Gay Erotic Stories

The first time that I met Simon, he was a freshman. He was raising a ruckus outside of my classroom and I stepped out and in my best teacher voice, I asked him what he thought he was doing. He was a handsome kid, with an affinity for sunglasses, and I thought he was trouble, in my limited experience as a teacher, but he came into the classroom and asked me to forgive him. I was impressed. He displayed an uncharacteristically mature stature, and self secure. I noticed him then and I knew to keep an eye on him.

The next year, I took the over the leadership of the school’s drama club and he had just gotten involved with the stage crew group. So I got to know him much better that year. What I learned was that he was a smart kid, all boy, who was interested in making things work and building stuff. He was funny and interesting and he took a liking to me. Every time he saw me he smiled broadly and waved. “Hey Mr. Connors!” It made me feel good to see him smile at me, not in a creepy way, but in a “I am making a connection with a great kid” way.

In his senior year, Simon was in my class, and after 2 years of working with him as the drama club, he felt he had a special connection and that he could get away with more than the other students, and I quickly dissuaded him of that idea. I think that only served to deepen his respect for me. By the end of that year, he had quickly become my favorite student. At graduation, he gave me a big hug and promised to keep in touch, like they all do. He went to college locally so he definitely had the opportunity to keep in touch with me if he wanted.

Shortly into the next school year, we were deep into our next production, when into the auditorium Simon walks in. Same smile and wave. Same big “Hey Mr. Connors!” this time accompanied with a big hug. Apparently that was our new normal. I was a bit uncomfortable, since I didn’t want any of my students to get the idea that hugging was an acceptable form of display of respect. Particularly since I never made any secret of my being gay. Simon came and went all for the whole time we were working on our production and everything seemed normal, but when the show was over, he disappeared.

A year passed, and we started production on our next show, and Simon returned. Big smile, big wave, and big hug. “Hi Mr. Connors!” only this time, the hug lingered. There was a genuine warmth in it. There was sadness too. He was struggling with his life. It happens. Students move on from high school, get into college and then lose their direction, become discouraged and look back to high school as better times, and try to make connections with their old high school people. Simon shared his concerns and we talked at length about what his future would look like. He was really torn. Nothing seemed to hold much interest to him. I shared with him my own experiences and mentioned my military service. His parents were both military so that had always been an option for him. They were tired of his lack of direction and were ready to force the issue. I always expected him to knock at my door at home and asking to stay with me and I was prepared to let him, but now there was something in his hug that felt… different. During the performances, Simon would stand in the back of the dark auditorium next to me. He was so close to me, so much closer than two guys should be. He seemed comfortable with the proximity. He would lean into me to ask me questions and linger longer than he should. His body would press up against mine. It made me uncomfortable, but I could tell he needed someone to listen to him and to care. Once again, once the show was over, he disappeared.

Then a few months later, I got a text: Can I use you as a reference for the Military?

I gave him the heads up, and my contact information, but part of me was sad that I wasn’t going to get to see him, even if it was just a couple times a year.

Then it was show time again and Simon didn’t show up. I had given up hope in seeing him this year, and then, on the day of the last show he showed up. Gone was the high school boy, and here in front of me was a man. He was never an athlete but he had an athletic build: broad shoulders, and narrow waist, a brown tussle of hair on top of his head parted on the side. He stood about 5’11” with a tuft of hair showing from the top of his crew neck t-shirt. He had piercing blue eyes that were lit up when he came in the door. He hugged me close, closer than he ever had before and it lingered a really long time. He smelled of lubricating oil, and I joked with him about that. He talked about his work on engines and how that had been keeping him busy. We watched the show from the back of the auditorium and again he stood close to me, even closer than last year, asking questions about the plot, leaning against me, and I started to feel a stir.

All night long, he stayed close to me, right at my side. During the show, after the show, during the set strike and even the cast party on the stage. More than once, he put his arm around me, and not in the way a friend does, but it was different. As the end of the night approached, I asked him how he was getting home. I knew that he had no car and I didn’t want him walking home that late at night. He protested at first, and I insisted, it was just too cold. He smiled and then agreed. Was there something in that smile?

We got into the car, and as we pulled out of the parking lot, Simon turned to me and said: “You know, Mr. Connors” “Simon, you graduated. You can call me Greg now!” “Ok, Greg. You are the only one who ever really believed in me” “What do you mean? Lots of people believe in you” “Yeah, but you were the only one who made me believe that you believed in me.” “That’s nice of you to say Simon, but you gave me every reason to believe in you, from the first time that I yelled at you outside of my classroom, do you remember that?” “Ha ha, yeah. Everyone else thought you were a bit of a hard ass, but I thought you were just doing your job.”

My hand was on the gear shift. Simon took his hand and placed it on top of mine. “Simon, do you know that song by the Police, Don’t Stand So Close To Me?” “Ha, yeah. I want to thank you for everything.” “You don’t need to thank me that way.” “I know, it isn’t that I need to. I want to. I have wanted to for a long time.” And with that he leaned across and kissed me hard on the lips. His rough hands grasping me firmly behind my head as he pressed my face into his. My lips parted as he pressed his tongue into my mouth. My tongue rose to meet his, and my intensity matched his. His hand reached between my legs and my already hard cock was straining in my khakis to be released. My hand went to his leg, and as I reached his dick I could feel through his jeans that he was a big boy! He was at least nine inches hard. He moaned at my touch. Abruptly, I stopped us. “No. We can’t do this.” “Greg… I want this. Take me to your place.” I drove with a purpose to get to my house, barely able to keep my hands on the wheel and my eyes on the road. Every stop light, he grabbed my face and kissed me hard. A couple of times the person behind us would honk to let us know that we were missing the light. After what seemed like forever, the car screeched into the driveway. Simon got out of the car, and followed me into the house, and once the door to the house was shut, he turned me around, and threw me up against the wall and kissed me hard. My hands were on the sides of his face as he pressed himself against my body, my 7” cock was fully hard and desperately trying to get free and I could feel his cock pressing against me. I reached down to try to undo his pants, when he grabbed my hands and pinned them against the wall above my head. “I am calling the shots, Greg.” “Ok” Still holding my hands together above my head with his left arm, he reached down and undid my belt with his right. He dropped my pants and then slipped his hand under the waist band of my underwear and took hold of my cock all the while kissing me. I kissed back hard. “Take us to your room” I took his hand in mine and led him to my bedroom. He followed me until we entered the door to my room and then he pushed me down onto the bed. I took off my shirt, exposing my hairy chest and well defined abs, and Simon did the same. I couldn’t believe this was happening. Here was this young man I had known for years standing in my bedroom with nothing but his underwear, a pair of snuggly fitting boxer briefs that were straining to contain his 9” he came to the bed and I pulled them down, releasing a perfectly shaped uncut cock curving slightly to the left. I quickly took it in my mouth, skinning back his foreskin and licking under the head. Simon groaned as my tongue caressed his dick. I then took his nine-inch member into my throat until it was down to the base. I was twice his age and had that much experience at sucking cock and he responded to my mouth with a firm hand at the back of my head, forcing his cock further and further into the back of my throat. He groaned and gasped as I worked over his cock, then finally pulled out and pulled me back up to his mouth and kissed me. Now it was his turn. He laid me back and took my dick in his mouth and sucked it deep into his mouth the way that I had just done to him. I wasn’t sure if he had done this before but if he didn’t, he took to it like a duck to water. He gave a mean blow job, and right when I thought I was about to cum, he pulled off. “No, not yet!” He said. “I want to fuck you.” He reached his hand up to his mouth and spit on it and then used it to lube up his dick and my hole. He picked up my legs and threw them over his shoulder, pressed his hard cock against my hole and then slowly began to press it into my hole. I gasped, since his cock must have been 5 inches around. In response he leaned down and kissed me. Once his cock was passed my sphincter, he slid it all the way in. There was a flash of pain, and then just pleasure. He filled me up perfectly. He pumped me that way for a while as I groaned and moaned and begged him for more. Suddenly, he flipped me over onto my stomach, and I popped up onto all fours. He slid back in and I buried my face in the pillows while he drove that monster into me. I loved every minute of him in me. He wrapped his hands around the back of my neck and squeezed tightly. The feeling of his strong rough hands on my neck drove me crazy. He fucked me hard and I could feel his rhythm increase, and I knew he was getting close. “Cum in me, Simon. I want to feel you cum.” “Ok, Greg, you got it. Here I cum. I am cumming!” With a final thrust, he emptied his load into my ass. Then he collapsed on top of me. I could feel his breath against my neck, and I was still so hard. I needed to cum so badly, and that is where Simon said “My turn. I want to feel you inside of me.” “Are you sure?” “Simon says!” He joked. ”And stop second guessing me! I am here because I want this!” I slid out from under him, his cock barely softening, and then rolled him onto his back. I lifted up his legs and began to lick his hole “Holy Christ! What the fuck was that?” He said “You’ve never been rimmed before I take it?” “No, but don’t stop! That is awesome!” I licked around his hole and plunged my tongue in deeply. He responded to my tongue pressing back into my face. I replaced my tongue with my index finger and began to enter his ass. He winced, but his cock remained hard. I pushed in further and began to massage his prostate. I added a second finger, and then he whimpered “Oh god! Please, I want to feel you inside of me!” I slid my dick into his waiting hole, and he screamed. “Do you want me to stop?” I asked “No! Please don’t” I pressed further into him and he started to push back into me. I couldn’t keep the pace up long, but I held off as long as I can. “I think I am going to cum, Simon” “Oh, yeah, Mr. Connors. Cum in me like I came in you! I want to feel you!” And with that I let my load go right into his ass, as he blew his second load all over his chest. “Oh god that feels good!” He said, and I collapsed onto him and kissed him. “I love you, Mr. Connors.” He whispered into my ear. “I have for a while” “When do you leave for boot camp?” “19 days” “Well, let’s make the most of it!”