I met Bill in the terminal of the Saginaw airport. I had only flown once before (well, twice if you include the round trip). While we were waiting to board, I told Bill that Sean and I were going camping next week.
"Good. I wish that I had thought of that. I'd love to get you in a two man tent."
I don't know why, but I was a little pissed at Bill. Before I left the house, I checked the surveillance cameras for the time that our "visitor" was there to impersonate Jim. Nothing. When I thought about it, it made sense. Bill knew that I would check the cameras if I were curious enough. So, actually, I don't know if I was pissed at Bill or at myself. But when Bill said this, I was no longer pissed. "Thank you, Bill."
We talked about where Sean and I were going. I really didn't have much information on that. Sean said he would get us there. We were taking his pickup. I only knew that the campground was in the Upper Peninsula. Living that far north, I've been over that bridge a bunch of times. I never liked going over that bridge.
They announced boarding for the first class passengers. That was us.
As we stood up, I asked Bill about the truck that Sean saw out front of the house. "Sean said he saw Jim's truck out front yesterday."
Bill and I walked to the gate, in front of all of the "coach" passengers. While we were waiting to scan our tickets, Bill leaned over to me and said, "What makes you think that I wouldn't rent a truck similar to Jim's, just in case?"
I've got to give it to Bill. He trumped my ace. There would always be that slight doubt, and I thought that was what Bill wanted. When it comes right down to it, it was what I wanted as well. The whole idea of the get together was to see how I responded to the idea that Jim was fucking me. I've only been having sex for a short time, but Bill was making sure that I had plenty of options. The short time that I was with "Jim" was in the top 5 or my experiences. If I knew it was Jim, it would be a solid number 2, behind the night that Bill took my virginity. Then I thought about Stephanie. Maybe that would be a tied for 2
nd
.
We arrived at O'Hare, and were met by a guy with a placard with my name on it. When I went up to him, he asked me for my ID. I showed it to him and he welcomed me to Chicago. He asked me if we had any luggage to claim.
Bill said, "There is one piece." He handed the claim check over and we waited while the guy retrieved our luggage.
I looked at Bill when he left. "This is unbelievable."
Bill looked at me. "We could've grabbed our own luggage, and taken the subway down to the hotel, but I thought you might like this better."
The subway? They have a subway? Detroit had a "People Mover", an elevated subway, but it was one track. I forgot that Chicago has a "subway system". "Can we ride the subway later?"
Bill laughed and gave me a hug.
We went to the hotel. It was called the Ritz-Carlton. Bill told me that Carl and his wife would be meeting us for dinner.
"Carl has a wife?"
"Yes. Most of the performers are married or have a steady partner."
Wow. I had so many questions. "Where are we eating?"
Bill laughed. "We're eating downstairs. Coat and tie are required."
Bill didn't tell me to bring a fucking tie. "I don't have a tie."
"Well, it's a good thing that I brought that extra luggage. It has a suit, shirt and a tie for you. You'll have to provide your own socks, underwear and shoes."
I can do this. "Thank you, Bill. How long before we have to go downstairs?"
Bill and I traded blow jobs, then took a shower. It was a spacious shower for a hotel room. We went downstairs at 7 and met Carl and Midge. Midge and I wound up sitting next to each other.
Midge leaned over and said, "I saw the video of Carl and you. I had to jump on Carl and ride him when you were riding him."
I didn't know how to react to that. I looked at her, and she hugged me, and said, "You are so fucking cute."
Bill laughed, and Carl said, "Midge, leave him alone."
Now Midge was laughing, and she said, "Oh shush. You told me that he was the most fun that you had on a shoot in 5 years."
Carl just shook his head. The conversation eventually got onto more generic things, although I couldn't give you the transition. I suspected Bill was driving the train on that.
When dinner was done, I was certain that Carl was not the pseudo-Jim from yesterday. I don't know what convinced me, but I was certain. I really liked Midge. She was funny and obviously in love with Carl and he with her.
When we got back to the room, Bill hung my suit up and fucked me long and deep. I loved these sessions with Bill. Bill seemed to know just how far to take me with the prostate stimulation, then he would back off. Bill fucked me doggie style on a regular basis, but our favorite was the missionary position. I always enjoyed looking into his eyes as he fucked me. There was a lot of kissing, and Bill sucking on and licking my nipples. He finally let me cum and was close behind. We started spooning. While Bill hugged me, I thought about Sean and Stephanie, and eventually fell asleep.
The Cubs game that we were attending was actually on Thursday afternoon. Bill said that was the only way to watch the Cubs. The photo shoot was Friday morning.
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We arrived at what looked like an industrial complex. "They'll be able to take your pictures here, and I will be talking with a Vice President in regards to an advertising contract," Bill told me.
When we went inside, Bill went with me as far as the studio. He dropped me off there and he was escorted to another location.
Before they left, our escort introduced me to the photographer. "This is Ian. He'll steer you through the shoot. He's handled a lot of newbies, so let him guide you."
Ian showed me to an area where I could shower and change into a jockstrap. He showed me 5 of them laid out. "Just wear the one on the left first. If it goes well, we may be able to get shots with all of these." He pointed at a doorway. "I'll be in there when you're ready. Walk right in."
I was thankful for the shower. I was worried that I would look sweaty, although that might be what they want in a jockstrap. Ok. Shower it is.
I was dressed and ready in a little more than 5 minutes. When I got into the studio, there were a couple of cameras and some lights set up in front of a screen. Ian showed me where to stand. When he positioned me, he had his hand on my ass. "Just relax, Jack. Think about showing that jockstrap to your boyfriend."
My boyfriend. The first face that came to mind was Sean. I was startled and it was gone. Bill rushed in to fill the void. I finished the shoot with this jockstrap with only thoughts of Bill in my mind.
Ian had me change into another jockstrap. "I want you to imagine showing this to an older lover."
Carl didn't even enter my thoughts, although he was the only older guy that I knew that had fucked me. I never considered Bill as an older lover. My "fantasy" Jim was all that entered my mind. I remembered that huge cock, and when I looked back over my shoulder, I think I licked my lips.
I was hard as a rock. "We need to take care of that Jack"
"I'm sorry." I went to return to the changing room.
"Wait. I can help you." Ian got on his knees.
I walked over to him, and he lowered the jockstrap. Ian took me in his mouth, licking from the bottom to the top. "I'd like to spend a long time on this, Jack, but we're on the clock."
Ian started jacking me off. He kept licking the tip of my dick, but his hand practically wrapped the entire 4 1/2 inches. In less than 3 minutes, he had me cumming. When it was obvious that I was close, he put my dick in his mouth and gave it a good suck. I was able to shoot my entire load into his mouth.
He looked around the ground when it was done. "Good. Looks like I got it all. Go get the next suit on."