*Quick intro note: I’m a handsome, vaguely articulate, well-educated, married and generally successful 39 year-old, pervert. I have a long history of dirtiness, and there’s something about the year and a half of basic confinement that has had me reminiscing about my past and some of my hottest experiences. I’ve decided I’m going to start chronicling them here, to keep them from disappearing altogether. Let me know if they’re enjoyable and feel free to say hello. I like penpals.*
Annika and I met on a dating app and quickly realized we were neighbors. In New York, you’re neighbors with a lot of people, but Annika and I weren’t neighbors in the sense that we both lived in the East Village with 700,000 others. We lived about 30 yards apart. From my rooftop, I could see into her living room window.
It’s easy to date in New York, and with dating apps, you could have drinks or dinner with a new person nightly if you had the desire. And while I wasn’t quite doing that, I also wasn’t far from it. So the reality is that I don’t remember much about our first date, except that we were lazy and went to the only restaurant between our apartments, and that she wore a very low cut shirt. Lower cut that you’re thinking right now. In retrospect, it’s obvious she was trying to signal something, but I missed it at the time.
We didn’t hook up that night, but continued to see each other from time-to-time, flirt, and would often pass the days at our boring corporate jobs by chatting aimlessly on Gchat. And that’s how we really got to know each other. It’s how, for instance, I learned that Annika had recently read The Story of O, and had been looking for the right way to explore her interest in submission. Once I got to know her, that made perfect sense. She was exactly the sort of woman I’d seen that desire in before: highly intelligent, successful, a fancy law school degree after a fancy undergrad degree, and a strong need to not be in charge outside of the hours of the day she was very much in charge. In my experience, it’s not uncommon for women who are Type A in their public lives to be quite the opposite in private. Annika always made me think of this Flaubert quote about adultery, and how it’s the most conventional way to rise above the conventional. I think it applies just as well to sexual deviancy; the most deviant people I know seem to be in search of a way to get beyond the conventional. Annika had done everything perfectly by the book. She had a great job, good friends, a lot of money, took vacations in Park City and the South of France. It didn’t add up to enough for her. In submission, she was looking for something that made her feel things accomplishing everything she’d set out to accomplish didn’t.
Over time, I came to see her as one of the sexiest woman I ever knew, but at first, the right descriptor was “cute”. She was tiny, maybe 5’1, with very obvious Scandanavian heritage, to the point that she seemed to literally always have slightly rosy cheeks. She had dirty blonde hair, which she wore just above her shoulders, and a body that was toned but also slightly thick, with curves, a nice round ass, that fell over her thighs slightly, and perfect, constantly-erect nipples that rose from b cup tits that sagged in a way that made them incredibly soft to the touch. I couldn’t get enough of those tits, and either could the people I’d eventually share her with.
We saw each other for years. Though it was never explicitly stated, and we never defined the titles, I was her Master and she belonged to me. Ours was a relationship that existed somewhere between dating and friends with benefits; we went out, talked often about all manner of things, but were oriented, always, around her submission and desire to learn herself, and her limits. Because she lived so close, it was easy, and nice. She was eager and willing, always. Instead of jerking off, even if I only had 30 minutes to distract myself from my work, I would walk over and she’d be on her knees waiting to suck me off. Always in expensive, sexy lingerie, her collar on, and toys lined up should I want to use them. And I used them quite often. A butt plug, a vibrator, a leather belt which left red welts across her plump ass, and for special occasions, a pair of vibrating panties with a remote control. Those regular, routine get togethers were interspersed with the occasional weekends devoted to exploring Annika’s fantasies and needs more deeply. Those weekends were often elaborately orchestrated to create the right environment for one of Annika’s many fantasies. One included a secluded cabin in Vermont with nowhere to escape to, others strangers that would pass through our bedroom as little more than toys for our enjoyment. Until we weren’t anymore, we were exactly what the other needed.
The first of those strangers was a tall, skinny blonde woman with a thick Jersey accent who worked in Recruiting and had sent Annikas and I’s shared OKCupid profile a message that said only “You can’t tell from my profile, but I’m anything but vanilla.”
Early on Annika made her curiosity about women clear. Like a lot of women, she’d had some limited interactions in college, but all in the context of public makeout sessions, a safe way to explore, guided by the male gaze, and in many ways detached from any real exploration of her sexuality. But as she’d gotten older she’d found herself wondering more and more, to the point that she’d even gone out for drinks with a couple of women from dating apps, though nothing had become physical. In me, she saw a way to make her nerves irrelevant.
I don’t remember the skinny blonde’s name. I doubt Annika would, either. She was a toy for us to play with and she knew that as well as anybody. When the three of us met for drinks, it was simply an exercise in ensuring she was hot enough for us, that she fit into the fantasy Annika and I had crafted together. She could have just as easily been a prostitute. In fact, Annika and I had considered that as an option. Thankfully, the skinny blonde was quite sexy. She’d recommended the bar, a place on the Lower East Side called Max Fish, and which at the time was a kind of notorious spot for artists, comedians, writers and others who liked cocaine. The skinny blonde looked the part.
After a couple of drinks we were back at Annika’s place drinking wine and sharing a spliff. Annika and I had orchestrated this ahead of time. At a certain point, when she felt ready, Annika was going to go into her room and close the door and get herself ready for us. She’d picked out special lingerie, black, with a garter belt and heels. She would, of course, be wearing her collar. She always did when we were alone together. It was a simple black leather collar, significant as a signal, but didn’t serve a purpose beyond that. She’d then wait on her knees for us patiently. Annika enjoyed the idea of being observed that way by a stranger. Being judged, even. And I liked ideas that Annika liked.
Once she was dressed, Annika waited in her room, on her knees. I was supposed to talk to the evening’s guest about wants and limits and set expectations and then bring her into the bedroom to find Annika waiting. I took my time, knowing everything occupying Annika’s mind, the way her heart was beating, her vulnerability, her excitement.
Out in the living room, I started to discuss limits and expectations with the skinny blonde. I needed to make sure she was game. It didn’t turn out to be a problem. Basically the moment Annika closed the door, the skinny blonde crawled into my lap. It was a bold move, considering it hadn’t been discussed, but a welcome one. We started kissing, and she was an incredible kisser. We kissed deeply, desperately, and I knew instantly she’d be quite fun. I grabbed a fistful of her hair and pulled her head away from mine, tilting her face up to force eye contact. I wasn’t rough, but firm, and held her hair tightly enough that if she fought in any direction it would be painful, but staying still was tolerable. For the next 30 minutes or so, we kissed, and teased, and she shared what she wanted out of the evening. It took a surprising amount of self control to not fuck her on that couch with Annika waiting for us in the bedroom. We opened another bottle of wine and smoked a spliff, kissing regularly, groping. Gradually, we started to undress each other. Her dark nipples were visible through a white bra, which cling tight to tiny little tits, just little triangles that might not have protruded at all without the weight of her nipples. Her pussy, which I’d been unable to resist playing with for a bit, was already wet enough that there was a visible damp spot on her white silk panties. I was shirtless, and my boxer briefs barely did anything to contain my erection. I took the skinny blonde by the hand and led her into Annika’s room.
Annika was kneeling in the middle of the room, looking up at us obediently. If she was surprised that we were already undressed and had gotten started without her, she didn’t show it. She always took so naturally to serving, and looking down at her, on her knees, minutes away from a woman using her mouth to cum, I was struck by how at ease she looked, how completely in her element she seemed. I had intended to orchestrate things closely, but the skinny blonde had other ideas. She immediately dropped to her knees in front of Annika, and started desperately kissing her. They looked so beautiful, so in need of this, like they’d both been holding back some essential part of themselves for so long, that it never even occurred to me to stop them even though this wasn’t what Annika and I had discussed. Annika caught my eye, now fully sprawled on her back on the oriental rug beneath the bed, the skinny blonde pulling on one of Annika’s nipples with her lips. I’ll never forget that look. The pleasure, the pride, the intimacy — somehow, despite the fact that it was another person entirely that Annika was playing with, that look made it abundantly clear that it was all for me.
I sat on the edge of the bed above them, and watched them makeout. Their hands started to wander, and the skinny blonde kept kissing her way down Annika’s tight little body, sucking on and pulling her nipples, kissing down her stomach, up her thighs, teasing her. I was content to let this go on indefinitely because I could see the sheer glee in Annika’s eyes. But I wasn’t ready for the skinny blonde to star licking Annika’s little pussy quite yet. To keep that from happening, I looked down at Annika and told her to show our friend how she sucks my cock. Eagerly, Annika scrambled to her knees in front of me, and slid my boxer briefs off. My cock sprung free, and the skinny blonde let out an audible gasp. She’d felt it earlier, but this was her first view of it. Annika said “I know, I love this cock.” She then proceeded to dutifully choke on it, taking me as deeply as she could, gagging herself aggressively. I pushed the back of her head down further, holding her in place, only letting her up when I was certain she’d gasp and breath in deeply. She looked up at me, her face covered in her own saliva, a slight smile on her face. I knew this is what she wanted. What she wanted to be seen doing. What she loved more than anything. Seemingly a bit jealous, the skinny blonde took a turn, and swallowed my cock until I felt it touch the back of her throat. She gagged a bit, and looked up at me, pleased.
I’d banked on Annika’s competitive streak taking over, but didn’t anticipate the extent of it. For the next twenty minutes they took turns sucking me off, pushing each other to take me deeper, gagging, gasping, both covered in saliva. I pushed them together, and they kissed, a mess of spit, barely bothering to keep their tongues in the other’s mouth. I could see something in Annika — it wasn’t quite anger, but something more like a competitive fire. I’d spent the last few months telling her that nobody had ever sucked my dick better, and I think she felt a challenge, and took it seriously.
If I’d let them take turns on my cock for even another minute, I wouldn’t have been able to stop myself from coming. So I pulled the skinny blonde up onto the bed and gestured for Annika to follow. The skinny blonde laid back, and I slid off her panties, exposing a tight little pussy, with a tuft of dark hair, and swollen lips. This is what Annika and I had talked about more than anything, the central focus of her curiosity. She had been longing, for years, to go down on a woman. To taste her wetness, feel her body contract and writhe in pleasure, to give into her curiosity in the most full, complete way. Annika had talked about how she wanted me to force her, to press her head into a willing cunt, but that didn’t turn out necessary at all. Annika eagerly leaned down and began frantically licking the skinny blonde’s pussy. She looked up and caught my eye and all that registered in both of us was pure contentment.
The skinny blonde ended up staying the night. The three of us drank and smoked and fucked until 5am, and took showers and passed out in a heap on Annika’s bed. There were a dozen insanely hot moments that night, but none more so for me than catching Annika’s eye the moment she finally got to be with a woman.
Source: reddit.com/r/gonewildstories/comments/smus8d/my_perfect_little_subs_first_time_with_another