The joys of discovering that sometimes ambitious, powerful women like to be completely degraded, too. [FM]

If anyone else had been in the park that night, and if they’d been paying close attention, they might have noticed our silhouettes: we sat on a bench tucked away from the path that wound past the tennis courts, just beyond the reach of the park lights. Nothing particularly unusual, maybe: two people sitting on a slightly secluded park bench after dark, minding their own business. Of course, if they’d been listening carefully, they might have had a better reason to wonder what we were up to—between the slow, distinctive grind of me unzipping the fly of my jeans and the jingle of the ring on the collar around Helena’s neck as her mouth bobbed up and down the shaft of my cock, they could probably have figured out just what had brought us out to the park so late at night.

I took a handful of her long brown hair in my fist and used it to make sure that she was taking me deep enough in her throat. Her bra was in her purse; both of her tits hung out of her tank top. From our vantage point in the shadows, I watched a brightly lit streetcar glide past on the road overlooking the park. I made a mental note to remind Helena later just how many people could have seen her sucking me off, and to congratulate her for being such a cooperative little slut—like she was reading my mind, she let out a little muffled moan.

***

Before we’d made our way down to the park, back before I’d fastened the collar around Helena’s neck and forced her to blow me in a public place, we’d been sitting in a cozy little restaurant and discussing her upcoming promotion at work. A young professional who takes no shit, Helena is ambitious, whip-smart, and easily one of the most magnetic people I’ve ever met—she’s also one of the absolute last people I would ever have expected to enjoy being treated like a mindless fucktoy. This isn’t the story of a specific incident (so my apologies if that’s what you’re expecting), it’s more of an exploration of how Helena came to find herself collared and on her knees in front of me—and both of us learning just how much she loved it.

Of course, I didn’t expect any of it, really. Although we hit it off right away, the really fun stuff—the throat-fucking, the collar, the bondage, the exhibitionism—that all came as a very pleasant surprise much later on. I met Helena at my night gig as a bartender. As a new hire to serve in the bar, she had to do a couple of mandatory training shifts with me behind the wood—and I was immediately smitten. Helena is exactly my type: she’s short and busty with dark brown hair that frames her face, and the kind of rich, expressive eyes that almost seem to shoot sparks. She has a sort of playfulness about her that goes from goofy and fun to very, very sexy at the drop of a hat, and that playful nature is complemented by a captivating smile—when she’s really having a good time, the tip of her tongue pokes out from between her teeth. It was enough to drive me crazy. She wore a low-cut black top that revealed plenty of cleavage and showed off the half-sleeve on her forearm; all I could think about was running my hands over her body, grabbing her by the hips and pulling her close. I’m not sure how much actual information I managed to convey about bartending that evening, to be honest.

To gloss over the less-interesting/more-depressing parts: Helena and I dated for a while; the relationship ended largely because I am an anxious moron. We stayed on good terms, though, and before we knew it we were getting together for movies and dinner again. It was shortly after that that the fun started.

***

In the Uber, on the way back to my apartment from the park, Helena is still wearing her collar, at first making a half-hearted attempt to hide it from the driver. If there are any people in her life other than me and a few of her closest girlfriends who know this side of her—the side that wants to be degraded and completely dominated—I’m not aware of them. As I called the Uber, Helena had taken my hand and guided it under her tights and between her legs—she was soaked. The threat of being discovered in public, I knew, drove her wild, so I couldn’t even begin to imagine how turned on she was feeling knowing that all the driver had to do was turn around and get a clear look at the black-and-red leather collar around her neck to know all about the slutty side of herself that she kept secret.

It wasn’t more than a minute before I found out exactly how wild it was indeed driving her: she took my hand and guided it up the inside of her thigh, pressing it in between her legs overtop of her tights. I couldn’t help but grin. Lately she hadn’t stopped surprising me with how far she was willing to have her limits pushed. I made small talk with the driver, my cock rock solid in my jeans, as Helena rubbed her pussy into my eager fingers as surreptitiously as she could manage without moaning. My apartment was less than 10 minutes away, but the drive felt like it was an hour at least. Just like always, I couldn’t wait to get her clothes off—and there was something especially sexy about having her splayed on my bedspread with nothing but the leather collar against her pale skin.

***

I’m embarrassed to admit it now, but during the entire time we dated, I didn’t really realize how much Helena got off on being degraded. It started slowly: when we were hooking up after we’d dated, I think both of us felt a little more free to test our own limits, which led to me whispering in her ear while we had sex about the things I’d do to her. I’d lean her over the bar in the restaurant while the dining room was packed, I’d tell her, and fuck her while everyone watched. I’d keep her blindfolded and tied spread-eagle in my bedroom, fucking her whenever I wanted over the course of a day, letting my cum dry on her tits without letting her up. By this point, Helena had started a day job of her own, and I threatened to come to her office and shove her under her own desk to suck my cock while I answered her phone. I quickly realized just how much talking this way got her off—and from that realization, it wasn’t long before I understood that we were both just waiting to push our boundaries.

We moved quickly. I started to probe her desires more deeply, and learned that she was very into the idea of rough throatfucking, spanking, and being forced to swallow cum. It was like a revelation: I had always worried that I would be demeaning her if I treated her roughly; I think she thought that I would be turned off if she requested it (always, always inquire about these things early, people—learn from my mistakes!!). Now that we knew that this was not only acceptable but something we both wanted, it felt like we’d each discovered entirely new people in each other. I had learned some basic bondage ties years before, but I suddenly found myself indulging in it with a newfound zeal. I made a spreader bar from scratch and propped her legs wide while tying her hands above her and spanking her ass until she was at the edge of tears. I strapped her down to my coffee table and set a full-length mirror in front of her so that she could watch me fuck her from behind without her being able to move. I fucked her roughly and then, when I was about to cum, pulled out and came in my hand—and then made her crawl over to me on her hands and knees and eat the cum out of my palm, the ring of the collar I’d bought her jingling as she did.

We would do the most depraved things we could think of for hours, often finding ourselves awake as the rising sun started to colour the night sky, and then grab an hour or two of sleep before Helena had to put on the pristine makeup and conservative clothing she wore to the office. I loved watching her get dressed up in the morning while imagining everything we’d been doing only hours prior. There was something about knowing that nobody in Helena’s office would ever have guessed what she had been doing the night before (then again, how would you ever guess that the strong, savvy woman sitting beside you had been down on all fours licking at cum like a dog the night before arriving at the office?) that set a fire inside me. I still find myself drifting back there every so often in my imagination: kissing her goodbye before she clambered down my fire escape in her work pumps, exchanging a knowing glance as the door closed, and then collapsing back onto my bed, the rumpled bedsheets still smelling like sweat and Helena’s shampoo.

For me, the sexiest night we had together was one that I had looked forward to for a long time. Helena showed up to my apartment for a glass of wine and we got dressed up. She wore a long dress that sat perfectly on her curves and heels that made her already fantastic ass even more eye-catching, while I wore a collared shirt, a tie, and some dark slacks. We looked like we were about to crash a wedding. We drove out to a restaurant near Toronto’s King Street, one far enough away from our neighbourhoods that we wouldn’t be recognized, and one busy enough that nobody would be paying much attention. I told Helena that I had gotten her a gift, but it wasn’t until after the plates from our appetizers had been cleared away that I finally revealed it to her: handing her a small box tied with a bow, I told her to head up to the restrooms, find a stall and open it—there were instructions inside the box along with the gift.

I waited very patiently for Helena to come back. I had left specific instructions that she was to remove her panties and place them inside the box, and then give me the box once she arrived back at the table. The gift itself was a ring gag I’d purchased earlier that day—knowing how much she enjoyed having her throat fucked, we’d discussed it before, and she’d mentioned how much she wanted to give it a shot.

Seeing her sit down alone made me want to fuck her right there: she had a slightly dazed expression on her face as she handed over the box containing her thong. I asked her if the gift had fit comfortably and she grinned in spite of herself, telling me that she’d do her best to handle it. Our entrees arrived almost immediately after that, and we didn’t waste any time eating them—we were both eager to get back to my place.

On the drive home, I unzipped my pants and told Helena to lean over and suck my cock while I drove. I took a detour into the quieter side streets around my neighbourhood, and every time we stopped at an intersection, I would grab her by the hair and fuck her throat. In fact, I made it a personal goal to hit as many stop signs as possible. I also took advantage of her not wearing anything under her skirt and had her prop her ass up in the air so that I could finger her pussy with my free hand as I drove. By the time I finally took us back to my apartment, she was dripping.

I had a few extra surprises for Helena when we got to my room: although she hadn’t evinced much interest in it while we’d officially been dating, lately she loved it when I would play with her ass. As such, I had a small plug and some lube waiting by the bed. I didn’t wind up needing the lube, though—I used the toy to fuck her soaking wet pussy first, and had her beg me to slide it into her tight little asshole… and after it was firmly inserted in her ass, of course, I was more than happy to use my cock to fill her twice. Eventually, once she’d had some time to adjust, I slid my cock out of her pussy and into her ass—I also made sure to take a video on my phone, promising her that I’d send it to her for her to enjoy, just so long as she promised me that she would find a time to watch it the next day while she was at work. (Being the good little girl she is, she’d already watched it at her desk several times before I messaged her the next day to remind her.)

We spent the rest of the night fucking each other like our lives depended on it, hardly sleeping at all. Helena wore her collar the whole time, only taking it off when we finally decided that we were both spent.

***

The night in the park with the longest ten-minute taxi ride I’ve ever taken wound up being one of the last nights that Helena and I would spend together. We don’t see each other as much now—her job is going extremely well and the restaurant has all but fallen by the wayside—but there isn’t a day that goes by that I don’t think about her. There’s something indescribably arousing about knowing that the person next to you in the cab, or across the table from you at a restaurant, is just as depraved as you are.

***
[if you have feedback, I’d love to hear it. Comment below and I’ll read everything.]

Source: reddit.com/r/gonewildstories/comments/cwg0wv/the_joys_of_discovering_that_sometimes_ambitious