(I wrote this as part of a conversation with an online friend, but wanted to share more broadly. Thanks!)
So … possibly the single hottest thing about anal sex is just realizing it’s on the menu. Not just on the menu, you have that sparkle in your eyes and you HAVE to have it and you won’t be satisfied until you feel that special, most intimate, most intense penetration of a large hot cock sliding into your tightest little hole.
It takes me a minute to pick up on it, you’re large eyes shining up at me, glancing over your shoulder as you walk by. I’m embarrassed that I mistake it for a standard affectionate mood until you push yourself gently against me, one hand sliding to cup my rapidly hardening member and whisper up at me “I need to feel you in my ass tonight.”
Things move fast for a bit after that – scrambling to the bedroom, frantic making out, getting naked and sliding your PJs bottoms over your full rear as you wiggle your hips in anticipation. Then taking a breath, making sure to slow down and start taking it easy and not letting the moment sweep us away. There’s important steps and it’s important to prepare.
This involves getting you on your hands and knees, ass presented appealing to me me. Taking a few minutes to play with your pussy as you purr in anticipation, then lubing my finger first and teasing it into your tight little rear, first just up to a knuckle and warming you up, being patient despite your eager little mews of delight in your need to feel more.
After sliding up to the second knuckle as your breath quickens and finger-fucking your ass for a spell, it’s time to move on to prep step two – a small-medium butt plug, well lubed. Again an appealing little wiggle of your hips when you feel the tip press up against you, and slowwwwly working it in, fucking shallow little strokes and stretching you ever so slightly wider and wider open until finely you stretch around the widest point and, as your breath catches in delight, closes around the far side, drawing it all the way in.
After some gentle play with the plug, pulling it out to nearly its widest point and letting you draw it back in again, as your anticipation at having an even larger and deeper item probing your depths grows to a fever pitch, it’s nice to take a small breather to let the you relax and settle into the plug and also to let the anticipation build. This can take many forms, but I admit its among my favorites to lie back, naked, and let you kneel between my legs, letting you suck my cock to rock hard stiffness while thrusting your soon-to-be-thoroughly-penetrated ass waggle eagerly in the air, the base of the plug peeking jauntily out from between your cheeks. Perhaps in anticipation of the deep and thorough penetration you are about to receive you suck me eagerly, deeply, burying your face in my pubic hair and taking my cock deep, deep in your throat. But sadly this must be only a pre-amble, because bigger and better things are afoot.
When NOBODY can stand it anymore, I rise to my knees and move behind you. Slicking my cock thoroughly with plenty of lube, I slowly and gently draw the plug out of your ass – drawing a gasp of surprise at its sudden absence and a slight popping sensation as it passes your tight sphincter on it’s way out. Before the absence grows to alarming it is replaced with the feeling of the swollen head of my cock pushing gently against your ass.
“Oh please please I need to feel you” you exclaim, barely able to contain your need, and I’m no better, breath ragged in my eagerness to experience what it is to come. With all the patience I can muster, I slowly but insistently provide rhythmic pressure, as you wiggle yourself back against me as if pulling out a cork in reverse. Each millimeter deeper I push into you draws more and more fevered moans of pleasure, stretching you gradually further around the shining and slick head of my cock until, like the plug before it, it stretches to accept the widest part and the closes around the back of it.
Starting to take shallow but increasingly deep strokes I’m now working the slick shaft further and further into you, Grasping your hips and plunging ever so slightly deeper with each carefully and agonizingly restrained thrust of my hips, at times almost restraining you from pushing back too hard against me and taking more of me than I can handle. But surprisingly quickly my hips are slapping against your ass with deep, measured strokes as my balls slap against your pussy, which you furiously work with your fingers and my cock plunges into your deepest and tightest recesses. While the ring around the base of my cock is still very tight, the pressure on the rest of me is surprisingly soft and gentle, and while the sheer dirty hotness makes it hard for either of us to last *too* long, once the rhythm is established its surprisingly natural and comfortable to let loose a bit, taking your full and bountiful ass with long, hard strokes. Against all odds you urge me deeper, bucking back against me and demanding to feel my cock pushing further and further into your insides. I can feel the wetness of your pussy where your fingers work against my balls with each stroke as they slap against you and the pressure builds and builds. I try to be patient though, I intend to wait you out.
Coming together while ass fucking is truly stupendous – as your orgasm breaks over you and you let loose with hoarse, wordless cries of pleasure, you spasm around my cock, gripping and releasing in powerful waves and I can hold back no more – spilling into your insides with thick, ropey spurts pouring deep inside of you. I have read that one of the joys of the recipient here is that you can feel your lover’s cum splashing wet and hot into your innards, a thought that never ceases to turn me on tremendously whenever I think of it.
Finally there’s the less fun logistics of extricating yourselves from this position, the unique feeling of your ass squeezing me out …. if we are feeling kinky, we can linger to watch the cum slowly drip out of your ass, or just cradle each other in mutual congratulation for the advanced feat we just performed.
Source: reddit.com/r/eroticliterature/comments/amkyna/musings_on_the_unique_pleasures_of_taboo_sex