Chapter 1: Introduction
Jamie found himself deeply drawn to the exhilaration that surrounded the discussion threads pertaining to various aspects of cross-dressing fantasies on the forum. Meeting a man seemed both taboo and exciting.
Intrigued yet nervous, he crafted an email to John, expressing interest in participating in a roleplay together. They agreed to meet at an isolated motel room under false names, promising discretion while satisfying these peculiar desires.
John is 5'10, athletic body, 6 inch cock that he says shoots a lot of cum when he gets off. He only dates smokers and he wants to get Jamie high and have sex with him dressed as a woman. John loves to smoke during sex and has a smoking fetish and wants Jamie to smoke with him when they have sex together tonight. John's cock is bulging out of his pants as he looks at Jamie dressed up with a pack of cigarettes in his hand.
Jamie wants to feel like a woman feels when a man uses her for sex. He wants to smoke, be sexy and feminine while role-playing a woman taking care of her horny man. He wants to role-play as Tamra and "she" wants to please John sexually, but secretly she wants to taste cum and feel a cock up her ass. John is turned on by Jamie/now Tamra and her smoking and told him by email that it would get his big cock hard every time she smoked.
In the dim light of the hotel room, they remove their clothes and both get on the bed. John lights a cigarette first, and starts smoking close to Tamra, teasing his feminine body with fresh smoke from a strong cigarette.
Both of them become aroused seeing the effect of cigarette smoke around Tamara's face. John takes control of the situation by exhaling smoke right into Tamara's face and asking him, "Have you ever kissed another man while he's smoking Tamara? It's nice. Very flavorful. I think you're going to enjoy doing it."
Tamara hesitated at the thought of having his tongue in John's mouth and tried to pull away after John had taken a big puff. John quickly snapped Tamara back into place with his big arms, the cigarette now inches from her chin with smoke rolling up her made-up face. John said sternly, holding onto Tamara's neck and gripping it hard. "Our agreement is that you're going to kiss, suck and be fucked like a woman," he reminded Jamie, "you're now Tamara, and you're going to taste me" as he puffed on the Marlboro again and this time he blew the thick cloud of smoke straight into Tamara's face and nose very deliberately and slow, making her breathe it in.
“Look at me, darling,” urged John gently, his voice laced with tenderness. “Try to imagine that you’re actually savoring these moments. Taste the smoke." Reluctant yet willing to comply, Tamara followed John’s suggestion and opened his eyes wide, feigning an enthusiasm he didn’t quite feel. In response, John took another deep drag on his cigarette, exhaling smoke into the air in front of her face, so that she had to breathe it in again. He clenched the lit end between his fingers and moved in closer to Tamara, bringing the burning tip dangerously close to her cheek so she could feel the heat. The moment was electrifying; Tamara could feel the heat from the ember starting to burn hotter and hotter against her skin. With calculated precision, John maneuvered the cigarette in such a way that it encircled her face, creating an intimate burn in it's path. Their lips finally met, initiating a fierce exchange of breath and saliva. As they locked in a passionate kiss, Tamara couldn’t help but taste the lingering essence of cigarettes on John’s tongue. The harsh tobacco flavor of his mouth only served to heighten Tamara's arousal, igniting a fire in her crotch that had her own cock throbbing and making her want him more.
"Open your eyes, sweetheart. Pretend you're enjoying this," said John. Tamara did so reluctantly, then John puffed hard again and passionately wrapped his hand with the cigarette around her face and pulled her forward until their lips met and they began kissing. Tamara tasted cigarettes all over John's tongue and it made her horny. John broke the kiss to puff his cigarette again and then went right back to kissing again, making Tamara take his masculine smoke as his nasty tongue slid down her throat and brushed against the roof of her mouth. They continued to trade sloppy kisses getting each others cocks very hard , kissing deep, swapping saliva mixed with the tang of Marlboros. Tamara felt prissy wearing women's lingerie, especially with a large muscular guy dominating her like this. But she was also turned on, imagining she was a woman being taken by a man. They continued their lip locking until John asks Tamara to smoke for him.
Smoke filled the space, drifting through the air around them. Tamara's heart raced as John licked his middle finger and then slid it up inside her ass, filling her slowly and deliberately, deeper and deeper until she felt him touch her prostate. She moaned, feeling John's rough finger probing her most private part, and using her body now to continue getting his dick hard.