It had been several days since Natalie and I had met with Tim. When we parted, I told her I would contact another buddy for a possible meet-up. It took me much longer than I thought to get the free time to contact him. Will and I met on one of the many gay cruising websites. Unlike Tim, I could only contact Will on the site, usually only on weekends. As I logged on to the site, I figured I would send Will a message and wait until the weekend to hear back from him. I was surprised when the green light next to his profile was on.
I quickly tapped out a message: "How are you doing? It has been a while since we've connected." I waited for a response.
A message popped in. "Yeah, it has been a while. We should get together this weekend. Are you free Saturday afternoon?" Will responded.
It was a perfect opportunity. My wife was scheduled to travel for work beginning Thursday and would not return until Monday night. I quickly replied, "Yes! That works for me."
I thought for a minute about how to ask if I could bring Natalie. I decided to be direct.
"I have a friend, a young woman, that is interested in watching. Would you be okay with her coming with me? She is very discreet. She has come with me to another friend's place." I hit send.
Several minutes passed before a response arrived from Will.
"Sure. The setup is designed to keep everything anonymous. I have two requests," he continued. First, do not show her my profile here. Second, she only watches."
I was shocked that he agreed. I sent my response confirming his requests. We exchanged a couple more messages, set a meeting time, and exchanged numbers for easier contact on Saturday. I logged off.
I texted Natalie, " Are you free on Saturday around 2?"
"Yeah." She responded. "I have a work thing but should be free by then."
I responded, "Okay, we can meet at the coffee shop near the fetish shop."
"Okay. See you then." She sent back.
The rest of the week went quickly. My wife left as planned on Thursday. I confirmed with Will and Natalie that we were still on as planned on Friday.
Saturday morning, I went to the local adult bookstore and picked up a fresh bottle of poppers. I knew that I would need them for the afternoon's planned fun.
I arrived at the coffee shop early. I got a coffee and sat down at a table where I could see the door.
A little after 2, Natalie arrived. I was surprised to see Julia, another student from Natalie's class, was coming in with her. The two young women walked to meet me at the table.
Natalie, "Mr. Kramer, do you remember Julia?"
"Yes," I replied as the two women sat.
My expression said a lot because Natalie quickly explained why Julia was with her.
"Julia is one of the friends I've shared our experiences with. When I told her she was dropping me off to meet you, she insisted on coming in to say hi," Natalie said.
I sat silently as Julia began to speak.
"Mr. Kramer, Natalie has told me about what you two have been up to these past months. I have to say; it is sooooo hot!" Julia said.
I looked her over as Julia told me about what she had been up to since she had been my student. She had kept her hair short like a young boy. Her clothes were masculine but tailored to fit her feminine shape. Much as I had remembered. Her pants were high-waisted, accentuating her hips. The blouse was fitted, hugging her breasts. I could make out some of the details of her light blue bra through her white top. Natalie was dressed professionally in black dress slacks and a dark blue blouse. Although modestly dressed, Natalie still looked sexy to me. Julia explained that she and Natalie now worked together at a local advertising agency. As she wrapped up her update, my phone chirped.
It was Will. "All set here. Are you guys on your way?"
I looked up from my phone and to Natalie, "Sorry to cut this short. He is waiting for us. We should go."
Natalie said, "Hey, Julia, I'll catch up with you later. Thanks for the ride."
Julia looked at us both, and a sly grin came across her face. "You two have a good time." She said. She got up and left the coffee shop. She stopped to wave to us as she opened the door and exited.
Natalie looked at me, and I nodded toward the door. The two of us stood and left the coffee shop. When we arrived at my truck, we got in. As we drove, I began to explain how the experience we were about to have would be very different from what we had done with Tim.
"So, I want to tell you how this will be different from what we've done with Tim." I started.
I began, "First, Will has a Gloryhole that he sets up between his kitchen and mudroom. So we won't see his face."
"Really, a Gloryhole? I thought those things were only in gay porn." Natalie said.
"No, they're real things, and there are even some at the adult bookstores around town," I responded.
I could feel Natalie looking at me and her mind processing what I had said. I kept my eyes focused forward on the road as I drove and continued to explain.
"Second, Will doesn't suck me. I suck his cock." Before I could continue, Natalie interrupted me.
"What! You suck his cock? That is going to be sexy as hell, Mr. Kramer!" She exclaimed.
"I've been fantasizing about watching you suck a cock. Is it big, like yours? Can you deep-throat him? Do you swallow his cum? I can't believe I'm going to get to watch you." She went on.
As I turned down Will's street, I looked at her and said, "I guess you'll have to see for yourself."