Myfirsttime anal

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I had met this guy who was a friend of my best girl friend… I knew that they had been sexual together, but I still kinda had a crush on him, even though I was living with my boyfriend.

So this made it difficult — and also, this guy was married, so that made it even less likely that anything would happen. Anyway, we got to chatting on msn one day, and it turned out that he was alone for the weekend and kinda bored.

My bf was out at work, and I got quite flirty and suggested that we get together for some drinks and movies at his place.

He agreed, and that evening he picked me up. We got out a few horror dvds and went back to his place to watch them on the big screen.

We also bought some of my fave bourbon to drink. Anyway during the first movie, we drank a fair bit and I was getting brave, so I cuddled up to him and he put his arms around me — just like I hoped!

I was pretty scared about what he would think of my body because my breasts are not real big, and my pussy has never really grown much hair even though I was 19 … But he was really really into it.

I took off his top and loved his bare chest pressed against me. So then I felt more comfortable. He said he wanted to lick me until I orgasmed so I told him to go ahead!

It felt so good and before long I was moaning with pleasure. Anyway, after a while, he begged to see me bent over with my cheeks spread apart.

I was embarrassed about him seeing my arse like that so I put it off… but after a few drinks I eventually gave in and I bent over and spread my cheeks to let him have a close look at my arsehole, like he wanted.

To my surprise, he held my hips and started licking my arsehole up and down. After a while, we moved onto the couch, and he started massaging my back.

It felt so so lovely having his strong hands massaging my shoulders — it relaxed me so much. Every now and then I would feel his hard cock rub up and down my arse crack.

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Nicole could sense what might be coming but didn't flinch until my tongue reached her puckered arsehole.

It danced around the ridges on her surface before quickly pushing inside her constricted muscles a few millimetres, but her reaction was instant and uncomfortable, "Not with your tongue.

To see every inch of hidden detail so close-up was scintillating! My fingertips once again tugged gently at the edges of her sphincter, spreading her asshole slightly more open.

I returned my fingertips to the horizon of her arsehole gently massaging the surface again. When her body resisted, my hands pinned her closer to my body whilst my tongue distracted her back into sexual oblivion.

Dipping my finger through the tight opening proved difficult, I only managed to depress it inwards slightly so I awkwardly removed my wet fingers from her pussy and brought them back up to her opening.

With the slightest of dirty lubrication the tips of my fingers were already making progress, pushing their way into her tight arse.

The sensation was alien and familiar at the same time, reminding me of the newness of feeling your dick in a warm pussy for the first time.

Nicole's body rocked at the foreign intrusion into her butthole, but my grip held fast and my tongue worked harder on her clit to continue to distract her.

Not only did the anal grip on my moist fingertip tighten, but her mouth's grip on the length of my penis also tightened. The feeling of my fingertip in her ass for the first time was both driving us to the edge of climax.

I worked the digital rhythmic movements in her ass harder in time with the licks to her pussy and felt the wave of orgasm start to rock her body. It was then a magical thing occurred.

As her body arched, her asshole momentarily opened up, fully relaxed and dilated I slid my finger quickly in, past the first knuckle, and then her anal muscles tightened again.

As the second wave of orgasm broke against her body, she arched her body again, and her asshole flowered open and sucked my finger into the second knuckle.

I gently pulsed my finger in and out, eager to soak up the sensation of movement and suction. As the third and final wave of her orgasm washed over her I made one last push, inching my finger almost midway past the second knuckle, once again pulsing and arching my finger to feel the darkest parts of her body that I had never touched before.

With my finger nearly entirely swallowed up by her asshole, my face covered in the juice from her pussy overflowing in pleasure and my cock buried deep in her throat, I finally exploded a powerful stream of cum into her throat.

Shooting multiple spurts until my cock was left twitching in her paralysed mouth. Was that possibly the best 69 ever?

But the deviancy hadn't ended there. As we lay in a post coital embrace, our bodies entwined more deeply than ever, Nicole asked, "How many fingers do you have up there?

The sensation was so unfamiliar to her she couldn't tell what was in her ass or how far it had gone.

This may be the reason for her braveness, however it would turn out there had been ulterior motives. With my finger still static in her ass, she turned round to me and said something I thought only porn stars say in my dreams, "Fuck me in my ass.

I didn't stop to contemplate it any further. Sliding my body and still erect penis out from under her, I kept my finger inside her arse, gently massaging it and feeling the inside walls of her.

She reached down the side of the bed for her small tub of Vaseline. I wasn't sure if it was still the recommended lube for anal sex but I wasn't going to quibble.

Taking a lump of the lumpy moist Vaseline she reached behind her to spread it generously on my still hard cock.

It throbbed at her oily grip. Her hand glided over my balls, which seemed a strange thing to lube until I realised where she was going.

She stretched back to try and slide a finger up my crevice and into my arse. She partly nudged her oil finger easily in which sent a shuddering sensation of anticipation through my body but the position was too awkward for her to maintain.

So I took the tub of Vaseline, smoothing out parts on my penis with my left hand. I then returned my left hand to her arse cheek, spreading it widely and inching a glistening finger back to where the other was still comfortably embedded.

I spread the Vaseline around parts of her bum and coated my right finger as much as I could before trying to prize a second finger in.

Her arsehole was still tightly gripping one so as I pushed the second finger in I slid the second out. She quickly opened and closed back on the single digit.

I applied Vaseline to the other finger, still warm from its cosy time in her arse, before struggling to squeeze it back in. Eventually I had to stretch her arse cheeks with both hands whilst trying to fit both in at the same time.

Nicole seemed impatient or eager to have me inside her so she turned back and said, "Just put it in. Fuck my arse now, please!

The fingers were still getting in the way so I had to quickly let go and push the head of my cock in with some force and speed. Nicole's face seemed to wince but not complain.

My head was still only partially in so I tried gripping the base of my cock and pushing it through the opening but with little give.

So I then tried spreading her cheeks apart, sitting a little higher and pushing downward. I was slowly gaining a few millimetres in traction.

Eventually I moved to the best combination. I pushed her back down and grabbed both of her hands commanding her to spread her arse cheeks wide, whilst I grabbed the base of my cock to keep it firm and steady.

With one hand on the base of her back, I slowly but forcefully pushed downward. Gradually my penis inched closer inwards, pushing globs of vaseline out of her opening.

Unrelenting, I pushed harder and deeper until finally with a satisfying grip, her anal muscles swallowed the head of my cock and gripped it like a vice.

She gave a groan of pain, satisfaction and pleasure.

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