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The Long Goodbye

Chapter 10: Cumming Back to Chicago for Jody

The flight to Chicago was uneventful. My mind drifted back and forth from my days at Vail and other places I skied earlier in the week and what was awaiting me in Chicago. It was one of those situations where time seemed to drag on because of the anticipation at the same time it was passing quickly because my mind was focused. After the plane landed, the taxi time seemed to take forever. At last the door was opened and I could get out and up the jetway.

I was still wearing my ski clothes including my stretch pants. Jody met me in the gate area with a hug and a very passionate kiss. When Jody saw me in my ski pants she told me "that ass of your looks good in them." She also wanted to get me out of them. We walked down the concourse with playful banter, sometimes arm-in-arm. My suitcase was on the carousel when we arrived in baggage claim. My skis arrived a few minutes later. We walked out to the parking area and put my gear in her car and we left for her condo. We talked more about my skiing than what she was going to do to me when we got to her place.

When we arrived (not too far from Catie's former apartment) we gathered all my gear and took it inside. She had me put my ski bag on the hallway floor and told me I could put my suitcase and boot bag in the living room. No sooner than I had put my gear down, she came to me, embraced me with a kiss and began pulling my clothes off. I reciprocated as I stripped her, too. When Jody's hands slipped down by back and past the waistband of my pants she found...my ass. I was wearing a thong, one that Catie had given me so that I had "no panty lines for my stretch pants." Plus, Catie loved to have my ass "assessible." It was funny that when we both got each other's pants off we were both wearing thongs.

I was hard and Jody released me from my thong. She was incredibly wet and that was visible at her crotch of the thong. I slipped my tongue into that warm and wet area. She was having none of that and practically pushed me down to the floor. She wasted no time mounting me and getting me all the way into her pussy. She started fucking me with wild abandon. So much so that she developed a bit or "rug burn" on her knees because she was fucking me so vigorously. After cumming in a long, continuous series of orgasms, she finally slowed down to gently rock on my cock, with one hand pulling her hair up to cool her neck after fucking me so hard.

"I've been thinking about this all afternoon," she said as she slowly picked up the pace. I wasn't going to disturb her sense of lust. She was a beautiful woman to watch when she was on top of me. Of course, I knew that from our time together with Catie. But this was our first time together without anyone else involved; just her and I. Nobody else watching, giving directions, or waiting their turn. Soon, she was bouncing up and down on me...hard. I watched as her breasts bounced and swung around with each stroke she took. I could tell that even the small of my back was beginning to have the effects of rug burn. But I let her continue until the next wave of orgasms subsided.

I suggested that we get ourselves to someplace more comfortable (like her bed). We got up, I grabbed my suitcase, and we went up the stairs to the master bedroom. She lit a number of candles around the room and in the bathroom and turned off the lights. We were going to be taking our enemas and fucking by candlelight. She took a couple of large pillows and put them on the bed. She then laid down, face down, with the pillows under her abdomen and hips to present her ass to me. I obliged her by getting in behind her and sliding my cock back in her pussy. I gave me a rather nice angle to give her nice, long strokes.

After several minutes and a couple of orgasms in this position, she told me she wanted to turn over to watch me cum in her. I pulled out of her, expecting her to toss the pillows and lay flat on the bed. Instead, she just flipped over with the pillows under her butt and the small of her back with her head lower that her hips. I slipped back inside her with a variation in stroke speed and depth. The angle was interesting as this was not a position I had experienced often. With Jody reclined in this way, the top of my glans was sliding along the front wall of her vagina.

As a sexual position, it wasn't an easy position to just lay down on her. Rather, it was easier to stay up on my hands and straightened arms like I was doing pushups while I stroked into her. But it was an easy position to draw her legs up around my shoulders looking down at her face as I continued my hip thrusting into her. She told me that she could tell I was getting closer to cumming and I acknowledged that I was.

"When you cum, I want you to give me that last stroke, push into me as deep as you can and then hold still and hold on. I want to watch your face and feel each pulse of cum you shoot into me."

Hearing such a request was almost enough to make me cum by itself. Of course, she knew that I'd stay in her as long as I could after cumming. It wasn't long after that my strokes slowed down and got long and deep. I was right there on the edge and it was a game to see how long I could hover there before going over the edge and filling her from deep within.

"I'm about to cum for you," I quietly said to Jody.

"I'm ready for you," she said as she gently grasped my head between her fingers. She asked me to look into her eyes as I was cumming. I pressed into her and then waited the few moments before the first spurt was sprayed out of the tip of my cock. It was the nature of this orgasm, the being still and being deep so that she could feel each contractions and the deep gaze into each other's eyes that made it so memorable. I knew then, as now, that it easy to "look away" and to get lost in the sensations and pleasures of orgasm. But to share with the person who is helping to provide the experience is something that is easily overlooked.

The smile on Jody's face probably reflected mine as I was cumming.

My orgasm was nearly over when Jody had a "pained look" on her face and short, quivering breathing. She didn't have to tell me...she was cumming. Could I feel her contractions? Not really. I just knew that her vagina was squeezing down on my cock and I was intent in staying in her just as deeply as I could. Now I was the one asking her to keep looking into my eyes to see their expressiveness.

It was a wonderful several minutes watching each other cum. Jody finally invited me to lay down on top of her. She unclasped her legs from around my shoulders and I lowered myself down.

"Why didn't we do more of this?" she asked.

I was confused by her question and asked her what she meant.

"Why didn't we fuck more?" she asked. "I thought we would have," she said.

I still wasn't quite getting it.

"Why didn't you, or Catie, or both of you have me play with you some more?"

Now I was starting to get it.

"I think it was because we were also so busy and lots of stuff happened that we really didn't plan for. But I know Catie wanted us to get together many times," I said. And that was true. The combination of Catie's dad having a stroke and then other schedule conflicts didn't have us get back into bed together. Besides, the relationship between Catie and I was evolving so very rapidly into something that I didn't expect with multiple partners for both me and for her.

"I had hoped that she would have sent you to me for a day, an evening, or a weekend," she said.

"You have me now," I said.

"Yes, I do, don't I?" she said. And for the next 20 minutes or so, it was just her and I. Not Catie. Not Mark. Just her and I. My cum inside her. My cock, semi-erect, staying inside her with an occasional push into her and a slight withdrawal just to keep me from going completely soft inside her. She could feel me getting hard again inside her and she was giving me a running commentary of what it felt like to her to have me getting hard inside her.

I asked her if she wanted to change position and she told me no. She wanted me to fuck her the same way and to cum in her the same way just in case she missed something the first time I was cumming, as she put it. Although I lasted a pretty long time between our screwing on the downstairs carpet and in her bed, this time I lasted longer and she had many more orgasms this second time we were in this position. Some of the cum from my first orgasm was forced or drawn out by my stroking in and out of her. But most of it apparently stayed in her (or was forced further into her by the angle of her back and hips on the pillows. My cum wasn't flowing uphill).

As I came in her the second time, she welcomed my cumming with very passionate kisses. And we laid there together for a long time before my cock finally slipped out of Jody.

"I'm ready for my first enema," Jody said to me as I lay on top of her after my cock slid out of her. I rolled off her and headed to my suitcase to retrieve my enema bag.

"I have one," Jody said. "It's hanging on the back of the bathroom door."

It was a red rubber open top bag that was maybe slightly larger than 2 quarts with a black curved nozzle. There was no place to hang the bag either over or beside the bed. The only choice was to fill the bag and hold it above her while emptying the enema into her. I turned on the water in the tub to allow the water to warm to the proper temperature before filling her bag.

"Bring a towel," Jody said. "No, bring two from the towel rack." As the water continued warming up, I grabbed two towels from the bathroom towel bars and brought them back into the bedroom. Jody had flipped over onto her knees towards the side of her bed; ass up, head down. There were even more pillows pulled to the center of the bed. She had me put one of towels across the pillows and the other one beside them. As soon as I did, I watched her crawl over to the pillows and get some of them under her knees while the others she pulled underneath her abdomen. I got up and turned off the water in the tub.

When I returned to the bedroom, I picked up the tube of lubricant on one of the nightstands beside the bed and opened it, applied a generous drop to my index finger and then closed the tube. Although the light level was dim from the lit candles, my eyes were adapted enough to see her pussy and her ass just waiting for me to play with. I leaned forward and ran my tongue up the slit of her pussy from her clitoris towards her anus.

"Not yet," she said in response to my tongue. "You'll be swallowing it all soon enough."

I pulled my face away and I took my lubricated index finger and slid it through her anus and all the way into her rectum. She let out a deep sigh as I penetrated her with the finger and then I started to swirl it around like I stirring a liquid in her rectum, running my finger along her rectal walls. She seemed very relaxed while anticipating what might cum next. However, after twirling my finger in her ass for several minutes she told me I should go get her enema or else she was going to have me fuck her in the ass right there and then and she had other plans.

I gently rubbed my other hand over her butt and then got up to fix her bag.

"How much do you want?" I asked. She told me to fill the bag even though she might take only half the bag. Once again, the water was on and I brought it to the correct temperature. Once the bag was filled, I hung it on the shower curtain rod and dried the outside of the bag. I unhooked and hung the hook over my finger.

"Looky, looky what I brought for you?!?!?" I said as I got on the bed and walked on my knees behind her.

"Did you bring me a full bag?" she asked.

"Just like you asked for," I said.

I slipped the curved nozzle into her and asked if she was ready. She told me she was and then added that she would tell me if she needed to slow or stop the filling. With that I let her know I was going to open the clamp and with a "click" I let the water begin to flow while I held the bag at about my head level. As the liquid showered her rectum she commented on how warm it felt. After about one-third of the bag had drained into her she asked for me to stop her filling. The clamp clicked shut and stopped the flow. I lowered the bag to a more comfortable level while waiting for her next request or set of directions. From my point of view was a wonderful sight by candlelight: the dimly lit red bag, the hose draped down and suspended between the bottom of the bag and the end of the nozzle in her ass.

She asked me to fill her some more after several minutes and I opened the clamp. She took another third of the bag before asking me to stop again and how much was left in the bag. I was holding the nozzle in place with my right hand and holding the bag up with my left. I asked if she was doing okay.

"Oh, yes. I'm feeling fine," she said and then described the feeling the warm water working its way further into her abdomen. After several more minutes she told me she was ready to take the rest of the bag. Once again there was the click of the clamp opening and the liquid drained into her. I raised the bag over my head to have it all flow into her before closing the clamp.

"Do you want more?" I asked.

"Yes," she said. "But I don't think I could hold it long enough."

"Long enough for what?" I asked.

"Long enough to cum in me again."

Of course, Jody and I had a longer exploration of enemasex the first time we were brought together by Catie than when it was her, Mark and I. And while the use of enemas for pleasant sensations and/or as preparation for anal sex was something that Jody had done before we met, I was the first male she knew who would have sex with her while holding enemas. She had told me she liked the sensation of having a cock inside her pussy and a warm enema in her ass as long as there wasn't too much pressure to hold (or worry about holding) the enema.

I slowly pulled the nozzle out of her rectum, got up and off the bed, and went back into the bathroom to hang up her bag. I was sure there would be more use of it later.

She told me that she wanted me to fuck her slowly and gently from behind as she was propped up on the pillows. Of course, I had been ready to do that for some time since we started out enema play. I slid into her now twice filled pussy from behind.

And for whatever reason (maybe because it could be pretty messy), it never occurred to me to try anal sex with any partner while he or she was holding an enema. It certainly was a lack of imagination on my part. I realize now that had she wanted me to push my cock into her ass full of water, she would have told me. No, I was where she wanted my cock to be.

Of course, I was prepared to pull out of her so she could get to the bathroom and to the toilet. And if that was going to fail, the other towel could be used to absorb the first gush of the expelling enema. We didn't need that towel (fortunately) though the enema challenged her ability to hold it in a couple of times. She told me later that the inability to control the angle that I was applying "pressure" made it more difficult to enjoy the full feeling she was experiencing. The slow and less vigorous fucking took me longer to cum and I finally did. As before, she had me hold "still" so she could feel the throb of each contraction. I stayed inside her as long as I could but we could both feel that my cock was going to slide out of her as I softened (though telling me what she wanted to do with me and sucking my cum covered cock slowed the softening process).

When my cock finally slid out of her, I moved down the bed beside her head where she took my cock in her mouth and gently sucked me clean. After a couple of minutes of playing with my cock, she asked me to go prepare the toilet for her. I got up and went to the toilet where I raised both the lid and the seat so that Jody could sit down on the porcelain as we had done before.

She carefully got off the bed and headed to the bathroom. Although I had just shot a gooey load of cum into her, the previous loads of cum had liquified. As she headed to the bathroom she told me that my cum was running down her leg. She quickly sat down on the porcelain, slid forward, spread her legs, slid forward a bit more and then invited me to "dive in." And I did! There was lots of my cum dripping/running out of her and I lapped it up as she was spraying the enema out of her ass into the toilet. She just leaned back to give me full access and the lapping of my tongue and the relief in the release of her enema caused waves of pleasure to wash over her. I licked the inside of her thighs to recover the cum that had run down her legs as she was headed to the bathroom.

When Jody had released all the enema that she thought that she could (and I had licked all the cum that I thought I could), she told me to go get my bag out of my suitcase and we got into the shower together and we gave each other multiple enemas. We concluded the last one (number 4?) by leaving both of us filled, drying off, and returning to Jody's bed. This time I was on the bottom while Jody rode me. Like Catie, she preferred this position when holding an enema and getting fucked at the same time because she could control so much of the action. Me, I just love this position to feel and to watch. And once again, I was cumming inside of Jody. We took our turns sitting on the "porcelain throne" and releasing our enemas (they were reasonably clear at that point) while the other was on their knees licking up the cum that had been shared.

We returned to bed. Jody was now well-cleaned-out and I slipped my tongue up her ass. That started the next rounds of anal, oral, and vaginal sex. It all became a blur because, as Jody told me, she had me to herself and she was going to use me as much as she could in as many ways as she could.

It wasn't fucking and sucking all the time, though. We took rest/recovery breaks. Some were us laying there in bed together with small talk. We had gone some time through the session before either of us mentioned either Catie or Mark. Sometime in the middle of the night, we came downstairs naked into her kitchen to grab a snack and something to drink where our conversation ran from the serious to lighthearted.

"You know that Catie was quite proud of you and very possessive," Jody told me while we were in the kitchen. I asked her to explain what she meant.

"She was proud she had you and wanted to show you off. You were hers and she wanted others to know that. You were like a special library book to her. She would loan you out but you belonged to her and she wanted you back."

I had known that in a different way, but the library book analogy was the best way to put it. Jody knew much about the way our sex life had branched out in very unexpected ways but if she knew everything that Catie and done, she didn't reveal it. She did know about out trip to Minneapolis and wanted to know more about that experience.

"You know that Catie wanted Mark to be the first in our exploration of her multi-partner sex?" She did. "We wanted to include you, too. But it was more about Catie experiencing sex with two or more men and Mark was someone she thought she'd be comfortable in sharing with. The opportunity on the train was just too good to pass up. And then you guys weren't really available and we had the invitation to go to Minneapolis and we accepted it."

She wanted to know more about it and how I felt about it. Besides a general interest there were some questions she had.

Did it feel competitive? Yes, in a way. Someone might and probably could out perform me on any given day or do something better that I could learn from. On the other hand, there was a reason why Catie and I were a couple and would remain so after this experience (library book, remember?}

Did I feel "jealous" watching other guys fucking and cumming in Catie? No. We did this for Catie and it was really hot watching her experiencing so much pleasure and having all her holes filled at the same time (which I couldn't do by myself). It wasn't about replacing each other.

Did it bother me to be in close contact with other guys or following that many guys? I told her that if you had homophobia, this was the wrong thing for you to be doing and it was almost impossible in multi-partner sex to avoid even incidental contact. And I knew from my experience that some of the guys were comfortable with bisexual situations. That was something that Catie and I hadn't fully explored but was "on the table" for our next Minneapolis trip...that didn't happen.

The thing I tried to make clear was that I wasn't trying to displace Mark (and I hoped that Mark realized that, too) and Jody was free to make her own choices about how to live her life. I was glad I was with her in that moment. But I had no illusion that Jody and I were about to become a couple after my loss of Catie. Jody told me that she was so happy that Catie had such a great time and love together, that Catie was so generous with me because she (Jody) probably wouldn't have had any of these experiences. We continued our conversation about Catie and though there was some guilt for both of us doing what we were doing after Catie's death, we also acknowledged just how much we both loved her. She would have wanted it to be this way we concluded.

We went back upstairs to Jody's bedroom and she continued use me (and I used her as well) throughout the night and well into the morning. We spent much of this time enjoying anal sex in numerous positions. Besides having my cock in her ass, Jody really enjoyed having my tongue probing into her and/or licking out the cum I had deposited there. Besides Jody's ass-to-mouth action with me, she also reciprocated with her tongue action up my ass. I told her that if she did that to Mark to show him how good it felt to be receiving that he should soon learn how to deliver as well as receive.

We knew our time together was cumming to an end and we cleaned up for one last oral and vaginal sex session. Although the pace was varied through various positions, it was a nice long session before I was cumming again. Women I've known are so lucky in this regard with their ability to enjoy multiple orgasms while I can manage one at a time with a break of several minutes before working on the next one like I could when I was younger. I was on top of Jody, her legs pulled up and squeezing my hips or wrapped around them as I came inside her for that last time. She rolled over on top of me right after that keeping me inside her. I softened a few minutes later and the tip of my cock slipped out of her. She brought her hips up to my head and settled down on my face to watch me clean her as she looked down (and I looked up) past her breasts. After she had several more orgasms sitting on my face, she realized that we really needed to get going if I was going to catch my scheduled flight home.

We went back downstairs to get a light breakfast before getting back in the shower together. Although I wanted to stay and leave later, maybe early evening, I knew that I had my son to see back home and that I needed to get dressed and prepared to leave. I packed my clothes and enema bags back in my suitcase and took it back to Jody's car. Then my skis and boot bag.

It was a cool and cloudy day. We left her condo late in the morning so she could take me back to the airport to catch my early afternoon flight. We rode together mostly in the silent afterglow or the previous night and morning, occasionally holding hands. Parting was going to be such sweet sorrow. I told her that I wished that she could have or would have joined me (with or without Mark) in Colorado. Maybe next time, she told me. Again, I didn't know that I'd be back out in Colorado in two months. We arrived at O'Hare and I checked my luggage, taking only my boot bag with me on the plane.

She wanted to come into the terminal with me and we drove and parked the car in the short-term parking area. We walked together; sometimes hand-in-hand, sometimes arm-in-arm into the terminal through security and then to the gate area where we waited for my flight to be called for boarding. There was that one last kiss in the boarding area where I thanked her for having me.

"Thank you for cumming, and cumming, and cumming," she whispered.

"Would you like me to cum again?", speaking in double entendre.

"I would. I'll talk with Mark," she said. I gave her one more kiss, told her I'd call her later and boarded the plane. Being well-fucked and mellow seemed to be a dominant characteristic of leaving Chicago.