Unexpected Affections - Cover

Unexpected Affections

Copyright© 2025 by BreaktheBar

Chapter 9

Romance Sex Story: Chapter 9 - 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  

The two of you had shifted, and you were sitting with your back to the pillows at the head of the bed while April was sitting just to the side of you, stroking your cock hard again as she kissed you. It was strange, feeling her naked body against yours. You were used to hugs, and Hannah often leaned against you, but naked was just something different.

“You’re almost ready,” April hummed softly as she smiled against your lips.

“Are you sure you want to do this?” you asked.

April leaned back a bit, looking at you with a little furrow to her brow, but didn’t let go of your cock. She did grab your hand though and brought it to her breast, encouraging you to squeeze it. “Ollie, do you think I’m lying to you?” she asked.

“Well ... no,” you said.

“Then I’m only going to say this one more time. I like the man I met earlier tonight. I liked him enough to invite him up to my room. I wasn’t joking - you swept me off my feet with our date. You are, intellectually, everything I want in a partner. Physically, yes, I won’t lie. You could lose a bit of weight. But that’s more because I want you to be healthy, not because I want you to be skinny or buff or anything. And this cock is a big surprise bonus. Do you believe me?”

“I do,” you said, still massaging her breast and revelling in the feel of it as her nipple bounced across your fingers.

“Then can I fuck you, please?” she asked.

You nodded.

April leaned forward and slurped on the head of your cock again, letting a big dollop of spit out that she rubbed into the head with her hand. Then she shifted to her knees and straddled your legs, getting close until your cock was pressed between her stomach and yours as she looked down at it with a little nervous smirk. She glanced back up at you. “You’re going to fill me all the way up, Ollie.” She leaned forward and kissed you, then got a foot up and positioned herself over your cock and used one hand to rub the head over her pussy, getting it into the right position.

Just that rubbing felt amazing, and seeing her lips spread and bulge got you even harder.

“Ready?” she asked you breathlessly.

You nodded.

April drew in a long breath through her nose, then let it out slowly as she sat down on your cock. The pressure was amazing as you felt her body give way for yours, resisting but also accepting, squeezing around the fat head of your cock until April stopped, just the head inside her as she breathed in deeply again. On the exhale she took more of you.

“Holy balls,” you groaned. You couldn’t process what this felt like - it felt like nothing you’d experienced before.

You were having sex.

She did that breath-out-and-lower thing a couple more times before she stopped.

“Are you OK?” you asked breathlessly.

She nodded sharply and leaned forward, putting her hands on your chest to keep herself still. “It aches. You’re stretching me out. I’ve never had anything this big inside me before, and I’m gonna be honest Ollie - I’m a nerdy girl. I’ve tried some of the Bad Dragon dildos that are in weird shapes and stuff. This is- this is definitely the size of the biggest one I own and I’ve always been scared to try it.”

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