Chapter 9: Tanya Gets Her First Anal Experience; Tim & I Contribute

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??”