Nothing’s Free from The Trickster
filed in Fan Stories on Oct.16, 1983
We agree. Condoms are a must. No anal. My place.
I’ve never done anything like this before.
Usually fuck buddies need to be found. They aren’t given to you. You find the right girl, the right venue, with the right set of personal circumstances for the both of you and her and you’re in the man’s ideal scenario: a booty call. Sex without commitment is just one drunken phone call away.
Only this time, the set up has happened through a third party. And I actually haven’t met the girl before.
Normally, I’d never go for an arrangement like this. Even for the horniest of guys, you at least want to get to know whom you’re fucking, even if it’s for only one drunken hour in a loud club. But I’m assured that her sexual history is clean, and she is more than willing.
I feel as if a lump of gold has just been dumped in my lap.
We exchange photos and chat over the Internet. You’d think arranging a session of purely physical sex would be a turn-on, but it’s not. We talk about logistics, rules, game plans, dos and don’ts, and our sexual history. It’s all very mechanical and very un-sexy.
I tell her that I’ve been around, but I just got out of a long-term relationship and that she doesn’t need to worry.
She tells me the same. Only she’s, in her words, “less experienced”.
I say, that’s fine. I can lead. I like to push girls around in bed.
I realize that this is the first flirty thing I’ve said to the girl I’m going to fuck in two days. This weirds me out.
But I push the thought out of my mind. This is a guys dream scenario! Sex, without any work!
But there has to be a catch. There always is.
I tell her to wear something sexy.
She arrives at my doorstep wearing a short skirt and a white top, both of which are just short and just tight enough to imply sexual intent, but not give away the whole story.
She’s not a bad looking girl, though she’s not generally the type I go for. But, I remind myself that she’s giving me sex with no effort and no commitment. I smile, I greet her, and I invite her in.
She seems nervous. I’m nervous too, so I understand how she feels. We go upstairs and into my bedroom and we sit on the bed unsure of what to do.
Seduction is normally a process. You meet a girl, you flirt, you get to know her a little, and if you play your cards right, you get lucky. But there’s no process here. We skipped to the end. There’s no context, no sexual tension built up, no nothing. I’m not even sure if I’m horny, I’m just confused.
She’s nervous now, and she has nothing to say… so I say the first thing that comes to my mind. Icebreaker, I think.
“So, how was your day?”
I immediately regret the words that came out of my mouth.
She gives me a confused look that telegraphs her thoughts. “Seriously?” I can see it in her eyes. She mumbles a response that I don’t hear nor do I care to hear.
I sigh. It’s game time, but I don’t know whether I can do this. I’ve always thought that sex without commitment would be hot, but this? I don’t even know this girl.
But, fuck it. She’s here and this needs to happen.
So I ask her, “Do you want to just cut to the chase?”
The look on her face tells me her answer.
I start kissing her, and start massaging her breasts. I can feel the nervousness in her body. She’s almost shaking. I whisper in her ear, “Take it easy baby, I’ll take care of you.” But this is an arranged fuck session, not a love-making session. I decide to get aggressive.
I push her up against the wall. Massage her breasts. She’s moaning now, and she’s into it. Now, I’m filled with sexual energy. This is kind of hot. I remember how I love making girls moan.
She turns around and unbuttons my shirt. She says to me, “Wow, you’re buff.”
I reply, “All the better to push you around, baby.”
Our clothes are off in an instant and I fall, back onto the bed. She kisses me.—strongly… an “I’m fucking you” kiss. She moves her way down to my erect penis and puts her lips around it.
And then, a searing sensation, and all I can think is, “Ouch.”
Teeth. All teeth. On all the sensitive parts.
Getting head with teeth is like getting massaged with spikes. You know the motion is supposed to feel good, and it kind of does. But then sharp pain radiates through your body and overwhelms what little pleasure might be had.
But she told me she was inexperienced, so I just assume she must not have given much head in her last relationship and I decide not to push the issue. I sit up, which forces me out of her mouth. She looks up at me, and I kiss her.
Then she grabs my cock and starts stroking.
“Ouch.”
Again.
A hand job is an elegant art, something I really hadn’t appreciated until now. You need to hold with just the right amount of pressure, and the motion needs to be fluid. Done right, a good hand job feels as natural as sex itself. Done wrong and it feels like you’re fucking a cheese grater.
She holds my cock like it’s a beer bottle, only she’s angry at it. Her vice-like grip combined with the mechanical up and down motion make it even worse as it rubs me in all the wrong places. Surprisingly enough, her hand jobs are even more painful than her full-toothed blowjobs.
I grit my teeth and tell myself, she already told me she was inexperienced, so this is to be expected. Even though the alarm bells are sounding in my head, memories of the familiar feel of a warm pussy override any doubts I have, and I gently suggest that we’re ready for sex.
She agrees.











January 15th, 2010 on 5:53 am
IF she messed up the hole or something of the sort… i hope you bolted
January 17th, 2010 on 10:12 pm
It really doesnt get much worse for a first time then that haha.
January 18th, 2010 on 6:54 am
I’m not gna lie. It made me really happy that he was such a nice guy about it. Like he coulda been a real dick. But he took care. Props to you man.
February 9th, 2010 on 12:45 am
true that i agree with Lauren – classiest he could have been in a f-d up situation