This chapter of the story is true. It was a bit of a clumsy first meeting on a weekday night. I had a choice before the second chapter. What happens in subsequent chapters is what I wished had happened. I haven't worked out the whole storyline, but it will probably delve into my many fetishes and what I wished had happened had I made only 1 different decision in my life.
To most of the world I am a vanilla straight male. If you met me, you would expect me to be a member of a church, working out at a local gym, maybe a part of a local sports team. I wear suits to work and even when dressed casually, it will be with a belt and my shirt tucked in and looking neat. No ring on my finger might give away the fact that I am not married but you would assume there was a girlfriend or girlfriends somewhere. This perception is almost entirely false but carefully maintained. I do date women, but I have always had the kinkiest deviant desires. At this point in my life, I had acted on a lot of these kinks with different women. I had only had oral sex with men a few times and in very discrete encounters, but sex with men was something I was craving.
I was traveling and in town for a week of work. Monday night after work I ordered room service and logged on to a chat room service. I wasn't looking for love or a dating relationship. I was looking for a dominant kinky man to use me and tie me up. I was wandering through the site looking at the different gay chatrooms and I ended up creating one called "submissive 32 y/o male". I quickly got a lot of attention. Most of it did not interest me and after about 2 hours, it was getting late and I was getting discouraged. I was contemplating just cumming to porn and calling it a night when John came into the room and started chatting. After about an hour trying to talk to him and multitasking between multiple other horny uninteresting men, I moved into a private chat to talk to John.
He was interesting. His profile said he was 41 and single. He was articulate, educated, and seemed very interested in a younger submissive guy and we were getting along chatting. He lived in Ithaca which was about 50 minutes away. We talked for a long time and it was getting me extremely excited. I made it clear that I wanted to be completely submissive and to please a dominant man. I did not need any reciprocation. I wanted to be used for his pleasure and I would do almost anything he wanted as long as it was safe. This was a fantasy that I had been thinking about for several weeks. I essentially wanted to be a sex slave to a man and be used. I admitted to him that I had never had anal sex with a man, but I did not rule it out. He said we could take it easy and see how it goes. All in all, he was very nice and put me at ease.
We agreed to meet the following evening. I could get off work at a reasonable time and I would drive to Ithaca and meet. We agreed to meet at 5pm at a CVS parking lot that he gave me directions to. I left work at 4pm and made the drive. I arrived a few minutes early and pulled up beside a convertible. I had not seen a picture, but I assumed this was John.
When I opened my door and stepped out, he smiled and said, "aren't you beautiful!"
I was flattered and stammered a reply. The chit chat didn't last long. He had wanted to meet here. I assume he wanted a safe public place to meet a stranger from the internet, but I also think he knew what he wanted and quickly decided that I was harmless. He told me to follow him to his house, so I got back in the car and we drove a short distance. A slight left turn led us up a driveway. The driveway stopped right in front of the front door of his house about halfway up the hillside in the woods. The driveway was between the hillside and his house. The other side of the house looked out through the woods with a beautiful view through the trees. It was a very private setting with no neighbors in view.
He got out of his little sportscar and I followed him into his front door. I could hear a road somewhere below the house but could not see anything but the trees. He noticed the camwalker on my leg for the first time. A camwalker is a boot that is used in place of a cast or after a cast. I explained that it was from a broken ankle.
Once inside he poured me a glass of wine and we sat on the couch to talk. He was friendly, excited, and much more comfortable being in this situation than I was. I was very nervous but also aroused. We talked for a while. I had been expecting to just come in and have sex, but that was not his agenda. I could tell he found me attractive, but he did not seem to be in a hurry. We were discussing a little of everything. He told me that he was divorced and had two daughters. He was 51 and not 41 as his profile had said. He did look older than 41. He was very interested in me and let me talk way too much. He would probe gently, and it was obvious that I had not had much experience with men. I did not know if I was gay or bi and could not decide. He was quick to reassure me that I did not have to decide. I should just go with it.
We discussed our kinks further. We had discussed some of these online, but I admitted that I cross-dressed a lot and I loved inescapable bondage, pain, spanking and submitting to dominants.
I must have been there at least an hour before he said, "so, you want to be submissive."
"Yes, I do."
"What do you want to do," he asked, staring at me as I sat beside him.
He smiled at this and said, "OK then, get to it," and he unzipped his pants. I leaned over and took his cock in my hand and started stroking it. He unbuttoned his pants fully and his cock was almost instantly hard.
"Go ahead. Suck my cock!
I could hardly wait. This is what I wanted. I pulled out a condom and quickly put it on him. I started licking the head of his cock and then sucking on just the head as I gently moved my mouth up and down. It was awkward sitting beside him, so I moved onto the floor kneeling. This was difficult with the camwalker, but I managed. The whole time John kept encouraging me, talking dirty to me, and telling me how good it felt. I was taking it farther and farther into my mouth and throat.
After about 15 minutes he stopped me and said, "let's get in the hot tub." He then remembered the camwalker and disappointedly said, "oh you can't with your leg, can you?"
I quickly reassured him I could. I could take it off and get in, I just could not walk on it. He smiled broadly and led me out the den door to his back porch. There was a big hot tub off to the right. He removed the top and started getting undressed. I followed and sat down and removed the camwalker and then my pants and shirt. He was already naked, and he bent over and kissed me and then stepped up two stairs and down into the hot tub. I hobbled up and eased myself into the tub.
I wanted him now, a lot, and moved over to his side of the hot tub and kissed him. My hands were busy under the water. He had never lost his erection. He sat up on the side of the hot tub and I took his cock in my mouth. I really wanted to suck his cock and I wanted him to cum. I was so horny just to please him. I went to work zealously using my mouth and my hands. He was talking dirty to me and telling me what to do. I would alternate between sucking his cock as deep as I could into my mouth while stroking him, then switch to sucking his balls into my mouth while I stroked his cock. Try as I might, I could not make him cum. My inexperience was showing and even though I was trying to do everything he instructed me to do he was not getting close to an orgasm.
With both balls in my mouth, I looked up at his face, let his balls slip out and said, "please fuck me."
"Are you sure?"
"Yes Please. I want it so bad."
He smiled and eased himself down in the water sitting. I rose forward and took his cock and placed it on my asshole as I straddled him. I should have eased it in, but I was too horny. I sat down on him as quickly as my ass would allow it and soon, I was bouncing on him and sloshing water everywhere. I had never really kissed a man before, but he was kissing me. I was loving every minute of it. I was sucking on his tongue and enjoying him, enjoying me. Even though he was never close to cumming he was enjoying me as I took his whole cock inside me. I have always played with extremely long big toys. His cock was nice but not nearly as big as my 10- and 12-inch dildos at home, so he was easy to take.
As I was getting tired, he slowed me down. He also kept talking to me as I slowly rocked back and forth on him.
"Let's go to the bedroom for some bondage," he whispered.
I wanted nothing more. I got out and we dried off. I put the camwalker on. I had done more damage to my ankle than I realized bouncing up and down on him, but I was focused on only one thing. I took his hand and led him to the bedroom.
He was not that experienced with bondage, but I was. He pulled out some rope and I quickly tied it to the corners of the top of the four-poster bed and the bottom at the foot of the bed. I tied my ankles spread and tied one arm. He took the other arm and tied it. I was standing there spread eagled and finally helpless like I craved. He stood behind me. Since he was not that experienced, he did not really know what to do with me. He teased me a bit and kissed my neck but when he tried to fuck me standing up it was not a very easy position. He tried to spank me a little bit, but he couldn't really figure it out and I could tell that he was not enjoying it much.
I was disappointed when he untied me and told me to lay on the bed, but I understood. I lay down as instructed on my back with my head off the edge tilted back. When I was there, he took my head and forced his cock into my mouth and started fucking my mouth. I was in heaven. He was gentle and truthfully, I didn't want him to be. I wanted to feel his cock ramming down my throat. I would not have been able to handle it at that time, so it was good that he was gentle.
As he was fucking my mouth, he was finally getting close to orgasm.
He was talking to me and he asked me, "what do you want me to do to you?"
I knew and answered immediately, when he gave me few seconds without his cock in my mouth.
"Please cum on my face," I begged. I really wanted it. I had always fantasized about this.
He pushed his cock back in my mouth and started fucking my face again. "I will cum on your face. I have really enjoyed you. I am so glad I was the first to fuck your ass and that you trusted me to tie you up."
With that he removed his cock from me, he removed the condom quickly, climbed up on the bed and straddled my chest and put his cock head in my mouth and started stroking. A moment later he pulled his cock from my lips and started stroking faster as he came all over my face grunting and moaning in pleasure. I lay there enjoying every minute of it.
The next few minutes are a bit of a blur. I was soon in the bathroom cleaning my face. He was down the hall in his own bathroom and then we were back in the den. He again was very comfortable, and I was very uncomfortable. He wanted to see me again soon and he asked me to join him on a weekend camping trip with his two adult daughters the following weekend. This was terrifying to me. Dating a man had not been my plan. Submissive sex had been my plan. I could not deny that the idea was appealing though. Also, since he was 20 years older than me, his daughters would be close to my age, which was a little disconcerting. At that point, I was rushing to leave gracefully and not commit to anything. I needed to think.
His last comment was, "please think about it," I would love to introduce you to my daughters, and it will be a fun trip."
On my drive home, it was all I did think about. I was still incredibly horny, and I had loved being fucked by John. The bondage and domination had not been that exciting, but I had really enjoyed being with him. I got back to my hotel and started masturbating, fantasizing about camping with John and his two daughters. I wanted to go. I could not decide if I wanted to go as John's young gay boytoy or cross-dressed. In the end I came to an incredible orgasm of being fucked in his tent.
Wednesday night I was chatting with john online and he was trying to convince me to join him for the trip. I was drinking in my hotel room and the distance, alcohol and chatroom made me bold. I admitted that I did want to join him, but I had fantasized about doing the weekend dressed as a woman.
I don't know what I really expected but I was shocked when he said, "Great. Let's do that."