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Leading Him Astray

Category: Anal Sex
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Reid and I had been seeing each other for many months. Our sex was awesome. I knew by his expressions, the feel of his reactions, I could read him implicitly and he me. Best of all, we trusted each other.

He knew how deeply I loved having anal, and as his first experience that way, I was happy he enjoyed giving it as well.

It wasn’t that he was put off by it, just that his upbringing, his previous experiences hadn’t, in all his 43 years, brought it into play. His thick, long cock took some getting used to, but he was intuitive about using it, and though I would end up a little overdone sometimes the next day, it wasn’t because he was overly rough, or insensitive. He loved giving me those kind of orgasms, and seemed to be a little in love with the sensations he got from it, himself.

I knew, however, that for me to get the priviledge of giving him HIS first anal stimulation, would take some more convincing. He’d stopped my hand a few times as my fingers had trailed back that way, or merely shifted away. When asked, he just said he didn’t think that was anything he needed to try. When I pressed a little further, he pointed out that it was “kinda dirty down there.”

I told him that I loved it, and loved the way a guy’s cock reacts, hearing him react to it as well as the thought of doing it. I convinced him we could work on the cleanliness issue beforehand in the tub.

Reluctantly he agreed to let me try fingering him. His very first time, not even having had a doctor probe around in there. I was surprised by this, a little, but honored, nonetheless.

We bathed together, first. He’s very fastidious, anyway, and my previous experiences had never really led to any unpleasantness, but it did help us both feel relaxed. I was very excited, and nervous that he’d not like it after all, and he was just tense.

I soaped him, his thighs, his great ass, and his hips, then his cock and balls. I was reading his expressions closely, enjoying the leisurely exploration. He knew where it was going, and I did sense building tension. I had agreed with him that if he couldn’t relax enough, or wasn’t enjoying it, we would just drop it. For now. He knows me also well enough to know I’m pretty stubborn.

I let my finger slide along the bridge of flesh behind his balls and before his ass hole. I pressed and circled along the seam, feeling his cock through his skin, following it back, naturally. The soapiness as well as the water helped my finger glide easily. He was hard as a rock.

My fingertips played over his sensitive skin. I made no hint at anything other than worshipping his fine, strong body, and enjoying the reaction of it to my touch.

I smiled at him, whispering, “Are you ready for me to try a little?”

He nodded. I gauged his expression to be a little wary, but certainly horny.

“I won’t hurt you, lover. I promise, this will feel so fucking good, baby…” I spoke low, sweetly to him as I let my soapy finger slide through his ass crack. He was tight, alright.

I leaned forward to kiss and lick at his belly. Nuzzling, I then took his cock into my mouth, watching his eyes as he likes for me to do.

My lips closed behind the wide, flared tip, and my tongue-tip probed at the slit at the end, then flicked back and forth over it. I sucked hard, then blew, alternating his cockhead in and out of my mouth, already tasting pre-cum.

He was distracted enough that I let my fingertip rest at the opening, and once the initial puckering reaction had quelled, I stroked, then circled with light pressure.

He came hard with just that. Since we were here in the bath, I let it fly, amazed at the distance, and lapping up the odd puddles which had landed in the hollow of his chest, or above his collarbone near his throat.

I whispered softly into his ear, “See…look how hot that got you and I didn’t even get in the door. Mmm…are you going to let me have your tight ass, Reid? Let me take your cherry, my love.”

He enveloped me in a hug, and we laid there in the bath a while, floating. Puns aside, he wasn’t going to get off that easily.

To say he is straight as can be goes without saying. He’d been conditioned to think that any play in that region was wrong, dirty, and all the rest. He was also fairly open-minded and very suggestible to a hedonistic good time. I figured I could win him over to the “dark side.”

I laid a towel across the bed, and propped a whole bunch of pillows near the headboard. I kissed him, and laid him back on the pillows, his ass on the towel.

I put a good portion of lube into the palm of my hand, and placed my middle finger behind his balls, letting the lube roll down off my fingers and into his crack, and over the object of my desire. He spread his legs and raised his knees.

Sucking his cock, I let my tongue tease his balls from time to time. My fingers were working around behind them, and I laid the index, middle, and ring fingers in a point, sliding them through his well-lubed ass crack. Every so often on a pass over, I would let my middle finger dip in and up, dragging it over his crinkled, tight star. He shuddered, tensing.

I began fucking him with my mouth, knowing the sensations there would take his mind off of what was going to happen. I could feel that his opening had relaxed just a little, having grown accustomed to the feeling of my fingers around it, over it.

I let my index finger rest there so that I could find the right timing. His hole was alternately tense and relaxed, though the difference between these two states was not patently obvious unless some bit of pressure was applied.

Flicking my tongue in a zig-zag motion back and forth over the underside of his shaft, I muffled hums of happy satisfaction as he throbbed and surged on waves of pleasure.

I glanced up: His eyes were closed, his dark lashes downswept. Cheeks were flushed, and his mouth was partly agape, then clenched as he inhaled through his teeth. He had never fully dried from his bath, and his hair appeared damp at his temples. I could see the underside of his chin where his beard was trimmed, and noted that he was swallowing exaggeratedly from time to time.

One of his hands was gripping a post of the headboard behind his head, the muscles of his arm flexing sexily in his tense condition. The other was tangled in my hair, urging me as I sucked him off. I was so aroused, lying alongside his leg, bent over him, and about to invade his body this way. I squeezed my thighs together and shifted around to try and ease the sensations building within me.

His legs were laid open as I soothed him, and soon I was letting the very tip of my finger press into his opening. It wasn’t easy, though, and he gave a small, whimpering groan, though his cock certainly showed its approval by getting harder, the skin was shiny for it’s arousal and I loved the way it felt as I sucked it, licked and kissed along its throbbing length.

His sphincter was pulsing, fluttering around my finger and I knew well from experience that my finger in there felt huge, and was sending shockwaves bouncing back throughout his body. His muscular contractions tried to reject the invasion, but I maintained light pressure and soon encountered the second ring of constricting muscles, even more tightly closed than the first, which were just beginning to accept my finger’s presence there, buried in his ass.

His breathing was rapid, shallow. I turned my head from the task of sucking him to urging him to slow down, to take it easy, relax….

I asked him if it was uncomfortable and he said, his voice somewhat gruff, “Fuck, no, it feels so goddamn good….”

His body was convulsing, now, with the rhythmic contraction around my finger, every muscle and tendon would tighten and lock, then release. I let my finger ride these waves, it was almost as if he was tugging me into him, then alternately trying to force me back out.

I worked with it, my mouth working his cock, lips riding up and down his shaft, taking him into my throat, tasting the pre-cum building and oozing out.

When I found his spot, he locked up tight, frozen in place, every muscle trembling. His head thrashed from side to side and he let out a long, groaning, “Noooooo…..”

I felt his explosive orgasm hit the back of my throat. Choking, I pulled back, taking some into my mouth, then letting him cum in my face, into my parted lips. I stroked softly over his spot and he shuddered mightily, unleashing spurt after spurt of hot cum. It seemed as though I could force more of the hot semen from his balls just by pressing on his g-spot.

His body was arced upward, straining, and his skin was on fire. I watched his muscles bunching beneath his skin, entranced by the sight of him in this state. I moved my finger slowly, circling, stroking and touching his spot, then easing off. I licked and cleaned his cock, which was still as hard as ever even if his balls were drained.

Finally, he sighed, settling limply back into the pillows, the sweat covering his body cooling, and his head turned aside, eyes closed. His face had the most calm, peaceful expression. Rare for him. I slipped my finger very gently from his quivering hole, and dabbed at the lube with a soft cloth, then settled against his side to watch him drowse, laying my head on his chest. His hand moved slowly up to smooth down my hair, and he said sleepily, “Oh goddamn, babygirl….that was damn fine. Damn … fine….” His voice trailed off. He was sleeping, and I would let him. I wasn’t sleepy, yet, and so I contented myself with gently caressing him, watching him, and just enjoying his presence, my senses full with him.

I knew later, when he’d napped, he would rally for more. More of everything, and best of all, I knew he was going to let me explore this part of his body more, give him pleasure this way again.

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