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Mr. Shepherd's Summer Vacation Ch. 4

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The Last Day of School------------

I was alone at my place when I woke up. I smiled as I thought about the past 48 hours. Thomas was an awesome kid/adult and I really had a good time. I decided I would send him a text and say good morning. I got a quick reply along with a dick pic next to a load of cum. He said his parents would be home soon and would text later when he could. I stared at the pic as I proceeded to jack off and shot my load on my belly.

I kept busy Sunday prepping for the week ahead and the day flew by. Before I knew it, it was dinner time and I was starving! I looked at my phone, it was 7:00. I also noticed a text. From Thomas. It was just a pic of a bathroom stall. I looked closer and I could see a load of cum on the wall. I decided to return the favor and jacked off on my kitchen counter and sent it back to him. I got a thumbs up emoji in return.

I had my dinner and got my stuff around for Monday. I couldn’t believe we were a week away from the end of the school year. I swear it was just winter break. I sat down to watch some TV and relax. Thomas texted. “Miss you. Hope it’s okay I say that”. I sent him a smiley and told him I missed him too. Big grin smiley back. I finished my brain dead TV watching and headed for bed. I curled up under the sheets and smiled as I fell asleep.

Monday started off with a bang, literally. I was driving to work and got rear ended at a stop light. Just what I needed. I got out of the car and the person behind me was just sitting there in shock. It was one of the students from my school. When I took a closer look I could see a cell phone on the dash. Stupid kids and their cell phones.

Both cars looked bad, but his car looked worse. He finally snapped to attention and got out of the car. When he noticed who I was his eyes got very wide and started apologizing profusely. I told him not to worry and as I looked up a police car was pulling up.

We finished with all the police report stuff and determined his car was not drivable. I could still drive mine so I offered to give him a ride to school. We went through the office and I let them know what happened so he wouldn’t be in trouble for being late. He was probably already in enough trouble with his parents.

I went to my room and tried to not think about the damage to my car. Thomas showed up as usual and as he walked by me he gave me a quick kiss on the cheek. He quickly changed his clothes and said he was running late for work. He left and I sat there smiling. What was happening?

The week flew by with the end of year school activities. Thomas seemed distracted by them all and was enjoying himself as he would run into my room, change and then run out. Each time he would give me a quick kiss on the cheek.
Finally, it was Friday, I didn’t see Thomas today, but remembered they don’t work at their jobs on the last day of school. The final bell rang and I was packing up my bag when Thomas walked in. He dropped his backpack, held his hands up like Rocky, jumped up and down and yelled that he was done!! I gave him a round of applause and congratulated him. He walked over to me and said, “ya, know what this means?” I shook my head. “It means that I am no longer a student here and you are no longer my teacher!” Then he stepped towards me and kissed me on the lips! He pulled away and had a huge smile on his face. Now I can officially say this. “Will you go out with me?” I grinned and nodded my head.

He smiled and said good, let’s go. Right now, I asked? Yup. Come on, you can leave your car here and I have it all planned. This reminded me about my car, so it was a good thing he was offering to drive me. I figured I could come back and get it later, so we headed out of the school and towards his car. He immediately put the top down and turned and looked at me. At the same time we said “dicks out” and took off out of the school parking lot.

He drove us back to the lake and as we got out he grabbed a bag from the back seat and we walked over to the dock. We sat for a few minutes before he turned to look at me. He took a deep breath and said he wanted to tell me something. I nodded. He said he thought a lot about what he was about to say, so to please let him finish before I said anything. I nodded again.

He took another deep breath and told me that he thought he was gay and had told his parents about him. They said they kind of figured it out a couple years ago. They said they just wanted him to figure it out in his own time. I started to say something and he shook his head and said he was not done. I shut my mouth and he took another deep breath and told me that he really likes me and would like to date me and have more sex with me and try new sex stuff and what did I think of that. Then he breathed.

I pointed to myself, asking permission to speak. He nodded his head yes. I smiled widely and told him I like him also. I reminded him that I was 30 years older than him and wanted to be sure he was ok with that. He was nodding his head. I told him I was concerned about what his parents would say. I don’t want to seem like the pervy old guy taking advantage of a younger guy.

Thomas couldn’t contain himself. He blurted out that he had already told his parents that he had a crush on someone, that he was older, and worked at his school. He said he didn’t tell them that we already did sex stuff, but that we spent time together talking about life etc. They asked for more details, but told me that who I dated was my decision and they just want me to be safe and happy.

I sat back a bit and couldn’t think of any reason why we shouldn’t date. I took his hand and brought it to my lips and kissed it. I smiled and asked him where he would like to go on our first official date. He smiled leaned in to kiss me and gave me a huge bear hug. We kissed some more and Thomas rubbed up my thigh and into my crotch. He pressed down on my bulge and I reached over and did the same. His cock head was sticking out the bottom of his shorts. I rubbed my thumb over his cock head and felt his precum dripping from his slit. We both looked at each other and said we should take this somewhere else before we get arrested for public indecency. Thomas grabbed my hand and pulled me up and towards his car.

As we drove around, yes, with our dicks out, I explained to Thomas that my car was out of commission. I was able to drive it to work this morning, but as I pulled in the parking the bumper fell off my car. I guess that meant I was without a car until I contacted my insurance and made arrangements to have my car towed and repaired.

I explained to Thomas what had happened and when I mentioned who had hit me, he told me he knew who he was. He blushed when he told me he always thought he was cute and had seen him in the locker room and admitted he was impressed with what he had seen. I shook my head and called him a little horn dog. What? He just seems so nice, and I may have seen him naked in the locker room and was curious about his dick. Curious?? Yeah, he is uncut, I had never seen one of those before, so I wondered how it all works. I smiled and said maybe we could find a way for him to figure that out.

Thomas smiled and said he would drive me home. His parents were out of town again and he was officially an adult and could do whatever he wanted. We headed towards my place and enjoyed the early summer afternoon. I turned to Thomas and gazed over his body. When I looked down at his dick sticking out of his shorts I reached over and wrapped my hand around it. He smiled. I unbuckled my seatbelt and leaned over the console and took his dick in my mouth. I rolled my tongue around his head and I felt the car speed up. I spit in my hand and started to stroke his dick as I sucked on his head. I felt his hand on my head and then felt the head of his dick swell and fill my mouth with cum. I swallowed as fast as I could and he unloaded his balls. I sat back up and re-buckled my seatbelt. I wiped the corners of my mouth and licked my fingers. I looked over at him and smiled when I said, “good sauce”.

We arrived at my place and I explained that this weekend was project weekend, so I would be busy getting my bathroom remodel going. He told me it was not a problem. He said he may have packed a weekend bag and would be my assistant. I laughed and said he truly was a horn dog! However, I told him that would be great as it would help me finish the project sooner than planned and I would happily pay him for his services.

I suggested we order some food and enjoy our evening before the work weekend. We ate our food and as we were cleaning up Thomas grabbed me by the hand and pulled me into him for a kiss. His hands were all over me trying to take my clothes off. I did the same to him. We were naked in seconds and Thomas pushed me back against the wall and told me he wanted to fuck me! I smiled and turned around to face the wall and pushed my ass out to expose my hole. He looked at me and asked if I really wanted to do it right here in the kitchen. I reached out and grabbed the bottle of olive oil and told him I wanted us to fuck anywhere and everywhere.

I poured the olive oil in my hand and spread around my ass and then rubbed it on his dick. I turned to face the wall and Thomas stepped up behind me. He grabbed his dick and aimed it between my cheeks. He pushed his head into my ass and I abruptly slammed back onto him taking his entire length in one motion. He grunted, and started fucking me immediately. It was only a couple thrusts and he told me he was going to cum. I told him to do it, to fill my ass. He thrust two more times and then buried his dick in me as he shot his load. I could feel his pulsing cock and then felt it slide out of me.

He told me he wanted to last longer, but the olive oil was really slippery and felt really good! I explained that our dicks have a mind of their own and to never apologize for cumming and personally, when a guy cums quick like that I take it as a compliment. It just proved he was enjoying my ass that much! I turned to kiss him and my hard dick was pressed between us. He grabbed the olive oil and poured it on my dick. He rubbed it all over my head and then started jacking me off. He was using both hands wrapped around my shaft and I started thrusting into his hands. It only took me a couple thrusts and I was shooting my load all over his hands. His eyes were fixated on my head getting covered in my cum. As I finished cumming he lifted his hands and licked them clean of cum. Mmmm, he said, Italian Sauce!

I told him we probably should head to the bathroom to wash off the olive oil and he grabbed me by the hand and led the way down the hall. I turned on the water and we both stepped in as the steam filled the room. We took our time washing each other and both enjoyed playing with each others soft, spent dicks while we kissed. The shower lasted a bit too long as the water started to become cold. We turned off the water, got out and dried each other off. I asked him if he wanted to watch a movie and he agreed, we went to my bedroom and got under the covers. I turned on a comedy and we snuggled together naked as we watched the movie. We both fell asleep wrapped together in each others arms.

The loud knocking on my door woke us both up with a start. I grabbed a pair of shorts and went to see who was at the door. It was the home store with my delivery. I opened the door and signed for the supplies and told him I would open my garage door and they could place all the supplies there. I closed the door and returned to the bedroom. Thomas was sitting up in bed and I let him know that the supplies were here and it was time to get to work. He smiled and looked down at my crotch and said he thought we should take care of that first. I looked down and hadn’t realized that I had morning wood. I guess that explains why I was getting such a strange look from the delivery man when I opened the door.

He crawled on his hands and knees across my bed and motioned for me to come closer. I walked towards him and he grabbed and lowered my shorts under my balls and took my dick in his mouth. He was getting much better and giving head and had most of my dick in his mouth and throat. I ran my fingers through his hair as he jerked and sucked my dick. After a few moments I was shooting my load in his mouth. He was able to swallow every drop. I told him it was his turn and he told me not to worry about it. That he had jacked off when I was talking to the delivery driver and showed me where cum was drying on his chest and belly.

We got dressed and began working on the bathroom. I was impressed with his skills as he knew how to use all the tools. We made quick work of putting up the walls in the bathroom and getting all the seams done before noon. We had a quick lunch then finished the bathroom to the point where it was ready to be tiled and add the flooring. I had expected this part to take me all weekend and now found that I had all day Sunday free.

I told Thomas and he suggested we spend the day at the lake. We could kayak and just hang out getting started on our summer tans. I agreed and lifted my arm as I noticed we both were extremely sweaty and had begun to smell. Thomas did the same thing and agreed. We decided to shower separately and while Thomas showered I ordered Chinese for delivery. A few minutes later I heard the doorbell ring. I thought that it was a very fast delivery. I opened the door and saw Sean, the boy who had run into me, standing in front of me.

Sean was about 5’ 11” with a very clean cut look about him. He looked as if he wasn’t sure what he was supposed to say, he looked back at my driveway and I saw his dad standing at the car. He looked at me and started telling me how sorry he was for the accident and admitted that he had been texting when the accident happened.

He explained that his dad had grounded him and as part of his grounding was that he was to offer his services for the next month. Whatever you need done, painting, landscape, cleaning, or whatever. He said that his dad owned a construction company and he had worked with his dad for several years and could do all kinds of work. I told him that wasn’t necessary, as accidents happen, but he said it was non-negotiable and the only way he was going to get ungrounded was to complete his dad’s punishment.

I looked out at his dad and waved at him. His dad approached and let me know that he was very disappointed in his son and wanted to make sure he learned a lesson from this. I thanked him and mentioned that I did have several projects I was planning for the summer so I actually could use an extra set of hands. He told me to let his son know when to be here and he would make sure he was on time and then walked back to the car.

I told Sean that I could use him the following week with some landscaping, and then next weekend as I was remodeling a bathroom. As I said that Thomas came walking into the living room drying his hair completely naked. He stopped rubbing the towel around and as he placed it around his shoulders he noticed Sean standing in the doorway. He quickly pulled the towel down in front of his crotch and gave a half wave to Sean. “Hey, um, what’s up?” I looked at Sean who’s eyes had doubled in size and said that Thomas was here helping me as well and we had just finished working for the day and he was cleaning up before heading home.

Thomas said he was going to get dressed and turned and headed back to the bedroom, leaving his ass exposed as he walked away. I looked back at Sean who was staring at Thomas’ ass. I cleared my throat and Sean’s face turned red and I said I would see him Monday morning at 9:00am. He nodded and shoved his hands in his pockets as he walked back to his dad’s car.

I closed the door and Thomas came back in the room, still naked. WTF he said, why was Sean just standing at the door? I explained everything and he said he can’t believe that Sean just saw him naked in my house. I told him I thought Sean liked what he saw and it appeared he had sprouted wood while he was staring at his ass. His eyes shot open wide and said, really? I nodded and laughed at Thomas as he blushed and smiled.

I mentioned to Thomas that I had some friends who lived on the lake and they had a boat we could use for water skiing and tubing. His eyes lit up and said he loves skiing. I called them and asked if they would be around on Sunday and if they would like some company. They loved the idea and we made plans to be at their place mid morning and would spend the day on the lake.

I hung up the phone when I heard the doorbell ring. This time it was the Chinese food. I brought the food in and set it on the counter. Thomas walked back in the room, I watched as his dick flopped back and forth as he walked. It truly was a beautiful piece of meat! When I stopped gawking at his dick and looked up at his face he was smiling. You like what you see? He asked. I do! And I am not just talking about your dick! He blushed. I smiled and said, let’s eat.

I ordered a variety of food and we made up our plates and went to the table to eat. As we sat down I told him I wanted to make sure he knew that the friends we were meeting tomorrow were a gay couple and very out. I wanted to be sure he would be comfortable with that. He nodded his head with his mouth full of egg roll.

Also, it would not surprise me if they made sexual comments and innuendos about his age. He smiled and told me it would be ok. He thought he would be able to handle it. We finished our dinner and cleaned up. We went into the living room and each had a beer. Thomas leaned against me and said it felt so good to be here with me and he really liked me and that I was a great guy. I hugged him and said I felt the same way.

He got up off the couch and took my hand and led me to the bedroom. He stripped off my clothes and then his own and we laid down in bed. It was obvious he wanted to be in charge of what we were doing so I let him do with me what he would. He was so gentle. He explored every inch of my body. He licked my lips, my neck, my chest and nipples. He continued down my body and went past my penis. He continued down my legs and when he got to my toes he sucked each one in his mouth, one by one.

He came back up my body and kissed me gently on the mouth. He took a deep breath and then asked me if he could try something. I told him he could do whatever he wanted. He rolled me over onto my stomach. He slid down between my legs and then I felt him between my cheeks. He gently licked and then pressed in harder. I lifted my ass and reached back to spread my cheeks. He went deeper and I moaned with pleasure as he ate my ass.
He came off my ass and moved up to lay on me. He whispered in my ear that he was so nervous about doing that. He said he thought it would be gross, but he really enjoyed it. I whispered back that I enjoyed it also.

I could feel his dick between my legs. I spread my legs wider and he raised himself up. Do you have any more of that lube?, he asked. I stretched out my arm and pointed to my night stand. Thomas reached over and opened the drawer and pulled out my bottle of lube. I heard him click open the bottle and felt a chill as he poured some on my hole.

I waited a few more seconds and then felt Thomas’ wet dick press into my ass. He entered me slowly, but didn’t stop. He pressed in until every inch of him was in me. Then he laid back down on top of me. We laid motionless, connected as one body. Slowly he started moving his dick in and out of me. Long movements, pulling his dick almost all the way out and then all the way back in. I had never felt this sensation before. He was just enjoying the feeling of the fuck and not just trying to get off.

He pulled himself up and told me to roll over. I started to move, but he held me still. “I don’t want to pull out”. I lifted my leg and he rotated my body around. It felt incredible as my ass moved around his dick. When I was on my back he pulled me towards him. His dick was again buried in my ass. He stared down at me and reached for my hands. He pulled them up and placed them on his nipples.

He adjusted himself a bit, readying himself. I flicked his nipples and he tilted his head back. I took both nipples between my thumb and index finger and pinched. He groaned and I pinched again. Twisting this time and not letting go. His head snapped up and he looked down at me. His eyes were dark, he didn’t just groan, he growled.

I felt his hands tighten on my thighs as he pulled me down on his cock. His first thrust was deep and hard, that was followed by more. He was fucking the shit out of me! I had a difficult time keeping a hold of his nipples, but did my best. Thomas continued to pound me. I felt my balls tighten and I shot my load. I came hard and felt it hit my face. Thomas was thrusting and sweating. I can’t describe the noise he made, but from the throbbing in my ass, it was apparent he was cumming. His animalistic noises were such a turn on.

I let go of his nipples and Thomas stopped growling. His thrusts slowed. He shook his head a bit and his eyes returned to their natural color. He looked at my face and then down my body. He looked back at me and grinned. His arms were shaking and then he collapsed, part of his body was on my and the rest off to my side. His dick still in my ass. Fuck, was all I heard before he fell asleep.


I woke up first and decided to wake Thomas up with a blowjob. I quietly crawled down the bed, under the covers and took his dick into my mouth. It responded quickly and I was rewarded with his load within a couple minutes. I came up from under the covers and Thomas had his eyes closed, but had a huge smile on his face and said that he would love to wake up like that every day! Duh, who wouldn’t!

He rolled over and pushed me onto my back and slid down my body. Your turn, he said and proceeded to suck my dick into his mouth, this time taking the whole thing into his throat. I moaned loudly as this happened and he moaned back causing his throat to vibrate on my dick. It was too much and I shot my load deep into his belly. He pulled off and was so excited that he finally took me down his throat. That is so cool, he said. I really liked how it felt when it went past my tonsils. I agreed and said he was really getting good at that!

We got out of bed and started getting ready to go to the lake. I realized I didn’t have a car and asked Thomas if he was ok to drive as it would take us about an hour to get there. He said no problem, but only one condition - DICKS OUT and grabbed his crotch. I laughed and we loaded up and headed to the lake.

Comments / Reviews

Posted by Mike Nice story, I want to try it find me there gay.mine.yoga
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