The year was 2007. I was dating a guy who played soccer all four years at Ohio State and was bummed that he had to work a job in the real world instead of playing soccer professionally. Such is life. I was bartending in Lincoln Park and he lived in the same neighborhood; I would come by his place after work sometimes so that I could mix drinks to get us tipsy and then we would have mind blowing sex. Adam had one of the best bodies that I had ever seen, and I'm not going to lie - it was pretty intimidating being naked in front of him the first few times. He didn't have a six pack, he had an eight pack. His arms were shaped specifically to make women swoon and men jealous. Don't even get me started on his legs. Wow, his legs! That ass! That full head of blond wavy hair... anyway, you get the point.
Since I was 18 men had been sticking their fingers in my ass because of something they read in Maxim. Guys, stop reading Maxim for sex advice. I'm not saying that it is wrong, but I am saying that sometimes you should ask the chick first before you randomly jam a finger (or dick) in there. Some women like it and some women don't. Us ladies are the fairer sex, we are complex, we can give you the ultimate pleasure, and we can also shut you down quicker than a fire grows when it's introduced to oxygen if you make the wrong move. What you use on one doesn't always work on the other. So, anyway, I'm done with that lecture. One night after giving Adam a blowjob I casually mentioned that because he has a prostate he should let me stick a finger in his ass the next time I go down on him.
Adam: I don't know. Wouldn't it... hurt?
Me: Of course not! I would use my pinky and lube.
Adam: I don't know...
Me: I read that it will give you the ultimate orgasm. So many men get erections when they have prostate exams because it is the male g-spot. Don't you want to experience the ultimate orgasm while you are in my mouth?
Adam: I do like being in your mouth. But if that's the case I won't have time to warn you before I shoot my load in your mouth.
Me: Adam, that is a good surprise. I won't mind.
Adam: I can't believe I am saying this, but yes, you can stick your finger in my ass. Don't let it be the next time you give me head though. In fact, make it a surprise, that way I don't have second thoughts about it.
Me: Awesome!
As you can imagine, I was super stoked. For years I had been getting a finger in my ass, and now it was my time to stick my finger in someone else's. This was very exciting to me. In fact, I was so excited about it that I discussed it with my roommates.
Tom: Straight guys are iffy about that sort of stuff. I know you like this guy so maybe you shouldn't do it. The chances are high that if you do it your relationship will cease.
Sue: Definitely wear rubber gloves and be careful which lube you use; like, you don't want to use a warming one. The rubber gloves are because of the bacteria in the anus.
I didn't care. I was sticking my finger in Adam's ass! I was going to be the cause of his most amazing orgasm yet. Besides, I was going to be gentle with him as I did it. Do you think any of those dudes who stuck their finger in my ass thought about lubing up beforehand? Yeah, right.
A month later was the night I decided I was going to do it. Adam had taken me out to a nice dinner and then to a nice martini bar afterward, so I was sufficiently drunk enough to randomly decide to do it. However, because it was so random I also didn't think to carry lube with me for his first fingering experience. Imagine the setting. Walking into his bedroom I stumbled over a pile of dirty laundry. I didn't care, I always stumble anyway. He pushed me onto his bed and took off his shirt, smiling broadly. I remember hoping that when he took my clothes off he wouldn't throw them on the pile of dirty skivvies. My eyes lit up thinking about what I was about to do to him. Cue to the fingering.
Adam: Whoa! Oh my god. Oh my god. What did you do? Wow. Oh my god. Oh, no! Oh, no.
Me: You liked it or you didn't. You told me to surprise you! What did you think.
Adam: Oh, god. I liked it. I wasn't supposed to like it! I wasn't supposed to!
Me: You came right away! I know how to cut bj's in half now! This is awesome.
Adam: Oh, god, I wasn't supposed to like it.
Adam and I didn't end up working out. Tom was right, but I didn't care. A year later I ended up checking to see who had me listed as a favorite so they could get emails to read my blogs. There was Adam's profile. I think he had me as a favorite because he wanted to know if I would ever write about it.
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