Dare

I am not sure if it was the shots of whiskey speaking or me starting to get turned on but I spoke up declaring, “DARE!”

“I dare you to go into your bedroom, open up that top dresser drawer of yours and bring out here the largest dildo you got. You know the one that is black with textured veins all over it. Looks like it belongs in a porno. I dare you to bring it out here, set it on the coffee table in front of us and slowly slide your greedy little ass down the entire thing.” Sam said with an evil grin on his face.

How the hell did he know I had that toy? I just got it a week ago and haven’t even told James or Tim about it. I bought it in a drunken horny late night binge. Was that what sam was doing while the rest of us were playing the video games? He was out searching my room for my toys to **** me with later? Fuck I bet Tim set this entire thing up knowing him.

“I uhm well maybe we should just watch a movie and call it a night…” I said

“Nope, a dare’s a dare and you can puss out at your own party.” Said Tim and a full agreement from the entire room of guest. Fucking pervs, they all worked this up ahead of time.

“Fine, but just so you assholes know I drunkenly bought that toy last week. So don’t get all pissy when I take my time sitting down on it.” I blurt out while stamering into my bedroom. “Is this why you pervs set this sleepover up? Just to see me play with my butt and toys?” grumply curse as I return to the living room with my big bottle of lube and the giant black dildo I still haven’t pulled out of the box.

“Shit L is really going through with it.” Zach said “James, you are the bestest roommate in the world. I’m so glad you invited me.”

“Haha yeah, I’ve seen the porn you watch. Figured L is right up your alley. But don’t thank me all that much, this was all Tim’s idea. He’s been planning this pretty much day one of meeting L.”

“Guilty” Laughed Tim “Sam and I have a few classes together and I overheard him talk about this cute little femboy and knew he would fit in so well with our little group… well maybe not fit in so well.” Tim looks down at Sam’s boxers barely able to hold back his bulge. “Let the show begin. L do you need a hand lubing up? I am sure there are a few of us here that wouldn’t mind giving you a helping finger or three. Or at least let us help you to remove your panties”

“Fuck off Tim. You all don’t get to enjoy this anymore than I get too. Now Let’s get this over with and move on to the next victim.” I slide my thong over my one butt cheek giving everyone a clear view of my little boy hole. With shaky hands I gently press the lube bottle up against my hole and squeeze a few ounces into my tight butt. Hoping to lube up deep enough that this toy slips easily in. Then I generously coat the dildo with more lube as I begin to line up my butt with the mushroom head. It wasn’t that thick of a toy, just good and long. I cheaped out and did not get the silicon ball attached, just the blunt back end with the stretchy hole. I guess it was ment to stretch over a plug on a fuck machine.

The dildo head pops into me and I slowly begin to push more weight down on top of it trying to gently slide further down. As I pass the halfway point I begin to forget that I am sitting on my living room coffee table in front of my friends and some other pervs. “Oh hmmm” Fuck did I just moan out loud? This toy is feeling really but I can’t let these pervs win.

“Hell yeah now we’re talking.” Sam said. I sturdy myself and push a couple more inches in. I have a few more inches till I am fully seated on the coffee table with the big dildo fully inside me. However, I am having a bit of trouble with getting any deeper. “Having a bit of trouble with the last bit, are we cutie?” I think you might need a little help.” Just as Sam finished his sentence I noticed him give the coffee table a solid kick.

Everyone in awe watched as the coffee table shook causing my feet to sleep on all the extra lube that I was worried I would need but now wished I hadn’t. Instantly my but slammed down to the table fully hilting the dildo deep inside my guts. 10 full inches of dildo was now touching un-touched depths inside me. I was panting heavily trying to figure out what all just happened.

“Wow! I really didn’t think that possible. I mean L is barely 5 and a half feet tall that dildo is like a 6th of his height. It has to be up deep.” Zach pointed out. “Well, at least I know with some **** I got a chance with that hole. haha”

“So, uhm.” ragged breathing “now that I was able to get it all in” more heavy breathing “I think we all can just move on and watch a movie or something.” I am barely able to speak as I slowly try to stand back on my feet.

“Hey now, where do you think you are lifting that little butt of yours off too? “House rules” am I right guys? “Must remain that way till morning.”” said Zach “If Sam and I have to stay like this till morning then that goes for you and that toy of yours.”

“What? That isn't a house rule.” Starting to get a little overwhelmed

“You said it yourself L. Rules are rules.” Tim chimed in. “Now who’s next?”

“Fuck all of you. Tim, Truth or dare?”

“Why truth, of course.”

“Did you really only become my friend because you wanted to see me naked?”

“Well maybe at first but you are really fun and sweet so it turned into a bit more of a thing then I thought.” Tim said with a sweet smile.

“Oh okay well I guess that's fine” I said.

Tim’s turn to pick the victim. “James, truth or dare?”

“Dare”

“I dare you to give everyone two or three of these Viagra pills so that this wonderful night won't end for a good long while. You needn’t give our little centerpiece any. I am sure L wont be using their little cock for anything anyways.” Everyone took a couple pills with a swig of their drinks and pocketed a few more for later. This is looking to turn into a really rough night for me.