I’m 50 and my step sister is 46. My step-sister and I have always been close. We played around a little when we were younger but never had sex. She wanted to but I didn’t want to be her first. I wanted her first being the guy she would marry.
As we got older we both married and divorced several times and last year she divorced her last husband. We only live a few miles apart and since she got divorced she has been stopping by at least one a week to hang out and talk.
So a few weeks ago she stops by and somehow we end up on the topic of sex and what we like and tell her that I’m kinda glad I’m not married because I was starting to have problems staying hard and hated the side effects of the pills. She said she was sorry.
We talked about things we never got to try that we wished we had. She said she always wanted to try anal but both her ex-husbands thought it was gross. I told her I always wanted to be dominated but neither of my ex’s where into it.
She asked me if I had wanted to whole Femdom thing where the wife wears a Strapon, makes you eat your own cum, pees in your mouth, and wear a cock cage. I turned red with embarrassment and nodded yes. She hugged me and said it’s nothing to be embarrased about. Lots of men are into that.
All the sexual talk was getting too me and when she hugged me she realized I was hard and reached down and squeezed me, laughed, and said it seems to be working OK.
I laughed. She looked at me for a moment and then said “You know we could make each of our fantasies come true if we each just bought a Strapon. “Would you want to do that I asked”. She smiled, nodded, and said “I want you to buy the Strapon you want me to use on you, and I’ll do the same. Let’s order them now. We should have them in a couple days with 2 day shipping.
I said “I can’t believe we’re doing this. I You know I always wondered what it would have been like if I had fucked you.” She said “I know, you were a gentleman, and we we too young, and it never would have worked, but we are going to make up for it this coming weekend.”
And then it was Friday afternoon. My step sister rang the doorbell. She had an overnight bag and several other bags. She pulled a bottle of wine out of one bag, laughed, and said I’m going to need this.
This is for you she said, and handed me a bag. I opened it and it contains a hardness and a life sized dildo. She smiled and said, I wanted to know how an average size cock would feel. I usually put a vibrator in my ass when I masturbate, so I don’t think it’s going to hurt me.
So let me see it she said. I handed her the bag I had on the counter. The dildo was about 7″. My step sister said, you know this is gong to hurt if you’ve never had anything in your ass, right?
I held up my glass and said, 100 proof Bourbon.
She walked over and looked up at me and asked, you want to do me first? I nodded. My step-sister said, let’s take a shower first and took my hand and we went to the bathroom. Standing outside the shower door, my step-sister looked up into my eyes and said, you never saw my tits after I had kids, and pulled off her top and removed her bra. My God, I said. Your Breasts are incredible. She held them up with her hands, smiled, and said yeah, they grew a lot since we were young.
We got in the shower and kissed. My step-sister said, I’m going to drink a lot of wine, the next time I pee, I want it to be right here, with you on your knees in front of me. Do you want me to do that for you? I blushed and she said, it’s nothing to be ashamed of OK?
We got out of the shower and she plugged in her vibrator, then got on the bed and put a pillow under her waist to lift her ass up. I got into the harness and tightened it up and lubed up the dildo, and positioned myself on top of her. My step-sister said my God, I have wanted this for so long. I put the tip of the dildo on her asshole and began to put my weight on it.
She gasped and pushed to relax her anus and the tip of the dildo slowly began to enter her. She switched on the vibrator and I gently pushed the dildo into her until it was all the way in. She said, Holy fuck, I feel so full, it feels so good, please… Please fuck me. I pulled almost all the way out and entered her again, a little faster this time, and then again, a little faster. My step-sister cried out. Omg! Harder! I pulled almost all the way out and thrust into her hard making her ass bounce and she yelled out, Yes! Don’t stop! I began pounding her and she cried out Omg! I’m cumming! And cried out as she came, her body convulsing.
I Held her for several minutes with the Dildo all the way in her ass before pulling out.
She moaned and said “I would let you fuck me like that every night”. I said there’s nothing stopping us.
She got up and asked me to get her some more wine while she cleaned up.
I heard the shower turn on and I went in the the bathroom and joined her. She asked me if I remembered what she had told me she wanted to do to me in the shower. I nodded.
She told me to sit down in front of her and I did. She asked, “Do really want me to do this?”. I quietly sad yes and she said, OK. Close your eyes and open your mouth. Try and relax, don’t think about what’s happening, and swallow.
A few moments passed and I felt her warm stream shooting down my throat. She pulled my head to her and I began swallowing. I managed to get about 3 mouthfuls down before started to gag. She stopped and gave me a second and then said asked if I was ready for more. I nodded and this time it was easier. I swallowed for what seemed like several minutes until she had emptied her bladder. I stood up and felt her piss sloshing around in my belly. I felt a little queasy and she asked me if I was OK and then turned the water cold and told me to put my face under the shower and after a minute I felt better.
“I am so proud of you! No one has ever asked me to do that for them. It felt so good having your mouth on me knowing what you were doing. Did you like it?” she said.
I said “Yes”.
“OK… You know what comes next. You ready for this?” she said. I nodded.
“Then go get on the bed and I’ll be in there in a minute”.
Will finish tommorrow…
Source: reddit.com/r/gonewildstories/comments/74b37a/mf_grown_step_sister_and_i_decide_to_make_our
Part 2