Amber left early in the week. I hope things get back to normal. Too many late night—drinking. I went shopping with her a couple of times. She helped me work on my 333 wardrobe. OK, she helped me reset my 333 wardrobe since I ended up ordering some different dresses online. She tried to convince me to free up some wardrobe spaces by sleeping naked, but we all aren’t shameless supermodels. I opted for a couple of sleep tees. I know I’ll miss her very soon, but right now I’m kind of glad to have my space and sleep back—what little I have of either.

I’ve been calling and messaging with Todd most of the week, even before Amber left. At some point it came up one or both of us were disappointed with our last ‘date’. It was kind of a relief to admit that because afterwards we started chatting about how to fix it. He asked if I liked the spanking. At the time I was mixed, but now I admit I kind of crave it. But that alone didn’t really seem as a viable strategy alone.

Then one time searching for some sexy underwear I came across a sexy maid outfit. I sent him the pic and he turned a thumbs up emoji. That lead to a discussion on role-playing, I wasn’t really into it at first. The only problem was I had a backlog of work and a short time to make up for it. I had no time for lunches or dates, it would have to wait. But the idea grew in my head throughout the week.

And this week was spent in meetings with my bosses and other managers. The rest of my time was spent with Enrique. Life might have been easier if I hadn’t seen that sweet side of him in London. It certainly would have been easier without the sexy time dream(s). And now I was spending a lot of time at work with him—in close proximity.

I was really coming to appreciate his creativity. We’d run into an obstacle and then I’d run the numbers. We repeated this lots of times until we found out something else had changed then start all over again. We were working through lunch the first couple of days. By the third he insisted we go out to clear our heads. So long as I was an arm’s length away from him, there was no way my head was going to be clear.

But on a rare warm day we sat out on a patio and ate and drank. The hostess mistook us as a couple which Enrique had no trouble teasing me for the rest of the afternoon. At first I was a bit embarrassed, but then realized it was kind of a compliment that she thought I was worthy of the super hot guy in front of me. It was really just flirting masquerading as juvenile humour. I actually enjoyed, no actually encouraged his teasing the rest of the day. I convinced myself that it helped dissipated the tension—of work.

And so the rest of my week was spent so close to him. I took short breaks to respond to Todd, but spent lunches with Enrique. I felt bad about the amount of time I was spending at work until Alicia reminded me that Todd had done the same thing to me, a couple of times. It didn’t help that I actually enjoyed my lunches with Enrique as much as I had with Todd. It didn’t help that Todd was sexting me as I was looking at Enrique.

I was in a really weird head space which revolved around perpetually working so as to try to forget about the two men in my life, one in close proximity and the other in close propinquity to me. It was not working out well for me. It’s not that I didn’t care or want Todd, but Enrique was just there and I wanted to reach out and touch him. On the flip side there was no sense that Enrique wanted anything to do with me except flirt. He knew I had a boyfriend, but if I was to believe office gossip that wouldn’t have stopped him if he wanted me.  I cleared off Thursday for my boyfriend.

We met for lunch. He commented on the dress that Amber had helped me order online. It was very business sexy with the bra and stockings she had also helped me pick up. I immediately wanted to cut work and go home with him. Instead we talked face to face for the first time in like forever. Near the end of lunch I realized I still didn’t have the agreed upon costume.

After lunch we kissed and I started searching on my phone where I could get such an outfit in short notice. So instead of rushing back to work to deal with Enrique and our European prospect, I instead made a bee line to the closest sex shop.

It was eye-opening to say the least. It was less a kid in a candy store and more like Alice in Wonderland. Although I saw the costumes near the rear, I couldn’t help to stop and look and wonder what half of the stuff was for. OK, I knew what a lot of it was for, but I wondered how—no, who would use it. I mean other than a vibrator or the clearly novelty stuff. Thank God the clerk—some tattooed girl who looked like she came to work on a Harley—left me alone. She watched me, but not like I was going to shoplift anything. No, she watched wondering when I was going to pick up something, something I’d never picked up before.

That something was, what according to the Internet is called a flogger. I knew what it must be used for, I don’t lead that sheltered a life. I just didn’t know why anyone would use it in this day and age. OK, maybe I did, but as someone who had just come to terms with enjoying having my bum spanked, I…

I stroked it a couple of time before a text from Enrique asking where I was brought me back to Earth. I raced over to the costumes. They varied in quality and taste. The first maid ‘costume’ I saw was little more than a sheer bodysuit with cheap hat, apron and ruffled cuffs. Next! The one thing I couldn’t complain about was lack of selection though. I mean the choices were subtle but there was a choice to be maid<sic>.

My mind raced at the pros and cons of each of them. I wanted front coverage. I wasn’t expecting a great underwire bra, but a little support would be nice. The ones that bothered to cover the top all had lots of cleavage, that wasn’t really a choice. And the skirt was really about how short you wanted to go.  Hint of panties was probably the most conservative skirt in this place. Merde! I needed panties. I got tired of losing them in handsome men’s apartments that I’ve been going without them. Another text from Enrique, asking if I’m OK.

I stepped up shopping. Covered my boobs and had a reasonable preteens of being a French maid. Had “panties” to match the outfit. Sold! As I made my way to the counter and the nonjudgmental judging clerk something caught my eye, hand cuffs. I didn’t realize they were more for show than something you’d actually use in the bedroom, but I grabbed them—I don’t know why. Maybe I did.

Then at the counter as I avoided eye contact with the tough girl behind the counter, she commented “lucky guy”? I failed to realize it was a question rather than a polite attempt at light banter. I agreed. It was true though, Todd was a lucky guy. And while avoiding her gaze I saw it just as she asked if that was all. I asked her what is that? It’s a †!††¥ flogger she responded like it was a totally normal thing. It was small and had latex stands and…I took it. I saw the smile of the cute girl’s face as I handed her my card.

I texted Enrique after I left the sex shop. I felt like everyone knew what I was carrying on my way back to the office. I lived in fear that when I finished walking across the marble floor and rode the elevator up that someone would ask me, “what’s in the bag”, before I could make it to my office. I made it all the way there without any incident only to open the door and find Enrique sitting in my chair. Out! I yelled at him, more embarrassed than angry. He peeked into the bag before I could stop him.

His response was a smirk and the comment of “Sexy maid”? “You don’t like it, you more a Playboy bunny type?” I couldn’t cover my mouth fast enough. It was my boss’ words coming out of my mouth. But it wasn’t. I had been rubbing shoulder with Nico and Christine a lot of late. They took no guff and just said what they thought. I had just done the same. My handsome co-worker has tried to wind me up and I gave it back to him. It felt…awesome!

Other than the fact he just nodded as if agreeing to my clearly sarcastic response. And if my intent had been to shut him down, I failed miserably. He didn’t say a single thing all afternoon, he didn’t have to. His eyes just had to look at me and the sides of his mouth turned up just slightly. I wondered how much of it was more teasing and how much as innuendo. Maybe the later was in my head, I mean we only had sex once and he didn’t realize it was me till later. Still I wondered if he was thinking of me in that sexy maid costume as much as I was thinking of being in it for him.

The end of the day couldn’t come fast enough. I raced out of the office after making sure to meet Todd at his place. We skipped dinner and went straight to dessert. He greeting me and we kissed and I felt his hands appreciating my body. He asked if I wanted anything. I said a stiff drink. I mean sure I wanted to do this for, no with him, but I wasn’t used to doing anything like this. I mean I totally froze in drama class. The best role-playing I ever did was a single game of Dungeons & Dragons with some World of Warcraft friends.

Strange that had I come over just to have sex, I’d have been OK. I mean it was just sex, but now with costumes. Erotic cosplay. That’s what I started to tell myself, it didn’t make anything better. The cocktail did, a bit. I wasn’t sure why I was so anxious. In reality it was no different than the last time I had been there to have sex—a few weeks ago. It was now just with a Halloween costume and a bit of a set up to pretend it just wasn’t my boyfriend’s apartment. Just pretend you are you, and he is him. It helped me more than the drink.

Todd told me to change and come up when I was ready. I remember thinking at the time he might die of old age if that was the case. Thinking back now it was probably the whole maid thing that was a bit of a dampener. Who thinks a domestic servant is sexy? Oh ya, boys! More than the costume, it felt a bit naughty getting naked and putting on the maid costume, alone in his living room. I don’t know why, but it just seemed indecent changing by the coffee table.

It was all one, but I’m glad I only had to walk up a flight of stairs. The top was flimsy and held up by elastic. The apron covered neither cleavage nor even reached the bottom of the short skirt. And a good thing it came with it’s own set of panties since you know the dress didn’t cover everything it should have. Not that the sheer panties covered anything really. The hat was kind of cute, but wouldn’t last first contact. I had picked up a cheap pair of stay-up stockings, which I had rightly guessed were not part of the costume, but sadly one of the best things on the costume photo.

I stopped to look at myself in the mirror. I thought it ranked somewhere between a Halloween and stripper costume. Though never having seen a stripper perform, I’m not sure why I thought their costumes would be better. It’s probably the idea of what motivated the person to don the costume. All said though, I looked good. Room for improvement, but not a bad start.

I went up the stairs like every other time wondering if he was sitting on the bed or I don’t know how he’d be waiting for me. What I didn’t expect was the place to be messy, like burglarized messy. At the time I didn’t clue in to the big picture, but instead thought, “wow, I’ve never seen his place like this”. He was standing and took steps towards me.

This is when I kind of clued in to what was really going on. He started yelling at me about how I was incompetent and such a lousy maid. I have to admit, at this point I was kind of glad it wa role-playing as a maid. I certainly don’t like being yelled at or being told I did a bad job. On the other hand, I was a pretty bad maid in my own apartment. It wasn’t exactly an Oscar worthy performance, but it was convincing enough.

And maybe it tapped into a small part of me because I immediately began apologizing and saying I’d make it right. I also was drawing on some of my own theatre classes and desperately trying to go method. And the key motivation of the maid that was not me was to keep her job no matter what. And the no matter what meant sex.

I pleaded with him to not be fired and I’d make it up and I’d do anything to keep my job. It was kind of fun when I was doing it, but a bit weird being removed from the moment. I never want to be in a position like the poor girl I was playing. Still, keeping your job by sleeping with your very handsome boss isn’t too hard to do—when you’re already sleeping with him.

He threatened to dock my pay, which I said I need to pay for my elderly parent. Not sure where that came from, my parents are not elderly nor infirm. I should call them tomorrow. I again pleaded that I needed the money and would do anything.

Luckily my employer acted on my pleas. He grabbed me by my hair—half-yeowtch, half-purr— and hauled me across his lap. I admit with the costume it was a bit different than the last time. Of course this time I had agreed to it, looked forward to it before coming over. I felt the short skirt come up, the panties did nothing to stop light or air. He started lecturing about consequences and good work habits. Maybe one day that will help get me off, but for now it was just the spanking itself. Warm at first then turning to a sting and finally to something that could be perceived as pleasure. Just as the smacks could have got routine He pulled down my panties, and then things got magical.

He let them hang around my thighs as he really got into tanning my behind. This was as the stinging turned to something else. The something else was being powered by monstrous spanks that echoed in the loft. That helped get me off more than the degrading banter. I focussed on the smacks, anticipating the next one. It got hard to tell how much pleasure was from the mental and how much was from the physical. Either way it was enough to make my orgasm. I may have hid it from him or it might have got lost in the consistent spankings.

Then it stopped, and I was left anticipating the next, last smack. I was sad he had stopped until he stood up and started to undo his pants. I knew what he was going to say before he said it. My nipples poked through the thin fabric as he told me that, the spanking, was for the messy room. He popped out his erection and said that this would be to keep my job. On my knees I guess I should have pleaded not to have to do it, but I was finally getting into everything, but mostly I was really horny.

So without any hesitation I grabbed him. At this point, being in a maid outfit with my panties around my knees and kneeling in front of my boyfriend, I finally felt something  more than just him in my mouth. Maybe because it wasn’t really my idea or possibly because it takes a while to get into it, I just didn’t feel that much into it. And as I gave my employer a blow job to keep my job, my head started to race through all the possibilities. Now my brain and my ¢∫!† were talking the same language.

My pondering of possibilities was interrupted my a slap to my face. It took me back. I wasn’t expecting anything like it. He called me a dirty whore, and that also was unexpected and had unexpected results. Unlike his first spanking, I didn’t intellectualize it. I put it in the same place as the maid outfit and the rest of the role-play. The second slap felt like the recent spankings. Apparently the oral sex was over.

He grabbed me and dragged me up over his bed. I saw two things on the nightstand as I struggled against him. They were my things. I let him cuff me to his head-board. Strangely I had zero reservations about that. Confession: It wasn’t the first time I had been tied up during sex. He pulled down the frilly elasticized top to suck on my breasts. The handcuffs made it even better. Closing my eyes that much more.

There was a short pause as his mouth left my chest and I felt his hand squeeze my breast. Then I flinched as the tiny tail on my novelty flogger lived up to its name. I was getting a lot more than I had signed up for that night. Even more interesting was how much I enjoyed it.

I’m thankful he didn’t spend too much time flogging my chest. As sensitive and intriguing as it was I needed a bit more time to acquire that particular flavour. I felt his mouth engulf my inflamed breast. His hand sat on my thigh and his fingers threatened to invade me. I wasn’t squirming from pain, but from expectancy.

I hadn’t expected the †!††¥ flogger on my ₽µ$$¥. Oh my God! Even the few half-hearted falls drove me incredibly crazy. But he abandoned that prematurely. I guess he was also going crazy. His banter was less in character and more a visual description of his actions, not that I didn’t enjoy him ⨍µ¢₭ing me hard. In fact I was pretty vocal about telling him how much I wanted him. I might be blushing as I write this now, but it was true at the time and true now.

He told me to come for him, about ten minutes too late. He was in his own world, not aware of how much I was selling him what he wanted to hear—not that I wasn’t having an orgasm. He pulled out and shot crossing me leaving little gooey trails up to my chin. Then my screams were real.

While I was still in what remained of my costume he had dropped his role. He lay down beside me and kissed me. Todd was 180 degrees from his character telling me how awesome I was while groping my sticky breast. I could have done that all night, but my body had other ideas. Luckily Todd wasn’t taken aback when I said I needed to attend to some less glamorous things. He actually laughed and then suggested we take a shower—together.

Naked in the shower he looked at my wrists. There was red marks around them from the thin metal cuffs. They didn’t hurt as much as they looked incriminating. He kissed them better as the water fell down on us. We ended up mutually masturbating each other in the shower as we kissed. He was very gentle then on my reddened body. When I couldn’t take anymore I whispered to him to take me to bed.

Our drying of each other was hampered by desire and this time I lead him upstairs, both of us naked. I took the handcuffs and gave them to him while I lay on the bed. I put my hands around the rails on his headboard. I knew I had improper equipment, but at that moment I had improper desires. Todd wasted no time restraining me to his bed. I made him pry my legs apart. He took me a second time that night. He failed to finished, which I didn’t blame him after everything else. I on the other hand was a virtual fountain. The role-play may not have been my thing, but the bondage certainly had been. Thank God he undid the cuffs before we fell asleep in each other’s arms.

He woke me as he was mostly dressed. I was still lying naked in bed. I looked at the watch on his wrist and scrambled to find my clothes—that were downstairs. I had lots o time to get to work, but no time to go home. I remember fixing my hair and make up before we walked out thinking, you wear the same thing every day, no one will notice you are wearing exactly the same thing today as you did yesterday.

After a kiss in the hallway we parted down on the street. I picked up something to eat with my coffee. The barista noticed the red marks on my wrists. I said, “rough night”. She winked back at me. I was becoming an unapologetic woman of pleasure.

I ran into Jemma in the elevator going up to the office. She looked at me with a critical eye then told me that if I was going o wear the same dress each day to at least change my accessories daily. This upset me and also gave me hope for the day. She did comment that I seemed to be using a different deodorant. That was true, it was Todd’s. But she never connected the dots and I thought I was home-free.

That was until later when I had a meeting with Enrique. We were getting close to a second attempt at our European prospect. He noted the same dress, the same accessories and a different scent. His conclusion was different from my former work mate. He never said anything, but his wink pierced my heart.

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