It had been so long since I last saw Anna. Our frequent meetings had tapered out to nothing after she separated from Rick. I had hoped for the opposite, but she told me she needed time to build a new life, so I reluctantly broke contact and tried to move ahead with my life too. The memories remained. Like her perfect ass, the time she fed me her husband's cock for the first time, the time she forced me to have sex with her husband and all the group action we had. Good times!
I had all but forgotten about her when I lined up for the start of the Chicago marathon. Training hadn't gone as planned so I was further back on the start line than usual when I saw an ass I couldn't miss. At first, it reminded me of Anna, but as I got closer, I saw it was indeed Anna! My heart jumped out of my chest with excitement. I took a moment, tried to remain calm and took a few faster strides to run alongside her.
"I'd notice that running gait from a mile away," I said as I jogged alongside her and smiled.
"Oh!" was all she said, with a surprised look.
"I didn't expect to see you here," she finally said as her surprised look turned to a smile.
"Yeah, I'm still getting them done. Two per year now."
We talked like that for a few minutes. Keeping the subject to running and general training, but all I was thinking about was who she was seeing, how she was feeling, and, most importantly, if she had any room in her life for me, I continued with the running chat until there was no more to say and finally brought up the subject I was interested in.
"So, Anna," I said, hesitating for a moment before continuing.
"How is your life, I mean, you know,"
"I'm good, Dave. My life is good," she replied, looking me up and down as she thought.
"You want to know if we can hook up again, don't you?"
"That's not exactly what I meant, but I would like to know."
"You'll be sad to know I am in a new relationship."
"Oh, good for you."
"You'll be happy to know that he claims to be bi-curios and that our encounter might be just what I need to test him."
"What have you got in mind, Anna?" I asked, my heart jumping out of my chest in excitement at the prospect of a new adventure.
"Do you remember the introduction that Rick gave you, Dave?"
"I'll never forget it, Anna."
"I want you to do that for Dan, my new boyfriend."
"And if I succeed?"
"One step at a time, Dave. Get him to suck your cock first. When you see his cock, you'll want to do the same."
"A monster or a beauty?"
"It's perfect, Dave. Big and beautiful."
"I'm so excited now, Anna. I can't wait."
We were separated somewhere mid-race but got in touch the following week to plan Dan's breaking-in session, as it became known. Anna planned to tell Dan she had to work late but had arranged a delivery for him. I was to arrive and give a message to Dan. "Anna arranged sausage for dinner. You need to call her when you are done."
The day arrived, and I arrived at Dan and Anna's house at the agreed-upon time. Dan looked a bit perplexed when he opened the door. He invited me in when I told him Anna sent me. I didn't deliver Anna's message, I just told him that she sent me to help him discover his bi tendencies.
"My what? What the fuck, man."
"Anna thinks you'd like this. Do you need to think about this?"
"Think about it? No. Well, maybe, I mean, ah! I don't know."
"Take your time, Dan."
"Who are you anyway?"
"Dave's the name. I used to hang with Anna some years ago."
"She told me she had some crazy times. You were involved in them?"
"I don't know what she told you, but we had some crazy times. And they all began just like this."
"What are you saying?"
"She also did this to me, Dan."
"I'm not sure about this, Dave."
"Nor was I, Dan. But you haven't kicked my ass. That tells me you are sure enough."
I looked him up and down. He was a handsome, fit-looking man. About my height, more muscular than I am, and piercing blue eyes. As close to my perfect guy as I had ever seen. I hoped Anna was right about this,
"Let's assume you are interested in men, in theory, Dan. Could you picture doing anything with me?"
"This is so weird. In theory, yeah. Let's go that far."
"Progress. So, in theory, what would be the first thing to do, Dan?"
"I don't know, Dave."
"I know what I want, Dan. How about I tell you and then you tell me if it's a good idea?"
"ok, Dave."
"I'm looking at your jeans, Dan. I'm pretty sure I'm looking at an erection trying to escape."
"It's pretty uncomfortable, Dave. You seem to have the same problem."
"How about we take the pressure off? Would you like to see my cock?"
"I would, Dave. Do you want to see mine?"
"There is nothing I would like more."
We unbuttoned our jeans and I pulled my jeans and shorts off in one movement. Dan was still wearing underwear when I stood up. My cock was happy to be free and Dan's eyes darted between my eyes and my cock.
"You like what you see, Dan?"
"I guess so,"
"How about you do the same? Drop those shorts, Dan."
He complied and his beautiful cock bounced to attention as he freed if from it's cotton captor. As Anna had said, it was perfect. Maybe slightly under eight inches, enough girth to make an impression but not so big that it would cause jaw pain. A nice, upward curve and a big, shiny, bulbous head, significantly thicker than the shaft. I was going to have so much fun with that cock.