Chapter 15

Heavily Illustrated version of this chapter available on request

I might have been in my sexual prime---recuperatively speaking, but Mrs. Bloom had certainly exhausted me. So when my Aunt Elaine met me at the door wearing a see through bra, garter-belt, black net stockings and high heels I wanted no part of her, even though she was dressed, or rather, undressed for sexual play.

“Where’s my mother?” I asked cautiously.

“She’s out, Howie.”

“She’s never out at this hour. Come on, is she hiding in the bedroom?”

Aunt Elaine moved closer and ran her hand over my face. “There are some new developments, Howie. We agreed to share you and I made up a schedule.”

She picked up a piece of paper and handed it to me. I read it. It was a sex schedule I was expected to adhere too. A sample of which would have been:

Weekday - 7 am – Rachel

8 am – Elaine

9 am – 3 pm School:

3:30 – 6pm – Reggie and/or possibly another girl.

7 - 10pm – Rachel and/or Elaine.

“This is impossible!” I declared.

“Oh, no ... your mother and I concurred that you were fully capable of maintaining a schedule of this magnitude. We can start anytime,” My aunt smiled wantonly and added, “Rachel won’t be back until seven.”

“And then I’m supposed to ... do her?”

“And or me as well. You can retire to your room around ten; do your homework, talk to your friends, or even go to sleep early if you like. We won’t bother you after ten, your mother insisted on that.”

If I felt trapped then, you can imagine how I felt when Elaine announced what she had planned for us.

“So do you like my risqué outfit?”

“You do look sexy in it, yeah,” I said wondering what she had planned for this occasion.

“I want us to do something ... um, Howie; I know you’ve never done anything like this. In fact, I’ve never done this before either. Um, it may sound nasty,” she said as her hands unbuckled my belt then lowered my fly. When my jeans hit the floor, Aunt Elaine was surprised I wasn’t erect and jerking wildly with excitement.

“What—what’s wrong with you?” she gasped.

“I had sex after school,” I said unabashedly. Perhaps I was thinking it would get me off the hook. Well I was a teenager after all.

“Oh no matter,” my aunt chirped. “What I want us to do doesn’t require a hardon.”

Well, now she had me intrigued. “What do you want to do?” I asked.

“I want you to lick my little asshole.”

I would have guessed a million other things before that line.

“You seem perplexed, Howard. Well I confess I was too the first time it was broached to me. Oh, not by that wimp of a husband. No—no. He won’t even lick my tight little channel, let alone touch my rosebud. It was at a cocktail party in Memphis ... oh, that doesn’t matter. The person volunteering to perform analingus—that’s what it’s called---was a woman.”

I continued to stare at my aunt in shock.

Aunt Elaine continued, “However enticing it sounded, I declined. Yes, I was shocked by the proposition, but she was extremely attractive and I admit I did want her. But it seemed rather unclean to lick someone’s rosebud, as she so delicately put it. However and asshole is an asshole and never a rosebud.”

“I’ve wanted to try it with a willing partner ever since.” Her finger was pointing at me as she uttered the words ‘willing partner.’

As if reading my mind, she continued. “You might be concerned about fecal matter. You needn’t be. I assure you that I performed a thorough enema earlier this afternoon. If you’ve never experienced one I can tell you it’s quite enjoyable after the first moment of discomfort. And of course, my anus is as clean as your mother’s dinnerware.”

Her spiel was so formal I almost forgot she was talking about me sticking my tongue in her ass. With her suggestion and assurances of cleanliness out of the way, she turned around and bent over, using both hands to spread the cheeks apart as she presented her rosebud for my viewing pleasure.

From where I stood, I didn’t see much, but what I did see was fucking hot. She had a tight little ass and the more I looked at it, the more licking it seemed only appropriate.

“So? We going to do this or should I put on panties for the first time today?”

I gave her a look, but strolled behind her nevertheless. I couldn’t miss an opportunity to rub against her ass with it bare and begging to be fucked.

She turned to look at me. “It’s never been fucked by anything more than an anal plug. You might be the first to do that, too. We’ll see how this goes.”

I forgot all about my new ‘schedule’ and looked down at my rising cock. Part of me was thinking about sticking my dick in there right now---what would she say? But the lizard part of my brain suggested that I might never have this kind of opportunity again and that I should go for it. “Oooo kay,” I said softly and dropped to my knees behind my aunt.

“Wait—wait,” she cried out, alarmed that I was going to start before she was ready.

“I ... um, I need to get set first, Howie.”

She took my hand and pulled me to my feet then led me to the guest bedroom and climbed up on the bed.

“I’ll get on my hands and knees with my rear up in the air. I’ll probably bury my face in a pillow because I think I’m going to scream when you start on me. You can just get behind me and make yourself comfortable.”

That said, my aunt assumed the position and I got behind her and stared at her asshole for a long moment. Admittedly I was worried about the smell, but there was none. In fact, there remained hints of a perfumery soap she must have used following the enema. There was a deeper smell ... though I was almost positive it came from her pussy. I could see her labia and thought about tasting that as well, but I was focused on following through on Elaine’s request. I mean, this had some importance for both of us; I was to be the first one ever to do her there. She was giving me her asshole.

When I touched her cheeks Aunt Elaine got skittish, girlishly skittish. I gave them a hard squeeze and she moaned excitedly.

“Yes ... tease me first. I’d like that!”

I responded to that by lowering my head a little and attacking her pussy by sending my tongue between them and nipping at her swollen outer labia.

“Oh, you little fucker! How delightful!”

That was music to my ears.

I left off her pussy and spread her ass cheeks until I had a perfect view of the hole I was going after. I noticed she was looking back and moved my head to catch her eyes. For the first time, there was a little hint of nervousness on her face. It made me even hornier.

I took a deep breath and exhaled. It wasn’t meant to get a reaction out of her---I was trying to ready myself---but my aunt moaned and shuddered. I blew lightly on her little rosebud and was rewarded with another moan and a longer shudder.

When I decided that I had teased her enough I flicked my tongue across her tight little rim, causing a chain of uneven moans to leave her mouth.

The taste wasn’t too unusual, or unpleasant, and her moaning was exhilarating. I took another couple licks from the bottom of the crevice to just above her tight hole to tease her some more and prolong what she ultimately wanted. Only to have her growl, “Quit teasing me. Lick my hole.”

Keeping her muscular cheeks spread, I began to swirl the tip of my tongue over her anus, effectively rimming it. Oh, yeah. I swabbed her saliva soaked asshole before poking my tongue into the still puckered bull’s-eye. Her ass was tight and squeezed my tongue like a vice. I had to plant my lips around her anus and push with all my strength to get any farther inside her ass.

“That’s it! Oh, Christ ... that’s it!”

The next thing I knew, Elaine was frantically rubbing her clit.

“Yes, you fucker,” she screamed and bridged up slightly. One of her hands joined mine in holding her ass cheeks open. I found it almost oddly tender how one of her outstretched fingers held onto my pinky finger.

“Lick that ass you nasty boy!”

I continued tongue fucking her asshole until Elaine began spasming with a massive orgasm, causing some of her love juice to flow from her pussy down to her ass. Hungrily, I lapped that up as it ran into the star-shaped pucker I was now slurping.

It was surreal to go from a rimming virgin to an enthusiastic player, but I wanted to please my Aunt and she certainly was enjoying riding my tongue. The more I pushed, the more her back hole seemed to relax.

Continuing to explore matters, I let her ass cheek go while she continued to hold onto one. Instead, I wrapped my arms around her waist and brought her body closer to me for leverage as I tried to push as deep as I could into her ass. But one’s tongue is only so long, and only part of it is available for what I was attempting anyway.

The fact is, the tongue tires quickly doing this, and so I found myself taking other measures to bring Elaine sexual enjoyment. Closing my lips around the anus, I licked and sucked at it, causing my aunt to moan much louder than she wanted to. I found I was really into rimming her.

“Fuck, Howie, keep doing that,” she pleaded. She hunched up, raising her ass higher to assist me in my rimming.

“Yeah---yeah, keep tongue-fucking my little asshole ... make it yours, baby.”

I was so pleased with myself that I doubled my efforts in sucking her ass.

“Fuckkk yeah! Suck that ass.”

I continued to do as asked, but sent a hand between her legs. Moving it up, I cupped her dripping mound and quickly found her clit. She bucked against the movement and screamed loudly again.

Not for the first time did I wonder what the neighbors might be thinking about the goings on in my house.

Aunt Elaine moved her body against me, fucking my finger before pushing back against my tongue.

“Make me cum, lover-boy!”

Planning on doing just that, I used my middle and ring fingers to play with her hard clit. Because of how I had cupped my hand, my palm was drenched in her juices to the point where it began to drip down over my wrist. My slutty aunt was ready to cum again.

I pushed harder while alternating moments of swirling my tongue around her hole. She continued to moan and groan. “I’m so close, baby. Don’t stop!”

I let my fingers slip into her pussy and fingered her hard. The sharp intake of her breath told me she wasn’t lying. Pulling my mouth from her asshole, I shoved my thumb into it and the sudden invasiveness of this triggered the volcanic explosion that followed. She went stiff as a board before screaming she was cumming! Next she began shaking and shuddering like someone having an epileptic fit. Her asshole was opening and closing like the shutter on a camera, and I longed to stick my cock into it.

Aunt Elaine let out one final gasp and fell face first into the pillows. She was now lying flat on the bed and lay there several minutes without moving.

“Well, that certainly went well beyond my expectations,” she finally croaked. “I thought maybe semi-fun and pleasurable. But that rewarding? I’m astonished, really. Maybe I’m some anal sex freak. I’ll have to ask your mother what she thinks.”

Popping a wet finger from my mouth, I let it travel down her crack before toying with the hole. “Does she like anal too? I mean, I’d be okay with that.”

“Mmm, I bet,” Aunt Elaine replied lazily. “Want to know what is so very odd?”

“What’s that?”

“I want to do that to you, too.”

My brain wasn’t working so well so I asked for clarification.

“Simply put,” she replied while licking my right ear lobe. “I want to lick your ass, too. I’m a firm believer in equality after all.”

I was smiling and nodded my approval at her while working my middle finger into her ass.

“Ohhh ... you’re not finished. Mmmm, very well, Howard. But I insist on returning the favor ... when you think it appropriate.”

That said, my aunt raised her ass up again and braced herself against the headboard, knowing my cock was entering her dark passage when I finished fingering it. As more and more of my finger disappeared she began shaking her ass from side to side.

“Ohhhh, Howard...”

“Yes, Elaine?”

“Fuck me now,” she moaned and braced herself for the sudden impact she knew was coming.

Removing my finger, I placed my cock at her little wet entrance. She actually sobbed once then grabbed my cock and guided it in. Her tiny pink ring began to stretch around my invading cock, opening for further penetration as a quiet squeal escaped her lips. As the head slipped in, I could feel her anus tighten reflexively. I almost fainted as I slid inside that tight little hole. I thought I was going to cum right off the feeling was so exquisite. But I didn’t, and the careful, slow going helped considerably She brought her hand to her pussy and rubbed her clit as I grabbed her slender hips and drove into her, filling her hole with my cock. I could hear the soft sucking sound of her pussy grabbing at her fingers.

I reached up and took a handful of her hair, brought my face to her ear and whispered nasty little things to her as I clutched her soft strands and slowly pumped my pulsing dick into her tight, slimy ass.

“Ooooooo,” she moaned as she reached back with one hand and clutched at my ass, urging me deeper. I felt her entire body shudder. A moment later her nails were scratching the length of my asscheek.

I slapped the hand away. She responded by raising her rear-end higher granting me an easier path to deeper penetration. She’s done this before; I thought and slammed into her two successive times before returning to the slower pace again.

“You make me feel so dirty!” she said.

“Not possible,” I replied.

“No! I love it. I like being your dirty little girl.”

I gave her a few quick little thrusts before pulling out almost all the way. Elaine gasped as I plunged back in, causing her hips to lurch forward.

“Yes!” she exclaimed, “Just like that! Fuck me hard!”

I gave her a few more thrusts, each one causing her body to sink down a little more until her face was pressed into the pillows. Her moans were now muffled as I continued pounding her ass. Reaching down I grabbed her hips, pulling her body back up to meet my cock. When she was fully impaled, I fell onto my back, taking her with me, my dick still surrounded by her ass. As we fell back, Elaine sank down farther on my dick. I let her body rest on mine as I reached around and grabbed her tits. I kissed at her neck, and rotated my pelvis, working my cock around in her butt.