Chris' Adventures Ch. 06

Chris woke up and rolled over to look at Christy sleeping next to him in her purple satin baby doll he'd gotten her last week. He stroked her thigh and she stirred. Over the last few months since Christy had found out his little secret of liking cock and dressing up in lingerie they'd made some big strides in their sex life. They were now fucking the neighbors, both of them, and Christy was enjoying her newfound bisexual side. They'd gotten together with Rob and Patty a few times since that night he was caught with Rob. Each time they'd fucked and sucked and swapped every way they could, and it was always hot.

Now he was wanting to take it to the next level. They'd talked about him dressing up all the way, even gotten him a couple of dresses and he'd been practicing at home with his makeup and a wig. He'd even gotten a pair of high heels to practice walking in. Christy rolled over and opened her sleepy eyes to look at Chris as he watched her sleep. "Morning beautiful." He said.

Christy smiled at him and snuggled her head into his chest. She ran her hands down his stomach and to his panty clad cock, which was rock hard as usual. "Good morning. I see someone is up and ready." She giggled.

"Of course. Last night was hot. Want to go for a repeat?" He rubbed her ass. "Or should I save it up for tonight? We could do what we'd been discussing last night before we fell asleep."

Christy looked up at him and smiled. "Really? You want to try that? It's an awfully big step." She thought back to the conversations they'd had about him going out dressed up. The thought intrigued her and she had to admit the idea turned her on a bit. Then last night Chris brought it up again and even talked about picking up other guys, or even other girls. That was the part that had her a little uneasy. Playing with Rob and Patty was all well and good. They'd known them for quite a few years. Total strangers were another matter entirely.

"Are you sure you want to make that jump?" She asked as she absently stroked his cock.

"You know I do." He came back quickly. "I love watching you with Patty and Rob. Why not expand out circle a bit? We'd have some ground rules of course."

She stopped stroking him and looked up at his face. Was this going to be rules that only helped him or would they benefit both? "And what are those?"

He leaned in and kissed Christy as his hand snaked up her baby doll and massaged her pert breasts. She let out a low moan. "Well for starters we both have to agree on the person, be it male or female."

"you're off to a good start." She sighed as his hands pinched her nipples. "Are we free to choose someone for each other? And what about if the other person isn't there?"

Chris was startled at this question. The thought of Christy picking up someone to fuck when he wasn't around was a turn on to him but he didn't think that Christy would go for that. "Really? You'd want to do that? Basically, have an open marriage." He trailed ff as she began to stroke his cock and he moaned.

"Well if we can do it together, why not separately?" She groaned as Chris pressed against her and pulled at her nipples.

"Mmm, that sounds hot. As long as we tell each other about it afterward. And the whole approval thing still stands. We send pics to each other if we find someone and the other still has to agree." Chris gasped as he watched his wife spread her legs and used her free hand to finger her pussy all the while stroking his cock.

Christy groaned and slid three fingers in her dripping pussy. All this talk of fucking other people was turning her on. "That sounds good. Uggghhhh." She moaned. "All this talk has gotten me horny, if you can't tell." She grinned at him as she sat up and straddled his hips.

Chris chuckled. "I'd never have guessed." He smiled up at her as he held her hips and guided her onto his cock. He watched as she reached down and held his cock up and then sank onto it, taking it in her pussy in one motion. "Ohh yesssss. That feels incredible." He raised his hips to drive his cock deep into her as she held herself above him.

"Uhh yesss is does. Especially your panties on my smooth pussy." She groaned. "God I'm glad Patty convinced me to shave it bald." She ground her hips in time to his thrusts.

"So, what about my proposition of going out tonight?" Chris hissed through his teeth as He felt Christy's pussy grip his cock. He held her hips and they rocked back and forth in time with each other. He let go of her hips and his hands slid up her body, over her round belly and small pert tits in her baby doll and caressed her neck. She didn't have a model's body he thought, but she loved him and he loved her. Nothing would change that.

He pulled her in and kissed her deeply as they lay there and made love to each other.

Christy moaned and groaned as He pushed himself deeper into her pussy. He felt so good in her pussy she didn't want to get off him. As she rode Chris up and down his hands roamed over her body. She loved the feel of his touch on her. It always drove her wild, just like it was now. She ground her hips in a slow circle on top of him as he probed once again with the question of going out all dressed up. The thought was all at once a turn on and a bit frightening. Her thoughts were interrupted when Chris pulled her in and began kissing her, his hands holding her close as they coupled with each other. She couldn't respond but just held herself there and relished the incredible feel of her body on his while he filled her wet pussy. She moaned into his mouth letting their tongues dance with each other as she neared orgasm. Finally, she broke his lip lock and answered.

"Yes. Let's do it. Ohhh that feels good." She ground her clit against his panties as they fucked. "Keep it up baby."

Chris grinned at her and pumped her pussy. "Ohh yess baby. You'll love it. Who knows, we might find someone who wants to fuck both of us." The thought of what might happen tonight was driving him over the edge. "Oh God Christy, I'm cumming!" With a loud grunt he let loose his load into her tight channel. He thrust hard and pumped her full of his load.

She gasped and moaned on top of him as his load splashed her inner walls. "Damn baby!" she cried. "I was so close." She hadn't cum yet and needed to. Without a word she slipped off him and slid up his chest, leaving a wet trail of pussy juice and cum behind her. She rested her tight meaty thighs on either side of his head, her bald mound directly over his lips, and sat on his face. "Lick it clean until I cum!" she commanded.

Chris let out a muffled "Yes Ma'am" as he got to work with his tongue. He lashed and licked at her smooth mound, drinking in their combined juices. It wouldn't take long to get her to cum as close as she was, he thought. Over and over he stabbed at her pussy and clit, making her moan and groan loudly. Soon she was arching her back and tossing her head around and gasping for breath.

Christy reached down and held his head in place as he ate her out the way she liked. "Uggghhhh. Yessssss. Don't. Stop." She stammered as her orgasm washed over her. Soon she was gasping for breath and shaking with her orgasm as Chris licked and sucked her. Soon enough she couldn't take it anymore, let go of his head, and slipped off his face. "Oh baby, that was wonderful, as always." She leaned in and kissed him, tasting their mingled juices as she did.

She smiled at him and caressed his cheek. "And yes, let's go out tonight with you all dressed up." Her fingers trailed over his chest and slight belly. "Like you said, maybe we'll find someone who's into me too. Not that I would care to much if he wasn't into me. I always have my toys to keep me occupied while I watch you have your fun."

Chris hugged her to him and chuckled. "You naughty girl. Now shall we get dressed and get things going for the day?"

Christy hopped out of bed and headed to the shower to get cleaned up. "Sure. Where shall we go? And we should get a hotel for the night too." She called from the bathroom.

Chris was already thinking that when she called out. He heard the shower turn on as he dialed up a hotel in the next city over. They lived in a small city so he didn't want to go out some place local even though he knew of a couple of bars that catered to the LGBT crowd in town. Even better the city had a college. So the odds they'd find someone to play with would be even better. And there were a couple of bars that catered to the alternative lifestyle.

After making a phone call for a hotel he also made a call to the restaurant at the hotel for some dinner reservations. He heard the shower still running so he decided to get some things packed for the night while Christy was busy. He tossed in some business casual clothes for dinner and then went to the lingerie for the rest of the evening's activities. He pulled out some thigh high nude hose, a black demi cup bra and matching satin bikini cut panties and tossed them into the suitcase. He also grabbed the garter belt and hose in case Christy picked something for him to wear that would go with that better. Then he dug deep in the closet for something he'd kept hidden for quite a while. This seemed the appropriate time to get them out.

From the back of the closet he grabbed a package that contained some false breasts, a size 38C. They matched his frame pretty well without being overly large. He'd bought them years ago and had never tried them out. Now seemed like the perfect time. He just wondered what Christy would say. The packing continued when he heard the shower turn off and Christy walked out with a towel wrapped around her body. "All fresh from the shower and ready for tonight?" He asked. "I made reservations at hotel near the university next town over."

Christy walked over the bed. "Why there?" She asked as she surveyed the contents of the suitcase. She spotted the fake breasts and wondered where those came from. Before Chris could answer her questions, she asked another. "What are these?" She held up the false breasts in an accusing manner.

"Well..." Chris trailed off sheepishly. "I thought that to pull off the feminine look I'd need a chest. So, I bought those a couple months back." He looked like he'd been caught with his hand in the cookie jar.

Christy stared at them. "They're bigger than my chest. Really?" She chuckled at the absurdity of it. "will these fit the bra you have there?"

Chris let out an embarrassed sounding chuckle. "Yeah. I bought that bra so it would fit. I haven't tried them on yet."

"You really are full of surprises lately." She tossed them back into the suitcase. "It should be interesting to see how they look on you. I'm still not one hundred percent convinced about this. But I'm willing to try."

Chris walked over to his wife and pulled her to him to give her a hug and kissed her on the forehead. "If you don't want to do it at the last minute I understand. But you're willing to at least head out tonight and let me get dressed up right?" He looked at her with hope in his eyes.

Christy let a smile cross her face and said, "Yes, we can get you all dressed up and we'll see how I feel about it then." She kissed him on the chin and dropped her towel to go get some clothes on and pick out and outfit for tonight. "I have a surprise for you too." She paused and then continued. "Two actually."

"Oh really?" Chris inquired; his curiosity piqued as Christy was getting dressed in the closet. "Oh, and while you're in there you can pick out a dress for me to wear from the ones that we bought." He ran off to the bathroom while Christy was busy and threw together some toiletries so he could shave at the hotel and grabbed a red wig that he'd bought to replace the old one. When he'd returned Christy was wearing a low cut, form fitting short sleeve top, hip hugging jeans, and a pair of white tennis shoes. And in her hands, she had a light blue dress that looked like it left little to the imagination, and a pair of mid-calf high heeled boots.

"Are those both for me?" He asked.

"Well one is." Christy answered. "One is yours to wear and the other is for me but I thought you'd get the benefit from it too." She handed him the boots. "Those are yours. I bought them a couple of weeks ago. I figured if you were to start dressing, you'd want a couple of pairs of shows. You already have one, now here's another." She smiled sheepishly. "I guess deep inside I want to see you all dressed up and out too."

"And the dress?" Chris raised an eyebrow at her.

"It's mine. I bought it last weekend when Patty and I went shopping. Both her and Rob think it looks good on me." She tossed out as she laid it into the suitcase.

"What's that supposed to mean?" He asked wryly.

"Well... You were busy in the shop so when we got back, I slipped into it for Patty and Rob to see what they both thought. Rob thought my ass looked great in it." Christy bit her lower lip as she continued. "Then I got a royal fucking from him while Patty watched. He stretched my ass out good."

Chris' eyes went wide. Not with anger but astonishment. "And you didn't tell me? Or let me come over and help?" He gave her a little pout.

"Christy walked over to him and squeezed his panty clad crotch and Chris groaned. "I knew you were in the middle of a big project so I didn't want to bother you. Besides. I knew you wouldn't mind."

"Well you're right about that." He reached around and smacked her ass. "You've been a naughty girl. But then again I guess I've been a naughty guy." He grinned at her. "Last Monday when you were working late Rob came over to help me with something and I was horny. So, we had a little fun before you got home."

She looked astonished and grinned. "So that's why you were too tired to do anything when I got home. Well I guess we're even then." Christy chuckled as she packed her things into the suitcase, tossing in some condoms, lube, and a few toys while she was at it. "Since it was Rob and Patty I don't mind. But that's not going to fly with anyone else." She admonished him.

"The same goes for you." He said as he came up behind her and hugged her tight to him. "I know better than that. Now come one. Let's get finished packing and head out to run errands and then off to the hotel." Chris let her go and bounded out of the room like a giddy school girl.

The rest of the day passed quickly with some errands they had to run and then it was off to the hotel for an early dinner. Chris suggested eating early so they could take their time getting ready so everything looked perfect on his end for what he hoped would be a wild night. They checked into the hotel and then got dressed for dinner. Over dinner the two of them chatted and talked in hushed conspiratorial tones about what was going to happen, what they wanted to happen tonight and teased each other. They skipped dessert and headed up to the room to get dressed.

When they returned to the room Chris stripped and hopped in the shower. "I'll get showered and shaved so I'm all smooth for tonight. Care to join me?" He grinned at Christy as he disappeared into the bathroom and started the water running.

"No, you go ahead. I'll get ready out here. I cleaned up this morning."

"Well in that case I'll grab my things so I can get ready in private and surprise you." He grabbed his clothes for the night and disappeared back into the bathroom.

While Chris was busy in the bathroom getting all smooth, she pulled out a pair of satin bikini cut panties and slipped them on over her smooth pussy. Taking a pair of sheer black thigh high hose from the suitcase she rolled them up one at a time and slipped them on her legs. She stepped into the dress and wiggled as she pulled the skintight dress up over her round hips and ass. She slipped her arms into the sleeves and tugged it up onto her shoulders. Smoothing it out she looked at herself in the mirror. The dress clung to her curves and it smoothed out her belly a bit. She knew she wasn't going to be able to compete with college co-eds but she knew she could beat them out with experience and the allure of being with an older woman. She also figured that leaving the bra at home would help. Her nipples poked at the fabric of the dress. Making tiny blue spots. As she stepped up to the mirror outside the bathroom, she began to apply her makeup and could hear Chris getting ready in the bathroom.

Chris had finished getting all smooth with a razor and a little help from some depilatory cream. He was glad he found some that was good for genitals, saved him a lot of time. He toweled off and stepped up to the mirror and took a deep breath. "Here goes nothing." He muttered to himself. "Time to see if I can pull this off." He opened up the false breasts and felt them. Surprisingly they felt real. They were soft and supple just like the real thing. He applied the adhesive and then applied the false breasts one at time. He stepped back and looked at himself in the mirror and admired his reflection. "Damn! If I was a girl and had these I'd never leave the house" he chuckled. Next came the demicup bra and a garter belt and nude sheer hose. He tugged on a pair of bikini cut panties and tucked himself in so he didn't leave an unladylike bulge in the front. Next came the dress. For tonight he picked a black, sleeveless, mid thigh dress with a flare. He stepped into it and zipped himself up.

Now all that was left was makeup and a wig. He donned his red wig and applied his makeup. He had gotten pretty good at it over the last few months with a little help from Christy. In the last month he didn't need any help from her and was doing a bang up job of concealing the fact he was a guy under it all. After the makeup he donned the wig for the finishing touch. He stepped back from the mirror and admired his reflection. He couldn't wait to get out there and see who he could fool, or who he could pick up.

Christy was finished with her makeup and waiting nervously on the bed for Chris to come out. This was a huge step in this little adventure they had started. She liked it so far, with a little cajoling, but this was a huge step from dressing around the house. As she sat there waiting and thinking to herself, the bathroom door opened and Chris called out.

"Are you ready for your first look baby?" He called out in a sing song voice.

"Ready as I'll ever be." She replied with a crack in her voice.

Chris stepped out into view and Christy drew in her breath. She couldn't believe how good Chris looked. The false breasts gave him great curves and his makeup was perfect. If she didn't know any better, she'd have though he was a woman. "Um. Oh wow!" she stammered. "You actually look great. Probably better than I do."

Chris took in the sight of her in the slinky blue dress and whistled. "No way baby. That dress is hot. Turn around an let me see all of it."

Chris twirled for him and he saw that the back plunged to the small of her back, almost to her ass. "Oh baby! I can see why Rob wanted to fuck you in that dress. Hell, I want to bend you over right now and fuck you." He proclaimed as he pulled her to him and kissed her.

"Promises, promises. Is my girlfriend going to fuck me before we get out the door?" She joked with him.

"If you want." He rubbed her smooth ass. "I'm your girlfriend with a little something extra underneath. Your own personal transsexual without the real breasts."

Christy rubbed him through his dress and moaned. "Mmmmm, and I love that little extra you have. My own personal transsexual. Transvestite actually, but who's keeping score. But I thought you wanted to save yourself up for what might go down tonight. If we don't find anyone, THEN, you can fuck me all dressed up." She pulled away from him and smacked her ass for emphasis as she got out their shoes. She tossed Chris the calf high boots she bought for him and she slipped into a pair of 5" high heels that she'd recently bought. "You like my knew shoes?" She asked. "They get me a little closer to your height." She giggled.