My Trainer Bobby

By Harry Rod

Published on Nov 29, 2023

Gay

"It is a true story," he said. He was built like a rugby player: stocky, ruddy complexion, uncut cock and reddish brown hair on his head. He had no hair below his neck. He blushed a bit before he started his story, and it made me think of the way Bobby always gets me to blush. Bobby accepted me! I was back in the house! I was not so fucked up at the moment!

He continued, "When I first came to college, I was living off campus and had a roommate. I had never met him prior to moving in with him. It was something the housing office had arranged. His name was Jeff. He was this blond jock, with blue eyes and a runner build, defined muscles and stood about six feet tall. He thought he was a gift to all women. I was definitely in the closet and didn't want anyone to know I was gay, especially my roommate.

"I was the kind of roommate you would hate to have. I went through all of his stuff when he wasn't home. I searched his drawers for porn. I knew he had to have some. I thought every guy had to have a stash. I went through his dirty clothes and sniffed his underwear."

There were some snickers around the room and the boys were shushed and prodded with feet. Bruce blushed. It was obvious that he was not proud of this statement, but he continued his story. "Yes, I would smell the crotch of his underwear looking for piss stains or cum stains. I also love to smell the hash marks in his shorts.

"I found his stash of porn. It was a collage of naked women, with lacy lingerie drawn on them. One weekend we decided to go an adult theatre. We went to the booths and I watched some gay films. Then we met up and went to the main theatre, which was showing a cheesy version of the Story of O. It had lots of bondage and mock torture and lots of naked women with fucking, sucking, etc.

"When we got home, I had an idea. I decided I would see if I could seduce him. I think the thought built up over a couple of days. At first I was just being an exhibitionist," he blushed. "I started faking dreams, dreams of being tortured and sexually abused. I would act as if things and people were fucking me. I would act as if I was being forced to jack-off for the entertainment of the other prisoners, actually jacking-off.

"I stated having the dreams in my bedroom. But then I would fake falling asleep in the living room and have my 'dreams.' I would rant about being forced to suck off prisoners. Being fucked and tortured, no matter what, I just continued to make it up, knowing he was either in the room or could hear me.

"After about a week of this, I was faking one of my dreams in my bedroom, when he came in naked and said that they had a new prisoner that I had to suck off. It was him! I wanted my hands all over him. But he kept pushing them back and continued to feed me his cock. All too soon he came in my mouth. And I swallowed every bit of his straight cum.

"I think he felt guilty because he went and got me a glass of water and told me in my dream to wash down the prisoner's cum with it.

"He had never said anything about my dreams during the day and he continued to not say anything about my dreams. Again, I think he was guilty, because he didn't come back for at least a week. Then he came back, this time he tied my hands behind my back with a tie (one of mine). Again he fed me his cock, fucking my face until he came. And once more he went and got a glass of water.

"This continued on for the remaining 3 months we lived together, him coming to my room about once a week and letting me suck his cock. He never mentioned it and neither did I."

Bruce looked up and around and blushed, "And that is how I seduced my straight roommate."

"Very interesting story, Bruce. Although, I think that now you are a member of this house, you don't have to do those things, is that correct?" Uncle asked.

"Yes, Sir, in fact Jason gave me a pair of his boxer shorts that he had "marked" for me. And I put them over a pillow and sleep with them every time he is not is town. And yes, Sir, I no longer have to fake anything to get sex." He blushed again and his cock spasmed in his lap. In fact, I looked around and several of the boys had hard-ons.

"Boys, I think it's time you went off to your rooms and get ready for when your Master arrives." With that, Uncle dismissed us. I headed out and upstairs with the other boys, no one seemed self conscious about the fact that they had a hardon.

I went into our room and straightened up, noting with satisfaction that all my stuff was back in the room.

I sat down at the computer and brought my journal up to date.

Bobby came in and I rose and he told me to get on my knees in the submissive position. I knelt and put my hands behind my back and lowered my gaze. "Good boy," he said and patted me on the head. He moved around the room ignoring me for the moment. My heart was thumping as I wondered what would happen next.

"Okay; we are going to work on training you to withstand more pain. Also we are going to work on this issue you have with cumming." I still didn't move, as he had not given me any direction. "Good, boy. Now come over here and lay down on the bed."

"Yes, Sir." I got up and moved over to the bed and lay down on it. Bobby came over and sat down next to me. I saw that he was naked, his beautiful body all on display. His cock was soft.

"Do you remember these?" He held up the clamps he had used on my nipples on the night of my testing.

"Yes, Sir."

"They are called clover clamps. They have no teeth on them, just padding, but they get tighter the more you pull on them. And if you pull hard enough, it locks into a secondary spot to keep them that tight. You kept them on for several minutes on that night. Tonight we are going to begin with two minutes and work up from there. But first I want you to get yourself hard."

"Yes, Sir," I said as reached down and began to massage my cock. It didn't take long for it to get hard.

"Good, buy. Now take these clamps and put them on your nipples yourself."

"Yes, Sir." I reached up and took the clamps from him. I looked down on my shaved chest and opened the clamp and put it on my left nipple. The pain seared through my chest. But I took the other clamp and put it on my right nipple. Again the pain lanced through my chest.

"Now, stroke yourself."

"Yes, Sir." I started stroking and was amazed how the pain changed. It added to the sexual rush coming from stroking my cock. It became sensual.

"Now take the chain and pull up on it a bit."

"Yes, Sir," I said as I reached down and picked up the chain. Just taking the tension out of the chain made it cause the pain to sear afresh. But I pulled up on the chain and winced at the pain.

"Thank me, boy."

"Thank you, Sir,"

"Now do it again, but without the histrionics. Just do it."

"Yes, Sir." I pulled up on the chain and fought the temptation to make a sound or a face. "Thank you, Sir," I said as I released the chain. "Continue to stroke yourself."

"Yes, Sir." I reached down with my standard left hand.

"No, with your right hand."

"Yes, Sir," I said as I switched hands.

"Now, stroke yourself and get close."

"Yes, Sir," I said as I continued to work on my cock using the pain sensations to heighten the pleasure.

I was totally focused on my cock when he said, "Okay, you time is up on your nipples, remove the clamps."

"Yes, Sir," I removed the right one first and then the left one and as the blood rushed back in, the pain increased and shot through me again. But it made my cock swell.

"Now, boy, take the clamps and clip them to the flange head of your cock head."

"Yes, Sir," I swallowed but reached down and took a clamp and with my teeth clinched, attached it to the left side of my cock. The pain seared through the length of my cock. Then I did the right side and held my breath as to not make a sound. The pain double and tripled, but my cock stayed hard as I was doing this for Bobby.

"Good, boy. Now take the chain and pull up on it." I tried not to think about what this would mean, but just to do it. Just lifting the chain caused it to hurt more.

"Yes, Sir." I worked hard not to let emotion into my voice.

"Now, boy, I want you to pull up on the chain," he said and I noticed he was rock hard as he instructed me. This was really turning him on.

"Yes, Sir," I said as I lifted the chain and gently pulled up on it.

"Good, boy. Now do that 10 times and thank me each time."

"Yes, Sir," I was blown away that my cock could still be hard through this.

I tugged up on the chain and without emotion said, "One, Sir, thank you, Sir."

Each tug, sent waves of pain through me, but I continued on and my cock swelled as I saw my affect on Bobby's cock. On six, I pulled a little harder and pain sprang through my groin and it showed in my voice. I tried to pace the tugs and keep my voice calm. When I finished the 10, my cock was throbbing, both from the pain and from the pleasure of pleasing Bobby.

"Okay, boy, 10 more but without the emotion this time," he instructed and his cock was dripping.

I repeated the process and this time kept the emotion out of my voice. My cock was a bit softer now, but still I felt the mix of pain and pleasure with each tug on the chain.

"Good, boy. Now jerk the clamps off of your cock." He cock swelled and throbbed as he watched.

"Yes, Sir." I hesitated for a split second, anticipating the pain. But I jerked on the chain and OH SHIT, OH FUCK! "OH FUCK!" I screamed. The pain was excruciating and the clamp was still connected to my cock! I grabbed my deflating cock and held on, curling up in a ball.

"Take the clamps off, boy." Bobby said without emotion and watched as I unbent so I could get at my cock.

"Yes, Sir." I gingerly removed the clamps and rubbed my cock as the blood rushed back into the abused areas. Tears had rolled down my face, but I was just worried about my cock. I wanted to make sure it was all right and no tears or holes or blood. But it was fine, but sorer than shit.

"You did well, boy," Bobby said tweaking one of my nipples.

"Now get yourself hard, again, boy."

"Yes, Sir," I said as I reached down with my right hand and began to stroke my cock back to rigid.

"Take yourself close to the edge. Get wet for me." He studied my face as I continued to stroke.

"Yes, Sir." I could only think of him and what we had done together to get me hotter and closer. I kept up and stroking, increasing the intensity. I found I used my thumb and first two fingers when using my right hand and my whole fist when using my left, but I was fast approaching the edge with this technique and my right hand.

"Sir, I am getting close." I said, with just a bit of panic in my voice.

"Stop, boy. Squeeze the base of your cock really hard now. And reach down with the other hand and squeeze your balls. Make yourself stop and DON'T CUM!"

"Yes, Sir," as I squeezed the base of my cock really hard and the squeezed my balls until I felt the ache in my stomach. My cock softened a bit.

"Okay, boy, release your cock."

"Yes, Sir." Just a drop of clear liquid came out.

"Just precum, boy. Lick it up."

"Yes, Sir." I wiped it up and licked my finger clean.

"Again, boy. Get yourself hard and get close to the edge."

"Yes, Sir." I began stroking again, looking at his cock as it dripped its own precum. It wasn't long before I felt that closeness. "Sir, I am close."

"Stop, boy, and squeeze your cock and balls."

"Yes, Sir." I did as he said and squeezed until I softened a bit and felt the ache of my balls in my stomach. I released my cock and a bit of cum, about a quarter teaspoon came out.

"Good, boy, now wipe it up and eat it."

"Yes, Sir." I tasted my cum.

"Your goal, boy, is to get to just a drop of cum on the head of your cock when you stop. Do you understand, boy?"

"Yes, Sir." I was worried that it would be so close to cumming but not cumming. A formidable goal and order from my Master.

He moved around and opened his legs and spread them wide while lifting them up. "Now let's see how well you can rim me." His hole was open to me. I could see the rose bud of it and I wanted it.

"Yes, Sir," I moved up between his legs and lowered by face to his crack. I loved the smell of Bobby. I closed my eyes to intensify the experience of tastes and smells. I licked his crack and enjoyed the feeling of the hairs on my tongue. I worked my tongue around and around his asshole, savoring the taste of everything. Then I went to work with my tongue on his asshole. I worked to get it inside, but couldn't make much headway, but that didn't deter my enthusiasm. I just kept lapping away.

I moved up to area between his beautiful balls and his asshole and smelled the musk and aroma of him that collects in this spot and licked the path between his balls and his ass, enjoying every taste along the way. I heard him moan a couple of times while I worked.

After a bit, "Okay, boy, now suck me off." He turned over and sat legs spread at the edge of the bed. "Take me where you are not allowed to go, boy."

"Yes, Sir." I eagerly licked my lips as I looked at his cock. It glistened in the light where the precum had dripped. I lowered my head and took the head into my mouth. I swirled my tongue around and under the flare of it, gathering all the juice I could find. I loved the taste. I wanted more.

I licked up and down the sides, like licking a Popsicle. Then I took the head back in my mouth and suck on it. Sticking my tongue into the piss slit trying to coax out more nectar. I began to work on the head in earnest then, sucking and licking and swirling my tongue around the head. I heard him moan and knew he was close. He pushed my head down on his cock and I felt him push into my throat. I fought my gag reflex and took him down until my nose rested on his pubes. I loved that smell, but then I felt his cock swell in my throat as he began to shoot.

He pulled up a bit then so his cum would fill my mouth. I tasted him cum, savoring every drop. I wanted it all, I wanted more. He moaned again as I sucked out every last drop. He then lifted my head off of his cock and brought my face up to his. He kissed me deeply and I didn't want it to end. But he released me and said, "Good, boy. Now I want you to change positions. I am going to lay back here and I want you to lie down and take my cock in your mouth. Just let it lay there and keep it there until I fall asleep. Then I want you to sit and watch over me. When you can no longer do that, then move to the floor there next to the bed. Sleep next to me on the floor, protecting me."

"Yes, Sir," I said as we moved around the bed. He arranged himself on the bed and then I moved up and took his soft cock into my mouth.

It was difficult to just let lay there. I wanted to suck on it. But I managed to just lay there with it on my tongue. I relaxed and lay there listening to Bobby's breathing.

It made me so happy just to lay there with his cock in my mouth giving him peace so he could sleep. I felt I could lay like this forever, that this was a perfect place for me. I belonged here.

After a bit, I heard Bobby begin to softly snore. I waited a bit longer and then removed my mouth from his cock. I moved up to the edge of the bed and sat and watched him sleep.

He was so perfect and he looked so peaceful lying there. I looked over his body, checking out every part of it. I loved the hair on his chest, how it bridged the span between his nipples, and the trail of hair leading down from his navel to his pubic hair. All in contrast to my shaved body. I loved how the hair in his armpits peaked out even with his arms down.

I don't know how long I sat there watching him, occasionally, I would massage my throbbing cock, but my focus was on Bobby and this new life I had. I wondered about telling others about it. I was not concerned about telling them. I wondered at what their reaction might be.

I thought of telling my parents, as I wanted to share this special person I had found with them. I would have to talk to Bobby about that in the morning and ask for his suggestions on how best to handle that. I sat there for hours watching him sleep. He would move his head a bit and his lips would move. His eyes moved back and forth under his eyelids, dreaming. I wondered if his dreams were as wonderful as the ones I was having. I looked at the clock and realized that it was past 4 o'clock and I needed to get some sleep, not that I felt that needed much any more.

I moved down and lay on the floor. There was a pillow there. I closed my eyes and thought of Bobby and how far I had come in a short time. I drifted off with thoughts of clamps, dicks, assholes, and cum.

Thank you again, faithful readers - I always appreciate comments, suggestions and ideas.

Harryrod575@yahoo.com

Next: Chapter 26


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