Back in the Big Apple. Things only seem to happen in one of two speeds: fast or light speed. Missed a whole bunch of yoga—and Todd. Enrique comes by at least once a day to try to engage in chit-chat. Jemma usually shoes him away. I know I have this thing with Todd, but it doesn’t mean I don’t like seeing Enrique. And even his attempts at small talk by fishing for something to do with the business is cute. But nothing good can come of that.

Speaking of Jemma, I get the distinct impression that she might be a bit resentful of me for going to Miami. I no doubt bumped her from a few days in the sun. It also didn’t help with her or Enrique when the pictures of me leaked out in the office. OK, Jemma got over it half a day and a mocha frappe later. It seemed to encourage Enrique to come by more. Jemma seems to be losing her “Not Boyfriend Material” repelling power. He stops by and lingers, interrupting my work. Jemma just smiles and continues doing her work. Yup, definitely upset with me.

My dresses arrived at the apartment. I’ve been wearing them with different shoes and accessories. So far no one has noticed that I’m wearing essentially the same thing every day. OK, a couple of people—my co-work, boss and Nico—have commented on being very monochromatic. I threw in some colourful accessories to they and throw them off my trail.

The dresses aren’t the only new clothes I got. I got a new cool running suit because I found out Todd was into Crossfit. I don’t have time (or money) for Crossfit now, but instead of doing yoga over extended lunches, we run and do some exercises in half an hour. Then I shower and change and am back to work. Note: I should get a few more dresses since I burn through two a day. The money I save on buying panties now can go to buying more dresses. Of course that isn’t the only thing I’ve been doing with Todd this week.

He was busy the first couple of nights I got back. It gave me a chance to buy some cheap lingerie. I should buy some of those $3 Victoria’s Secrets panties then put my name on them, with my phone number and email address—might be cheaper than business cards! And then I wouldn’t feel so bad about losing them at cute guy’s places. I’m turning into a tramp. Yay, me! Actually I found this neat store—on the web—and bought a complete three-piece set (bra, panties and garter belt) for $55. But we did hook up during lunch to start running.

Three and a half days after I got back from Miami, but who’s counting, I finally got to see him ‘after dark’. Another different little restaurant. How many of these crazy out-of-the-way places does he know? He asked my about Miami over drinks as we waited for a table. I have to confess, I used my privilege to enter the Black Hole of Couture and find a nice simple dress…by Valentino. It was black and had a tight bodice, good thing I got a bandeau bra, and a ruffled skirt which came down just above me knee—or just below the top of my stockings. Jemma helped me pump up my hair. All in all, Todd seemed to approve of it. And by approve, I mean kept on staring. Just before we were seated he got a call. From the look on his face it looked important. He said he had to take it and would meet me at the table. I was a little worried, though a second Cosmo calmed me down—only a little. I knew it was just work, but the look on his face. And then five minutes later he joined me with a smile on his face. I was so relieved.

I showed him the ‘money shot’ picture from Miami. He kept looking at it on my phone. I’d say it was a hit. It seemed doing the photo shoot was worth it for this attention alone. I told him I had a surprise to show him back at his place—a second dessert. That certainly had him intrigued. My ploy was to make the dinner last as long as possible. This mostly was done by a bottle of wine. He asked me numerous times about the surprise. I guess I technically had two…

After he paid in cash we walked back to his place. I asked what he did other than work, Crossfit and taking girls to dinner. He cheekily responded, “Dream of sleeping.” I bit my lip. Tonight I intended to give him something else to dream about. He asked me about work and I kind of complained about all the work I was doing, but still getting the same wage as I started. Todd was kind of taken aback when I told him the things I was doing. He said that was more like what a junior manager should be doing, not a personal secretary. He asked me to refresh him about my academic background. He dropped platitudes on me and told me I should get a raise or get a new job. I think I might have complained a bit much, you know how you do when you’re venting.

The walk was short and talk of boring daylight stuff came to and end as we entered his place. I noted I really saw his neighbours. Todd said he had noted that too. He asked his real estate agent. The agent had said that a lot of the units in the building were owned by companies for the use of executives or guests when in town. A few were owned by people who lived here during the week and went home during the weekends. My thoughts temporary slipped to the weekend.

I was brought back to planet Todd with a final cocktail and his enquiring about a ‘present’. In my borrowed Louis Vuitton bag I had a small envelope. It was full of 5x7s of the photo shoot from Miami. I handed it to him nervously. Everyone had complimented me on it at  work—but that was work. I wanted someone who wasn’t kissing up to my boss to tell me I was pretty, no, sexy! He took his time studying each of the photos. My nervousness turned to confidence. This time it wasn’t the vodka, cranberry juice and contra; it was that he was really into sexy pictures of me! I coyly asked him which were his favourites. He smartly said all of them, though he seemed to have put a few in a separate pile. Tonight, I was going to do it right.

I sat next to him as he cycled through the pictures one last time. I rhetorically asked him if he liked them. Rhetorically, because I could see the bulge in his pants. I just wanted to get this show on the road, but wasn’t sure how. Some how grabbing the pictures out of his hand and dragging him up the stairs, while seemingly practical did not seem the appropriate thing to do. He was cycling through the smaller pile—the more provocative photos. He asked if he could keep them. I of course said yes. And then I got an idea.

It wasn’t the Cosmos or wine this time. Added by a $5000 dress an equally expensive bag and knowing he really liked the pictures of me, I asked him to take some new one—just for him. That apparently was a very good suggestion. I had to go touch up my hair and makeup as he found a camera. I told myself to breathe. I mean I had done this with a complete stranger and no experience for little more than a favour to my bosses. Now I had a very low pressure photo shoot with a guy I actually wanted to se me in my underwear. I channeled my inner model—or call girl—and met him back in the living room.

He had his smart phone. He said he couldn’t find his point and shoot. I was a bit nervous, no self-conscious as he started just taking pictures. There was no way these pictures would be anything like those ones, but that was OK. These ones were for him and him alone. I found myself posing after a little while. And then a bit later he started to pose me. That was more exciting. In hindsight it was the beginning of foreplay. He had me pose in all these vintage pin-up poses. He was mocking fashion photographers pretending to be some German expressionist—though I don’t think Todd really realized that. At some point I think the top of my very expensive designer dress ‘accidentally’ unzipped itself.

The digital shutter on his phone sounded like a machine gun as I peeled out of my $10000 Italian dress to uncover $65 lingerie. I didn’t even make it sexy, I just basically got out of it. Not that I would have known how to do that. I only once saw a stripper because of a mixed up with my friend Amber. She said we were going to se a stripper—and I forgot she was a lesbian. We both were to blame for that. I buried my face in my beer and never looked up. But Todd was certainly looking up. Actually, I was. Up to his loft.

I pulled him up he stairs. Right behind me and not looking at his phone screen he for the first time saw the back of my panties were just strings. A week ago, I wouldn’t have been comfortable with any of this. And near the top of the landing I felt his hand slap my bare bottom. It made me jump. I wasn’t expecting it—from him. I remember thinking, that it hadn’t been so bad. In his bedroom, I asked him where he wanted me. The bed of course.

I jumped on the bed and crawled around like a cat. There was that machine gun shutter. I didn’t want to ruin it for him—me—that the lighting was terrible up here—for taking pictures. As fun as it was pretending to be a sexy model, I wanted something a bit more physical. Tonight was the night. Then he asked me to take off my bra because he ‘wanted to see my big tits’. Normally the vulgar words and that tone would have been a real turn-off, but not that night. I didn’t really think anything through, I just un did my bra and dropped it on his nightstand. I of course kept my breasts covered with my forearm. This frustrated and aroused my voyeuristic date.

He tried to convince me to do some classic pin-up poses on the bed, but I was reluctant—at first. I got an agreement that the pictures wouldn’t be shown to anyone and that after this he’d put the camera down. And with the verbal agreement of a horny photographer I shyly removed my arm and revealed my breasts with a look somewhere between “Tada” and “WTF”. The shutter sounded like a movie camera as the cinematographer wasn’t even looking at the hundreds of shots he was taking. He was in stead staring at me—mouth open. O know my boobs are good, but that was a huge ego boost. It also makes the end of the photo shoot as Todd literally dropped the camera on the floor and rushed to the bed.

We started kissing. I felt kind of like some high-class call girl practically naked on his bed while he was pretty much fully clothed. It wasn’t a bad feeling, just a new one. I felt his hands touch my skin. I smelled him as he kissed my neck. Tonight. In spite of him being in awe of my girls, his hands roamed further south. I remembered him after coming up the stairs with his eyes as wide as a cartoon character. He firmly grabbed my ass and then asked me if I trusted him. I said yes, but nothing came out. He took my head bob for the correct answer. And the next thing I knew, I was across his lap.

Todd raised his arm up and brought it down with a thunderous sound. It sounded much worse than it felt. It was also ambiguous feeling for me. I once got a spanking on Catholic school. It had been very embarrassing, it also hurt. I was taken out of that school and put into another without corporal punishment. That first, maybe second spank brought me back to Eighth grade and an undealt with tarball of emotions. At first it had been very humiliating. Bent over some old guy’s desk and he hit me with a paddle. A nun lifted my school skirt and I think I was more embarrassed by having my panties exposed than the actual spanking. It scarred me, in an unexpected way. Slowly that humiliating experience found it’s way into my subconscious. It leaked into my fantasy world. The old priest got younger and younger until he was whatever movie star I was infatuated with at the time. The nun faded away—mostly. By the fifth smack my bottom was warm and it was beginning to hurt, but…

By lucky number seven a familiar aura replaced the priest in the back of my mind. By the tenth spank I was wiggling on his lap, he had to hold me down. He didn’t stop and I didn’t ask him too. My mind faded in and out of the present sensation and an imaginary fantasy until the two coexisted with each slap of my bottom. He stopped and rubbed my tender cheeks. It hurt, but it felt good at the same time. I looked up at him. I said a single word, drunk on the sensation, “More”. He grinned and continued. I squirmed more, but this time for the paradoxically feelings of pain and pleasure wrapped in a Swiss roll> I didn’t know when to stop him, but luckily he did.

He rubbed my now burning posterior and told me how good I was as he pulled down what passed for my panties. I was very cognizant of the liberty he took rubbing is fingers far below my tushy. A week ago I would have been upset that he had touched me there, not I was upset he didn’t continue. I was unsure of what to do next. I was also kind of emotionally spent from my first adult erotic spanking. My head tried to remember what happened in that like one porn I had accidentally/on-purpose watched. Thankfully one of us had a plan.

Todd grabbed me and tossed by up onto the bed. He was still fully clothed and I was only left in my stocking, suspender and heels. The asymmetry excited me when I realized it. Todd climbed on top of me. I was very happy about that. Not that I wanted it to end, but rather I had been waiting for this since talking to him in Miami. He grabbed both my breasts and pushed them together. He motorboated them. I remembered that term from a country song my mother had listened to a couple of years ago. But in other news, he motorboated me! It was the second kinkiest thing I had done in my life, tonight.

But then came the part I had been aching for. NO, not the kissing, which was very great. It was the intermeshing of our bodies. I didn’t care that my sore bum was being driven into the satin sheets. Satin can feel a lot more scratchy after a thorough spanking. He kissed and groped me and I felt him between—in me. The night had gone nothing like I had planned in my head, but it had still been awesome. I wrapped my arms—and legs—around Todd as he rabbitted in and out of me I was so close to having an orgasm when I heard him ask me something. I instinctively said yes and then realized shortly afterward one of us was having an orgasm. He rolled over after he was done. I was still horny, but didn’t really know what the protocol was on something like that. He said it was a great and I smiled and nodded. And then the near silence of the space was destroyed by tiny snores.

It had been a perfect night right up until only one of us had a happy ending. I was conflicted. I was also in a place that was not mine at a late hour. I needed to get back home and shower and get my request 3.5 hours sleep before my next 12 hour work day. I looked around for my clothes. Found my bra just where I left it. Searched for my panties. Even began to wonder if I had actually worn any. Saw his phone on the dresser and decided to exercise my editorial rights. I grabbed it and then realized it wasn’t the phone he had been using to take pictures of me. I know because I kind of saw his passcode to get into the phone. It was then I realized I was holding a Samsung and I was pretty sure Todd had used an iPhone the whole time I had known him.

I put the phone down wondering how much I really had to drink when making a last futile attempt to find my backless panties I literally kicked another phone. I picked it up and tapped in the code I had seen him use. There was his life unlocked, for me to see. But I resisted the urge to snoop on my new…obsession. I went directly to Photos and was a bit worried that I would find something I shouldn’t or didn’t want to know. Strangely the only photos on the phone were the ones he took tonight. I immediately deleted any unflattering pictures of me, so basically all of them. I kid. I deleted half of them. Ironically the best pictures were upstairs in the loft with slightly better lighting. I Airdropped a couple of nice, but very topless pictures onto my phone before deleting all the topless or ass shots. I then permanently deleted them and left him with the least sucktacular and PG-13 nudity photos. Still a nice moment of the evening. And if he wanted to get some more photos like the ones I deleted, he’d have to invite me over agin. 😉

I grabbed my borrowed dress and handbag and made a hasty retreat back to my place. Another imperfect evening, but at least the progress was in the right direction. There was no lights on except for the bathroom light when I got home. I had a quick shower and resisted the temptation of giving myself the ending I deserved. Mostly out of the fear that I’d slip in the tub and die or worse be left a quadriplegic all over an orgasm. More likely it was my fear of waking my roommate under such embarrassing circumstances.

The next day I returned the borrowed items without anyone realizing they were gone. At my desk was a cheque for the modelling I had done. It was good, not great; but it was like free money. Jemma and I decided what I should do with it. I wondered if I should text Todd, or wait from him to text me for once. Jemma told me she was aware that I not only did all the hard business work, but that was better at it than she was. She wouldn’t let me console her. She just wanted my to know she knew in the middle of her mango smoothie. And while down in the lobby, I got a call. Thinking it was someone else, I cheerfully answered only to find out it was someone offering me a new job.

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