Super Tight
I had two dates last night. The first one was tight. When I say tight I mean his asshole was like a cement wall.
Everything had gone according to plan: he was a new customer, he was polite and well-mannered, he had good hygiene, he was into my shit, and he did a great job giving head. But as we moved into the main act I literally ran into a brick wall.
He was on his elbows and knees, doggy style position, pucker hole pointed at my candy. My candy was hard, the condom was on, we were lubed up and ready to go. His spincter stopped my candy cold. It reminded me of those armored bank vault doors. The words Titanium interlocking bolts come to mind. So I lubed up my fingers and tried to pry open that fortress.
Big mistake.
The good news is that I made it past the sphincter. The bad news is that I came *this close* to losing a finger in the process. His rectal muscles nearly tore my index finger off! The finger joints felt painful while inside him and when I took them out they were sore. His rectal muscles did a number on my finger, twisting and mangling them, leaving a message in no uncertain terms: STAY THE FUCK OUT!!!
Can you imagine if I actually stuck my candy in there? It would have been bruised for weeks!
I tried. I really tried. He really wanted to get fucked. He’s been fantasizing about it for a while, and my lewd and lascivious ads on CraigsList made him want to try it for real.
I’m sorry, I apologized. But I don’t think I can get inside you. Not tonight, anyways.
Is there anything I can do to prepare for next time? he asks me.
Yes, practice with a dildo.
He explained that he is married. He has kids. He can’t risk his wife finding a hidden dildo.
How about practicing with a zucchini? I offer.
Wait, they’re too easily breakable, I thought to myself. But how about a CUCUMBER?
He nods his head. His eyes light up. Clearly, I am on to something. I begin compiling a grocery list of natural, bio-degradeable objects that he can use to shove up his ass without arousing his wife’s suspicion. (And, YES, this conversation really happened. Welcome to the absurdities of my life as a Crossdresser TOP to discreet married straight men.)
Oooooh! I had one last burst of inspiration as I walked him to the door. It was the perfect produce to stick up his tight ass:
You can start with BABY Carrots!
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Tags: sleazy
i did not know it was even possible for it to be that tight!
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Chris: I hear you. I think he may be the exception rather than the rule. I’ve had some tight ones before but at least I’ve always managed to fuck at least a little. Thanks for writing, Cass
How you are such a great story teller!
I am in my late 40′s slender and have those same fantasies. I would love to hear from you.
I will send pics if you like. I want you to own me baby!
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Baby, your ass is mine! Cass
Hi Cass, Married with children and a brick wall too. Long eggplant works for me. Less chance of breakage than zuc or cucumber and skin is pretty smooth and slick.
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HAHAHA. Oh I do love guys with a sense of humor. I thought about recommending a banana but you don’t get that many curved cocks in real life. An Eggplant!?! The Asian variety, I”m assuming. The Western kind will leave you wearing adult diapers for the rest of your life! xoxo Cass
I’d like to recommend wine bottles… solid as can be (though somewhat fragile if seriously abused), not too long, not too short, slips in like a rat up a drainpipe and it really doesn’t matter what year it is !
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LOL! Let’s just hope that there are no chips on the lip of the bottle… : ) Cass