"Do you need another enema?" I asked from outside the bathroom.

After a moment or two, Sheryl said she thought maybe just one more just like the one I had just given her. I came back into the bathroom and prepared her third enema with my bag.

"Just like the last one?" I asked for clarification.

"Yes, just like it," she repeated with a wink and smile.

We returned to the bed with her on her back while I administered her enema. Once again, she was was stroking my cock (this time a bit more vigorously) while the bag drained into her. For her, having me as a "young lover" and as her enema giver, so willing to be involved in her preparation was, in some ways, a reminder of what she had lost and what she had missed after her husband had died. In the moment, it was more important to her that she was experiencing and enjoying this level of intimacy once again. I sensed this and she later confirmed her thoughts and feelings about this time that we spent together.

The bag was drained into her and I closed the clamp and laid the bag down on the bed while she continued to stroke my cock. I asked her if she wanted to make me cum and watch my cum shoot all over her. She admitted that she'd love to see my cum shooting out of the tip of my cock to splatter her. But what she really wanted was to have me inside her (ass) and to feel me cum inside her. I let her know when I was getting really close to cumming and she released my cock and told me that she'd go and release her enema.

From outside the bathroom I could hear the streams of water shooting out of her ass. No plopping, just water streams and drips. Finally, the air trapped inside her came farting out indicating she had largely discharged all the enema inside her. I asked how she was doing and she indicated that with the enema she had taken earlier, and the ones I gave her, that she seemed pretty well cleaned out. That was good to hear as I was wondering what surprise she had for me. She was curious about my enema experiences. They were much more common when she was growing up but seemed to taper off with my generation.

"Oh, I have friends that I know were given and gave enemas," I said. "We just didn't talk about it very much." But I also guessed that it was something that was becoming far less common. As far as I knew, my ex-wife had never given our son an enema. I certainly hadn't; though, if he had ever asked me about them, I certainly would have answered his questions. As teenagers, those enema experiences became much more erotic for us with the flood of raging hormones.

I heard the toilet flush (again), this time for the last time. Sheryl emerged from the bathroom. When she went in, she was naked. When she walked out, she was wearing black stockings supported by a garter belt. Nothing more. It was really quite sexy, I thought, and I told her so.

"Is this my surprise?" I asked.

"Only part of it," she replied. She had a warm and wet wash cloth in her hand and she wrapped it around my cock to clean it off. She seemed to take such great pleasure in cleaning me and inspecting my cock as she wrapped the wash cloth around it and and used it to clean it. When she was done, she took my cock into her mouth for a moment to taste and suck on it. She then walked over to her bag, reached in and pulled out what looked like a long black dildo with a smooth rounded head. Upon closer inspection, I realized that it was actually a vibrator made of a hard plastic material, maybe about 8 inches long and 1.5 inches in diameter. She turned it on at the base and then turned it up in down in the range of vibration.

"Sometimes, I used this on Steven," she said. And then, with a twinkle in her eyes, "Now, I'm going to use it on you." There was something special to her about that vibrator and I didn't realize the full significance of that in the moment. She told me that she looked forward to using it on me. I thought about the way my ex-wife and Catie had both used vibrating toys in my ass. I think I got a bit harder at the prospect of what Sheryl might do.

"Is there more?" I asked. Sheryl indicated that there was more to the outfit that she was wearing. But she figured that it would just be removed anyway. And then she reached into the bag once again and pulled out a small bottle of cooking oil.

"I know the lubricant doesn't taste great," she said. "So, why not use something that provides lubrication, doesn't have a horrible taste, and is edible." Now the washcloth cleaning made sense. That wouldn't be the first time I had used a cooking or salad oil before. I had even used shortening in a pinch. But it had been quite some time since I had used this lubricating technique. And it was a little more difficult to clean up since it was oil-based rather than water-based. She wrapped her arm around me, holding the bottle of oil in her hand and whispered in my ear "that way, if you want to clean me up, you won't have that awful taste to contend with."

That suggested to me what she was thinking about tonight's anal session and that she wanted to feel my tongue up her ass after I had cum in her. It was a subtle but effective way to ask for what she wanted and I was open to indulging her request.

I was so ready to either push her down on the bed or to have her push me down. Instead, we took our own sweet time in finally getting on the bed as we stood beside it and explored each other with our hands, our lips, and our tongues. I don't know how long we did that slow exploration. We knew when we were ready to get into bed and start our preparations. When we got on the bed, the towels were already in place and we faced each other on our knees. She opened the bottle of oil and poured a quantity into the cup of her hand. She snapped the top closed and put the bottle on the bed. She took my cock in both her hands and spread the oil over my cock and around my balls.

"You like doing that," I said.

She admitted that she did and that she liked connecting the sense of touch and feeling of my cock and balls in her hands with what she already knew and felt when I was inside her. The amount of precum dripping from the tip of my cock was pretty remarkable. I let her continue stroking and lubricating my cock until she felt like she was done. She picked up the bottle of oil, handed it to me, and then turned away from me and got on her hands and knees so I could lubricate her ass.

I started with a few drops of oil on my index finger and then traced it around her waiting (and available) slightly puffy rosebud of an asshole. As I spread it, I would replenish the oil on my fingertip and gradually worked my finger toward the center to slide it into and through the opening. Sheryl was practically purring at the sensations of my finger tracing around and then into her anus. Once my finger slipped in, I added more oil and ran it around the inner wall of her anus and rectum. Then I added a second finger to gently stretch and lubricate her even more. I spent much more time doing this with her compared to Saturday/Sunday morning.

I did something that she didn't expect after lubricating her. Before I slipped my fingers out of her rectum and anus, I brought my lips and my tongue down to where I had "opened her" and slipped my tongue into and through her opening. She jumped and moved forward in reaction to the touch of my tongue to her anus. Yes, it was much better with the oil. No bitter taste. Only the neutral taste of the vegetable oil and her nice, clean asshole. I was mindful not to take my lips and tongue down to her pussy after doing this. But I loved playing with her ass this way. If only I had a longer tongue, like a dog's tongue, I remember thinking.

Sheryl finally reached back to move my head away from her ass.

"You can do that later," she said. She was ready to have me slip my cock into her ass.

As I have mentioned earlier, Sheryl was no anal virgin. She and her late-husband had enjoyed anal sex throughout their marriage and had a bit of a ritual to it from what Sheryl had told me. And I had also inferred from Sheryl that her late husband's erect cock was slightly larger than mine, so she had a marriage full of deep penetration, both vaginally and anally, and I wasn't so afraid of "hurting her." I did start off slowly and gently as I put the tip of my cock against her anus and began a gradual penetration to allow the head of my cock into her ass.

I savored the slow penetration from my point of view above and behind her as I watched the tip and then the head of my cock slowly disappear inside her. Getting her stretched open with the head of my cock was the first hurdle. The oil helped and once the head popped through her sphincter muscles, they gripped my cock just below the head. She seemed tighter to me than she felt the other night. Still that didn't restrict my ability to press into her and eventually get the full length of my cock into that warm and soft cavity that we had just cleaned out.

We were in no hurry and the stroke rate was indicative of that. Besides, as much as Sheryl had stimulated me with a rise and fall of an imminent orgasm, I figured that I wasn't going to last all that long inside her before I coated the walls of her rectum with a rather large load of my cum. I stayed behind her as I fucked her. Sometimes her head was down on the bed as she submitted her ass to my strokes. Other times, she was up on her hands and knees bringing her hips back to meet mine with a light jolt at the end of the stroke.

But the best part about fucking this way was having her come upright on her knees while I was stroking both up and forward deep into her ass. I could wrap my arms around her and bring my chest to her back, coddled and squeeze her breasts, or have her guide my hands where she wanted them. I could kiss her neck or her ears from this position and with a bit of a twist by both of us, our lips could meet for numerous kisses. It was during one of these upright times that I could feel myself getting close to cumming.

"Are you ready for me to cum?" I whispered.

"Mmmm...hmmm," she cooed.

A few more slow strokes and then an upward press to be all the way inside her as I felt myself go over the edge.

"Here I cum," I whispered in her ear. She felt the first couple of contractions and then guided my left hand down to her pubic area. I hardly had to do anything as her hand, over top of mine, reached her pubic mound and our fingers found their mark near her clitoris. That's all it took to set set her off as she started shaking and quivering in my arms, pressed against my chest. She finally fell forward to prop on her arms, all while each contraction that I had pumped more cum into her ass. As my contractions diminished and got further apart, she slid down onto her stomach and I "followed her down" to lay on her back. I moved my legs outside of hers so I could remain pressed deeply inside her. Even after two minutes, I was still having these random pulses as I shot just a bit more of my semen into her.

We lay there several minutes in this position, me on her back, my head over one of her shoulders, our hands clasped together (when did we clasp hands? I wasn't even aware that we had until we were laying there like this) without saying a word. My cock was still firmly in her ass acting as a butt plug holding my cum in her rectum. After a few minutes more, I could feel that my erection was fading and I would soon slide out of Sheryl. Before I got too soft, I had her and I get up off the bed with at least our hips up while on our knees. That was so, if and when I did slip out of her, we could address my cum that would likely drip out of her ass and prevent it from running down to her pussy.

"That was so nice," Sheryl said to me. Of course, we weren't done yet and few minutes later my cock did slide out of her. This what Sheryl was anticipating and the reason we used the oil rather the lubricant we had been using. Looking at her ass, there was no evidence of a crappy mess to deal with. There were a couple of "pearl drops" of my cum forming where my cock had been. I brought my tongue to swirl around those drops and to do a tongue massage of her rectal tissue, though not pounded, was slightly swollen.

After a doing the initial cleanup, I repositioned myself so that Sheryl could get on top of me to let my cum drain out of her rectum. The fact that I was doing it was an erotic turn-on for her and soon she was ready for a second round of anal sex with me. She spread more oil on my enlarging cock and positioned herself above me so that this time, she could control sliding me into her ass. She inserted me much quicker this second time and rode me with more vigor than I had applied during our first session.

She added something to this, too. The vibrator that she had brought with her, the one that she and her late husband had used, was going to be slid into my ass. Soon, she had it lubricated and, reaching around behind herself, pressed it into me. Insertion was a little painful because the angle wasn't quite right at first. But once it was inserted such that the head of it was aligned properly, it slid in smoothly. She turned it on and adjusted the vibration. The vibrations in my rectum traveled up my cock and into her rectum.

From her experiences with her late husband, she knew there was a placement where the head of the vibrator would sit and press upon my prostate while transmitting the maximum vibration up the shaft of my cock. It's hard to hold the vibrator there while sliding up and down on a cock (and mine was no different in that regard), so it's really about angles and having the base of the vibrator pressed against the mattress or the towels and not sliding out.

My ex-wife liked to do this same type of thing with me, so this wasn't new for me. What I also knew was when positioned just so, the vibration would "milk" me in such a way that I would produce a continuous stream of what looked like partially mixed semen. It was an intense sensation that felt wonderful and it didn't seem to preclude me from having a "normal" orgasm at the end of all of this. I know what it feels like when it hits the spot that triggers this continuous flow. It didn't happen right away but it finally did and I tried to hold the vibrator in position for as long as I could before I had to give myself a chance to recover from the intensity.

Sheryl was unaware of the constant stream of cum that was flowing into her but I was. My heart races with this level of stimulation and I was aware of that. All she could feel was the vibration being transmitted though my cock into her ass. But she did notice that suddenly she was very wet back there because of all the cum that was flowing into her. With the oil and cum acting as a lube, it became very easy for her to ride me even harder. There was a "pool" of my cum forming at the base of my cock and running down my balls and my ass crack. Sheryl, on the other hand, was riding me in such a way as to bring her pussy down on my pubic bone and mound to stimulate herself in addition to having my cock up her ass. The combination was giving her these great orgasms that she would ride for a moment before continuing.

And although she didn't realize it in the moment, during one of those orgasms, she called out her late husband's name, saying "Oh, Steven!" I think it was only after she was coming down from that orgasm that she thought that she may have said his name rather than mine. I didn't say anything about it in the moment and neither did she.

I was finally ready to cum (normally) if there was anything left to pump out. I pulled Sheryl down on me by her hips and held her down while I felt like my cock was shooting straight up into her. I had her turn off the vibrator, though she could leave it in my ass (which she did).

It didn't take me long to slide out of her. She asked me if I would or wanted to clean her again. I was pretty spent by the vibrating orgasm. But I told her that I would and helped her settle onto her face and slipped my tongue into her rectum as far as I could to take in the cum that was leaking out of her. She loved the eroticism of being cleaned this way and when she was finally satiated, she got off me, used the wash cloth to wipe my face and then laid down beside me while we had a very intimate conversation about some of our sexual experiences; her speaking about her late-husband and me speaking about my late-girlfriend, Catie.

We did finally drift off to sleep like this, or at least I did.

When we awoke on Wednesday morning, Sheryl told me that she had placed the room service breakfast hang tag on the door when she got up to go to the bathroom and that she had ordered us breakfast. We had another 90 minutes or so, before breakfast would be delivered and Sheryl suggested that we get in the shower to clean up from our anal sex sessions the previous evening. We enjoyed a warm shower together as we washed each other and after drying with towels, we crawled back into bed together. Sheryl promptly got on top of me and because I was erect, slipped my cock inside her pussy for some slow, intimate lovemaking.

What made this much different was that it was much like a continuation of the conversation we had before we went to sleep, where we were sharing about our deceased love partners. To say it felt strange to be talking about them while Sheryl and I were doing this slow fuck, her talking about Steven and me talking about Catie, would be an understatement. There was no sense of betrayal or at least none that I felt or that I could discern. Rather it was sharing about the things we loved and/or experienced that were so powerful in our relationships that we missed. In the end, it was still about us as two people still processing the losses we had and finding a path forward from those losses. And in that moment we were substituting each other for the one we lost.

She asked if she had called me by her late husband's name during the previous evening, not certain she had actually done that or she had imagined it.

"Yes," I said.

"I'm sorry," she replied.

"Don't be. I'm glad that I was making you feel so good and in a way that reminded you of your husband. I'm not offended," I said. It was true. There was nothing to be embarrassed about. We could certainly laugh about it and we did. My ego wasn't hurt by being called by his name.

As I joked, "I don't care what you call me, just as long as you call me in time to eat you."

I finally came inside Sheryl and we laid there together in the shared warmth and closeness.

"I want you to come (or was it cum) for supper tonight at my house. That's also part of your surprise. Do you think you can come?" she asked.

"I can cum and cum and cum," I replied.

"I'm counting on it and I'll hold you to it!" she said.

Our breakfast finally arrived and we ate it in a light hearted way. I did get into the shower again to rinse off before getting dressed to head to my conference. Sheryl gave me her address and a time for me to arrive for the evening. She told me that she'd be leaving shortly after me. We kissed goodbye and I headed down to my conference with a smile on my face.

My day at the conference was a good one and yet, I was impatient with the sense of time passing slowly. I could hardly wait. At the end of the day, I was asked about supper plans.

"A friend invited me to cum for dinner," I said, though I'm sure they heard it as 'come.'

I got back to my room to change clothes into something other than my business clothing of a coat and tie. I called Sheryl to ask how I should dress and if there was anything she wanted me to bring.

"Just bring yourself," she said, "and something that's easy to get off you," she said.

"How about getting me off?" I asked playfully

"I think we can handle that," she said. "You might want to bring what you need to wear tomorrow morning because I plan to have you here all night," she added.

I thought seriously about just wearing sweatpants and a sweatshirt, then I thought I should probably go with something business casual and I could bring the sweats with me for something more casual. The weather had been warm during the day (even though I was inside). But, a weather front was moving in and the warm weather was going to be swept away; something to consider for the next morning.

I rode the elevator down to retrieve my rental car and then drove to the address that Sheryl had given me. It was a beautiful house from the outside and it certainly made mine look like a wimpy thing. In some ways it reminded me of the home that Ted and Annie had in Minnesota. There were numerous cars in the driveway. I didn't see Sheryl's car, although it could have been parked in the garage. I parked on the street and then walked up to the front door. I could hear the doorbell, when I pushed the doorbell button.

The door opened.

"Megan?!?!"