This series of stories are all standalone so can be read in any sequence. They are about my favourite fantasy --- my first time wearing, or first time being caught wearing panties. Obviously then they all involve lingerie wearing men and the consequences may include cuckolding, creampie eating or cock sucking men amongst other things. If any of these are likely to offend you I suggest you stop now ... Otherwise please read on and enjoy. I do appreciate your comments and constructive feedback.
The Personal Assistant
At the age of 20 I was involved in a car accident that resulted in me being unable to concentrate for long periods of time. I had to give up my studies and look for a job in another field. About this time by 22 year old sister had to leave her job as a Personal Assistant (PA) to have her first child.
Although males rarely work in that field she convinced her boss to give me a chance. He agreed to give me a three month trial. I found I enjoyed the work and could easily handle the levels of concentration required. David was also very happy with my work and one month into the trial confirmed the job was mine until my sister was ready to return.
Two years later I still had the job as my sister now had two children and had decided to remain a stay at home mum.
I travelled with David to an interstate conference that went from Wednesday to Friday and we had booked to also stay the Friday night. I had booked David into a large suite so if needed he could take potential clients back there to discuss business to have some privacy away from the conference area. It was a very successful week.
Friday evening we celebrated his success over dinner and continued over a bottle of wine or two in the bar until a band started playing. Neither of us enjoyed the music and it was too loud to talk to David suggested we head back to his room to finish the final bottle.
As David and his wife were obviously very much in love and also enjoyed a very healthy sex life I had been surprised when David told me to book the Friday night also as I expected she would want him back as soon as possible. Back in his room I asked him.
I was very shocked at his reply. This was the first Friday of the month and she always attended a family orgy! Her parents and two brothers and sometimes some uncles and aunties always got together from midday Friday until midday Saturday!
If he hadn't had a couple of bottles of wine I'm sure he never would have told me. But now that was out in the open we began a very frank discussion. I was fairly inexperienced but admitted the best think I had ever experienced was eating my own cream pie from a girlfriends pussy. David admitted his only disappointment with his sex life was that despite loving sex his wife hated the taste of cum so although she had sucked his cock frequently she had never let him cum in her mouth.
I then told him that I definitely thought of myself as mainly straight but had wondered ever since my one cream pie eating experience what it would be like to suck a cock until it came in my mouth.
We looked at each other. Without a word I slid to my knees in front of him and undid belt and then the fly on his pants. His cock was already hard. I eased it out of his boxer shorts and looked up at him. He nodded.
I opened my mouth wide and slid his cock in as far as I could; initially only a few inches. I found my own cock growing hard as I started to suck on his. All to quickly I felt him start to throb and then his cum spurted into my mouth. It was delicious. I quickly started to swallow to make sure I got it all.
Almost as soon as I finished I headed back to my room.
In the morning we were both a bit embarrassed by what we had told each other and what had happened. But after another frank discussion we agreed that we would never tell anyone else about the conversation or my cock sucking. I also admitted how much I enjoyed it.
The first Friday of the next month I walked into his office at the end of the day and asked, "Since your beautiful wife is off having fun with her dad and brothers, would you like me to blow you?" He barely hesitated. Every month since that day I sucked his cock at least once and often two or even three times.
Then one Friday although we didn't know it his wife's orgy was delayed until the evening. She dropped into the office which was locked up but of course she had keys. She walked in on us just as he came in my mouth.
She was angry not because of what I was doing but because he had never told her. Also the fact that I worked for him meant maybe I was doing it more than once a month whilst she never met any member of her family unless either he was present of it was in public except for at the orgy. So she forced him to sack me.
A few months later and many interviews later I still hadn't got another job. Although I had an excellent reference from David the reason I had left couldn't easily be explained and on top of that was the discrimination against males in the PA world.
I called for yet another role advertised for a small private company. The initial phone interview went well and the job sounded interesting. It was long hours and extensive travel butcher pay rate she was offering was very generous. Karen asked to to come in for an interview but did warn that she did have a few unusual requirements that I would have to comply with but she would only explain those if the first part of the interview went well. She told me to dress casually as she never wore formal business attire and didn't like her PA dressed that way either. She worked from a home office.
I arrived at her house and rang the bell. The door was opened by a short fat woman about my age. She was dressed in a short red skirt and a lacy yellow top. It didn't do a very good job at hiding her large tits and the fact she wasn't wearing a bra. "Neil?" she asked, "I'm Karen."
With that she led me towards the office.
My still quite limited sexual experience had never included a fat woman before, but the sight of those large tits through her top and now the way her large arse swayed in front of me as she led the way had my cock growing.
The office comprised a desk with her office chair and then two seats for clients, then a sofa. Karen chose the sofa but sat right in the middle not giving me any room to sit beside her. She indicated that I should sit on the floor in front of her on a large soft rug.
As soon as I sat I realised I was looking straight up her skirt and her slightly parted thighs. She wasn't wearing any underwear! Her pussy was hairless and also obviously very wet!
She started the interview as if nothing unusual was going on. I managed to answer all of her questions and kept my eyes on her face rather than either her wet pussy or those beautiful tits that showed so readily through her top.
Having examined my resume and references she asked the final question as to why I had left my previous job if they were so happy with me and I didn't have another role to go to. This had always been the problem question, but this time having seen her wet pussy I decided to be totally honest and gave her the full story.
A little way into the story her hand slid under her skirt and she began fingering herself! Right then I thought I had an excellent chance of landing the job and was hoping some of her unusual requirements would involve her pussy. I made it quite clear in my story that I preferred pussy.
Karen advised I had the job as long as I could agree to all of her terms. She explained that my job would be very different to my previous role. She was a very rich woman as a result of a recent lotto win and really didn't run a business at all. My role was to organise lots of travel all over the world, but no flying. I would travel with her and stay in the same room or cabin on the ships as she would always cruise between continents as she hated flying. I would organise all sightseeing and all meals. All my costs would be covered and I still was to be paid very generously.
