Alice’s Wonderland: Chapter 6: Pegged For A Pegger [F/M 20s, femdom]

I had woken up extra early. The little research I did on the usage of enemas, had taught me that the preparation, execution, the wait after the execution, and the aftermath, would take a considerable amount of time. Not something one should do when in a rush. Thankfully, the simple mixture of water and salt that I had mixed up, made for an easy and effective homemade enema. All-in-all, the procedure took up about an hour, giving me some extra time to mentally prepare for today’s training.

Suddenly, the phone lit up. “Hey babe!” the notification read. It was Laura. I quickly unlocked my phone to open our chat. A follow-up message appeared, “What have you been up to? You’ve been so quiet! When I told you to surprise me for Valentine’s Day, I did not mean for you to ghost me!”

I quickly typed back, “Sorry, love. Working on your surprise took more effort than I thought it would! But it’ll be done soon and then I can show you! I think you’d be surprised to learn what I did for you!”

“I’ll let you get back to it then! Looking forward to finding out!” Laura’s message read.

The most epic pegging fail… Shit happens [FM]

I’m always fascinated at how y’all respond when I write about pegging because they tend to be popular stories. My theory is that A LOT of y’all have pegging fantasies you’re reluctant to voice, so let me start by saying that pegging (any ass play generally) is fucking awesome. If you’re curious and with a consenting partner, try it. I truly feel bad at how many men are afraid to voice this because I think it’s wrapped up in unhealthy stigmas that shouldn’t exist.

I’ve been so reluctant to write this story out of fear it might dissuade some curious readers, but I also like to take moments to use this account to discuss some of the more “real” intimate parts of sex. It’s not always seamless.

Plus… This story is pretty fucking funny.

I’ve been lucky with ass play generally because I first experimented with a bisexual man. He was very into prep, communication, and general tenderness. The first time I pegged him I immediately understood the appeal. He came so hard his body started convulsing.

It prolongs ejaculation and stimulates a lot of nerve endings. It was super fun to give someone pleasure that way.

(M24) Bi – An amazing birthday present 🤤 – part 1 [MM] [Group]

This story is going to be pretty fucking gay 😂, so if you’re not into that, maybe skip this one.

It’s been a while since I posted a story. Sorry about that 😅, but life got a bit hectic.

I turned 24 last September and to help me wind down and return to basics, my girlfriend got me an amazing gift. She helped me live out one of my most anticipated fantasies.

You know the drill. I like my stories the way I like my cock…long!

Enjoy 😉

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So I’m in uni as an engineering student and it’s not going well to be honest, so I picked up an apprenticeship in case college falls through. This has left me with almost no time at all and has spent all my energy for the week before it even starts. I leave the apartment at 6:30 to drive an hour and a half to college, then at 5, I leave for my welding and fabrication gig to then go home for the day at 21:00 for food and then straight to bed. It’s been this way now for too long and it’s exhausting me. My beautiful girlfriend has always been super supportive and has been a pillar of strength for me to lean on during all of this stress.

A Night of Free Use (part 2.5) [M22|F29,39,26,19,19] [Femdom] [Free-Use] [Anal] [Spit Roasting] [Body-Writng]

(Part 3 of this story is coming out soon, but there were to many things to explore where “Training Day” left off. So here are a few short vignettes. Check out the previous two parts on my page)

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“Your first night must have been real fun. It was all the patrons could talk about for the next few days. ‘Oh the new server is going to be very popular’ ‘Have you tried out the new boy-toy, very special piece of ass'” a little bit of jealousy came across in my coworker’s voice. It was early in the shift and we were going to be working the bar together. He was wearing a tightly fitted white button down shirt that was cropped just above his stomach, a pink bow-tie, a thong that crept up his hips, and high boots on his feet.

I was still walking funny from that evening. “I enjoyed most of it. Though there are some customers I’m a little scared to see around the lounge.” Mistress Christina had dressed me similarly to that night, black short shorts and thin suspenders. It was her favorite look on he at the moment. Though she added a few touches, you could see the bands of my g-string poking out above the waist line of the shorts and around my neck was a thin black tie. She also had me stop wearing contracts and start wearing my thick glasses again.

Tale of Two Friends: Part 8 [college] [femdom] [fm] [ffm] [anal] [creampie]

Our sophomore year was progressing well and about a month had passed since Kate and I had our midnight conversation. During these weeks Sarah or I had been fooling around with Jon at least once a week to take off his cage and let him cum. During this time he’d also progressed somewhat. We had taken him to get a Brazilian wax with us once and then, while still caged, helped him to explore anal more. Beyond that Sarah and I had recently both chosen to start taking the pill.

This week was my turn to unlock him and I was excited to try something new. I was enjoying being submissive to Sarah but dominate over Jon and I had found that when I was the one to unlock Jon I truly enjoyed making him squirm. We started as I usually did by feasting him and stripping us both leaving only his cage and my necklace from which the key hung. As he ate me out I watch his duck struggle against the cage I leaned down and happily discovered the plug in his ass. “Good boy,” I moaned, “are you excited for goddess to let you cum today?” “Yes goddess,” he spoke muffled by my wet pussy on his face. Once I had cum myself I moved him to his hands and knees. I removed his plug and began to eat his ass. She moaned and teased his balls. I had gone out and bought a dildo just for him. It was glass and had a few ridges but most importantly it was curved to reach his prostate. I showed it to him and his eyes lid up and he nodded, “Please goddess.”

Training Day [Femdom] [Pegging] [Free-Use] [Anal] [M22|F29]

(This is a continuation of my last story. Some Kind of Interview)
When I showed up the next day for my first shift, I was nervous. The event of the previous day had left me shaken, but eager to come back. I was hoping that I could see Miss Mary again and show her how thankful I was for the opportunity. Maybe she would see me in her office again, maybe she would use me like she did during my “interview,” maybe she would return the favor I did yesterday. But when I entered the lounge, empty as I had shown up hours before open to get trained, I could not see her and the door to her office was closed.
Christina, the younger woman that had lead me out yesterday, probably 29 and similarly tall as Miss M, was cleaning behind one of the bars when I came in. “Oh good, you are here early,” She kept cleaning and beaconed me to come over and sit at the bar, “Are you ready for tonight? Big crowd expected for the weekend.”
“How bad can it be, I have worked during Super Bowls and other stuff.” I am trying to act confident, though I’m not sure she is buying it.
“Oh sweetie, the super bowl wherever you worked is going to be a walk in the park compared to a slow Tuesday here, believe me.” As she finished her sentence, she set her rag down and exited the bar. “Come on, we have to find you something more presentable to wear.”
She lead me to the back of the restaurant to a set of three doors and pulling me into the one on the far left. The room was some kind of backstage or dressing room area. There were clothes hanging from rails, mirrors with lights, and some weird looking furniture. While I was looking around, she began thumbing though the outfits on the hangers. I took a seat on a black leather couch that looked like a strange S-shape or an uneven infinity sign.
“What is going on with the furniture in here?” I asked Christina, as I took a seat on the couch.
Not noticing or not caring, Christina held up a few small pieces of fabric, and yelled, “Why do you still have clothes on? Stop waisting time, we have a lot of stuff to cover before the lounge opens!”
“Is there like a changing…” I was cut off almost immediately.
“This is the changing room, now drop you pants or you won’t have a job.”
I quickly undid my belt, took off my pants and shirt, and squeezed myself into the very small and tight short shorts, then Christina helped me with the suspenders. “Okay, now show me how you look in them.”
Conjuring the same energy that I had used yesterday when I stripped for Miss M, I began to play with the suspenders, run my hands over my body, and turn around to shake my ass. But this time when I turned around, I felt a sharp sting on the lower part of my back.
“Arch that back!” Christina commanded. When I turned around I saw she was holding a long thing wooden crop. *SMACK* She hit me on the side of my hip, “Turn back around and do it right!”
I obeyed her orders, and turned around to show off again. I arched my back and poked out my butt, then came another smack, this time on my ass.
“I saw what kind of slut you are yesterday! Now shake that ass like you mean it, or you are going to be running drink covered in bruises!” She bellowed at me, nearly in a rage. I was slightly scared by her demeanor and knew she was serious about inflicting pain if I messed up much more.
I turned around for the third time, dropped my ass to the floor, and shook it as well as I could. I heard a whistle behind me and Christina called out, “Now that’s more like it. Really shake that thing in the air!” I placed my hands on the couch in front of me and threw my butt into the air shaking it as well as I could. Christina continued telling me to keep it going as she shuffled around with something behind me,
Suddenly I felt her hands on my hips behind me. Feeling slightly emboldened by the outfit and Christina’s encouragement, I leaned into the moment and back into Christina. I ground against her for a moment, when I felt something strange. It was something long and bendy… The realization hit me like a ton of bricks. My stomach did a flip and my heart almost stopped.
“You look so good in that outfit, I just can’t resist that ass!” As she said that, I felt her nails push into the fabric of my shorts and tear them open, exposing my hole to her.
I was freaked out, but so turned on at the same time. Something about the way she said she couldn’t “resist” me, caused my fear part of my brain to shut off. “Mmmmmm, go slow at first. I haven’t done anything like this before.”
I felt press gainst my hole with a finger, “You never even stuck a finger down there?”
I responded with a gasp and a mumbled, “No.”
I felt her put a warm liquid on my entrance as her finger pressed into me. The second the tip of her finger pushed into my ass I moaned loudly, surly you could hear it from outside the changing room. I wondered if anyone had come in since and heard me. Though these thought were short lived.
Christina slide the rest of her lubed up finger into me and began pressing against my prostate. My dick was now pressing against my shorts so a clear outline was visible. As she pressed on my P-spot, a small stream of pre-cum began to drip from the end of my dick.
She then removed her finger from my ass with a pop as it exited my tight hole. “Stop being such an attention hog!” she shouted as she spun me around and pushed me onto my knees. Now I could get a good look at her. She was wearing the same black tank top as before, but now instead of pants she had on a harness and a big pink plastic dick. I had never seem one in real life before.
“Open up baby, you gotta get it ready to deflower you little bussy.” she laughed as she grabbed a chuck of my hair and began pushing my mouth towards the strap-on. I kissed the end of the dildo, and slowly opened my mouth to let it in. “How about a little effort here! It’s not like I’m pulling finger nails, it’s just sucking cock!” She grabbed my hair harder and pushed the dildo halfway into my mouth. Knowing that she would just keep pushing, I loosened my jaw and let it slide to the back of my throat. My nose touched her pelvis for a second.
Then I choked hard. I pulled back off her strap and gagged for a moment. I felt slobber running down my chin and a bead of it still connecting my bottom lip to the tip of the shaft. I looked up at Christina as my mouth hung over. “Holy fuck, you are so cute when you give me that face.” She let go of my hair for a second and kept my head up with a grab on my chin.
In a firm but obviously exited tone she commanded, “Lay down on the couch, with your legs above your head, and make sure I can get to that ass.” As she said that last part she gave my left ass cheek a smack, inducing a small gasp from me.
I finally realized what the strange shaped couch was for, as I quickly assumed the position she demanded. She walked over to me and put her hands on the back side of my knees, folding me almost in half and spreading my ass as wide as it would go.
“You are going to love this!” She said with a possessed look in her eyes. As she slammed the cock into my ass. I let out a half moan half scream. I felt like I was being split open at first, but that soon dissolved into a wave of pleasure from the stretching of my hole. “Yea I bet you like that you slut! That ass was made for being fucked!” She said as she continued to fold me in half. She slowly withdrew until she was most of the way out, before slamming her hips against my ass. I moaned and yelled again, but it was already mostly moaning. She continued this motion of slowly pulling out and thrusting violently back into me, each time I moaned louder and louder and it churned inside of me.
“Holy Fuck! I can feel it in my guts!” I manage to yell in between the moans.
Slowly the up stroked begin to speed up, until the match the down stroked in pace. The room fills with the sounds of her harness hitting my flesh, the constant moans coming from me, and the occasional “Holy shit, i could fuck you for days” coming from Christina.
Slowly I feel something building up inside of me. I haven’t ever really felt this way. It’s like a pressure from inside my ass that builds and moves towards my dick My moans become more high pitched and desperate. My dick, which I have almost forgotten about at this point, is throbbing and shaking with the tempo of Christina’s thrusting. She can tell I’m getting close to something I don’t even know is coming.
She grabs my neck and squeezes. “Let it out baby. Be a good little slut and just let it out.”
My eyes roll back in my head. A wave of pleasure rushes over me followed by shaking and shivers. I start to see spots and feel light headed. Christina keeps her hand firmly around my neck and pushes the pace of her fucking even faster.
Finally my dick spasms and shoots a hot load all the way to my face. I don’t even notice as few ropes hit all over my face and even more on my chest, before finally my now limp cock is just leaking slowly. Things get blurry for a moment. I am awash in a sea of pleasure and ecstasy that prohibits much thinking at all.
I realize my eyes are closed. I keep them that way for a moment as I recollect my self. “Oh my fucking god, I’ve never cum like that, felt anything like that, before in my life. What the hell was that?” I ask hoping Christina will respond.
Two clicks in rapid succession cause me to open my eyes suddenly and try to get up. But I can’t, my hands are cuffed together behind my knees. Another two clicks and cuffs are around my ankles. “Don’t worry. You just said that was the best thing you’ve ever felt, don’t you want to feel that way again, and again, and again.” She said as she made sure I couldn’t get out of the cuffs, and was securely held folded and open to further penetration. Not giving me a chance to protest she continued, “Trust me, no one has ever been where you are and not come back to work early the next morning.”
I tried to formulate a protest, but the loose feeling in my ass and the pleasure I was still feeling radiate through my body kept me speechless.
Christina continued, “So as the first part off your training, you have to learn that you are here for the enjoyment of others. Not yourself. That is what good customer service is all about. For the rest of the night when the women running this place get irritated at the service boys or one of our regulars want to try out the new meat, they will come back here and use your tight little hole. Sound good?”
I nod my head and say, “Yes, I understand Christina.”
Christina turns and walks towards the door. As she opens it she turns around and tells me, “I almost forgot! For the rest of training, you will refer to me as Mistress. Nothing else.”
As she turned to open the door, the handle turned and I could hear someone enter the room.
In a strange friendly and cheerful voice that must be for customers Mistress spoke, “Olivia, you are just in time. I just broke him in so she is still tight as all get out.”
The other lady mumbled something and Mistress responded, “Anything for a valued customer. Remember to tip to service.” The light flicked off. I head the door close and the sound of heels approaching. Another plastic dick pressed against me, though this one felt even thicker and with a lot of ridges and contours. Hands gripped the spot behind my knees.
The lady then slipped a roll of cash under my suspenders and a raspy voice said, “I tip in advance. I always get my money’s worth.”
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(Hey like I said at the top, this is part 2 of a hopefully long running series. I’m always open to critic/input/suggestions. Hope to get more out soon.)

I dominated a client at a massage parlour [F]

In my other stores ive talked about a few, they always finish with a happy ending and this one is no different, but the way we got to the ending was not how i was used to lol

Every massage usually ends with me giving them a handjob or giving a prostate massage, they always let you know beforehand so i can put on a latex glove and not to disturb the atmosphere, let them close their eyes and drift away while i get to work on making them cum. I had seen many things while i was there an had probably been working there for 2 years at this point, I had a guy come in looking totally normal nothing out of the ordinary and when i asked what he was looking for he requested a happy ending.

That was fine, I then asked how and this is when it took a wild turn lol, He requested that i slap his cock and spit in his mouth until he reached an orgasm, I asked him was he sure and he nodded, i let him know that i wasn’t comfortable spitting in his mouth that close and he was okay with that he just wanted his cock slapped

[FM] Drilling McDaddy (A Pegging Tale)

On a warm August night last year at my favorite inn on the north side of town, I gave my new FWB McDaddy a proper buggering for the first time.

McDaddy, just separated from his wife, had recently achieved silver fox status in my eyes due to some cosmetic improvements and was really starting to enrapture me. Yes, OK, he was still in a state of long-term unemployment. And yes, he was temporarily homeless too. But hey, at least he looked good, had weeknight availability and was adventurous too! I wasn’t in the market for a husband after all, just a fun fuckboy.

And fortunately for me this particular fuckboy was down for some pegging.

I was pretty amped because 1) I find pegging to be empowering AF and 2) I already owned a designer harness that I’d used on just one other person at that point.

My harness was shimmery and sliver and had a fur lined interior. I’d bought it at a sex shop in D.C. so whenever I wore it, I felt like a leader of the free world understandably. And I was especially excited to see how it would look with the hot pink dildo McDaddy had brought with him that trip.

[MMF] How I Achieved the Pinnacle of Slutdom with Roller Skating Injuries and a UTI

It was a crisp, cloudy Fall Monday morning in the Upper Midwest, and I [F44] woke up in the boutique hotel room feeling a lot of discomfort.

Sadly it wasn’t soreness from all the fucking I did the day before but from the fall I took at a kids’ birthday party at the roller rink attempting a crossover turn.

On top of the knee twist pain and bruising, I realized I felt a constant burning sensation in my urethra. Then I remembered. “Fuck! I diddled my pink after playing up in his stink yesterday!”

The timing couldn’t have been worse. My slutty ass had big plans for the evening.

To back up for a second, I’m probably more, ahem, progressive, than your average middle aged married mom. I’m in an open marriage and have not one, but two quality friends-with-benefits in my collection.

And both of these guys can fuuuuuck.

Minnesota Mike aka MNM [M38] was there in the hotel room with me that morning. It was his pretty cock I’d been riding at the time I made the terrible awful decision to move my right index finger from his taint directly to my clit.

The Best Sex EVER?! That’s What He Said … [mf] [oral [squirt] [creampie] [swallow]

**If this story makes you cum, DM me and tell me what part you liked the most!**

I love working from home. I was sitting on my sofa, an episode of Below Deck playing in the background while I edited a memo. On my coffee table, a glass of champagne. It was 11:45 in the morning. Why not?

Once I finished the memo, I sighed.

Now what? Another episode of Below Deck was ready to go, but I was feeling a little horny. I went into my bedroom and pulled my vibrator out of my nightstand. I tossed my laptop into the bed, pulled up some porn and got to work, pressing the toy lightly against my clit while it buzzed away.

I was particularly creamy. I scooped up some of the juices that ran down my thigh and licked them clean, tasting myself. Porn was great. My vibrator was great. But I needed a DICK. There were a couple of guys I had on rotation. One text and I could be on my back, legs over their shoulders, getting the deep dicking I needed.