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I [M36] finally groped my grandma roommate tonight
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I live with two fifty year old ladies in an apartment downtown close to the water. They both love to take walks by the sand and I get to see them in modest bathing suits all the time. One is a grouchy, skinny, annoying bitch who I don't care for at all but act respectful towards anyway because she's my elder.

But the other?

She's a late fifties gilf packing a juicy fat ass and a pair of heavy tits with perpetually tight nipples that are only just starting to sag. And when I say "gilf," I mean it. She has shoulder length chestnut hair that's lined with streaks of silver, a chubby yet curvaceous figure that erotic photographers would kill to snap photos of, and dainty feet with the hottest high arches you've ever seen. She never paints her finger or toe nails (which I like) and almost never wears makeup.

Why?

Because she's told me she hasn't had sex in almost a decade and has all but given up on men. She's beyond sexually frustrated and has openly admitted to me that she's gotten so good at masturbating that it's not hard for her to get herself to orgasm.

I've been working her for a few months now, giving her compliments on how well she's kept herself in shape and even groaning and grabbing my swollen crotch in front of her when I can see down the partially open front of her bath robe at her pale, creamy tits and pink nipples that always seem to be stiff and dotted with goosebumps.

I don't know why, but I never thought about using her phone number before. Maybe I was just too nervous to ask for it (which I know sounds stupid because I'm her roommate but her sexiness can be intimidating). Anyway, she ended up giving it to me (I didn't ask for it) about five or six months ago, and I didn't use it until late one night after we'd had an exchange about nutrition as she was making dinner. That was about a week ago. I told her that it was important for her to put the right things in her body because a person's diet meant everything as they aged, and then her face went red as she opened the fridge and whispered loudly, "I definitely need to put SOMETHING in my body!"

We both knew she meant cock but I didn't take advantage of the moment and ended up smacking myself back in my room. After about an hour (it was after midnight) I texted her this...

Me: What was the joke you were gonna make when I said you need to put the right things in your body?

Her: You said good things, speaking of food. I just have a dirty mind, and made the joke about what I was thinking. You got what I meant, eventually.

Me: There's nothing wrong with having a dirty mind. I've got a dirty mind too. Sometimes it's too dirty.

Her: My mind or yours?

Me: Both. You got an itch that I know needs some scratching.

We went back and forth for a few more minutes before she said she was tired and had to go to bed, but I left my room and walked over to her door to listen through it and heard her moaning from where I know she sleeps. She ended up touching herself because of our messaging! You have no idea how hard that made me and how much I came all over myself back in my room.

Fast forward to tonight and we've been doing some intense flirting for the past few days. Our latest texts have gone like this...

Me: I'll just say this: your neglected pussy would thank you if you let me into your bed. We don't have to move fast but I know kissing and licking your pussy with the entire length of my tongue would send you over the edge. There's only so much you can do with your hands...

Her: All of that is probably true. More than probable. I've been friends with lovers, but never lovers with a friend. You know my background (she was abused by a man that she was supposed to get married to) and I have never felt comfortable around men since. You have helped immensely with overcoming that anxiety. It's made me curious about how I would react to a man. For now, it's easy to fantasize and open up on the phone. But it's alot different (and "safe") then actually being together. It would be easy to take advantage of our situation and fill in that void.

After more back and forths, I couldn't stand sitting in my room with one of the hardest boners I've ever had and walked out into the kitchen where she was, stood behind her as she stirred a soup she was making on the stove, and grabbed a handful of her fat ass. She didn't react physically, but I heard her gasp as I groped her jiggly gilf booty with my right hand and shook it while sinking my fingers into her unbelievably tender flesh.

I'm back in my room now and my heart's beating so fast it might explode. I'll give updates if more comes out of this, but I have a good feeling it isn't over.

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1 year ago