Keith's First Bondage Experience



I don't know why I am turned on by bondage, I just am. I have always had an interest in bondage ever since I accidentally handcuffed myself to me bed. (That's another story.) Let me first tell you a little about me. I'm 19, a senior in High School, love football and I'm the captain of the basketball team. I'm also bi but I have always acted straight. My parents don't even know about my sexuality. I'm 6'2", and in good shape. I really look like an athlete. After every football game, at least five girls ask me out. I really don't go out much though. Usually, after school, I go home and fantasize about being tied up securely and having some guy have his way with me. He would massage me, explore my body, run ice cubes up and down my chest, jack me off, stuff like that. I never played out any of my fantasizes though, until now. I recently had my first bondage experience and I'd like to tell you about it.

There is this adult bookstore in my neighborhood that I would frequently visit. They had a nice selection of bondage videos and books and adult toys. I picked up this magazine and thumbed through it. In the back of the magazine they had some personals. Some sounded hot, others sounded very dull. One ad though caught my eye.

                   Top looking for a bottom for bondage fun
                   Limits respected and expanded
                   I will keep you hard and cumming
                   If you'd like to play, call me
                   Tony (555)555-2289

His address was also listed and I noticed he lived in my area. I bought the magazine and went home. I immediately called him.


"Hi. Can I speak with Tony?"

"This is him."

"Hi. My name is Keith and I found your number in a magazine and I was thinking that maybe we could get together?!?"

"You have an interest in bondage?"


"Have you ever been tied up before?"

"No. I'm still kind of new at this."

"I see. Well, would you like to come over this evening?"


He gave me the address and I said I'd be over soon. Now comes the hard part. How was I going to get out of the house? My parents are very strict and they keep a close eye on me. I decided to tell them that I was going to a friend's house. It was Friday night, maybe they would cut me a little slack and let me stay out longer. I borrowed my mom's car and I drove over to Tony's place. He gave me clear directions so it only took me twenty minutes to get there. I rang the bell and waited.


"Hi, I'm Keith."

"Ah, come in."

He was very attractive himself. He looked maybe 25, 26. He was wearing a tank top and jeans. He looked like a model. He told me to sit on the couch and relax. He sat in his recliner and we talked for a bit.

"So, you say you never had a bondage experience?"

"No but it's something that has always fascinated me."

"Do you have a fantasy?"

"Well, in my fantasies, someone would tie me down, fondled me, feel me all over and then he would start jacking me off. I'd ask him to stop but he wouldn't. I want to experience that feeling of being powerless, to have someone else call the shots."

"Hummm. I think we can play, if you're up for it?!?"

"Yes I am."

"How long can you stay?"

"For a couple of hours I guess."

"Good. Follow me."

He led me to his bedroom. Wow, he had a queen-size bed! I noticed he had some rope on the floor and he had some wrist cuffs attached to the bed.

"Why don't you lie down."

I lied down, still fully clothed.

"Stretch your arms up over your head."

He attached the wrist cuffs to my wrists. He then tested them to make sure I was securely tied down. He then straddled my chest and he started talking to me while feeling my chest though my clothes.

"How old are ya?"


"How many times do you jack off in one day?"

"About twice a day."

He then started unbuttoning my shirt. He pulled apart my shirt and messaged my chest. My nipples got hard immediately. He then got up and undid my jeans. He felt my cock through my underwear.

"Let's get you nice and hard."

He slid my jeans off and he tied my ankles to the bed. I was spread eagle. I laid there with my shirt open, chest exposed and my hard cock poking through my underwear. He went back to feeling my cock. He slid his hands under my underwear and he felt my balls. What an erotic feeling.

"Hummm you do have a nice body. Nice tight chest, great legs..."

He then ripped off my underwear.

"...and a nice cock! I think it's time to go to work. Would you like me to jack you off?"

"Yes please!"

"Have you ever jacked off repeatedly, like two or three times in a row?"

"No, I never did."

"Well, tonight you'll experience what it like. I'm gonna start by making you cum a couple of times, OK?"

"OK I guess. What's the safety word?"

"Ah, don't worry about that, just relax."

He sat on the side of the bed and he started touching my cock. He messaged my balls. He then concentrated on my cock head. With his fingers, he traced my cock head all around and then he started rubbing the tip of my cock. I was floating on air. He played with my cock head for a while. Pre-cum started oozing out. He use used it as a lube and continued messaging my cock head. Ah, what a feeling. He then started jacking me off. He gripped my dick and started jerking up and down. More and more pre-cum was oozing out. He fondled my balls with one hand while he jacked my cock with the other. The feeling of not being able to stop him was too much. I was so turned on that I soon started cumming. My muscles tightened up.

"I...I think I'm gonna cum."

"Good, cum, let it out."

He sped up the pace and I erupted. I came all over my chest and legs. He made sure I was empty before he stopped.

"Wow, that was something else. Thanks."

He cleaned up my chest and legs.

"Remember, you have to cum again."

"Ya, I remember."

"We're gonna do it differently this time. I want to see how you control yourself. This is a test OK? I'm gonna jack you off again but you can't cum until I say you can. When you feel like your gonna cum, tell me and I'll stop. OK?"

"This is a strange test. I don't know if I can hold out."

"When, you gonna have to try. If you do cum before I tell you too, then I'm gonna milk you."

"Milk me? What do you mean?"

"Don't worry about it now, just don't cum until I tell you too. Remember, tell me when your feel like cumming and I'll stop. OK?"

"OK, what choice do I have?!?"

"You can take it, just relax."

He when to his dresser draw and took out a small plastic bottle. The contents looked clear, like water.

"What is that?"

"You never jacked off with any lubricants before?"

"No. I have seen them at this store I go to but I never bought any."

"Well, relax, it's not going to hurt. It's just going to make your dick slicker. It's sort of like grease. My hand will glide better around your lubed shaft."

He poured the gel over my hard dick and then he messaged it in. I closed my eyes because the feeling was so intense. Hummm...I gotta buy some of this stuff. He held the base of my cock with one hand while his other hand was stroking me off. He kept a steady pace, not too quick, not too slow. I really felt high. I was totally helpless. I couldn't escape his skillful hand. The feeling was too much. I started to pant a little.

"Relax. You're doing fine. Just keep still while I work you cock. Remember, don't cum until I say you can."

His words got me harder. This feeling of being powerless was incredible. My cock belonged to him. He paused to relube my cock. Each new coat felt so cool and wet. The gel really made my cock feel sensitive. Tony' fist was just keep riding my cock up and down from the base to my cock head. He never a beat. He was stroking my dick for about an hour. I then felt a stirring in my cock. I felt like I was going to explode.

"I'm gonna cum!"

He stopped.

"Good. Just relax. I'll give you a moment to rest."

He still held onto the base of my cock. With the other hand, he poured more of the gel on my dick.


"I guess so."

His hand again engulfed my cock. He messaged the fresh lube into every crevasse of my cock. This time his fist was a little tighter. Again I felt like cumming.

"Stop, I gonna cum."

He stopped.

I panted, "Oh.. please let me cum."

"Not yet. Just relax. I'll let you cum eventually. Get ready, I'm gonna start again."

He started stroking me off again. I closed my eyes again. I started sweating. The feeling was too intense. When was he gonna let me cum? My dick was harder than before. Again he brought me to the edge.

"Oh...stop. You have to get me off, I don't know how much more I can take. It's getting late, I really gotta go now."

It was around 9:30 and I told my mom I'd be home around 10ish.

"Not yet. Relax."

He started stroked my lubed dick again.

"Can I cum now, please? How much longer are you gonna do this to me?"

"I'll tell you when you can cum. I don't want you to cum yet. Be a man and take it."

I felt like cumming again and I told him to stop. He kept this up for a while. He didn't let me cum for another half-hour. I was going crazy inside. My balls felt like they were gonna explode.

"Please, I gonna cum, let me cum."

Tony stopped. I was still in a sexual high but I was also very frustrated. He relubed my cock and he continued. This time his fist was very tight. His tight fist ran up and down my lubed dick. I thought I was gonna pass out. I felt like cumming. I tried to tell him to stop but it was too late. Cum came gushing out. I started buckling up and down as he drained my cum out of me. He stopped.

"I'm really sorry. I was gonna tell you to stop but it was too late."

I was panting and feeling scared.

"Oh, don't worry about it. Your endurance level is low. But we got a whole night to fix that."

"Oh...I really gotta go. I told you I can only stay for a little while."

"Oh I'll let you go after I milk your cock. Remember, you came before I told you too."

"But that was an accident! Let me go!"

"I'm sorry but I told you the consequences if you came. Now I'm gonna milk your cock."

"What is this 'milk my cock'? What is milking?"

"It means I'm gonna jack you off over and over until nothing comes out. I won't stop jacking your cock until you 'dry shoot'."

"You said in your ad you respect limits. I'm new to this, I don't want to be milked, and I told you it was an accident. Let me go!"

"But in my ad I also said I would help people expand their limits too. Don't worry, it's not as bad as it sounds. Your young, you can talk it."

"I really can't, at least not today, I really gotta go."

"What's your phone number?"

"What? What for?"

"What's your phone number?"


He picked up his cordless phone and he dialed the number. He put the phone next to my head and I held onto it with my arm. He sat back down and grabbed my balls.

"Make up something. Tell your parents your staying at a friend's house. If you start screaming, I'll crush your nuts. Got it?"

My mom picked up the phone.

"Hi mom...."

As soon as I said 'Hi mom', Tony lubed my dick and started stroking me off. This was really embarrassing. It's hard to talk to your mother while someone is jacking you off.

"I know I'm late....uhhh...No I'm OK. I just wanted to let you know that I'll be staying over Frank's house. Uhhh... I said I'm OK, we're just horsing around. So I'll be home tomorrow, OK? ... OK, bye."

He took the phone from me.

"Good, very good. Now just shut up and relax. Your job is just to keep cumming. Don't resist or give me any problems."

"Can't I take a break, please?"

"You don't need one. You're a jock, you're young and loaded with cum. Just relax."

He blindfolded me. I couldn't see anything. I felt a cool sensation on my dick, he must have poured lube on my shaft again. I then felt his fist close around my hard dick. He started stroking my dick up and down but this time he was stroking my cock ever so slowly. I was screaming inside.

"Oh please, this is torture, please don't do this to me. Please speed up a little, please. I can't take it!"

He ignored me. His talented hand just continued slowly gliding up and down my hard dick. I was wet all over. I kept testing the cuffs, I couldn't take it anymore.

"Lie still and relax, your gonna be here for a while."


I didn't know what time it was or what day it was. Maybe I passed out. I woke up still tied down but I couldn't see Tony. I heard water running. I looked down my chest. Cum was all over me. I heard footsteps.

"Ah, your awake. I just took a shower, now it's your turn."

"What time is it?"

"It's about 5 in the morning. It's all over."


He started untying my ankles and he took off the wrist cuffs.

"I said I'm done milking your cock. You must have came around 12, 14 times. I told you it was not that bad."

I was glad it was over. I was tired and week. I really wanted to hit him or something for what he put me through, but I was too weak. I got up and headed for the shower. After my shower, I went back into the bedroom and I put on shirt and jeans. We then talked for a bit.

"So, was your fantasy fulfilled?"

"It was and then some. It was really intense. You did push the limits a little too far but it was worth it I guess."

"So no hard feelings?"

"I guess not."

"Do you think you'll be back?"

"I don't know."

"Well, if you do come back, maybe we can switch roles and you can get even?!?"

I smiled when he said that.

"Well, OK, I have your number, maybe we can play next weekend. I'll be in touch."

I hopped in the car and as I drove home, I reflected on what happened. I realized that my fantasy did come true. I really don't know if I could do it again but then you never know.

So there you have it, my first bondage experience.