[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 ways. 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 share a shower before turning in. The apartment seems to have endless 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 always 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 kind 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 kind 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 start 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 huge 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 beautiful, 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 kind 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 huge. 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 going to 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 thought 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 beautiful 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 important 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 huge 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.
Elle put her hands down in front of her, between my legs, and said, “open up.” I moved my legs apart, knees up, and she reached down to play with my balls. With the other hand, she wiggled the Aneros, side to side, up and down, in and out. That had me bucking hard under her, up into her and back down. She sensed when I was about to come, and sat down hard and upright; I felt myself bottom out within her. At the same time, she pushed hard on the Aneros, which pushed hard on that spot inside me. It almost felt like she was using the toy to push me up into herself. My first eruption surprised me, it came so hard and fast. I tugged her hips down onto me and lunged up again and again, pumping more semen into her at each stroke. When it looked like I was done, she got up turned around to face me. “You’re still hard. I like that. Now it’s my turn.”
She leaned forward and put one hand on my chest. The other went between her legs, jilling off with me inside. Her breasts have a wonderful softness, so they hung low and swayed as she rocked on me. I couldn’t reach to kiss those lovely things, but I took one in each hand. I cupped her breasts, feeling them pour into my hands, and scissored the nipples at the “V” next to my thumb. Her orgasm built, one moaning gasp at a time, until it crashed within her. I squeezed harder at that moment, pinching her nipples tightly. She looked down at me, open-mouthed and open-eyed, and squeaked out something with the last breath that was hers to control.
Last time, her orgasm left her slowly, visible step by visible step, This time, it was like someone cut all her strings at once. She leaned down onto my chest, and I had to release her breasts. That freed one arm to go around her shoulder, the other around her rear. For the longest time, she just quivered, occasional tremors grasping me within her, eventually squeezing me out. She reached down between her legs then, just to hold my softened penis, keeping the contact a little longer.
She sat up after a while, happily sweaty and tousled. “I can’t believe you did that to me twice in one day.”
I offered her own words back to her. “I just found what you already had inside you and set it free. You did all the doing.”
She smiled at me. Then she got a look on her face and reached a cupped hand between her legs. “Oops. Dribbles. I’ll be right back.” That can be the awkward moment. She almost ran bow-legged to the bathroom. I think she managed to catch the dribbles, except for a little left on me. A tissue took care of that.
When she came back she sat on the bed next to me. Her hand traced a line on my face, and she said, “You’ve had that Aneros in for what, about six hours now?”
I looked at the clock. “Something like that. It feels like six days.”
“Okay. Turn over. Lift your hips, and let’s get it out of you.”
Up on all fours, I did as she asked. I saw her open the nightstand and take something out, then saw her reach for the tissues. The Aneros stretched me open as it came out, then left me with some mix of feelings: relief that it wasn’t demanding my attention any more, and something more wistful about the feeling of emptiness, the feeling that my anus was no longer being held open. Elle wrapped the toy in tissue, to be cleaned up later, and used another tissue to wipe the lube off my rear and out of the crack. I started to roll over, about to say, “That’s a relief,” when she delivered a quick spank to my bottom.
“Stay put, you, I’m not done with you yet.” I remember her saying it took her weeks to get herself ready for her first butt sex. She was going to get me ready in two days, and wasn’t wasting a moment. There was the familiar feel of slippery finger at my backside, pushing the goo into me. Then there was another pressure, another toy. This was wider, way wider, and I gasped as the biggest part passed and slid the rest of the way into me. Whatever it was, it didn’t go nearly as far in. It did, however, hold me open — a lot more open than the Aneros. The stretched feeling bordered on uncomfortable. Another light tap on my rear, and Elle said, “Okay. You’re done.”
I rolled over, flinching a bit when I rolled the new toy onto the bed, pushing it into me.
That extra pressure went away when I rolled off it, then I asked, “Wow. What’s that?”
“A dilator. It holds you open, and gets you used to being open back there.”
“And you did this to yourself, getting ready for me?”
“You’re a lot bigger than that dilator, and I had a harder time with it than you seemed to. I think that made it possible to take you in.”
‘bigger than that dilator.’ The phrase rolled around in my mind, right on the edge of something I wasn’t quite ready for.
Elle distracted me, saying “Let’s clean up the Aneros and get something to eat. Could you pour a merlot for me, and a glass of water?”
This new toy didn’t distract me the way the Aneros did, but it still distracted me. Distracted, I made my way to the kitchen and poured drinks for each of us. Distracted, I rummaged in the fridge for finger food. Distracted, I set the food and drinks at the table next to the patio window-wall. Very distracted, I tried to find a comfortable way to sit in the wooden chair. The thought occurred to me that the wood would be easier to clean up than something with a cushion.
Elle sat across from me with that impish smile on her face. She was enjoying this. Well, on the whole, (or ‘in the hole,’) I was too. ‘”How are you doing?” she asked.
I thought for a moment while she sipped her wine. “Okay, I guess. I think I’m starting to get used to it.”
She answered with that smile again, and a knowing nod. We chatted and watched the birds in the yard. After a while she got a thoughtful look on her face, and said, “I want to say something, but I don’t want it to come out wrong.”
“Okay, go ahead.”
“Just listen, and let me finish, okay?”
“Right.”
“When you pinched my nipples right at the end, there, that hurt…”
“Oh my god, I’m sorry! I didn’t mean…”
“Just listen, right?”
I nodded.
“It hurt a little, but just enough. You know, like the burn in tobasco sauce. That hurts, too, but it hurts just right. You pinched me just right.”
I nodded again, remembering my promise to ‘just listen.’
“And you can do that again some time. Just be careful, like you were this time, okay?”
Wow. Elle has a lot more depths in her than I’ve found so far. This added a whole dimension to the kinks we’d been playing at today. “I’ll be careful, for sure. And you’ll tell me if that’s not what you want.”
She nodded. And I added. “Or if it is.”
She flashed that big impish smile again and gave me a huge hug. She echoed, “Or if it is.” She glanced at the clock again, as she’d been doing, and said “Back to the bedroom. You’re ready for the next size up.”
I must have had a panicked look on my face, “You mean…”
“Yes, back there. You can call quits any time, you know.”
I braced myself. “Today, you’re the boss. Lead on.”
She grabbed my penis and led to the bedroom. “Hands and knees, on the bed. I’ll be just a moment.” She rummaged in the nightstand again, leaving me wondering just what the hell she kept in there.
I got into position. Elle grabbed a handful of tissues and positioned herself behind me. I have to admit, the dilator came out easier than it went in. Elle wrapped it in tissue, cleaned me up, and put another big blob of lube on her finger. This time, the finger went straight in. I guess the first dilator had left me gaping open. That made it easier for the second one to get in, but it felt a lot bigger. This one really stretched me, and was definitely uncomfortable. Elle patted me on the rear again, and said. “Okay, You’re all set for now. How are you doing?”
“You’re sure you did this to yourself?”
“That, and two more sizes up. It took me a few days, though.” I groaned, as much for her as for myself. What took her days was happening to me in hours. The things people do for love. Or for sex.
The dilator didn’t have the same effect on me as the Aneros, keeping me half-erect. Elle did, though. Most of the time we sipped our wine and munched our snacks, she had her hand in my lap. I tried to reciprocate, but she wasn’t having it. She picked my hand off her lap, gave it a squeeze and a kiss, and put it back on the table. Well, no means no, even if it’s a very nice “no thank you.”
A couple of hours later, the sun was low and we decided all that snacking took the place of supper. She teased me to full erection again as we put things away. When we were down to the wine glasses in our hands, she took command of my erection again and led the way to the bedroom. She sat me down, told me to wait just a minute, and went into the bathroom. I saw her turn on the light in there, and rustle in the cabinets for a moment. I saw a double layer of towels spread on the floor, and a Fleet enema box on the sink deck. I remembered having seen them before, but had never made the connection. “Lie down here,” she said, pointing to the towels.
“Really?”
“Really. It’s not so bad, and it feels nicer when you don’t start full. It’s nicer for me, too, when there’s less mess to deal with. It’s what I do when we do butt stuff.”
Well, if she could take it, so could I. I laid down as directed and moved my legs where she said. She knelt next to me and leaned over, breasts swaying. She spread my rear open with one hand, and said, “Here we go.”
The dilator went in hard and came out hard, but it came out. Elle set it aside and picked up the enema. The nozzle entered easily — the afternoon’s entertainments had made sure of that. When the nozzle was all the way in and the top of the bottle pressed against my rear, Elle squeezed it. I felt the water rush into me. It felt unfamiliar, but my ass was getting familiar with the unfamiliar. “Now,” she said, “squeeze and hold it in.” The nozzle withdrew, and I did my best to make sure nothing leaked out. “You need to hold it for about five minutes, the let it out. I’ll let you know when time’s up.” Elle got up discarded the used enema, and withdrew to the bedroom. The next five minutes felt like the longest hour of my left, especially when I started to cramp up. Elle soon called time, and I carefully levered myself up off the floor. The moment I sat on the toilet, it all came rushing out of me. Elle and I are pretty casual about the bathroom, but I was glad she left me alone for this. I soon knew that not all of it had come out. Another big pulse poured out of me, and another a few seconds after that. It seemed like a lot more came out than that little bottle could have put in. I gave it another minute, to make sure I was really empty. I looked in the toilet before I flushed. Yeah, I wouldn’t have wanted that mess in our play. When she heard me flush, Elle called to me, “There’s another in the towel cabinet. I found that it takes two to get me really clean.” I gritted my teeth and did as she asked. Doing it by myself was a lot less embarrassing, and I called to Elle, “It’s in. Let me know when time’s up.” She did, I unloaded, and yes, it was a lot cleaner. I thought to myself, “If I ever ask her to kiss me back there, I’ll be sure to do at least one more.” Already, I was thinking about future occasions of butt play, my butt or hers.
I returned to the bedroom, where Elle waited with a tube of lube and a new toy on the bed. It’s purpose was pretty clear: about 20 centimeters long, most of it was a tube about as wide as my two fingers together. It narrowed down near one end, then flared out again — the neck would hold it in; the flare made sure it wouldn’t ‘get lost.’ (How many toys did this woman have, anyway?) It looked a little intimidating but, after all we’d done this afternoon, approachable. I got up onto the bed and down on all fours, backside to Elle. With plenty of lube it went in easily, and I silently thanked the dilators. Elle wiped of the excess lube, and I turned over on my back. “What’s the plan now?”
Elle picked up something smallish; it fit into her hand. “Now it’s my job. You just roll over, relax and let Auntie Elle take care of you.” Easy enough. Elle took my erection in one hand, then reached the other toward my balls. I moved my legs apart to give her easy access. Elle poked at the toy in my rear and giggled, then got down to another blow job. She’s always been willing, even if it wasn’t her favorite, but it felt like she was going out of her way to give me a happy experience. The top of my penis felt wonderful in her mouth, and her hand encircled the lower part. I lay back to enjoy it.
After a minute or two, she took her hand off my balls. I looked down. She still had me in her mouth, but had something in her hand, a little bigger than a car clicker. Still holding me in her mouth, she turned her head to look at it, then pressed something on it. I almost hit the ceiling when that toy came to life in my rear. It wasn’t really doing much, but felt like it was throbbing, longer and shorter, in the darkness of my bowel. My erection must have thickened, because Elle looked up and asked, “You like?”
“Oh, yes.” We returned to silence, with a little slurping from her and a little humming from the toy. Every few minutes, she’d look at the toy again and dial it up. The toy’s pace stayed about the same, but the motions became broader and more abrupt. Elle knew me inside and out — literally — and paced her loving mouth accordingly. She was getting me close, very close. My hips bucked harder and harder and, no matter what Elle did or didn’t do, I was coming. I groaned it out to her, just in case, and she fiddled with the control again. In addition to the pulse, it felt like something rotating in my rear, at just the right rate. I arched off the bed, filling Elle’s mouth, still pumping well after I had nothing left to pump. Then I fell back on the bed totally spent. Elle continued to nurse at my penis, but I felt it shrinking in her mouth. Suddenly toy was way too much for me. “Off,” I groaned. “Turn it off.” Elle let go of my penis to comply, her mouth pursed around the load I’d given her. She pushed a button, and the presence in my ass went dead. It still filled me and its rigid shape resisted the grasp of my inner muscles, but that was OK. Elle milked the last drop out of my penis, like milking a cow, licked it up, then smiled at me and swallowed conspicuously. I know she never used to like doing that; it must have been part of the show for me. We kissed again, long, slow, and slick with my semen. I could barely talk. “Elle, do you want your toy back?”
“Oh, I almost forgot it was there.”
Right, I thought. It’s not in your butt. I rolled onto my stomach, and she tugged it free of my rear. It came readily, far more readily than that smaller toy this morning. It seemed Elle’s plan was working.
She returned after cleaning the toy and brushing her teeth. I took my turn in the bathroom, then turned out the lights and joined her in bed. We spooned, me on the outside, and that’s the last I remember. Sexual exhaustion overtook me, both physical and mental. I remember thinking, “What happens tomorrow?” but fell asleep before I could even guess.
—
The sun was up when I awoke the next morning, and I smelled fresh coffee. I also felt Elle’s mouth on my balls. The morning was warm, so they were hanging loose. That made it easy for her to enclose one with her lips and tongue, then the other. I’d never actually felt that before — nice but not something I’d be asking for. Her stimulation was plenty to get an erection going, though, and her mouth moved to that as it grew. She nursed at it for a while, then moved up beside me, her hand still grasping my erection and tugging on it gently. “You know,” she started, “I mostly kissed dicks because guys liked it so much. I guess I even got fairly good at it.”
“Believe me, you did.”
She smiled and continued. “I never knew the best part: getting to it small and soft, and feeling it grow in my mouth. I know it’s not really voluntary, mostly a reflex. Still, feeling it grow makes me feel like I’m doing something special, like I actually made it grow. It’s like how you feel when someone really likes a present you’ve given them.”
“Elle, I can absolutely see how you had so little experience with them small and soft. And yes, your mouth on my cock is a gift.”
She giggled. I added, “Any time I’m small and soft, I’m all yours.”
“Watch that ‘any time’ thing, big boy, or I might believe you. And swallowing is easier, too. It used to get halfway into my throat and I’d gag. I’m not sure what happened.”
Maybe it was being given the choice. I never pressured her about swallowing, and never complained when she dribbled it out. From other things she’s said, it’s sounded like lots of her guys were a lot more coercive. Gawd, I’m glad I never dated men. “Well, almost any time, night or day. And swallow or not, making love with your mouth is still better than with any part of some women I’ve known.”
“You really make it tempting to believe you. We have a busy day today, lots to do.”
I tried not to imagine. I signed up for it, and I was determined to carry it through. That said, she’d already given me plenty of reason to carry on. “Can the day wait for our coffee?”
A fake pout (she never pouts). “Well, I guess. It is coffee after all,” as if no other excuse would satisfy We sat up in bed and sipped, each with a hand in the other’s lap and playing softly. We’d both spread our legs some, to given plenty of room to play. I think I oozed some pre-come; I know her labia got thick and pillowy, and the crease of her clitoral ridge had risen.
I finished my coffee first, and shuffled around so I could put my head in her lap. You know, right under those magically soft breasts. They sit low and move easily, so I had a soft pink nipple in my mouth when she lifted it and offered it to me. I don’t know if I mentioned, Elle’s breasts have this softness that flows into my hand. They’re not ‘bouncy’ or ‘perky’, they’re low and soft the way every bust becomes in time — she just got there early. If you don’t like the idea, well, you’ll probably be very lonely when all the women around you have boobs like hers. The sweetest fruits are the softest.
She set her empty cup aside, lifted her nipple out of my mouth, and said, “Are you ready?”
“Well, probably not, but that hasn’t stopped me yet. Ready for what?”
“Dilators. We’ll start where you were yesterday.”
My head still in her lap, I gave a three-fingered Boy Scout salute. “Yes sir, ma’am.”
Half resigned to my fate and half eager for it, I knelt on hands and knees on the bed. Head down, really, more like elbows and knees. I pretty much knew what to expect from yesterday. Elle greased her finger with some slippery goo and massaged my anus until I stopped twitching. More goo, pressed into the hole back there, and her finger at the opening. Then in. She slid in easily. I had learned to relax, at least a little, and the surprise of it gave me no time to tense up. Once I was well lubricated, I felt the toy at my rear. It felt bigger than yesterday, or I had contracted back toward my original size. But, with some extra pressure and some grunting on my part, the dilator was in. It held me open, a little stretched, no matter what I could do, so I acquiesced. I signed up for this, remember, even if I didn’t know this was what I signed up for. The next hour or so passed in two different realities. In the reality you’d see, I collected the breakfast things, Elle washed, and I dried. In my mind, everything flew in orbit around the plug in my ass. How could I stand or move? How could I sit? Was it getting easier? And what would come next?
Elle teased me gently in the kitchen. She’d stop, lift my limp cock in her hand, and stroke it with a fingernail until it stiffened, maybe until it oozed a crystalline drop of pre-come. Then she’d turn her bare back and bum to me and go back to the mundane chore at hand. She unloaded the dryer and I folded, and she’d stroke me as I worked since her job went quicker. I was just imagining being comfortable with the plug in my butt, when she took hold of my erection and tugged me toward the bedroom. Time to size up the dilator, I guessed, and was not enthusiastic.
First stop was the bathroom again. Elle put towels on the floor, and had me face down and butt up. She tugged at the plug, and I felt the ‘pop’ when the widest part came out. Then I lay on my side, and Elle put the Fleet into me. It felt so small after the dilator. We finished that part, I wiped myself clean, and joined her in the bedroom.
I got onto the bed, up on hands and knees. Elle hummed quietly as she rummaged in the nightstand’s drawer, and put two things on the bed. A fold in the blanket hid them, but I’d find out soon enough what they were. She lined up behind me. I saw her put a blob of lube on her finger — no, on her fingers, two of them side by side. I gulped when I saw that, but the two went into my rear easily. The dilators were doing their job. Elle was doing a job on me, too. Her two-finger touch on my prostate had me shivering. She put her other hand on my hip to steady me. Completely focused on my asshole, I saw that impish smile on her face. She took her fingers out and picked something up from the bed. I couldn’t see what it was, but I saw her pick up the lube, too. A moment later, I felt the new toy press against my rear. Elle pushed slowly, and I felt it open me up as it entered. Elle kept pushing, and I kept opening, wider and wider. I really felt stretched, but it kept coming. It started to get uncomfortable, then I felt the widest part pass and it popped in by itself. I didn’t realize I’d been holding my breath until I felt it leave in a rush.
I rolled over onto my back and just stared at the ceiling for a minute, while my body tried to figure out what just happened. Elle moved up toward the head of the bed and stroked my face. “You really took that well. I needed three tries before I could get that one in. We’ll get there soon. You’re almost there.”
I heard the words and remembered them. At that moment, though, full and stretched til it almost hurt, I couldn’t actually listen.
“Lunch?” she asked, and brought me back to the real world. It had been a while since breakfast.
The plug in my rear had most of my attention. Even so, I mentally inventoried what we had in the fridge. There were a bunch of leftovers, some desperate to be used up. Elle set the table and poured chardonnay while I microwaved things..
We sat next to each other and ate quietly. I really couldn’t think of much to say, with that monster plug in my ass. Elle’s hand on my penis didn’t help the conversation either, but worked me up into a drippy erection. I squirmed in my seat, trying to find a comfortable position. Elle saw what I was doing and understood. “You’re doing really well, you know. The first time I got that dilator in, I had to take it out after about five minutes. It was the third or fourth time before I could keep it in as long as you have.”
I appreciated the encouragement, but was still too distracted to come up with an answer. We finished lunch and stood up. I started to collect the dishes, but Elle took me by the hand. She turned me to face her, and closed in for a whole-body hug. We rocked together for a moment and she said, “This is really special for me. I’ve been thinking about it for a long time, and you’re taking it better than I ever imagined. Let’s go to the bedroom.”
She led me by the hand and sat me on the bed. Around on her side, she went back to the nightstand. The first thing she pulled out was obviously a dildo, a bit nerve-wracking in size. It’s ‘L’ shape made it pretty clear that the long arm was for me, and the short arm would go up into her. The lube came out next, and something strappy looking. The dildo fit through a hole in the harness. She started to pull it on, paused to put some lube on her end of the dildo, squatted to put it in, then pulled the harness up and tightened the straps around her waist. She turned to me and waved it at me, hands on hips and a big smile on her face.
She patted the bed and said, “You have no idea how much this means to me. Come on up and let’s get going.” I got on the bed, up on hands and knees again. Elle pulled the dilator out, and I grunted when the wide part came out. My anus must had stayed open, because I felt Elle squirt the lube right into me. I looked back and saw her smear it on her ‘cock’. She had a serious look on her face as she lined up behind me, put one hand on my hip, and used the other to guide the dildo toward my rear. I felt it touch, gently, and Elle closed her eyes. Her hip pushed toward me and pushed into me, just a fraction, and backed off. Another push, slightly deeper, and back again. She got into a steady, slow rhythm with both hands on my hips, deep in concentration.
The dilators had gotten me ready for the thickness of the cock, but not for its length. It entered me easily and filled me from the first, but it kept going. Deeper and deeper into me, I grunted as it advanced. It didn’t hurt, or not much, but none of Elle’s preparations had readied me for this reality. It bumped my prostate and my back arched in response, and it kept coming. Soon, I felt Elle’s thighs against mine. I looked back again and saw her eyes still closed. She leaned against me for a moment, the opened her eyes. “Are you okay?”
“Yes. I can’t believe how deep you are in me, how much you fill me up. Is this what it’s like when I’m in you?”
“Pretty close, I guess. I picked a toy as close to your size as I could.” She rocked softly against me as she spoke. I remembered her end of the toy in her, and tried to imagine how that felt.
“Is this what you imagined?”
“Oh, it’s better. Way better. There’s something about seeing my ‘cock’ enter you, seeing it in you, seeing you taking it in. I’ve always loved being the receiver. Being the giver is a whole new experience for me. I think it will make receiving even better.” Gentle rocking as she talked, gentle movement inside me, gentle touch on my prostate. Being the receiver was new for me, too.
Elle said, “Let’s try a different way.” She pulled out, leaving me empty, and said, “Roll over.” I complied, and she added “Knees up, way up.” I curled up, knees nearly at my shoulders. She had to scrooch down a little, but aimed her cock at me and started in. She knew, from her own past experience, to go slowly and give me time to adjust. Soon, though, her hips were up against mine. She started rocking again, in and out.
“Play with yourself. I want to see that.” I already had a streaming erection. I wiped the pre-come around the tip, wet my hand with saliva, and started stroking myself. My other hand cupped my balls, just a little extra feeling that I really liked. That, and the different angle meant she was up against my prostate a lot more.
“That is so hot, seeing you play with yourself, getting yourself all excited. And there are all those little details, like the way you wet your hand and spread the slickness around. I can see you getting tense and tight, too.” Elle kept rocking into me as I jacked myself, and kept up a patter of encouragement. I saw her hand moving under the harness, pressing her clit. Our eyes seemed locked on each other. Elle’s bucking against me became sharper and harder. I knew that feeling from when I was the one doing the fucking. It meant she was getting close. I was too. I wet my hand again and said, “Elle, I’m coming.”
“Yes, big guy, yes. Come for me. Show me what happens when you’re up inside me, show me how you fill me up.”
I came like never before. I didn’t ejaculate a lot, not after emptying myself so many times in the last two days, and it barely came as far as my navel. That doesn’t matter. It felt as big as any I ever had. Feeling so full and watching her watch me made it a different experience, one I knew I’d have again.
“God, you’re so beautiful.” Elle’s voice sounded breathy. She took that blob of semen on my stomach, and lifted it to her lips. I saw her hand moving under the harness, jilling herself, as she pumped her hips against mine. Then her mouth opened wide in a silent shout, her back arched, and she shoved the dildo into me. Back and then in again, hard. It got uncomfortable for me, but I’d take a lot more to see her come the way she did. After a few more pounding thrusts, she relaxed. She leaned forward. My knees were still up toward my shoulders and she put her hands on the back of my thighs, supporting herself. She panted and her body heaved as she recovered. She might not even have been aware that she was still, just a little, thrusting in and out of me.
“I never thought about it from your side, but there’s that moment when you have to pull out.” Action suited word, and she left me empty. I got some idea what that was like from her side, too, feeling her penetration end, like mine just did.
Elle unstrapped the harness and detached herself from the dildo. She offered the short end of it up to me: “Take a taste?” Exhausted, I shook my head no. She dropped the gear on the floor, then came over and lay on top of me, full length.
“Thanks. I don’t know how to say it, but thanks. These two days have been the most incredible experience, and I’ve never seen anyone give themselves the way you’ve been doing. Thanks.” She rolled off me and we tangled our arms and legs together. That armful of warmth made it easy for me to drift off.
Elle napped too, and was still asleep when my eyes opened an hour later. I brushed a wisp of hair away from her face. Is it weird to watch someone sleep? Okay, then I’m weird. After all the intensity we had together, it was lovely to see her so relaxed. She didn’t have a penis for me to suck on as she slept, the way she did for me, but I put my finger between her labia. I just held for a moment, enjoying the soft warmth of her most intimate self. Then I started small motions with gentle touch, way up where her labia parted. It was small and soft, but I still found the shaft of her clit, safe under its blanket of pink skin, and rolled it back and forth under the tip of my finger. Gods, I love how that feels. A few minutes later it wasn’t so small or soft, and I pressed more firmly as I played. Elle made little noises in her throat and rolled onto her back, still asleep. That gave me a chance to lean over and take her nipple between my lips. It stiffened in my mouth, and I felt her labia thickening around my finger. Her hips tensed and relaxed, then tensed again.
Elle groaned as I licked her nipple, and I saw her eyes open. She clutched my head to her chest as the orgasm came over her. It wasn’t big and exciting, the way others had been, just warm and slow,. a perfect way to wake up. Her orgasm retreated as quietly as it had arrived. She hugged me and we kissed, warm and slow kisses, and I reveled just in having her body up against mine.
“Are you hungry?” she asked.
“No. but I could use a glass of water.”
She brought one for herself, too. We sat up on the bed, sipping, and looked into each other’s eyes. She said, “That had been a fantasy of mine forever, and you made it come true. You don’t have to do it again — that was wonderful all by itself.”
“What if I want to do it again? I mean, after my butt recovers. It had an awful lot going on.”
She giggled. “I know what you mean. But what do you want now? From me?”
I took her glass from her and set it next to mine on the nightstand. I pushed her back down onto the bed and pushed her knee to open her legs. I got between them and leaned over her. She reached down to my erection and guided it toward her vagina. She played with it, rubbing the tip on her clit and moistening herself with my pre-come. Then she placed the tip at the edge of her vagina. “I already came. This one’s for you — you’ve already given me so much.”
I slid in easily and started a slow rhythm, pushing into her and pulling back. She wrapped her arms around me and looked up at me. I had already come so many times in those two days that it would take me a while, but that wasn’t about coming in her. It was just about being in her, and that went on and on.