Chris' Adventures Ch. 10

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Chris gets dressed up for Christy for night of fun.
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Part 10 of the 23 part series

Updated 08/03/2023
Created 01/25/2018
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Chris had finished work early Friday and began to prepare dinner before Christy got home from work. Working from home had its perks. After their separate adventures last weekend they had come home and showed each other the pictures and videos that they had each taken ad had gotten Chris thinking about his next steps, which he'd acted on while working this week. Chris loved seeing Christy act like a little slut with another man and he noticed that Christy started to squirm when he and Patty had mentioned being fucked by a transsexual. Even though they were tired the videos had reinvigorated them and they fucked each other one more time before falling asleep. During which Chris asked her if she would like to be with a transsexual. Christy moaned and nodded and that drove Chris over the edge.

Tonight, he would see if that's what she still wanted, among other things. He'd worked int eh shop off and on all week to devise a reverse strap-on harness to use with Christy. It would keep a dildo in place inside her, hands free. He even tried it out on himself one day in bed and the results were incredible. Tonight, he'd use it on Christy. Putting dinner on the stove to simmer he headed upstairs to get dressed before Christy got home.

All the times he got dressed up and gone out with Christy they'd never come home and made love while still dressed. She'd always waited for him to get undressed. He never broached the subject and just figured that Christy wasn't into having sex with him dressed up. She was fine watching him with other men and going out all dolled up but just not sex. But after last weekend he wasn't so sure. So he decided to get all dolled up for tonight.

Working quickly, he tugged off his jeans and polo. He'd already slipped into a garter belt, hose, and panties so he was partially dressed already. If he hadn't had any video meetings today he'd have dressed up all the way. Retrieving his new breastforms from the closet he applied the adhesive and attached them. These were a better grade than his previous ones, softer and more lifelike and they were made for long term wear, swimming, and sleeping. They were even makeup safe so he could blend them with his skin. Once they were attached he applied his makeup, transforming his face from a man's to a woman's. Now to try blending his breast forms. He wanted to look as natural as he could tonight. Working with some concealer and foundation he managed to blend the seams to his skin tone. The forms themselves were almost a perfect match to him and with the makeup made the transition between his skin and the forms nearly invisible.

He shook his chest and marveled at how they looked. Rubbing them he sighed. "If only they were real. Then I could feel people tug on these nipples and manhandle my breasts." He chuckled and marveled at how good he looked in the mirror with his smooth skin and breasts. What a thought to have. He retrieved a new wig from the closet now and put it in place. This one was red with straight har that hung to his lower back. Now the illusion was complete. He looked all woman, with the exception of the bulge in his panties. He was a woman with a little something special between his legs, he thought.

Next up came the corset. He'd only worn it once before with Christy when they went out one weekend. He'd gotten a lot more looks with it on. And loved the extra attention it gave him. Not to mention how good the tight satin felt as it hugged him. He wrapped the corset around his stomach and chest and fastened it into place. The demi cups pushed his breasts together and gave him some fantastic cleavage, the kind you wanted to tit fuck. He admired himself in their full-length mirror, running his hands over his sexy body and moaning, thinking of all the things they were going to do tonight.

Heels were the last thing he needed to complete his transformation. Stepping lively to the closet he slipped on a pair of three inch, open toed strappy heels and grabbed a box with things he'd need for tonight. He glanced at the clock on the nightstand. Christy would be home in about fifteen minutes so he busied himself with the final preparations.

First came the camera stand and the camera. He trained it on the bed for starters. He planned on filming the whole thing. Chris knew that Christy liked being seen and filmed so he was going to record the whole thing. He'd even picked up a new camera with a remote so he could zoom in from where he was on the bed. Setting it up he flipped the view screen to face the bed so he could get it set to record all the action. One of these times they should explore some exhibitionist sex. And he wasn't thinking of just leaving the blinds open so Patty and Rob could see them, the four of them do that all the time. He was thinking, in public, strangers watching, and was sure that Christy would love the idea.

Next he laid out the harness he had made in the shop from another strap-on harness. He'd cut and sewn new buckles on it and reversed the strap-on portion so it would face inward when put on. New clips were attached near the strap-on junction so he could remove it and leave the leg and waist straps in place for easy access to her pussy and be able to put the dildo back in place easily. Next came on if their dildoes for the harness, a butt plug, and a new small cock shaped gag for her mouth. Lastly, he set a bottle of lube on the nightstand, grabbed the box with a surprise for Christy in it, and headed downstairs. Just as he set the box in place in the living room, he heard the door to the garage open and Christy walked in.

"Something smells good." Chris heard her call out.

He stepped into the kitchen, his heels clicking on the tile floor. Christy looked up and drew in her breath.

Christy was shocked, and a little angry, to see a tall woman in lingerie standing at the island and asked, "Where's my husband Chris? We'd agreed that neither of us was to bring home a new partner, especially without contacting the other person." The woman on the other side of the island just smiled. "Well?" She said as she put her hands on her hips.

Chris smiled at Christy and was amazed that she didn't recognize him. He did a better job than he'd thought. "Christy, it's me. Chris." He stepped back from the island so she could see him from head to toe and the bulge of a hard cock was evident in his panties.

"Oh my god!" Christy gasped. "You, you look incredible. I truly didn't know it was you. What did you do? And what is the occasion that you are all dressed up?" She looked him up and down as he stood there. The corset gave him a sexy hourglass figure and some great cleavage. She could hardly tell where his chest started and the breast forms began. The bulge in his panties was straining at the fabric and it was then she noticed that the wig he had on hung down almost to his ass. Her pussy got wet thinking about what he had planned for later if he was already dressed up like this.

"I got a new wig and some new breastforms that were makeup compatible. So I could blend them with me skin. And they're more lifelike and I can wear them longer, even swim in them." He shook his chest at Christy. "As for the reason, I have a little surprise planned for you tonight."

Christy smiled as Chris walked closer to her. "But why are you all dressed up? Are we going out for some fun?" She asked quizzically as she kicked off her shoes to stand there in her stockinged feet. It felt good after walking around in them all day.

"No. We're not headed out. Our fun will be here tonight."

"Oh my. So, should I call you Lisa then?" Christy asked. "I take it you're going to do me while dressed like that? We've never done that before."

"Yes." Chris said as he pinched her ass. "All the other times I got dressed up you didn't seem to interested or never stopped me from getting out of my makeup before we ever fucked. But after last weekend, when we got it on watching Patty and I fuck and talk about fucking a transsexual. I could tell it turned you on, especially when I asked you about it. So, I thought I'd make an effort at it, even though these aren't real." He shook his chest at her for effect.

"You should have said something." Christy replied. "The thought of you doing me dressed up has always intrigued me, not totally turned me off. I figured you didn't want to do it." She reached out and caressed her corseted breasts. "To bad they're not, Lisa. You can't feel my hands on them or my lips sucking those nipples." She cooed, batting her eyes, hoping she wasn't overstepping. She couldn't believe she had just said that and wondered if she's taking this new lifestyle to far, even for Chris, but he didn't flinch. He just grinned at her.

Chris couldn't believe that she mentioned him having real breasts. "Oh? Don't tempt me." He arched his eyes at her last statement and chuckled but let it drop for now. "I wasn't so sure you wanted to make that jump right away. Besides. We are going to test something else out tonight."

"You also mentioned that you wanted to be the center of attention for a group of guys. So I thought we'd see just how you'd like all your holes stuffed, all the time. Because you talked about more than three."

Christy beamed at her. "With you all dressed up?" Did she have some guys waiting upstairs for her? But then why would she be all dressed up? She was already slipping into thinking of Chris as a woman now. She was surprised at how easily she did it even thought they'd only gone out with him dressed up fully a few times.

"No." He laughed. "But I am going to fill all your holes tonight. Starting with your pussy right now." He pulled out a string with two balls attached to it and held it up for her to see.

"What's that?" She asked.

"Remote control vibrating balls." Chris answered as he held them out to Christy. "Go ahead and drop those panties and slip them in." He grinned at her. "I'm going to keep you on edge tonight."

Christy smiled at Lisa and moaned. She was already dripping wet from their short conversation. Apparently she was going to tease her all night. She slipped off her panties and dangled them by one finger in front of Lisa. "How about you put them in?" She said.

"Bend over then." Chris said, putting a hand on her back and bending her over at the waist on the bar stool near the island. She did as she was told and hiked up her skirt. Chris spread her pussy lips. "Oh my, you are dripping wet. All this talk has gotten you excited hasn't it?" She nodded. Chris slipped the balls in easily and watched as Christy's pussy swallowed them up one by one. He them on using the app on his phone and Christy began to moan and squirm on the bar stool

"Oh God Lisa!" Christy gushed. "That feels incredible." She stood up and straightened her skirt out as the vibrations ran through her body. She hoped that Lisa didn't turn up the power much, she might have an orgasm while eating dinner.

"That's just a little taste." Chris said as he turned off the balls. "Now let's eat so we can get to the real fun."

Christy retrieved the skillet and saucepan form the stovetop and set them on the table along with some serving spoons. The smell of sausage and rice wafted to her nostrils as she took the top off the skillet. "Mmmmm. The same dish you made for our first date." She smiled at him and looked in the sauce pan. It contained honey glazed carrots, her favorite. Now she really wondered what he had up his sleeve for the night. The hadn't had these dishes for quite a while. She dished out the sausage and rice casserole and the carrots, followed by some mixed fruit.

They sat and began to eat. "So just what do you have planned tonight?" She asked

"You'll see." Chris said as he hit the button on his phone to start the vibrating balls. Christy jumped slightly in her seat and groaned. "I see you're already turned on by how it's going already. I'm sure you'll enjoy what I have in store for you."

Christy moaned and took a bite of food. "I'm liking it already." She squeezed her legs as Lisa turned up the intensity of the balls a bit.

"There's a surprise for you in the living room." Chris said as they ate. "After dinner go open it up and do what needs to be done. I'll head upstairs and wait for you.

"Well then let's hurry up. I want to get to the good part." Christy said as she squirmed in her seat.

They finished dinner and Chris quickly cleaned up while Christy went into the living room. There she found a box with her name on it. She opened it up and found a small package inside. She pulled it out of the box and noticed it was a body stocking. The picture on the package was of a woman in it. It had long sleeves and an open crotch. Under it in the box was a note and another box. She read it as she heard Lisa head upstairs. "I'm going to introduce you to the feel of nylon hose on your body tonight among other things. You've always gotten off seeing me in it, now I want you to feel it. Slip this on and then open the other box and put on what's inside it. Then come on upstairs."

Easing the bodysuit over her hips it hugged her curves and squeezed her round belly. A sigh escaped her lips when she put her arms int eh sleeves and pulled it up over her chest. The nylon rubbing her nipples made them instantly hard. Now she knew why Chris loved it so much.

She smoothed out the nylon on her body and moaned. It felt so smooth and tight, like a vise gripping her. And every move she made caused the nylon to move and caress her nipples. The urge to reach down and finger herself to orgasm was strong but she resisted the urge. Chris had turned off the balls but they were still stuffed in her pussy and moving around with every step she took. Now she opened the other little box. Inside was a pair of large nipple clamps connected by a weighted chain. They had rubber coating on the ends. She knew what to do. Adjusting the screw she opened them wide and pinched a nipple through the nylon suit. She moaned at the feel of the nylon rubbing against her nipples. She let out an even louder moan when she let the clamp tighten it's grip on her engorged nub. A flash of pain and then pleasure washed through her. God that felt good. She'd always used these on Chris but never on herself. She was missing out. She attached the other clamp. Every time she moved the weight shifted, tugging at the chain. She quivered with pleasure as the weight tugged at her nipples.

Chris waited upstairs after quickly getting dishes going after dinner. He'd heard a moan from Christy after, what he assumed, was her putting the nipple clamps on. Which meant she would be headed upstairs soon. He turned on the camera and aimed it at the foot of the bed to start just as Christy came walking in.

"How does this look Lisa?" Christy asked, seeing her adjusting a camera. "What's that for?"

"A little something I picked up. We needed a new one so I got a new webcam with a remote. I hooked it up to the laptop so we can record our fun." Chris looked up and saw her standing there, the body suit hugging her curves and the clamps making her nipples protrude even more than usual. "Mmmmm, I like that very much. You look so sexy." He walked over and rubbed her pussy as he kissed her. A moan escaped her lips as he pulled the balls from her pussy. "Don't worry, I'll replace it with something soon."

Christy rubbed Lisa's cock through the panties. "I hope it's this."

"At some point." Chris replied. He saw Christy give him a funny look.

Christy moaned and surveyed the scene before her. She loved performing in front of the camera. If someone was watching it was even better. "You naughty girl. Intending on broadcasting our sex life on the internet?" She chuckled and saw what was sitting on the bed. "I see we have some new toys too."

"All part of the fun tonight." Chris said as he took Christy's hand and guided her to the bed. She laid down and Chris saw her look over at the toys on the bed and then over at the camera and laptop. She could see herself on the screen and a shiver of excitement ran up her spine.

"So what do you have planned for me tonight?" She asked as she spread her legs wide and began fingering herself.

"Well, you also mentioned that you wanted to be the center of attention for a group of guys. So I thought we'd see just how you'd like all your holes stuffed, all the time. Because you talked about more than three." He picked up the butt plug and waved it at her. "So I have some toys here to keep you stuffed whether it's my cock or not."

"Now bend over and show me that ass." Chris commanded.

Christy moaned as she got on all fours. "How's that Lisa?" She wiggled her hips. The weighted chain of the clamps swung around and she groaned as it tugged on her nipples. Chris told her to move so her ass was pointed at the camera and the looked over her shoulder to see the laptop screen. She moved until her ass was framed nicely in it. She felt Lisa rub her ass through the nylon and then push her ass cheecks apart. Cool lube dribbled down her crack and then she felt the head of the plug tease her tight opening.

"Take it Christy. Push yourself back onto it." Chris held it steady as Christy eased back on the plug and then rocked forward with a loud moan. She repeated the process and took more of the plug into her ass. On the third try she did it faster and the plug stretched her hole wide and closed around the large plug. She let out a loud grunt and then sighed.

"Oh god that feels good!" Christy cried out as she arched her back and raised her ass in the air. She rolled over onto her back and the plug pressed farther into her as she lay down, making her moan again. "What's next?" She looked over at the strap-on harness trying to figure out how it worked as Lisa picked it up.

"My little contraption here." Chris said as he unbuckled the dildo from the harness and handed Christy the waist strap. "Put this on around your waist. I devised this so you can put the harness straps on around your waist and thighs, and then put the dildo in and attach the holder to the harness."

Christy put the waist strap on and then the thigh straps as she was handed them. "Then what?" she cooed.

"I can slide this into your pussy, or ass, and then clip it into the harness to keep it there." He grinned at her as he teased her slit. "And then unclip it to get the dildo out so I can slide in." He pushed the head into her wet pussy.

Christy groaned as Lisa slid the dildo into her. "Oh yes Lisa. That feels so good." She spread her legs wide and Lisa slid more of the dildo in her. She had picked one of their fat long ones. She could feel it rubbing against the butt plug in her ass through the membrane separating the two. God it felt incredible. It had been a while since she'd been double penetrated like this and she loved it. The dildo stretched her and slid in easily. When Lisa had it buried in her she clipped it in place.

"How does that feel?" Chris asked. "I tried it out myself one day. Every time you move, the dildo will move inside you. It's wonderful. Try it out." He watched as Christy loved her legs back and forth. The dildo would move ever so slightly in her and she started to moan.

"Ohhh, that feels good." Christy cooed. I may have to put this to use when you and Rob aren't around to take care of me. Lisa leaned in and kissed her as she squirmed with the dildo in her and hen pulled back with a smile on her face. She wondered what was coming next.

Chris picked up the phallus shaped mouth plug and grinned. "Now to fill your mouth. I told you that I was going to fill all your holes, and keep them filled." He held up the gag so Christy could see it better. It was a two inch long cock with a strap on it. The head was bulbous and the short shaft was veiny, perfect for fitting in her mouth.

Christy moaned. "Oh my. You really are going all the way aren't you?" She smiled. She couldn't believe how she was taking to this. It all felt so good, the dildoes, the camera, Lisa all dressed up in front of her. She opened her mouth wide as an invitation for Lisa to slip it in her mouth. She did so and fastened the gag behind her head. It was wide enough and long enough to fill her mouth without gagging her or being uncomfortable.