It was the dead of winter in a town known for its dedication to skiers. My regular job took me around the country to service the needs of medical centers. There always seemed to be a need for medical centers in ski resorts! I wasnt looking forward to spending several weeks in this cold, snowy town in a hotel, but maybe I would find something to pass the time.
Fortunately the hotel had a high speed Internet connection and I had my laptop. I began looking up sites and services in the area that catered to the needs of guys who enjoy the company of other guys. The bigger cities have ample services of this type, but the smaller towns often have very little. I was quite surprised to learn of a highly used chat board in the town where guys could hook up with each other.
After reading a while, I came to an ad that interested me. "First Timer age 27, seeks older man to introduce me to the joys of male-to-male _s_e_x_." I noted the address and shot off an e-mail. "I would love to introduce you to your first male encounter. I am gentle and respect limits. We can meet in my hotel."
I continued to read the board and came to one that really caught my attention. "College student, age 25, seeks older male to administer blistering spankings to help me keep my focus on my schoolwork. Not looking for _s_e_x_, not looking for nice guy. Just looking for strict daddy type to make me do my work and not spend so much time drinking and playing around. I want to be made to lie over the bed, stark naked, while you hit me hard, fast, and long with a wooden hair brush until you are convinced Ive learned my lesson. I hate pain, and I wont be able to take it, but make me do it anyway. Tears and crying are assumed to be part of my lesson."
I couldnt dash the e-mail off fast enough. "I would love to meet your disciplinary needs. You will be truly sorry you did not focus on your studies when I and my hair brush finish on your sorry ass. We can meet in the privacy of my hotel. Trust me, this is going to hurt you far more than it hurts me!"
I had left e-mail addresses in both cases, but I didnt hear any responses for several days. I was finally getting used to the cold weather, and there were a lot of clubs and restaurants in the area that enabled me to meet a number of people. I appreciate the beauty of both _s_e_x_es, so I was never at a loss for a conversation partner during the evenings.
On the fourth day, I finally got a response to my first letter. "Can you meet me for breakfast at Cocos tomorrow?" Unfortunately, the hotel served a free continental breakfast, so my company would not reimburse the cost of going to Cocos. Also, there just wouldnt be enough time.
"Sorry, but breakfast wont work for me. I am only free in the evenings after 6 PM."
The next day came another reply from "First Timer."
"I dont know if any other time than breakfast will work. You see, Im married, and I cant usually break away without my wife becoming suspicious. Well see, though."
"First Timer, I fully understand. I am staying at the XYZ hotel, and my cell is 123-4567. Give me a call if things work out for another time." I really was hoping things would work out. There is just something wonderful about being a guys first time and watching the expressions of joy when he discovers that men really know what they are doing with other men.
The next night, I was encouraged to see another e-mail. "Sir CT. I got your e-mail almost a week ago. I chickened out. It took me a long time to have the courage to put out an ad on the chat board, and I have been scared _s_h_i_t_less ever since. When I got your e-mail and realized my ass might soon be heating up, I got even more scared. I decided that I would just try to improve on my own.
"This morning, however, I got notice from the college that I am on probation. I realized that I needed this spanking really bad. Gawd, Im scared, though. I just want to make sure that you realize this is a punishment spanking, not a _s_e_x_ual thing. I need to come away from the session feeling the sting in my ass for a good week.
"My dad used to spank me with a wooden hairbrush when I was young – really hard and long. He passed away when I was eight, though, and I havent had proper discipline since. Im trying to do good by my mom, but the lure of the bars and the women, etc. etc. is just to strong.
"One thing, though. Will you be around if I need another one? I always felt that the worth of a spanking was in the fear of getting it again. Yours truly, Mike."
"Dear Mike. I fully understand your need. I went to a very competitive college myself," I wrote back, "and I understand how easy it is to get off track. I am at the XYZ hotel, room 213. My cell is 123-4567. Give me a call when we can get together. Ill put you at ease first, then make you get naked while I blister the crap out of your backsides. Ill make sure you feel it for at least a week. Sir CT."
Mike wrote back later that evening. "Sir. I will call you when I can arrange to meet you. Gawd _d_a_m_n_ Im scared. Still, do it right. Mike."
I really was looking forward to spanking Mike. Nothing pisses me off more than college guys taking their folks hard earned money and wasting it _f_u_c_k_ing around. And this young man was taking it from his widow mother. I was going to enjoy spanking Mike, but he was NOT going to enjoy a single second of getting it.
The next morning, I went out to a local department store to look for a good wooden hair brush. I dont usually carry spanking instruments on the road. I was able to find a wonderful one that looked like its designer knew of its disciplinary use. Mikes ass was really going to hurt from this one!
A couple of days went by and I didnt hear from Mike. I was certain that he had chickened out. I wrote him another e-mail.
"Mike. You get your sorry little ass over to my hotel and take this spanking youve been needing NOW! You know my room number and my cell. Im adding ten swats for every day you put this off. Sir CT."
I got an answer back in 10 minutes. "Sir, please forgive me. I dont have a car, and I have been having trouble getting a ride. I need the extra swats anyway, and I will be there."
The next night was Monday night. Around 7:00 I got a phone call. "Hey, this is Mike from the Internet. I can be there in 10 minutes. Is that good for you?"
I was getting excited about the thought of Mikes red ass. "Great. Room 123 at XYZ hotel. Just knock."
In two minutes, I got another call. "This is Mike. Im on my way over. Room 123, right?"
"Yes, and get your ass over here NOW!" I commanded.
"Yes sir!"
I rushed around the hotel room to make sure everything was in order. I hid my newly purchased hairbrush, minus the tags that had come on it, under one of the bed pillows. Seven minutes later, there was a knock at the door. I opened it to find a very attractive Irish-Italian young man waiting anxiously.
"Mike, right?" I queried. "From the Internet?"
"Yes," replied Mike, nervously.
Mike stood about 57", with wavy black hair and light freckles. He was a very handsome fellow, nicely toned, slightly muscular, and very clean cut. He stood there looking quite innocent and tender. As he stood looking me over, it became obvious just how anxious he was. His hands were shaking and his voice cracked as he spoke.
I wasnt surprised. Mike knew he had set himself up for a major piece of discipline, and it was time to pay up. I would have been nervous in his shoes.
I escorted Mike into the bedroom and had him set on the bed. I told him I would begin by putting him at ease with a massage. I excused myself for a second to use the bathroom. I also removed my shirt and t-shirt, which was my traditional spanking habit. When I had returned, Mike was fully undressed. That disappointed me for a minute, because I always liked to be the one to yank down their underwear. But I quickly got over it looking at this young man in his innocent, muscle-toned perfection.
"Roll over on your stomach," I requested. Mike quickly complied.
Mike had a perfectly formed ass, with just enough light hair to recognize that this was a grown man. It was pure white and could have served as a model for a statue. I was thoroughly going to enjoy turning that ass multiple shades of red!
I climbed on the bed next to Mike and began rubbing his shoulders. I could tell that Mike was active in some kind of sport, because his shoulders had well-formed muscles that were well-proportioned to his build. He wasnt hunky; just toned and nice. They felt rich between my fingers. My plan was to get Mike relaxed just enough that he could focus on his discipline.
Without Mike suspecting, I reached under the pillow and brought out the wooden hair brush. Mike was looking at the opposite wall the whole time. I raised the brush high over Mikes ass. I then brought it crashing down quickly and forcefully, three times on the right side, three times on the left, in less than two seconds.
Mike must have jumped three feet in the air, and he landed face up on the bed with a look of sheer horror on his face.
"What the _f_u_c_k_ are you doing?!!!" he screamed out extremely angrily. He looked like he was going to punch me in the nose.
"Im giving you the spanking you asked for," I replied, bewildered by his sudden change of heart.
"I didnt ask you for a beating. I asked you to introduce me to gay _s_e_x_!" Mike replied.
"Oh, my Gawd!" I exclaimed. "Youre First Timer and wanted to meet at Cocos, arent you?"
"Yes! Who did you think I was?" he asked, now totally confused and rubbing his stinging ass rapidly.
"Mike, there is another guy named Mike on his way to my room right now, expecting to get a major ass whipping. You just got his first six smacks!"
He looked at me even stranger now. "You do that too?" he asked with amazement.
"Yes, I do," I replied, "but only when guys want me to. I never would have hit you if I had not gotten you confused with another Mike."
He got a look of relief on his face.
"What I will point out, Mike, First Timer, is that those smacks turned you on big time. Your dick is rock hard."
Mike looked down at his 7" growing shaft. "You know, youre right. If you had told me I was going to get a spanking tonight, it would have freaked me out. But it does make me horny. Maybe I could watch the other guy get his ass whipped. Maybe I could help you hold him down?"
Suddenly there was another knock on the door. "Looks like thats how its going to work," I said. Hurry and get your pants on.
I went to the door and let college Mike in. He was one hot dude, let me tell you. He was Scandinavian, blond, blue, very muscle toned like First Timer, but about 3 inches taller. He too was shaking, but he had a worried, guilt-ridden look on his fact.
"Hello, Sir," he began. "Sorry Im late, but I ended up having to hitch hike over here. I dont mind telling you that I am one scared dude."
"Well, your tardiness earned you an extra element of discipline," I responded, quickly realizing how I could work First Timer into the situation. "You are going to get spanked in front of my friend. His name is Mike, too." It would be interesting to see how college Mike responded.
"Right now, I am so ashamed of the way Ive wasted my Moms hard earned money that I feel like I should be spanked in front of the whole school. Im afraid I wont be able to take all of the medicine Im in for, so youll probably need someone to hold my hands." I had never seen a kid so ready and almost begging for a spanking.
"Well, young man, go into the bedroom, introduce yourself to Mike, and get your clothes off."
College Mike quickly obeyed. As he bared his adorable body, I could see that he had a golden tan from head to toe. His ass was considerably lighter than his chest and legs, but he had spent a little time in a tanning salon naked. He had no hair on his ass whatsoever. Except for the tan, it was almost a babys butt.
I spoke to First Timer. "Mike, I want you to see what happens to young men who waste their mothers money for education on drinking and running around with the women. Hold this Mikes hands while I teach his little ass a lesson he wont forget for a while."
College Mike lay there with his silky ass quivering in anticipation. "I definitely deserve this," he explained to First timer. "Just hold me down good, because I dont handle pain very well. I need this, but I dont think I will be able to take it."
I was totally going to enjoy this. I raised the now-broken-in hairbrush over college Mikes butt and began the six-swat opening exercise with him. He too jumped about a foot in the air and attempted to turn over. He was unsuccessful, however, because First Timer held him tightly in position. "Ow, that really hurts!" he cried out. True to his promise, he wasnt handling his pain well at all. He began crying openly.
First timer piped in. "Mike, I know how much this hurts." I wanted to chuckle as to how true that statement was! "And I know it is going to get much worse before CT is done. But you are going to feel wonderful when it is all over."
"Ill be OK," replied college Mike through the tears. "This isnt supposed to be fun. It just hurts. But I need it to hurt." Would that all young men took their spankings with the resolve that this boy did.
I began to hit him again with the brush, three swats at a time on each side, hard and rapid, back and forth. Mike started to kick and tried several times to put a hand over his behind. First timer did his work well, however, and he bent one hand behind Mikes back and forced it painfully upward. Mike continued to cry, but quite forcefully at this point.
I climbed up on top of Mikes legs and sat on them. I cranked up the force and speed a bit more, increasing to five whacks on each cheek before moving to the other side. If Mike had been any stronger, First Timer and I would have had serious difficulty holding him down. He was bucking and stiffening out alternately. Finally, I realized Mike had taken about all he could stand without a break.
"All right, lets let him up for a break," I decided. "This isnt over, Mike. But you can have a few minutes to gain some composure."
College Mike leaped to his feet and began one of the fastest ass-rubbing sessions Id ever seen. He looked like he wanted to say something, but he was crying so uncontrollably that he couldnt speak. First Timer and I sat on the bed admiring Mikes tender and sore ass. What looked like a light suntan was looking more like a severe sunburn!
To be continued.