Meeting Charly - Back in the Room

...Jamie thought for a minute, she had never went outside anywhere fully dressed but the motel was secluded and not busy this time of day and she was feeling randy and daring. "I'll go get them" she said.

Handing her the keys he said "it's a blue Prius and the rest of my things are in the back including some toys"

"You did come prepared didn't you sweetie?" Looking in the mirror and straightening her dress and hair she walked to the door, hopefully swinging her hips sexily enough, looking back over her shoulder with eyes narrowed she said "be right back, you can play with yourself thinking of what is happening to me while I'm getting your things."...

Chuck..."No Charly" he thought, "I'm Charly today" was shaking after Jamie walked out the door. Her (his), again the confusion, jaw just about hit the floor when she walked out, he couldn't believe she actually was going outside! She looked OK, you would definitely be able to tell she was not a woman if you were right up close however from a distance he was sure she would not have a problem. What if she were approached? Someone seen her in the hall? Damn! He was in the same room, how would she explain that? She? The use of the pronoun for himself was strange yet exciting! She looked in the mirror and saw her dress was hiked enough to see her panties and her cock was stiff with a little precum wetting the panties, very excited but nervous she reached down and started stroking herself. Where was Jamie? It had only been a few minutes but he wanted her back.

His wife dressed him up and played with him and fucked him but he was pretty sure it was going to be nothing like they were going to do today. Feeling her boobs through her dress and playing with her cock in the panties he relived the recent kisses and Jamie kneeling between her legs licking her cock and balls she started to moan and realized she needed to back off before she let lose a load of cum in her panties. Thinking of Jamie coming back and seeing that, would she go after it with her mouth? Charly was even more excited and she gave her cock one last rub and brought the fingers up to her mouth and started to lick when all of a sudden there was a knock on the door!

She stepped out the door for the first time in the daylight dressed completely. Squinting into the sun Jamie saw the Prius, letting the door go and in a split second panicking, she hadn't taken a key card! She grabbed the door before it could close completely and eased it shut just enough so it would not lock. "That was close" she thought, thinking of having to go back through the lobby to the room was not all that comforting but again, that sly smile crossed her lips it might be interesting. Headed for Charly's car she forced herself to come back to reality. No one was around and when she reached the car she pressed the button to release the locks.

Opening up the driver's side rear door she saw a bag on the seat, thinking this must be Charly's things she leaned in conscious of her backside sticking out of the door and her nyloned covered legs in heels visible to any passerby. She wiggled just a little glancing back in both relief and disappointment when she didn't see anyone. Slowly looking through the bag she saw some toys, a vibrator that looked way to big and one that was a little more reasonable, some lube and other clothing and a couple of wigs. Closing up the bag she stood up with the bag in hand, closed the door to the car and set the lock again.

Walking back to the side door all of a sudden she seen it open, almost there Jamie felt like a deer caught in the headlights of an on-coming car, what should she do?! Not thinking about it she proceeded to the door looking straight forward. The guy, handsome enough was lost in thought but seen her coming so he held the door. Not daring to say anything she just smiled at him thanking him with her eyes and stepped in, she could feel his eyes following her smiling she swayed her hips the best she could, feeling excited she glanced over her shoulder smiled and waved. He waved back and was gone. Heart thumping she proceeded to the room feeling her juices running, damn she was horny! Knocking on the door and thinking shit Charly will probably panic but a few seconds later the door opened and there she was, sexy as ever even without the wig it was time to play!

Stepping into the room and hearing the door close with a firm click Jamie strode over to Charly, reached up and kissed her on the lips "miss me?" she said smiling her free hand straying to Charly's private parts feeling the bulge and said "mmm, it appears you might have sweetie. Lets see what goodies you brought with you!" Taking Charly's hand they walked over the bed and Jamie set the bag down on the bed "I want to get a wig on you right now cutie, I'm very horny want to see a lover with nice hair and red lips to kiss!"

Charly took one out of the bag, it was a little longer than shoulder length, black and curly, saying "will this do?"

Jamie reached out and felt it with one hand while her other hand went to Charly's backside through the dress she caressed and squeezed her ass and breathed "yes, that will look very sexy on you. Sit down in the chair facing the mirror so we can get it on you."

Charly sat down in the chair keenly aware of Jamie right in back of her with the wig in hand. Jamie slid the wig on Charly's head and began straightening it, fluffing it out running her hands through it and over Charly's shoulders. With the look the way she wanted it Jamie leaned down taking Charly's chin her hand turning her head "beautiful" she whispered kissing her slowly and feeling their tongues start to come together Jamie's hand slipped further down and started playing with Charly's cock through the dress. Charly for her part had a hand on Jamie's breasts kneading and caressing as they kissed her head spinning, lost in the feeling of another crossdresser kissing her Charly felt thrilled this was happening.

Breaking away for just a second Jamie planted another kiss on Charly's lips and said "lets go over to the bed but don't get on yet. Turn and look at us in the mirror." Turning, Charly saw the two of them; Jamie's hair was shoulder length a light ash blond in contrast to hers which was a little longer and black.

Charly's hands started exploring Jamie's body, she moved around to her back and brought her hands up to her breasts while leaning down into Jamie's neck kissing and nibbling softly while still looking straight in the mirror. "No marks" she said.

She heard Jamie breath "yes, no marks" but he couldn't resist and gave her a little nip, she squealed and jumped a little but pressed her backside harder into him their dresses and nylons meshing as she continued kissing Jamie's neck. One hand left her breast and started exploring Jamie's backside again and he heard her moan; taking this as acceptance he parted her panties feeling her legs part as his fingers reached deeper into her ass "please" he heard her moan.

"please what sweetie?" Charly asked. Without words Jamie reached back and put her hand on top of Charly's and pressed it further into her ass "you like that huh?" Charly said, it was more of a statement than a question because he could tell she was enjoying it greatly. Taking a lead he usually didn't do she told Jamie to lay down on the bed, laying next to her facing her Charly kissed her, Jamie's arms going around his neck Charly's hand reaching back around to continue to caress her ass and explore.

They continued in this position for some time, Jamie's hands were exploring as well. She wanted to feel Charly's cock so she reached down under the dress while Charly continued to caress her ass and that finger kept probing deeper into regions only hers had been before. Jamie's panties were wet with precum and when she reached under the dress she felt Charly's were as well. Pulling them aside a little Jamie reached in and caressed her cock getting her fingers wet with the precum Charly was moving her hips along with her hand and enjoying the feeing. Taking her hand out of Charly's panties she brought it up to their lips, opening her eyes she started to lick a finger and pressed another one to Charly's lips letting her taste her own precum while kissing her; that made that finger even more active in her ass and she could feel Charly's fingers wanting to enter her and she wanted it badly pressing back against that finger almost begging for it to enter her.

"Hang on" Jamie said lifting her head and putting one hand under it. Still Charly's finger continued probing and she guessed that was OK; concentrate on her, you can hold off Jamie thought, damn that was hard to do! She pecked her on the lips again "you like playing with my ass don't you" she asked Charly. Charly smiled and nodded wiggling that finger around. Jamie reached down and again smeared them with his precum and then reached into her own panties with the same hand and stroked her own little clitty mingling the juices and getting her fingers even wetter. Bringing them up to his lips again she let Charly lick them off. She leaned down again and kissed her this was so nice, no rush just playing, touching, kissing Jamie wanted this to last a long time.

"Can we lube that finger up you have exploring my ass? I also want you to pay a little attention to my nipples as they are tingling and really wanting your lips on them!"

Charly reluctantly pulled his fingers from Jamie's ass and reached for the lube "would you like to try this?" he asked as he reached for the smaller vibrator, turning it on it hummed and he put it against her thigh and ran it up and down her nyloned legs watching her reaction

she shivered "maybe." Charly smiled and opened the lube and spread it along the length of the toy, reaching back he slid Jamie's panties down to get to that sweet ass she had turning on the toy again he slid it down slowly between her crack and she moaned. Stretching her dress and pulling a breast out Jamie pulled Charly's head down to her nipple feeling his lips on her nipple along with that vibe traveling in her crack pushed her close to the edge. Damn! This felt so good she thought "bite them baby" she whispered to Charly and felt his teeth on her nipple, she was spreading her cheeks and all of a sudden she felt the tip on her hole and Charly was pushing it in. "aaahhh" she bit her lip and lost control, cum filled her panties and she pushed back on the vibe and pushed Charly's head down on her breast "fuck yes!!" "fuck me with that Charly!" He pushed it in deeper and she felt like cum was flooding out of her. She felt Charly's hand enter her panties and scoop up cum and all of a sudden his fingers were in her mouth making her clean them off while continuing to fuck her with that toy! Shit, this is the best feeling I've ever had, she wanted Charly's cock in her mouth her head was spinning "Please give me your cock Charly, please fuck my mouth!"

Taking his hand off the vibe Charly pushed her down to his cock lifting his dress and pushing Jamie's face into his crotch she moved the panties aside and swallowed his cock. The vibrator was still humming in her ass and she was working Charly's cock with abandon, she wanted the cum, she wanted Charly to fuck her face she refused to let go burying her face in Charly's cock & balls rubbing her chin against the balls.

Jamie felt Charly tense and knew it was coming, reaching up and grabbing Charly's hands she put them on top of her head, Charly knew what she wanted and started fucking Jamie's face. She knew she was not going to be able to stop and didn't want to at this point. Charly felt the cum rising up in her shaft and said "hang on baby it is coming!"

Jamie doubled down on her efforts wanting it all feeling Charly's hands on her head, suddenly without warning cum started filling her mouth the vibe humming, the cum flooding it was too much and she felt herself spurting again! Swallowing all she could Jamie felt some run down her chin as she continued to suck Charly's cock, when it seemed like it was subsiding, she came up and falling on top of her kissed her deeply sharing the cum still on her lips. Charly reached back and pulled the toy from Jamie's ass she moaned into her lovers mouth the feeling left her empty but she was so relaxed and fell beside Charly wrapping her legs and arms around her and kissing her all over.

"That was so great!" Jamie exclaimed, touching her and caressing her crossdressed lover she knew they would have to relax a little but also knew the fun was not over, she wanted more and from the look Charly was giving her it was clear she did as well.