Stretch My Tight Hole

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Mistress takes him with a strap-on.
848 words
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I'll never forget my first meeting with Mistress Ophelia.

I went to her house on the outskirts of the city in a modest suburban setting. On knocking on the door she opened it. She was stunning - at least 6 foot tall, with dark ivory skin, long flowing hair. She was wearing a black lacy top and shiny trousers.

She lead me into the house and commanded me to strip naked in the bathroom. I trembled as I removed my clothes. She then led me into her dungeon where she commanded me to kneel before her. She then explained the rules that I would have to follow if I was to submit to her. She was firm and intimidating and I found myself drawn to her in a way I cannot describe.

After a time She told me to follow her on my hands and knees. She led me into her dungeon and commanded me to climb up onto her bench lying on my stomach which she called her whipping and fucking bench. I trembled as I did what she said. She then strapped my arms to the side of the bench and my legs apart at the rear.

The bench raised my arse up and the way she strapped my legs meant that my tight little hole was at full view.

Before I knew what was happening I felt her strong hand spank my backside. She rained blows down on my cheeks repeatedly telling me how she loved sluts who liked pain and how she could tell I was a complete whore.

Her hand moved away and she then replaced it with a paddle. She told me she was going to give me 10 strokes with the paddle. She started to count each one as she beat my arse black and blue. It was agony and I was itching to use to the safe word but desperate to please her by not doing so.

After the 10th stroke she gave me an 11th, 12th, 13th it just went on and on until after she had counted to twenty she stopped and laughed at me for innocently believing that she would give me only the 10 strokes she had initially said.

Then the whip followed. The first I felt was an exquisite feeling of a whip being run through my balls causing my cock to instantly spring to attention.

Blows with the whip then came hard and fast. By now I was really in agony. My mind had gone to a place it had never been before knowing that the pain I was receiving I was actually LOVING but at the same time I was desperate for it to stop.

Before I knew what was happening the pain did stop to be replaced with a new sensation of a rubber gloved hand inserting 2 fingers into my tight little arse. I was being lubed up good and proper and before I knew it the fingers were replaced with a butt plug.

Desperate to hold it in the lube in my arse gradualy pushed it out until I could feel the plug fall out of my hole and I heard it land on the floor. My Mistress turned round and said to me that she would punish me later for not keeping the plug in.

She came up behind me and I could feel the tip of her strap-on cock pushing against my arse until she slipped it in and started fucking me. I was being completely and utterly used. She fucked me hard and fast like the slut that I am. Throughout the fucking she told me what a dirty slut I was. How I must be a sissy whore to like it up the arse so much. She told me next time she would fist my arse and have me begging for more.

She then pulled out and turned away. When she came back I felt the most enormous fat dildo stretching my arse walls. The pain was real but the pleasure was greater.

She rammed my anus with her dildo - grabbing on to the side of me until she pummelled my arse. It was agony, it was exctasy. I was desperate for it to stop but was also desperate for it to continue.

In the end, pathetic slut that I am I said the safe word. Disappointed my mistress pulled out. She then beat me with her paddle again for being such a wimp and a sissy.

Tired and exhausted she unstrapped me from her bench and told me to kneel before her and wank. I felt utterly degraded and humilated as I wanked in front of her and she told me what a pathetic sissy slut I was. When I came I was so exhausted I could have fallen asleep there and then.

I left thanking her profusely and promising to return. Since then I had to leave town so I never did see this Goddess Ophelia again. That was two years ago and I would dearly love to find another mistress to worship.

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AnonymousAnonymousabout 13 years ago
a delightful romp !

The slut boy did not realize how much his hole could be stretched so that the mistress could fist him perhaps.

Thank you for encouraging me to give you helpful feedback that feel good about articulating dear author of the literary piece.

AnonymousAnonymousover 16 years ago
WOW

Sounds like a good time to me, I Have never used a "Safe" word, the only word I know is "More"!! Please write more soon

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