[Continued From](https://www.reddit.com/r/eroticliterature/comments/10n2wd4/another_play_night_pt_3_of_5_mf_20s40s_gfe_fdom/)
Another Play Night Part 4 of 5: It’s a Hard Lesson to Learn (She Sure Has You Pegged)
I was about to apologize again when she began to speak in that I’m-not-angry-just-disappointed voice. “I even put my titty in your mouth, and at the first sign of push back, you pulled away. Did I use the safe word? Did you yellow light and ask what the deal was? I really thought we were making progress…”
At this point I would honestly rather go back to the slapping. At least then I had something to distract from the turmoil of doubt and guilt brewing inside. She wasn’t happy and it was, of course, my fault. Just like when I accidentally found the stethoscope, it seemed I’d developed a penchant for ruining things.
The ashamed look on my face only seemed to make her irritation worse. “Nothing else to be done for it, then. I’ll just have to lead by example. Go fetch the footstool while I get things ready. You know the one.” she ordered.
I went in to the living room and returned with the same footstool that I had tied her to when I’d used the large paddle to turn her ass purple. When I got back to the bedroom, she was putting back on her soft flannel shorts, having removed her panties for some reason. “That’s the one.” She looked at my face. “Oh my god. Look at you, feeling sorry for yourself.” It was that obvious? “Stop moping and get over here, silly boy.”
It took a little longer for her to secure me after I bent over the footstool than I’d taken with her. She was much more precise in her positioning, making sure my butt was pointing up in a particular way, that my legs were a certain distance apart. She even had to undo the bindings once to reposition me when the results weren’t to her liking. She knew what she was doing and was putting some real thought in to it.
I could see the Slut Paddle still sitting on the floor and knew I was in for a beating (or maybe whipping? She did have a Catwoman thing, and already had the tail in). This suspicion was supported when, after tying me down, she gently removed the plug that I had almost forgot was there (‘almost’ being the operative word). It was a strange feeling, my stretched hole slowly closing after being filled for so long. It was time to close my eyes again while she began doing something behind me. I could hear her messing with the plastic bag, and some shifting and clinking sounds. I was resigned to my punishment. I’d brought it on myself, after all. I was sure it would hurt, but I deserved it.
Eventually, she walked in front of me and told me to open my eyes. “Tada!” She exclaimed, posing with one hand on her hip and the other up in the air at an angle, like a swimsuit model showing off for the judges.
Around her waist, secured with black harness over her shorts, was a purple, slightly upturned, strap on. “You like?” She wiggled her hips, causing it to shake back and forth along with her boobs and the cat tail still hanging from her ass.
I didn’t know what to say. A plug was one thing, but this was something else entirely. We hadn’t ever really had any discussion about this before and I’d expressed some hesitation towards things going into *my* butt, even though she, in contrast, hadn’t had the same reservations when it came to me putting things in hers. Some distant memory bubbled up slightly, making me feel sick for a moment, but then the thought sank back down.
She smirked at me with a raised eyebrow. “Cat got your tongue? Shit! I should have gotten cat ears too. Well, maybe next time. Oh, here.” She walked over to me, the end of the strap pointing at my face. “I just want to see what it looks like for a sec. Open up.”
Not giving me much of a chance to respond, she pushed the end into my mouth, not going in very far but filling it none the less. “Mmm that is kinda hot. Get some of that spit on it ‘cause I hope you know where this is going.” After rolling it around a bit, she slid it out, then patted it against my cheek playfully. “Anything to say before we go on? Any questions or concerns?” She knelt down closer to my face. “See this is what communication looks like.”
“No, Miss.” I tried not to sound like a guilt ridden child. I sort of succeeded.
“Okay then, say ‘ah’.” With my mouth open, she placed the ball gag that I hadn’t even noticed was in her hand, being understandably distracted, in my mouth and secured it to my head. “I’m pretty sure the neighbors don’t want to hear you screaming this late at night.” I was *really* starting to get nervous about this, as evidenced by the sweat almost dripping into my eye. With how aggressive she’d been, I didn’t know how far she was willing to go. At least as far as sodomizing me while I was bound and gagged it seemed.
I stopped myself. Even though I had my doubts and hangups, I’d already fucked things up enough as it is. I wasn’t really afraid that she’d do (too) much damage and reminded myself, trying not to constantly catastrophize for once, that she had up to this point been pretty careful in her planning. I told myself that I needed to trust her.
I was brought back by the sensation of cold lube dripping on to my upturned ass. I exhaled sharply as I felt a finger slide inside me, spreading it around as much as possible. The plug had done it’s job, seeing as how normally when someone tried to slip a digit into no-mans land (that phrasing takes on a lot of meaning in this context), it would cause me to tense up all over, but it went in without too much resistance. I took it as a hopeful sign for things to come.
“Now, notice how I didn’t just *assume* that this would be an issue and forget about the whole thing.” I felt her tip rubbing against me as she said this, making me involuntarily whimper, “And rather than just miss out on the whole experience, I took some initiative and ‘trusted’ that if you had a problem with it that you would have said something, or use the safe word after we get started if it gets to be too much.”
I didn’t have the ability or inclination to point out the flaw in this plan, seeing as how I was gagged at the moment, but, well, we’d both been through this situation together before at my instigation. “I intend to give you a live example,” she grunted a little as she shifted, lining up with my slippery opening, “of what I mean when I tell you to not hold back so much. And I can bet that you won’t be forgetting this lesson any time soon.”
With that she began applying pressure, slipping the end into me, followed by the rest of her shaft. I let out a low wail as she penetrated me, taking my anal virginity. The first part wasn’t that bad due to the plug preparation, but as she got deeper I started to feel it more. My insides were filling up in a way I’d never imagined before and my eyes felt like they were bugging out of my head. It was like I was taking a big, satisfying shit but it was going the wrong way.
It was then that I realized another reason behind her careful position of me on the stool. I don’t know whether it was the feeling itself or the concept of the woman I loved taking me from behind, but my cock was responding with enthusiasm, despite the uncomfortable stretching pain I was experiencing. I was tied down so that it was able to rise freely underneath me, rather than rub up against the stool, leaving it to grow unobstructed.
At a little over the half way point, she paused to give me a moment. “Fuck it looks good going in you…” she said more to herself than to me. “I didn’t really expect it to rub up against my pussy like this, either. I’m glad I sprung for the one with ridges on this end.” I could feel her hips wiggling and rocking slightly as she explored the sensation, causing her cock to shift in me. “I love how it feels pushing the flannel on my smooth pussy…” My breath was a little ragged as my brain tried to figure out whether this was pleasurable or not, despite what my erection was telling the world.
“Okay, lets see if my… I guess I can’t call you puppy anymore since you don’t have a tail. Hmm.” She pondered for a second, slightly wiggling her hips from side to side, before letting out a laugh. “I guess I’ll start calling you my ‘bitch’ then.” Her hands clamped on to my hips. “Let’s see if my *bitch* can take the rest.” The pressure resumed as she continued the steady insertion, as did my moaning, though slightly softer now that I was more familiar with what was happening.
By the time she was fully inserted, my eyes were watering as five inches had taken on a whole new meaning. She let out a satisfied grunt at her accomplishment and began massaging my cheeks and sides before drawing her nails across my bare skin again, a technique she’d apparently added to her regular repertoire to heighten things. It caused me to clench on her as I arched against my restraints, trying to control my breathing as she overwhelmed my senses. She must have been paying attention to it, because she waited until I reached a more calm state that allowed my muscles to relax before she started to move again.
It was slight at first, her hips only shifting a few inches back and forth and I was able to stabilize my panting, for the most part. The sensation seemed to shift as her movements increased. With my insides becoming more accustomed, a strange new pleasure began to register. It was originating somewhere up between my hole and my balls, and I realized it must be coming from my prostate. I’d heard about how it was supposed to be the male g-spot, but it didn’t feel how I’d imagined it would.
“Mmm my little bitch seems to be getting used to my cock. Maybe I need to pick things up a little.” With that, she began fully fucking me, going in and out. I groaned into the gag as she bent down, the softness of her breasts, still covered by her top, brushing lightly against my back. She reached under and felt my cock. “Looks like I might be able to, ugh, turn you in to a little anal slut yet…” The pressure she was applying inside felt like it was traveling all the way up my shaft. My head wretched back when her finger began spreading my pre-cum over the head.
My groans of discomfort were turning to moans of pleasure as she began to pick up the pace. She was grunting as she pushed fully into me and then pulled most of the way out. I couldn’t stop twitching in her grip. “Shit, you *are* enjoying this, you fucking whore. You like it when I call you a whore? Call you my little bitch? Yeah?”
Her enthusiasm was causing her to become rougher, thrusting harder into me. This brought some of the pain back to swirl in with the feeling of her rubbing my bulb. “Fuck, this is fucking great! I’m getting close just from it rubbing against me and listening to the slutty sounds you’re making for me. I don’t even give a fuck if you like it or not anymore.” My head was bobbing up and down in time to her motions.
“I wanna cum this way so bad… Be louder, bitch!” I felt a loud slap my ass, adding the stinging to the mix. She shifted from her knees up on to squatting on her feet, almost fucking down in to me. This new angle caused her to jab almost right on to my a-spot while I was practically screaming into the gag as she pounded me, trying to get herself off.
I couldn’t stop my sphincter from contracting, causing the pain to increase. “Yeah! Yeah! Take it bitch! Take that cock!” She slapped my ass again, and again. Then stopped to squirt more lube on me. “You better not fucking cum, you little shit! This is about me!” I wouldn’t have thought I was able to with just anal penetration, but the way she started moving in me again was making me less sure. I tried to focus on the pain (hello Trent Reznor) to tamp down the build up in my balls, but I couldn’t tell if that helped or not. Yelling desperately in to the gag did seem to help some, however.
Trying hard to block out what was going on around me, I was about to just let go and suffer the consequences when she stopped moving and shouted, “Fuck! I’m cumming in your ass!” I felt her wrap her arms around my middle, the sweat from her face dripping on to my back as she began to grind in to me while panting. I could feel the ache begin as everything else slowed to a stop. “Ohmygod… So good…” was about all she could tell me about the experience.
With a satisfied sigh, she pulled out of me, causing me to gape briefly and left me gasping at the emptiness she left behind. It wasn’t till then that I realized from how wet my face was that I’d been crying, though my cock showing no signs of softening. I tried to beg her to make me cum, but it just came out as a muffled, unintelligible moans.
She seemed to ignore them and after letting out an exhausted breath, she said, “Well, that was a successful night, don’t you think? Looks like it’s time to get you untied and get some sleep, don’t you think?”
Continued in Part 5: Won’t End It There (You Can’t Undo What You Did)
Source: reddit.com/r/eroticliterature/comments/10omlea/another_play_night_pt_4_of_5_mf_20s40s_gfe_fdom