As my tongue penetrated Stephanie's ass (penetration may be a bit of a misnomer but it is the best descriptive term of trying to get the tip of the tongue through that muscle ring), the tension of anticipation transformed into the pleasure of penetration (for both of us). Though other guy's fingers may have explored her rectum, mine was the first tongue that had been here to explore. One thing that helped, of course, was our the previous night and early morning experiences. It helped her knowing how I was as a lover. We weren't having to establish that from scratch.

Her hips were just slightly broader than Abby's and her ass was a bit more muscular. I reached forward and grasped her hips with my hands to help draw my face and her ass together. There was no real rush or urgency as my tongue probed and swirled in her as far as I could go or as I gently licked her perineum (an often overlooked erogenous zone). I was aware of Abby to my right, Ann to my left. Delaney was behind me watching this show.

After a time, Stephanie pulled away from me, moved forward and then spun around on her knees. Facing me, she grabbed my cock and then slid her mouth over most of its length while sucking and gently playing with it in her mouth. She started to rock back and forth so that she could slide it in and out of her mouth. She didn't do that for long because she wasn't trying to get me to cum in her mouth. Rather, it was a short interlude before what came next. She pulled away and got up on her knees, asked for the tube of lubricant, took off the cap and squirted some on her hand. She then spread the lubricant over the length of my cock while telling me it was time for me to be inside, fucking her in the ass.

After she finished applying the lube to my cock, she spun around and presented her ass to me once again. I took some lubricant on my fingers and then inserted and applied it to her anus and into her rectum. Stephanie (like Abby) knew what to anticipate from her previous experience with anal sex. But this was the first time for me to enter Stephanie anally. Although she was experienced, I wasn't going to just plow straight into her.

"Okay, are you ready for this?" I asked as I got into position.

"Let me have it!" Stephanie said. While some would take that as permission to slam into her ass with force, I was not interested in hurting her.

The tip of my cock slipped in easily. There wasn't a lot of resistance as I slipped further in and within a minute my cock was buried in her ass.

"You feel bigger than I thought you would," Stephanie said as I pushed all the way into her. I checked to see if she wanted me to stop or to keep going.

"Definitely keep going!" she exclaimed.

Over the next couple of minutes I picked up the pace and the depth of strokes until I was fucking Stephanie with the same level of intensity that Abby and I shared. From over my right shoulder, Abby asked how Stephanie liked it. Between strokes she got out "He... really...fills me...up!"

But Stephanie wanted more. She wanted me to stroke harder. She wanted me to stroke deeper. Not (necessarily) with speed but with each stroke being an impact within her. Abby moved further to the right and below so that she could get a view from front as each stroke I gave Stephanie not only rippled her legs and ass, but rebounded through her face and breasts. My cock isn't monstrous in size, just above average, and yet I was afraid that I was going to hurt Stephanie if I fucked her this way for very long. There haven't been many women I've known who like anal sex with such intensity. Catie certainly grew to like it as our relationship deepened. And off the the top of my head, I've known only three other women (and did partake in hard anal sex with two of them) that liked it this way.

Stephanie asked for the vibrator. Ann turned it on and passed it to her. Bracing the impact with her right arm, she pressed the the length of the vibrator up against her pussy with the tip pressed against the underside of my cock. Fortunately, the lubricant let my cock slide over the tip of the vibrator. Stephanie asked me to press all the way in hold myself in her and moments later she had this incredibly intense orgasm. She dropped her head to the bed and held on to the vibrator. She pressed the end of the vibrator harder against the base of my cock and had the vibrator at maximum intensity so that the vibrations I felt were from the perineum all the way through my cock.

This wasn't the first time I had experienced something like this. My ex-wife and I had played with this type of vibrator a few times while doing something like this. She liked it best when the vibrator was inside me sending the vibrations down my cock and inside her.

Sometime after my ex and I had separated, I had discovered that I could cause a continuous, non-spurting orgasm if a sufficiently long vibrator was inserted inside me such that the head was placed at or near my prostate. Catie was fascinated by seeing me do that and, more importantly, knowing that I was "continually cumming inside her" while feeling the vibrations from my cock if I was inside her anally or vaginally. But Catie experienced more powerful orgasms when the vibrator was outside of me where she could control the placement and pressure on her parts while making my cock vibrate inside her. And that placement at or near the base of my cock and the vibration could make me cum.

I could tell that Stephanie had moved the vibrator away from her clitoris and vulva and that she was holding it so that the head was placed firmly at the base of my cock. She was very rhythmically saying "Stay there!" to me in an increasingly labored fashion as she held it in place. I didn't think I could press in any deeper to Stephanie than I was. But it felt like (and Stephanie later confirmed) that something "opened up" and I slipped in even deeper than I already was. I was getting pretty close to cumming with this vibrator pressed against me and I think my cock was expanding that last little bit it usually did just before I started cumming.

As soon as I felt myself go in deeper (again not stroking), Stephanie's monolog went from "Stay there" to "Oh, Fuck!" and after the third "Oh, Fuck!", Stephanie's eyes rolled backed and she started shaking (it was a great bit of videography on Abby's part to catch that eye roll because I couldn't see it from my position). Stephanie dropped the vibrator and it rolled to the side. I had Stephanie by her hips so that she couldn't get away. I was taking this in when I suddenly felt my own orgasm.

"Oh...Here I cum!" was what I managed to say and then the spurts of my cum started to coat the top of her rectum. Stephanie started to make cute little cooing sounds as she felt the last of my contractions inside her. Finally, we slid down onto the bed together with her on her stomach. I was still in her ass but not as deeply as I had been.

"Are you okay?" I finally asked as we laid there and my orgasm subsided.

"Yes. I've never felt that before. It was soooo good," she said.

In those moments, it was just Stephanie and I. My awareness of the other three women or the camera, and the vibrator that was still turned on were out of mind. Slowly, they re-entered my consciousness as I softened in Stephanie's ass. I asked Ann to get the vibrator from between our legs and turn it off. A minute later, Stephanie asked me to carefully pull myself out of her ass and then roll over on my back.

As I did she said "I need that tongue of yours to give my hole some tender loving care."

Abby didn't really change her position much as she was in a great spot to see Stephanie spin around to straddle me and set her (now puffy) asshole down on my mouth as we had agreed. I know it felt soothing to her but the first thing I had to contend with was the taste of the lubricant with its slightly bitter taste. I figured that I would just have to lick that away. My cum was pretty deep inside her and I couldn't taste that, yet. I wasn't soft yet and after a minute or so of licking Stephanie's asshole, she leaned forward and took my cock into her mouth. She wasn't going to miss a good ass-to-mouth moment. Her mouth action certainly kept me from getting any softer.

Although I could rim her from this position it was easier if she rose back up to have some more direct touch of my mouth and tongue. When she did, I could tell my cum was traveling down her rectum to my awaiting tongue and mouth because the taste and texture changed to something that was more bland. As my tongue probed and swabbed her well-used hole, she put more weight upon my face as she gave me more "access." She seemed to enjoy this treatment as no guy (until me) had ever done this for her. Over the next several minutes, I was aware that there was a fair amount of cum draining out of Stephanie (I guess the combination of not cumming in Delaney and the vibrator action had me shoot a rather large load into her). But I also became aware of another subtle change. There was a bit of a metallic taste that I sensed.

I asked Stephanie to raise up a bit. I couldn't see anything. I asked someone to get a tissue. Delaney got one and brought it back to me. I dabbed at Stephanie's ass to look at what was dripping out of her. It appeared that there were little streaks of blood mixed in with my cum. I told her and then showed her what was on the tissue.

"Nothing serious," she said. She had experienced this before with her other anal lovers. It was evident that the hard fucking that she desired had caused some minor internal damage. I had no idea where inside her she had been damaged and whether it was from stretching, abrasion, or internal impact. She asked me if I was willing to continue and I was. There no evidence (at least as far as I could tell) of any serious internal bleeding and I finished cleaning her and massaging her for another 10 minutes or so.

I wasn't paying attention to Abby as she got up to put the video camera back on the tripod. She got back on the bed facing Stephanie but positioned to take my cock in her mouth (which she did). She was ready to get me hard again and for us to show her friends what we liked to do. When Stephanie finally lifted off me, Abby slid down beside me and across my chest to kiss me while reaching back to my stiffened cock. She was whispering in my ear what she wanted us to do. I agreed.

But before we did, I wanted to know how her future roommate was doing. I had Stephanie move up beside me on the other side so she could cuddle up next to us. She told us that she knew that she had been fucked hard and that she "had never cum like that," explaining that she really liked the sensation of the vibrations in her rectum (being sent by my cock in her ass).

The orgasm, she explained, "came from somewhere else much deeper" and spread through out her. She really wasn't telling me this. She was telling her friends about her first anal orgasm and I just happened to be beside her. She finally turned to me and said:

"And you! You're such a nasty boy!"

"Who are you calling a boy?" alluding to the fact that I was 14 years older than she was.

"You know what I mean!" Stephanie retorted. "No guy I know would eat me after my pussy was full of cum. No guy would give me enemas, eat my ass, fuck my ass hard, and then eat his cum out of my ass."

"Now you know one. And you've got it all on tape to show those 'boys' how a real man does it."

We all chuckled at that. Abby finally suggested that we "get started" after a few more minutes in bed together. She and I got up and went to the sink where she washed my cock very thoroughly with soap and water. With that task completed, I filled the red enema bag and Abby and I walked out to the bedroom area. The other young women moved out of the way so that Abby could take her place on the bed. Since I was holding the bag and nozzle with my left hand, I couldn't take the cap off the tube of lubricant. Abby unscrewed the cap and squirted some lubricant on my right fingers and then got on the bed presenting her ass to my fingers.

I quickly slipped two of my fingers into Abby's rectum, playing with her nerve endings as I lubricated her. Where this was a new experience for Ann and Delaney, and the first time for Stephanie and me, this was familiar to Abby and I built upon the experiences that Catie and I shared with each other and with Abby.

I withdrew my fingers after spreading the lubricant and then slipped the nozzle into her rectum.

"Are you ready?" I asked Abby. "Yes," she said. And with that I opened the clamp and let the warm water flow into her. Although the bag held just over 2 quarts, I filled it with somewhat less liquid. This was larger enema than the ones that I had given the other three young women. For someone who thought they were a bit strange and even a bit gross, Abby had come to like the sensuous play that was part of what we (Catie, her, and I) did.

Abby took the whole bag without any issue. As the bag drained, I closed the clamp and then withdrew the nozzle. I handed the bag to Ann to hang up since she was the closest to me. Abby kept her head down on the bed while I rubbed her back and her buttocks. Abby turned to me a few minutes later and asked me if I was ready and I told her I was.

"Who wants to give him an enema?" Abby asked. She got instant volunteers. Abby got up and led the three women to the sink. The plan that Abby and I had was to allow each of them to give me an enema of about one-quart. I would hold the enema and take the next one until I was holding about 3-quarts in me.

Ann was first and she got to lubricate me. She had a lot of fun with her fingers in my ass (It was the first time she had ever done that). After a few minutes of playing in my ass, she withdrew her fingers, was handed the nozzle, slipped it in, took the bag and opened the clamp so that it would empty into me. I heard the gurgle about a minute later and the closing of the clamp. Ann asked "who's next?" as she withdrew the nozzle. Delaney was next and Abby went with her to fill the bag.

I stayed in position on the bed while waiting for Delaney. She didn't have to lubricate me and when she got on the bag carrying the bag and the nozzle, she slipped it right in me. I felt the warmth of the water in my rectum spread and in a little more than a minute, the second bag was drained into me. I heard the clamp click shut though the nozzle stayed in me. There was commentary among the four of them about the look of my ass in that position and the nozzle that was inserted into me. Finally, the nozzle was withdrawn and Abby and Stephanie went to prepare the third enema.

Stephanie got on the bed and slipped the nozzle in me. But she didn't just put it in and leave it in. She slid it in and out of me a bit. Abby asked if I was ready and when I affirmed I was, Stephanie opened the clamp to allow the third quart of warm water into me. It went in a little slower and I was starting to feel the effects of filling. After the bag drained, the nozzle was withdrawn and Abby took the bag.

"Are you okay, hun?" Abby asked. I told her that I was doing fine.

"I've got to go empty out but I'll be right back," Abby said. She took the bag with her and scurried off. So, there I was with my ass up in the air while on the bed filled with three quarts of warm water in front of these three young women. A few moments later, we could hear Abby releasing her enema into the toilet in long streams. While Abby was releasing, I had hands stroking my cock and my balls. I was totally vulnerable in the moment and yet, trusting.

A few minutes later there was the toilet flush and then hearing water running in the sink. There was the telltale sound of the enema bag being filled once again. From the other side of the wall Abby asked if I was still doing okay holding my enema (I was). "Turn over, I'll be there in a minute."

I turned over with a towel under me waiting for Abby. Abby came around corner with the nozzle already inserted, holding the bag in her left hand. It looked pretty full to me.

She was quite a sight from my position. She came down the side of the bed and asked Stephanie to hold the bag while she got on me. Abby straddled me and reached down to position my cock to enter her. She was telling me and her friends that watching me fuck them in the ass one-by-one made her so horny and she needed me inside her.

I watched the head of my cock slip inside her pussy lips and then disappear as she slid down my cock. She reached back for the clamp and released it to allow the warm water to flow into her rectum. She carefully rode my cock (and came) while being filled. I could feel the warmth of the enema from the inside. It did feel a little different to me but I think most of the sensation came from knowing that she (and we) were holding some quantity of an enema inside us while we were making love. This was not (comparatively speaking) vigorous sex because we both were holding enema and I realized how special that was because it certainly wasn't something that every woman would like or tolerate.

The original idea was after us spending some time with vaginal sex (and several orgasms), Abby would get up and release her enema while I held mine and then return with her clean rectum to finish me and have me cum in her ass. The fact that she had to release her first enema wasn't in the plan. Her friends got to watch us have this kind of kinky enema sex in person rather than on videotape (though the video was recording a new tape of her and I doing this). It felt really good to me and I wanted to cum. Getting close to orgasm actually made it easier for me to hold my enema. However, as I felt that being a possibility, I told Abby that she should get up and release her enema. She slid me out of her, got off the bed and took the empty bag from Stephanie, and walked away to the bathroom.

"Don't go anywhere," she said. "I'll be right back."

As sexy as she looked to me carrying the full bag towards me with the nozzle already in her ass, it looked even more sexy with the nozzle tucked in that cute ass of hers, as she carried the empty bag away. A minute later we heard Abby expelling her enema in the toilet with low quiet moans. She was trying to hurry it along but it still took a couple of minutes for her to release most of the enema. In the meantime, the other three woman were sitting around me on the bed, playing with me. It was "fun to have a naked man in the bed that we can play with."

Abby emerged and asked if I was going to be able to hold my enema until we were done.

"I think so," I said. She took my cock in her mouth briefly and then proceeded to lubricate my cock for anal insertion. Once lubricated, she slipped my cock in her ass and started to ride me again. With three quarts of liquid in my gut, it was a little more difficult for me to raise up and take her nipples and her breasts into my mouth but I did manage. She asked for the vibrator and applied to her clitoris while I was sucking to produce some pretty intense orgasms. She moved the vibrator further down and over my pubic bone to vibrate my cock from the other side. It didn't have the same intensity as when Stephanie applied the vibrator to the underside at the base of my cock, but Abby did like the vibrations she felt in her rectum. But she was also get more direct clitoral stimulation from this position and she rode me as hard as she dared.

"I'm getting really close," I said to let Abby know that I was about to fill her rectum with cum. With one hand above my heart, she sat upright and told me to fill her up. Moments later, I was cumming in Abby. As my contractions subsided, she gently laid down on me.

"Do you need to get up?" she asked. I told her that I could stay there with her for a few more minutes. As I softened inside her, I could feel some liquid flow down past my balls and down my crack to the towel under me.

"Too much water and not enough time for you," I said to Abby.

"I know, I'm sorry. It just felt so good," Abby said. It was okay and I told her so. After a couple of more minutes, I told her that I had better make my way to the bathroom.

I settled down on the toilet and let the enema stream out of me while Abby was out there talking with her friends. A couple of minutes later Abby came into the bathroom and asked where I was taking them to dinner.

"Where do you want to go?" I asked. They had a couple of places in mind. I told them to choose one and I'd buy them dinner. I came out of the bathroom a few minutes later and Abby went in to release the bit of enema liquid (and my cum) in the toilet. We all had a brief conversation about larger enemas and the time it takes to release and be cleaned by them (and hence the release I wasn't sucking my cum out of Abby's ass).

We headed for the shower (we all couldn't fit) do it was one after another. Stephanie packed up the video equipment and we all get dressed and left the hotel for dinner. It was a casual dinner experience as the five of us sat together at a booth/table combination. On the booth side, I sat between Ann and Abby. Stephanie and Delaney sat in chairs on the opposite side of the table. The day of being on the nude beach hadn't worked out and we sure had a fun time together all afternoon.

During dinner, Ann leaned over towards Abby and I asked if she could spend the night with us like Stephanie had the night before.

"I'll let Abby decide because we were going to have some alone time for us before I have to leave," I said.

"We have all day tomorrow and tomorrow night," Abby said to me.

"Sure," she said to Ann. Ann got up to make a phone call. A few minutes later she came back and told Abby and I that she was all set.

After dinner, I drove them all back to the hotel to get their cars so they could go home. We didn't have much on the schedule for Sunday (if the sun came out, maybe a trip up the Gorge). Ann and Abby both left to get some clothes and to make their presence known to their families. It was still early in the evening as they all drove away.

I went to the front desk and asked if I could have a couple more towels as we had used all that the hotel had supplied. When I returned to my room, I straightened things and then laid back down on the bed that we had all spent the afternoon in. I made a couple of calls back home before it got too late in the Eastern time zone.

I was extremely mellow. I had spent the past 24 hours fucking four young women. Nothing like this had happened since my college days. I drifted off to sleep in the bed, thinking about the surreal experience with both a degree of pleasure and sadness.

None of this would have happened if I hadn't met and then taken a chance with Catie.