Bad Babysitter

He was a divorcee whose apartment looked like sitcom shorthand for an absent lady of the house-piles of dirty laundry, dishes in the sink, beer cans and pizza boxes everywhere. I wouldn’t have been surprised if a goat had wandered through the living room.

I was in one of my role-playing phases, where I had experimented with advertising myself in different fantasies other than friendly young coed. Daddy’s little girl, teacher’s pet, and the naughty babysitter. These kinds of posts are attention-grabbers; they tend to get potential clients excited and make them click on your ad/email you, but I found that most guys didn’t actually want to play out the fantasy on the call. I kept my knee socks and plaid skirt on standby in case they ever did, however.

This particular client had responded to a babysitter ad, and he wanted to smoke pot and persuade me through our encounter. As an aside, I have a disease in which I actually hate smoking pot but am unable to refuse it when it is offered to me. I always say yes, and soon afterward I always end up thinking, “Oh yeah, I hate this feeling.” But it doesn’t stop me from saying yes the next time somebody offers. The only time I really enjoy it, actually, is during sex, because everything that feels good feels like its happening for like an hour and everything that can be kind of tedious like performing oral sex comes into really sharp focus and seems more interesting.

He told me about his actual children, currently with his ex-wife, and suggested that I might actually want to baby-sit for them one day. I’m a nice girl and everything, and I can turn on Dora the Explorer and eat chocolate cake from their fridge as well as anyone else, but what kind of father entrusts a hooker to watch his children? More than you would think; in my life as a callgirl, a lot of guys made this suggestion. I guess it’s the impulse to help a poor college student out mixed with the desire to trick me into having sex with them for 10 dollars an hour. One guy even suggested I be a live-in nanny/sex slave for the summer – taking care of his child during the day and servicing him through the night. Sounds great, but a total lack of sleep would make anyone shake a baby.

So we smoked and I let him “talk me into” letting him put his hand on my tits, then under my shirt, then over my panties, then on my bare pussy. I let him guide my hand to his crotch, interspersing a few “I don’t know if we should do this”s and “I have to be home soon”s. At one point in our dry-humping I ended up with the top half of my torso hanging upside down off the edge of the bad staring at his children’s crib and toys while he slid his fingers a bit aimlessly between my labia.

Eventually I let him convince me that none of the other boys at school would find out if I let him take my virginity, and we got down to business. I grabbed hold of the bed frame and positioned myself skinny while he pushed my legs onto his shoulders and fucked me like child support was due.

From that position he was able to jam his cock all the way up my cunt and really pound me, and when he was done, he rolled off sweaty and satisfied. Until he looked down and saw that he was no longer wearing a condom. Slightly panicky, we searched the bed and surrounding floor area and scanned each other to see if it was sticking to moist flesh. I stuck my fingers inside myself and felt around; nothing seemed to be unusual, but I was self-conscious really jamming my hand up there so I told him I would investigate further in the restroom.

After shutting the door, I got all Nancy Drew on the Case of the Missing Condom. I slipped a finger up there and felt inside – nothing. I slipped my fingers up a little farther – still no sign of the little guy who was supposed to be protecting me from pregnancy and STDs. Finally, I pushed my fingers as far as I could get them up my vagina and only then, with the very edge of the tip of my finger, could I feel a little brush of latex.

Fuck. All that pounding had pounded the trojan practically up into my womb.

With none of the aplomb of a poised and sexy sleuth like Nancy, I had to walk back out into the bedroom and explain that the condom was currently adrift in my vaginal sea, too far out for the rescue boats to reach it.

With the same degree of sexiness, he told me to lay down and spread my legs.

Let me tell you, nothing kills the fantasy like an impromptu gynecological exam from the man who hired you for sex. He dug as far up in my snatch as he could while I held up my pelvis and only after a good 10 minutes of getting ahold of it enough to pull it down a quarter of a millimeter did he finally manage to pull the limp, useless condom out of my blushing vagina.

I have never put on my clothes more quickly. We had the obligatory "I'm clean, are you clean?" conversation, but there wasn't really much we could do at that point. The only thing that could have made the situation more unpleasant would have been starting my period. And, strangely enough, he never called for my babysitting services.