Solo Submission Pt. 04

It'd been over a year since he got them but had never pulled them out to play but once and only for a few minutes.

He'd just put them inside one of his bras without glueing them to his chest.

Debbie had given him a free pass to play while she was gone so what the hell he thought.

He got them out along with the tube of special glue. They felt pretty heavy in his hands.

He followed the instructions and was soon standing looking in the mirror. Having a smooth chest made it easier.

He jiggled up and down to see them bounce. He remembered that he'd picked out ones with extra large nipples.

He always got turned on seeing women in wet T-shirt contests and was going for that same look.

He went to the master bedroom closet and got one of Debbies wife beaters and put it on. It was really tight but looked incredibly real. The nipples stuck out obscenely.

Having the panties and tight T-shirt on made him want more.

He thought for a moment then decided to dress the rest of the way.

It took Matt about an hour.

He used his wife's makeup and did the best he could. He was ok with the results but thought after some practice he could do better.

The blonde wig framed his face nicely. He'd found some large clip on hoop earrings in Debbies costume jewelry box and put them on.

With a little work he might even be more passable.

He pranced around the house then decided he was ready to jerk off. Hell it was early enough he might even be able to rub two out tonight before going to bed.

Matt poured a glass of wine took a few sips then picked up the key to the chastity.

Debbie was watching the security app with Cindy and Eric.

The three of them had fucked each other senseless for the past few hours. It was raw passionate sex. Eric's endurance was incredible, he'd cum four times and could still get hard.

Cindy and Debbie had brought Eric up to speed on all the details. Eric hadn't believed what they were telling him about Matt.

They decided to peek in on Matt to see if he was up to anything to prove it to Eric.

None of them expected to see Matt dressed like he was. They followed him from room to room watching him on the security cameras.

Debbie was almost embarrassed for him as he pranced in front of the mirror shaking his fake tits.

"I told you he wouldn't be able to resist locking his dick back up again," Cindy said with excitement. "I'm so happy I told you to switch the key out."

They all watched as Matt tried in vain to unlock the device on his penis.

Matt couldn't figure out why the lock wouldn't open. He strained, pulled the key out and tried again to no avail. He went to the garage and got a pair of pliers and ended up twisting it so hard that the key broke off in the lock.

He spent several panicked moments with a pair of needle nose and finally got the broken off piece out of the lock.

He was fucked.

Matt paced the house trying to figure out what to do next. His fake tits bounced in unison with his caged penis. It was almost comical to see.

Finally he calmed down and realized he had a desperate need to cum.

He knew the only way to get relief would be with his prostate toy in his ass and a vibrator on his caged cock.

He'd done it many times before and he was desperate to do it again.

He got his toys from the play room, he saw his pussy mask and decided to grab it too.

Matt returned to his office. The place where he had performed his little ritual many times before.

He opened a drawer in his desk and pulled out a bottle of poppers that he still kept hidden, opened them and took several long hits.

Feeling the rush, Matt got on his knees and attached the dildo to the side of his desk.

He took a few more hits of poppers then pushed the toy up his ass. He moaned loudly.

As he fastened the pussy mask on his face he wished he could see how it looked.

He held the vibrator on his encased cock and pushed his pussy mouth onto the dildo.

His tongue piercing made the experience quite a bit more challenging. The ring built into the mask kept his mouth wide open, he liked the helpless feeling it gave him.

He remembered what Debbie said earlier about the the mask making a cock feel good.

Matt wished he had a real cock to suck right now.

His mouth slid over the dildo repeatedly as he rubbed the vibrator on his chastity. He was getting close to cumming.

Back at Cindy's house they were still watching Matt. "We gotta get him some real cock," Cindy said.

Debbie agreed saying, "every hunch you've had so far has been on spot Cindy, I don't think your wrong on this either."

Cindy replied, "the problem is, he won't cheat on you with a real cock unless you tell him it's ok."

"With your permission he's going to be an obsessed cock whore... I'm sure of it," Cindy said as a matter of factly.

Eric was still in disbelief and kept quiet. Seeing Matt and hearing Cindy's comments, he knew for sure she was going to make him part of it somehow.

They continued to watch Matt desperately trying to get himself off.

When Matt did finally cum he cried in frustration at his unfortunate situation. His orgasm was restricted from the cage and felt incomplete. Not what he was hoping for tonight.

Most of the time he liked cumming this way but tonight was supposed to be different. He wanted to watch himself in the mirror all dressed up. He wanted to jerk off, actually stroke his penis.

Cindy watched Matt trying to come up with an idea to get Matt some real cock. Her pussy got wet thinking about it.

She loved to dominate men. She did it with Eric to some degree but seeing him submit to another man was out of the question. She would only allow it if Eric was the top.

Cindy broke the silence, "Debbie, I know this guy that would be happy to make Matt suck his dick. He's a really nice guy, clean and discrete guy and I've known him for years."

Debbie listened interested in what she had to say.

"You need to initiate a conversation with Matt about how hot it would be for you to watch him to suck a real cock."

"Once he knows you'll cool with it tell him you want to start looking for opportunities to make it happen."

"What do you mean, make it happen?" Debbie asked.

"Tell him that if a good looking guy were to approach him, you know hit on him, that he should let it happen."

"Cindy," Debbie said. "Matt's not ever in that kind of situation, shit he's hardly ever out of the house working from home and all. He shops for everything online for Christ's sake. When is he going to have a chance for something like that to happen? It's not like he's out cruising for guys."

Cindy said. "Just leave it to me dear. I'm going to bring the cock right to his front door."

Cindy continued, "Tomorrow morning your going to go home to Matt. Your going to get him all dolled up again in some pretty feminine outfit. Make him think you two are going to have sex."

"Figure out a way to tell him how sexy he looked sucking on his dildos the other day, how it made you so hot and excited."

"Tell him that if he ever gets a chance to suck a real cock that you want him to do it for you. Give him permission to suck cock, Debbie. It's the only way he'll do it."

Matt cleaned up from his play session. Put his fake boobs back in the box. Took a shower and finished his glass of wine.

He was so tired he fell asleep in minutes after his head hit the pillow.

Meanwhile, Eric was pounding Cindy doggie style while Debbie was on her back beneath them. She licked at Cindy's pussy and Eric's balls.

Once in a while Eric pulled out and put his cock in Debbie's mouth, she struggled with its size but managed to get half of him in her mouth. She could taste Cindy's juices.

Cindy was eating Debbie's pussy, about to bring her to yet another earth shaking orgasm.

Eric finally shot his last load of cum in Cindy and pulled out.

His cum gushed out of Cindy's pussy and all over Debbie's face.

Cindy turned around and licked it off her then stick her tongue in Debbie's mouth to share Eric's load.

The three slept together that night while Matt slept alone.

Matt woke early feeling pain from his cock trying to get hard in its cage.

He sent Debbie a text to check in on her that went unanswered right away. She was sucking Eric's cock while Cindy was in the shower.

She was still sucking and stroking when Cindy walked into the bedroom drying off.

"I told you his cock was amazing," Cindy said without a second thought. "I bet Matt would like to get some of it too."

There it was Eric thought. He knew Cindy was going to somehow get Matt to suck him and she had just planted the seed for Debbie.

After about 10 more minutes of Debbie's manipulation on his cock he shot his first load of cum for the day.

Debbie licked her lips and offered to share with Cindy who declined saying, "I just brushed my teeth girl. It's all yours."

Debbie showered and finally answered Matt's text saying, "sorry honey, late night with Cindy, going to take a quick shower but I'll be home in about an hour."

Matt didn't suspect Eric was home. He hadn't even asked, figuring Eric was out of town on business as he frequently was.

He was still clueless about anyone besides Debbie knowing their secret. He couldn't wait for Debbie to get home so he could get his chastity off his cock.

He made himself busy doing things around the house until she got home.

Debbie made a few stops on the way home. She went by the mall to Frederick's of Hollywood and picked up a few costumes in Matt's size.

One was a French Maids uniform and the other was just a slutty looking outfit with a purple wig and glue on purple finger nails.

She confided with the girl in the store that they were for her husband. The girl was happy to help her with the sizes and said she'd love to see pictures of him all done up.

Debbie thought about it for a second then and asked for the girls email address. "I'll send you a couple, maybe it will help with sales," she laughed.

Matt was waiting for her at the door, ready to explain his situation with the chastity device back on his penis.

Debbie played it well saying that she must have got the keys mixed up and looked through her purse to retrieve the one that fit.

Matt was so relieved to finally get his chastity off, his cock sprang to attention immediately.

Debbie took pity on him and dropped to her knees and gave him a blowjob in the kitchen. She easily deep throated Matt's dick, it was tiny I'm comparison with the one she'd been fucking and sucking.

Matt erupted in minutes, his blue balls releasing an impressive load. Debbie was surprised how much he came.

She got off her knees and kissed him pushing what was left of her sperm into his mouth.

"You'd like it fresh from a cock I bet," she said, taking Matt a little off guard. "I'd love to see how you handle!a real one instead of that rubbery ole dildo you've been using."

She took Matt off guard once again. Planting ideas in his head.

"I've got a few surprises for you," Debbie said changing the conversation.

Matt looked as saw where the shopping bags were from and his curiosity peaked. He's first thought was that Debbie got some kinky outfits for herself.

He loved to see her dressed up sexy. That's where he got his inspiration for some of his collection of panties and lingerie.

"Follow me dear," Debbie said in her sexiest voice. She picked up the bags and walked out of the kitchen.

Expecting her to head for their bedroom Matt followed her, staring at her lovely shaped ass as she sashayed down the hallway.

When she turned toward the play room he paused a bit but continued behind her.

Debbie put the bags down on the bed and sat in the vanity chair. Matt stood not knowing what to do.

"Honey, I've been giving our new sexual relationship a lot of thought. I think I understand your needs and want to help you explore them."

Matt didn't know what to say so he just nodded his head and listened.

Debbie told him to open the bags on the bed and he did.

"Those are for you Matt... I want you to dress up for me and I'm going to help." She paused for a moment watching his reaction.

Matt was as speechless as held up the frilly maids outfit. He turned to look at himself in the mirror. He was surprised that Debbie was taking things this far and was beyond just ok with it. She was encouraging it.

He was finally getting to live out some of his most private fantasies. He was excited but nervous.

Debbie got up and took the other outfit out of the bag. "I want you to try this one on first," she said.

Matt's cock stirred at the thought of dressing up for his wife.

She noticed and put her hand on his bulge and said, "I've always wondered what it would be like to have sex with a woman," knowing full well it was a lie. She'd already been with Cindy multiple time during the past few weeks.

Over the next hour Debbie helped her husband with his make up and got him dressed.

They talked about how to put on foundation, lipstick and mascara. Debbie even plucked his eyebrows. He felt comfortable and opened up to her about what he'd done last night.

Debbie felt good that he was being open about things so she had him put on his fake breasts again to put on a show for her.

When they were finished Matt looked like a perfect slut. The purple wig was a perfect match for his face and makeup.

He practiced walking in a pair heels as Debbie gave him pointers.

She lifted his skirt a few times and stroked his cock. She wanted to make dressing up as pleasurable for him as she could.

"How's that tongue of yours feeling today," she asked.

"It's much better," Matt replied. "I put ice one it yesterday and again this morning."

Debbie was wet, excited by what she was doing, taking control

of Matt's sexually identity.

"Why don't you come over here and lick my pussy for a while then," she said opening her legs wide for him.

Matt was excited. He placed his purple lipsticked lips on Debbie and pressed against her.

Remembering the commands for the vibrator she gave the command, "Alexa, turn vibrator on medium."

Matts tongue began to buzz. The little cock in his mouth sent pleasurable vibes directly on Debbie's clit.

She moaned loudly and grabbed her breasts as her slutty dressed husband knelt between her doing his best to lick her pussy and keep his wig on.

Matt's cock was fully erect and he thought about reaching down beneath his skirt to play with it but decided against it. Maybe Debbie would want to fuck and he didn't want to ruin it.

Debbie had other plans. She ground her pussy into Matt's face and came in a gush.

"Wow that was awesome honey," she said.

Matt pulled back and gathered himself and said, "Alexa turn vibrator off."

Debbie chuckled, "sorry about that, it was just so good to feel your tongue on my pussy."

Debbie looked at his face and noticed his make up was smudged. "You need to freshen up dear..." making motions with her hands around her own face.

As Matt sat at the vanity Debbie said, "we need to have a dress up name for you don't we?"

Matt hadn't thought about it but it made sense to have a girls name if he dressed up like one.

"How about Amber?," Debbie suggested. "Or maybe Sasha, that's sexy isn't it.

Matt thought for a minute then said, "I've always liked the name Tiffany."

Debbie smiled ear to ear, "That settles it then, your dress up name is now Tiffany," she said as she reached for Matt and pulled him down on the bed with her.

They cuddled together and talked about everything that happened during the past few weeks.

Debbie reassured Matt that she loved the new direction their relationship was going. She dropped more hints that he should experience what a real cock feels like in his mouth.

Matt confessed to her that he'd sucked a cock along time ago when he was in collage. He'd got drunk with a buddy on a camping trip during spring break and ended up experimenting on each other.

Debbie use this new information to her advantage. She made Matt promise that if he ever got the chance to do it again, even if she wasn't there to watch, he should do it without hesitating.

Matt promised he would, thinking to himself it'd be impossible for that situation to ever happen, he hardly had contact with anyone outside the home.

He and Debbie spent the rest of the afternoon getting Matt dressed in the maids uniform.

He put on his platinum blonde wig and went around the house with a feather duster.

Matt was preparing dinner when Debbie got the call from Cindy.

Cindy was excited to tell her that she'd arranged for a friend to come over and pay Matt a visit.

She told Debbie that he was wide open to have Matt suck his cock and would help make it happen any way he could.

Cindy told her that the guy, whose name was Brad, loved to humiliate guys while they sucked his cock. "It should make for a great show," she added.

They talked for a while and came up with a plan for Debbie to get out of the house and come over to Cindy and Eric's.

Debbie would tell Matt to stay dressed up until she got home later that night so they could play some more.

Instead, Brad would show up pretending to be a utility worker checking for gas leaks that were been reported in the neighborhood.

He would catch Matt dressed up and seduce him into sucking his cock.

They would watch everything on the security cameras. Brad would even use his phone to record the action up close.

Debbie could not believe Cindy had come up with a plan so quickly. She loved how confident and commanding her friend was.

She finished the call with Cindy and broke the news to Matt.

She told him that Cindy needed her help for a couple of hours. That Cindy was remodeling her kitchen and wanted Debbie to help go through some design books before tomorrow's meeting with the contractor.

Matt bought it hook line and sinker. He was thrilled that Debbie wanted him to stay dressed and be ready to play when she got home. He figured he would prance around the house and get himself all worked up in a sexual frenzy.

Before Debbie left she went into their play room with being noticed and put a bunch of Matt's toys from the closet and on the bed. She made sure to put his pussy mask in plain view.

Debbie called Cindy once she was out of the house so she could put the plan into action.

Cindy called Brad immediately.

"Hey Brad, get ready for some action," Cindy said excitedly. "I got a little sissy primed and ready to suck some cock."

She gave him the address. "Can you be there in an hour with your utility man uniform?"

She shared the entire plan with him so he knew all the details.

Brad said, "Anything for you Cindy. I'll be sure to get some close up video for you with my new phone. It takes really high quality stuff."

Cindy told him about Matt's tongue piercing and gave him the lowdown on how it was integrated with the Alexa home assistant. She told Brad about Matt's pussy mask and that it would be in their playroom.

Brad laughed so hard when he heard about the piercing and the mask he choked on the beer he was drinking. "I'll see you there" he said and ended the call still choking a bit.

As Matt wandered around the house in his maids uniform and he noticed the stuff that Debbie put on the bed before leaving.

He assumed that they were some of the things she wanted to play with when she got home.

Her strap on cock was laying next to the pussy mask and his cock twitched as he played out different scenarios in his head.

"Tonight is going to be so much fun," he said out loud.

Once it got a bit dark out Matt decided to walk around outside. The back of their home was completely secluded. They had no neighbors to speak of.