Been a while  

JillIsTheOne 38
76 posts
5/10/2006 11:10 pm
Been a while

Hiya everyone. It's been a while, I had been in a steady relationship for a bit, which just ended. *SIGH*

So this story, while pretty hot, is kind of funny too.

So I went to chaperone for the East High School prom. My job was simply to patrol the hallways, looking for kids causing trouble and keeping them out of the hotel rooms. Nothing more. And don't ask how I got stuck volunteering for this.

I'm wearing a form-fitting red long sleeve shirt, low cut int he front, but still appropriate. Also black slacks, that hug my ass well if I do say so myself. And red silk thong with a red bra.

So it's around 10pm, the party's in full swing. I decided to take a break and sit at one of the tables and rest my feet from all the patrolling. A kid walks up, decked out in some dress clothes but also wearing his letter jacket. (Odd, but okay.) He is a senior, judging from the "Class of 2006" stitched on his coat.

He's actually attractive, but somewhat young for my standards. So it was cute when he walked up and said "Well hello beautiful, do you not have a date?" I laughed. C'mon. I don't look 18, and I know it. I rolled my eyes and said "Thanks for the flattery but you know I'm a chaperone." He nodded, and then walked away. I thought he was leaving after the subtle shoot-down.

To my surprise he comes back with some punch, sits and says "I brought you a drink because you have to be parched, you've been running through my mind all night." Oh...dear...God... I laughed, said "thanks" and drank my punch.

So anyway this banter continues for what must have been 15 minutes. He would hit me a pickup line, I'd laugh and he would try again after a minute.

To my sheer shock, he leans over and whispers in my ear "I may be 18, but I bet I can make your toes curl and you'll beg for more." My eyes go wide, I turn to face him, and the crafty bastard dangles a plastic card key in front of me. He smiles and says "it's to room 130."

After a few seconds, I recover and say "You wouldn't know what to do with me." He retorts "I could think of 20 different things to do TO you." He put emphasis on "TO". I'm sitting here thinking this is just a horny 18 yr old who would back down when put to the test, so I say "prove it".

"Cmon" he says and I follow him over to the room. Sure enough, that was the key, and we walked in the door. He immediately stood behind me and started kissing my neck. Shit. I know it's a common thing, but it really is my kryptonite. I decided I would let him play a little and then let him down gently.

He did it for a while, like 10 minutes. And he was running his tongue up and down my neck, then up to my ear and nibbling on it. Mmmmm god I love that. He had quite the erection going, and at this point I'm guessing he's well endowed because it was pressing pretty hard against my ass. He moved his hands to my waist as he started grinding against me. It was becoming a crisis...he's a bit young, but not illegal...perfectly well equipped to please my needs...decisions...decisions...

His hands move for a second, his lips and tongue still seducing me via my erogenous zone on my neck, and his slacks drop to the floor. Next I know, his hands are pushing down my pants, just a couple of inches, and between my legs slides his cock still covered in his silk boxers. I was correct, he's a big boy. Probably about 7 to 8 inches, enough for it the head to peek up at me when I looked down. I reached down, and slid my fingers up the underside an inch and pressed it up into the crotch of my panties.

He puts one hand on my waist, the other on my upper back and pushes forward, bending me over so that i put my hands on the bed. He kneels down behind me, pulls my panties to the side, and I feel his wet tongue slide up and down my lips. Mmmmm okay, I can't in good conscience let him get this far, and end it here. That would be fucked up. It looks like i'm committed at this point.

His tongue is making some rapid circular motions around my lips, and occasionally checking in on my clit. He slid 2 fingers in, making the "come here" motion. It all felt good - but you know me, it doesn't happen with me. I pushed him away after a few minutes and knelt down in front of him.

He was all too happy to drop his boxers, and I started licking him. His cock wasn't really thick, enough to be worth mentioning, but it was nice and long. No upward curve though

This is the point where it gets pretty hot. He puts his hands on my head and starts fucking my mouth. I mean as if it were my pussy. I gagged at first but adapted by relaxing a bit and deep-throating it. When he came, it was all I could do not to choke, as he was cumming right in my throat. It was erotic, I liked how he took charge and took what he wanted. But you guys know that.

He pulls out then helps me stand up. He firmly spins me around, faces me toward the bed, and bends me over again. Before I can even protest the lack of a condom, he thrusts inside me. I swear, I felt it inside my cervix. Oh my god. Next thing I know, he grabs both of my wrists and pins them against my back. He holds them down with one hand and starts slapping my ass as he starts just pounding me. And I mean they were loud slaps that stung. But it was SO hot.

It was so erotic and so new that I orgasmed after maybe 30 seconds. I've never been fucked so hard and so deep. Even the sound of his pelvis hitting my ass was loud like a slap. We fucked like this for about an hour. I orgasmed 3 times total and when he came, i think it may have been the most cum that I've ever had. Even when I got home, after wiping off most of the excess cum in the hotel room, I still had some in my panties.

So we left the room discreetly, and that was that. I was a little sore the next day. Kinda hurt to sit down LOL.

Thanks for reading

silkdawgg 39M
43 posts
5/11/2006 11:32 am

sounds nice i would love to have you chaperone me anytime

rm_Entro1963 54M
9 posts
5/11/2006 8:10 pm

Dear Jill,

You are a talented belletrist. And, I think you write about experiences that masculine men appreciate. I am not convinced this story actually took place. Anyway, you're a wonderful writer.


rm_kneel_be4me 50M
457 posts
5/12/2006 7:02 pm

HMMM maybe I should have gone to more school events. It sounds like they might have been fun.

Cowboy_Deluxe 39M

5/14/2006 1:06 pm

Evil grin here.. Thanks for sharing.

JoelG1967 50M
89 posts
5/14/2006 9:05 pm

I wish that guy was me, but I am not 18 anymore.

panthersdreamer 48M
295 posts
5/16/2006 10:19 pm

wow! if only i was 10 yrs younger!!


fukmesilly79 39M

5/27/2006 9:31 am

one of the hottest posts i've seen in a while. wow! that's all i can say. wow! very hot jill.

GentlemanLeisure 55M
192 posts
5/29/2006 11:32 am


Excellent! Nice to see a change from the usual, 'Older guy gets young filly'-type story. This really had my admiration for your writing rise... to the ocassion. Lolol.

Can you imagine what that 18yr old will be like by the time he hits your age?

More, please...

rm_dazzlebum 35M
1 post
7/10/2006 2:36 pm

damn this was my favourite blog. What happened to Jill ?

hornyguy4u1975 43M

7/21/2006 4:02 pm

I can only imagine how sweet that mouth would be on my dick. That guy was sooo lucky. Glad he fucked you well... you deserved it..

rm_Travis1232 35M
2 posts
7/30/2006 8:05 am

wow that is hot. i have a couple stories like that if you are interested in them let me know. t h 1 2 3 3 America Travis

SirMounts 103M

8/3/2006 11:27 am

Well, it always wise to have good relations with the students. *winking*

rm_ulikemy9in 36M
30 posts
8/8/2006 2:49 pm

wow sounds hot wish i could go to the next prom you chaperone

rm_1stymersd2 49M/48F
5 posts
8/10/2006 6:31 pm

hi jill...pinoy couple here, would you like to chat?

B0wflex 44M
294 posts
11/26/2006 6:03 pm

Nice story... reminds me of me... Maybe I should go back to High School again... Hmmm I'll have to think on that some more...

B0wflex 44M
294 posts
11/26/2006 6:04 pm

Oh sorry to hear about your relationship... it does suck doesn't it, feels like you wasted your time... Well it did for me anyways...

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