So, I’m still cuffed, but I managed to stand up and sit on a stool, my erection mostly subsided but after all of today's erotic activity, sporting a bad case of “blue balls”. After what certainly felt like a long time, Gina emerged in her new costume. (looking like this from the front - https://m.media-amazon.com/images/I/71nAoxZP7DL._AC_SY550_.jpg and this from the back https://m.media-amazon.com/images/I/61L8gCUlinL._AC_SY550_.jpg ) Her costume highlighted her lovely bottom and the double-breasted topcoat had all it could do to hold in her big tits, started to feel a tightness in my loins again looking at her! I got a decidedly naughty secretary vibe, but after the last aggressive encounter, I realized she might be in naughty BOSS mode. I was left wondering what was in store as she approached across the room, doing a teasing turn so I could view the back of her outfit. She jingled the handcuff keys in her hand and wondered aloud standing directly in front of me, “Should I un-cuff you…. Mummm I don’t know. It might depend on whether you think this costume makes me your boss or secretary.”

Frustration of all kinds motivating me, I immediately forcefully said, “Secretary get over here and un-cuff me now!” Trying to sound as commanding as I could muster given the situation.

“My, so polite boy is also capable of switching to command mode, how fun!”, grinning over her black glasses before moving behind my stool and unlocking the cuffs, laying them on the table with the keys.

“Is there anything my boss needs help with? Your needs are my needs. I’m very good at aural dictation. I’m told I have no problem catching every bit.” She suggestively offered, tracing her index finger down my chest, and licking her lips. She then backed away out of my reach and asked, “So what does this outfit evoke for you Art? Wanting to take control and command your secretary to do your bidding? Is the boss a bit frustrated?”

“Yes, I think my secretary needs to pull the last file from the bottom drawer, and then bend over my desk to hand it to me. But oops she dropped it, and it went under my desk, so she will have to get on her knees under there to retrieve it. While she is under there, there is something else very pressing for her to do.”

“ Mumm all very vivid ideas, I can use that. So poor frustrated boss, does he need something like this?

Gina dropped to her knees and unbuckled my jeans and quickly yanked both them and my drawers down, freeing my quite frustrated hard member. She began licking around the tip, then took it deep in her mouth sucking very hard as she squeezed my sensitive and aching balls, right up near the pain point. Releasing my cock from her mouth, she worked my wet cock up and down with one hand and with the other slapped my ass hard saying, “Boss shouldn’t work so hard, he gets too frustrated.” And slapped and stroked some more before diving my cock deep in the mouth sucking hungrily and squeezing my balls.” Being quite revved up from all the previous sexual stimulation and not having cum yet, I know I couldn’t take much more before exploding. Her mouth and tongue worked my cock like an artist, and she would periodically suck almost painfully hard while squeezing my balls to the brink. That was when she teased my asshole with a wet finger and when she could feel I was about to cum shoved it in my ass, I bucked and moaned as I came all over her face and tits, while she milked my cock and fingered my ass. My god what an amazing orgasm!

She got up and said with a mischievous smile, “Is the boss feeling better, more relieved, I hope? He has more work to do after all.” She tossed me a dish towel and said, “Why don’t you wipe down Mr. Happy and I’ll be back in a minute.” And turned and walked to the bedroom, closing the door behind her.

I did as she suggested then pulled up my pants. Wow, Gina was certainly a red-hot woman. I was afraid that after all the buildup of the outfits and servicing her, talk about “edging”… I might be sent home with blue balls, but she sure gave me an epic orgasm. I couldn’t even imagine what might come next. As I was reflecting on all this, the door opened and she came in dressed in a black shoulder strap casual dress. It looked to be made of T-shirt-type material that clung to her figure, her nipples distractingly evident, carrying a cardboard box.

“Art, you have some homework for our next get-together the day after tomorrow”, she began “I need you to try these products, they’re for men so I can do it, and I need to know if they work as described, and your review of them. I need you to take at least basic notes on each one that I can use later for reviews and updating the packaging copy.”

She placed the box down on the counter and I began looking at the contents. The first box was a set of anal plugs of increasing sizes. Holding the box, I looked over at her, with a sort of “You’re kidding right?” expression on my face.

She smiled and said, “Art, don’t even bother with the virginal expression of perplexed innocence, I quite doubt your bottom is virginal by any stretch.” laughing, pleased with herself about the stretch reference. I perused the contents more finding three masturbators, making different claims to stimulate pleasure on the packaging, a few tubes of lube, and two devices that were designed for stimulating the prostate. So she was correct that these were almost all designed for male stimulation, aside from the plugs, so I commented,” Don’t all the rest of the devices sufficiently cover the male-exclusive territory, is it really necessary for me to review the plugs too?”

“Art, as you know male anatomy is different, and so the plugs affect males differently than females. So yes they remain part of the assignment. Anyway, off with you. You’ve been a good worker so far, so keep up the standards, and don’t disappoint me on your homework, there’s no telling what the consequences of poor performance might be. I’m off to a nice soak in the tub, and another glass of wine, so let yourself out and be back at 3:00pm sharp Monday. OK?” And grabbing the wine bottle and glass from the counter, she gave me a quick peck on the cheek and turned towards the bedroom waving goodbye.

Somewhat reluctantly, I picked up the box of “toys” and headed off, perplexed, stimulated, and ambivalent about my homework assignment.