Introducing the innocent girl to anal [m/f]

Over the last week or so I've had a great time writing about my time dating this sexually repressed woman and how insanely hot it was to break down her sexual barriers one by one. I'm sad to say I'm just about out of stories about her… but this final (or maybe penultimate) installment might be my favorite one yet. If you want to read the rest of the stories for some background, here they are:

Making her beg / Making her squirt / Eating her out

We'd been dating for ballpark five months, and the sex continued to be phenomenal. I kept pushing the boundaries, she kept resisting and eventually caving in. I came to realize that she loved the process of being corrupted as much as I loved being the corrupter– she was a sub to her core and came the hardest when she was being "forced" to do something that she felt was degrading or wrong. The hottest part was how she'd always end up begging for it– watching this nice Catholic girl implore me to choke her, to call her a whore, to make her squirt– those times remain some of the hottest memories of my life.

But there was a final frontier, one I'd tried to cross many times with no success– her tight pink little asshole. I'd be taking her from behind and the brown eye would just be winking up at me as if to say "you never get this, you never get this". But one day, I get this.

We were drinking– it was Labor Day weekend (Memorial Day? Whichever one's at the end of August) and we were at a friend's lakehouse. It was the whitest preppiest weekend of my life and I fucking loved it. Waterskiing, lawn games, kayaking, grilling– if you can picture a shirtless dude doing it in Chubbies and Wayfarers, we did it.

Anyway it's Sunday night and people are pretty wiped– the last two nights we were up late getting drunk– and most people pass out by midnight. Now this lakehouse was great, but it was crowded, and Caitlin and I hadn't gotten any alone time all weekend. I'd been teasing her all day, grabbing her ass when no one else could see (or, fuck it, even when I knew people could see), kissing her hard up against a wall if the room we were in was suddenly vacant, running a finger up the inside of her thigh at every opportunity, appropriate or not– you get the idea. I'd had to jump in the lake to deflate a boner more than once.

Caitlin was looking damn good this weekend– I feel like I haven't done her justice in previous posts so I want to recap for y'all. She had the prettiest face– gorgeous, even. This quick white smile that could charm the habit off a nun, wide dark eyes that were at once innocent and sultry, a cute little nose with a tiny stud (her only outward sign of rebellion). Her legs by the end of the summer were tan and toned– she'd been running (and crushing) 5ks all summer and was in great shape. Her legs swelled into just a perfect round little ass– tight, smooth, ample… goddamn. Her stomach was flat and toned, and her tits were more than handfuls. She'd been a dancer, and she moved like one, plus she had a ton of residual flexibility. She had amazing curves, but was certainly light enough for me to pick up and throw around.

So needless to say, when everyone else passed out and the two of us were left sitting by the fire pit, the little head took over. I grabbed her and pulled her on top of me, straddling me on this long cushioned bench. We started an aggressive match of tonsil hockey, and I circled her little waist with my arms and pressed her body against mine. I fucking love that first torso-torso contact– we were each in our bathing suits, so it was just skin on skin. I looked around to make sure we were totally alone. Everyone else had gone up to the house, which was up a hill from this fire pit gazebo thing, and it was quiet except for the bullfrogs, the occasional loon, and the crackle of the fire as the flames collapsed into embers. It was one of those perfectly comfortable nights– where you could walk around naked and if someone asked you if you wanted it one degree warmer or one degree cooler you wouldn't be able to answer. Ok, poetry session's over, back to business.

I pulled her top off and her boobs bounced free, nipples standing up straight despite the warm weather. I attacked them with my mouth, and she moaned and shoved her chest up at me for better access. I flipped her over so she was on her back, and licked my way down to her thighs. She was breathing hard now– I'd shown her the light and now she couldn't get enough oral. I slid off her bottoms and dropped my face to her little shaved pussy. My tongue flicked over her clit, then plunged inside her, then I sucked her little nub into my mouth. She came fast and loud, and I quickly clamped a hand over her mouth in case people were still awake. She sucked my index finger into her mouth and swirled her tongue around it, and my cock somehow got even harder. I lowered my head back down to her sex and suddenly got an idea. The way she was positioned her hips were rolled up towards me, so I could see her pussy as well as her little asshole. I start eating her out again, rubbing two fingers on her G-spot as I devour her cute pink clit. Just as she starts to come, I drop a finger down and rub it over her asshole. Her thighs tense up around my head and I hear a muffled "mmmmphh".

When she comes down from her orgasm, she turns to me and says "now what the hell do you think that was? I've told you, that's a no-fly zone."

I smiled at her and said "You're going to be begging me to fuck you in the ass by the time tonight's over." Her eyes went a little unfocused, her mouth went a little slack, and I could tell she had just gotten turned on beyond belief. Like I said, she was all about getting dominated and being made to do the taboo. Anal was a big step for her but we were both pretty drunk and worked up from the weekend of forced chastity, so I felt confident about it.

I lowered my head to her pussy one more time, and could tell from the fingers in my hair that I was hitting all the right spots. She sucked on my finger harder, and I felt her legs start to tremble around my head. Just as she started to come, I licked my way down, flicking into her vagina, dropping lower– and, to my surprise, she rotated her hips up to meet me. I circled my tongue around her asshole and felt her whole body go rigid. As I lapped at her backdoor she started convulsing like she was in an exorcism. After a solid 30 seconds or a minute, she pushed me away and sat up. It was pretty dark but I'm sure she was redder than the Rosenbergs.

"That was… how…" she started, then shook her head "That was too dirty. You can't… you can't do that."

"Mmmmm I think I can," I responded. "You didn't like it? It looked like you did."

"That's… not the point. It's dirty! You can't… not back there."

Seriously, this was like some sort of porno (but I poop from there!). But she seemed to be holding firm– she even made me take a swig of beer to "wash my mouth out" before she'd kiss me.

We started getting back into it, and before long my trunks were off and the one-eyed monster was right at her entrance. She was on her back, legs wrapped around my waist, and as I slowly pushed inside of her her eyes closed and she let out the sexiest whimper I've ever heard. I started pumping in and out, slowly at first, then faster and faster. I leaned back so my cock was hitting her G-spot, and gave her clit a quick rub. She tensed up and gasped. "Oh my god, baby, right there, I'm right on the edge". I pounded into her three or four more times and she clamped her arms and legs around me as she started shaking and moaning. Before she was done I'd grabbed her and lifted her back up so she was straddling me. I plunged back into her, deep, and she screamed. I grabbed her throat with one hand and started rubbing her clit with the other, gyrating my hips so my cock swirled inside of her. She came hard, her hand pressing mine harder around her throat. I started fucking her, bouncing her little body up and down on my cock, and all of a sudden I felt a gush of liquid on my lap. Her whole body was trembling now, and it felt like forever when she finally tapped my hand and I let the blood flow back to her brain.

She stared me in the eyes and said something that I've never forgotten: "Holy shit, you're far and away the best I've ever had. How the hell are you able to do that to me?" One of the best compliments I've even been given, hands down.

I flip her over so she's on her hands and knees on this cushioned bench, and I'm standing behind her on the ground. I start fucking her, and then transition into one of my favorite positions– I grab her wrists so her head gets forced down, and use her arms for leverage so I can fuck her with the fury of Zeus. She's gasping now– she loves being fucking ravaged– and I'm having a staring contest with her brown eye. Her fingers scrabble against my wrists, clamp down, and she starts coming again. I can feel her tight little pussy clenching on my cock, and as it does her asshole pulses as well. I release her arms and give her a hard smack on the ass with one hand. As I keep fucking her with long hard strokes, extending her orgasm, I pop a finger into my mouth, lubing it up, and slide it right into her clenching rosebud.

It's deliciously tight– almost too tight for my finger– and as it goes in she lets out a wanton moan.

"HOLY FUCK that's so fucking… fuck" (her vocabulary condenses down a bit when she's mid-orgasm). I slow down– I'm dangerously close at this point, and don't want to break this momentum to give me time to recover– and just ride out her long orgasm.

"Oh my god I'm still coming… how… holy shit" she gasps as I gyrate my hips. I can feel my cock with my finger and vice versa.

Finally I pull my cock out of her and replace it with my other hand. I keep my finger in her ass. As I start playing with her pussy, she begins to rev up again. I'm a little shocked that she doesn't complain about the finger in her ass, but I'm certainly not going to make it an issue.

"Oh yeah," she moans, "just like that. Fuck baby, I don't know how this is possible, but you're gonna make me come again." If you've read my other stories, you know what's next. I stop.

"No," she whines, "no, no, no no no. You're not fucking my–" I rub her clit a few times "–holy shit, right there, oh god. No, don't fucking stop goddammit no I'm not going to beg–" I circle my fingers on her G-spot as I slowly pump my finger into her ass. "–oh my god OH MY GOD don't stop, please please don't stop, I'll be a good girl for you, I'll suck you off, I'll let you come on my face, but I'm not letting you fuck my ass." I redouble my efforts, and she squeals as I bury three fingers inside her pussy. Her ass is trembling and she's starting to sweat. Her fingers are digging into the cushions and she's moaning a little with each quick breath. Her left leg begins to spasm and I stop. She looks back at me over her shoulder, eyes hooded and dark with lust, and gasps "please fuck me"

I pull my hand from her pussy and slap her ass– I can feel it clench on my finger as I do.

"Where do you want me to fuck you?" I ask. I pop my finger out of her ass and quickly slide two in from the other hand, wet with her juices. She gasps and mutters "holy fuck" before spreading her legs a little wider. She's loving this way more than I expected her too, and I can see her resolve crumbling.

Finally, she whispers. "My ass".

"I can't hear you" I reply, my free hand smacking her ass again.

"Please…" she whines. "Please fuck my ass."

My cock is beyond hard at this point. I thrust into her pussy in one go, and she gasps. Then I pull out all the way and pull my fingers from her asshole. It doesn't gape open at all, snapping shut as my fingers leave it. This is going to be fucking tight.

I spit on my hand and rub the saliva all over my cock, and scoot her to the edge of the bench to get her in position. I line up my cockhead with her little rosebud and start to press forward. Her mouth opens up in a little 'o' and her hands clench the cushions. There's a moment where I'm not sure that it's going to work, but then her sphincter yields and she lets out a long low moan. I start pressing into her, slowly sinking my shaft in. She's writhing under me, panting in a very good way. I reach a hand underneath her and start circling her clit.

After what seems like ten minutes I feel her ass pressed against my pelvis, and realize that I've just taken her anal virginity. It's the tightest thing I've ever felt– she's still adjusting and so she's intermittently clamping down around my cock. It's pure distilled heaven.

After a minute she starts to relax, and I start fucking her. Slowly at first, then a little faster, then faster and faster. She's pretty into it at first, but this gets taken to the next level when I grab her arms and just start punishing her ass. I'm fucking her hard now, and she's just letting loose.

"Holy shit right there, oh my god you're so fucking big, you're so deep, holy shit. No one's ever done this to me before, oh my god it's amazing"

I'm of course loving this (as an averagely-endowed guy, it's fun to feel like I've got a porn star dick). "I thought.. you were… a good little… Catholic girl," I managed to get out between hard deep thrusts. "You're… just… a… dirty… whore… aren't… you? You… like… when… I… fuck… your… ass?"

"OH FUCK YES, fuck my little asshole, I'm your little slut, use me, fucking use me. Oh my god you're just filling me up, filling up my tight little ass."

With that she starts to shake, and then she just lets out this noise that's part scream, part sob, part moan, and her upper body goes limp. I can feel her ass pulsating around me and it's just too much. I explode three days worth of cum into her tight ass, and her contractions just milk every drop right out of me. I collapse onto her, breathing hard, and we lie there for several minutes before my cock slips out of her.

We roll over so I'm on top of her and have the most intimate, passionate makeout session I can remember. We jump in the lake to clean off, and sneak back to the house and slip into bed. As we're about to fall asleep she wriggles her ass against me and whispers "thank you".

The next morning we learned that half the house had heard us fucking. She was embarrassed, of course, but it just made the whole thing that much hotter for both of us.

Source: reddit.com/r/gonewildstories/comments/39pd8t/introducing_the_innocent_girl_to_anal_mf