Hey. I am a 39 year old man, and my sister Callie is 38. More than a year apart but not much more. I’m 5’11”, 150 lbs .. slim, fit, handsome with olive skin and dark features described often as beautiful. I’m also blessed down below with a legit 8″.
Callie is 5’5″, not as slim as she used to be as a teen, but a still trim and active size 6. She was a 2 until her second kid ten years ago, but the trade up from b to c cup makes it worth it.
We were the two youngest of 4 in an upper middle class family with another close pair of sisters 5 years older than us. So we spent a lot of time together, same friends, same parties, same party drugs.
We were both wild child types and grew up as our dad was making more money than he did when the older 2 were coming up. He still made a lot back then, but we moved from a nice house to a nicer town and a snobby high school.
We talked about our hookups graphically and were both popular in our way. We were mischievous and a little bit depraved. Open. I always made sure my towel would drop “accidentally” and sometimes she would do the same. Fueling my jerk off fantasies through high school.
One time we were talking about something she did with a guy senior year. Some girlfriends of ours in my grade, now freshman in college, took her out for her 18th. She went home with a 25 year old and his 23 year old friend showed up with some cocaine. They were both hot professional types, and she described how they just did cocaine and fucked her all night and the next day. That was yesterday ( back then).
“Damn that’s hot.”
“I know but I feel like shit today and just want to lie down and drink water.”
“I’m gonna go lay down and jerk off ” I said. “Wanna come lay down in my bed and tell me more?” I asked, waiting for the no thanks reply.
“Ok,” she answered. I didn’t say anything, just went and made my room dark and put in a CD. I took off my shirt and pants and laid in my boxers
She flopped down next to me with her eyes closed. I pulled my cock out and started working it slowly. “,Tell me more ” I said. “Where did they cum?”
“Mostly in my pussy. Once in my mouth and twice on my tits. But like 4 or 5 times each in my pussy.”. I was stroking harder.
“Oh my god that’s so hot.”
“Mmmhmmmm it was. My pussy was just full of cum all day yesterday.” She turned her head to face me. We locked eyes.
“I would love to do that,” I admitted. She smiled and yawned
“I bet. Well definitely not today because I’m sore and probably still full.”
“Ok, can I cum on your tits?”
“That’s fine. But I’m too tired, I’m not doing anything. I can’t move.”. She clasped her hands behind her head. I pulled up her hoodie and tank top and knelt beside her, salivating over her perfect nipples thinking about how I was the third guy to cum on her tits in less than 24 hours.
I tensed up and shot so much cum on her tits and associated region.
“Mmmmmmm…” She smiled as she felt the first shot hit her tits.
After the best orgasm of my life I crashed next to her.
“Thank you so much for that,” I said.
“No, thank YOU,” she replied. “Any time.”
“Really?” I asked.
“Why not? You love me sometimes. Least I can do. I’m gonna take a nap in your bed. I feel like shit from last night.”
“That’s fine. Me too,” I replied as I took my underwear off and spooner her. “But these have to go,’ I said pulling down her sweats. “I want to feel our legs.” Her last act before falling asleep was to help facilitate her pant removal. Then snuggle back into me. Her shirts were still up and her tits out. I felt them and rubbed my cum in as we spooned then fell asleep.
I woke up an hour later so hard and horny and naked. I ground into her ass, but just laid back and jerked off. I pulled her panties down under her ass and felt it with my left hand as I jerked off. After 2 minutes of this I got back into spoon position and put the head of my dick against her ass and pussy when I came. It was so good.
I took a shower and dried off and laid back down naked. I was hard again. She was now on her back sleeping. I took her right hand in mine and used her hand to jerk off again.
I realized that I didn’t care if she woke up. I realized that she did when I felt her squeeze a little. I took my hand off of hers and she kept going. Uninspired, but the message was in the delivery itself; she kept going.
It took 3 minutes of that until she felt me tense up and perfectly squeezed my cock as she stroked me all the way through my orgasm.
“Ok? Let me sleep,” she said as she wiped her hand on the sheet. She rolled away from me and went to fix her panties.
“Did you cum inside me?” She asked.
“No, I just put it up against your pussy when I came.”
“Its so wet. It was so much, I can feel it sticking everywhere.’
Maybe next time I can put it inside you?_” I asked hopefully.
“Let me sleep,” she said finally. I let her sleep and did some regular stuff that day.
Two days later. Tuesday night, after school and sports and dinner, getting ready for bed, I asked if she would give me a handjob again, and she said maybe.
She came in at 11:30ish, got on the bed next to me on my right, got under the blankets, laid on her left side and slid her right hand into my underwear. She took my cock out then flipped down the blanket and gave me an awesome handjob.
She let me talk dirty and played along with whatever.
“I want to cum in your pussy so bad.”
“Your own sister?” She faked shock.
“Yep. I want to look in your eyes while I cum inside you.”
“Oooh…naughty.”
“I want to lick your pussy for hours then fuck you and cum inside you. All night, over and over…can I do that sometime?”
“Yes. I want you to. Sometime.”
“, Promise?”
“Yesssss….”
She gave me handjobs all the time after that, or watched me jerk off and let me cum on her. She liked doing it for me.
After a crazy night of ecstacy in our 20s, the first time I got to fuck her and cum inside her, we briefly had a fuckbuddy period.
Until she missed her period and I got my sister pregnant. She had an abortion, of course, but it was so hot knowing that I had. We went back to hand jobs and still do to this day.
The only person who knows is her husband, and he likes watching her jerk me off and cumming on her naked pussy. Then he will fuck her with my cum all over her pussy
Source: reddit.com/r/Erotica/comments/sqmpel/20_years_of_secret_handjobs_from_my_sister