Tiffany's Deal Ch. 01

PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

Again she tried to hook her thumbs into the waistband of her underwear and again he stopped her.

"Oops," Stephen smiled wickedly as he tore a little hole in the gusset of her pantyhose.

"Oops indeed," Tiffany smiled back at him and opened her legs and pulled the gusset of her panties aside for him.

She took him in her hand and guided him to her puckered bud. The lubricant gel caps has dissolved but she grunted as his girth slid inside her.

"Are you ok? Am I hurting you?" Stephen looked genuinely concerned.

"It's lovely," she smiled up at him and pushed herself upwards to impale herself on his big cock.

She wrapped her arms around his shoulders and nuzzled his neck as her ankles locked behind his back, her nylon-sheathed thighs rubbing on his flanks.

"Now fuck me. Nice and slow," she whispered in his ear and playfully bit his earlobe.

Stephen required no further invitation and began to fuck Tiffany slowly and deeply, pulling almost all the way out of her and then driving himself all the way inside her. He could feel her hard penis pressing on his belly and the slippery pre-cum leaking from her.

"I can't hold back I'm sorry," he mumbled through crushed lips.

She urged him on, rising to meet his quickening thrusts. His huge cock filled her anus and elicited the most wonderful, pleasurable sensations, especially from the ring of her sphincter and her prostate when his bulbous glans pressed against it.

"Fuck me Stephen! Fuck me!" Tiffany moaned as she writhed and bucked beneath him, meeting his thrusts.

The pleasure was indescribable, nothing in Stephen's life could compare. Tiffany's anus clung to his cock like a velvet glove. Her silken-sheathed legs grazed his tender flesh, her lips pressed to his, her tongue squirmed in his mouth; Tiffany was a sexual entity lying under him, pleasuring unlike anything he had ever experienced.

"I coming!" Tiffany clung to him, raking her nails on his back.

"Oh god! Me too!" Stephen pressed his mouth on hers and drove himself inside her as far as could.

The pressure of his penis against her prostate and the taut flesh of his belly pressing on her penis trapped between their bodies triggered Tiffany's orgasm and she literally screamed as she climaxed. This triggered Stephen's orgasm and he clung to her and smothered her cries with kisses as he ejaculted deep inside her. She drummed her heels on his lower back.

The two lovers held each other in a powerful embrace, kissing and nuzzling as simultaneously ejaculated. Stephen felt Tiffany's hot semen squirt against his belly and she felt his scalding seed fill her anus.

They kissed and writhed against each other until their passions were exhausted but neither wanted to break their embrace. So they didn't. Stephen lay on top of her, kissing her, stroking the bangs out of her pretty eyes and she kept him trapped against her body with her legs locked behind him.

"That was pretty awesome," Stephen broke the silence.

"That was pretty fucking monumental," she smiled up at him and stroked his face.

"I'm probably going to ruin the moment but I have to ask. Is it like this on all of your dates?" he stroked her face too.

"I'm going to be honest with you since you asked. Sometimes it's good and sometimes it's bad but it's my job to ensure the client has a wonderful experience."

"This does not feel anything like that," she said seriously.

Stephen frowned.

"This feels like we are lovers," she kissed his cheek.

"Me too. I've known you only a few hours and I already feel a deep affection for you," Stephen softly kissed her eyelashes.

He reached down and pulled the covers over them. It was chilly in the bedroom but that only encouraged them to cling to each other. Stephen was still inside Tiffany, he hadn't become fully flaccid, and in fact he was becoming fully erect again.

"Already?" Tiffany smirked.

"Already," Stephen began to slowly fuck her.

Tiffany put her arms around him and kissed him.

On the occasions that Tiffany stayed overnight with a client it could be awkward in the morning but not so with Stephen.

Tiffany got up to use the bathroom and came back to bed still dressed only in panties and pantyhose because Stephen wouldn't let her take them off. Then Stephen used the bathroom and came back to bed and they made love again.

They lay in each other's arms exhausted.

"Did we get any sleep at all last night?" Tiffany lazily stroked his chest.

"I'm sore," Stephen grinned.

"You're sore! My ass feels like it's been fucked by a bull elephant. I mean that in a nice way by the way. And how did you stay hard all night for goodness sake?" she playfully waggled his penis which had finally become flaccid.

"With the help of my little blue pills," Stephen grinned.

"Well they certainly work honey," she squeezed his cock.

"Oh no. Most of that was you. You are so gorgeous and sexy that I probably didn't need the pills," he turned on his side to face her.

"I bet you say that to all the transsexual prostitutes," Tiffany giggled.

When she saw the look of disappointment on his face she regretted saying it.

She moved in close to him and searched his eyes.

"I didn't mean that. You are a wonderful man and last night was one of the most wonderful nights of my life," she leaned in and kissed him.

"Thank you," he sighed and kissed her back.

"No. Thank you. Now let me out of this bed so we can order breakfast I'm starving," Tiffany grinned and threw back the covers.

Stephen admired the view as she gathered her clothes and purse and padded to the bathroom.

Tiffany emerged freshly showered but she had taken time to put on her makeup; nowhere near as daring as last night, but she had done her eyes and put on a light coating of lipstick.

"You know you even make that white terry-towelling bathrobe look good," Stephen lay back in bed with hands behind his head.

Tiffany slipped into her heels and paraded coquettishly across the room. She did a little burlesque for him, laughing the whole time.

"Bravo, Stephen applauded her.

"Ok mister get out of bed and get showered. I'm calling room service and I want a big breakfast," Tiffany sat down in the lounge and lifted the receiver.

"Order me what you're having," Stephen called through the door.

They had breakfast together chatting about nothing in particular and then Tiffany went back to the bedroom to change. She gaffed and put on clean panties and the Wolford pantyhose she had bought for backup. She retouched her lipstick and slipped into her dress.

She gathered all of her belongings and checked her phone. Nothing important. She came out the bedroom ready to depart.

"Wow! You look amazing," Stephen was still taken with her.

"Yeah. Well it won't be that amazing doing the walk of shame through the hotel lobby dressed in a cocktail dress and high heels at ten in the morning," Tiffany teased him.

"You could always stay," Stephen said solemnly.

"I could come back later tonight. I have things to do today," she bent down to kiss him on the cheek, he was still dressed in his bathrobe.

Stephen grabbed her arm and pulled her into his lap.

"Please stay. I'll put another two thousand into your account," he nuzzled her ear, his hand strayed to her thigh.

"Look Stephen, I have to go, but when I come back tonight you don't have to pay. It won't be a business proposition," she struggled to get out of his lap but he held her there.

"I actually have a business proposition for you," Stephen went on.

"Have you ever heard of Lyle and Tina Brinkman?"

Tiffany paled.

To be continued.

Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
4 Comments
BrendaNWBrendaNWalmost 5 years ago
wonderful ❣️ and hot

You write very well and I enjoyed Tiff's story very much .. can't wait to read the next part .. I go by Tiffany :) but want to be all woman

locotumblerlocotumbleralmost 5 years ago
Amazing use of the English language.

I've read many a literotica. I will be looking into the rest of you works. You varied use of such sensation inspiring adjectives without seeming to try to hard and sound like a thesaurus is amazing.

AnonymousAnonymousalmost 5 years ago
Excellent

I cannot wait for chapter 2. If it is anything like your other stories it will be amazing

Bi47Bi47almost 5 years ago
WOW 😍😍😍😍😍

Very very good can't wait for chapter two. I hope it will soon . Love to hear more.

Share this Story

READ MORE OF THIS SERIES

Similar Stories

Glory Beyond the Hole TS Rose releases sexual frustration.in Transgender & Crossdressers
BBC Shemale: A Beginning Lonely white woman in befriends new black neighbor.in Transgender & Crossdressers
In Time for Summer A boy gets seduced by his "lesbian", packing roommate.in Transgender & Crossdressers
My Transgender Neighbor Mike falls for his blonde transgender neighbor, Caroline.in Transgender & Crossdressers
"What Does She See in Him?" A high school boy finds the girl of his dreams is a bit more.in Transgender & Crossdressers
More Stories