I mentioned my niece, Ally, in another story–I’ve got more to tell about her, but this one is about her mom from a few years ago. Dani was my ex-wife’s baby sister–7 years younger and completely different appearance. My ex-wife was legitimately beautiful in a classic sense–she had long legs and long brown hair to go with deep blue eyes. She was tall with curves and her ass was hard to ignore. Dani was cute, short, and physically fit but unremarkable. I always enjoyed seeing her walk by in a bathing suit during family gatherings, but she never was the type you’d break stride trying to get a look at. Still, whether it was the taboo aspect or just curiosity about how she compared to her sister, I had thought of her more than once when I was on the road and needed some inspiration.
Over the years, I think my apparent indifference to her took on more significance as she got older and had two kids–she wasn’t getting the minor attention she had before. Her husband, David, had taken advantage of her long shifts as a nurse to make time with the babysitters and then their daughter’s friends with teasing remarks that later turned out to be more involved. No plunging necklines or short shorts could change the fact that her sex appeal seemed to be fading fast.
I’m 10 years older than her, which I think led to her comfort around me–even as she became more self-conscious. We had some good talks and even flirted here and there, but I never gave the impression that I wanted more than banter. I mean, I did–I genuinely liked her and found her little mom-body kind of hard to stop thinking about, but I tried very had to keep that locked away due to the family situation.
The pretense was dropped around the time my ex and I shared news of our separation with her family during the annual beach vacation. It was all very amicable and we wanted them to know that I still wanted to be involved with their kids, but the coldness between us and our separate sleeping quarters made it clear that we were done.
The tradition at the beach had been a post-dinner pool party–we’d all hang out in and around the pool, playing with the kids, having some drinks, and relaxing. As it grew darker, the kids would head to bed, the drinking would accelerate, and the pool would give way to the hot tub. We usually went around Labor Day, so the evening could get a bit cool.
I love a cool breeze blowing over the hot tub–warm sensations on the inside from the alcohol, warm below the water from the heat, and growing colder above the water. No one else shared my appreciation for the warm/cool dynamic and I often was the only one in the hot tub at the end of the evening. Before our break, my ex would join me for a bit–as I spread my arms over the edge of the hot tub and looked at the darkening sky, I sighed and thought that I’d be doing a lot more things on my own again now.
I took another pull from the beer bottle and dropped down into the water, until only my head was above the swirling surface. I enjoyed feeling the bubbles pop against my face–I know I’m weird, but I like to indulge. My meditative state was interrupted by the sound of a sliding glass door and the footsteps on the deck behind me. I didn’t feel like turning around and figured someone was retrieving something they forgot outside. I turned around when I heard steps on the ladder to the hot tub. I was Dani with a dark one-piece (she ditched the bikinis after her kids) and a half-grin.
“Hope you don’t mind the interruption,” she whispered. “Half the house is asleep. Other half is watching a movie.”
I matched her volume. “No, not at all. Just drinking some suds while sitting in suds.” I sat up and put my arms over the edge of the hot tub.
She laughed louder than intended. The light caught her suit as she turned to cover her mouth and I noticed her hard nipples. I tried to ignore the interest this caused and averted my gaze. She gathered herself then dropped down the ladder into the water. She lost her footing and slid into my leg–immediately mouthing “I’m sorry” in an exaggerated fashion with hands raised.
After a few minutes of enjoying the jet massage, Dani scooted over beside me. I kept my arm on the edge and she put her head back against it, her short hair brushing against me. I could smell the scent of a strange shampoo as I felt her left hand against my chest. I didn’t move away and that was all the encouragement she needed.
She leaned into my ear and I could smell the wine on her breath. “You know, David is a piece of shit. No offense to you, but I wish I had the nerve that Jenn did to leave you.”
I snorted. “So this is going to be a nice relaxing conversation…”
She playfully splashed water at me. “I just mean, I wish I had the guts to leave a bad situation.”
“It’s a lot easier without kids involved,” I muttered as I took another drink. “I mean, we thought of your girls, but in the end it’s nothing like messing up your own kids.”
Dani shook her head. “Yeah, for sure. But that piece of shit has been chasing tail at the beach all day. Tail at best that is just out of high school. With his daughters watching. Oh yeah, and me too.” I felt her hand move across my stomach. “Then he has the nerve to 2-pump chump me after dinner. Fills me up and then goes to sleep. So I had an idea.”
I was genuinely curious where this was going, so I nodded to move the story along.
“I want a real man to take what I will never give him.” Her hand moved down inside my swim trunks. “He may have my ruined pussy by knocking me up.” She grabbed my shaft and squeezed my rapidly expanding cock. “But my asshole is yours.” She bit my earlobe. “And his cum is still inside me. I want yours to be too.”
Instinctively, I turned around to look at the house. The bedrooms were mostly dark and the living room only had a couple of silhouettes in front of the TV. She grabbed my head and turned me to face her. “They can’t see shit out here. It’s dark.”
“Dani, are you sure about this? I’m getting to the point where I’m not going to be very rational about this, so don’t rely on me to stop.”
She nodded, bit her lower lip, and then grinned. “You’re old. Your prostate needs to be exercised at your advanced age and my sister isn’t doing that job anymore. It doesn’t sound like anyone is. So, for medical purposes, fuck my virgin asshole.”
I moved in to kiss her and she stopped me. “No, sir. No mouth. Kissing would not be professional.” She moved over the ladder. “Now as a medical expert, I come prepared.” She laughed quietly and pulled out a bottle of lube. “I found this in the bathroom cabinet. I bet we’re not the first to use this hot tub for therapeutic exercises.”
She moved back over to me, pulling off my trunks, and sat on my lap. She playfully used her hips to grind my fully erect shaft into her bathing suit. “Mmmm…such a good patient. First, I want you to feel something. Just to get you a bit more focused.” She guided my hand against her hip, towards her stomach, and then under her suit. I felt her pussy against my palm and then she guided my fingers inside her. She squeezed and I confirmed her story about David. “How ordinary,” she said with a smile.
She rose off my lap and pulled the top of her suit down. I grabbed her slightly sagging breasts and she didn’t fight me as I pulled her closer. I kissed her skin and pinched her right nipple before sucking on it a bit. She pulled me in by the back of my head as she used the other hand to pull the suit down the rest of the way. I leaned back as she stepped out of the suit, admiring the full view. She splashed at me again. “Stop it–I’m almost 34 and I’m a mom, you can’t look at me like that.”
I just smiled. “You’re still looking good to me, Dani.”
“Well, that is completely incidental for your medical procedure, but I thank you anyway,” she said with a wink.
She grabbed the lube and poured some out into her hand. “I don’t know what the fuck I’m doing with this, but it says it’s waterproof.”
I grabbed the bottle and pulled myself up on the edge of the hot tub. “Here, why don’t you take care of my cock and I’ll get your asshole ready.”
She stared at my cock a beat. “You are definitely a grower. Jesus. I didn’t expect that. I’m starting to have second thoughts.” She nervously laughed.
I pulled her in and stole a kiss quickly. She resisted at first and then her lips opened. Our tongues met as I ran my hand down her neck. Then she pulled away. “That was…something. But not now. Okay? This isn’t that kind of thing right now.” Her hand lingered on my forearm. “You jerk. I’m going to have that on my mind now.”
I shrugged my shoulders. “Who knows if I’d ever have the chance again. I just wanted to know what it would be like.”
“Well, now you know. It’s not enough that I offer you anal. You have to get all kissy-kissy as well. Now enough of this–I need that cock.”
She started stroking my cock with the lube until it was shiny. I could tell she was still a bit worried. “Look, it’s not going all the way in. It’s too big, you’re too small, and I’m sure you’re very tight. But we’re still going to have some dirty fun.” The tension left her face and she nodded.
I patted the edge. “You should lean over this so I can lube you up.” She pulled herself up until her ass was above the water. I poured a generous portion of lube into my hand and pushed between her tight pale cheeks. I was surprised by how firm she was and the way I lingered made her laugh.
“Not the sloppy mom ass you were expecting? I do my squats, you dick.” I have her cheeks a light smack.
“Indeed you do.” Then I poured the lube directly from the bottle to her crack, rubbing it against her puckered asshole. “One finger is going in,” I said before pushing my pinkie into the pucker. She sighed and pushed back into my hand.
“You can do better than that,” she sneered. I pulled my pinkie out and then pushed it in with my ring finger. “There we go…you’ve got to get me ready, big boy. My worthless husband hasn’t even tried to use this hole.” I slowly slid my fingers in and out until I felt her muscles relax.
After some maneuvering, I found a way to use one of the seats of the hot tub to be at a good angle to fuck Dani’s asshole. I gave her right cheek a louder smack than I intended and she moaned her approval. “I want all that cum that’s been building up in you to come out. So use this ass like you paid for it.”
I had moved beyond words at that point and just gave a lustful grunt as I pressed my slick cock between her cheeks. I paused with the head of my cock on her asshole and gripped her hips for a moment. Everything was going to get really complicated after this–I wanted to enjoy this. All the nights I shot cum into sheets, towels, tissues, and one-night hookups thinking about my ex wife’s baby sister taking my cock. And this was it.
I pushed into her as I pulled her hips back. I noticed she had covered her own mouth as I took her asshole. It was slick, warm, and tight. The head of my cock was inside and my shaft grew harder. I could already tell I wouldn’t be able to get in much further. I could hear Dani moaning in pain and pleasure, but this was clearly a new sensation she wasn’t quite ready for.
I stroked my cock while the head inside her, which was fun for a bit and bless her heart she tried to get me deeper by relaxing and pushing into me. In the end, I decided to make it more intimate. She was family, after all.
I patted her hip and she turned her head around. “I want you to flip over. It will be less painful and less messy if you can do that without my cock coming out. Do you think you can keep me inside you?”
“You’re rammed into me with an airtight seal. I’m concerned you’re never going get it out.”
“Well, if you do your job, my cock will get smaller.”
She laughed and raised a finger. “Great point, patient. Let’s get this position change in motion. My knees are kind of killing me right now anyway.”
I was able to do most of the lifting to get her turned around. She held her legs wide while I continued my limited assault of her asshole. But now I could watch her face and see her tits bounce, which would make this a faster finish.
I wrapped my hands around her neck as I started pushing the limits of her ass again. She let go of her legs and held onto my big hands with her tiny finger. Nothing like her sister. I leaned down and kissed her again. This time she enthusiastically engaged. As I pulled back, she had the sweetest look on her face. “Am I going to make you cum? I wasn’t sure I could.”
“Yes, Dani. I’m going to fill your ass.”
“Good, I want to make you feel better. I’m going to worry about you.”
I increased the pace of the thrusts. Dani kept talking. “I don’t want you fucking every slut that comes along now that you’re single again. Wait for the right one. Use me until you find the right one.”
I started groaning, feeling the pressure build in my shaft.
“Only you’ll have to use my mouth and my pussy at home. My asshole is only for the beach.”
Oh god. My knees buckled. I felt my blood pressure rise.
“Oh, my dirty assfucker. You’re fucking my husband’s cum out of me. You own me now.” With that, she started frantically rubbing her clit. And indeed, there was cum exited her pussy when I pushed in.
I grunted loudly as I exploded into her once virgin asshole and stroked my hot cum into her asshole. I loosened my grip on her neck and she started stroking my cock hard. “Every fucking drop. All of that cum needs to get out.”
She squeezed her asshole to tease the tip of my cock and aid in the cum extraction. Finally, I was empty and collapsed back into the water pulling her with me. In the warm bubbles, we disconnected but then embraced. I pulled her on top of me and I felt her rock hard nipples and her heart beat against my chest. I grabbed the back of her neck and we had a slow kiss. I reached around and grabbed her ass once more and she wrapped her legs around my hips.
As we remained entangled and watched the stars emerge from the twilight, she kissed my cheek and leaned into my ear again. “I’m trying really hard not to make a very bad decision, but that was as good as I always hoped it might be.”
“Yeah, I was thinking that earlier.”
“Well, let’s just say this is a great incentive to stay close.”
I laughed and we found a corner where we could just hang on between the jets before the demands of the world separated us again.
Source: reddit.com/r/sexystories/comments/ikc1z6/for_medical_purposes_mf_cheating_anal