some porn sites that showed cucks and sissy's putting them on. The vice had great reviews and she really liked the anti-pullout mechanism to prevent easy removal.

Liam was slowly pumping his hips forward and back, trying to get some stimulation. His hands were twitching, almost unable to restrain from touching himself.

Allan had put some ice in a bowl and half filled it with water. He was swirling the water around with his finger. He passed it to Suzanna. She grabbed Lianne's testes and squeezed as she had previously.

"Ahh fuck, that hurts." Groaned Liam. But he didn't stop her.

"It's all in a good cause. Imagine how good I will make you will feel in four days. It will be over in no time."

She squeezed hard and placed the bowl under his sissy parts. Liam squealed as the ice water rose up over his genitals. His cock rapidly shrunk from the combination of ice water and having his balls painfully squeezed. She took the second largest ring and slipped it over one ball and then squeezed the other through. Lastly, she pushed his now limp cock through the ring too. She pushed the ring against his groin and pulled his parts out. This ring was too large. She slipped it off and put his cock and balls back in the water to keep them limp and small.

Allan was intrigued watching the process. Suzanna had him under her thumb. How could any real man let this happen to himself?

The second smallest ring worked well Suzanna thought. Not too tight but held everything in just so. She left all the spacers out as Lianne's sissy cocklet was so small. She was glad that he was hairless. Navigating hair would have made putting the cage on more difficult. The short shaft slid on and into the appropriate grooves and slots. She tried the middle sized anti-pullout. Hard to tell if it was the perfect fit, but whatever. That would do for the first fitting. The internal length of the sleeve was 1" or 25mm. Lianne's little frozen and limp cock didn't even reach the end with no spacers.

"Lianne, you have a really small cock. Even this cage is too big for you." She actually thought it was sized well but under the circumstances some small penis humiliation was appropriately timed.

Liam felt embarrassed and humiliated. Suzanna was right, his penis didn't even reach the end. Close but not quite. His cock was tiny. So tiny.

She jiggled the cage around and put the tiny metal padlock through the hole linking the ring and sleeve that would keep the two parts locked together. She didn't lock it yet.

Now that Liam's cock was out of the ice water and with Suzanna handing the cage, his cock started to grow. It expanded into the end of the sleeve. And kept going, pushing the cage out from his body. But the rigid casing restricted his erection limiting it to 1".

Liam groaned again. His cock wanted to get bigger. He felt around the cage. There was a hole at the end and there were some small slots in the sleeve near the base but his fingers couldn't touch the skin of his shaft. His balls hung down between the ring and short sleeve. It was plastic and not very heavy but it did pull down on his genitals. The sleeve was angled down and completely prevented his cock from rising. Or expanding. From the name "Micro" he thought this must be one of the smallest sizes. Damn, how embarrassing.

Allan couldn't resist. "Hey sissy that tiny pink cage looks really cute on you. A perfect fit."

"Let's see if your gaff still fits. You can't tuck your cock, but maybe you can pull the cage down. Let's find out." Suzanna offered.

Liam stepped into the gaff and pulled it up. They didn't really work together. The cage bulged out the front of the gaff. His penis couldn't be tucked between his legs and his balls had to be in the ring and hanging down. No chance to push them into his body wearing the cage.

She admitted reluctantly, "Nope, gaff and cage don't mix. It's either one or the other, Lianne. To help you through the next four days before your surprise reward, you will have to wear the chastity cage."

Liam looked resigned.

"There are two keys. I'll keep one and Allan the other. If there are any problems, check in with Allan and you can call me too."

"Ready, set, go!" Click. She locked the padlock and pulled it to check it was engaged. "Allan, here is your key."

"It feels funny, but not too tight except when I try to get an erection." Liam admitted.

"Lianne you'll be fine. I think it suits you. It's a really cute pink. I love it. Just wear your panties for now but keep your gaffs in case we need them again. I have something else for you too tonight. Allan, sit down on the bed."

Suzanna pulled out a spray bottle of perfume and sprayed some on Liam's neck. "I bought this for you. Spray some on every night before you get changed into your lingerie. It's really feminine scent. Suits you perfectly."

Liam sniffed it. A bit overpowering and definitely feminine. Nothing a man would use.

Suzanna ran her hands over Liam's body. "Are you using moisturiser every day? Don't forget to shave twice daily and use the hair removal cream every week or if you feel any stubble. You feel so smooth and soft. Just like a girl. I love it."

Liam loved having Suzanna touching him, even if it wasn't sexual. His cock was trying to get bigger. But couldn't.

She pulled down Allan's underwear again as she sat down on the bed next to him and exposed his cock. It flopped out and quickly expanded, rising up. She fondled it again until it was hard.

"Kneel down Lianne and watch me stroke his 8" cock."

He followed her command. He was very close to Allan's cock and could see every detail of her hand moving up and down on his shaft. Allan may as well have been naked. Suzanna was fully clothed making her seem more dominant and in charge. He was dressed as a women watching Suzanna and Allan in a sex act next to him. So close he could touch them. His perfume overwhelmed any other odours.

Allan moved closer to Suzanna to kiss her while she continued to caress his cock. Liam could hear them kissing. Lips smacking wetly together. They were using lots of tongue. He stayed focused on her hand and his cock. Such an intimate expression of their sexuality as boyfriend and girlfriend. He wondered what exactly his status was now? Blackmailed sissy? Something more? Suzanna was being nice to him lately and not demeaning or rude. What did she have planned for him in session 8 in four days time? How would he feel after being in chastity for four days? It was frustrating enough now with the two of them making out now. Right next to him.

Suzanna pulled back from their kiss. "Tell me before you come stud." She had been stroking his cock now for almost ten minutes.

"Getting pretty close babe."

Liam had been noting her technique. Firm and fast, Slow and tender. Thumbing the head. Twisting up and down. Caressing and fondling his balls. Wetting her palm with her saliva for lubrication. It was a virtuoso performance. He would have come again in 20 seconds. Or less. Allan was a stud with real staying power.

"Ok, that's it then." She pulled away from Allan. "I'll see you tomorrow night Al baby. And you Lianne for session 7 in two days time. Get ready for bed Lianne. Lingerie and lipstick off. Hand wash your panties. Nightie on. Have a shower tomorrow as I want you to have your perfume on overnight."

Allan sighed deeply. Suzanna had told him earlier that she wasn't going to get him off. He would have to wait for tomorrow. He had said, no problem, but didn't realise how frustrating it would be to be so close and then denied release.

Liam was already getting ready for sleep as Suzanna had told him. He realised he was being a pushover but she really had a hold on him. He wanted to obey her and continue their playing. Wherever that went. He could see it was escalating but he was so erotically charged by her. It was intoxicating.

In the bathroom, he heard Suzanna leave as he hand washed his panties as directed. He tried to go to the toilet and piss before he went to bed. There was a hole in the end of the cage sleeve but when he released his stream of piss it sprayed everywhere. He swore and stopped the flow and cleaned it up with paper towels.

"What's up Lianne? Allan asked from in the room, hearing Liam swear out loud.

"Nothing, just the cage makes me spray everywhere when I piss."

"I believe that you have to sit down like a girl now. You can't piss standing up any more." Allan chuckled at his predicament.

What next, Liam thought. He sat down, pointed the cage down into the toilet basin and successfully relieved himself. The clamp thing that Suzanna had added to the sleeve at the end before she locked the cage on seemed to compress his penis and slowed down his flow somewhat. He had to rinse the end of the cage in the sink to clean it and his cock. He realised he would have to clean the cage and his cock in the cage in the shower every day. That must be what the holes in the side of the sleeve were for.

He tried to pull at the cage to see how restricted and locked he really was. The ring was tight but not painfully so, hardly any slack between the ring and his flesh. He could possibly get his balls out one at a time, likely painfully. Lubrication would help. Not sure how the clamp worked if he got his balls out as that compressed his cock near the base. Anyway, not going to try now with Allan in the room. Soon. He wouldn't die from wearing a chastity cage. It was only going to be four days.

===

The cage was annoying when he woke up in the morning. His penis had tried to harden and it hurt slightly when it expanded and pressed tightly into the end of the cage. It had woken him up. He got out of bed in his nightie. He wasn't wearing any panties and he could see the bright pink cage through the transparent material. He sat on the toilet again to relieve himself and then had a shower. The panties he washed last night had dried overnight and he put his lingerie on before he dressed to head to breakfast. He had been wearing socks over his stockings to hide them and their feminine shades and floral, lace designs. Long pants of course and dark shirts to hide seeing the garter being seen through his shirt. The clear varnish on his nails wasn't particularly noticeable but was glossier than his unpainted nails. Or so he thought.

He was more aware of men wearing gender neutral clothing now. He was picking up things he had never noticed before. There were a couple of guys who had painted fingernails in his lectures. Like bright colours and not clear. One who wore lipstick in a neutral tone. A gothic looking guy who had dark black eyeshadow and black nails. Several had piercings and tattoos, not necessarily feminine though. Many girls had tattoos and piercings too. More than the guys probably. He realised that if he didn't try to hide his stockings, likely no one would notice and even if they did, they probably wouldn't care anyway.

He caught himself checking out cock sizes too under clothes. Was he undersized? He was 4" and Allan was 8". He queried AI and yes, he was well under average size. The 1st percentile for penis size was 4"-4.7". Shit! He was at the bottom range of that. 99% of men had bigger cocks than he did. He checked Allan's cock size. He was at the opposite end of the spectrum. 99th percentile. Lucky bastard. And now he was wearing a chastity cage that limited him to 1". Micro dick territory. He didn't want to confirm officially that he had a micro dick. Being at the bottom 1% of erect penis size was bad enough.

He knew he wasn't very confident or outgoing. He had made very few friends at Uni so far. Allan's attempts to get him to meet his friends had ended badly.

His strange evolving relationship with Suzanna and Allan. What was it exactly? He doubted they were going to let up on him any time soon. Suzanna appeared to be really getting into it. They were very pissed about his secretly videoing them initially although they were treating him better currently. Being submissive and doing what they said had helped. Whenever he argued or refused they had resorted immediately to threats without backing down.

He was enjoying being a small part of their dynamic even if it meant crossdressing. They hadn't exposed him or turned him into the chancellor. Would they really do that or expose him to his parents and the uni? He didn't really know and couldn't judge. For the moment it was best to play along. At some fundamental level it was sexually exciting and he wanted more.

===

Liam was dressed in his lingerie with lipstick and perfume studying at his desk when Allan arrived back late. Probably from fucking Suzanna after she left him high and dry last night. At least he wasn't in chastity.

He heard Allan go straight to the toilet and have a shower. He came into the room naked.

"How's it going Lianne?" They usually ignored each other prior to the blackmail commencing. Now Allan seemed to take every possible opportunity to target his crossdressing and to use his feminine name.

He didn't rise to the bait. "Fine." He didn't even turn around, although he had glanced at Allan's naked body when he entered the room. A quick glance at his 99% dick hanging down between his legs. He could feel his own chastity. He always felt his chastity. And he had only been locked up for a day. He wondered where Allan kept the key. No chance to get Suzanna's key as she always had it with her.

Allan was a jock. A player. With a big cock. Almost a foot taller than he was. Here he was sitting at his desk dressed as a sissy in lingerie with lipstick and doused in perfume.

"Hey I like that scent that Suze gave you. Very femme. Stand up, turn around and show me your chastity."

Liam looked back. Allan was still naked, facing him. He looked away quickly. He pushed his chair back and stood up slowly before turning around. He avoided looking at Allan's cock or in the eye. He pulled down his panties to expose his cage. He looked down submissively at the floor.

"No discomfort? Suze asked me to check."

As if he cared. Suze maybe. "It's not exactly comfortable. But no pain. I feel it all the time. Whenever I move."

"Well if it hurts let me know." He didn't think Allan was being reassuring or conciliatory, simply following Suzanna's request to follow up.

"Do you really care? Why are you treating me like this?"

"Hey, don't get your knickers in a knot with me. It could be a lot worse remember. I'm trying to be nice and you take it the wrong way, Lianne."

Liam looked up to see if he was being sincere. He couldn't help looking at Allan's cock as he scanned upwards. Fuck it was big. And fat. Veiny with a large head. Manly.

"Don't call me that, my name is Liam."

"Not for the moment it's not Lianne." He took a photo of Liam, panties pulled down, cage exposed in lingerie and lipstick. He turned his phone around and showed the image to Liam.

"As I said, you look like a Lianne to me."
 Allan was smiling.

"Ok, Lianne it is for the moment. Whatever. Can I get back to work? I've got a lot to do tonight."

"Sure. Don't mind me, I was just checking on you. Suze wanted to know everything was ok."

He turned back to his desk but not before stealing one last glance at Allan's cock. Was it slightly erect? Fuck why did he keep on looking at it. Why was Allan parading around naked? Tormenting him?

"Keep the light down, I'm going to bed."

He went back to the bathroom to clean his teeth, before moving to his bed. Liam resisted looking at him this time.

"Night Lianne."

"Good night Allan."

===

Liam woke when his alarm went off this morning. Needed to piss. He was getting used to the chastity. A bit. He rose, wearing only his nightie and cage.

Allan was sitting on the side of his bed. Naked still, legs spread wide. Cock half erect with morning wood. His equally big testes hanging below his manhood. You couldn't miss them nor his massive member. He scratched his balls and got up.

"You can have the bathroom first Lianne. I'm going down for breakfast." He threw on a pair of pants and a t-shirt with thongs and left.

Liam didn't answer and went for a shower and get ready for the day. By the time he was changed in his secret, hidden female lingerie underneath his boy clothes and went for breakfast, Allan arrived back. Liam had his backpack with him and was planning to go straight to lectures.

"See you tonight Lianne."

Liam sighed and walked out without answering.

===

Session 7

"Only two days to go Lianne until your big surprise." Suzanna reminded him.

Liam was in his lingerie of course. And chastity. Allan was naked, with Suzanna fully clothed. Liam hadn't seen her naked since their last video he had recorded, more than two weeks ago. And he no longer had access to any of their porn videos. Not that he could masturbate with his cage on. And what was up with Allan being naked all the time these days?

Suzanna took every chance to hold and stroke Allan's 8" tonight. Suzanna had told Liam when she arrived to watch her playing with Allan's cock. So he did.

He wondered what was in her bag for him this time. She had a big bag tonight.

"Take your panties off for the rest of the night. I want to see your cage." She turned to focus on Allan's member while Liam took them off. He stepped out of them and put them on the bed.

"Come close and kneel. Watch me working Allan's 8" cock. Isn't it magnificent?"

"Compared to mine sure, especially locked up."

Allan smirked.

Liam was fascinated by Suzanna. He just wished that she would stroke his cock. But his surprise was still two days away and for the moment he was still locked up. Running on memories.

She stopped wanking him and turned to the bag. She pulled out a wig with lustrous black hair, the same colour as his. It looked like real human hair. Full bodied. long and shiny. It came with a fake mannequin head to store the wig on when not being used.

"Stay there and keep watching Allan's lovely cock." She moved behind Liam with the wig and arranged it carefully on his head. Allan was now stroking his own cock keeping it erect until Suzanna returned.

Suzanna was quickly finished adjusted the wig. Liam could feel the weight on his head. It was straight like his own hair but considerably longer.

"Ok, stand up Lianne and look in the mirror."

Longer hair made him look more femme, as if he expected anything less. Everything Suzanna did made him more femme. It seemed to change the shape of his face.

"Yes that definitely makes you a better looking sissy Lianne. I like it."

"Me too." Chirped up Allan.

His bright pink chastity still looked incongruous hanging between his legs. Not quite matching the rest of his outfit. Which now included a wig.

"You can wear this every evening as well."

Of course he could. It wasn't an order but it could turn into one. It would be futile to object. Allan was taking photos with the wig on.

"You need to brush it and store it every night before you go to bed. I'll leave instructions for its care."

He had to admit to himself. It did look good and matched his own hair perfectly. Suzanna had told him not to cut his hair but it would take months to grow it to the length of the wig.

"I like it too." Liam admitted, staring at his reflection in the mirror, the wig framing his face and hanging down his shoulders.

"Lianne, I love it that you are really getting into the spirit of things. Things will go so much better that way. Please kneel back down and watch me play with Allan's beautiful cock."

Will go so much better? What did she mean by that? He hesitated to ask. Afraid of the answer perhaps.

She was pumping his cock hard and fast. Gripping him tightly and trying to get him off quickly. He could see every moment perfectly, every detail of her hand and his cock. Right in front of him

Allan lifted his hips off the bed and groaned as he came. Multiple spurts high into the air, landing on his legs, the bed, on Allan, on Suzanna's hand and arm. Thick and creamy, coagulating.

Suzanna continued to stroke him and more sperm came out, gradually slowing in volume. Far more than any ejaculation of Liam's.

Liam could smell it. Very distinctive. Similar to his but a stronger smell. Suzanna's hand hadn't stopped but Allan's tumultuous ejaculation had dribbled out.

Suzanna asked. "Do you want to taste some Lianne?" She held her hand, covered in sperm next to his mouth.

He didn't answer but his tongue came out and licked up a tiny amount cum and took it into his mouth.

"Good girl. That's what I like to see. Try some more, share it with me."

Allan was sitting back, propped up by his arms watching the two of them. He started to take photos of the two of them cleaning his spend.

Liam and Suzanna slurped up Allan's sperm. She left her hand out for Liam while she cleaned up around Allan's cock. Sucking it into her mouth. Once she saw that her hand and arm were clean, she gently guided him down to lick and suck any cum off the bed between Allan's legs while she cleaned off around his groin. He didn't resist her.

He avoided making contact with Allan while Suzanna finished off any remaining sperm. Savouring it. He thought for a moment she was going to kiss him and they would share Allan's spend but she pulled back as their lips almost touched.

"Very good girl," she repeated. Allan took another perfectly incriminating photo of Liam licking white sperm from his lips and swallowing.

Liam felt good about being praised and was in a haze of arousal. His dick was as hard as it could be while being restrained in chastity. He felt submissive and compliant. Any release he got was dependant on Suzanna. He wanted to please and obey her, to receive her praise. To eventually have an orgasm. Two days to go.

"Try not to get any on your new hair," she advised.

She kissed Allan and he had no problem with her mouth having cleaned up his sperm. "You taste good babe." In fact he revelled in it.

Liam could taste the lingering bitterness of Allan's sperm. That was the most he had ever had in his mouth.

While Suzanna and a naked Allan made out on the bed, he was left watching them, kneeling close. The faint residue of his perfume mixed with the much stronger smell of male ejaculate. They continued kissing and caressing each other for a while and Allan's cock started to rise again. Liam was tempted to touch it.

"Stud, I would love to do more, but I will go and save it for tomorrow."

"Lianne, your best effort ever. See you in your sissy lingerie and wig in two days time for our nest session. I'm so looking forward to it and so should you.

She grabbed her bag and quickly left.

Allan told Liam. "Sissy Lianne, get cleaned up. Time for bed."

He rose and headed for the shower. Liam watching him from behind as she stood and undressed. He stored the wig on the head Suzaanna had left for it. Washed his panties that he had removed before and hung them to dry. Removed everything else and slipped into his nightie. He hadn't rinsed his mouth, a slight residue of sperm lingering.

Session 8 to follow...