Road Trip

“Over here! Throw it here!”

Caleb ran as fast as he could. He didn’t spare a second of attention for the action around him. He dropped to the ground and slid into third base right before he was tagged out by Charlotte.

Coach Katie hollered, “SAFE!” as she waved her arms in front of her body.

Caleb stood and dusted himself off as Charlotte threw the ball back to Holly. He took a step off the base and got ready to run again. The score was tied 2-2 and class was nearly over. Caleb's team needed one run to win.

But Holly was a great pitcher. Her large breasts did not hinder her ability to make a softball dance in the air. Caleb knew Holly had gone easy on him. That was the only way he had gotten a double off her. Michelle, the current captain of his team had only scored a single which got him to third base.

Caleb smiled to see who was coming out of the dugout. Chris would have made a good player on the school team, but her main interest lay elsewhere. The horticulture club spent a lot of their free time working in the school gardens, and Chris was president of the club.

She was also very muscular for an eighteen year old woman. If Holly let her get a piece of the ball it could very well be a homerun hit.

Holly held the ball in front of her stomach and shook her head at the catcher's signal. With a quick nod she accepted the second signal from the catcher, turned her body sideways and checked both runners. She grinned at Caleb before turning her head back toward the catcher. She pulled her arm back and snapped it forward, releasing it as it crossed her belly button.

Caleb couldn't see the trajectory of the ball very well from his angle, but he had seen enough of Holly's pitches to know when she threw a curveball. Chris took a swing but missed by a few millimeters. The sound of the ball smacking into the catcher's mitt was loud even from third base.

Holly caught the return throw and retook her pitching stance. She went through the motions of accepting the catcher's signal and checking the bases before throwing a pitch Caleb wasn't familiar with. She had her fingers on top of the ball when she released it. She even fell to her knees as the ball left her hands. The ball seemed to wobble in the air much slower than Holly's normal pitches. It dipped just as Chris began her swing.

*CRACK!*

Caleb began running as the ball zipped through the air past the pitchers mound. The catcher threw off her facemask and stepped in front of the plate but it was clear to Caleb that she wasn't expecting the ball to come to her any time soon. He crossed home plate and turned to see what was happening in the outfield.

Chris stood on first base, not bothering to run to second. It was a good thing too. The shortstop caught the ball and relayed it to third base, but it was too late. Michelle stood on the plate with no interest in trying to score another run in. They had scored a point and breaking the tie was all that mattered.

Coach Katie blew her whistle calling an end to the game even as Holly stomped over to Chris.

"That's cheating! You cheated! I can't believe you would do that to me!"

Caleb made his way over towards his two lovers and saw Holly with tears in her eyes. The rest of the class gave each other questioning looks. As far as they could tell Chris hadn't done anything wrong.

Chris held her hands up and said, "I'm sorry Holly. I didn't mean to. It just happened, I swear. I love you. You know that."

Coach Katie rushed over to stand in between the two and held her hands up. "Everyone hit the showers. Now!"

The class dragged their feet as they slowly made their way to the locker rooms. Katie stayed between Holly and Chris as they walked. She looked between the two of them and said, "Holly, I'm sure Chris didn't meant to cut you off from her harem link. Chris knows better than anyone how much it hurts. You know she would never do it on purpose."

"I really am sorry Holly. I didn't even know I could do that. I was just really focused on hitting the ball. I'll do anything to make it up to you." Chris pleaded.

Holly felt the harem link with Chris flood with Chris’s love. She already knew Chris loved her and that it had to be accidental. But it had hurt. A lot. She looked over at Chris and said, "I want a night alone with Kathy. The whole night, just me and her. And I want to wake up with her beside me too."

Caleb shook his head as he peeled off to head for the men's locker room as Chris and Holly made up.

"ROAD TRIP!" Angie shouted as she piled into one of the armored SUVs in front of the high school.

Caleb smirked as Holly, Chris, and Kathy took turns kissing each other. Holly would be staying behind because she had a softball game on Saturday. Caleb had already said goodbye to Misty, Heather, and Marilyn.

He leaned against the side of the SUV and grunted. Sierra was on her knees slurping his dick. She wore pigtails in her hair and he held them as she slobbered on his cock. “Gluck Gluck Gluck” came from her mouth as his fat cockhead hit the back of her throat.

Melanie grinned at him as she finished saying goodbye to June and promised to look after Harold's sister. She came over to him and gave him a peck on the cheek before she pressed on Sierra's head, forcing her to take more of his cock into her mouth, causing her throat to bulge slightly. "That's it sweetie. Caleb won't cum if you don't get it in there deep."

The angle was bad for Sierra to take any more but she struggled on like the naughty little girl she tried to be. She gagged for a bit and Caleb felt his cock release a bit of pre-cum into her mouth.

She pulled back and looked up at Melanie and whined, "Auntie Mel. I'm trying to say goodbye to Daddy. He promised to give us a cum bath if I do a good job."

"Oh, Well then. You better put in your best effort baby girl. We want plenty of his little spermies for our snacky." Melanie said. Then she bent over and spit on his cock while Sierra jerked him. Sierra smiled up at her as she her hands slid up and down his shaft mixing Melanie's spit with her own.

Melanie let her go back to sucking Caleb's cock. She brought Caleb's hands up to her breasts and held them there until he gave them a good squeeze. She leaned in again and kissed his lips before looking at him wistfully and stating, "I wish I could go with you. Unfortunately I have to stay and attend the prom committee meeting. When you get back I have something to discuss with you. Nothing to worry about, but the school board is giving me shit."

"You need me to do anything?" Caleb asked. Sierra was doing a good job of distracting him. It felt like she was sucking on him like his dick was a straw in an extra thick milkshake. His pre-cum was flowing freely now and she gulped it down as she tried to get him to release a load for her.

Melanie shook her head and said, "It can wait. I'll put a note in the harem meeting book. Have fun on your trip Caleb. Make lots of babies and heal lots of women." Then she gave him one final kiss and walked over to Kathy to give her queen her own goodbye.

Caleb focused his attention on Sierra. She was really giving the blowjob her all. He merely held her hair as she slammed her head up and down his shaft. She wasn't trying to gag on him, but she still did it occasionally by accident. At the speed she was bobbing her head it was inevitable.

Her blowjobs were different from everyone else's. She was intentionally clumsier and acted as if she was inexperienced, even though he knew she could do much better. It was all part of her naughty daughter roleplay. No matter what they did together she never dropped the act. Whenever she had sex she always pretended like it was their first time. Sometimes she was a horny little minx that wanted her a cock or strap-on to take her virginity, other times she pretended that her lover was forcing themself on her.

He had seen her do it multiple times with the women at the orgies. His mom told him it was a little freaky when Sierra called her grandma and begged her for a spanking for being naughty and fucking her daddy, only to turn that around and beg her 'grandma' to fuck her too.

Kathy stepped beside him and kissed his cheek. "You about ready to blow my love?"

Caleb grunted and nodded. It was all the noise he could make. Sierra had gone back to sucking him extra hard. He was afraid when she finally released his dick it was going to have a hickey on the head.

"Girls! Everyone that is staying here, line up! Caleb is going to give you all a cum covering before we go!" Kathy shouted.

Melanie untucked her blouse and pulled it off over her head before kneeling beside Sierra. She left her bra on and cupped her tits from below, with her head tilted back slightly she was presenting him with some nice targets. Heather, Misty, Holly, Lu, Katie, and finally Marilyn joined her in a group around Sierra.

Kathy reached between Caleb's legs and lightly gripped his balls with one hand and tapped Sierra on the head with the other. "Get ready girls."

Sierra pulled her head back so that Caleb's cock could slip from her lips. Kathy grabbed his shaft and began jerking him slowly while she fondled his balls. Caleb actually felt them contract and knew Kathy had cast a spell on him.

"OH FUCK!" he shouted as his dick sprayed cum like a firehose. He fell back against the SUV as cum rocketed out of his pisshole. Kathy and the rest of the girls laughed as Sierra took the initial blast right between her eyes. But Caleb wasn't cumming in large spurts like he normally did. Instead it all came out in one long stream, almost like he was pissing cum.

Kathy never let up on stroking his cock. She simply aimed it this way and that as the girls that they were leaving behind were covered in his jizz. It landed in their hair, on their faces, in their mouths, and all over their upper bodies. Melanie tried to catch some in her cleavage and the cups of her bra to save as a snack for later. She was mostly successful. Misty saw what Melanie was doing and cursed herself for taking her bra off. Her big bra cups would have held more.

Finally Caleb felt as if his nuts had nothing left to give. His stream of cum began to slacken even as Kathy dropped to her knees and took his cock into her mouth to clean him up and take the last little bit of cum for herself.

For the first time since Caleb found his reality altering watch, his nuts were sore. The aftermath of his eruption was a whitewashed mess of women. It looked like he had cum as much or more than one of his morning loads.

Kathy gave his tip a final kiss before she put his cock and balls back into his boxer briefs and pulled his pants back up his legs. She smiled up at him as she redressed him. She opened her mouth to show him the cum resting on her tongue. When she closed it he noticed she didn't swallow. It wasn't uncommon for his women to savor his cum for a while before they finally sent it on its way to their bellies.

As the SUV's left the school grounds the girls they left behind were still standing by the side of the road licking his cum off of each other.

Caleb woke up groggy and knew Kathy had cast a sleeping spell on him. He wasn’t upset though. He knew he needed the rest. Between the orgy the previous night and all the sex he had that morning and during school he was thoroughly exhausted when they left the school. One good thing about Kathy's sleeping spell, his nuts didn't hurt anymore.

Before he opened his eyes he heard what sounded like someone stirring macaroni. Then the scent of fruity flavored pussy invaded his nostrils. Taking a peek he saw a bare ass up in the air between him and the seat on the opposite side of the vehicle.

Looking towards the front of the SUV he saw April in the drivers seat where he expected her to be. In the passenger’s seat his mother looked back behind him. She had one hand on an exposed breast pinching her nipple, and the other hand between her legs. She had an expression of wide eyed shock but he didn’t know why. Obviously from the sounds someone was getting played with in the back seat so why the surprise?

“Chris! No no no. That's not… I don’t… oh fuck. Hhhnnnn uh… that’s so dirty… uhhhnnn fuck!”

Caleb looked back behind him and his jaw dropped. Kathy was twisted up like a pretzel. Angie and Gabbie sat on either side of her, holding her legs up in the air and against their bodies while they each nipped and sucked on one of her tits each. Kathy’s arms were pinned by their bodies, keeping her completely immobile and spread wide. This put her ass pointing towards the front seats, with her pussy angled slightly upward.

Angie was rubbing Kathy’s clit while Gabbie finger fucked her. That was the source of the noise that had woken him. Kathy’s creamy pussy was sloppy wet and Gabbie rubbed her G-spot in time with Angie fiddling her clit.

But that wasn’t the reason why June had a shocked look on her face. Or why Kathy was complaining even as her pussy cream spurted out of her gash. He couldn’t even see her face because her huge boobs were in the way.

The reason Kathy struggled was because of what Chris was doing. It was Chris’s ass that was wedged between the seats. And her face was buried in Kathy’s ass crack.

Caleb rose up from his seat for a better look and saw Chris holding Kathy’s cheeks apart and tonguing around her butthole. He felt his cock instantly harden and strain against his pant leg.

Kathy squirmed but try as she might she couldn’t break the hold Angie and Gabbie had on her. The best she could do was rotate her ankles in her struggle to break free while begging Chris. Caleb wasn't certain if Kathy wanted her to stop, or keep going.

Caleb could just barely see her hungry cunt over Chris’s head. It looked to him like her pussy was trying to eat Gabbie’s fingers. He’d love for that to be his dick, but there was no way he could get to her, not with Chris in the way.

Kathy’s body was already bent as far as it could go so she was unable to do her signature hip humps as she came. Instead her cream splashed across Chris’s face and hair while Kathy let out an unintelligible scream.

Caleb really wanted to join in but saw no way that he could. Not without forcing one of Kathy’s lovers to move. Instead he looked down at Chris’s bare ass and got an idea.

He stripped his pants off in a hurry and moved behind the muscular woman. He felt it would be fitting to fuck her up the butt while she tongued Kathy’s ass.

Unfortunately he didn’t have any lube, and both Tina and Sonia had repeatedly told him not to use his big dick back there without it. He took their warning to heart. Tina was a self proclaimed butt slut, and Sonia is a Sisterhood priestess. The chief requirement to become a priestess was extensive training in all sexual activities. If they were warning him, it was for good reason.

So instead of aiming for her ass he guided his dick down a bit and pressed his cockhead against her drooling pussy. As her swollen pussy lips began to part and allow his fat cock to open her up she raised her head and moaned, “Hell yes! Do me Caleb. Fuck me hard.”

Chris resumed tonguing Kathy while Kathy pleaded, “Caleb! Caleb! Do you see! Chris is... She's... I don’t want to get fucked back there. Please. Not there.”

Caleb chuckled. He could tell she was trying desperately to break free. He also knew that if she really wanted to she could get out of that easily. Even with her body twisted the way it was she could cast her magic at any time. “Sorry babe. Chris is YOUR girlfriend. You only asked ME not to do you in the butt. You never said anything about one of the harem LICKING you there. Hell, from where I am it looks like you’re loving it. Honestly I think it’s cute that Chris gets to have one of your holes all to herself.”

As Kathy came again, spraying her cream, Chris’s pussy clamped onto his dick as if to say she approved of his statement. He flexed his pelvic muscles and it caused his cock to twitch as it swelled slightly inside her. Then he tapped his thumb on her butthole and said, "You know Chris, if you get Kathy's ass, I should get yours. How's this sound? You get to be the only one to finger or eat her ass, but in exchange I get to fuck yours. No one fucks her back there though. She said she doesn't want that. What do you think?"

Her moan as she pushed her ass back at him sounded like a deal was struck. Kathy’s ass was hers to play with, but Caleb would get to fuck Chris in the ass in return.

He grabbed Chris’s hips and fed more of his cock into her tight little honey hole. The way her ass was wedged between the seats meant she couldn’t spread her legs. This made her pussy much tighter than he expected. Not that he would complain.

Whatever she was doing to Kathy was driving her wild, although Angie and Gabbie could have been the source of her squealing. He liked to think it was a combination of all three.

Chris had asked him to fuck her hard so as soon as his cock had worked its way to the back of her fuck tunnel he used the leverage of her hips to drive into her quick and deep. Unfortunately she couldn’t maintain her attention on Kathy’s ass with the rhythm he had set.

Chris lowered her face to the carpet of the SUV and grunted each time his cockhead slammed against her womb. This position put her head directly under Kathy’s ass and also made his dick drag along the back of her slit while his balls slapped her clit each time her pounded into her.

Gradually her grunts turned to moaning. He watched as Kathy’s cunt honey slid down her ass crack to drip into Chris’s hair. For some reason he found that funny and had to stifle a laugh as he continued his attack on her tight snatch.

June plopped herself into his vacant seat and reached for Chris's ass. Caleb saw that her fingers were shiny. When he looked her way he saw a small bottle of lube in her lap. Meeting her eyes she giggled, "I wanted to be prepared for anything."

Chris's head shot up as June began pressing her fingers into her ass. "Whoa! I'm not ready for your big dick Caleb! You'll kill me with that thing!"

"That's not me." Caleb said at the same time June said, "Just relax honey. I'm just going to play back here a bit. You need to train your ass if you want Caleb to fuck you back here."

Looking back at her son she said, "Make her cream your cock sweetie. It will help me break her ass in."

Caleb gave Chris full length strokes while he watched his mother slowly work her lubricated finger up Chris's ass. Chris began to cum but Caleb paid her no attention aside from relishing the joy of her spasming cunt. He was far more interested in what his mother was doing.

He didn't notice that Angie and Gabbie had let Kathy go and the three of them were watching June work one, then two fingers into Chris's bum. Chris whimpered at their feet as her back passage was slowly opened. For his part, Caleb kept his strokes slow and steady. Every time Chris came June would have to stop as her butthole clamped too tightly for June to move.

"Oh my goddess Chris. I can't believe you're letting her do that to you," Kathy exclaimed.

Angie nudged Kathy and said, "Well yeah, but I bet you never thought Chris would eat your ass either."

Kathy blushed at the reminder. Her butthole still tingled from the tongue lashing Chris gave her. She still didn't want to try anal, not with Caleb's huge cock, but Chris's tongue was incredibly intense. Something that small she didn't mind at all.

Chris began to cum repeatedly as June worked a third finger into her. She babbled incoherently and would have dropped down to the floor of the SUV if her hips weren't wedged between the seats. She couldn't get away from June's digits or Caleb's stretcher if she wanted to.

Caleb stared into Kathy's eyes as he fucked her best friend, her girlfriend, and her primary lover after him. He tried to convey his love for her with his look. Kathy's smile turned into a smirk. It was time to pay Chris back for not listening when Kathy told her not to tongue her butthole. "My love, what do you think about making Chris the designated ass eater in the harem? I know Tina would love to do it, but she isn't in your harem."

Caleb grinned and sped up his strokes a bit, driving himself all the way to Chris's womb with each plunge. His mother seemed to have decided that three fingers was all she could put up Chris's ass. He never thought she would do more than one when she started. He could feel her invading digits on the other side of the thin wall separating his shaft from her fingers. Chris whimpered as June began sliding her fingers in as Caleb withdrew.

"That sounds like a great idea. I'm not really big on anal anyway. I much prefer fucking your pussies, tits, and mouths. Someone needs to be the one to play with your asses. What do you think Chris? You wanna eat Angie and Gabbie's asses too? Or how about my mom?"

Chris whimpered, "Yes! Yes! I'll do anything you want. Fuck! Holy hell that feels sooo good. I feel so full."

Kathy put her arms around Angie and Gabbie and said, "You have to protect my ass though Chris. Anytime someone wants to fuck my ass you have to take my place. Is that what you want?"

Chris threw her head back as a new orgasm rippled along her fuck tunnels and shouted, "YES! Oh goddess yes! I'll be a horny little butt slut just like Tina."

Kathy looked back at Caleb and said, "Fill her up my love. Pump her full. I want to eat your cum out of her."

Caleb didn't have to be told twice. He was already on the verge of cumming. He slammed himself as deep as he could go and let loose inside her. One last orgasm shattered Chris even as his cum hammered against her cervix.

A few minutes later Kathy crawled up Chris's body and shared the last of Caleb's cum with the woman she cherished almost as much as she did Caleb. Chris groggily said, "You aren't really going to make me become an ass eating butt slut are you?"

Kathy giggled even as Chris fell asleep. Only time would tell.

Thank you for reading. Please leave a comment if there is something you would like to see. If you loved the story please consider buying me a cup of coffee at https://ko-fi.com/samus1001