I Love Anal Sex

I love anal sex. I love to watch it, read about, and especially have it. You could say I’m an anal fanatic so when I find a woman willing to give her ass to me I know I’ve found something special. As I’m sure you know, not every woman today lets a man stick his big, hard cock into her tight little butthole, but thanks to porn and the growing depravity of the world, more and more women are curious and willing to give it a try. Some take to it like a fish to water, some, once they’ve had it, prefer it over vaginal sex… that’s the kind of woman I can get behind (pun intended).

I’ve discovered it’s usually the middle aged woman. Women that have been married and divorced. See, what I think happens is the marriage and sex gets boring so they experiment and dabble in a little anal during their marriage and get a taste for it. Then, life happens, the marriage doesn’t work out and they find themselves single and for some reason horny again. They remember the anal… that’s the sex that they remember having with their x-husbands… for some reason it’s the most memorable… maybe it’s because of how he acted, how it made her feel… the taboo, the excitement… but they remember it.

So they find themselves single, horny and ready to get themselves back out there. Maybe have even started going to the gym, tightening up that thirty something body that’s popped out a couple kids already. They start losing the flab, getting their bodies back, seeing good things in the mirror after six months to a year after the divorce. They start to think, “I’m hot… I’m a catch now… my stupid x-husband will be so jealous when he sees me again, oh and man I’m horny, I need a good hard cock!”


Next thing they know they are out on the town the weekend their x-husband has the kids. All dolled up in their new skin tight, short mini dress trying to blend in with the 20 something’s at the clubs. I can spot them a mile away. Tonight it’s a blonde, on the edge of the crowd, trying to dance like the younger girls but failing miserably. She realizes it after a couple more songs and I watch her try nonchalantly to work herself out of the crowd to the bar. She sits down, orders a drink and looks around, hoping someone will come by and offer to buy her a drink. I let her sit until her drink is gone, the doubt shows on her face. I begin to wander my way toward her, making sure she can’t see me yet.

She’s about to leave, probably thinking to herself what a fool she is to come to a place like this at her age. Just as she stands to leave she turns and almost bumps into me. She has to raise her head to look up at my face and as she does her eyes widen slightly and she suddenly can’t speak. She mumbles an apology before trying again to leave.

“No need to apologize, it was my fault,” I say, catching her eyes again and keeping her planted to her spot.

She’s speechless again.

“Name’s Jordan,” I say, holding out my hand.

“Umm. Sam… Samantha,” she stutters.

“Can I buy you a drink, Samantha?” I ask.

“Umm… what? Me? umm, sure… I guess,” she says, totally discombobulated.

I kind of have this effect on women. It’s less with younger girls my age but with these more mature women it’s potent. Just the fact that I’m speaking to them at all is incredibly flattering. Yeah I know what you’re saying… what a conceited prick… I’m not bragging even when I say it’s just a fact. I’m just painting the picture for you.

So there we are, sitting at the bar again and Samantha finally gathers herself, smiles at me and remembers what kind of drink she would like. I can see the veins in her neck pulsing. Her heart must be pounding but she starts to relax and begins to comprehend what’s happening and that yes… I am truly interested in her. She is after all a beautiful woman… Her natural blond hair is curled for tonight’s ‘night on the town’ and the fake breasts her x-husband bought her are on full display in her low cut mini dress. Her skin shows signs of age on her face and above her beasts where she’s seen too much sun at the kid’s soccer games or whatever sport they play. Her blue eyes aren’t as bright as I’m sure they were ten or fifteen years ago but they are still beautiful. Smile lines show distinct around her mouth and the corner of her eyes, but all in all she’s taken good care of herself.

Her toned legs are crossed and I can still see the tiny outline of where her wedding ring used to be on her left hand. We make pleasant conversation, mostly about me because she doesn’t want to tell me how many kids she has, how long she’s been divorced or how horny she is. After we finish our drinks I ask her if she wants to get out of here. The relief on her face is blatant as is the excitement.

Once we’re in my car the thing I love about these older women comes bursting forth. She’s mature enough to know why we are both at the club and what we want tonight. The younger women make it way too hard and the chances of getting what I really want is severely diminished with girls in their twenties who haven’t had enough years of normal sex to be bored enough with it to try anal.

As I get in the driver side and sit down, she reaches across the car, grabs my head and pulls me in for a kiss. It’s hot and wet and I can tell she isn’t used to drinking much alcohol because she’s already half-drunk with just two drinks. The kiss lingers, sloppy and wet but tells me everything I need to know… sex is a lock and anal is more and more a possibility.

The kiss breaks, she’s still holding my face as we look into each other’s eyes. I say, “My place?”

“Yes, and drive fast!” she responds.

Samantha can’t sit still, she’s fidgeting with her dress and trying to figure out what to do with her hands as I drive, toward my place. I finally reach over and grab her left hand, placing it on my leg before returning my hand to the steering wheel. She gets the hint and soon inches it closer to my crotch until she finally bumps into my trapped cock and balls. She hesitates before moving again but soon is caressing my shaft through my thin slacks and jockey’s. It plumps up at her touch but can’t fully emerge.

“Are we almost there?” she asks.

“Almost,” I kind of chuckle.

Pulling into my driveway, she removes her hand as the car stops. I get out, walk around to her side and let her out. Inside, Samantha attacks me with the ferocity of a woman who hasn’t had sex for over a year it seems. As we kiss and tear off clothing, I lead her toward my bedroom and she pushes me over onto my bed when I bump into it. The mini dress is already off, she’s standing over me in just a matching black bra and panties that look brand new like the dress. She knows her x-husband paid good money for her rack and that’s the next thing she wants to show me. Unclasping her bra, she takes the straps off her shoulders, covers her breasts with her hands and lets the bra fall to the ground. She’s teasing me now as I lay shirtless on my bed with my cock still wedged in my pants. She bites her lip and removes her hands to show me her gorgeous c-cup enhanced breasts with small areolas and nipples. The surgeon did an excellent job. I smile, staring at them as the nipples gather and raise slightly. She climbs on the bed, hands find my pant legs and run up my thighs to the black belt she begins to work on unbuckling. She’s interested in the present she has yet to see beneath.

I’ve learned it seems to matter more to these older women. It’s almost like unwrapping a present to them. They never know what to expect but are looking for something the world and their own minds have built up to be important. With the belt and zipper undone, Samantha yanks down my pants leaving me in just my jockey’s but with a better view of what she wants to see. She grabs the waistband with one hand, pulls it down and with the other grabs hold of my cock, flipping it up onto my stomach. The smile appears, a large one. It’s at least as big as her x-husbands, maybe bigger from the look on her face, but it’s nothing to brag about.

As it grows, I take her by surprise and raise up, grabbing her around the waist and rolling her over onto her back. She giggles, moves some hair out of her eye and looks up at me. I kiss her, first on the mouth then neck, collar bone, upper chest until I’m bathing her breasts with small kisses as my hands move down her midsection to her black panties. She’s breathing heavy with anticipation, I make her wait a few more seconds before my fingers trail under the material to find a shaved mound and a very wet pussy. She moans loudly and arches her back into my hand as my fingers spread her open and dive deep into her hot and soaked insides.

I keep them deep as I suck on her nipple for the first time and find her clit with my thumb. She is already shaking, trembling in my grasp, so horny and wet I think she might explode before I even penetrated her with my cock. It has been so long since she’s felt the hands of a man on her she’s absolutely putty in my grasp. My fingers leave her body drenched in her juices. I rub them around her sex, coating her clit and lips with herself before testing the waters below. I can usually tell how good my chances of anal are with a simple brush of my fingers below the woman’s pussy to see how she reacts. I switch breasts, taking her right nipple in my mouth, pinning it amid my teeth and flicking it with my tongue as my fingers trail down toward her ass.

Samantha coos and responds encouragingly as my fingers brush her tightly puckered asshole. If she would have flinched or tightened up, I would have been worried. My fingers slide back into her and I suck her nipple harder before descending lower with my mouth, kissing her stomach slowly until my head’s between her legs and her fully ripe sex is before my eyes. She’s so smooth, I would guess she’s had a Brazilian wax or has taken a lot of time shaving herself for this night out. With my fingers deeply entombed in her sex, I suck on her clit and begin flicking it with my tongue. Her hands find my hair and she grips tightly, screaming she’s going to cum already.

I don’t stop and Samantha’s convulsions soon start as a powerful orgasm takes over her body, one that has been begging to be released for a long time. The fingers in my hair become painful but I ignore it as she shakes and screams her orgasmic grunts. I feel her contractions pulsing on my fingers as I try and continue licking her clit amid her movement. The climax continues for perhaps a minute before easing down. Her hands fall from my head and lay limp at her sides as she melts into my bed with euphoric bliss.

Her clit shrinks slightly, I stop licking it and remove my fingers from her sex with a downward motion so they glide over her anus again, which elicits no ill response once more. I raise my head and look up at her, her breasts are rising and falling rapidly on her chest, the nipples both hard and pointing to the celling. She opens her eyes and sees me looking at her.

She smiles, gathers herself and sits up slightly but is still too weak to fully rise. Instead her hand clumsily searches for my cock until she finds it. She pulls me up with it and I roll over onto my back. She holds me with all four fingers and her thumb as she rolls over onto her side before stroking me gently. It’s a bit awkward at first, but she soon remembers how as her grip eases and she uses the loose skin to stroke my cock. She gains more energy back and soon moves into positions to start sucking me. This is when I can really tell her lack of practice. She’s so timid it seems like it’s her first time sucking a cock. I’m sure she wasn’t sucking her x-husbands much after the first few years of marriage because she really had to remember how to do it.

I’m not complaining and I let her slowly remember and it begins to come back to her. She has me humming with my balls nestling up soon after getting used to having a cock in her mouth again. That’s when I rise up and spin her around so her pussy is in my face in the classic 69 so I can munch on her as she sucks on me. I play with her butt checks as I lick and tongued her hole and clit. Always with the thought of anal in my head. My hands inch closer and closer to her tightly puckered rosebud as she continues to suck my cock and stroke it as well.

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