Any similarities to any persons in this story living or dead are purely accidental and also if you are not old enough or allowed to read such stories of a sexual nature in your place of residence/country and then please leave this site now.
This story does depict sexual activities between male / female and male/male persons but no one was hurt or suffered throughout the making of this story and in fact they all enjoyed it because they told me so.
This story is fictional and has never happened although who knows, maybe one day
Ok just to let you know a little about myself; My name is James and I live in the UK just outside London on the Surrey and Kent border, I'm about 6' 2" tall with dark hair, clean shaven with a slight tan and reasonably fit since I joined a gym 5 years ago and kept going 2/3 times a week which helped keep me in shape. Now I have always realized from an early age that I kind of felt different and never really enjoyed boys stuff growing up. I am now in my forties and for many years I have enjoyed some cross dressing. A girlfriend many years ago actually encouraged it when late one night suggested I try her pink lace knickers on so she could check me out in them. I was very keen to get them on as soon as possible and after I pulled them up and got comfortable in them the feeling was total satisfaction and they just felt right. It was not just a sexual kick either although that was good too being honest.
Anyway I soon discovered my level which was black lace thongs, stockings and skirts and so I always keep my body hair neatly trimmed especially just above my cock, below that it all has to be smooth right underneath and up in between my bottom cheeks as hairy arse does nothing for me. I never felt I was trying to be a woman I was just happy to wear these items as a man sometimes all together and sometimes one at a time and I only ever wear my lace thongs now everyday. I have of course often wondered about my sexuality and I feel I might well be Bi-sexual but I have never yet had a male encounter. I do so love the soft warm body of a woman with her curves and of course her choice of clothes too, well the underwear most of all! To sum up I am very happy with my body and my cock gives me a lot of pleasure but I do love to cross the line and dress in some very comfortable feminine items.
Moving on with the story.
I was scanning the papers for a new job one day when I stumbled across one that caught my eye; "Personal Assistant required for Company Director. Applicants will need to be PC literate, organized, very presentable and be prepared to work long hours for a good salary and special perks. Please forward CV by email with current photo to Stella at the address below"
It was the special perks that caught my eye and I imagined perhaps having personal use of a company car or such which would be ideal as mine had just died making it difficult for me to get around and I don't mind wearing a uniform as long as it looks and feels good. It all sounded worth checking out. I sent my email and photo off the same day and got a confirmation of receipt straight away and a reply from Stella later that day asking me to attend an interview in 2 days time at the address given which was fortunately only 24 about miles away. She stressed that I must be on time very smart and presentable and I would also be asked all sorts of personal questions to assess my suitability for this position. If successful at the interview I should be willing to have a uniform fitting at the same time so all could be settled the same day. Stella stated that there were just 3 possible candidates for the position and I was going to be the last to be seen.
I arrived at the address given in the email at my allotted time and the venue turned out to be a very large detached house set in several acres of garden set well back from the road with a enclosed garden beautifully set out with trees and shrubs all very neatly trimmed and kept "very presentable" kept coming to mind as everything obviously had to be neat and tidy from the garden to whoever worked for this Company director, whoever he was. I expected Stella to be the HR manager in all of this and to be well groomed as well by all I had seen so far. I took my humble hire car for the day up the gravel drive once I was let in via the gate intercom and the automatic gates closed behind me. An expensive BMW was the only other car on the drive at the front of the house and I parked my little Vauxhall corsa nearby and walked to the front door with an easy 15 minutes to spare before my interview time. As I rang the door bell it was quickly answered by a very attractive 30 something woman who was as tall as me at 6'2" and dressed in a smart navy blue fitted suit with a skirt just above the knee and a white silk blouse. Her blonde hair was quite short but nicely styled and it showed her face off almost to distraction. I could not help but notice her slim figure and her long legs as she invited me in with a smile and the lovely nude stockings she was wearing only given away by the fitted skirt showing the garter clips under the tight skirt. I pride myself on my keen eye for detail and this woman was immaculately dressed. She spoke for the first time and told me her name was Alex and I should be meeting Stella shortly but at the moment she was on the phone to some difficult customers so I should follow her to the lounge for tea, coffee or something else that I fancied. If I told her what I fancied there and then I'm sure I would have got a slap but the erection I had was beginning to make quite a bulge down below since meeting Alex and I needed to sit very soon to help hide it. I relaxed on the sofa whilst Alex poured me a coffee decaf and proceeded to sit next to me after she placed the cup on the coffee table in front of me.
She sat very close almost touching each others thighs and smiled as she spoke about her position here, " I am the chauffeur here and housemaid when no driving was called for but we all kind of do whatever is required to get the job done here. There is just me and Stella at the moment and soon a PA for the Director which I'm sure you will get as you have just what we are looking for, you are on time, you dress very well, well spoken and polite and as long as you can organize and use a PC I think the job is yours as long as you don't mess up with Stella. Don't be put off by her direct methods or questions and just do as she asks in the interview and it will be just fine, in fact I should not tell you this but the others that came earlier were not successful because of their attitude to the uniform Stella wanted them to wear so you are our last hope" She smiled when she finished speaking and leaned into me with our lips just touching and she spoke quietly again saying "There is so much fun here when the work is done" her slender fingers had now found my excited erection and I was breathless as she stroked me through my trousers and I was alerted to someone watching from the open doorway to the hall when they spoke "Alex, if you are finished with James for the moment I am ready to conduct our interview he has come here for" Alex slowly took her hand away from me and stood up and introduced Stella. I then stood with a deflating erection and some degree of embarrassment having been caught with Alex on the sofa and her slender hand. Stella was as tall as Alex and myself, very refined, elegant and possibly 35 or 45 yrs old with a sensual figure, 38" bust, slim waist and a generous J-Lo bottom that makes you really want to reach out and touch it when she moved. She had a mature but beautiful face with full red lips that longed to be kissed and was wearing some modern designer glasses; she wore very little jewelry but had a simple pearl necklace which stood out from her tanned neckline. She was dressed almost the same as Alex but in a black suit with black stockings with shoes to match. With her dark raven hair down as it was she reminded me of a seductress moving in for the kill. I ought to try and keep my active imagination under check here. Stella escorted me to the second floor where we walked into a plush office for our interview she gestured me to a soft armchair near the window and took one opposite with just a small coffee table in between us.
Stella then spoke" Well James I see you have met Alex and her wandering hands but its OK don't be at all embarrassed here it's all perfectly natural in this house as we all operate as a family team: no perhaps family is not the correct term but lets just say friendly team shall we? I cleared my throat and agreed but still felt caught out with what had happened downstairs in front of Stella. "Alex must really like you as she has never done that to anyone for at least 2 years or so but let's move on as we have some things to discuss"
"Now the position you have applied for is for my Personal Assistant, I won't beat about the bush as I have earlier today with the others; suffice to say you will be working for me, you perhaps did not realize you would be working for a woman did you? Never mind you need to know this right away but I have a good feeling about you and I feel you may be just the person we are looking for. We just need to check a few things and we shall see. I need to tell you that I speak and act my mind and I expect you to do the same in fact we all do here and that is how we all get along. You will always refer to me as Stella and you will be available to me totally throughout the day and night only if necessary. I expect you to always be clean tidy well dressed unless its at night or the weekends when you can be a little more casual. I expect my uniform to worn at all times through the week whilst working and be available to help out in any capacity here at my country retreat when you are not busy on the PC or helping me personally. I will continue talking and you can ask anything that is on your mind afterwards. I am very insistent about my uniform and that we all wear the same thing and that way we all feel equal even though you work for me. I wear the same clothes as my PA, Chauffeur, butler and so on and therefore you must wear the same" I speak eventually and say that is fine with me and ask what exactly is it I would be wearing. " Well I hope you have been taking notice of what Alex and I both are wearing" I pitch in and say of course the dark navy blue suit and you in a black version of the same. "Good, then lets move on shall we I will begin you on a months trial at 25,000 plus all expenses with living accommodation here. Either of us can terminate this arrangement with just a few days notice or then you will become one of our team. Welcome James. Now just to ensure you are better then the rest I met today would you please stand and remove all of your clothes as I do need to check you over, I do this to all who work for me. Some did others did not and when it came to the uniform I was obviously wasting my time with them" I slowly stood wondering why I had to remove my clothes but was not going to mess this up just at the moment by refusing now but then I remembered! SHIT, SHIT, SHIT. I had to get out of this now somehow and stopped undressing. " James is there a problem I don't know about if not then please continue" I thought well if I lose this job now by not undressing I may as well continue, I left my trousers until the last and finally dropped them to my embarrassment as it left me standing there in just my favorite black lace thong knickers. How could I be so stupid to wear them today, I knew about the possible fitting but did not realize of course about having to strip off in a open office in front of my prospective female boss. Stella looked at me for what seemed like hours and finally spoke with a smile on her face "James, I absolutely love your choice of underwear in fact I could not have chosen better myself. You are definitely just what we are looking for" I relaxed somewhat but still felt embarrassed at being found out in my favorite thong. Stella rose from here seat and came over to me and whispered "I think it is time you checked out the uniform with me in the adjoining room" She took my hand and led me to the room off to the side which had several uniforms hanging in an open wardrobe all in different sizes either in navy blue or black as she and Alex were wearing. "Now she said I think this size should do you just right, please change into it as quickly as possible James. I realized it was identical to theirs in every way. White silk blouse, fitted jacket and over the knee skirt. I put them all on and was so pleased with how I looked and felt I actually forgot Stella was even there. It was only when she came up to me from behind I saw her reflection in the mirror that I was glued to. I came to earth with a bump. Stella, you really want me to wear this as my uniform everyday "Absolutely she said and you look damm good in it too. I was right you are the one for us. When I saw how you keep yourself in good shape, neat and tidy and you have very shapely legs for a man and of course your preferred choice of underwear. I felt you were just the one to be my PA. Now it is obvious you like to crossdress which is wonderful but you are a man and so I suggest that you keep make up to a minimum, just a clean shave each day with a light dusting of powder, no need for lipstick and no painted nails and a spray of my best perfume and you will look just perfect as my PA. Now tell me more about yourself and your crossdressing and how much do you like to do? No wait there is something missing" She darted off and returned with a pair of suburb expensive nude hold up stockings and shoes with 4" heels and insisted on putting them on me which I have to admit I was more than happy to oblige as I love the feel of stockings on my legs and the shoes finished it all off. When she had finished she stood back and said "Perfect. Just what I love to see; a good looking fit man in a smart suit and stockings. If you prefer you can wear a suspender belt and stockings instead of the thigh highs but just as long as you wear this everyday I will be very happy" I smiled and said what would you like me to do first. "She said go and get all your belongings and get back here as soon as possible. You are moving in tonight! When I returned some hours later Alex met me in the hall and told me she had not seen Stella so excited for several years like she was tonight, She realized I had taken to the uniform and insisted I go upstairs with her and change into it with her and get used to going around the house dressed in my new clothes. Alex rushed ahead to show me my room which now had 3 matching sets of navy blue skirt suits and 3 black suits the same style and size, various lace suspender belts and different colour stockings including holdups, an assortment of lace and silk knickers, panties and thongs all in my size. Alex was so excited for me she could not keep still wanting to see me dressed up in my uniform. No wait she said "there is something I need to finish first and proceeded to push me down onto the bed taking my clothes off in the process. When she got to my black lace thong she stopped and squealed" I just love them and you were wearing them earlier downstairs and I didn't even know she said. She was all over me faster than I could keep up, next thing my thong was off and on the floor and she had me pinned to the bed with such amazing strength with my cock pointing straight up into her soft clothes. In a flash she was naked except for her knickers and bra which by the way were in blue lace. She grasped my aching cock and eagerly took me in her mouth and moaned so loud I felt it vibrate all through my body. I had gone several months without a good fuck and Alex's mouth took no time bringing me to an almighty but rapid orgasm. She still had her bra and panties on and when she stood up and unhooked her bra her breasts just stayed there with no support at all. I lent up and took the left breast to my mouth and suckled the nipple which now was so hard I just played it with my tongue and she begged me to move to the other one and continue there before she pushed my down without a word and said "its your massage time now, turn over" I did not need much effort to do so but she gave me a helping hand anyway.I just flipped over in a blink of an eye. God she was so strong! She must really work out I thought and I'm glad she did as when she started to massage my shoulders and lower back I just relaxed and almost started to drop off. Within minutes she had my entire body so relaxed I could not give a care about anything until she had found my lower back boring and had moved to my bottom and then decided to insert a finger into my hole when they then became two and then three fingers at which point I was fully alert and pushing my exposed hole back up to her" That's it James, push back and fuck my fingers I'm well lubed up so push harder and faster and fuck my hand. After some minutes she withdrew her fingers leaving me feeling empty but she returned and pushed them in again just a little to tease me or maybe it was four fingers I'm not sure but I soon became aware that both her hands were holding either side of hips pulling me back to her thrusts which were going much deeper now, that was beginning to feel very very good. She obviously had put a strap on dildo on herself and decided to have some fun "She whispered do you like my cock fucking you?" Hell yes I said just push it in some more and she did just that, right up to her balls which were now banging against me. I reached back and felt what was there!! Alex had a huge cock buried in me and a set of balls banging against me!!!! She was a he !!! Fuck it felt so good I just did not care, I looked over my shoulder at her and she smiled sweetly and looked so beautiful behind fucking me senseless. She teased me by stopping to check my reaction so I quickly pushed back on to her engorged cock to continue this great fucking that I was getting "That's it baby fuck yourself on my hard cock, push back harder, faster that's it, make me shoot my sperm into your tight hole, fuck my cock with your tight pussy, you know you love it don't you!" No doubt about it I fucking loved it and all she was saying to me as well. She began to get more forceful in her thrusting and fucking and I swear she was bigger now inside me and I felt every thrust of her cock , balls and now hips banging into me from behind, her hands moved off from my hips and under to my stomach and then moved up to my nipples where I got a brief pinch until her hands moved further forward to my shoulders where her hands held me back tight to her thrusting cock buried deep in my man pussy which was really getting a pounding. She started to breath deep behind me and her cock was so deep and hard I can't describe it SUDDENLY she blurted out FUCK FUCK!!!! I'm cumming I'm cumming!! And unloaded a huge amount of cock juice into me with each spasm, 4, 5 shots and still coming inside me she withdrew suddenly and continued to shoot up my back for a few more seconds before slowing down and collapsing to my side. I felt well and truly fucked, covered in cock juice up my back and inside my well fucked behind which now was oozing cum like a dripping tap. I looked at Alex beside me who was regaining her breath and she just smiled and sweetly said" Sorry James I just could not help myself. Don't be angry with me I wanted to show you my cock later in a few days but I was so horny the male side of me took over and I needed to cum and fuck you. It's the way I am. With that she slid her hand up my back scooped off her juice and brought her fingers to her mouth and sucked them dry and then lent into me and kissed me allowing me to taste her tongue with my cum on it. She is so beautiful I smiled and said I'm not angry and don't you be sorry either. It was fantastic. When do we do it again? The voice that spoke was Stella's from across the room who had been standing there for most of the time watching the action and dressed in only black stockings and suspender belt, bra and knickers with a glass of wine in her hand. " Well James now Alex has fucked you senseless this evening you will have me to attend to tomorrow. First we work and then we play don't we Alex" who just grinned at me with a twinkle in her eye. "Breakfast at 8am and we start work at 9am and I want you looking your best in your navy blue uniform, stockings and shoes. Alex please remove all of James's man clothes to the cellar he won't need them anymore" She wished us goodnight and left the room, I swear my cock gave a twitch when I watched her bottom disappear out into the hall.Why did I love her bottom so much I thought I was just a leg man?? Alex by this time had decided to do a much slower job with her mouth on my rising cock.
More to come?
Let me know what you think so far. Kind words appreciated.
hermaphroditus07@gmail.com