Open marriage..and the Prep pill

My wife takes the prep pill and so far so good and she’s had a lot of guys even a lot of creampies she fixed so no babies I’m not aloud to have any sex do I don’t need it just watch her

I was going to a family get together out of town. My 4 months pregnant sister asked to ride down with me. When I got to my motel and got checked in she surprised me when she followed me to my room. She said she didn't have a room and asked would it be okay if she stayed with me. I was thinking, this is really fucked up, who does this, but just waved at the one bed and said if you want to. We got settled, went and got something to eat, then went to bed.
I woke up spooned, with her rubbing my dick between her cheeks. I did everything I could to not get hard, I didn't want to tell her to stop or move away from her. I think I wanted to show her this wasn't me, but my dick betrayed me. This went on for probably half hour, she was very gentle but consistent, when I got all the way hard she slid it inside her wet pussy. She was slowly grinding against me I joined her and even rubbed her pussy which sent her over the edge, and I followed her.
Afterwards she cleaned herself up, got back in bed and went to sleep, never said a word to me. The next morning she acted like it never happened, like we had a normal night. She did ask me how did I sleep, which I thought was a reference but I just said I slept okay, how about you, she said I slept like a rock. And that was it, not one more word, just like it never happened. We stayed in the room 2 more nights but she never did it again. This was 2011

When I was still living at home, and one weekend afternoon, she walked in on me masturbating (I had fantasized about my mom a few times. But had the hots for my sister, who had already moved out of home). She apologised to me looked for a few seconds, smiled and quietly shut the door. I found it highly hot that she saw me hard.

So for quite a few months I tried to get caught but the timing never worked, or she knocked on the door. I did get her to see me naked about 5 months later when i had walked out of the shower, as she was bringing laundry in to put away. She was in the closet and had the basket of clothes in there with her. So i got to have a chat with her nude until she was finished. I was semi hard while talking to her.

It wasnt until a couple years later, when i was masturbating one night and heard my mom come home from work, thinking i potentially could set it up for her to watch me.

She was a nurse at the time, and would work late and get home around midnight. I would often come out and say hi and give her a hug and talk to her about her shift and have a midnight snack.

Test come back negative for aids and stds. How i am not sure. Very thankfull. It was like me and him kept turning each other on.

I had a bathroom attached to my bedroom, but there was also another door that led to a living area which the garage stairs came up. I thought maybe if I left the door to the bathroom open from the living area, but leaving mine almost all the way shut, but enough to look into my room where she could peek through the door frame and the hinges, she could watch if she came to check on me. Since I normally came out when she got home, she would probably find it weird and check on me if I didn't. The first week that she worked i had porn playing on my TV and I could hear her go directly upstairs and she didn't check on me. The 1st night of the second week she did.

Thst night i heard her come home and come up the first set of stairs, but didnt hear her go up the second flight. I could tell, she was there, as there was a night light in the bathroom that was visible through the door crack and out of the corner of my eye, the light was no longer lighting up the door crack.

I masturbated for the next few minutes before cumming. When I finally finished oozing, I looked over and the light was back. So she had left.

I ended up doing this every few weeks, but still go out and say hi all the other times , and my mom would watch a lot of the times i did it, before I left home. It was about 6 years in total. Never had the courage to try anything with her and she never gave me any queues as if she wanted to.

Would love to have gone all the way with her, but would have been quite happy with a helping hand.

I had been divorced a few years and my sister was a widower, both in our late 40s. She lived about 7 hours from me but called one day and said she was moving back in town and asked if she could stay with me for a minute while she got herself together. I agreed, it was just me so I didn't mind the company. She had been there maybe 4 or 5 months and works from home. I came home one day and she was sitting on the couch talking on the phone. She had on this short robe, one leg was on the floor and the other one was crossed in front of her and I was staring straight at her blue panties. I didn't say anything I just let it go and went to get cleaned up when I got back I couldn't see her panties anymore so I let it go.
Another time she came walking through the house in a robe that was sheer enough that I could tell she didn't have anything on underneath. This kept happening and for a long time I didn't say anything I just felt she was comfortable around me but one day she modeled this dress for me and asked what I thought. I said, you look good enough to eat. She said yeah prove it. We laughed it off but it didn't go any further. She continued to dress scantily around me but I got used to it and it stopped being a thing.
She had been staying with me just over a year and one night she knocked on my door and asked to sleep with me saying she was cold. I do keep my heat low so I didn't think a lot of it other than it was a bit odd.
I think we both knew where it was going tbh but it was a matter of who was going to move first. She started by putting her cold foot on me saying she wanted to warm up. From there it was a touch here a touch there until I was between her legs. I asked was she okay and she said I'm okay. That was our first time.

I was out of town for the weekend with a buddy and we stayed at the house of a woman that he'd fool around with when in town. She brought a female friend over one night, we were all drinking, smoking and whatnot and eventually, the friend got so shitfaced that the lady decided it was time to take her home and I'm the designated driver.

She had been flirting a little all night. She wasn't a quite the best looking girl, and I wasn't breaking my neck to jump her bones, but here we are in the car. She's talking out of her mind, much of it sexual or insinuating sex. She would kiss me, grab my hand and was sucking on my fingers while looking into my eyes. Eventually we made it to her place and she got half naked and laid down. She'd still suck on my fingers and let me fondle her and allowed me to slide her panties off, but by the time I had my dick out and ready to penetrate, she was pretty much passed out drunk. I went ahead and fucked her. I cleaned up and left my number on her counter because frankly, I didn't know what to do and it felt weird if I didn't at least go through the motions of acting like I was interested in talking to her.

When I got back, my friend told me that she pretty much recruited her annoying friend for me because she knew she'd put out and wanted to be a good host and make sure my friend wasn't the only one getting his d*ck wet. I look back and feel kinda creepy because I've never fucked a woman I just met that's passed out, before or since. She did call me when I got back in town but I didn't answer.

Was that an "in-bounds" play in your opinion?