Young Tommy and Mature Cindy

PUBLIC BETA

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

Cindy lifted her hands up to Tommy's face. Cupping his jaw, she drew him close. Once again, his tongue slid into her mouth. As they kissed passionately his finger slipped between Cindy's wet pussy lips, then up and up over her clit. CIndy lost her composure, and they stopped kissing.

"You feel so good Tommy." She groaned.

Cindy knew she couldn't hold on for much longer, so she reached down, grabbed Tommy's middle finger and guided it deep into her quivering pussy. As she did this Tommy's left hand slid behind Cindy, between her and the wall, and he grabbed her ass cheek firmly. He held her tight with his left hand as he finger-fucked her with his right hand. Slow at first, but within a few seconds his finger was sliding in and out at a faster pace. Each time his finger penetrated her pussy it made a wet squelching sound. Cindy's heaving breasts jiggled next to Tommy's head. His finger plundered her snatch. Then, suddenly, an erotic bolt of lightning emanated from Cindy's pussy and flowed throughout her body.

"Oh Jesus!" Cindy groaned loudly. "Yes Tommy!"

Tommy bent down further. He sucked firmly on Cindy's nipple as her hefty breast smothered his face. Cindy's arms pressed against the wall. She struggled to keep her legs straight. As his finger glided in and out of her wet snatch, Cindy's pussy tightened and convulsed around his finger. Her hips were uncontrollable, but somehow Tommy managed to keep finger-fucking her without missing a beat. She was overcome with pleasure. The noises coming from Cindy's wet snatch were as loud as her groans. Cindy had lost control, not only of her body, but also her desires. Tommy's finger had turned her to putty, and each time he slid it deep into her hole she groaned. Cindy's orgasm lasted for what seemed like an eternity.

"Don't stop Tommy." Cindy gasped as her hips shook violently.

Tommy let her left nipple drop from her mouth. He stood up a little and let her head fall against his body. Tommy slowed his rhythm, but kept finger-fucking her as she groaned repeatedly. Gradually, the trembling of her body subsided. Cindy began to regather her senses. Tommy looked deep into her eyes and she looked back into his. Cindy kissed him again and savoured the moment. Still breathing deeply, her large, soft breasts heaved up and down against his thin, youthful torso. Cindy was pinned against the wall and they kissed in that position for another couple of minutes. Tommy then pulled his finger out, but he gently held her pussy with an open hand as they held each other.

"My God Tommy." She groaned as she leaned against the wall. "You're quite the natural aren't you."

Tommy let her go, then stepped back and just smiled. He looked down at Cindy's pussy juice dripping from his hand. Cindy remained propped up against the wall with her mouth half open. She didn't know what to say. They just looked at each other. Tommy had a bit of a smirk on his face. Cindy was struggling to comprehend what had just happened. Meanwhile, Tommy was just as surprised

"Was that OK?" Tommy asked with raised eyebrows.

"Yes Tommy." She sighed as she stepped forward and hugged him, resting her head against his chest. "That felt wonderful."

Cindy was still in a state of shock, not only because of the orgasm, but also because of Tommy's skills. Every movement of his finger touched her exactly where she needed to be touched. It was as if he could feel what she wanted. She had never experienced anything so erotic, nor as satisfying. Cindy could feel the wetness between her thighs and she looked down to see droplets falling from her knees. Suddenly, she realised Tommy was semi hard again. Not as erect as before, but almost. His thick cock pressed between them as they held each other.

"And you enjoyed it too, didn't you Tommy." She said as reached down and grabbed his cock.

Tommy looked down at her and smiled, as if to say 'of course'.

Tommy clasped his hands on her big, soft ass cheeks and held her tight. They stood there for a minute or so in a post orgasmic embrace. With her head against his chest she gently tugged his stiffening cock.

"Let's go back in the Jacuzzi." Cindy suggested as she walked towards it, dragging young Tommy once again by his dick.

They stepped down into the Jacuzzi. Cindy waited for Tommy to sit down, before straddling him. She shuffled closer until she could feel Tommy's thick pole pressing against her snatch. Their faces were only a few inches apart. Her breasts pressed against Tommy's young, bare chest.

"You're such a naughty, young boy Tommy." She whispered in his ear as she leaned into him. "You made me so wet."

Cindy ran her fingers through Tommy's short wet hair. Tommy's hands massaged her big, rounded ass under the water. They kissed again. Cindy loved the feeling of him holding her ass, almost as much as she enjoyed his tongue in her mouth. Then, she leaned back slightly and lifted up her weighty breasts, before guiding her left nipple into Tommy's mouth.

"Kiss me here Tommy." She groaned.

Tommy started sucking passionately on her stiff nipple, and as his tongue swirled around the tip of her oversized breast, he manhandled her ass. Cindy arched her back and groaned slightly as she looked up at the ceiling. It felt so good, but she wanted her mouth around the head of Tommy's cock again. She could feel it pressing against her and she wanted to taste him again. She wanted more of his youthful cum squirting in her mouth.

"Sit on the edge Tommy." She instructed as she stepped back slowly and stood in the water.

Tommy silently followed her orders and sat up on the edge of the Jacuzzi. He leaned back and propped himself up with his arms on the ground behind him. He opened his legs slightly. Cindy crouched down and moved towards his legs, admiring the enticing view. Tommy's smooth balls dangled on the edge of the Jacuzzi and his big, erect penis pointed upwards on an angle. As Tommy leaned back his abdominals became more clearly defined. Cindy reached out and put both hands between his knees, parting them further as she glided between them. Her small, pudgy hands then moved up the inside of his thighs. She kneeled on the seat, and as she did this her big, beautiful breasts emerged from the water. Then, Cindy clasped his cock with both hands - her right hand on the base, and her left hand near the tip. Tommy looked down at Cindy and smiled. A smile of satisfaction.

"You're such a tease Tommy." She purred seductively with a cheeky smile. "Waving this big thing of yours in an old lady's face."

Cindy released her grip at the base of his cock, but she held onto the head with her left hand. She leaned down, placed her right hand on Tommy's left thigh, and licked his shaft.

"Ohh." Tommy groaned as his body clenched.

Cindy's tongue worked his stiff pole, up and down, before then moving down to his balls. She slowly licked his balls, then let one slide into her mouth. Her tongue over it, back and forth, back and forth.

"Ohh Ms Santos." Tommy groaned again.

Cindy began switching from one ball to the other, slowly swirling each one in her mouth, while rubbing the head of his cock with her left thumb. After a while she pulled her head back and looked up to see Tommy staring down at her. Cindy could feel the pre-cum on the head of his dick - the unmistakable slimy texture under her thumb. She let go of his cock, kneeled up straight again, and lifted her big, pillowy breasts onto his thighs. Young Tommy looked as eager as Cindy felt.

"Tell me if you're about to cum Tommy." She instructed.

"Um, OK." He mumbled.

Cindy leaned forward and kissed his bare, youthful stomach. Her wet, soft breasts slid further up his thighs. She could feel her stiff nipples slide against his skin. Then, she leaned back slightly, pressed her breasts together, and smothered his virgin cock. The tip of Tommy's dick peeked through the deep, soft crevice of her big, mature tits. Cindy's hands slid further forwards along the outside of her breasts until her fingers reached her nipples.

"Does that feel good Tommy." She asked, knowing of course that it did.

"Y...yes." He stuttered with open eyes.

Tommy leaned back slightly, pushing his dick up a little more. Cindy began wanking his big hard cock with her soft, fleshy tits. She pinched her nipples at the same time. For Cindy, it was a glorious sight to see - Tommy's young, pink head disappearing, then reappearing between her big, brown breasts. For Tommy, it was as if he was dreaming. He looked down in awe at the glorious sight of Cindy's bosom pummeling his cock. Tommy's pre-cum was visible on her tits. When she looked up at Tommy he shifted his gaze from her breasts to her eyes. Cindy smiled.

"I love the feeling of you between my breasts Tommy." She purred as she held his gaze.

Heavy breathing and a smile was the only response she received. Cindy's big, caramel breasts enveloped his stiff prick again and again. Up and down, up and down. Watching Tommy's young dick disappear, then reappear, is a sight she will never forget. Her pussy was aching again for his touch, but she wanted to feel Tommy's cock explode in her mouth again. Then, she would get him to deal to her needs.

"Are you going to cum for me again Tommy?" Cindy asked.

"Um, yeah." He stuttered in response.

Just a few minutes before young Tommy couldn't handle the slightest touch, but after cumming once, it was clear Tommy had developed some staying power. This made Cindy happy. When the time came, Cindy wanted him to be able to fuck her properly. She knew Tommy would become hard again, even after cumming a second time. She looked up at him and saw a more confident look on his face. Previously, when she was kneeling in front of him on the sun lounger, he looked unsure of himself and hesitant. However, when he was sitting on the edge of the Jacuzzi, and she was titty-fucking his cock, he appeared more at ease. He was going to make Cindy work for another mouthful of his tasty jizz, and that was fine by her.

"Do you like seeing your young cock slide in and out of big breasts Tommy?" She asked as his dick slithered between her crevice.

"Yes." He said quietly with a slight nod.

"I like it too Tommy." She moaned, as she continued to pinch her nipples.

Then, she moved back and allowed her tits to fall into the water. Cindy placed her elbows on his thighs and gripped his cock with her right hand. Leaning down, she wrapped her lips around the head and rolled her tongue over his throbbing helmet. As she did this she pumped his shaft with her right hand, while sliding his cock further and further into her warm, eager mouth.

"Your big, young cock feels so good in my mouth Tommy." She moaned as she pulled it out briefly, tapped it on her plump lips, before sliding it back in her mouth.

Cindy paid close attention to the head of his dick with her tongue. As she slid her lips up and down the shaft she sucked more firmly on the tip.

"Are you going to be a good boy and give me another load of your cum?" She asked as she rubbed the tip of his cock over her pouty lips. "Be a good boy for Ms Santos Tommy. Cum in my mouth again."

After she said that Tommy's dick started to flinch, and she could feel the movement in his hips again. This only encouraged Cindy.

"Please Tommy. I want to feel your cum splashing inside my mouth again." She whispered as her right hand massaged the head of his cock. "You can't keep teasing me like this."

Tommy looked a bit shocked, but also excited. Cindy was also shocked with the words that were coming out of her mouth. She'd never talked this way before, but at that moment she had no restraint. She was 64 years old, she had a young 18 year old boy naked in her Jacuzzi, his cock was in her mouth, he'd just fingered her to a massive orgasm, and a few minutes before that he'd drowned her with his jizz. The whole situation was out of character for Cindy. But she was lost in the moment. She rubbed the tip of his cock against her lips as she wanked him

"You naughty boy Tommy." She moaned as she looked up at him. "Seducing an old lady like me. First you came all over my face, and now look at me. I can't stop sucking your big, young cock."

Cindy's mouth returned to the head of his dick. His thick shaft slid in and out of her mouth as her head bobbed up and down. Her tongue circled the head. As she did this she could feel his hips and cock shuddering more and more.

"Oh Ms Santos, I don't think I can..." Tommy groaned before trailing off.

Cindy knew he was about to blow again, so she moved her right hand to the base of his shaft, and increased the tempo.

"Mmmm." She moaned as she excitedly waited for another blast of Tommy's young sperm.

"Urgh." Tommy grunted loudly as his whole body flexed

Suddenly, his quivering cock spurted a load of warm, sticky cum against the top of Cindy's mouth, and down the back of her throat.

"Mmm." She murmured as she swallowed quickly.

Then another shot. It was just as big, if not bigger. Cindy only just managed to keep her lips wrapped around the tip of his cock as he filled her mouth. Again, she swallowed his jizz greedily. Tommy gently held Cindy's head with his hands. She released her hand from his cock. Cindy's arms locked around Tommy's thighs to keep him from moving too much. He bobbed her head up and down on his dick, fucking her warm mouth, as he ejaculated more cum into her.

"Argh!" He groaned loudly as his body writhed around on the edge of the spa.

Tommy let go of Cindy's head. His placed his hand behind himself. Cindy's lips continued sliding up and down his shaft. She swallowed again, and again. Tommy's body kept moving and Cindy had to concentrate to ensure his cock remained in her mouth. She didn't miss a drop. Before too long Tommy's body spasms subsided, but she kept sucking on his cock and enjoying the occasional shudder. Cindy looked up at Tommy to see him looking down at her with that stunned look on his face again.

"Ohhh Tommy." She moaned as she let his stiff cock slide out of her mouth. "You taste so good."

Tommy looked down at her and smiled. She smiled back at him. Cindy's hands returned to Tommy's shaft. She gently rubbed the tip of his cock over her mouth, against her lips and slightly protruding tongue. As she guided it back in, her pouty lips slid down Tommy's erect member. His cock slowly disappeared into her mouth again. They both looked into each other's eyes. It was extremely erotic, but also sensual. Cindy lifted her right hand and ran it over his stomach up to his chest until her fingers ran over Tommy's nipple. When she squezzed his nipple his cock flinched in her mouth.

"Mmmm." She groaned, slightly amused at his flinching cock inside her mouth.

Tommy appeared to like it, so she kept squeezing his nipple. Again and again. This went on for a couple of minutes until Tommy began to lose his hardness. He sat on the edge of the Jacuzzi, leaning back, with his slowly deflating cock sliding in and out of Cindy's mouth. She couldn't believe her luck. Tommy was such a nice young boy - polite, gentle, handsome, and sensual. Cindy was old enough to be his grandmother, but they had a connection. A warm, tender connection that seemed at odds with what they were doing. Yes, they were having dirty, hot, steamy sex, but there was something more between them. It was as if the age difference didn't exist. However, it was also the age difference that made the whole experience so erotic. Tommy put Cindy at ease. He allowed her to open up in a way she never could before.

"Well." Cindy said, finally breaking the silence. "That was amazing. Again."

Tommy just smiled. He was speechless. His smile said everything. Cindy wanted Tommy's young cock in her pussy, but first she wanted him to taste her. She had no doubt that with a few pointers Tommy's mouth would feel amazing on her snatch, and she was sure he wanted to taste her.

"Come with me." Cindy said as she stood up and held out a hand to Tommy.

Tommy stepped down into the water and grabbed her hand. They walked out of the Jacuzzi, through the gym, and towards the house.

"Let's go to my room." Cindy said as they walked through the corridor.

Tommy smiled and nodded. The cute smile Cindy couldn't resist. Cindy let go of his hand as they entered the lounge. She walked over to the kitchen.

"Would you like a drink?" Cindy asked as she opened the fridge. "I've got some Champagne in here."

"Yes please." Tommy responded, as he watched her get two Champagne flutes from a cupboard.

Cindy quickly removed the foil and wire cage at the top of the bottle. Cindy gripped the cork firmly and pulled.

'Pop!'

Tommy watched Cindy's tits jiggle as froth squirted from the top. Cindy lifted the bottle to her mouth to catch some of the foam. She looked up at Tommy who stood naked in front of her.

"You've seen me do that before, haven't you?" She said quietly with a mischievous grin.

"Haha." Tommy laughed quietly.

Cindy blushed. She felt a little embarrassed. Cindy poured the Champagne into the glasses, then handed one to Tommy.

"To new experiences." Cindy said with a smile, as she lifted her flute to Tommy.

"To new experiences." Tommy replied.

Their flutes clinked. Cindy stepped forward, pressing her left breast into Tommy, then she slid her left hand around his waist. He smiled down at her as he sipped the Champagne.

"Come with me." Cindy said as she walked towards the stairs.

Cindy walked in front of Tommy. She wanted him to view her from behind as they climbed the stairs. He looked up in awe at her generous ass cheeks as they bounced from side to side with each step.

"This is my room." Cindy said smiling over her shoulder at him when they reached the door.

She pushed open the half-closed door and Tommy stepped through. Cindy followed him in. Cindy's bedroom is large, but simple. A clean, modernist look. There's a king size bed, with a small table next to it, and a white leather sofa against the wall. It was getting dark outside, so Cindy turned the lights on. She dialed the dimmer down slightly, but ensured it was still bright enough to see clearly. Tommy stood at the end of Cindy's king-size bed looking a bit unsure of himself. She grabbed Tommy's Champagne flute and placed them on the dresser next to her bed. She then pulled back the heavy duvet until it fell to the ground at Tommy's feet. The red sheets and the charcoal colored pillowcases looked enticing. Then, Cindy climbed onto the bed, and positioned three pillows against the wall, before lying down with her upper body propped up on an angle. She leaned back and lifted her legs slightly, before spreading them. Cindy looked up at Tommy who was still standing at the foot of bed. He didn't say a word.

"Come join me Tommy." Cindy purred as her left hand slid down towards her wet, gaping snatch.

Tommy moved forward, climbed onto the bed, then crawled towards her on his hands and knees.

"Come lie down here." Cindy whispered as she patted the silk sheet between her open legs. "Do you want to be a good boy and pleasure me properly?"

Tommy nodded with raised eyebrows. He lay down on the bed between Cindy's thick, brown legs.

"Come closer Tommy." Cindy purred, as she ran her fingers up and down the puffy lips of her slit.

Tommy shuffled forward until his face was right in front of Cindy's bare cunt. She reached down and lifted his face slightly with her hands, before running her fingers through his hair. Tommy looked up at Cindy nervously. He would be lying if he said he wasn't a little frightened. Cindy knew her pussy was wet, and she knew he could smell the scent of her snatch. She lifted her hands off Tommy's head and placed them on her pubic mound. Cindy's fingers returned to the lips of her wet slit. She gently pulled them apart, just inches from Tommy's wide eyes.

1...345678