Jimmy continues his relationship with Lizzy and learns something new about his buddy Max…
Jimmy came home from doing his yard jobs hot and sweaty, ready for a shower. Of course, he was ready for a fuck too. He saw that both Sean and Sand’s cars were gone next door. He was hoping for another go-round with Lizzy. He wouldn’t have minded a go with her mother again either. That woman was a freak!
He headed into the house and up to his room, intending on taking a shower. His mom Lisa was the only other person home, and she was in her room packing for her trip with Frank. It was just a few days away for her as Frank would be working at his company’s other location for a while. They had missed each other while he had been away before, so she decided to accompany for a few days.
“Hey, Mom! I’m home! Hopping in the shower.”
“Oh, okay, sweetie! Just packing. Got any plans while we’re gone? I’m sure a certain little redhead will be involved.”
Jimmy laughed and said, “Yeah, Lizzy is gonna be a part of a lot of my plans from now on. But other than that, Max invited me over for a sleepover tomorrow night.”
“Oh, that’ll be nice! You do still need to be with your friends. I’m glad to hear that. Say! I could use a shower and I need to pee. Wanna have a little fun with your old mom before I leave for a while?”
“My old mom! Pffft! All women should be as sexy and beautiful as you! Fuck yeah! I wanna have some fun with you!”
“Oh, such language,” Lisa gasped with mock indignation, “I should wash your mouth out with soap!”
Then she continued with an evil grin and a wickedly arched eyebrow, “But I think I’ll use pussy juice and pee instead!”
She started stripping and they were both nude as they reached the shower in her master bath. They stood, kissing, groping, hugging, as they waited for the water to heat. They were pretty heated themselves by the time they got in the shower. Lisa put her hands on Jimmy’s shoulders and pushed him gently to his knees. Jimmy opened his mouth as Lisa spread the lips of her hairy pussy open.
Her stream started and Jimmy caught it on his tongue, tasting that salty bitterness that he had come to love. In the back of his head it occurred to him that by indulging him in his fetish, Lisa was expressing her maternal love in just another way. A very kinky, incestuous way. He appreciated that love, every single drop of it.
After Lisa’s stream had stopped, Jimmy clamped his lips down on her clit. He ate her hairy cunt until she had a squirting orgasm right in his face, flooding his mouth again. When her orgasm had subsided, she turned around and presented him with her juicy, round ass. Jimmy loved the sight of all the hair that spread out of the crack and onto her cheeks. She made the view even better when she reached back and spread those cheeks open.
“Fuck my asshole, baby!”
Jimmy was happy to comply. He put some soap on his cock and some on her asshole, then slid his 6 inches in easily. He pounded his mother’s hairy shit hole until he flooded it with his creamy cum. Lisa had been rubbing her clit and came again herself.
After they got out of the shower and dried off, Jimmy grabbed his phone and texted Lizzy.
J: What r u doin’, hot stuff? Was hoping 2 c u when I got home.
L: Hey, luvr! Had to go to my other grandparents’ house. Grandma sick. Won’t b home 2nite. ☹
J: I hope ur grandma is OK. I’m just gonna hang with Mom 2nite. She’s leaving 2morrow with Dad 4 a few days.
L: Maybe we can hang 2morrow nite if I get back.
J: I told Max I’d spend the nite at his place 2morrow.
L: Oh OK. I probably won’t be back anyways. Miss u!
J: Miss u 2!
His phone pinged again. When he looked there was an attachment. He opened it to find a picture of Lizzy’s pink, bald pussy. The phone pinged again.
L: My pussy misses you 2, luvr!
He stroked his teenage cock back to hardness and sent her a picture in return. To his surprise, he got a message from Sandi.
S: I wanna get a hold of that again myself! 😈😋
J: 😛🍆🍑
Frank came home and packed his stuff, then loaded it in his car. Jimmy was hoping that they could have a three-way or a foursome if Brit came home. Unfortunately, Frank had to get on the road. So Jimmy and Lisa spent the evening together, having dinner, watching TV, fucking. He showed her the picture Lizzy had sent and Sandi’s messages.
“I’ll be so glad when I can lick that little slit myself! Damn! I envy you, baby! I’ll have to settle for her mama, I guess. And your sister, of course.”
“Don’t forget April!”
“I could NEVER forget that hot ass piece of pussy!”
They both laughed and went back to fucking. They finished the night with Jimmy straddling his mother and fucking her massive tits. He came on her tongue as she dildo fucked herself to orgasm. She shared his load with him, their tongues twisting together in one last good night kiss.
When Jimmy woke up in his mother’s bed, she was sucking his cock. He had her swing around for a 69. After they had both cum. She jumped up, telling him she needed to get going. She jumped in the shower, got dressed and made up, kissed him goodbye, then headed out. He found his phone and checked his messages. He saw that Brit had texted to say that she was staying with April at her family’s lake house for a few days. He texted her back to tell her to have a good time.
B: u know I will 😉
Then he saw that Lizzy had sent another attachment. It was a video of her peeing, then blowing him a kiss. Someone else had obviously been holding the phone. He assumed it was Sadie until he saw an attachment from Sandi. It was a video of her peeing, then blowing him kisses. They had recorded each other. He took video of himself beating off and cumming, then sent it to both of them. More pussy pictures followed. Sadie was in a few. He told them that he had to get to work already!
Jimmy went and did his lawn jobs. One of his clients, Mrs. P, seemed to be flirting with him. She was a nice looking woman, probably late 40’s to early 50’s, about 5′ 7″. She had long blonde hair, piercing blue eyes, long legs, and a nice rack. He wouldn’t mind a tumble with her if the chance presented itself.
He got home, stashed his gear, then took a shower. It felt weird to him being alone in the house. He noticed that it wasn’t even 4 o’clock yet and he wasn’t due to be at Max’s until 6 o’clock. He grabbed a snack and flipped on the TV. He nodded off for a while, then grabbed his change of clothes, his wallet and keys, locked up the house, and headed out on his bike to Max’s house.
Max was next door at his “Uncle” Chris’s house. Chris wasn’t actually an uncle, just an old family friend Max had known his whole life. In fact, Chris was the best friend of Max’s dad, Danny, since college. He was the best man at Max’s parents. He moved next door at the urging of Max’s mom Maria when the house went up for sale. So he had been like a second father to Max his whole life. Chris had never married himself, so there was no “aunt”, though he did date a lot.
Max saw Jimmy pull up to his house, and met him at the door. Uncle Chris popped his head out the door and said hi to Jimmy. Jimmy greeted him back. Max opened the door and they headed in to the living room. Jimmy noticed that Max was carrying a plastic grocery bag, which he stashed in another room. Max came back in and flipped on the TV and gaming console.
“Do you want to order pizza now, Jimmy, or play for a while?”
“Let’s play for a while, if that’s cool with you?”
“Yeah that’s cool. Let’s do this!”
After a couple hours of blood and mayhem, they ordered their pizza, going back to the game while they waited. Once it got there, they shut down the game and ate. Afterwards they decided to watch movies instead of playing more. They put on an old slasher flick, the kind that showed a lot of naked girls. Max remarked that none of them were as hot as Brit. Jimmy laughed and agreed. What else could he do? Max was right. His own sister was probably the hottest girl he had ever seen, and he got to fuck her whenever he wanted. He wanted badly to tell Max that fact.
After the slasher was over, Max said, “Wanna watch some porn?”
Jimmy agreed, figuring that if he got too horny, he could excuse himself to the bathroom and take care of himself, provided Max was squeamish about jacking off in front of each other. He hoped that wasn’t the case. He had thought before that Max was attractive, almost pretty like a girl, with his shoulder length hair, high cheekbones, dark eyes, and full, red lips. Max was Mexican on his mother’s side and he took after her more than his dad.
They were sitting next to each other on the couch. They could hear each other’s breathing getting deeper and slower. They each kept discreetly glancing at each other’s crotches to see if the other was hard. The piles of breasts and pussies and cocks onscreen were all very enticing but Jimmy was now experienced with the real thing. He would’ve rather seen Max naked and make something happen with him. When Max stood up and told Jimmy that he would be back in a few minutes, he figured that his friend was going to take care of himself in the bathroom. Jimmy heard the door to it close and latch.
Jimmy figured that if Max was going off to masturbate by himself in the bathroom, he would do the same thing there in the living room. He didn’t care if he was still going at it when Max came back or not, he had gotten over being shy. He pulled down his shorts and started stroking his 6 inch boy cock. He had been going at it for several minutes when he heard the bathroom door open. He wondered what Max’s reaction would be when he came in to find his friend stroking his cock. Jimmy didn’t look up when he heard Max enter the room. In fact, he was surprised that he didn’t hear any reaction from Max considering his current state.
“So, did you beat off and cum,” asked Jimmy, still not looking up. “I figured, why be shy? Hope you don’t mind me just doing it here.”
“Ummm… no, I didn’t beat off, and no, I don’t mind you doing it here. Actually, I’d like to help you.”
Those words were music to Jimmy’s ears! He had satisfied his curiosity about bi sex thanks to his dad Frank and neighbor Sean, but he still had wanted to hook up with one of his friends. He had been wanting that for years, and now it was going to happen. Still, he wasn’t prepared for what he saw when he finally looked up at his friend.
Max walked in front of Jimmy and Jimmy saw that Max was completely made up as a girl! He wore full makeup, his eyes shaded light green, eyeliner and mascara applied, cheeks rouged, lips painted and glossy. His long hair pulled into two loose pigtails hanging along his neck, a delicate necklace encircling that long, elegant neck. He wore a gingham patterned sundress and white sandals, an ankle bracelet on each leg. His fingernails and toenails were painted pastel pink. There was a toe ring on the middle toe of each foot.
Jimmy had always thought Max was pretty like a girl, but he now saw that Max was pretty AS a girl! He was speechless and Max looked scared. Neither spoke but Jimmy stood, his shorts dropping to his ankles. He pressed against Max, his erection prodding against the boy/girl’s hip. They embraced, Jimmy’s arms going around Max’s waist, Max’s going around Jimmy’s neck. Their lips came together, then so did their tongues. They made out like that for what seemed like an eternity. Finally they broke the kiss, and Jimmy spoke first.
“I’d be happy to have you help me cum. I want to do the same for you for a long time. You look beautiful!”
“I’m so happy to hear that! I…I… worried that you’d freak out and leave… or worse…”
“Worse?”
“Hit me. Tell people my secret. You know, worse.”
“No. Not me. I doubt any of our friends would either.”
“I’m not worried about them right now, Jimmy. Right now I just want you. I want you to fuck me like you would a girl. Are you a virgin?”
“No. Actually, Max, I’ve been with both females and males. But you’ll be my first… the best of both worlds, let’s say.”
Max smiled at Jimmy’s kind words and was relieved that Jimmy was so open minded. (S)he was no virgin either, as she would reveal to Jimmy later. They started kissing again and Max grasped Jimmy’s cock. She stroked it gently as they mashed their mouths together, tongues doing the tango in each other’s mouth. Jimmy groped her ass. Max dropped to her knees and started to give Jimmy expert level head.
Jimmy could automatically tell that Max was no stranger to sucking cock. He… no, she… Jimmy would think of Max as she, at least when Max wanted him to… she sucked cock almost as good as Brit, Lisa, or Sandi. Jimmy held her head in his hands, running his fingers through her hair. If he hadn’t already cum twice earlier in the day, he would’ve already been blowing his load in his friend’s mouth. That delicious, sensuous mouth.
Max alternated between sucking Jimmy’s cock down to the root, licking up and down the shaft and around the crown, flicking her tongue at that point under the crown where the ridges met, sucking his nearly hairless balls, and then repeating it all. Jimmy could feel his knees shaking, his climax bubbling up. This was so erotic! One of his best friends was giving him some excellent head! And the way he… she looked!
“Max, I’m gonna cum if you don’t stop! Do you want me to cum in your mouth, baby?”
Jimmy was caught up in the moment, and surprised himself by calling Max baby. Max never took her mouth off Jimmy’s cock, just answering with a muffled “Mmmm-hmmm!”
Jimmy couldn’t take it anymore and emptied his balls in Max’s mouth. Max held the creamy deposit in her mouth and stood to kiss Jimmy. They passed the spunk back and forth between their mouths until it was gone. Jimmy stepped out of his shorts and pulled off his shirt. Then he took Max by the hand and said, “Let’s go to the bedroom! I want you naked!”
The pair rushed hand in hand to Max’s bedroom. Once there, Jimmy started stripping Max down until she was as naked as him. He started by pulling off her sandals, then her dress. He found that Max was wearing a cute, matching bra and panties set, white with little cherries decorating them. He reached behind Max while kissing her to unhook the bra. Brit had taught him how to do that. He sucked Max’s tiny brown nipples, first one then the other, twisting and teasing the one he wasn’t sucking at the time.
Jimmy got down on his knees in front of Max to take her panties down. He noticed that she was completely hairless from her eyebrows down. He knew Max the boy was on the school swim team and he kept himself waxed clean for for that, but he wondered if this alter ego had more to do with it. He also noticed that there was no bulge showing in Max’s panties. When he pulled them down, he found that Max the boy had tucked his cock between his legs to become Max the girl. Looking at Max’s smooth pubic mound, Jimmy briefly thought of Lizzy.
Jimmy stood and guided Max to the bed, sitting her down and gently pushing her back. Her legs hung over the edge of the bed, and Jimmy spread them open for her. Max’s cock sprung up then, the only masculine thing about him/her right then. Jimmy grasped it and stroked it. It was about the same length as his 6 inches, but thinner. He wanted it in his mouth. He reflected on what he had learned from sucking his father’s and Sean’s cocks, what the adult women in his life had done to him when they sucked his cock, what Max had done to him a few minutes prior.
Jimmy licked the shaft of Max’s girl cock, up and down, around and around. He flicked his tongue on its tip, poking his tongue tip in the piss slit. He took the whole thing in his mouth, swallowing it to its root without gagging. His dad would’ve been proud. He would tell him about it the next time they talked. How many boys were lucky enough to talk to their dads about their cocksucking skills? Probably not many, definitely not enough.
Jimmy moved down to Max’s balls, nibbling and sucking each one into his mouth. He pushed Max’s legs back and ate her puckered asshole like it was a pussy while continuing to stroke her cock. After several minutes, he went back to work on the cock, replacing his tongue in Max’s asshole with two of his fingers. He thrust them in and out of it as he resumed his oral assault on Max’s girl cock.
Max was starting to tremble. She grabbed Jimmy by the hair as he bobbed up and down on her cock while swirling his tongue around it. She started bucking her hips, face fucking her friend as her climax built. Then she suddenly arched her back as she held Jimmy’s head down on his cock as cum erupted from it. She emptied a massive load from her balls into his mouth. Jimmy almost gagged then. He wondered if she would ever stop cumming. Once she relaxed and straightened her back to lie flat on the bed, Jimmy pulled his mouth off Max’s cock with a pop. She had cum so much that some of it dribbled down his chin.
Jimmy climbed on top of her to share the load like she had done with him. Their lips locked together and Max greedily swallowed every drop Jimmy passed to her, not passing it back like they had done before. She could feel the erection Jimmy had never lost pressing into her.
“Fuck me, Jimmy! I want to be your slut tonight! I want you in me! I’ve wanted this so long!”
“Me too! I’ve wanted to fuck you for a long time, Max! I’ve been attracted to you for a long time! You look so beautiful tonight!”
Max had tears her eyes, her mascara started running. Most of her makeup was smudged from all the intense kissing they had been doing. Jimmy still thought she looked beautiful. Years of pent up sexual longing between the two was now being fulfilled. Jimmy pushed her legs back, exposing her boy pussy. He spit on it, then rubbed some on the tip of his cock. He pressed it against the opening of Max’s boy pussy and pushed slowly.
There was some resistance at first but not much. Max was no virgin there either, Jimmy thought. She was still tight though, and felt so good as her back hole enveloped his invading fuck stick. Max wrapped her legs around him as he fucked her. She pulled him down and wrapped her arms around him, kissing him again. Jimmy couldn’t get enough of her sensuous lips and sinuous tongue. He returned the kiss as he thrust his cock in her.
Jimmy was very excited, very aroused, but he had already cum several times that day, once just a little while ago, so he was nowhere near cumming now. They changed positions, Max getting on her knees so Jimmy could pound her from behind. He was nice enough to provide a reach-around too. He relentlessly pounded her ass in this position. Max’s knees were starting to give out so they changed positions again.
Jimmy laid on his back and Max straddled him, guiding his cock back into her boy pussy. She rode his boy cock like a cowgirl as she stroked her own girl cock. Jimmy finally reached his peak and came in her ass. She shot off her own load, spraying Jimmy’s chest and face. They were in this position when they heard a voice from the doorway.
“Well, isn’t this a delicious sight?”
They turned to look and saw Uncle Chris standing there completely nude, his huge cock erect…
