The following happened. All of it. So, I remarried when I was 46 to a woman who was in her late 30's. She had two kids, one of each sex. Turns out, prior to us meeting the son had exposed himself to his sister a year prior to me meeting his mother. Skip forward to high school and the Merissa was caught give head to several boys. Her mom lost her mind of course. The stepdaughter then gets engaged to a real twat. He ended up abusing her cats and that was the end.
She moves in with us. The very first week she is here, he mom went to visit one of her sisters in Iowa and we were here alone, which I spaced out. I came out of my room, about 4 in the morning, naked, as I am wont to do, most nights, since that is how i sleep. I did not even see her on the couch, until I turned around and heard a gasp. Oops. I apologized and went back to bed.
Later than morning, I went downstairs to talk to her, only to find her on her bed, with the door agar and rubbing her pussy. I started to walk away and then heard her whisper my name. I returned and she was still quite engaged. I kept watching and seeing her fuzz covered pussy getting really wet. After about 5 minutes of this and hearing my name three more times I just walked in. She looked shocked once she realized I was there, but then took her hand away, at which point I replaced it with mine. I leaned in to kiss her and my god, her lips were so good. Her pussy was so wet and swollen, after a minute or so I quit working on it and just went to licking her, from her neck to her back and legs and after 30 minutes or so of finding all her erogenous areas, finally landed on her pussy. While licking it and teasing her swollen clit and her little anal pucker, I inserted a finger into her pussy. She finally started to come and with a little bit deeper into her, I found a spot which while not gushing/squirting, she became like a swamp she was so wet. at this time she took my cock out and sucked it deep into her mouth. After a few minutes of this, she looked into my eyes, took my cock out and begged me to fuck her. I spun her around and had her glide it in. She was so amazing. I am not going to lie, that first time in her pussy I only lasted a few minutes, but WOW was it awesome.
As noted before, her mom had gone to another state to see her sister and during that time me and her 19 year old daughter had hooked up.
The next day was a bit odd in that I had to work and so did she and at opposing hours so neither was home while the other was. On the third day, in the evening i decided I needed a soak in the hot tub, so went for it. after about 5 minutes in the tub, I heard the screen door open and close and then saw the Merissa coming to the tub. She was wearing a bikini, which was good. After entering and some small talk she finally addressed the fucking of two days prior. She asked how i was doing with it and said ok, but that we really needed to try not to repeat the mistake. To which she removed her top and said, "nope, I think that the remainder of her time gone, I am going to get the most out of this, since it will be over, forever when she comes back!" she then took off her bottoms and then proceeded to sit on my lap, which was sporting a hard on. We proceeded to make out in the tub and I suckled on her ample tits for quite a while.
We then exited the tub and went into house. While drying off and stripping I asked her what had got into her, no pun intended. She said that the previous episode had shown her that older men knew what the fuck they were doing and while it was hot and heavy, she also appreciated the time i had taken in finding and exploring her erogenous areas. I asked her which one she wanted to explore more, in depth. to which she replied she had always wanted to try anal, but the boys she dated were always just. a little too anxious and never felt good beyond just the touching. Who was I to argue.
We got in the bed and I had her suck me off, and she swallowed it all, which was just fine. I then proceeded to again lick her all over and of course ending at her pussy. This time, I turned her over in a bit of a 69 and went a head and spent some time on her clit and pussy lips, which if I haven't said, are long and dangly, which I fucking love. after she came I then started playing with her ass with my tongue while fingering her pussy and clit. She came a couple of more times and then asked me to fuck her.
This time instead of some missionary-ish position, I had her face down and ass up. she asked if I was going to fuck her ass, and I said yea, eventually but not today. Today is all about getting you used to and relaxed around anal play. since we are going to be going at it for some of this week, we will get there eventually.
Going at it this way, I was going really nice and slow and a couple of times just stopped, forcing her to rock back on my cock, in order to fuck. She really liked using the whole length of my cock. During one of these times I placed my hand in such a way that the thumb was right next to her little starfish and just touched her there, to which she clearly jumped a bit. I told her as we were fucking to just relax and enjoy the sensation as I played with her asshole. Lubing my thumb up a bit with her pussy juices, I then started rubbing it pretty vigorously, which then drove her a bit crazy, as she was loving it. She actually asked me to put my cock in her ass, and it took a bit for me to decline, as I wanted two things. A, her to really want it, to point of begging for it and B, for her to enjoy it, so I could get it more than once. To that end I pulled out, as I was close to coming and wanted to extent the game. During this time out I explained, as I was rubbing her clit and pussy that the best way to have something enter your ass, is to gently push out a bit, and as you relax that is when it is best to have something then enter. I also warned her that in order to get to point my cock, about 6" in circumference would best fit would be to start small and eventually get to 2-3 fingers, then the cock.
I got back behind her and again started slow stroking her cunt with my cock and playing with her asshole with my lubed thumb. I then told her, I was going to push in, after I saw her push out a bit, which with my thumb placed perfectly, she then did and I slid it in to first knuckle and she startled a bit, but kept bucking onto my cock. I then said, how about again, and she did, which got my whole thumb into her ass. I asked how it felt and she could barely talk. I noted her pussy was soaking wet. I then for next 5 minutes proceeded to fuck her in as long and hard as strokes as I could, trying to bottom out in her pussy while at same time started to run my thumb in and out of her ass. after a minute or two of this, she basically screamed to put two fingers in, which I did using same technique as prior. For about two minutes of both my cock and fingers fucking both her holes, she started quivering and coming, at which point I couldn't take it anymore and filled her pussy with my cum.