Mr. Shepherd's Summer Vacation

The Weekend-------

I awoke first and had to take a major piss. I slid out of bed and sat on the toilet to relieve my bladder and empty my ass. I felt very wet back there and needed to clean up a bit. I finished and went back and crawled under the covers with Thomas who was still sleeping soundly.

I slid my hand down his body and found a semi erect penis. I wrapped my hand around it like a security blanket and fell back asleep. I awoke a second time to Thomas moving away from me. His hard dick sliding out of my hand as he ran to the bathroom. He returned and said he had to pee so bad, he almost didn't make it as he couldn't control the stream as he had such a hard on.

He jumped on top of me and told me that last night was incredible! He couldn't believe that he finally fucked someone! I never imagined I would lose my virginity to a dude! Do you think girls will let me fuck them that hard or am I going to have to be all gentle and shit? I smiled and said based on my experience, girls can get into some rough sex, but usually they are more interested in the slow passionate type of love making.

He jumped off me and flopped onto his back. I noticed his dick was filling out and he looked at me and asked if we could do it again? I kissed him and crawled on top of him. I found the bottle of hand lotion and slathered his dick. I raised my body up and positioned myself over his dick and slid myself down his pole. His face told me that he couldn't believe this was happening again. He kept looking down at his dick as it disappeared into my ass.

I placed my hands on his chest and tried to pinch his nipples, but my hands were too slippery with lotion so I just massaged his chest as I rode his dick. I didn't slam down on him or anything, I just rode up and down his long shaft. I never looked at him, keeping my eyes closed. I focused on his dick in my ass. Taking every inch. Then started quickening my pace. He started thrusting to match my bouncing. He was moaning loudly and then shoved himself into me as I dropped down on top of him. I could feel his dick expand and contract as he emptied his second load into me. I laid on top of him and he wrapped his arms around me and pulled me tight.

After our heart rates were back to normal I sat up and stared into his eyes. I started to say I should get going, but he cut me off and asked if I was hungry. I said yes, and he told me he would go get us something to eat and to take a shower and freshen up!

He ran out of the room and I heard him opening the fridge and making a bunch of noise in the kitchen. I got out of bed and walked into the master bathroom and turned on the shower. There were a few framed pictures of his mom and dad on the vanity and I felt awkward thinking about all we had just done in their bed. The steam started coming from the shower, so I stepped in and let the warm water run down my body. I could feel where cum had dried on my chest and could feel Thomas' load running out of my ass and down my legs.

The shower had a hand held unit and I used it to clean all of my crevices. I was spraying water up my ass as Thomas came in and said breakfast was ready. He paused as he watched what I was doing. I laughed and told him this is just part of the clean up process as I didn't want to feel his cum oozing out of my ass all day. He blushed like he got caught watching something he wasn't supposed to and turned and left the room.

I got out and dried off. I walked out of the bathroom wrapped in my towel. When I got to the bedroom Thomas was laying naked on the bed with a tray of food next to him. I dropped my town and crawled on the other side of the tray and took a piece of fruit and fed it to him. He did the same and then we laid back and relaxed as we ate our breakfast. Thomas was quiet as we ate. I tried not to worry about what he was thinking. Does he want me to leave? Does he regret what we did? Why do I always think of the negative?

He jumped up and said he needed to shower and smelled his pits to demonstrate that he thought he was beginning to stink. He turned and bounced into the bathroom and I heard the water turn on. He was in there for a few minutes when he called for me to come in. He was holding the sprayer and asked if I could show him what I was doing earlier.

I told him that he probably didn't need to do that as he hadn't gotten fucked and usually guys only did that if they were planning on getting fucked or cleaning up afterwards. He looked up at me and smiled, I thought maybe I want to try it and see what it feels like to get fucked as it felt so awesome to fuck! I told him I would show him the cleaning out part, but we would talk about the other when he was out of the shower.

I stepped into the shower with him and held the sprayer up to his ass. He fell against the wall and moaned loudly. He looked back and down at what I was doing and then reached down and took a hold of his dick and started jacking off. I pulled the sprayer away and he turned and told me to put it back, that it felt amazing! I sprayed him some more, but then pulled it away again and quickly buried my face between his cheeks. He fell against the wall and I shoved my tongue to his hole. His hands reached around and pulled my face deep between his ass cheeks.

His moans echoed through the shower and I could feel him beating his dick as I kept my face buried in his ass. His moaning became louder and then I felt his pucker pulse. I reached up and pulled on his nuts. Another loud moan/grunt as he pushed his ass back towards me and shot his load all over the shower wall. He fell against the wall and as I stood up I wrapped my arms around his waist, he leaned back on to me as he came down from his orgasm.

He reached over and turned off the shower and we both stepped out and grabbed towels to dry each other off. I grabbed at his dick, but he pulled away and said he was still sensitive from cumming. I, on the other hand, was sporting a very hard dick. Thomas kneeled down and took the head of my cock in his mouth. He rolled his tongue around and around the head. Then he started taking it in his mouth. I moaned loudly as he got about half my dick in his mouth. He used his hand to jack me as he sucked what he could into his mouth. I placed a hand on his head and told him I was about to cum. He sucked harder and as I shot my load, his lips squeezed around the head of my dick and he drank my cum like a shake through a straw. He milked my dick until there was nothing left. He stood and kissed me and said to follow him.

We left the bathroom and we walked out of the master bedroom down the hall to his bedroom. Quite the typical boys room. Clothes thrown around and posters on the wall of Star Wars and Video games. He went to his dresser and pulled out a pair of underwear and then a pair of shorts and threw them over to me then grabbed some for himself. Then, he walked over to his closet and grabbed a couple t-shirts and threw me one. He said that he wanted to take the car out and figured we should probably be dressed if we were going to drive around town.

I put on the clothes and told him that I would love to go for a drive, but really needed to get home and had a few errands I needed to get done. He told me that worked for him and he would be my personal chauffeur for the day. He reached up in the closet and grabbed a baseball cap, put it on and told me to get my stuff and he would meet me in the car. I asked about my car and he said just to leave it where I parked and I could pick it up later. I gathered up my clothes and headed out the back door to find him putting the top down on the car. I got in the passenger seat and noticed he already had his dick sticking out of the side of his shorts. He smiled and put it in drive and pulled out of the driveway.

The drive to my place took just about 30 minutes. A bit quicker than when I drove as Thomas was exceeding the speed limit for most of the drive. I had a modest town home, but loved the amenities the community offered. We went inside and I showed him around. I showed him the guest room and the bathroom that was attached. He asked what had happened, and I told him there was a water leak and I was in the process of re-doing the entire thing. Currently, it was a blank slate and two walls were down to the studs. He looked around some more and said he is pretty good with his hands if I wanted his help. I thanked him and told him he would be helping me today as I needed to pick up a few supplies for the remodel.

We went back to his car and I told him to head to the local home store where I needed to pick some tile and other pieces for the bathroom. We buckled up and sure enough, Thomas reached down and pulled out his dick. I smiled and decided why not and pulled my shorts aside and let my dick free. He smiled and we were off with a mighty, DICKS OUT! I have to admit, the breeze did feel nice!

We got to the home improvement store and I told him I would need a minute before I could get out of the car. He looked down and noticed my hard on. He told me no worries as he had the same problem. We started talking about the remodel and my plans and within a few minutes we were both under control and able to go into the store.

I met with the design consultant and chose the tiles, tub, commode and vanity that I wanted and set up a date for delivery. Then I went to the building area and ordered some sheet rock and other supplies I needed to be delivered the following weekend. I was trying to keep within a timeline and needed to get walls up before I would be able to start the rest of the remodel.

We were done with what I needed to do, and I told him that I needed to use the bathroom, so I headed towards the back of the store and Thomas followed me. We got in the restroom and Thomas pushed me into the end stall. He closed and latched the door and pushed me against the wall and started kissing me. Dude, seeing your cock all hard in the car has had me so horny I wanted to bend over and suck you in the parking lot. I pushed him back and smiled. Then told him to hold that thought, as I really did need to pee.

I stepped up to the bowl and pulled out my semi hard dick and began to pee. This must have triggered Thomas as he stepped up next to me and pulled out his dick and started peeing with me. Of course we had a stream/sword fight as we pissed. Just something that guys do.

We were just finishing up when we heard the restroom door open. Thomas jumped up on the commode and I quickly turned around and sat on the toilet like I was taking a dump. That way if the guy looked under the stall he would only see one set of feet. The guy went in the stall next to us and proceeded to do his business. Not very romantic, but didn't stop Thomas from nibbling on my ear and kissing my neck. I had to keep myself from making noise as my neck is a spot on my body that really gets me turned on.

Our neighbor finished, flushed and walked out of the stall. He stopped and washed his hands and then left the restroom. Thomas and I got off the toilet and both had our hardons sticking out of our shorts. Thomas sat on the toilet and grabbed the shorts to pull me towards him and began sucking the head of my dick. He tried to take more of my dick down his throat. He didn't get it all the way, but did much better than the first time. I was a bit nervous and came quickly. He swallowed every drop and stood up to kiss me. We rotated our bodies and it was my turn to return the favor.

We exited our stall, went to the sink and adjusted our clothes and washed our hands. We left the restroom and noticed a man do a double take as WE walked by. I had to wonder if he was the guy who was in there before and how he only thought one guy was using the bathroom, but two came out. We left the store and I told Thomas that I was hungry and we should go get some lunch.

We drove through a fast food place and I told Thomas to head down the road and make a left. We drove for a few minutes and I told him to turn again and right in front of us was a beautiful lake. This was the access road.I had come here many times to kayak and it was never busy. He pulled into a parking spot and we walked over to the lake and sat down on the dock and ate our lunch.

When we finished our lunches Thomas looked at me and asked what I wanted to do next. I told him I really liked spending time with him, but I did have some work I needed to do at home for school the next week. I realized I had left everything in my car, which was back at his place. He said no problem. Let's swing by your place so you can get some stuff and we can go back to my place and you do your work and I will do my homework. We threw away our trash and got back in the car and Thomas looked at me and said "dicks out"!

We drove back to my place. I ran in and got a change of clothes and some toiletries, along with a couple things we might need, and went back to the car. Thomas had reclined his seat a bit and was getting some sun. I looked down and he still had his dick out and was oozing precum from his slit. I got in the car and told him my neighbors could see in the car. He sat up, looked around, and waved. I shook my head and we were off again.

We got back to his place and we got our stuff around and sat at the dining room table to do our work. We worked for a couple hours and both said we were done at the same time. Thomas put his books etc in his backpack and set it on the floor. He headed to the kitchen and grabbed us each a beer. He waved for me to come to the living room and we both sat on the couch drinking our beer. He looked at me and then looked away then looked at me again. He took a deep breath and then said, can I ask you something? Of course, anything. I think we don't have any secrets at this point. He laughed and said good point.

He looked down and then asked me if I thought he was gay. I asked him what he meant and he said that we had been doing a lot of gay sex stuff, so does that mean he is gay? I told him I couldn't answer that question for him, but that I could say he is a normal horny male enjoying getting his rocks off. He smiled and then asked if he could ask me another question. I just looked at him and raised my eyebrows. He looked down and asked me if I liked him. I immediately told him yes, that he was a great guy.

He shook his head and said no, like, do you like, like me, like you would like a boyfriend to like you? I shook my head at how many times he used the word like. I asked him to be sure. Are you asking if I like you as a boyfriend? He nodded his head, but didn't look at me. I grabbed his chin and lifted his face. I told him I would be lucky to have him as my boyfriend, but he was a student, so we wouldn't be able to date out in public or anything. He nodded his head and agreed, but said school was almost out and then it wouldn't be an issue. I hesitantly agreed, then looked him in the eye and asked. Thomas, are you gay? He stared at me and tears started to form in his eyes. He said he didn't know, but he really liked all the stuff we have been doing and how it feels to be with me. He has dated girls and it never worked out, but he always blamed that on his dick size, but he never felt like he does right now with any girl he had dated.

I took his hands and told him he didn't need to make any decisions right now. He was young and had the rest of his life to figure out who he was and what he wanted. He looked at me and said that he thinks he knew who he was and who he wanted, then leaned in and kissed me before I could respond.

I let him kiss me and then felt his hands roaming across my body. He found my nipples and pinched them hard. I yelped and told him that would get him in deep trouble if he kept that up! He smiled and pinched them again. I jumped up and pushed him back on the couch. I lifted his legs up over my shoulders and positioned myself like I was going to fuck him. He was laughing the entire time, but stopped when he could feel my hard bulge rub against his ass. I lowered his legs and leaned down to kiss him. Rubbing our hard dicks together through our shorts. He looked in my eyes and told me to fuck him.

I backed away and asked him if he was sure. He nodded and I stood up and took his hand and led him to the bedroom. We stripped our clothes off and climbed back in bed. We began kissing again and he pulled me on top of him then raised his legs up like I had done to him before. I pulled off of him and went over to where I had placed my overnight bag. I pulled out my dopp kit and opened it up to get a bottle of lube. I went back to the bed and showed him the bottle. I took his hand and put a small drop on his finger. He rubbed it around and I told him this would help better than lotion. We got back into position and I slicked up my dick and rubbed some lube into his ass. He moaned quietly as my fingers probed inside him. I made sure to press against his prostate to excite him even more. Every time my finger hit it his body shook.

I got between his legs and put my dick at his entrance. Our eyes were transfixed on each other. I began to push my dick in him and his face showed the pain. I backed away and then tried again, telling him to breath and push out when I was pushing in. He took several breaths and I tried again. I could feel my head begin to enter, but then his ass clamped shut again. He let out his breath and said I was too thick.

I jumped off the bed and went back to my bag. I returned to the bed and showed him my shiny silver bullet vibrator. His eyes got huge and I told him this should slide in easily and help loosen him up. He nodded and I placed it at his hole and applied some pressure and sure enough it slid right in. His mouth dropped open and his eyes were squeezed shut. I kept telling him to breath and after a few seconds he opened his eyes and I could feel the vibrator sliding in and out of him easier.

I slid it in and out a few times and then turned it on. He about shot off the bed and grabbed the hand that was controlling the vibrator. I stopped sliding the vibrator in and out and just let it be in his hole. He settled down and I started sliding it in and out of him as it vibrated. I kept this up until I felt his entire body relax, his legs open wider and the vibrator slide in and out without any resistance. I kept this up for a few more minutes and then pulled it out. He had his eyes closed up to this point and opened them as if begging me to put it back in.

I repositioned myself between his legs and put my dick against his hole. This time as I pressed the head of my dick against him he pushed back and I slid in. First the head popped through his hole and he gasped, then I pushed the rest of my dick into his virgin hole. We had locked eyes and I watched his face as he lost his virginity. The look of pleasure was apparent on his face. I was going slow and letting his ass get used to my girth. He closed his eyes and wrapped his legs around me and then I felt his hands grab my ass and push me into him. He looked at me and nodded and said "fuck me". "Hard" I started speeding up and his moans increased. "Harder, fuck me harder!" I pulled him down and my cock and shoved me into him and started pounding his ass. He was so tight I only lasted a couple minutes. I looked down at him and said I was close. I felt his legs tighten around me and he nodded again, "cum in me, please" "Please cum in me!" "Please!!" On his third please my dick released and I filled him up with my cum. His eyes rolled back in his head and I felt wet between us. I looked down and his cock was shooting a load between us. He had cum, hands free. I collapsed on top of him and nuzzled in his neck placing my entire body weight on top of him. He kept his legs wrapped around me and gently stroked my back with his hands as my dick slipped out of his ass.