After The Train
Part 1, Chapter 9: "Train"-ing Enemas, The Train to Chicago: Rolling to Chicago
"As I write this, I am holding two loads of his cum in my ass. I never imagined it would feel like this."
After stating that she had met this "cute guy" on the train on the way to Chicago, she wrote a quick synopsis about the experiences we'd shared since Portland. It didn't take long for her statement about loads of cum in her ass to show up in her writing. It was, however, a quite erotic and sensual account of our previous couple days, especially the anal sex portion of it.
"I'm not done, yet."
"Writing or sex?"
"Both!"
Remember now, as I write this, I am writing both from memory and the my own journal entries, so it is naturally influenced by everything that happened after this point in this relationship (and that was what was developing, a relationship). But I will attempt to convey the range of feelings that I had at the moment and what she shared with and about me.
First, she wrote about what the experience was like and what she felt physically. And she also shared what she was feeling for and about me emotionally. So let me start with the first part: the experience and what she felt physically.
While she had talked about her previous relationship(s), the one thing I didn't know was that she was an anal virgin. I thought her questions about my anal sex experiences were interesting prior to the previous night. They all hinged on whether I was able to get my cock all the way in. "Size" was a concern.
The other thing thing she wrote about was what her girlfriend Jody (and others) had told her about anal sex (and that she was confirming the information shared with her about what it was like). Jody had told her that it could and probably would "hurt like Hell!" But after a while the pain would fade and it would likely start feeling good to be filled (if she wasn't handled too roughly). She described the "Yes...No, No...Yes!" sensation with each gradual push deeper and deeper inside her. I had offered to stop all along the way and at each step she wanted me to keep going. She noted that in her journal about how gentle and caring I was as I was sliding ever deeper into her ass.
Yes, according to her, it hurt a lot. And yes, it did start feeling better. Jody had told her that "bearing down" would help to allow deeper and deeper penetration. I felt her doing that while I was sliding into her and didn't have to suggest it. The fact that I could feel her "squeeze" to allow me to go deeper indicated she might know what she was doing. She wrote that cumming, with the help of the vibrator, while I was in her ass also felt very different in how she normally experienced her orgasms. She and I would talk about that later.
That's where she wrote about me as a lover where she felt that whatever we were doing, it didn't feel like it was about me (cumming). Rather it was about my concern about how she felt (mostly physically). The other thing that was notable about what she wrote was this: (my) cumming wasn't an ending. She just loved the way I "stayed with" her and the level of intimacy that she felt after I came inside her. As I've stated earlier, I've never felt the need to jump up after cumming as if that's the end of an intimate encounter. I've always wanted to stay right where I was and "be with" whoever I was "in" at the moment. It's so much more intimate and sensual that way.
I was very touched about what she wrote about me. It wasn't just about the physical action(s) that she shared, it was the emotional side. When I was younger, some of what she shared might have scared me (and certainly some of it did at that moment), but what I had discovered at a personal level, as a result of the divorce, was to give of myself much more fully than I had ever before. For some, that was extremely attractive. For others, very scary to be quite that open with my/our feelings.
With breakfast done and paid for, she stood up and told me to "come on." Or maybe it was to "cum on." We passed back through the train to spend our last hours onboard together and intertwined. As I mentioned, we had already planned for me to stay with her over the weekend, so there wasn't quite the sense of urgency that might have been present had the end of the train trip been the end of our time together.
It wasn't until we got back to my room that we could really talk about what she had written in her journal. The bed had been folded back so that the room was more a sitting area than a sleeping area. And what better way to have a conversation than to strip each other out of the other's clothes. But it was a gradual and gentle undressing. Although I wasn't keeping score about anal virgin sex, I was curious about why she gave up this aspect of sexual virginity with me. She told me that in the short time that we had known each other, as much as she had opened herself to exploration of sexual taboos, I had demonstrated that I was a kind, considerate, and caring lover (and my ex-wife was still crazy to give me up). I was just the kind of person her friend Jody (and some of her other friends) told her that she should have in order to explore that part of her sexuality. There was much more to the conversation than this and it was extremely erotic and there was no hiding the sexual excitement even though the expression of this excitement was "delayed."
Again, this reminded me of the types of conversations I had numerous times while visiting in the women's dormitories particularly when I was hanging out with my then girlfriend (and later my wife). But that's another story in and of itself.
With her new found discovery of some of the pleasures anal sex, I asked if she wanted me in her ass again, to cum again. She told me no and that she was a bit sore from her experience the night before. But she did want us both filled with enemas once again, "to make love again" (her words) with our bowels warm and filled. We were no longer "fucking," we were "making love."
She had me assume a position on my knees while she filled the bag with warm water, rubbed some petroleum jelly on the nozzle and around my anus. She pressed the nozzle in, open the clamp, and I felt the flow of warm water flowing into me. It didn't take but about two minutes to empty the bag and she closed the clamp.
"Okay, do me!" She handed me the bag while she got some towels into position on the couch. I washed off the nozzle, filled the bag and readied it. I prepared her with some petroleum jelly and she indicated that she was a bit tender "back there." I carefully slid the nozzle in and opened the clamp fully for just a moment before setting it back one click. At the slower rate, it took about 4-5 minutes to empty the bag into her. Although the warm water felt good inside her stretched (and bruised) rectum, she told me that there was no question that she had been fucked by a big cock.
I closed the clamp and hung the bag up by the hook. She patted the towels on the couch and told me to "sit here." I carefully settled down on the towels and leaned back. I wasn't sure where we were on the train route but knew we had plenty of time. She straddled my legs, reached down to position my cock between her very wet pussy lips. Her nipples were erect and were so very inviting. As she started sliding my cock into her pussy, I gently cupped her left breast with both hands to extend the nipple and took the nipple between my lips. I gradually increased the suction to pull the nipple and then the areola into my mouth, pressed between my tongue and the roof of my mouth. The combination of this and her sliding down my cock triggered an orgasm that had her quivering before me.
I moved to her other breast and did the same thing and that continued her orgasm. Back and forth I went. She finally pushed me back and sat straight up on me, her full weight pressed against my hips to bury me deep inside her as she completed this series of orgasms. This is certainly one of my favorite sexual positions and it was one that I had rarely shared while two of us were holding enemas inside us.
The tracks were not as smooth as they had been crossing the far west and there were more switches to pass over. This gave the train much more of a sway (and noise) than what we had become accustomed to riding the rails across Montana, for example. Speed is deceptive on a train, but we were probably travelling at about half the speed as were were as we crossed Montana, North Dakota, and parts of western Minnesota. But this enhancement of the motion added to the experience of fucking on a train. Somewhere along the way I remember saying something like "forget the mile high club!"
We continued in this position for a while. I felt no urgency in the release of my enema and neither did she. It was a good volume to be holding. Enough to feel the fullness but not excessively so. At some point, though, she wanted to switch positions. I stayed in place but she got off me, turned around and straddled me while facing away from me. We were now both facing in the direction of the train travel as I lay back on the couch. After positioning me to enter her again, she placed her hands on my knees and was leaning forward while trying to slide down my cock (which was "bent forward" to enter her). Rocking her pelvis, she gradually slid back down on me. I couldn't watch my entry so much as feel it, but it was quite a sight to watch her firm buttocks respond to the train motion.
I was probably about halfway in her when she went "Nope! Too much pressure!" I told her to sit up and that I'd hold her. She did, and with that motion I was once again all the way inside her. While the position that she had initially tried put some very nice pressure on her clitoris, the head of my penis was pushing back on her rectum and she wasn't sure she'd be able to continue to hold her enema inside her (that's one reason the towels were there, but why tempt fate). However, I could support her by her shoulders and I could reach around and gently squeeze her nipples while she was riding me this way. She would either have her hands up around her head as she orgasmed or wrapped across her abdomen.
There was a lot more "friction" in this position for me and her as the head of my penis rubbed one side of her vagina and the base of my cock was rubbing the other side of her vaginal entrance near her clitoris. I could feel my own orgasm building as she continued to ride me this way.
"You're getting close...."
"Yes, very close."
I was thrusting my hips slightly from this position and pulling her down on me by her shoulders. I was getting slightly more engorged trying to go deeper inside her while approaching another one of those delicious edges to cumming. Suddenly she leaned left, slid her right leg from beside me and lifted herself off me and, placing her foot on the floor, stood up on her right leg. I had no idea what was happening as she swung her left leg across me to stand on both feet. Before I could ask, she spread my legs with her hands, got down on her knees and with one hand holding my balls and the other holding my cock, slipped her mouth down over my cock.
It usually takes a lot of stimulation to get me to cum from a blow job (it isn't my most favorite way to cum anyway), but I was so close that the warmth of her mouth, the grasp of her hands, and the gentle (and not so gentle) suction took me right over the edge. All I could see at first was the top of her head as she tried to take me all in. As I continued to pump out my cum, she slid her mouth back up towards the tip of my cock and looked up at me with a wicked twinkle in her eyes and a smile that couldn't be missed, even with my cock in between her lips. She sucked my cum out of me, taking the last few drops into her mouth, licking the tip of my cock and being careful not to overstimulate my now sensitive cock.
She got up and straddled me once again and placed her face and lips against mine. She may have swallowed some of my cum when I first started squirting, but she still had a mouthful when her mouth met mine. We shared a warm, wet, and cum-filled kiss between us. Ultimately, we both ended up swallowing part of my load of cum.
"Delicious!"
(to be continued)