“Woah! Riley, slow down!” Michael was practically tripping over his feet as the short woman dragged him past the night market stalls by his arm. “The festival’s here all week, we have time!”

“That’s not gonna happen!” Riley let go of her friend's hand, continuing a few steps in front of him before she turned to face him. Her chest rose and fell as each exhale formed small clouds of fog that wistfully floated away, she wasn’t used to all this running around and exercise. “You know not every stand stays open throughout the week! I told you that last year.”

“Yeah, yeah. I remember.” Michael slumped his shoulders forward, Riley did point that out last year but… He lifted his head up and looked at his friend, his eyes lingering on her chest, she wasn’t like this last year. A few months ago Riley caught his ex-girlfriend cheating on him and when he confronted her about it she somehow turned him into a woman. At first Riley freaked out about the sudden change, having to buy a whole new wardrobe to fit his much smaller feminine figure, but he eventually came to terms with his new body. In fact it seemed like he was enjoying it, even requesting for Michael to use she / her pronouns and continuing to hang out after work like they used to.

Michael heard Riley clear her throat as he broke his eyes away from her chest and was met with her smirking at him. “I see you like these puppies! WIll you hurry up if I…?” She turned her head, making sure no one was watching before she unbuttoned the middle part of her sweater and pulling it open. Riley stood in front of Michael with her cleavage exposed, her expression changing from its smug smirk to flushed and embarrassed as she refused to make eye contact with him.

“Oh, uh… Wow!” The cold air hit her warm bosom as puffs of steam floated from her breasts. Michael hated to admit it but his friend was hot and not just because she now sported tits nearly twice the size of her head but her manners and the time they spent together. She seemed happier these last few months, almost clingy as they hung at the theaters or went out to eat. It was as if they had been going out on- “Wait!” Michael shook his head, pulling his attention away from Riley’s boobs and to her instead. “Have these all been dates?”

“What? I-” Riley’s head swung to face forward as her hands pulled her sweater closed. “I mean… I kind of wanted them to be…”

It was Michael's turn to feel flustered as all the small things they did prior hit him like a truck. Riley wanting him to join her to buy new clothes. Her clinging to his shoulders when they watched that slasher flick a month ago. The constant invites to some nicer restaurants in the city. “I wouldn’t mind this to be a date. We can see all the market stands and… well I guess we can talk about it?”

“We could?”

“Yeah. And let’s get you rebuttoned up.”

--------------------------------------

“Agh~! Be gentle~ Oh fuck~!” Riley passionately moaned as Michael pistoned his cock between her tits, his fingers digging into her soft and warm boobs. At first their impromptu ‘first’ date started out awkward but as the night went on the tension that had built up subsided. They saw all the stands like Riley wanted, buying snacks and food from various stands. It wasn’t until Riley saw a plushie that she gushed over that Michael really saw how much she had changed as the old Riley would never fawn over some stuffed animal. And he couldn’t help but think of how cute she was so he bought it for her. From that point onwards they walked about the night market, arms looped around each other as they walked from stall to stall. It was easy to talk to her, as they had been friends for so long before dating, but even so Michael learned so much about Riley. Like he learned that he had always felt a bit more on the feminine side but was too afraid to show it but once he was transformed by his ex he felt like a burden was lifted from her shoulders.

“Ngh~ I’m sorry Riley~ I can’t hold back any more~!” Her squeals and yelps only further excited him as he pressed her tits around his cock. Her large, puffy, and suckable nipples taunted him as they bounced up and down in front of him. But best of all was the adorable flustered girl underneath him who couldn’t make up her mind if he was being too rough or not rough enough.

“Mmm~! Can you play with my nipples~?”

“Gladly~!” Not letting his grip on her breasts falter he pulled his hands upwards, feeling her breasts slide out from his squeeze. Once his hands were at the base of her areolas he held them in the air, her breasts pulled up as the tips spilled from his fingers. With the tit in his right hand he moved his thumb up to her nipple and pressed down on it, causing Riley to moan as he twirled the erect pink flesh with his thumb. For the tit in his left hand he lowered his mouth towards it and, rather than suckling on it, gently gnawed on the tantalizing nub.

“Oh my god~! Don’t do~” Riley clenched her mouth shut as she shook underneath Michael, her back attempting to arch but the weight of the man pinned her to the mattress beneath her.

“Fuck~ You’re so hot I’m gonna~!” Michael felt his hands tense up as he squeezed her boobs with all his might. His penis twitched within the canyon of flesh as he coated Riley's face with his seed. “Ugh~ uh~!”

Michael, unable to hold himself up, fell onto Riley, pressing her chest pillows into his chest. His hands unclenched from her breasts and laid on either side of her head as he watched Riley still reeling from her orgasm from underneath him, her eyes rolling to the back of her head from behind the semen plastered on her face. “Michul~! Ugh~!” 

Michael felt his dick grow hard from the site before him, rubbing against Riley’s crotch which was now soaked with her juices. “Fuck~! Are you ready for round two?” Riley panted, her chest heaving as she simply nodded her head. “Round two it is!” He pulled down Riley’s pants and positioned himself over her, it was going to be an eventful ‘first’ date.