Cumming to Chicago

We were laying there together. The train had left Milwaukee just a few minutes before and were now turned south to Chicago. We still had about two hours together on this train. Things outside the window were very urban now, though we'd run stretches were the train seemed to be out in the rural countryside, if only for a short time. The sun was out and we had outrun the rain, at least for the moment.

I was laying on my back, with my left arm around her. She was on her side, up against my left side, head on my shoulder, her left leg pulled up and laying across my legs. With her left hand, she was gently stroking me. Sometimes up my chest and down my abdomen, other times stroking my cock and balls. I was hard again after our little "luncheon" of cum. Little dribbles of pre-cum were showing up at the tip of my cock, which she played with.

I was laying there with my eyes closed, feeling the rocking of the train along the tracks, listening to the wheels roll with their staccato "clack-clack, clack-clack."

"Tell me what you're thinking."

I'm going to be honest here. Most guys I know, including myself, are afraid of this question when a woman asks us that. Why? Because it's likely to be "the wrong answer." We've been trained, no programmed, in the dangers of this question being asked. Part is the male socialization around feelings and emotions, the other part is the negative reinforcement (and punishment) for "the wrong answer." We can make it worse by trying to figure out the "right answer" or trying to give an answer that the other person wants to hear. That's okay if it reflects your real feelings. It can be a disaster, otherwise.

After being blindsided by an affair, and not just an affair but a replacement; going through all the emotional challenges of a divorce from a person that you know, in your heart, that you truly love, can provide a stimulus for looking at and even sharing what you are feeling, even if it's NOT the answer the other person wants to hear. It's the authentic sharing of one's self that will ultimately win out anyway and show up in ways that we have difficulty imagining.

Okay, I'm off my soapbox now. I did answer the question without really thinking about it. I don't remember thinking "what am I thinking? What is the right answer?"

"I can't believe how surreal this trip has been. I can't believe I met you and all that we've done. I love laying here with you beside me. And I'm thinking about how much I've missed being physically and intimately in touch with a beautiful woman...."

As I answered, she had propped herself on her right arm and elbow. As those last words came out of my mouth, she gently placed her left index fingers across my lips to stop my words

"We need to do this again."

Immediately, my mind leapt to: the next time we'll book a room together so we won't be worried about sneaking one of us in or out of the Sleeping Car, we'll have all our meals delivered to the room and we'll spend the entire trip in a state of sexual ecstasy....

"No, I need you inside me again."

"Oh!"

She told me what she wanted. This time, instead of fucking on the couch/bed, she wanted to fuck in front of the windows starting with the "chair." She wanted more than that. She wanted me to start by fucking her pussy and then, when I was ready (to cum), to slide my cock into her ass and cum. I asked her if she was sure because of her soreness and she told me she was. She wanted her last fuck on this train to be memorable. And she wanted to walk off this train with a load of cum in her ass and her insides thoroughly coated in my cum. That was such a pleasing mental/visual concept I could hardly argue with it.

This time, she coated her anus with petroleum jelly rather than letting me do the honors. I settled back in the chair next to the window which had me facing towards the back of the train. She straddled me to insert my cock into her pussy. It wasn't quite as easy as it sounds or would first appear, but she did manage to get me part way into her. The chair dimensions were just a bit "off" for a complete insertion.

Eventually, she turned herself to be seated on my lap where she could have me penetrate her more deeply. She rocked back and forth more than moving up and down on my cock. That wasn't quite doing it for her and so she stood up, had me get up, bent over in front of the two windows and invited me to slide back into her from behind while she was bent over (which I did enthusiastically). Her palms placed against the windows, I was pumping away in her and it was hard to tell where one of her orgasms ended and the next one began.

We were fucking our way across southeast Wisconsin, passing through Racine and into Illinois on the way to our next stop in Glenview. The further south we went towards Chicago, the more suburban and urban the setting became. Somewhere north of Glenview, in some local community, she told me to put my cock in her ass. I told her I wasn't really close to cumming and asked if she was sure. She was sure! She wanted me in her ass (now!). I was trying to be slow and careful. She wasn't, as she was trying to force her ass back onto my cock. Bent over this way, she probably had me all the way into her in less than two minutes, maybe less than one.

Her orders she was commanding were basically "Fuck me!" and "Fuck me harder!"

As we continued, she slowly walked her legs closer to the window so that she wasn't bent over. Rather she was standing nearly straight up with her hands, face, and chest pressed up against or near the window. I imagine what anyone saw, if they were looking, was a naked woman, pressed up on or near the glass as the train sped by. From this position, my thrusting was more upward than it was forward like it was when she was bent over. My ex-wife and I called this "upfucking" because each thrust was nearly vertical. And with each thrust, I was lifting her off her heels. She leaned up against the window, face turned to the side, hands and arms outstretched, breasts pressed against the glass as we approached the Glenview Station. The station was on the left side of the train and so the exhibition of her body pressed against the glass as she was being fucked in the ass would be visible to anyone who might look up at the window on the second level of this car.

"I think we should take a step back," suggesting that we position ourselves beside the seat where we had started, in front of bathroom. If she needed something to grab onto, there was a shelf above the seat with a ledge that she could hang on to.

I thought she said "I want them to see!" but she kind of mumbled at the third word and "them" could have been "him." I responded as if she had said "them."

"They can. It's just a little more difficult and a little less obvious," I whispered in her ear and continued to stroke upward into her ass. I was getting closer to cumming. After a minute or two, the train began to move again. The next stop would be Chicago in about 45 minutes. She moved back toward the window dragging me with her.

Under her breathe there was a string of "fuck me, baby!", "cum in my ass!", "don't hold back!", and assorted other guttural moans and exhortations. I slowed down for a moment to tease her because I was one or two strokes away from cumming. I pulled my cock as far out as I could without pulling out.

"Are you ready for this?"

"Um-hmm" acknowledging yes.

"Here I cum!" as I pushed my cock up into her as far as I could. Just one stroke. She didn't scream so much as she just let out a long set of growls as she shook. I held her and held as still inside her as I could (on a moving train) to allow her to feel each pulse, each contraction as my balls emptied once again. They had been working overtime over the past two days. I was glad that they still worked! She seemed to be going a bit limp in my arms. I couldn't tell for sure whether she had been cumming or just enjoying the thrusting. She wasn't using the vibrating butt plug this time to trigger orgasms.

"Do you want to sit down?'

She shook her head yes. I carefully lowered us both to the couch with my cock still inside her. We leaned back with her on top of me. The train continued rolling toward Chicago.

"You've now had me in every state of this trip," she opined.

"Not Oregon."

"I didn't know you then."

Painfully (for her) I slipped out of her ass. But nearly all my cum was held tightly inside her.

"You're going to have a very sore ass after this."

"Promise to kiss it and make it better?"

"I promise."

"How about now."

Before I could answer, she told me that before we stepped off this train, she wanted to feel my lips and tongue plying her tender, but filled, hole. She rolled to her and my right, onto her side. After a moment, I thought "sure, why not?" I maneuvered around to where I could indeed get at her and lifted her left leg to reveal a lot of puffy tissue where her once tight rose bud had been just hours before. Most of my cum was still inside her but there was a small amount of cum that had made its way out of her when my cock slipped out.

A clean ass doesn't smell unpleasant and she had certainly been cleaned out earlier. The stronger scent was actually the petroleum jelly. Petroleum jelly doesn't have much taste, but the scent of it can overwhelm one's sense of taste since taste and smell are so closely connected. I took my lips right to the puffy tissue and planted a kiss on and around it. I pointed my tongue and pressed the tip to the center and then ran it around the rim. But it was when I pressed my tongue in that she really shivered followed by my lips pressed against her anus.

Although I don't think there were any huge squirts of my cum from out of her ass, I'm fairly certain I took in more than the little dribble I first saw. We both realized pretty quickly that we needed to stop at this point and we could do this later (with some other lubricant other than petroleum jelly). I joked that at least I wouldn't have chapped lips. She asked how we tasted together and I pointed out she could have a taste from my softened cock (which she did). A quick kiss and we agreed that we needed to explore each other this way later.

We needed to get cleaned up and ready to leave the train. She got up and took the two-minute shower. I got in right behind her and quickly washed off while she was dressing. I told her that I'd meet her out on the platform in a few minutes and to remember that I had to go to baggage claim to pick up my trunk. She left our shared room to gather her stuff in the Coach Car. I quickly repacked anything that was out, put on my clothes, shoes and socks and sat down to consider this trip in the solitude of my room. The car attendant came through to announce that we'd be arriving in Chicago in just a few minutes.

Yes, it was nice to be cumming to Chicago. The train pulled into the station and came to a stop. I did a final check of the room, picked up my suitcase and my daypack, and walked out into the hallway to descend the stairs. The room had been a very good investment though the way I used it was very different from the way I thought I'd be using it.

I stepped onto the platform to find my lover. Once again, it felt strange to be on solid ground in a fairly open space. I was looking forward to the next few days with her in a spacious bed where the only motion was what we imparted to it, in it.