Covid - Crossdresser - Conundrum

robz314

I work for a large construction company that has one owner. He just celebrated his 70th birthday a few months before this all began. He is in good shape and health and we always had a great working relationship.


Back at the start of Covid when we were all told to work from home, my company would let one woman work from Monday thru Thursday. The office would be vacant and quiet all day on Fridays. I would go in and do my weekly reports and scheduling on Fridays just to have the place to myself.


As a closeted crossdresser during covid I amassed one of the most sexy wardrobes and shoe collections a girl could ever dream. When I seen the oppurtunity to dress up on Fridays I immediately jumped at the chance. The first week I parked right by the steps and ran in and started my day. Oh, and in my mind I was the sexiest girl in the office and everyone wanted me. I would walk around and hear my shoes on the floors and just be so into the whole office girl scenario.
At first I hid from the delivery guys. Then after a few weeks and better makeup I started to let them in and they would do all they could to flirt with me and get my attention. Some I even gave my number and received a few vulger pics of them but, they were just boy toys to pass the day.


My Conundrum... Unbeknownst to me the building we are in had cameras. I knew the yard had cameras but, not inside the building. Well one Saturday there was an accident in the yard doing some damage to a machine and no one would own up to it. When the company controller ( an older very reserved professional woman ) asked me, I told her the place was clear when I left Friday at 6pm. So, she went to the video tape and found the culprit and everything was resolved in a matter of days. Thinking I was in the clear, I was spending every Friday and as the office sexpot. The delivery guys seemed to show up all day and I was loving being the center of attention.


So, 3 weeks after the accident, I was in the office with my gaurd down just being the sexiest secretary on earth. I had music on and I was wearing a short silky dress, thigh hi's, sexy netted panties and short black booties. I was going about my day when at about noon I heard the lock in the door open and the owner walk in.


FREAKING OUT -


So, the owner walks in and and I am FREAKING OUT and hide. I watch him go into his office and I take off my shoes and run to the door. I hear him intercom me and I just bolt out of there. I get in my truck and he calls me. He says Darling, how about you grab us both a coffee and we can go over a few things. HMMM ? Darling ? He is a sweet and kind 70 year old man but, he just invited the crossdressing operations manager of his company for a coffee.


So, I go back in, put my shoes on and play the part that I am CAUGHT. I make the coffees and go into his office. He is behind his desk looking at his laptop. Dressed as always Work boots, buttondown shirt and loose blues jeans.


He grabs the laptop and gets up and says meet me on the couch. Now, I'm really freaking out. We sit and I cross my legs, my dress is so short and slit up the front and I know he can see the thigh high bands. He puts his hands on my thigh and rubs it gently and says calm down, I just want to talk and go over a few things. He proceeds to tell me how sexy I am and that he is sorry he hasn't noticed or acknowleged me sooner. He says, I haven't seen you on the payroll reports, what's your name dear? I freeze and he says, " Why don't we call you RONA". I had chills.


He turns the laptop and presses play and he shows me numerous clips of me with the delivery men. I went to talk and he touched my thigh again and said DARLING IT's OK.
He then tells me I wish I had known sooner. I said explain. He said, he and his wife hadn't been intimate in over 10 years. I went to talk again and he leaned in and started to kiss me strong and firm. He slid over ran a hand up my skirt and grabbed the back of my neck and really started to kiss me. We kissed for what seemed like forever and his hands were all over me. He was palming my crotch and poking a finger against my love button. He bit my neck and as I reached for his groin and he was a solid rock. ( I figured with him at 70 this wasn't going to happen).


After he felt my hand there he kissed me harder and grabbed both my ass cheeks and got on top of me and grinded himself against me. He whisperd in my ear ( I have to have you right now) He stood up and his groin was and inch from my face. I unbuckled his belt and undid his button fly jeans and slid his pants and underwear down together. And there was his member and inch from my mouth. With a pile of grey hair surrounding it. Then he pulled me in and filled my mouth with it. He started encouraging my work on it and he got so verbal and forcful. He pulled out and fed both his nuts into my mouth telling me to suck them and not to neglect his boys. He had full control of the back of my head and he used my mouth as he pleased. Then the he told me it's coming and he exploded in my mouth. 10 years worth was spilling into me and out the sides of my mouth. Dripping down my chin on my dress and stocking and then finally he pulled out and dropped next to me on the couch.


I tried to clean up a bit and look respectful. I took a sip of coffe and we had a moment of small talk and he told me that was sooo good and a decade over due. He held my hand and then was rubbing my thigh. I was soooo excited and dripping in my panties. I couldn't contain my erection when I noticed he wasn't going soft. He seen me staring at it and put my hand on it and said honey your next, I took the little pill. He reached into the drawer next to him for some lube. Applied a ton of it. He grabbed my hand stood me in front of him unbuttoned my dress slid off my panties then he sat back and told me to get on him. When I was on top of him he grabbed my shoulders and drove me repeatedly down on him then he unbuttoned my dress and removed my breast inserts and sucked and teased my nipples so much. He reached around grabbed my ass and bounced me up and down on him. He was so hard and with every thrust he was hitting my spot and I had a huge anal orgasm all over his chest. He grabbed my clittie and teased and stroked me while he bounced up and down on him. I started to shutter again and exploded. He was deep in me he was rubbing my stocking covered legs and tugging me in by the high heels of my booties. Then he started to kiss and tease me again and he started telling to to ride him harder and his words were more and more vulger and he made me ride him so hard and then he was about to explode. he moaned and screamed and then we both came. I fell into his arms and we kissed and he clenched my ass and caressed me. I fell off him and tried to sit and not get it all on the sofa but there was nothing I could do there was cum all over us. He looked at me and laughed. He said if I would have known you a few years earlier we could have been doing this all along. ( Embarrased and feeling Awkward - I worked there for 6 years) I leaned in and kissed him so he wouldn't say another word.


I told him that was awesome and hoped we could do it again soon.


He and I started to get dressed and clean up when he grabbed me and kissed me so deep. I was sticky and covered in cum and he said why don't you go make yourself presentable and clean up, we both have work to do.


I dressed and walked to my office and went back to work. I was sticky and dripping and seriously feeling like the whole world knew what I had just done. My clothes were covered in cum. I was so nervous and wondering what he was thing of me. I knew my job as a man was safe but as RONA????
About an hour went by and I heard him walking to my office. He told me that my secret was safe with him and the office manager. He said he addressed it with her and it was beneficial for me to have Fridays alone.
Then handed me a disk and said this is a copy of the session we just had. ( WHAT ???? HE videoed us ??? PERVERT !!! ) I should have known. He told me he has a copy for his spank bank to get him thru the week. HUH ? He then handed me an envelope and said there is a list of things to get before we meet again next week. There was some money in there and a list of what he wanted me to wear.
Then he said, See you for lunch, here Friday at 1pm. Be dressed and ready for me.


And just like that I became the office SLUT !

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