Hayley Asks For My Help

"Hey, Ben! How are you doing?"

I look up and smile at Hayley. "I'm great, how are you doing?"

"I'm good. Ready to do this 10 miles." She exclaims happily.

"I wish I shared your enthusiasm." I respond jokingly. "It's nice to see you here, I know you haven't been able to make it the last couple of weeks."

She pulls her hair back into a ponytail and then pulls it through her hat. "I know. School has been keeping me busy." She smiles at me, her light green eyes sparkling in the early morning light. "I was hoping you'd be here today. I always enjoy running with you."

The look she gives me is one I can't quite put a finger on, but I know it sends a shiver through me. A shiver of excitement. Sexual excitement. It's a look I've never seen from her before.

"I enjoy running with you as well. I'm always happy when you're here." I say smiling.

"You just like looking at my butt." She winks, smiling.

Wow, she's never said anything like that to me before. She's never flirted or hinted at flirting with me. This is new. "Well, what can I say? You wear those sexy tight shorts." What the heck, she brought it up, so I'm just going to go with it.

"Even when I wear split shorts, you stare at me." She laughs, clearly not offended by me oogling her.

"Oh, well, I'm mostly staring at your legs when you wear those." I joke. It's true, though. I'm always staring at her ass and legs when we run because they are the best ass and legs I've ever seen.

She keeps going. "I wear these tight tank tops and sports bras all the time. Are you saying you don't like my breasts?" Her eyes are playful as she watches my response.

"Now that's not what I said at all." I laugh. "I think you have fantastic breasts. Hell, Hayley, everything about you is sexy as hell." What the hell, we've gone this far, I may as well be honest with her.

She smiles, even blushes a little. "You really like them? I think they are small." She pauses. "And thank you, I think you're sexy too."

I had no idea she thought about any of this. We've been friends for 3 years now, and nothing like this has ever come up. "Big breasts aren't everything. I like small breasts, and yours are perfectly proportional to your body, and they have great shape."

She perks up and gives a big happy smile. "You just made my day. Thank you for that." She puts her hand on my upper arm and holds it there.

Before I can respond, the group leader announces that we are ready to start the run. Hayley and I start out with everyone else, and she speeds up just enough that she's in front of me. She then looks back and smiles. "Is this good?"

"Perfect!" I say as I take in the sight of her great ass and sexy legs. God, she is so hot.

Hayley is 35 and an absolute bombshell. 5'3", 110 pounds, long, wavy blonde hair.  She has the most shapely and amazing legs you've ever seen. Nice firm ass. Nice, tear drop shaped B cup breasts. Nice golden tan. Gorgeous light green eyes that I mentioned before. She's easily one of the sexiest women in the entire city we live in. She's a member of the run club, which is where we are now. She has a large following on Instagram, and she's also the assistant principal of the high school that my son attends. I should mention she's also married and has two children of her own, which is why we've never flirted like this before. The whole thing has me a little off guard, but she is very much into it, so I'm going to flirt back. Let's see where it goes.

"I have a question for you." Hayley asks over her shoulder and then slows a step so we are now running side by side. "I know it's late notice, but is there any chance you could help chaperone for the dance tonight? Is Patrick going?"

I steal a glance at her breasts as they bounce up and down. "He is going, so yeah, I'd be happy to help you out." Patrick is my son, and he's going to the dance and then staying at a friend's house for the night.

"Thank you so much. We had someone drop out, and I thought of you." She smiles at me as we continue running.

"What should I wear for this?" I ask as we move along.

"I'm going to wear a nice but casual dress, probably just a simple little black dress. Dress pants and a shirt are fine. A tie would look nice on you." She adds, smiling.

The thought of Hayley in a little black dress and heels makes my cock twitch. "Sounds good. What time?"

"Dance starts at 7, so if you could be there by 6?"

"No problem."

"Thank you so much!"

We finish the run with the group. No more real flirting, but there were also a lot of people around, which could have had something to do with it. As we are standing at our cars after, and most people have left, Hayley smiles at me.

"I think that's the most we've ever flirted on a run. I enjoyed it."

"I enjoyed it too." I respond while opening my car door. "I always kind of treated you as off limits for flirting."

She opens her door and slides into the seat. She starts the engine and looks at me. "I'm not off limits." She pauses and then smiles. "I'm just choosy and very discrete. Are you cool with that?"

"Of course I am. I can be totally discreet." I reply, then add. "Choosy is good too. Means, I'm worth it."

She winks. "I think you're worth it. Don't let me down." She then puts her car in gear and drives off with a big smile on her face.

I'm trying to process everything that just happened as I drive home. I'm divorced, Hayley knows that, but she's still married. Is she unhappy? She must be. I have to admit, I've never heard her talk about her husband, and she never includes him in her Instagram.  She's clearly made it clear that she wants someone else. Could this lead to a relationship?

I spend the afternoon getting ready for the dance. Patrick is staying with his mom this weekend, so I message him and tell him I'll be chaperoning and he seems indifferent to it all. Teenagers.

The time to leave finally arrives, and I get to the school 5 minutes before 6. I walk inside, and Hayley is talking to a group of adults. Most are teachers, but a couple are parents like me. I know most of them, but she makes sure that everyone gets an introduction. She gives us assignments, and I smile to myself as she informs me I'll be helping her most of the night.

Did I mention that Hayley looks stunning? She is indeed wearing a little black dress, and wow. All the men were sneaking peeks. That's how good she looks. She's also wearing bright red 4-inch stilettos that make her calves pop and lift her ass. Combine it with the tight dress, and it's incredible.

"You look stunning tonight." I whisper to her as everyone disperses to their stations.

She smiles at me. "Thank you. Is it weird that I feel nervous being around you?"

I didn't expect that. "No, I feel it too. Like we crossed a line this morning, and now it's a matter of do we keep going?"

She looks at me with an earnest look. "Do you want to? You know, keep going?"

I smile and look around. "Of course I do. You're the sexiest woman I've ever met, and you're also an amazing person."

She smiles and puts her hand on my arm. "I'm leaving my husband, but I know you've been single for a while, and honestly, I felt like I needed to make my move before someone else snatched you out from under me."

"Wow. I had no idea you felt this way, Hayley. I feel the same about you, so I'm glad you said something." I look over at her. "I kind of wish we weren't here right now because you're making me crazy in that dress."

Her eyes sparkle as she glances around. "Crazy enough to be a little wild?"

I just grin. "Oh hell yeah."

She starts walking out of the gym and I follow her. We go down the hall and into the teacher's lounge. There is a small sofa along with some tables and chairs, coffee machine, microwave, and refrigerator.

"I know it's not romantic at all." She starts to explain, but I don't give her a chance to finish as I kiss her hard on the mouth and guide her to the sofa. She lands on her butt and then onto her back with a small yelp and a giggle as I lay on top of her. She opens her legs and I grind my hard cock against her pussy, which is barely covered by her very thin g string. Her hands fumble with my pants as she frees my cock, and grabs my shaft. She uses her other hand to pull her panties to the side and then rubs my head on her slit. She's soaking wet, and I slip inside her without much trouble. I get about halfway, pull out to the head, and push again. This time, I sink to the hilt, and I can feel her heels digging into my lower back as she squeezes me with her legs.

"Oh fuck yes! That feels so good." She cries out as she grinds her pussy against my cock.

I kiss her hard on the mouth as I start fucking her. She moans as my tongue dances with hers.

"You're so tight. Jesus." I say as I keep pumping into her. Her pussy is dripping and I can feel her juices soaking my shaft with every thrust. We both know we need to hurry, so it's all very rushed and intense. I reach between us and rub her clit with my fingers as I keep fucking her.

"Yes! Don't stop!" She cries, digging her heels in harder. They are sure to leave a mark on my skin, but I could care less. She cums with a loud groan, muffled by my mouth on hers.

As she cums, she tightens like a vice around me and I can feel my cock start to swell ahead of my own orgasm. "I'm going to cum." I say, looking into her eyes.

"Cum inside me." Is her answer as she kisses me again.

With that, I push as deep as I can, and unleash a torrent of hot cum inside her. My orgasm triggers her and she cums again, her entire body tightening beneath mine. We both exhale deeply as the adrenaline pumps through us. We kiss hard and I look at her as we start to relax.

"That was fucking crazy. Holy shit." I pull out and move to the side as she makes room for me.

"That's the most intense quickie I've ever had." She breathes heavily.

We both stand up and fix our clothes. Hayley grabs some napkins and cleans herself off and then smiles at me. "You came a lot. Jesus."

I just smile and kiss her gently. "I've wanted you for so long, and it was even better than I could have ever hoped."

"Mmmm, just wait till we have actual time to really explore." She looks into my eyes. "I can be free tonight after the dance, if you want?"

"I would love that. Patrick is with his mom this weekend. We can go to my place." I say, kissing her again. "I want to take all night pleasuring you in every way possible."

"That's the best thing I've heard in a long time." She kisses me on the neck. "We need to get back." We check the hallway and then head back to the gym for the dance.

The evening goes by quickly. Patrick has a great time, and I even see him dancing with a cute little brunette a couple times, which makes me smile. I also notice for the first time just how much other men check out Hayley. Watching her, flirting with her, out right hitting on her at times. She demurely turns them all down though. I catch her looking at me throughout the night and it makes my heart beat faster. I never knew she was interested in me in this way, and I can't deny that it's a huge boost to my ego.

At 50 years old, I do okay. I'm relatively handsome, still in great shape with the running and working out. I also enjoy golf. My hair is gray, so I keep it shaved at this point. I have blue eyes that I've been told are sexy. I'm 6 feet even and weigh 165 pounds. I have a nice cock, so I've been told. 8 inches and thick. I do okay with the ladies, but I haven't met anyone that really strikes my fancy until Hayley.

As the dance winds down, I say goodbye to Patrick and have a short conversation with my ex when she picks him up. Thankfully, we still get along well. As the last of the students leave, I find Hayley inside the gym.

"Ready to go?" I ask.

She smiles at me. "I am. I told my husband I wasn't coming home tonight. I can get a hotel room after we go to your place."

"Don't be silly, you can stay with me." I respond.

"Are you sure? I feel like I sort of just threw myself into your plans."

I can tell she is nervous, and so I hold her hands. "I want you there with me for as long as you want to stay. I promise."

"Thank you, Ben." She smiles, looks around, and then kisses me quickly. "I'll just follow you?"

We get to my house, and we both park in the driveway. Hayley pulls a bag out of her car and smiles. "I packed a bag just in case."

I put my arm around her as I walk to the front door. "You're welcome to just remain naked all weekend."

She smirks at me. "I don't know, I think you might be interested in what I brought."

I open the front door and let her in. I shut the door and pull her to me. "I can't wait to see it."

I kiss her hard on the mouth, and the same frentic energy from the teachers' lounge is there and even stronger. I push her against the wall, my hands pulling her dress up, and my fingers finding her wet pussy. I push two fingers into her as she moans and undoes my pants. She jerks me off as I finger fuck her snatch, both of us driving our tongues into one another's mouths. We're like two sex starved teenagers.

I guide her to the couch and lay her down. I then pull the straps of her dress off her shoulders and down her arms, freeing her breasts. She's not wearing a bra, and her breasts look amazing. Small, perfectly shaped. Her pink nipples jut out, and I take one into my mouth. It hardens instantly, and I suck on it as I flick it with my tongue. She moans softly, her back arching slightly. I kiss my way down her body, taking in her firm, strong abs. I get her dress off and then remove her tiny g string. Her pussy is beautiful. Shaved smooth, her lips hanging out ever so slightly, creating the perfect flower. I suck gently on her lips and then spread her with my tongue, tasting her sweet juices. She moans and spreads her legs wider, pulling her knees towards her chest. I put my hands on her legs and push them back, tongue fucking her gorgeous pussy.

"Oh god." She moans softly as I pleasure her with my mouth. I close my lips around her swollen clit and flick it with my tongue, making her moan and squirm on the sofa. She plays with her breasts, squeezing them and pinching and pulling on her nipples. I take two fingers and slide them into her opening, her walls squeezing me as I move my fingers around inside her, massaging her cervix and her g spot. She starts to buck, her body getting stiff as I find the right spot. I flick my tongue faster and fuck her harder with my fingers. When her orgasm hits, her juices flood around my fingers and her back arches, her hands grabbing my head and shoving it into her pussy as she grinds her hips in little circles. Her moans are loud and erotic, and when the second orgasm hits, she cries out.

"Oh, Ben!!!!" I feel her thighs tighten against the sides of my head, and she's grinding her pussy into my face so hard that breathing is becoming an issue, but I don't stop. I keep sucking on her clit and start to jackhammer my fingers in and out of her pussy as fast as I can. I make sure to curl them so that I'm constantly hitting her g spot. She looks down at me with a strained look on her face and I know she's getting close. She finally pushes my hand away and with a loud cry, she squirts all over the couch, with some of it landing on the hardwood floor.

"Holy fuck!!!" She exclaims as she collapses back on the couch, her breathing heavy.

I smile and kiss her stomach gently. I can feel the aftershocks rippling through her. "Have you ever squirted before?" I ask, looking up at her.

"No! Never." She says, still catching her breath. She takes a deep breath and lifts her head, looking at me. "I've never even had multiple orgasms until tonight. Jesus."

I move up and kiss her hard on the mouth and hold her face in my hands. "That is an absolute crime. I'm going to make you cum till you can't walk straight."

She moans and pulls my body against hers. "You can do anything you want to me."

I smile at her. "Anything?" I ask, my eyes playful.

She gives me a bit of side eye but then kisses me. "Anything."

With that, I move back down her body and push her legs up and back towards her chest, giving me a perfect view of her rosebud. I then lick the puckered skin around her hole, getting it nice and wet.

She moans loudly, wrapping her arms around her knees and holding her legs in place. "Oh god."

I tongue fuck her asshole, getting it nice and wet as I finger her pussy. She has another orgasm soon enough. After she cums, I move up along her body and kneel between her legs, rubbing the head of my cock along her slit, teasing her.

"You have such a gorgeous pussy, Hayley." I push into her, sinking deep into her tight, wet, canal. She moans and puts her hands on my chest as I hold her legs open. I love watching my cock fucking her pussy. Her juices making my shaft glisten as I start to move in and out. She still has those sexy red heels on, and they look sexy as fuck.

"Your cock feels so good. Oh god. Fuck me, Ben." She holds onto the back of the couch with her hand as I start to pick up the pace. Soon, the sounds of my hips slapping against her body with each thrust fill the room. As we fuck, she gets louder and louder till she has yet another orgasm, her body tightening and then exploding with intense pleasure. I push deep into her and hold my cock there, watching her cum. She looks beautiful.

I pull out and turn her over to her hands and knees. I push into her pussy from behind as she rests her arms on the side of the couch. I run my hands over her firm ass, admiring how sexy it is.

"Fuck, you have a great ass." I say as spread her cheeks and watch my cock impale her. Her pussy is dripping, and I scoop some  juices from her folds and smear it on her puckered rosebud. "Have you ever had it in the ass?" I ask as I tease her with my thumb.

"No, and I'm not ready for your monster cock tonight, but if you give me time, I'll let you fuck my ass anytime you want." She breathes, looking back at me.

I reach out and pull on her hair as I push deep into her. I kiss her hard on the mouth and look in her eyes. "Deal." I take my thumb away and hold her hip with one hand as I keep hold of her hair with the other, and I start pounding her pussy. She groans loudly, putting her cheek on the arm of the sofa.

I can tell from her moans that she's building towards another orgasm, so I give her everything I have, my balls tightening in anticipation. As she cums, I bury myself inside her and paint her insides with rope after rope of cum. She keeps milking me, and I keep cumming. Finally, I give her my last drop and collapse back onto the couch. She's breathing heavily, her body shaking with little aftershocks.

"Push." I say gently as I watch my creampie start to leak down her folds. I watch her pussy open and shut as she starts to push. I then lean forward and use my tongue to take a nice big scoop of our combined orgasm from her pussy. She moans loudly as I do it and then she turns and kisses me hard on the mouth as I push the mass into her mouth. She swallows and looks at me.

"That's a first for me." She smiles and kisses me again. "I had no idea you were so dirty."

I just laugh. "You've only seen the beginning."

She moans and throws her head back, laughing. "Oh god, why didn't I make a move earlier??"

I smile and pull her to me. "Guess we better make up for lost time."

We head upstairs to the bedroom and I glance at the small bag that she brought with her. "Are you going to show me what's in the bag?"

She smiles and jokes. "Don't tell me you're ready to go again?"

I take my cock in my hand and start stroking it slowly, making it hard again. "I should warn you, it doesn't take me long to recover and I can fuck a lot in one night."

She watches me stroking myself and takes a breath. "Good to know." She smiles at me. "Wait here. And keep that monster hard."