I Become My Coworker’s Secretary Part 2


Sometimes in life timing just doesn’t work out and this is one of those times. This story could have happened, but it’s a fantasy because we both had already left the company. But in this story, I’m going to pretend that we still worked together and that these things really did happen. When in reality we just chatted about them and flirted and teased each other with “what if” scenarios. This is why I say it could have actually happened if life’s timing wasn’t so bad. I was on a website called “doublelist,” which is like craigslist personals after craigslist did away with those ads. I had posted a couple pictures and took an ad out looking for someone local. I’d leave the ad up and wait for responses and would take the ad down if I got too many or if I found a match that I wanted to continue talking with.Like usual I got a few responses, many of which were one-liners and no picture. I usually just ignore and delete these unless they are really close by and at minimum included a picture. I opened a couple that did have pictures attached and was shocked to see one of my ex-coworkers had responded.For the story, we will call him Keith. Keith is a good amount older than I am. I was in my mid-twenties and he was in his early fifties more around my dad’s age than mine.I knew it was him because he very boldly responded with a face picture of him out at some bar and his email name included his first name in it. I was mortified at the thought I had been caught like this. No one knows my secret that I like to wear women’s clothes and act like a woman for a guy’s pleasure, except for the lucky few that have received that pleasure.I had a bit of a panic attack at the thought of my secret being out at work, but then I realized the ad I posted only had pictures of me from the neck down. Realizing this my anxiety calmed down and I read his response.He was actually responding to the ad because he was interested. Not because he recognized me. He had no clue it was me in the pictures as far as I could tell. I started to debate with myself on responding back.Do I just chat and flirt and relish in the fantasy without telling him I know him? Do I tell him I work with him? Will it scare him off and make him feel the same dread I felt just now if I do tell him we work together? I could always keep myself anonymous and just chat and it would be my secret. But that wouldn’t be fair to string him along with no chance of ever meeting.The idea of chatting with someone I knew personally made me very flustered. It was exciting but made me very worried. Then I thought, what if I told him we worked together and he would be excited about it too? What if we could flirt at work and give each other those subtle suggestions or jokes or winks. It was so hot and naughty to think about. How hot it would be to flirt all day at work and then go get dressed and please him after or even during work!The thought of wearing panties to work and purposefully showing him what I had on under my work clothes for him. I had always fantasized about being a secretary and doing some duties to help my boss, or getting caught wearing some panties by a coworker or boss and getting blackmailed, or any of the other typical scenarios. I relished the thought of wearing leggings/fishnets and skirts and playing and dressing for those roles. It really turned me on, so I decided to risk it and respond.His initial response was actually pretty short so luckily he included a picture otherwise I would have just ignored it. So my first response back was just a message asking what he liked and what he was into. Asking if he was more dominant and if he liked role play, I also asked if he could send a picture of his cock. I just had to ask because I really wanted to know what he was working with.Along with my questions I also included more about me and what I was looking for. Which was someone close by that I could talk to and develop a trust with. Someone who was more on the dominant side, either a pure top or mostly a top, or someone who was “straight” and wanted to explore with a girly counterpart. Pretty much I wanted to take on the role of a girl and be used for their pleasure only. I had no interest Side escort Bayan in topping them, but was open to receiving oral as part of the foreplay before I took on my role completely to make them finish. I get off on making others get off. That’s what I like and want.Keith responded within the hour, kind of a typical slow email response, which I get because people are busy and want to be discreet and not have their phones blow up with notifications that might cause suspicion. I know this cause that’s how I feel about giving out a more direct line of contact.He answered my questions saying that he loved how I felt about my role. He said he was bisexual and had a thing for gurls like me, that he had some experiences already with gurls but that it had been a few years since the last one because he had moved to this area. He was looking for someone to be a regular thing with if we both clicked. Again he was a bit short with his response not quite answering or responding to all of my questions or info I gave him and he sadly didn’t send the cock picture like I had requested.But still, this response had me excited. It gave me more confidence that he was actually seeking a girl like me and not just leading me on for kicks cause he recognized me. We talked back and forth a couple more times before I mustered up the courage to admit to him that I actually knew him in real life. My actual response back to his latest email was:“I hope this doesn’t weird you out, but I actually know you. We work together and it really turned me on thinking about what if you knew about me. I’m not trying to out anyone and I want to be discreet and I’m hoping you will be the same way. I’m not sure if you already recognized me somehow in my pictures and I kind of secretly wish you did and didn’t at the same time. But these pictures are 100% me and I’m not catfishing or anything weird. I hope this doesn’t scare you away, and hope that it’s more of a turn-on for you.”I also included some more pictures in this response. This time including my face even though I was dressed and was wearing a wig I figured he could still recognize me. Some of the pictures I sent were the ones I posted here on Lush. I sent these to him to promote trust and hopefully not scare him away with what he had just read. I was hoping he would share in my desire to continue talking and maybe even bring a flirty dynamic to work or even just keep it outside of work.I swear I refreshed my inbox every minute for what felt like forever, waiting on a response. God, I hoped that didn’t freak him out and scare him off, or worse, give him more ammo to drag my name through the dirt at work. I finally got a reply maybe fifteen minutes later with:“Well, that was unexpected. Thanks for telling me but I don’t really recognize you from your pics.”I don’t know if he was just being nice or just trying to ease my mind with the thought of still being anonymous. But I was flattered that he thought I looked that much different as a gurl. The email continued with:“It is a turn-on for me. You are gorgeous! I love the pics and I’d love to meet you in person. Maybe we could meet for a drink in plain clothes so I can see who you are and you can be more comfortable.”Oh, the sweet relief while reading this. My anxiety went down a lot after and now I was turning a bit giddy at thoughts of what’s to come. I was glad he wanted to meet and I preferred to meet not dressed because I hadn’t actually gone out in public around other people like that.We continued to talk back and forth a few times and set up a place and time to meet in public at a bar for what was going to be some much-needed drinks. This all luckily happened on a late Friday evening and we set up to meet the following night at a local bar at the port.I was so excited and nervous. I knew we were just meeting to talk and for him to see me as who I normally am. But I still wanted to be prepared for anything potentially after. So after fantasizing and jerking myself off into a coma at the thoughts of dressing up for Keith I fell asleep to continue my adventure the next day.The next day I tried my best not to jerk off Escort manavgat about the coming evening because I didn’t want to get that hit of dopamine that might cause me to feel satisfied with what’s occurred so far. For fear of second-guessing meeting up and chickening out.I decided to wait and distract myself most of the day until the early evening when I would start my routine of preparation. I swear I didn’t eat all day except maybe a couple of light snacks because I was so excited.Once about six PM rolled around I jumped in the shower and made sure to use all my girly soaps: shea cocoa butter and vanilla-scented shampoos, body washes, and lotions. I shaved my entire body smooth using the lotion as a shaving gel to avoid razor burns and bumps.I liked doing this because it made me smell so girly and it felt intoxicating to feel myself be so smooth along with those smells filling the air. I even hooked up an attachment I have for my shower head. It’s literally just a long hose and a valve to control the strength and I made sure to flush myself out so I was nice and clean inside and out., just in case anything would happen tonight. I also love doing this because it gives me a super full feeling, comparable to being filled with cock and taking the biggest load of cum possible before it fills you and comes rushing out because there is no more room.After I made sure I was nice and cleaned out and cleared of everything, I took my favorite silicone-based lube and a small syringe and gave myself some artificial wetness. I also love the way this feels because it makes things so slippery and feels absolutely amazing like I had taken a load of cum and was trying to hold it in. While walking around it would make me feel wet.My routine had me feeling more excited and confident about meeting Keith which is what I was hoping for. It was getting close to eight PM by the time I had finished and picked out what I was going to wear. We had planned to meet at nine PM at the upstairs bar.For my girly outfit, I chose to wear a lacey bright red thong along with some thigh-high black fishnet stockings. I would have worn the matching bra underneath my actual clothes but it was a little too warm to layer a lot to hide it. So I included that along with my wig and makeup and a couple of outfits in my to-go bag that I would keep in the car.I then grabbed my favorite plug, a stainless one with a smaller neck and a black jeweled base, and put a squirt of lube on it rubbing it all around and slowly worked it into my ass. I threw the lube into my bag and then slid my panties up over my legs and onto my hips, followed by bunching up my stockings and rolling them onto my feet and up my legs.Looking in the mirror I checked to make sure that my stockings were aligned evenly from front to back around my thighs, adjusting the sticky backing they use to stay up as needed to even them out. I put on a pair of dressier jeans to cover up my fishnet-clad legs and a nicer shirt that I made sure would be long enough to keep my thong from peeking out in case we sat at the bar.At this point, I started to get anxious again and took a couple of pre-game shots of tequila to save some money and loosen myself up before going. Even though the lube in my ass already had me feeling plenty loose.I put my shoes on then grabbed my bag and left for the bar. In my excitement, I showed up there a few minutes early. We had exchanged personal phone numbers last night and I told him to text me when he was inside. Apparently, he had shown up a little early as well because I already had a text waiting for me saying he was upstairs at the bar.He was also asking me what I wanted to drink. So I told him to order me a shot of Cuervo and a tequila sunrise. I nervously hit send letting him know I was there. I left my car and while walking up to the restaurant’s bar I could feel my fishnets rubbing against my jeans. The feel of my jeans brushing against my smooth legs and ass along with the freeing feeling of wearing a thong in jeans was blissful. My jeans were a little loose on my hips so I could feel my thong poking out as my jeans would slide down on my alanya escort hips and a breeze would blow under my shirt and across my lower back.I went upstairs to the bar, nervous that someone would walk behind me and see my thong sticking out if my shirt blew open just right. This helped distract me for a second before I realized I was at the top step and Keith and I were looking dead at each other from across the room. I’m sure he was patiently staring at the entrance, waiting for me or maybe wondering just who would walk up that he would recognize from work.He immediately smiled and raised his arm up to do a slight wave and grab my attention. This kind of made me second guess his response last night saying he didn’t recognize who I was from the face pictures I sent. I walked over nervously smiling back at him and we awkwardly said hi and he led with “the drinks I ordered for you already came” and he pointed to them sitting at the bar as he waited for my response.That was the last chance I had to back out. I could have said “what drinks?” and pretended that we ran into each other by circumstance. But I took the leap of faith and replied with a thank you, confirming that I was the gurl in the pictures, that I was the gurl messaging him to meet up, that I was the gurl that he unsuspectingly worked with.I went for the shot first and threw it back signaling to him that I was still anxious/nervous. He proceeded to calm my nerves by saying it was good to see me and how he was looking forward to our meeting. He also led the conversation after that with how he needed both of us to be as discreet as possible because he didn’t want anyone finding out just like I didn’t. This along with the pre-game shots from earlier eased my mind some, and we got up and left the bar side and went to sit at the outside seating area.It wasn’t as busy out there because it was kind of windy that night. So it was more secluded and private with only a few patrons walking past every so often to go order more drinks. We sat and talked and opened up to each other some more. He asked me how long I had been dressing for and what got me into dressing. So I told him how I started in my sister’s underwear when I was a teen and that porn is what introduced me to the idea of dressing like a girl. (Pause here and go read my other stories if you want more detailed recollections of my past.)I told him I had only dressed up for a few guys over the years and that I didn’t just sleep around all the time. The last time was over a year ago and that was why I was looking to find someone more regular to trust and try new things out with.He told me about his couple of experiences with gurls in the past which chalked up to be somewhat similar to our experience so far, meeting online and talking back and forth before meeting in person and going back to his place or to a hotel. He also mentioned that he regularly chatted online sexting and fantasizing with gurls, gay guys, or other bisexual guys and I empathized with him and told him I do the same. Talking about past experiences with each other while slowly sipping our drinks had us both loosened up and we started to flirt more with each other. I’d touch his arm and laugh at a joke or grab his knee and squeeze when he made a crude remark. He even laid his hand on my leg and rubbed my thigh with his fingertips while we both flirted and tried to hide what we were doing from any others outside walking by.I wondered whether he was able to feel the small bumps in my jeans from my fishnets underneath. We both finished our drinks so I got up and said it was my turn to go buy the next round. As I got up he grabbed my side with his hand stopping me and protested that tonight was on him and insisted that he continue paying for drinks. I looked back at him and smiled and protested back that he already bought the first round and that it was only fair if I paid for the next.I slipped out of his grip and he then grabbed my wrist to turn me back towards him saying “No, I insist. Be a good girl and just put it on my tab.” He said this with a smile which I was a little mad at him for saying it like that because I told him in an earlier conversation that I liked it when I was told I’m a good girl during sex. So he knowingly used that against me to get his way.I just rolled my eyes and smiled back at him. I responded with “I’ll just have to make it up to you another time,” before he finally let go of my wrist so I could head to the bar.

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