There are times when you're doing something that would have been unimaginable at an earlier stage in your life, and a crystalizing moment begs the question -- how the hell did I get here?
I'm having one of those moments right now. I'm a 35 year old woman, with a good job, a ton of self-esteem, a loving husband, and a life going just the way I want it to. And yet at this very moment, I have a plug in my ass, my pussy is throbbing and, I haven't checked, but probably making a literal puddle on the floor. I haven't cum in... I don't even know how long, and I'm moving in to lick the little pink ass hole of a twenty-year-old girl. Who is bouncing on my husband's cock. Because she ordered me to.
And I can't believe how lucky I am.
---
It all started maybe six years ago, but before we get to that -- I have to tell you a little bit about myself and George. My husband George and I met in college in various groups on the fringes of left-wing politics. We were both dating other people at the time, but the attraction was powerful, and the length of time between us getting out of our relationships and with each other was indecently fast. Even then we were clearly very bad at monogamy.
I'm bi, but in college I had drifted into lesbian spaces, and didn't really hook up with men. Women were just more exciting. When my girlfriend dumped me, however, it was really easy to fall into bed with George. He was exactly my type -- 6'1" with a dark beard, and piercing blue eyes, George was a rugby player, and a small layer of chub over a whole lot of muscle. I'm 5'8" and had always leaned towards the curvy side, though when I look back at pictures of myself in college I have to admit I was a slamming hotty -- D cup breasts, an ample ass, wide hips... a look that's much more in style now than it was then. When I was with women I was very toppy, loving to get them off, but when I was with men I loved when they could make me feel small and delicate. And George did that -- he could really throw me around.
He was also kind, charming in groups, and I later found out... very good in bed. His dick is an average length but girthy with quite with a nice upward curve, but more than that -- he knew how to use everything else to get women off. His high school girlfriend had been an "everything but..." kind of virgin, so George could just tease your nipples until you were ready to break something in half to get more of him, or finger you into oblivion, or find a way to lock his lips around your clit providing just enough suction to keep it this side of too much, while his tongue would lap it and juices would run down his face.
Our first night he did all those things to me, leaving me a puddle of a human being. I told him, honestly, he fucks better than most lesbians I know, and said he'd earned "50 points," which became a running joke for excellent sex in our relationship. It was only then I realized he hadn't actually stuck his dick in me at any point, and invited him to use me to get himself off -- when he climbed on top of my exhausted body, adjusted my hips up into the air, and found this position that let the head of his cock drive against my g-spot, earning the title of first man to ever make me cum through penile intercourse, and, I told him, another 50 points.
---
My cake -- I think this one's name is Abby, though it's hard to keep track - lets out a guttural moan as I started tonguing her ass. George slows her down, rocking her, so that her ass is easy to lick. I don't even like giving rim jobs, but in this moment it feels like the sexiest thing in the world.
"Please..." I moan, each word punctuated by a lick to my cake's ass hole, "I need --" lick... "to touch -- " lick...
George's tone is gentle. "Soon love, you're doing so good. Let's get Abby off one more time, then maybe it'll be your turn."
With that he flips her over, onto her hands and knees, then grips her breasts and pulls her up so that her back his against his front. His hand slides down her bare pussy, and between her legs. His hand slides up from her breasts to close around her neck. Gentle at first, but when it's clear how much she likes it, he squeezes tighter. Her face starts to flush. I sink to my knees, squeezing them together, rocking, doing anything to give my aching cunt some sensation and some relief. I love seeing him like this. Seeing how he can transport another woman to throws of ecstasy they haven't experienced before. I saw the eyes roll back in her head, as her body convulsed, an orgasm ripping through her, rendering her putty in his hands.
Poor girl, this might be the best sex she ever has. I hope not. It would be tragic to peak at 20.
Seeing her pleasure drives me even wilder. Humping the air, pushing the plug in my ass against the mattress, grinding my wet cunt into anything I can.
---
I think it was seeing the other woman's pleasure that really pushed me into being a cuckquean. As I'd said, George and I were never really good at monogamy, and we didn't even really try. Both of us would go on occasional dates or hook-ups, but all I really wanted to know about them was that he had enjoyed a good time. I didn't get too turned on.
In our late twenties a friend of mine from high school was coming to visit -- we were going to go camping at a music festival together. Erin had always had an interesting relationship with sex. She was never the prettiest, though extremely fit. She was that girl that would give her guy friends blowjobs because she didn't see what the big deal was, and it was a nice favor for them. We had fallen a bit out of touch and re-connected. Erin and I had hooked up, once, back when I visited her in college, and I had very fond memories of that event. Part of me had wondered if she might actually be fully gay, but just continuing with men because they were available and her very uptight family wouldn't accept her as a lesbian.
She arrived the day before we were set to leave for the music festival, and we instantly fell into our old ways. Drinks were flowing, and we got to talking about relationships.
"Was he good in bed, at least?" I asked about the most recent childish asshole she had broken up with a few months ago.
"Eh," she said, "no worse than usual."
"C'mon, you have to be more specific than that. Big dick? Small dick? Good with his mouth? What percentage of times did you cum?"
"Average dick. Barely used his mouth. He was obsessed with anal play, and most time we fucked one or the other of us had a vibrator in our ass, which really didn't do it for me. And zero percent, you know that!"
I did know that -- but I had forgotten! Erin had never cum. Not once in her life. I had assumed that in the intervening years someone would have finally pushed her over the edge, or she would have finally found the right electric toothbrush -- but apparently no.
"Wanna try with George? He's pretty fucking good. He might be able to do the deed." I was very casual but completely serious. Like I said, we saw other people, and he could really do Erin a solid.
"Haha, maybe," Erin said, and I could tell she wasn't taking it that seriously. "Geoooooorrrrge," she called, summoning my husband, who had stayed sober and was dutifully packing all of our camping gear for the next day. "Geooorgeyyyy booyyyy!"
"Yes?" he inquired, the tone of the sober one having to deal with the drunk bitches, as his head appeared around the corner.
"George," Erin asked, stumbling a bit as she got to her feet. "George, do you think, do you think you could give a woman -- in her late twenties -- who had never cum, not even with a vibe -- do you think you could give that woman her first orgasm?"
"Maybe," he said, simply. "I mean, I have before." Not a brag, just a statement. It brought Erin short, and there was a silence. "Anything else I can do for you ladies?" Seeing our blank faces and silence as the only response, he turned and left the room.
"He's shitting us," Erin finally insisted. "Just toying with the drunk girls."
"I don't think so -- actually, it's coming back to me. Last year. There was this woman who said she had never cum. They met on Tinder, and he thought it was just a line, a way to get people to bring their "A" game. He told me about it though, because it started getting weird. She cried afterwards, and then got really clingy, not really respecting any of our boundaries. That's why he filled me in on the details."
Our talk got more serious, and it was clear Erin was considering it. I told her it was fine by me -- at this point I wasn't turned on at all, just checking in on feelings. Re-assuring her it was okay, we played around all the time with other people. Wouldn't be a big deal. When I climbed into bed with George, I filled him in on the conversation. Asked if he was interested. He made a joke about it being an act of charity, but I could see he was excited by the prospect. I told him not to push for it -- Erin would initiate if it was something she wanted.
---
Abby collapses to the bed as George's hot seed spills from her pussy. God, the sight of my husband inseminating a girl almost half our age... it turns me on in ways I hadn't thought possible. Knowing my job, I crawl up on me knees, spread her legs, and start lapping my husband's cum from this tight younger pussy. God the mix of their juices tastes so good. She is so fucking hot, with her tight young body... even hotter than I was a this age. I would have wanted to finger her and suck her clit even if George had nothing to do with it.
I am so focused on the delicious pussy in front of me, I lose track of what George is doing. Until I feel him kneeling behind me, wrapping his burly arms around me. I keep licking, not wanting to lose focus. He kisses the back of my neck, shooting electric impulses down my spine. His hands grab my hips -- fuller and jigglier than this per young thing in front of us, but he still seems to love them. He reaches around, and oh god. Oh god. He's going to touch me. We agreed I was only allowed anal play so long ago, thus the plug in my ass. But his hands wander down, through my bush, and slowly trace my outer labia. They feel more sensitive than I could imagine that part of my body being, but I want, I need him to do more.
His lips brush against my ear as he growls: "did you like seeing me fill up this tight young pussy?"
"Yesssssss..." I moan, not moving my mouth from the wet slit.