One more tale from the vault. This is the last really insane one. I’ve had plenty of other experiences at events, but they are usually more mundane, never getting much crazier than a clandestine quickie against a forklift in the service corridor or a rousing game of Celebrity Strip Cards Against Humanity.
This is another one of those stories that has a postscript to the action that makes it all the better IMO. Not sure why, but I seem to have a thing for knowing what happened when others don’t.
*Shrug*
Anyhow, here it is.
I was at a con one year that had a maid cafe. I somehow pulled the short straw, and had to report for setup duty at 6AM on Saturday morning (This is the WORST shift imaginable, since you can’t stay up on Friday night.) I was assigned to help set up the maid cafe. I head to where I am supposed to be, and a friend of mine (Deacon) is there. We start setting up, and he tells me that he brought his 18 year-old sister, Elly, this year, and that she was going to be participating in the cafe. I told him that was cool, and we kept on working.
At about 745, most of the setup was done, and the maids for the morning shift were starting to filter in. Deacon ran off to get some breakfast. The cafe didn’t open until 9, so there was not much going on. I had a cute, short-haired brunette girl come over and thank me for setting up for them. I start chatting with her, and after a few minutes, Deacon comes jogging up, and says “Hey, nice to see you two met, this is my sister, Elly.”
We exchange all the expected pleasantries, and Deacon gets a call on his radio. He scampers off to attend to whatever needs attending to. After a few more seconds, Elly looks at me and asks “This is my first big con, is it true what they say about big cons?” I ask her what she’s talking about, and she replies “That there’s a lot of sex and drinking going on.” Being the smartass I am, I came back with “Drinking? Absolutely. Sex? Well, There’s just over an hour before the cafe opens, how about I show you?”
She looks me dead in the eye and says “Let’s go.” HolyShitWhat!? I go from joking to dead serious in no time. This is my friend’s sister, she was barely even 18, I have 5 other people sharing my suite, and it’s not even 8AM. Despite every rational idea in my head, I grab her hand and off we go.
Now for purposes of visualization, Elly was probably about 5’4″, and I’d guess about 160lbs. She had shoulder length brown hair (as mentioned before) and hazel eyes. She was not large chested, but had enough to make the outfit look appropriate. She was pleasantly soft in build (in not really a fan of rail thin women.)
We now return you to our regularly scheduled programming.
When we get to the room, I’m trying to play James fucking Bond, getting into the room as silently as I can. She laughs a little at me, and follows me inside. Everyone else had been up partying until about 3AM, and was still stone asleep. My bed is just not an option. I take stock of the room, and come to a conclusion, it’s the dressing room / bathroom or nothing at all. We dash into the dressing room and slide the door closed. At this point, the counter is totally full with supplies and costume bits and bobs, so there’s no surfaces handy. That’s when I spot my friend’s rolling luggage. I back her up and sit her on that.
We start kissing frantically, hands rummaging all over each other. I never got to see her breasts naked, but they were shapely and firm under that little maid dress. My hands ran over her perfect little ass and eventually down to her already moist panties. I started slowly rubbing circles on her clit, speeding up a little at a time. Eventually she just lifted her skirt, pulled her panties down, then tugged down my shorts and grabbed my cock. I was incredibly shocked by how forward she was being, but who am I to complain? This was not going to be a long affair, but hell if it wasn’t steamy as can be. After a few more seconds of fumbling, I bend her over the luggage, and position myself at the entrance to her now-soaking pussy.
I give a little push, and she lets out a little squeak. I haven’t even gotten any of myself inside her yet, and at this point, noise may be a problem. I tell her we have to be quiet, and she doesn’t say anything, just nods enthusiastically. I line up again and give a push. The head of my cock slowly begins to push inside her. She’s incredibly wet and tight, it feels like I’m pushing into heaven. She lets out another couple of little sharp squeaks as I get an inch or two in, and I pull back and start to push inside her again slowly. She looks back at me and whispers “Go slow.” I oblige her, despite my insane desire to just shove myself into her, and fuck her as hard as I can, pounding her until we both cum.
After 8 or 10 super slow thrusts, I am buried in her to the hilt. She looks back at me and just nods. I begin thrusting in earnest. I keep going slow for a few moments, slowly picking up speed. As I start to move faster, she starts squeaking and moaning softly. She uses one hand to cover her mouth, to try and keep herself quiet. After maybe a minute or two, I’m thrusting in and out of her like a hammer driving a nail. This isn’t going to last long, but it’s probably the tightest pussy I’ve ever been inside, and I’m doing remarkably well already, considering that. After a few more thrusts she lets out a larger noise, and I see her clap her second hand over her mouth. She’s now being held up only by the luggage.
A few seconds later, her legs start to shake violently. I know what’s coming, and I want to get there at the same time. I stand up a little straighter, so that the bottom of my cock is now grinding directly against the front wall of her pussy. She starts shuddering harder and faster, and breathing irregularly. I’m feeling like I’m going to explode and it’s time I did. I start to pull out, and she reaches back with one hand, grabs my hand, and pulls me in. She doesn’t want me to pull out. I oblige her. I push myself in one more time, and we both cum together (or very nearly anyway). A few waning thrusts and I pull out, spent.
We begin to put ourselves back together, and Elly gives me a very strange look.
“I, I’ve never…” she stutters.
“Shit, we can go get Plan B.”
“I’m on the pill, that’s not it. I’ve just never…”
“Cum from penetration?” I ask.
“No… Well yes, but that’s not…”
*Oh shit*
“I’ve never done this before…”
*Oh Shit*
“Con sex?” I ask?
“Well, yes, but again…”
*OH SHIT*
“Was this your…” I trail off.
“First time.” she finishes, and proceeds to blush fiercely.
I stand there gawking at her. She just smiles and says “Thank you, it was amazing.” I am completely lost for words. And when I have nothing to say, I always manage to say something stupid. “Um, we better get you back.” I say. She just lets out a soft laugh and nods. It’s at this point that I become completely filled with panic that Deacon is going to find out that I just fucked his sister, and that she was a virgin, and he was going to kill me in my sleep. Apparently the panic was evident on my face, because she looks at my expression and says “Don’t worry, it’ll be our secret.”
After a second James Bond like set of maneuvers, we are out of the hotel room, having apparently not roused a single person. I walked her back to the maid cafe, and no one seemed to be the wiser for it. She got back with 10 minutes to spare, and Deacon was nowhere in sight. “Can we do this again later?” she whispered in my ear when I gave her a goodbye hug.
“Absolutely!” I whisper back. We break the hug, and she grabs my hand and squeezes it. I walk away, feeling like I just won the lottery. I head back to the room, just in time for two of my friends (Rob and Jen) to start working on getting up. They walk into the dressing area, and give each other a rather puzzled look. It probably smelled like an orgy in there. I went about my con day, and when it was over, met up with Elly again, this time in her hotel room while Deacon was at a party. We fucked for the better part of two hours this time (in probably 20 minute increments, with breaks between to recover.) After we got through, she kissed me and we parted ways.
A few months later, I wound up running into her and her new “boyfriend” at another event. He was the completely ridiculous, holier-than-thou religious type with a cross tattoo, WWJD bracelet and boy band hair. I only talked to them for a couple minutes, but I noticed that she was wearing what I had to guess was a purity ring. I couldn’t help but smile as I walked away, knowing that I got to her purity before he had a chance to tell her she needed to save it.
Edit: Fixed some spelling and added the word “clandestine” near the beginning. I like that word.
Source: reddit.com/r/gonewildstories/comments/58o8qc/mf_could_this_be_called_maid_service
That epilogue is great, you’re right
Hot
Okay I’ve seen these con stories and I’ve always wanted to do a cosplay anyways. Is sex REALLY that common there or are you just the luckiest fucker on the planet (no pun intended)?
That was fucking hot, especially the epilogue. Amen