This story contains gay sex between consenting adults. If this story offends you or it is illegal for you, please leave this site. If not..enjoy and let me know what you think!
The characters and events in this story are fictional. The story may portray some real people, events, or places.
This story follows two of the characters in Mr. Shepherd series. You can find the other stories here on Nifty.
1 - https://www.nifty.org/nifty/gay/adult-friends/mr-shepherds-summer-vacation/
2 - https://www.nifty.org/nifty/gay/college/go-gv/
3 - https://www.nifty.org/nifty/gay/adult-friends/mr-shepherd-moves-to-dallas/
4 - https://www.nifty.org/nifty/gay/adult-friends/mr-shepherds-friends/
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Sex Ed 101
Thomas was making breakfast in the morning and Lucas was pouring cups of coffee when Ryan appeared in the kitchen. So, did you come up with answers to my questions? I tried my cum last night, so no need to answer that question. Lucas handed Thomas a cup of coffee and each took a big sip.
Thomas pointed to the empty seat next to him. Ryan sat and Thomas took another sip of his coffee then began. If, or when, you and Jimmy do anything sexual you will discover what each of you like. Don't worry about not knowing anything. It is special when two people learn from each other. Be patient and don't rush anything. If something isn't working, try something different. Listen to each other. Ryan sat and thought about what Thomas said. He nodded, then replied. But, how does my dick fit in his ass, I mean I am really big. Thomas looked at Lucas. Lucas took a deep breath. That's more a dinner conversation than breakfast.
Then Erik picked Ryan up for school Thomas and Lucas explained what was going on. Erik laughed out loud and said he would help guide the conversation and have a discussion with Ryan at school. Erik went on to say he was happy that Ryan could be so open with them and they were handling everything ok. Maybe it would be better if you showed him some things instead of just telling him. He is a visual learner! Thomas and Lucas gasped a bit. But then Thomas said he has already listened to us having sex...Lucas' head dropped and he walked away.
Thomas and Lucas knew that Ryan would be expecting answers at dinner. They opted out of doing a live show for Ryan and risking jail time, but did pick up a few items at the adult bookstore that may help Ryan experience some of his answers. During dinner Ryan was a ball of nerves. Thomas and Lucas could feel his anticipation and after Lucas took his last bite Ryan started shooting off questions. Lucas suggested they clean the table and then all would be revealed. Thomas laughed. Well not all! Lucas cocked his head and gave Thomas a dirty look. With everything put away they went into the living room and Lucas started the conversation. Ryan, Thomas was right. It's ok if you don't know anything. If Jimmy is the one he will be understanding that he is your first and will be patient. Ryan nodded. He explained what they discussed the other day and how Jimmy stopped what they were doing. Thomas and Lucas were pleased and surprised that Jimmy had done that.
Lucas looked at Thomas. Thomas pulled a bag out and said they had bought Ryan a few things that may help him get a better understanding and answer some of his questions. First, condoms. You will want to practice putting on condoms. It can be difficult, but you and your partner should make it part of the experience. Based on what you said about your penis we bought you magnums. Second, Thomas pulled out a dildo. The silver bullet. The same kind he used to experience anal play the first time with Erik. Then he pulled out a bottle of lube. He explained how to use the two together and Ryan took the vibrator in his hand and Thomas reached over and turned on the vibration switch. Ryan's eyes opened wide.
Thomas took a deep breath and then pulled out the remaining items. Three lifelike dildo's of varying sizes. Ryan grabbed the largest one. This looks like my dick size but I am uncut. Thomas and Lucas both shifted in their seats. Ryan then grabbed the mid size and said based on what he felt this would be about the size of Jimmy. Lucas said Ryan could practice oral with the dildo, but a real penis feels a bit different. Ryan looked over everything and was rubbing his crotch. Thomas asked if he had any questions. Ryan shook his head. Then looked up at them. He grabbed all the items and ran down the hallway. About 15 minutes later Thomas and Lucas heard a loud moan from Ryan's room. Thomas and Lucas smiled and leaned in to kiss each other. Lucas pushed Thomas back on the couch and opened his pants and pulled out his cock. He began sucking the head and then went up and down the extra long shaft. Thomas looked down and rubbed his hand through Lucas' hair. Lucas was really getting into it and had most of Thomas' cock down his throat when they heard Ryan exclaim HOLY SHIT!
Lucas jumped up and Thomas covered himself. Ryan's eyes were wide. Your cock is HUGE! Thomas stammered a bit. Lucas' bulge obvious Ryan said it looked like he was big too! How did you get so much of his cock in your mouth? I was just trying to suck one of the dildos and kept gagging! Thomas was trying somewhat unsuccessfully to cover himself. His hands pulling down his shirt but his pants dropping further down his legs. Lucas was trying to cover himself but Ryan, very erect, made no attempts to cover himself and then pulled down the front of his sweats to reveal a very erect 8" uncut cock with the foreskin half covering the head. He looked down and said that compared to Thomas I look like a pre-teen. Lucas raised his voice a bit. Put that away! Thomas snapped and said he was trying! Lucas turned toward Thomas. I was talking to Ryan, but you put yours away too! Finally they all busted out laughing.
Ryan did put his cock away and Thomas let go of his cock long enough to pull up his pants. Ryan stared intently as he watched Thomas' cock get stuffed into his pants. Ryan apologized for interrupting them but had some questions. But now has even more. How did you get all of that in your mouth and do you get fucked by that? How big is that? Can I see it again? Lucas held his hands up and told Ryan to take a breath. We shouldn't have been doing what we were doing out here. Ryan shook his head. It's no big deal. I have listened to you two having sex, now I understand why you moan so much! Lucas' face flushed. Thomas smiled but then got the evil eye from Lucas.
Seriously, how big are you? Can I see it? Thomas and Lucas looked at each other confused. Thomas stood and dropped his pants. He was still semi erect and it was very impressive. Not his full 13 â...ž" but still hefty. Thomas pointed to his tattoo and Ryan's mouth dropped open. SERIOUSLY? Thomas nodded and then worked at putting his cock away. Ryan looked at Lucas. How? Lucas exhaled. Patience, practice and trust. Can I watch you do it to Thomas? Lucas shook his head emphatically no! Ryan ran down the hall and returned with the large dildo. Can you show me how to do it with this? Lucas hesitated. Thomas walked over and took the dildo. He held it up and looked at it. He opened his mouth and inserted the dildo until it was completely buried in his throat. Ryan stood and watched with amazement. Thomas pulled the dildo out and then reinserted a couple more times. His cock responded to the oral stimulation. Ryan noticed.
Lucas told Thomas to stop. Thomas realized he was getting a bit too turned on. He walked over to the sink and rinsed off the dildo and took the opportunity to adjust himself so he was a bit more comfortable in his pants. He returned to the living room and returned the dildo to Ryan. Practice. Ryan took the dildo and then hugged Thomas. He pulled away and then hugged Lucas. You two are awesome! I could never talk to my family about any of this and Mr. Shepherd is cool, but he said the school limits how much they can discuss in sex ed. This is so much better! Jimmy is gonna freak when I blow him! He put the dildo in his mouth and took off down the hall yelling at Thomas and Lucas to finish what they started. Thomas and Lucas looked at each other and took off running to their bedroom. Ryan smiled as he heard the moans coming from their bedroom and got another inch of the dildo in his mouth.
The following morning the three were in the kitchen. Ryan nonchalantly asked if Lucas top or bottom last night. Lucas told Ryan that was private. Thomas was behind Lucas and mouthed bottom and winked at Ryan. Ryan smiled as he ate his cereal. When Ryan went to put his bowl away his sweats did not hide his erection. He tugged at it and said he would be ready for school in a few minutes. Erik arrived and was waiting in the kitchen. He finished his coffee and asked Thomas and Lucas what was taking so long. They both just smiled. Ryan came around the corner with a pep in his step and flushed cheeks. Erik looked closely at his face and then at Thomas and Lucas. He turned back to Ryan and pointed to his right cheek. You missed some. Ryan wiped it off his cheek and licked his fingers. Erik shook his head and the two were headed to school.
The rest of the week was a constant flow of Ryan spending an hour in his bedroom and then coming out asking Thomas and Lucas questions and then running back to his bedroom. On Friday he came running out of the room and exclaimed that he did it. He held the mid size dildo up and took it all down his throat. He pulled it out and said he still couldn't do the big one, but was getting closer. Thomas and Lucas weren't sure if they should be proud or concerned. Ryan smiles. Jimmy is gonna be one lucky guy! His hand had been in his sweats the entire time and his bulge led the way back to his bedroom. Thirty minutes later he returned to the living room. His cock deflated and swaying in his sweats. Thomas and Lucas were snuggled together on the couch watching a movie. Ryan sat on the chair across from them and sighed. Thomas asked if everything was ok. Ryan shrugged his shoulders. Lucas and Thomas sat up and asked Ryan what was wrong. Ryan looked up. Jimmy asked me out on a date and I'm nervous. I want to go out with him, but I don't know how everything will work. Thomas scooted over and patted the couch cushion. Ryan came over and sat between them. They both put their arms around Ryan and told him if he feels a connection with Jimmy it will all work out.
Ryan laid his head on Thomas' chest. Lucas pulled his legs up across his lap. Thomas put a pillow in his lap and Ryan moved his head down. Lucas grabbed a blanket and covered him. Ryan felt the most relaxed he had ever felt. He felt safe. Secure. Supported. They watched the rest of the movie and Ryan sat up. That felt good. Just being together. Lucas told Ryan that when he really likes someone it will feel like that. Ryan hugged the two men and then went to bed. Lucas snuggled back into Thomas. This really does feel good. The two snuggled closer together and watched the news.
The next day Jimmy was working at the restaurant. Thomas asked if he could speak with him. They went to the office and Thomas explained that Ryan was very nervous about their date. Thomas also explained that Ryan really wants to experience sex. Jimmy moved a bit nervously. Thomas told Jimmy it was ok. He and Lucas both know teens have sex. But, he also knew Jimmy was older and probably had more experience and hoped he would be patient and kind with Ryan. Jimmy nodded. Thomas asked what their plans were and Jimmy said it was just going to be a nature walk. He couldn't really afford anything else. Thomas pulled out his wallet and gave Jimmy $100. Do something fun.
Jimmy smiled huge then frowned a bit. Thomas asked what was wrong. Jimmy asked if he could be totally honest with him. Thomas nodded. I have been with a few guys and they weren't really good experiences. A car blow job and a quickie in the restroom and pointed to the employee restroom. Thomas' eyes widened and Jimmy blushed. Anyway, I really want Ryan to have a pleasurable experience but we really don't have any place private. Thomas hesitated. Well, it just so happens Lucas and I will be working till close tonight so won't be home until after midnight. Jimmy hesitated. So, we can... Thomas raised his hand...I am just saying Lucas and I won't be home tonight until after midnight. Thomas told Jimmy to get back to work. Jimmy smiled and then shook Thomas' hand.
Thomas and Lucas were busy at work and the evening was coming to an end. The restaurant was now closed and they were making sure everything was put away and ready for the next day. Thomas had driven the convertible tonight as he knew it would be too dark to drive the boat after work. It was a beautiful night and as he put the top down he smiled at Lucas. They both pulled their dicks out and Thomas took off driving home. During the drive they each had their hands on the other's cocks and they were both fully erect Lucas bent over and took Thomas in his mouth and slicked up his cock so he could jack him off better. Thomas took his time driving home and was on the verge of cumming when Lucas bent back over and took Thomas' load in his mouth. Lucas sat up and Thomas began stroking Lucas' cock faster and faster. Lucas lifted his shirt and sprayed his load all over his chest and stomach. Thomas pulled his hand away and licked the cum that had oozed on his hand and Lucas wiped up the rest and fed it to Thomas and then licked his own fingers clean.
As they pulled into their driveway Lucas noticed Jimmy's dad's car. Thomas explained that he had told Jimmy they had to work late. Lucas looked at the dark house. Lucas shook his head. We will be getting an ear full after tonight for sure! The two headed in the house and found Ryan and Jimmy lying next to each other asleep and naked from the waist down. Lucas flipped on the lights and the two jumped up startled. Both dicks were semi hard and Jimmy quickly covered himself. Ryan didn't seem to care that he was on display. Jimmy pulled on his shorts and then looked at his watch and said he should be getting home. Ryan walked him to the door still naked and they kissed goodnight. Ryan watched Jimmy drive away and then shut the door. He walked back into the living room fully erect, said good night and then walked to his room. Thomas and Lucas were shocked that Ryan wasn't bouncing off the walls with details of his evening. They were looking at each other when Ryan came running out of his bedroom and jumped between them, still pantless. OMG! It was incredible. We didn't have sex sex, but we did a bunch of other stuff. Did you know your nipples were sensitive? Thomas and Lucas about gagged.
Ryan said the night was so much fun! We went to play Top Golf and had some great food. Then Jimmy mentioned you two were at work and asked if we could come back here. Of course I agreed! But, when we got back here we were both so nervous we didn't know what to do. We were sitting on the couch and finally he leaned over and kissed me. We kissed forever! His hands rubbed my chest and pinched at my nipples. I think I could cum from that alone! So, I did the same to him. He moaned a lot! Then we started rubbing each other down there. He looked at me and asked if I was sure I wanted to do this. All I could do is kiss him. So, he undid my pants and slid them down and .... And ... and....Thomas and Lucas were holding their breath....gave me a blow job! Right here where you were giving Thomas a blow job the other day! Thomas and Lucas coughed a bit. Ryan grabbed at this dick a bit and it plumped.
It was amazing! So much better than jacking off. But it felt too good and I came. Like in 30 seconds. He swallowed it and came up smiling. I told him I was sorry for cumming so quick. He shook his head and said it was a compliment and kissed me. Then he sat back and I looked down and his cock was really making a bulge in his pants. I reached over and unzipped his pants and pulled them off. He is bigger than I thought! I got between his knees like you did Lucas and started sucking. He told me I was a natural. I didn't tell him I had been practicing. He told me to do some things like lick his balls, which really turn him on. Then he took my hands and put them on his nipples. When I pinched them his cock got really big and he groaned and said he was going to cum. I kept sucking and he shot a huge load in my mouth. It was fun feeling it pulse as it shot. He makes a lot of noise like you two do! Thomas and Lucas blushed. Then he saw I was hard again so he sucked me again! I lasted longer this time. When he was done he was hard again so I sucked him again. He really likes his nipples played with! After that I was hard AGAIN! He smiled and, YUP, he sucked it AGAIN! After that one we kind of fell asleep and .. well then you came home.
Thomas and Lucas both felt a bit awkward listening to the details and sitting next to Ryan who was now fully erect. Ryan looked at his dick. This thing has a mind of its own! He jumped up and said he needed to go to bed. Moments later Ryan's moans could be heard through the house. Lucas looked over at Thomas. Well, the cat is out of the bag. Thomas laughed. And it is a very large cat! Lucas acted shocked Thomas made a comment about Ryan's dick, but couldn't disagree! Thomas moved over to Lucas. How many more times do you think I can make you cum tonight?
Ryan floated into the kitchen the next morning. He had a huge grin on his face. Everyone at school would know he had sex. There was no denying the look of someone who had sex for the first time. He showed Lucas his phone. There was a message from Jimmy. Maybe next time we can go for four? Lucas pushed the phone away. Some things can be kept to yourself! When Erik arrived to pick up Ryan he laughed as Ryan glided by him as he went to the car. Erik looked over at Thomas and Lucas who both avoided his gaze.
Saturday was meet day. Jimmy showed up at the house and the foursome headed to the pool. Ryan was hyper focused and wanted to show off a bit for Jimmy. His meets were all personal bests and his coach pulled him aside and pointed to the bleachers. The scout from SMU was there. When the meets were over the scout, coach and Ryan headed over to Thomas, Lucas and Jimmy. Lee, the scout, reached out and shook everyone's hand. He didn't hesitate and said he had a letter of intent for Ryan. This would be for a full ride scholarship and he could actually start his senior year with some virtual classes that would get him ahead of the game and get some classes out of the way. Ryan was beaming and came over and hugged Jimmy. Jimmy pulled away realizing he was soaking wet. The two boys laughed and Ryan handed Jimmy his towel.
The drive home Ryan couldn't stop talking about the scholarship! He was so excited and never thought he'd be able to go to college! He couldn't help himself and moved over and kissed Jimmy hard on the lips. When Ryan pulled away Jimmy nervously looked at Thomas and Lucas. Ryan told Jimmy not to worry they make out all the time, and more! Jimmy saw both heads drop and shake back and forth. Lucas was slightly turned and noticed Ryan's hand was in Jimmy's lap and there was a noticeable bulge.
Lucas looked at Thomas and said he felt like a boat ride around the lake sounded good. He asked if Ryan and Jimmy would mind if they left them alone for a little while? Ryan smiles big and Lucas notices Jimmy's hand on top of Ryan's giving it a squeeze. When they arrived home they all got out of the car and the boy's bulges were straining against their shorts. Jimmy attempted to cover himself, but Ryan on the other hand groped at his boner openly. Thomas and Lucas loaded up a cooler and headed out on the boat. Ryan pulled Jimmy into his bedroom and the boys completely stripped naked. Both erections slapped their stomach as their underwear pulled over their cocks. They wrapped into a deep kiss and felt their bulges against each other. Ryan dropped to his knees and took Jimmy into his mouth. He sucked like an expert and then went down to Jimmy's balls. Jimmy was moaning in pleasure. Jimmy pulled Ryan up and went down. He sucked Ryan hard and Ryan was pleased he didn't cum as quickly as the first time. Jimmy pulled off Ryan's cock and turned him around. He pressed Ryan forward towards the bed and Ryan leaned on his elbows at the edge of the bed. Ryan looked back as Jimmy moved between his cheeks and began licking his ass. The intense feeling sent a shock wave through Ryan and cum through his cock. He moaned loudly and Jimmy felt the wetness as he reached up to stroke Ryan's cock. He pulled away and said, well there is one down. Only three more!
The boys lost track of time as Ryan returned each sexual favor that Jimmy did to him. He knew Thomas and Lucas were right. He felt very comfortable with Jimmy and everything just flowed. There were awkward positions, but they just worked through them. The two were spent and lying next to each other in bed. Ryan looked at Jimmy and said he wanted him to fuck him. Jimmy leaned in and kissed him. His dick couldn't get hard at the moment if his life depended on it. He told Ryan they would do that soon, but it wouldn't just be a fuck. The two made out more until they heard Thomas and Lucas come in the house. The two slid on their shorts and walked out into the kitchen. Ryan looked at Lucas and held up his hand indicating 5 orgasms. Lucas' mouth dropped open.
Jimmy stayed for dinner and the four decided to play a game. They were sitting at the table and Thomas felt a leg brush by his under the table. He acted like he dropped a card and saw Ryan's foot in Jimmy's crotch. Thomas could feel the movement and by the look on Jimmy's face he was enjoying the attention Ryan's foot was giving him. Jimmy's eyes rolled back in his head and suddenly he excused himself to use the restroom. His face was still flush when he returned and took his seat. Ryan couldn't stop smiling. The game ended and Jimmy said he needed to get home. Ryan walked him to the door and, as expected, when he returned there was a noticeable bulge in his shorts. He was in a trance as he walked past Thomas and Lucas to his bedroom.
Ryan came into the kitchen the next morning and bluntly stated. Can you two leave Jimmy and I alone so we can have sex sex? Thomas and Lucas were kind of speechless, but knew this was coming. Ryan said he thought he wanted to bottom, but Jimmy said he wanted to feel me in him too. Is that ok? Thomas and Lucas nodded. Just see what feels good. Lucas asked if Ryan had any questions about having anal sex. His telltale head dropped and he shrugged his shoulders. Lucas and Thomas both knew what he was thinking. Thomas stood and he and Lucas took Ryan to the bathroom. Lucas pulled out the shower attachment they used and showed Ryan how to use it. Ryan listened intently and then asked if they would stay in the room while he used it just in case.
Thomas and Lucas agreed and Ryan stripped and stepped into the shower. This boy was not shy, but definitely had nothing to be shy about. Ryan said there was no water coming out. Lucas reached in and turned the lever. Water flowed out. Ryan looked nervous. Lucas asked if he was ok. Ryan nodded and Lucas stepped back. There was a gasp and then a moan. Thomas and Lucas waited and then the water turned off. When Ryan stepped out of the shower he was fully erect and had an amazed look on his face. That felt incredible! Any questions? Ryan grabbed his erection and said he thinks he can handle it from here. Thomas and Lucas smiled and stepped out of the bathroom. They stood at the door and heard a vibrating sound and then light moaning. A few moments later a couple grunting sounds.
Erik arrived and asked how things were going. Thomas and Lucas said they thought "things" might progress to the next level with Jimmy and Ryan. Erik raised his eyebrows. He asked if we could leave them alone for an evening so they could have sex sex. Erik smiled. Yeah, that does sound like things will be happening. Erik suggested dinner at the house and maybe they could have a few things progress too. Ryan walked out as he said that and smiled as he grabbed his backpack. Erik smiled at Thomas and Lucas and headed out with Ryan.
Ryan said that Jimmy would be coming by around 3:00. He asked if I could pick him up at work. Lucas mentioned that they would be going to Erik and Javier's and probably would be out very late and may even spend the night. Ryan's face began to glow. He grabbed his phone and texted Jimmy. Ryan was about to get Jimmy when he said that Jimmy got permission to spend the night, so I want to make sure if you will be home or not. Lucas smiled and said he could make that happen. Ryan smiled and ran to the wave runner.
Thomas and Lucas told all to Erik and Javier. Erik said as a teacher he thought Thomas and Lucas were handling everything very well. You can't stop teengers from doing things, so it's better to teach them healthy things. Then Erik took a big swig of his drink. From a man's view, FUCK, I am totally turned on and rubbed his crotch. The men were stripped and filled moments later and for the next several hours!
Ryan and Jimmy arrived back at the empty house. Ryan pulled Jimmy in for a kiss and admitted to Jimmy he was nervous. Jimmy hugged Ryan. You know this is my first time also? Ryan almost cried when he realized they would be losing their virginities together. Jimmy hugged him and said we will only do what you want and can stop whenever you want. Jimmy went on and said they had all night. Ryan took Jimmy's hand, but I want it now and pulled Jimmy to his bedroom.
The boys stripped and soon Ryan was on his back with Jimmy kneeling between his legs. Ryan nodded as he looked up at Jimmy and reached over to his night stand and pulled out the bottle of lube and condoms. Ryan took control from there and was pressing at Ryan's ass a moment later. Ryan had been practicing and it felt familiar. Jimmy told him to breath out. As he did this Jimmy pressed forward and Ryan felt his virginity leave his body. He pulled Jimmy down into a kiss and Jimmy stayed still inside Ryan's ass. Jimmy pushed up and away from Ryan's kiss and looked deep into his eyes. Ryan nodded and he felt Jimmy start moving in and out of his ass. Ryan pressed into Jimmy's chest and gently pinched at his nipples. Jimmy moaned and his pace picked up. Ryan wanted more and his hands pinched Jimmy's nipples harder. Jimmy made a noise and Ryan had heard this before coming from Thomas and Lucas' bedroom. Jimmy was thrusting harder and gazed deep into Ryan's soul. Ryan wrapped his legs tightly around Jimmy and pulled him deeply into his ass. Ryan didn't want this to end. The bond he felt with Jimmy was intense. Jimmy didn't want this to end either, but his balls had other ideas. As Ryan released his nipples to pull Jimmy in for another kiss Ryan felt a pulsing in his ass. Jimmy's head dropped and raised with his eyes closed. Ryan was definitely not a virgin any more!
Jimmy lay on Ryan and regained his composure and felt his dick slide out of Ryan's ass. Ryan groaned at the empty feeling. Jimmy pulled the condom off and tossed it in the trash can. Ryan looked down at Jimmy's deflating cock and took it in his mouth. Jimmy's whole body spasmed with post orgasmic sensitivity. Ryan pulled off his spent cock and moved up to kiss Jimmy some more. My turn, Ryan said. Jimmy smiled. Give me a few minutes! Ryan snuggled into Jimmy's armpit and played with his nipples. Jimmy snapped to attention and pulled Ryan on top of him.
Ryan felt Jimmy open his legs and raise his ass. Jimmy grabbed a pillow and slid it underneath him. This will help, he said. Jimmy grabbed a condom and as the two made out Ryan felt Jimmy roll the condom over his head and down his shaft. Jimmy didn't break his stride as he raised his legs and applied lube to his ass and Ryan's cock. Jimmy moved down and positioned Ryan's cock at his entrance then grabbed Ryan's ass and pulled him down and into him. Ryan moaned as he felt his cock wrapped by Jimmy's tight ass. This was nothing like he had ever felt before! Jimmy's legs pulled Ryan all the way in him and held him in place. Jimmy moaned in delight as the long thick cock spread his hole wide.
Jimmy loosened his grip and pressed his hands into the front of Ryan's hips. Ryan moved back and then Jimmy pulled him back in. Ryan knew what to do from that point and all too soon felt his cock release and fill the condom. He was so disappointed. He wanted his first time to last longer. Jimmy pulled him in tightly. We have all night. You feel incredible in me. Don't pull out yet. Jimmy's ass squeezed and milked Ryan's cock. Ryan actually felt his cock reharden from this manipulation. Jimmy smiled. Do it again. Ryan started moving in and out, Jimmy's moans filled the house and this time after several minutes filled his condom again. This orgasm he felt in his toes and his moans could be heard outside. He shuttered causing his cock to pop out of Jimmy's ass which caused Jimmy to shutter a bit.
Jimmy rolled over and gently pulled off the condom, tossed it, and then cleaned off Ryan's dick. Ryan moaned loudly as Jimmy did this. He was beginning to understand the sounds that he has heard from Thomas and Lucas' room. Ryan lay on his back and told Jimmy that was the most intense orgasm he has ever had! So different from anything else! He rolled on his side. I want you in me again. Jimmy took Ryan's hand and slid it down his torso. Ryan felt the wetness and lifted up to see cum still dripping from Jimmy's cock. Ryan was amazed and smiled at Jimmy. My fucking you did that? Jimmy nodded. Ryan rubbed the cum into Jimmy's chest.
They rested for a bit and as soon as Ryan felt a stirring in Jimmy's cock he had it in a condom and the rest of the evening Ryan tried multiple positions and as they went for their last fuck found that the box of condoms was empty. Ryan had to have Jimmy in him one more time. Jimmy wanted to fuck Ryan one more time. The intensity took over them and Jimmy entered Ryan bare. The bareness felt incredible on Jimmy's dick. His thrusts seemed faster, his cock felt warmer, his cum came quicker and Ryan's ass was filled. Ryan felt the wetness and Jimmy told him he wanted Ryan's load in him now! They flipped over and moments after Ryan felt the warm wetness of Jimmy's hole he was releasing his balls.
This was their final fuck of the evening. They were spent. The next thing they remember was hearing Thomas and Lucas knocking on the door. The door opened slowly and the boys moved slowly not bothering to cover themselves. Lucas smelled the sex in the air. He suggested the two boys shower. And open a window! An hour later the two boys came into the living room. Ryan hugged Thomas and Lucas. Best night ever! Jimmie seemed a bit embarrassed but when Thomas and Lucas suggested a wave runner race he perked up but rubbed his ass and said maybe they could just cruise around in the boat. Ryan rubbed his ass and agreed. Lucas smiled at Thomas and nodded in agreement!