Mr. Shepherd's Summer Vacation

Mr. Shepherd

My name is Erik Shepherd. I am a 38 year old, divorced, high school teacher. I am 6'1, 230lb., Dad Bod, above average, 7" cock with ample girth. I left my wife after coming out to her 6 years ago. We tried to make things work, but in the end, it was better that I leave.

I am a Behavior Specialist at a small high school located in SW Michigan. This is a low income school with several students having behavior issues due to their life circumstances. My job is to help them learn how to deal with their current situations and prepare them for post secondary life, hopefully keeping them out of jail.

Throughout the school day I work with a variety of students. Mostly students who should have graduated, but needed a few more credits to receive their diploma. The students are either 18 or 19 years old, however, I do not, nor have I ever, acted upon any fantasies about students as I do not want to end up on the evening news as the perv teacher that took advantage of a student.

We were in the final stretch of the school year and today started off nicely with no major behavior issues to resolve. A student, Thomas, came into the room and asked if he could change into his work clothes in my room. Thomas was 5'9, slim build with dark blonde hair. He normally uses the staff bathroom, but it was occupied. I have an area towards the back of the room that is more private and on a few occasions other students have done a quick change back there. Usually, the students just change from pants to shorts for PE and they are done in a couple seconds.

Today was a bit different. Thomas was changing all of his clothes as he had come from PE and was leaving school to go to a job. When I glanced back he had removed his shoes, his pants were undone and his shirt off. He was putting on deodorant and adding some Axe body spray. A bit too much in my opinion and mentioned it to him. He looked up at me and laughed.

He stood there for another second putting his deodorant and spray away then put his thumbs in his pants to pull them down, and in a blink of an eye he was naked! Oops, his underwear came down with his pants. He quickly tried to grab his underwear but they had become twisted in his pants, so he was bent over squirming around and I couldn't help but notice his dick! Holy HELL! He was huge!! The fact that he wasn't very tall only added to how big his dick looked. His dick hung several inches down and over a set of massive balls and there it was flopping around as he tried to recover his underwear.

All of this happened in less than a minute, but definitely long enough to leave an impression on my brain! I had known this student for 3+ years and definitely did not ever imagine a dick like that on a body like his!

When he finally got his underwear untangled and pulled up he looked over at me and his face was flushed red and apologized for flashing me. I laughed it off and said no problem, but was glad no one else walked in during his strip tease. He laughed, but said, hey, if ya got it, flaunt it! I wondered how I should reply, and decided I would go for it and said, "Well, you definitely got it!". And gave him a wink.

I turned away and he finished getting dressed for his job and as he walked out of the door he looked back at me, "Next show at 11:30" he said. I laughed, but have to admit, my brain started imagining him doing an actual strip tease.

I was pretty busy after he left with a couple meetings. I looked at the clock and it was 11:30! I had a quick thought that I was bummed he didn't come in to change again, I figured he was just joking and that it was just my pervy brain making it into something more than it was.

It was lunch time, so I went to the back of my room where I have a mini kitchen set up and prepared my lunch. I had just pulled my food out of the microwave and turned around and bumped right into Thomas. Not only did I bump into him, I dumped my lunch down the front of him. A full plate of spaghetti went all over his shirt and I watched in horror as it slid down his body.

We both stood there dumbfounded and then he started laughing! I was mortified that I had done this and apologized as I looked around for a paper towel or something to give to him to clean up. Thomas was not upset and said he could just change back into his other clothes.

I told him the school had a washer and dryer and I promised to get his clothes clean or I would replace them. He thanked me and went over to where he had left his backpack and pulled out a change of clothes. I was on my hands and knees cleaning up the spilled spaghetti and when I looked up he had already removed his shirt and was just starting to pull down his pants. I quickly looked down and finished wiping up the floor.

As I stood up Thomas was looking at me. "I have a bit of a problem." he said. He looked down at his underwear. During the removal of his pants the spaghetti had gotten all over the front of his underwear as well. I told him it was no problem and I could get those washed also. He shrugged his shoulders and pulled them down and off his body and threw them with his other clothes.

He stood there naked for a second and looked over his body for any other bits of spaghetti, which he found on his belly and cock. He used his fingers to wipe up the mess and then licked his fingers clean. My mouth had dropped open at the sight and he looked up at me and simply stated "You should never waste a good sauce!" I think I actually drooled as he said this.

He turned his back to me and bent over to pick up a pair of shorts. He rummaged through his backpack for a second. "Crap, I don't have another pair of underwear, guess I am going commando." He said, He slid his shorts on over his beautiful ass and then grabbed his t-shirt and slid that on as well.

He turned around and sat in a chair to put on and tie his shoes. He crossed his leg to tie his shoe and his shorts fell open, I had a perfect view of his dick. He shuffled his legs to tie his other shoe and I snapped myself back into reality.

He gathered up the dirty clothes and brought them over to me. I told him I would have them ready for him by the end of the day and he could come back and pick them up before heading home.

I headed to the utility room and when I returned I found him still sitting at a desk playing on his phone. I asked why he hadn't gone to class and he blushed. He said he started to, but then realized he kinda had a problem. I asked him what it was and he blushed some more and looked down at his crotch and back at me. He said he didn't have any underwear on and that when he walked in these shorts things moved around quite a bit and it was pretty noticeable. Then he stood up and shook his hips back and forth and sure enough it was VERY noticeable.

I blushed and told him that I understood and would contact his teacher and ask that he be allowed to stay with me to do his work in my room due to some personal issues. He laughed and thanked me with a huge sigh of relief. He said guys always talk about wanting a big dick, but when you actually have one, it can be a bit cumbersome. I laughed and replied sarcastically "yeah, I know the struggle". He smiled.

We sat for a bit and I said his clothes were probably ready to be put in the dryer. I suggested he come with me to change his clothes over, but he just looked down and said he was having a moment and it would probably be illegal to walk around school in his condition. I looked down at his crotch and sure enough he had a huge tent in his shorts. So, I went to move his clothes into the dryer by myself. When I came back in the room he quickly pulled his hand out of his shorts.

He blushed and apologized. It's just hard to ignore my dick when it's hard and loose inside shorts like this. It's like the material is making me even harder! I just looked at him and said it was all good, just us guys here. He seemed relieved and went back to his class work.

A few minutes later I glanced over and his hand was back in his shorts. Not moving too much, but he obviously had his hand around his dick. A second later he took a deep breath and said he couldn't handle it. My dick is so fucking hard it is driving me crazy! I have to bust a nut or I am not going to be able to get on the bus home.

Admittedly, I wanted to offer to help him out with his problem, but to keep it professional I told him I was going to go check on his clothes and would be gone for several minutes. He looked at me and then smiled. I got up and walked out of the room. I imagined him quickly ripping off his shorts to masturbate and release his load and felt a surge of blood flow to my penis.

I stayed gone for an acceptable amount of time and as I walked back into the classroom he was sitting at his desk reading a book. He looked up at me and smiled with a flushed face. I smiled back at him and asked if everything was all better. He smiled again and turned the page. As he turned the page he brought his hand up to his mouth and licked the back of his hand. "I told you, ya shouldn't waste a good sauce!" My mouth fell open and he just laughed.

I told him his clothes were not dry yet, but it shouldn't be much longer. He nodded and said he didn't mind and that he preferred working in my classroom anyway as he could focus better without being distracted by other things.

The next hour went by and we both kept to ourselves. I went down to get his clothes and brought them back to him. I said I would give him some privacy so he could change. He laughed and stated at this point it wasn't a big deal as I had seen him naked and let him jack off in the room, so at this point, seeing him change his clothes wasn't an issue and with that he stood up and dropped his shorts exposing a very girthy, meaty, piece of meat that made my mouth water.

He grabbed his dick and gave it a squeeze. He looked over at me and giggled, "watch this", he said. He proceeded to make his dick do a helicopter motion. I wondered if he was going to take off as the propeller spun around! He stopped and I could tell his dick had enlarged a bit. I laughed at him and told him to get dressed. Boys are all the same!

The bell rang, Thomas left, and in seconds I was in the staff restroom jacking my dick with images of Thomas, his dick and all the transpired during the day.

The next few days were normal. I didn't see Thomas until Friday when he said the restroom was occupied and needed to use my room to change again. I nodded towards the back of the room and he went about getting changed for work.

I looked back a few minutes later and I saw him tuck his dick into his pants, it appeared he was going commando. He looked at me and said he had gotten very sweaty during PE and his underwear was wet. I told him I could wash his gym clothes while he was at work, so he would have underwear when he returned to school. He thanked me and handed me a pile of sweaty gym clothes. The aroma took my breath away and I felt my cock pulse.

Thomas left for work and I headed to the utility room. Before dropping his clothes in the washer I grabbed his underwear and held them up. They were visibly damp from sweat, but there was also a very noticeable wet spot in the front. I pulled the underwear to my nose and took a deep breath! His scent was incredible! My dick hardened quickly in my pants.

I thought about it and decided as I was going to wash them anyway I may as well have some fun. I locked the door and then I opened my pants and wrapped the underwear around my dick and began to jerk off with them. The excitement was so much I only lasted a few seconds and then blasted my load into his shorts. I quickly cleaned up my dick and threw the underwear in the washer, zipped my pants back up and headed back to class.

Thomas returned from work a while later and showed up to change out of his work clothes. I had his clothes ready for him and when I looked at his crotch there was a very noticeable bulge. He saw me looking and said he is lucky that he wears an apron at work, or the customers would have been getting a show as he walked around the restaurant.

He hesitated, took a deep breath, then asked if I minded if he took care of his teenage moment before changing his clothes. I smiled and told him I had to run to the office and would be gone for a few minutes so to take his time getting changed. He had a huge smile on his face and I left the room.

When I returned he was fully re-dressed and had his work clothes in a pile on his desk. He asked if I would be able to wash these clothes. He said he may have made a mess while changing his clothes. He lifted the shirt and there was a huge load of cum all over the front. I gasped a bit as there was so much and asked him how long it had been since he shot his load. He blushed and said he had jacked off before school, and this was a normal load for him. I guess with a big dick comes a big load! I just shook my head and told him to leave his clothes where they were and I would have them ready for him Monday.

I took his clothes home with me and used them to jack off multiple times over the weekend. I put his shirt on me, and laid them out in my bed as if he was next to me. I even humped his pants like I was fucking him. I came so many times I lost count. I don't think I had jacked off that much since I was a teenager. I finally washed his clothes Sunday night and had them ready for him Monday.

Thomas showed up Monday and I handed him his clothes. He went to change but paused a moment, took a deep breath, and asked if he could talk to me in the back of the room. We walked back to the private area and he said he had a problem with his dick and would I take a look. I asked him if he had talked to his parents and he shook his head and said he can't talk to them about this kind of stuff.

I agreed, I mean he had a concern. I was just helping out. Not perving on seeing his dick, right?? He opened up his pants and pulled out his dick and it was very, very red and chaffed. I kind of laughed and then asked him if he had jacked off over the weekend. He blushed and looked down and said he kind of went off the deep end this weekend as he was home alone and felt horny all weekend and admitted he jacked off more than normal. Having been busy with my own dick over the weekend I had the same problem. I just told him he needed to give his dick a break for a few days and it would be back to normal.

Thomas came and went throughout the week and we chatted more and more when he changed his clothes. He did not even attempt to hide his dick as he changed and would stand naked while he applied his deodorant and body spray. His dick flopping around with every movement.

By the end of the week he said his dick was back to normal. He said it was a good thing too as he needed to bust a load or was going to go crazy! He told me it seemed his dick was hard more often than it was soft. He grabbed his bulge to make his point. A very hard penis was struggling to fit within the confines of his pants. I laughed at him and said he is a normal boy. He scowled and said he wasn't a boy. He was a grown ass man and just turned 19 this week.

I wished him a happy birthday, but he didn't seem excited. He shrugged and stated that it really wasn't a big deal. He had broken up with his girlfriend, his parents were out of town, and they would be celebrating when they returned. He figured he could guilt his parents into a better gift as they weren't home on his actual birthday. He thought he was going to get some from his girlfriend but she told him that she just wasn't ready and he was too big to be her first. He said he would just spend the weekend at home alone again and jerk off, but try not to overdo it again and rub his dick raw!

I felt bad for him and told him I wanted to buy him lunch, he said thanks but that he had eaten at work, but he would be available for dinner, the groceries his parents left for the week were running low and choices were limited. Not a normal thing I do I thought, but it was a Friday and I would have to eat, so, I agreed and told him I would meet him at the local pizza place at 7:00.

We showed up at the same time and entered the restaurant together. We talked about his work and school and he said he was very ready to be finished with high school and get away from all the drama and cliques. We enjoyed our meal and I excused myself to pee and headed for the restroom. I barely made it to the urinal when Thomas walked up next to me. The bathroom was small and there were only two urinals right next to each other without a divider. We both pulled out our dicks and let our stream flow.

He finished before me and gave his dick a few shakes. He held out his dick to show me it was back to normal and ready to be abused again. Then he looked down at my crotch. I was just finishing up and was shaking my dick. He said that I was shaking it too much and more than two shakes meant I was playing with it.

I have to admit, I had plumped up a bit when he was showing me his healed dick, so I was a bit bigger than my normal size. I am definitely a grower! I laughed and said I guess we all do it and I knew for sure he does as I have seen the evidence! He laughed and tucked his dick back into his pants. I noticed he was commando again.

We washed our hands and headed back to the table. I paid the bill and wished him a happy birthday and was ready to leave. When we got to the door we both noticed it was raining pretty hard. I asked him how he got to the restaurant and he pointed to his bike chained to the bike rack. I shook my head and said he should just leave it and I would give him a ride home. He agreed and we made a dash for my car, getting very wet along the way.

He only lived a few blocks from the restaurant so we made it to his house in no time. He mentioned he wanted to get inside and get out of his wet clothes and rubbed his hand down his body and across his crotch where I could see the outline of his dick. I agreed, but said I would have to wait as I lived a good 40 minutes from the school. I would have to turn the heat up and blow dry. He told me I could come in and he would throw my clothes in the dryer. It was only fair considering all the help I have given him with laundry over the past few weeks. He didn't give me a chance to respond and told me to come in and get out of the car, I shrugged my shoulders and took off after him. The rain was still coming down pretty hard so we got even more wet as we headed to the house.

When we walked in the back door we were in the mud room. The washer and dryer were right there and he said we could just take our clothes off here and throw them in the washer for a quick spin cycle before throwing them in the dryer.

He didn't hesitate and started taking off his clothes. I on the other hand felt very awkward and wasn't sure what to do. He struggled getting his wet shirt over his head, and when he succeeded noticed I was still fully dressed. He told me to hurry up as he didn't want to be standing there buck ass naked waiting on me.

I proceeded to strip down to my underwear and threw my wet clothes in the washer along with his. He looked at me and said to take the underwear too.. I was definitely not ready to do this as I was a bit wet and cold and knew my dick would not be flattering. He crossed his arms and tapped his foot. I pulled off my underwear and my hands quickly went to cover my dick.

He turned and threw them in the washer and set the machine to spin cycle. He turned around and had his hands on the washer giving me a full frontal view of his body. He had a typical teenage body, light hair on his chest and a full bush of hair around his dick and balls. I still had my hand covering my dick and he looked at me and laughed. No need to be shy at this point. I had seen him naked and it was just us guys. I agreed, but mentioned, I was very cold and he knew exactly what I meant. Shrinkage??, he asked. I nodded. "No biggie" he said and turned to walk into the kitchen.