The second night Brenda came by in the Uber was a rough day for me. I was feeling stressed and needed an outlet. I greeted her at the door in my boxers and told her to come to the bed and massage me. She used some oils I had on hand to give me a full body massage. She took all the cramps and strain out of my shoulders and back. I had her rub my feet, as they felt cramped and achy. I slid off my boxers as my dick was fighting to be released.
She massaged my heels and the soles of my feet thoroughly. She asked if I had food for her tonight as she hadn't eaten all day. I told her to suck on my toes and I would order her anything she desired. She obediently sucked all 10 of my sweaty toes one by one, sticking her tongue in between each one at my request. She then licked every inch of my right foot from top to bottom, using her nails and fingers to scrath and rub my left foot.
I spread my ass cheeks and told her this was part of her appetizer. She flicked her tongue against the opening of my anus while pleasuring my feet and toes with her hands. I told her to dig deeper and the price of her meal would go up. Even I was taken aback at how aggressively she penetrated my asshole with her tongue, salivating as she gave me an oral prostate massage.
I grabbed Brenda's hair and fed each testicle into her mouth. She sucked and slurped on my balls and moved her hands from my feet to my cock. She used one hand to stroke the base and the other to massage the head as she devoured my ball sack. Without warning, I grabbed her head and impaled my cock down her throat. She wasn't ready for the oral assault and her throat seized up which made me pump harder.
I skull fucked her furiously as drool and spit leaked out of her mouth and her nose started running. I pulled her face off my erection and told her I wanted to fuck her in the ass. She begged me not to as she said she had required surgery after my friends and I violated her previously. She said she had never fully healed there and that the doctors back home couldn't do anything to alleviate the pain. She pleaded me to leave that area untouched as even bowel movements now caused her extreme discomfort.
I took mercy on her but told her I had a friend coming over and she would have to be extra obedient as he was one of my managers and I was giving her a break by not insisting on anal sex. She reluctantly agreed. I told her to get into doggystyle position and plunged my cock deep into her while I massaged her ass cheeks. She moaned out of both pleasure and pain every time I inserted my full length inside of her.
I put on some R&B and had her sensually grind her increasingly wet pussy on me as I sped up the pace. Brenda was soaking now. She orgasmed three times in the next 40 minutes while I kept switching up the tempo of my thrusts to the music. I began fucking her pussy furiously as she told me it was hurting and to please give her time to heal before the next round. I could feel the orgasm coming as Brenda's discomfort grew more visible. I pulled out and ejacualated all over her ass cheeks. Seeing her jet black booty covered in my semen was a major turn on.
I placed the Uber Eats order while Brenda took a shower. I spent $200 on food for her because she was showing great initiative and I wanted her well nourished. As she exited the bathroom and toweled herself off, I presented her with her steak and seafood meal. She ran over and hugged me. "I'll make your work friend happy tonight, baby" she promised me.
She her food and sipped champagne, as I filled her in on my life. I was waiting for my meal, which was delivered separately, until my guest arrived. She still despised me but I didn't care. I had her right where I wanted her. Right as we were about to polish off the bottle, the door bell rang. It was my work associate Rick. I told her to dress up in the lingerie I had laid out for her in the bedroom while I entertained my guest. I had also set aside some expensive lipstick, eyeliner and makeup in the bathroom, which I told her to utilize.
When Rick arrived, we got down to business. I knew he would appreciate my gesture as he had a reputation for indulging in sex workers, primarily women of color. I laid out my business proposals over the meal. He said that he was impressed but might need time to mull it over. I offered Rick post-dinner champagne and cognac. I advised him to stay seated as I had a special surprise.
I went to the bedroom to make sure Brenda was ready. I was blown away when I opened the door. She had pure African princess vibes and was ready to do what she needed. She wore an elegant dark blue dress and looked intoxicating. I gave her a kiss and told her to go out there and make me proud.