Weekend at the Cabin Ch. 09

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Tanya gets her first anal experience; Tim & I contribute.
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Part 8 of the 15 part series

Updated 06/11/2023
Created 11/07/2021
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cvandrews
cvandrews
363 Followers

Weekend at the Cabin: IX

Then Sandy said, "It might be easiest, for this first time, if you lie on your side, like we're doing, and pull up your top knee, like this ... now a little farther ..."

* * * * *

... and that's what I told Tanya, how we should do it, this first time.

"If you're ready, lay down on the bed, on your side, facing away from me, and lift your top leg and take your knee and pull it up -- there, just like that." She followed my instructions, but she seemed hesitant, like, "Are you sure this is the way to do this?"

I got onto the bed with her, but before I rolled onto my side, Tim came over with the jar of lube and kneeled on the bed beside me and said, "Here, Chief -- T might be good and ready, but you better put a bit of this on before ...," and he put a generous glob of the lube on the head of my cock, then spread it around -- quite lovingly, I might add -- and down the length. Pleased with his work, he got off the bed and told Tanya, "There, Hon, that should make you two good and ready for each other."

Now lubed and ready, I moved in behind T and wiggled my cock in between her bumcheeks, 'til I felt the tip touch Tanya's slippery, wrinkled butthole. She flinched a little in surprise, but quickly returned and pressed back against me.

I wanted to be sure that my cock was hard and stiff and wouldn't squish around when I tried to penetrate Tanya's asshole, which I knew would still be tight despite all the lubrication and all our efforts to prepare and relax her. I made a ring with my thumb and two fingers, then squeezed my cock a few times before sliding them up and down the slippery shaft.

To help, I closed my eyes and thought about what was going to be happening -- picturing my cock, its crown shiny with lube, up against Tanya's little brown hole, pausing, then penetrating, just a little at first, then entire head popping through her resistance, feeling her tight anal sphincter squeezing my cock -- and then that indescribable feeling, of the full length of my cock, sliding through her warm, silken, caressing rectum.

Now I was hard and ready to help Tanya experience what anal sex is like.

"Ready, Tanya?"

"Yeah." I could barely hear her. "I mean -- yes." Tim was lying on her other side, facing her. He kissed her softly on the forehead, then took her hand in both of his and said, "This'll hurt at first, but Chase'll take care of you -- you're gonna love this, T, trust me."

My left arm was under Tanya, her head on my bicep. My right hand held the head of my cock in place against her pucker. No more delays -- it was time. I moved my hips forward, just the slightest bit, and worked the tip of my cock around against her, and I felt the slickness as the tip pressed into the softness. She didn't move, so I pressed more firmly, and I felt my tip force its way even farther, and I could feel that I was actually penetrating her anus.

I paused, waiting to see if Tanya wanted me to stop there. Sensing nothing bad, I pressed on. Now I -- we -- were at the point where things get serious -- the point where I had to force -- and Tanya had to take -- the whole crown of my cock inside her anus. Gentle as I wanted to be, I knew that doing this slowly would just prolong the discomfort for her. I pressed, and I felt the familiar "pop" as I got past the ring. And I was in.

"Oh!"

And it wasn't Tanya's familiar "Oh!" of surprised delight. I knew that it hurt, and I felt terrible. Fortunately, Tim knew what she was experiencing. He squeezed her hand and kissed her forehead and told her, "You're doin' great, T." (Later, Tim told me that she made a pained smile.)

I didn't move. I think I was waiting for Tanya to say something -- to let me know that I should go on -- or stop.

"I think it's OK Chase -- go ahead." Tim.

"You sure?"

"I think so."

During the pause, my cock had lost a little of its "determination," if you know what mean. I moved back and forth, just a little, so my cock could experience some friction, just a little of the feel of my crown sliding against the tight, slick asshole.

And that did it. That slight sensation got me stiff again and I started the drive into ... all the way into Tanya. I pulled back a little, then pushed steadily, 'til maybe two inches of my cock were now inside her ass. I stopped.

"How does it feel, T?"

"Weird -- but good." The right answer. Then the words I was hoping for. "More, Chase?"

More. I slid my cock out, then in, a few times, to get T used to the feeling of a cock moving inside her ass. Also, because it felt so damned good! Her ass was silky, and tight, and the feel of it sliding along my cock was incredible.

But even more incredible was the thrill -- the thought, that I was moving around in the ass of a young girl, a young girl who'd barely had a cock inside her anywhere, and now I was in her, inside her young ass, fucking her.

Time to go on. I shoved, and another two inches of my cock went into Tanya's ass. I stopped again, and I waited -- this time to see if T would do anything.

She did. After she decided that I wasn't going to move, she thrust her hips back against me. It didn't make me go any deeper into her, but it let me know that she was ready for me to do more. And where we were now, "more" meant "all the rest."

I put my free arm around her and pulled her to me, and I kissed her shoulder. "You're doing great, T. I feel so good, being inside you."

I didn't expect a response from her, but I got one. She took my hand and pulled it to her, and she kissed it.

That was the reassurance I needed. A slight in and out, then the final push -- 'til I bottomed out in Tanya's bottom. My groin was pressed tight against her slim ass and the tip of my cock felt like it was pressed against the end of her rectum.

To put it crudely, I was balls-deep in little T's little ass.

I squeezed her, and I whispered, "We did it! You did it, T, I'm all the way in you -- you took me all the way inside you!"

I heard her as she almost squealed delightedly to Tim, "Tim -- he's all the way inside me, Tim! He's in my bottom, just the way you guys do."

"Yeah, T -- exactly like Chase and I do. I'nt it great?"

"Full. I feel so full." Then she added, "Is that right -- that I'm feeling so full?"

Tim quickly assured her, "That's right, T -- feeling full is right, exactly the way it feels." Then he added, "That feeling of being full is why Chase and I -- and other people -- love it so much."

"Will it always feel this way, every time I do it?"

"Yes, it does -- it will."

Yes -- every time, our little darling.

Now that I'd done my job, carefully and lovingly initiating T's ass, I felt I'd earned the right to get a little pleasure for myself and I started the steady in-and-out that makes ass fucking feel so damned good. I did it slowly, out of consideration for T's virgin ass, but it also allowed me to savor the incredible feeling -- the feeling of my cock sliding in and out through the hot, wet velvet of a young ass. I half-closed my eyes and let myself get lost in the whole thing -- Tanya's warm, smooth body in my arms, my groin pressing into her slim ass, and, of course, her rectum, holding my swollen cock in its soft, tight grasp. I kissed her shoulder and thrust into her again.

Tim, though, was laying facing Tanya, looking in her eyes, and he saw something.

"Chase."

"Yeah."

"Chase, I think maybe it's time to bring it on home."

I immediately knew what he meant. Tim could see the signs that things were starting to get uncomfortable for Tanya, and he -- we -- didn't want that to be how she remembers this. I moved my free arm from Tanya's shoulder and slid my hand down to her pussy -- to find Tim's hand already there, helping T with his finger on her clit.

With Tim taking care of that I could finally focus on myself, and I began taking the long in-and-out strokes that I knew would bring me off. That stimulation combined with picturing my cock sliding through T's young asshole, and in ten or twenty seconds I felt the familiar pulsings in my cock.

A final thrust, and I felt myself releasing -- one-two-three-four-five spurts, deep in Tanya's ass, and I heard her cry of "Ohhhh ... that's ....."

Tim intensified his efforts on Tanya's clit and was rewarded -- we all were rewarded -- when she cried "Fuuuuckk," and her body started jerking, as hard as we ever saw her cum before.

I managed to hang on -- and stay in -- through her climax, and after she settled down I stayed in her, my cock just "lounging" there in the warm bath of her rectum and my cum. Finally, slowly, I eased myself out, feeling the small "pop" as my shrunken cock came free of her sphincter, accompanied by a little "Oh!" from Tanya. I just had to hug her a little tighter for that.

We realized that we were thirsty after ... after what we just did. Tim held out the Mason jar full of water that was on the bedside table and we both took long slugs. Then I laid back on the pillow and T laid on her side, her back still toward me, snuggled up against me. I put my arm around her, and the two of us drifted off to sleep for a few minutes.

When we woke up from our little nap, Tim was the first to say something. He knew better than to ask "How was it?" or "What was it like?" Those answers are sometimes just too hard to find the words for. Instead, he asked, simply, "So, T -- didja like that?"

I figured she would have trouble finding words to describe how she felt. Instead, she surprised both of us by answering quickly -- and economically --

"Yuhhh!! I mean, yes." Then she added, "I can see why you guys like to do it so much."

Well, slightly impertinent, but Tim and I smiled -- at her obvious pleasure, and at her revelation that she now understood "why we like to do it so much." So I guess that's the best outcome we could wish for, and that our preparations had worked like we hoped, and apparently it was a good -- a really good -- experience for Tanya. Our Tanya.

So Tim cautiously asked, "So now that you've tried it, is that something you might want to do again sometime ...?"

And to our relief, and to our delight, she blurted out, "Sure -- yeah! When?"

But then she thought about it more and asked, "Can we wait a while, 'til I don't ... 'til it doesn't hurt as much, and then we can do it some more?"

What were we going to say -- No? "Of course, Hon, whenever you feel it's right and you're ready to do it again, right, Chase?"

"Absolutely. And T, there's no rush at all. It's for you, whenever you want to do it."

She exhaled, and it was almost like a sigh of relief.

"That's good. 'Cause next time I think I can do it better."

God bless this strange, surprising girl.

* * * * *

We rested there in bed a little longer. Then I turned to Tanya. "Ya' know, T, now that you and I have finished, there's something that you can do for Tim ..."

I was about to explain just exactly what it was that she could do for Tim when she spoke up.

"I know what Tim wants -- now that we're finished, Tim wants to know if he can lick my bumhole."

Tim and I busted out laughing.

First, because she's learned so much about us, and especially about Tim, that she knew exactly what it was that Tim wanted. And second -- the way she burst in with her extremely "candid" description of what Tim wants.

She turned red, her pale skin blushing all the way all the way down her neck and to her chest. "What? Did I say something wrong? What??" I thought she might cry.

We threw our arms around her and hugged her. Tim kissed her. "No -- no! You didn't do anything wrong -- you said everything right -- just perfect! Chase and I were laughing because you surprised us -- we were just surprised you know us so well already, weren't we, Chase?"

Once we were sure that she was reassured, Tim brought things back around to the original subject.

"So -- how about it, T...?"

"How 'bout wha... Ohhh -- I know..."

She pivoted around on the bed and carefully positioned her leaking bum -- right over Tim's face.

Now, I know that I don't have to tell you all the details of Tim licking Tanya's butthole.

I don't have to, but I will.

Tim was all set to grab Tanya by her hips and guide her down over him, but before he could, Tanya squatted on her knees right above Tim. Then she lowered herself into an almost-sitting position, with her bum just two or three inches above Tim's mouth.

And she sat like that, and she waited for Tim to do his thing.

Tim turned his head to look at me, like, "Do you believe this is happening??"

It looks like we're past the point where it's up to us to guide young, naive, inexperienced little Tanya through her part in our sexual activities. Instead, it seems that in her brief time with us, she has learned how to behave ... well ... pornographically. Not that we're complaining, mind you. But it seems like we've created our own little libertine.

Tim used both hands to spread those slim butt cheeks, then stopped, like he just wanted to enjoy the sight ... the sight of that little red-brown orifice, not quite gaping but still enlarged from taking my prick up inside it -- and still leaking that irresistible blend of my cum and T's ass juices, with just a bit of liquefied lube.

Tim lifted his head a little, but then he surprised me -- and probably Tanya -- by not inserting his tongue directly into her bum or slurping up the juice that was leaking from her. Instead, he extended his tongue, but only enough to run it around the rim of Tanya's hole -- to literally rim her ass. I could see from this that Tim was going to be taking his time enjoying our young girl's asshole and its juicy bounty -- that he was going to make things last just as long as possible.

And speaking of pornographically. The way he was doing it -- the extended tongue, the slow excursions around the outside of her bum hole, the quick darts into the dark opening before withdrawing and making another trip around the rim -- I could practically feel the resilient, wrinkled flesh, the oily drippings, the faint, erotic taste of ass on my own tongue. The way he was doing it, I could close my eyes, and in my imagination I was pulling her hips, her ass, down to my mouth and lips. The feel of her smooth skin on my nose and cheeks, and my own tongue, penetrating, probing her hole and lapping up the juices that I had helped put there -- it was all so real ...

... and then my reveries were penetrated by an unfamiliar voice. Even more, that voice was saying unfamiliar things.

"That's it, Tim, suck it. Suck my bumhole -- yeah, like that."

Tanya -- our little Tanya -- was talking filth to Tim!

"Yeah, do it -- stick your tongue up my dirty little butt ..."

In one way this shouldn't be surprising, after we saw how T took charge of the current situation, getting over Tim and placing her dripping asshole right over his face and his mouth. To say that she's become more comfortable with Tim and me and what we do is looking like a colossal understatement! To put it in street lingo, it seems she's down with what we do and how we do it, and she wants to be a full partner in it. Before, I wouldn't even have thought of it, but now that it's happened, it's like ... like the fulfillment of a nasty fantasy I didn't even know I had.

Well, since I was knocked out of my previous fantasy, I decided to get into the current one -- the one that was going on right next to me in bed. Tanya was sitting over Tim, her spread ass cheeks pressed against his face. Her right hand was between her legs, frantically grasping at her pussy, shoving three and even four fingers inside her, while her other hand was on one tit, squeezing, pinching the nipple, then pulling on it before squeezing her tit again.

And all the time pouring out a totally unexpected stream of filthy talk:

"Oh, you dirty man. You like that, don't you? You like sucking the dirty juice from my little-girl butt hole, don't you, Tim." The way she said it, it wasn't a question.

There's no way I could just sit and watch this. Tim's labial and lingual explorations between Tanya's butt cheeks was obviously turning him on, and I watched as his cock thickened and started to rise from his shaved crotch, enough for me to know what it was that I wanted to do now.

I got down in between Tim's legs and took his cock between my thumb and fingers and held it steady as I put my mouth down over it. What surprised me was the taste. There wasn't any. Or at least, not much. Then it dawned on me -- while I had been getting my rocks off deep inside Tanya's ass, Tim's cock hadn't been 'anywhere' since we'd all bathed together in the lake.

But that was OK, because he still tasted like Tim -- male, with just the slightest bit of sweat. Then the pre-cum started to leak from the cute little hole at the end. I dragged my tongue tip through the leaking slit, and Tim's hips bucked slightly in response, and that was my cue that my attentions would be appreciated.

So I probed his pee-slit a little more, then rolled my tongue around the crown of his cock, then put the whole crown into my mouth, and by then he was hard enough that I could start sliding my lips up and down his cock, feeling the satiny skin slide along my lips as I took the hard bundle of flesh deeper and deeper into my mouth ...

... and that's when I felt something on the back of my head.

Tanya had her hand on the back of my head, rising and falling as I moved my head up and down the length of Tim's now fully-hard cock. It was OK, and in fact, I liked the contact, liked that way T was helping me to suck Tim's cock.

But then she got more ... I don't know exactly how to put it -- "assertive." What I mean is, instead of just resting her hand on the back of my head, she started using it, to push me farther down Tim's cock. She'd apply some pressure, 'til I was all the way down, and then relax, just resting her hand so I could pull back off, then she'd push again, 'til I was all the way down again, then lighten-up once more.

Then I realized -- she was doing more with her hand than just "riding" my head up and down. Nope, she was actually forcing my head, farther down Tim's cock each time, forcing it deeper into my mouth -- into my throat. She was helping Tim to throat-fuck me. I don't know if that was her plan, or if she was just getting so turned-on by the whole scene, but the idea of what she was doing -- it excited the hell out of me!

One time when I was pulling back off Tim's cock, I tilted my head back, as much as I was able and rolled my eyes up to see T, her one hand still groping and grasping at her kitty while her other hand was doing its job on my head, and again I was able to picture it all:

Tim, his face and tongue buried -- burrowing -- into T's ass, still working to extract whatever goodies were still in there; T, sitting over Tim's face, one hand alternating between her tits and her pussy, the other hand forcing me down on Tim's cock; and me, between Tim's legs, my face buried against his shaved pubes, with T's hand forcing me so his cock is pressing against the back of my throat.

Then T starts saying things to me, encouraging me -- "That's it, Chase -- suck it. It's so exciting, watching you ... with Tim's -- Tim's thing in your mouth."

And it was. And then T said, "Is Tim going to cum? Are you going to make Tim cum in your mouth, Chase?"

Of course I was going to make Tim cum in my mouth.

And then, "When ya do ... can I have some too?"

And that did it ... for all three of us. Yes, Tim was going to cum, because I felt the familiar pulsing, first with my fingers, then the stiffening and swelling inside my mouth.

cvandrews
cvandrews
363 Followers
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