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12 March 2005


Jason the College Boy

Friday night. I crawl between the sheets around midnight. My phone rings at 12:45. Does this sound familiar?

Lui: What are you doing?
Je: I am sleeping, Jason.
Lui: Would you like some company?
Je: You know, I really just want to sleep. I’m very exhausted. My mom had surgery this morning, I had a full client load and I had to deal with insurance and tags for my new car.
Lui: I would really like to join you. Just to sleep.
Je: Are you drunk?
Lui: No, I’m just alone.

Yes. I know the angle. It's been worked a million times. And this? This boy has got the cockiest attitude on any given day. He is a swimmer, has an impossibly lean body, is very cute, and is excellent at hiding his insecurities.

Except late at night, when he calls me.

I rouse myself, go unlock the door and get back into my warm bed. About 10 minutes later he walks in, takes off his shoes by the door and locks it behind him. He passes into my room, turning off the dim lamp I’d left on out of habit. I poke my head out of the covers.

"Hey. Scoot over."

We fall asleep. For an hour. Then there is an erection pressing into the small of my back. Okay, it was there before, but we said sleep only, right?? He needs me to tell him I've missed him. To feed his ego; make him feel better about himself. He needs to learn that it’s okay to be vulnerable.

He is kissing my neck. It’s nice. He wants to know if I want him inside me. I tell him that would be nice, too. I help him with the condom, and take him in. Two minutes later, he cums. He apologizes. I appreciate this, and I’m curious. I ask him when he last had sex.

Two months ago. Huh??

But what about all the blondes at school?? You need to have more sex than that, man! Also, I was fine with the whole sleeping bit before, but now I am primed for some serious pounding.

We lie together, talking about school, his friends and my kids. We laugh, and have an easy conversation. I am resting my left hand on my pubis, and my right reaches down to his limp dick- cos limp dicks are fun.

“Is this okay?”

“Yes…god, yes.”

I scoot lower down. “And this?” I lick his shaft, kissing the tip, then take his cock into my mouth.


No problem, there. I love it when a dick gets hard in my mouth.

I tell him I want him to fuck me from behind. A few minutes in, he tells me he wants my ass. Now, Jason the College Boy and I never had any assplay; he is a virgin giving as well as receiving. He wants to fuck my ass, and then let me play with his. He wants to give me his anal virginity.

Tempting as it is, I am not in Training Mode at 3 AM; it is too delicate a procedure to navigate with a novice. Plus, if I get assfucked, I will never sleep. And wasn’t that the point of this visit?


Blogger Jefferson said...

Such a wise teacher.

It must have been tempting to go at it, but you are right: it's just smarter to give yourself time when taking on something like Jason's virgin ass.

Being a straight boy, and an insecure one at that, he may be a little uncertain about why he finds it hot to want you to bend him over.

Rushing it might spook him. What if it "hurts" and he doesn't want to go there anymore? What if he likes it too much, and that's "gay"--even with stunning gal like yourself?

So now the challenge: to make a date with his ass, at a time when you have the time and energy to really give him your best effort.

Blogger Madeline Glass said...

Sound advice, as always. Lube at the ready, condoms and finger cots within reach...(thanks, Jane!) Rock on.


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