There I was, handcuffed to the bed, wearing only a bra and a pair of stockings. His massive arm was draped over me, and he was just snoring away, oblivious to my predicament.
I had just been fucked within an inch of my life. I wasn’t able to fit the head of his cock into my mouth, and yet he was able to penetrate me and sink his entire length into me. It hurt me in such a wonderful way. Once he finished, he fell asleep, and I really needed to wake him to uncuff me so I could go to the bathroom!
While fidgeting around, I remembered who was responsible for getting me into this situation.
It started simply enough. My stepdaughter Ellen and her friend Liz talked me into going to a charity event with them. They promised a good time and convinced me that I would have no problems passing as a female. I believed them; I have had a lot of practice recently.
I remembered getting ready: fresh shower, hairstyle, and make-up. I slid into a pair of black stockings with a garter belt and black lace panties over the top. I fastened the black strapless bra over my glued-on breast forms and was ready for the dress.
There wasn’t a lot to this little black dress. It covered my legs to mid-thigh, which wasn’t too long or too short. My entire front was covered with a strap going around my neck. My shoulders were bare, and the only cloth between my waist and neck was a swath wide enough to cover the bra.
I thought it was too risqué, but the ladies convinced me otherwise. I grabbed my purse and headed out the door with them and took a cab to the event at a hotel convention center. So far, everything had gone well.
We arrived at the event, got cocktails, and found our seats. The room was full of well-dressed people mixing and mingling. Playing it safe, I stayed at the table while Ellen and Liz socialized.
When it was time for dinner, they were nowhere to be found. I sat there alone and frantically looked around the room for them. Unfortunately, I had forgotten my cellphone and couldn’t call them.
At this point, a gentleman walked up and asked if he could join me. He took my silence as consent and sat down. My silence was actually due to my awe at this gentleman. He was truly massive and well built. I stammered out an introduction and he introduced himself.
At this point, the dinner started, so we engaged in small talk. He really made me feel comfortable, though the several drinks I had may have had something to do with it. I was really enjoying myself.
As dinner ended, he asked me back to his room for another drink. All I could say at this point was that I was drunk, hot, and horny. I wanted to see if his penis was proportional to the rest of his body.
In the room, he poured two drinks, took his jacket off, and sat down next to me. I tried to play hard to get, but failed miserably. Within minutes, I began making out with him and had a hand between his legs. He wasn’t offended as I stood up, kicked off my shoes, dropped my dress to the floor, and bounced onto the bed, wiggling a finger for him to join me.
His clothes came off as he walked over. When his boxers came off, I almost passed out. He was huge. His member was outsized in proportion to his massive frame, and he was hard.
I wanted to suck his dick, but he told me that it probably wouldn’t fit in my mouth. He was right, I couldn’t fit the head of his penis into my mouth. He offered an alternative solution, and suddenly I was lying on my stomach while he handcuffed me to the headboard and pulled my panties off.
He began running his hands up and down my body, and I began to beg him to fuck me. He inserted one finger and then two into my backside, gently massaging and stretching. I then felt the lube and knew what was coming.
He gently aligned himself, and I screamed as he quickly inserted himself. The pain was overwhelming, yet I loved it. He slowly slid in and out until he was completely in me.
What happened next took me to new levels of passion and pain. He started thrusting harder and faster, I almost couldn’t take it. I felt him swell and the massive burst of cum into my ass,
At this point, I think the alcohol took over, and he fell asleep on top of me. This brought me back to my dilemma.
I was still handcuffed to the bed and had to pee!
Before letting it loose and ruining the bed, I decided to try waking him one more time. I bounced as best as I could. It knocked his arm off me, and he finally woke up. I was almost there.
I explained the emergency, and thankfully, he knew where the keys were. He uncuffed me, and I rolled my feet to the floor and tried to stand.
I promptly fell to the floor. My hero was there in an instant. He easily picked me up, rushed me to the bathroom, and set me on the toilet.
The relief I felt was incredible. I resolved to satisfy him again as a way of showing my appreciation. I staggered back to the bed after I wiped and promptly wrapped both hands around his member. Rubbing and licking with my tongue, he quickly grew hard.
Once again, the pain and the ecstasy as he shoved the massive cock in and out drove me nuts. At some point, I passed out.
I woke in the morning with the sun hitting my face. He was gone.
Next to my purse, I found a note and an envelope. The envelope held several large banknotes. The letter started with an apology that he had to leave. It also has his phone number and a multitude of “Thank You’s” for the great time.
I definitely won’t forget the fucking of a lifetime, and I may have found a side-gig!
There’s more to follow. I promise.
