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Grabbed my bag of grass, bottle of poppers, stuffed that also in the duffle. I pack a double-ended dildo i have along with two large bottles of lube. I fill my plastic anal syringe with some J-Lube and squeeze into my sissy hole two nice fillings of the thick slippery goo. I cap it off with a long, soft and flexible butt plug to keep all the goo inside and to loosen up my hole cause I knew I was gonna need it. I put on the tightest underwear I have to resist the plug from naturally popping out, get dressed and out the door I went with my duffle of naughties.The train ride was only 20 mins but it seemed forever, especially with my sissy hole full of lube and the butt plug happily keeping everything in. I was thinking, 'what if the cops came on board and wanted to peek in my bag or frisk me?' The thought of it was making me hard I had to try real hard not to cum in my underwear. Every time I moved, every jolt and turn the train would make, the plug would rub my prostate to the point of. I’d been aware that John seemed to have an interest in me. He was always talking to me about my progress on the job and seemed to linger in discussions on business topics longer than necessary as if to just “be with me” longer, but I never seemed to get a spark going long enough to start a fire. Occasionally, John would compliment me on my dress or my hair, but it never seemed flirty or sexual, just polite banter. This guy is really slow, I always thought to myself. So when John asked Debbie out to a private lunch without any of the rest of us being invited I got a bit jealous, maybe even downcast. Debbie took him to her favorite local spot which I knew was a quiet, dark, sort of romantic restaurant. Things didn’t seem to be going in my direction. Debbie outranked me at the company and it was beginning to look like she might get the first “raise” out of John.When they returned from lunch Debbie came over to my desk and I could tell she really wanted to talk. She and John had.
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