Author's Note:
I'm Tom, and the following is a true story about a guy I met on Craiglist. To preserve anonymity and increase readability, some details will be changed, but the story itself is true.
You can email me at TomTheDom80@gmail.com to ask questions or provide constructive feedback. I also respond to questions and comments from readers, post shorter stories of encounters with guys I meet, and reblog stuff I think is hot on Tumblr. Follow me, ask questions, or submit hot stuff to me at tomthedom80.tumblr.com.
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Part 10: Coaching Kyle
Sometimes I post ads on Craigslist looking for guys who want to be spanked. I usually post those ads when I've had a bad day or I'm feeling particularly aggressive and I want to take it out on someone else. Yesterday was one of those days.
The day started off great. Then last night I was at a sports bar with a buddy, drinking beer, eating wings, and watching college football. It's one of my favorite things to do this time of year with all the bowl games.
The problem is that I also like to bet on college football. Since I'm not stupid, I never bet more than I can afford. However, I do bet enough that my wife would be seriously mad if she found out I lost.
Last night I had $200 riding on a game. It was my biggest bet of the season, and by halftime, my team was down by more than 30 points. To put it mildly, I was pissed off. And I was in the rare mood to hurt someone. So I placed an ad on Craigslist looking for a volunteer.
Since this is an ad I've used several times before and will probably use again in the future (it gets great results), I won't share the actual text with you. I'll simply say that it's an ad seeking a sub who wants to be spanked, whipped, beaten, or abused in some other fashion for my entertainment and that I'm open to role play.
The football game was in the middle of the third quarter when the ad went live on CL, and I got my first response.
Said he was an older guy, but didn't provide any stats, pic or location. Deleted.
A few minutes later, a young twink who wanted to get spanked by "daddy" over his knee emailed me with a nice ass pic. I told him to email me back when he could host, and I'd spank him good for not reading the ad carefully and wasting my time.
Next I heard from a guy who wanted me to shout at him, punch him in the face, and kick him in the balls before making him lay on the bed to flog him. No stats or pic, but he wanted more information about me and a pic before I made his fantasy come true. I marked him as a time waster and deleted his email without responding. (It's a good thing I'm writing this the next day so I can still look back at the messages in my deleted emails folder.)
After the first few emails, I got several responses in quick succession. A couple of guys were too far away. Another boy at home from college couldn't host. Others didn't provide the information requested, or I decided I wasn't interested in meeting them for some other reason. I also heard from a guy I've met before. You might recognize him as story idea #2 from Part 3 (the guy who wanted to be tied up and left alone in his hotel room for a few hours until I was ready to come back and feed him my cock).
I've never thought of a good pseudonym for him, so I'll just call him "cowboy." Trust me, the name fits. He wears western shirts, a cowboy hat, jeans, boots, a belt with a huge buckle, and carries around plenty of rope for guys to lasso him.
Cowboy wanted me to "tie him up and spank him mercilessly." I strongly considered the offer, but I didn't really want cowboy to know that this ad belonged to me. Better to email him later, figure out a time we can meet, and then ask if he has an interest in discipline as well as bondage. I'm sure he'll jump at the chance to be spanked mercilessly later on.
While these messages were coming in, the football game was also turning around. My team was making a comeback. When I finally got Kyle's email in the 4th quarter, they were only down by 7.
I emailed with Kyle but told him I was watching the game and wouldn't be able to come over until it was finished. After an amazing comeback, my team won the game in triple overtime, and I won my $200 bet. You'd think that would lessen my desire to hurt someone. In some ways, I suppose it did. I no longer wanted to beat the shit out of anyone in anger. However, I was also super horny and ready to give Kyle the spanking he needed.
Kyle is a 27 year old white boy who always fantasized about his coach spanking him. At first he seemed hesitant to share his fantasy, but as soon as I told him about a couple of role plays I've done in the past, he immediately laid out a full scenario.
Kyle wanted to get spanked by his high school coach. He wanted Coach to walk into his apartment, catch him sitting on the couch watching porn and jacking off, and give him a hard spanking over my lap to "teach him a lesson." Kyle wanted to start by hand and move up to a belt if I felt like he could take it. He told me it was his first time to try spanking, and he was really excited but also scared.
On the drive over to Kyle's apartment, I gave him my standard safe word and told him how to use it. I explained that I would not respond to words like stop, no, please, don't, etc. unless they were prefaced by the safe word. I told him that using such words would only make me think he hadn't learned his lesson and encourage me to spank him harder. I would not stop spanking him until I believed he had truly learned his lesson and that he would be a good boy afterward.
I sent Kyle an email when I pulled into the parking lot so he could make sure he was in position for me to catch him in the act and start his fantasy off on the right foot. When I opened the door to his apartment, sure enough he was sitting there on his couch with his hand in his pants and porn playing on his computer. He has good taste in porn too. He was watching straight porn from one of my favorite pay sites (one of the few I've ever actually paid for a full 1 year subscription).
"What are you doing, boy?" I asked as I walked over to the couch and turned to look at the computer screen. "Watching porn? You know you aren't allowed to watch porn and jack off without permission, boy! Apparently, I'm going to have to teach you a lesson."
I grabbed his arm and pulled him off the couch.
Kyle started saying, "I'm sorry coach . . ."
I interrupted, "You aren't sorry yet, boy, but I promise you will be. Pull those pants down!"
As I was saying this, I sat on the couch where Kyle had been. As soon as his pants were at his knees, I yanked his arm to pull Kyle across my lap and pulled the band of his underwear down to reveal his ass cheeks.
Let me pause to say that Kyle has a beautiful bubble butt lightly covered in blond hair. The perfect kind of ass for grabbing, massaging, and spanking. Oh, I was going to have fun!
Before Kyle could prepare himself, I started slapping his ass cheeks with my hand. Left, right, left, right, left, right.
I started with about 10 swats on each cheek before I gave him his first little breather and disciplinary speech.
"I can't believe I come in here to check on you in my spare time and find you watching porn and jacking your cock, boy. What do you have to say for yourself?"
"I'm sorry, Coach. Please don't hurt me."
"Oh, I'll hurt you boy. I'm going to turn your ass red. I'm going to make sure you learn your lesson tonight, boy."
Left, right, right, left. Two on each side. Three on each side. Five hard swats right down the middle. Switching sides, back and forth, again and again.
"Your ass is starting to get a little bit of color, boy. Can you feel that?"
"Yes, Coach. It hurts."
I started grabbing and massaging his ass, rubbing it hard.
"You have no idea what it feels like to have your ass hurt yet boy. That's the lesson you're going to learn tonight. You're going to learn what it feels like to have your ass hurt. I'm going to give you a spanking you'll never forget."
So I started spanking him again. I tried to mix it up and make it hard for Kyle to anticipate the next smack on his ass to keep things interesting. Sometimes I would use slow methodical strikes across one cheek or the other. Sometimes I alternated back and forth between the sides. Sometimes I hit the same cheek several times in a row before switching to the other side. Sometimes I hit his ass 10 of 15 times in a row very quickly to make sure he felt the burn.
When I hit him particularly hard, Kyle would rear back and cry out. Since he was new to spanking, I gave him some coping tips early on in the process. I told him to grab hold of my shin through my jeans with his right hand and focus on squeezing it. Grabbing onto something with your hand and squeezing helps redirect your attention from the burn or sting on your ass cheeks.
I also used my left hand to run my fingers through his hair and calm him between swats and let him grab that hand and squeeze it with his left hand while I spanked his ass with my right.
While the spanking hurt, I could tell Kyle was enjoying it. His dick was rock hard against my right leg. Finally, I decided to address how hard he was.
I moved my hand down from Kyle's ass, grabbed his cock and said, "You're enjoying this, damn it! Your dick is so hard it's leaking all over the place. How long have you been sitting here jacking off hoping I'd walk in and catch you? Clearly spanking you by hand isn't going to teach you the lesson you need to learn tonight."
I reached down to where Kyle's jeans were resting around his ankles and started to pull his belt out through the loops.
He pleaded, "No! Coach, please! Not the belt! I'll be good!"
"Too late for that, boy," I said and brought the belt down hard across his ass.
I'm not sure if his ass was just so warmed up by then that the strike of the belt didn't surprise him or if he just realized it wasn't as bad as he expected it would be, but Kyle barely reacted. He squeezed my leg with his right hand, but he didn't cry out as I thought he might. To be fair, it's difficult to spank very hard with a belt on a couch in that position. You have to fold the belt awkwardly and can't get enough space to swing your arm for a good hard lashing. Kyle's belt was also especially thin and flimsy (not like the thick masculine leather belt I wore for the occasion).
Before I really went to work on Kyle's ass with the belt, I wanted to give him a little time to prepare himself mentally for the ass whooping he was about to receive. I took a couple minutes to rub the leather across his ass and balls and dick, teasing him with it.
"I'm sure you're going to enjoy the feel of leather on your ass as much as I will, boy. This belt is what you need to really learn your lesson, and you're going to thank me for it later. Do you believe that, boy?"
"Yes, Coach."
"Good boy. Before we get started, I want to show you something."
I grabbed his right hand and pulled it up along his side and rested it on his right ass cheek.
"Feel how warm your ass is getting?"
"Yes, Coach."
"It's only a little bit pink. Not very warm at all yet, boy. To learn your lesson, it needs to be red hot."
As I spoke those word, I raised the belt with my right hand, shoved Kyle's hand away with my left, and swiftly brought the belt down so that it landed across both cheeks with a crack. Then I did it again nine more times, fast without stopping.
By the tenth lash, Kyle was up on his knees, wiggling his ass around, and gripping my leg and free hand as hard as he could with his hands. However, he didn't use the safe word or even yell for me to stop. I put the belt down for a minute and rubbed his ass with my hand.
"You took that like a good boy."
"Have I learned my lesson then, Coach?"
I laughed, "No, boy. Not even close. I just needed you to feel a hint of the pain I can give you if I feel like you deserve it."
"Please, Coach. I don't know how much more I can take."
"Don't worry boy. I know how much you can take. You aren't even close to your limit," I told him and gently stroked his almost throbbing dick a few times.
Let me explain something to you boys. If you're dick is rock hard, you aren't at your pain threshold. If the pain is small enough to turn you on, you can take more. A lot more. Since Kyle was new to the whole pleasure/pain dynamic, I didn't want to push him too hard on his first session, but I did want to make sure he got the general point.
I continued spanking Kyle with a combination of hard and medium lashes with the belt for a while and then switched back to my hand so I could even out the color on his cheeks (the belt struck the far cheek more forcefully even though I tried to keep it even). Altogether, I spent about 30 minutes reddening Kyle's ass.
For a first session, Kyle did remarkably well. He got spanked for a long time with minimal thrashing about, crying, and begging. He also stayed hard right until the end, which is when I knew it was time to wrap up the spanking portion since we were doing it for erotic purposes rather than disciplinary reasons.
Kyle also started changing his verbal responses to the spanking without me having to tell him. Instead of asking for me to stop or begging, he showed remorse. He said he was sorry for being bad, that he'd work really hard to do better next time, etc.
As I was finishing up with the spanking, I told him, "It's important for you to learn your lesson so you remember not to do this again, boy."
He answered, "I've learned my lesson, Coach. I promise I have. I won't do it again without permission."
"I'm glad to hear that, but you still need to show me how sorry you are, boy. I'm very disappointed in you. What are you going to do to make this up to me?"
"Anything you want, Coach. Please let me show you how sorry I am."
"Okay, boy. Then get on your knees."
Kyle was off the couch and kneeling in front of me in record speed.
"Are you ready to take care of Coach's cock now, boy?" I asked as I unbuckled my belt and started taking off my pants.
"Yes sir, Coach."
"Let's see if I can teach you to focus on someone's dick besides your own, boy."
I stood up, grabbed Kyle's head, and pushed my hard dick into his mouth.
"Oh yeah, boy. I always knew you'd be a good cocksucker for Coach."
Kyle was obviously inexperienced. I wasn't sure if this was the first time he'd ever given a blowjob, but he was certainly acting like it.
"Come on boy. You can do it. Just do what feels good when your girl does it to you."
He was sitting there with his mouth open as if he had no clue about oral sex.
"Close your lips around my dick and suck, boy. There you go. That's a start. Now move your mouth up and down. It's not hard, you know what you feels good. I know your girlfriend sucks your dick sometimes."
I let Kyle work on my dick for a minute and focused on getting my pants and underwear the rest of the way off.
He looked up and asked me, "Does it feel good, Coach?"
"You're getting there, boy. Keep doing what you're doing but also let me feel your tongue. Don't be afraid to taste my cock boy. Feel how soft it is on your tongue. Make love to it. Show me how sorry you are and how much you want to make it up to me, boy."
After that, Kyle really started getting into the blow job. He sucked like a champ. He gagged a little, but always went right back to work.
"I want to make you feel good, Coach. Tell me if I'm making you feel good. Please, Coach."
"You're being a good boy now," I told him and ran my fingers through his hair. "This is just what Coach needed tonight, boy, and it's the other lesson you needed to learn. You need to learn how to use that sweet mouth of yours to please a man, baby."
When I said that, Kyle reached down and started jacking himself off furiously. I thought he was going to rip his dick off he was jerking it so hard, but he stopped himself after just a few seconds before I even had to tell him not to cum.
"Good boy. Don't make yourself cum yet. You've gotta take care of Coach first, and then you can cum, boy. Coach's dick is your priority right now, so keep working that tongue for me."
Kyle kept sucking my dick. When he'd forget to use his tongue (usually when he started stroking his own dick), I'd remind him. After a little while, I finally started getting close to cumming.
"Fuck yeah, boy. You're getting Coach close now . . ."
And then the fucker pulled his mouth off my cock and said, "Don't cum in my mouth, okay?"
"Fuck, boy. Are you serious?"
"Yeah, man."
"Your ass is going to pay for this, understand?"
"Yes, sir."
"Fine. Get your mouth back on my dick, and I'll warn you before I cum. Then I'm going to teach you the difference between erotic spanking and disciplinary spanking."
Kyle got back into his role and told me, "Okay, Coach."
He seemed to work extra hard to make my dick feel good after that, but I was not appeased. I took my time and made him suck for a good 15 minutes as I sat back and relaxed on the couch before I finally told him I was ready to cum.
When I pulled out of his mouth, I grabbed his hair to hold his head in place, but the fucker turned his head. So I shot part of my load straight into his ear. I'm still laughing about that today.
After I was done stroking out my cum onto the side of Kyle's face and chest and into his ear (LMAO), I got up, bent him over the couch and grabbed my belt.
He looked at me with a little bit of fear and asked how many spankings he was going to get.
"As many as I feel like you deserve for leading me on and then making me jack off. Count them out."
With my real man's belt in hand, I swung back and unleashed a lash on his ass with all the force I could muster. A loud crack rent the still air of the apartment as the belt struck home. Kyle jumped and grabbed at his ass with his hands.
"Count, boy. And stay in position. You don't want the belt to hit your hands. Trust me."
"One, Coach."
Another crack, not quite as loud as the first.
Kyle stayed in position this time and answered, "Two, Coach."
The routine held for the third, fourth, fifth, and sixth, lashes. I had decided seven would do it and was determined to make the seventh another hard one. But I wanted him to think about it first.
"I think you've almost learned your lesson boy. You cannot tease a man, make him think you're going to give him a blow job, and then tell him he needs to jack off instead. This is the last one, but it's going to hurt. Are you ready, boy?"
"Yes, Coach."
"I want you think for just a minute about how much the other lashes with my belt hurt your ass. The first one was pretty hard, but the others have been softer. This one is going to be the hardest of all. It's going to be even harder than the first one and it's going to hurt worse because your ass is sore from the other five hits in between. Your ass is going to really sting after this."
The whole time I was giving this speech, I was rubbing the belt across Kyle's ass to drive the point home that he was going to feel the leather tan his ass one last time.
"Put your hands back there and feel how hot your ass is getting now. It's finally getting nice and red like I told you it needed to be, boy. You've finally almost learned your lesson."
Kyle followed my directions and felt his ass. When he did, he started to cry for the first time.
He said, "I'm sorry, Coach. I didn't mean to lead you on. I just can't do that."
"Shh. Be quiet, boy. I don't want to hear excuses. What's done is done. It's time to move on. You've taken almost all of your punishment. You just have this one last stroke of the belt to get through. You can do it, boy."
Kyle was really starting to tear up now. I had been intentionally torturing him with the wait, making him think about how much this one was going to sting and I was starting to think he'd call out the safe word if I didn't hurry up and finish the spanking.
Since I believe in mercy and don't like giving needless punishment, I decided to give Kyle a little test. I didn't think there was any way he'd pass it, so it was pretty low risk from my perspective.
"Look at me Kyle."
He turned his head.
"Do you think you've learned your lesson?"
"Yes, Coach."
"Do I need to give you one more lash with the belt or was six enough?"
This is kind of a trick question. There is only one answer that can possibly save a sub's ass from one more strike with my belt. If he says six is enough, I will disagree and spank him. If he says he needs one more, I will agree and spank him. Kyle stunned me by actually giving the correct answer.
Looking into my eyes, Kyle said, "It's up to you, Coach."
I was so surprised that it took me a moment to react. I dropped the belt, patted Kyle on the head, and told him, "That proves you learned your lesson. Good boy."
I sat on the couch next to Kyle and told him to crawl on top of me on his hands and knees so I could feel how hot his ass was. I rubbed his ass and gently smacked it a couple of times. I told him he had done a good job with his first spanking session and made lots of comments about his ass (how great an ass he has for spanking, how firm it is, how tight his hole feels when I rub my fingers around it, etc.).
Within a couple minutes, Kyle's dick was hard again. I told him to put the porn video back on (it had long since ended). Then I let him sit on the couch next to me and jack off. After all he'd been through, I figured Kyle had earned the reward of getting to cum while sitting on the couch next to Coach and hearing some encouraging words.