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A Running Partner

Category: Anal Sex
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It was a nice, cool day out. It was a perfect day for a run, and even though I’m terrible at it, I felt like I really wanted to, because I love exercise – just not running. But, I wanted to run, so I did. It’s better for me if I run with a partner so I called up my friend Cheryl – Cher for short. She is one of the most beautiful women I know, making running way more difficult and uncomfortable, but she’s also very sweet and takes it easy on me, unlike other people I could ask.

“Hello?” Cheryl asked.

“Hi Cher! It’s me. I need a running mate, not for the presidential bid, but just so I stick to it. Can you join me?” I said.

Cheryl said, “Sure. I’ll be over in a few minutes; we can run the trail by your place.”

“That’s what I was thinking too. I’ll talk to ya then.”

When Cheryl got to my place, I happened to see her drive up as I was looking out my bay window. There’s a nice trail by my house – rails to trails – that is very flat, and fairly soft, for what it is. That makes it nicer on the knees.

We started first with a little jog. We ran to the beginning of the trail – about a half a mile in total. I always do this so that I can warm up and stretch before the bigger run. As I began to stretch, I looked up and saw Cheryl bend over. Her butt was so supple, so curvaceous, and so attractive. My penis immediately stood at attention. Uh-oh. Better turn around.

We began our run very lightly, jogging at a comfortable pace. Cher’s breasts bounced a little, though she was (smartly) wearing a sports bra to hold them in place, copious as they are. That didn’t help with the halfie in my pants at all though. We went another half a mile when I decided it was too irritating and asked for a stop.

“Already?” She asked.

“I’m sorry – you’re just too hot. I can’t run with an erection. It hurts too much. They don’t make sports bras for penises.” I said in reply.

She barked out a laugh and said, “Well, I guess. I’ll try not to be so hot.” With that, she sat down next to me on the bench we’d stopped at, patted me on the half-hardened crotch and I just grinned like a typical boy does when he’s getting attention from someone so beautiful.

Slowly, over time, the erection goes away and I test it out – it isn’t chaffing against my shorts, so it should be fine for the rest of the run. “Okay, let’s roll.” I say.

We begin again, running slowly but evenly. It’s a fun run, with occasional jokes going back and forth. At some point, I take Cheryl’s hand and slow down and then turn us around and we head back.

It was only about a mile in – the limit of my run-endurance these days – but it felt good. The run back was less eventful, and slightly less painful for me. When we got to the house, we were both sweating and stinky.

“Come in, we’ll get some water and clean up a bit.” I say. I unlock the door and we go in. I go straight to the kitchen and fill two glasses of water with ice cold water from the refrigerator. It almost hurts to drink because it’s so damn cold, but it feels so good.

“Do you want to shower first?” I ask her.

“No, why don’t you?” she says. “I’ll just wait, no problem.”

I grab some clothing and quickly hop into the bathroom. I turn on the water – I don’t really like it cold, even right after a run in which I get really hot – and put it to just somewhere between hot and cold. It’s a bit warm, anyway, and feels really good.

As I begin to soap up my hair (with my eyes closed), I hear the door open. I scramble to cover my genitals and ask, “Hey, you need somethin’?”

Cheryl says, “I was bored. Can I join you?” There’s a hint of coy curiosity in her voice.

“Um, sure, if you really want to, hop in.” I say, not knowing what to expect, or what she is expecting. My penis began to tremble again, though – you don’t even have to really be looking at her in order to be turned on by her, that Cher. By the time she got into the shower with me, I was at full salute.

“Hey! Nice cock. I like it – completely shaved down there! You clean ‘im yet?” She asked. Since I was still washing my hair, I imagined her staring at it hungrily.

I said, “No, just got started,” as I washed out my hair. I heard a little click, the soft sound of soap being squeezed onto a hand. Suddenly – when I’m still unable to see – I felt her hand begin to jerk my cock up and down, up and down. She made sure to wash around my balls and up my perineum. I even felt her reach up my butt a little and began lathering it up. I let out a long sigh, feeling out of breath as if I’d just finished a long run.

I finally finish washing the soap out of my hair and look at her like a wolf looking at a sheep. Her eyes are alight, and there’s a big smile across her face. I put my hand behind her neck and pull her toward me, smooshing her breasts into me. She can feel the hard cock against her stomach. I kiss her deeply and passionately. My mouth is a force to be reckoned with, my lips fighting hers, my tongue out-dueling hers. I feel her legs start to buckle ever so slightly and move my hands to her butt, holding her up. I slowly let up and lick her lips just a bit.

At this point, she removes my hands from her ass and let’s herself go down. The soap has been washed off of my penis, and she grabs it by the base. She licks the tip and I immediately hunch over in ecstasy. Her tongue is so hot, so wild. She puts the tip in her mouth and sucks a little. With one hand she starts massaging my testicles, and with the other she starts to reach around behind me and finds my butt. She presses a little bit, using a little bit of soap that was still there and didn’t wash off completely, and inserts her finger into my hole. I am gasping for breath now. She’s causing such intense feelings inside me.

As she begins to move her head up and down on my cock, and her finger in and out of my hole, I realize it won’t take me very long to cum at all. She licks the shaft up and down and slows down with the balls, knowing they’re still sensitive from the vasectomy. Her finger leaves my butt.

Given this chance, I grab her by the shoulders and force her to stand up. I feel the wall to make sure it’s not too cold, and then set her against it. I kiss her again and hold myself against her against the wall. I grab a little soap myself from the bottle, which she left open, and put it on her breasts. The shower head isn’t facing directly on her, so it doesn’t wash off right away. I begin washing her breasts in circles, cupping underneath them, then moving over top them and gently pressing down. When I get to her nipples, I caress them gently and move my fingers around her areolae, just loving the touch of her big, soft breasts on my hands. I pull her just away from the wall and into the water, rinsing off her chest.

Since I’m so tall at 6’4″, and she’s relatively much shorter, I have to go on my knees in order to get to her breasts, but I’m fine with that. I look into her eyes with innocence, rather than my wolf look, and put her hands in my now-clean hair. She grabs it and rubs my mouth on her breasts. She moves it to one of her nipples and, in a husky voice, says one word: “Suck.”

I begin gently, sucking on her right nipple and lapping at it with my tongue, flicking it up and down, left and right. I’m looking into her eyes the whole time, seeing her with power over me and loving it. I slowly increase the strength of my sucking, and eventually she starts to pull away. “Fuck kid. Sucking that hard, you should have been a gay man!” I laugh and sit backward full on my ass.

She looks at me perplexed, and I adjust myself so I’m sitting with my torso just out of the water. Her legs are the perfect length, I think, and I pull her over to me so that she’s standing above me. I stick out my tongue and begin to lick her labia. I lick all over, and she’s so turned on that she starts panting. She reaches down and grabs me by the hair again, pulling my tongue into her folds and lips. I begin to suck on the lips, and very, very, very gently nibble on them with just my lips. While I’m sucking, she decides she wants that feeling on her clitoris, and moves me to that little spot above her vagina. I know what to do – I suck gently while slowly moving my tongue, not directly on her clit, but near it. The feeling is quickly mounting inside of her, and I can feel it on my tongue – she tastes wonderful, and is getting wetter as we speak, and not from the water.

I reach around and begin massaging her buttocks. Within a few minutes, I hear her start to get very short of breath, and the look on her face is so beautiful as she begins to cum. She’s smashing my head into her now, my mouth, nose, cheeks and chin rubbing against her clit and vagina.

Slowly she pulls away from me. She beckons me up, and as I rise, she kisses me full on the lips. “Let’s go into the bedroom,” I say. She smiles and shuts off the water. We quickly towel off as much as we can and head into the attached bedroom.

Cheryl lays down on the bed, putting her hands behind her head lazily, staring at my body, hairless around the genitals but with hair on the chest and stomach. The muscles in my arms are obvious as I throw the towels into a hamper. “Roll over!” I say with a wicked grin. She rolls onto her stomach. I reach around the top of the bed, above her, and pull out what appears to be cooking oil. It’s actually delicious olive oil, and really very good for the skin.

I cover my hands in it after setting the bottle on the floor. I get on top of her, straddling her bare back, and begin rubbing my now-well-oiled hands into her back. I’m massaging her all over, focusing on her neck region, her upper-middle back, and her lower back. She can feel my still-hard cock on her butt cheeks. I’m not pressing too hard – don’t want to hurt her – but just enough that she starts to sigh and let out long breaths, almost as if falling asleep. When she’s totally relaxed, I use my hands to begin massaging her butt. It is so beautiful and sexy, her ass. I am only rubbing around the outside of it, and eventually I go up the slit and rub just over her butthole repeatedly.

My hands are starting to get dry again, since olive oil isn’t particularly known for its lubricative effects. I reach up to the top of the bed again and take out a different bottle this time. It is a bottle of my favorite lube – H2Jo. It works very well and is water-based. I open the bottle and let some drip onto her butthole. She lets out a small whimper because it is comparatively cold.

“If you get to do that to me, then I get to do it to you!” She says, laughing.

“Well, if you insist! But I take you first!” I say with a wicked grin. The lube is cool but not cold, quite comfortable. I put some on my penis and rub it around. Straddling her, I wipe off my hands on a nearby pillow and rub my penis up and down the crack of her butt. She is gently biting her bottom lip. I lean over her and start to kiss her back and neck, pulling her hair out of the way. I kiss her ear, her shoulders, her neck, between her shoulders, and her back. I put the tip of my penis up to the entrance of her butt, and slowly press down. She lets out a moan and puts a hand on my leg, to guide me.

I only have just the tip in, not wanting to hurt her at all, but she lets up on my leg a little and I go in another inch. She presses back and I wait a bit, despite my testes screaming to continue. She lets up again and I slide in another inch. It goes on like this for my whole length until she is breathing shallowly again, and can feel my scrotum nudging against her vagina. She leans back a little bit, and grabs my balls from underneath. She pulls on them until they rub against her clitoris. I start to move in and out very, very slowly. It is hotter than hot, like a white-hot fire. I lean over her again and begin kissing her on the lips as I slide inch by inch out, and then back in. I can feel her lightly pressing back, and eventually pressing back with some force, eager. I put my hands on her hips and am helping her to rock forward and backward now. I can feel my balls tensing up, getting ready to shoot. Suddenly my pushing in and out gets erratic, and my hands are squeezing her ass while simultaneously holding the cheeks apart. I start to moan, and as the fire builds, I reach a point where I can no longer hold it in, and I start to cum. I cum in her ass, and she keeps pushing back, as if trying to suck it all out with her butt. My whole body is convulsing in sheer ecstasy, my hands pulling back on her hips hard. I lean forward and collapse, slipping out of her.

She just continues laying there, but puts one of my arms around her. I hold her tight against me, the smell of sex strong. I reach over and hand her a rag from the side of the bed – where I store my sex rags. She uses it to wipe and clean off and throws it into the nearby hamper. She rolls over and kisses me lightly on the lips, smiling, putting her arms around my neck. I kiss her and hold her tight.

“Well, after that, we’ll have to shower again, dope.” She says with a snarky smile.

I laugh and say, “Yes, I suppose so. You wanted to do me, too? That’s a nice place for it, if you were serious.”

“I was! You got any way I can do that?”

“Yeah, let me find it.” I start to rummage around in a suitcase under the bed. I bring up a strap-on dildo that has a vibrator in it. The harness also has a dildo in it that sits inside the woman, inside of her while she penetrates her partner. I hand it to her, and she begins to put it on, slowly sliding the rather large dildo into her. It is a fat, pink-jelly dildo. It fits inside her snugly, and is wide enough to stretch her a little. She masturbates it in and out of her first, to ensure that it’s slick enough to get in, and slowly slides it all the way in. Once it’s in, she does the straps up and grabs the lube. The dildo that she will be using on me is about 6 inches long, and about an inch and a half wide at its widest – the perfect size for my ass. It is also the perfect texture – shaped like a series of ever-increasing anal beads, but one whole piece.

We get up and walk back into the bathroom. I grab a couple towels and set them on the edge of the tub, where I then kneel down, just low enough for her hips to reach my ass. She spanks me hard, and I let out a little yelp. I look back with hunger in my eyes, and she uses the lube first on the dildo, and then spreads some on my ass. She uses a finger to push it into me, rubbing near my prostate with her first finger, then slowly inserting a second. “Ahhhh,” comes the moan from me. She stands up and puts the tip of the very slick dildo on my ass.

She turns on the internal vibrator by turning the dildo, and presses very gently on my butthole. I can already feel myself starting to stretch and accept her greedily into my ass. I keep squeezing periodically, then letting go so that it can go in just a bit more. She gets to the full length, and has me well-stretched out and nearly cumming again.

She starts to move in and out of me slowly, each piece of the dildo stretching me a little more on the way in, a little less on the way out. The feeling is quite intense now, filling my whole rectum. I start to push back against her too, and she can feel my ass against her hips. The vibrator is vibrating both the dildo in me, and the dildo in her, and she can feel the pressure building up inside of her. She is slipping the fake cock in and out of me faster now, the vibrator tickling my prostate, and the pressure is building up inside of me, too.

As she starts to feel the energy getting ready to burst from her, she reaches around me and starts to stroke my cock. It’s hard to reach, but hard as hell. As she begins to cum, so do I, and we cum simultaneously, powerfully, and I can feel the cum squeezing out of my penis so hard, her hand not rough on it, but squeezing and masturbating it so hard. I carefully turn around and kiss her full on the lips just as she turns off the vibrator. She holds it in me and puts an arm around my neck and pulls me to her, kissing me harder. “Did you like that, my little boy toy?”

I am just breathing hard and kiss her again on the lips, so completely satisfied that I’m actually speechless – me, speechless, can you imagine that? She slowly pulls out and I stand up, filthy but feeling good. Also very weak in the knees. I take her arm and keep her balanced (and myself) while she undoes the strap-on and takes it off. We hop into the shower again and this time wash off completely. When we’re done, we go into the bedroom. I say, “Good night, beautiful, sweet princess.” We fall asleep in each others arms.

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