One for the Team Ch. 03

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She had bought a pair of tight blue nylon full-cut panties to wear with the dress and she slipped them on too and smoothed them out. She didn't have a blue bra but she had a white satin bra with padded cups that would go perfectly under the dress giving her a bit of shape where she needed it. She slipped on the dress and zipped it closed with a little difficulty and then she pulled down the hem and smoothed out the seams. The dress was very short indeed. She slipped on her white high heels, accessorised, and was ready to go.

Charlotte had to admit that she quite liked being able to transform in the privacy of her own bedroom with the convenience of just walking through the adjoining door to make her assignation. What she didn't look forward to was the hours that she would spend on her knees sucking cock and if those boys wanted to ejaculate over her bottom and legs as they often did she would damn well be taking off this dress!

She set her resolve and opened the adjoining door to Robert's room and walked confidently through the door. She stopped dead in her tracks when she realised that they were alone.

"Where are the others?" she peered around the lounge and then through the open bedroom door looking for Steven and Wayne.

"They're not invited," Robert said straightforwardly.

"Really? Does that mean they are waiting at the inner sanctum? Did you just not tell them?" Charlotte asked.

"What do you care Charlotte? Wouldn't you just rather it was just you and I?" he had turned his back to her to pour them both a drink.

Charlotte walked over to him and placed her hand on his shoulder.

"Is this wise?" she stroked his shoulder affectionately.

Robert turned around and took Charlotte in his arms and gazed into blazing green eyes and surveyed her luscious red lips. She lifted her face to his so that he could kiss her as he moved into her. The kiss was wonderful; just like she remembered from the last time. It was lusty and passionate but there was also genuine tenderness. Robert no longer wore his sling and he put his arms around her and held her close, inhaling her scent as his tongue searched her mouth. There was no roughness, no wanton urge to defile her like when they were in the sanctum. He stroked her hair and then her cheek as they kissed and caressed.

There was no need for Robert to rush. No need for him to seek instant gratification before he passed her on, they were alone and had all the time in the world. He was crazy horny for her and as much as Robert would have loved to have dragged Charlotte to the bed and used her mouth on his manhood, there was a feeling of tenderness. He realised that she was being genuinely affectionate rather just submitting to his will and that was better... so much better.

"I like that dress," Robert smiled at Charlotte and offered her a drink.

"Thank you. I really can't wear the pencil skirt and blouse anymore; they're... well they're ruined," Charlotte blushed.

"Spunk stains don't wash out once they've dried," Robert grinned at her mischievously.

"Don't be flippant Robert; you were so nice up until now," Charlotte batted her eyelashes at him playfully.

"But you're not here to be nice; you're here to be naughty," Robert pulled her back into his arms and kissed her again.

Charlotte out down her drink and put her arms around him.

"Do you like it when I'm naughty?" she said around crushed lips.

"I like both naughty and nice but yes, I like naughty best," Robert grinned.

"I can feel it," she squeezed the erection poking her in the belly.

"Oh my!" Charlotte squealed when Robert picked her up and carried her to the bed.

"What about our drinks?" Charlotte teased.

"They're not going anywhere," he said and laid her on the bed, her blonde hair fanned out on the pillow.

He gazed at her. Her pretty face framed by the long blonde locks, the tight-fitting blue dress which had crept up her thighs revealing her long legs clad in shimmering hose. She was trim, curvy and girlish; he knew that the small breasts that gave her shape were fake but they helped make her look feminine. He was smitten with her.

She lay there smiling up at him as he stripped naked and then lay down beside her.

"You are so lovely," he closed his mouth over hers.

They pressed their bodies together and Charlotte folded her leg over his and held him tight. They spent some time just kissing but Charlotte wanted to feel him. There was something not only erotic but powerful about taking him in her hand. It was she who had caused his tumescence and she who would provide release... when she was ready.

Robert rolled on top of Charlotte, her dress had ridden right up around her waist and he put his cock between her thighs. Charlotte closed her legs and he began to hump her loins while he kissed her. He felt her smile.

"What are you grinning about?" he asked.

Charlotte had remembered what William had said to her about getting-by by offering the occasional 'Oxford rub' to a generous upper houseman.

"Nothing. Kiss me," she pulled his face to hers.

Robert kissed her passionately and ground against her. She could feel her pantyhose becoming damp where he humped her, he was leaking and she liked it. In fact she was leaking too, she was getting uncomfortably hard; her cock becoming engorged trapped between her thighs. It soon sprang free and filled the front of her pantyhose. It was hidden under her blue satin panties but the bulge was noticeable. She hoped Robert wouldn't be repulsed.

But on the contrary, Charlotte gasped when she felt him remove his cock from between her thighs and press it against hers, he moaned as he rubbed his cock against her through her panties and pantyhose.

"That feels so good," he mumbled into her mouth.

"Mmm," was all Charlotte could respond.

The feel of the gossamer pantyhose and slick satin panties pressing on her penis as Robert slid his cock up and down her shaft was incredible. She knew that the French word for it was frottage but words couldn't express how wonderfully decadent it felt. She arched her back to meet Robert's thrusts and ground herself against him. She could feel her orgasm approaching.

Robert suddenly slipped his cock back between her legs and she was a little disappointed. Maybe he found what they were doing unnerving. Maybe it was against their stupid inner sanctum rules. Maybe it was too 'gay'.

But Robert didn't leave his cock between her thighs; he burrowed it under her panties and rubbed it on her buttocks. That was cheeky she thought and very, very decadent.

Robert lifted Charlotte's legs and opened them so he could press his erection into the crease of her buttocks, enjoying the sensation of his cock rubbing on her pantyhose-clad derrière. His belly was pushing on her cock and it felt rather nice, as did the feel of his cock rubbing on her buttocks. This was very adventurous and very naughty. Charlotte sighed with pleasure and looked up into Robert's face.

His eyes were half-closed and he was concentrating, his face lit up with bliss. She figured he was close to orgasm as he rutted at her faster and faster.

Without warning he slipped a hand inside her knickers and tore out the gusset of her pantyhose and began stabbing at her sphincter with his engorged weapon.

"No Robert don't" she screamed and beat her fists on his back.

But Robert had her pinned to the bed, her legs high and wide, and even though she squirmed and struggled beneath him she was no match for his size and strength. She felt his cock digging into her perineum as he tried to find her entrance but he couldn't find it because she was struggling so much. Charlotte just hoped he would come soon; he had to be close.

And then it happened.

Robert's glans pressed against her tight puckered sphincter. It was smothered in his pre-ejaculate otherwise he would never have pierced her tight bud. Charlotte was to some extent responsible for her own undoing because she bucked at that exact moment causing Robert's cock to slide inside her.

"Oh my god!" she cried.

The pain was almost unbearable.

Robert suddenly realised what he had done and he lay still. Charlotte was crying and had given up the fight. But even though he regretted what he done he couldn't help but enjoy the feel of her tight velvety flesh clasping his cock and her tight sphincter clenching the base of his shaft.

"I'm sorry. I got carried away," he said genuinely contrite.

He tried to withdraw but Charlotte locked her legs around him. The pain was receding and what replaced it were the most wonderful sensations she had ever felt. Robert's glans was pressing on her prostate and the girth of his cock triggered the delicate nerves in her sphincter releasing little ringlets of pleasure.

Charlotte relaxed. Her makeup had run and she could feel her tears drying on her face.

Robert looked down at her and she looked so sexy and vulnerable that he couldn't help but begin to fuck her. Charlotte held onto Robert gasping with the pleasure and the pain as he drove his cock in and out of her tight anus.

Robert plunged himself all the way inside her and pulled her hard against him and ejaculated deep in her anus and Charlotte climaxed with him. Her cock convulsed and filled her knickers as she felt Robert's cock quivering inside her as he spent his load deep in her back passage. They both lay still, their bodies quaking as they clutched at each other. Robert tried to press his mouth to hers but she tried to move away and he followed her with his lips until she capitulated and opened her mouth and drove her tongue into him. She clung to him and shuddered; whimpering until her orgasm began to subside.

Charlotte lay underneath Robert, she could feel his heart pounding and he was gasping for breath. She could feel him becoming flaccid and his penis slipped from her anus. She eased herself from underneath him and sat on the edge of the bed, pulling her knickers back into place. Robert's spend was leaking from her, soaking into the gusset of her panties.

She silently arose from the bed and went through the door that adjoined their dorms and when she returned she had changed out of her cocktail dress and was wearing a negligee. Robert was lying on his back with his hands under his head smiling contentedly. Charlotte walked up to the edge of the bed looked down at him indignantly.

"I'm not going to be able to stop you doing what you just did to me so I'll do you a favour and make it easier for us both. From now on I'll make sure I'm prepared and I'll wear stockings so you don't have to tear my tights but you have to do something for me in return."

"Use this... and use plenty of it," she dropped the tube of KY jelly on his hard belly.

"Now shove over and make room for me," she said.

Charlotte climbed onto the bed and Robert folded her into his arms and kissed her as she snuggled up to him.

"Sorry Charlotte," he whispered.

"No you're not," she squeezed his flaccid member and felt it begin stiffen.

To be continued

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5 Comments
DeborahAnneDeborahAnnealmost 4 years ago
More please

I am a cross dresser and have been so for many years, started as a teen, and like Charlie I had purged many times. I finally decided that I would never purge again in 1968, I now have a wardrobe worth more than $25,000.00, overtime helped me get it done. Was not to keen on them more or less forcing Charlotte to suck them off, but really that is a dream I would like to come true for Deborah. Now that her and Robert have progressed to this point I hope Charlotte is happy. da.cd@frontier.com

AnonymousAnonymousalmost 4 years ago

I'm really enjoying this story but at the same time it brings back some strange memories. operation whinthorpe. it happened in my boarding house and I remember hale and his "unofficial" punishments.

smoothsatinsmoothsatinalmost 4 years ago

Thank you so much the story is delightful I am looking forward to the next chapter. Isabella.

AnonymousAnonymousalmost 4 years ago

Wonderfull as usual Michele.Expetcing the next chapter.A good 5 stars for you.

AnonymousAnonymousalmost 4 years ago
wow!

Another Michelle Nylons masterpiece, I have only just come across it and read 1-3 in one go! certainly a good way to while away some lockdown time. I look forward to more. thank you Michelle

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