Sometimes life gets to be a lethal combination of lonely and boring. When it does, horrible things can happen. It can lead to hilarious abominations like backyard wrestling and I'm fairly certain it's responsible for 2/3 of all incidents of arson in the United States. For me, it resulted in a fateful Autumn night of pretending to be a girl on craigslist. The following is a play-by-play account of an actual exchange I had with a young man who posted in the Strictly Platonic section. Keep that in mind throughout our correspondence. STRICTLY PLATONIC.  

His Original Post

Let's chat, talk, flirt, or whatever - m4w - 27 Reply to: pers-872249915@craigslist.org hi, I can't seem to sleep right now...let's have some fun by exchanging emails. care to flirt? My Response I just went on craigslist for pretty much the same reason. Late-night person, bored, some talk would be nice.

(what follows is a standard salutary exchange. Then I get serious)

me Jessie here. I'm a student at (college). I don't usually do stuff like this. Most of the time, my friends and I hang out and watch movies and stuff. What's your fave movie? (He buys it)  

him ohh good question...I can't say I have a favorite movie, but I do have movies I like alot.  Jerry McGuire, Independence Day, Transformers, Juno, among others... What are you studying at (college)? hmmm...what's the craziest thing you've done at (college) so far?

(I restrain myself)

me That's cool. I totally love Jerry McGuire. It's probably one of the reasons I became a business major.  (<--this is one of my favorite lines of the night.) Freshman year when I definitely didn't know how to drink, me and my friend Suze got trashed on goldschlager and stole a bunch of lawn chairs from a sorority house. I dunno, I guess maybe I don't have a normal definition of crazy. I don't get into trouble, I just have fun.

I immediately regret not sending a question back. He'll probably respond anyway. He sends this somewhat perplexing response:  

him When I was a sophomore in high school, my friend and I went to a frat party pretending we were students from Montana State U.  they totally bought it.  I think it was the first time I saw a woman's cleavage.   Anyway, I went to school down in CA where they didn't allow partying or drinking.  But I still had my fun.  I mean "fun" What year are you at (college)?

(I mean, is he really conservative, Christian, something? I mean, the cleavage bit? Seriously? I don't know what he means by "fun" but I'm starting to get worried)

me I'm a junior. That sucks your school didn't allow partying. What kind of "fun" did you have?

(I decide it is my mission to bring out this guy's inner creep. If I can get him to whack off a little, that'd be just swell)

He opens the door... finally We'd have parties and go dancing.  i was dating a girl from that school (very brief) and she couldn't understand how strict my school is, and so we'd go over to her place. what kind of "fun" do you like to do?  innuendos...lol

(And I step right on through)

me Hey, I'm a pretty liberal girl. I don't have any problem talking about sex. No innuendos needed, unless you're into that sort of thing :-) Sadly, I am painfully single right now. I'm so sick of college guys. It's like, can't you shower more than once a week? Like I said, I don't usually go online, but it's lots of fun to flirt.

(And he starts delivering)

him I suppose you can [say] I'm painfully...single, too.  I can't complain about college girls, although I'm a bit older than the average college aged girls...so I go for grad school girls.  they're smarter too. I shower every day and like today, twice.  once when I woke up and the other after game.  I'll shower tomorrow, too. originally I thought about asking if anyone would be up for truth or dare...don't know why I like that game.  it's fun I guess.  it is fun to flirt. ok, first question...what do you most hate about guys?

me Hygiene seems to be an issue for a lot of guys. I mean, if we're gonna be intimate, I need you to smell good and be clean, ya know? What's your favorite part of a woman's body?

(I need to find some amateur porn pics right now so I can send them, maybe. We'll see where this goes)

him my favorite part of a woman's body that I like to look at is her face, especially if she has lovely eyes and nice lips.  The part of the woman's body that turns me on is her butt.  Speaking of smelling good. 

(I don't know if the smelling good comment refers to the ass comment or the perfume one that follows)

When a girl wears a nice springy fragrance, that's a major turn on.

(the emails proceed in this fashion, with the usual questions about "does size matter" and other softball stuff. Then he insists we enable chat. Note the time stamps)

him: ok, so here's my question for you...where do you like to be kissed?   

2:12 AM me: Where don't I?   

2:12 AM him: lol   

2:12 AM good answer. I like to kiss the girl right above the breast and in between...so it's almost like as I'm teasing   

2:15 AM me: That's what makes it good.   

2:16 AM him: see it's not about rushing into things, it's about building it up, building it up   

2:16 AM me: What's your favorite way to "build up"?

(Things start to get hottt) him: I'm really good at massages, so I'd massage your neck, and shoulders, and as I'm rubbing your back, I'd go lower and lower and put my face closer to your neck so you can almost feel me breathing, and massage the arm, the chest and tease around but each time get closer to certain points for the sake of anticipation...and as I'm kissing, I won't slobber. I'd be gentle and rolling my tongue just right, but also with my lips brushing by, too.    

2:19 AM me: Then what, man with the plan?

him: wouldn't [you] like to find out...   

2:21 AM (he asks me about my cup size, so I have to do some research with some compare and contrast to the webcam girl I selected to be "Jessie". He proceeds to offer me a massage several times. He then asks me what kind of undies I wear)

me: I actually do bikini underwear  

(...because the webcam girl does. I decide to go for broke. I ask him to start trading pics and he obliges. The following are samples of what he sent)

(I send him this and several other, racier pics of "Jessie")

 

(At first he completely buys it. He comments on the sexiness of my legs and offers me more massages. By about 3:00 AM he starts to get suspicious. He eventually finds the watermark for the webcam site. It's time to bail. I feed him a line about my Facebook page and then I placate him by telling him I'll send a face pic. Even in this moment of doubt he's still trying to convince me to come meet him. I finally send the following pic and block him from my puppet email account)

 

All in all, it was a good night.