Dressing Up Night

Sam shut the room door with a sense of anticipation. He had been planning this for weeks, ever since he had signed up for the conference and booked his room in a nearby country inn. He put his holdall on the floor and pulled out the special bag he bought on the way.

From it he pulled out a satin teddy, stroked the fabric against his cheek and then laid it carefully on the bed. Sam had always been fascinated by women's clothing, getting turned on in unexpected ways when his wife slid her flimsily clad body against his, but he'd never gone as far as to try any of them on while she was out, fearing her early return.

He admired the fabric again before leaving the room and heading down for a quick meal. The food was good and the barmaid chatty, but he was desperate to get back again and finished up quickly. Back in his room he stripped and held the teddy against himself, the cool satin causing goosebumps down his body. He gently led it back down and went for a cold shower making himself as clean as possible before succumbing to the teddy.

Finally the time came for him to try it on. Standing over it he stepped in and pulled it up. He couldn't help but become aroused as it slid up against his body and he slid the thin straps over his shoulders. He stood in front of the mirror and ran a hand over his chest.

All of a sudden there was a key in the door and as he looked in horror at the "Do not disturb" sign still on his pillow the barmaid walked in with a stack of towels. "I've brought you those..." she started before stopping, "oh my. Does your wife know you're wearing that?"

Before Sam could say a word she shut the door behind her. "It's okay Honey, I had a friend at college did just the same." All Sam could do was shake his head. "I think we've some wigs in the cellar from last New Year. Would you like to try one on? I could glam you up a bit if you like. My friend used to like that."

Completely thrown by the upset to his plans all Sam could do was nod. "I'll be back in a moment Hun, don't go anywhere." Sam just sat down and waited. Although she had kept speaking in a soft voice, he couldn't help but follow her lead.

She returned a few minutes later with a bag and told him to stand in front of the mirror and shut his eyes. He could sense her behind him and then felt her place a wig upon his head. "You never told me your name Hun," she said. "I'm Sam."

She leaned in closer and he could smell her perfume. "Mmmm," she whispered, "let's call you Samantha tonight. Open your eyes Samantha." Sam open his eyes to see he was now sporting a red bob. "I guess you won't want to shave you legs, but I could hide them. Would you like that?"

Sam nodded and to his surprise she hitched up her skirt slightly and rolled off the stockings she was wearing. She slowly slid them up each of his legs and he let out a slight sigh at the caress of her hands smoothing the nylon up his legs. As she reached the top of each leg he found himself stiffening in front of her. "Not very lady like Samantha."

She sat him down again to do his nails, carefully applying a bright red coat as he found himself looking straight down her top. She then lifted herself up on her knees and produced a bright red lipstick. Sam let out another sigh as she lent forward and applied it to his lips, before applying more make up to his eyes. "You'll do," she said, "go look."

Sam went to the mirror again and could not believe the transformation. "You look pretty hot Samantha," she said, "now about my payment." She sat on the bed and waved her feet at him. "I've been on these all day. They could do with a massage."

Without a word of dissent Sam knelt down at he feet and took the first in his hand. It was surprisingly soft and as he worked it in his hands he realized he wasn't the only one who'd had a good wash. She gave out a sigh of her own and whispered under her breath that it felt good. Sam swapped to the other foot and glanced up to see she had led back with her eyes closed.

Sam held her foot closer to his face and then, as if possessed, took her big toe into his mouth and gave it a suck. He was awarded with a little gasp and so he continued with her other toes. She parted her legs slightly and he began to run his tongue between her toes. He could hear her breaths quickening and then felt her other foot rubbing through the satin between his legs.

"I saw you looking down my top earlier," she said parting her legs slightly further, "and I bet you're trying to look up my skirt now." Her foot was working harder against him and all he could do was signal agreement by running a hand up the inside of her leg. "You're good with that tongue." She parted her legs more and Sam could finally see to the top. "I can't believe you've turned me on so much."

Sam took that as a signal to start kissing along her leg. As he did so she parted them further and reached down to run her hands through his hair. She pulled his head between her legs. "I think Samantha is a bit of a slut." In response Sam drove his tongue against her, tasting her sweet juices. She let out a moan and held him tighter. "Do it," she said and he probed further. As she became wetter he began to suck her juices from her until she bucked and writhed with pleasure under him.

She sat him up and kissed him. "Thank you," she whispered, "how would you like to be repaid?"

Without a word, Sam pulled her top off exposing her breasts he'd failed to see before. He pushed her back and led on top off her. With just a thin layer of satin between them he began to rub his body against hers. She ran her hands down his back and dug her nails through the material. "Just this?" she asked. Sliding against the fabric, and her, Sam felt the tingling sensation build and overwhelm him. He rolled off her moments later a damp patch forming in the fabric. "Thank you," he whispered, "tonight was better than I ever imagined."

She got up and dressed. "Keep the hair Samantha," she told him, "tomorrow I'm going to take you clubbing...."