Ann was such a sweet and delightful surprise as she took the whole enema without stopping. I did slow her filling by lowering the bag somewhat. But, I did not use the clamp to slow the flow or to stop it. I closed the clamp only when the bag was drained.

"How are you feeling?" I asked.

"Good. Nice and warm inside my tummy?"

"Remember, you're going to want to release it and that urge might happen fast. I'm going to slowly pull the nozzle out," I said to Ann. I was still holding the nozzle in place with my thumb and forefinger. I had Abby hold the bag as I removed the nozzle. Once the nozzle was out, Abby took the bag back to the sink.

I let my hands glide lightly across Ann's ass as she had her head down facing towards me.

"Do you want me to slip me finger back in you? Only one finger," I asked. She told me that she'd like that and I slipped my index finger that still had the coating of petroleum jelly back into her all the way to the bottom knuckle. I pivoted and moved my finger inside her warm, wet rectum. It took only a couple of minutes before the first urge to expel hit her. She squeezed her anus down on my finger to hold the enema in. After the urge passed, I asked if she wanted me to remove my finger or leave it in as she walked to the bathroom. She thought that she could walk to the bathroom without my finger holding her enema in.

I helped her get off the bed and held her hand as she walked into the bathroom to sit on the toilet.

"Do you want some privacy while you release?" I asked. She indicated that she did. With that I gave her a kiss, told her to call if she needed anything, and closed the door. I came back to the bed and sat down with the other three women who had been quiet while I was giving Ann her enema but who were now chatting about the enema. Abby asked if I was going to give her (Ann) another one and I told her that I planned to because it felt like she was going to need one (from my finger insertions).

In the meantime, Ann was releasing her very first enema. We heard the toilet flush a couple of times and the door finally opened and Ann returned to the bedroom area of the hotel room.

"Everything okay?" I asked Ann. She said it was. She also noted how unusual it felt to "have all that stuff" coming out of her so quickly. I asked her if she was ready for her next one of about the same size. She enthusiastically told me yes and we repeated the process. The second time she held the enema longer and she wanted my finger to stay in her all the way to the bathroom. It was actually quite amusing as we walked away from the bed, I had my right index finger stuck in her rectum, she had her left hand wrapped around my erect cock as if she was leading me to the bathroom with her.

When we got in the bathroom, and before she sat down, she turned slightly towards me and said (quietly) "Abby tells me that you usually like to stay in the bathroom with her as she releases her enemas."

"Yes, if she wants me to," I said. "She tried it after she learned that from her sister and me."

"And she sucks your cock while she's on the toilet?" Ann asked.

"Sometimes," I said. "More often than not, I will have her slide way forward on the toilet, spread her legs, lean back and I'll eat her while she releases. We haven't done that too many times. But her sister and I did that all the time. And her sister would suck my cock while I was expelling or straddle me and fuck me while I was expelling." I paused.

"Would you like to try that?" I asked.

"Not right now," Ann said. "Abby told me about it and I'm just curious." I could tell Ann was thinking about it.

"I think Abby thought it was kind of gross and yucky until she saw her sister and I do it and she then she tried it and found that it can be pretty erotic. But it's not something that everyone would feel comfortable doing," I said.

I had Ann turn so that she could sit on the toilet and had her sit forward so that I could remove my finger from my position leaning over her. I had to lean over without falling over to keep my finger in her rectum.

"Are you ready?" I asked. She indicated she was. I slow extracted my finger from her rectum and then stood up. She took my cock back in her hand and pulled it towards her face where she took a playful suck and kiss. The she let go with a playful smile.

"I'll be out there if you need me or want me for anything." I stepped out and pulled the door closed (but not latched) and started to walk back to the bed where the women were discussing something among themselves. Ann did not push the door closed. I stopped at the sink, washed my hands (particularly my fingers), flushed out the bag and hose, and cleaned the nozzle with soap and water before rinsing it again. I carried the bag and nozzle out to the bed with me and told Delaney "You're next."

After a few minutes and a couple of toilet flushes, Ann came back to join us.

"Are you still up for this?" I asked her. She assured me she was.

We waited a few more minutes to make sure that she was well drained. After one last quick trip to the toilet, I had her get back on the bed with her ass up. Whatever inhibition she seemed to have at the beginning seemed to have dissolved away. Her anus was still well-coated with petroleum jelly (like I said, it doesn't wash away with water). I told her that I would be using a water-based lubricant to go along with what she already had inside her. I was really quite focused on her in the moment.

I opened the tube of lubricant and squeezed out a large dollop onto three of my fingers. I leaned down beside her and whispered in her ear "just like before." Her eyes were closed as she nodded her head. Although she couldn't see where I was, she could feel me move on my knees behind her. I could see the slight sheen from the petroleum jelly on and around her anus. I was curious about how she would react and I took my recent experiences and brought my tongue and my mouth to her anus. While everyone else could see what I was doing, Ann could not and she thought my finger was tracing its way into her anus like it had before. Only when my nose and my lips made contact did she realize that it wasn't my finger in her ass, it was my tongue.

Now, Abby knew what was coming and what I was doing because it was something that she and I had already done. I heard Stephanie ask Abby if we (meaning Abby and I) did that.

"Oh, yes," Abby replied to Stephanie.

"I want him to do that to me," Stephanie said, rather emphatically. I was tempted to pull away Ann's anus to tell her that I would. But I kept my tongue as deeply implanted and twirling inside her anal muscle ring as I could. Ann seemed totally relaxed and perfectly happy to have my lips pressed to her anus and my tongue playing with her. Although petroleum jelly has a scent it is mostly tasteless. I later joked that it was a unique way for preventing chapped lips.

As "well-trained" and "conditioned" as my tongue was to such activities with a woman's vagina, it took my effort to keep my tongue inserted into her anus. Over a period of a few minutes I started to experience a tongue muscle fatigue further back towards my jaws. But Ann was relaxed and I still had the lube on my fingers. So, slowly pulled my face away from being buried in her butt crack, asked if she liked it (she did), and then told her that I was about to insert the first finger to lubricate her.

I got the first two fingers in her relatively easily. I partially withdrew my two fingers and added more lubricant. Abby and Delaney were watching intently while Stephanie brought the camera closer to watch my fingers stretch Ann open. I pulled my fingers further back and extended my third finger to start the insertion of all three fingers. I told Ann to let me know if it was too much or it hurt and I'd back off. It took me a little more than a minute to work my fingers in, but they were all the way in her. I rotated my arm and wrist around the touch and stimulate the nerves at the base of her rectum in addition to stretching Ann and preparing her for my cock. It was nice and slow, just what she needed.

Feeling that she was adequately stretched and lubricated, I told her that I was withdrawing my fingers. When they were out of her, I had her get up on her knees so she could lubricate my cock (which she did with a certain level of vigor).

"I think we're ready," I said. "Are you ready?" I asked.

"Yes," she said. "So, get back down," I said.

She positioned herself on her knees and elbows with her head up. I told her that if things felt a little tight with some resistance that she could "bear down" like she was trying to push me out and that would sometimes help overcome the resistance. I reminded her that at any point, if she wanted to stop, I would. If she wanted me to withdraw, I would. If she just wanted me to stay in place until she got accustomed to my cock being inside her ass, I would.

Stephanie was to my right with the video camera as the tip of my cock made contact with her anus.

"Here we go," I told Ann and the other women watching Ann give up her anal virginity.

Yes, I wanted to get inside her; all the way inside her. But I knew to take it slow. With each little bit of pressure the tip of my cock went in a little further and the head of my cock began to be taken in as I stretched her open. I gave her updates on the progress and I checked in with her.

"Okay, the head of my cock is about to pass through the outer muscles and disappear inside you. Bear down a little if you need to help its passage into you. It's going to feel different once the head is all the way in," I told her.

Very short strokes. A millimeter or two at a time. I felt her squeeze down on the tip and suddenly I was inside. That got a reaction from her.

"Are you okay?" I asked.

"I'm okay," Ann responded. "Just stay there!"

"You're not an anal virgin any longer."

I held still for her. After a minute or so, she began to move to have me get deeper inside her. I applied a bit more lube to help the passage through her anus and then began to move with her to press further in. I was about three inches into her when we ran into some major resistance to further penetration. Abby and I had the same thought at the same time; to have Ann get on top of me so that she could control the penetration and the angle. I told Ann I was going to pull out of her, add some lubricant, and then have her get on top of me so she was in full control.

With Ann on top, she could control all of the penetration (if I didn't thrust up into her). She quickly got me back into her and just as quickly ran into the same resistance with me about halfway in her. I told her to just keep stroking at her own pace and applying pressure as much as she could tolerate and occasionally bearing down. I told her that if and when she opened that one area in her rectum that passage through that spot would be quite quick and probably very intense.

She kept taking short strokes. One of the things about this position was that my hands could glide across her front and sides and I could fondle her breasts and playfully pinch her nipples. Suddenly, she found the correct angle and with a hard bearing down squeeze on my cock, she bottomed on my cock. I think the sudden nature of entering her this deeply was so intense she immediately had to rise up off me. But that lasted only a few seconds before she bottomed out on me again, this time for a much extended period of time. She grabbed my hands, interlaced her fingers with mine. and she sat straight up to take me in very, very deeply.

She was shaking as she did this quietly saying "I'm okay" over and over again. I didn't know whether that was meant for me, her friends, or trying to tell herself that she was okay. Eventually the shaking subsided and she leaned forward.

"Are you okay?" I asked after she had whispered it so many times.

"Yes!" she said with a long exhale.

"Intense?" I half asked and half stated by my intonation.

"Now I understand the pain and pleasure part," Ann said. And with that she began to stroke up and down on my cock to feel it slide in and out of her ass. She wasn't going to orgasm this way and one of her friends gave her a vibrator to use. She came hard. Multiple times as she rode me with my cock in her ass.

About 7 minutes later I let her know that I was about to cum in her ass.

"I'm ready," was all she said. She put her hands on my chest as she continued to ride me. She felt me tense up and she settled all the down on me and stopped moving. A moment later...

"OH...I FEEL IT! Oh, cum in my ass. Cum in my ass! Cum in my ass...." Her voice trailed off.

She turned on the vibrator and slipped between my abdomen and her clitoris/vagina. It took her only a moment to reach her own orgasm again. She kept holding the vibrator in position to prolong her orgasm before she finally pulled it away. She laid down on me to catch her breath.

"How did you like it, Ann?" It was Stephanie asking her the question from behind the camera.

She turned to the camera. "It was great!" Ann was still breathing pretty hard. She laid her head back next to mine and I gently stroked her hair and her back. Her breathing returned towards normal but her heart was still beating pretty fast. She whispered in my ear.

"Do you lick your cum out after cumming in my ass?"

"Sometimes," I whispered back. "Do you want me to do that?" She nodded her head.

"Whenever you're ready, just turn around and sit your ass down on me," I whispered. I was pretty sure that no one else had heard what was said, though Abby knew that we might do this because she and I had. She knew that licking my cum out of her ass was quite erotic, though not necessarily my favorite thing to do because of possible bacteria issues and the taste of the lubricant. But, as I had explained to Abby, it seemed so erotic because it was also so taboo (and I hadn't had any real complications).

Ann didn't move immediately as my cock was still in her ass. But I was softening and I was going to slip out of her. Another minute or two and I felt myself slowly slipping out. She sat up, lifted herself up off me, turned around and positioned herself, and then lowered herself down. As she lowered herself, I stuck my tongue out to hit the center of her anus and to press into her as she settled down on me. I could tell what was flowing out of her was a combination of my cum and lube. But it was the lube I could mostly taste.

Other than "that's so nasty," I was unaware of the commentary. I could feel Ann lean forward and I felt my cock in someone's mouth. It was Ann to start off with, the Abby joined in and then Stephanie put the camera back on the tripod and she joined in. I didn't know exactly what took place until I later watched the videotape. It was mostly Ann taking my cock in her mouth. Delaney just watched. I heard Stephanie say "I want him to do that (to me)!"

We didn't stay this way for long as Ann raised up off me, turned around, and then curled up beside me.

I asked if she was doing okay. She told me that although she knew something big had been in her ass, she didn't hurt.

"Your first anal sex, anal creampie, and first ass to mouth," I pointed out. She said something about if I was sucking and licking my cum out of her ass, it seemed fair to take my cock in her mouth after cumming in her ass. Even Catie and I hadn't done that the first time. But I liked the "erotic nastiness." My new girlfriend wasn't interested in anal sex, so I was taking what I could get from these young women.

She needed something to drink and I got her a ginger ale and some water. We cuddled together on the bed amidst Dee, Abby, and Stephanie, before I finally gave her a kiss and offered a hand for Ann to get up and follow me into the bathroom to clean up. Ann used a warm wash cloth to wash my cock. I used another warm wash cloth to gently wash her anus and the area surrounding it.

We returned a few minutes later and I beckoned to Delaney. We went through much the same routine that Ann and I had. Where Ann seemed to have a heightened sense of anticipation and apprehension, Delaney seemed like she was just doing each one of the steps and, perhaps, going through motions. I thought that it might have been because she had seen the whole sequence from enemas through anal insertion to orgasm.

She took the initial lubrication and enemas with no issues and what seemed to be a neutral opinion. It was easier to get my fingers into her than it was Ann both before her enemas and after, in preparation for anal insertion. I asked if she wanted to do this and reaffirmed that if she didn't want to do this, it was okay to opt out. She said that she was ready and wanted to do this. Like Ann, I thoroughly lubricated her and had her lubricate my cock.

She got into position on the bed and spread her legs. As with Ann (and any first timer), I went slowly and described each step of the way. Stephanie was recording the whole sequence.

It was much easier to slip into Delaney than it was Ann. Still I went slowly and we didn't have to resort to her being on top to penetrate her fully. After about 5 minutes of slow pushing and very short strokes, I was fully inside her. I told her that I was going to start stroking her with longer strokes and if it got too intense to let me know.

About two minutes into this somewhat more vigorous stroking, she told me it was too intense and that I needed to slow down. I did and wasn't pressing as deep as I stroked in and out. It helped but she was still feeling uncomfortable.

"Do you want me to stop?" I asked.

"Yes, I think I do," she said. I told her that I was pulling out of her (slowly). When I finally pulled out of her, she laid down on her stomach. I slipped beside her on the bed and asked if she was okay. She told me she thought she was. I was just too big for her and it felt too uncomfortable once I was all the way in her.

"Well, you aren't an anal virgin any longer," Stephanie said. "Welcome to the club." Then Stephanie turned to Ann and said "Welcome to the club."

This seemed to be a good place to take a break and Stephanie turned off the videotape. In retrospect, I wish she had left it on because the discussion between the four of them and with me was fascinating and very sexual. A lot of it had to do with my experiences when I was in college (though I had graduated 11 years earlier).

Finally, after all this talk Stephanie said to me (and the others) "I don't know about you, but I'm ready to get fucked in my ass."

"Ooo Kay!" I replied and I got up to head to the sink with Stephanie. She went over to the video recorder, turned it on and started recording. I extended my hand and she took it and we walked to the sink to fill the red enema bag with about a quart of warm water. Stephanie was no stranger to these types of enemas for clean out for anal sex. I told her that since she prepared Abby for her first time with me, I felt like Abby should be preparing her (instead of me). Abby would assist, however.

"Oh, that so sweet," Stephanie said.

I used the water-based lube on Stephanie since she wasn't a newbie. And my fingers slipped into her quite easily. "Any guy ever have his fingers in your ass like this?" I asked Stephanie. She told me that she'd had guys insert fingers in her but not to lube her like this for enemas. I slipped the nozzle in her ass and opened the clamp.

"Ever had a guy give you an enema?" I asked her.

"You're my first," Stephanie said as the warm water was flooding into her.

While the enema was flowing into her, I suggested that this might be something she might want to add for her anal partners (though I figured that I might be the exception rather than the rule). I knew that Abby and Stephanie talked about our anal play, so Stephanie had an idea of what Abby and I did together (and what Catie and I had been up to). When Stephanie was ready to expel the first enema, I took the nozzle out of her, held the bag and nozzle in one hand, held her hand with my other hand as she got off the bed and then led her to the toilet in the bathroom. I signaled to Abby to get the camera before I took Stephanie's hand.

By the time Abby got the camera and off the tripod and came to the corner, Stephanie and I were nearly to the bathroom as she got a nice view of us walking away from her. Because of the cable connection between the camera and the recorder deck, she could only stand there at the corner to record the scene. I laid the bag and the nozzle in the sink as we passed by and we slowly entered the bathroom area with the toilet and the tub.

I asked Stephanie how she was doing as we entered the tiled area of the bathroom and she indicated that she was doing fine. Stephanie quietly asked if we could do that thing that Abby and I did when Abby was expelling enemas.

"You mean eat your pussy while you're expelling?" I asked.

"Yes," she said.

"Of course," I replied and I raised the toilet seat so that she would be sitting directly on the toilet bowl porcelain. She knew how to get into position, moved forward so that the contents in her rectum and colon would end up in the toilet but her pussy would be accessible, spread her legs and then leaned back against the raised toilet seat. I looked to my ight and saw Abby with the camera to her shoulder looking through the viewfinder, and Ann and Delaney standing off to her left side and behind her. I gave them a little smile and then turned back to Stephanie.

"You can hold it or release it however you want," speaking of the enema. With that I got down on my knees between her legs and worked my lips back and forth up the inside of her thighs. And when I finally got to her pussy, I extended my tongue to press between the lips of her vulva and slid it up to her clitoris. She grasped my head with her hands and pulled towards her hard with low, persistent moans that reverberated in the bathroom. I continued my tongue action and added a little suction to the action. She was cumming and still holding the enema. She finally, released my head and with that came the splashing of the first stream of the enema against the porcelain bowl. She pushed my head away from her as she continued to release the enema and let her orgasm pass.

Finally, she said "That was amazing." She'd had orgasms before when releasing enemas when she was preparing for anal sex ("just thinking about a cock up my ass") but had never had a guys lips and tongue (or any lips and tongue) probing and exploring her as she released an enema. I told her that when Abby and I did it this way, Abby usually had a pussy full of my cum and a larger enema inside her that she had held while we were making love (I usually was holding an enema, too, and there was a certain choreography between the two of us releasing our enemas. It was still pretty new to Abby and me. For Catie and I it had been an easy thing to do, even "natural" because we were so attuned to each other).

I asked if she wanted more (of my licking). She said "No, I really want your cock up my ass." She got up, got cleaned up, flushed the toilet and we went to fill the bag the second time as a following rinse out enema. The girls moved out of our way and Abby placed the camera back on the tripod. Ann held the bag for me as I prepped Stephanie for her second enema.

Everything went smoothly with her second one and in a few minutes she was ready to release it. This time she put the toilet seat down and sat on the seat to release her enema. But, she also pulled me up to her so that she could suck my cock while she was expelling. I positioned myself in front of her so that she had easy access. She rubbed my balls and fondled my ass while she was expelling. Once again Abby was filming this and we were being watched.

"Are you empty?" I asked a few minutes later.

"I think so," Stephanie replied. She had massaged her stomach a few times to help the enema find its way out of her. She cleaned herself first with toilet paper and then with a washcloth, flushed the toilet and I took her hand to lead her out of the bathroom.

She hopped up on the bed and positioned herself on her knees, spread wide, head down.

"I'm ready," Stephanie said.

I got on the bed behind her positioned between her legs. "Such a beautiful sight," I said.

I brought my tongue and lips to her anus and gently pressed my tongue in through the center.