"Oh, it can get much hotter, dear," as Annie went on to describe some of their anal escapades with their swinging friends at a level that was different from the night before. Annie told us that in addition to her liking anal sex, Teddy did, too.

"Giving or receiving," Catie asked before I could.

"Both!" Ted replied. Annie liked watching Ted both giving and receiving anally. One particular thing they did like was to have Annie receiving anally either from Ted or from some other male partner. Either way, that male or Ted would also be receiving anally, and Annie told us it was a wonderful feeling to have a cock driven into you by the person at the back of the train. Catie told Annie that I knew what she was talking about. I acknowledged that I did having experienced all three positions myself. Annie described some them as some of the fun aspects of having multiple partners at once.

Annie told us that the women weren't just on the receiving end. They had strap-on dildos to give their male partners an anal pounding. Unfortunately, Ted and Annie hadn't pack any of that equipment (grandchildren didn't need to find that and ask questions).

With all this talk of anal sex and ways to give and receive, I was already hard again and Ted was getting there. Annie realized that Catie and I hadn't had a chance to cumplete our anal task for Minnesota yet and thought we could try to do that before we reached St. Paul. We started out with Ted in Annie's ass. We watched as his cock disappeared into her. Once he was in, Catie slipped a condom onto my cock and helped guide me into Ted. The trick to completing what we were attempting was for neither Ted nor I to cum. We got into a rhythm between the three of us. After a couple of minutes Annie told Catie to get on the bed beside her and told her to get ready and lubed (she already was).

Annie told me to pull out of Ted, to remove my condom and go ahead and enter Catie (which I did). Once I was in Catie, she had Ted pull out and don a condom to press his cock into my ass. I accepted his cock pretty easily thanks to my practice with some fairly large objects that I was capable of inserting. Once he got stroking inside me and and helping me drive into Catie, it was a race to see which one of us was going to cum first. Under most circumstances, I would have outlasted him. However, the stimulation was intense from the inside my ass and feeling Catie's rectum surrounding my cock. I let everyone know I was about to cum and that Ted starting pounding my ass driving me deep within Catie. As I began to cum in Catie, he drove himself in me as deep as he could. This took Catie over the edge.

As our orgasms began to subside, he pulled his cock out of my ass, removed his condom and drove his cock back into Annie's ass. It didn't take him much more than a minute to start cumming in Annie's ass. As we all were in the afterglow of such intense sex, we realized that we were approaching the suburbs of Minneapolis / St. Paul. Ted and Annie knew that we were about 25 minutes away from St. Paul. I offered our shower so that both Anne and Ted could get a quick shower before getting off the train (one in each room). Catie took Ted back to our room while Annie got a shower in their room. Fortunately, there wasn't much packing to do because you're already living out of your suitcase.

It's really too tight for two people to take a shower in the combination shower toilet, but Annie and I tried. You have to be quick with a two minute shower. But Annie made sure my cock was clean before we got out. We dried each other and after a couple of minutes of our naked bodies pressed together, we separated when there was a knock on the door.

"Twenty minutes! Twenty minutes to Minneapolis/St. Paul," the conductor said. Annie responded with a "Thank you, dear."

"Are you sure that you won't reconsider? We could spend a couple of days running around our house naked. And I'm sure you and Catie would have a good time with our friends."

It was tempting and it meant that we'd have to move quickly and inform the conductor that we'd be getting off at the next stop. We'd also not have a room on the remaining trip back to Chicago. Maybe a roomette. But that wasn't guaranteed. It was definitely a decision that Catie needed to give her consent to.

"Let's see what Catie says."

A couple of minutes later, Catie and Ted returned to Annie's and Ted's room. Catie had much the same response to Ted as I had to Annie on considering getting off the train in Minneapolis/ St Paul. Catie and I agreed that it was probably something that we needed to spend more time thinking and talking about between the two of us before going all-in. The option was there for a future visit, though.

We got ready to say our goodbyes and exchanged contact information. They extended the offer to stay come stay with them for a couple of days if we changed our minds after we returned to Chicago and before I had to go back to Raleigh. With hugs, kisses, and handshakes, we left them on the platform and got back on the train. We got back in our room and started to talk about our encounters with the two of them. As we rolled on towards Wisconsin, we decided to get out of our room and went to breakfast. Once again, like we experienced in September, the train was now more a commuter train with (mostly) businessmen filling the seats in the coach car.

"Remember that guy who had the seat next to yours?" I asked.

"Yes, he looked so disappointed. I wonder if he's on the train today?" Catie mused.

"Maybe we can show him the train version of "hump day," I said.

"You're so bad!" Catie shot back.

We sat at a table and ordered our breakfasts. As we sat and waited, I asked Catie if she had a good time the previous evening. She quietly told me that she did and thanked me for being so open and willing to letting her explore her desires. She said that it was nice to share her first multiple male experience with me, as a person who loved and would protect her, and someone who had lots of experience in multiple partner sex (Teddy).

"I'm pretty sure that it wouldn't be the same with random younger guys without the same level of appreciation that you and Ted have," she said. She explained that it would only be about sex (and how much sex) to push boundaries. I understood what she meant. That sex for the sake of sexual release could be fun and exhilarating, but it was the closeness of relationship that really made it special. We agreed on that point.

She asked about me about my experience with Annie. I explained that while it was fun and pleasurable, it was also different from the times that she had left me with Abby. She asked about that. I told her that it felt like I had a different relationship with Abby and that when I was with Abby, I knew that she (Catie) was waiting for me and knowing that I would return. What felt different was knowing that she was having her own sexual encounter at the same time that I was. She asked if I was "worried." I told her that I wanted her to be "safe" and was having a good time being with someone else.

"Do you want to walk through the train and see if that guy is onboard and maybe invite him back to our room?"

"No, I think I want to spend the rest of the trip with you beside me and inside me." We finished breakfast and thanked the staff before leaving to go back to our room.

When we returned, our bed had been changed and returned to the couch position. We opened it back into the bed position and we undressed each other before crawling back into it together. We were in Wisconsin and I slipped into Catie's ass to continue our anal exploits. I came inside of Catie and the two of us fell asleep in the bed that she and Ted had shared just a couple of hours before.