Couples Teaching Couples Again

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You show your friends the joys of anal sex.
3.9k words
4.25
42.9k
9

Part 2 of the 2 part series

Updated 10/10/2022
Created 01/22/2005
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It's the week of spring break, and the weather is beautiful. Your old college friends Eric and Kathy have invited us over for the day, to catch up on things. Well, I shouldn't say they're just your friends. After all, the last time we visited them, I got to teach Kathy how good cunnilingus felt, while you showed Eric how good a blowjob could be. I think we all thoroughly enjoyed that visit, but it's been a while since we've heard from them. We thought they might be a little weirded out, so we'll take today as it comes.

We've all eaten lunch, and passed the time playing cards and talking. Gradually we got less interested in cards and more in talking, and somehow the conversation turned towards sex.

"So, were we able to help you guys any last time we were here?" I ask, wanting to see if they'll be cautious about the experience.

They smile at each other. Eric speaks. "Well, the next day we were really weirded out. I mean, we practically had sex with you guys. We didn't know what to say to you, which is why you didn't hear back from us for so long. But the past few months have been just, like, amazing for us. You really did help us out a lot. And looking back, we really did both enjoy it very much."

Kathy picks up. "I don't know if it's wrong of us to ask, but is there anything else you might be able to teach us?" You are somewhat surprised by her forwardness. "I mean, it's not like we're having any problems now, but things can always get better. And I don't know why it is, but when I think about that day, and imagine the possibility of something like that happening again..." Here she falters, and does start to blush. "It-it kinda turns me on." You glance at her chest, and see that she is indeed telling the truth.

I smile. "Well, I know that we enjoyed it, and it definitely turned us on. Now, if this is something that both of you would like, we wouldn't mind doing a little semi-regular 'teaching nights'. And maybe some 'wife-swapping' mixed in with that. But we would have to lay down a few ground rules." They nod, interested in spite of themselves. "First, no penis-in-vagina intercourse with the other's partner. That's something we reserve for our own marriage bed. Second, if at any time anyone is uncomfortable with anything, simply say stop and that will be the end of it until we discuss more. This applies to both actual activities and general emotions.

"Now I know I love my wife, and I know you love yours, and I think we can handle a little fun without getting jealous. But if anyone, at any time, doesn't think they can handle it then that is perfectly fine. And there will always be communication, first and foremost. Do you think we can handle that?"

You and I start to step out of the room, to let them discuss it. But Eric stops us and says, "Wait. We, er, already kinda discussed this a few times. And you guys basically just stated the rules we would have stated. So, I think, we're in." We go over to them, and shake their hands. Then I embrace Kathy, as you embrace Eric.

"So," Kathy asks, with a bit of a hungry gleam in her eye, "what can you guys teach us today?" You can see her nipples, hard, poking through her tshirt. She's wearing a bra, you're certain, but you remember how good she looked naked, and how big her nipples are. You wonder if you might ever get to play with them...

I return to my professor-mode. "Well, we've already helped you out with oral sex. Have you guys ever thought about, or tried, anal sex"?

Eric's eyes perk up, but Kathy's jaw drops. "Oh my gosh! Doesn't that HURT? And it's gross...Ew!"

"Actually, no," you smile at her. "It's really not that gross at all, no more than any other sex. And if you're worried, there are ways to make it cleaner. And if you do it right, and slowly, not only does it not hurt, but it feels absolutely amazing. Mmmmmmm," you shiver in delight at the memories. "And the guys love it, because it's so tight back there. Isn't that right?"

I smile at the memories as well. "Looks like Eric wants to see what it's like," I mention, referring to the grin he is now wearing. "Shall we retire to the bedroom?" I pick up your bookbag as we head back there, knowing what we had packed in case of this eventuality.

We all arrive, and you start seductively stripping your clothes. Eric stares at you, while Kathy quickly turns away, looking at me with a questioning face. I explain, "I think that the best way to go about this will be to let Eric fuck my wife first. She's used to it, so it will be easier. You can see how enjoyable it is, and then we can show you how enjoyable it is." You have now discarded your shirt to reveal a very skimpy black bra, a kind of mesh that we can see the nipples through if we look carefully. Eric has his arms around Kathy, but his eyes are locked on you. Kathy is now observing also, still looking a little embarrassed, but also curious.

You shimmy out of your jeans, revealing that you are wearing underwear this time, but only barely: a piece of string that covers basically nothing. It's very easy to see the treat that Eric will be enjoying soon, and both of us guys gaze lustfully at you as you wiggle that hot ass. You glance over your shoulder seductively, "accidentally" looking right at Kathy as you untie the string and let it drop. Now naked, you crawl up onto the bed in a doggie-style position.

I tell Kathy to undress Eric. She does, pulling off his tshirt and tossing it aside, then undoing and pulling down his jeans and undergarments. Looking at his erection, happy to be looking somewhere other than at your naked form, she remarks, "Whoa there big boy, looking forward to this, are we?"

"Well, aren't you?" he replies, glancing away from your rear for a moment.

"I don't know...yeah, I guess I am. It just seems so...weird that a girl could enjoy that."

I chuckle. "Watch and learn. Because enjoy it she most definitely will." I reach down into the bag and pull out a box of condoms. They're a larger size, and should fit both myself and Eric comfortably. I explain, "Now, these are nice to use during this activity, especially for your first time. It can, and often does, get a little messy. If you're wearing one of these, you can simply dispose of it afterwards and then you're ready for anything. If you go 'bareback', you will want to shower almost immediately afterwards, and definitely before you do anything more with it in her body." I pull one out and toss it to Kathy. "Go ahead and put it on him."

She fumbles a bit, then takes it out of the wrapper and clumsily puts it on. Meanwhile, you are on the bed with your knees apart, totally exposing your ass and your pussy. Your fingers are sloshing in and out of yourself, very clearly wet. I reach into the bag and pull out a tube of lube.

"Now, lubrication is very, very important. As we can see, the female body usually provides quite a bit herself. But there is never, never too much. Too little can hurt. So in addition to her own natural juices," and at this you bring your dripping fingers up to your ass, "we'll also use some store-bought lube. This is K-Y Jelly, a pretty popular brand. You can also buy the generic Wal-Mart brand for a couple bucks a tube, or go to a sex shop and get some really good stuff. Astroglide is some of the best, but it's a little more pricey than this. You guys can experiment with what you like best.

"Now, Kathy, go ahead and put this all over Eric's cock. Pretend like you're giving him a handjob." While she's doing this, you have your hand between your legs, rubbing your juices all around your asshole. You slide your finger inside, getting yourself ready. You can see Eric's thick cock, and you can't wait to feel it inside you. You've never had another guy in you like this, and you're very curious. His 7" cock won't reach as deep as my nine inches, but since it's thicker around you imagine it will give you more of a filled sensation. You are moaning softly in anticipation.

Eric, his cock all lubed up and quite erect, comes over behind you. You reach back and grab your cheeks, opening them wide to display your waiting rosebud. "Now even though she's very ready for it, Eric, you have to go slowly. Start off by sliding your finger inside her, first one and then two. You'll see how tight she is." He does this, his one finger sliding in just as smoothly as butter, and the second one as well. You feel the sensation of the unfamiliar fingers, and you give them a little squeeze to show what his cock has waiting for it. He grunts in pleasure, and starts sliding his fingers in and out, slowly assfucking you with them.

"OK, Eric, I think she's ready. Go slow, be careful, and let her do most of the work." He removes his fingers, and you feel the head of his dick sliding along your crack. You spread your cheeks, and relax the muscles, opening yourself up for him. You feel him reach the right spot, and slowly, slowly push forward. You get the familiar stretching sensation, and the head of his cock is inside you. He stops there, courteously.

"You only want to go in maybe an inch, at most, at a time. And then stop, and let her adjust to the intruder in her body. You have to spend a lot of time, but believe me, it's worth it." Kathy and I are both staring intently at the scene that is unfolding before us. I am enjoying watching you be penetrated by a different dick, filling you in ways that I cannot. And at your obvious enjoyment of it. Kathy is amazed by your enjoyment, and that Eric is fitting inside there. And slowly but surely, inch by inch, his cock is fully inside you. You feel his balls resting against your pussy and you moan.

"Now, once she has adjusted to the full amount of your cock inside her, only then can you start to thrust." And, a little too eagerly, he starts doing so. You experience a moment of pain, then quickly adjust and enjoy it. His cock is filling you up, stretching you out. His balls are slapping against your cunt with every thrust, your breasts swaying underneath you.

"Now, before Eric blows his load here, there is something that I want to try. If you have two guys and one girl, you can do something called 'double-penetration', which as it sounds is a cock in each hole." I am pulling off my shirt as I say this. "We've never done this before, but it's supposed to be an intense feeling." My pants and boxers fall to the floor, revealing my quite erect 9" cock. Kathy gasps, having never seen mine or anyone else's penis before other than Eric.

I slide on the bed underneath you, my cock sticking up into the air. You clench your rear muscles, holding Eric in place, and move your body over mine until you slide your wet pussy down over my cock. I slip inside you, your pussy even tighter than usual, feeling the strange object through the wall of flesh. I kiss you passionately, and we all start fucking.

Eric and I quickly get a rhythm going, and soon all three of us are moaning in time. It doesn't take long at all before Eric can't handle any more, and we can both feel him exploding into his condom in your ass. The feeling causes you to orgasm, and your clenching cunt makes me cum as well. We all kind of collapse onto one another, temporarily exhausted.

But Kathy is still dressed, and now quite horny. Eric pulls out of you, and peels off the dirty condom, throwing it away. We separate, and I ask Kathy if she's ready to try yet. She nods, and tries to imitate your strip show. She's not nearly as good at it as you are, but she does have an amazing body being revealed, almost as good as yours. She removes her shirt to reveal a lacy red bra, a vast improvement over her white cotton of the previous time. Sliding it off, she once again reveals her small breasts with their incongruously large nipples. She cups them, enjoying the admiration, and doesn't seem to notice that you are admiring as well.

She then slides off her jeans to reveal a nice red thong, matching her discarded bra and tight enough to show the outline of her cameltoe lips. As she removes them as well, we get another surprise - her lips no longer have the light golden blonde hair. Instead, they are as bare as yours. She smiles, no longer ashamed of her naked body being displayed, and says "You were right, this does feel very sexy! I like it, no, WE like it a lot!" She winks, and then comes over to sit on the bed. Her nipples are hard, and her bald pussy is glistening.

"What now? It doesn't look like either of you two guys are going to be able to fuck me like that," she remarks, looking at our spent cocks. I smile inwardly at her unhesitating use of the language, and tell her, "Well, you're going to help with that. I'm going to lay here on the bed, with you on top of me in a 69. You'll use your new skills to get me hard again, while I use my tongue to get you wet and ready. Deal?"

She nods eagerly, and crawls over to throw her leg across my face. I get a good look at her wonderful pussy, before it covers my field of vision. My tongue comes out to taste her juices, and I remember how good she tastes. Not as good as you, but quite enjoyable. Someday you'll have to try it...

I then feel her tongue on my limp dick, and realize that she's definitely been practicing. She swirls her tongue all over my head, and then takes the entire limp thing into her mouth. "Mmmm, this tastes really good. It's not quite like Eric's cock, it's more like-" She stops, blushing furiously as she realizes what she is tasting. Your pussy juices, smeared all over my cock as I was fucking you.

You giggle and tell her, "It's OK to like the taste. I like the taste of myself quite a bit actually. I'll take it as a compliment." Kathy stutters, and moves her mouth back onto my penis before she can say anything embarrassing. She does seem to enjoy it, though, and takes great pleasure in licking me all over.

She knows just the right spots to hit, and my tongue probes her in return. With a few judiciously places tongue caresses, she's loudly coming on my face, but not staying away from my cock for too long. It is quickly coming back to life.

After she comes a few more times, and her body is more relaxed, I start changing my focus. My tongue is now exploring her rear, and dipping to rim her asshole a few times. From the muffled moans she is making around my cock, she must be enjoying it. I reach my hand around, dab some of her juice on it, and slide my finger into her asshole slowly. She stiffens at first, but then relaxes and lets it enter. I give it the time it needs, and then stretch my middle finger to lubricate it as well. Sliding the first in and out slowly, I join the second with it and the both enter. Again the stiffening, and the relaxing.

By now my cock is quite hard again, and she is losing her ability to concentrate on it. I slide out from under her, my fingers still in her ass, her still on her knees facing out. I get behind her, and you are already waiting for me with the lube and a condom. You slip the condom on easily, and start rubbing down my cock, teasingly slowly so as to not get me off yet. Meanwhile, with my fingers I am lubing up both the outside and the inside of her ass. I ask her how it feels, and she only moans in ecstasy.

My fingers are giving her orgasms, and she is loving it. When I remove them, she continues to shake, starting to come down from her high. She then feels my cock against her ass, and she tenses up.

"It's OK, it's OK. I'm only going to go as fast as you can handle. Eric, play with her boobs there to distract her some." He does, and she starts to relax again. I press my dick into her crack again, holding her cheeks to the side with my hands, and slowly, slowly press inward. Centimeter by centimeter, the head goes in and I stop. I ask her how it feels.

"Oh, gosh, it's almost like it hurts, but it's a really really really good kind of pain. I want more, but very carefully."

"Of course." As she relaxes, I slide a little further inside her, gliding fairly easily along all the lube we put there. Every time she tenses, I pause and let her relax, never going too fast to hurt her. It takes an interminably long time, and while I'm working at this, you decide to perk Eric up with a little blowjob. You use your skills, honed by all our time together, to get him rock hard but not allow him to come. His eyes are glued on his wife's ass, where my long cock is now just about all the way in.

A little more, a little more, a little more, and then I am inside Kathy to the hilt. Her cheeks are pressed to my thighs, her mouth open in a mixture of pain and pleasure. I wait, allow her to relax, then slowly start moving my hips back and forth, fucking her very lightly. I do this a couple of times, until she is used to my cock moving inside of her, and then I come almost all the way out and suddenly thrust in hard. She lets out a huge scream, and comes extremely hard. Her ass clenches my dick inside, her body spasming. I continue thrusting inside her, not as powerfully as the first one, but continuous hard fucking. She keeps coming, cresting wave after wave of pleasure.

I'm getting close to coming, and she's had more orgasms than I can count, so I slow down and just hold myself in place inside her. Her body keeps spasming, racked with pleasure, and I sit back on the bed, pulling her into my lap. Keeping myself deep inside her, I scoot forward to the edge of the bed. I lay back, with her sitting on my cock facing away from me, a reverse cowgirl position.

You give Eric's cock one last lingering kiss, before you get up and come over to me. You straddle my face, looking towards Kathy's back. I start licking at you, loving the sensation of one gorgeous woman's cunt on my face, and another gorgeous woman's ass on my cock. I hold Kathy's hips, rocking her on me. You reach out in front of you, and put your hands on Kathy's chest, cupping her tits from behind.

She's still on a high, and it takes her a few moments before she realizes that there are two pairs of hands on her. She looks back over her shoulder nervously, to see you smiling at her. "It's OK, Kathy. You have amazing breasts, and I just wanted to feel what they are like. Just enjoy it, Eric seems to be enjoying the sight." She turns her head to see Eric in front of her, gazing down lustfully at his wife. She is sitting on another man's cock, with another hot woman fondling her tits, and her pussy is wide open, wet, and waiting. He is erect and knows exactly what to do.

With one thrust he is inside Kathy, and we can all feel her orgasm. She is screaming again, clenching both of our cocks, and the feeling is similar to when we were double-penetrating you. The four of us are on the bed in a sweaty mess of fucking flesh, me laying on my back, you sitting on my face, Kathy leaning back onto your chest while your hands are on her tits, and Eric and I double-penetrating her. Kathy is coming repeatedly and loudly, and Eric can't take it for very long. Already worked up by your oral skills, and now by his wife's tight pussy, he comes hard into her.

All the action between her legs had brought me to the edge as well, and I finally let myself go. I explode into the condom, my first time "coming inside" anyone other than you. I moan into your pussy, my tongue on your clit. That sensation, and the feeling of your good friend Kathy's large, hard nipples under your fingers makes you come as well, orgasming all over my face. That, of course, makes me thrust harder into Kathy, making her come stronger, and squeezing a little more out of Eric as well. We then all collapse in a pile of flesh on the bed.

I remove myself from Kathy's ass, making her squeal one last time as the pressure is relieved, then throwing away the full and dirty condom. I embrace your naked body, utterly worn out from a whole afternoon and evening of fucking. Eric and Kathy embrace as well as she finally comes down off her high, and we all smile at each other.

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