As the questions started to wind down, Jill decided her friends should see a different side of me. My backside. She had me turn around and bend over feet apart while holding my ankles. This left my cheeks wide open so they could have a proctologist's view of my asshole and balls. After everyone got a good look, she turned me sideways and told me to "assume the position." This is basically the downward dog yoga position - ass up, head down. Perfect for humiliating bare bottom punishments.
With great flourish, like a ring master at a circus, she circled around me waving our well-worn black leather paddle as she described how we frequently use the paddle and riding crop as foreplay to get me hard and compliant. Taking her time, she administered ten heavy blows, five to each cheek, while her friends urged her not to hold back. After all, as a man I'd surely done something deserving of punishment.
My ass was on fire by the time she switched to the wide-tip riding crop, where she swatted me 10 more times in rapid succession and then a quick tap to my cock which was my signal to stand with my hardon exposed to her and my hands behind my back. She then swatted my cock back and forth with practiced precision to send the perfect blend of pain and pleasure that kept me hard and wanting more.
"See? Even after all that he's hard as ever," Jill smirked while her friends captured it all on their phones for posterity.
"Kneel." Jill disappeared into the bedroom for a minute and re-emerged wearing our 8-inch long, two-inch thick realistic dildo with balls. She stood legs apart, hands on hips and her cock just an inch from my face. "Suck."
Keeping my hands on my thighs, I took her cock in my mouth like it was the real thing, trying to give her the blow job I would want, the kind that would make any cock explode. As I focused on pleasing Jill with my performance, her friends had fallen nearly silent, their jaws dropped at the sight of our kinky role reversal. Well, if they thought a man sucking a woman's strapon was something you don't see every day, wait till they see what comes next.
After sufficiently demonstrating my cock sucking skills, Jill ordered me on all fours. She knelt behind me, lubed up her cock and slowly but forcefully sunk it balls deep into my ass. It always feels like she's going to split me in two, but I always manage to take it. She then began pistoning in and out. Slowly at first, but gradually building speed and force till she was slamming me hard with every stoke.
In this position, Jill's friends had a perfect side view of the action. They could clearly see Jill's cock sliding in and out of my stretched asshole with the rubber balls slapping against me. At the same time, they could see my hard cock hanging down in front and bouncing wildly with each thrust.
I desperately wanted to jerk off and cum while Jill was fucking me, but I knew better than to take the initiative. Jill usually forbids me be to touch my cock while she's fucking me. When I'd steal glances at Jill's friends to see their reactions, they were mesmerized. I was pretty sure none of these women had ever fucked a man in the ass, but after today, I knew this would be a femdom fantasy that would play in their heads for the rest of their lives. Maybe they'd even get to live it one day.
Jill ended her fucking me with a simulated climax of hard, fast fucking and a final thrust that she held deep inside while grinding her hips against me. Then she pulled out, and leaving me on all fours, went to the bathroom to take off her cock and clean up.
When she returned, "Well ladies get your phones ready, it's time for the big climax." Jill had me get up and stand in front of the window again facing her friends. "Now jerk off till you cum all over the glass, then kneel down and lick up every drop."
This wasn't how I thought the evening would end, but at this point I didn't care. This was the first time I'd been allowed to touch myself in a month. I grabbed my cock in my left hand and went to town. Within seconds I'd shot five or six spurts of cum all over the glass. I didn't think cumming could be so intense just from masturbating, but I'm sure going a month without release had something to do with it.
Before my spasms had subsided, I dropped to my knees and started slurping the cum off the glass. By the time I'd finished, my face was wet and sticky and I was coming down from the high of my pent-up orgasm. I realized tonight's performance crossed a new threshold in my relationship with Jill and her friends. I loved it, feared it, was embarrassed by it, totally excited by it -- and would do it all over again. I can't wait to see what Jill and her friends have planned next, especially when they tease me with knowing smiles and say "We should all get together again soon."
