The annoying chubby chick seduced me [MF]

People liked my other story so I figured I’d give you another one.

Stephanie was a very poor fit for the people I usually hung out with. In contrast to our artsy, stoner-y friend group, she was buttoned up and high strung. She had absolutely no taste in music but loved luxury things like jewelry and designer fashion. Rude and loud with a voice like nails on a chalkboard. She seemed to be cursed with constantly committing social faux pas—it was almost comical. I knew that she had been able to quickly climb the ladder at her corporate job, but in person she seemed so ditzy and ignorant. Honestly she was a bit insufferable. But we put up with her because she had been childhood best friends with Laura, another girl in our circle. I think Laura brought her around because Stephanie didn’t really have another way to meet guys.

Stephanie wasn’t like obese or anything. She wasn’t even really what I could consider fat. But she had more than just a little extra on her. And she was tall (but not towering) and big-boned, with a large frame. She dressed in a lot of sweaters and baggy clothes and had a long mop of disorganized curly blonde hair. Her figure wasn’t an hourglass but I could still tell she had massive breasts and a huge ass. Still, my friends gave her the unfortunate distinction of the chubby, annoying chick behind her back. That “fat bitch.”

I knew Stephanie had her eye on me out of all my friends. It wasn’t something I was too pleased about. I wasn’t attracted to her at all, not least because of her personality. But she continued to aggressively, clumsily, flirt with me. Meanwhile Laura kept telling me how great we would be together. How Stephanie hadn’t had much luck with guys lately. How I should just give her a chance.

One day Laura said she needed to ask me something. Stephanie was still very involved her in sorority via the alumni chapter. They claimed to be a “charity,” but it was basically an organization for rich high society types to mingle and network while occasionally raising money for hungry children. They were having a fancy fundraising event and Stephanie wanted to ask me as her date but was super nervous. Would I say yes? I felt like I was back in middle school. I was noncommittal—normally something like this was not my scene at all—but Laura begged, trying to sell me on the concept. It was just one night and it was at a really ritzy place. The food would be great. There would be an open bar. And then on a certain level, and especially after hearing how nervous she was to ask me, I really felt for Stephanie. She deserved to be around people who liked and cared about her and it was too bad that she hadn’t found that. I knew how important this event was to her and I knew showing up with a date would make her night. I figured at the very least I would get dinner and some drinks out of it and still be done early enough to catch up with my friends after. So I agreed.

The night of, I put on a suit and tie and hopped on the train to Stephanie’s house. When I got there she was still getting ready with some other women, their dates plopped on the couch with glazed over expressions staring at the TV. Not a whole lot of enthusiasm here either. Eventually Stephanie came out as we got ready to call a car. The whole mood flipped. Woah, I thought. Stephanie looked better than I had ever seen her before in a tight lilac dress that stopped well above her knees. It plunged at the neckline, showing off her generous cleavage. She had just gotten a fake tan, manicure, and had straightened her hair. Standing there in her strappy heels, I noticed for the first time how long and sexy her legs were. She came over to me and said “hey” in her raspy voice and leaned in for a hug. She smelled juicy and intoxicating.

The next part of the night was a blur. Dinner was quick. I think there was some sort of awards show or auction—can’t remember. Then a brief happy hour as they cleared the dining tables for dancing. We took advantage of the open bar several times, and I have to admit the drinks were great. Then the DJ came on and people started migrating to the dance floor.

Stephanie seemed more natural mingling with this crowd of people. And I came to realize that despite my reservations, I was having a pretty good time.

We headed to the dance floor and started just joking around, doing dumb dance moves to make each other laugh. She led me around to meet more of her colleagues, shouting introductions to them over the blaring music. The drinks kept flowing as we subconsciously got more and more comfortable with each other. She started grinding on me to some hip hop song and I laughed thinking she was just messing around again. She looked back at me and smiled like “What?” and kept at it as I wrapped my hands around her hips. We kept dancing over the course of a few songs, getting closer and closer. I was drinking in her scent and loving the heat of her body against mine. I was surprised. Stephanie could be sexy. And she was turning me on.

I really had not intended to do anything with her that night, but once I started getting a little excited, she ran with it. She sensed the outline of my cock begin to swell and bounced her ass over it to the beat, grinding up and down. I felt her thong underneath the thin fabric of her dress and traced it with my finger over her thigh. Soon I couldn’t help but start breathing hot and heavily on her neck, and then kissing it, working my hands over her ass, hips, and up to her midsection to draw her in closer to me. She closed her eyes as she grabbed my hand and slowly drew it up to her breast. As soon as I touched it I felt her nipple stand up and stiffen. We kissed, then walked outside and hailed a cab back to her place.

Right after we gave the driver her address, we basically attacked each other in the back seat. I kissed her and rested my hand on her bare thigh and slid it just under her dress. As we turned onto her street I felt her hand on the top of my cock over my pants. Her touch unleashed what felt like a burning hot jolt throughout my entire body. She gripped the head and used her thumb to stroke the underside of the tip. I desperately moved her hand away after a minute, not wanting to cum in my pants in the back of a taxi. She giggled and stared at me with longing eyes, satisfied with herself. We arrived and I threw a few $20s on the passenger seat—fare plus a generous tip. At that point I had completely lost control. My body was aching. I needed to have her.

My cock throbbed hopelessly in my pants as she took me inside and led me to her bedroom. We stood next to her bed and kissed more as she pulled off her dress, revealing lacy black lingerie. I threw her onto the bed, then roughly unhooked her bra and pulled off her panties. Her big breasts were ripe, so much firmer than I had expected. In spite of her large frame she had the tiniest, cutest little pussy. It was freshly waxed, a bare slit anchoring her wide thighs. I stood, took off my clothes and she sat back up and started sucking my dick. She didn’t really know what she was doing, but she was trying hard to please. I gave her a break and tipped her back onto the bed, then got on myself and started licking her pussy. It was mild and sweet. She moaned loudly and screamed “harder, harder!” I picked up the pace and mustered as much pressure I could with my tongue, working it in and out as she continued to shake the walls with her moans. Finally I had enough. I stood up and grabbed a condom from the dresser and slid it on my rock hard cock. “I’m tight…” she whined, laying on her back and spreading her thick thighs. I slowly slid in half way and made sure she was ok, then grabbed her hips to drag her down onto the rest of my shaft. She wasn’t lying—she was tight. I started fucking her hard anyway. She grabbed onto my tensed arms and let me do all the work, pumping her in and out as she laid there on her back gasping and squealing. I came much quicker than usual, burying myself deep inside her as I unloaded into the condom.

She continued to lay there catching her breath as I tore off the condom and got dressed, not really bothering to clean up. I said I had a nice time in a jokey way and she smiled, donning a robe to walk me to her door. We said goodbye and she kissed me on the cheek. I went back to my place and later met up with friends, but I was withdrawn, fixating on what had just happened. I was a little ashamed. I knew what they thought of her. Going into this, I had completely disregarded the possibility of hooking up with Stephanie at all. But the way she had teased me throughout the night made me hungry. And pounding her curvy silhouette outlined in he dim light of her bedroom had felt so good.

I didn’t see Stephanie much after that but Laura still brought her around now and again. She ended up getting super into dieting and those cycling glasses and got very fit. We periodically called each other to fuck over the next few years before I moved and lost touch with her.

Source: reddit.com/r/gonewildstories/comments/kgdc55/the_annoying_chubby_chick_seduced_me_mf