(this is a consolidation and more polished re-write of a story I wrote in three several posts a couple of years ago…)
Disclaimer and Content Warning: The following story is based on real events, with some minor changes to protect people’s anonymity and to improve the narrative flow. It involves repeated occurrences of a dangerous sexual practice: ass-to-pussy switching (also known as “a2p” or “atp”). While it was very much consensual, it was definitely not “safe or sane” and only somewhat “risk aware” at the time. I’d be a LOT more reticent about that practice nowadays – at the very least I’d have a pre-negotiation that involved an explicit discussion of risks. But back then, I was a lot less knowledgeable about these issues, and I must confess, I wasn’t really thinking with my brain at the time. And also, this was a series of bareback hookups – another massively unwise thing to do. So yes, the narrator in the story is me, but a younger, more selfish, more irresponsible version of me from years ago.
Anyway…
Her name was Alice. (Well, actually it wasn’t, but that’s what I’m going to call her.)
A runner and a hockey player and a gym junkie, she’d graduated with flying colours from a prestigious private girls’ school and embarked on an intellectually demanding course at an equally prestigious University. Type-A as fuck, she was popular with her peers, active on campus, and impeccably dressed in that “private school girl experimenting with a little bit of boho hipsterism” style. The perfect daughter her parents boasted to their friends about.
But secretly, she was a deliciously nasty little slut.
And yes, of course she was a redhead. About five foot six with a runner’s build, slightly broad shoulders that lined up with her slightly wide hips, she had lots of lean muscle but just enough fat on her firm round ass and even firmer C-cup breasts. She had a very sweet, freckled and innocent-looking face and, I distinctly remember, one pierced nipple – the right one, I think.
I met her on a BDSM-ish dating site, where she was very careful not to show her face or reveal any identifying details. We were chatting on that site for a long time. She was skittish. She deleted and then restarted her profile at least once while we were talking. I won her trust by not being a pushy or invasive creep. Or maybe I was just the least invasive, least pushy and least creepy of all the kinky older dudes she was chatting with. In any case, eventually our chat moved to text messages, and she opened up and sent me photos of her face, and even some lewds.
Despite a pretty feverish porn and erotica habit involving dominant older men, she had never been dominated, and only ever had sex with boys her own age. She got her boyfriend to reluctantly(!) try anal once and confessed that she LOVED it, especially the feeling of cum leaking out of her arse afterwards. The boyfriend, on the other hand, discovered he didn’t like anything to do with anal. She was totally paranoid about her friends or family or boyfriend finding out about her “secret filthy desires.” But she was desperate to be dominated.
* * * * *
When she arrived at my doorstep that first time, we were supposed to go out for coffee to see if we clicked. But in the uber on her way over she had confessed by text to being very wet and very horny. I told her that, when I opened my front door, I would say “Hello” and if she didn’t say anything for a silent five count, I would take that as her consent to forget about coffee and instead be taken the way we had talked about. She agreed, but warned me that, despite how turned on she was, she was almost certainly going to say something and we would almost certainly be going out for that coffee.
So a few minutes later the doorbell rang and I walked to my front door, opened it and said “Hello,” with what she later told me was a very smug “shiteating grin” on my face. She opened her mouth to say something, then paused, and closed her mouth and looked at me, half bratty, half terrified. I motioned her to walk in and stepped back form the door to make space for her to do so.
The instant I had closed the front door behind her I grabbed her by the throat with one hand and slammed her against the nearest wall, my other hand behind her head as I kissed her. Hard.
I reached under her skirt and, as promised, she hadn’t worn panties. She was so wet my fingers slipped in easily, one after the other, and then two and three at a time – I even got my little finger in her ass, once I’d gotten it wet in her cunt.
I pulled back, looked her in the eye and told her to kneel. It was the first word I’d said to her since “Hello” at the door. She said “Yes sir” and dropped to her knees as I unbuttoned my fly and took out my cock.
She was tentative at first. She was kneeling “high” and I prefer a submissive to kneel lower, with her ass on the ground, so I pushed on her shoulder and said “All the way down” – but she misunderstood me, and suddenly I was all the way down her throat, her nose was in my public hair and she was trying not to gag. Total natural sub.
When I was hard enough, I took her to my kitchen table and said “You know what I’m going to do to you now?” “Yes sir,” she said, and I bent her over the table
My cock slipped easily into her dripping wet pussy and while I fucked her I started using my fingers, and some lube I’d deliberately left ready on the table, to open up her ass. It didn’t take long.
I took my cock out of her cunt and asked her “Do you know what I’m about to do to you?” And in a slight non-sequitur she just moaned “Please!” I pressed the head of my cock against her ass and, much to my surprise, it gave way quickly, and I was in to the hilt in maybe three gentle strokes.
On the last one, when I had fully bottomed out, I leaned over her and hissed into her ear, “Ssssssllllluuuuttttttttt!”
And then I was increasingly less gentle.
A little later I reached under her and her cunt was literally weeping. I jokingly said, “Oh! Does your poor little cunt want my cock back?” and she just moaned “Anything you want”. I’m a bastard, I know, but that’s the moment I discovered I really love ass-to-pussy aka a2p… She didn’t complain. In fact, as stupid as it was for her health, the next time the little slut actually asked for it.
Of course I finished in her ass, once she begged for it. She even cleaned my cock with her mouth before she said “Thankyou Sir” with a mischievous, slightly bratty look in her eyes. I’d wanted her to stay and cuddle, but she’d gotten what she wanted and so she bounced out he door with my cum slowly dripping out of her arse.
—————————
The second time Alice and I played was arguably the most fun we ever had. It was a few days later and I’d planned to work from home that day, but I woke up with morning wood. In a mischievous mood, I texted Alice:
Me: “Why aren’t you here? I need somewhere to cum…”
Her: “I’m at the gym!”
Me: “Then come here after. I’ll send you home with my cum leaking out of your arse the way you like it ;-)”
Her: “I have a 10 am class :(”
Me: “Come here *straight* after the gym. Then go home or to class.”
Her: “But I’ll be all sweaty!”
Me: “Good, I’ll make you even more sweaty. I want to send you home with my cum leaking into your panties…”
Her: “That would be pretty hot…”
Her (a few minutes later): “Okay. I’ll be there about 8.30.”
When she arrived she was wearing black and pink gym shoes, pale pink lycra yoga pants and a bright pink cropped shirt over a sports bra. And her hair was in pigtails. Pigtails!
As before, as soon as she was through the door I grabbed her by the throat and slammed her against the wall as I kissed her. I spun her around to face the wall, and reached into the back of her yoga pants and underwear to feel that she was already wet. I worked two fingers into her cunt and then used one to tease her ass.
“Are you going to be a good girl?” I asked as I unbuttoned my fly with my other hand. “Yes Sir” she replied. The “Sir” became a sibilant hiss of pleasure/pain as I pushed the finger that had been teasing her ass in to the first knuckle, then the second, then all the way.
I took my fingers out of her cunt and arse and my hand out of her yoga pants as I spun her back to face me. I made her lick my fingers clean and then she watched as I took out my cock, half hard. “Then impress me,” I said and she immediately sank to her knees.
Had she been practicing? Or just thinking about how to please me? She basically did everything the way I liked it. Deepthroated as long as she could. Then sucked the head while maintaining eye contact. Then licking the shaft and looking at it and me before devouring me down her throat again. I started to use her pigtails as handles as I fucked her sweet, innocent-looking face.
Eventually, when I started to get too close, I pulled her up from her knees by her hair and throat and again pushed her against the wall, face-first. “Stay” I commanded. I stepped back, took off my belt and made it a noose around her neck, with the long end used to tie her hands high behind her back. The length of belt between the noose and her hands made a convenient “handle” for guiding her into my living room.
As before, I bent her over my table. I pulled her yoga pants down to mid thigh and then knelt down and slapped both asscheeks hard, which prompted a gorgepus little yelp. I spread her asscheeks with both my hands and then devoured her cunt and ass – licking, sucking, and tongue-fucking her clit, cunt and asshole – with an occasional break to slap her pale asscheeks until there were perfect red handprints on both of them. Through it all she said nothing, just moaned and yelped and breathed very loudly. Towards the end, I put one lubed-up thumb all the way in her ass and moved it around while my other hand held one asscheek open and my mouth concentrated on her increasingly wet cunt and swollen clit.
When I’d had enough play, in one movement I stood up, entered her cunt and pulled the choke belt back so her torso was lifted off the table and my mouth was at her right ear. “Missed me?” I asked.
“Yes Sir,” she moaned.
Then, as I worked up a rhythm in her cunt, using the belt as both a “fucking handle” for leverage and as a mild choke rope: “Please Sir, can you,” she coughed through the choking, “can you, can you take me both ways like you did before? Back and forth?” she asked, her tone an intoxicaticating mix of meekness, lust and shame.
I chuckled. “Reallly?” I asked as I pulled out of her cunt, slid some lube on my cock and lined up with her ass, “You want this in your ass?”
“Yes!” she shouted, almost commanded, as my cock entered her ass. “Yes. Yes. Yes,” she chanted with each thrust as I pushed further in, eventually to the hilt.
“So, little whore, where’s my cock?” I asked. She just moaned. So I slapped her ass, hard. “Where. (Slap!). Is. (Slap!). My. (Slap!). Cock? (Slap!)”
“In my ass! In my ass Sir” She yelled, just as I pulled out and shoved my cock back into her dripping wet pussy.
Her moan was astonishing, a mix or relief and pleasure and disappointment and self-loathing and lust.
“Where is it?!?”
“My pussy.”
Slap!
“You don’t have a pussy slut, you have a CUNT! Now try again, where is my cock now?”
“In my cunt…”
“Where?”
“My cunt!”
“Good girl. Now, call it as I change, and if I have to ask again, I’m going to find my riding crop. Understood?”
“Yes Sir.”
And then, for quite some time…
“Ass”
“Cunt”
“Oh god, ass.”
“Ugh, ah, cunt.”
“Ass!”
“Cunt”
“Ass”
“… cunt…”
And then, “Oh god, I think I’m gonna cum!”
I pulled her up by the choke belt and growled in her ear, as I reached around with my other hand to play roughly with her clit, “Do you seriously think I give a single damn about your orgasm?”
Apparently those were the magic words, becauae she started literally squealing as her body convulsed underneath me, the muscles of her recrum spasming around my cock. I later realised that she’d squirted a little, all over the table cloth and my rug.
By then I was very ready to cum. I executed one last switch to her ass, pulled her up to me by the choke belt and grunted in her ear with each thrust, pounding my swelling cock deeper and deeper into her guts.
“This…”
“Is..”
“What…”
“You…”
“Are!”
“Just holes…”
“For me…”
“To CUM. IN!!”
“Fuck!!!”
“Faaaarrrrkkkkk!!!!!!!!!”
“Take it you little whore, take it all…”
Through all that, Alice was giggling uncontrollably. Laughing and squeeling and coughing from the choke belt, which I’ll admit I probably pulled too hard as I came.
When I’d emptied my balls inside her arse and caught my breath, I untied her hands, pulled out – to a delicious whimper of mixed pain and disappointment from her – swiftly pulled up her yoga pants and panties and stepped back to lean against the wall.
“And now I believe you have a clean up job to do young lady,” I scolded her as she looked back at me from where she was still lying bent over the table, this petulent half-glaring, half-admiring look on her sweaty, pretty face.
She immediately stood up, got on her knees and took my cock in her mouth, licking me clean.
“I just came a river in your ass!” I exclaimed, looking down at her angelic face as she licked my cock clean.
“I know! I can feel it!” she smiled, with a disturbingly girlish enthusasim as she held my cock in one hand and looked up at me. She reached into the back of her yoga pants and pulled out her hand, a glob of my cum starting to drip from her fingers. “See!” she said, smiling, just before she slurped up the mess from her hand, swallowed lustily and went back to sucking me.
If I’d been ten years younger, that alone would have been enough to get me back to fully hard again right there and then…
When her mouth became too much for my sensitive post-orgasm cock, I pushed her away and lent against the wall to recover.
She looked at her phone, which had been lying next to her on the table. “Shit!” she said, standing up, “I have to go now if I’m going to get home to have a shower before I go to class!”
“Go to class like that!” I suggested as I walked her to my door, “I’d love to imagine you sitting in your leture with my cum slowly dripping out of you.”
“Not a chance!” she taunted, as she skipped out my door, jogging to her car looking to all the world like an innocent, naive young girl on her way home from a run or the gym.
——————-
The only real competitor for the best time I had with Alice was the time I fucked her in my office. That had apparently been a fantasy of her’s for a long time.
So, eventually, we arranged it.
One day she was working at her part time job in the city and I was in my office. We both worked late. About 9pm she sent me a text and I went down to reception to let her in. Most people in the building had gone home, but a few were still around. Alice was dressed in business clothes so, aside from her apparent youth, no eyebrows were raised – late night meetings were not unheard of with various court cases ongoing.
I wanted to ramp up the tension so, even though we were alone in the elevator, I just engaged in small talk about her work and studies. Luckily, the only people still working on my floor were at the other end, on the far side of the elevators.
I let her into my office, locked the door behind us and just advanced on her, my eyes suddenly hungry, backing her up against a big bookcase/ cupboard wall unit.
I kissed her, hungrily. Pulled her hair and squeezed her throat as I did so.
“On your knees, slut” I whispered in her ear.
She knelt and looked at me hungrily as she took out my cock, then started to lick the head deliberately holding back, looking up at me with a bratty smile. She got what she wanted when I grabbed her by her hair and forced my cock down her throat and held it there until she tapped my thigh. I gave her a moment to breathe and then began fucking her face, giving her time to breathe between strokes down her throat…
I looked down at her, “Impress me little girl,” and let go of her head.
She forced her head down on my cock, taking me into the back of her throat, with her nose in my pubic hair, and held me there. And held me there. And held. It felt amazing.
It felt even more amazing when I felt her gag and retch, but still she stayed down there.
She wimpered and tears started down her cheeks, but still she stayed down there.
Just as she began to pull back, I grabbed her head and held her there with my cock all the way down her throat. I expected her to madly tap my thigh (our pre-arranged signal from previous times), and she raised her hand, but she didn’t tap – she held it there, poised to tap but not tapping, her pride and competitive nature demanding she give me every last second she could. So I held her head down as she struggled and gagged and retched and the tears flowed down her cheeks.
I don’t know how long she stayed down there, but it was certainly the second most impressive deep throat performance I’d ever experienced (the first was just freaky, and will the the topic of a later story).
Eventually she tapped out and, rather than our normal cruel routine of me holding her there for one or two extra seconds, I immediately let her up. She came up gasping, but smiling with an filthily triumphant look on her incredibly youthful & usually innocent-looking babyface.
“Are you going to FucK me now sir?” she asked sweetly, but with a cock hardenedly filthy emphasis on the “f” and “k”.
“When I’m good and ready,” I replied and pushed her head back down on my cock.
But in reality I was *so* very ready to fuck her.
After a moment, I pulled her up and bent her over my desk and pulled up her skirt. “Panties?” I asked in a disapproving tone.
“I’m sorry Sir, I didn’t get a chance to remove them before I came here,” she replied as I pulled them down.
“Ahhhh,” she exhaled as I slipped my fingers into her sopping wet cunt.
I quickly pulled off my belt, wrapped it around her throat and used the end to tie her hands behind her back, then used the “handle” created to pull her up so he ear was next to me mouth. “ASK me to fuck you,” I whispered. “Please fuck meeaaah!” she whimpered as I slid my cock into her to the hilt in two swift, hard strokes.
While luxuriating in her warm wet pussy, I reached into my desk draw and retrieved a small tube of lube I bought earlier in the day when wed been planning this evening’s adventure. I squeezed some on my thumb, which I slowly worked into her ass as I pulled on the choke/handle and fucked her cunt.
By this, our third tryst, our dynamic was well established. I spread her ass with my thumb while I fucked her cunt and choked her with the belt. Given where we were, she was quiet; but her pussy was dripping. “You know where it’s going next don’t you?” I asked. “Yes please, Sir” she whispered as pulled out and pushed my cock against her quickly yielding anal sphincter. She groaned loudly as my cock penetrated her ass in one long, slow but relentless thrust, all the way to the hilt – but she quickly issued a muffled yelp and quietened down when she remembered where she was. My colleagues were far enough away that I doubt they heard, but she was a good girl for being conscious of staying quiet.
“That’s it,” I teased, “stay quiet. I’m going to use your holes however I want and you are going to: Stay (thrust). Fucking (thrust). Quiet (I pulled out of her ass and thrust back into her dripping pussy).”
To her credit, she made only the quietest moan of pleasure when I surprised her with the switch. And she continued making only quiet groans when I switched back to sodomising her a moment later.
Once I was sure her ass was open enough to take it, I stopped caring about Alice and just enjoyed her holes, ass-to-cunt-to-ass, back and forth as my pleasure took me, choking her with my belt and using her as a kind of two-holed living fleshlight to build myself up to an orgasm.
Eventually, I felt that tell-tale tingling and what felt like a mountain of cum building up at the base of my cock. I executed my last switch back to sodomising her and pulled her up so her ear was next to my face as I grunted myself into it an eye-watering orgasm and ejaculated a river of cum into this tiny fit 20-somethibg’s perfect little ass.
When I had caught my breath, I lifted her chest up off my desk by her hair, untied and took off my velt from around her hands and throat. Then I pushed her back down and slid my cock out of her ass as she let out an almost-disappointed-sounding sigh.
“And now I believe you have a job to do Miss [surname],” I whispered imperiously.
She dropped to her knees and took me in her mouth, cleaning my cock as she reached under herself. Once my cock had subsided in her mouth, I pulled out and got dressed.
“Can I use your bathroom to clean up?” she asked, licking my cum off her fingers and looking at me brattily.
“No,” I replied while handing her her panties, “you can go home to mummy and daddy with my cum leaking into your underwear.”
She gave me a mock look of shock and disgust, but she put them on and let me walk her out of the building to the nearby train station. We chatted about her work and studies and my work as we walked, as if I hadn’t just comprehensively defiled her in my office. She even chastely kissed me on the cheek and waved goodbye as she went down the stairs to catch her train home, giving no outward sign of the puddle of my cum that had to be pooling right then in her cute little boyshort panties…
——————-
It wasn’t long after that that the whole fuckbuddy relationship just petered out – but damn it was fun while it lasted.
Source: reddit.com/r/gonewildstories/comments/qb7nmk/mf_alice_in_anal_land