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Be sure to know what you wish for By Tvstar My Roommate and I had been living together for 14 or 16 months, we both had landed in crappy jobs that barely payed the bills, but we were having the time of our lives. The good thing about crappy jobs is that the responsibility goes down to a minimum and that's good for the sloth. We both had business degrees, but he had the job of a sales man and I was just an office clerk in the headquarters of a big department store. We spent most of our free time playing video games, drinking inside the house or in Bars and he spent a little more time with his boyfriend either in the house or hanging outside, I spent every time I could in dresses, skirts and heels, yes I was a closet crossdresser and that was one of the things that helped us band together. The best thing about a gay Roomie and his boyfriend is that they never hassled me about my crossdressing. My room had cost me a lot of time and money, it was worthy of a Princess. It had pink and purple all over it, in the bed, the comforters, pillows, I had a white vintage looking vanity with pink and gold details, a very big closet and the walls were covered in books and shoes, I loved my room. Whenever my parents or brother came to visit I had to tell them it was the room of another inexistent roomie, but my mom had never bought it, my father and brother just decided they didn't want to know. Our days were very normal, we woke up very early, got cleaned, have breakfast and get to work; we usually used only one car either Roman's or mine, we worked a little far from each other, but my work was in route to his and I could save on public transportation and gas that way. When it was my turn on the wheel, he just took the subway a little more to his job, it worked either way and that kept expenses low. I finished work every day at 5 and was always by 6 in our house, the first thing was always to get out of the required office suit and into a dress, skirt, leggings or whatever I wanted to, but in the house I always used female outfits. By the time Roman arrived I always had my feminine look complete. My job allowed me to use longish hair and they never said anything about my pierced ears, maybe because I was so low in the food chain. Every third day I shaved my legs and sometimes painted my toenails, I didn't use panties every day because it was a risk at work, but sometimes I went to work with a pair. Today (Friday) when I arrived at home I decided it was a little cold so over my lacy bra and panties I decided to wear black tights, denim short shorts, black leather flats a cotton pink t-shirt with small puffy sleeves and a long black sweater with lace back, my look was very comfortable, and I looked very girly, something that I craved every day, I loved wearing tights or pantyhose, with my shaved legs they looked fantastic, I liked heels more than flats, but this looked demanded for this also I wanted to be at ease. When I was putting my panties on I remembered the first time I had decided to buy a pair, how should I approach the sales girl? Where? What size? I had fumbled with those questions many times, the very first time I tried to look demure and as a very sissy boy; the girl saw me and looked very uncomfortable, and so was I. Of course she had sold me the panties, but It didn't feel right so the next time I bought something feminine I just went there with a lot of confidence and nonchalantly ask for this or that, if they asked me I just say is for a girlfriend, sister, etc. it always depend on what I'm buying. Sales people want to get rid of and make the sale, they really don't care or maybe they will gossip later, but on the mean time they don't even know you and sometimes they suspect something and they will gossip, but in the meantime it's not your problem or theirs. When I finished dressing up I always laughed a little at how I looked like a girl with a guy's head so I decided to wear a deep red lipstick and some mascara, not heavy eyeshadow or foundation today, just laying back and resting a little, later I combed my hair straighten it with the iron and pulled it in a high ponytail, some long dangly earrings and I was ready. Less than 15 minutes (even with the hair) and I looked very girly, very nice. I thought in the coming weekend and decided to complete my look with deep red painted fingernails, of course they were short, but with polish they looked very feminine. While drying my nails I went for a beer in the fridge and found out we were out of it, damn I'll have to get some, luckily there's a convenience store just outside of our building and they have known my female persona for months so I wasn't really worried, just annoyed because I was lazy and cheap. "Good afternoon," I said in my very best, very practiced female voice. "Hi, Dana, how's everything?" answered Horatio, the son of the store owners, I quite frankly couldn't stand him and rolled my eyes in a girly expression. He always sort of hit on me, made jokes and tried to make small talk, always at Dana and not to my male side Dylan, of course he knew both aspects of me, but I was sure he was attracted to my girly side, but I wasn't so I just smiled and got out as fast as I could. I bought a six pack of Coronas and some groceries for dinner, yes this was as typical weekend start as it could get. I left the groceries in the counter and opened a beer, I loved smearing the bottle with lipstick, I tried to remind myself as much as possible of my girly look, by feeling the breeze through my tights or moving the head with the earrings or checking my makeup in the mirror, I loved every second and tried to experience it as much as I could. The first times I had been able to dress up my pulse and everything went into high gear, I stopped being hungry and couldn't even have a bite, I sweated profusely and couldn't concentrate in any task, with time I got a little more used to it so I tried to remind me of my look to remember it and to better experience it. I turned the TV on and the console then started playing the new game we had just bought that weekend, Roman would be pissed if I advanced through the levels so I played online for a while. Then my cell phone rang. "Hey man, how are you doing? I am playing the Assassin's creed, don't fret or I'll start the campaign," I told Roman. Before he said anything then he answered, "Hey man, ummmm Jimmy is bringing a friend, I don't know if Dana is there or just you?" That was our cue to either stay in Boy mode or do something. Roman and Jimmy (His boyfriend) were cool with my Dana persona, but meeting new people was always a little scary. You see now homosexuality is mildly accepted, yes there are always some bigots, but society has been slowly opening up to it, but almost no body accepts a man in girl's clothes we have even been denied of gay bars that openly don't allow crossdressers, can you believe it? "How long till you get here?" I asked. "I had no signal until now we are less than 5 minutes time." This was a problem, I hadn't time to change back into Dylan, so I decided to amp on my girly side, and pray to be convincing in a very close inspection. I ran to my room and decided what I should wear. I decided for a flared black skirt that would help with my figure, the same tights, a nice white long sleeved silk blouse to avoid hairy arms and a turtle neck lycra top under the blouse to avoid Adam's apple questions (which was very small, but noticeable), black patent heels to help my posture. I was seated in the vanity redoing my makeup for a more complete effect when I heard the door. "Is anybody there??" asked Roman, more in a warning kind that anything else. "Yes dear, I'm just finishing here and I'll be out in a minute." He knew I had no time to change and Dana would be emerging from that door. I heard them chat and opened the beer, damn I should have waited they would have been the ones buying me drinks. I hadn't been edgy about my girly looks in a while, I had been out a lot of times and most of them I had been able to pass, but something in Roman's speech made me worry, I was very worried. I was even trembling slightly. "There she is." Roman stood up and kissed me in the cheek, Jimmy also stood up, and did the same. This is Frankie and old childhood friend of Jimmy we were having lunch and we sort of bump into each other, Jimmy told him we were coming for beers so he tagged along. "How do you do?" I asked in my best manners, he approached, leaned towards me and gave me a big kiss in the cheek, yes it is customary in Mexico to friendly kiss in the cheek, but rarely is done with strangers or people who have just met, very uncomfortable that was my first impression. We sat and I just let them chat for some time. I played the dumb bimbo and smiled with every joke or witty remark, but didn't participate in the conversation. I stared at Frankie a moment, because he looked a little familiar, but quite frankly I couldn't place from where. So Dana, he asked me, "What do you do for a living?" "Nothing fancy, I work at Sears headquarters some miles from here." "You kidding right? I just got in there! This is my first week." Roman almost spit all his beer, I almost pee on my panties. Oh fuck, This is the new golden boy from the HR department, that's why he looked familiar, I worked directly under the construction and maintenance department, but sure I had seen him some times in the last week in the common mess room or walking in the aisles. "I'm a consultor so I NEVER go directly to the offices," I harshly answered. "Yes that must be it, I couldn't have missed if I had seen you." We continued the small talk, but I deviated the subject of work every time it rose. After one hour, beers ran out and Roman volunteered to go for more, but Frankie stated, you know what, better yet. I'm hungry let's go for dinner, some tacos or a steak, I was really hungry, but I declined politely. "I have to work tomorrow morning, maybe next time." "Ahh come on it's not even nine, don't tell me you will get in bed this early." Damn, what else should I say, "Um no, but it has been a very hard day, I'd rather just stay at home." "Come on don't be a spoilsport let's go." And he grabbed my hand, THAT was really awkward. Roman was so surprised he couldn't find a proper excuse, until Jimmy said, "Come on Frankie, the lady said no, maybe you can see each other later on, we will go with you." "NO offense Jimmy," Frankie said, "I love you like a brother, but if I go out with a friend AND his boyfriend I will never live it down, I'll rather go with a beautiful girl on my arm." I blushed to this comment I knew I was passable, but outside the common Internet stalker nobody had said that to me. We three almost laugh in his face, but I made my best poker face. "Ok, ok some tacos that's it," I said. "Roman, and let's go to 'Hot sauce,' ok?" I specifically asked for that place because it was shady and the clerks knew me well so if got caught or singled out there wouldn't be any fuss. Jimmy rode shotgun and I was stuck with Frankie in the back, which sucked big time. Yes he was very nice and his chat was amusing and entertaining, we both liked the same books and games, but I didn't reply on these subjects, because I didn't wanted him to have a wrong impression, even though I loved wearing women's clothing I was not gay. I had had some run ins with girls and I knew what he wanted. Some years ago, I had been very confused with my gender identity, if I liked girl's clothing I surely was gay or so I thought, I tried to date some guys, but never found myself attracted to them. Roman even lent me some sex toys and gave advice in anal sex, all that because I said I wanted to try and to see if I liked it, but I didn't find it enjoyable, I found it painful and my stomach was queasy for a day or two after it. Later on I met Jessica, she was the greatest, she was funny, intelligent and beautiful, we hit it off really nice and we dated a lot of times, I even stopped shaving my legs on her account. I couldn't let myself go of the girly clothes, but I found love and care with her. So the dilemma arose, should I tell her or what? So I made up my mind and told her about my crossdressing. She didn't like it of course, but accepted that if she never saw me we would continue the same and I could indulge in my private time it was perfect at that time a sort of accepting girlfriend whom I loved. It was a great passionate time, we made love almost every day and we loved each other, I was even thinking in asking the "The question" even though we hadn't finished College, but tragedy had to strike. After we finished College she got a full scholarship for a PHD program in London, of course she took it and it meant the end of our relationship I was down for a month or so, but then I recovered and we spoke through skype in a regular basis. It taught me two things, yes I loved girls and Yes I loved Crossdressing, so I let myself indulge in my feminine interests, while I could or while I found the correct girl. When we arrived at "Hot sauce" Frankie was a gentleman and I had to let him be in order to keep the charade. There was a really awkward moment when we all stood in front of the door. "Letting the girl pass," so Jimmy pushed me gently to remind me that I WAS THE GIRL, so of course I passed and let Frankie pull my chair. The evening was nice, really nice, after some more beers I let myself go on the conversation and I had a real nice time, as I said before Frankie and I had a lot of common interests, so I had a good time as two guys talking to each other. About 2 hours later we got back to the apartment, we continued our chat in the car and the air started to get lighter, we had a really good time. Jimmy and Roman went ahead kissing and chatting like the couple they were, Frankie stood by my side and when we reached the door leaned very close to me and grabbed my hands, I began to get very nervous, "Dana, I had real good time, you are truly wonderful. Can I ask you something?" I was almost sweating (which could ruin my makeup of course). "Yes of course," I stuttered. "Are you a dude?" I felt hurt. Yes I knew that my disguise wasn't perfect, but for a moment I felt like I was failing and he saw my pain and hesitance. "Don't be upset, it's the way you hesitated in the door, the topics we spoke of, it was a little of everything, but your appearance is flawless." "Yes," I answered, "I am a guy, I'm sorry, I didn't mean to upset you or mislead you." He continued with the hand grip and that surprised me a lot. "It's ok, you weren't expecting me and I forced you to go out, your life style is your decision, I'm not attracted to guys, but I don't know why I find you VERY interesting, would you mind if we see ourselves a little more?" This surprised me, I really was expecting him to get aggressive if he found out, but I never expected this. "Ok, was my answer, let's try out." I surprised even myself with my answer. He leaned a little more and kissed me in the lips, then a little deeper in the mouth, I was very surprised and of course I reciprocated. After some minutes I could feel his erection and mine! So I broke it off. "It's better to leave it this way for now," I said while turning red, he smiled sincerely and nodded. "I'll find out your cellphone with Jimmy. Go princess, and have a nice night. I'll be in touch." Again he kissed me slightly in the lips and left, it was very weird, but I had to admit that I liked it. That night my confusion was evident, I didn't feel sad or angry, but conflicted. Of course since I started living here I hadn't used boys pj's to sleep, but today for some reason I wanted something extra sexy, so I slipped in a sheer black and red baby doll that barely covered my ass with the matching G-string, I tied my hair with a nice red ribbon and went to bed, that night I masturbated two or three times and somehow wanted something else, but I couldn't quite think of what. I had my beauty sleep and woke up late, about 11 or 12 in the morning, I was a little hungovered, but everything looked nice, my room was prettier than usual and when I saw myself in the mirror with the lingerie on, I thought I looked perfect. I had heard Jimmy and Roman in the night having sex and was happy for my friends, maybe I could surprise them with breakfast. That morning I chose spandex leggings with a hounds tooth design, I loved them because they were very comfortable and my legs and ass looked really nice and girly, then a sleeveless gauze mint sheer blouse, it showed a hint of my black bra beneath it, I brushed my long black hair and let it loose, a hint of pink lipstick and flats completed the outfit. I squished some orange juice and cooked some eggs and bacon, fresh coffee of course, the smell should be enough to wake them up. As on cue, both rose fast and in no time they were eating the breakfast, "Wow this is great Dany, thanks!" Jimmy then leaned and kissed me in the cheek, he had never done so, but I found it cute so I let him. "You know, Frankie is asking your number, should I give it to him?" This made me nervous, but it made me think that my worries, came from not knowing from him rather than the opposite, so I shrugged like indifferent and said, "Yeah, ok he's a nice fellow." They both saw each other in an accomplice look (the one you see in couples everyday) and just shrugged "Ok, I will." And with that he sent a text. The rest of the weekend passed normally, we cleaned the house, we played games and had our normal routine, but on the back of my head there was the little voice telling me, "Why hasn't he called me?" Sunday evenings are always the worst, the realization that the weekend is over is very upsetting, in my case I had to clean my finger and toenails and get mentally ready to cross-dress as a boy as I sometimes said. I felt a lot better using women's clothes and sometimes I felt that the suit and tie were the costume and not the other way around. Also that Sunday morning my annoyance was evident because Frankie hadn't called, not even a text, so reluctantly I turned the TV in my room off at about 1 am and let myself sleep, I even felt cheated for using the sexy silk slip I was wearing. The alarm clock rang ant 6 like every morning I took a shower, got dressed, and checked my appearance to look as manly as possible, today it felt very phony and ureal. Mondays are always packed with work, my mind started on a whirl of action and I let myself get immersed into the mundane, until at lunchtime my cellphone rang, I didn't know the callers Id so I answered like always in a manly voice. "Come on Dana, don't talk to me like that," said the voice on the other side, it was Frankie. I was very embarrassed, I really wanted to talk girly with him, but I was in the employees mess room, surrounded by 30 or 40 coworkers and I didn't want to be outed by something as trivial as this. I stood up and went to the door, were there was a little more noise and people just passed by. "Hi, you," I said in my best and demure voice. "That's more like it, I'm sorry I didn't call sooner I was busy with my moving and stuff, but is nice to hear your beautiful voice." I knew he was sweet talking, but it did the trick; I wasn't angry anymore and found myself wanting to see him I even had a hint of an erection, is weird to have male feelings thinking as a lady. "Do you want to meet for lunch?" he asked. "Now, you serious? I'm at work I look like a boy, you wouldn't want to see me." "You know is not true, I want to know every aspect of your life and as a matter of fact I am watching you right now." Colors went straight to my face and started nervously looking everywhere and true to his word he was about 20 feet in front of me sitting alone in a four people table, he saw me again and waved with his hand, so I approached him. "I knew it was you, you look good as this also." Thankfully he chose his words, but I felt really out of place. He started talking about last Friday, but he avoided a lot of details so he wouldn't give away any piece of unwanted info to an eavesdropper. As last Friday he was a good chatter and soon I got caught in the conversation, again we had a good time. Frankie was a really good guy, big, about 6 feet tall, broad shouldered he practiced swimming and was a very social person, he had just moved from Queretaro about 200 hundred miles to the northwest and he felt lonely, he had had his shares of girlfriends and love deceptions so that Friday when he met Dana he erased any prejudice; he liked this person, he wasn't sure he could like him/her in a romantic way, but it felt natural and he was willing to give it a real try. We talked like longtime friends, but also as coconspirators on a big secret and it was very amusing. As any work conversation, it derived into business soon enough and as HR guy Frankie asked me my opinion about the job. I told him that it was crappy and a waste of my education, but it allowed me spare time and money to expand my wardrobe, also that I loved the workers discount and had bought a lot of clothing in the SEARS, always in different places so I couldn't be tracked down and I told him about a lot of things that could be better in the office to this he just nodded. He asked me if I liked the sales girls uniform. I thought it was a common question for a girl or a trannie like myself and I told him that I didn't quite like it, that the skirt was too all fashioned and heels weren't mandatory so the girls sometimes looked scruffy and not classy like in other department stores. Then asked me again about the Office manager's uniform. "It is a lot better," I answered it is elegant with the above the knee cut, also the jacket fits nicely and of course all the girls use heels. "Would you like to use one?" he asked me. "Of course, I have bought some skirt suits that look like it, but I just have them there I never use things like that, because the situation hasn't presented itself," I answered. "I have to hire a manager in HR for a store south of the city that is not performing well, I know you have the profile and is easier to promote someone than to hire from scratch." I was surprised. "Yes, it would be a good leap for me, but what are you implying about using the Girl's Uniform? It's a nice position and I can fill it I'm sure, but are you implying something else?" I asked skeptically. "Yes, here is the win-win point. Company policies are getting updated, that means some office romance are now allowed, a casual day in the offices, some festival and cutback on office hours, but most important they want to hire a transgendered manager and here in Mexico is almost impossible, due to strict political issues almost no transgender people can demonstrate their studies or allowed to work in big companies, so here is the best opportunity I have to fill that position." He gestured me in open arms. It was the best way to really know if I wanted to be Dana full time, and not in secret. That sounded almost impossible. "So what do you say, will you do it?" "Can I think about it?" I asked. "Yes you have 30 minutes 'till break time is over." "I have only one worry." I decided to tell him fair and square. "Didn't you wanted to 'Get to know me' in a more private way? Or was this just a recruiting ploy?" "Yes I want to know you more intimately, didn't you hear me this is not in HQ is in the store, this way we will be even in different places and it makes it even easier to work, same office affairs hardly ever work, I think this is a better opportunity to try it out." "Ok, I'll do it, what next?" "Perfect I'll clear everything and I'm sure you'll I'm start by next Monday, I'll also clear you out with your boss this week so you can get ready; my bosses will need an interview of course. I'll set it up on Wednesday, so be ready AS DANA and I'm sure everything will add up." It was a whirl of words, but it sounded like he had everything ready, I was sure he had planned it since the weekend. Frankie sealed the pact with a handshake, but for a moment I thought he could lean and kiss me, maybe if he had done it I would accept it. True to his word he talked to my bosses and to his, I had a Dylan interview that same afternoon and they were a little suspicious that I could be passable as a girl or even that it was a possibility, they wanted proof; Frankie nodded at me and I showed them some pics that I had in my cell phone, they couldn't believe that it was me and scheduled the Dana interview for Wednesday. When I got home I was marveled by the weird day I just had. Suddenly I had a possibility to stay as Dana 24/7 without having to lie and could I have a possible boyfriend in my future? That thought was almost too weird to think about it, but I tried to keep it in my mind as long as possible. Strangely that was the part that made it more interesting and I couldn't believe I was thinking like that. The next morning I woke up early even if I didn't have to go to work I had lots of things to do and first things first, so I dressed up in a comfortable loose short sleeve romper and open wedges, just pulled my hair back in a ponytail and left for the beauty salon. I had been at the salon lots of times, I was friend with Johana the owner and she taught me a lot about makeup and hair dressing, but today I was going to fulfil one of my wildest dreams, I was to going to be feminized in a little more permanent way. Should I change my hair color? How trimmed should my eyebrows be? Bikini waxing? How long fingernails? For the first time all this little perks were not only in my grasp, but I was required to do them. As I said before I had black straight hair that goes to middle back and is really difficult to style, so I let them perm it and gave me a little curly structure also they painted some crimson highlights, I trusted in them and they delivered my hair looked really nice and very feminine. I chose half inch French tip fingernails, they looked elegant and helped my hands to look slender, my feet were with a similar design, of course I shouldn't use open toe at work, but maybe some peep toes or at home I could enjoy them, I really loved looking at my decorated toes any chance I got. Later came the waxing, I always shaved my legs and underarms, but today I was for a complete body waxing and I got carried away so I asked for a Brazilian, these people were pros and weren't fazed by my male parts so the waxed everything and also waxed my eyebrows leaving a very narrow and feminine arch. I had a very measly beard and waxing it wasn't a problem either I just had to maintain it regularly. When I left I felt like a different person, it was something I had wanted to do my whole life, but then it downed on me, yes my work was safe, but what will I tell my family, they might suspect it, but now I'm confirming it. There's no way to break it slowly for them this is a total war declaration, well maybe I could blame work, meh I'll just think about it later on, today I look like a princess. It was late when I arrived to my home, I laid some skirt suits on my bed and some office dresses to check what would look better on my interview. I wanted to look professional but pretty and very feminine of course. I had some outfits that would be work safe, but if I was going to pull this off I really needed more formal clothes and of course heels. That made me smile I had to do shopping sometime in the future. My new look also invited me to try again a lot of my older stuff and see how it looked with the new me. Unmistakably I looked really nice, and I didn't have to change back into boy mode before sleeping on a work day, this was something different no doubt about it. It was near 9 o'clock when my phone biped with a text, it was Frankie. "How r u? U rdy for ur big interview?" "Yep, I'm all dolled up." "rly? Send pic" I took a selfie with pouty lips and a sexy pose I had tried many times and sent it, by this time I was trying a very sexy, very small, very tight black dress so the picture was very enticing. "U look rly hot, can I go?" This took me by surprise, it wasn't late, I was about to turn in, but I wanted to see him and I couldn't deny it. "Ok *blush face* I'll see you here." My face was still made up and the hair was great, I just had to put on some sexier panties and platform heels, just a have a leopard print jacket nearby in case he would want to go out. In less than 5 minutes there was the doorbell, he was nearby, and just teasing me. He entered with a six pack in his hand. He didn't want to leave and that was fine with me, Roman was with Jimmy watching some Netflix in his room and I had just told them that Frankie was coming, they just send some conspirator smiles and wished me good luck. He stared me in an amazed way for some minutes "Wow you look stunning, the changes are very slight, but the result is incredible". I blushed profusely to this comment, he was hitting hard on me. Yes I knew his intentions, but nevertheless I found it to be new and interesting. We sat in the living room and started to talk, it was so easy to chat with him, very soon we had an ongoing conversation and very strangely we didn't even had to talk about work or the interview. After an hour or so he had taken his jacket and tie off and felt very relaxed with the situation, he started leaning closer to me as I let him do it, in a little more than 10 minutes he was next to me and took my hand. I was the one who couldn't wait so I sat in his lap and started kissing him hard on the mouth, lots of saliva, lots of tongue. His hand moved expertly to my ass and started fondling it. He did a great job and I found it very arousing; he was an expert and I understood why girl's found it so erotic. He then tried to squish my inexistent boobs, my bra wasn't even stuffed and he understood it wouldn't be at all interesting for me so he returned his hand to my ass and groin. The sexy black lace thong had been a very good choice. My dress was almost all the way into my waist and my makeup was all over his face, of course I had a very big erect cock, but he didn't seem to care about it he was avoiding to touch it but didn't seem disturbed by it. Later on he started caressing my legs with one hand and my ass and anus with the other. He looked like a hungry octopus on a willing prey. My hands also started playing with his upper legs and through his open fly with his dick, when he started to insert his fingers through my hole I got scared and the remainder of pain was enough for me to cool down, he noted it and slowed down. "Are you ok babe?" he asked. "Yes, but I'm not ready to go further." I saw the deception in his eyes and the very big and fully erect cock through the fly of his pants, so I knew I had to take one for the team and kept stroking it. Immediately he reacted and let me continue with the hand job. Then I fell to my knees and started licking the head, I didn't even thought about it, I wanted to make this guy happy and this was the better deal. It didn't have a bad taste, it was clean and felt very smooth, my tongue explored every part of the head, the shaft and even the balls, his pubic hair felt funny as it brushed my mouth and chin. After some moments I felt that he was deflating so I inserted the whole thing in my mouth and started pumping. The monster sprang to life soon enough. I wasn't ready for this. I had never done it and maybe in some fantasies I had considered it, but nothing could have prepared me, it was very tiring. My neck started hurting and it was very big, so soon it started touching the back of my throat and with a very light touch I almost puke, it was the gag reflex and I had never felt it. I struggled to contain it, because I really wanted to make him happy, then resume on the task at hand (or mouth). Soon enough the head started pouring the thick liquid of precum, I had no choice and had to lick it, but it surprised me a lot, it felt really nice in my mouth, it was slightly salty, but I loved the consistency, it was very tasty and I liked it. Then after my gag reflex was subdued I continued with the deep mouth fuck, at this moment he started pumping my face and that eased my work on the neck, this made me enjoy it a little more than I thought. After some more minutes he started to moan and got a little tense, I knew what was coming so I waited patiently. He poured like a gallon of cum, even though I tried to take it all, it poured through the sides of my mouth again the taste was nice, but the consistency got me hooked, I loved semen and became embarrassed by the realization. My dress, my face and my hair were all a mess, he took his cell phone out and took a picture, I looked ghastly, but somehow it made my own dick stir. It was past 11 and we both had to work tomorrow so I waved a goodbye as a gesture that I wouldn't expect a kiss with my smeared face, nevertheless he leaned to me and kissed me tenderly even tasting his own cum. I found it romantic. After a quick bath and donning a beautiful purple silk and lace slip I fell into heavy slumber. The alarm clock sounded at five, I ussualy woke at six, but my usual man grooming was ready in 20 minutes, now I had a lot to consider and it would be a lot more time. I decided to use a grey skirt and jacket women's suit, a white gauze long sleeve blouse, natural pantyhose and conservative 3 inch heels. My hair was styled loose, but very formal, my makeup was natural and decided to use a silver scarf to conceal my Adam's apple when needed, small hoop earrings a small sized purse with makeup, money and my IDs, for a moment I thought about taking some guys clothes with me, but with my new hair and nails that would look even weirder. Roman woke up at six and was getting dressed when he saw me, of course he knew everything about the promotion and checked my attire, "You should use more padding in your hips, that skirt isn't flattering your small ass... aaaand speaking about ass, how was yesterday?" "A lady never tells," was my answer and he just laughed. "Well sooner or later you'll talk, you'll see princess." I loved it when he called me princess and today I felt it more real than other times. I drove to the office, I have always liked to drive in heels not only it feels completely different also it adds a little torque to the foot, believe it or not is easier to drive in heels than with flats. I was early for the interview, but I really needed time to chill, I had been in the office for almost a year and the interview would had been enough to be afraid, but I was now in full drag around a lot of people who knew me well, hell they even knew my car, right from the start they would see me and mock me. When I arrived at the security checkpoint, the guards saw my car's ID and then looked at me inside, they asked me to stop and my trembling was now very noticeable. "Yes?" I asked in my sweetest voice like trying to imply I was another person here inside. "Good Morning Mr. Ayala. We have been briefed in your coming and appearance, please park through the back entrance, my partner will be there and escort you to conference Room B, so nobody will disturb your work. Let me just tell you that you look very nice, please come in." This was absolutely surreal, I was been treated as a VIP and even complimented in my looks those reforms Frankie was talking about really were really happening. To?o the other guard escorted me and said, "To be truthful, I thought you would look really bad in a dress, but I was wrong. You didn't even needed my help escorting you. You would have passed through and the only looks you would have met would be of approval and jealousy from some girls, you look great Mrs. Ayala." He finished with a female surname and that was a very nice gesture. I won't bore you with the details of the meeting, it was long and tiresome, they thought that even though I was qualified I lacked the experience for the job, of course they didn't question my commitment when they saw my appearance, Frankie wasn't among the interviewers and when I asked about him, they told me he shouldn't be present because he was just the recruiter. They asked some very personal questions, and of course about my gender identity, I told them the truth, I was just a Trannie and hadn't considered being a woman full time, but that I would do what they asked, they of course were satisfied. They didn't dwell a lot on the issue they gave me some papers, I signed them and told me that there would be orientation in HQ tomorrow and the day after. That I should present myself on the store by next Monday, Of course the Job was mine. When I got back home Roman and Jimmy asked about the interview, so I told them everything and they asked again, it was surreal also for them. I had only kicked my heels and was relaxing in the couch when Frankie arrived, again I repeated the whole story and we laughed a little about it, we made out with some kisses and fondling, but I was very tired so I excused myself, he understood like a real gentleman and left with a very big and passionate kiss. The rest of the week passed slowly, every day I woke up got dolled up and went to the office to get my orientation. It was really hard work filled with 12 or 14 hours of continuous work, there were four of us managers in training two guys and a girl, but I was the only transperson. They found out before lunch the first day; there was surprise and in lunch there were a lot of questions, but I was respected, something that I never thought would happen. After lunch of course they talked about human rights and equal job opportunities so it became obvious that my presence was derived from a change in policies this made my classmates suspicious of my qualifications and I had to work hard to show them that I was as competent as them. Those nights after work I studied everything they gave us and was sure to understand and remember all to show them I wasn't there just to fill a position, even the girl (Martha) had seen me as a ladder chaser, that I was just there because I had a penis and looked good in a dress. Frankie just called on Thursday he said that he had a lot of work and wouldn't be coming on Friday he passed by but again I was too tired to do nothing more than have a beer and talk. Weekend wasn't better, I had to show that I was the best person suited for the job and not some politically correct poster child, because of that I studied a lot those two days, by Monday I would be an expert. The weirder part of the weekend was that I was tired of using heels and skirts, I became a little frustrated that I even didn't want to use informal skirts or shorts I took sweat pants and found them even more comfortable with boxer shorts than lingerie so my craving for feminine things was a little off for the moment. Monday was difficult, I used a very form fitting navy dress, black pantyhose and a long coat, my hair was in a cute bun and small earrings, my heels were higher than they should, but they helped me adding some inches and of course authority. I met my staff and made a tour of the facilities, everything was ruined down and crappy, the sales figures were in a deep plunge down the general average and everything looked shabby and disheveled, people were unmotivated and there was a lot to do. This was a man's job, even though I looked great in this dress. Again that week had 12 and 14 hour shifts. Of course in a store like this the busiest days were Saturday and Sunday so I decided (because it was my decision) that my free days would be Mondays and Tuesdays and of course not on weekends like almost all the store managers, so this week I would work the seven days and would take my free days only if the workload allowed it. Even at night I didn't feel sexy. I was just too dammed tired and for the first time since I lived in that apartment I went to sleep with a pair of boxers, also I asked Frankie not to come, I didn't feel like it. Of course this caused turmoil. Frankie called me every day and tried to subdue my mood swings, but his pleading wasn't really helpful. Sometimes he came at night and we talked and made up until I sucked him. I really wasn't ready for another thing, but at least it was nice to have a boyfriend. I didn't have a free day in four weeks, weekends, Mondays and Thursdays were all the same, just trying to plug the holes in the office. Yes of course every day I looked fantastic and not being worried about people finding out about my dressing, I began to feel respected because at last results were showing. Sales started picking up, the place was a lot cleaner and people were happier, I got to use the girl's managerial uniform and it felt really nice, I also upgraded the sales uniform and people liked it, as I said I was respected, they stopped feeling that it was just a PR stunt. Women liked me, because I understood about fashion and shopping. Men started respecting me because I talked to them in a harsh way, of course like a man and I also understood their language. In my first day off I planned a romantic evening with Frankie, I had bought with my employee discount the most expensive sexy lingerie and also a nice evening gown, everybody knew there was a man in my life and they wished me luck, even the men! On Monday I asked Frankie if we could go out to dinner, he agreed to go for me at 6:00 o' clock a little early because for him it was a work night and I had to be sensible about it. I gave my 100% to this date, my black tight sequin dress was long and elegant it had sheer sleeves and shoulders it finished almost at were my heels were and it was tailored to my measurements, it looked like I had some curves and didn't even need padding, this helped me use the silky black G-string and garter belt, the matching panties over the hips, to help support my male parts. Then the matching bra and filled it with very expensive breast forms glued to my chest. Jimmy Choo black stilettos and a very beautiful necklace that was lent to me by store, of course silver dangling earrings and a great salon hair style for the occasion, with the dress I looked really nice and without it I looked spectacular. Frankie was there at 6:00 pm sharp, we went to a very fancy restaurant and had one of the best meals I had ever tried, every look was on me, people really liked what they saw and Frankie was puffed like a peacock but behaved like a gentleman of course the main dish was to be served later on. I had asked Roman and Jimmy to leave the apartment to me and they complied. When we arrived Frankie hastily grabbed me by my waist and started kissing me all over my mouth, my neck and then licked my ears and upper chest. I unzipped the dress and let it fall; he gave a few steps back to see me. "My god, you are beautiful, you are the most beautiful woman that I've ever been with." This made me really happy, I liked that he could see me as a complete woman that and the feeling of the lingerie which intoxicating, and of course I started to have an erection, his was already at his peak. He reached my panties and started rubbing my sex, this startled me because I thought he was really averse to it, but he didn't look like it and touched really gently nevertheless. Silk against my cock was really incredible and of course I had felt it many times, but his ministrations made it great, I continued kissing and of course gave him the same attention, he then proceed to lower my panties and expose the G-string, my cock was at its peak and the flimsy garment couldn't contain it so it moved sideways and liberated itself from the constriction. My groin was of course completely waxed and the string rode up my ass showing only the small black bow on my upper cheeks then with his right hand he continued stroking me but his left moved to my ass and starting proving with one finger inside my hole. It didn't surprise me; I knew he wanted it and I did also. His finger started by feeling invasive but soon it felt better, my ass was kind of lubricating itself, but I knew that it wouldn't be enough later on. I began getting a little worried and he noted it in my trembling and the decrease of my erection so he pushed gently my head to the front and to the couch so my ass was completely exposed, he then started licking my anus. I wasn't at all prepared for it and it felt very nice. I knew this part was very erogenous, but as a guy I had never felt horny by anywhere else than my dick. By this time he was stark naked and also for the first time I started to find attractiveness in a man's body his toned muscles and the strength that he projected was very sexy, he withdrew for a moment and reached his pants, he took out a small bottle of some fluid and tarnished his fingers with it, of course it was lubricant. He was expecting this or maybe he had had it with him for a while. He inserted two lubricated fingers and started masturbating himself, the small drops of precum that came out of his penis were used also as lubricant or recovered and fed to me with his other hand. Soon he reached my prostate and again my erection was at its fullest. It was time to pop my cherry. He started inserting his very big tool and I was surprised about how easily it entered. All that massaging had prepared me really nice, of course it wasn't painless, but the ache was brief and very soon I started felling a great sensation a fulfillment, then he started pumping. All his strength was focused on his member and it was like I could feel all his might inserted on me, it was sexy as hell. How could I have not experienced this? After some minutes his balls started ramming my butt, I knew he had reached his limit and not too soon, maybe I could have taken it more deeply and I started to crave for it, but for now it was perfect. His thrusting was slow and deep, tender and every time he inserted it my own sex stood. After about 20 minutes (that's why he was the man, I would have come in about 5) he tensed up, I was sweating profusely and couldn't wait more, I started feeling his semen inside me, I liked very much how it felt, it was fulfilling, but missed it from having it in my mouth so I reached with one hand and tried to recover as much as possible and licked my fingers with it, then with my hand covered in seed I tried to masturbate, but when I touched my cock my own semen poured out, I had never felt an orgasm so intense and it felt sooo right. I laid there in the couch for some minutes, everything was very dirty with both of our semen, my dress was all stained and my panties were in the floor, I was there in the remaining underwear and still looked sexy. I thought I would get embarrassed or uncomfortable, but I didn't it felt romantic. "Do you want to spend the night?" I asked him and I laid a hand for him. We went to the bedroom. He left his suit there in the living room, he laid in the bed and quickly fell asleep, I removed my makeup and put on very sexy electric pink baby doll that left my ass evident. I adopted a little spoon position and he hugged me. This felt very nice and his dick rubbed my sore asshole that was a huge bonus. At about 3 in the morning he was hard again, he positioned me and fucked me once more I went on with it of course it was nice, but a little of the magic had been lost, he came and fell asleep it was just mechanical so after it I had to masturbate to discharge I found that tasteless. At five in the morning he gave me a kiss in the forehead and fled. That Tuesday I caught up with a lot of chores I hadn't been able to do because of my workload cleaning, laundry, dishes, dry cleaners, bank, etc. I felt fine, but a little cheated. Of course I had enjoyed it and I discovered I loved being penetrated, but again I felt disconnected with Frankie, he was a great fuck buddy, but didn't feel a bond like I had with Jess; I missed her a lot and felt more alone than ever. That day didn't even wanted to use girl's clothing, I put on some old jeans and T- shirt and looked very weird with this clothing and a girl's head almost like a reverse way of how I felt before with my women's clothing and a guy's head. That afternoon, Roman and Jimmy asked me how it was, I told them every dirty detail and told them that I had liked it, but that I didn't feel at ease with Frankie. "Well Dana, a relationship is not only sex, Jimmy and I are happy because we complement each other, ok sex is great, but the other 95% of the time is what makes it tic" I knew he was right of course, I couldn't relate romantically to Frankie and I thought he neither. For the first time in about two and a half months I called my mom and told her about my job promotion and how I started a relationship, but I wasn't at ease with neither of them (The job and the relationship) I purposely avoided gender pronouns and my looks, but of course she knew something was different, while she doesn't talk to my father or brother I should be fine. Also I sent a mail to Jess, Her perspective would help me. She knew me better than anybody and when I was sending it she replied me with a request for a live skype feed. Shit I really didn't want her to see me with my dyed hair and trimmed eyebrows. She loved me as a man and she wasn't thrilled with my feminine side. After 5 or 6 denied requests I typed to her that she wouldn't like what she might see, she replied harder so after 9 or 10 intents I let her see me. Of course she was surprised with my look, but kept silence I explained that it was all a ruse from work and that I felt very lost. I omitted my dealings with Frankie of course. She listened and tried to encourage me, but I could see the deception in her eyes. I was no longer the man she had loved, she looked cheated and hurt. When we finished the conversation I knew I had lost her and that I would never speak with her again. I finished my day with regret and the major feeling of loneliness I had ever felt. Frankie didn't call me all day and neither did I. Wednesday was my week starter and there was a lot to do. Cleaning, distribution, finance, everything was off and I had to run all over the store in my highest heels. That day I overcompensated and I used the smallest proper skirt, the prettiest stilettos, the sexiest blouse and my most form fitting underwear. I was only allowed in one bathroom in the store to ensure girl's privacy and that also proved difficult running from here to there all day. By the end of the day everybody was happy with my results, respect again was on the rise, my bosses loved me and my staff was at ease with my leadership.... Yes everybody was happy except for me. I left work as early as possible. My daily results gave me this chance to once in a while leave early so at 6:00 o'clock I really wanted to change my clothes and slip into something more relaxed. The driving home was done shoeless and I didn't even put the shoes back when I got home. I walked all over the parking lot in very sore pantyhose encased feet. When I slipped my key I noted a weird atmosphere, something was amiss and I would have called it feminine intuition if I had been a girl. When I opened the door my mother, father and brother were waiting for me and Roman was there. They must have forced their way in after my distressed call to my mom, I could have died just then and there. "Dylan, what the fuck is happening here?" my Dad shouted at me, my brother was laughing hysterically of course because of his shattered nerves. In a twisted way he couldn't believe my look. It was not possible. "Shhhh Dad, let me explain," I told him while I seated in a noticeable feminine way straightening my skirt, it was quite evident that I was no newcomer to women's clothing. "It's you, right," he said pointing a finger to Roman. "You recruited him, I knew you fag were a bad influence to my son, are you screwing this fucker?" he then asked me. "You know what Dan... Dylan this is your problem you fix it, bye." And with that Roman stormed out. I was on the ropes, and I was also broken, so I let everything out, I told them that I was interested in crossdressing, but just in a personal and private way, yes I liked wearing this but what had happened on work wasn't at all what I wanted. They listened to me and anger started subduing, then David my brother asked about Roman, "So are you a Fairy now like that guy?" First it made me angry that he was so closed minded and stood by my friend; then I told him that of course I was not having sex with him, but then my mom asked "And another one? Are you having sex with Men?" I couldn't lie to my Mom and she read my expression she had known about my Crossdressing, but on her mind this was too much. "Son, you know I respect you and any decision you make, even this one I will accept it, but I'm not sure this is really yourself." When she finished I was on the brink of tears. When they left they looked a little better. I knew that they might in the future accept my crossdressing and even if I chose it they would accept me being gay, but they loathed looking me miserable as I really was that was the real problem. The rest of the work week passed by with a crawl. On Sunday management was allowed to use informal clothing, a little like casual Fridays. That Sunday I went to work with Boy jeans and a formal work Shirt, without makeup and my hair pulled back in a ponytail, I looked as manly as I could, everybody flipped out. I worked as hard as any day, but all my staff looked at me like a freak. It was unbelievable everybody knew I was a man, but they couldn't stand looking me without a skirt, to them this was treason; I was a crossdresser now for looking as a man, and not the other way around. So fuck them they were able to accept me with a dress, but this was the truth. Of course the contract I signed binded me in female garb, but on casual Sundays I could wear whatever I wanted, just like them. At the end of the day I gathered all of them and told them, "Guys it was a good day, we surpassed sales and did everything in the best way possible." They all clapped, I wanted them in a good mood. "I have seen the look on your faces, my looks are in the general gossip, I find it very amusing that I earned your respect even though all of you knew I was a man and men shouldn't wear skirts but this is who I am, I don't mind wearing a skirt I like it. So think, my heels are not what have made this success. It is the essence of me and of you, it's not what I wear, it's how we all work together and we all need to take our roles, mine is to lead you and is something I do with all my might not caring what I wear." Everybody clapped after this and from that day on the workforce found a peak, some guys even asked if they could become sales girls, I said that like everybody they have to take the tests and be approved by human resources, but if they cleared out why the hell not. My job life became better and steadier, now it was time for my love life. In two weeks I hadn't heard of Frankie, not even a phone call. I called him a Friday and asked him to meet me, when we saw each other it was on a Caf? outside my job, I understood. He was breaking up with me. "Dana," he started, "I don't know if I'm the right man for you." "Frankie, before you continue..." I interrupted him. "You never told anybody we were seeing each other, you never expected it to last, and neither did I. You did your job, you found your Trannie for the job, that's what you wanted from the start," I continued. "But is not like that, I set you free you were hiding in your house," he said. "Truth will set you free." "Yes," I accepted. "I no longer hide my dressing, I was honest to everybody... except for me. You see I liked being a closeted crossdresser, I liked the thrilling of being discovered, the cleverness of buying the 'wrong' clothing, I liked looking at that clandestine girl in pictures and the mirror, it stopped being fun when I got forced into it, I grew tired of having to look perfect every day and the loneliness that comes when you can't relate to anybody." "Yes I didn't have to hide that I like dresses, but I had to hide my feelings, and you know that's worse." "I never wanted to hurt you," he started to say in a rehearsed speech. "No I know, you didn't, you thought only in you. In your career, in your desires." "So are you quitting the job?" "No I won't, my gender issues are way past my team and me. They want me as their leader even if I'm wearing a skirt or not, maybe sometime I'll find a middle ground." "But you liked the sex," he said. "Yes, I enjoyed it, maybe I'll find a lover or a dildo I really don't know about it. Once I thought that I couldn't relate romantically with men, but I maybe it was only with you, you showed me to keep my mind open I'll go out more meet men, meet women I don't know who I will be with, but I'm sure it is not with you." Said that I stood up, with my heels towered more than 6 feet tall and quite looked menacing, he was seated and that made him quiver a little. "Goodbye Frankie, I won't be seeing you and I won't be missing you." Epilogue Sometime later I reached an agreement with HR, I had some employees that were better transpeople than me so the quota was filled, I was released from my obligation and was allowed to go to work as a Man, I preferred that I was a crossdresser not transwoman, sometimes I bought dresses and other female clothes in the store and the sales people even allowed me to try them in the dressers and gave me some pointers, the alterations department were always really helpful my crossdressing wasn't a secret, but it was on my terms. At the Christmas party I was asked to go with a dress and of course I complied with a beautiful evening gown. My love life is not complete yet, I've dated some men and the sex has been great, I've dated some women and the sex has also been great. Maybe I like both strawberry and chocolate, but the most important thing is that I haven't found my soulmate and when I do I'll have to settle in that form choosing means resignation I intend to choose carefully. In the mean time I'll keep looking and have a great time wearing whatever I feel like at the moment and maybe, just maybe find someone who does the same. It's a really big world out there and considering gender issues it's getting bigger.