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The time had come: I was ready for my new boyfriend to give it to me in the ass.

I have always considered anal sex something above any ordinary carnal act. It requires care. It’s an intimacy that really can’t be matched. I have to seriously trust the guy I’m letting into my backdoor. So I save the anal experience for men I feel most comfortable with.

Noah had definitely earned his right of passage. We’d been hooking up for several weeks. He was a smart, sweet, decent guy. He was also ridiculously gorgeous — like a swimmer crossed with an underwear model — and he had a big cock.

But not so big that I couldn’t accommodate him in my rear.

Problem was, I’d given him every opportunity to fuck me in the ass. But he wouldn’t take me up on the unspoken offer.

I told my troubles to my best pal.

“Well,” Tiffany said, over wine at her place, “maybe you’d better make it a spoken offer.”

I sighed and admitted, “I just prefer the subtle dance. There’s something terribly romantic and magical about it.”

“But not if he doesn’t get the hint.”

“I can’t see how he’s missing it.” I set down my wineglass as I explained. “Last night, I’m on my hands and knees, facing away from him. I reached around myself, dipped a finger in my dripping pussy, and then rubbed it in a circle around my asshole. All the while I’m grinning at him back over my shoulder.”

Tiff raised her eyebrows and responded: “And he didn’t take the hint?”

“Nope. He shoved his cock in my pussy and did me doggy-style, which was awesome. But not the exact awesome I was really hoping for.”

We talked awhile more, but Tiff didn’t have any other suggestions for me.

But the next night, when Noah and I were getting ready to go out, I considered that he might be averse to anal sex. Maybe he thought it was dirty or sinful? Who knows? People can develop strange hang-ups when it comes to the many mysteries of sex.

We went out to dinner, but it was just the prelude to him coming back to my place. All throughout the meal there was a crackling anticipation between us.

When we got to my apartment, it was plain the evening was heading straight for the bedroom. He took me in his arms, and we locked lips. Noah was a hell of a kisser. He was also fantastic in bed, with all the stamina and imagination a girl could want.

There was just that one gaping blind spot. Anal. Maybe Tiff had it right. I should just come out and say it.

“Noah.” I held his hands and looked up into his eyes. “I’d like something different tonight.”

“Like, uh, what?”

“I mean,” I began but shut up. I was hesitant; I feared I might touch a nerve.

Mustering up my courage, I announced, “I want you to fuck my ass.”

He visibly flinched, and I felt a flutter of panic. I definitely didn’t want to spook this man. Oh hell! Why couldn’t I have kept my anal urges under wraps? Was it really such a big deal?

But it was. At least to me.

He swallowed anxiously and sputtered, “I — I don’t know if I can.”

“Why not?” I asked, keeping my voice gentle.

He hesitated, then admitted: “I had a bad experience with it once. I wanted to do it with this girl I was seeing. When I asked, she made this sick face. I told her to forget about it, but then she insisted we do it.”

“And you did?”

“Yes. Sort of. She bitched the whole time, muttering how gross and uncomfortable it was. Finally I just pulled out and split. Later, we broke up. I figured she’d been looking for an excuse to end it, and that was it.” He shook his head. “I guess I have a bad association with anal sex.”

I felt a flood of sympathy — and not a little anger toward the bitch who’d screwed with his head.

But an innovative solution occurred to me. I led him to my bedroom and told him to strip. I undressed as well, with excitement of a decidedly naughty variety tingling through me.

I gazed with fresh appreciation at his sculpted body. His cock was rising as he looked at me.

“So,” I said, “some part of you really thinks anal sex is nasty, maybe even painful. Right?”

He nodded.

“I’ll show you it’s not. That it’s wonderful. Will you trust me with this?”

Again, the nod. His cock was fully hard.

I told him to get on the bed, on his hands and knees, facing the headboard. Nonplussed, he did.

I got behind him. I licked my middle finger until it dripped with spit. In a soothing tone, I told him what I was going to do.

He tensed, but didn’t object when I slowly swirled my fingertip over the crinkled ring of flesh waiting in the valley between his perfect ass cheeks. He took a deep breath, and I saw his body relax.

My touch was soft, but I heard him gasp just the same. Tension seemed to leave him, and he subtly rocked back toward me.

“There,” I cooed, “isn’t that nice?”

He let out a soft moan, and I grinned.

I rubbed him with a little more force, going clockwise and counterclockwise. His asshole was firm but pliant, and he was groaning rhythmically.

“You ready for a little more?” I asked.

“Yes!” he gasped.

My plan was working! I pressed even harder until his hole opened just the tiniest bit. I let my fingertip sink inside, going a centimeter at a time.

“Oh fuck!” he uttered.

I stopped immediately and asked, “Are you OK?”

“I fucking love it! Finger me deeper, Cindi.”

This experiment was going better than I could have expected, so I drove my digit further into my boyfriend’s butt hole.

He could have freaked out right away, but he hadn’t. He’d kept an open mind. He had trusted me, and that warmed my heart.

I was being warmed elsewhere as well. This had started off as an instructional lesson, but now my pussy was flowing and my pulse was racing. I was totally turned on, and I was finger-fucking Noah’s ass!

His passage was tight, but his muscles were growing ever more relaxed. He took more of me, up to the first knuckle, then I sank in to the second.

Finally, I was in all the way. I curled my finger to stimulate his prostate. The action had an instant effect on Noah. He tossed his head, grunting with pleasure. He said “fuck, fuck, fuck” like it was some kind of carnal prayer.

I slid my middle finger in and out of his hole until he at last panted, “Cindi, let me put my cock in your ass!”

As quick as could be, I squirted some lube on my finger and greased up my hole, stretching myself with my slippery digits. Then I assumed his former position, on hands and knees. My body quivered with intense excitement.

I’d been wanting to get butt-fucked for some while, but the fact that I’d had to finger Noah’s asshole to get to that point made the victory all the more delicious.

My boyfriend hurried in behind me, still making lovely growling sounds. I felt him press his swollen cockhead against my lube-slick hole. The moment had arrived!

He pushed forward without hesitation, and I felt him pop inside. My hole gripped him lusciously, a lover’s sweet embrace. Familiar pleasure radiated outward from the point of contact as his hands closed over the globes of my ass. More of him drove into me, and I gratefully took every inch of his shaft.

It was the purest bliss — inventive, cooperative and trusting.

Vulnerable and horny, I was taking Noah’s big cock in my tiny rear hole, desperate to feel him pounding me hard.

Before long, his balls were pressed against my body. He was all the way in. I was speared deep, my ass channel clasping him like a fist.

He started stroking in and out of me, and I groaned in encouragement. My words appeared to have the desired effect. Soon he was giving me long strokes, pulling nearly out, then hammering all the way home in one unbroken plunge.

The orgasmic buildup began quickly. An anal climax was always a different beast for me, gathering in its own unique way. The deep-seated ecstasy started out as tendrils of arousal, moving about at my inmost point.

Sexual energy flooded my being. My nipples throbbed with an almost painful hardness as gooseflesh pebbled all over my body. My pussy overflowed with juice, and I felt heat pulsing along every inch of flesh.

Noah fucked me harder and faster. I felt the slap of his balls and heard his primal grunts as his pelvis slammed against my cheeks. He was no longer being delicate, and there was no need for him to be. It was perfect.

His breath huffed, and his fingers sank into the flesh of my ass. I cried out as a climax started in the well of my being and exploded outward. My howl was matched by his.

Hot jets of come erupted inside me, adding to my frantic elation. Noah pounded me until his last spurt of jizz had flown. Then we collapsed.

The good news is, he’s definitely no longer squeamish about all things anal. He still even likes me to finger him now and again. One time I did it while going down on him, and he came so furiously cream ran out of the corners of my mouth.

Maybe one day I’ll put on my strap-on and really give him some fun. But one thing at a time.

" />

Turning The Other Cheek

Storyline

The time had come: I was ready for my new boyfriend to give it to me in the ass.

I have always considered anal sex something above any ordinary carnal act. It requires care. It’s an intimacy that really can’t be matched. I have to seriously trust the guy I’m letting into my backdoor. So I save the anal experience for men I feel most comfortable with.

Noah had definitely earned his right of passage. We’d been hooking up for several weeks. He was a smart, sweet, decent guy. He was also ridiculously gorgeous — like a swimmer crossed with an underwear model — and he had a big cock.

But not so big that I couldn’t accommodate him in my rear.

Problem was, I’d given him every opportunity to fuck me in the ass. But he wouldn’t take me up on the unspoken offer.

I told my troubles to my best pal.

“Well,” Tiffany said, over wine at her place, “maybe you’d better make it a spoken offer.”

I sighed and admitted, “I just prefer the subtle dance. There’s something terribly romantic and magical about it.”

“But not if he doesn’t get the hint.”

“I can’t see how he’s missing it.” I set down my wineglass as I explained. “Last night, I’m on my hands and knees, facing away from him. I reached around myself, dipped a finger in my dripping pussy, and then rubbed it in a circle around my asshole. All the while I’m grinning at him back over my shoulder.”

Tiff raised her eyebrows and responded: “And he didn’t take the hint?”

“Nope. He shoved his cock in my pussy and did me doggy-style, which was awesome. But not the exact awesome I was really hoping for.”

We talked awhile more, but Tiff didn’t have any other suggestions for me.

But the next night, when Noah and I were getting ready to go out, I considered that he might be averse to anal sex. Maybe he thought it was dirty or sinful? Who knows? People can develop strange hang-ups when it comes to the many mysteries of sex.

We went out to dinner, but it was just the prelude to him coming back to my place. All throughout the meal there was a crackling anticipation between us.

When we got to my apartment, it was plain the evening was heading straight for the bedroom. He took me in his arms, and we locked lips. Noah was a hell of a kisser. He was also fantastic in bed, with all the stamina and imagination a girl could want.

There was just that one gaping blind spot. Anal. Maybe Tiff had it right. I should just come out and say it.

“Noah.” I held his hands and looked up into his eyes. “I’d like something different tonight.”

“Like, uh, what?”

“I mean,” I began but shut up. I was hesitant; I feared I might touch a nerve.

Mustering up my courage, I announced, “I want you to fuck my ass.”

He visibly flinched, and I felt a flutter of panic. I definitely didn’t want to spook this man. Oh hell! Why couldn’t I have kept my anal urges under wraps? Was it really such a big deal?

But it was. At least to me.

He swallowed anxiously and sputtered, “I — I don’t know if I can.”

“Why not?” I asked, keeping my voice gentle.

He hesitated, then admitted: “I had a bad experience with it once. I wanted to do it with this girl I was seeing. When I asked, she made this sick face. I told her to forget about it, but then she insisted we do it.”

“And you did?”

“Yes. Sort of. She bitched the whole time, muttering how gross and uncomfortable it was. Finally I just pulled out and split. Later, we broke up. I figured she’d been looking for an excuse to end it, and that was it.” He shook his head. “I guess I have a bad association with anal sex.”

I felt a flood of sympathy — and not a little anger toward the bitch who’d screwed with his head.

But an innovative solution occurred to me. I led him to my bedroom and told him to strip. I undressed as well, with excitement of a decidedly naughty variety tingling through me.

I gazed with fresh appreciation at his sculpted body. His cock was rising as he looked at me.

“So,” I said, “some part of you really thinks anal sex is nasty, maybe even painful. Right?”

He nodded.

“I’ll show you it’s not. That it’s wonderful. Will you trust me with this?”

Again, the nod. His cock was fully hard.

I told him to get on the bed, on his hands and knees, facing the headboard. Nonplussed, he did.

I got behind him. I licked my middle finger until it dripped with spit. In a soothing tone, I told him what I was going to do.

He tensed, but didn’t object when I slowly swirled my fingertip over the crinkled ring of flesh waiting in the valley between his perfect ass cheeks. He took a deep breath, and I saw his body relax.

My touch was soft, but I heard him gasp just the same. Tension seemed to leave him, and he subtly rocked back toward me.

“There,” I cooed, “isn’t that nice?”

He let out a soft moan, and I grinned.

I rubbed him with a little more force, going clockwise and counterclockwise. His asshole was firm but pliant, and he was groaning rhythmically.

“You ready for a little more?” I asked.

“Yes!” he gasped.

My plan was working! I pressed even harder until his hole opened just the tiniest bit. I let my fingertip sink inside, going a centimeter at a time.

“Oh fuck!” he uttered.

I stopped immediately and asked, “Are you OK?”

“I fucking love it! Finger me deeper, Cindi.”

This experiment was going better than I could have expected, so I drove my digit further into my boyfriend’s butt hole.

He could have freaked out right away, but he hadn’t. He’d kept an open mind. He had trusted me, and that warmed my heart.

I was being warmed elsewhere as well. This had started off as an instructional lesson, but now my pussy was flowing and my pulse was racing. I was totally turned on, and I was finger-fucking Noah’s ass!

His passage was tight, but his muscles were growing ever more relaxed. He took more of me, up to the first knuckle, then I sank in to the second.

Finally, I was in all the way. I curled my finger to stimulate his prostate. The action had an instant effect on Noah. He tossed his head, grunting with pleasure. He said “fuck, fuck, fuck” like it was some kind of carnal prayer.

I slid my middle finger in and out of his hole until he at last panted, “Cindi, let me put my cock in your ass!”

As quick as could be, I squirted some lube on my finger and greased up my hole, stretching myself with my slippery digits. Then I assumed his former position, on hands and knees. My body quivered with intense excitement.

I’d been wanting to get butt-fucked for some while, but the fact that I’d had to finger Noah’s asshole to get to that point made the victory all the more delicious.

My boyfriend hurried in behind me, still making lovely growling sounds. I felt him press his swollen cockhead against my lube-slick hole. The moment had arrived!

He pushed forward without hesitation, and I felt him pop inside. My hole gripped him lusciously, a lover’s sweet embrace. Familiar pleasure radiated outward from the point of contact as his hands closed over the globes of my ass. More of him drove into me, and I gratefully took every inch of his shaft.

It was the purest bliss — inventive, cooperative and trusting.

Vulnerable and horny, I was taking Noah’s big cock in my tiny rear hole, desperate to feel him pounding me hard.

Before long, his balls were pressed against my body. He was all the way in. I was speared deep, my ass channel clasping him like a fist.

He started stroking in and out of me, and I groaned in encouragement. My words appeared to have the desired effect. Soon he was giving me long strokes, pulling nearly out, then hammering all the way home in one unbroken plunge.

The orgasmic buildup began quickly. An anal climax was always a different beast for me, gathering in its own unique way. The deep-seated ecstasy started out as tendrils of arousal, moving about at my inmost point.

Sexual energy flooded my being. My nipples throbbed with an almost painful hardness as gooseflesh pebbled all over my body. My pussy overflowed with juice, and I felt heat pulsing along every inch of flesh.

Noah fucked me harder and faster. I felt the slap of his balls and heard his primal grunts as his pelvis slammed against my cheeks. He was no longer being delicate, and there was no need for him to be. It was perfect.

His breath huffed, and his fingers sank into the flesh of my ass. I cried out as a climax started in the well of my being and exploded outward. My howl was matched by his.

Hot jets of come erupted inside me, adding to my frantic elation. Noah pounded me until his last spurt of jizz had flown. Then we collapsed.

The good news is, he’s definitely no longer squeamish about all things anal. He still even likes me to finger him now and again. One time I did it while going down on him, and he came so furiously cream ran out of the corners of my mouth.

Maybe one day I’ll put on my strap-on and really give him some fun. But one thing at a time.

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