June 1- Sarge + Third Base Report

Approaches: 11
Conversations: 9

Dress: torn jeans, red sneakers, black polo shirt.

4:30 pm
Approach a 4-set sitting in Union Square Park. I think they're very cute and look like they're in college. "Hey has someone come up to you asking to draw you yet?" They're smiling, laughing, I'm center of the group, when I ask them which college they go to. "We're in highschool." Eject.

5:00 pm
Meet IWWK. And walk with him to Soho. He's leaving for Israel later that day and he's tying up loose ends. I approach two women while I have his bag. "Hey, want to buy a suitcase?" Get one person laughing, another totally ignores me.

5:30 pm
Walk up to St. Marks and stoop it for a bit. Meet up with Velvet. Approach 3 sets of women. Shot down. Biggest tragedy of the day though. This woman with two ridiculously hot 20-something year old daughters asks me where they can buy belly-button rings. I SHOULD have recognized that the game was on and charmed the mother and asked for the daughters' numbers. MISTAKE Instead I crack some jokes and they leave.

7:30 pm
Velvet and I head up to his friend's apartment. It's raining, so we ditch the idea of going to this art party that should legitimately be pretty hot. A couple of my female friends go ahead of us expecting to meet me there, but I flake out.

9:30 pm
Get a call from a girl I hooked up with when I was in college to see a movie screening. Flake out due to rain.

11:45 pm
Arrive at a frat-type bar on the Upper East Side where some friends are. I approach a couple of the girls we are with and then some hanging around the bar. No dice.

1:00 am
A friend of the girl who invited me up there arrives and I chat with her. Lets call her Faceshot, just for the sake of foreshadowing. Talk to her about what she would "REALLY like to do..." blahblahblah and try not to laugh when she talks to me about political stuff.

1:20 am
Approach a couple more sets. Go outside the bar. Approach some more sets outside. "Some friends and I are having a debate and we were hoping we could get your wise opinions... Would it be better to have an extra set of arms, or a third eye on the back of your head?" Get into good conversation with a two-set and the guy who was already hitting on them. Then the guy they were talking to senses they are enjoying the conversation and tries to start a fight. The girls pull him away.

2:30 am
Girl I was talking to about politics and I change locations to another bar down the street. She talks some more and I listen. I go to the bathroom, return, and she's bought us a round of drinks. I wasn't sure before, but now I know she wants me. She's about a 7 (thin, nice skin, push-up bra, no tank top, but nothing special), and it's late, so I figure why not. She buys us another round. We go dutch on a third round and play a game of pool. Bar's closing. I figure I might as well make out with her here since the night's ending anyway.

4:00 am
Faceshot suggests we break into a closed playground and hook up there. I'm nervous, but say ok. However I explain to her that I am nervous and will only do it on the condition that she play with my penis once we get there.

4:15 am
We've broken into a park with a playground in it and she's playing with my penis underneath a kiddie slide. I get all weirded out and suggest we go back to her place. She doesn't want to because it's a small place and she lives with her brother and his wife. PUA Slacker, who's been an excellent wing the whole night, picks up his phone and says it's ok for us to go over to his girlfriend's place where there's a small gathering going on.

4:30 am
We pick up 40's. She offers to pay for this also, but I'm a gentleman and cover my own 40.

4:45 am
We arrive at Slacker's girlfriend's place. While everyone is partying in one room, I extract this girl to the living room. I rip off her shirt and she shows resistance regarding giving me a blowjob. She wants to go all the way. I refuse because neither of us has a condom. She eventually agrees to giving me a blowjob but does not want to finish. She gets on her back, lies down and I breast fuck her. At this point my two male friends get kicked out of the room they were chilling in and get a nice visual of me on top of this girl with my penis out. They go into the bathroom to give us privacy. Then she gives me more head, downgrades to a hand job, and starts complaining that she's not getting anything from giving me head. I stop mid-hookup, say

"Having my penis in your mouth should be reward enough."

(show-boating for my friends in the bathroom) Fast forward a few more minutes she says she doesn't want to swallow because she just met me. A gentleman, I notify the lady that I'm about to cum and ejaculate on her face to the tune of "That's my eye you asshole!" and raucous laughter from the peanut gallery that has been listening this whole time. They bust out of the bathroom and laugh their asses off. They laugh. I laugh. She doesn't. Topless girl with cum in her eye goes "Hurry up and get me a towel! If I don't wipe this off soon it's going to start to sting." I get a towel, but don't make it all the way back to give it to her because I fall on the floor laughing too hard. She stands up and gets the towel herself.

6:30 am
Slacker's girlfriend gets out of her room and starts yelling at us for waking her up and kicks us out of her house.

6:45 am
I get Faceshot's number. She says she doesn't care if I call her, but make sure to leave a message because she works a lot, but she had a good time and make sure I call her. "Ok, whatever. Just make sure you wait by the phone; I only let it ring ONCE."

7:00 am
I buy a blueberry muffin at Dunkin Donuts, hop on a train, and go home. There are some cute teachers on the train, don't approach. I giggle to myself and then fall asleep on the train.