Friday Night First

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His first anal adventure.
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It was not a Friday like any other I had experienced, and I was on my way to work. I work as a bartender at a busy nightclub and with this particular night I was extremely horny.

I was awoken today around 4pm by Jenn, an acquaintance of mine, nibbling on my cock. It's time keeping isn't quite as accurate as an alarm clock, but it gets the job done. As she started bobbing her head down further on my cock, she began to caress my hairless balls gently. I could feel her teeth gently against my shaft as she continued to suck on my hard cock. I let off a low pitched moan as my eyes closed. It's what happened next that threw me for a loop. She pulled off of my cock and reached on to the floor and pulled out a medium sized purple vibrator and just smiled at me. As I opened my eyes I looked up at her then grinned and went to reach for it.

Jenn said, "Ah ah ah, We are going to do a little something different today"

"What do you mean by...different?"

"Well you see, I'm going to use this on you today." as she grinned evilly at me.

She noticed the puzzled and uncomfortable look on my face.

"I'll be gently with you, I promise"

Having never had anything inside me, I didn't know what to expect from this. She began to put some lubrication on the end of the vibrator and some on my extremely tight hole right now. As she brought the vibrator closer to me I could feel myself clenching my ass.

"You're going to have to relax a little or this is really going to hurt."

I thought to myself, great this is going to go real well. To relax me she began to flick her tongue around the head of my cock a little. Once she realized I was more relaxed it happened. I felt the vibrator penetrate my tight hole. At first it hurt pretty bad, but as she slowly pushed it in, it began to feel better.

Jenn said, "Do you want me to continue, or does it hurt to much?"

"It's ok I can take it..."

She began to slowly moving it in and out of my ass while slightly twisting it. I let out a loud moan as she just giggled at me.

Jenn, "Feels good doesn't it?"

"Yes...please don't stop"

I could feel myself getting more turned on by the moment, but it wasn't the normal feeling building up, this was a lot more intense. After only a few minutes I could feel my cum building up and getting ready to squirt. She began to slow down sensing what was to come and smiled as her tongue licked my balls for a little while. As she began to once again slide the purple vibrator inside me, my back started arching in pleasure as the moans became very frequent and very loud. Jenn began to sense that I was ready to cum and began to once again lick my balls up to the head of my erect cock.. Within a few seconds I had the biggest orgasm I have ever had, and right into her mouth. This wasn't the thin watery cum either, this was a huge thick load. She looked so sexy with my hot cum dripping from her mouth as she swallowed what managed to stay in her mouth.

Jenn said, "You need to get ready for work now." As she winks and walks away.

I then got up and went into the shower to clean myself up, as I was showering I reached down and felt my hole that was just filled with a vibrator and gave me that orgasm. I couldn't believe what happened and what it did to me. I actually became aroused again thinking about it in the shower. After I got out of the shower I looked around for Jenn again to help fix my slight problem quickly before work, however, she had already left.

So now you see my dilemma as I head into work. It's bad enough that I have to deal with a ton of hot women flirting with me to get cheaper and free drinks all night, but now I have to do it while extremely horny! I wonder which one of them I will be taking home tonight.

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