I have a friend with benefits that I've been seeing on the side for many years, he seeing me on the side too. We meet up quite regularly. Both of us are in our 60's but we're very fit and active. Before this meeting he sent a text message: EmojiEmojiEmojiEmojiEmoji. And yeah, it got my attention. Now, we enjoy anal sex often but it's still a special occasion because anal isn't as, um, spontaneous. It requires preparation on my part as the fuckee. I like to make sure I'm squeaky clean including a shower and everything nicely shaved. One thing I do that makes things go smoothly is I get myself all lubed up with a silicone gel and put in my butt plug. It's extra excitement driving over to our meeting place too. I dressed for the occasion with some silky black stay ups and sexy white panties. I wear a skirt and a pull over top, no bra, they're easy to strip off. Fix my hair, a pair of CFM's and I'm out the door.
I let myself in, he's waiting on the sofa, wearing his robe, I strip off to my panties and stockings, straddle him and we kiss. His hands find all my special places, fingers pinch my nipples, pushing on my butt plug as if reminding me of what's in store. I can feel his cock rising. He's very large. I get off, kneel between his legs and take his cock in my mouth. He's fully erect now and wearing a cock ring, the head is purple and enormous, already leaking precum. I suck him slowly, all the way to the back of my mouth and out and again in and out, soon he's breathing hard. I play with myself while I'm sucking. It doesn't take long before he stops me and we go to the bed. He rolls my panties off and goes down on me. It feels so good. I want him in me, I tell him, fuck me now.
We have one of those wedge shaped sex pillows, we use it on these occasions. I said we were fit and active, we're still 60 something and not so flexible. LOL He lifts me up and pulls my hips up on the pillow. He plays with my butt plug, slipping it in and out of my ass. Are you ready for me to lube up? Yeah. I can hardly talk. He does and pulls my plug out slowly then tosses it aside. I feel his cock pressing against my asshole, it's hot and insistent. He pushes into me, his head pops past my muscles. Oh! This is my favorite part. When he first fills me up. Sometimes it hurts a little, but it's good. Other times he slides in so easy. Today is so easy. I wrap my legs around him, pulling him all the way in until I can feel his balls on my ass. I let up and he slides back and then in again, a little faster, then a little faster still in a relentless rhythm towards his orgasm. I squeeze down, making myself as tight as possible He plays with me too. When he does I cum hard. Hearing me cry out with my orgasm is always too much for him and he cums in my ass. He's stopped pumping and I can feel his cock jerking. I love that. I grip him with my legs, holding him in me while he's still hard and stretching me completely. As his orgasm subsides I let him slide out. I reach over and touch his cock coming out and then my asshole. I'm stretched wide open, I feel lube and cum spill out. Anal sex is a hot mess. I couldn't be more satisfied. We get reorganized and comfy for some sweet cuddling then it's off to the shower.