Messin' With The Wrong Trannies free porn video

Messin' With The Wrong Trannies By Texzilla Milo Schullenberg stumbled into the apartment first, followed by his equally tired and sweaty roommate, Dave Angelo. The two athletic young men drop their racquetball paddles and head towards their living room area. "Not on the couch!!" Dave yelled. "Use your video game playing chair. It already smells like your sweaty ass." "Good point," Milo said falling onto the couch anyway. "I'll do that next time." "What were the advantages of rooming with a straight guy?" Dave said collapsing into a chair. "My being straight has nothing to do with this. My being a slob does," Milo said lying down with his face on the couch cushion. "We're going to kill each other with these racquet balls games one of these days." "Yea, but we're going to leave great looking corpses," Dave said beginning to get his breath back. "I call the shower first," Milo said gatting himself off the couch, heading towards their bathroom, pulling his sweaty shirt over his head as he went. "Oh yea. I know it's few weeks off but my company always has this big Halloween party. We HAVE to buy tickets, we HAVE to attend and we HAVE to wear a costume." "And you're telling me this...because you want an excuses to start wearing an adorable Pooh Bear outfit you bought yourself around the place?" "Telling you this, smart ass, cause month's ago I bought a ticket so Jenny could go with, but since we broke up...was wondering if you wanted to go?" "I don't know. Office parties are bad enough, but when it's not even your office..." Dave said "Free food, open bar," Milo countered. "It's mine." "Besides no one will know who anyone else is. At least we're not suppose to. That's how good the costumes need to be. We're all in the financial world so we should all make enough to get something better than off the rack at Walmart. Last year I spent almost $200 to go as pirate, but then so did 5 other guys." "Shit, my first thought was pirate," Dave said actually sounding fairly disappointed. "And see how I've progressed, even though you're gay I'm not going to suggest you go as a girl. You can go as your favorite cast member of Glee. Besides, you ins a dress....HAW!!!!" With that Milo headed off to the shower, leaving Dan alone to think. He and Milo has become really good friends. They'd bonded over their love of computer games, and it didn't hurt that Dan was a digital designer and knew all the tricks. But if Dan had to think who his best friend was, it came back to Milo. Sure they had this crazy competitive thing going on. Started with the video games and carried over into the rest of what they do together. Such as both of them trying to drive the other into the ground of the racket ball court. And Milo had come a long way with the gay jokes. Didn't even seem to be an issue any longer. His jokes were never mean, just stupid dumb things that Milo always said. Dave had gotten hammered with Milo when he broke up with Jenny, and Milo returned the favor when Dave broke up with Eric. But this was something else, something big. Well, Dave thought, might as well see how far the big goofy dope has come. "So..." Dave said lowering the toilet lid and sitting on the edge, a towel in his hands. "You don't think I'd make a good looking girl?" "You? That would be a major fail right there," Milo said shutting off the towel and beginning to dry himself off. "Well it's just I....." "You are NOT telling me you dressed in drag for Halloween before," Milo said as he ran the towel over his head. "No, I'm telling you I...... lived as a girl for a couple of years through high school and off and on in college.......," Dave said as confident as he could, knowing it came out sounding pretty weak. Milo stood in the shower for a minute. Still drying his hair. Looking at his roommate for the past year. The long curly black hair, the full thick beard, the hairy chest so thick he could barely make out the guy's nipples, the hairy legs... "Lived as a girl?" "Yea." "With the plan being to get your own titties and a vajayjay?' "Never got that far of course but, yea." "Noooooooooo...." Milo said leaving the shower and the bathroom and heading to their kitchen. Dave also exited the bathroom but took a left down the short hall to his bedroom. After fishing around in his closet for a minute he sat on the other side of the kitchen counter, flipping through two books. "Here you go," Dave said turning the first book around to face Milo. "Freshmen year, Dave." Milo looked at the classic high school picture. The young guy in the photo had Dave's name under him. What with Dave's long hair and full beard, plus the years in-between it was kind of hard to tell but, yea it had to be Dave. Milo was surprised at how much the two of them looked alike at that time. Even now, like at the gay bar they hung out in during the Eric dumped Dave drinking days, a few people thought they were brothers. Not tall, both in their early 20's, both almost exactly 5'6", good builds not a ounce of fat on either one, but not overly muscled. Milo started calling them the little guys with big dicks club since, well, they were little guys with bigger dicks than most of their dates would have expected. "And Junior year....Debbie." Took Milo a second or two to focus in on what he was seeing. Young girl, long blonde hair, smiling more than Dave had in the first picture. and the name under the photo, Debbie Angelo. But there was something about that smile that Milo has seen on the present day Dave, through al the hair from the beard and mustache. Something that told Milo... "No way. You did this as a gag..." "OK, Understand, I'm just gay, I'm not transgender or a transvestite. But I was really confused as a kid. Figuring out I was gay, right when my parents had that bloody divorce. My stress and anxiety manifested itself as gender confusion. Can you tell I've had a lot of therapy over this? Get a load of this," Dave said flipping a few pages to show Milo the group photo he was in when Debbie was on the cheerleader squad. "My best buddy was a cheerleader?" "Would have made head cheerleader but I couldn't' do splits. Still had a kickstand, if you know what I mean." "You're like.....cute........ I would have fucked you back then." "Thanks, I guess... You sprouting some wood back there?" Dave said looking over the counter top to see indeed that the towel around Milo's waist was tenting a bit. Milo said closing the book. "Playin' Halo." Dave knew that for right then, that was it for now. If Milo was going to play a game on their system he wasn't going to be thinking about anything else. At least that's what Dave thought at first. He'd gone in, taken a shower, got dressed in his usual Sunday afternoon playing games the rest of the day sweats and joined Milo in front of the multiple screens they had set up for their gaming rituals. Dave being something of a computer genius meant they had the fastest system with the coolest extras of anyone they knew. But Milo kept doing something that he never usually did, something Dave didn't think was possible. He kept looking away from the screen and looking at Dave. Just flash like quick looks. Over and over. "WHAT! Stop it," Dave said "Stop what?" "Looking at me like my chest is suddenly going to explode with titties!! You're still freaked, aren't you?" Dave said pausing his portion of the game. "No, no,.......no........a little," Milo said as his distraction got his guy killed, something that also never happened. "More like curious. I mean, really, Debbie? That's the best you could come up with?" "It's a family name and look, it's over with. I know who I am now. I'm a man, I like to wear men's clothes. I was just confused. I'm not ashamed that I did it, I got pretty good at it actually, I dyed my own hair that blonde. But I have no want, need or desire to do that again," Dave said hoping this would be enough for Milo to get over his revelation. "Didn't you folks freak? And the school?" "It was a high school in San Francisco, not the first student to go trans on them. As for my folks, they blamed themselves due to the divorce so they went along with it." "Did you....go on hormones." "Ummmmm..."Dave said knowing this would be the most uncomfortable part for them to get through. "For a few weeks. Beginning to get breast buds was nice, but then I couldn't get a hard on anymore. I think that's when I figured out I was more confused than trans. I knew I like my dick too much to ever have anything else." "That's true, what would do you thinking for you if you didn't have a dick? It's just....I see you, the guy I've known for...I mean we're like brothers man, and then I see that picture of that girl and..I'm trying to put the man I know into the girl I see and it just doesn't add up." "Well, thanks for thinking of me as a brother man, that means a lot. But like I said, I was just confused, I've figured things out, and that's not me any more," Dave said wanting to wrap this up and get back to their game. "And besides, as you said, you couldn't do it again anyway," Milo said hitting the pause button and going back at it. "No, I said I didn't want to do it again. I still could if I wanted to. Like I said I got good. When I switched back to being a guy by Senior year, there were people who did know I always HAD been a guy all along. I could still do that." "No. You're TOO much of a guy now." Neither man said anything for a few minutes. Milo because he was into his game mode. Dave because he was thinking. "What to bet?" "On the game? I'm about to destroy you why would you..." "No, on if I still have the skills to make a girl out of a guy. I bet you that I can make us up a girls for your Halloween party. And do such a good job that you'll get in trouble for not attending, cause no one will believe it's you." "There is no fucking way I am going to let you make me up to look like a girl. Not going to work. Not going to do it," Milo said with a little uneasy laugh. "Bwaaaaaakkkk-bak-bak-bak..." "Let's say IF I bet and WHEN I win, what do I win?" "Loser has to be the other's bitch for a month, do the laundry, clean up, cook. All the winner has to do is sit back and game play all night and day." Milo sat there for a moment. This was something he wanted no part of. But then Dave had made the chicken noises. And Milo couldn't let him get away with that. "Bet," Milo said holding out his hand. "Bet," Dave said slapping it. "You have to trust me and do what I say when we get dressed. No balking." "But If I'm not believable I'm not leaving the apartment." "I'll have you cuter than a Disney Princess and twice as fuckable," Dave said "I better be. Wait a minute........," Milo said getting distracted again so his on screen character got killed again. Things were kind of quite for a week or so. Dave measured Milo for clothing. Milo tried to get out of it but Dave insisted they weren't going to be wearing Milo's usual two sizes too big type of clothes. By the end of the week Milo started finding things like skin cream on the bathroom counter near the sink. Then the make up started showing up. Some on each of their sides of the sink. He knew what most of it was, just had no idea how to use it. Milo got a little shock in checking the make up out, finding that while what was on his side of the sink was all untouched, some of Dave's looked like it had been used. Boxes in Dave's name started showing up and quickly disappeared into Dave's room. Milo wanted to ask but was afraid of the answers. As the day came close Milo got up the nerve to ask about shoes. That if he was going to be expected to wear high heels he'd have to be given a chance to wear them, get used to them. Not that he wanted to wear high heels around their apartment. But if the bet was that no one would guess who he was, and he spent the night tripping over his own feet....didn't want that to happen. Dave assured him that for what he had planned, they wouldn't have to deal with heals higher than those of the dress shoes he wore with his suit to work everyday. Dave had let Milo know that the day of the party they would need a couple of hours in the afternoon to get ready. Milo had to run a few errands but returned to the apartment before the timeframe Dave had given him. Entering their apartment Milo was kind of surprised to find some longhaired blonde teenager hanging out in their kitchen only in his very small underwear. Milo wasn't aware that Dave had brought a 'friend' home the night before. "Can I help you?" "Dude," the teen said in a perfect surfer dude voice. "Just came to fix your sink." "In your underwear?" "Milo, it's me." Milo couldn't believe his eyes. His formerly dark curly haired hairy roommate was now a straight haired blonde, no beard, no mustache, no body hair from the neck down. He sort of looked like the younger brother of the girl in the yearbook picture. "Holy crap. You going to do that to me?" Milo said with his jaw almost hitting the floor. "Not going to bleach your hair. I want us to look alike and yours in too short. Got you a wig that should work. You OK?" Dave asked seeing the look of shock has not left Milo's face. "Yea, it's just so.....different." "You ain't seen different yet. Let's get started. Strip and get in the shower," Dave said patting Milo on the shoulder and heading into their bathroom. Milo put his things away, and stripped out of his clothes, leaving them on his bed. Not without a sigh he headed to face his transformation. "Hey, here's an idea." he said as he entered the bathroom. "That surfer dude voice you did was great!! Let's go as surfer dudes!!! I'll spring for beach clothes at one of the trendy surf stores down by the ......." "Bwaaaak-bakbak - bwak....or would you rather admit defeat and be my bitch." "What's first?" Milo said stepping into the shower. If he was going to lose this bet, he was going to lose trying. Not because his now blonde twink of a roommate was calling him a chicken. "Losing the fur. Start covering yourself from the neck down in this," Dave said handing Milo a bottle to Nair. "I got two bottles for you." "Smells like shit," Milo said beginning to cover his chest. "And even better, it burns as it works. Come on, get busy. Make sure to do your arm, hand, toe and don't forget you ass, including the taint." "No one's going to be seeing my ass or...you know,.... that area..." "We're going to be wearing undergarments that might be sleek and smooth on the outside, but will grab and pull any hair it finds. Trust me, it hurts, and not in the good way. Lose the hair. I'll let you decide on the pubes. Either you can lose them like I did, or I can trim them up for you." Milo thought for a minute and then covered his dick in the light pink goo. He covered his legs and despite still having reservations, slicked up his ass and just between his legs with the last of the second bottle. "Now what," he said from the shower, his arms out to his side and trying to stand still as not to slip. "Setting the timer for a few minutes. It should start to tingle soon." "You said burn." "Tingle then burn. That means it's working. You know what's going after this?" Dave said holding up a said of scissors. Milo lowered his hands to cover his cock. "No, not yet. Girls with 'stasche tend to stand out. While you're waiting why don't I start trimming it down." "No that's OK, I can do it when I'm out of here." "Milo, man, my hands are going to be places today that they normally wouldn't be. But if we're going to do this, we're going to do it right. You have to trust me on this. Dude, it's me, relax, you're going to have a blast before tonight is over." "Clip away," Milo said leaning forward and sticking his lip out. In the corporate world of high-level money management and investment, Milo's 'porn 'stasche' as he called it was his one attempt at individualism. The bosses hated it but they couldn't do anything about it. He felt a little bad that it was going away for such a silly reason as dressing up for Halloween. With the ding of the kitchen timer Dave reached over and started the shower. Quickly the pink goo started washing away, leaving smooth skin behind as it has done on Dave. After he'd cleaned it all off with a washcloth Dave handed him a razor so they could catch any straggling hairs. As Dave put it, Milo took the upstairs, Dave too the down stairs. Looking up from running the disposable razor along Milo's calf Dave said. "Those pecs are going to make a great set of tits." "How's that." "Oh, you'll see." Milo wasn't sure if it was just the touch of another man's hands on his legs that was giving him a charge, or the touch of anyone's hands on his now perfectly smooth body. He didn't even jump that much when Dave moved his dick around to shave along the side and get rid of any hair still left above it. Once he was sure that all the body hair had been removed, Dave allowed Milo out of the tub and had him shave the remaining hairs from his upper lip. Whipping away the remains of the shaving cream Milo looked the results in the mirror. The youthening effect of removing the body and facial hair wasn't as dramatic as on Dave. But Milo found himself looking not only like someone else, but a stranger that was a few years younger than him. "Christ, we look like little boys now." "Well we're going to be looking like girls pretty soon. Sit down and let's get started." Dave felt a little bad lying to Milo when he said he wanted to do Milo's nails first to get back into practice. The real reason was he wanted the nail extensions on his roommates hands because he knew Milo would have trouble dealing with them for a while. Thus keeping him from messing around with the makeup with he was getting them ready. Except for the nails, which Dave waited till the end to apply to himself, Dave would go through the step first, and then do Milo. Kind of giving him an idea of what was coming. Soon enough, eyebrows were being covered, foundation being applied, any remaining remnants of beards were covered. The fake eyelashes and mascara didn't go anywhere as smoothly as Dave would have liked, but the end result was flawless. Dave used something on their lips before he added the lipstick to make them plump up a little. He had to threaten Milo that he'd remove the covering over his eyebrows and pluck them if he didn't stop licking his slightly larger, deep red lips. Milo of course could see the transformation on his buddy's face, but the quick glances he would take in the mirror were even more amazing to him. It all became even more real when Dave left for a minute and came back with the wig. After a little tugging and fitting, Milo had shoulder length straight blonde hair like Dave did. Standing next to each other, being the same height, with the makeup, they had to be at least cousins if not sisters. "Ready to complete our un-maning?" Dave said breaking the almost trance Milo was in. Dave grabbed a couple of pieces of make up off the bathroom sink and they headed into their living room. Anyone looking in would have seen a strange sight. Two naked hairless men with faces expertly made up as women standing in a room that was one half computer game equipment and the other covered in women's clothes. "Could have gone a couple of ways with this. But I wanted to give you the full treatment. Might at well get the most important part over with first. It would be harder to do after I add our boobs" Dave said handing Milo want looked like some thong undies. "Just our underwear?" Milo said sliding it up his legs, following Dave's lead. "Not just underwear. Watch me. We have to adjust..........our......junk like so and .....pull up the back a little. Make sure the nuts retreats for safety......and there." "Your dick is gone," Milo said seeing his male roommate now completely smooth in front. And with the make up, he looked like an overly muscled, flat chested teen-age girl. "We're going to be wearing really short skirts. It's got to go or we'll be found out. Come on, I've already switched my sex, now it's your turn." It took Milo a couple of minutes longer to get his dick in place. Dave was helpful and reassuring as the strap in back was pulled up, making the last hint of a manly bulge smooth out. Dave then brought out a couple more lacy white things for them to wear over the foundation garment. Having gone this far Milo didn't hesitate to slip them on and part his ass crack for the back strap as if he'd done it for years. "That's really incredible. Not uncomfortable at all. Wow, it even feels like a pussy," Milo said rubbing his long fake fingernails along the front of the fabric. Looking down he was getting a buss not seeing his dick bulge out from his underwear, but knew it was still there, just hidden. "I wouldn't know what a pussy feels like." "Well it does, here feel," Milo said taking Dave's hand and rubbing it on his missing crotch. "Oh shit, might not be able to see it but my dicks still in there." "Try not to get a woodie, it's painful when the dick's stuck back like this. You seem to be getting into this now." "Kind of getting fun." "You want fun? Let's get the tits going," Dave said. It took almost as much pushing and prodding, both of their pecs this time, for the guys to have the lacy bras and breast forms all in the right place. With his slightly larger build Milo got a set of Ds while Dave was not far behind with a good set of C's. The lacy garments continued as garter belts were put in place with sheer stocking rolled up, very carefully with his new long nails. With a final clip in place Milo was pleaded he hadn't snagged his. With all their underwear in place the guys took a moment to check each other out too see if they were missing anything before going to the outer garments stage. Milo wondered at Dave's handy work. There was no hint of maleness left, nothing but sugar, spice and other assorted girly bits. "OK, now, you're really going to have to trust me. Just want to point out what a great sport you've been, how great you look and how much fun we're going to have. Open you mouth," Dave said taking a small glass bottle with an old-fashioned bulb sprayer on top. "So far this female thing is kind of fun. I've got some plans to goof on some people tonight like....open my mouth?" "Just for a second." "Is my breath that bad?" "Just do it." Milo shrugged a little and did as he was told. Quickly Dave gave Milo's mouth two really good shots from the little bottle. He could feel it hit the back of his throat and slide down. There was an immediate slight burning then coolness to his throat. "Didn't have any real flav........what have.....," Milo said grabbing his throat as it seemed to tense up inside, causing his voice to start to go higher. "It's temporary. It'll wear off. See..." Dave said spaying his own throat. After clearing it a couple of time Dave came out with "It's doing the same to me." that was octaves higher than before. "What is going.....on," Milo said now sounding not at all like a woman, but exactly like a teen girl. "Now you know one of the better secrets of drag queens around the world. It's just a tauntener for the vocal chords," Dave said is an adorable high squeaky voice. "We couldn't' pass ourselves off as girls with out regular voices. And no time to take voice lessons. Come on, it's fun!! Listen to me. You try it. Say something stupid." "OMG did you see Gossip Girl last night. Holy shit!!!" Milo said at the voice out of his mouth. 'If you thought you were going to be able to goof on people before." "Umm, when will this wear off?" "By tomorrow morning, afternoon at least. For sure Monday," Dave said not sounding totally convinced himself. "Like you're totally reassuring me here," Milo said trying to make it sound as dippy as possible. "We've got to get dressed. The cab will be here soon," Dave said getting the rest of their 'costumes' ready. "Why are we taking a cab? It's just my work. I may look like a dumb blond now but I still know how to drive to work." "Our tits are going to be in the way, we have these nails, not to mention new shoes. You want to take a chance getting into an accident looking like this. It's on me, and the ride home." "Whateverrrrrrr..." Milo said beginning to twirl some of his blonde hair around his finger. "OK, now you're scarring me." Milo didn't quite get the idea behind their clothes till Dave explained it fully. They couldn't JUST go as girls, then people would wonder what the costumes were. BUT if they went as girls dressed up as sexy Catholic school girls, then everyone would think THAT was the costume and maybe not look deeper to see they were guys. Knee high white stockings with frilly tops were rolled up over the sheer nylons already in place, black patent leather school girl shoes with big silver buckles on them, pleated tartan shirts that barely reached low enough to cove the top of the garters. Dave decided they didn't need padding for their asses. Between their workouts and sitting for hours playing video games, they were firm but beefy enough as is. Everything was toped off with white dress shirts, unbuttoned to reveal their well crafted cleavage and tied just below their newly formed busts, exposing their mid drifts. The long sleeves covered up their slightly too manly arms. Some cheap jewelry, clip on earrings and bracelets. Black silk chokers around the neck with a little cameo on the front to cover the Adam's Apples, but still very much in character. Final touch was sheer white fingerless gloves. Not only cute, but covered the calluses on their hands from their workout sessions. Dave had been pretty sure that Milo would accept carrying a purse, but wasn't sure the lunk head wouldn't forget it somewhere. So instead, keeping with the theme, he got them cute backpacks they could just throw their wallets into. There was also some back up make up in case they needed a touch up. Dave's backpack was a bit larger than Milo's, but he explained he'd never been to a party with an open bar and not made it home without a few bottles of the good stuff. The big backpack was mainly for that reason. Taking a deep breath the went back into the bathroom with it's couple of mirrors. "You know how I said I'd have fucked you as a teen age girl?" Milo said. "Yea." "I'd fuck you and me right now." "Told you I still had it. I'd say I won right now." "Nights not over bitch." "Sure as hell ain't bitch." Dave didn't exactly have to drag Milo out of the apartment, but it did take some reassuring. The cab was waiting for them, and knew the route without having to get directions. Being one of the biggest financial firms in the country, it was well known by cab drivers picking up and taking people from the airport due to all the high level wheeling and dealings the place did. It didn't take long for 'the girls' to see that the cab driver was keeping almost one eye on the road and one eye on the rear view mirror so he could watch them. With a gleam in his eyes Dave started running his hand up and down Milo's inner leg, getting closer and closer to going under his skirt. Both of them keeping their eye contact with the eyes in the rear view mirror. "You two.....you two ain't sisters are you?" he choked out after a few minutes. "Not tonight we're not," Dave said slipping his hand under Milo's skirt who, after a second, rolled his eyes in his head and let out a cute gasp. It was only the chorus of car horns that got the driver's attention back on the road and them out of an accident. Dave was beginning to remember the plus side of being a girl around horny straight guys. And Milo was beginning to find out. The cab was able to drop 'the girls' off right in front of Milo's office building. It was an unseasonably warm Halloween but, downtown with the wind whipping along the high rises, the breeze up their skirts was a bit more than they has expected. "How do women do this?" Milo asked as the walked briskly to the front doors. "Do want?" "Wear dresses with just skimpy silky panties underneath? There's like nothing between my jewels and the elements. It's almost worst than being naked." "I think that's called part of the attraction," Dave said as they reached the door and entered the building. Usually the place was all business like, but down the main hall came the sound of music and there were a few other people, all costumed out, mingling around. The girls turned just about every head as they walked towards the check in table. "Look at you girls, very well done," the older woman behind the table said getting two nametags ready. "Thank you Marlene," Milo said taking out his tickets from the backpack. "Oh, do I know you girls?" she asked. "Now, now, no telling. It's suppose to be a secret," Dave said, hopefully reminding Milo that part of the bet was that he couldn't give out any clue as to who he really was. "Well I have to put something down on the name tags." "Cinderella," Milo said, remembering Dave's comment about being a Disney princess. "Snow White," Dave followed with. "Snow White might be stretching it a bit," the older woman, Marlene said giving Dave a shifty eye. "By the end of the night, probably," Dave said picking up his nametag, peeling off the back and pressing it far to close to the tip of his breast. He was giving every man the excuse to stare at his tits all evening by pretending to read her name. As Milo was finishing putting his nametag on the guy dressed as Zorro sitting next to Marlene asked. "Are you girls part of the Administrative Assistant's pool?" "I am no body's secretary," Milo said briskly and with Dave at his side headed into the party. "Meow back there Cindy," Dave whispered. "Craig Timko. Had to come as a Zorro because coming as a giant asshole would have been too spot on. What do girls like us drink?" Milo said as they made their way through the parting crowd towards the bar. "Champagne sweetie, nothing but the bubbly." The party was in high gear by the time the girls hit the room. A couple of other male employees had come dressed as girls, but the were caricatures. Basically didn't look like shit compared to Cindy and Snow. Milo had a brief panic attack of suddenly finding himself dressed like a girl in a room of his co-workers. But all he had to do was look to Dave for inspiration. Because Dave....wasn't Dave any longer. He knew how Dave moved and talked and interacted with people. And this wasn't Dave. This was a confident sexy young woman. Seeing his best friend act like this, become a new person, gave Milo the confidence to do the same. He might have been able to dress up like a girl by convincing himself it was just a costume, but now was the time to take it to the next level. Maybe stop acting like Milo and start figuring out who Cinderella was. Dave stared having the time of his life. Remembering all that was great about being perceived as a girl. His height, or lack there of, had always caused him to be intimidated some. But as a girl, he was the perfect size for people to react to naturally. He found himself being more open. Dave felt more natural and relaxed standing in a room of strangers dressed like a girl than he usually did in a gay bar filled with other guys he knew well. Plus it was nice to be able to flirt with straight guys and not get worried about being pummeled. Milo was getting a little clingy and Dave wanted him to experience being a girl on his own. He made an excuse to head to the bar and left Milo talking to three of his coworkers who had no clue as to who Cindy really was. "Another Champagne?" the Bartender asks as Dave reached the bar. Dave couldn't; but help notice the smile on this guy. Had to be a rental bartender, this place didn't hire guys this cute. Well, except for Milo. The guy was tall, thin, looked like he was of mixed family background black, white and maybe a few others thrown in, but it all came out damn cute. "I think I'll switch to rum and coke, please." "Normally I would card a girl like you," the bartender said sliding her the drink. "They wouldn't have let me into the party if I wasn't old enough." "Not that. I'd do it to see if your name was really Janet, and Betty," the bartender said leaning over the bar to whisper in Dave's ear. "Or Fred." Dave almost dropping his drink at the revelation he'd been outed. "Shit, what gave me away," he whispered. "Nothing, darling, trust me. You. Are. GORGEOUS." The bartender turning his flame up a bit. "The ONLY way I knew, the choker. Only because I umm,......I do the same thing when I go out as La'trelle." "Sister!" Dave said holding up his hand. "You got it," the bartender said returning the high five. A few people around them looked over but no one had heard their conversation. "Who did you? Was it that place downtown that..." the bartender asked "Oh no, this is all me." "You are GOOD girl. Maybe we can get together sometime and trade tips." "Well, this was just for tonight, to help out my buddy with this stupid party. We have like this bet going. I don't think I'll be doing it again," Dave said not knowing how to take the compliment really "Shit girl, shame to waste that talent." "Maybe, maybe. I'll think about it. Hey, do me a favor? Can I leave this behind there? Getting tired of dragging it around," Dave said handing the bartender his backpack. "Sure thing. How about I put my card in there, just in case." "Sounds good. And if a few of those bottles back there make their way in...... Wouldn't object," Dave said with a wink. A wink that got returned. Dave turned around with the thought of rejoining Milo when he found a young guy, drunk out of his skull, dressed like a spaceman stumbling his way. Maybe Milo wouldn't be the only one to get to goof of people that evening. While feeling a little abandoned at first, Milo soon found himself at ease when he remembered that the people who were talking to him weren't relating to him as Milo, but a cute teenage girl. Or at least someone who looked like a cue teen-age girl. Because there were a lot of the guys in the building he knew who were making their interest known. And if Milo was as young as he looked, it would be pretty creepy in some cases. At the moment he was being none too subtly being hit on by Cellistino Gomez from down in the mailroom. They knew each other enough to say Hi when passing in the hall. Tonight though, Milo was learning a whole lot more about Celli. Or maybe it was Cindy who was finding out. About how often he goes to the gym, how much he can lift, his years in the military.... While at the same time those nice caramel brown biceps kept finding a reason to pop up and had and get the vein going down the top. Milo got distracted for a second long enough for Celli hand to find a way to his hip, and stay there. It was an odd feeling. Not so much to have another man touch him, Dave had touched him when they were getting ready tonight. Celli was did it to send a signal. He wanted Cindy. Milo was convincing himself that it was Cindy that wasn't removing the hand and not his true self when a small commotion started heading toward them. "We have to find a lady's room. Now." "Is this one of those girl things were we have to go to the bathroom together, because that's more in character than I need." "We have to go to the lady's room so I can tell you about how you might be in jail by Monday afternoon." Dave said seriously as they headed out of the ballroom and Milo directed them down the hall to a bathroom he was sure wouldn't be used. Once in the secluded bathroom and after making sure all the stalls were empty, Dave calmed down enough to tell Milo what he's heard. "There this guy at the party, young guy from India, dressed as a spaceman. Robbie, maybe? Any idea?" "Sound like Ravi, one of Timko's pets." "Drunk as can be. Got me in a corner and wouldn't let up. I was playing along, thought it was kind of funny. Starts telling me how I should be nice to him because come Monday morning, he and a couple of other guys were going to be rich. Here's the important part, and I made him repeat it. He kept saying how they were going to a able to blame it on some idiot they work with and his fucking porn 'stastche." "Holy....... That's got to be me. What they hell could they be talking about?" "Something about a big stock trade or sale going down but it's not a sale. Make sense?" "Maybe." "I swear to you. Get me to a computer and I can find out. They've messed with the wrong trannies." Knowing the Dave's computer skills were second to none, Milo knew they had to get up stairs to the offices and log on so Dave could do his things. Leaving the lady's room though they ran smack into a very drunken Spaceman/Ravi. "Where's you run off too?" he slurred as he tried to remain standing. The young man from India obviously had more to drink than his body could hold. "And what's ya do, go clone yourself." "Grab him," Milo whispered. "That's right baby," Dave said taking one arm. "Going to need two of us to take on a stud like you. How about we go have some out of the world fun Mr. Spaceman? That sound good?" "You ever dream of doing it in your office, cutie. You know, throwing all the papers off your desk and showing a girl just what kind of man you are? Sounds hot doesn't it" Milo said taking Ravi's other are and heading them towards the elevator. The doors opened and the all but dragged the young man in on his tiptoes. "Does it ever!" Ravi mumbled before throwing up and passing out. The elevator ride seemed to take forever, mainly due to the stench of Ravi's puke. But they reached the floor both men worked on soon enough. When it came to entering the office area, Milo pushed Ravi against the wall and started feeling up his pockets. Ravi let out a little laugh but was still out of it when Milo pulled his wallet out. "Now if they check the records to see who came up here, they'll only have his key card." Milo waved Ravi's wallet at the security door and waited for it to beep to pull the door open. "Clever girl," Dave said as they dragged Ravi along the carpet. "Think we can get into his office?" "I know we can but let's lose him first. Don't want his coming too or chocking on his own vomit while we try to figure this out. Down here." Milo said as they turned right and found a maintenance closet just down the small hall. After a couple of minutes they had the unconscious young man bent over a large box of toilet paper rolls, face pointing down to a bucket in case more of his party snacks were headed out the wrong exit. As a last minute touch Dave undid Ravi's belt and pulled his pants and underwear down, leaving his exposed bare ass being the first thing the cleaning crew would find when they came in the next day. Again using Ravi's wallet with its key card they got into his office. Dave quickly went to work at the computer on the desk. "Not sure how far you're going to get since we don't have his log in information." Milo said as he hovered over Dave's shoulder. The light from the computer screen the only one in the office they dared have. "I'm already logged in with his passwords and usernames. I cracked your company's codes months ago. When you brought that laptop home to work remotely that weekend." "Why did you do that?" "I'm a computer geek, it's what I do. And have you noticed, long fake fingernails means I'm not leaving my fingerprints behind. Wait I think I have it. Look here." Milo looked at the screen and over the next few minutes, with Dave's help they found the plan. Somehow they had set up what looked like a major purchase of junk stocks, something that they couldn't do with all the reforms going on. Made it look like Milo was the one submitting the trade, but in fact, there would be no sale. The stocks would implode almost at the same time, making them totally worthless. It would look like Milo spent millions then lost it all within minutes. And in the confusion no one would be able to notice that the money didn't actually go with the sale but went into Timko's, Ravi's and a couple of other guy's bank accounts. Leaving Milo looking like the guy who cost the company and their clients millions and millions, while in fact it was Timko and his pets who would pocket the money and become multimillionaires. "And they'll do it all leaving me to take the blame. What the fuck did I ever do to those guys?" "Like I said, they've messed with the wrong trannies," Dave said starting to type. "What are you doing?" "Going to take this apart. Remove you from it completely but leave it so it everything else goes through. Except now it'll send notices to all these important people on this Timko's guy's contact list when the sale goes down. Giving details as to where the money was actually sent and deposited. Going to take some doing, who ever set this up is almost as good as I am. But no one is as good as I am." As Dave went to work Milo found it almost funny to hear the usual muttering his roommate care out with while working on a computer, but said in his new high cute squeaky voice. Dave had been clacking at the computer keys for about 5 minutes when they heard the elevator door chime far down the hall. Meaning that someone was coming onto the floor. "Hurry up," Milo said. "Doing the best I can but I need at least 5 more minutes," Dave said stepping up his work. "Shit," Milo said moving to the door. "Guess I'll have to distract them." "Any ideas how?" Dave asked. "How do you think?" Milo said adjusting his set of tits before quietly leaving the office. "That's my girl," Dave said getting back to work. Milo quietly closed the office door behind him. Seeing a shadow down at the end of the hall he hooked around the offices so that he came to the person that just walked onto the floor from a different direction than Ravi's office. He was never more thankful for the thick carpet on the floor since it meant his new shoes weren't making too much noise as he hurried along. Turning a corner his heart as much sank as much as it flared up seeing a guy in a Zorro outfit wandering towards Ravi's office. Fucking Timko was on the floor, and might catch Dave before he was done. "So are you like suppose to be Batman or someone. Batman doesn't wear a hat." He said coming up behind Timko, the man who was trying to set him up. Timko turned around. His walk turning into what he must have thought was a cool saunter when he saw "Cindy". "I thought I saw you come up here. Weren't you with someone?" "My sister and some little guy, Ravi. My sister has the hots for those overseas types. But he's dealing with getting his drunk on in the men's room right now." "You don't have the same hots for the same guys your sister does?" Timko said getting a little too close. "Guys dressed in skin tight black from head to toe ain't bad," Milo said reaching up and taking off Timko's Zorro hat and placing on his head. "I've seen you around the building, in your suit. I thought you had a good build." And with that he started running a long fingernail along the row of button his Timko's shirt, letting them unbutton as he went. "Didn't know it was this good." "So you do work here." "Ummm-mmmm, not that you would see me. Oh I get it, Zorro right. Didn't Zorro have a whip?" "A sword." "Oh, a sword." Mio said reaching down and cupping Timko's crotch. He wasn't surprised that it was already getting a stiffy. Arrogant prick. "So how about a little..." Timko said reaching down and beginning to pull his stiff little dick out of his pants. Milo's mind raced. If he brushed Timko off now he'd cause a stink. Dave would still need some time. And if he couldn't finish up, it was jail Monday morning. Oh well... "Tell you what, it's, you know, that time of the month.....but ummmm," Milo said licking his lips. There in the hallway where he'd worked for the past 5 years. Making decisions on an hourly basis that saw millions of dollars invested and moved just by his instruction. Milo Schullenburg dressed as a teenage girl squatted down some so he could take the cock of a man he wanted dead in his mouth. There was only a slight hesitation before he grabbed the dick and licked the head. He tried to remember the few times his former girlfriends went down on him. But there really wasn't anything that prepared him when the dick was forced past his teeth and headed down his throat. He tried not to gag too much, at least it didn't taste like he thought it would. Hated to admit that it tasted OK. There was also something cool about the thickness and the texture that Milo couldn't believe he was enjoying. Timko brought Milo back to reality by grabbing the back of his head and really pushing him down on his cock. The balls in his hands were beginning to pull up, which Milo knew what that meant. Later on he wasn't sure what caught his eye but suddenly he could see, to the back of Timko, down the hall, Dave looking out of the office door. A look of shock on his face as if he couldn't believe what he was seeing. Not that Milo could blame him. But standing in the doorway meant Dave was done. "Hold on," Milo said pulling the cock out of his mouth. "Hold on before you blow." "I just about was!!!" Timko said a little too loud and desperate. "No no keep it going big guy. Come on." Taking Timko's slick cock in his hands he walked his adversary down the hall. Dave quickly closed the door when he saw they were heading his way. "My sister.....my sister's been waiting for the Indian guy in this storage closet for a while now. He's not going to be fucking her anytime soon. How'd you like a ride?" "You sure she won't...I mean...don't want...." "Oh trust me. She'll LOVE this. Look, she's in the closet cause she thinks it's kinkier to do it in the dark. When you go in, you'll see she's ready. Just close the door and do her in the ass in the dark. She's a party just waiting to happen" "This is so cool," Timko said. Milo opened the maintenance closet door and saw that Ravi was still in place. "Snowy, you ready? Yes? OK, I got you another guy for you, a better guy," Milo said to the obvious unconscious Ravi, and then turned back to Timko. "She's all set, go get her." Milo made sure that Timko could see a figure, make out an ass, but quickly closed the door the second he steped in. Shutting the door he could hear some fumbling but then the unmistakable sound of flesh against flesh and Timko's groans of "Oh yea!!" Running down the hall Milo knocked on the door and grabbed Dave the second he looked out. "We gotta run!!" "Why is your hand so slimy?" Dave said running down the hall behind Milo. "You know why my hand is so slimy, bitch." "I am so proud of you," Dave said without too much of a laugh in his voice. Thankfully they didn't need a security card to get out of the area they were in. Dave stopped them for a moment and removed the Zorro hat from Milo's head, leaving it in the security doorway so it couldn't close completely. "Why do that?" Milo asked as he pushed the button for the elevator. "When I saw what you were doing I used the info I got from that Timko guy's database to text his wife at the party. Using his account I gave her directions to the storage closet and told her to come up and join him for some naughty party fun." "Holy shit. Remind me never to make you angry at me." "Hey, I took your dick away earlier today and you're my best bud. Think about what I'd do if I got mad?" 'The girls' watched the elevator indicators above the doors. Luckily their down elevator came just seconds before Timko's wife's up elevator reached the floor. They got to the ground floor, made a pass by the bar. The Bartended had kept his word and filed up Dave's backpack with more than a few bottles. He got a kiss from both girls, not more than a peck, before they ran off again. Just as they stepped out their ride for the trip home was pulling up. Dave had splurged and gotten them a stretch limo. Milo's reward for the evening adventure. The girls got in the back, settled in and let the driver know he could leave at any time. "So Cinderella, you ready to turn back into a pumpkin?" Dave asked settling in next to Milo. "Not just yet," Milo said reaching over and hitting the button that raised the solid partition between the driver's seat and the back of the limo for privacy. "Don't know about you but my dick needs to get the blood flowing again. We should be able to..." Dave said beginning to pull his cock out of his gaff only to be stopped by Milo reaching in aggressively and doing it for him Dave was too busy trying to figure out why Milo was doing that when Milo went in for a kiss. Not just a polite thank you kiss like the bartender got, but a long deep meaning business kiss. "This isn't part of the bet. I didn't bet you couldn't act like a horny girl, just look like one," Dave said stopping the kiss, even though he had wanted to have it keep on going till they got home. "Yea, but I turned into a horny girl anyway," Milo said tweaking the cuteness in his new voice 'I'll only ask once, you sure about this?" Dave said giving Milo one last chance. Without saying a word Milo reached out and pulled at Dave's panties and gaff till they were low enough to completely release his very swollen cock. "That's a big dick you got there baby," Milo said before going down on Dave's cock. This was a very different cock than the one he went down on earlier that evening. For one thing, he WANTED this one in his mouth. He wanted to give it pleasure. Dave was both in ecstasy and incredibly confused at the same time. Because Milo was giving him the best head job he'd ever had. His roommate's mouth was doing things to his cock, while his long fingernails were working his balls, both in ways no other guy had ever done. Milo's hand left Dave's balls and worked their way up to his chest. At first grabbing a fake tit, old habits dying hard, but then going beneath the bra, undoing the tape and beginning to play with Dave's real nipple. Dave couldn't help but just lean back and enjoy the attention he was getting. Eventually Milo pulled off the cock he'd been sucking. It was almost purple and larger than Dave had ever gotten it before. Milo started shifting around till he was hanging off the end of the limo's back seat, his knees resting on the floor. "You made me into a girl," he said pulling down his own panties to expose his ass. "Now make me a woman." Dave was far past trying to figure out what got into his formerly straight roommate. Or himself! Here in front of him was, by everything he could see, hear and smell was a young girl. Yet Dave was harder than a rock. Maybe it was enough for him to know that under all the lace was the cock and ass he'd secretly lusted after for the past two years. Kicking of his shoes Dave positioned himself behind Milo. He lowered Milo just a little but the angle was perfect from there on. Letting out a great squeal Milo took the head of Dave's dick with one thrust, then purred like a kitten as Dave slowly pushed his thick dick into the shaved white ass of his roommate. Needless to say, it was the tightest ass Dave had ever fucked. Dave grabbed Milo by the hips and started pile driving him. Milo had started this wanting the full experience for the evening. Just to experiment. With Dave's cock pulling in and out of his ass, he was now wondering why he'd waited for such a lame excuses to try this. Dave knew what he was doing and was hitting the mark inside Milo's butt better than Milo had ever hit one of his old girlfriend's clits. Milo reached down with a free hand and pulled his hard cock all the way out. He never figured he'd ever get fucked and never though anyone could get hard while being fucked. Now he never wanted it top end. But is dick was just as big and purple as Dave's was when it entered his hole. He was close to shooting too. It only took a few more strokes for both girls to make them cum. Dave shooting his entire load deep within his roommate's ass. He quickly pulled out and turned Milo around in time to be the full force blast for his new lover's cock all over his cleavage. The two men knelt in the back of the lime quietly for a few minutes trying to catch their breath. Cum dripping down Dave's fake tits. Cum dripping out of Milo's no longer virgin ass. "I'm going to have to tip the driver like a muther fucker for the mess we made back here," Dave said in deep breaths. "Have you seen my shoe?" "Yours are over there. I think that's my panty. You know, besides whose wardrobe is who's I think we have a few things to work out," Milo said trying to pull herself together but still enjoying the ass rocking she just got. "All we have to figure out is, which bedroom were going to use tonight, and from now on," Dave said kissing Milo again, just as passionately, just as deep. "Let's just switch back and forth between the bedrooms each night, that way we'll never have to clean them." "Yea, you're still Milo in there," Dave said tapping Milo's forehead with his fingernail. The two men collapsed into each other on the back seat. So tired that just the motion of the limo was strong enough to keep them from moving. "Did you have fun tonight?" Milo asked. "Are you kidding? I got to get my fem on again. Industrial espionage. And I fucked my best friend. Better than sitting around playing computer games, that's for sure." "Can we do the girly voices all weekend?" Milo asked playing with Dave's blonde hair "You like the girly voices?" Dave asked truly surprised. As if he hadn't been surprised enough that night. "I'm digging sounding like this." "Then we'll do the voices. You want to stay dressed like this?" "We don't' have to. Not this weekend. But I think both of us getting our fem on again is going to take the place of Halo once in a while." Milo answered "I'll start shopping." "I don't think I can call myself straight anymore. You, even though I have a dick, you just fucked a girl, so you just failed the Gay test. You know more about the terms. What does this make us? Bi? Trans? Is there a mix? Straighbigaytrans?" Milo asked, feeling that the limo was coming to a stop at their apartment building. "What it make us..." Dave said going in for another kiss, "is very happy." "Oh yea," Milo answered, returning the kiss. By the time Milo got to work on Monday morning, most of the action was over with. The bad guys were found out and hauled off by the police. Milo immediately got a promotion and major raise, although they were disappointed that he was not at the party. He was able to explain away his not being there on a cold he was fighting. Which was also the reason his voice still sounded a little funny. When he returned to his job on Monday, Dave got a lot of questions about the blonde hair and no beard. But it had been the Halloween weekend and eccentricities were kind of encouraged among the creative staff. And being their smartest and most talented programmer, nothing was said when the blonde hair remained from then on. With Milo's new paycheck it wasn't long before the guys moved out of their apartment and into a large house in the suburbs. Not many people could afford a house that large, but he neighborhood was happy to see the two married couples that had moved into the house that has sat there empty for so long. Although the more sharp eyed folks up and down the block couldn't help but notice that they never saw all four housemates at the same time. Just either just the two guys, or just the two girls. As for the bet, the girls are still taking turns being each other's bitch.