Transitioning

As he watched the woman approach his building’s front door, he assessed her. She was just like he’d asked for “ a stunning redhead with an elegant and subtly muscled body. He couldn’t tell anything else from his window on the second floor, but he was more than willing to buzz her in. He hoped she would like him as much as he liked her.

As the woman entered his apartment, he got a better look at her. She had a lovely, slightly shy smile and the beginnings of crow’s feet around her eyes. He’d always thought of them as “laugh lines “ they didn’t bother him in the least. After all, he’d asked the agency to send someone who was past the age of thirty, because he felt uncomfortable sleeping with women who were too much younger than he was. Yes, she was certainly what he’d asked for.

“I hope you don’t mind if I ask you to pay first? she said. It wasn’t a question, but it wasn’t exactly an order, either.

“Certainly, he said, handing her the envelope he’d already filled with hundreds. This agency had steep prices, but the price was worth it “ oh, was it ever. He’d never been anything but delighted with the women they sent to him.

She counted the money, then slid it into her slim, leather purse, placing it on the coffee table. “Shall we head to the bedroom? she asked him, trailing her fingers down his dress-shirt, stopping mere inches from his dick, which was rising from her touch, filling with blood, and getting ready for the main event.

“Yes, I would like that, he said. Surprisingly, he found the need to clear his throat. Why was he nervous? He’d done this millions of times. But there was something about this woman, something that made his breath catch in his throat. She almost glowed, he realized now, and she was almost the most beautiful woman he’d ever seen.

She followed him down the hall and into his bedroom, the crisp click of her heels showing she was only inches behind him. And then, once they entered his room, she closed the space between them, pressing her full breasts against his back. She wrapped her arms around him, slowly slid them down “ lower, lower still “ until they reached his belt, which she undid with ease. His pants slid to the ground, and he couldn’t help smiling as they did. She was good.

He turned around then, stepping out of his slacks, now just a mess of fabric beneath their feet. Then she unbuttoned his shirt, taking her time, kissing him as she did. She tasted minty, and maybe a little sweet, and her lips were so, so soft against his. And then, before he knew it, he was naked “ naked, and very hard. And here she was, still wearing her dress, still wearing her heels.

But this was how he’d wanted it.

And he had felt her dick through her skirt, felt it hard against him. No, this wasn’t a strap-on, this was real flesh-and-blood. Because, years ago, he’d met someone, and fallen in love, and she had fucked him, fucked his ass, with her dick. She’d opted out of bottom surgery, and he’d learned all these terms, these things he hadn’t been aware of. Her dick had surprised him, the first time he saw it, but then it just became another beautiful part of his girl “ his girl who became his wife.

She was gone now “ that was all that could be said on the matter, all that could be thought of it. And now, he had to find these women, these copies of her, to bring her back, if only for a few naked, sensual moments.

“Do you want me to fuck your ass, sweetheart? the woman asked.

“Yes. He didn’t hesitate for a second in going over to his bedside table, and there he picked up a condom and a bottle of lube, which he placed on the bed near where she stood.

“Good boy, you’re all prepared. And then she stripped off her dress, and took off her panties, and there it was “ his lover’s body, in front of him once again.

“You’re so, so beautiful, he told her, and he knew she understood that he meant it, fully.

“Thank you. Now, what position would you like me to fuck you in?

“With me on my knees, maybe?

“Oh, I’ve always loved that one. You must be the submissive sort, then? Do you like getting spanked?

“I mostly like getting my ass fucked, but we could try that. He smiled somewhat shyly now, hesitant about trying something new, something that he might not like. But it was well worth a try.

Then, “Can I suck it a little first? he asked her, hoping desperately for a “yes.

“Sure, sure you can, just with a condom on. She removed the condom from its packaging and rolled it onto her dick, and he got down onto his knees, his eyes skimming her beautiful, beautiful body. Her breasts were just the right size, just like he’d asked for, and he wished, for just a second, that he was sucking on her nipples instead, moving his lips from right to left, left to right, bringing moans from her mouth as he did. But instead, he placed his lips at the tip of her cock, kissing it once, and then he slowly opened his mouth, and began to suck.

He’d learned to be very good at sucking cock with his wife. She hadn’t wanted him to, at first, but after awhile, after she’d taught him to refer to it as her “clit, to say he was eating her out, then she’d really gotten into it, and after he’d eaten her out for the first time, she’d told him that she’d never let anyone do that before. It was then that he knew she loved him, and he told her how brave it seemed to him, to be willing to let him do that. She’d smiled at that, and blushed a little, and told him it was only because she loved him, but that she’d enjoyed it, and¦could they perhaps do it again at some point?

He felt a little bad now, sucking this woman’s cock, bad because he hadn’t discussed what she liked, because he hadn’t asked her if he could eat her out, or what she wanted him to call her dick. But she hadn’t looked offended when he’d said what he said, and from the sounds she was making, she certainly wasn’t offended now. No, she was deep in the throes of pleasure, from the sounds he heard her making. And then she placed her hand on his head, and withdrew her dick from his hungry mouth.

“I’m going to come if you keep that up, sailor, and we have a few things to check off your to-do list before the night is through.

“Sounds¦sounds good to me. He got up off his knees, and then he crawled on top of hers, both of them on the bed now. She started by slowly, slowly running her fingers from cheek to cheek, and his ass had never felt so sensitive, so exposed. And then, smack! Down came her hand, a thunderclap of sound, a lightning strike of pressure. It was almost too much, almost, but not quite, not yet. And then the storm grew worse, her hand coming down hard, hard, harder, and he started squealing at each strike, but each strike also rubbed his cock against hers, in the loveliest way possible, and then he was close, so close. And one more smack, and then he was coming, he was coming, and his squeals turned into a long, stuttery growl of a moan. This was¦this was amazing, he realized as he slowly crawled off of her lap, leaving clear signs of his pleasure in a puddle on his thousand-dollar comforter. But who cared about such things, when a gorgeous woman was about to fuck you in the way you wanted most, in the way you needed, the way you hungered for.

He got down on his knees, heard her squirt out some lube, and then he felt her entering him, easing her way into his ass, and he moaned again, quieter this time, but deeper, the way he always did when his ass was being fucked. As she eased her way in, she began to spank him again, too, and he found this added to the pleasure of her dick inside him, a perfect storm, a contrast like no other he’d ever felt.

The pain “ oh, and it hurt, it motherfucking hurt “ was so beautifully contrasted by the feeling of her cock inside him.  Yes, so beautifully that his dick took practically no time before it was rock hard again. And then it was how it was with her, with his wife, because he came again. He never did any more, never came from a dick in his ass like he used to, but this time “ this time, he did.

She had been nervous the first time she’d fucked him, the first time she’d fucked his ass. It had been her idea, and she’d insisted he call her dick a dildo, insisted that they say she was wearing a strap-on. He’d been more than happy to agree, just like he always did. She was a woman to him, his woman, and nothing could stop him from thinking of her that way. He told her this, and she turned her chin down, a shy smile on her lovely face. And then, there, right on the kitchen table, she’d slammed him down, fucked his ass, and it had hurt, but it had also felt so, so good. He’d thanked his lucky stars later that, not only had she been willing, not only had she loved it too, but that she’d happened to have a bottle of lube sitting right there. Only later did she tell him that she’d been planning to agree to it right then, no matter what he said. It was then that he knew she’d say yes, were he only to ask her.

After he came, he thanked her profusely, and she looked surprisingly happy, unlike all the others. “You¦you’re something else, mister. I hope I can see you again at some point?

“Oh, certainly. You’re the best I’ve had so far.

“Thank you, then. I’ll be off now, then, unless you want to pay a little extra for a GFE.

“GFE? he asked, as he wasn’t familiar with the term.

“Girlfriend experience. You know, with a little romance thrown into the sex.

“Maybe¦maybe another time.

She paused for a moment, seeming to assess him. He wondered what she saw, as her eyes met his. Could she see what he was thinking? But then she just nodded her head at him and said, “If you wouldn’t mind showing a lady to the door, I’ll be off, then.

So he did just that, shutting the door behind her, and for once, he slept quite well. In the morning, he made his breakfast, drank his coffee, and got ready for work. It was different than usual, this morning, though. He felt like a huge weight had been lifted off his back. He felt light, light and free for the first time in a year. Maybe he would start dating again. Maybe now he could finally move on. But he still kissed the photo of his wife goodbye right before he left for work. Not everything could change at once, after all.

Maggie Morton

Maggie Morton's first novel, Dreaming of Her, is published by Bold Strokes Books - it's an erotic, lesbian, fantasy novel, and has a fair share of romance as well. Her gay, fantasy novella A Fairy's Embrace is published by Xcite Books, and her writing appears in various anthologies, including Eve's Big Bang, Kinky Girls, and Dark Desires. She lives in Northern California with her partner and their Japanese Bobtail.

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