Cuffing Season

I have known Ben for almost 10 years and we have never been more than just friends. He does yard work and odd jobs for me. Oh yes-- Ben is 6'8, 225 and looks like a body builder. He's also 30 years younger than I am.

Last week he came over, got rained out, and sat on my couch asking how he can become a male escort. I didn't believe him but he was serious so we looked at some stuff online. I told him he would need a full frontal nude picture and he asked if his dick is big enough. I laughed but when I looked over, he had a huge erection sticking out of his sweat pants and slapping against his belly. He immediately asked "Can I fuck you with it?" "Look, bro, don't think you got your first customer. I pay you for yard work, not fucking me." Ben informed me that he likes older women and wants to practice on me. I told him I don't think so because I'm seriously kinky and not at all into vanilla sex

He asked me to explain and I turned kind of red but told him I like to be spanked- naked, my ass turned up over a guy's lap. Spanked hard, until I cry. I like to be tied up - cuffs, spreader bars, 4 pont restraints, panties for a gag. He nodded. After a hard spanking, open my pussy and ass with a dildo so the cock slides easier when I get pounded in the ass a few minutes later. I didn't even mention some of my wilder kinks.

"I can do all that to you" He said as as he stroked a very hard and very attractive cock.

And that is now a week later I watched him walk in my front door and take a seat on my couch. On the table in front of him was a pump bottle of lube, an 11" fat dildo, a round wooden hairbrush and pink leather paddle, and a pair of clean, pink lace panties. He looked at me and patted his lap, but I didn't know yet if I would or I wouldn't. This man is huge and fucking strong.

Finally I said oh, fuck it, YOLO mufuckers, walked over to him and pulled off my shirt. I sort of didn't have on a bra, so I guess I had already decided. I took off my shoes and shorts but left my panties on.

He pulled me over his lap, my clit twitching and my face flaming red. He spanked each side lightly- nothing hard. His spanks got a little harder and I squirmed. I felt him pull my panties below my butt, and realized he meant to do this. I gasped. He smacked harder and told me my bottom was getting red-- and then he pulled my panties completely off and tilted my ass up.

I died, knowing he could see my genitals-- but it made me hot as fuck to know that. He picked up the wooden hairbrush and cracked it down on my ass cheek. I raised my head up and said OW! out loud, and he pushed my head down. He alternated sides with spanks I could definitely feel as my bottom started to heat up. The hairbrush was landing on every part of my ass but mostly on the round part right in the middle. He spanked even harder. "Damn it" I yelled and tried to reach back and protect myself-- so he promptly pinned my hand in front of me and started spanking in earnest. The brush smacked each side, alternating fast now. I was squealing OW OW OW stop, it's not funny anymore you fucker! At that, he absolutely blistered my ass and stopped. I was gasping in pain when I felt him part my legs.

Aw shit, he didn't forget a thing! He pushed down on my head and ran a finger up and down my slit... teasing and playing with it, not penetrating me. I moaned as his finger circled around the entrance to my vagina and felt myself grinding on his lap and on his cock. The finger plunged all the way into my pussy and was followed by a second finger. I gasped and moaned. "Uh huh, that's it. I know you want it." He withdrew and I felt a finger slide up my rectum, and a second one. I moaned louder. "Oh yes, I'm gonna fuck that ass so hard." I was writhing like a slut on his lap.

The fingers withdrew and he closed my legs again and paddled me even harder and faster, pinning both legs down when I kicked and tried to turn from side to side. My butt was literally on fire with pain. I was close to sobbing.

The spanking stopped and he rubbed my ass, telling me he had never seen anybody's bottom so red. I relaxed for a moment, letting myself go limp over him-- and felt the fat head of the lubed dildo start sliding into my vagina. He made me cum within a minute. Horrified, I felt the head pop into my asshole and start opening me up. I gasped and moaned loud, absolutely mortified. It wasn't bad enough that I was buck naked over his lap, giving him a good look at my holes- not bad enough that he held me down and fingered me, then held me down and paddled me until my bottom was flaming crimson- no, now he was putting an 11" dildo all the way in my ass, knowing he would soon be shoving his own cock up me. I have never been so embarassed in my life... or so turned on.

I pushed my face into the couch as he pushed the dildo in deep then pulled it all the way out- and shoved it back up my ass. I may have been embarassed but I kept writhing and grinding on top of the erection he had in his pants. He picked up my panties and stuffed them into my mouth. I was trembling now, afraid of what I suspected was coming.

Ben pushed the dildo as far into me as it would go, and held it there- and picked up the pink leather paddle and brought it down on my ass. I couldn't believe he was going to spank me with a big dildo shoved all the way up me! He spanked me very, very hard while rapidly going from cheek to cheek. I screamed, muffled by my panties. I writhed, I kicked, I desperately turned from side to side-- but the paddle continued to blister my bottomas the dildo held my cheeks apart. Overcome by pain, I began to sob. He kept spanking me for several more minutes and finally put the paddle down, rubbing his hands over the blisters and welts on my swollen ass cheeks. He leaned over to me and softly said "I'm going to fuck you so hard you can't walk." My legs clenched together as my clit pulsed.

He pulled me up and walked me back to the bedroom, placing me at the foot of the bed, ass hanging over-- and his cock slid right up my smooth, open ass with no resistance.

Let me assure you that a 6'8 225 lb man can sling you around and turn you into a pretzel. Your body will do things it hasn't done in years.

Ben's cock pounded into both holes, raising my legs above my head then changing to pushing me face down on the bed and pinning me while he slammed his cock into my ass. He fucked me for almost an hour, twisting and turning me and I lost count of how many times I came no matter what hole he was sliding in and out of. Finally he jackhammered into my ass- pulled his cock out, and came all over my rosy red bottom. A little while after that I fell asleep.

Maybe another hour passed and Ben walked back in the bedroom and saw me passed out, wearing only a long, loose tank top and no panties... and I woke up to him sliding his rock hard cock into my pussy from the side. He fucked me again, while I gasped and moaned and circled my hips, grinding against him and milking his cock with both holes. I held on for dear life, hoping nothing would break as his cock pounded my cervix and then slid in and out of my rectum. I could feel the head of it force both passages open.

He came again and slipped his soft penis out of my ass. Both my holes were tingling and throbbing and the next day-- which was today-- I looked like the mother of all whores the morning after. I turned my alarm off and was almost an hour late for work and sat down very carefully all day.

This evening I got a text from him: "I'm going to put you in those handcuffs with your ankles and your hands together so you can't close your legs and I'm going to suck on that clit until you cry ."

Get you a big boy for cuffing season, no better advice ever given.