Not long...

Once you feel your 8" Sissy Tamer get completely soaked in Nicki's drool, you withdraw from her grasping mouth and tell her to lie down and spread her legs. She eagerly follows your instructions as you lie down and start rimming her perfumed virginal butthole, after eating her through a couple of mini orgasms, you kneel in between her legs and rub your lubed up cock up and down her hole before the head catches in her opening.

"When I push in Nicki, you push out, that way it won't be so painful, OK?"

Nicki nods as she starts breathing heavily as she feels your thick cockhead breach her maidenhood, letting out a sigh as the hardest part was over as she feels the rest of your shaft enter her tight butt. Pulling out halfway, you grab your phone and take a picture, showing Nicki the erotic contrast between your ivory invader and her ebony pleasure hole, she begs you to send it to her phone so she can use it as her home screen.

One hour later...

An exhausted, sweaty Nicki, who was now being bounced up and down on your cock by you as she had no energy left, looked back at you and begged you to fill her with your seed.

"Please Daddy, breed your little Sissy bitch... I can't take it anymore, you've broken me... UGH!"

Taking pity on her, you lean forward and get her into doggystyle before asking if she had a buttplug.

"I-in my b-bag, l-left h-hand p-pocket... OH FUCK!"

She screamed as you hit her prostate for the umpteenth time since you took her virginity and came for the last time, the weakest of her loads. That had the effect of tightening her asshole so much it caught you by surprise and you came hard, flooding her bowels with your scalding hot cum, leaving Nicki with a cumdrunk, goofy expression on her face, you make her whimper again as you give her a deep hickey on the left side of her neck, marking her as yours.

Finding the buttplug, you carefully withdrew your cock before quickly inserting the plug into the gaping orifice. Once you'd caught your breath, you grabbed your phone and took a photo of your semi-flaccid cock, with a couple of drops of cum on it next to Nicki's goofy face and sent it to Simona with the tag of 'Got 'em all!'.

Simona replied with a blushing emoji and a quick message: "Meet me at the exit of the forest, I've got what you need to beat Brock, please make him your bitch as well, Daddy!"

After you received that message, Nicki started coming to and quickly realized her place, sucking off the last drops of cum before you show her the picture you took, which she asked you to send to her. After some post-fucking cuddles, Nicki kissed you on the cheek and said that you could call her any time for another 'match'.