Hall Pass

She went over and pulled a cardboard box off the cabinet beside the fireplace chimney. I hadn't seen it, there, and I don't think anyone else had, either. She began making the rounds of the room. "Everyone reach into the box and take one without looking, please."

We all did as we were told and each of us pulled out one of those drugstore enemas. I thought that there would be ornery comments but the room was silent.

"We're going to start by playing doctor," she said. "As you know, Jan and Kyle's seminar is going to be about anal play and anal sex. We want this to be a clean and safe evening so, everyone is going to get cleaned out. And given the size of that dinner we had, there's a lot of cleaning for some of you to do."

Finally, everyone chuckled.

"You will notice that there is a name written on the box of your enema." Everyone examined their enema box and began to look around the room. "That person is going to be your doctor. He or she is going to administer your enema. And here is the catch: three times. That's right. We want you to use the enema, refill it, use it again, and refill it and use it again, at least three times. That should clean you out sufficiently for the evening's play which will follow. Questions?" There were none. She picked up another box and began tossing rubber surgical gloves to all of us. "Well, okay, let's get going, then. Brad, you're my doctor, tonight."

"And you're my doctor," Melany said to Carol.

"Oh, can I watch?" Brad said.

"No, you can't. Well, maybe for a few minutes but, remember, someone will be waiting to administer your enema," Carol said. "Everyone, when you're ready to be the patient just step out onto the balcony and your doctor will find you."

I looked at my enema box and my doctor was Elaine, Chet's wife, the swimmer with the short blond hair. My fantasy girl of the group. I walked over to her and stuck out my hand and feigned a German accent. "Good evenink, Doctor Elaine. It is my pleasure to be meeting you."

She shook my hand and held up her enema to show me my name. "And it is like-vise, a choy to be meeting vis you this vine und lofely night." We both laughed and I held out my hand. "What are the odds we'd get each other's names?" She took my hand and we headed up the stairs to her room. "Whatever they are, I'm glad we did."

Once in the room we both got undressed. "So, who's first?" I asked.

She smiled shyly. "Uh, to tell you the truth, I've never done this before."

"By this do you mean giving or receiving?"

"Both."

"No kidding?"

She nodded. "Sorry. I guess you could say I'm a butt virgin."

I brushed off her concerns. "Not to worry. I'm a veteran of the enema game. My mother was one of those nut cases who believed that enemas were the secret of good health. From my 18th birthday on, every Saturday was enema night for her, my sister and me. Probably why I have an anal fetish."

"Who cares, why," she said. She went into the bathroom and came out with one of those huge bath sheet towels, folded it in half and laid it out on the bed. That done, she went to the bedside table, opened the drawer, and pulled out a tube of lube. "Anything else we need?" she asked.

I put on a pair of the blue gloves. "That should do it," I said.

She climbed onto the bed, pulled over a pillow and put her head on it with her cute little butt sticking up in the air. "Do your worst, doctor," she said.

I put a large gob of lube on my middle finger and rubbed it around her tight little butthole. I massaged around her rim, hoping that would relax her sphincter at least a little. I slid my middle finger into her ass and let it rest there. Her butthole tightened and then, after a few seconds I felt it relax. I slid my finger further in, up to my second knuckle and she moaned. He anus tightened again and relaxed again. Finally, when I thought she was sufficiently relaxed, I slid my finger all the way up as far as it could go and began to work it back and forth, in and out. When she began to rock back and forth in rhythm with my finger thrusts, I quickly slid my finger out and slid the enema in. She tightened a little but didn't seem to mind.

I squeezed the bottle and the liquid washed into her colon. "Wait, a minute," I said. "I have an idea." I picked up my enema, took it out of the box and replaced the one which was sticking out of her butt with the fresh one. I squeezed it and another bottle full of water was forced into her.

She moaned even louder, "Oh, God. I don't know if I can take it all."

"You're doing fine," I told her. "Just hold it as long as you can and then, when you feel like you can't hold it any more, just run into the bathroom and push it out." As I was talking, I reached under her and massaged her stomach and she moaned some more. I let my hand move up to her pussy which was soaking wet, and massaged her vulva as well.

"Okay," she said. "That's it. That's all I can take." She scooted off the bed and ran into the bathroom and I heard her evacuate her bowels. After a minute, I heard the toilet flush and the water in the sink running and she came out wiping her butt with a wet, warm washcloth.

"Again?" I asked.

She shrugged. "You're the doctor."

So, we did it again and this time she was more relaxed and even began to enjoy it. The anus has a lot of nerve endings and can be highly erogenous if we can just get over our hang-ups about it being "dirty" and taboo.

When she came out of the bathroom the second time she was washing her butt, again, with the washcloth. She smiled at me and pointed at the bed as she snapped on a pair of gloves. "Okay, mister. Now I'm the doctor. On the bed."

I got on the bed, head down and ass up, and had barely assumed the position when I felt her lubed finger slide into my ass and begin working back and forth and around my sphincter. I moaned and it must have shocked her. "Too rough?" she asked.

"Not for me but it might be for a butt virgin," I said.

"Good." I felt the enema nozzle enter my ass and the water being forced into me, then the second bottle. "Just so it doesn't leak out, don't you think I should plug the hole?" She said, playfully, and I felt her finger, no, her thumb, stretch my asshole. She began moving it about, massaging my sphincter and she noticed that I had a hardon. "Whoa? Is that supposed to happen?" she asked, taking it in her other hand and stroking it slowly.

"Usually does," was all I could manage to say. Then I had to evacuate and immediately. I told her and she backed away, letting me off the bed.

When I came back out of the bathroom she was waiting for me, smiling. "This is kinda fun," she said. "Do you and Jan do this?"

"Yeah," I said. "The thumb is a new twist, though. I'll have to tell her about that."

"Really? Wow, I've gone from butt virgin to butt sex innovator," she said, and giggled. Then she pointed at the bed. "Round two."

And so it went. This time, when I got the boner, though, I didn't let her stroke it for fear that I'd cum and I'd be done for the night. I could usually make two shots per session and, if I was really at the top of my game, maybe three over a three or four hour period, but I wasn't taking any chances.

We cleaned up the room and the bathroom, got back into our nighttime attire, kissed each other, and headed downstairs. We were the last ones to arrive and received a polite round of applause. Everyone else was drinking wine and beer and cocktails and eating snacks and talking and laughing, sharing their adventures in enema land and they invited us to tell our stories.

Elaine said, "Oh, my God. He got the biggest erection but he wouldn't let me touch it because he didn't want to go off too early. Now, is that self-discipline or what?"

Carol, always the leader, addressed the group. "How many of you experienced your first enema, tonight?" It took a couple of minutes but Bret, Melody, Elaine, Chet and Dick, more than half the group, raised their hands. "The verdict?" Carol asked.

There was some discussion but most agreed that, if it was done gently and patiently, as it had been done tonight, it might be something worth considering as a part of a couple's sexual repertoire.

"That's why I didn't want your spouse to be your doctor," she said. "I figured that if it was someone else they would be especially sweet and gentle whereas familiarity might lead y'all to be a little less careful with your spouse." We all agreed that she was probably right.

"Well," she said. "Now that we're all cleaned out and a little more comfortable with our buttholes being looked at and played with by someone other than our physician and our spouse, I guess we can proceed with the seminar. Jan? Kyle? Is that okay with you?

Jan held up her empty wine glass. "One more and I'll be more than ready," she said. Everyone agreed that one more drink would be just the thing.

______________________________________________

Jan stood before the seven of us and pointed to a medical poster showing an anus with all the various parts labeled.

"The word, anus, means ring or circle in Latin. It is, as you know, the external opening of the rectum. Two round muscles control the anus and keep it tightly closed unless it needs to be opened for evacuation purposes. These muscles are the internal anal sphincter and the external anal sphincter. The inner sphincter is involuntary and relaxes when you poop, whether you want it to or not. The outer is voluntary and is the one you, uh, pucker to keep something from escaping when you don't want it to.

"The anus has lots of nerve endings which make stimulation of that area pleasurable if it is done correctly, that is, gently and patiently. The pudendal nerve runs here," she pointed to the diagram, "and branches to supply nerve receptors to the external anal sphincter. It also branches to the dorsal nerve of the clitoris and the dorsal nerve of the penis. So, basically, you have one big nerve controlling your clit, or your dick, and your butthole. They're all connected.

"Because the sphincter muscles are basically designed to keep things in, they naturally contract whenever something - a finger, a dildo, a penis - tries to get in from the outside. As I said, however, the outer sphincter is a voluntary muscle and can be controlled with practice. And, while the Inner sphincter is an involuntary muscle it, too, can be controlled and taught to relax with lots of patience and practice.

"The best trick for making those muscles relax is to bear down and push out, like you do when you're pooping, when you want something to go in. This makes the sphincters both relax and expand easily. And explains why we all had enemas tonight."

Everyone exchanged knowing glances and giggles.

Jan went on. "It is possible for both men and women to derive pleasure from having their buttholes stimulated and/or penetrated, but it's usually men who initiate this activity as they are always searching for a newer and tighter hole to stick their boys into." The guys all bumped fists as the women rolled their eyes.

"And since you guys are the ones who are always pressuring us to do it anally, we've decided that you should go first. We fuck you in the ass and then you can fuck us in the ass. Sound good?"

The guys all looked around at each other and, given the reward we were being promised if we went along, we all agreed, some more enthusiastically than others.

"And, please let me make this one last thing perfectly clear," Jan said sternly, then she smiled. "Male anal stimulation is not exclusive to homosexuals. Straight guys have nerve endings in their butts, too. So, here's a rule to follow: If you like having your ass stimulated or penetrated by another guy, you're probably gay. If you like having your ass stimulated or penetrated by a girl with a dildo or whatever, you're probably straight. If you fantasize about fucking a girl in the butt, you're straight. If you fantasize about fucking a guy in the butt, your gay. There are always some rare exception to every rule, however, what with bisexuality and non-binary sexuality and all that, so please don't judge. Sex is complicated. Just enjoy it and let God do the judging. Thank you."

She curtseyed, and everyone gave her some polite applause. She sat down next to me and I gave her a kiss. I was proud of her. Talking in front of a group, even a group of friends who love you, can be a stressful experience, compounded when the topic is sex, and she had handled it perfectly.

Carol resumed her place at the front of the room and fielded questions for about 30 minutes, all but one of which were serious and respectful. Thanks, Brad.

"Well," Carol concluded when all the questions had been asked and answered, "Why don't we refill our drinks and then we'll get on with the demonstration? I think we can safely assume that everyone has received a hall pass for this weekend form their spouse, so we're going to proceed on that assumption, okay?" There were no objections. She looked at Jan and me, "Are you two still okay with this?"

Jan and I nodded. We were oaky but we were both a little nervous. We'd never done any of this with an audience.

___________________________________________

I was lying on my back on the floor on a sheet that was covering a comforter that was covering the big area rug in front of the fireplace. I was totally naked, and my legs were spread as far as they would go, my feet up on two chairs. There was a pillow under my ass, making me as exposed as I had ever been.

Initially, we had thought that Jan would do the prostate massage demonstration but, after talking, we decided that it would work better if she could walk around and point out things so we recruited a volunteer to do the actual massage. Melany's hand shot up first so Jan picked her to be my prostate partner.

"The prostate gland is about the size of a walnut and lies just above the penis on the front wall of the abdomen about two or three inches inside the anus. It supplies the liquid that comes out of the penis in ejaculation and provides the swimming medium for sperm except Kyle doesn't have any sperm because he got a vasectomy about twenty years ago, didn't you, sweetheart?"

"Yes, dear," I said. Everyone chuckled.

Jan went on. "A prostate massage can be pleasurable when done by itself but the pleasure is compounded when combined with stimulation - oral or manual - of the penis. Some couples manage, with practice, to even combine prostate stimulation simultaneously with intercourse - vaginal or anal - but I would not recommend anyone try that tonight. We don't want any dislocated joints or trips to the ER."

Everyone laughed a little uneasily.

"Now, Melany is going to demonstrate as I walk her through it. Ready, you two?"

"Yep. Yes."

'Okay, as always with butt play we begin with lube. Lots of lube. Remember, the anus does not produce any lube of its own so we have to supply it, ourselves. When you think you have enough lube, double it."

Melany squeezed a gob of lube onto her gloved fingers and spread it onto my butthole, slowly inserting her middle finger as she rubbed.

"If the man is amenable to it, you can often increase the sensations by using two fingers. How about it, Kyle? Are you amenable?"

"Oh, yeah. I'm amenable." I cold hardly talk, it felt so good. I had nearly forgotten that I was being watched by six horny adults but, oddly, when the fact came back to me, it was a turn on that I wasn't expecting. I could feel my dick getting hard as Melany inserted her middle and index fingers into my ass and began to massage my sphincters.

"Now, to find the prostate," Jan said to Melany, "just curl your fingers up in what we call a 'come hither' motion like when you're motioning for someone to come to you. You should be able to feel it."

Her fingers squeezed against my prostate and I moaned. "Oh, wow!"

"I found it!" Melany said, as though she had found her lost engagement diamond. "I found it! It's really easy, girls. It's right...there." She squeezed and I groaned again.

"Kyle's response is pretty common," Jan told the group. "That's often how you know you've found the prostate gland if you're not sure when you feel it." She took my erect penis in hand. "This is the other way, but not as fool proof. Some men get almost immediately hard when you stroke their prostate. Some men don't get hard or even lose their erection. Not to worry, however. It will come back." She stroked my dick as she talked and I started pumping my hips almost involuntarily. "Some men can actually even cum from prostate stimulation alone. Some men do sometimes and don't others. I, personally, believe it's a matter of foreplay and the amount of time between ejaculations. If he hasn't cum in a long time it's more likely he'll cum from prostate stimulation alone. And speaking of cum," she said and smiled down at me, "We don't want that to happen just yet." She stopped stroking, Melany stopped squeezing, and I groaned in frustration. "Let's get these chairs out of here and show them the other position for prostate stimulation, Kyle."

We moved the chairs and I got in the classic head down, ass up, doggy position with my head and chest resting on pillows and my butthole on display for everyone to see, my ball sack dangling between my legs.

Jan cupped my balls in her hand. "This position is my personal favorite because I like the view but, what can I say, I'm a perv. Isn't that right, Kyle?"

"She's a perv," I confirmed. "We're both pervs. Look at us right now. Total pervs."

Everyone laughed. I noticed that they were no longer seated in the furniture. They were all sitting on the floor, closer to us, so they could get a better view at what was about to happen.

"The goal is the same from this position," Jan said. "It's just the technique that changes and only a little. Of course, we begin, here as well, with lube. Melany, if you please?"

Melany squeezed a glob of lube onto my asshole and rubbed it around and in while I groaned as usual. What can I say? I'm a groaner and a moaner. I like to give feedback to my sexual partners. I felt her two fingers enter my anus and grope around for my prostate. The groping was almost as pleasurable as the massage, itself.

"The pleasure can be enhanced when toys are brought into play," Jan said. "A vibrator like this one can be especially helpful. You'll have to negotiate the size you want to use. Trial and error is both effective and fun. I suggest you start small and work you way up. I also suggest one like this one because of the ball end. It feels good going in and out and it helps in massaging the prostate. I felt Melany's fingers withdraw from my ass and the vibrator go in. She hesitated as the ball end pressed against my sphincter then gave a little extra shove and it popped into my rectum. It touched my prostate almost immediately and the vibration felt amazing. I felt my erection coming back.

"Girls, this position also allows you to massage both the prostate add the penis simultaneously from the side." She positioned Melany beside me on her knees. I looked back and saw that Melany had taken off her baby doll nighty and was wearing only a pair of thin, see through, lacy panties. Her breasts rubbed against my hip as she pumped the vibrator in and out of my ass and reached around with her left hand and began stroking my member.

This time it didn't take long. I said, "I'm going to cum," and Jan told me to roll over onto my back so everyone would have a better view. Melany was getting into it, now, and she pumped my ass even harder and faster while Jan stroked my cock faster and faster and my hips pumped along with her.

Finally, mercifully, I blew with a loud moan. My first shot of cum landed all the way up on my chest, between my nipples. The second just above my navel. The rest in a puddle on my lower abdomen. I had not shot that hard or that much for a long time. It was amazing and I wasn't the only one who thought so.