"Fuck. God, that was good, baby." He leaned over Anna, trailing his fingers lightly up and down her body. He bent his head so his lips almost met hers and whispered. "You like taking my cock up your ass, don't you?"
With a shy glance, Anna giggled and blushed. They'd been going out for six months. Anna was 21, in her last year of college; Rob was 28, an attorney who frequented the coffee shop where Anna worked part-time. He'd flirted with her relentlessly until she agreed to go to dinner with him. To her surprise, he was soft-spoken and solicitous, very unlike the brash persona he projected when he stopped in for his morning pick-me-up.
They had a second date, and a third, and Anna found herself falling for him very quickly. On their fourth date they scrapped their plans to have a picnic in the park and spent the night at Rob's apartment, fucking until the first rays of sun began to peek around the blinds. By the time they'd been dating for two months, Anna had practically moved in.
In addition to being kind and gentlemanly, he was the best fuck Anna had ever had. Guys her age were more into getting themselves off than getting her off, but Rob took his time and made sure Anna had come once, usually two or three times, before he did. He had a kinky, dominant side in bed that made Anna blush at first; but she'd come to love it and eagerly went along with the new positions and acts that Rob introduced her to.
They'd been having sex for about a month when, in the middle of licking her pussy, he'd moved down to circle his tongue around her asshole. Anna's first instinct had been to gasp and close her legs, but Rob had gently but firmly held them open as he continued rimming her, gradually pushing his tongue inside. It wasn't long before Anna was moaning and pushing her hips towards his mouth, her embarrassment forgotten.
Her moans grew louder when Rob slowly pushed a finger in and began fucking her, eventually adding another as Anna writhed and made noises she'd never heard herself make during sex before. She whimpered in frustration when he slid his fingers out just as she'd felt her orgasm building. He lay beside her, speaking quietly into her ear.
"You want me to keep going, don't you? Have you ever had a cock in your ass, Anna?"
He'd fully expected the timid shake of her head. "Well, I want you to be a good girl, and take my cock there. You liked my tongue and my fingers — you'll love my cock. I'll make you come harder than you ever have. Are you ready for that, good girl?"
A shiver raced down Anna's spine as she nodded. She loved it when Rob talked dirty, and being called a good girl made her pussy instantly wet.
"That's my girl... Stay on your back, just like this. I want to watch your face as I fuck you." Rob smiled and knelt between Anna's legs, running a finger from her glistening slit down to her asshole. He fingered her for a few minutes before lining himself up and pushing against her tight, virgin hole.
Anna drew in a sharp breath as Rob slipped inside and paused. "Mmm, fuck, Anna...You're so hot and tight. I'm going to be fucking this sexy ass as often as I can."
As he pushed in deeper, Anna gradually relaxed, enjoying the strange sensation of fullness. She moaned as he pulled back and thrust back in, fucking her in earnest as she relaxed and got into it. With one hand working her clit he fucked her harder, until she arched and cried out. Feeling her muscles ripple around his cock as she came pushed Rob over, too; he spurted deep inside Anna's ass, rolling off to the side afterwards and pulling her close.
After that, anal became a big part of Anna and Rob's sex life. Anna enjoyed it, especially being on all fours with Rob whispering filthy words as he fucked her. She'd found that she loved feeling submissive and slutty, and she never felt that way more than when Rob's cock was balls deep in her asshole.
One night, Rob called to say that he would be home late. He was going out with a friend who needed some support after a bad breakup. Anna was sound asleep when she finally felt the bed dip as Rob got in. With a sleepy sigh, she rolled over to kiss him.
"Hey, babe... I didn't mean to wake you." Rob pulled her close, running a hand down her back to cup her ass.
"S'okay. How's Luke doing?" Luke was one of Rob's closest friends, another up-and-coming young attorney at the same firm. Anna had felt bad when Rob told her about his breakup with his girlfriend of several months.
She could smell the liquor on his breath as Rob sighed, running a finger between her cheeks. "Oh, he'll be okay. He really liked Emily, thought that it might turn into something serious...but they had some incompatibilities in the bedroom. They just couldn't work it out."
Intrigued, Anna asked, "Incompatibilities? Like what?"
"Emily was very conservative, I guess, when it came to sex. Flat on her back, missionary sex was about all she was willing to do. Luke practically had to beg for a blowjob once in a while. You know Luke — he's a good guy. He tried to talk to her, he was patient... she just wasn't interested."
"That's too bad. I like Luke — he seems really sweet. And he's hot." Anna gave a flirty grin as she reached down to stroke Rob's cock.
"Mmm... he needs somebody like you, baby. A good girl who's a horny little slut in bed."
Anna was a little shocked at that. Rob had never called her a slut before, but it made her cunt tingle. She continued stroking, eager for a good fuck now. "A girl like me, huh?"
"Yeah... He couldn't believe it when I told him you let me fuck this hot little ass of yours. Called me a fucking lucky bastard... but I already knew that."
Anna slapped his arm in mock indignation. "You told him that? Rob!"
With a laugh, Rob planted a sloppy kiss on Anna's mouth. "You don't mind, do you? He thinks you're sexy. Hey, you know what would really cheer him up? If you let him fuck that sweet ass of yours."
Anna pulled back to stare at him. "What? Are you serious?"
Rob backpedalled. "Nah, of course not, baby. C'mere and ride me..."
As Anna sank down on him she moaned loudly, and she couldn't help but think of what Rob had proposed as she rode his cock to a shattering climax.
The next morning, Rob groaned as the alarm went off. "Fucking Luke, man... making me go out drinking in the middle of the week."
Anna laughed. "Oh sure, he twisted your arm. You were helping a friend. Drink some water and get going."
"Yeah, yeah..." Grumbling sleepily, Rob got up and went into the bathroom.
When he returned Anna was sitting pensively on the side of the bed. "Rob, what you said to me last night... did you mean it?"
Rob looked at her blankly; then it hit him. "Oh, about Luke and you...? No, baby, I was kidding. I mean, I'm sure he'd love to...and you'd look hot with another guy's cock in your ass..." He wriggled his eyebrows, grabbing a shirt from the closet. "Damn, I'm late. See you tonight."
He grabbed a tie and his jacket and bounded downstairs, leaving Anna still wondering.
That night, in bed, Anna brought up the subject of Luke again. She hadn't been able to stop thinking about it.
"Baby, I was kidding. But I won't deny that it would be hot, seeing you with another guy... if that was what you wanted." Rob watched her carefully. "Is it? Do you want to fuck Luke?"
Put so bluntly, Anna wasn't sure. She blushed as she tried to answer. "I — I never thought about it until you said that. If you want me to do that...