The Office Party And Pleasing The Client free porn video

The Office Party By RogerGirl "Come on," my girlfriend Tina says, "it will be fun. Besides you know they already joke about it anyway." "I don't know," I say, "nobody else is going to be dressed up. It isn't a costume party." "By the time I'm done with you," she says as she strokes my long brown hair, "we'll look like any couple at the party, except I'll be dressed as a man and you'll be dressed as a woman." Reluctantly I agree. Tina is ten years older than I am at thirty-four and since she is the only one working she has more power in our relationship. The truth is I probably will make a pretty convincing woman. I've always been pretty thin and since I lost my job I've let my hair grow out. My voice is also higher than most men my age and I have no visible Adam's apple. I think I'm more afraid that I will end up looking too good as a woman. Tina's co-workers already joke that she's the man in the relationship, what would they think if I show up dressed as an attractive woman? In the weeks leading up to the party Tina has me practice dressing like a woman, including working on putting on makeup, speaking in a feminine voice, and practicing feminine gestures and body language. Having no job I have a lot of free time while she is at work. After a while I find myself getting pretty good at it and even start to enjoy keeping my body smooth and hairless. After spending some days dressed as a woman while Tina is at work, I dare to venture out one day to see how well my disguise actually holds up. Nervously, I drive to the nearby grocery store and walk around the store doing my usual shopping. As I walk through the store, I notice guys checking me out and surprisingly I find myself enjoying the attention. I begin flirting with one guy who I find myself thinking is very attractive. To be honest, I've never had any attraction towards men before, but in my new role I quickly am discovering a side to myself I never knew existed. I panic a little and hurry away to pay for my groceries and head home. On the evening before the party I decide to surprise my girlfriend by showing her how good I've gotten at pretending to be a woman. First I prepare us a homemade dinner, then I go into our bedroom and take a long bath. Once I'm clean and smooth, I attach the prosthetic breasts and vagina we ordered and I put on my sexiest lingerie. I work on my makeup, hair, and nails and once everything is ready I spray on some perfume and put on my highest heels. I check myself in the mirror and I have to admit I look pretty hot. I return to the living room, set the table, and mix a martini for my girlfriend. I stand by the door as it opens holding a martini out to her. "Welcome home baby," I say in my sexiest female voice. "Oh my god," she responds in shock, "you look amazing. Maybe you look a little too good. You might have to dial back the sex appeal tomorrow night. I think I should change for dinner." She goes off to the bedroom and closes the door behind her. I curl up on the couch and wait for her. At this point I'm in full female character and any signs of my masculinity are tucked far away. For now I'm no longer Noah the unemployed stay at home boyfriend. In his place is Naomi the sexy girlfriend. After waiting a while the door opens and out steps a man. Tina is wearing a suit and has her hair tucked under a short male wig. She has always been taller and more muscular than me, and I have to admit she looks more masculine than I ever do. Tina, now Tim, comes over to me and pulls me in for a kiss. I feel so vulnerable as his strong arms hold my tiny waist. He sits on the couch and pulls me into his lap where we stay making out for quite a while. For the rest of the night we stay in character as Tim and Naomi and even sleep together that way. Although we've both gotten pretty comfortable playing these roles, we still feel strange doing anything sexual like this, so we just kiss each other and go to bed. I must admit though that playing these roles has made me curious as to what it would be like to be kissed by a real man and feeling Tim's prosthetic penis against my thigh has definitely got me feeling strange new urges. The next evening as we enter the party at the hotel banquet room, everyone's attention is on us. Tim is wearing a suit and I'm wearing a little black dress that shows off my stunning long legs and plenty of cleavage. By their chatter it is evident they don't recognize us and are more interested in who this mysterious couple is. Tina's boss walks over to us and greets us. "Excuse me," he says, "this is a private event. I'm sorry, but it's for employees only." "Joel," Tina responds in her female voice, "it's me, Tina. We decided to get in on the joke tonight." "Wow," Joel says, "I had heard rumors you would be doing this, but I never expected you two would look like this. What should we call you tonight?" "Tonight I'm Tim and this is Naomi," Tim replies in a male voice. "Well I must say you look gorgeous, Naomi," he says as he looks me over. "I know you're straight, but would you like to dance?" I look to Tim and he gives me a nod of approval. I take Joel's hand and he leads me to the dance floor. I may be straight, but I have to admit I have sort of a man crush on Joel. He's everything I've always wanted to be. He's tall, good-looking and successful, has a nice car, and can get any woman he wants. Ironically, tonight I'm that woman. I must admit I'm flattered he finds me so attractive and I have to say I find him attractive as well. As we dance he continues to tell me how good I look as a woman and how much better I look than the other women at the party. As I look around, I realize he is right. At the end of the dance he gives me a kiss on the cheek and leads me back over to the table where Tim is talking to some co-workers. As the night goes on, everyone treats us as Tim and Naomi. Several men ask me to dance and the women even invite me to join them when they go to the restroom. Tim is enjoying being one of the guys and getting to chance to be included in conversations with the other guys in the office. Joel, however, is more interested in me and continuously places his hand on my bare thigh as we sit at the table and talk. As he gently strokes my skin and flirts with me, I feel conflicted. While the attention feels nice, it does feel strange to be getting such attention from a man. Tim turns and notices what is going on. He asks me to dance to save me from the situation. "Sorry about that," he says as we dance. "Should I say something to him?" "No, it's fine," I reply. "Let's just get through the night." After the dance, we return to the table and find it empty. There is a note near my plate with a message left by Joel. It says to meet him upstairs for some fun. On the back is a room number and a room key is tucked in the pocket. I show it to Tim and he tells me it is up to me. I don't think I'm gay, but after seeing how incredible it feels being a sexy woman I am feeling a little curious. I doubt I would do this as Noah, but the thought of being with a guy like Joel as Naomi is starting to turn me on. I tell Tim and he tells me that it might be good for me to explore these feelings, but to be careful. I go upstairs and discover the room is a suite. I enter and find Joel wearing only a robe. He hands me a glass of champagne as the door closes behind me. "I'm glad you came," he says smiling. "I know this is probably the first time you've been with a man and you're probably just curious. If you feel uncomfortable at any point just let me know and we can stop. Personally I don't view beauty in terms of gender. I have been with men and women, and you are by far the most beautiful person I have ever met." "OK," I respond nervously as I sip my champagne. He takes my purse and champagne and puts them on the dresser, then he puts his arms around me and leans down to kiss me softly on the lips. Even though I am still wearing my heels, he is still much taller than me. As he kisses me I begin to feel a strange sensation. While I know I still love the feeling of kissing the soft lips of a woman, there is something equally enjoyable about being on the other end of a kiss. The experience of being held by his strong, muscular body and feeling the stubble of his strong jaw against my soft skin leaves me wanting more. I open my lips and invite him in. We standing kissing passionately for several moments and I know I want more. For now I don't care if this means I could be bisexual, all I want is to get out of this dress and let him take it from there. "Should we stop?" he asks as I break our kiss to unzip my dress. "No," I reply smiling, "I just wanted to get more comfortable I say as my dress falls to the floor. As I stand before him in only my thong, since the dress required me to go without a bra, I catch my reflection in a mirror. For the first time in my life I'm glad to be smaller and shorter than the other guys. My features are undeniable feminine and the realistic breasts make me appear to be all woman. I step out of my heels and untie Joel's robe. He stands before me in only his boxers as his chiseled body and rock hard abs are on full display. I can feel my penis strain beneath the prosthetic vagina I am wearing. Joel's penis, which is probably twice as long as mine, is stiff as a rail and eagerly awaiting my sexy body. At this moment my only regret is that my breasts and vagina are not real so that I can fully enjoy this experience. Looking at the size of his penis, however, immediately gives me doubts and I am afraid of letting something so big inside of me. Joel carries me over to the bed and soon we are lying on top of each other. I let out a soft moan as he kisses me down my body from my lips, to my neck, to my breasts, to my stomach, and up and down each leg. What he does next though surprises me. He takes off not only my thong, but my fake vagina as well, and begins to suck on my tiny penis. Compared to his, my penis seems so feminine. It quickly gets hard in his mouth and then he stops and removes his boxers. Soon I find myself giving him anal as he screams out in pleasure. The image in the mirror of a sexy girl with a strong man bent over in front of her makes me cum instantly. Soon after I release him and we are lying on the bed once again making out. It seems somehow he could see my hesitation upon seeing how large he is and makes due with pleasuring me in other ways. Soon we fall asleep with his strong arms around me. The next morning I wake up alone in bed. I look at the time and realize it is late in the afternoon. I sit up and see a note on the nightstand. I must have been really out last night. My breasts, acrylic nails, and makeup have been removed and there is a set of male clothing near the bed. I sit up and look around the room. Everything I was wearing the night before is gone. My purse is also gone and my wallet and cell phone are on the nightstand. I go to the bathroom and take a piss. As I catch my reflection in the mirror, I see my regular male self. Except for the lack of body hair, it's as though last night never happened. I go back to the nightstand and read Joel's note. "Dear Noah," it says, "Thank you for a wonderful evening last night. I understand you may be feeling confused or conflicted about last night's events. I have left some clothing for you to wear and when you go to the lobby my limo driver will take you home. For now we can pretend nothing ever happened. If you would like to become Naomi again, however, just call the number I have programmed into your phone. I have all of your female attire and accessories from last night if you would like it back, as well as an entire wardrobe for you to wear if you choose to come to my home. For now, think things over and get ready for the job I arranged for you at one of my other branches. A position similar to the one you previously held with your old company recently opened up and I have already set you up to begin working there tomorrow. Thank you again." Since that day, things have returned pretty much to normal. I've been doing well at my new job and my relationship with Tina is the same as it was before we dressed up for the party. She never brings up that night and never asks me to dress as Naomi. When Joel visits my branch he treats me as any other worker and hasn't brought up anything we did that night. Strangely, as strongly as I felt toward him that night, I haven't gotten any of those feelings as my male self. Sometimes I secretly dress up as Naomi when I'm alone and the feelings I had that night come rushing back. I have thought about calling him many times since that day, but I am afraid of the path it may lead me down. I don't want to become a woman full time, but it would be fun to be Naomi every once in a while. Pleasing the Client By RogerGirl "Mr. Fitzpatrick, could I see you in my office please?" my boss Joel says one afternoon. "Yes, Mr. Simmons?" I ask as I enter his office. "Please, sit down Noah," he begins, "We have an important potential client that we are looking to sign in Los Angeles. Signing him would bring millions of dollars to the company. I'd like to send you to Los Angeles this weekend to woo him?' "Wow, that's great sir," I say, "Don't worry I won't let you down." "I'm sure you won't," he continues, "but there is one other thing. This client has a secret affinity for special girls. Girls like Naomi. Unfortunately, with his career he can't let this kind of thing become public knowledge. I would like you to go to him as Naomi. You will be given a company ID and your hotel reservations have already been made in this name." "But, Mr. Simmons," I begin nervously, "I don't know if I can do this. What if I am caught? I don't want to do anything that will ruin his reputation." "Don't worry Noah," Joel replies calmly, "I've been with Naomi many times since that night, there is nothing to suggest you aren't a real woman, and quite an attractive woman at that. I may be stepping out of line here, but each time we meet Naomi grows more and more convincing as a woman." "Thank you," I say shyly. "It's settled then," he continues, "I've already spoken with Tina and we've sent all your luggage to the hotel. All you have to do is transform yourself into Naomi the morning of your flight. You will be picked up in my private limo and driven to the airport where you will be flown to Los Angeles in my private jet." I stumble out of his office and back to my desk in a daze. This is what I have been dreaming of since I first became Naomi. Of course I eventually gave in to my urges and would often join Joel in private, but for so long I have longed for the chance to step out into public as Naomi once again and finally I will have that chance. The next few days go by in a blur as I begin to mentally prepare for my trip. I have already been photographed for Naomi's ID and what felt like a dream only a few days ago now feels more and more like reality as I see Naomi's pretty face on her new company ID card. Of course to avoid my secret coming out around the office, Joel used my middle name, Tyler, as Naomi's last name. Being the boss, he has certain powers to make it look like Naomi is a real employee at the company. Finally, the morning of my trip arrives, and Tina and I are busy with last minute preparations for my trip. Tina has been amazingly supportive through this all and even supports my cross-dressing and Naomi's relationship with Joel, although she hasn't dressed as a man since the party. When the limo arrives, I grab my purse and step out of the house as Naomi for the first time since the party. I am wearing a long blonde wig that falls in thick waves on my shoulders. My face is made up in a manner that is professional, yet at the same time very sexy. I am wearing a tight low cut blouse that does nothing to hide my ample cleavage. My pencil skirt is tight, yet professional, and ends just above the knee. Under my clothing I am wearing a black bra, matching bikini panties, black stockings, and suspenders. On my feet are a pair of 5" black opened toed heels and you can just make out my polished nails through the tips of my stockings. "Good morning Miss Tyler," the driver Roger says as he reaches out to take my hand. "You look quite lovely this morning." "Thank you Roger," I reply as I offer him my small ladylike hand with its long red painted nails. Roger helps me into the car and I sit with my legs crossed. He closes the door and I begin to look around the limo. Sure I've been in a limo when I went to prom, but this is different. A bottle of champagne is chilling in ice and a glass has been poured for me. I don't normally drink in the morning, but today I am feeling so happy I decide to go for it and take a sip. As we drive to the airstrip, Roger chats with me casually. Although he knows my true identity, he refers to me and treats me as the woman I appear to be. Roger is very loyal to Joel and has been very good at keeping all his secrets throughout his many years of service. When we arrive at the airstrip, Roger helps me out of the limo and Joel meets us. He kisses my hand and tells me how gorgeous I look. I blush at his compliment and thank him. Together we board his private jet, where we are met by the captain, Stan, co-captain, Frank, and two beautiful flight attendants in sexy uniforms, Monique and Natasha. Surprisingly, these flight attendants are also ladies like myself. If I were not dressed the way I am, I would never believe these two gorgeous women are really men. They guide us to our seats and soon we are in the air. Once it is safe to remove our seat belts, I find myself in Joel's lap and we are making out in a passionate embrace. Sure I am comfortable working together with Joel as a man in the office, but now that I am Naomi, all my old feelings have come rushing back. Surprisingly, Monique and Natasha are in a similar position not far from us. Watching the two sexy girls, I find myself turned on even more. After all, I am still attracted to women. As I watch the girls remove their tops and bras and their very realistic breasts press together, I feel the urge to take things further with Joel. We begin to remove each other's clothes and soon I am straddling him once again wearing only my stockings, suspenders, and heels. He begins kissing my soft breasts, bare shoulders, and slender neck as I this time allow his huge cock into my artificial vagina. Sure it is not as satisfying as sex with a real vagina, but I'm not ready for him to enter my ass just yet. I turn again and see Monique on her knees sucking on Natasha's tiny cock and I begin to cum. Our pleasure is interrupted, however, when the captain announces that we will be arriving soon. Sadly, the four of us begin to get dressed and take turns using the bathroom to clean ourselves up and for me to wash out my vagina. I return to my seat looking professionally once again and fasten my seat belt as we prepare to land. I look over at Monique and Natasha and they are now dressed in sexy mini-dresses and heels. Like me they are wearing prosthetic vaginas just in case we run into any paparazzi. When the plane lands, Joel takes my hand and I am led to a limo where a large bodyguard is standing. Monique and Natasha follow behind us holding hands. Joel tells me that the two of them are a couple and are engaged. The bodyguard checks our IDs and lets us into the limo. We settle inside, and to my surprise I see Brandon Grayson sitting with a grin on his face. He is wearing a pair of baggy jeans, a Lakers jersey, and a baseball cap. If you who don't know who Brandon Grayson is, then you're probably not a teenage girl. Brandon, who recently turned 22, is a pop singer and the celebrity crush of teenage girls all over the world, or Branatics, as they are known as. I have to admit he is cute in a boyish way, but he isn't really my type. I prefer my men strong and rugged like Joel. Brandon, on the other hand, looks like he has never had to shave a day in his life. Of course I understand how important it would be to the company to sign a client like Brandon Grayson, so I will try my best to win him over. "Mr. Grayson," Joel begins, "I'd like to thank you for giving us this opportunity. Hopefully this goes well and we can begin a long partnership. This is Naomi Tyler, my top agent." "Well, I'm still going over my possibilities," Brandon says as he puts his arms around Monique and Natasha, who sit on either side of him, "but so far I have to say your chances are looking good. Although not as good as you look right now, baby." "Thank you, Mr. Grayson," I reply trying to remain professional. "Please, call me Brandon," he says while looking me over. The limo drops us off at our hotel and Monique, Natasha, and I check into our rooms. Joel, of course, will be staying at his mansion in Beverly Hills. I find out that Monique and Natasha will be sharing a room and that I will have a large suite all to myself. The man at the desk informs us that our luggage is already in our rooms so I return to the limo while Monique and Natasha go up to their room. Once back in the limo, Brandon turns his attention to me now that Monique and Natasha are gone. I begin going over our company and the benefits of signing with us, but it is clear that Brandon is in no mood to talk business. He begins rubbing my leg and starts kissing me as Joel sits by going through paperwork. Kissing Brandon feels like kissing a girl. His face and lips are so soft and his kisses are so delicate. Sure I like women, but when I kiss a man I want to feel like I'm kissing a man. I want to feel his stubble on my face and his skin to be a little rough. I expect a man to be in control and to make me feel powerless in his strong arms, but Brandon is so submissive I am forced to be the dominant one. Even his voice sounds like a woman and his penis is so small I can barely feel it when I rub his crotch. How could so many girls fall for a man so girly? The limo drops us off at his mansion where we are served a lunch prepared by his private chef. Throughout lunch we try to make our presentation, but once again he is more interested in me. He asks me out to dinner and reluctantly I agree. Despite his interest in me, he still seems no closer to signing the contract. Maybe going on a date with him will win him over. Joel and I get back into Brandon's limo and after dropping Joel off at his mansion, I soon find myself back at the hotel. I go up to my room and take a shower, then begin the process of getting ready for my date. I put on my favorite little black dress and go to work on my hair and makeup. With my hair and makeup finished, I add a few pieces of jewelry and spray some perfume. When I get a call from the front desk informing me that the limo has arrived, I put on a pair of 6" heels and grab my purse. I go downstairs and Brandon's driver helps me into the limo. Brandon compliments me on how I look and I thank him. He is wearing a suit, but still looks quite boyish. He begins kissing me again and touching my bare thighs. I climb onto his lap hoping he will take charge, but even in this tiny dress I still feel like the man here as once again I am forced to take control. It's going to be hard to keep this up all night. How am I supposed to act like I'm interested in him when he gives me so little to work with? We arrive at the restaurant and Brandon grabs my hand as his bodyguard leads us through a crowd of paparazzi. The dinner is very delicious, but I find myself bored trying to continue to feign interest in Brandon. Yet, I know how much this means to Joel so I push through. After dinner we push our way back through the crowd of paparazzi and head back to my hotel. "Can I come up?" Brandon asks. "Sure," I reply trying to hide my true feelings. We go up to my room and begin to kiss. I let my dress fall to the floor and begin removing Brandon's clothes. As I see him standing before me in just his boxers, I try to hide my disappointment by kissing him again. His body is so skinny and he has such sparse body hair. I push him onto the bed and pull down his boxers. His penis, even erect, is so small and puny. As I begin to pleasure him, my disappointment grows as I quickly discover how bad he is in bed. He soon has cum before we even barely begin. I roll off of him and we lie together in silence. "Sorry," he says a little shyly. Suddenly his cell phone begins to ring. He answers the phone and I see a wave of terror come over his face. He hangs up the phone and lets it fall to the floor as tears begin to roll down his face. "What's wrong?" I ask concerned. "That was my agent," he says as I try to dry his tears. "My driver let it leak that I was in a hotel room with a tranny. My career is over." "Maybe not," I say as I begin to form an idea in my mind, "If I can get you out of this, will you sign with us?" "Yes, of course," he replies, "but I don't see how you can fix this." "Well, if I can get you back to your mansion without anyone seeing you," I begin to say, "then you can probably get the media to think it is just a rumor made up by a bitter employee trying to get attention for himself." "Yeah, I might," he says, "but how am I going to get out of the hotel? The exits are covered by paparazzi." "You just leave that to me," I say. "You will have to do everything I say though. Understand?" "Yes, ma am," he answers. After calling Joel to pick us up, I take him to the bathroom get him into the shower. I get my shaving gel and razor and begin shaving off all of his body hair. He didn't have much body hair to begin with, but now his skin is even softer and smoother than before. As he finishes his shower, I remove my wig and prosthetics. I help him dry off and attach the breast forms to his chest. He looks unsure, but goes along with it. Once the breasts are firmly in place and blended to his skin, I help him put on the vagina. Luckily we wear the same size clothing, so after helping him put on his bra, I begin removing my makeup and nail polish. It isn't long before I am Noah again, and I change into Brandon's suit. Once I am dressed, I return to Brandon, who is now wearing a bra, thong, and one of my sexiest mini-dresses. Unfortunately for Brandon, the only clothes I have with me are sexy ones. I sit him down and begin working on his nails and makeup. With his soft features, he already looks like a pretty girl even with his short hair. Finally, I go to work putting the wig on his head, adding some jewelry and spraying on some perfume. I help him into a pair of 5" heels and stand back to admire my work. He stands before me teetering around in his heels with an uncomfortable look on his face. While he was not much to look at as a boy, he is beyond gorgeous as a woman. As I look over my creation, I feel my penis begin to grow and it takes all my restraint not to bend him over and fuck him right there on the table. Being dressed as a man again, all of my masculine urges have come rushing back and I can hold back no longer. I grab him and pull him in for a kiss. He tries to resist at first, but soon he is putty in my arms. We make out passionately as he submits completely to his femininity. Our kissing leads us to the bed where I soon find myself with my rock hard penis in his cute little ass. "Oh, Noah," he moans, "Fuck me! Fuck me hard!" What would his Branatics think if they could see him now on his hands and knees with his panties around his ankles letting out soft girly moans while being taken forcefully from behind by a man? I quickly release my load inside him and soon we are making out again as we lie together on the bed. "That was incredible," he purrs in a sweet sexy voice. "Anything for a client, Brandon," I say as we kiss again. "Call me Brandi," he says seductively. Before we can go for another round, I get a call from Joel telling me he is waiting downstairs. I take Brandi's hand and we head downstairs. Brandi is nervous at the prospect of being discovered and she squeezes my hand tight. We pass through the paparazzi with relative ease and make our way to the limo. "Who was that?" I hear one of the paparazzi ask another. "Probably just some spoiled rich kid and his slut girlfriend," the other guy replies, "Don't worry about them, we're here for Brandon." We get into the limo and I can't help but laugh at their comments. If only they knew they just let their prize walk right past them. The limo drives off as Joel looks in shock at Brandon's transformation. Brandi cozies up to me and thanks me with a kiss. It isn't long before we are making out again and my hands are all over those sexy smooth legs of hers. She is definitely much better at this when she is playing the female role. When we arrive at Joel's mansion, Brandi and I have sex one more time before I change him back and we take him back to his mansion. The next morning he signs the contract after discovering our plan has worked. The media quickly discredits his driver and Brandon fires him. Brandon's reputation remains in tact and his secret remains safe with us. It has been two years since we signed Brandon and we have both made each other a lot of money. Joel has opened a new L.A. office and I was selected to run it. Tina, unfortunately, wanted to stay in New York to remain close to her family. We tried making the long distance work for a while, but eventually we broke up while remaining friends. I've seen been forced to cut down on my time spent as Naomi with my busy schedule running the office and dealing with clients. That being said, I haven't given up dressing entirely. With full access to Joel's mansion, I am able to carry on my dressing in secret. When Joel is in town, we often get together for a little private time with me as Naomi. Of course, I still have to fulfill my masculine side and Brandon has been more than happy becoming Brandi time and again to fill those needs. I guess you can say I've become a Branatic too.