Shitty Date

Martin was from up North. He called me a day in advance to schedule a meeting at his beach side hotel room. On the phone he was stoic, which made it difficult for me to make charming conversation.

I confirmed with him the following afternoon and then drove the half hour drive to see him. I bought a street parking pass from a homeless man, who lied to my face – “I just bought this ticket for four dollars but now my girlfriends gone and I don’t need it.”

“Yeah yeah Mr. I stole someone else’s credit card and bought a whole bunch of parking tickets and am now trying to sell them on the street to naive tourists, or intelligent locals like myself who know that you’ll take any price – including just a single dollar.” Sadly, I still paid him four dollars like an idiot when I could have bought a ticket five feet away for $3.

Anyways, I slithered into the quaint little hotel in my tight jeans, black collared shirt with rolled up sleeves and black beanie and by-passed the normally vigilant hotel security, who probably thought I was too well dressed to be any trouble.

I knocked on the hotel door and felt the normal wave of anxiety roll through me as a few seconds of silence ticked past. The door finally opened and a good looking, middle aged guy answered the door. He looked a lot like Christian Slater, only middle aged (because Slater will forever remain young in my eyes) and adorned with a pair of glasses.

We sat down on a couch, he offered me a Sprite (which I had requested earlier) and we started talking. Conversation was not easy with him. His initial statement to me was “God, you’re a lot taller than I expected you to be.”

But after awhile he warmed up and told me that he was married and had several young children. “You monster!” I wanted to say as I jumped out the five story glass window in my imagination.

Actually, the idea of a married, dorky yet attractive father seeking the companionship of a young boy kind of aroused me.

He told me that kissing and fucking were his two primary interests when he had paid company. After hearing that I moved my head towards his and started kissing him.

He enjoyed himself immensely as he removed my clothes, one item at a time, until I was left standing in my boxers. “Keep those on, “he said, “for now.”

We moved onto the bed. My dick got hard. He sucked me off for a few minutes and then said he wanted to fuck – not just one way, but in “three or more different positions.”

“Lets start with you on your side” he said. I handed him a condom and he unrolled it over his cock, which was quite large and nice looking.

It took awhile for my ass to accept it, but once it did I was having a precum-oozing good-time. He nibbled at my shoulders as he fucked me – he obviously was used to the intimate, married way of having sex.

I had to completely let go of my dick to keep myself from cumming. Even so I almost came from the shear pleasure of his dick pounding away at my ass.

Then he wanted to fuck in the shower. We tried but immediately found it to be nearly impossible.

We moved back to the bed and tried to fuck with me bent over the bed. This position was too painful and I couldn’t take it.

Then he wanted me to sit on top of him – a position that everyone wants to try with me. As always, I said no.

Then we lay in bed together for awhile. He told me I could play with his hole if I wanted to. I thought about it and assumed he had cleaned himself, so I went for it. Fingering him was okay – then he suggested I go ahead and try fuck him. I have never topped before, but I thought – “what the fuck?”

I put a condom on and pushed it into his ass. His asshole was so loose it didn’t feel like anything, probably the same sensation as sticking your dick into a bucket of mayonaise. There was hardly any friction. For a self-proclaimed top he sure seemed to have been well worn out- though he claimed he never got off from bottoming.

After a few minutes I decided to pull out. I did and then looked down at the condom.

AAAAAAHHHHHHHHHHHH

It was covered in shit. Not just a little bit, I mean a lot of shit. I tried to hide the condom from him as he leaned toward me. Like a Charlie Chaplin skit, I was somehow able to swing it around so that I was holding onto it behind my back.

“Whats the matter?” he said. “Nothing!” I exclaimed.

I tried to think of a way to hide him from shame and embaressment. “Lets fuck again” I said. “Just lean over and grab a condom and lets get started.” He looked into my eyes and was about to turn around when he looked down at the bedspread. “Whats that?” he said. I saw that some of his shit had speckled onto the sheets.

“I don’t know” I said.

“Is it poop” he asked.

“I don’t know, I don’t even want to look at the condom” I lied. I through the condom onto the floor, hoping it would vaporize on impact. Instead it landed with a splat. He got up, picked it up and brought it into the bathroom.

Funny how I seemed more embarrassed than him, though I’m sure he felt deeply shamed. I felt like his balls had been chopped off before my very eyes.

I, understandably, lost my hard on. He fucked me a little bit more and then told me he was tired.

I tried to forget what happened but all I could see in my head was the shit covered condom hanging from his hair. “Oh, is that where I put it?” he might say.

I jacked him off until he came and then quickly dressed. He paid me, plus a nice tip, and then told me he had a great time.

“Yeah, you’re the shit.”

To all people who are planning on having anal sex, CLEAN YOUR ASS OUT BEFORE HAND.

To learn how read my comment on The Secret Confessions of a Horny House Wife ’s blog titled Crossing the Line