Family time with the sister-in-law [M28, F30]

This is my first story here, so here is a little backstory on me. I am your average married guy with too much time and not enough self-control when it comes to keeping it in my pants. My friends say I am probably a sex addict, and I’m inclined to agree but never been diagnosed. Either way, my lifestyle has led to me having a laundry list of sex stories that to be honest are kind of mundane. However, there are more than enough that are exciting enough to share with this community. This first one kicked off what is my most morally bankrupt sexual relationship I ever had, but damn it was fun while it lasted.

My wife and I had been together for 8 years at this point in our relationship. Despite the years together I had never been that close with her family until my father-in-law passed away. My wife and her older sister, Jennifer, were devastated as it was an unexpected passing. Throughout the ordeal I kind of took point on getting all the estate stuff in order, I was contacting lawyers, talking to county clerks, dealing with the funeral home, etc. I wanted my family to be able to grieve and wanted to keep their stress level as low as possible. During this time, Jennifer and I began to talk more and became closer than we’d ever been as I would do my best to try and be positive and comfort her and my wife. This culminated in me and Jennifer having about an hour long conversation in my car as she broke down crying one day and I talked her through it. From that point on we had a connection, an understanding, that I cared for her and she could talk to me about anything and everything. At the time I was working overnight at my job and Jen was unemployed and staying at her late father’s house, so a lot of our bonding happened while my wife was working…

A little description of Jennifer, she was 30 at this time (I was 28). She is around 5ft tall, her mexican heritage gave her a darker skin tone and very long black hair that she almost always wore up in a bun, small b cups, a little chubby mom tummy, and an average sized butt. She was your average mom type, not stunningly attractive or anything. Just a genuine person who didn’t look like she stepped out of a porno. On occasion she would doll herself up and take some heavily filtered Instagram and Facebook photos, before going out to the club or bar. She was a single mom for as long as I’d known her and never really had any steady boyfriends, just guys that would come in and out of her life and her ex-husband was living a state away and pretty much gone no-contact outside of the annual birthday call to his son. Overall, her relationship status was pretty dire.

Fast forward about 8 months after my father-in-laws death, and Jennifer sends me a text asking if I could bring over a copy of the death certificate to clear out an account in her dad’s name. By this point we had a strong rapport and we had gotten very comfortable around each other. Some playful flirting but nothing over the top. I get to the house and give her a quick hug as I walk inside. She smelled so good that day, like the typical body spray perfume every woman has in their collection. She was dressed so casually, in a pair of jeans that made her butt look bigger than it is. I hand her the papers she needed and we exchange a few words and then we both sit down on the big L-shaped sectional couch in the living room. A few minutes of chatting go by talking about back-to-school shopping for her son and how she needs to get some new clothes too. Without thinking I drop the line “you should get more pants like the ones you’re wearing, they make your butt look good”. She gave a little smile and said “oh shut up, it’s not even that big, I wish it was.” Sensing the mood change, I doubled down, “it’s big enough to give a good spank” I said as I motioned and made a silly smack sound. We both chuckle and change the topic for a bit before Jen gets up to grab her phone from the kitchen. I watch her walk over and don’t even hide that I’m staring at her ass. She comes back after a few moments and sits even closer to me than before. She places her head on my shoulder and starts showing me some facebook videos and some room decor she was looking at getting for the house. This goes on for about 15 minutes, just us shooting the shit and enjoying each other’s company. The conversation dies and we are just basking in each other’s company at this point, each of us on our phones, slowly building more and more tension.

I decide to make my move and do the old ‘stretch and place my arm around her trick’. No objections, in fact, she actually gets in closer but just keeps scrolling through her facebook feed without saying anything. I adjust my arm to get more comfortable, placing it just above her hip and give the slightest squeeze to bring her in even closer. Still no words between us at this point. My heart is racing as my mind can’t decide whether to risk it all or just play it cool. Fuck it, I thought. I use my free hand to turn her face towards me and I go for the kiss. For a split second I thought time had froze and then it happened, she began to kiss me back.

We made out like teenagers for a good few minutes before we both realized what was happening. We pulled away from each other, had an awkward laugh and pretended that it wasn’t a big deal and that we shouldn’t do that again. We were both cracking bad jokes to try and lighten the mood until I jokingly said “damn, can’t believe you got me this hard, I’m about to pop my zipper.” I pulled her in close again and just moved her hand to my crotch. “This is bad” she said as she squeezed my hard-on through my pants. I brought her in to kiss me again but there was a bit of resistance on her end. I thought that was the end of this session and we would compose ourselves, but then the hottest phrase comes out of her mouth, “Pull it out.” If my dick wasn’t hard enough already, it was diamonds at this point.

I unzip and pull out the little guy. She starts stroking it while we kiss some more. I have precum leaking out almost instantly and my mind is racing with all the things I want to do with this woman. Passion had overtaken us, we were pretty much swallowing each other’s tongues by this point as she started stroking me faster and faster. Without saying a word I put my hand behind her head and gently guided her towards my dick. She placed me in her mouth and got to work, slowly at first and then sped up as she got into a rhythm. I moaned as she started hitting that sweet spot where the suction is just perfect, and my noises seemed to have got her going as she started going faster and faster. I grabbed a handful of her cute little ass and started rubbing her over her pants. Her toes curled and she let out a “holy shit” as she took a quick break from sucking me off. I pulled her back up to me and began to passionately kiss her before whispering in her ear “Take off your pants.” Within seconds I helped her throw her pants to the floor and she was bent over on the couch, ass up in the air. Was I really doing this? Was I going to fuck my sister-in-law on the couch where my wife and I watched movies with her family? You know the answer to those questions by now.

I grabbed her by the hips, gave her a hard spank, and slowly entered her from behind. “Oh fuck” she gasped. I started going slow as she buried her face into the couch cushion, her hands gripping onto whatever they could as I picked up speed and went faster and harder with each thrust. It had only been a couple minutes but I couldn’t hold it anymore. I grabbed her by the back of her hair and pounded her a few more times with enough force to smash through a wall it felt like. One last rough spank and I grabbed onto her hips and held on for dear life as I blasted one of the hardest loads I’ve ever had inside of her. The kind of orgasm where words don’t even come out, just guttural caveman-like grunts. I pulled out and collapsed back into the couch. Jen’s ass is still in the air at this point and I see cum leaking out. We both catch our breath, get dressed and cuddle for a bit. Nothing needs to be said during those first few moments just smiling at each other and little kisses punctuating the silence.

Eventually we compose ourselves and Jen says she has some Plan B so not to worry about cumming inside her. I ask the million dollar question “Was this just a one time thing?” We both look at each other in the eyes, knowing that we need to say yes and admit this was a mistake, both of us knowing the risks of my marriage and her sisterhood. It had to end right here, right?

“I’m down again, if you are” Jen says to me with a shakiness in her voice. “Hell yeah, just text me whenever” I happily reply, like a kid on Christmas morning. Jen comes in and then gives me another kiss as I make my way out the door and head home.

Jen and I had an ongoing relationship on the side for about 4 years until she finally met her future husband. I have a few more stories of note with her I’d love to share if you guys are interested