Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.
You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.
Click here
He flipped her over, "I wanna see your face when I slide my cock into your virgin pussy." He gripped his cock and swept it up and down her slit. He pushed the head into her tight hole and the head popped in. He saw her lips puckered up and let out a gasp.
She nodded, "Give it to me Daddy, I need to lose my virginity. I can feel it stretching me. It's so fucking fat, but you got me so hot, I should be able to take it with ease."
"Oh don't you worry Sweetie, I'll be gentle and make sure it doesn't hurt too bad." He leaned in and planted a hot, passionate kiss on her lips. He reared back and slid further into her. He felt it press against her hymen. He wiggled his hips, causing his cock to brush against her clit. It drove her to higher heights of excitement and as she trembled, Leonard pistoned his hips forward with one savage thrust and he heard her let out a scream as his cock tore through her hymen. He plastered his mouth to hers and kissed her roughly, accepting her tongue and muffled her moans and groans as he he shoved deeper into her. He held it there until her pussy stopped fluttering and as her legs lost the tension in it, he began to move.
Halley began pushing back as the pain receded and the passion and itch began to grow, "Come on Daddy, fuck your little girl's pussy. Fuck me as hard and as fast as you want. I don't want you to stop until you make me cum again and then I want you to pump your hot, potent seed deep in my unprotected pussy."
Just hearing that made Leonard crazy. He fisted her hair and kissed her. He fucked her slow, and steady. He moved to her gorgeous tits and sucked on one and then the other. He steadily picked up the pace and as he went faster, driving into her deeper. He felt her urging him on and knew she was a natural. Her legs came up and wrapped around his waist. Her heels kicked at his ass as she screamed out, "I'm cumming, please, please Daddy, cum in me. I need to be a real women, give it to me."
Leonard went over the deep end and slammed into her as hard as he could. He ground his cock against her, sending her into an even stronger orgasm. He started to cum and he felt her quiver and tremble.
As he started filling her with his potent cum, she screamed out and thrashed around, screaming out, "OH YES DADDDY! I LOVE YOUR HOT CUM FILLING ME! MORE, GIVE ME MORE DADDY!"
Leonard enveloped her shaking body in his arms and their hot, sweaty bodies clung together. They stayed together for what seemed like forever.
After a long period of kissing and caressing, they separated and she curled up in his arms and drifted off to sleep.
While all of this was happening, in the guest house, Michael stepped into the living room and stopped when he saw the women of his dreams sitting there, her legs crossed and he stared at the white flesh above the top of her thigh-hi sheer black stocking. He looked up and saw her smiling as she sipped on her wine.
She took in his youthfulness. She still thought of him as a young Rob Lowe, "Why don't you stop staring and come over here and settle down and have a glass of wine with me."
He could feel his cock swelling in his pants as he came over to sit beside her. She handed him a glass of wine..
He sat back and took a sip and he nearly choked on it as Penny kicked off her heels and moving to the corner of the sofa. She sat back and raised one of her nylon covered feet and ran it up his calf, to his knee. He took another sip of is wine and glancing down he felt his cock stiffen even more. He loved her toenails scraping against his overheated flesh. He saw the painted nails, they were red, almost as red as his face, he was blushing thinking about what was going to happen.
Penny turned more on the sofa and her feet reached his groin and he drew in a deep breath and released a groan deep in his throat. She saw him squirming and chuckled, "Okay Michael, whip it out, I'm dying to see what I have to work with."
He managed to unzip his pants with one hand, he wasn't letting go of the wine, he knew he'd need a refill soon. He nearly choked on the wine as he watched Penny's large feet wrap around his cock. He couldn't believe how gorgeous her feet were and his cock was now rock hard. He knew, if her feet were that beautiful, he couldn't wait to see the rest of her.
Penny had a grin on her lips as her toes curled around his shaft. She knew it was his first foot-job, she was going to be giving him his first blow-job and first-fuck. A lot of firsts and she couldn't wait for then to begin.
He couldn't keep his glass steady and he placed it on the end table, not wanting to spill it all over the both of them. He leaned back and just watched, not wanting to screw things up by getting ahead of what she was doing.
Penny pushed his stiff cock against his belly. She had talented feet and slid one up and down. She tickled his nuts with her other foot and she chuckled when he pushed his pants and shorts down to his ankles.
He was squirming around and she was breathing heavily. She knew if she continued, she'd have a mess all over her stockings. She reached over and picked up a vial of pills. She opened it and handed one Michael, "Here take this, I think you're gonna need it."
He shook his head, "I don't take drugs, Aunt Penny."
She shook her head, "It isn't like that!" She popped one into her mouth and washed it down with the wine. She knew with this virile young man, she'd need one to keep up with him. At the same time, she knew he wouldn't be able to restrain from cumming and she didn't want a one or two shot wonder. "It's a sexual enhancement medication. It's the one your mother and I promoted several years ago. It will insure that just like the Energizer Bunny, you'll be able to go on and on and on. Just one thing, never, ever take more than one in any twenty-four hour period. It could result in permanent damage."
He popped it immediately in his mouth and washed it down with his wine. He put he glass down and as he turned, Penny stood and reached for his hand, "No need beating around the bush. What do you say we take this to the bedroom?"
He hopped up and nodded, "Oh yes, Aunt Penny!"
She giggled, "I think for tonight, you can drop the Aunt crap and just call me Penny. Or whatever you think you should." She gripped his stiff cock in her hands and tugged at him as she tried to lead him to the bedroom.
He tripped and nearly fell. His pants and shorts were still around his ankles. He toed off his shoes, kicked off his pants and shorts and removed his socks.
She giggled, "Nice move, if you left your socks on, you could be a leading man in one of the old porno movies they used to make." She tugged at him and led him to the bedroom where she already had the bed turned down and had set the mood with several candles.
He came up behind her and enveloped her lush body. His hands immediately traveled from her hip to her large, firm unencumbered tits. They filled his hands to overflowing. He squeezed and pulled her back to him as she chuckled on his clumsiness. She let out a giggled and she shivered when he dipped his head and kissed her neck. He wanted to devour her and lick, and eat every inch of her lush body.
With his stiff rod pressing against her plush ass, he began unbuttoning her silky blouse. He loved she wasn't wearing a bra. He slid it off her shoulders and it fell to the floor. He looked over her bare shoulders and saw the two most exquisite tits he's ever seen. He saw them so many times in the videos he couldn't count, but in person, they looked even better. He reveled in her round and luscious aeroules with those stiff dark nipples, just aching to be sucked and nibbled on. His hands ran all over her exposed flesh and couldn't believe how lucky he was to sample the flawlessness of her body. He felt how soft it was and he couldn't get enough. He cupped both tits, he was in heaven. Despite their ample size, they were standing high on her chest. He scissored those fat nipples between his fingers and tugged on them. He peppered her neck, shoulders and upper back with soft kisses. He moved to her ear and bathed it with his hot breath as he captured her lobe and tugged at it.
Penny spun in his grasp and before she could react, his face was buried in the mounds of flesh he adored. He couldn't get enough as he licked and sucked at every inch of them. He inhaled her scent and sucked avidly at each rosy nipple causing the bumps around the nipple to perk up too.
Penny was excited by his enthusiasm and breaking free, she moved to the bed and climbed up onto it. She spread out and stretched lazily, trying to make her look as sexy as possible. It worked and she saw the look of pure lust in his face, "You know, I wanted to take it slow with you Michael, but it isn't working. Let's Fuck!"
His remaining clothes flew off, just like in those funny cartoons. He couldn't tear his eyes from her as Penny skimmed out of her skirt and slipped her sopping panties off.
He approached the bed and ran his hands up her squirming legs. He got his hands on the tops of her thigh-hi black stockings and moved to the bare flesh above them. He listened to her purr as his knuckles brushed her thick, fleshy cuntlips. He turned his hand and his fingertips curled inward and traced a line from her clit to her dripping hole. He shoved inward and sank a couple fingers into her tight, juicy cunt.
She let out a gasp, "I thought I was gonna have to train you, but it seems you're well aware of what to do."
He released a throaty chuckle, "I learned a lot about you by watching your videos, over and over and over again."
She scoffed, "Okay smart ass, let's see how well you fuck."
He continued to explore her pussy with his fingers. He finger fucked her and he grinned when he heard her let out a gasp. He licked his lips as he inched forward. He had countless dreams about eating her pussy. He lowered his head and was about to feast on it, but was stopped.
"Sorry Michael, with all of that tit play and all the time I spent giving you a foot job, I need to be fucked and fucked now. We'll leave that for another time. Just fuck me now, stud!"
He hovered over her and watched as her hands darted down and spread her fleshy cuntlips. She patted her juicy hole with a thumb, "Just shove it in there and fuck my cunt, just like in the porno you watched of mine."
Michael all of a sudden was tentative. He gripped his stiff shaft and nearly began to drool as he stared down at the pink flesh just inviting him in. He shivered and released a groan when he felt the warmth envelope the head of his cock. He slowly eased it in. He savored the feeling of her flesh surrounding his shaft. He couldn't believe how incredible it felt. After seeing numerous of her videos, actually shoving his cock into her was sure bliss.
Penny's pussy was dripping wet, lubricating his shaft as he shoved more on his length into her. With every inch he sank into her, more feelings of overwhelming need to fuck her overtook him.
He began to pump his hips, sending his cock into her depths. He finally had his entire length in her and he stopped to feel the exquisite sensations coursing through his shaft.
Penny wrapped her legs around his body and began to squeeze his shaft with her talented cunt muscles. She heard him groan out and she captured his mouth as they kissed like two long lost lovers. She realized this was their first kiss on the lips and it turned her on even more.
He began to move, starting off slow, he picked up the pace. He wanted to go hard and fast, but he knew he wanted this to last, to last all night, even though he knew it wasn't possible. He hovered above her, his hands clung to the damp sheets as he began to use every part of his body to fuck this famous porn star.
She raked her nails over his back and kissed him again. She tore her mouth from his and called out, "Harder Michael, fuck me harder!"
He gave her what she wanted and the bed shifted with each downward thrust.
Her body was shaking, her tits swayed and shook with each thrust. She closed her eyes, opened her mouth, and the only thing that came out was a moan.
Michael pumped her hard and with such intensity, his balls slapped her tight ass cheeks. He got to his knees, and the her legs spread wide, he fucked her as hard as he could. He clutched at her sweaty tits and pressing them together, he leaned in and sucked at both stiff nipples at the same time.
Penny lost it and started cumming. She coated his ramrod with her creamy cunt juices. Her talented cunt muscles tightened and milked his cock and before he could slow it down, he lost it and began pumping his heavy load deep into her spasming pussy.
He slumped against her, peppering her face, neck and chest with hot, wet kisses, "Oh thank you Penny, I am no longer a virgin!"
She wrapped her trembling legs and arms around him and hugged him and kissed him back, "You are more than welcome Michael, that was intense. There is nothing like the youthful exuberance of a stud like yourself. After I get feeling back in my extremities, we are going to take a nice shower and then I'm going to give you something much better than a foot-job."
He chuckled and kissed her long and hard. He hovered over her and stroked her tousled hair, "My God Penny, you may be retired, but you will always be the most desirable porn star on the face of the earth. So what is better than a foot-job?"
She giggled, "No need for flattery, I'm yours for the night. And for your question, one of my famous blow-jobs. I can't wait to see your face when I get that cock of your deep in my throat." She groaned when she felt his cock swell as it came awake again, still in her pussy.
Just as she promised, she took him into the shower and after washing most of the cum he deposited in her, she fisted his cock and stroked him. He was stiff throughout the shower and she wanted him in her mouth and throat. She didn't want to spend the evening with her hair wet. She turned off the shower and after drying one another, she hurried to the bedroom where she licked and sucked at him as she did all those black porn stars. She had saliva dripping from his shaft as she slowly took him into her mouth. She slowly allowed him to fuck her face. She relaxed her throat and let him enter her throat.
Michael pulled out and guided her onto her back. He stared at the gorgeous blonde, her hair hanging off the side of the bed. He smiled down at her, "Penny, I've seen you do this so many times, I can't count the times I came just watching it."
She giggled, "So you want to fuck my face and see my saliva cover my face. Do you wanna cum all over my face and tits?"
He grinned down at her and all he could do was nod his head. He stepped closed and groaned out when Penny's hands grabbed hold of his tight ass and drew him to her bent head and opening her mouth, she guided his cock into her mouth. A gurgling sound escaped her throat as it was replaced with his cock.
Michael was in nirvana. He began slowly, savoring every exciting moment he was experiencing. Her mouth, her tongue, the heat coming from her mouth. Her dark green eyes staring up at him as as she took him deeper and deeper. He clung to her messy hair as he picked up the pace. The erotic sounds coming from her sucking mouth already brought him to the cusp of cumming. He slowed, not wanting this to end. He closed his eyes, but she continued to suck and tug at his ass as she swallowed his cock over and over again.
Penny was blowing bubbles as large strings of saliva ran out of her mouth and into her hair, her cheeks and to her neck.
Michael allowed her to suck him as he continued to thrust his hips, fucking her pretty face. He reached down and mauled her tits and after a few minutes, moved to her pussy and found a sloppy mess. He knew after he finished all over her face, it would be her turn. He shouldn't have been thinking about that, because it sent him over the top, "Oh fuck me Penny, I can't! I want this to last longer. FUCK! FUCK! I'm too far gone. Oh take my cum you gorgeous fucking slut!" His first blast coated her tongue. Pulling it out, he began painting her face, neck and tits with several thick blasts of cum. His legs began to shake and he had to clutch at her shoulder as he aimed his cock at her gorgeous face.
Penny blew bubbles from his thick load and licked her lips as she giggled, "Too bad you came so quick, it's still early. After I clean up, what would you like to do next?"
He was smiling like a kid in a candy store, "You stopped me earlier, but I still would love a taste of that beautiful pussy of yours." She groaned out, "Okay, it is your day and I would love to see how you can eat pussy."
She cleaned up and she got what he promised. She came several times and by the third time she was exhausted, she pulled him to her and she rewarded him with another great fuck. This time in multiple positions, doggy and ended up with her riding him where he emptied his balls deep in her.
They clung to one another as they drifted off to sleep.
The following morning, the four of them had brunch in the kitchen. Michael was raring to go again. He couldn't wipe the smile off his face. Halley was just as happy. Both Leonard and Penny were exhausted and gave it up to their age and the two virgins ability to be raring to go again.
After they cleaned the kitchen, Penny went to the bedroom and screamed out, "What the fuck happened in here."
An ashamed Halley came in and let out a gasp, "Oh my God, I know I made a mess, but I didn't realize it was this bad."
Penny drew her into her arms, "Sorry Halley, I wasn't expecting this, what happened?"
She was blushing, "Aw well, Dad sorta went down on me and I got so excited, I thought I peed all over him. He comforted me and told me I didn't pee, but I squirted. I was still embarrassed. He told me it was something to be proud of. He said not many woman could do this."
Penny hugged her and kissed her gently on the lips. "He's right. I've only did it a couple times. Would you believe both times were by the talented mouth and tongue of Leonard. He's known as..."
Halley cut-in, "He's "The King of Foreplay." I've heard it many times from my mother."
Penny chuckled, "She's right and I have to agree. Don't be ashamed. You are a very, very lucky woman to be able to do that."
"Yeah, maybe, but I don't wanna do it all the time. What would a guy, or girl who doesn't know what is happening think of me?"
She giggled, "You can control yourself. You just need practice." She looked to the dried mess on the bed. She walked over to the bedroom. She closed it and locked the door. She came back to Halley, "I sorta remember you saying something about trying out a woman. All of this talk has turned me on. What do you say we mess up this bed a little more before we strip it and do the laundry."
She giggled, "Oh, by the way, Dad took me to the guest bedroom afterwards and we sorta made a mess there too."
Penny guided Halley into the bed and she stood there staring at the tiny blonde. Halley rose up and rested her blonde head on the palm of one hand as she stared at the gorgeous older woman.
Penny planted one knee on the bed and she reached out and tucked Halley's light blonde hair behind her ear. She leaned forward and planted her lips firmly on Halley's parted lips. They both opened their mouths and soon the both of them were making slurping sounds from the intense French kiss they were sharing.
Penny broke the kiss and slipped the strap from her dark blue camisole off one shoulder. She ran her hand across the upper portion of Halley's chest and slipped the other strap off too.
Halley struggled to slip her arms out of the camisole and in doing so, the top fell to her trim waist, leaving her firm, full tits exposed to Penny's gaze.
Penny rose up on her knees and with one swift motion, drew her thin t-shirt up and over her head, leaving her upper body completely naked. She leaned back over and cupped Halley's firm, rose tipped tits. Her hair fell over her face and covered half of Halley's upper body as Penny's plush lips closed over one ripe nipple. She began kissing and sucking on both nipples. She smiled when she heard Halley squeal out in pleasure and her hands came up and ran her fingers through Penny's hair, pulling it back so she could watch the experienced woman sucking avidly at her puckered nipples.
