Welcome to another big damn long event report. (Even ripping large chunks out of the first draft, this still ends up being over 5000 words. I’ve got to work on that ‘brevity’ thing.)
My ride to-and-from this party was the same one kind enough to give me a lift to-and-from Darklady’s Masturbate-a-Thon back in May. His name is JeannieJ, and I’m now wondering about proper pronoun usage for a guy in full drag temporarily using a female name. Huh. Well, considering that later in the party I’d see him slide his cock into a very horny woman, I think I’ll stick with the whole he/his/him thing in this case.
JeannieJ was dressed schoolgirl, with an incredibly short skirt. (There were a lot of schoolgirl outfits at the party, but I’m pretty sure that JeannieJ’s had the shortest skirt of them all.)
My planned costume hadn’t happened, so I was just there with a backpack full of school supplies and a notebook filled with (naughty) homework assignments.
From Back to School to Detention
The party had originally been announced as Darklady’s ‘Back to Reform School’ Party. It looked like it was going to be the same basic format as her other big events (at least, those few I’ve managed to attend) have been. Both floors of the venue. With socializing, milling about, dancing, etc. on the upper floor. And more intimate shenanigans on the lower.
But low RSVP return caused her to alter the plan beforehand. She canceled the Back to Reform School thing, then announced a smaller event for the same day: Darklady’s ‘Detenion Hall’ Mini-Party.
When this information first got to me, I would have described it as her ‘downgrading the event from party to mini-party’. But that turned out to be almost stupidly incorrect. What instead happened (at least, from the point of view of my personal party experience) is that Darklady – being the fine social alchemist that she is – took all the potential of a big party, crammed it into a centrifuge, and somehow created a form of ‘party concentrate’.
I always have fun at these things, but it’s usually mostly voyeuristic fun, with maybe a little bit of ‘almost’ participation thrown in if that seemingly rare occasion presents itself. But this party . . . this party was something else entirely.
Welcome to Detention
We arrived early (JeannieJ had volunteered to provide music for the event, so he had to load songs and set up playlist and whatnot before the doors opened at 7:00).
It was interesting being down in what is normally the ‘Rubitorium’ space (where most of the actual sexual interaction at a ‘big’ Darklady party takes place) and seeing a wholly different layout. The entire party condensed to one level instead of it’s usual two. There were the usual couple of mattresses behind dark gauzy curtains for semi-privary, as well as one “Hey, Everybody! Watch Us Fuck!” mattress set up. But in place of all the other fuck-me beds were chairs and benches and so on.
A giant sheet hung down from the ceiling in place of a screen to catch images from the projector. Throughout the night it treated us to old black-and-white health-class sex education films, and porn. (Mostly this really weird thing involving Japanese women competing to see whose pussy was physically strongest – a set of physical challenges including spoon bending (NOT using the Uri Gellar method), pencils-breaking (not just A pencil, but a whole pussy-full of them), hauling a trailer filled with other woman, and so on. Other bizarre tasks included dart launching, and some kind of crazy vaginal fire-breathing. (And you thought vagina dentata was scary – “A fire breathing cunt burned down my house!”)
The aforementioned music was a mix of 70s, 80s, and 90s. There was a pot-luck buffet, and a cash bar. Table and chairs, with a stack of party games. All sorts of shindiggy goodness.
A lot of people were in costume. There were a lot of schoolgirl outfits (which got my approval). Some juvenal delinquents with the cigarette pack twisted up in the short t-shirt sleeve. A couple of people showed up in teacher-wear. There was even a nun.
Most of those that didn’t wear a costume matching the party’s theme dressed somewhere along the SEXY to FETISH line.
Oh, and the lovely blonde tending bar was topless.
“Are You Going to Continue to Talk in Class?”
Shortly after the party began, the spanking bench was brought out. A couple of BDSM players (man and woman, don’t know if they were a ‘couple’ or not) went over and set up an impressive array of implements of impact. [Sorry, couldn’t think of an ‘imp-‘ word to use in place of ‘array’. Alliteration FAIL.]
They laid out their tools and toys for easy reach, then laid out their victim on the bench. She was a black BBW, and she was seemed both ready for a spanking and still hesitant about the whole thing. She stripped down to her bra and panties, got on the bench, and then one of the spankers removed her panties, giving her a, “Wait—what?” moment. But she didn’t cry foul and didn’t call her safeword.
They started her out with the standard warm-ups – light tapping the prep the skin, and so on. And after a little bit of that, well, then it was game on. Paddles. Floggers. Canes. Was there a whip? I didn’t actually watch the entire performance, so I can’t attest to their full set of impact toys.
Periodically, the BDSM woman would get into the theme of the evening, and ask her spankee questions like, “Are you going to continue to talk in class?” To which the spankee would, of course, answer, “No!” (Well, usually “No!”. Sometimes it was “Maybe.” At least once it was “Yes.”)
After it was all over, the spankee took her no doubt very sore ass over to a couch to lie down, get a blanket draped over her, and recover.
In the information sent out prior to the party, one of the things mentioned was Strip Poker. This is another item on the big long list of things that I’ve always wanted to experience, but never have.
In addition to just wanting to play Strip Poker, I also have occasional exhibitionist tendencies that usually lose the battle to my body-esteem issues. It occurs to me that one of the very few ways I’m ever going to be naked in a room full of people is if I HAVE to be. For example, if the rules state that I have to remove my clothing for losing at Strip Poker.
So I promised myself that if the opportunity arose to join a game, I would.
At some point during the evening, while I was watching the hot redhead that I haven’t mentioned yet (Yeah, that’s linear continuity for you!), one of the schoolgirl-attired women walked by carrying her shirt. Someone nearby commented on her lovely bra-encased breasts, and she explained that the reason they were out was because she had just lost her shirt playing strip poker. Lost her shirt, then quit, not really wanting to lose anything else.
Ah ha! Strip poker! I vacated my chair and found the game, then grabbed an unoccupied chair and . . . set it off to the side, sat down, and watched. What a chicken.
The game was Texas Hold’em, and whoever had the lowest hand each round lost an article of clothing. There were three guys playing (not a huge draw for me), and the spankee who I’d already seen mostly naked earlier in the evening when she was bent over the spanking bench.
A couple of hands after I started watching, the dealer asked me if I wanted to play. So I gathered up my courage and moved my chair from the sidelines to the player’s side of the table.
I wasn’t playing to watching my fellow players strip. (Occasionally, women that I’d be interested in seeing wearing less clothing would wander over and watch, but none would ever sit down and play.) No, at this point, I was playing to lose. The exhibitionist desires thought they’d finally found a way to defeat the body-esteem issues.
The game ended as a result of all but one player losing ALL of their clothing. That one player – the last man standing, or ‘last man clothed’ – hadn’t had the worst hand in a round all game. He hadn’t taken off a single article of clothing. That last player was, of course, me.
What the fuck?
Hot Detention Hall Redhead
There’s a standard piece of sex furniture at Darklady events called a ‘monkey rocker’. It looks kind of like a mutant, mostly-headless rocking horse with a dildo poking up through its saddle.
To use the monkey rocker, you put a condom on the dildo (it is a shared toy, after all), lube it up if necessary, and then climb on top (making sure that you’re either properly partially naked, or at least have an appropriate orifice exposed to the rocker’s ‘business end’). The dildo then slides up inside you (I’m assuming it works equally well vaginally or anally). You grab hold of the handle where the head would be on a traditional rocking horse, and then begin to rock back and forth.
And what does the act of rocking do? It pushes and pulls the dildo up into and down out of you. The monkey rocker fucks you.
After the spanking, flogging, whipping, caning, et ceteraling was over, the spanking bench was moved out of the way, and the monkey rocker was brought out. And it wasn’t too long afterwards that this sexy plump little redhead walked over to it and prepped it for use. Then she climbed aboard and started a-rockin’. “This is one of the reasons I come to Darklady events,” she said to nobody in particular. “I can’t afford to buy one of these for myself.”
I watched this Hot Detention Hall Redhead (which is now officially her ‘not her real name’ name – and I’ll call her HDHR for short) fuck herself on the monkey rocker for awhile. I could have stayed there and watched her for as long as she wanted to ride, but . . .?
One of Darklady’s rules (and I’m paraphrasing here) is that respectful watching from a distance is fine. Creepy leering is not. And I haven’t yet figured out the distinction. I’m kinda creepy looking to begin with. Plus, with the ever-present dark glasses (thank you, extreme light sensitivity), it probably looks like I’m trying to look like I’m not trying to look. (Man, I want to have someone set the last half of that previous sentence to music.) Which is creepy in and of itself.
So I watched for awhile. But then I got up and wandered the perimeter of the party. When I got back to the monkey rocker, she was still riding it, but the guy that she’d come to the party with (husband, boyfriend, owner, slave, fuckbuddy, or whoever) had now joined the action. She was still straddling the monkey rocker, rocking away, but now he was behind her, fucking her as well. (Anally, I’m assuming, although I suppose it’s possible that he and the rocker were giving her a double vaginal penetration.)
I sat in a different place to watch this time, because somebody was sitting in the chair I had vacated. Sitting, creepily leering, and slowly jacking off. It didn’t take too long for her to look over at him and . . . invite him over. He traded his hand for her mouth, and now she had either phallus or phallic-shaped objects in all three holes.
I watched that for awhile before moving on to the Strip Poker table.
After becoming the big Strip Poker winner (?) I ended up standing outside the bathroom door, needing to pee. And guess who should step into place behind me? That’s right: HDHR and her partner. By this point, all she was wearing was her shoes and a pair of red stockings and garters.
While waiting for the bathroom to become available, I told her, “You are incredibly hot. I just thought you should know that.” She thanked me for the complement, and before further small talk could happen, the bathroom door opened. So, in I went.
After I was done, HDHR and I switched places, and I took up a position where I could see the bathroom door, but not so close that it would seem like I was waiting to ambush her. She left the bathroom, engaged in two bouts of conversation with other people, and then I made my clumsy awkward move.
“If I asked nicely, could I get permission to play with your nipples?” She thrust her breasts out at me, which I took as permission. As I started to take hold of them, she said that I’d need to be a little bit gentle – while she normally liked rough nipple play, they’d already had a lot of play that night, and were starting to get tender.
So, as I’m standing there lightly pinching and rolling the nipples of this mostly naked sexpot, there’s a thought bubbling up from the back of my brain. The question that I’ve wanted to ask every woman whose bare breasts I’ve ever played with at one of these events, but only ever think of after we’ve parted ways.
While still playing with her nipples (and now also moving my hands outward, squeezing her breasts), I look her in the eyes (again: very effective with the dark glasses) and ask, “Is there anything else I’m allowed to do?”
She asks me what I have in mind, and I suddenly realize that saying, “One or more of the following:” and then rattling off a long list of sexual activities probably won’t be the most endearing move. So I say, “I don’t know . . .” while my brain stumbles for a better response.
I’m about to tell her that she is incredibly sexy and I am woefully inexperienced, and that what I have in mind is pretty much anything she’s comfortable letting me try. But then before I can marry that phrase to the pause at the end of “I don’t know”, she tells me that she’s tired, and needs to eat and then rest for a little bit. But then maybe she’ll find me later on in the night and we can do something.
Of course, being told “not now, maybe later” is a familiar answer. It means, “Good Lord, no! I don’t want you touching my sex parts! You’re just lucky I’m far more well mannered to scream out what I’m thinking instead of giving a polite-but-nebulous answer.” So, I figured that was the end of it.
Later on, I see HDHR talking to JeannieJ for awhile. Then she disappears again. Eventually I start talking to JeannieJ about the inflatable dice game that was going on (I think that maybe I was in Detention for writing non-chronological event reports). While he’s telling me I need to go play the game, HDHR comes back over, leans over to him, and says something very quietly in his ear.
Then she leans in toward me and quietly says, “. . . and you can come along and do some touching if you want.” I follow this procession to the one exhibitionist mattress, where HDHR lays down on her back, and JeannieJ starts playing with her right breast. I lay on my side next to HDHR and start playing with her left. Still wondering just what the definition of ‘some touching’ all entails.
Playing with nipples, squeezing breasts, rubbing and stroking any and all of her exposed flesh (and stocking-encased flesh, for that matter). It’s very, very nice. I’m liking this a lot. JeannieJ is doing the same, and at one point his hand goes down between her legs, and she makes a noise of protest when he slips a finger up inside of her. So, the finger retreats, and he continues doing what he had been. Same thing I’ve been.
Then he starts sucking on her nipple. There’s a little while where he sucks on right nipple while I merely twiddle with her left. (“Some touching”.) So I ask, “Am I allowed to suck, or is it JUST touching?”
She tells me to suck on her nipple. I lick it a couple of times, then vacuum it into my mouth, which makes her gasp. I’ve got the nipple, areola, and some of the surrounding farmland in my mouth, and I’m alternately sucking it in and pushing it outward with my tongue.
The second time that JeannieJ’s hand starts to work between her legs, there’s no protest. And as the pleasure-noises HDHR was making increased, JeannieJ abandoned her breast and concentrated fully on what he was doing between her legs.
So for awhile, I was sucking on one breast, groping and fondling the other, then switching between the two (as best I could from my position on her left side). For awhile, anyway. We’d attracted the attention of another horny-looking guy, and when HDHR noticed that, she told him, “You can join in, if you want,” which sent him immediately mouth-first to her right breast.
JeannieJ used his fingers to bring her to orgasm a couple of times, based on the screaming, thrashing, writhing, and, “Oh, God, Yes, Yes, Yes!”-ing she did. Then came the point at which she let out a low moan and said, “I need a cock in my cunt . . . and one in my mouth.”
She rolled over onto her knees and elbows, and my brain is now going a mile-a-minute. I’ve got a huge stomach and a small penis. I love the size and shape of HDHR’s ass, but it’s not conducive to someone with my body type fucking her from behind. So that’s out. But her mouth . . . I could find my way in there. Could this be it? Could this finally be my first real blowjob?
And as I’m about to tell my body-esteem issues to fuck off and strip from the waist down, the other guy turns to JeannieJ and asks, “You want the front or the back?”, stripping down himself. It’s amazing how I can weigh 450 lbs and sometimes be practically invisible.
It was quickly agreed that JeannieJ would start out as the cock she needed in her cunt, while the other guy would put his in her mouth. JeannieJ went to put on a condom (which he had to have me open for him, as his hands were too slippery from having been up inside of her), and the other guy positioned himself in front of her. Before she started sucking on him, HDHR told me that I could still keep my hands on her, which I did. (Yes, it felt like the consolation prize. But the consolation prize was still a naked redhead, so . . . )
JeannieJ fucked HDHR while she sucked the other guy’s cock. Then, after awhile, they switched – the other guy fucking, and JeannieJ getting sucked. It didn’t take very long for the other guy to fill his condom and pull out. I’d been stroking her bare back and the side of her ass. I thought about asking permission to finger her, but her mouth was full, and I figured that if she didn’t want me there, she’d let me know.
So I slid a finger inside of her, and let it explore. In and out. Around the walls. With a second finger, I was able to do more, and she started making interesting noises around JeannieJ’s cock, still in her mouth. Better noises came when I had three fingers working in her. I had a fourth finger on that hand, and I sent it in search of her clitoris. I found it fairly easily and stroked it a few times, and that’s when she broke her oral rhythm on JeannieJ – to tell me that the clit was too sensitive, and to leave it alone. So, while she took JeannieJ’s cock back in her mouth, I tried to figure out where to put that fourth finger. Guess where I picked? Right alongside the other three.
At this point, all I wanted to do was to grab the bottle of lube and continue pushing my hand inward. Add my thumb into the mix, then slide my hand into her up to the wrist (and maybe beyond). Finally fulfill my longheld fisting fantasy. But I didn’t know if she’d be into that. Didn’t want to stop and ask permission. Didn’t want to be exiled from the play area (so to speak). So I just continued the four-digit fingering that I’d been doing.
Eventually, JeannieJ came and when that happened, I pulled my fingers out of her. She got up into a kneeling position, and looked like she was done. The other guy (still watching the scene) tossed me a towel so I could wipe the combination of natural and artificial lubricants off of my hand.
After wiping anything resembling thick goo off of my hand, I went to the bathroom to actually wash. When I came back, the other guy had apparently recharged, and was double teaming HDHR along with the guy she came to the party with.
The Inflatable Dice
There were a pair of inflatable dice at the party. Naughty dice. The kind where one die lists an action, the other die lists a body part. So you can roll results like ‘Kiss Lips’ or ‘Tickle Ass’.
The first dice (which would quickly become known as the ‘noun’ die) had the following written on its faces: Ears, Lips, Neck, Chest, Ass, and Your Choice. The ‘verb’ die’s six faces read: Rub, Massage, Lick, Kiss, Tickle, and Surprise. Each dice was inflated to about a foot in all its little cube-like dimensions.
Starting early on during the party, you could almost always find a couple of people playing around with them. But at some point, ‘a couple’ morphed into a group, and there was a rough circle of chairs and couches holding a dozen (give or take) players. Whoever got to the dice first rolled them, performed the action on whoever rolled the dice previously. Then that person became the recipient of the action that came up on the next dice roll, and so on.
I’d been thinking about joining the game earlier. Straddling the wallflower/active-participant-in-life barrier. That’s when HDHR came over and offered me tactile access to her gorgeous frame, which seemed like the better deal. But once that whole encounter was over with, it was to the dice game I returned. Only not just as a lookie-loo this time. I sat down in a currently unoccupied chair in the circle, and made a grab for the dice as soon as I could.
I honestly can’t remember what my first roll was, or who I had to deliver the action to. (It was probably either rub or massage lips – I know that I racked up an inordinate amount of those rolls throughout the evening.) But whatever it was, I took the roll, did the thing, and then sat down.
Then Darklady took up the dice, and rolled ‘massage ears’. She walked over to me, and massaged my ears. With her breasts. (Hey, it didn’t say WHAT to massage ears with, after all.) That’s probably why I can’t remember my first roll. Darklady’s breasts erased my short-term memory before it hit long-term storage. She rubbed her tits on the side of my head, and then leaned in and thanked me for coming to her party. Yeah, uh, it’s great to be here. No, really – GREAT TO BE HERE!
[Let me say right upfront that I had fun with that dice game. There were some women there whose nouns I was very eager to verb. But in all honesty, I’d have been perfectly content at that point to send all of the other players home, and just continue the game with Darklady and myself. Why? I don’t know. Maybe because I have this giant fucking crush on Darklady, and I was in a situation where it was possible that ‘naughty touching’ might ensue? Perhaps.]
I tried not to hog the dice. Moreso – and this was the difficult one – I tried not to lunge for the dice immediately after Darklady took a turn so that I could verb some of her delicious looking nouns.
There was one woman who was very ticklish, and every time I rolled after her, the verb was ‘tickle’. And whatever that virus was, it spread, because soon everyone was rolling ‘tickle’ for her.
I rolled ‘tickle your choice’ for another very lovely lady, and when she asked me what I wanted, I told her that ideally, she’d need to take off her shoe. She said, “I can do that, it just takes a few minutes.” (Very high heel, lots of straps and buckles.) So she removed her shoe, and I tickled her stocking-clad foot. And, of course, complimented her on having very nice toes.
I had my someone surprise my ass with a one strike, double handed spanking. I had someone surprise my chest with a purpling of my nurples.
I rolled ‘massage chest’ after one of Darklady’s rolls once, and since it did say massage chest and not massage bra . . . she removed said support garment for the duration of my massage. And as I’m standing there pretending that groping and fondling qualifies as a massage, something occurs to me. “Wait a minute,” I exclaim as I slowly begin sinking to my knees. “It didn’t say WHAT to massage your chest with!” And as Darklady agrees that, “No, it didn’t” I begin using my mouth.
So there I am, on my knees, sucking on Darklady’s breasts, thinking to myself, “This is the best Darklady party EVER.”
Afterwards, we both sit down again, and not too many turns afterwards, someone rolls ‘surprise your choice’. Which makes my brain light up. I respectfully wait for someone else to take one more turn verbing Darklady’s nouns. But after that, the next time she throws the dice, I snag them before she even carries out their commands.
Of course, once she’s done that, she excuses herself to the restroom, so I have to wait. When she finally gets back and sits down, I stand up. I make a big production of moving the dice around, but then deliberately place them on the ground so that they read ‘surprise’ and ‘your choice’. Then I look around at the other players, and ask, “That’s a legitimate roll, right? That counts?” I figure the worst that will happen is that I’ll be made to reroll, and still get to do something to/with Darklady.
But no demand for a reroll comes. A couple of people laugh, but everyone seems okay with it. So I walk up to Darklady, who asks, “Which of my ‘nouns’ are you going to ‘verb’?” And I just sadly shake my head at her illiteracy, and point at the dice which I inform her clearly read, ‘suck toes’.
Again, I’m half-expecting her to veto this and make me choose again. Or roll again. She momentarily gives me a look like she’s going to veto it. But then she starts removing her shoe, and asks, “One foot or both?”
So now I’m sitting cross-legged on the floor with both of Darklady’s fishnet-covered feet at my disposal. (I was really hoping to get bare toes, but the stockings, it appeared, were staying on.) Since it’s kind of difficult to suck on individual toes through stockings, I started off by putting all five of the toes on her right foot in my mouth. Running my tongue over and underneath the group of them. Licking up and down them. And so on. Switching back and forth from foot to foot.
She’d occasionally lurch forward. Shudder. Make a noise that I couldn’t interpret as being good or bad. Despite having the opportunity to suck on Darklady’s toes, I wasn’t going to force her to endure this if she wasn’t into it, so I asked, “Is this okay?”
Turns out, the noise was a good noise. The lurching and shuddering were very good lurching and shuddering.
Whenever it wasn’t her turn in the game, she’d been in conversation with the people around her, which is the only reason why I didn’t suggest that the two of us leave the game and move to a couch or mattress where I could do a more proper job. (Maybe even a job where I could play my fingers up between her legs while her toes were in my mouth.) But every time her turn was over, she returned to her conversation, and however good it looked like getting her toes sucked was making her feel, I DID NOT want to be told ‘No, thank you’ by Darklady.
Later on in the game, she rolled the dice following one of my rolls, and the dice came up ‘kiss chest’. Again pointing out that it read chest and not shirt, she had me go topless (apparently proving that her requests are at least as powerful as strip poker), and then proceeded to lick, suck, kiss, and bite my chest for what seemed like several minutes. Yes, please.
“Blog, Baby, Blog!”
The party, originally scheduled to end at midnight, finally started to break up around 1:45 or so. JeannieJ went and retrieved his music, I went to the buffet table and reclaimed my sister’s cake pan, and then we prepared to depart.
Before we disappeared, Darklady reappeared (she’d disappeared about twenty minutes earlier – poof!) She thanked us for coming, I thanked her for having us there, told her that I’d had an incredible time, and so on.
And then she said it. She grabbed me by that arm, and exclaimed, “Blog, baby, blog!”
Now, she was visibly ‘a little drunk’ at this point, but since she went on to praise my writing, telling me that I was intelligent and articulate, I’m choosing to believe that it was the Dark One talking, and not the bottle.
In fact, at that moment I thought that my brain was going to cum in it’s pants. (Yes, my brain wears pants. You think I want it running around inside my skull bare-assed naked? Think again.)
I’m a big lonely, horny, fetishy pervert, and I got to suck on (among other things) her toes. But having her praise my writing? That’s tied for 1st place.
The rest of the party wasn’t so bad, either . . .
I CURRENTLY HAVE (YET ANOTHER) LEG INFECTION. ONCE IT GOES AWAY, EXTRA MATERIAL FROM THE FIRST DRAFT (“AND YOU THOUGHT THIS POST WAS LONG”) ALONG WITH OTHER ADDENDUMS WILL BE AVAILABLE FOR PERUSAL AT THE OVERFLOW BLOG HERE.