With a choked groan, Rob pushed deep into Anna's ass and came, feeling her squeeze his cock as she cried out with her own orgasm. He stay buried in her velvety warmth until his breathing slowed, then rolled onto his back and pushed his hair off his forehead.
"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... to let Luke do that...I'll do it."
"I want to," she whispered earnestly.
Surprise morphed into lust on Rob's face. "Yeah? You'd let Luke stick his cock in that hot little ass? Mmm, I've seen him at the gym. He's bigger than I am."
Anna closed her eyes as Rob worked two fingers into her cunt. "Yes. Yes, I want that."
"Mmm, that's my good girl... my good little slut. You're going to make Luke a very happy man."
No more was said on the subject until two days later, when Rob came home from work. Removing his tie as he leaned against the kitchen counter, he casually said, "So, I saw Luke today."
Anna stopped stirring the pasta sauce she was making, a frisson of desire running down her spine. "Oh? What did he have to say?"
She jumped as Rob wound his arms around her waist, resting his head on her shoulder. "He said he's always thought you were hot as fuck, and he can't wait to slide inside your tight little asshole."
"H-he did?" Anna absently rubbed her thighs together, unable to stop thinking about Luke's taking her there.
"Well, not quite like that. He didn't believe I was serious at first. But he's on board, and I asked him to come over this Saturday. Are you still okay with this?"
Anna rested her cheek against Rob's. "Yes. I want to do this for him... for you
"Mmm, baby... you don't know how fucking happy that makes me. And horny — get your ass upstairs." With a hard smack to her ass, Rob sent Anna running for the stairs.
Saturday came slowly. Anna was excited, but her stomach flipped every time she thought of what would happen in a just a few short days. She rifled through her drawers, trying to decide what to wear, until Rob quipped that he and Luke both would both rather she just be naked.
Finally it was Saturday night. Anna wore a pretty, filmy black nightgown anyway, wanting to look and feel her best. She smiled to herself as she wondered how long she'd be wearing it, and who would be the one to take it off of her. Rob had set out lube, some toys and towels on the nightstand. As Anna brushed her hair, the doorbell rang. With a start she put down the brush and waited until she heard Rob talking to Luke.
She walked to the top of the stairs and paused before gathering her courage and heading down.
"Anna." Rob stopped talking as she entered the living room, giving her a warm smile and appreciative once-over. Luke smiled, but waited for Rob to get things started.
"Come here, baby, and say hi to Luke." Anna felt her freshly shaven cunt grow wet at the command. She walked over to stand in front of the men, and shyly raised her eyes to Luke.
"Hello, Luke. It's good to see you again." She knew her nipples were rock hard and poking through her sheer nightgown, and it made her even wetter.
"Hi, Anna. It's nice to see you, too." Luke cut his eyes to Rob in question. At the other mans' nod, he reached out and ran his index finger from Anna's shoulder down her arm. "Thank you for this... you look beautiful."
Blushing, Anna replied, "Thank you."
"So..." Rob stepped in, his arm encircling Anna's waist. "Why don't we head upstairs? Anna, you can go first, so we can have a look at that sexy ass of yours."
With a nod, Anna started upstairs. Knowing that both men were watching her made her horny, and she made sure to swing her hips as she walked. In the bedroom, she sat on the bed, scooting up toward the headboard and parting her legs. Closing her eyes, her head swam with possibilities, and her left hand crept down toward her glistening pussy.
Luke and Rob were right behind her. Figuring there was no point in being shy, she continued playing with her wet slit.
"Fuck." Luke said in a strangled whisper.
"Mmm, eager to get started? That's okay, I'm ready to watch you take another man's cock up your ass...and I'm sure Luke is more than ready to get inside your tight little hole." Rob sat beside her. Cupping her breast through the nightie, he leaned in and kissed her deeply. "I love you, Anna."
She moaned as Rob began leaving soft, sucking kisses on her neck. A moment later she felt her legs being pushed apart, and then the wet warmth of a tongue parting her pussy lips. Throwing her head back, she submitted to the attentions of her lover and his best friend.
"You like Luke eating your pussy, baby?" Rob squeezed her breasts as he whispered in her ear.
Luke kissed Anna's thigh. "Fuck, Anna, you taste so good..." And then his tongue moved lower, circling her asshole as she bucked and squirmed. She gasped as he pushed it inside, licking and sucking her hot hole.
With a groan, Luke sat up and pulled his shirt over his head. "Christ, I want to fuck you."
He hastily unbuckled his belt and removed his jeans and boxer briefs, revealing a long, thick cock that was indeed larger than Rob's. A wave of lust swept over Anna, and she crawled over to the edge of the bed, grasping Luke's cock and taking a long lick up the shaft.
"Oh, fuck, Anna — get on your hands and knees," Luke panted. As Anna complied she saw Rob sitting on the chair in the corner, naked and stroking his cock with a look of pure lust on his face.
"Do as he says, Anna." Rob looked at her pointedly, a smirk curling his lips.
No sooner was she in position in the center of the bed than Luke slid two lubed fingers into her ass, twisting as he thrust them in and out. Anna dropped her head between her shoulder blades and moaned, pushing back onto his fingers.
Just as she felt her orgasm starting, Anna's ass was suddenly, achingly empty. As she keened in frustration, Luke grasped her slender hips and rubbed his cock along her asshole, finally pushing in just a bit. Even so, she could feel the difference in girth between him and Rob.
She tensed as Luke groaned, sliding deeper into her asshole. When he was balls-deep inside her, he paused before pulling out almost all the way and thrusting back in, starting out slowly and working up to a frenzied pace.
As Anna's heavy tits swayed and bounced, she moaned and mumbled unintelligibly. All she wanted was for Luke to keep fucking her, faster and harder, and to come deep inside her. She cried out and begged as he pounded her harder, his balls smacking against her with every thrust. At last he pushed in deep with a grunt, and Anna could feel every spurt of his cock as he came where only Rob had come before.
"God, Anna, that was fucking amazing. Rob, you're a lucky fucker." Luke pulled out, leaving Anna dazed and feeling strangely empty. She barely had time for the thought to register before Rob slid inside her used hole and drove in and out of her. She'd been right on the edge of coming with Luke, and as Rob fucked her she cried out as her orgasm raced through her, the contractions of her muscles milking Rob's cock.
When he slipped out of her she collapsed, lying across the bed feeling the come of both men leak out of her. Sleepily, she turned to see Rob propped up on one elbow, smiling down at her.
"Thank you, baby. That was even hotter than I imagined it would be."
The bed dipped behind her, and Luke spoke. "Yes, Anna, thank you. That was — you're incredible. I won't be forgetting that any time soon."
With a tired smile, Anna snuggled into Rob's chest and reached back to take Luke's hand, clasping it against her stomach. "I had an amazing time. If Rob hadn't brought it up, it never would have occurred to me to do something like that, but... I'm really glad I did."
"Mmm, my good girl. You're tired. Sleep, and maybe when you wake up and feel rested..." Rob's words trailed off suggestively.
Anna giggled as her eyes closed. "Mm, maybe..." And she drifted off imagining the possibilities.
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