Jimmy has added 2 more names to his growing list of lovers; now he’ll add another…
Jimmy was riding his bike home after his night with Max and Uncle Chris, feeling the discomfort in his ass from the reaming it had taken from Uncle Chris’s monster cock. He repeatedly lifted his battered butthole up off the seat of his bike in an effort to give it some relief. It seemed like the ride took twice as long as it was. Once he got home, he parked his bike in the garage, figuring that he wouldn’t be riding it until his tender anus was healed up.
He went into the still empty house, threw his dirty clothes in the laundry, and started a load. He heard his phone go off. He had messages from both Lizzy and Brit. Brit was just checking in. She was spending some time at her friend April’s family lake house. Jimmy wondered how many other people were there, and how much fucking was going on. He had had plenty himself, so he wasn’t jealous, just curious.
Lizzy’s message was good news:
L: Coming home today! I can’t wait 2 c u!
J: YAY! I miss u 2!
L: I need some dick! I have only fucked Sadie and Joey the last couple days.
J: So you only miss my dick? 😲😜
L: Funny. Not. 🤨🤪
J: Jk. I’ll be home alone. Maybe you can stay the night.
L: That would be awesome!
L: Mom and Dad both said OK.
J: Sweet! See you 2nite, hottie!
L: 🥰😍😘
Jimmy was happy at this turn of events. He could spend the entire night with his best girl and favorite pussy. He had really grown attached to the 8 year old. It was more than just sex with her, it was much deeper than that. But he didn’t have to time to dwell on that now; he wanted to get his work done before the day got too hot. He gathered up his gear and headed out.
After finishing up for the day he headed home and hopped in the shower. After he got out and dried off, he applied some ointment to the tender ring of his assaulted asshole. He had enjoyed the fucking Uncle Chris had given him, but he sure hoped it wouldn’t hurt afterwards like this if the man ever fucked him again. After performing first aid on his most intimate place, he headed to the kitchen for a snack. He took a nap after that, waking up to make some dinner. He checked his phone and saw another message from Lizzy, saying that she would be home around 7 o’clock.
In the not so distant past, if left alone at home, Jimmy would watch porn and jack off. He didn’t need to do that anymore with all the sex he was getting. He especially didn’t want to do that with Lizzy coming over to spend the night. So he just watched videos on the couch and nodded off again until he felt someone shaking him awake. He opened his eyes to find Lizzy standing there wearing a big grin and nothing else.
“Well, I can see what you have in mind already, lover.”
Lizzy grabbed him by the hand and helped him up. She led him up the stairs and towards his room. He stopped her and said, “Let’s go to my parents’ room. The bed is bigger and they have a TV in there.”
“Okay. What are we going to watch while we fuck?”
“What do people usually watch when they fuck? Porn! I’ll grab that flash drive your mom gave me.”
“Okay. I still don’t know how much we’ll be watching since I plan on keeping you distracted all night.”
He gave her a playful swat on her little ass as she headed to his parents’ bedroom. He went and grabbed the flash drive. When he got to his parents’ room, he found Lizzy spread out on the bed, idly rubbing her tiny clit. He took in that sight, thinking that he would never tire of seeing that oh so pink cunt. He popped the drive into the TV and pulled up the menu. He hit the “Play All” option and jumped on the bed and on Lizzy. She wrapped her arms around him and they French kissed like they hadn’t seen each other in months instead of a couple days.
Jimmy started kissing his way down his little lover’s body. When he got to her chest, Lizzy stopped him, saying, “You need to spend more time on my titties, mister. I may not really have any yet, but I still have nipples, and I like them sucked and played with too.”
“Duly noted, ma’am. I won’t make that mistake again.”
So he paid extra attention to her nipples before making his way down to her bald pussy. He could hear the action on the screen and thought to himself that Lizzy was right, they were too distracted to watch it. He made his way down to Lizzy’s soaking wet pussy, finally, and ate it until she had a screaming orgasm. And so it went for the rest of the night. They sucked and fucked all night, occasionally taking breaks and watching the homemade porn that Lizzy’s mother Sandi had provided. Lizzy would point out the different family members she recognized. Jimmy was pretty impressed by what a freaky bunch her family was.
Things went on like this for the next few days. Lizzy’s parents let her stay with Jimmy while he his family were all gone. He fucked Sandi one day; Sadie stayed the night and they had a threesome; he fucked Sean one day. He told Lizzy all about his night with Max and Uncle Chris, even showing her pictures that Max had sent of him done up as Girl Max. She agreed that Max made a pretty girl, but she seemed a little jealous. To take her mind off it, he licked her pussy and fucked her. She settled down after that.
Jimmy was starting to feel kinda like a married man, going to work, coming home, having dinner, fucking his woman. They even had a kind of open marriage, with the agreement that they were free to fuck other people. When he was due to cut Mrs. P’s lawn and do her yard work again, he would get to exercise that agreement.
Mrs. P had been quite flirty the last few times he had been to her place. She was definitely an attractive, older woman with seductive, brown eyes, her hair streaked with different shades of blonde, falling past her shoulders in waves, her tits large but not huge, only sagging slightly, her legs long and toned from the yoga and pilates she did regularly. Her shapely ass benefited from the exercise too. She was definitely the epitome of a cougar or MILF, having two grown children in college. She was just beautiful, beautiful enough to have probably any man she wanted. It seemed that the man she wanted was a boy, our guy Jimmy.
She was recently divorced and didn’t want to be bothered doing the yard work her ex used to do. She could have hired some outfit to do it, but she decided to hire Jimmy at her neighbor’s recommendation. Why not, she figured, she’d rather help out a neighborhood kid than some business anyway. She hadn’t intended on seducing the boy, but she just started feeling this strange attraction to him. He was only 13!
If she had wanted to seduce a younger guy, she would have hired one of the local landscape companies, with their hunky workers covered in sweat and tattoos, not some scrawny middle school kid. But lately, something about Jimmy had her radar up and her pussy wet. She had fucked several guys, and a few women, since her divorce almost 2 years prior. It had been an amicable divorce, just two people drifting apart, not becoming hateful adversaries like so many couples.
He was pretty cute, she thought as she watched the boy work from her pool deck. Cute, not hunky. And she was sure that his cock was nothing special, probably just an average boy cock. But damn! She wanted it in her pussy, mouth, and ass! She made sure to wear her sexiest bikini to sun herself as he worked. She hoped he noticed.
Jimmy noticed. How could he not? Mrs. P had a bangin’ body for a woman her age! He had known her casually for several years, and started doing her yard right after her divorce a couple years back. In that time, she had just been a nice neighbor lady, treating him like a nice neighbor boy. But now, there were sly smiles and veiled comments, incidental touching that went on longer than it should. She giggled like a schoolgirl at his comments and lame, little jokes.
When he had finished her yard for the day, he went over to her lounge chair on the pool deck to collect his fee. His usual fee was 40 bucks, but Mrs. P usually gave him 50. That day she gave him three $20 bills. He was surprised and tried to tell her it was too much.
“This is too much, Mrs. P! You don’t have to do this,” he protested.
“Nonsense, Jimmy! You deserve it! And please, it’s Kathryn. Kathy, actually. No more of this Mrs. P silliness! Now, have a seat and I’ll grab you something to drink. Lemonade good?”
“Sure! Sounds great!”
Kathy sauntered away and Jimmy was surprised to see that the bikini she wore was a thong. He admired the sway of her hips and the jiggling of her firm ass cheeks as she walked into the house. He could feel his cock coming to life. It was totally obvious now that she was looking for something more than yard work from him. Soon, she returned with a tray containing a pitcher of lemonade and two glasses. She poured him a glass and handed it to him, her touch lingering on his hand she smiled slyly.
“Thanks, Mrs. P.”
“Kathy!”
“Sorry. Thanks, Kathy. It tastes really good.”
“Nothing better on a hot day. Except maybe a swim, of course. Would you care to take a dip?”
“I don’t have a bathing suit, Mrs… Ummm… Kathy.”
“That’s okay. I won’t tell if you don’t,” she said with a leer. Jimmy actually blushed at the comment, and his dick responded by getting harder. Then he was blown away when she said, “You know what, Jimmy, to hell with the sexy comments and come-ons. I’m just going to come out and say it. I want you to fuck me. I usually don’t go for boys… sorry… guys your age. Actually, I never do. Never have. But I don’t know what it is about you. I just really want you to fuck me. I want to suck your boy cock. I want you to lick my cunt until I scream and squirt in your face. My pussy is freaking drenched right now!”
Still shocked, Jimmy stammered, “Real… really?”
Kathy pulled aside her bikini top, exposing her ample tits capped with large brown nipples and areola. Then she pulled aside her bikini bottom, exposing her very wet pussy, the juice running down to the crack of her ass. Jimmy saw that it was a beautiful, mature pussy, much like his mother’s, just not as hairy. Nowhere near as hairy, actually. She waxed the area around her vulva, just leaving a triangular patch of light brown pubes on her mound. The inner lips were red, full, and pouty, the clit surprisingly small. She spread herself open to show him just how wet she was.
A few short weeks ago, Jimmy probably would’ve ran away scared, or passed out from shock at a beautiful, mature woman exposing herself to him. But he was a different person now. He was no longer that virginal boy, but an experienced cocksman. He may still have been a boy physically, but in all other aspects, he was a man. He answered this sexy lady wordlessly, by setting down his glass of lemonade, kneeling in front of her, and proceeding to lick her mature twat.
“Oh, fuck! I knew I was right about you! Let’s take this to my bedroom, sweet boy!”
She led him to her spacious, well appointed bedroom, which was conveniently located right off the pool deck with a glass doorwall overlooking it. She pulled her bikini off completely then walked over to Jimmy, pulling down his shorts and underwear as he pulled off his t-shirt. She dropped to her knees as she undressed him, then took his sweet boy cock in her mouth. She had been right; it was just an average sized boy cock. But what was it that made her want him so bad? She hadn’t lusted after a 13 year old boy since she was 13 herself! She knew what she was doing wasn’t even legal! She didn’t care! She had to have him!
She sucked him for a few more minutes, then stood up, embraced him,, and kissed him deeply, her tongue darting in his mouth. He responded by shoving his tongue into her mouth. He was slightly taller than her 5’7″, so the embrace and kiss were a comfortable fit. Their hands roamed each other’s bodies, caressing, squeezing. Jimmy’s right hand made its way back to her pussy, pushing his middle finger in it. His left hand worked the taut, firm cheeks of her ass. She moaned into his mouth.
She broke the kiss and beckoned him to the bed, spreading her legs and pussy lips. She said in a husky whisper, “Finish what you started, baby boy! Mama needs this! Mama needs to cum!”
Hearing her call herself Mama got Jimmy revved up even more. For her part, Kathy was shocked at herself for saying it. She never had talked like that with any of her other lovers, not even the younger ones. This boy, though. Damn! He really stoked the fire in her cunt! Now he was trying to put that fire out with his tongue. His talented tongue! His VERY talented tongue! Holy fuck! He had obviously done this before! That tongue was everywhere! And he used lips and teeth effectively too! Licking, sucking, nibbling, biting! She was right before, she had a screaming, squinting orgasm all over his face!
Kathy had to push Jimmy’s head away from her too sensitive cunt. She was trembling and panting as she pulled him up to lie on top of her. She licked her pussy juice from his face, savoring the taste of herself. She did love the taste of pussy! Jimmy was kneading her tits, pulling and twisting at her nipples. He moved his head down and sucked her right tit, then the lift. She wanted him in her now!
She shoved Jimmy onto his back, then straddled him, guiding his oh so young cock into her oh so mature pussy! He was 13, dammit! 13! She was 50! Fifty fucking years old! She could be arrested for this! Right then, she didn’t care! They could drag her away in cuffs for all she gave a damn, but not until she came on his dick, not until he came in her pussy!
She rode him hard! Like her life depended on it! Bounce! Bounce! Bounce! The sound of their flesh slapping together filled the room, as did their moans, gasps, sighs, and yelps. Kathy whimpered as her next climax hit, but she kept going, wanting as many orgasms as she could before he shot off his creamy load into her fevered hole!
Jimmy looked up at his newest lover, admiring her body as she bounced away to yet another orgasm. He particularly liked the tan lines that emphasized her tits and bikini area. It was very retro and sexy, the skin so white against the dark tan of the rest of her body. She had a light dusting of freckles across her chest and face. She was a beautiful older woman, she must have been a complete goddess when she was younger.
Jimmy was surprised at his own stamina. He hadn’t even fucked Lizzy that morning. This would be his first cum of the day. He had become a lover of some skill and maturity since his sister Brit had taken his virginity just recently. Here he was, fucking this beautiful, experienced lady who had just had her second orgasm from riding his dick, plus the one he gave her with his tongue, and he hadn’t even cum yet himself!
It was starting though, he could feel it bubbling up in his balls. She was building again too. By the way she was trembling and thrashing around, it was going to be a powerful one. And it was! Kathy stopped her bouncing and riding when it hit. She threw her head back and let out an animal like howl. Her pussy clamped down on Jimmy’s cock as he felt wetness flooding his belly. She was squirting again. This triggered his own orgasm, finally. He sprayed the walls of her snatch with his jizz. He was grasping her hips as he drove his hips up, holding her in place as his balls emptied into her.
When they both had come down from their respective climaxes, Kathy tumbled over to her side, sliding off Jimmy’s dick, and slumping onto her back. Jimmy dived into her pussy to suck his cum out of her. This shocked the hell out of her and she shouted out in surprise. She had another quick cum. Jimmy crawled up on her to kiss her, passing his load into her mouth. She swallowed it greedily. Then she planted small, sweet kisses all over his face.
She held his face and stroked his hair, smiling at him as she said, “You are damn good, young man! I don’t remember the last time someone gave me that many orgasms! I have to tell you, I don’t go for underage boys, as a rule. I have fucked a few guys in their 20’s since my divorce, but not one barely a teen! I don’t know what it is about you, Jimmy. I really don’t. It’s only been recently that I started feeling attracted to you. And you’re a little kinky. That sucking your cum out of my pussy? I’ve never had a guy do that before! Where did you learn all this?”
Jimmy was reluctant to spill all his secrets to her. He had no reason to. It was one thing opening himself up to Max, since Max had revealed all his secrets to him, but he didn’t owe the same to her. He was happy to just fuck her, and that was that. He just noncommittally told her that an older, experienced lover had been teaching him. She caught the reluctance in his response, and didn’t push any further. She did feel the right to ask him if he had any other kinks, as she might be happy to indulge them.
“So, what do you like? Bondage? Do you want to tie me up and fuck me? Maybe spank me? I like that! A good bare ass spanking until it turns red! What do you like, my young lover?”
“Honestly? I like pee. I like to watch women pee. I like to be peed on too. Love it, actually. Do you think that’s gross?”
“Nope. Let’s go.”
She got up off the bed and held her hand out to Jimmy. He took it and got up, they walked hand in hand to the bathroom. They got in the shower stall and he laid on its floor. She stood over him and spread her pussy open. Jimmy could see some of his cum still oozing out of it as her piss stream started emanating from her urethra. The hot fluid splashed his chest and face. He opened his mouth to take some of it down his gullet. She moved her hips to go up and down his body, finishing on his once again erect cock.
Kathy smiled, thinking about the resilience of youth. Jimmy smiled back up at her and made one simple request.
“Can I fuck you in the ass now?”
Kathy laughed and said, “Of course you can, dear boy, but let’s rinse you off first.”
She helped him up, then turned on the shower. She poured some body wash in her hand and washed him head to toe, including his ass. He was relieved that his anus had recovered from the punishment it took from Uncle Chris’s horse cock when she stuck a soapy finger up it. She started thrusting it in and out as she stroked his cock with her other hand.
“Do you like that, kinky boy? I have a strap-on I could fuck you with! I bet you’d like that too! I bet you’ve had the real thing up there too!”
Jimmy laughed inwardly. She had no idea the things he had done. He just hissed out a “Yeeeeesssss!”
“I knew it! You’re a kinky boy! But I told you I’d let you fuck my ass! Let’s do this!”
She pulled her finger out of his ass and quit stroking his cock. She turned around and presented her ass to him, spreading her cheeks. He could see that her ass crack was as hairless as her vulva. He figured she waxed that too. He put some of the body wash in his hand, lubing his dick with it. Then he shoved one, then two soapy fingers into her shit chute to lube and loosen it.
He pressed his cock against her sphincter and pushed. There was a minimal amount of resistance. His cock slid in easily. This was obviously well used asshole, but it still felt good and tight to him anyway.
“Fuck my ass hard, Jimmy! Go for it! I can take it!”
He pounded her ass relentlessly. The water pouring down their bodies enhanced the sound of their bodies slapping together. She moaned and groaned and diddled her clit as Jimmy continued his assault of her tight back hole. It didn’t take long before they were both cumming again. Jimmy pulled his cock out of Kathy’s asshole. It briefly gaped open, then snapped shut. The woman turned around and passionately French kissed the boy again.
“I don’t know who taught you to be such a good lover, and I won’t ask. It’s not any of my business. Whoever it was though, please give them my regards. I hope as you get older, learn more, and grow more, that you’ll still fuck me. You probably think I’m an old woman now, and I’ll be ancient by then…”
“Stop. You are one sexy, beautiful lady. I’d be happy to keep fucking you for as long as we both still can. And I’m happy to learn anything that you can teach me too.”
Kathy smiled and kissed him tenderly. She turned off the shower, stepped out, and grabbed some towels. They dried each other off, then Jimmy got dressed. Kathy walked him to the door, still nude, and kissed him sensuously before he left.
“I hope we can do this again next week, sweet boy!”
“I don’t see why not, beautiful lady!”
“Please be discreet. I could get in a lot of trouble…”
He put his finger to her lips to shush her.
“I know. I will. Don’t worry.”
He kissed her one last time then left.
He headed home with a big smile on his face. Seven. Seven different females had fucked him now. He still couldn’t believe his life right now. He was just debating whether to tell Lizzy about the day’s events or not…
