A bit of …anal sex…
Introduction:
I learn something new!
You’d be surprised.
As we enjoy the bubbles and heat, we sip a bit of smuggled wine. We’re not supposed to bring anything in a glass bottle in, but we come here a bit and the girl on duty’s pretty nice.
“As usual, sir, you have made me one very happy girl. You’re a very good lover you know that? Quite the hot fuck if you know what I mean?” as I adopt a Monty Python accent. “Nudge, nudge, wink, wink, say no more!”
He laughs out loud at that.
“You’re not so bad yourself sweetie, a bit of the old all right there, know what I mean?” as he tries it but he lacks my gift of mimicry. Still the compliment is much appreciated. We’ve been together almost 6 months, and in my heart, he’s THE ONE. We’re negotiating moving in together, which he’s never done, so I’m convinced it’s a matter of time.
“Mmmm…seriously, you’re an amazing lover. You never push, you never try to force me in any way. Women…appreciate that a lot as most guys will try to do the old “Oops, it was an accident…”, but you’ve never done anything that wasn’t 100% wanted by me…it’s very sweet.”
“Well, it’s pretty damn good the way it is, why push the issue?” he asks.
“Exactly.” I reply, but a look on his face makes me think. Is he totally happy with what we do? Is there something he’d like to do, but won’t ask? I love the guy, so I’m going to keep all lines of communication open.
“OK, I might be wrong here, but is there something we don’t do that you’d like to? I’m not exactly a prude here. I don’t know if being chained to a wall while you beat me with a piece of farm equipment is something I want, but let’s keep our communications open here, baby. I love pleasing you so much, so tell me if you want to do some new things.”
He gives me a questioning glance and shrugs.
“How did you know that? You are the most perceptive woman, I swear. There’s a…..few things I’d like to at least try and explore.”
“Like what? You can TELL me anything, doesn’t mean I’ll do it, but you can tell me!” I laugh.
He actually blushes! “Um, we’ve never discussed, uh, anal sex.”
“Oh. I’ve um, never done it myself. Isn’t it kind of er, messy and painful?”
“Not if the guy’s very gentle, and proper preparation prevents the mess.”
“How much experience do you have with it?” I ask.
“The woman I dated before I met you was sort of into it once in awhile. It’s a very different feeling for a guy, and I did enjoy it. I’ve been sort of wanting to touch you a bit in the shower or whatever to….oh jeez, feel you out on the subject.” he giggles at his bad pun, but I’m smiling, too.
“Hmmm….touch away, boy, fingers only here…” I get up from next to him and sit down straddling him and kiss him. “Touch away, sexy…”
He runs his fingers up and down my back, and as always, a thrill runs through me. He softly squeezes my butt, and he gently runs a finger up and down my asshole, before he leaves one finger on the hole itself. He then gently parts my ass as his finger slips in, no more than a half inch, and it doesn’t hurt, it feels kind of good as he holds me close.
“That’s not bad at all, you can go a bit deeper if you want.” but he pulls out.
“Not without a little lube, it might hurt then.”
He’s ever so considerate, and I like that a lot. I stand up and reach for my bag which has a few things in it. I grab a bottle of lube (not needed of late, he gets me so wet) and hand it to him. He pours a drop on his fingertip and then slips it back into me, this time about an inch or so deep, and it still feels good. I’d never even thought of my ass that way, maybe this might be fun? He turns his finger and softly flexes it and it still feels good. Mmmm…..I’m going to have to give this a try.
“That’s different than I expected. I think we can give it a try. When do you want to do it?”
“Next weekend would be fine, you do need to make a few preparations, there’s actually a book on it that she had.”
“Can we stop at Babeland and get it?”
“If they’re open, sure.”
“Then let’s do that on the way home. What else do you want to try that we haven’t done yet?”
He blushes again. “Out with it!” I demand.
“Well, there is that Princess Leia outfit…..I could be the space pirate or Empire officer…”
The man gets a handful of water splashed in his face for that one and we settle back into the water giggling. We finish up and as we shower he’s somewhat hard and just runs his cock up my ass crack with lots of soap as lubricant, and I realize that I like that feeling. He’s not in me, just rubbing it up and down, but I like it. A lot. Next weekend will be mighty interesting.
The book is purchased and read cover to cover. VERY interesting stuff I think. I learn quite a bit, and a very small butt plug is bought and inserted. It’s smaller than his finger, but hopefully it will make the initial penetration easier. What my lover doesn’t know is that I’ve got a few other surprises up my sleeve for him that night. I know he’s got a late meeting on Friday, from which he will go directly to my place, and I know he’ll be dressed in his best, which gives me a few ideas.
Friday night comes and he does show in his finest, (which I love, but he hates dressing up) and we have a lovely dinner before heading back to my place. We’ll do a movie tomorrow night, tonight we’re doing each other. Small talk last about thirty seconds, and off to my bedroom we go.
“You, stay right there mister! I have a few…things to get ready. Put the green sheets over, will you? And DON’T get undressed.” I ask him. (We’re actually both kind of tidy about the whole thing, and it’s easier to just throw a set of other sheets over the bed and toss those in the hamper when we’re done.) I scamper into my bathroom and get ready. I dive into the shower for a last minute scrubbing of the area to be explored. Then I dress very carefully and make myself look as good as possible for my man. He’s got a few surprises coming tonight.
“You ready, sexy?” I call out. He’s ready, and out I step.
I hear his breath let out, ending in a low whistle. “Oh. My.”
His reaction is not unexpected. I’m not wearing lingerie, my usual, and I’m not naked. I’m dressed in a white and plaid schoolgirl outfit, but it’s not the slutty kind, it’s a legit, and somewhat conservative one. White knee highs, plaid skirt, white top, and underneath it’s equally conservative, plain white cotton bra and panties. I’m wearing only a touch of lipstick and eyeshadow, and my hair is in a very plain ponytail, with only a white scrunchie and a white plastic barette with only plain silver studs in my ears. My contacts are out and my old glasses are back. I look so nerdy and plain, and hopefully, innocent.
“You wanted to see me Headmaster? Miss Taylor said it was about some rules that had been broken?” I leave this wide open for him, and I hope he has fun with it!!
“Why yes, yes, I’ve heard that some of you girls had been getting well, a bit rowdy. Now I don’t know what’s going on, but I know we have very high standards here, and I expect all girls to live up to them.”
“I don’t want to be in trouble, my parents will kill me!” I whimper.
“Well, let’s see, right off the bat, I do smell wine on your breath. Janet, do you think this is acceptable behavior for young ladies?”
“No, I just wanted to try it. I’ve never drunk before.”
“You also realize we check out girl’s computers? I know you’ve been looking some things are very inappropriate for you!” He’s getting into his role quite well. I’m also getting wet, this is kind of fun!
“Headmaster, I’m so sorry, please don’t tell my parents! Please!”
“I have standards I’m supposed to follow, too, you know. Last month, you served two detentions, and that didn’t seem to stop you. I think maybe a different punishment is needed.”
“Anything, Headmaster, anything! Please!” I’m not so bad of an actress, I think I’d be pretty plausible here.
He shakes his head. “I’m not sure what to do, nothing seems to work for you….unless we try something old fashioned.”
“I’ll do it, I beg you.”
“Well, then we’ll try it. Over my knee young lady. We’ll see if some old fashioned discipline works for you.”
I’ve never done anything like this, but I’m soaking wet now! I assume the position over his knees and he yanks up my skirt, and softly caresses my ass. Then his palm slaps it hard! I let out a yelp as I didn’t think he’d spank me that hard, but another follows quickly! I started this game, I’ll see it through!
A total of 20 and he stops. “Well, let’s see if you’re ok, I do need to be concerned about my girls’ health.” He slips my panties down and caresses my ass again, and this time a finger slides into me as I’ve got a bit of lube in me. It feels soooo good. Then his fingers go further and he slips them into my soaking pussy.
“What is this? This is supposed to be punishment, young lady, not some sort of….kinky fun! What kind of….loose girl are you??” He demands. “Your parents should be notified immediately!”
I go to my knees. “Please no sir! I’ll do anything. It’s just….that I have a problem.”
“What problem is that?”
“I liked…that….because it was….you sir. Please don’t get me in trouble with my parents!”
“Well, I suppose we can let a bit of a schoolgirl crush go, there’s no real harm in it, is there? However, if you do feel that way, I still think you need to be punished so….” he pulls his shirt up and unzips his pants and pulls his rock hard cock out.
“If you’re going to be that kind of girl, you’ll need to be taught. Put that in your mouth sweetie, and lick it.”
I take his cock in my mouth, and I suppose for the role play I shouldn’t be as experienced as I am, so I suck it slowly, only taking a bit in my mouth at a time.
“Oh, now there’s a well behaved young lady, that’s it baby, suck it, suck it good. Yesss….very good, and now let’s see what else you’ve got my dear…” as he pulls me to my feet and kisses me roughly. I kiss back, but he’s well into character. His hands feel my pussy and he strokes me as I get wetter and wetter, and he pulls two fingers out of me and puts them into my mouth and I suck them clean.
“You’re a VERY good girl, aren’t you?” He unbuttons my top and squeezes my breasts and unsnaps my bra (having a little trouble as all of mine are front snaps and this one’s a back snapper) and he takes my left nipple in his mouth and sucks it hard. I spurt a bit as I’m incredibly hot now, and he kisses the other, and sucks them roughly, he’s making me his little slut now, and I love it….
Not sure of his area, he looks around and pushes me towards my dresser, and I sit on the edge and spread my legs for him, leaving my skirt on. He pulls it up, and drives his beautiful cock into me as deep as he can! I let out a gasp as I’ve been hot and wet, but a little anxious as the lines between the game and reality are blurring a bit, and he takes my pussy hard. He continues to kiss me and suck my nipples as he fucks me deeply and I raise my legs up to wrap them around him.
“You are such a good girl, but you still need a good fucking, and I’ll give it to you!” The stuff on my dresser is flying everywhere, but I don’t give a damn! I’m getting good and fucked by my man! He changes his strokes, his speed, and It drives me wild as this position allows him to take me deeper than he ever has. My first orgasm hits me like lightning and I scream out.
“OHGOD! YESSS! Fucking yes!!” as I erupt, and it know it’s a wet one as he grunts out a yes as well, and he keeps slamming me as deep as he can! The dresser groans, and eventually I hear cracking noises, but who cares? I’m loving this! I know he’s not far away from his breathing, and I’m starting to dig into his back and I’m hearing no complaints!! One, two, THREE! He slams to a stop and I feel his orgasm as he comes inside of me! He groans out his pleasure and our lips lock together.
We kiss passionately for a few moments and he pulls out of me slowly.
“Oh, god, I’m sorry, your dresser-” I put my fingers on his lips. “Stay with it, baby, stay with it!”
He grins. “Well, I hope you realize how important it is for you uphold our standards, and I…” he says nothing more as his cock is already in my mouth, I know it’ll take a few minutes, but I’m up to the challenge. I gently lick it, lick his balls, caress his thighs with my fingers as he cools off, and then I can get him hard again. It’s only a matter of a few minutes and he’s growing in my mouth, and work him gently and he’s rock hard again, and it’s time for my introduction….to a bit of anal play……
“That’s excellent work Janet, and I think you understand, but I really want to make sure this lesson sinks in properly.” He pushes me to the bed. “Get on your knees, if you’re going to be that kind of girl, you’ll do it properly!” he snaps. He gets on the bed and gets behind me and I feel him squirt some lube on my ass as his fingers gently rub it in to me. Even in a role playing scenario, he’s gentle where it counts.
“If you’re going to take cocks, you’ll take them every way your headmaster wants them, is THAT understood?”
“Yes, Headmaster!” I feel the head of his cock line up with my waiting ass and he ever so gently pushes it in a little at a time.
“You okay?” he whispers.
“It’s all good baby!” I whisper back. “OOohhh Headmaster, it’s so big! You’re hurting me!”
He drives his cock all the way inside me, but carefully, and holds it inside of me so I can get used to the situation. It feels….wonderful, and he does feel huge, but I like the sensation of my ass being full. He slowly starts to fuck my ass and I push up against him to get all of his cock in me.
“You like your ass fucking? You like being that kind of girl?”
“OOhhh yes, Headmaster!” He starts to pick up the pace, and now he’s giving me a good ride. I LOVE having my ass fucked by him, and then his hand slaps my left ass cheek.
“You like it when your Headmaster fucks you good, you little slut, DO YOU??”
“Yes, yes I do, fuck me harder!!” he does and he does and he does, after his first, he’s good for a bit, and I’m getting all of it!!! The slaps add to it as each one is like a little electric shock to me, and I wonder what else might feel like that?
As good as it feels though, I don’t feel like I’m going to come, I feel….like my orgasm is somehow blocked? He’s pounding away and I enjoy each deep stroke, but coming may be an issue as I realize he’s not far off from coming himself and I really want to come from this! Just as he goes into his final strokes and I hear him groaning I reach back and rub my pussy for a second and I……explode with an orgasm that I shriek out as he pounds me to a stop.
“Aaaaaaaahhhhhhhhhh!!!!” He holds me tight as I come and we’ve almost achieved simultaneous orgasm from anal sex!
We sit there for a moment and he very carefully pulls out of me and I notice he’s got a towel at his side in case there’s any mess but there is none. He wipes himself off but I don’t want to wipe off. I lay on my belly and roll to one side.
“Is it all stretched out like in pornos?” I ask. He looks and shakes his head.
“Not like that, but it is open and I can see, um….the cum dripping out.”
I shiver with pleasure. It felt so good going in, I’ll savor it coming out for a few minutes. He lays next to me but I push my ass directly to his crotch.
“Baby, that was so good, did you like the schoolgirl fantasy?” I whisper.
“I did….you look sooo hot, and um, barely legal….”
I giggle at the compliment as he wraps his arms around me. We shower and spend a most wonderful evening together and in the morning?
I make him go buy me a new dresser as mine is cracked in several places. I think from now on I should only buy high quality, solid wood furniture if our sex life keeps going like this.
This one’s pretty much true! It added QUITE a lot of fun to our relationship!
