Anal Sex with Stranger on a Train 05

Roberta stood from her knees and dabbed at her lipstick with a tissue before reapplying it.

"Thank you for trying to understand my point of view," said Roberta. "Most men never make the logical connection. Thank you for understanding," she said. "Anyway, so what's your entire point Peter?"

Roberta looked at Peter as if she had heard it all and no doubt she has.

"Anal sex is my point. Forgive me and don't take this the wrong way but I don't want to cum in your mouth," said Peter. "I mean, I do, of course, but I don't. Not now anyway."

As if ready to get dressed and leave before being thrown out, Peter looked at Roberta apologetically.

"Okay," said Roberta laughing. "That's a strange request when most men want to cum in my mouth while I look up at them with my big, blue eyes before swallowing their oozy load."

Roberta looked at Peter with short-lived disappointment that he was rejecting her in not wanting to receive a blowjob from her, that is, until he said what he said next.

"I want to cum in your ass," said Peter.

Peter revealed the original, sexual excitement he had when he first raised Roberta's dress and pulled down her panties on the train before fucking her up the ass.

"Of course. I should have known. We're back to anal sex again," she said rolling her eyes before tossing her beautiful, blonde hair. "Okay, I can do that, only you make me wish I had a vagina instead of an asshole," said Roberta laughing a sad, little laugh.

"Sorry," said Peter. "I meant no offense."

"None taken. Let's take our little party to my bedroom, shall we?" She escorted Peter to her bedroom and patted the bed for him to get on the bed. "Do you have a condom?"

"A condom? Oh. No," he said. "So used to having sex with my wife, I didn't even think of that. I haven't used a condom in years."

"Don't worry. I think I may have a condom," she said opening her nightstand drawer that was filled with condoms of every size, style, and color. "Here's one," said Roberta holding it up in his hand as if he was a priest about to give Peter communion.

"Wow! I've never seen so many condoms," said Peter.

"A woman must always be ready when the moment strikes," she said with a laugh. "Do you need my help putting it on?"

She took the condom in her mouth and ripped it open with her teeth.

"No I can do that," said Peter looking at her as if she was a sexual animal and at that point in time, she was.

"Did you bring lube or are you going to lick your fingers before sticking them up my ass again as you did on the train," she said with a laugh, "and before you force your cock up there too?"

"Lube? Shit. No, sorry, I didn't think to bring lube. Actually, I didn't know what to expect when I called you. I mean, I certainly didn't expect I'd be having sex with you now," said Peter.

"Don't worry. I have plenty of lube," said Roberta with a laugh.

Peter looked at Roberta with more nervousness than sexual excitement.

"Before we have anal sex, I'd like to talk," said Peter."

"Talk? Seriously?" She looked at him as if he was nuts. "Talk about what?"

"About you being a cross dresser and a pre-op transsexual. I'm as curious as I am interested why you had the urge to dress as a woman."

"Urge to dress up as a woman? You make me feel as if I'm a drag queen or dressing up in costume for Halloween," she said looking at him as if she could hit him. "I'm a woman. I've always been a woman inside. I never felt comfortable being a man as I have needing to be a woman."

"Is it okay if I ask you some questions?"

"Okay, this should be interesting," said Roberta with a bored smile. "What would you like to know?"

"When did you first start want to dress like a woman?"

"For as long back as I can remember, I used to wear my mother's and my sister's clothes when they weren't home. It made me feel so naturally sexy to walk around the house wearing their panties and bra that I'd masturbate in front of the mirror while staring at myself."

"Why though? I don't get it," said Peter looking at her with sensitivity in his inability to fully understand. "Why did you feel the need to cross dress?" said Peter.

"Why? That's easy. I don't see me dressing as a woman as cross dressing man as I do just being myself. In the way that you're gay man's brain is trapped in a heterosexual body, my female brain is trapped in a man's body. Just as all of your thoughts are all male, all of my thoughts are all female. Just as to live my life as a man is a horrible mistake, to live my life as a woman instead of a man is my dream," said Roberta.

To be continued...