Fuck her ass, of course

I grabbed the lube and applied some to my cock. Then, I got behind Stacy. Jess grabbed her ass and spread it. "Take it easy at first," Jess warned me. Before tonight, I had never had anal sex. Now, I was about to take this girl's anal virginity. To say I was excited was an understatement.

I put the head of my cock against her asshole and pushed. I met some resistance, but eventually her asshole opened up and the head of my cock slid in. Stacy tensed up but Jess said, "Just relax" and pushed Stacy's head down to her breasts. Stacy started sucking on one of Jess's tits which seemed to calm her enough to relax her asshole. I slowly worked my entire cock into her so very tight asshole. She was even tighter than Jess!

"Mistress, it hurts...." Stacy whined.

"It'll get better. I'll help!" With my cock still buried in Stacy's ass, Jess repositioned herself to where they were in 69 position with her on the bottom. Then, she started to lick Stacy's pussy.

I started fucking her wait slow, long, and deep strokes causing her to whimper. Soon, the whimpers turned into moans. I grabbed her tits, which were soft and yet firm and had small, erect nipples. Either she was starting to enjoy my cock up her ass or Jess's tongue in her cunt was making her feel REALLY good. Either way, her tight, no longer virgin ass felt heavenly wrapped around me cock.

I sped up, my self control wearing away. As I thrust into her ass, she would cry out. I wasn't sure if that was in pain, pleasure, or both. Either way, I was soon pounding her ass.

"Let me taste her ass on your cock, John," Jess said with lust in her voice. I pulled my cock out of Stacy's ass and slid it into Jess's open mouth. So much for "I don't do ass-to-mouth"! I fucked her face while she sucked and moaned on my cock. Then, she tapped on my thigh and I pulled my cock out of her mouth.

"Let's rearrange a bit." She had me sit up against the headboard of her bed and Stacy's sit in my lap facing away from me. Jess got out of bed and grabbed her phone. "I know you're close to cumming, Stacy. But if you want to cum, you're going to have to cum from riding John's cock in your ass."

"Yes, Mistress." She raised up and I put my cock at her rear entrance. She took a deep breath and slowly lowered her ass onto my cock. "Ahhhhhh!" I could tell I had stretched her but she was still very tight. She leaned back into me and I grabbed her tits, again. She started moving slowly at first but was soon bouncing on my cock desperately trying to cum.

My own orgasm was rapidly approaching as I squeezed her tits. Her tight as felt too good. "Fuck, I'm cumming!" With a loud groan, I pulled her all the way down on my cock and came deep inside her ass.

"AAAAAAAAAAHHHHHH!!!!!!!!" That finally set off Stacy and she had a screaming orgasm. After we both came down from our orgasms, we just sat there spent.

"We're not done yet," Jess said as she put down her phone. She had recorded that last part! "I want you to taste your ass on his cock!" Too tired to verbally answer, Stacy raised up off of my softening cock, turned around and took it into her mouth. Jess got behind her and started eating my cum out of her ass!

This was unreal! I always knew Jess was freaky but this blew away all of my expectations. I barely even noticed my cock was hard, again.

"Go to the bathroom and wash your cock off right quick. You're getting some pussy for Round 3."

I pulled away from Stacy and walked to the door. Round 3? More like Round 5. Only reason I managed to cum four times already is the two hour wait after I fucked Jess. Still, I was hard already and would keep going as long as I was able!