Author's Note:
I'm Tom, and the following is a true story about a guy I met on Tumblr. 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.
Thanks to all the doms, masters, subs, betas, kappas, faggots, cocksuckers, and other guys who have emailed me. Keep sending the hot pics, links to your favorite videos, and stories about your own experiences. Hearing from all of you encourages me to keep writing these stories, so keep the comments coming.
This work is copyrighted, and commercial use is prohibited without written permission from me, the author.
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Part 11: Making Ivan Pay
I travel a lot for my job, and I'm constantly getting messages from tumblr followers asking if I ever travel to their city. If I say yes, they inevitably ask if I'm interested in meeting them.
A lot of the guys who contact me, I'm not interested in meeting. No offense faggots, but if your tumblr is all about you getting high and fucking bareback, we aren't a match. I'm happy for you to follow me and jack off from a distance. If you only want bondage and discipline without any sex play, I might even be interested. However, if I think you're likely to be a walking disease factory, I'm not letting you anywhere near my cock. My wife puts that thing in her mouth (rarely) and then kisses my kids.
I also have additional rules for meeting tumblr followers that don't apply to purely anonymous Craigslist hookups. When I post an ad on Craigslist, I give subs a relatively small amount of information about myself. The only thing they know about me is whatever I put in the ad. They're looking for an anonymous hookup with a straight married man, so I'm willing to provide a couple of pictures. However, I never share face pics with anyone. Never.
My tumblr followers are a different story. They have a hundred tumblr posts each month and 10 prior true stories here on Nifty to get to know me. They've seen my personality and know that I can dominate them the way they need. Plus, I won't agree to meet until I've chatted with them a bit and feel pretty comfortable with them. They should know me well enough to meet without needing a picture.
Dom/sub sex is largely mental. I admit up front that I don't have a perfect body, so if you need that, look somewhere else. If you absolutely have to see a picture of a man before you feel comfortable meeting him . . . I'm sure you can find another dominant alpha man somewhere to meet your needs, faggot. Good luck with your search.
The point is, I don't need to hookup with tumblr followers. I have plenty of other options. I can be "unfair" and set different rules for them because I don't want any pictures of me to be associated with this identity. I've already had one psycho faggot from Craigslist threaten to tell my wife he was sucking my dick (my loyal readers remember Matt from Part 6). I'm not going to give any tumblr faggots who have a lot more ammunition from all of my posts there and here on Nifty any pictures to help them blackmail me if they decide they want to reenact scenes from Fatal Attraction.
Anyway, "Ivan" is a tumblr follower who contacted me a several months ago. He was engaging, smart, funny and respected my boundaries (in spite of initially begging for a picture), so I've been chatting with him off and on.
While I didn't have any plans to visit the area where Ivan lives when he first contacted me, by staying in touch we figured out that we were both going to be visiting Tulsa at the same time back in January. He was in town most of the week, but I was only going to be there for one night.
We agreed to meet at his hotel Thursday night at 7:00. I prepared an agenda for our session based on things Ivan and I had previously discussed. Although I'm the dom and I'm in control, I like to find out what each sub I'm going to meet enjoys and tailor a meeting accordingly.
I've mentioned here before that it annoys me when a sub only says he wants to do whatever I want to do. A few readers have complained that it's an honest answer. The problem is that it doesn't tell me anything about you. So I have to ask follow up questions like, "What turns you on?" "What are your limits?" "What have you tried and liked or not liked?"
I do not meet subs who will not answer questions like these. If what turns you on is to be told what to do and obey my orders no matter what they are, that's fine. Tell me that. That's a different response from "I like whatever turns you on."
I'll make sure my needs are satisfied when I meet you, don't worry. If I can do it in a way that ensures you enjoy the meeting as well, we both win. So when I ask what turns you on, what you want to try, what limits you have, etc., answer the fucking questions. If you give me honest answers, I'm sure there will be common ground. If there isn't, you really don't want to meet me anyway because it isn't going to be a fun time for you.
Enough of that soapbox.
I didn't have a problem getting Ivan to tell me about his interests in sex and domination. So a few days before the appointment, I emailed Ivan to tell him what he'd need to do to prepare for our time together. In the email, I told him how I expected him to dress and what supplies to have on hand. He responded by saying his boss had given him a huge deadline for Friday morning following our scheduled appointment for Thursday night. He didn't say that he would follow my instructions or provide other details.
Based on Ivan's response, I assumed our meeting was off and made plans to have dinner with a business associate Thursday night. Then Thursday morning, Ivan sent me a message telling me he'd be ready at 7 "as planned" and giving me his hotel info and room number.
I responded, "I must've misunderstood your email the other night. In response to my message telling you what to do to prepare for our session, you told me you had a big deadline the next morning. You didn't say anything about meeting or complying with my directions in your email. I thought that meant you were canceling on me so I made other plans."
He wrote back about ten minutes later, "I didn't say I couldn't meet! I worked hard all week and was up until 3:00 this morning to make sure I could meet my bosses deadline and still see you. After all that you aren't even bothering to meet me? Just so we're clear, my email the other night was NOT intended to be a cancelation."
Now I was pissed. If Ivan wanted to convince me to meet, this was not the way to go about it. He should have been apologizing for the misunderstanding, not blaming me! How could he not see that he was wrong? Even putting aside dom/sub roles, he couldn't expect me to hold my night open for him after the email he had sent. You don't tell someone you have a huge deadline, imply that it will affect our plans, not confirm that you are still available, and then expect them to sit around hoping for the best, especially if the person you're talking to is an alpha male. I'm not waiting around to see if you work your shit out. If you don't affirm that you're in, I assume you are out. I deal with too many flakes to assume that you aren't wasting my time.
I wrote back, "Just so we're clear? It's a little late to be clarifying your email faggot. You didn't write me again for three days after sending me a vague message saying you had a huge deadline and failing to say you would follow my instructions. The time to be clear and tell me that the deadline wouldn't affect our appointment was three days ago. Better yet, if the deadline wasn't going to keep us from meeting, don't mention it at all. I don't need to know every minor thing that happens in your life asshole. Just so we're clear, if you give me information, I assume it affects me and that you aren't wasting my time with useless facts."
It took Ivan a while to respond after that. I assumed he was mad and had accepted that we wouldn't meet. Maybe he'd even flame me on tumblr, which is one of the reasons I had originally hesitated to meet followers.
I headed to the airport to catch my flight to Tulsa assuming the matter was resolved. However, when I got off the plane, I had a new email from Ivan.
"I'm so sorry, Sir. Your right. My email wasn't clear. I should have told you I would do anything to make sure I still had the time to see you. Please make time for me, Sir. I've worked so hard to avoid disappointing you. Please."
Aside from writing your in place of you're, it was a good email. It had the right tone, but I was still upset.
I emailed back: "I'm not canceling my other plans for you."
He quickly answered: "Please, Sir. I'll do anything you want."
I told him: "That's nothing new. The answer is still no."
For a long time, Ivan didn't respond. When he finally did, the message read, "Please, Sir! I'm begging you!! I've been looking forward to this so much. You have no idea how much you mean to me. I've never found another Dom like you. We don't even have to have sex. I just want to meet you and talk in person. You can punish me for being so disrespectful earlier. I'll pay you tribute! Anything you want, Sir! Please!!"
Now this was interesting. I've had a few tumblr followers ask about sending me Amazon gift cards as tribute and a few have asked me to set up a wish list so they can send me gifts. The whole cash fag concept doesn't do much for me most of the time, but when Ivan offered to pay me to come over to his room and punish him, I have to admit it made my dick jump.
I emailed Ivan two questions: "How much punishment are you prepared to endure? What did you have in mind for tribute?"
He responded almost immediately: "Thank you, Sir! Please don't be insulted, but I only have $100 on me. Will you accept that? I will accept whatever punishment you feel is appropriate for my behavior."
I didn't see Ivan's response when it came in because I was taking a shower and getting ready for my dinner meeting. While I was in the shower, I was trying to think up appropriate punishments for him, and my dick was getting hard as I engaged in the creative process. From chatting with Ivan, I knew he liked to be spanked and whipped, but endurance punishments were less fun for him. He tolerated them, but said he didn't especially like them. I also knew piss was not one of his limits, but he didn't enjoy drinking his own piss. With that information in mind, I was able to devise appropriate punishments for him.
I read Ivan's email after drying off but decided to keep him waiting while I got dressed. Making subs wait is another good form of punishment. His presumption that I had agreed to meet and thanking me before I had actually agreed annoyed me and ensured some additional punishment.
After I was dressed, I sat down at my computer to write my response:
"Dear faggot,
"You have convinced me to meet tonight after I'm finished with my colleague. I'm not sure when that will be, and you will have to satisfy certain conditions in the meantime. I hope you finished all of your work for tomorrow already because you will not have time to do more tonight until after I leave your room which will probably be late.
"Remember the bottles of water I told you to have on hand for when I get thirsty? You will have the honor of drinking the water you bought for me. Congratulations! Do it now! Both bottles. Then refill them from the tap and do it again. When you need to piss, do it into the bottles. If you need to piss more after the bottles are full, hold it. If you cannot hold it, you may empty a bottle by drinking. You do not have permission to empty a bottle any other way or to piss anywhere else, and both bottles had better be full when I arrive so I can watch you chug them in person.
"After you finish drinking the 4 bottles of water, get undressed except for the jockstrap and wrist/ankle cuffs I told you to wear. Kneel on the floor with your nose against the wall. Use your phone to take a picture when you are in position and text it to me at xxx-xxx-xxxx. Since we were supposed to meet at 7, I'll give you until then to get in position and text me. Set an alarm on your phone to remind you to take another picture every five minutes. You will stay in this position until I arrive. Make sure to bring the empty water bottles with you so you don't have to move when you need to piss.
"If I do not get 12 pictures every hour, I will add more punishments when I arrive, or I will decide that you are not serious about meeting and not show up. Oh, and leave my money on the bedside table so I see it when I walk in the room.
"One last thing. Open the door and leave it unlatched so I can push it open when I arrive. I'm not going to warn you before I show up. If the door isn't open for me when I get there, I'll leave. If you aren't in position when I open the door, I'll leave. If the bottles aren't full of piss or my money isn't on the table, I'll leave and you'll never hear from me again.
"Sir Tom"
I sent this email at 6:37 and headed off to dinner with a huge smile on my face. I got to the restaurant a few minutes before 7, but my business associate was running late. At 6:58, Ivan's first picture arrived.
Ivan had positioned his phone on a chair where he could reach his hand out to push the button to take the picture. The photo showed him on his knees, nose against the wall, back straight, and jock strap on. I could even see one full and one empty water bottle. I couldn't tell if the bottle had already been filled with piss or if he was saving a drink for later. I would have to ask when I saw him and punish him if he had failed to drink all of the water when instructed.
Since it looked like Ivan had done pretty much as commanded, I promptly texted back, "Good boy."
I received a quick, "Thank you, Sir! :)" and wondered if he'd still be smiling in an hour when his knees were sore and his back was cramping from holding the position.
My dinner companion arrived soon after. We had a good meal, and I achieved my business goals for the evening. I discreetly checked my phone throughout the meal to make sure Ivan was sending pictures as required. When I used the restroom, I took a moment to examine the pictures and noticed some slouching in Ivan's form. That helped reassure me that he was staying in position and not getting up to lay on the bed between each picture. His back was definitely starting to feel it. Of course, I'd check his knees to see how red they were and feel his back for knots in the muscles when I arrived to decide if I believed he had obeyed me and been punished sufficiently.
After dinner was finished, I went to a bar with my business associate for a couple of drinks. We chatted and relaxed, and I spent some time chatting with "Greg" on tumblr (the prior day's "Sub of the Day"). I explained Ivan's predicament to Greg and, in doing so, realized I should have only left Ivan with one bottle to relieve his bladder to ensure he would have to drink more often.
I texted Ivan to tell him to drink one bottle of urine and toss it out of his reach. I also told him he had to send me pictures of him drinking every time he emptied the bottle and that I would not arrive until I decided he'd had enough to drink. Before leaving the bar, I received 5 pictures of him drinking. One set of 2 pictures, and one set of 3 pictures.
I got to Ivan's hotel room around 10:30. I pushed the door open swiftly, and it immediately swung open. I was glad to see that Ivan had followed directions to leave it unlatched. However, the door had a noisy latch, and Ivan almost jumped out of his skin when he heard the sudden clatter. I expected it to make some noise and thought it would startle Ivan a little, but the racket was more than I had hoped for. I laughed and reminded Ivan that he didn't have permission to move.
"Nose against the wall, faggot. Back straight. Have you been maintaining form all night?"
"Sir, yes Sir," he answered without moving.
"Stay there while I have a look around," I told him.
I walked across the room to collect my money from the bedside table and looked around the room.
"Does your back hurt, faggot?"
"Sir, yes Sir!"
"Good. You deserve to feel some pain for being so disrespectful to me earlier. Next time, you'll remember your place when writing to a superior, won't you?"
"Sir, yes Sir. I'm very sorry I insulted you, Sir. I'm glad you took pity on me to teach me this lesson."
I walked over and stood behind Ivan, "I'm not sure you've learned your lesson yet, faggot. What do you think?"
"I don't know, Sir. That's your call, Sir."
"If you don't know the answer, then obviously you haven't. I think some lashes with my belt will do the trick. But I need to take a piss first. Turn around."
Ivan turned around on his knees and opened his mouth. I unzipped my pants, pulled out my cock, and told Ivan he'd better not spill. Then I put my dick in his open mouth, grabbed him by the hair, and let the piss flow.
I don't have a lot of experience pissing in a fag's mouth and sometimes it takes a minute to relax and let it go. Trying to piss with your dick in a warm mouth is a strange feeling at first. Fortunately I'd had a lot to drink at dinner and after at the bar, and my bladder was extra full. That helped tonight.
Because there was so much, I expected Ivan to spill at least some down his front, but he managed to take every drop.
"Damn, you make a nice urinal, faggot. Now suck," I told him.
Ivan started working my cock with his lips and tongue. I expected him to be skilled, and he didn't disappoint me. His mouth was nice and warm, and he used his tongue to stroke the underside of my cock just the way I like.
"Enough," I said after a minute and shoved his head away. "Your mouth feels dry. You must still be thirsty faggot. Drink," I told him as I touched the bottle of piss sitting next to him with the toe of my shoe.
Ivan bowed his head, muttered "Yes Sir," and grabbed the bottle. He unscrewed the lid and quickly chugged his own piss. I loved it.
I ruffled his hair and said, "Good boy. Now that you've finished degrading yourself to show penance for being disrespectful, it's time for me to show you how it made me feel. Get up and bend over the bed."
Ivan stood and walked to the side of the bed. I walked up behind him and ran my hands over his back and ass. He's a petite Hispanic guy with thick black hair on his head, brown eyes, and a nice round slightly hairy ass.
"This ass is so nice. It's a shame I have to beat it. Well, actually it's not. I'm sure it'll look even better with a little color."
"Yes Sir. I'm sure you will improve it, Sir."
"You're being such an agreeable faggot now. Why couldn't you have been like this earlier?"
"I'm sorry, Sir. I was so upset at the thought of not getting to see you that it made me forget to treat you like you deserve."
I unbuckled my belt and pulled it through all of the belt loops with a snap. Folding the belt in half, I traced the leather down Ivan's back and across his ass cheeks.
"How many lashes do you think you earned, faggot?"
"As many as you want to give me, Sir."
Smack! I struck his ass hard with the belt, and he yelped from the unexpected hit.
"That isn't a real answer. I want to know what you would do in my place."
"I don't know, Sir. I can't think like a real man."
I hit him again, even harder.
"Listen faggot. I want a real answer. You got pissed off when I told you I'd made other plans, so I know you understand what it feels like to be mad when someone doesn't give you the respect you think you deserve. Tell me how many lashes with my belt you think is an appropriate punishment for the disrespect you showed me. This is your last chance."
Ivan started to cry, "Please Sir. I'm so sorry. I didn't think before I emailed you. I was upset."
"The next word out of your mouth had better be a number or my safe word. I don't want to hear anything else. I don't need you to describe the situation. I know exactly what happened. It's obvious you weren't thinking. Now tell me a number or say my safe word."
Ivan remained bent over the bed crying a little. I knew his biggest fear was that he'd pick a number too low and make me angry (and Ivan confirmed that fact after the session). Finally, after about 30 seconds, he said 20.
"I think 20 is an appropriate number, faggot. I hit pretty hard with the belt, so that is more than enough to redden your ass and get it warmed up. Count them off."
Ivan counted each strike across his ass. He tried to be stoic but I wasn't going easy on him. He'd told me before we met that he liked his ass to be bruised, so I wanted to give him that gift. After we got to 20, I tossed the belt on the bed and Ivan thanked me for punishing him and teaching him to respect me.
In spite of his naturally brown skin, Ivan's ass was bright pink. And it felt nice and warm to the touch. He yelped a little as I kneeded his cheeks and spread them to get a look at his fag pussy.
Ivan told me he likes his hole to be used rough, so I stuck a dry finger inside without warning. He started to jerk away but caught himself.
"You like having my finger in your pussy, faggot?"
"Yes Sir."
"Let me feel you flex that hole."
Ivan squeezed my finger, and I shoved it in deeper.
"Good boy," I said as I started pushing down onto his prostate.
Ivan moaned half in pleasure and half in pain and said, "Sir, I really need to piss. May I please use the restroom."
I laughed, "I guess I'll allow that, but I need to piss again too. Get on your knees urinal boy. I'll let you use the toilet when I'm finished using you."
Ivan turned and dropped to his knees. My cock had gotten hard, so it took a little more time for me to relax and let the stream of piss flow into Ivan's mouth this time. Apparently unable to help himself, Ivan also kept licking the underside of my cockhead with his tongue while he waited for his drink. I pulled my dick out and slapped him.
"I'm already hard, faggot. You playing with my cock and licking it while I try to piss isn't helping."
I shoved my cock back in his mouth and went back to trying to piss. Ivan kept this tongue still now, but it took another minute for me to begin pissing anyway. That's one of the few times I ever feel awkward with a fag, but I figure it just means that I need more practice pissing in a warm mouth.
After Ivan swallowed my recycled whiskey from earlier in the evening, I gave him permission to use the restroom and sat on the bed. He took one of the longest pisses I've ever heard. I wish I would have timed it. He was probably going for two full minutes.
When I heard the stream weaken, I walked to the restroom. Ivan shook the last drops from his dick, and I saw some splatter the rim of the toilet.
I sighed audibly and said, "That won't do faggot. You can't leave a mess for the maid. Lick the toilet clean."
Ivan instantly dropped to his knees and began cleaning his urine from the toilet rim.
When he was done, I grabbed his hair and tilted his head up to face me, "Good little faggot. Now follow me."
I pulled Ivan along by his hair to the edge of the bed. Then I picked him up and tossed him onto the bed. I don't think I've ever seen such a joyful expression as the one Ivan had while he flew threw the air. Little faggots always like being tossed around.
I gave Ivan a moment to enjoy the sensation and then commanded him to roll over onto his stomach. I walked over to the dresser and grabbed the 3 clips I'd spotted when I looked around the room earlier. I carried the clips to the bed and dropped them on Ivan's back. Then I pulled him to the edge of the bed and put his wrists behind his back so I could clip the leather cuffs he was wearing together. Next I clipped his ankles together and pushed his feet up behind his back. I used the 3rd clip to attach Ivan's wrists to his ankles, and he was in a perfect hogtied position.
Once Ivan was restrained the way I wanted him, I grabbed the pillows and stacked them against the headboard. I turned Ivan so he was facing that direction and then got myself undressed. I climbed up with my back against the pillows, then leaned forward and gripped Ivan by the armpits to yank him toward me so that his head was in my lap.
"Suck faggot," I told him and grabbed a fistful of hair to direct his mouth to my dick. "This is the time to prove I didn't make a mistake by coming over tonight. Now you can show me how good you are with that tongue."
Ivan quickly got to work with his lips and tongue. It must have been hell on his neck, but he diligently worked my cock for about 15 minutes without complaint. I ran my fingers through his hair and complimented him throughout. Sometimes I held his head down to get him to gag (although making him gag was difficult because his throat is so well trained). I basically used his mouth as I would any cocksucker's while engaging in my typical style of dirty talk.
When I figured Ivan's neck was starting to cause him too much pain, I rolled him onto his side and got up. I pulled Ivan to the edge of the bed and continued using his mouth standing up. While I was standing there thrusting in and out of his mouth, I told Ivan that he'd done a good job atoning for his disrespect but I wasn't sure that he had earned the honor of tasting my cum. Pulling my dick from his mouth, I asked if he thought he'd done enough.
"Please, Sir. Please, I want to eat your load so bad. I'll do anything."
"I don't know," I answered. "It's really an honor to get to eat man's seed. I prefer to cum inside a warm mouth but I'm really conflicted."
Ivan moaned, vigorously licked my cock, and looked at me with pleading eyes. I continued shoving my dick in and out of his mouth without responding for a bit.
"I'm getting pretty close to cumming, so I've gotta make up my mind. I really think I've done enough for you already tonight without giving you that gift. And it's been a while since I painted a cocksucker's face with my load. You want to please me, right?"
"Mmm hmm."
I patted his head, "Good. I'm going to shoot my load on your face, and I want you to wear it all night long. I want you to text me a picture of you in morning by the window so I can see that it's daylight. If I don't see traces of my cum still on your face, I'm going to publish pictures of you drinking your piss that you texted me earlier."
Did I mention that Ivan also has a blackmail fetish? He moaned loudly in response, obviously loving this turn of events.
I laughed and said, "I thought you'd like that idea."
About 2 minutes later I shot a nice big load all over Ivan's face.
"Now lay still and give it time to dry while I take a shower."
I left Ivan laying on on the bed with his arms and legs still bound while I went to take a shower. I took my time, allowing the warm water to wash over me. After I dried off, I walked back to the side of the bed and told Ivan I had one final treat for him.
"I considered pissing in the ahower, but I thought you might be thirsty again, so I decided to save it for you. Open up faggot."
Ivan had a huge smile on his face and opened his mouth to receive my third load of piss in the last 90 minutes. This time I had little trouble letting it flow.
"Ahh, that feels nice using your mouth as a urinal. I could definitely get used to this."
When I had completely drained my bladder, I got dressed. Then I climbed on the bed and unfastened the clip binding Ivan's right wrist to his left wrist and ankles.
"I trust you can get yourself free the rest of the way," I told him.
"Yes, Sir. Thank you for such a terrific night, Sir."
I left Ivan laying on the bed with one free hand as he fumbled with the clips to release his other wrist. I've rarely seen a faggot look so happy. He also looked quite content when he texted me his picture by the window in the morning. It wasn't easy to make out my dried cum on the side of his face in the photo, but I could see some traces.
Because I've been so busy at work lately, it took me almost 6 months to write this story. Hey Ivan, since it's been so long and since I know you're going to jack off 50 times while you read this over and over again, it's time for you to give me more tribute. Send me an Amazon gift card to thank me for making your fantasy come true. Maybe I'll get my wife something nice with your money. I know you'd like that.