I began to understand that I had crossed into a different and undiscovered place.
What came into focus was how I thought about what just happened. After meeting Tommy, and now knowing who he was, I let myself dive into the deep end, so to speak.
Tommy was the assistant to the President of the Company that I had been working so hard to close a deal that would make my job finally secure. He was, as I was to learn, somewhat of a stalker, Gloryhole shadow, and regular cock worshiper.
Tommy was a regular at the Arcade where I became a regular when in town and wanting a release. Tommy was a bit of a stalker and would lurk outside the booths after finishing me and then follow me out which is how he came to know who I was. He was always very professional in the offices but was waiting when I went to the Arcade.
Now here I was, having spent the night together. Both of us enjoyed several blowjobs with each other and my first fuck of a man’s ass. And now, with my cock deep in his throat, I was about to dump another load before I even had coffee.
As I am getting comfortable with my sexuality and feel like being a bit more adventurous.
One night while traveling, I let myself be picked up by an older businessman who thinks he is winning the night. He starts with his tales of never having an attraction to a man before. He says he hasn’t ever seen a man that he thought was hot in a way that made him want to ask me back to his room.
I let him blow me. And while he is jerking me hard, again he says he wants me to fuck him. Though he says that he has never done this before he has already lubed himself up and the plug he was wearing a few minutes ago is soaking in the sink.
I tell Tommy that I still have some stuff to figure out. And as much as I continue to fuck him and give him head in return I wonder about himself.
Work continues at a rapid pace.
I had to fly down South. It’s a pretty awful trip. Bad flights, bad hotels, bad food. A really shitty bar, with bad music and lots of people smoking. I stood at the door with my beer, and a woman comes and stands next to me because we can’t take drinks outside.
She is pretty in the way that we all are when we are free of our anchors. I was feeling a need to push away from my want to fuck Tommy, so I took the time to talk to her, to listen, and to seduce her.
She was married but unhappy. She said that she wanted to feel excited, so I asked her what she would like if she could do anything and no one would ever know. She says that she wants to fuck herself with a huge cock while someone watches. She had never had an orgasm that she didn’t do for herself. and her husband was too fat and lazy to lick her pussy.
I said to her that I would love to watch her get herself off. This blew her mind. She said that she only started watching herself bring herself off in a mirror a little while ago. I asked her if she wanted to use a dildo anytime soon and she grabbed my arm and squealed.
We had a plan.
I told her that I was going to the store nearby to get a large vegetable and a bottle of oil. I gave her my room number and said that I would love to watch her make herself happy.
When I got back to my room, she was waiting outside in a hotel robe. I invited her in and we both rubbed her down in olive oil. She got herself off in seconds and then fucked herself with the large zucchini that I bought while I joined in to lick her clitoris and massage her asshole.
Her orgasms were incredible.
When she was relaxing she asked me to lick her another orgasm. I started at her toes and up to her ear lobes. Keyed in on her engorged clitoris and then spent a long time laving and fingering her ass.
She got on her belly and brought herself up to her knees parting her cheeks. I slowly introduced the zucchini into her ass. Slowly opening her to the task.
Soon she was pushing back and allowing her ass to receive the fucking that she wanted. We pushed her to a huge orgasm which left us both panting and sweating.
She asked me to please fuck her ass with a man’s cock and I did. Later after we had showered and napped I fucked for the last time and as the sun was coming up I licked my cum out of her pussy.
We were both in heaven. I got her a cab back to her husband and life.
About a month later Tommy couldn’t come to meet me in Toronto and I was kind of pissed off.
I was determined to pick up a guy and fuck him as a fuck you to Tommy.
Right away, when I went down to the bar, there was this really good-looking guy and when I sat down, he offered to buy me a drink.
I felt lucky and accepted the offer thinking that this would be the mouth and ass I would enjoy all night. He then told me that it was his wife who had challenged him to pick up a man to fuck them both and was waiting upstairs. The wife wanted him to pick up someone and watch her get fucked. Then she wanted him to lick the cum out of her after and then see what happened next.
I was all for it and we had a nice time at first, the usual stuff of the amateur swingers. Him jerking off while I fucked his wife and she asking him to eat my cum after I blew my load.
She then told him to suck me off so I could get hard again so I could fuck her again. I held off long enough with him sucking me to cum in his mouth which really turned her on.
She said that her “real thing” was to watch me fuck his ass. I did and enjoyed a few more things with them.
Back home a while later at my house, I was finishing fucking Tommy one morning. And feeling in a more adventurous place I asked him about having anal sex. I said that wanted to finally experience it myself. Tommy wrapped his legs around me while I was cumming deep in him and looked me in the eyes.
“Oh, yes Sam is the cock for you.”
I was soon to meet Sam.
In the shower after, Tommy was a dervish. He washed my cock and washed it again until I was rock hard. He put two soapy fingers up my ass and twisted them around. He got down on the floor and tongued my ass. “Oh, Sam is the cock for your pretty ass.” Then he got me off again.
Tommy made a plan and a date for me.
The date was soon set. I was nervous.
Preparing for Sam was the order of the day.
Tommy and I had each taken the day off work so that I would be ready to meet Sam.
Sam, as it turned out, was an executive in the company that I was finalizing our deal with. He also was clearly fucking Tommy on a regular basis.
I was showered and cleaned head to toe. My cock and balls were shaved clean, my ass was cleaned and filled with lube.
Then dressed in my best suit I headed to Sam and my undoing perhaps.
I was now sitting in my office, my cock drooling and my ass leaking lube when the Head of Sales walked in. He was a tall fit older gentleman. I was quickly introduced to Sam by my boss. Sam was very brisk with introductions and told my boss that we had some paperwork for us to manage and to leave us to it.
My boss was cowed and quickly left the room.
Sam turned and locked my door and walked to my chair and opened his fly. He pulled out the largest cock I had ever seen and put his hand on the back of my head. I opened my mouth and then my throat and let him fully fuck my mouth.
I don’t know how long he fucked me but suddenly he was cumming down my throat and bubbling up into my mouth. He gripped my ears until he was finished. My eyes were tearing up and I was trying to catch my breath when he pulled me up and told me to drop my pants.
“No, no please, I can’t be caught being fucked on my desk.” He covered my mouth and bent me across my desk and put a large cold lubed plug in my ass, and had me suck him again. It was even better the second time. I was being shown how I was expected to please his cock. I held him deep in my throat this time as he fed his load into my belly.
Later that night, when the company had our reception for the finishing of the deal, I was a complete wreck. I didn’t know if anyone knew what was happening to me and Sam. I was afraid to take this plug out of my ass and was worried about even going to the party.
I went to the party anyway but had too much to drink too fast. I excused myself and went back to my house. I undressed and took a cold shower. Somewhat revived I began to toy with the plug. I was soon rock hard and fucking myself with the plug. There was a message on my answering machine telling me where I was to meet Sam. I didn’t even think about it, In the morning I dressed and took the address in hand, and went to meet Sam.
Sam, dressed in a robe, opened the door before I even knocked. He told me to remove my clothes at the door. I did and when I walked into the suite where Sam was standing alongside a man about his size also only wearing a robe.
“This is Steve, you are to take care of us and we will take care of you, now go to the shower and follow your cleansing directions and come here when you are finished.”
So, naked, cleaned inside and out, I walked forward and Sam put a hand on my shoulder and lowered me in front of Steve. Steve opened his robe and presented me with an equally beautiful cock. I did what was expected and was soon taking him into myself. Sam was behind me pressing the plug into my ass with his foot and guiding my head up and down Steve’s penis.
After I had made Steve cum in my mouth they walked me to a low couch. Sam poured oil on my cock and balls and we all rubbed it in. I was rigid. Steve was fucking me with the plug while I was now sucking Sam as he stood over me. Steve would take the plug nearly out of my ass and plunge it back in again over and over. Sam was standing over me with his balls bouncing off my chin. As he erupted in my mouth he asked me “Are you ready?”
“YES, I hissed, yes, please.”
Steve pulled the plug out of me quickly and eased his cock in my ass for what seemed like a week. Sam started to fuck my mouth again with his softening cock at the same time. I really didn’t know what I was feeling. It was surrender. For the first time in my life, I was the point of pleasure for something else. Steve came quickly into my ass and Sam took his place with his revived erection and continued fucking me until he too finished in my ass. As he stood there panting and shrinking inside me, Steve started to suck me. I came in an instant. He stood up and kissed Sam with a mouth full of my cum.
I was fucked one more time by each of them that night. Tommy was right.
Which leads to the third part.