Lynn and Lee: First Anal

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Author’s Notes:

This is a stroke story, so if that isn’t your sort of thing, this is your warning. This is more or less a true story, although the build up to our broaching the subject was actually a dance of several days. I simply applied a little artistic license to the actual events in order to tighten up the retelling.

Odds are, this will be part of a series of stroke tales that build into a greater story, putting into words the experiences and fantasies I’ve shared with my Baileykins over the years. The names have been changed, naturally, and I decided to put these stories in third person, as first comes out sounding like Penthouse Letters.

Hope you like it


Lynn erupted into a loud, quavering scream as she came again. Her orgasm simply refused to let her go, spiking repeatedly as Lee’s cock continued to slam into her at an ever-increasing pace. Her face was burning hot, and her whole body was alive with energy. Auburn hair covered her brown eyes, tossed there by the bucking of her body with each wave of ecstasy.

Lee smiled and growled, nearly at the point of no return. He jerked his head to one side, getting his long, dark brown bangs out of his face from where they had fallen as he pounded into her tight, wet depths. Lynn’s creamy juices were squirting out around him with every thrust, as she lurched beneath him. He let his eyes rove to her pendulous breasts, bouncing and jiggling sharply from his powerful strokes, and then to her face — flushed bright red and pinched tight in a mask of orgasmic release.

A loud, growling scream burst from Lynn, signaling yet another wave of climax gripping her. She gripped Lee as well, clamping down tight on his thrusting cock, pushing him over the edge. Grabbing her thighs tighter where he held them, Lee slammed home one last time, screaming as he reached his peak.

Lynn’s eyes opened wide and she moaned in delight as she felt the thick spurts of Lee’s cum erupting inside her. He jerked with each pulsing spurt, his cream welling up in her depths. After a couple of days of bad-timing abstinence, and a marathon session of giving her multiple orgasms, Lee filled her full, nearly to overflowing.

With a loud gasp, Lee collapsed down onto his hands over her, and Lynn let go of her legs, allowing them to fall at his side. Her walls were still rhythmically contracting around him, causing him to throb and gasp, which in turn caused her to squeeze again involuntarily. For long minutes, they both lay trapped in the endless cycle, gasping, moaning, and panting for breath.

“I need to move,” Lee gasped out, a long pause between every word, as he forced them out between quick, shallow breaths.

He started to slowly withdraw from her, and Lynn let out a disappointed moan, “Oh, don’t go.”

Sucking in a slow breath, Lee pulled free with a loud scream, immediately falling to the bed next to Lynn and moaning. Lynn immediately felt the pool of his seed inside her seeking an exit — quickly.

In quick, clipped bursts, she said, “Oh — towel — I need a towel.”

Lee responded, “The bed’s already soaked, Babydoll. God, you were wet.”

Lynn moaned, clamping her muscles tight in an effort to keep his cream inside her. A dollop dribbled out despite her efforts, and she gathered it up on her finger, bringing it to her lips. A sharper moan, coupled with a shudder, shook her body, as she tasted their mingled juices. “You came a lot baby. I love it when you come so hard, deep inside me.”

“And I love watching you just keep coming, and coming,” Lee said, getting up with a groan. On weak knees, he took a couple of steps to where his shirt had landed on the floor, as she had torn his clothes off nearly two hours earlier, collapsing back on the bed after handing it to her.

“If this is what happens when we go without for a couple of days, we should try it more often,” Lynn said, lifting her firm bottom up off the bed to slip the shirt under it, pressing the tail of the garment against her sex once her ass settled to the bed again. She could feel the pool of his semen flowing from her like a river as soon as she let her muscles relax.

“Nah,” Lee replied, and then laughed.

For a time, they lay in silence, Lee draping his arm over Lynn’s tummy as she scooted over closer to him. Finally, Lynn sat up and said, “I need to go pee. This shirt is about done for, and I think I’m still going to be dripping for an hour.”

Lee asked, “Can you get me a washcloth?”

“Mmm hmm, Baby,” Lynn replied, and then leaned down to kiss him softly before waddling to the bathroom with the shirt still held tight over her pussy. She dampened a cloth and tossed it to Lee before hurrying to the toilet.


Lynn smiled when she walked back out, finding that Lee had changed the sheets and mattress pad. Her smile widened when he admired her, dressed in only a white thong, and twitched his eyebrows provocatively. Sitting down on the bed, Lynn said, “Thank you, Baby menderes escort — and for changing the sheets too.”

“You’re welcome, for both, and thank you too. Damn, you felt incredible.” Lee rolled over and kissed her as she lay down, wrapping his arms around her. “I’ve got the whole day off, and if you keep running around looking so sexy like that, we’re going to mess these sheets up again.”

He was still naked, and a tingle shot up from Lynn’s sex, to arch through her whole body, when she looked down at his clean-shaven manhood. She was still a little afraid of the subject she was about to broach, but she had been thinking about it constantly the last few days, and it was about to drive her crazy. She didn’t know how he was going to react, and she felt more than a little worried about trying it, even if he wanted to. Lee was quite a bit bigger, and thicker, than any man she’d been with before.

Summoning up her nerve, Lynn kissed him one more time and said, “I sort of started without you while you were at work.”

Chuckling, he responded, “That’s okay. That’s why I buy you toys, so you can keep that pretty pussy happy while I’m gone.”

“I was watching that video that came free with my rabbit,” Lynn continued, punctuating it with a suggestive moan.

Lee asked, “Oh, is it good? What was it?”

Now Lynn had her opening. “Anal adventures or something like that. Do you like that sort of thing?”

“Mmm Hmm. We’ll have to watch it together some time,” Lee replied.

“Have you ever done that?”

Shaking his head, Lee said, “No, you know me, I wouldn’t even know how to bring it up.”

“Do you want to?” Lynn let all her desire flood into her voice with those words.

Kissing her, Lee asked, “You want me to fuck your ass, Babydoll?”

Lynn shuddered, letting out a gasp. “God, yes. You’ll have to be careful; I’ve never had a cock as big as yours in my bottom before.”

“Do you like it?”

Lynn shivered again, saying, “I love it, I come so hard that way. It’s not something I want to do very often, because it takes so long to get ready for — and I always sort of regret it for a while afterward — but I love how hard I come when I’m getting my ass fucked.”

“I want to. I’ve always thought about it, but I never thought I’d actually get the chance,” Lee said, kissing her hard.

“Let’s take a nap. I know you’re tired from work…” A crooked smile crossed her face as Lynn continued, “and other things. I want you to have plenty of energy.”

“How am I supposed to sleep, thinking about that?” The yawn that gripped Lee almost instantly after speaking took a little bit of the conviction out of the words.

Lynn laughed. “So, dream about it. That way you’ll have lots of cum for me again.” She kissed him tenderly, and then curled up next to him. They were both soon asleep.


Lynn woke up a few hours later, her pussy aching and soaking wet. She’d told Lee to dream about taking her ass, but even if he didn’t, she had. Slipping out of the bed slowly, so she didn’t wake him, Lynn walked to the bathroom and stripped off her damp panties, starting the shower.

Once the water was hot, she stepped into the shower, letting the spray splash against her pebble-hard nipples and tingling sex. Soon thereafter, she leaned back against the wall, gasping for breath and trembling in orgasm. The pent up need from her dream spent, she got down to the business of actually showering.

Once she toweled dry, Lynn walked back into the bedroom, still naked. Part of her wasn’t dry, and it had nothing to do with the shower. The thought of having Lee’s cock in her ass dominated her every thought, and she couldn’t have shaken it if she wanted to.

Lynn licked her lips when she saw Lee had kicked the covers off in his sleep. He was rock hard, and completely uncovered, almost calling out to her. Crawling into the bed, she slipped out her tongue the moment she could reach him, moaning as his hard flesh twitched beneath the wet caress.

It only took a few licks to awaken him, and Lee chuckled sensually when he saw Lynn lovingly lapping his hard cock. “I love when you wake me up like that. God, I’ve got to pee bad, though.”

Lynn pouted extravagantly, but then smiled and said, “Go, and get in the shower. I’ve already had one. Don’t be long.”

Once Lynn heard Lee get in the shower, she grabbed the bottle of lube from the nightstand drawer and walked in to the bathroom. Turning on the hot water in the sink low, both to avoid freezing Lee and so he wouldn’t hear the water running; she slowly filled the basin with quite warm water. As soon as it was full, she put in the lube bottle, and then reached under the sink for an enema. This followed the lubricant to float next to it in the steaming water.

Grabbing a pair of towels, as well as a box of moist wipes, Lynn took them to the bedroom and put them down next to the bed. She wanted to be prepared this time. The shower shut escort menderes off, and Lynn waited until she saw Lee drying his hair in the bathroom mirror reflection before she walked in.

When he pulled the towel away from his eyes, Lynn immediately pressed her body tight against him, kissing him hungrily. He returned the kiss with equal passion, squeezing her buttocks as the towel fell forgotten to the floor.

When their lips parted, he continued to knead her bottom, as she looked up into his blue eyes and said, “Do you want to fuck my ass, baby?”

Squeezing tighter and growling, he replied, “Fuck yes. You are so damn sexy.”

Pulling away from him, she nodded toward the sink and the two floating bottles. Turning around, she put her hands on the wall and bent over, jutting her ass out toward him, and then slowly slid down to her knees. Lee’s cock started rising even as she was turning, and he was nearly erect by the time she completed the slow drop to the floor.

Nodding at the sink again, she asked, “Do it for me?”

Lee understood what she meant, and fished out the enema, drying it off a little with a hand towel. Lynn moaned, and got down on all fours, pulling her knees in tight and thrusting her butt out to him. Lee knelt down and stroked the taut flesh of her ass, letting his finger trail through the cleft between her buttocks, drawing a shudder from her.

He pulled off the safety cap, knowing what to do, as he had done this for her before. The experience had certainly not felt this intimate and arousing before, however. Parting her cheeks with the fingers of one hand, he guided the nozzle of the enema toward the puckered iris of her ass.

Lynn clenched for a moment and gasped when the stem slipped inside her. After a moment, she was able to relax, allowing him to insert the enema fully into her. “Remember, just do it slow, but not too slow, and get out of here as soon as it’s done. I don’t think you want to be here for that part.”

Lee shook his head in the negative, and then started to squeeze. Lynn moaned for a moment, and then let out a little yelp and fought the urge that almost immediately assailed her. She kept in control, letting the fluid fill her to bursting.

Thoughts of fucking Lynn’s tight ass had Lee throbbing almost painfully. As soon as the bottle was empty, he pulled it slowly free and immediately stood. Lynn clenched up tight and said in a clipped voice, “Go, go.”

Stepping quickly out of the room, Lee shut the door and turned on the television in the bedroom, cranking up the volume a little. As he sat down on the bed, he wrapped his hand around his throbbing erection for a moment, to take a little of the edge off. He then settled back on the bed, anxiously awaiting Lynn’s return to the bedroom.

The bathroom door opened a short while later, and Lynn walked into the room, her hips swaying sensually and her hard nipples pointing out at him. “I’m all cleaned up for you, Baby. I want your cock in my ass.”

They quickly fell into a tongue wrangling kiss, Lee’s hand spreading Lynn’s buttocks as they did so, causing her to moan into the kiss. They broke from the kiss, and Lynn handed Lee the warm lube bottle. She got on her hands and knees again, bending down until her large breasts and face pressed against the sheets. She then reached back and parted her cheeks wide, giving him access to lube her bottom.

Lee pumped a small squirt of the slippery stuff onto his fingers, rubbing it over her forbidden entrance, which puckered tighter in response. Drizzling more lube onto his pointer finger, he slipped it into her tight embrace.

“Get it nice and slick, Baby,” she instructed.

Lee soon had two slick fingers almost completely inserted in her, and when he pulled them free, he pumped a generous dollop of lube into her ass before it could tighten. Lynn lifted her head from the bed, spinning around to take the bottle from her man.

Pumping twice, she filled her palm with lube, and then wrapped her hand around Lee’s cock, stroking it and covering his entire length in a thick coating. Grabbing a towel, she wiped off her hand, and then handed it to Lee so he could clean his fingers as well.

As he wiped his fingers clean, Lynn lay back, propping her upper body up on several pillows. Lee moved closer to her as she pulled her legs up and back. “I want to watch, Baby. Put that gorgeous cock in my ass.”

It took Lee a couple of moments to get in position, and then to figure out the odd new angle, but the purple helmet of his cock finally pressed up against the dark ring of Lynn’s ass.

“Easy,” she admonished, though she had no real need to do so.

Lee pushed gently, steadily adding minute amounts of pressure, keeping the slippery head in position. He felt just a little slip, and then his cock popped inside her.

Lynn gasped as he penetrated her, fighting the natural urge to clench up. “God, so big! Give it to me, Baby, give me more!”

They both menderes escort bayan growled as Lee pushed through her resistance. Lee paused, letting Lynn pant and grow accustomed to the stretch for a moment, and then edged forward again. Half buried in her tight ass now, he closed his eyes tight.

Lynn watched him vanish inside her, a tight knot building in her womb and a slight burn permeating her violated bottom. All the while, her clit throbbed and her juices flowed in a torrent from her depths, filling the air with the scent of her arousal.

“So fucking tight,” Lee growled, only about an inch of swollen shaft still showing outside of her. With a final push, he broke through the last of her resistance, burying his cock in her ass.

Lynn sucked in a long, slow breath, and then blew it out in an equally drawn out whistle. She slipped two fingers between her wet labia, stroking them softly. “Fuck my ass,” she told him in a breathless voice.

Animal-like growls that didn’t even sound like Lynn’s voice burst from her as Lee pulled back, and then slid back into her. With each stroke, it got easier to reach her depths. After only a few pumps, he set his hips in a steady rhythm.

“Oh, yes, so good,” Lynn growled, her fingers starting to flash over her sex, rubbing her lips and the bud at their apex. The knot in her womb grew larger, and tighter, even as her fingers sent electric pulses shooting from them toward the pressure deep within her. She could already feel the inevitable explosion building, and knew it wouldn’t take much to bring her to orgasm at this rate.

Lee built his speed, delighting in the feeling of the incredible squeeze. The way her juices were flowing, a few drops even splattering over both of them as Lynn stroked her pussy, Lee knew she was going to come quickly. He found that the tight fit held off his own itch, allowing him to keep thrusting without fear of creaming her ass before she came.

Lynn’s mind went numb with bliss, her fingers continuing to rub her clit on pure instinct. She had absolutely no control over the animalistic grunts and growls that each stroke of Lee’s cock in her ass drew from her. The pleasure — tinged with pain — just continued to build, welling up inside her like a dam about to burst.

Her scream of release was ear piercing, and Lynn’s muscles clamped down so tight on Lee that he was held stationary in her contracting ass as she came. The scream went on and on, becoming staccato as she was forced to suck air into her starving lungs. Her face, chest, and even her breasts were flushed a bright red. A trickle of her juices running from her pussy and over his cock let Lee know that she’d squirted. As soon as the pressure relaxed slightly, he reached down and parted her nether lips, starting to thrust again.

Lynn’s eyes popped wide open and she gasped for air as Lee’s cock once again assaulted her ass. She’d distantly noticed the hot tickle as she came, the telltale signal of her pussy squirting, as it often did when she had someone taking her ass. She closed her eyes again, panting for breath as another wave of climax swelled within her. She only dimly noted Lee’s fingers leaving her pussy, but a sharp scream of surprise burst from her when his cock popped out of her ass. Her head snapped back as the cool lube drizzled over her burning flesh, flowing into her still-gaped hole. A grunting gasp accompanied Lee’s cock easily sliding back inside her to the hilt.

Parting her labia again, Lee stroked his cock even faster in her tight ass. Her head lashed back and forth, even as her fingers continued to rub haltingly over her swollen clit. A few thrusts later, he got his reward, a short spurt of juices squirting from her to splash over them both as she came again.

Fighting against the tight contraction of her muscles, Lee kept rocking his hips. He barely managed to move at all, but it was enough to send Lynn to a higher plateau. Her eyes pinched closed even tighter, and her mouth opened into a silent scream. A moment later, her scream gained voice, and a fountain of her girl cum splashed against Lee’s stomach. The fitful stream changed angle as he pulled back, soaking her from hips to breasts, and a few drops even splashing against her face.

An edge of pain creeping into her screams of ecstasy caused Lee to pause, and let her settle slowly back to earth. Lynn’s eyes were misty when she opened them, and Lee started to pull free. Although he was painfully close to his own orgasm now too, he didn’t want to hurt her.

A groan of relief accompanied his cockhead popping free of her ass, but it was quickly followed by a moan of disappointment. “I want you to come in my ass, Baby,” Lynn pleaded.

“But, Babydoll…”

“I want it. Do it, Baby. Come in my ass.”

The unusual angle had been helping to stave off his climax, along with her tight squeeze, and so Lee said, “Get up on your hands and knees.”

Rolling over quickly, Lynn did as he asked, looking back over her shoulder and again telling him, “Come in my ass.”

Lee quickly pumped lube into her, and then edged into position, starting to push slowly inside her. Lynn thrust her hips backward, engulfing him in her ass with a loud growl. Responding to her obvious need, Lee grasped her hips tight and started thrusting full speed.

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