After The Train
Part 2, Chapter 7: After the Train - The Weekend in Chicago - First Time w/ Jody Under Catie's Direction
When we arrived at the bedroom, a single lamp was lit to the left of the door over in the corner away from the window. There were pillows on the bed and the filled enema bag was hanging from the floor lamp placed beside the other side of the bed. Catie had moved the chair close to the bed, the lamp and the enema bag. At this moment, I had no idea of what was going to happen next. This was a "Director's" call.
Catie had Jody get on the bed, first on her hands and knees, and then down to the pillows to elevate her ass. I thought what was next was the second enema for Jody. But Catie has something else in mind.
"Okay Lover Boy, up on the bed," Catie commanded.
"Yes, ma'am!"'
I got on the end of the bed on my knees behind Jody waiting for the next set of directions. Catie instructed me to place my legs outside of Jody's and to move up and position myself so I could slide into my cock inside her.
"Anally?" I asked quietly.
"No, not yet." she whispered.
Catie asked Jody if she was ready and Jody indicated that she was. I had never been directed this way. I slid my cock towards those wonderful vulva lips that had just been at my lips and subject to my tongue a few moments before. Of course, Jody was already well lubricated and I was leaking so much pre-cum that being lubricated really shouldn't be a problem. The tip of my cock made contact and I slid it up and down her open slit. With gradual pressure, my cock slid towards her opening as the head was slowly engulfed by those wonderful wet lips.
I continued to press into her. I raised up, repositioned my knees to get a better angle, and then pressed into her. She orgasmed as I pushed in. That gave me an even better angle to press all the way into her. I held myself at that position to let her enjoy that feeling and as her orgasm seemed to subside, I began to stroke in and out. With my legs positioned outside of hers I was able to stroke inside her very, deeply. In addition, this allowed the underside of my cock, particularly around the head, to rub the front wall of her vagina in a way that I had discovered a long time ago could be quite stimulating to some women.
For the moment, I was totally with Jody, not just inside her. If Catie was saying anything to me or to us, I wasn't aware of it. I thought about that later on and felt a little weird about that. But it's consistent with how I've felt about intimacy and being with the person in the moment. I think Catie was watching the show and enjoying it. All I knew for sure was that Jody was enjoying herself.
Eventually, I moved Jody so that I could flip her over and we would be face-to-face. I pulled the pillows from underneath her and moved them out of the way. Pulling out of her, she flipped over beneath me and I quickly reentered her while lifting her legs over with my arms. This allowed me to spread her legs open and to penetrate her more deeply. As I continued to stroke into her, I raised her legs up towards my shoulders. I could put more of my weight into my strokes and continue to push into Jody very deeply from this position.
I became aware of Catie on the bed behind me. It started when I could tell the mattress was being depressed behind me as she crawled up on her knees. When I thought about it later, I thought about how it might be on my waterbed at home, even though the brass bed frame would have made for a slightly different approach (mental note to self, invite one or both of them to my home and we'd do this on my waterbed). Catie "walked" forward on her knees to get herself into position for what she wanted next. I could look over my shoulder and tell where she was and that she was in a sort of cat-stretch crouch position behind me. I continued my strokes into Jody and it occurred to me that Catie was positioned to watch each stroke in and out of Jody from a close-up position.
Catie began describing what she was seeing from her position. It was a mixture of erotic observation and blunt vulgarity as she was telling Jody what it looked like with each stroke of cock in and out of her. She was particularly enamored by the way my balls "slapped" Jody's pussy as I reached the depth of each stroke. Catie instructed me to fuck Jody harder to watch a more pronounced ball slap. With these harder and faster strokes, I could feel the early signs of a building orgasm. My assessment of Jody was that she was lost in a continuous state of orgasm punctuated by larger waves. When those larger waves came, I would stop stroking and press deeply into her and hold her as she quivered beneath me.
Catie asked me if I was getting close to cumming at the end of one of Jody's orgasmic waves and I told her I was.
"Good! I want to milk your balls for every drop of cum you have in them!"
Immediately after she said that I felt her fingers wrap around my balls. It was an interesting sensation. It was one thing to have someone sitting on your cock and being able to reach around behind and grab my balls. This was an access with more dexterity. She wasn't rough as the manipulation was more like a massage.
"Will that help you cum in her?"
"Yes," I said.
"How about this?"
At first, I though she was inserting the enema nozzle into my rectum because I still knew the bag was hanging up behind and beside us. But it only took a moment for me to realize that she had slipped a finger into me. Besides twirling her finger inside the walls of my rectum, she curved it to press on my prostate through the rectal wall. Suddenly, there was a flood of sensations deep inside me. I was not going to last much longer with this stimulation even if I wanted to hang on to the edge just a little longer.
"What did you do?" Jody asked. It was the first time in a while where she looked focused rather than a more dreamlike state.
Catie explained that she had my balls in one hand and a finger up my ass with the other. Jody told her that she could feel me get larger and stiffer ("as if that is possible").
"The better to cum inside you, my dear." I was hanging on by a thread and trying to stroke inside of Jody with this level of stimulation was a challenge. It was almost too distracting.
Jody told me she was ready for me and that's really about all I remember about the conversation though there was one going on between Catie and Jody. It's hard to describe the sensations of my cock stroking in and out of Jody, Catie with my balls in one hand and her finger(s) pressed deep inside my rectum against my prostate. And here I was on this edge, wanting to drop over and take the plunge while, at the same time, trying to draw it out as long as I could.
I took that one last deep stroke and pressed in as deep as I could. I figured I would go over that edge at any second because I could feel the rush cumming. I quietly moaned "Here I cum!" and felt the "freefall" moment. Whether it was Jody opening her legs more, her grasping my butt to pull me in deeper, or Catie pressing me in deeper from her position, I felt like I went even deeper into Jody than I had been just a few moments before. It was warm sensation and her pussy was grasping my cock very tightly. I could feel Catie's finger or fingers pressing against my prostate with each pulse. Catie exclaimed how neat it felt.
As my orgasm intensity began to subside, I became aware once again of Catie massaging my balls.
It took a couple of minutes for the final spurts of semen to be issued from the tip of my cock.
"Are you okay" they asked?
"I'm fine. But I'm going to stay right here like this for a few minutes, if that's okay." I wasn't softening very fast and I knew that with Jody in this position, my cum wasn't going to leak out right away.
Eventually, Catie withdrew her fingers from my rectum and then released my balls. She got up off the bed while Jody held me tightly.
Catie made a comment like "Don't go anywhere." I can't remember exactly what she said as she left the bedroom.
Jody and I quietly spoke with each other while Catie was gone, the general gist being how good this was.
"Do you cum here often?"
"Not like this!"
My sense of it was that I had produced and shot quite a bit more cum into her than I would have normally expected. That was based more on the intensity of the pulsating contractions and how long they had lasted more than anything else,
Catie arrived back in the room with some refreshments. I passed on the beer and went directly for the water, trying to sip it while not spilling it on Jody beneath me AND while holding my cock inside her. I wasn't completely flaccid but I could have easily slipped out of her if I wasn't careful. For the moment, I had Jody "plugged" and full of my cum. My understanding was that this was the load that Catie had planned for Jody's ass but changed her mind and directed me to fill her pussy. It would become clear in a few more minutes why.
Catie was sitting up beside us. She told us how "cool it was" to feel me cumming inside Jody. My ex-wife would do something like that when riding me and the reaching back to insert a finger or two in my rectum and grabbing my balls to feel me cum. I didn't mention that.
"I can feel you swelling again," Jody said.
It was true, I was becoming erect again as my refractory period was passing. It's not as rapid swelling as my original erection but it gets there soon enough (and with it the desire to start stroking again). It would help me remain a plug in Jody's filled pussy.
"I think it's time to clean you up," Catie said without being specific.
Catie directed Jody to spread her legs wider and then had me spread mine as well. She went behind me and was laying on her back between our legs. She tapped my butt and told me to pull out of Jody.
I asked Jody if she was ready without telling her what I was going to do. She indicated she was. I slowly withdrew my cock from her pussy and when I finally popped out, I quickly moved my face down her body and plugged my lips and mouth to her pussy to capture my cum as it started to flow out. Because I had been inside Jody for quite some time after cumming, my semen had gone from creamy white and thick to a clearer and thinner liquid. Jody shuddered the moment my tongue made contact with her pussy.
At the same time, Catie took my cock into her mouth from underneath me. Her mouth engulfed much of my cock from an unusual angle. It was a feeling I had not experienced in a long time...my lips and tongue to a wet pussy and a different set of lips applied to my cock. Catie's cock cleaning was a wonderfully intense for the several minutes she was under me. She eventually slipped out from under me and moved up to where I was lapping up my semen that was leaking out of Jody's pussy.
"Move over!" Catie said to me.
I raised my lips from Jody's pussy to allow Catie to "dive in," and did she ever! It was such a great sight. I moved beside Jody to watch the interaction between Catie and Jody. I had watched Barbara and Cindy pleasure each other on my birthday more than a decade before, but with much less "intensity" between them. I watched Jody's body tense and relax as Catie lapped up my semen that was draining out of Jody.
IT WAS HOT! And fascinating to watch. But I had no intention of being a spectator for long (unless Catie really wanted me to be and then...maybe).
"How's that pussy taste?" I asked Catie.
Before Catie could pull her mouth away and answer Jody said "She's tasted it before."
That confirmed what Catie had told me about the occasional sexual interactions between her and Jody.
Catie quickly quipped "But never filled by my lover's cum!" before putting her lips back to Jody's pussy. It was indeed an amusing thought as well as erotic.
I leaned over and took Jody's right nipple into my mouth and gently (and not so gently) sucked her nipple and then more of her breast into my mouth. The suction triggered another larger orgasm. And then leaning over to her other breast and doing the same thing with her other breast.
Eventually, I got back beside Catie and we started taking turns licking Jody's pussy as well as sharing between sharing between the two of us. This whole scene was so incredibly erotic, I thought I might cum again without any direct contact with my penis.
It was evident that the rate of drainage of my semen from Jody's pussy was diminishing in this position. Catie directed me to get on my back beside Jody, which I did. She asked Jody to get up and then sit on on my face in a "69" position. I knew, of course, that this position would allow even more of my semen to drain out of Jody. The thought of that and the position of these two women so that they could both suck on my cock was just too delicious.
Of course, Catie knew what would happen with Jody positioned this way above me, having experienced both on the train and in her apartment. Jody rolled over and then positioned her knees on either side of my head and lowered her hips down to my face. I was looking up at her ass and her back as she lowered her vulva lips down to my mouth. My line of sight vision was limited by this position. I could tell, of course, when Jody was leaning forward towards my cock and I could tell by the angle whether it was Jody sucking on it or whether it was Catie. Or when they were both licking and playing with it. And there were times when they were apparently kissing.
It didn't take long for the flow of my semen out of Jody's pussy to increase and I willingly lapped it up. I know that some guys have real difficulty with this and I've always been thankful that I didn't and don't. I was in heaven, imagining what this looked like from all the sensations I was experiencing.
I felt fingers positioned at my anus and then sliding into me. The anal stimulation was quite enjoyable. I wasn't sure whether it was Jody or Catie (or maybe both?), but it made me want to have my cock in a warm and wet space. For the moment, that warm and wet space was being shared by Catie and Jody as they took turns with my cock into their mouths.
I sensed Catie's movement away from me and it became apparent why a few moments later as I felt the nozzle from the enema bag (which was still hanging on the lamp) slide into me. Not a word was said about this as I had Jody's pussy at my mouth. I heard the click and felt the cool water flow out of the hose and into my rectum. A few moments later the temperature changed to lukewarm flow. It didn't seem to be filling me at a fast rate.
As the 2+ quarts were flowing into me, I became aware of Catie positioning herself to slide my cock inside her and gradually she did. Fucking while being filled with a 2 quart enema was certainly manageable for me. I wasn't sure at the time, but it felt like she positioned herself to slide me into her rectum because it was both tight as I slid in and not tight as I penetrated deeper. My assessment was correct as I heard the conversation between Jody and Catie about being fucked in the ass. Catie was sliding up and down my cock very vigorously while I was being filled quite slowly by the enema. At one point, she sat all the way down on me with her full weight as she changed position and with it, the angle of my cock inside her. I realized that her legs were now in front of her and she was leaning back as she slid my cock in and out of her ass. I was aware of more pressure on the tip and head of my penis as I rubbed along her rectal tissue wall.
This change in position by Catie gave a clear view of her pussy to Jody and Jody took the opportunity to lean forward and take Catie between her lips and tongue. This action brought Catie to multiple orgasms.
The rate of my semen flow out of Jody's pussy had dropped substantially with her above me as I had lapped it up. My nose was pressing against Jody's anus occasionally and I suddenly had an urge to press my tongue against and then through her anal opening. With Jody leaning forward, I could raise my head to "follow" her. I grabbed a pillow and placed it under my head.
The contact of my tongue to Jody's anus was "electric" for her (her description later) as I traced around and then into her opening. In the meantime, I was becoming aware of my enema spreading throughout my lower colon. The enema wasn't uncomfortable and, in some ways, was easier because it was lukewarm. Anilingus wasn't something I did often, but it seemed so natural under the circumstances. As Jody and Catie played with each other, I could feel myself being drawn to another orgasm with each stroke into Catie.
Somehow Catie and Jody agreed to change positions. When Jody lifted off of me, I got the view of Catie's legs spread open and the wetness of her pussy and vulva lips. I could also see where my cock disappeared into Catie's ass. Catie slowly lifted herself off of me and my cock flopped forward onto my belly. Catie crawled off me to give up her position to Jody. I could see that the enema bag was more than halfway emptied but still had a ways to go before being completely emptied. I remember thinking that the bag needed to be higher in order to empty into me.
Catie took some lubricant and applied it to my cock. She had Jody lean over and applied some to her anus. Jody straddled me and from behind, Catie positioned my cock to slide into Jody. If we had thought about, we probably would have taken the time to wash my cock before sliding it into Jody. But our lust didn't let us slow down for that.
Jody slid down my cock and sunk it up her ass. It wasn't fast but it was fairly constant pressure. I could watch and see myself penetrating deeper and deeper until Jody bottomed out on me.
"GOD, it's big!"
"I told you." Catie said.
Jody sat still for a minute or two while she squeezed down on me. It allowed her rectum to adapt to my penetration and to allow her to take me a bit deeper.
"You sure picked a nice cock for your first anal fuck."
There was more bantering between Jody and Catie about my size and depth. It was surreal to hear these two women describing the sensations of my cock in their asses, particularly when one of them had me deep inside her ass. Catie was standing off and behind Jody's right shoulder while this was going on. I reached forward to Jody's breasts and began fondling them while raising my hips to begin a thrusting action. Jody took the cue and and began sliding up and down my cock.
Over Jody's shoulder, I saw Catie unhook the enema bag from the lamp and raise it to a higher level. This increased the enema flow rate into me out of the bag. It didn't take long for the bag to flatten to empty. Catie moved the clamp to the end of the hose near the bag and then closed the clamp once the bag was drained. As I propped myself up to suck Jody's breasts, the two quarts of enema solution were sloshing around inside me with each of her strokes. Catie unscrewed the connection from the bag and walked away towards the bathroom telling me not to cum yet.
Jody fucked me more vigorously and rode me to have each stroke slide deeply inside her rectum. Somewhere between our legs the hose was laying on the bed with the clamp holding the enema inside me. Two quarts was well within my normal holding capacity. But in the background, we could both hear the water running in the bathroom and the sound of the enema bag being filled and I certainly knew that it was meant for me.
Catie came back into room carrying the bag and it was clearly full.
"Look what I brought for you!" Catie carefully screwed the connector back into the bag and presented me with a predicament challenge.