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My Transgender Secretary
I am your typical 28 year old shy, skinny comic book nerd at 5ft 5in and 145 lbs with green eyes, long red hair, minimal body hair and a shy somewhat introverted personality. I have a full mouth and a ready smile. I think it is my best feature beyond my green eyes. I live alone and have 2 cats and play World of Warcraft with some buddies when not working as an accountant at the high end lawyer firm of Bennet and Darcy making way more money than I probably should at my 30 years of age. My name is Kevin and this is my story on how I crossed over into the girlfriend zone.
I am a serious crossdresser and am pretty proud of my ability to pass. Not as some over the top drag queen, but as a honest, every day girl with minimal makeup and foundation gear. OK, I do have some nice "D" cup mastectomies as I have bought into the bigger is better aspect of today's social media, but I can pass pretty well I think. Typically during the week, I wear panties under my men's clothes but on the weekends I am all femme and have a medium sized wardrobe at home just for my femme personality named Kandi. The usual items of skirts, blouses, dresses, jeans, makeup, lingerie and maybe a few too many pairs of shoes. I mean, if you can have too many pairs of shoes? As I said, I think I am passable if I spend time on it, but it is mostly just a thrill to feel the sensualness of female clothing against my skin and adopt that female personna. I am not into men, but love being with girly girls and one who understood my desires would just be a dream.
At the firm, we have several paralegals who are the daughters of the one partner Mr Bennet. Janet, Liz, Mary, Kitty and Lydia. They are all young, pretty, 20 to 30ish, and obviously looking to marry a Lawyer and strike it rich, so the accountant guy over in the corner is never flirted with, or hit on like the lawyers are. Well, except for Janet who is the overall office lead and seems to flirt with me on a regular basis.
Janet is a cute Hispanic girl with long dark and lightly frosted hair that stands about 5ft. 4 inches and weighs maybe 135 with "C" cup breasts that are just magnificent. They are only overshadowed by her witty and nerdy personality. We usually flirt and talk gamer stuff, Comic books or the latest Marvel Cinematic and every time I ask her out, she politely turns me down with something about not dating guys from work. We do end up flirting most days and Janet has even been known to accidently lean into me and have her breasts brush against me while she is trying to show me something, or maybe bend over a little too much at the hips instead of squatting when she knows I am behind her. Once she even bent over at the waist while in a short skirt to pick up a dropped pencil, presenting a total 'upskirt moment' and then turned around quickly to see me looking at her ass and she just smiled at me with a slow, sly wink.
With the constant flirting and suggestive moves, I started to think it was all a tease or set up for a harassment case, but she just did not seem like that kind of girl. She never talked about a boyfriend, fiance or husband ( and no ring ) so I always thought she was single, but maybe she really was just a tease.
Finally one day while she was flirting with me, I just asked her, "OK. Whats the deal? You flirt outrageously, but turn me down when I ask you out, so is this a tease thing or a set up? I like you, but am getting uncomfortable with this yes and no activity."
Her response floored me, "Kevin. I am not like other . . . I like you too, and don't understand . . . I'm. . . You don't know that I may be . . .I like girls! OK. I said it! I like you and that is what has me so flustered. I just don't understand why I am attracted to you since I like girls and you're a boy....errrr, man, sorry!"
With that, she quickly walked away and I sat stunned that she was attracted to me, but also that she liked girls and that maybe my being a crossdresser was something she 'saw' and that added to the attraction I wondered. For the rest of that week and through the next, we played it pretty cool, with minimal flirting and stricktly business during meetings to calm the situation down.
We ended up one week later having a big office celebration for winning a huge client and also to celebrate that Elizabeth Bennet and Mike Bingley, a Paralegal and the young hot shot Lawyer new to the firm, announcing their engagement. The entire office shuts down early and we went to dinner at a big Japanese place to eat, drink and celebrate. Janet ended up sitting next to me while wearing a cute little grey pinstripped pencil skirt and a white top with grey heels. I thought she looked fabulous and as she was downing her second drink, I leaned in close and told her how lovely she looked and I was glad she was no longer avoiding me.
Janet smiled, and spoke in my ear about just needing time to figure out her head and then she lightly kissed my ear and whispered thanks for the compliment as she had worn the outfit with me in mind hoping I would like it. I then felt her leg softly press against mine just for a moment and thought, 'wow is this girl hitting on me again!?'
The team took up an entire grill table and we enjoyed the show as our server cooked, flipped shrimp and did all his 'egg tricks' to entertain us and the drinks kept flowing. I stopped after my third but noted that Janet had about four glasses in front of her, so knew she was past tipsy! When she got up to hit the ladies room, you could see she was drunk and that she was weaving while still trying to shake her hips. A coworker noted that she was almost stumbling drunk and that we may need to call a cab for her.
When Janet came back to the table, we finished up eating and chatting and as it was close to the party being broken up, I leaned over to her and told her that since she seemed to intoxicated to drive, I could take her home if she liked and to my surprise she agreed.
Janet actually held me close while we walked to my car and then as I opened the door for her to get in, she pressed against me and lightly kissed me before saying,
"You're such a gentleman and thanks for taking me home Kevin."
Janet told me her address after I got in and started the car and as I drove her home, she seemed remarkably more sober than I would have expected as her words, now, did not slur. She spoke about how she had known the other new lawyer, John Wicham at another law firm and how he had constantly hit on her and the other ladies or treated like they were just a sex object. Now that he was with Bennet and Darby, he was doing it all again and she hated how Lydia was just eating his attention up. It took me back a little on how angry she was at the new guy as he seemed not to act that way since he joined the firm just a few months ago. I knew the ladies were all gaga over him and his good looks, but surprised that Janet actually had a history with him. I also had to admit that with her grey pencil skirt hiked up to mid thigh, she was displaying a lot of leg, and I almost could not help but check them out. I must have been caught, because as we neared her house she commented with a smile,
"I knew you would like my legs in this skirt. I am still a little drunk, so can you walk me to my door and help me inside Kevin?"
"For you, I can do that." I told her
Pulling into her driveway, I noted she had a nice one story flat, and turned off the car and got out so I could get her and we walked again arm in arm up to her door while she leaned on me slightly. When we arrived at the door, she pulled away, reached into her purse to get her keys and then slid them into the lock. Before turning the keys to unlock the door, she turned to me and looked at me for a long second, and then as if making some decision, wrapped her arms around my neck, pressed against me and kissed me in a passionate, rolling, slow, wet, kiss that had me hard in no time. She pulled away after that and said,
"I have been wanting to do that all night. Your lips are so kissable and I can tell you liked it too. Now come inside and let me reward you for being such a gentleman and bringing me home. She opened the door and led me inside where she sat me down and hiked up her skirt so she could straddle me and show off her legs encased in suntan thigh high stockings. She began to kiss me and grind against my hard cock, making me moan into her mouth while our tongues danced a duel against each other.
My hands came up and carressed her breasts while she unbuttoned my shirt to find a light chemise, which raised an eyebrow almost Spock-like in fascination. Then she leaned back and pulled down my pants and saw the womens bikini panty I had on and smiled saying,
"NOW it makes sense to me why I am so attracted to you! You're a dresser aren't you? I was picking up on that feminine side of you or maybe it was that I saw the chemise through a work shirt. Oh, this is so hot. I hope you like me sucking your cock and maybe you can suck on me after!?"
Her mouth on my manhood was all I could hope it would be, and after only a short while I was spurting my load into her hungry mouth. She licked me clean first, then her own lips and asked,
"Did you like that baby? I know I did and I hope you don't mind my not being like other girls....you see, I am pre-op, so I know what it is like to enjoy the other genders clothing."
She lifted her skirt all the way up onto her hips and dropped her skimpy dark grey lace panty away from her hips to reveal a dripping 5-inch cock that was totally bald of any hair and looked so sexy between her thighs I could only smile and pull it close to my face. Inhaling her scent, I stuck my tongue out and tasted her and to my happiness, I liked that musky, sweet flavor and promptly pushed my lips over the head and started to suck on her cock like I liked mine done. She spurted in my mouth in short order blasting her sweet ejaculate down my throat and crying out as she held my head against her in her orgasm.
"Oh yeah, that was just like I dreamed about. Now come to bed and make love to me as a man does to a woman so I can feel you in my boi pussy, baby."
Janet led me to her room, with us both dropping clothes along the way and her leaving her bra and stockings and heels on while I got naked. Sex that night was as good as a porn movie and as dramatic as some great american love story where in the end, they both see stars during sex. Yes, it was that good, with us falling asleep in each others arms.
When I woke in the morning, I had to pee and slipped out of bed, used the lavatory and slipped into my panties and shirt so I could make coffee and maybe some breakfast as I was famished.
Digging through the cupboards I found the coffee, started that, and then got some eggs and toast going when Janet came out wearing just a pair of panties with her stockings still on looking sexy as hell.
"Morning lover. You rocked my world last night and I never thought a man would do that for me! I guess since you're a dresser, you aren't a typical man though, are you? Can you take me to your place today and introduce me to your femme personna after we get my car? I would love to meet her and maybe we can do lunch if you want?"
"I think I can arrange for you to meet Kandi. After breakfast, lets shower and dress and see what you think of her." I responded.
We ate, showered together and then put on some clothes and I took Janet back to get her car and then she followed me to my place. When we got inside, I sat her down and got her a drink and told her she could relax while I changed or just come watch. She chose to watch, so I stripped down and put on a fresh thong panty in black with a black t-shirt bra after attaching my falsies. She had on jeans and a blouse with low helled ankle boots, so I decided on the same casual kind of look and got out a pair of my tight designer jeans with the fancy pockets and stitching, a white blouse with a draped hankerchief hem sweater in black. I put on some black wedgies to show off my toes and did my makeup lightly with some dangle rinestone earrings in my only piercing and soft pink matte lips. I styled my strawberry blonde hair and combed it out to create some bangs and heard Janet wolf whistle me and then ask if she could make a few adjustments.
She shaped my brows a little more finely, but not enough to look obviously femme when at work...just more metro / androgenous, then added a spritz of her perfume and said,
"We need to get you your own scent and maybe some more ear piercings, but you look scrumptious baby!"
"Thanks. Glad you like it and now what do you want to do now that you've met Kandi?" I asked.
"Kiss you and then take you shopping!" She responded, and then she did just that by kissing me with plenty of tongue and a sexy nip of my lower lip.
We got into her car, after I got my little shoulder strapped clutch with my ID and some assorted makeup and keys, and headed to the local mall where we got me some Obscession for women, since I loved the musky sweet smell, and then had the kiosk pierce my ears again so that I had 3 sets in each ear. The bottom dangly set and then 2 studs each. We shoe shopped, but ended up buying me a blouse, some 3 pocket, super tight, lowrise jeans and then a little green and black minidress. We had a blast shopping, chatting, being checked out by the guys and catching lunch at the food court. We even hit a movie and were able to hold hands and sneak a couple of kisses during the movie that had me squirming when I started to harden at one point.
When we got back to my place, we romped like new lovers in my bed and then went out for dinner before I sent her home. Sunday afternoon I just could not get her off my mind so I had an order placed for flowers to be sent to her place Monday afternoon. I spent the rest of Sunday smiling and recalling what a wonderful time I had as Kandi with Janet and hoping we could keep it secret at work.
Monday I got dressed as usual in my panties and a male undershirt since I had all the new bling and put on my suit. When I got into my office I found a single bud vase on my desk with a red rose and a few people asking about what I did all weekend to earn it. I responded casually,
"It must be from Janet as a thanks for bringing her home and then helping her get her car the next day, isn't there a note on it? I am sure at least one of you Nosie Rosies have read it!" I laughingly responded and then looked at the note that said exactly what I thought it would: "Thank you for the help and time out of your weekend. Sincerely, Janet"
Of course, when I saw her, we both smiled and did our normal 'flirty' routine and moved on as if nothing happened. Inside, I was all a flutter and knew I had to see her again. Trying to play it cool, I did not hit on her or call her back that night. I did wait till after work on Tuesday to call her after she left and set up a date Friday night for dinner and a movie.
That same Tuesday, in the morning, I got a meeting request from Janet to meet her in my office on Wednesday at 11am to review some expense items from Wicham on his current case. Accepting the meeting I wondered why she needed me to help her approve his expenses, but maybe she wanted to see what I thought as some of his expenses were on the high side lately.
Wednesday at 11am prompt, she entered my office looking like a dream angel in a white leather skirt, tan hose, light grey heels and a soft creame top that was slightly unbottoned and showed some cleavage. She locked the door and laid some paperwork on my desk and then came around it and sat in my lap and started to kiss me while her hands were running through my hair. She finally came up for breathe and said,
"Damn, I like kissing those sexy lips of yours baby. They make me want you and I want them on my sex so badly I can't wait for Friday. Can I see Kandi again on Saturday for a girls only date too?"
"You sure can. I am pretty sure she is as anxious to see you again as you are to see her! Besides, I think she wants to show you her new dress!" I agreed.
"Oh, yeah, that sexy black and green number? I can't wait to see her in it!" she purred.
After that she got up, straightened her skirt and showed me Wicham's expenses and they did seem a bit out of line especially when she shared it was something she noted at their last firm. It came out that he was inflating his expenses so he could use the money to woo the ladies and that got him terminated. But we both reasoned if he was dating an owning partners daughter, he would not need to do that. We approved his expenses and then I made a note of it for future reference if needed.
Friday, I left work just a little early so I could go home and change into some date clothes instead of the khakis and polo shirt I had on for casual Friday and then pack a bag for Kandi so she could show up Saturday morning if things went like last week.
Once home, I showered and put on some grey slacks, a green, short sleeved, button shirt with nice shoes and packed my bag for Kandi with shorts, jeans, tops and undergarmets. Then I added, more undergarmets for the date, the dress, some heels and makeup and the rest. Then I hopped into the car and headed to Janet's house. When I got there, I parked and then knocked when I got to the door. She opened it right away, did a pose showing me her short wine colored minidress that was low cut and skin tight, dark hose and red nails, heels and jewelry with smoky eyes and dark lips and I just did a once over and gushed,
"Wow! You look amazing! I am maybe under dressed for you now, I am thinking!"
"This old thing!? I thought you said dinner and a movie, but maybe I can con you into dancing?" she smiled at the compliment.
"I am glad to go to either as long as you go with! Now I have us reserved at Cafe Ole, the little Mexican place that has the very best fajitas and margaritas in town! Vaminos Chicas!"
We went and ate maybe too much and drank just enough to feel happy and then we went to the movie as I promised she could dance with Kandi tomorrow at the club.
We went back to her place, spent the night together making love in a manner that gave us both exquisite pleasure and whole body orgasms! In the morning, I quickly changed to Kandi while she was still asleep. I put on my falsies, a crop top t-shirt with no bra and a gaff panty under my short shorts with some slippers and then made breakfast and coffee like I did last weekend. I had just poured the coffee and fluffed my hair out to a more feminine fashion when I heard her come into the kitchen, so I turned to greet her.
When she saw me dressed as Kandi, she squealed like a teen aged girl and bounced a few times before running and flinging herself into my arms and kissing me multiple times while trying to tell me between kisses how she missed me and was looking forward to spending the day and night with me! I laughed and kissed her back and told her she was silly as we had just spent the last 10 hours together. Well, she was with the other me. I mean the male version of me....as opposed to this female version I guessed she liked better?
"You silly goose. I like you both equally, but the Kandi version of you is not my coworker, and as such, you know I don't date people I am working with!" She smiled to take the sting out.
"Now let me show you how much I missed you darling!" She said with a twinkle in her eye.
She pushed me against the counter, pulled my shorts and panties down and promptly started to suck my cock until I came in her mouth and then tongue kissed me so that we could share the creamy reward. I naturally had to return the favor and pushed her into her chair after pulling down her panties and reciprocated the blow job and kiss while looking up into her eyes while blowing her.
We spent the rest of the day lounging, shopping, and working on tans until it was time to dress for dinner and then the club. Janet put on her dark brown leather mini with a light green silk top and dark stockings and heels and I put on my crotchless seamed hose with a gaff thong panty, no bra, the black and green minidress we bought last week with 5-inch black heels and big hoop earings and golden studs. My nails ended up being glued on French Tips with smoky eyes and dark lips as well.
At the club, we drank a few glasses of wine, danced together and had several men hit on us, but we always declined. We were having a grand time until we saw Lydia with Wicham dancing and drinking. We left after that as I asked Janet not to start anything here, as I did not want anyone to know of our dating in case either one read who I really was and that would get me fired for sure.
We ended up back at my place and I spent the rest of the night slowly making love with Janet like two ladies would. Well ladies with a little something extra to share. Janet lingered in the morning with me over coffee, breakfast and more snuggling and kissing and some further gossip.
We dated regular for a month more before I gave her a key to my apartment and she gave me the key to her flat. It became apparent to both of us that something was up wiht Lydia and Wicham as they would sneak out to lunch together or be found chatting in the break room. I was starting to get some smiles and comments from Janet's sisters and a few of the lawyers about looking a little 'worn, but happy' on Monday's and that Janet also seemed to be suffering from the same ailment. I once said we were not a couple like Liz and Mike or Lydia and John were, and that last part got some raised eyebrows as I do not think people actually knew about them and I had to talk fast about just a comment I had overheard them saying to each other about a date and my making an assumption.
Two more months of dating and it had become obvious to many that we were indeed seeing each other as we went to the wedding of Liz and Mike as an actual couple with her father wondering about me, I am sure, since he must know that Janet is Pre Op. Since Janet is part of the wedding party, I am sitting on the Brides side and close to the front so I can see her in a lovely pink Brides Maid gown that shows off the curves of her and her sisters while the gents are all in grey tuxes with pink ties and the Bride and Groom are in white with little splashes of Grey and Pink. It is a short, but romanticly themed wedding ceremony that has Janet looking at me several times with tears in her eyes and I am smiling at her hoping that she is enjoying the ceremony.
At the reception, She does manage to catch the bouquet while I actualy somehow get the garter. When we are set up to do the garter and bouquet dance, I wait till about half way through it and whisper to her, "I have a secret to tell you. I set up that you and I would get the garter and bouquet as I have a ring I want to give you if you will marry me?"
She stopped dancing for a moment and looked at me searchingly before responding, "I love you Kevin. I love Kandi too, so of course I will say yes!"
Happily, I dropped to my knee there in the middle of the dance floor and pulled out the ring I had purchased a few days earlier and offered it to her while asking that time old question,
"Janet Bennet, will you do me the honour of accepting this ring as a token of my love and our pledge to marraige?"
"YES!" she replied tearily to many shouts and cheers.
We spent the rest of the reception in celebration as a second Bennet girl was also getting married. Kitty and Mary were prowling the single guests and I am sure they recieved numbers form multiple available gentlemen, but shortly after Janet and my announcement, Lydia and Wicham were nowhere to be found.
Extensive searching finally found them at the Justice of the Peace using embezzled money to purchase a wedding liscence and a honeymoon in Puerto Rico. Mr. Bennet was furious and actually halted the process before it could be signed, and terminated Wicham right there in front of all of us. He then angrily stated that a restraining order would be issued for him to stay away from his daughter.
About two weeks after I proposed, We cleared out my apartment and I moved in with Janet at her flat. The evenings were like two college girls living in a dorm together as we played games, drank, played dress up together and often spent time cuddled on the couch watching the latest movie or catching our breathe after sex. One of the things I noticed was that Janet's dress at work stayed conservative to a degree but on the weekends it was much more risque and alluring, while my work attire did not change, my weekend wardrobe as Kandi become more sexy, tight and revealing....OK, kind of slutty with the extra short skirts or lowrise fitted jeans and crop tops showing plenty of cleavage. Oh and did I mention I was in heels or tall wedgies as much as I could? We both ended up getting our belly buttons pierced and I also had my tongue done as I know it just thrilled her to feel it on her cockhead when I blew her.
We started to spend time working on the wedding and settled on a Mexican theme as that was one of our first dates and while Janet would wear a traditional white gown, I would wear a white womans tux with mens shoes and a pair of blue thong panties. Her sisters would again be Brides maids and Elizabeth was her Maid of Honour, while I had 5 of the lawers as my backups as they were the ones seeing all the daughters anyways! Our ceremony was short, sweet and to the point with the reception party a long, loud party that had a live band and lasted for several hours with all the dancing and eating and cake and more dancing.
When it all ended, We were driven home in a limo and I carried Janet over the threashold and intot he bed room where I lifted her dress and swallowed her sex till she came in my mouth and then I pushed into her ass pussy and fucked her for several minutes making her come again and then as I was about to come, pulled out and fed her my organ so she could swallow my seed as I had hers. In the morning we reversed the rolls and she sucked me off and then pounded my ass with her meat until she was ready to feed me her creamy goodness. We showered, dressed and finished opening gifts and gathered up the cash to take with us on our honeymoon to Hawaii!
Once we got off the plane in Hawaii and checked into the hotel, Kandi ended up being brought out for the week and she was the one who had the honeymoon with Janet. Much time was spent in bikini's working on tans, being flirted with and treating each other like openly gay lovers and actually being accepted as such. The entire honeymoon ended to soon and we went back to being Janet and Kevin on our way back. The Father gave me a raise after about 3 months of marriage and we now live comfortably, with a challenge of maybe making the change to dressing as Kandi full time our next adventure.