Unexpected Affections - Cover

Unexpected Affections

Copyright© 2025 by BreaktheBar

Chapter 3

Romance Sex Story: Chapter 3 - Oliver is surrounded by friends and loves his nerdy life, but after entering a silly Dating App contest his life starts to turn upside down. This is a slow-burn harem story about a big (in size and quality) nerd and the various women in his life.

Caution: This Romance Sex Story contains strong sexual content, including Ma/Fa   Mult   Consensual   Romantic   Lesbian   BiSexual   Heterosexual   Fiction   Humor   Sharing   Group Sex   Harem   Polygamy/Polyamory   White Male   White Female   Oriental Female   Cream Pie   Exhibitionism   First   Facial   Oral Sex   Petting   Squirting   Tit-Fucking   Voyeurism   Big Breasts   Public Sex   Size   2nd POV  

You were nervous as hell. Not because you were going out or anything - you’d long ago gotten used to the occasional looks you got for your size, and while you didn’t usually eat at fancy places like the restaurant the town car was pulling up in front of, it wasn’t like you were worried about getting your forks wrong or something (mostly because it wasn’t that fancy).

No, you were shitting bricks because you were about to meet April Freaking Vilanova.

The week and a half since you had gotten the message that you’d won the raffle on the app had been a bit hectic. Your coworkers at work either didn’t care, or really cared because they were also fans of the different TV shows and games that she’d voiced characters for. Hannah and Hikaru were relentless in getting you ‘prepared’ for the date, and you’d had a couple of ‘practice dates’ with both of them at your apartment over dinner. You felt like those had made you more nervous rather than less as both women insisted you learn to be more direct at flirting.

Even Margot, your friend from the apartment next door, had been in on it. She’d helped pick out your outfit along with the others, and had sat in on one of the ‘practice dates’ to help give you encouragement. All three of them seemed to think you should know all of these different signals and gestures and things that, deep down, you knew were silly.

Yeah, this was a ‘date.’ But it wasn’t a date. It was more like a meet-and-greet at a Comic Con - April Vilanova was getting paid to be the face of the App, which meant she was getting paid to be on this ‘date.’ And that kinda felt a little gross to you, and also a little bad.

You still didn’t want to waste the opportunity to meet her though, and you’d already been sweating a little when the town car that the App ‘event manager’ had booked for you showed up in front of your apartment. Now you were getting out in front of the steakhouse and had to blink a couple of times because of all the extra lights. There was a red carpet leading from the parking lot which definitely wasn’t usually there, and they had erected one of those background walls that had the app logo and the steakhouse logo and a couple of others repeated over and over.

There was a photographer already taking photos of you coming out of the car, and that made you immediately feel self-conscious, but you did the first thing your friends had told you to do and you fixed your posture and smoothed out your suit jacket, then put on a smile.

Fake it ‘till you make it, Ollie, you could hear Hannah’s voice in your head.

You were approached by the event planner, who shook your hand and then led you down the short carpet to the photo-op wall. You already knew everything she told you since she seemed to just be repeating the instructions she’d told you on the phone, and over email. Twice.

Then she left you there in front of the two photographers and you felt awkward as fuck. They also seemed to be feeling awkward.

“Sorry if I have a nip slip, fellas,” you said. “This dress just doesn’t want to cooperate with me.”

One of them smirked and the other smiled and snorted at your stupid joke.

At some unheard cue, both of them raised their cameras and started snapping pictures off to the side, and you looked around and realized April was coming up the red carpet from the other direction as you had where a walled production tent had been set up.

Holy shit, she’s actually here.

“Wow,” she said with a grin as she walked up to you. “You’re a lot taller than I expected.”

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