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Jenna’s Anal Tryst: Part 2

Jenna’s Anal Tryst: Part 2

Update: 2025-03-15
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Jenna Teaches hubby.

Based on a post by m jar65, in 2 parts. Listen to the Podcast at Steamy Stories.



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One week later Nick and I were in the same hotel again and quickly we were naked and fucking. Again there was lots of oral and I sucked his cock nice and long and Nick ate my slit till I was cumming all over his face.

I was so ready and so wanting that cock in my backside that Nick had to calm me down. Soon he was eating my slit and slipping a finger in and out of my ass. It was just as sensational the second time and I loved the stretching and the rubbing inside my little hole. Nick was so wonderful and he just kept going till I came in his mouth twice. Then he flipped me onto my front and straight away I got myself into the right position for him.

This time my rim job felt better and lasted even longer. I was moaning out loud for him and really I loved every moment of that ass licking, the feeling of having a man focus so much attention on my delicate anus. I came nice and hard for Nick as he thrust two fingers into my slit while his soft, warm tongue lapped at my hole.

Nick was such an expert he knew just how to handle me. As soon as that orgasm flowed out of me I was flipped back and this time I had two pillows under my hips. I was panting hard and it wasn't the after effects of my receding orgasm. I knew the moment had arrived and I was about to take a rock hard cock deep into my asshole.

He pulled on a condom as I stared at his hard cock and tried to imagine that bulk stretching out my backside. He didn't go straight to my ass though. First he dipped his cock into my slit. I admit I felt a little disappointed but soon enough I was huffing and panting as Nick did his magic and made my body ready to explode. I thought briefly how exciting it felt to have a different man take my body.

I was so close to cumming again when Nick positioned the head of his cock against my rear entrance. I was horny and desperate and wanted that cock so badly. I watched him apply a little lube and then he told me 'rub your clit for me. Make sure you are giving yourself some pleasure in case it's too big the first time.'

I understood just was he was saying. Just the head of his cock pressing against my hole felt like the biggest thing I had ever taken. I still wanted the rest of it, to take his whole cock. So I strummed my clit just as he asked. I wasn't scared but I was worried we might fail at the first hurdle.

I was panting and playing with my clit and the whole time Nick never took his eyes off mine. This was it, finally taking a hard cock up my ass.

'Here we go,' he said quietly. 'Try to relax for me.' I felt him press forward and I knew even then my anus was struggling to open up for him. The trouble was that I was so excited I really couldn't relax anything. I was going to have a hard cock shoved into my ass and even the thought that it could hurt didn't slow me down a bit.

Nick applied a bit more lube and with a sudden push he was inside me. Oh shit, his cock suddenly felt enormous and for a moment I was sure I'd never take the whole thing inside me. I kept playing with my clit, trying to adjust to these new sensations. I wanted that cock to go all the way.

After taking a tongue and then a finger, the head of his cock was really stretching me. I was scared but I was loving the feeling already. Carefully Nick started pressing deeper and the 'filled up' feeling got stronger. I was amazed that I could take so much in there. It felt weird but so good at the same time. A big hard cock in my backdoor and it was so new and so sexy at the same time.

He was pushing deeper and I was getting more and more filled up in that weird way. Each time he pressed forward I knew I was taking still more of that big hard cock inside my forbidden little hole. I was amazed at how much I could take and how good it felt. Oh fuck, I was loving it even though I also felt like using the toilet.

Suddenly there was a tearing and burning sensation. Nick must have recognized my expression because he actually withdrew a little and applied some more lube. I was still panting madly and so worried that this was my limit.

'Keep rubbing that clit,' Nick told me. 'You are so close so let's go slow and gentle.'

'Don't stop,' I gasped and panted at him. My slit was feeling so good and I was experiencing the weirdest and sexiest sensations I had ever known. Having even a part of his cock in my ass felt so dirty and erotic that I was anxious to take him all. I was being stretched and filled in the 'wrong' place but my body was telling me that everything was exactly right.

Women know the sensation of a big hard cock filling up their vagina. Instead of that I now had that cock in my ass and although it was a weird feeling my body was heating up and my tits were tingling.

Slowly Nick started to pulse his cock in and out of my ass. I was such a newbie I didn't even know what that meant. Slowly he was working himself deeper and deeper into me and soon I realized things felt very different. He felt huge in there and part of my brain worried I might burst. But the excitement from that big thing moving in my ass overwhelmed everything else.

'You've done it,' he said to me with a smile. 'My whole cock is inside your ass. How do you feel?'

'I don't know,' I panted. 'It’s weird but it feels so great. Fuck me now. Fuck my ass with your cock so I can feel everything.'

Nick started to pulse back and forward again but this time his cock strokes were longer and he was starting to use a little more force inside me. 'Does it feel good?' I asked him anxiously. 'Does my ass feel good?'

He smiled and went on fucking my ass. My first ever anal sex, first ass fucking, first ass reaming. I was in a kind of heaven but still I wanted it to be perfect.

'Your ass feels great to me,' he said with a big smile.

Nick's thrusting got longer and stronger and soon I was in a kind of reverie. The weird feeling was turning into an amazing glow right through my body and the 'filled up' sensations were starting to make me feel like I really needed to cum. It was the strangest feeling ever but somehow I knew that I was loving taking a cock in my ass.

An orgasm was approaching and now I didn't even need to rub my slit. The feeling of that hard cock and the truth that I was being fucked up my ass was all I needed right then. The sensation of him moving inside my backdoor and the rubbing against my insides was becoming more and more exciting. My whole body was starting to feel turned-on.

Of course I had no idea of what to expect or what would come next. But I knew what was happening when I started being overtaken by a massive new sensation and I realized that I was cumming while Nick had his cock up my ass.

Holy shit, I came with a cock up my ass. I'd never believed it could really happen. It happened to me, though, and on that very first time. It didn't explode like most of my orgasms. It just kind of erupted from some other part of my body and it swelled up inside me and suddenly my whole body was on fire and the most incredible release just came over me.

I tried to stay focused on Nick's cock thrusting into my ass hole but I just couldn't. It was the weirdest orgasm I'd ever had and even now I can't really describe it. But I felt so full and so sexy and so alive right then. I know I

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Jenna’s Anal Tryst: Part 2

Jenna’s Anal Tryst: Part 2

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