Emancipation Ch. 09: Anal Lesson

"Ummm, what part? Where you scrape the skin off my back and feet? Or something to do with my holes?"

"Definitely the holes, but I'll service your back and feet too." [180] Lois did a thorough job on my feet and hairy back. She said she was anxious to toy with [181] my butthole. "To me, hair always meant 'dirty', so I always hated hairy men, yet I like running my hands over yours. [182] I didn't realize you were so pileous or calipygous... look it up so I can be the teacher for a moment! I'll wash this sweet hairy rump, but then what do I do?"

"Show off! Anybody know what those words mean or can look them up? I'd like to know if I was just insulted! Well! Brace yourself, I'm going into teaching mode! Of course, this is mostly my personal opinion, YMMV. If you use soap in my crack, flush it all clear. Start with a wet cloth in my butt crack. Hold the bottom from the front, under my balls, the top against my back. Gently pull the cloth into my crack and forward. Reverse when you reach bottom, adding a little more pressure. Keep the full thrust drag slow. Repeat until you feel the drag make you start/stop then maintain that pressure and repeat several more times.

"Now drop the cloth and take a close look at my asshole. Check for redness, friction burns, bleeding and distended sphincter. Lube a finger in your mouth, leave lots of spit on it and push it against the hole muscle to gently spread the spit over all of it, especially if you saw a problem." [182]

"Did you do all that for me? I wasn't aware of it."

"You weren't supposed to be. I wanted you to just feel the pleasure while I watched for your safety. Next time you do this to me or Joe, or Sue, you'll need very little direction. By your fourth time, it will be obvious what to do."

"I don't want to do this to anyone else [183] until I'm sure it's safe. So I guess you have three more ass invasions to go."

"Son of a bitch!!!!" Joe again. It seems these acts were uhmmm... unexpected?

"Hon, why didn't you train me with these tips?"

"I wanted to, Sue, but you resisted or were never ready. I'm happy to train you whenever you are ready, though I don't think you eed any basics. Don't pout. I love you. Isn't that an odd thing to say as another woman is fingering my ass while you watch? Hmmmm! OK, Lois, once lubed, use the long stokes again, then check again. Keep an eye on my reactions too. Just check if it's hurting or fun for your victim, ummm me. You should build to a strong, lustful reaction. Before I peak, check and lube the hole again. This time use the whole side of your finger to roll over the muscle, wetting and rubbing it.

"Now you can start the 'shoeshine' strokes. Get the cloth deep into my crack and pull it snugly against my hole. Carefully pull it up an inch and quickly reverse. Limit the strokes to an inch each way. Do that for half a minute, but keep an eye out for any signs of pain. Check for damage, lube and repeat. It takes earned trust to allow that muscle be pulled in and out and feel the pleasure, so don't expect a strong reaction your first two times trying this."

"I'm glad you told me all this after my initiation, but now I'm afraid I'll hurt you."

"I trust you to watch out for me and stop at any sign of pain or BLOOD, or I wouldn't have let you get this far."

"Wow! Now I'M flattered."

"In the showerless world, you'll probably need a better lube than spit. Don't use Vaseline or hand lotions if you use a condom. KY is still the best choice. You can still start with a dry cloth, or just a dry finger. But don't push too hard until you've well lubed the area and your probes. Once you have the feel, you'll mix up the order, pressure and styles.

"What I'm showing you now is a gentle introduction. You may want to be more direct or aggressive later. Remember you want to continue trust and INFLICT pleasure. Soon you'll be a great butt pirate and ass kisser! If you're ready, you can move on to pushing fingers inside starting with your smallest during your training."

"OK, [184] but slowly, this is all new to me."

Joe piped up, "OK? What does she mean OK? Son of a BITCH!!!!!"

"Keep using the shoeshine until either I start breathing heavy, I'm hurt, or you feel I'm not going any further. Ummmm, I forgot to check you since I never expected to get this far, so check your cuticles and nails now for sharp spots. They'll make blood spurt and you don't want to see that. Me neither! Soak your pinky in lube, push the pad of the first joint against the bottom of my hole, slowly rotate the finger and apply as little pressure as it takes to breech the fortress. Don't force it too hard or fight a clenched muscle. If the asshole won't relax and open a little, let it go for another time. If everything's clean and relaxed, you can also apply spit directly and use your tongue to lick and try to enter the anus. The heat and intimacy of a warm tongue can encourage relaxing and NOT relaxing! I so look forward to feeling that from you."

"My tongue? Yeah, right! Really? Last week that suggestion would have made me violently sick. Somehow, I'm looking forward to shoving my finger up your ass... eeeeek! But I'm not sure I'm ready to do that, forget licking your butthole. So, you used your spit on me too. Again, I'm not sickened, but oddly pleased. I feel another kind of truly intimate connection now thinking about your spit and mouth on and in my rectum."

"With experience, you'll try pushing a little more with more lube. When your pinky slips in, the muscle will probably grab it tightly. Just pause until it loosens again. Don't force it in or out. As it relaxes, you can slide the finger in more. There isn't much feeling inside, so the bulk of the pleasure comes from the muscle rolling over itself. Slight friction rubs many nerves and that's your goal. You'll know you're doing it right when I'm not able to give you directions. Pump slow or fast according to my reactions until the muscle relaxes too much to hold that finger snugly. Then you can escalate up to more, or bigger, fingers. We'll talk later about other things people shove up there, but I doubt we'll get to butt plugs, anal beads or other toys too soon."

Sounding worried Lois asked, "Did you get to a second finger in me?"

"No, you weren't ready. I did replace my pinky with my ring finger for a minute and you didn't notice. We'll get there another time unless you want this to be your last asshole experience."

"Joe, close your ears. I don't believe I'm saying this... HELL NO. I want more of this too." [185]

"Oh, fuck... me!"

In stereo from Sue and Lois, "Later dear!"

"Wow again. Lois, you keep astonishing me, us, not only with the huge turnabout from the prude you were, but with the enthusiasm you have to try these 'unthinkable' things. If you keep going like this, I'm going to make a certifiable pervert out of you yet! Hey Joe, how do you rate your beautiful and sexy wife now?"

"Ummm, 90!" Lois used the cloth well, got some good strong reactions and incredibly began fingering me. [186] I could tell she was afraid since she was so hesitant and gentle, yet I felt her pinky pressure inside. She stepped up the pumping when I asked and brought me closer to climax than expected. I lost focus and speech! When the friction began to burn, I had her stop.

"I'm so sorry. Did I go too far? I want to know what that '90' is about. Are you hurt?"

"No, I'm fine. That '90' is a rating I asked Joe about before you started your brave trek. It's up from 10 then and tells you how far Joe thinks you've come. Take a close look at my round muscle. What do you see?"

Lois washed my hole again and put her face amazingly close to my asshole. "It looks a little sore, but there's no blood and the puckers and the hole itself are loose and relaxed. Given how tender that tissue seems to be, it looks fine." She held my cheeks spread widely then, as gently and lightly as possible she kissed my sphincter then soaped her hands and lips.

"Did you just kiss my butthole? OMG! Overall Lois, an excellent advance, you earned another gold star, and two more for the kiss! The redness happens when there isn't enough lube for the stimulation. It burns a little, but feels great. The histamines, I think. I am so impressed with you. You take my breath away!" She turned me and warmly rubbed my dick again, gave me her beguiling bright smile and a lingering wet kiss before we left the shower. "She KISSED it! WOW!"

"Yes, I did. I just HAD to kiss it. It was as clean as it can ever be, so it was now or still never. I didn't ENJOY it, but I wasn't disgusted either. THAT was hard!"

Lois and I dried each other off and watched our mates step into the shower. Of course, we played a bit more while drying. "Your nipple has a 'smudge' on it. Let me lift this squeezable, silky mound of delights to my gluttonous mouth and lick it clean for you." I pursed my lips around a spiking, pebbled knot and its halo. With my varying suction, my starved tongue lapped at the tasty red tip until her other nipple hardened too and we both moaned. "Was that too much silly banter?"

"Dopey, but appropriate. Such a now minor thing on my formerly hated tits feels exquisite." Lois gently squeezed my dry cock and again could not get under the foreskin. Pearls of pre-cum already coated my GLANS. Lois happily licked the sweet drops and milked for more.

"I can't get enough of you, sweets." I moved one, two then three fingers into her swollen and well moistened honeypot. "Just checking your wetness, and getting a snack. Your sweet, hot puss is just too hard to resist, but I don't want to arouse you again right now since we should watch our mates perform. You do know that I thoroughly washed all fingers before putting any back in here?"

"Of course I know. I trust you to do that, and THAT's UNHEARD OF. I agree and I want to watch what they do also. My germ phobia hasn't gone away, it just doesn't apply in every case it used to. Isn't that something?"

Joe mimicked what I did and confirmed the surprise of the sweet tasting water off Sue's nipples and pussy. He soaped her well and focused extra long on Sue's tiny tits and big nipples. Joe gave her downy brown bush some extra attention too, rinsed off her pussy and sucked her clit. She pretended not to notice his affections and kept soaping her hair, so he lifted a leg and spread her lips open for a peek inside. Two fingers pushed inside her, dragged on her clit and made her cunt deliciously slippery. Her twitching betrayed that she could not ignore the stimulations. Joe flicked his tongue against, then inside my wife's pouting pussy.

"I know all too well just how sweet her wet bush tastes. The surprise was how different your denser and coarser plumage tastes despite your being sisters. What a great fantasy survey this would make for a statistics class! We can start with 1000 naked women, flush their bushes and do a taste test. Wanna help with a second opinion, Lois? Extra credit for titty tastes?" Lois gave me a scornful look, yet her eyes twinkled at the possibility.

Before turning her, Joe pushed as many fingers into my wife as he could fit. He got to four before she shuddered in a mini orgasm. He slowly wiped her pussy again, kissed her clit and sucked his nectar laden fingers clean. Joe scrubbed Sue's back, pits, legs and ass. She bent over and offered him her asshole. Knowing that she had some ass experience, he started with a wet index finger against her sphincter. "Lois, watch closely." After a few seconds of rotating his wet finger around her sphincter, he pressed it against her hole. Sue relaxed it and his finger easily popped inside. Lois was surprised at how quickly and painlessly his big finger entered her sister.

"Didn't you say her asshole was small like mine? How did he do that?"

"Sue's hole closes as tightly as yours, but her experience lets her loosen her hole faster and wider than you can... so far. If it loses tone, she'll need bigger and coarser stimulation to keep the same intensity." Joe pushed a second, unlubed, finger into her and ramped up his pumping. He was grinning broadly. He's seen all Sue has to show, much more than he ever dared fantasize, so why shouldn't he be happy? Sue slowly approached orgasm, but couldn't quite reach it until he used his thumb to tap her clit. Then she shuddered uncontrollably for just a moment then let out a long low growl of pleasure.

Sue quickly but completely washed every bit of Joe's body, especially his stiffening joint. She tasted the water off his nipples, then tried it under his balls and pecker. She later agreed that the water tasted sweeter off his cock too. Sue studied his dick closely in the bright light, said nothing. Her hot box had earlier aroused him so much that, with some gentle squeezing of his boys, she sucked him to climax in seconds and swallowed his swimmers. She sampled his second burst of cum with a mouthful of water and said even that tasted different. Once licked clean, she turned his back to her and rubbed him head to toes. When he bent over, Sue pressed a lubed finger easily into his ass. "Joe, who's been pounding your ass? It looks and feels pretty lose."

"Ooops! I was afraid you could tell. I have, hon. That was one of my dark secrets. I use my fingers and some bigger things. My own anal toys have often visited back there. But I didn't bring any with me. Surprised? Now you all know." Sue easily moved two fingers deeper into his ass then massaged a third inside. He was groaning already and declined a fourth.

We were all surprised. "You never told me about that. Why?"

"Because you would have called me a pervert and thrown me in the doghouse again. Now I can show them to you and how I like them used. Isn't that incredible?"

Lois and I smirked, both thinking that will be handy to know later when we decide what to push up his ass during lunch. After working the three fingers in as far as her knuckles, Sue called to her sister to watch. "Lois, have you ever seen a prostate enhanced climax?"

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