My Bosses Halloween Party

Its Halloween time! My life has become predictable at best. But this time of year I flashback to all the mischief I used to get into, and I remember those times fondly. Maybe longingly if I'm honest. How old I am now doesn't matter. I just thought I would share a story from my youth. My first Halloween party as an adult.

I used to work at a theatre. Every Halloween my friends and bosses and coworkers all would dress up and have a big party before going out to the clubs, drinking literally all night, and I never could go until I turned 18. I would hear stories of how this girl hooked up with this guy or this guy woke up naked in the yard. I needed that kind of fun in my sheltered life. I needed to let my wild side out. My FOMO, which wasn't a term back that I knew then but one that applies, was intense. Finally, I turned 18 September 1st, and I was excited. Beyond excited. October was knocking on the door.

My friends Chelsea and Danielle were older than me, and had gone at least once each to these unofficial work parties already. There were like thirty of us, so I can't get into everyone's names, or even pretend I could remember them all. But the three managers that hosted and encouraged the club scene on us impressionable were Jenny, David, and Thomas. Jenny was beautiful, always bright eyes and positive the youngest of the managers. David was handsome and super gay. Like, you didn't meet him and not know he was gay, but he was very handsome and charismatic. And Thomas was... Amazing. He was in his late twenties, pretty much 30, country as hell, but he looked like a male model, way hotter than any guy I had ever really flirted with. And he was... huge. That was an open secret at work. Open amongst us girls and David anyway. Even soft the thing dented his slacks when he walked in a way that was hypnotizing. Dickmotizing.

The problem was Thomas was also married. I knew his wife. She came in often with their child, Anthony, visiting Thomas at work or to see a movie. I got along with her, sort of. But she always came off as a little colder to me than with the other women Thomas worked with. I never was sure if it was because I was a dark skin Hispanic.. or if it was just that Thomas was a tit guy, and my boobs even in my teen years outdid her cheap store-bought ones, or if someone had maybe told her I can be kind of a slutty size queen... Or if she could just sense the things I was willing to do with her husband. I don't know. I did know he was way out of my league. Or so I thought.

So Halloween comes, and boss Jenny formally invited me and a bunch of girls to come pregame at her house before her party. We could come straight after work, as early as six-thirty to drink and change and do makeup and hair and everything. The men, needing less time, were allowed to come after 9:00ish. Then the party would officially start around 10:00/10:30. We would leave for the club around midnight or one.

I carpooled with Chelsea and Danielle, since I had never been to Jenny's before. Danielle was already somewhat dressed up in a cheerleader outfit, since she had had the day off, but Chelsea and I were in our work clothes. Maybe that's an unimportant detail? Yeah that's unimportant. Ok so we get there, and drinks are had immediately! And I took to vodka like a fish to water. That was my first time drinking and I didn't know my limits, but I fell for vodka that night and we started a romance that survived for years to come.

Jenny was a stylist when she wasn't working at the theatre, and she took me under her wing that night. She made my hair look amazing, and she did my make up. By the time the guys showed up I still didn't have my costume on, but I was already drunk. My costume wasn't much of one as far as originality goes, slutty maid, (a Latina sub in a French maid outfit) but I picked it with Thomas in mind. I had heels, fishnets, which I heard he liked once, a short skirt that almost failed to cover my ass, and my tits were, essentially, uncovered. The top I put on last. It was designed for someone busty, but with smaller boobs, that was obvious. Way too much of my bra was visible, more than I expected. My glitter covered tits looked like two disco balls about to bust free. I was having a mini panic attack about it. I wanted to look like a hot snack, not an open whore. Being drunk off my ass for the first time didn't help either.

Jenny, David, and Danielle were all crowded in the upstairs bathroom trying to calm me down. David had his hands literally on my boobs, standing behind me, telling me how gorgeous they were, bouncing them in his hands. Jenny was urgently telling me not to tear up and ruin my awesome make up. Danielle was holding my hand and trying to calm me down. "He is going to think I look like a whore!" I said to Danielle, intentionally not using Thomas' name but saying more than I should have.

Danielle had been drinking too though, and it wasn't her embarrassing secret crush.

"Thomas is such a tit guy oh my god he is not going to hate what he sees."

Jenny smiled genuinely, "Ohhh someone has a crush on our handsome Thomas?"

David laughed, still bouncing my boobs with both hands, "Girl big dick Thomas would love these more than I do."

"My ears are burning," Thomas said, poking his head in from the hallway, leaning against the frame, holding a beer, looking smug. His costume was... a t-shirt, jeans, and fangs. That was it. But he made it look good.

I died. Any fear of crying disappeared as my whole body just.. stopped. Shock set in. Danielle froze too. Jenny beamed complimenting his timing. David looked Thomas in the eyes seriously, bouncing my boobs as high as he could, out of rhythm with each other. "Will you tell her these boobs are amazing?"

Thomas laughed and took a casual drink. "Not in front of so many witnesses." He smiled this crazy charming smile. Danielle turned and made eye contact with me. Her eyes were screaming in excitement and encouragement. Mine were still in full panic.

Jenny took the lead and shoved David and Danielle out the door towards then passed Thomas as she spoke. "Will you cheer her up? She isn't used to drinking and is having a bit of a panic about how she looks."

Thomas stepped aside to let them pass. "I guess... as long as you three don't tell my wife downstairs that im locked in a bathroom with a lusty maid." His smile, it was magic. Like, it made his joke into a reasonable request and implied he wouldn't do anything untoward at the same time. There was a reason I was crushing so hard. A million reasons, actually.

So then Thomas, my boss, my crush, stepped into the bathroom, and shut the door behind him. He stepped behind me, reached up and swept my long hair off my shoulders, exposing my neck. He leaned down, being over six feet, and rested his head on my shoulder, and openly stared at my chest in the bathroom mirror. "They really are breathtaking," he whispered.

I was frozen. I couldn't move. I couldn't reply. "I mean," he continued, "you are more beautiful tonight than ever before, and the maid look is extremely sexy with your tan and all, but they really are spectacular. They steal the show. My wife is going to hate you even more. I'm going to be staring all night. May I?" he asked.

I mean, I assumed he meant "may I stare all night," and my heart went from frozen to thundering as I nodded yes. I told myself he was probably just being nice, even as I nodded. But apparently, he meant "may I take over where David left off" because his hands came up and fully groped my chest.

David had had his hands on them, but he wasn't groping, he wasn't really sexual about it, just bouncing them for fun, seeing if they would hoist out of the maid top. Thomas made it beyond sexual. He squeezed them. He bounced them. He pinched them. Thorough the bra, but in the area my nipples were for sure. My eyes were huge. My heart thundered. And I just stood there while this hunk of a married man's hands had their way with me. He straightened up, standing up straight, pulling me back against his chest as his hands devoured my chest, explored me, and made me soaked like you wouldn't believe.

"I don't even care if I get fired for this these tits are worth it." He said, voice totally casual, conversational, and he pinched down on the nips as hard as he could manage through my Victoria Secret bra.

I laid my head against him, eyes rolling back in my head, knees giving out. "I won't tell anyone," I mumbled blissfully.

Then he smiled that damn smile. "Feel better?" he asked casually. Sooo casually.

"Much," I purred drunkenly.

"Good," he said. And literally kissed me on the forehead, like I was just a daughter or something. His hands went from pawing to straitening my shirt so it didn't look ruffled far, far too soon. I whimpered. He kissed my cheek. "You should consider losing the bra," he added, conversationally. "The pads are just thick enough to make the top seem even more strained than it should be, and you're young enough not to need the support."

"Ok," I said, dazed, thinking there was no chance in hell I would risk wearing this tight costume without a bra around everyone I know. And he had switched modes so quickly I was entirely lost. Had I done something wrong? Did he just grope me to make me feel better and stop my panic? My intoxicated mind couldn't keep up.

He put his hands on my shoulders, squeezing firmly, and added something sensual in to his voice as he met my eyes in the bathroom mirror. "Promise me?" He looked... sincere. I nodded, committing. "Good!" He continued. "Just make sure the sexy maid shirt doesn't burst open with my wife around." And he laughed, and again I couldn't tell if he was being serious or kidding. I mean, of course he was kidding. But how much was he kidding? I was so confused but I was happy. Vibing. Loving the mood.

"Actually, since you won't have the bra, Im going to push my luck." my handsome employer stepped back from behind me and dropped to a knee, lifted my skirt from the back, at eye level with my ass. I tried to half turn to see what he was doing, but his hands went to my hips and held me facing away. His hands slid over my ass, examining it up close. They roamed up and down my legs and my cheap costume fishnets as if they had every right to do so. His hands went to my black and purple thong ( the matching set really was the most expensive thing I was wearing) and he tugged them down, down my legs, over my heeled boots.

I stepped out of them for him. My mind was screaming, "This skirt is way to short to go without panties!" but I stepped out of them, and he brought them to his nose and as he stood and stepped to the door, he took a whiff before putting them in his pocket. "I'm keeping these. Oh and one more thing." He stepped back into me and, reaching down under the front of my skirt, he very intentionally ran a finger along my wet slit, longways, back and forth, until he brought his finger up to his lips and tasted me. "Exquisite" he said, then he left the bathroom and back down the stairs.

Me? I just stood there in shock. I may or may not had a mini orgasm, standing there alone processing what was happening. His dick had felt so big and hard against my ass. His hands had roamed my ass. His hands had roamed my tits. He had almost finger fucked me. All to make me feel better? Holy shit maybe?

I was still standing there when Danielle and Chelsea came up looking for me, desperate for the gossip. I admitted he had said he likes my boobs, but nothing else since his wife was just downstairs. The girls squealed, and their excitement soaked into me. OMG that really just happened! I told them he recommended I lose the bra and they agreed I absolutely had to if big dick boss hot Thomas said it was a good idea. It was soon in Chelsea's purse, and I had to admit that the maid costume felt less like it was going to explode, and I could pull it up a little further around my chest.

So we went downstairs, and the party was amazing. The music, the weed, the drinks, the food, the flirting. I tried not to overdue it with my drinking, but it would be a few years still before I learned where my limits were or how to pace myself.

Things went on swimmingly, until my next crisis, which sent me running from the fire pit back into Jenny's house, upstairs to my safe place bathroom. As I shot up the stairs I heard Chelsea say "Hey Thomas! Can you go and check on her? I don't know what's wrong."

I stood there, door cracked, staring at myself in the mirror trying to get myself calm. I was high, drunk, and I had a pot brownie hitting me hard Would he follow me? It had been hours since we were up here last. Then Thomas was there, bathroom door shut, and he was brushing my hair from my eyes. "I need my panties back." I told him, so grateful he was there to save the day.

He laughed shaking his head, as if I had said the most ridiculous thing in the world. "Of course you do, no chance," he said. Adding "Why?" a few seconds later as an afterthought.

"Omg I was down by the fire pit in the backyard and I realized everyone across the fire was looking at my bare fucking pussy every time I moved around." I said, probably too loud.

His laugh was booming, full bodied, and he shook his head, "You know every one of them wanted to bury their face in it."

"Yeah well I wouldn't let just anyone."

"So Im special then?" he asked with a smirk, one that happened to annoy me at that moment.

"What makes you think I would let you?"

"Lets find out." He said, not missing a beat.

What? My brain asked, and again I froze up like a dear in headlights as her turned me to face the mirror. Again, my hands were on the sink and again he knelt behind me, pulling my waist back. Hiking my skirt up. Arching my back and spreading my legs so that my pussy and ass had to both be visible from his low angle.

Then he licked up my thigh, my mounds, my slit. I was in shock, on fire, and drenched all at once. My insanely hot married boss buried his face in my bare ass, his nose against my asshole, his tongue really penetrating me, unlike how his finger had only teased me before. My fluffy skirt was up over his head. "God damn you you're delicious." He said as he tongue fucked me from behind. I gripped the sink to keep from collapsing into the mirror.

Then like before he changed modes, hopped up and said "Yeah no I am absolutely keeping these until you earn them back," he padded his pocket, "and I can't be gone long, wife knows I'm in here with you." He went to the door and opened it, checking outside, the he leant back in and pseudo whispered "Listen, my wife isn't going to the club with us. She never does. The plan is I will drive her home midnightish then before I meet everyone downtown."

"Ok," I said, knees still too weak to support myself. Head swimming. I can't change modes quickly when I'm sober, and I was far from that. I could still feel his face pressed into my ass as I looked at it speaking to me, trying to follow its words.

"After I leave here and everyone is heading downtown, tell them you are too sick to join them yet. Too drunk or fucked up. Trust me its believable. Say whatever you have to say to be left alone in this house, a friend or relative is coming to get you, you'll join later if you feel up for it, whatever. And text me when they're gone so I can come back." Holy shit was this happening? I didn't even see when he left the room. But I was alone in the bathroom again for some time before I realized I was, then I pulled my maid's skirt as low as it would go, grabbed my silly duster, and went back downstairs.

Everyone believed I was too drunk to go to the club. Apparently, it would have been a big deal convincing the bouncer to let me in if I'm 18 and look drunk? Jenny was too sweet, offering to stay with me again and again while I waited for my friend, but I assured her I would be okay and would be miserable if I thought I was a burden to the night. I felt so bad lying to her.

Then I was alone in her house. I texted Thomas that they all left for the club. He replied to leave the maid outfit on. Like... obviously right? Then I waited. And waited. Then I must have fallen asleep. The doorbell woke me up. I ran to the door eagerly, jerking it open. And there was Thomas.

He had changed into a suit, like he would wear to work, but the shirt was vibrant red, his tie, jacket, and slacks were black as his shoes. "I thought you would appreciate at least a little bit more effort than my wife got." I smiled ear to ear. I was blushing.

He drank me in as I drank him in. "You were always pretty but Jenny made you look like a fucking goddess I swear."

"I felt bad lying to her." Inebriation causing me to be more honest than I needed to be.

Thomas pulled out his phone and showed me a text. He scrolled up a bit and handed me the phone.

Thomas: "Jesus did you see those tits?"

Jenny: "Ha, like I could miss them. Did you see that ass?"

Thomas: "Tasted it."

Jenny: "Liar! Kinky liar."

As I read the short exchange, Thomas helped himself to my neck and ear with his lips, and my heart woke up, beating swiftly.

Thomas: "Hey im leaving for a bit to take the misses home. Let me know when you all head downtown."

Jenny: "Leaving. Can you swing by my place before you come to the club and check on Rachel? Im sure it would mean a lot to her. We left her there alone. 😉"

Thomas: "Lmao are you trying to get me fired?"

Jenny: "Just don't get her pregnant dork. Have fun xoxo."

"Woah," I said, as Thomas trailed down my neck and started kissing my chest, his hands eagerly coming up to cup my breasts towards his lips, "she wants us to?"

"She knows Ive been frustrated and that you are absolutely my type."

He took me by the hand and pulled me down the hall to the couch. He sat, and pulling me by the hand then thighs sat me straddling him on his lap. Then he pulled me by the back of the neck for a kiss. And fuck what a kiss. It was like... sex. If you could put all the sensuality and intimacy of sex into a kiss, it was this kiss.

And it lasted a while. His hands roaming from my ass to my tits, pulling my maid's top down for better access. I had been grinding my hips that whole time, his massive cock throbbing beneath me, my bare pussy against his slacks, and I had been grinding on it for who knows how long. Eagerly. Wantonly.

The kiss broke, and he reached between us, eager to get his own cock out, and I was eager to see it. I scooted back, and I had clearly soaked his pants with my need. Those were stains, and the slacks expensive looking. To keep his mind off of it from realizing I ruined them, I lunged forward, wrapping his head in my tits. Soon, beneath me, that big cock was free from its confines, his hands flew up to my chest, tugging my top out of the way and taking my breasts between his lips. His cock, unrestrained, felt around my thigh, way high on my thigh, moving up and down in a caress already under my floofy maid skirt. His mouth was on my tits. I was in heaven.

I felt its length, confirmed it was circumcised, as I had suspected. I slid it against my slit, eager to feel it pierce me and teasing myself with the idea. I nearly fell back off of him I was so drunk with pleasure, not to mention just drunk.

This was happening.

His hands returned to his cock, eager to slide it in me, one hand gripping my hip to guide me down onto it, but I was far from ready to move on to that yet. I mean, I was ready, but I wanted more first. I slipped of his lap and to the floor in a swift motion. I tried to cover the stain with my hands wrapped around its base, but I was distracted.

For a long while this would become my favorite cock. It was gorgeous. Love at first sight. I should have started with a kiss, maybe, a romantic slow building one, but I was hungry for this for so long. I licked it, from base to tip and dove onto it orally, brushing past my uvula and trying to throat it fully on my first go.