Ron's POV

That evening Neville and Dean stopped by, thank goodness Harry and Seamus were stuck in night laps. We had a lot of fun watching the game, had a few beers and chatted. I was distracted, the plug in my butt reminding me I had to complete the challenge. "Guys, Hermione and I have become more adventurous when it comes to sex."

"That's usually the opposite of what happens, isn't it?" asked Neville.

"Adventurous how?" asked Dean.

"Have any of you ever done anal sex?".

"Actually, I tried it with Hannah last month after your party," Neville said.

"How is it? Hermione and I are going to try this weekend and I want to make sure it goes well. Do you have any advice?

Neville said: "I advise you not to just try to switch holes when you're both drunk"

Dean finally said "I hate this misogynistic shit. You know when it comes to anal sex they sometimes call it painful when you watch porn and guys treat the woman like some kind of sperm container and it's like hurting her, it's part of the arousal. Yet if you browse, people can have orgasms from anal stimulation. Who's going to have an orgasm while getting hurt? Well, that's a whole different matter. Sorry." He waved his beer and slumped back in his chair, like he was sorry to have to fuss and make a speech.

"No no no. You're right,' I said, waving my beer like cheers. So we all took a sip. "So any additional assistance?"

"Get her in the mood, relax her, make her feel good, make sure she's loose and lubed up. Anything you would do before you fuck her pussy, you can do with her ass before you fuck her there."

Neville said: "I'm sorry to think of your wife like that, but Hermione has a great butt. He then turned to Dean, "That's part of what I did wrong with Hannah. So I guess you don't just stick your dick in there either. You could start with something else, like a finger, and work your way up to it over several sessions."

"You could try talking to her about it before touching her there again, and then slowly." That's when I told them about the plugs.

"Wait!?" asked Neville, amazed.

"The prostate, man. I've heard that getting the prostate stimulated is really something. Hermione wants to do it and I figured fair is fair."

Dean nodded his head. "You know, we don't do anal a lot because it's a big production. Regular sex will get you there with a lot less effort. But maybe we'll try fingers." A little later, Hermione came home.

The light in her cheeks, the light in her eyes, her half-open mouth and the firmness of her nipples moving beneath her thin top told me immediately that she was excited about what was happening during the evening. The guys saw it too and reacted. The room was filled with sexual excitement.

They got up to greet her, but I think they got up a little too - in their pants.

She came over to me, hugged me, kissed me, held it a little longer than the usual public greeting. Then she did something similar for each of them, a little more intimate than in the past, the kind of hug and kiss that would make a jealous wife or girlfriend wonder at the slut turning on her man.

I was sitting in a chair, Dean and Neville at the ends of the couch. As we sat down again, Hermione stepped between them. "What have you guys been up to?" She asked. She gave me a knowing look, a tiny smile, and a tiny nod.

I gave the answer she wanted: "We talked about anal sex."

She was giggling, her neck and face flushed and her head bowed, all the signs that she was about to say or do something that both embarrassed and aroused her. "Did I come home a little early? Did you want to stick your penises in each other's butts?"

"The only butt around here that gets a penis in is yours."

"Have you all been talking about fucking MY butt?" She turned, rested her head on Dean's shoulder and looked into his eyes. Her hand fell into his lap. Her hand lightly brushed his visibly hardening cock. "That sounds like fun, Dean, but what would Cathy say?" Before he could say anything, she turned to Neville. She managed to get her butt pressed against Dean's side. One hand rested on Neville's shoulder, the other was kept still on HIS cock. "Isn't it going well with Hannah, Neville?" She quickly leaned back again. She looked at me, one hand now resting in each of their thighs. "You probably want to watch your friends fuck my butt, don't you? Please don't make me take someone else's cock up my ass – I like it better that your big cock burst my anal cherry." She jumped off the couch and sat on the arm of my chair. "I'm sorry for teasing you. It's not fair." We all stared at her. "See, it's just a challenge. We're not virgins in our ass."

"What got into you tonight?" I asked her.

"Four margaritas and that big plug you stuck up my butt this morning," she replied. "Did you tell them about the plugs?"

"I did."

"Do you want to see?"

Dean said, "I think we'd better go." Neville looked disappointed at what Dean had said.

Hermione said, "Relax, folks. I'm not trying to tempt you, I'm just trying to tease you." She looked at me. "Can't we show them before they go?"

"Well, okay."

"Awesome!" She jumped off the back of the chair, leaned in to kiss me, then went back to the boys on the couch. "You go first."

"What!"

"Show us your butt and butt plug."

"Hermione, these guys don't want to look at my butt."

"But I do, and then I want you all to look at mine." She said tipsy.

So I dropped my pants and leaned against the chair for a good view. Then I pulled up my pants and sat down. Hermione moved across the room and into the same position, her hands on the arms of the chair on either side of me. With her face inches away from mine, she said, "Pull up my smock master and show your friends the plug you put up my ass if you want."

I wanted and I did. It was incredibly arousing and my cock was rock hard. But then we had no choice but to Apparate the boys away, knowing that as soon as they walked out the door we would have sex.

When they were gone and we were in the bedroom we separated from each other like we had every night this week, I took her to the bathroom to clean her up for tomorrow.

Hermione begged me, "I'm ready and I want it so bad, honey! Can we do it tonight?"

I played dumb. "What should I do?'

She grabbed the sides of my head and hissed inches away, "I-want-your-dick-in-my-asshole!"

"I love that you are so eager and that you loosen up on how you talk and who you talk dirty to, but not until tomorrow. But let me lick your asshole."

We went into a 69 position but curled up tight so our asses slapped each other in the face. I licked Hermione's ass crack, running my tongue around the hole, pressing down on the rubbery muscle and feeling it tighten more easily than it had a week ago, so I dug my tongue into the hot center of her ass.

She did the same to me, then moved her head to take my scrotum in her mouth, sucking and licking each ball eagerly and thoroughly.

When she started licking the shaft of my cock, I shifted my attention as well. I ran my tongue from her asshole over the blemish to the wide wet lips of her pussy. My chin pressed against the mound above her clit.

Soon she started rocking against me. I slapped my tongue across her silky, soaked slit, then curled up and plunged her inside. She took the flesh of my glans in her mouth, sucked and licked like eggs.

I pulled my face out of her pussy to suggest, "Stick a finger up my asshole and I'll do the same to you."

Her finger slipped through the ring and worked its way to my prostate. I shoved a finger deep inside her, then Kork screwed it in there. Encouraged by her panting and faster breathing, I sucked on her clit and added a second finger. Soon she was gasping and squirming. My forgotten cock lay unattended as she rocked and rolled through a series of powerful orgasms.

When she was done, she pulled her pussy away from my mouth. I still rested both fingers in her asshole. She reclaimed my cock, sucking hard and driving it deep down her throat. Our training sessions have paid off. The spasm of her throat around my cock and her fingers digging into my ass brought me to a violent orgasm of my own. She swallowed it all and then gently held my shrinking cock in her mouth.

We were in a 69, heads on each other's thighs, fingers in each other's asses. After a few moments I realized the margaritas had taken their toll and she had fallen asleep. Without moving, I dozed off myself.

The next day was the longest work day in history. When he picked up Hermione from her work and ate some snacks in the cafeteria, I felt like the plug in my ass had grown three times and so had my cock. She ran to me. "Oh my god! Can we please go home now?" she asked before putting her hand on my lap. "I need that rock hard cock up my ass!" She almost yelled at me.

We stumbled into the bedroom, eagerly undressed, and collapsed onto the bed in a passionate embrace. Her nipples were erect.

I stroked and fondled her. I ran my hands over her large breasts, her rib cage to her tender stomach, then around her to tug on her round ass cheeks. I felt the tip of the butt plug, twisted it, and gently pulled it outward, allowing her rectum muscles to contract to suck it back in. I did everything again.

I moved around behind her and played with the plug a little more. I got some lube and rubbed it all over her ass cheeks to give them a shine. I dripped more into her asshole while rubbing the plug. I played another anal tug of war with the plug and let it rub in some lube. Then I pulled it out.

The ring stayed relaxed and glowed in the bedroom light. The red interior trembled and a drop of grease collected on the floor. I dipped my face on it to suck on her anus, licking it and thrusting my tongue in as deep as I could.

"Oh my god! Cute face in my ass!" Hermione babbled. When she's aroused, she strings almost obscene things together in the most delightful way. "Lick it! Eat my ass!" She looked back over her shoulder and grinned. "Honey, let me see you lubricate your penis! Grease your tool and shove it in my back door."

I stepped back and rubbed lube all over my cock. I dribbled more onto her butt and watched it run down her saggy asshole. I took two of my lubed fingers and rammed them in there. I turned it and pulled on the edge and said, "Are you ready Hermione? I want to own your asshole. Are you ready for my cock?"

"Pick it up! I need it now."

I rubbed my head up and down on her forked cock. Her cunt was gaping and soaking wet, the lube glistening onto her ass balls and into the heavenly valley. I paused with my head in the hole and then pushed in.

"Oh, ahh, um," she moaned as the ring stretched inward and began to give, then "Oh, fuuuck, yeah!" as my head slipped through.

I paused there as I reached around to work her clit with the fingers of one hand. As she began to gasp, tremble and push back, I slowly and steadily pushed the length of my cock into her until I was buried. Her asshole disappeared behind my pubic roof.

As I thrust into her, I grasped her pubic bone with my fingertips, touched her clit and entered straight into the opening. Passion overcame us both. She trembled and sobbed and grunted; I growled, moaned, and slapped her. Her ass cheeks bounced and wobbled; my heavy balls swung between my sweaty thighs. She squealed as an orgasm welled up deep inside her to take her to an eye-rolling, leg-shaking level of near-unconsciousness I'd never felt before.

"Oh my darling, ass looting... damn cute... gosh!" she blurted out.

I erupted like a volcano, squirting violent jets of cum deep into her plundered ass-tube, befitting her incoherence. "You sweet ass Hermione, fuuuck you fucking ass bitch!" We collapsed together, me on top of her and lying in a sweaty heap after the fuck.

My cock softened and slipped out of her greasy asshole. I pushed away from her and stared at her pale buttocks, her dark slit and gaping hole oozing cum and lube, deep secrets that were bright and red. Irresistibly drawn to it, I bent down and began licking and sucking.

Hermione sighed with pleasure and relaxed. "You love to lick my butt - my asshole - don't you darling?"

"I do. I feel particularly naughty when I lick up the cum that's spilling out."

"It feels so - so damn good when you do it," she sighed. "I want you to lick my asshole and never stop. Would you lick my asshole, Ron" - she seemed to enjoy saying asshole now - "in the morning when I put my ass in your face?"

"I would love to wake up and lick your asshole." I pressed my face into her ass and sipped the lube/cum mixture that oozed out.

"If I came into your office at noon, would you stick your head up my skirt and lick my asshole?"

"I'd rather eat your asshole than have lunch." I mouthed her anus and sucked the still limp ring into my mouth.

"If I sat on your face at night, would you lick my asshole?"

"I would stick my tongue in your asshole as far as possible." I jabbed my tongue in the middle.

"Would you lick my asshole while I fell asleep for the night?"

"I would lick you gently and love you forever." I dabbed at them with the tip of my tongue.

Then she pushed my head away. "But now it's my turn to fuck, lick and worship your ass.

I followed eagerly. Now it was time to enjoy the anal pleasure and prostate stimulation I had been preparing for all week. I sighed as she manipulated my butt plug and again as she pulled it out. The air cooled my open anus as she lubricated it, massaging and stretching the muscular collar.

She said, "I want to lick and suck your ass too. And then I'm going to fuck it."

She licked and rimmed my asshole, dipping her tongue into it. Then she slipped in two greased fingers, sheared and twisted. As she pushed them in, I moaned with pleasure; When she pulled them out, I groaned in disappointment. My head rested on my arms.

"Look," she said.

I turned my head to look back. She ran her hand up and down the large double dildo and smeared it with lubricant.

She said, "I'll fuck your ass with this big cock until you scream with pleasure. I will bang your prostate until you cum. I will own your asshole."

"Do it now and make it hard!" I put my head on my arms. When I felt the smooth dong head squeezing my tight hole I had a moment of apprehension but I pushed through by pushing out and straining like I was trying to push it out. My ass opened and the head of the cock slid inside. "Ahh," I exhaled.

"Oh my!" Hermione exclaimed, "It's been so long." Then she pushed it further up my ass. The fullness and craziness of it was exciting after so long and the week of wearing the butt plug and lube made it painless.

Soon she was ravaging my asshole, sawing the silicon bone in and out with wild abandon. I looked at her; her face was a picture of lustful concentration: eyes focused, nostrils dilated, mouth slightly parted, cheeks flushed.

Lube flowed down my balls and the shaft of my cock. Hermione ran her other hand through what they call the blemish and over my slippery balls. She grabbed my shaft and pumped it. Her two hands worked to the beat, one milking my cock and the other working the dildo over my prostate. The prostate orgasm was less intense but the ejaculation was more prolonged than I was used to. For what seemed a long time, each tug of one hand and thrust of the other brushed another strand of cum off the end of my cock. It was a unique feeling and I loved it.

Finally I collapsed in front of the penetrating dildo. Hermione couldn't pull my cock any longer as I pinned it against the bed. "Not anymore," I said. "I'm done."

She lay next to me and kissed me. "Did you like it?" She asked.

"I did. I love you and I love your cock up my ass."

"So can we go buy a strap on one tomorrow?"

"Okay"