We have been together for over a decade and it took a while to get into butt stuff but in the last 3-4 years she and I have both allowed our bums to relax and have really begun enjoying anal play (I’ve even begun to really enjoy her explorations of me too!). On occasions she will ok a night of anal sex and I always hurry home. Sometimes in the past our attempts at anal have ended in me getting off but more often it ends in her saying “ow” (even after taking it reeeeeally slow) then running off to shower.
The last 2 weeks she has really opened up (pardon the pun) and allowed me in for a decent period of time in two attemps a couple days apart. God it was hot. I had to take it real slow easing myself in and then gently thrusting but any anal is great anal when you don’t get it too often. After a bit of this I am amazed she isn’t in pain, I am turned on enough but can’t thrust fast enough to get off, so I pull out and with about 5 strokes I blasted all over her upturned ass.
Then there is tonight. After a workday text offering another night of anal(extremely rare she pursues it without my asking), and a nice dinner, we went upstairs, to have some fun. I start by point blank telling her I want to go down on her for a good while and she happily agrees while undressing her amazingly athletic 5’6″ body. She leans back and spreads her long runners legs allowing my tongue to enjoy her pussy. She got it lasered a while ago and licking every inch of that soft hairless skin is absolutely my favorite thing on earth. Within about 10 minutes her thighs are clamped onto my head and she is grinding on my face. My spit and her developing wetness is everywhere and I am finally released only to trail a never ending thread of clear, thick wetness from my tongue to her clit. Flashing a naughty smile she flips around, lays on her back, and hangs her head over the side of the bed. I know this position. It’s heaven on earth. The curve of my shaft fits the curve of her throat and after a little warm up she can fit my whole 7″ down her throat. 5″ are easy for her, but in this position I can get the last 2″ in and when the mushroom head of my cock pops past and goes the last few inches into her throat I can only groan. After a few tries she can suppress her gag so I can fuck her face properly. Picture this: I lean forward onto her body and lay on her chest while her head hangs off the bed teasing my cock. My tongue teases her clit in this twist on a 69 position. With both hands grab I can then reach back, grab her hair and force her head up and down my cock. She doesn’t control this at all and as a well trained sub should, her hands lay patiently on the bed while I, rather violently at times, jerk her head up and down my shaft. She is a hot mess, hair everywhere, drool everywhere, wet gagging noises everything I pull her away long enough to suck in a breath. Looking back I see her tongue is out past her lips trying to tease my shaft even further as she chokes on my cock. (Jealous?! You should be, this is porn star deepthroating we are talking here!) After a few minutes of alternating my groans and her gasps I lift her up against me and kiss her deeply, allowing for deep breaths between kisses. She is a smiling, happy, turned on, drooley mess and we are both giggling. My hand finds its way to her pussy and it has gone from mildly wet to literally dripping her thick, slippery wetness down her ass crack in less than 5 minutes. Sometimes I feel a little bad about the extent of the face fucking but then I get this reaction every time and I remind myself she is loving every second of it and can speak up if she isn’t. My tongue is instantly back inside her to taste the new found wetness while my other hand fumbles in our bedside Drawer Of Sin for a jewel plug. For anal night she has washed very thoroughly and it is my absolute pleasure to slowly let my tongue drift from her pussy lips to her asshole. I love lapping at it and getting it slippery, flicking it and watching it contract while she giggles and moans. After a moment of this she asks for the plug so I add some silky silicone lube and slide the plug in eeeeeeever so slowly. Then we fuck. Hard. She starts by standing over me as I am on my back so I can get a good view of the diamond in her ass, then she lowers her pussy down onto me and bounces up and down slowly, all the while maintaining a (somewhat strenuous) squatting position so I can see the outline of her perfect round ass and pussy wrapped around my shaft. Dear God it’s heaven. Next she lays on her back and pulls out her favorite pink toy and starts teasing her clit while I pump away at her pussy. My cock shimmers and glistens in the dim light every time it leaves her wet hole. She gets close to orgasm but stops and says she wants to cum with me in her ass, but I won’t allow it yet. I want to feel her pussy clamp down on my cock while I fuck her before entering her ass. She complies and in no time she is bucking her hips against my hands, arching her back in that oh-so-sexy way, and groaning in ecstasy… Enough to put a man over the edge, but I manage to slow myself enough to resist an orgasm. Gotta keep my eye on the prize. And what a sexy, tight, soft prize her asshole is! In that laying position I slip a towl underneath her and then gently slip a lubed up finger inside her tightly clenched little hole, all the while the vibratory makes slow circles around her pussy lips. I wiggle it around and add more lube several times, pushing as much as I can inside her. Then it’s my cock’s turn to explore. The first 3″ is rarely a problem and over a few minutes I work myself slowly inside her, enjoying that first ‘pop’ as my engorged head pushes past her outer ring of muscles. The next ten minutes or so are spent ever so slowly inching my way deeper. It helps that I got slightly softer and less girthy. Her tight little asshole is literally squeezing the blood right out of my dick. It feels amazing. I notice this softness seems to make her more receptive to my entry so with a little gentle rocking back and forth I push deeper. Then my pubic bones are suddenly wet with her pussy juices. I am ALL the way in. Buried to the hilt in her ass and she is smiling still! She is proud of herself, I can tell. After a bit of tender thrusting in and out I ask how her pain level is and she insists there is none. Hard to believe, but she insists…And asks for more. I oblige happily and start a slow, deeeeep grind into her. With each thrust I pull out just to the point that the inner/lower muscles of her opening cradle the rim of my cock head, then I push back in until I can go no further. A string of her cum sticks to my stomach and I stretch it back and forth with each thrust until I slide two fingers into her wetness. I can feel my cock slide past my fingers through the thin wall of skin separating these two heavenly tunnels of pleasure. Her groans urge my fingers on and she asks for me to please “try to give her a proper pounding.” to see what it feels like. Her words not mine, I’ll remind you. I shift to a more athletic kneeling position and really start going to town, knowing that I won’t last very long. No resistance, no toes curled in pain, no furrowed brow, just her head back, mouth in a perfect ‘O’ and her hand furiously whipping the buzzing toy back and forth across her clit. “You better cum, slut, or I will instead” I tell her, and she wastes no time. In thirty seconds her breathing reaches a crescendo and all at once she clamps her legs together, her ass tightens noticeably on my cock, and she moans out a very long, drawn out orgasm. I’m instantly sent over the edge and immediately after her I clench down, beginning my orgasm. Normally I would have to control my thrusting so as not to cause her pain but tonight I slam my cock deeper and harder into her stretched asshole than I ever have before. By pressing on my perineum I can simultaneously stimulate my prostate a bit and hold back any ejaculate, and in doing this I lengthen and intensify the feeling quite a bit. Just as it starts to subside I pull out, release my hand, and let flow a massive flood of white cum onto her already cum covered pussy lips. Exhausted, we collapse onto the bed side by side and revel in the reality that we had achieved total pornstar status. No mess really, just lube, and cum everywhere. We giggle and cuddle for a while. She confirms that she wasn’t just tolerating it for my pleasure, but she was really, truly, loving it. She came while I fucked her tight little ass. That. Just. Happened.