I had become online friends with a woman 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 Lisa 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. Lisa 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 a bit straight laced and was married, the thought of another woman wanting to see my cock, intrigued me. I continued to post pictures of myself fucking other women and sending private messages to Lisa.
Lisa explained that, although she lived a conservative lifestyle, she enjoyed the fantasy of being submissive to men and said if she ever had the courage to live out this fantasy, she would enjoy for me to be the one that dominated her, 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
Lisa and secretly, of her request to me. I contacted Lisa and told her that I was being put up in a hotel and asked if she 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 Lisa and arranged the dinner visit. I was extremely nervous when Lisa’s phone began to ring. I felt that I could not speak.
Dinner went great. Lisa 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 Lisa offered to pay the check, I stopped her and joked, “I got it. We’ll just have to come up with a way you can pay me back. If you were that kind of woman, I would expect you to at least put out.”
With that, 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 Lisa thought that picking up the bar tap would be a great way for her to pay her way.
When we arrived at my room, I told Lisa 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 Lisa, “I believe this is the portion of the night that you have the opportunity to pay for your meal.”
Although surprised, Lisa was quick to agree and ask me what I had in mind. Lisa allowed me to lead her to the side of the bed, where, I lifted the bed spread to reveal restraints, secured to the frame of the bed. Lisa quickly undressed and prepared herself to be my submissive sex toy.
After having Lisa kneel on her hands and knees on the bed, I used the soft rope to tie Lisa by her ankles. I then instructed Lisa to lie faced down across the bed, but not before placing two pillows under her 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 Lisa’s wrists.
Lisa looked incredible, as she laid across my hotel room bed, with her ass sticking way up into the air, just waiting for me to abuse her. She looked helpless, as well as quite nervous. She knew that she was at a point of no return. All that talk about being held down and sexually abused by a man had become a reality. Lisa 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 Lisa, there came a knock on the hotel door. I explained to Lisa that I had ordered some food from room service, in case we were to get hungry later on. With that, I excused myself to Lisa and walked towards the door.
I opened the door, leaving Lisa 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 Lisa.
Without a pause, Michael, who was of 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 Lisa’s exposed ass, he paused, gave Lisa’s large, round ass a gentle squeeze and asked Lisa what her safe word was. When he heard Lisa state in a low, almost inaudible voice, “Violet”, he release her ass and continued his journey to the bed stand, where I had just put condoms on top of.
I closed the room door and watched quietly as Michael picked up one of the condom packs and returned to Lisa’s exposed ass.
With no objection from the ever so quiet Lisa, Michael began to work his thumb into Lisa’s ass, while he gently returned to squeezing Lisa’s large but firm ass cheeks. When he heard Lisa release a low moan of approval, Michael assured her that there will be plenty more to come. Michael released Lisa’s ass and reached down and took hold of Lisa’s large clit. Michael turned to me and said, “You were right, she does have a very large clit.”
When Lisa looked back at me with a bit of a confused look, I felt I should explain what was happening. I told Lisa 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 Lisa if she 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 Lisa’s rectum with the thumb of his left hand, and reached between her legs to work the two middle fingers of his right hand into her cunt, I walked around to the side of the bed where Lisa’s head was located. I watched as Michael began giving Lisa gentle but firm smacks on her ass, while he continued to alternate between probing her ass and cunt. I knew Lisa was enjoying herself because each time Micheal’s hand made contact with her ass cheek, Lisa would let out a soft whimper, while she bit down on the bed spread beneath her.
I raised Lisa’s head up to look at me and told her that it seemed to me, that she had gotten herself into a tough situation. I could see tears of joy, as well as pain, as Lisa received another palm strike to her now red ass cheeks. I explained to Lisa that her submissive ordeal was about to taken up a notch.
I opened my robe to expose my erect cock to Lisa for the first time. I stepped in closer to Lisa’s head and guided my cock towards her welcoming lips. The warm feeling that Lisa’s mouth was giving my cock was incredible. Slowly, I began working my cock in and out of Lisa’s mouth.
Michael stopped striking Lisa’s ass, removed his probing fingers and began opening his pants. He took the condom that was awaiting his use, off of Lisa’s back and placed it onto his swollen cock. As Lisa worked her mouth around my cock to satisfy my needs, Michael guided his cock at the entrance to Lisa’s cunt and slowly worked it in.
Lisa began to whimper from all the attention she was getting. Although she knew she was in for a night of fun, she never expected she was going to be used in such a lewd capacity. She was in heaven. What started out as a night of curiosity, turned out to be a full blown submissive outing.
I was torn. Although I had never thought of myself as ever getting satisfaction from sexually controlling a woman, I was feeding my cock to the hungry mouth of a bound woman 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 Lisa from behind. I kept pace with his smooth rhythm, as I worked my cock in and out of Lisa’s welcoming mouth. When I saw Michael stiffen up and lean into Lisa, I knew he was now filling his condom, still deep within Lisa’s womb, with his heavy load of come. It was too much for me to take. I held Lisa’s head still and I shot my own load of thick come deep into her 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 Lisa’s cunt 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 Lisa and I were once again alone, I began to remove Lisa’s restraints. when I went around to untie Lisa’s ankles, I discovered that Lisa had her own climax from all the excitement and came on the bed. I joked that Lisa must have truly enjoyed herself, gauging from the large puddle of nectar that had run down her thigh and gathered below her.
After getting dressed, Lisa and I decided that we should go back 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.
