This story contains gay sex between consenting adults. If this story offends you or it is illegal for you, please leave this site.
Most of the characters and events in this story are fictional. The story may portray some real people, events, or places. This is a continuation of another story posted in the Adult Friends section called Mr. Shepherd's Summer Vacation. The boys in this story had quite a summer and are now starting their college adventure. References are made to characters in the previous story.
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Spring Break
The next few weeks the boys developed a good routine. They focused on school during the weekdays, each other at night and Saturday afternoons were for Chaturbate. Sundays were lazy mornings and studying. The neighbors still let Thomas and Sean know they were too loud.
They had called Austin and turned down the porn offer. Sean said he understood and he had another check for Thomas. Your dick is still our top seller! The new model will be out in a month and that will only help sales. Maybe talk up your dildo on a couple videos to keep guys interested.
Nolen and Carrie were spending a LOT of time together and Nolen was much more confident than before. Travis and Lisa were living together and the boys would get together with Travis at least once a week to relieve his stress. Turns out Sarah and Amber were Lisa's go to for her relief.
Parent Weekend came and Thomas waited for his parents to arrive. He was nervous about their visit and stared at the picture on the wall that his dad had seen in one of their videos. He wanted to talk to his dad about it. There was a knock on the door and there was his dad. They gave each other hugs and Thomas looked beyond his dad for his Mother. His dad told him she was not able to make the trip. But sent her love.Thomas was thankful for some man time and just then Sean and his dad walked in. Looks like both our moms bailed, so it's an all guy weekend.
Thomas' dad, Jack, suggested dinner and they headed to a nice steak house. They were on their third bottle of wine when Sean's dad, Jerry, asked us how much money we were making on our website. Thomas spit out his wine and Sean choked on the piece of meat in his mouth. Thomas looked at his dad who smiled and shrugged his shoulders.
Jerry leaned in and said he said it was hard to see at first, but had to admit the sex was hot and he and Jack had shot several loads watching the boys go at it. The boys' heads snapped back and forth between each other and their fathers. They stopped at each other and mouthed WTF? Jack paid the bill and told the boys he thought they should head to the hotel they rented and continue this conversation.
They left the restaurant and the second they were in the car Thomas told the dads to spill. Jerry said that during a couples dinner one night the discussion of tattoos came up. Jack admitted to having one and showed it off. Jerry realized that he had seen that tattoo before. Then admitted that he enjoyed watching other people have sex and jack off and admitted to having an account on Chatterbate. When he realized the big dick he had been watching was Jack. He couldn't believe it.
Jack started speaking and said Jerry approached him outside one day and mentioned he had seen a tattoo like the one I had. Jack said he knew he had been discovered so he just asked if he wanted to see it live and in person. Long story short. We have been playing around together for a couple years. When we found out you two were a couple it really blew our minds. We felt dirty and confused. But when we saw your videos we couldn't deny that there must be something about the men in our families that just needed to be together and we agreed that it would just give us more opportunity to play around together. Also, your mom's both know. That is why they are not here this weekend. They said it was time to come clean.
They arrived at the hotel and walked to the room in silence. When they got to the room they noticed there was only a king bed in the room. Sean was the first to speak. So, when you say playing around? Jack replied. We are nowhere near the level as you two, but we have done more than jack off. Sean shook his head and Thomas spoke next. Mom knows? Jack said she actually encouraged it. She loves my dick, but is happy she doesn't have to take care of it all the time. Sean looked at his dad. Yes, your mom knows too. Since your mom hit menopause early she has no interest in sex so is glad I can still get my rocks off with someone but not fear an emotional affair.
The boys both took a deep breath and said as long as no one was getting hurt and their moms were ok with it, who were they to judge? Both dads smiled and Jack said it was time for a night cap and poured each a drink. So, back to my original question. How much money are you two making on your website? Jerry asked. Sean pulled out his phone and opened the app and showed his dad their current balance. His dad choked on his drink. Thomas laughed and said that doesn't include the money I am making off my dildo sales! This time Thomas' dad was the one choking.
Thomas and Sean were sitting on the edge of the bed when Jack noticed Sean staring at his crotch, he rubbed his dick helping it grow in his slacks. Thomas was looking at Jerry wondering what level Sean's dad and his dad had gotten to. Unconsciously Sean was rubbing Thomas' thigh and had worked his way up to his crotch. Thomas turned towards Sean and saw the glazed look in his eyes and then saw that his dad was rubbing his extra long bulge. It was surreal to see the wanting in Sean's eyes but realizing it was his own father creating the lust.
Sean pulled his gaze from Jack's crotch and looked at Thomas. Thomas smiled and kissed Sean then whispered in his ear. Time to meet my maker. Sean slid off the edge of the bed and crawled in front of Jack. He reached up and undid Jack's pants and pulled out the cock that made his boyfriend. It was almost a mirror image of Thomas'. Sean stroked it and felt its weight in his hand. He looked up at Jack and saw the future as he looked like an older version of Thomas, then leaned in and took Jack's cock into his mouth. Jack inhaled deeply as he felt his dick slide into Sean's throat.
Thomas was snapped out of his trance when he felt hands slide across his crotch and looked down to see Sean's dad kneeling in front of him. Jerry opened Thomas' pants and Thomas lifted his ass off the bed and allowed Jerry to lower them down and slide them off. Jerry got in place and took the head of Thomas' dick in his mouth. He was nowhere near as the master cock sucker as Sean, but the fact is was Sean's dad sucking his dick was a huge turn on. Jerry moved all around Thomas' dick and down around his balls. While he didn't deep throat he did suck every part of Thomas dick.
Thomas looked up and locked eyes with his dad. They both moaned and groaned the same. They both had their hands on their head givers. They both gasped as they shot their loads. Sean and Jerry both swallowed as they felt the cock in front of them and shot their loads hands free as they felt the cock pulse a load down their throats.
Sean stood and kissed Jack, sharing his load. Jerry did the same. Sean pulled Jack towards the bed and as Sean sat next to Thomas, Jerry stood and kissed Jack and Sean leaned over to kiss Thomas. Thomas could taste his father's cum in Sean's mouth. He wasn't sure if he was turned on or grossed out, but he didn't stop kissing Sean.
As the men regained their composure Jack poured each of the men a drink. They drank them down in one gulp and each pulled themselves together. Sean and Thomas put on their coats and went in to hug their dads. It was a long, lingering hug. The men separated and Sean and Thomas turned to leave the hotel room.
As they walked out of the hotel Sean looked at Thomas. HOLY FUCK! Did that just happen? Thomas just nodded as he texted his request for an Uber. The boys stood in silence as they waited for their car to arrive. When they got back in their room they stripped and got in bed and next to each other. FUUUUCCCKKKK!! Sean said as he wrapped himself around Thomas' body.
Before they knew it, Spring Break was upon them. Thomas and Sean got a message from Leo. Get together in Miami. Be there! The boys looked at each other. What do you think? Should we go? They both agreed it would be fun and replied for more details. Leo said to book a flight and he would take care of the rest.vThe boys asked if they could bring some friends. Leo agreed and said the more the merrier!
The boys texted Nolen, Travis, Aaron and Vic to see if they would be up for it. Travis replied, yes, if Lisa can join. Nolen said yes, if Carrie, Sarah and Amber could go. Aaron and Vic were a yes. Thomas texted Leo and said they had a group of 10 and explained who they were. Would that be ok? Leo said no problem and he would make the arrangements.
They all boarded their flight and when they arrived in Miami Leo was waiting for them at baggage claim. When they exited the airport a large shuttle van was there to transport them to their home for the next week. W. South Beach Condos. We pulled up and all mouths dropped open. Leo took us to the 15th floor and he opened the door to a beautifully decorated 4 bedroom condo.
He showed everyone the bedrooms and they were quickly taken by each couple. Thomas and Sean were the only ones without a bedroom. Leo told them to follow him and they walked next door. Leo opened the door and the boys saw a naked, Steve, Cal, Mark,Mike, Larry and Alex. I thought you two could stay here with me, or us, he said. Thomas and Sean smiled and nodded.
The boys put their luggage in Leo's room. A huge master suite with a massive bed. The room was overlooking the beach and had a wrap around balcony. The boys hadn't closed their mouths since they arrived. Leo explained that all the guys were part of a group that owned several businesses and had acquired these units several months ago and had them renovated. This is the first chance they got to use them and thought we should all break them in.
Thomas and Sean went back to their friends' condo and by the sounds of it, they were all breaking in their bedrooms, except for Travis and Lisa. We told Travis to come with us and Lisa smiled as she went to Sarah and Amber's bedroom.
When the boys returned to Leo's. They quickly undressed and became the center of attention. Two men had Travis' dick in their mouths, Sean was pulled into a group on the couch and Leo took Thomas' hand and led him to the other couch.
Leo went down on Thomas and worked the head of his dick. Thomas watched as Sean positioned himself on his hands and knees. Mike and Mark were on either side of him and entered Sean's holes at the same time. Steve and Cal were working Travis' dick, while Larry and Alex were feeding Travis their dicks. For a straight guy, Travis can sure suck a mean dick or dicks!
Leo came up from sucking Thomas and rolled Thomas onto his belly. Leo started eating Thomas' ass and when Thomas lifted his head to moan Alex had come over and fed Thomas his 11" dick. Thomas took it to the base and bobbed up and down on it. Thomas felt Leo move and then the head of his dick entered his ass. Leo's thrusts helped Thomas swallow Alex's dick.
Thomas looked over at Sean who had switched positions and had mounted Mike and Thomas watched as Mark entered Sean's hole next to his friend. Sean moaned in delight as he was being fucked by both men.
Larry started moaning and Thomas turned as he saw Larry's load spray across Travis' face and down his chest. Travis released his load, but was swallowed between Steve and Cal's mouths. Larry dropped down and licked his load off Travis and then kissed Travis sharing his load. Mike and Mark were next, filling Sean's ass. Thomas could tell that Sean was cumming as the men filled him with their load. Alex grabbed Thomas' head and emptied his balls into Thomas' throat and Leo collapsed on Thomas' back as his load filled Thomas. Sean looked over at Thomas and said this is going to be a great Spring Break!
The men peeled themselves off each other and went into their bathrooms to get cleaned up. Sean, Thomas and Leo shared his walk in shower and enjoyed washing each other's bodies of sweat and cum.
Thomas and Travis walked back over to the other condo and found everyone in the living area having a drink. Travis walked over to Lisa and they gave each other a very passionate kiss. Nolen mentioned being hungry and the others agreed. Thomas said he would check in with the others and see if there was a plan.
Leo explained that he owned a Steak House around the corner and had made arrangements for all of us to have dinner there. He thought the rest of the week our friends would probably want to be on their own and his friends were looking forward to relaxing by the pool. We can discuss details at dinner.
They all headed out for dinner and Leo let Thomas and his friends know the condo had a private beach area and as long as they wore these bracelets drinks were included. He went on to say there were two clubs across the street for dancing and would be packed with college students on spring break. The group of college students all agreed that they wanted beach time and the clubs sounded great.
After dinner the college students headed to the bars. The first two were fun, but overly crowded. The third bar was The Palace. This was the place! As they walked in a 6'2 Cher walked down the runway singing Believe. It was a drag night! The group paid the cover and found a couple tables to sit and enjoy the show.
The waiter came over. He was HOT. The short shorts barely contained his ass and the outline of his bulge was practically imprinted in the fabric. He advised that their house specialty was a Drag-a-rita and he could bring over a couple pitchers if the group would like. Everyone agreed and then turned back to the stage to see two new performers walk on stage. They stood and told dirty jokes to the crowd and Travis was tearing up, he was laughing so hard.
The ladies' on stage took notice and asked Travis to come up on stage. They asked Travis where he was from and who he was there with. Travis pointed to his girlfriend. They asked Lisa if Travis was good in bed and she shrugged her shoulders, answering honestly. The ladies' joked that Lisa should know what she is getting into, then asked if anyone at the table knew if Travis was good in bed. All the boys raised their hands! The `ladies' were speechless and the audience went crazy.
The ladies' began to clarify. So you are here with your girlfriend but you fuck the boys. Travis nodded. Then the ladies' said there is only one reason a boy has a girlfriend but needs a boy to fuck. She looked at his crotch and made an exaggerated motion as to his size. Are we right? The ladies asked. Travis nodded.
The ladies' asked how big Travis was. He leaned in and whispered in their ears. Both of their mouths dropped open. Then he leaned in again and pointed to Thomas. The ladies' looked at Thomas and called him up on stage. Ladies and Gentleman, we have two boys claiming they have endowments that would rival our own Long Dong Diva. One of the ladies' walked over to a larger ruler painted on the wall.
All of sudden the music changed and Chuck Berry was singing My Ding A Ling. Then a 6'7 black man dressed in a full evening gown walked on stage. Long Dong, we have two boys here that have made a claim to your place on our ruler of fame! We think we need to call them out and have them pull them out to find out who is truly the Long Dong in the house!
Long Dong nodded and the `ladies' explained the rules to the crowd. She reminded the crowd that this was a family establishment so some modesty would need to be provided. A screen was brought out and the boys stepped behind it. The three of them stood sideways so their bodies would cast a shadow on the screen. The crowd could see the boys all pull out their dicks.
Three waiters walked behind the screen and got on their knees in front of the men. Based on the shadows all the men were receiving a blow job to get them all erect. Long Dong Diva was the first to reach his full erection and the crowd screamed with amazement. His waiter walked around to a huge ruler on the wall and pointed to the 12.5" mark where Long Dong's name was written.
The boys were now erect and Travis' fluffer came around the screen and pointed to the 13" mark. The crowd went crazy. When Thomas' guy came out, he rubbed his jaw and walked over to the ruler and pointed to the 11", the crowd booed, but then he slid his hand up, and up, and up past long dong, then past Travis' mark and to the 13 ¾ mark and wrote his name.
The crowd was going insane and the three men walked around the screen, having replaced their members inside their pants, to a huge round of applause. The evening gown offered much better coverage to Long Dong's bulge than the boy's tight jeans! The boys thrust their pelvis' to the crowd and received another huge round of applause.
When the boys returned to their table the waiter, who happened to be Thomas' fluffer, brought a round of shots to the table. As your prize for ousting Long Dong as our reigning size queen, you and your friend's drinks are on the house tonight! He leaned down to Thomas and told him if he wanted more fluffing to meet him in the restroom in 15 minutes.
Thomas nodded and the group all did their shots. Thomas told Sean what the waiter had said and both boys headed to the restroom a few minutes later. The waiter arrived and was surprised to see Sean, but didn't hesitate and pulled both boys in the farthest stall. He yanked his shorts down and bent over to undo Thomas' pants. He pulled out Thomas' semi hard dick and started sucking it hard.
Sean was standing behind the waiter and bent down to eat his ass out. He tongued his ass until he heard the waiter say "fuck me!". Sean pulled out his dick and the waiter turned to see Sean's hard uncut dick. Yes! The waiter moaned. Sean soaked his dick with spit and entered the waiter's hole. The boys spit roast the waiter for a couple minutes and then the waiter pulled off both dicks and turned around.
He took Sean's dick in his mouth and Thomas pressed the head of his dick into his ass. The waiter pushed Thomas back and pulled off Sean to tell Thomas' slow! Thomas pushed his head back in, he felt the waiter loosen up and pressed as much of his dick as he could inside the waiter's ass. Sean and Thomas' alternated thrusts like a woodsman sawing a tree. The waiter moaned in delight.
The boys were fucking both ends hard when someone banged on the door. Kyle, if you're in there get back to your station, someone yelled. The waiter pulled off the boy's dicks and quickly pulled up his shorts. Fuck, my boss! He said. He adjusted himself and exited the bathroom. An older, very older, man was standing outside the stall door and saw the boys with their cocks hanging out. Woof, he said. At least he has a good reason to be off the floor and turned and left the restroom.
The boys looked at each other and Sean turned around. Thomas approached and wet his dick and Sean's ass. He entered his boyfriend's ass and fucked him. Sean jacked his cock and came in the toilet. Sean pulled off Thomas and finished him in his mouth. No need to be leaking cum from my ass the rest of the night, Sean told Thomas.
The boys returned to the table and found another round of shots. Kyle came by and gave Sean his number and told him he lives close by if they want to finish what they started. Sean winked and told him they had already finished. Kyle frowned.
The show continued and the impersonators were incredible. Some of the outfits were very revealing and when Long Dong Diva came out in a bodysuit we all looked at each other wondering how he hid his huge dick. That must take some serious tape Sarah said. The group hung out for another round and then all headed back to the condos.
The next few days were fun in the sun. Thomas and Sean spent their nights with Leo and enjoyed sharing many loads between each other. Travis made a few appearances and after unloading his balls would return to Lisa. Nolen and Carrie spent most of the time hand in hand and every night fucking their brains out. Sarah and Amber were there for Lisa as needed and enjoyed teasing all the college boys at the bar as they became very sexual on the dance floor.
Aaron and Vic also kept mostly to themselves, but found time to make a couple quick beach blowjob videos for their viewers.
Thomas and Sean had found a secluded area of the beach next to some cave formations. They took advantage of this and made out under the sun. Their suits could not contain their erections and the boys gave each other a blowjob as people walked by. A couple guys stopped to watch and pulled out their dicks and stroked as the boys sucked on each other. Thomas and Sean loved putting on a show.
The boys wanted to create a video for their viewers, but didn't have their ski masks. Sean laid on his stomach and pulled a towel over his head and raised his ass. Thomas panned the camera to show the ocean off in the close distance and then down to show his dick enter Sean. Thomas raised the camera again to show people walking by. The boys groaned and Thomas pulled out to shoot his load all over Sean's back. He rubbed it in like suntan lotion and ended the video with him saying Goodbye from sunny Florida. The boys pulled up their suits and ran into the ocean rinsing Thomas' load from Sean's back.
The boys returned to their towels and could hear moans. They peaked their head over the ridge of the rocks they were under and saw Aaron and Vic fucking each other. They both yelled at the boys to get a room! The boys turned and flipped them off!
Their last night in town they all met at Leo's for a farewell dinner and drinks party. After several cocktails the group started loosening up. Sarah and Amber started making out and Lisa joined them. The rest of the men stripped and moved from dick to dick sucking, rimming and fucking each other. Thomas noticed Nolen and Carrie were standing near the kitchen bar watching the events unfold. Carrie had her hands in Nolen's shorts, then got on her knees in front of him and started giving him a blowjob. Nolen stared at the sex happening in front of him and smiled as he looked down at Carrie sucking his dick.
Thomas was getting a blowjob and watching Aaron and Vic in a 69 and caught Vic looking at him and winked. Thomas winked back and Vic pulled off Aaron's dick and mouthed, I want you, to Thomas. A cock presented itself to Thomas and Thomas took it in without even looking up to see who it was. The sounds coming from the room were intense. As men, and women, orgasmed the sounds diminished and bodies started heading back to their rooms. Nolen remained with his spent dick sticking out of his shorts as he kissed Carrie. Soon everyone was back in their own rooms and the evening came to an end.
The flight back to Michigan was quiet. All were tanned, drained and hungover. They all stopped at the bar for their final Spring Break drink and cheered for their great vacation. After a couple rounds they all separated and headed back to their own places. Thomas and Sean enjoyed being back in their own bed and after an hour together their neighbor pounded on the wall. Welcome Back!
The boys became very busy with school projects and March and April flew by. They were in the last month of school and Thomas was studying in the library one night when Vic approached him. He asked if he could join Thomas and Thomas nodded. Vic got out his supplies and after 30 minutes of studying Thomas felt Vic's foot rubbing his leg.
Thomas looked up at Vic who didn't make eye contact. Thomas asked Vic what he was doing and said he thought he and Aaron were monogamous. Vic looked up and frowned a bit. The whole monogamy idea was Aaron's. I agreed to it when we first started dating as I hadn't really experienced anyone else, so I was just happy to be getting laid. Since I have met you, and some other guys, I think I would like to broaden my experiences.
Thomas told Vic he understood, but didn't want to do anything to come between him and Aaron. Thomas asked if Vic and discussed this with Aaron and Vic said, Kind of. I brought up you and Sean and Vic will always say he could never do what you guys do. So, I just dropped it. I am thinking I am going to have to break up with him just so I can see what having sex with someone else is like. I really want to see what your dick would be like.
Vic said he had gone on Grindr a couple times, but is always afraid of running into someone Aaron knows and having it blow up in his face. He just wants to try another dick. Maybe I won't like it and will realize that I am happy with Aaron, but if I like it, maybe it is time Aaron and I broke up. Vic shook his head. I am just curious.
Thomas felt bad for him but he could understand. Thanks to Erik he had had experiences he never would have been able to have. But, he didn't want to be a part of breaking Vic and Aaron up either. Thomas got an idea and asked Vic to come back to the dorm. When the boys got there Thomas pulled out his dildo. He suggested Vic give this a try and introduce it to Aaron. Then if they liked it, you could bring up that you wonder what the real thing would feel like. Vic held the dildo and agreed. He put it in his backpack and headed off to his apartment.
The rest of the semester the group got together often and became a great group of friends. They were a mixed bag of friends and somehow they all accepted each other and never judged. It was the best year of college the boys could have imagined.
One night at the bar, Vic came up and said that he and Aaron had tried the dildo. It was WAY too big for either one of them. But Aaron said he would like to try a smaller one, so we got an 8" one and we both really liked it. I did what you suggested and mentioned Sean. Aaron still isn't sure, but said he would think about it. Baby steps!
Finals were approaching and they all focused on finishing up projects and preparing for exams. They were all excited to finish on a Thursday and made plans for an epic end of semester celebration. Aaron and Vic offered to host and we all agreed it should be an epic `naked' end of semester celebration.
The group met around 7:00 and the girls suggested a game of Never Have I Ever. The questions were not tame and Thomas and Sean had to take small drinks to avoid getting too drunk too soon and the rest of the group were starting to call them sluts. Sean raised his glass and shouted, No Regrets! Thomas noticed Aaron looking at Sean's dick.
The game ended and Vic brought out a bag of weed. He rolled a couple, very fat, joints and we proceeded to all get extremely stoned. Sean and Thomas went to get a couple more drinks and Thomas mentioned Vic's dilema. Sean smiled and said he would make it happen.
Sean placed himself in view of Aaron and Vic and exaggerated his movements so his dick was flopping around and he was groping himself more than usual. He had plumped up quite a bit and Aaron and Vic obviously noticed. Sean walked over to Aaron and told him he had a question about some new setting on Chaturbate and could he help him out.
Aaron agreed and the two headed into the video room. A few minutes later I looked at Vic and nodded my head towards the hallway and winked. Vic got the idea and headed to join Aaron and Sean.
Thomas looked over and noticed Nolen, Carrie, Travis, Lisa, Sarah and Amber were all having a conversation. Carrie was openly stroking Nolen's hard dick as they and the rest of the group looked over Travis' cock. He was inflated, but not hard. Thomas watched as the girls compared Nolen and Travis' dicks.
Thomas joined the conversation and Sarah asked who he would pick to have sex with. Travis or Nolen. Can't I have both? Thomas asked. They all laughed. Thomas admitted he was a bit of a size queen, so HE would probably choose Travis. Thomas heard Carrie tell Nolen he has all she needs. Nolen smiled and they kissed as precum oozed out from the head of his dick.
The three boys returned to the living room with three flaccid dicks hanging between their legs. Thomas looked at Sean and received a wink and then looked at Vic who couldn't stop smiling and touching Aaron. Sean came over to Thomas and said Mission Accomplished.
Sean and Thomas began making out, which started a chain reaction. Nolen and Carrie were on the sofa groping at each other and the other three girls were on the floor doing the same. Travis was masturbating watching the girls until Sean waved him over to join him and Thomas.
Aaron and Vic were making out next to the boys when Thomas felt a hand on his leg. When he looked down it was Aaron's hand. Thomas looked at Aaron, and got a wink. Aaron then proceeded to go down on Vic's hardening dick.
Thomas looked around the room and watched everyone. Thomas looked at Nolen as Carrie lowered herself onto his dick. He smiled at Thomas and began thrusting into his girlfriend pussy allowing himself to be watched.
Lisa had joined the boys and kissed Travis as he fucked Sean. Travis had one hand on Sean's ass and the other in Lisa's pussy.. He was enjoying the best of both of his worlds. It was as if he was fucking Lisa as he fucked Sean. When Travis shot his load in Sean, Lisa grabbed Travis' face and held him tight as he finished his orgasm into Sean. When Travis pulled out of Sean he pulled Lisa into a tight embrace and fingered her until she moaned into her orgasm.
Soon all bodies were spent and relaxed in a naked heap on the couch and floor. Thomas spoke up and said he was a lucky guy to have such an incredible group of friends. They all agreed and couple by couple they headed back to their own places and began their summer vacations.