The Old Jail

The old jail looks dark and forboding, but we're crazy young adults who are skipping school, so what do we have to lose?

I comment, "Based on there only being one cell in the jail, they must have had an insanely low crime rate in the old days."

Eric says, "Well, back then they were still hanging people or exiling them."

Lewis pulls the cell door open. The screech of old metal scraping is painful. He says, "Hey, let's take turns getting our pictures in here."

Eric and I laugh. I say, "Sure, why not?" and Eric and I ready our cell phones. This will make for great insta fodder if nothing else.

Eric closes the door with Lewis inside. Picture taking ensues. Eric even grabs a video of Lewis begging for his one phone call. Eric says "Dude, they didn't have phones back then."

Lewis comes out and Eric goes in, pulling the door behind him. More pictures. Exciting? No, but still better than a science test any day of the week. It's kind of neat to be standing in the middle of ancient history, or at least ancient compared to modern-day Littletown.

Then it's my turn. Eric comes out and holds the door open for me. I walk in and he closes it behind me. I turn around just in time to see him slip a padlock through the lock assembly on the door and snap it into place.

They're only role playing, but I don't like this. I hope they have a key. I glare at Eric with my best what-the-fuck look. He pulls a key out of his pocket, waves it, and puts it back in. He says, "We thought you might like to have the real jail experience. Go ahead and pose and look unhappy about being locked in a jail cell."

They have their phones ready, and it isn't hard to look unhappy because the feelings are genuine.

Lewis says, "Take your top off."

"What?"

Eric says, "You heard the deputy, take your top off."

I look at Eric like he's crazy. He pats his pocket where the key is. Okay, fine. I take my shirt off. He says, "Now, pass it through the bars to Lewis. And by the way, that red looks really good on you. It almost matches the red in your face."

Lewis laughs and snatches my tee shirt out of my hand. He says, "Now pose again."

More pictures. God this is getting humiliating. I know what's coming next before Eric even says it. I go ahead and unclasp my bra and hold it out for Lewis.

Eric muses, "She learns fast. Good girl. You're making a great prisoner, Riles."

I pose, the bars are spaced wide enough that my breasts fit between them, so I give them what they are wanting and then some. More pictures. I will have to make sure those pictures get deleted later.

I back away from the bars with my arms crossed under my breasts. More pictures. Seriously guys? Now I wonder how many candid pictures of me they've taken without me knowing. Eric says, "Okay, now you can get on your knees right there, and put your hands through the bars. I wait for the zippers.

The zippers don't move. Instead, they each grab a wrist and I have no idea where he got them from, but Lewis slaps a pair of handcuffs on them. I can move my arms up and down the gaps between the bars, but my hands are stuck outside.

Then the zippers move. Lewis says, "Continuing on with the jail cell experience, you will give our cocks some pleasure."

I open my mouth and in goes Lewis' cock. There isn't much for me to do other than let him fuck me in the mouth. It's a little on the vigorous side but he is sensitive to his depth. It swells to a healthy girth, just short of causing jaw discomfort for me. Lewis pulls out and slaps Eric on the back. Eric gets his turn and while he doesn't have quite the proportions that Lewis does, it comfortably fills my mouth.

Then Eric pulls out and they look at me momentarily, their members firm and erect. I can't reach them but I would love to touch them. I also know another place that would like to touch them, but that isn't possible right now.

Eric says, "Okay, time for the final phase of the jail cell experience. Lewis, if you please?"

Lewis unlocks the cuffs and takes them off. I pull my hands back through.

I ask, "So what next?"

Eric says, "Now, you need to drop your jeans and thong, they are obstacles on the journey."

Oh god, a poet you are not. I loosen my belt, undo my jeans and pull them down, snagging the waistband of my thong with my thumbs as I go.

"All the way down to your ankles. Then walk back over to the bars."

I comply and then waddle back over to the bars.

Lewis says, "Picture time!" and the machine gun of clicks from their phones lasts a solid minute.

Eric says, "We are almost done. Turn around and back your ass up so your cheeks rest on the bars. Bend over and put your hands through the bars.

Dreading the headache I'm going to get in this position, I follow Eric's instructions. Lewis snaps the cuffs on my wrists again. I am able to bend the upper half of my body up a little. It's a little uncomfortable with the cuffs bracing my wrists on the outside of the bars, but I can maintain this position. More pictures. And I'm feeling a little wet down there with anticipation as the only thing left is for them to fuck me in this pseudo-bondage position.

Eric walkes over and slides his cock in between my thighs, teasing my clit, rubbing against it. It's getting me hot and bothered inside and I'm begging for him to just put it in already. I hear the sound of something squirting and then something cold and wet between my ass cheeks.

I can't really see what is going on back there so I ask, "What is that, and why?"

Eric sighs, still rubbing that rock hard shaft against my clit. He says, "This is a jail, not a brothel."

Something slips into my asshole. Everything clicks all at once. Oh god, he's going to take me in the ass. A sense of relief fills me when his finger moves the "right" way, but then it's coming back in. He repeats that several times, then it slips out all the way. I sigh happily, but it is cut short when something bigger slips in. It must be his thumb because his cock is still teasing my clit. Same deal, he slips it in and out for a minute then slides it out.

A sense of dread mixed with anticipation and the sexual buildup from the clit stimulation rises up as he pulls his cock back and then I feel the pressure of something much bigger than a thumb. "Relax, Riley, it makes it easier."

How do I relax at the prospect of something the size of a cock trying to push into a hole the wrong way? I take a deep breath, nod, and say "Okay."

I feel it push past the barrier. The feeling of my sphincter spreading is indescribable, not to mention the feeling of his cock going in as deep as it can. Then he slides back out, almost all the way, but not quite. Back in. Back out. The nerves in my sphincter are on overdrive and I can't help the moans that get progressively louder as he increases both speed and ****. Oh god, I have never wanted to have something shoved there and not shoved there at the same time.

After a couple more minutes of fucking me in the ass, I feel him pull out all the way. Then I feel something hot and sticky glopping all over my back. I breath a sigh of relief.

The sigh is cut short when I hear more squirting. Then I feel Lewis pressing in. He pushes in and with his thicker girth, it's like having my asshole opened for the first time all over again. He starts slow and easy, but he ends up going a lot faster than Eric. I am shuddering from the waves of pleasure as I am blessed with a double orgasm of extra proportions. One before he comes, and the other shortly after he blows his load. I feel the convulsion of his cock in my ass, he thrusts in as far as he can go, and lets it all go. After the last tremor, he pulls out and unlocks the handcuffs.

I rub my wrists for a moment. I squeeze my sphincter to make sure it still works and am rewarded with some of Lewis' cum oozing out. Well, I'll have to deal with that later because there isn't a bathroom here to clean up. I dress, Eric removes the padlock from the door and we head back to the center of the site.