God bless the motherfucking Air Force. I’d been killing my entire day off alternating between riding my knock-off Sybian and napping- a 20 year old Airman on Tinder hits me up and wants to spend some quality time with me. I told him I was busy napping. He asks to join, and I clarify I’m actually interested in said napping activity- after 30, those naps become increasingly valuable. I’m not saying I wouldn’t cum on his face when I woke up, but god damn it I was exhausted after another successful ride and I need a power-nap to go round 4, 5, 82- whatever. He says that’s fine, he’d like to nap with me. Yeah yeah, I know how this goes- you’re gonna crawl into my bed and those wandering hands are just going to oops their way into my naughty bits. I’ve already prepared my litany of No’s leading to the inevitable GTFO. Whatever, come test my patience adorable baby-faced man. Now that I’ve lost 50lbs I might just fuckin’ eat you– I’m hangry. The drive from base to my house is a solid 30 minutes so I dozed back off by the time I hear the knock on my door.
I sleepily answer the door then mosey on back to the rape cave. I look like it’s my day off; hair up in a pineapple, no makeup, no bra, shorts, and a tshirt. My skin is somewhere between puberty and meth addict. Needless to say, I’m not feeling sexy or interested in pretending I do. I’ve got the attitude of Patty Bouvier right about now. (I’m Selma when I’m pleasant.) Straightaway we snuggle up and I’m already half asleep when he cups a tit, marveling at my piercings. Shiny! I grumble at him we’re supposed to be napping and he apologizes. I don’t know how that transitioned to us chatting a bit, but somewhere in the hazy mumbles he mentions being very sexually adventurous- having dated a woman who got him into anal. I scoff “giving or receiving?” Both, apparently. I’m suddenly more alert; the light’s are flickering on upstairs. Oh really… pegging? He’s never had the pleasure, but he has his own toys and plays with his ass. You have my full attention, airman. Have I got a treat for you!
We matched on Tinder because he’s absolutely adorable- he looks like a young 20, for sure. His body is on the thinner side of average and I can’t get enough of his babyface. He asks me what he should call me and of course I tell him “Mistress.” I tell him I want to show him a magic trick. Rolled onto his back I remove what clothes he has left on. I put some lube in my hands, rub them together to warm it up, and begin to edge him. This is for both of us, I’m still learning how to edge because my technique is efficient- many finish quickly. I want to see him hold on but I also want to watch him cum. I have a deep seated love for watching a man’s O face, and I get noticeably aroused if they’re vocal when they cum. Face contorting reflexively and flushing with color, primal growls or soft whimpers, then release. Hot. As I’m stroking him he’s clearly enjoying it, but mentions he’s got stamina. I can hear “FINISH HIM” clear as day in my head so I begin actively trying to end the hand dance with a climax. His cock is average in girth and above average in length, not my favorite combo but he’s in the range that is comfortable should I decide to sit on it. I want to sit on it. My plan as of now is to knock out his first orgasm and then fuck him when he gets hard again. I just assume he’ll get hard again, that’s the whole point of youth. As we near the 30 minute mark of me jerkin’ his gerkin’ I decide to shift interests. It’s time for me to get dressed.
Earlier I had no interest in getting gussied up, now though… I want all the pomp and circumstance that comes with how I enjoy dominating a man. Skirt, corset, clingy top, heels. I even half-ass fixed my hair into a bitchy looking boss-lady bun. He’s patiently, obediently, sitting on my couch naked staring at my knock-off Sybian while I prepare myself. The tighter I cinch my corset, the more like a Goddess I feel. I’m not happy until I can barely stand unassisted. Once I’m properly situated and feelin’ myself, I fit the fuck machine with the attachment of my choosing for my good boy to sit on. It’s bigger than he’s accustomed to and we didn’t properly warm him up first. I don’t care. Sit. He straddles the machine and takes the attachment to the base, knees cushioned by the same pillows on the floor I had been using all day. I pull a short chair up to face him, prop my high heeled foot up on the matching stand for the machine base, and slowly turn the vibration control on. I continue stroking his hard as a diamond cock while I kiss him, biting his lip as I turn the vibration up. He whimpers he’s going to cum. I turn it up some more, still stroking, still kissing. He’s holding on but not intentionally. So close. I turn it up a little more, again he says he’s going to cum but there’s urgency in his voice- moments later he announces he’s cumming, he’s cumming. And he does. 3 shots, up my leg. I turn the machine off gently and allow him to dismount and compose himself while I clean his hot cum off me. Now it’s my turn.
I removed the attachment he had his fun on, and replace it with the g-spot and clitoral stimulator that I favor just after the double penetrator. I’d been using the double all day, it was time for a change-up. I had him sit in front of me like I had done for him, instructed him to kiss me and nuzzle me while I focused on getting my orgasm. “Yes, Mistress.” Good boy. I position myself onto my fuckstick and manned the controller for myself- I don’t have a single interest in someone else turning the knobs for me, I know how to get me off. Once I start the vibration I signal my new pet to assist in servicing me, he eagerly kisses me and runs his hands up my leg, thigh, skirt, across my tits, over my throat. He nibbles and nuzzles as I throw my free arm around him, I’m getting close. He asks permission to touch my asshole, I give it. Reading my cues he touches the outside gently before pushing a finger inside me, I almost came right then. Triple stimulation is my motherfuckin’ kryptonite. I hold him tightly to me as I feel myself approaching that beautiful edge, so far he’s been exceptional at assisting and he took me all the way over the edge in a loud, wet, shaky orgasm I’m sure my neighbors will never recover from hearing. I turn the machine off quickly and tumble off the side of it, breathing heavy, sweat on my brow, heart racing. I can’t feel my body, I’m floating. Fuck yeah. We’re not done yet, though. This was just pre-gaming.
Once I come down a bit and compose myself again, we sit on the couch and chit-chat. He’s still naked. I’m fully dressed sans panties… they’re on the floor next to the other pair of panties, discarded near the fuck machine from my earlier solo sessions. He becomes hard again and I can’t resist, I straddle him and we kiss deeply. He wants inside me. I want it too. Having already knocked out the first orgasms, I’m feeling pretty confident this will goal in my favor very well. I want him to top me like a work horse. Fuck me until I tell you to stop. Fuck me how I tell you to fuck me. Fuck me how I want to be fucked, without having to give constant direction. He’s intuitive as a partner, we have great sexual chemistry. Time to hit the bed, my vagina is evil and must be punished. I strip down to nothing and we get down to business (to defeat the Huns…? I’ll stop.) Please me, boy. He moves down and tongues my lady piercing, I tell him to put fingers inside me while he licks and massages everything thoroughly. Fuck me. He rises from the deep and pushes himself inside me, hard and fast he takes me with vigor. I bet he’s a fun dom for the girls who enjoy him that way. I enjoy him topping from the bottom. I wanted my work horse and I got him. Just my luck, he mentions it’s somewhat difficult for him to cum during sex. What magical, magical words to hear. We took a break shortly, then back at it, this kid fucks like a champ. From behind was good, next time I want more aggression. I’ll teach him how I like it. Be my personal fuckstick. He wants to fuck my ass, I’m open to it. I try to avoid anal the first time I’m with a new partner, to better gauge if they’re suitable for it. He had the hallmarks of a match, so we proceeded. This is where his shape and size is greatly appreciated; by being average in girth and just a bit longer, it’s more comfortable. Insertion was slow and somewhat clumsy, I was on my back. He pulled too far back after we’d really started going at it, and completely came out. In his haste, and showing his inexperience, he pushed himself back in quickly. I yelped like a kicked dog and instinctively reached behind the pillow for the glass handle of gin I keep tucked between the mattress and headboard. If he hadn’t stopped immediately at my pain indication I would have brought it down on his head. I’m not into painal. But, he stopped immediately. We took a breather with him still inside me, until it could relax enough to continue. We finished without him cumming, I was satisfied and done.
Aftercare time, snuggle me while I drift into sleepy. It’s getting late. Before the window of opportunity closed, he asked if I would peg him. Absolutely, pet. You fucked me like a good boy, I can return the gesture. I put a towel under him, he’s on his back. I pull my Pandora’s box out from under the bed and sift through the silicone and leather until I find the right strap-on. The way it was sized, QuarterRican wore it last when she fucked me. I also pull out my thigh restraints, and slip it on him to hold his legs up so he can better focus on enjoying himself instead of holding the V for Victory pose. I find the 6.5 inch attachment, the smallest of my collection, clean it up just to be sure it’s safe, and attach it. I lube the dildo up first, then his eager asshole. I slip a finger or two inside him, and touch his prostate. Oh yes, this will be quick. I love a nelly bottom. I kept him on his back for a reason- I wanted to watch his face while I slowly pushed into him; both for my own pleasure and also to make sure I was being gentle enough. Slowly, gently, until there’s give and I slide all the way in. Pause. He reaches down and pulls himself open to accommodate every inch of me inside him. More lube on my hand and his throbbing, rock hard 20 year old cock. I take it easy, deep penetration but not long thrusts as I grip and stroke his slippery manhood. He took it for only a minute or two before he erupted cum on his stomach and face. Not gonna lie, I liked making him cum on his face. I back out of him gently and he excuses himself to take care of cleanup and whatnot while I unstrap and get back into my bed. Once he comes back we agree we should see each other again, soon. I’m going to push some boundaries with this boy. I ended up talking to Charlie Sheen about him and we have… plans… heteroflexible boys are fun.
If you’d like to read more of my true encounters, I keep a collection of them on my public blog All The Dicks. This story has a picture with it, which I have permission to share and post at my discretion. There’s also hyperlinks available. Link below is for this story directly
This story was originally published here
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