The Humiliating Experience I Had

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How Do I End Up In These Embarrassing Positions?

My wrists hurt! I feel the metal handcuffs ripping into my flesh as the car shifts from side to side through what I assume to be hills. I must have been in here for a few hours now but I can’t be sure as I was knocked out for the last hour or so. Was this the doing of the woman I met at the bar? It couldn’t be, could it? I mean she was a bit rough but not this rough. The car slams to a halt as the driver gets out and opens the trunk demanding me to get out in a familiar voice. I stand up while being lead by a leash, blindfolded and wrapped around a chastity device that was placed on me.

Hearing a door open, we both walk inside. The soft carpet feels relaxing on my feet.

  • “We’re inside now so get down on your hands and knees slave. Now you get to crawl!”

I do as she says quickly to avoid any repercussions. My chains hit the ground reminding me of the pain from the cuffs. Really, how did I get into such a humiliating position? Like how?!?

She leads me further in the building.

  • “Lucky for you no one was outside when we got in which I find to be very unfortunate. Now do you know why you’re here?”, she said.

Stopping, I swallow hard before answering,

  • “No ma’am I don’t”.

She yanks the leash,

  • “Of course you don’t because you are a  pathetically stupid male, you’re all the same only thinking about yourselves never anyone else and it’s always with that humiliating penis too. Oh don’t worry about your pathetic cock, I’m sure you’ve already felt that we’ve taken care of your little problem already haha!”



My Female Doctor Teaches Me A Humiliating Lesson

My dick did its best to get hard in the cage without any progress. I always thought my dick was average size, well until I had my annual physical last year with a female doctor. She was older but still had it going on and needless to say, I got a bit excited by her touch. That is before she started laughing at me commenting how cute my “little guy” was, and though humiliating it sent me over the edge to which she commented how unprofessional that was and that I needed to be taught a lesson. With the doctor’s hand squeezing my balls, instead of the hernia exam, she was about to do, she dragged me to the floor with them and made me clean up my mess with my tongue for being such a naughty patient.

My mind came back to my current situation when I felt a sharp pain hitting my balls. As I collapsed to the floor I hear,

  • “Pay attention you stupid sissy, now get moving”, she said.

We continue moving through different parts of the building. My only way of knowing we’re moving is that we go from carpet to tile and back. The light is brighter in the tiled rooms. Finally, we stop in a tiled room. She removes my blindfold as I look up, I see now why the voice was so familiar, It’s one of my sister’s friends from high school.

A Familiar Person From the Past Dominates Me

I knew we had crushes back then but the three-year age gap was too awkward for us. But now with both of us being out of college and establishing our careers, it’s a completely different story.

  • “Susie what are you doing, where are we, how did w….”

Mid-sentence she kicks me square in the balls again knocking me over.

  • “Shut up!! You’re in no position to be speaking, now listen up. We’re at an adult bookstore. Why? Because you’ve been a bad boy that needs to be punished. I know you’ve been sleeping around, well at least trying to. I’m not sure how well that’s going with your almost three inches of wood but you’re mine now. No questions asked! I know we liked each other back in the day but things have changed. Don’t get me wrong you’re still cute and all, but cute is the operative word here, hehe.!! You’re doctor, bartender, and that girl you were hitting on earlier are all my friends, and let’s just say they’re not too fond of your actions.

My Glory Hole Adventure

I see a red light come on and notice a hole in the wall with a finger poking through it.

  • “Perfect! Just in time, I invited three of my “old friends” to come to teach you a lesson and if you’re good you may get to keep something special but three strikes and you’re out, now lick his finger to tell him you’re ready.”

I couldn’t believe this!! She brought me to a glory hole! Wait, what do I get to keep if I obey..maybe her. I thought for a second and stuck my finger through the hole. Apparently, it was a second too long as she yelled, “strike one!” delivering another swift kick to my balls still aching from the last two.

A slightly bigger than average penis slides though and I look at Susie.

  • “Wait for one more second and that’s strike two now suck and hurry, we have somewhere else to be so you have five minutes per guy otherwise it’s a strike.”

I get sucking applying all the techniques women have used on me throughout the years. He must have been waiting because I went to lick the underside of him and he came all over my face much to Susie’s delight.

  • “Very good 3:22 looks like you’ve done this before sissy”

I blush at her humiliating comments and repeat the process when the next finger pokes through.

Continued Forced Sissification

This one is bigger than the last by two inches at least but thinner too. I get going as he moaned,

  • “Better hurry he only has ten seconds left”

to which I respond by sucking harder and he finished in my mouth. I spit it out never having eaten someone else’s cum before, she kicked me again.

  • “That’s strike two for not swallowing, every sissy knows to swallow now lick it up.”

I lick it up and when I bring my head up the biggest dick I’ve ever seen is staring me in the face. It must have been ten inches and wide! I got to work quickly barely able to contain the monster in my mouth.

He finally filled me up all running down my throat.

  • ” Well it’s about time, eight minutes three seconds,” she says delivering yet another kick. “Well looks like it’s time to go now, don’t want to be late now that you’re for sure not keeping that special thing but that’s ok, it’ll be more entertaining for me and humiliating and painful for you.”

She sets me up and leads me back outside…


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