Getting What He Asked For
Add: 5 August 2015 / 17:46
A few years ago, my company sent me to Chicago to speak at a convention. Although I was a bit nervous about speaking to the large group, I was a lot more nervous about the plans I made to meet up with someone I met on line.
I had become online friends with a man that lived in the Chicago area. Although we seemed to have lived two very different lives, we enjoyed sharing e-mails and text messages.
It all started when Tom saw a photo I uploaded to a website I visited. The picture was of me getting a blow job from a woman I had just met. In it, the woman looked quite content while, sucking on my cock. Tom saw the photo, complimented me on the size of my cock and requested that I post more.
Although I have always thought of myself as being straight and was married, the thought of another man wanting to see my cock, intrigued me. I continued to post pictures of myself fucking other women and sending private messages to Tom.
Tom explained that, although he lived a straight lifestyle, he enjoyed the fantasy of being submissive to men and said if he ever had the courage to live out this fantasy, he would enjoy for me to be the one that dominated him, if ever we had a chance to meet. Although we continued to write back and forth about what we would do, if we were to meet, I felt sure that it would never happen.
With that said, when the news came that my company was going to send me to Chicago, I immediately thought of Tom and secretly, of his request to me. I contacted Tom and told him that I was being put up in a hotel and asked if he would like to meet for dinner. Deep down, I knew I was getting myself into more than just a dinner bill.
After the convention, I planned a few more days to stay, knowing that anyone that might have known me from my line of work, would have left the area. I called Tom and arranged the dinner visit. I was extremely nervous when Tom's phone began to ring. I felt that I could not speak.
Dinner went great. Tom and I talked about our careers, as well as our spouses. it seemed we had a lot more in common than we both originally thought. When the bill came and Tom offered to pay the check, I stopped him and joked, "I got it. We'll just have to come up with a way you can pay me back.If you were a woman, I would expect you to at least put out."
We both laughed. An uneasy silence came over us, knowing that the dinner was over and we would have to part ways. I broke the silence by offering to visit the hotel's bar, for a few more drinks but stated that I would really like to get into more comfortable clothes before we did. I was pleased to hear that Tom thought that would be a great way for him to pay his way.
When we arrived at my room, I told Tom that I would only be a moment and went into the bathroom to get changed. However, when I returned from the bathroom, I was dressed in only a robe. I explained to Tom, "I believe this is the portion of the night that you have the opportunity to pay for your meal."
Although surprised, Tom was quick to agree and ask me what I had in mind. Tom allowed me to lead him to the side of the bed, where I lifted the bed spread to reveal restraints secured to the frame of the bed. Tom quickly undressed and prepared himself to be my submissive sex toy.
After having Tom kneel on his hands and knees on the bed, I used the soft rope to tie Tom by his ankles. I then instructed Tom to lie faced down across the bed, but not before placing two pillows under his stomach. I then walked around to the other side of the bed, pulled up the other restraints tied to that side of the bed and secured Tom's wrists.
There was Tom. laying across my hotel room bed, with his ass sticking way up into the air, just waiting for me to abuse him. He looked helpless, as well as quite nervous. He knew that he was at a point of no return. All that talk about being held down and sexually abused by a man had become a reality. Tom watched as I removed some items for the bed stand drawer and placed them on the nightstand and bed.
Just when I was about to start my domination of Tom, there came a knock on the hotel door. I explained to Tom that I had ordered some food from room service, in case we were to get hungry later on. With that, I excused myself to Tom and walked towards the door.
I opened the door, leaving Tom tied across the bed and vulnerable. I greeted the man from room service, who told me his name was Michael, and instructed him to set the food we ordered, by the window. This would cause the man to walk past Tom.
Without a pause, Michael, who was medium build and looked to be in his mid fifties, pushed the food cart across the room and set up the utensils. When Michael was done, he turned towards the door to leave. However, when he reached the side of the bed nearest to the door, Michael turned and walked towards the bed stand.
As he passed Tom's exposed ass, he paused, gave Tom's large testicles a gentle squeeze and asked Tom what his safe word was. When he heard Tom state in a low, almost inaudible voice, "Violet", he release his testicles and continued his journey to the bed stand, where I had just put condoms on.
I closed the room door and watched quietly as Michael picked up one of the condom packs and returned to Tom's exposed ass. I thought it odd when Michael placed the unopened condom on top of small of Tom's back. Oddly, it was I who seemed like the foreign person in the room, as I watched Michael pick up the anal lubricant from the bed and apply it generously onto Tom's anus.
With no objection from the ever so quiet Tom, Michael began to work his thumb into Tom's ass, while gently returned to squeezing Tom's massive testicles. When he heard Tom release a low moan of approval, Michael assured him that there will be plenty more to come. Michael released Toms balls and reached down and took hold of Tom's small dick. Michael turned to me and said, "you were right, he does have a very small dick."
When Tom looked back at me with a bit of a confused look, I felt I should explain what was happening. I told Tom that since I had booked this hotel room for the last five days and had ordered room service several times during the week, I had gotten to talk to Michael on several occasions. On one occasion, I had asked Michael if he had ever walked in on any crazy situations while doing his job
Michael told me that he has seen just about anything I could have thought of, from horny women answering the door naked, in hopes of having sex with him, to a full out orgy. Michael also admitted that he had joined in on the fun on several occasions. That is when I asked Michael if he would be interested in joining in on some fun I had planned on having.
With that said, I asked Tom if he was still interested in allowing our friend to stay. When I was answered with an eager yes, I asked Michael If he could stick around a little bit longer. I was assured by Michael, that he would have at least another thirty-five minutes before someone would wonder where he was
As Michael returned to probing Tom's rectum with first his thumb, and then the two middle fingers of his right hand, I walked around to the side of the bed where Tom's head was located. I watched as Michael began giving Tom gentle but firm smacks on his ass, while he probed his ass. I knew Tom was enjoying himself because each time Micheal's hand made contact with his ass cheek, Tom would let out a soft whimper, while he bit down on the bed spread beneath him.
I raised Tom's head up to look at me and told Tom that it seemed to me that he had gotten himself into a tough situation. I could see tears of joy, as well as pain, as Tom received another palm strike to his now red ass cheeks. I explained to Tom that his submissive ordeal was about to taken up a notch
I opened my robe to expose my erect cock to Tom for the first time. I stepped in closer to Tom's head and guided my cock towards Tom's welcoming lips. The warm feeling that Tom's mouth was giving my cock was incredible. Slowly, I began working my cock in and out of Tom's mouth.
Michael stopped striking Tom's ass, removed his probing fingers and began opening his pants. He took the condom that was awaiting his use, off of Tom's back and placed it onto his swollen cock. As Tom worked his mouth around my cock to satisfy my needs, Michael guided his cock at the entrance to Tom's ass and slowly worked it in.
Tom began to whimper from all the attention he was getting. Although he knew he was in for a night of fun, he never expected he was going to be used in such a lewd capacity. He was in heaven. What started out as a night of curiosity, turned out to be a full blown homosexual outing.
I was torn. Although I had never thought of myself as ever getting satisfaction from another man, I was feeding my cock to the hungry mouth of a man and I was loving the feeling. The very fact that my mind believed this was wrong, made it feel that much greater. The feeling of being so far from my normal life and able to experiment was liberating
I watched as Michael pumped into Tom from behind. I kept pace with his smooth rhythm, as I worked my cock in and out of Tom's welcoming mouth. When I saw Michael stiffen up and lean into Tom, I knew he was now filling his condom, still deep within Tom's bowels, with his heavy load of come. It was too much for me to take. I held Tom's head still and I shot my own load of thick come deep into Tom's throat.
When Michael and I recovered from our climaxes, we both looked at each other and complimented each other on a job well done. Michael removed his cock from Tom's ass and pulled the used condom off his cock, deposing of it in the bedside waste basket. Michael then pulled his pants up and said he had to return to work, before he was missed.
Now that Tom and I were once again alone, I began to remove Tom's restraints. when I went around to untie Tom's ankles, I discovered that Tom had his own climax, from all the excitement and ejaculated onto the bed. I joked that Tom must have truly enjoyed himself gauging from the large puddle of semen that had gathered below him.
After getting dressed, Tom and I decided that we should go beck down to the hotel bar to have that drink. On the way, we passed Michael in the hall, as he traveled to another room to deliver that guest's room service, as well as any another service he could provide.