[28F] I went on a “sugar baby” date with a hedge fund manager after my “girl with big boobs” stories [FM]

As a little bit of context – I get pigeon holed into “that girl with big boobs,” and I totally embrace it! At some instinctual level, I love the attention they demand in a crowd, the inevitable stares, and the idea that someone is going home and masturbating to the memory of my body. I like when my partner plays with them, uses them, obsesses over them, and objectifies me for them. Anyway, I say this all as context because that’s what started my journey on Reddit. I made a few posts on GoneWildStories and SluttyConfessions talking about my “explorations.” I would post and just delete them thereafter. A cathartic ad hoc outpouring to purge my conscious and cleanse the soul. And then I started leaving them up as a figurative online Eat Pray Love journal into my adventures.

My recent GoneWildStories posts about my roommate brought a lot of… attention. A lot of DMs asking questions (hence my FAQ), what happened next after my stories, asking for some videos, etc. And there were the occasional offers to be a “sugar baby,” but it’s always in fragmented grammar and in vague abstract with extraordinary and lavish abundance. Except for the one Mr. Reddit.

Mr. Reddit spoke eloquently, politely, and he had all the proof to back up his generous, but realistic, promises. He claimed to be a hedge fund manager, which I still don’t really know what it fully entails – but it was clear in conversation with him that he wasn’t some made-up amateur. He could speak intelligently and at length about high finance, acquisitions, culture, and about the intricacies of companies highlighted on the front page of the WSJ. He wanted to “support me,” but I think he also liked just sharing with me. We both lived in the same city and we both shared the same love of sushi, so he offered up an intimate date night over omakase at a very particular sushi place. For sushi fans, it’s derivative to Jiro Dreams of Sushi. And for the date, he advanced me a healthy “stipend” for my time.

I wore a summer-inspired sundress from Rent the Runway. Long and elegant enough to fit in at the bar at a high-end sushi restaurant, but fun and casual enough for a first date. Importantly and very strategically, it framed the key feature and objects of his desire. The bra and dress tactfully chosen a size too small to squeeze the cleavage out ever so slightly to grab his attention. He messaged me because I’m “that girl with big boobs.” I couldn’t fail to deliver on my one claim to fame! The sundress just tight enough for a bit of quad-boob popping out for him to see as we sit side-by-side next to each other at the bar counter. A bit of strategic eyeful in his periphery.

Mr. Reddit ended up being everything he claimed to be. He was average looking in appearance and probably even a bit shorter than average from what I’ve dated in the past, but he was extremely generous, open, and just a good conversationalist. We talked about his recent travels to Peru, his best Catan stories, his relationship with his siblings, and what a hedge fund actually does. He was sweet. I could tell he was trying to not let his eyes drift down to my chest, but he was clearly interested and enamored with the view. Those are always the best kind of guys, in my experience. The ones who want to stare, but won’t at first.

Things heated up and he told me about a recent sex dream he had about me following one of our late night Reddit texts. Apparently, we were alone in a movie theater together. The new Top Gun movie was playing on screen as we’re sitting there next to each other. He’s eating popcorn out of the bag in his lap and he asks me if I want any. Naturally, I oblige and suddenly I reach for his pants. Not the popcorn bag. In his recollection, I look into his eyes and I ask him, “Can I have some?” And then in his dream, I fall to my knees in the theater and I start sucking his dick. I pull out my breasts and as he dreams about titfucking me, Top Gun disappears and it’s like a movie of us now on screen as it’s happening to him also in the theater. Before he could cum, the dream ended.

When he told me about the dream, I was flustered. I like the idea of people thinking about me, masturbating to the thought of me, and obsessing over my chest – but telling me about it is another level. I felt deeply empowered and oddly proud, in a weird way. That this part of my body I used to hide and stress over since it always made me different – could now give prompt this complete Reddit stranger to such extremes. It was a weirdly thrilling moment for me. In return, I tried to squeeze my chest out just a little more for him to return the favor.

We went back to his place after dinner. It was a minimalist one-bedroom bachelor. A desk with many monitors placed around it and a stack of thick text printed out. A wall-mounted TV, but clearly installed lopsided. A pile of food delivery bags to be recycled placed neatly to the side.

Shortly after we got situated on his couch, he quickly went for my dress. I suspect after all the talk about his dream and the long walk back, his mind was already calculating his next moves. The outline in his pants pressing into my stomach as he pushed himself forward onto me. He kissed me on the mouth first. His hands roaming over my body. Mostly, my chest. With more insistence, he worked his way down my neck and onto my chest. He pushed my cleavage together with both hands. The sucking, squeezing, kissing. The enthusiasm was impressive.

As he worked on my chest, I undid his belt and pulled down his pants. A little shorter than average maybe, but thicker. And very hard. Pre-cum already leaking out profusely and staining the front of his boxer briefs. As he popped my breasts out of my top, he was aggressively playing with my nipples. Assertive, but careful. I told him to go harder as I wrapped my hands around his dick. It was clear I could make him finish quickly given his excitement, but the situation called for a slow build.

I pressed my hands into his behind and motioned for him to bring his dick closer to my face. I gave him a wink (or my best attempt at a flirtatious wink) and I wrapped my lips around his dick. Ample saliva dripping down out of my mouth onto my exposed breasts for him. I wiggled out of my top a bit more to not dirty the rental sundress too much. I told him to use my mouth. Soft gagging as he started to fuck my face. Copious amounts of saliva now collecting in my cleavage as he rubs his dick over my face. Smearing me like a paint brush. As he was looking down at me, his hand just guiding his shaft back and forth across my face, lubricated with a mixture of pre-cum and saliva – I asked him if he wanted to fuck my tits now like his dream.

I let a last dribble of spit fall out of my mouth and onto my chest and I wrapped my hands around both sides to let him start fucking my tits. He wasn’t big enough to pop out the other end, which I found sexy in itself. And even more aggressive, he kept thrusting away at my chest. One leg up on the couch and the other on the floor. His hands up against the wall bracing.

After some while, I told him that I wanted his “fat cock to cum on my fat tits.” I cringe as I write it. It sounded sexier in the moment. I promise! And soon after, I could feel the contractions between my breasts. Ropes of thick wetness coating my cleavage. Not enough to piston thru, but enough to know there was action going on inside.

He collapsed onto the couch nearby and kept telling me how this was money well spent, he was so happy we could do this together, it was better than the videos or the dreams. And then I cleaned up in his bathroom and he called me an Uber home.

It’s funny how this “girl with big boobs” story arc and exploration took me to go full circle to then because of the story, meet a stranger on Reddit, to then create more stories for Reddit lol. Also, it’s worth clarifying I am posting this with Mr. Reddit’s permission!

Anyway, hope you all enjoyed and looking forward to more adventures and journaling with you all!! ❤️

Source: reddit.com/r/gonewildstories/comments/wxhcbm/28f_i_went_on_a_sugar_baby_date_with_a_hedge_fund