First (and only) Anal

Submitted by on Wednesday, 25 April 2018, 04:56 PM | Confession | English
Categories: Anal, Fetish, First Time, Taboo, Mature   Tags: , ,

When I was single, I had anal sex with a prostitute.

She was a bargirl, but not a girl, really. She seemed old to me then, probably 30s... which seems young to me now. She looked kind of worn, and I could tell she had "been around".  I had not really ever thought much about anal, so it was spur-of-the-moment.

Just to see her reaction, when she brought my beer, I asked her if she would do it. Her response was humiliating;  before she answered she stuck her hand in my pants and gave a squeeze. She left it in there for a few seconds until I hardened up some, then pulled it out and said "Sige".  I was a little insulted!  But now I was intriqued...

We went into the short time room in back, and engaged in some foreplay. I love foreplay, even with a prostitute. It's really my favorite part of sex; playing, teasing, getting to know each other sexually, body response, etc.  She was petite and felt good in my hands and arms. We kissed and felt each other, then she sucked me expertly. I got on top and pussy-fucked her in the missonary position for a while. When I withdrew, she handed me a condom and a tube of jelly and told me to put it on. I did as she requested, the condom seemed very small and didnt go on very far. 

I tipped her legs back and played with her butt. It didn't seem to faze her much when I slipped my finger in.  Then I tried to get my dick in, but it wouldn't go despite her feet being almost at her head. The angle just wasn't working. She finally indicated to me to let her turn over, doggy. It went in fairly easily then and I began fucking her ass. She wasn't into pretending, there were no oohs, ahhhhs or oh babys . I could tell she was just waiting for me to cum and be done with it. I wondered what she was thinking about; lunch, sleep, math, science, world-affairs, etc. (haha)

I kept fucking, looking down to watch it sliding in and out of her. On an out-stroke,  I noticed the condom was gone! I looked and it was uhmmm... hanging out of her butt. I was a little repulsed, so I pulled it out and found it was split. I tossed it on the floor and went into her pussy again. After a while, I felt like I wasn't accomplishing what I came for, so I withdrew and went back in her ass. She held still throughout, pretty much frozen on all fours patiently while I fucked her holes. I ended up cumming in her ass, because I wanted to feel like I got my money's worth.

To be honest, it wasn't that great. I thought it would be like what I read; hotter, tighter, etc. It wasn't. It was just fucking. I really couldn't tell that great of a difference. That was my first and last experience with anal. 

I'm glad I did it, but it absolutely didn't blow my mind. Granted, it may have been different with a different partner. But still, it wasn't something that I felt I need to do again. Even when I watch anal porn occasionally, it always seems kinda stupid to me...

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