Three Day Weekend – Anal


[This continues the story of Ian and Elle, started in ‘Progressive Dinner’ and ‘After Dinner’]

We started the three day weekend by celebrating our second anniversary about the same way as our first. That meant a leisurely tour of the city, stopping at different places for food and drink. This time, we started with a few appetizers at a nice Italian place, hefeweizen at an open-air beer garden, and a few more stops before winding down for desert. I had calvados, espresso, and some sherbets; Elle washed down her tira misu with a cup of spice tea.

Other than the details of what we ate where, that trip differed in two methods. First was that, instead of a hotel, we went back to the apartment we’d shared for the last few months. And second was that Elle started the adventure dressed the same way she ended the last one, wearing a summer-weight jacket, a wide knee-length skirt, flat shoes, and nothing else. When she leaned over or turned a certain way, the lapel of her jacket opened to show some of her soft, low breast, sometimes as much as a nipple. At the end of our first anniversary tour, I sported a raging hard-on. This time, I started with one, and held it almost the whole time until we got home.

We stopped for an open-air concert on the way home, so it was late when we got home. The day had been hot so we agreed to distribute a shower before turning in. The apartment seems to have infinite hot water, so we lingered and played as we washed each other. At one point, I was leaning against the shower wall. Elle was behind me, soaping my back with one hand and reaching around to my erection with the other. Her hand slid easily over my soapy back, hips, and thigh, still holding and stroking my penis.

Out of nowhere, she asked, “Have you ever thought about anal sex?” It was the same question she asked a year ago, when we were celebrating our first anniversary. We tried it, and it’s been a once-in-a-while treat for us ever since.

I smiled and answered, “You mean like last week? That was amazing, and you…”

She cut me off. “No, silly, I mean receiving.”

I started “You mean, uh,…” and she cut me off again.

“I have the lie detector right here.” She gripped my erection. “And that says you have, haven’t you.”

“Well, I guess so.”

Her hand on my back had dropped to my rear, still holding me in front. “I’ve been thinking about it, too.” A soapy finger slid between my cheeks.

“And I think it might be fun.” I lurched forward when that finger touched my anus. Her hand followed me though, and the tip of her finger entered. “What do you think?”

To tell the truth, I could barely think about anything but her grip in front and her finger behind. “Uh, yeah, uh.”

“Nice! We have all weekend. Remember when I offered my butt the first time?” How could I forget? “I spent about two weeks getting ready for that, a little at a time. I think we can do all that for you in the next two days since there’s nothing else planned. Sound good?”

Her finger had gone a little deeper into me, shifting, tilting, and rotating that digit in the soapy slickness. It felt a bit strange but, combined with the grip on my erection, strangely erotic.”Um, okay.” She had me in such a daze I’d agree to a root canal.

She sounded excited. “Great! Leave it to me. We’ll go slowly, and we can stop any time you want to. That’s tomorrow, though, right now, I think this big boy has been at attention all day and needs a little loving.” Fingers tight around my erection made it clear which big boy she meant.

We rinsed off with a little more play with the shower wand, dried each other, and went to bed. A bright moon gave us some light after we turned everything off. I laid down in the bed, but Elle say on her heels, knees forward, next to me. She leaned over and took my cock in her mouth, cupping my balls with one hand. The soft licking and suckling had pre-come streaming out of me, and I felt the the slickness spread across her tongue and lips. She kneaded my balls gently, too, with special attention to that spot just behind.

“Elle, I’m going to come.” She redoubled her efforts, with stronger motion of her mouth and firmer touch with her hand, just back of my balls. My hips bucked as I shot into her mouth, and she followed my motions. Again and again, a bit less each time, I wet her mouth with my own fluids. Finally, I sagged back onto the bed. One more lick, with a squeeze to get the last of my come into her mouth, and she sat up with a big smile. Then swallowed. She’d never done that before, so this was special for her.

I pulled her down for a big kiss, and tasted myself in her mouth. Somehow, that’s all the time been especially intimate for me, tasting her tasting me. We settled into a warm spoon hug and drifted off. Just as I was about to fall asleep, I remembered what Elle had planned for me.

What had I gotten myself into?

I woke to bright sunlight, the sheet turned down with me bare to the day, and a half-erection growing in Elle’s mouth. She sat up and smiled when she saw me wake up. My erection firmly in her hand, she said. “Good morning, lover. This is a special day for you, a special weekend, so let’s get started.”

I still found the prospect daunting, but I had agreed to it. “Ok, what do you want me to do?”

“First, lift your hips up so I get this pillow under you.” We did that. She turned and got some things from the night stand. “Now pull your knees up, way up.”

I did, feeling very exposed. Exposed to Elle, which made it exciting, but still. My scrotum had already pulled in tight — excitement, chill, or nervousness, I couldn’t tell. Elle reached down and cupped her hand over it, warm and soft. The funny position made it a new experience for me, and I liked it. I felt something tender in her gentle massage. Her thumb ranged down across my taint from time to time, and that felt good too. Elle picked up the tube of gel she’d taken from the night stand, and squeezed a little onto her finger. She put the other hand back over my balls, and stroked the slick gel across my sensitive hole.

She just rubbed at first, keeping her other hand warm and comforting on my balls. Her eyes were really on my anus though. Her slick finger drew little circles around it, and I could feel each wrinkle shift under her finger. Soon she added some pressure. She hadn’t entered me yet, but I could feel her getting ready to. Another blob of lube on her finger, and she pressed again, and in.

My breath left in a whoosh, and I felt myself clench around her. She looked at me and reached up to stroke my face. “Okay?” She held her place, only the first joint of her finger inside me, not moving.

I nodded, all I could do at that point. Her free hand went back to my balls, lifting them out of the way, and the touch in my anus moved. Out a little, then back in, out and then in a bit more. Soon she touched that inner ring of muscle, the last barrier to real penetration. (You know what I’m talking about, right? I mean, hasn’t everyone experimented at least a little?) She looked back at me with a smile, then withdrew both hands.

It was just for a moment, though. She had that little applicator full of lube already, and touched the tip to my hole. I knew what it was, having used it on Elle so many times: an easy way to get the lube all the way inside. She pressed gently but steadily into my pucker, opening and entering a millimeter at a time. With a concentrated effort, I relaxed as much as I could. Suddenly, it was in, all the way in. I felt it at my body’s entrance, as I had felt her finger a minute ago, but this was way up inside, too. She pressed the plunger on the applicator. The tube shifted inside me and where it entered, and there was some additional feeling where the blob of slickness had been pushed into me. It actually felt sort of nice, but I had tinge of anticipation about what would come next.

Elle reached down between my legs, her hand too low for me to see below my stomach and erection. I saw a look of concentration on her face as her fingertip centered itself within the opening, then pushed. I must have made some sort of noise; she looked up at me in concern, then smiled as I relaxed and started to breathe again. With a single stroke, one finger was in deep and her other knuckles pressed against my rear. Her finger probed inside me, curling up toward my belly button. Then she found something and pressed. Even in my awkward position, my hips bucked.

“That must be your prostate. That bump feels just the way I’ve seen it described. I’ve heard it can give pretty intense feelings.”

“Intense? I though you were turning my dick into your finger puppet.”

“You seem to like it, though.” At that her other hand took control of my erection. “Now just lie back and let me take care of you.”

Between her perfect hand job and the magic she worked by massaging my prostate, I was trembling in seconds. She’d drive me to some insane peak, my rectum pulsing around her finger, then stop. Both hands would stay still until she felt me unwind a bit. Then her massages, inside and out, would begin again — but maybe with just a tad more pressure than before. I lost track of how many times she took me to the edge, then left me hanging. When she finally decided to let me come, I think I roared. She turned everything up to eleven, and I ejaculated like never before. The first burst came nearly to my chin. The next five or six landed successively shorter, but felt just as intense. My orgasm had supposedly finished, but Elle kept her hold on me, inside and out. She started stroking again, and soon a gigantic aftershock ran through me. I didn’t ejaculate. It felt like I had nothing left, but I saw another drop of semen grow and fall from the tip of my cock. I had never felt like that before, but she did it again and again, stop and restart, until my body had nothing left to give. I lay there, boneless, grinning and panting, and saw the satisfaction on her face.

“You’re a mess,” she declared, “A delicious mess. I’ll be right back.”

I heard water run in the bathroom. She came back with a wet washcloth in one hand and a dry towel in the other. She wiped and dried me, an affectionate bit of grooming that sustained the moment. I rolled over when she asked, and got up on hands and knees so she could clean the extra lube off my rear. The she returned the towels to the bathroom, came back, and lay down next to me. Elle lay on her side, head supported on one hand, the other hand warm and strong on my soft penis.

“What do you think so far?” she asked.

“Witchcraft. There’s no physical explanation for what you just did to me.”

She laughed. “I didn’t really do anything, Ian. I just found what you already had inside you and set it free. You did all the doing, and you were amazing.”

“Whatever you set free, I hope it comes back soon. I’m wiped.”

“You sleep.” She pulled the sheet up over me. “You’ll need to rest up. We’ve barely started.”

That sounded exciting, mysterious, and ominous all at once. She was right, though. I was too drained to think much of anything and my eyes closed.

I woke some time later with a full erection. Elle sat on the bed next to me stroking it gently. She’d run her fingernail up the length of it, back down to my balls, then up again. Bare and gorgeous, I admired her curved hip, slender body, soft breasts, and mischievous smile. “Hey, sleepyhead. Ready for more? We have a lot to do.”

“I know. You said you’d get me ready for butt sex, and I’m still not so sure about that.” She was still running her fingernail along my erection, the gentlest tease I could remember.

“I think we got off to a pretty good start, don’t you?”

“Oh, yes. I could never have imagined what you just did to me.”

“There’s more to come. And you can still say ‘no’ whenever you want.”

“I’m all yours, at least for now. What’s next?”

“Up on your hands and knees. I have something special for you.”

“Okay.” I complied, wondering what my poor ass had coming next. Elle crawled across the bed, breasts dangling and swaying. She came back with the tube of gel in one hand and something, I couldn’t see what, in the other. Sitting behind me, she rested her hand on my butt.

“I really like this view of you, dick hanging down, scrotum bunched up,” She ran that teasing fingernail along my raphe, that line down the middle of my scrotum. “and this lovely dark star.” She poked my anus gently, and I felt myself flinch. “So many possibilities.”

Elle took her hand away from my rear for a moment, did something I couldn’t see behind me, then put it back. She poked my anus again, this time with a blob of lube. I felt her spread it around, then push some a little way inside me. I still flinched, but was learning to loosen up. The next thing I felt certainly wasn’t a finger. Wider and harder, it was some sort of toy. Toy for my ass.

Elle cooed, “Now open up. This is a little bigger, but you should do just fine.” Bigger, for sure. It felt gigantic. Even with the lube, it took some pressure for that thing, whatever it was, to open me up.

I panted, “Elle, I…” She cut me off.

“Shh, shh, shh. You’re okay. Just a little more…”

“Oof.” Once the widest part had opened me up, the whole thing slid in quickly. It narrowed considerably after that, but still held my anus open. Another little push, and something pressed against my perineum. I held still for a moment, gauging the feeling of the toy inside me. It went in about as far as Elle’s finger did, maybe a little deeper. Wider than her finger, for sure, and stiff. It didn’t move in me the way Elle’s finger had done, but touched that same spot, my prostate. Elle’s touch had been far more intense, but it was that same spot, for sure, pressure right at the back of my penis.

Elle pulled a tissue from the box and wiped extra lube off my rear. “There,” she said, “how’s that?”

“What is it?”

“It’s called an ‘Aneros’, a prostate massager. What do you think?”

I started to get up, and felt it shift inside me as the muscles moved around it. “It’s kind of nice, but will take some getting used to. Now what?”

“Just the usual. Breakfast, read the paper, clean up.”

“With this inside me.”

“Yup.” She leaned forward with a big smile and wiggled something I couldn’t see. I felt the whole length of the toy, from where my ass gripped the unyielding material to that thing trying to control my penis from inside. This was gonna be an experience.

“Wow. Okay, I’d better get dressed then.”

“No, silly. Do you know what day it is?”

“Sunday? July fourteenth? Bastille day?”

Nude Day. I want all of you available all day. And I want to be available. This is turning me on like you wouldn’t believe.”

Oh. I had been so focused on what I was feeling that I hadn’t wondered much about Elle. She was standing, facing me. Her lower lips swelled, with sweet pink ruffles peeking out. “I think I’d better do something about that,” I said.

One of the nice things about a small lady is that she’s easy to pick up, even for someone like me. I took her in my arms, carried her through the bathroom door, and sat her on the sink deck. I knelt on the tile in front of her, and she spread her legs. Her vulva opened to me, like a flower in bloom, and I caught her warm animal scent. I leaned into her, kissing along her thighs, then nibbling at her outer lips.

Elle sat back on the counter and pulled her heels up onto it. That tilted her hip toward me and opened her all the way. She took my head in her hands and pulled me forward. I leaned in again, tongue out, and licked her from perineum to clitoris. Her flavor, musky and sweet, made me want more. I tongued her vagina, pulling out more of that nectar, and Elle started to moan. I tasted each crevice and fold, nibbled, kissed, and licked. And the whole time, I felt that toy inside me. It was a presence I couldn’t ignore, shifting within me as I moved. The sensation wasn’t enough to drive me to orgasm, but an ongoing tease of my newfound erogenous zone. Maybe that tease was what made me draw out her arousal.

Still, it wasn’t long before Elle’s response built up. Her breathing became ragged, I saw her toes curl, and her whole body started to wind up. Then, with one soprano roar, it was on her. She pulled my head hard against her core, and I pinched her clit between my lips. Then, when she seemed at her peak, I pushed two fingers into her. They went in fast and deep because of her slickness, and I felt her inner muscles clamp down on me. Head back, her voice froze in her throat as I curled my fingers inside her. She relaxed for a moment, tensed again, and relaxed again. By steps, her body released her from that gorgeous tension. I had stopped moving, but kept my mouth pressed against her until she gasped, “enough, enough” and pushed my head away. Keeping my fingers inside her, I stood (feeling the toy shift again), and hugged her close. Her head turned toward me as I held her, demanding a wide, sloppy kiss. It was one of those loving, animal moments between us, too essential for spoken words.

We held each other for a few long minutes, then she leaned back and said, “I’m hungry. I’m a wet mess, too, and so are you. Let’s clean up and eat,”

I answered, “Sure. And what about the, uh…”

“Aneros? I think I like it where it is.”

I wasn’t so sure, but, “Well, okay” The stimulation was nice, mostly, leaving me in a warm erotic fog. I figured I could live with the distraction.

Elle wiped herself clean between her legs, down her thighs, and behind. We both wiped her scent from our faces — I left a lot on her during that kiss. Then I realized I had been dripping pre-come, as another bead grew on my penis and started to fall. There was some on the floor, too, so I cleaned the tile with a tissue. Oral sex is pretty exciting for me, too, so that wasn’t a surprise.

The fridge offered some cooked spinach, cheese, and eggs. It looked like an omelet to me. I put two potatoes in the microwave to cook while I got the rest together. I’d pan-brown them when they were done. When I put butter in a pan for the omelet, I realized the big drawback of Nude Day: kitchen spatters. Elles’s frilly apron might look silly on me, but not as silly as burns from the stove.

I had popped a gigantic erection giving Elle a good time, but was surprised I was still at half-mast. Then I realized, that toy was having an effect on me. I looked down and caught another clear drop before it fell. Elle saw me and said, “Oh, you drippy boy.” She caught my hand and licked it clean. “Are you going to be like this all day?”

“I’m not sure. Maybe. That Aneros doesn’t let up.”

“I should have gotten it for you long ago. That big, fat cock looks good on you.” The next drop of pre-come was already building. She took hold of my penis, wiped the tip clean, and held her finger up to my lips. I licked it clean for her, and the slippery sweetness of it lingered in my mouth. Perhaps this was why she wanted “all of me available.”

As I said, the Aneros didn’t let up. I had that half-erection into the afternoon, with Elle attentive to my slow stream of pre-come. Sometimes she’d wipe it clean with her finger, sometimes she’d kneel down and lick it off. The half-erection turned full when she did that, much to her delight. When she did that about three in the afternoon, she lingered over it, kissing and playing, taking the crown into her mouth to suck out whatever she could. She looked up from her kneeling position and said, “I bet you’re ready to pop.”

“I’ve been simmering since you put that thing in me, and now you have me ready to boil over.”

“You’ve been a good boy. Let’s take care of you.”

Still holding my penis, she led the way to the bedroom. I felt like some overgrown pull-toy. She pushed me down on the bed, and said, “Scoot over.” Her breasts dangled and swayed as she swung a leg over me, facing ‘reverse cowgirl’ toward my feet. Straddling me, she knelt up and leaned forward, one hand on the bed by my legs. Her other hand took my erection and guided it as she sat down on me. Once I was in, she leaned back. Using the strength of her legs, she lifted herself up, then back down onto me.

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