First Time

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 bring 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 one 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.”

“Do you want to stop?”

“No!” She said, “No, baby. I just need to get used to it. I feel like- God, maybe I shouldn’t say this, but I feel like you’re making my pussy form around your cock and it’s so fucking good.”

She got all the way down and the two of you sat like that for a bit as she got used to you. While she did she took your hands and gave you a little silent tour of her body. No words were traded, just slowly guiding your hands and fingers to explore her breasts and down her sides. To squeeze her ass. Then she took your thumb in her mouth and brought it down to tease against her clit hood, making her eyes roll a little.

“That’s good,” she whispered. Then she blinked her eyes open. “I’m ready for more, Ollie. But… remember how I said I liked your confidence earlier?”

“Of course,” you said.

“I need you to be that for me here. I want you to take charge. I love that you’re sweet and caring, and I love your heart, but if we’re going to do this more I need you to be a Man. And maybe that’s not fair to ask you in the middle of your first time but it’s what I want from you. Is that OK? Do you think you can do that?”

You took a breath and wrapped your fingers in her hair, pulling her into a kiss for the first time. She hummed happily and melted against your body, her tits pressed to you as you traded spit and your tongues teased and touched. “I’ll try,” you said as you broke away.

She smiled happily, looking you in the eyes, and you realized she was waiting for you to start.

“Get onto your back,” you told her. “I want to fuck you, and look into your eyes.”

She kissed you quickly and then slowly pulled off of you, her pussy not wanting to let you go. The two of you shifted and you ended up standing next to the bed as April spread her legs, her ass right at the edge. You took your cock in your fist and grazed it between her pussy lips like she had, then thrust forward and ground the underside across her mound and clit.

“Mmm, yes, Ollie,” she said. “Like that.”

You shifted the head back down and got it into position, then put a hand on her warm thigh and shifted it further out of the way before pushing your cock into April.

“Gaaawd, yes,” April moaned. “Take me with your big cock.”

“Is that what you want?” you asked. “You want my big, nerdy cock ploughing into you?”

“Yes, baby,” she groaned, feeling every inch you pushed into her stretching her again. “I want your whole fucking cock. Every inch. Fuck my brains into hyperspace, my pussy at warp speed and- and-”

“Can’t think of another one? you chuckled, pressing your thumb to her clit like she’d shown you.

“No,” she laughed. “Not with the glorious dick-straction inside me.”

That made you laugh.

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