I Bet You'd Be Better As A Woman free porn video

I Bet You'd be better as a Woman By Gail Blue "Hey Karen, what'cha watching?" I had surprised her. Her face flushed red with embarrassment, and she was breathing heavily. "Sorry, I didn't mean to sneak up on you. I just finished up on the computer and was about to turn in..." Karen was fumbling with the remote, trying desperately to turn off the television. I could see sweat pouring from her brow. Her pants were off. Curiosity overcame me, and I turned to watch the screen. It was a talk show; three women were just sitting and chatting. I listened in. One woman was telling the hostess about how their relationship had changed since her husband had gotten a sex change. Evidentially, the third woman used to be a man. Karen finally managed to get the remote to work, and the show flipped off. "Honey, are you okay?" I asked. She looked miserable. Her face was pale and confused. "God, I'm sorry Max. I swear it won't happen again." "What are you sorry about?" I looked down and saw she was moist between the legs. "Oh that. You're way more embarrassed than you need to be. We've only been living together a few months. People masturbate. That's what they do. It's healthy." "Yeah but... Oh, I'm sorry I didn't mean to. I just got so... horny all of a sudden." "No worries. Seriously, I'm not mad, and I won't be mad. But what were you all excited about." She started speaking timidly. "You saw the show. I didn't know what the topic was going to be. Then when I found out that the lady used to be a man, I got really turned on all of a sudden. Look Max, I have a little confession to make." "Okay." I wasn't sure what she was going to say, and then it hit me. I suddenly felt very uncomfortable. "I think I find trannies really sexy." "Oh, thank god!" She looked at me sideways. She was relieved, but curious. "Why do you say that?" "I thought you were going to tell me that you used to be a man." "No, I've always been a woman, except I guess when I was a girl. You know what I mean." "Well then, let's go to bed. We'll talk about it tomorrow. You might be a little weird, but all the best people are." We tried to go to sleep, but Karen was nervous and edgy. Eventually, she got up and went to the bathroom. Even from the bed, I could hear her running her vibrator, and she moaned more than a few times. I turned our bedroom fan on high to try and give her some privacy. The next morning at breakfast, she wouldn't make eye contact with me. She seemed to be waiting for something, almost like she was holding her breath. It's the way she acts when she's expecting bad news. "Feel like talking?" I asked. "I guess." "You don't have too, not if you don't want too. But... I think we're going to need to talk about it eventually. Otherwise you're going to drive yourself nuts." "Okay. But it feels really odd for me to say this. I've never told anyone this." "You can tell me." "Well, you know how I have certain... kinks... from time to time. Like that time I asked you to tie me up?" "Yes. That was a lot of fun. I enjoyed it." "One of my um... kinks... is trannies, I guess. They've always turned me on a little. I thought it would go away, but then I saw that show last night, and I just can't stop thinking about it. It's turning me on so badly." "You want me to throw on a dress for you?" I was just joking, but as soon as I said it, Karen's face looked like it does right before she goes into orgasm. "I'm just kidding." Her face flushed beat red, the same way it had the night before. "Don't mess with me like that. I know you're kidding, but anything to do with that is really turning me on." "You want to have sex?" "Maybe... but I'm distracted." "We can do it out on the couch. You can turn your show back on while we do it." "God yes!" She grabbed me, and practically dragged me out the living room. We turned on the show, and played at taking each other's clothes off. They started showing sexy pictures of the transsexual woman on TV, and Karen lost it. She pushed me down and straddled me, mounting me and doing most of the work while she continued to watch the television. Afterward we flipped off the show. "See, that worked out okay," I said. "Thank you, thank you, thank you." "I know you go through phases. Why don't you see if you can get it out of your system?" "What do you mean?" "I don't know. Watch a lot of programs about trannies today. Masturbate until it gets boring." I spent the rest of the afternoon playing video games and Karen spent most of it out on the couch. She'd gone at it at least six times, and there wasn't much sign of her letting up. I went out and had sex with her a few times, but she just kept going. She wasn't really getting any more relaxed. She seemed like a nervous wreck by supper time. "How's it going?" I asked. "It's freaky. I've never been this turned on. I mean, I've always liked trannies a little, but it's like a switch flipped in my head." "I'm worried about you. We should get out tonight. Get some air." "I don't know. I feel really exhausted." "I thought maybe we could go to a drag show." Her eyes widened again. "Oh, thank you, thank you, thank you." It was strange to see Karen so attracted to trannies. She'd always been a fairly down to earth woman, and we had a healthy sex life. Still, when things turn her on, it starts to mess with her head. Last year, we'd seen an adult movie on bondage, on Skin-a-max, and she couldn't stop thinking about it for weeks. She'd always find a way to work it into the conversation. After we tried it a few times, she calmed down and went back to normal within a few weeks. While we were at the drag show, she rubbed my leg constantly under the table. There were several performers. Some were more feminine than others. The more like a woman the performers were, the more they turned her on. When we got home, we started getting ready for sex, but Karen wasn't so into it. "What's wrong honey?" She had the disturbed look on her face again. "Don't take this the wrong way. But I'm really turned on by transsexuals right now. A regular man is a little distracting." "You always liked regular sex before." "Not when I'm in one of my moods. God, this is so embarrassing. Look, don't get upset, but I keep thinking about dressing you up. It's making me miserable." "If I let you put a little lipstick on me, would that help?" Karen's head whipped around and her eyes got huge. She grabbed my hand and led me into the bathroom. There she applied the thinnest coat of pink lipgloss to my lips. It didn't look all that bad, it was kind of cute actually. I played at making a pouty face in the mirror, and something odd happened: I began to get aroused. Karen saw this and immediately mounted me. We had sex on the bathroom rug. She grabbed a tube of red lipstick, and we want back to the bedroom. We made love several more times, my arousal heightened whenever she reapplied the lipstick. The next morning at breakfast, Karen was glowing. "You seemed to enjoy yourself." Now I was the one embarrassed "Yeah, I'm surprised. I didn't expect that to do anything for me." "The lipstick?" "Yeah." "You won't get any argument from me. Have you ever been turned on by wearing makeup before?" "No, I've never tried it before." "How did it feel when you put it on?" I could see her eyes glistening, and I felt my pants tighten. "This is really embarrassing to say, but it felt electric. Kind of like what you said, like something had been switched on in my brain. I suddenly found my face really sexy, almost like it belonged to someone else." "Well, you know I did have this little fantasy. I thought I was just going to keep it to myself. Don't get upset but, here goes... I bet we'd both like it better if you were a woman." "You want me to get a sex change?" I was still aroused though taken a back. "It's just a fantasy, but I was thinking more like a bet, a challenge." "I think with the lipstick it might have just been the thrill of trying something new. It doesn't mean I want to stop being a man." "Well maybe not..." She smiled in a dismissive way. "But don't worry, this is more a wait-and-see kind of bet. And I bet, if you tried it, you'd prefer being a woman." "What's a wait-and-see kind of bet?" "I was thinking about this last night. I was thinking, maybe every week, you start doing something only a girl would normally do. We'll start off with small, things other people won't notice. Then at the end of the week, if you don't like it, we stop. Bet over, and you go back to doing manly things." I was apprehensive but still very much turned on. "Sounds weird." "I thought you said weird was good? And if at the end of the week, if you do like it, then without knowing what's next, I give you something new to do. And you have to give it a try for at least a week." "What if I don't like it?" "That's what makes this interesting. You have to do it. Like I said it's just a fantasy... But if you want, we could start off really slow and easy, just things to get us going in the bedroom, things that won't show." "When does it end?" "Whenever you say 'no', or a year from now when we go to Thailand for your sex change. But there's a catch." "You mean besides getting my penis removed?" "Ha, like it's going to go that far." She winked. "The catch is, if you quit, and then you start doing any of the girlie things I gave you to do. You have to start up again immediately, and you can't say no for two more weeks." "This is really pretty extreme isn't it?" I was sweating. I could see her see me sweeting. "Come on, only if it goes all the way. We'll probably just try it for a few weeks until the fun wears off. But what if it does go all the way? What if we like it? That's what makes it thrilling. It's all about the possibility, not actually going through with it." "You really want to try this?" "I hadn't thought we would. I was just fantasizing, but god yes! It'll give me something to fantasize about. Besides, I do think you'd be good as a woman." "How so?" "We'll for one thing you're really cute, especially in the face. And while you're not a wimp, you're kind'a small and thin, so you could pull it off. It won't look gross on you. Also you really like clothes, I mean you're always buying designer stuff, so being a girl might be a bit of an upgrade for you. Honestly, I think I'm turned on by... um feminine men. I think one of the reasons I like you so much is because I can almost imagine you as a girl." "Are you kidding?" "Kind of. But it's not going to hurt anything to try. It's mostly so I'll have something to think about to turn me on. And you really seemed to enjoy that lipstick." She winked again. "Is that so bad? Doing something that turns us both on? I blushed, "Okay, so what's the first thing I'd have to do?" "You mean the first thing you get to do... If I tell you, you have to do it, and you have to take the bet. That's the rule." "But it's only for one week right?" "Yes, if you want to stop, and we won't start off with anything overtly girlie. No one will notice." "How do I know that if you don't tell me what it is?" "Just trust me. You liked last night, didn't you?" "Yes, but it's just so embarrassing." "Like having you tie me up wasn't? And I loved that." "Okay, I'll do week one." "Great! Go up and get naked in the bathroom, I'll be right up!" It turns out week one was shaving off all my body hair. Karen explained that it wasn't just a one-time thing, I couldn't have any stubble while the bet was going on. We had sex immediately. The next few weeks were easy. Week two was that I had to start growing my hair out. It didn't have to look like girl's hair, it just had to be getting longer, and if I got it cut I had to tell them, "Just neaten it up, I'm growing it out." Week three, I had to start taking care of my nails. Karen wanted me to grow them out, just a bit. I had to start filing them rather than clipping, and I had to keep my cuticles clean. "Are you ready for week four?" "Well, I haven't decided if I'm going to keep going." "Aww, you're not supposed to decide rationally. It's whether or not you're enjoying it. Does it make you you feel better?" "You mean do I like doing my nails? They do feel good I guess." "Then welcome to week four." "What's week four?" She led me over to the couch and lifted up my legs. She slid my shoes and socks off, and started massaging my feet. "Week four doesn't feel too bad so far." "No it doesn't. Does it?" She placed my feet on her lap and started by wiping off my toe nails. Next she applied a base coat of clear polish, followed by a color coat of pink, and another top coat of clear. "Don't worry, we'll leave your finger nails clear," she reassured me as she started the process on my hands. "Don't you think people might notice?" "They probably won't, but they might. This is week four after all. Really, no one will think anything about a clear coat. If your finger nails are slightly shiny, only a total homophobe would care, and they'd never notice. It's more about how they feel at this point." "They do feel thicker, and kind of slick." "Kind of like your hands are wearing lipstick?" "Kind of." I got hard, and Karen rubbed me through my pants, avoiding touching my nails, until the polish had dried. Week five turned out to be ear piercings. No one said anything about it, but I considered it a bit much and was starting to wonder when a good time would be to stop. But, honestly, every time I got home and put those sparkly diamond studs in my ears, I found myself wondering how long it would take for my hair to grow out so that it would lay across the back and accentuate the earrings. *** "Okay, okay, I'm still enjoying myself, let's do week six." Karen touched both my hands with hers and looked me in the eye. "We're going to love week six." "Why what's week six?" "Week six is the start of the first permanent change." "Are you putting me on hormones?" Her eyes got big again, but she narrowed them. "No, something more subtle, we're going to start to get rid of all your male hair. But don't worry too too much. We're going laser not electrolysis, and before you freakout, let me tell you that the first couple times don't really do anything permanent. You'll go down to the clinic once a month. They'll zap you and a week later, all your male hair will fallout. But it'll all grow back until you go three or four times." "We're not doing my privates are we?" "Oh no, not to start. Just your body, your legs, your face. We might get rid of some of the mess near your privates though." "What if I don't want to?" "You have to. You agreed, remember?" She turned her back. "You can always quit next week. No real harm done. Besides I already paid for the appointment." That afternoon we want down to the clinic, and a few hours later my entire body was red and bumpy. A few days after that, the hair started falling out in the shower. In the mornings, Karen would pinch my checks and see what came out. My face felt a lot softer and looked pinker. I'd never noticed that even the few beard whiskers I had, had given my complexion a strong gray tone. Without this, and with my hair starting to get shaggy, my features looked downright cute. My face was starting to look foreign to me, like it belonged to someone else. But it was someone I liked looking at. *** We were in the bedroom. "Are you ready for week seven?" "I don't know. After the hair removal, I'm starting to have second thoughts." "Oh come on, it'll be a few more weeks before your next session." "Is week seven as bad as week six?" She reached into my shirt and started stroking my smooth chest. She stopped her finger tips on my nipples and nudged them around in little circles. "Come on, week six wasn't so bad. It feels pretty good to me right now. And you know I can't tell you what week seven is. That's half the fun." I closed my eyes. "Okay I guess I'll do week seven." She kissed me. "Good girl. Week seven is easy. All you have to do is to start wearing girl's underwear." Before I could react, she pulled out a white box filled with panties. Most of them looked quite plain, black or white cotton panties you might mistake for trendier men's underwear, but some were fancy, red or pink satin with lace. She helped get my pants off, and ran a pair of pink satin panties up and down my legs. It felt wonderful. She lifted my legs and slid the panties up along my thighs and used them to caress my erect penis. Then she opened another box filled with women's tops. Again, most were plain black or white baby doll tees I could wear and get away with, but some were lacy camis that matched the satin panties from the other box. She smiled and pressed her finger against my lips to keep me from talking, then lifted my arms and pulled a pink satin cami down over my torso. For the next hour, she caressed me through the pink satin. She mounted me, and I let her hold me down. Until finally she slid my penis into her pussy and we climaxed. It wasn't until we were lying in bed the next morning staring at the ceiling that she spoke again, breaking the silence. "You can wear the more normal looking stuff whenever you like. I figured we'd save the frilly things for the bedroom. I don't think anyone will notice. So I take it you like your new panties." "Last night was amazing. I don't know how to describe it. I think I like it when you treat me like that. Somehow it makes me feel... wanted." "Desired you mean. That's part of being a girl. Men value themselves based on what they can do, women do that, but they also value what they are, how they feel. Look at yourself in the mirror. Is there anything wrong with being desirable?" *** Week eight was simple. Karen suggested that we both start eating a little more like girls, to trim down our figures. I didn't have much objection. With week nine looming, I started to think about the next hair removal procedure. In my mind, I'd decided that week ten would be the end of it. I felt sad, but things were going too far, I didn't want anything permanent. Week nine was simple. She had me wearing women's pajamas and nighties to bed. Again some were simple cotton pajama sets that could easily be mistaken for men's underwear, while others were satin and lace, meant for special occasions. A few times Karen wore my old male underwear to bed: Boxers, a cotton tank top, and tube socks. She'd explain that "someone ought to get some use out of them," before helping me on with something frilly. Then week ten came around. "That's it, I think I'm out." "Aww, really?" At first she looked at me like I was kidding, then after a few minutes of silence it sunk in, and she looked at me like I'd canceled Christmas. "It's just that I think things might be going too far. It unsettles me." "So you're not having fun." "No, I am. But something maybe feels a little wrong." "Okay, okay. I guess I knew this day would come. You know the rules right?" "I need to quit all the girlie things then?" "Yes, but it's not like you need to go out and get a buzz cut right away. Just the next time you do something, go back to the male equivalent." "What if I like my hair long?" "The rules are the rules. That's part of it. But you can always just slip up and do something girlie if you want to keep going." "So if I put on a night gown, it's on to week ten?" "Yep, plus then you have to do week eleven and twelve, no arguments. Rules is rules." "So what was week ten?" "I'm not saying. But it's easy enough to find out." I lasted all of about two hours. The end of one of my nails felt rough, and I simply reached down for an emery board to file it smooth. We were out in the living room watching TV, and as soon as I realized what I'd done, I looked up to find Karen smirking at me. The smirk became a warm smile. Her eyes were elated. "Welcome to week ten Sweetie!" "Oh, crap." "Don't worry you'll like it. But first we gotta get you down for your second skin treatment. You haven't quite missed it yet." The session wasn't so painful this time. I think there was less to zap. Afterward, Karen hurried me home to show me what week ten was all about. She had four shoe boxes. The first contained a pair of simple black leather sneakers I could wear almost anywhere, it wasn't until I examined the tag that I realized they were women's shoes. "I figure you ought to see those first, But Sweeite, wait until we open the other boxes." She said while throwing all my old male shoes into a storage box. The second box contained a pair of black patent four inch heels with a strap that latched around the ankle. She pulled these out and started caressing them. "Did I ever tell you I have a little bit of a shoe fetish?" She asked, and ran her tongue along the stiletto heel. I was lying on the bed, and she lifted my legs and very carefully, placed the first shoe on my right foot. The shoe was open toe, and I could see my red polished nails displayed at the tip. She was sitting next to me, and as she latched the buckle around my ankle, I couldn't see her face, but I could feel her tongue glide over the tips of my toes. She kept her rear to me, and as she did the same thing with my left foot, her spine shivered when she licked my toes. I spoke, not quite sure if I should admit this. "God, my legs look like women's legs. I always get this weird feeling like I'm watching someone else." "Someone sexy?" "Yes." "Hehe, it's like I'm plotting with Maxie to get rid of boring old Max." She pulled out a pair of white silk pumps and started running them, up and down my body. She gently ran them across my cheek, and I sucked at the heel. When we were done, she pulled out the third and final set, a pair of black leather booties with 3 inch heels. "I can't wait to see you walking in these, Maxie. You'll have to try them out at home." "Is walking in heels hard?" "Not really, you just need to work at it a little. You know what else I can't wait for... Maxie?" "What's that?" "As per the rules... Boring old Max has to agree to everything for two more weeks." I got a lot of use out of the black sneakers out and about; no one ever gave them a second glance. The heels I saved for home. It was the first thing to really, make me feel woman like, and often times I'd wear them when I was in lacier underwear along with a satin nightie so the feeling would be more complete. I didn't even try to hide my joy when the next week turned out to be stockings and pantyhose. We repeated another session in the bedroom with Karen rubbing my legs through the flimsy silken fabric. They felt great under my pants, and one day I started to wonder what it would be like to walk around outside in them. We have a fairly private backyard with an awning covered patio where no one could see me. I did however have to make it out to under the awning without being seen, so I wore an old winter coat and sweat pants over my lingerie and crept quietly back to where I could enjoy just sitting around in the warm weather. I did this while Karen was out shopping, and when she got back it took her a while to find me, but when she did, she came out with two mint juleps, undressed down to some lacy black underwear, and joined me. *** Karen looked glum. "Well, Sweetie I guess this is probably the last week. It's the last compulsory one at least." She rolled her eyes mischievously, "unless you slip up again." "I have been having fun. But it is starting to worry me." "How so?" "Just that we're having a lot of fun in the bedroom, but I don't know how the rest of my life would fair with it. That trip to Thailand doesn't seem as much of a joke anymore." "Yeah, that's what I figured. But hey, you have enjoyed all the girlie things we've done to you so far haven't you, so overall it's been a good experience hasn't it? I mean you don't regret it?" "Oh course not. It's been a lot of fun. The sex has been crazy good. And women don't seem so foreign to me anymore. I get the fun of being pretty... and desirable. I'll be a little sad when this is all over, but also relieved." "So are you ready to go out with a bang?" "I'm a little scared you put it that way, but yes I'd rather end with something good." "Okay then, we're going to go get your hair done! I think it's just long enough now where you can get some of the shorter girl styles." "Oh, man." "What? What's wrong?" "Well people are really going to notice that." "That's kind of the point. Look, Max doesn't need worry too much. I've spent the last week looking at hair styles, figuring out which one is the most feminine of the ones I could see a guy wearing." "So what are we going with?" "A nice pretty shag. Maxie will love it. It's one of those styles you see surfers with from time to time, but it will really feminize your face." She started playing with my hair, running her fingers through it. "But of course it's up to you. Well not entirely, I mean you have to get a female hairstyle, but if you want to go with extensions, maybe something a little Marilyn Monroe, that's your choice." "No no, your plan sounds just fine." Karen had it all arranged. We went down to her stylist, and I spent the next hour and a half playing hair model. I was surprised when they started talking about dying it, but they didn't do anything too noticeable. My hair had always been light brown, and they simply added a few blonde highlights too it. My hair was cut while it was wet, so I didn't have much of an idea what the final results would be until it dried. Somehow the cut actually made my hair seem longer. It was fuller and poofed out to the sides rather than lying straight down. They'd cut very soft bangs into it too that blended into the rest of my hair and hung diagonally across my brow so that a few tips of hairs fell in front of my right eye. It looked completely different from any way I'd ever seen my hair before, almost like I was wearing a wig. If my face looked cute before, it was now definitely pretty. When we got home, I changed into something lacy, and, of course, Karen wanted to toss me into bed immediately, but instead I stood by the full length mirror and just looked at myself while Karen played with my hair. The whole time, we silently smiled without the need for either one of us to say a word. Needless to say, being tossed into bed came soon after that. *** A week later, Karen had the same nervous jitters she had right before she told me she had a tranny kink. She hadn't slept much the night before, and I could see it was really bothering her. She was sitting cross-legged on the couch, and I plopped down beside her. "Hey Karen, I guess it's that time of the week again isn't it?" "Guess so," she said with a sigh. "What's got you down?" "Oh nothing. I guess I was just still enjoying it." "Did the kink ever wear off at all?" I nudged in beside her, but she didn't touch me. In fact I thought I felt her subtly inch away from me. "Not really. I guess maybe it's changed a bit though. Before I just wanted to throw you into bed and fuck your brains out. Now I think more about... well... more emotional stuff, you know just sitting close to you, like this." "So why are you so upset?" "You know, It's got to end. I mean last week was really the last week. If you hadn't slipped up it would have been a month ago. I guess I should just be happy about the extra time." She nudged my shoulder and tried to smile. "Those were the rules." "We still need to do this today. Let's get this over with." "Okay, are you having fun? Would you like to move on to the next girlie thing?" She said this like she was apologizing and looked away from me. "Sure, why not? Max can wait a while." I couldn't help but smile. She looked back startled, and her eyes deepened. They were open so wide and she leaned in to brush the tip of her nose against mine. "I mean the next skin treatment isn't until next week, so why not wait until then?" "Why not?" She shrugged and gave me a hug, "Oh Maxie, thank you, thank you, thank you." "So what's this week?" "Well this week, I have to go shopping, because I didn't get anything ready... but I know exactly what to do, it's going to be fantastic. Just give me a few hours." Karen rushed off to the store, and returned a less than an hour later. "Welcome to week thirteen Sweetie..." She announced and started pulling cosmetics out of a bag "No hiding anymore, from now on, you're going to be wearing full makeup!" I was shocked and aroused. Karen had her hand on my pants and felt my reaction as soon as she said the words. "Don't even pretend you don't love the idea. I've been wanting to do this ever since that first night with the lipstick. Hehe settle down, I was just trying to startle you. Don't worry, you won't be found out, come here I'll show you." She led me to the bathroom and explained that although she now expected me to wear makeup fulltime, it didn't have to be very noticeable makeup, and it didn't have to be very much." "In fact, I got you a bottle of tinted moisturizer, and a slightly tinted lip balm so that you can technically be wearing makeup without it really showing. But tonight we're going to have a bit more fun." She continued by applying a smooth coat of foundation to my face, followed by blush and way too much eye makeup. "But what I really like, my dear Sweet Maxie, is the lipstick." She twisted open a tube of light pink and swept it over my lips. "It the same color as the first time you let me put this on you. Of course, Max has to let you put it on now, those are the rules." My face was almost completely feminine. Between the haircut and the makeup I didn't look much like a man. "Wow, I can really see Maxie now." "I know. Don't you just love that face?" "Yes." I said trying to look slyly at the mirror. After we finished in the bedroom, we spent the rest of the evening and then the rest of the weekend with Karen showing me makeup techniques. We cleaned out a drawer, and she set me up with my own kit. After we settled down, we started thinking about how I was going to pull this off day to day. Karen was quite adamant that I had to wear every kind of makeup, not just the easy stuff, but that it didn't have to be very much, nor even a noticeable amount. The important thing was to go through the motions. Of course I wore the moisturizer and balm, during the day. But I also had to add a very light eye liner, a faint touch of eye shadow, and what they call translucent mascara to the mix. I tried to put on as little as possible, but a few times, when I didn't expect anyone to notice, I put on a little more, just to see how pretty it made my face. *** Unfortunately and predictably the next week, I told Karen I was quitting again. She moped around the house most of the day while I took my male underwear and shoes out of storage. That night, we went out to eat, and the conversation, while pleasant seemed to be between two friends, not two lovers. We went home and had sex. I think we both thought it was a little bland, though Karen made jokes that it was good to be with Max again. That night she didn't get much sleep. I could feel her tossing restlessly in bed, and I wasn't doing much better. I kept thinking of that first night, and wondered if she was going to get up and masturbate, but she didn't. The entire situation felt tense, and I realized I was feeling very uncomfortable about it, so I woke Karen up. "Wake up," I said. "What is it? I'm trying to sleep." "No you're not, you're tossing and turning." "So? I'm still trying to sleep." "I wanted to ask you something" "Can't it wait until morning?" "No it can't." I got up and led her by the hand into the bathroom. I pressed my finger gently across her lips to keep her from saying anything. I opened my drawer and pulled out a tube of red lipstick. She was mesmerized, almost frozen. Her hands dropped to her sides and she started breathing heavily, but she didn't say anything. I pulled her close to me and very gently applied it to her lips, then moved in close like I was going to kiss her, and ran it across my own lips. "What do you think of that?" I asked, with a raised eyebrow. "I think you're mine now girlie, girle." We kissed for a while and made love all night. The next afternoon, I awoke feeling Karen licking my belly. "You do realize, Maxie, I'm not going to give you up now. Not without a fight." From the tone of her voice I couldn't tell if she was being serious or playful. "You have me for this week, and two more at least." "I think I have you forever. Come on, I was right. You do prefer being a girl." "It really hasn't gotten dangerous yet. We've been very careful to make sure it doesn't really affect my life, so what's the harm?" "Are you going to say that, when we're in Thailand. Right after your sex change?" She said this coyly, with smug satisfaction. "Come on, you're not serious about that." "I'm not? We'll see. We're into the third month. And I have you for at least three more weeks. I'd say it's time to start getting serious about it. Put you to the test." "What kind of more serious exactly?" She opened another box, this one filled with bottles and medical syringes. "What's all that?" "Female hormones. I got them from the doctor that runs the hair removal clinic. I told her you were just too embarrassed to ask. She's had other trans customers before, she was happy to be... accommodating." "You're really going to give me female hormones?" "Yes, I am. I took a class last weekend on how to help with injections. It's normally for spouses of diabetics, but it'll work for this too. And don't worry too much, it takes a long time for the hormones to actually do anything. But I figured if we were this far into it we better get started." "Oh, god." "Come on, I know you're going to like it. You just need to give it a try. Maxie's not gonna sprout breasts for a few months. All it's gonna do right away is mess with your emotions. But Sweetie, I see the way you look at yourself in the mirror. You will like this." I didn't say anything, and Karen gently coaxed me over on my belly. She cleaned a spot on my ass with alcohol. "Are you scared?" "Hell yeah." "Let me ask you something. If I could give you a pill that would magically give you breasts for half an hour, would you take it?" "Yes, I guess I would." "Why?" "I don't know. It'd just be fun to have boobs. I love your boobs. I never get to touch them enough." "Do you ever look at yourself in a nightie, and think it doesn't fit quit right?" It was hard to admit. "...I guess so." "Have you ever looked at your face and wished it was softer?" "I guess so." "Since we started, have you ever looked at your face, and not wished it was softer, more feminine?" "No." She gently pushed the needle in. I could feel the cool fluid flow into me. Over the next week, Karen was very firm about giving me daily injections. I was still in shock, both that it had gone this far, and that Karen was so eager. I didn't want to piss her off, and it would take a while for it to take effect, so I went along. The hair removal was coming along really... effectively, and I didn't have to shave more than once every couple days. The weeks after that were both about clothes. The first she had me get all woman's tops, then the next week all woman's bottoms, so that I wasn't wearing any male clothing at all anymore. Of course we mitigated it by getting a lot female clothes that looked like men's clothes. Anything was fair game, as long as the label said "women's." None of my clients had noticed anything, or if they did, they didn't say anything. I tried to quit the game again a few weeks later, but Karen caught me with lip palm on my lips. I hadn't thought much of it, I put it on while she was away because my lips felt dry. But that night when she kissed me, she licked my lips and announced, "You're mine for another three weeks Maxie!" She took to rubbing my nipples during sex. She said she was just "Encouraging them to grow." In the next three weeks, she bought me dresses, had me start using courier bags (or purses if I would prefer to call them that), and she got me a pink phone (which I could leave in a black protector case, if I really wanted to.) I tried to quit again, and made it through most of a week, before Karen caught me wearing a women's jacket. In the beginning, she'd been careful to help me separate out the two, the male from the female, but now she seemed apt to leave little traps around the house, nail files on the coffee table, my keys on top of a purse. She'd put the women's jacket in with my men's stuff. *** When I got home the next day, I had something to tell her. "Hey Honey, I think this is getting serious. I met a new client today, and she joked that she'd expected me to be a man, because Max is usually a man's name." "I can see that." "But she thought I was a woman." "Well you are, aren't you? You dress like one, you look like one. You've got more female hormones in you than male. What's the big deal?" "This isn't really a game anymore." "Let me ask you something. This new client, did how did it go?" "Fine I guess." "So, even though she thought you were woman, everything else was the same." "Yeah..." "So what's the big deal?" "I don't know. It's just different." "Does it feel wrong?" "No, just different." "You want to know what else is different about you? I think your boobs are starting to come in. I mean look at your nipples." I was wearing a white shirt, and when she said this something odd happened. Yes, I got turned on, but it wasn't only my penis; I felt my nipples tighten up, and when I looked down I could definitely see them though the shirt fabric. Karen gently unbuttoned my top, reached in and started massaging them. "You like how that feels?" "Oh god yes." "Well then Sweetie. Welcome to week twenty." She pulled out a box and gave me my first set of training bras. *** "So, I've been thinking, Maxie. About how last week you said one of your clients sees you as female." "Yes, I saw her again this week, and she's still under that impression." "Well, for week twenty one I was thinking, you've only been out in public in very subtly feminine things, and if your client thinks you're a woman anyway, then why not go dressed as one?" "I'm already wearing girl's clothes." "Yes, but only the ones that could pass as guys clothes. I think we need to get you out in more skirts." "That's a big step. That's embarrassing." "Why do you think being a woman in public is embarrassing? I mean fifty percent of all people do it." "Yeah, but they all have vaginas." "Not all of them Sweetie. There are a few trannies who get out just fine." "I've never seen one." "Exactly, how would you know? You can be one of those." "What if somebody sees me?" "That's the point." "No, I mean someone I know." "Look, we'll cross that bridge when we come to it. For now let's just get you out and about. We'll be careful." Karen had me go up and get dressed in a white blouse, a floral skirt, and heels. We did my makeup with a very distinctive dark red lipstick. Then we hopped in the car and took a long country two-lane highway over to the next town. I drove. "See you're out in public, looking a total hottie, and no one is the wiser. If anyone is staring at you, it's because they want to ravage you." She started massaging my thigh as she said this, and I noticed that she was the one staring at me. The car went over the centerline, and I had to swerve back to the right. "Don't distract me. I'm driving." "Well then, don't distract me with how hot you look." She rubbed my thigh one last time, and sat back in her seat. "Anyway, we've been driving for a while. Why don't you pull over at the next exit and get gas." "Dressed like this?" "Of course. What do you think is going to happen anyway?" "I don't know. Maybe everyone who ever made fun of me in high school will be there, and they'll all start chanting 'crossdresser, crossdresser' in unison." "Crap, and I went through all the trouble of arranging that, only to have you figure it out. Look Sweetie, I know it's scary. But it's also a thrill isn't it? Besides it's all automated. You don't have to talk to anyone. You just need to jump out, pump gas, and jump back in." I pulled into the nearest gas station, and did just that. My heart was pounding when I hopped out, and I managed to stumble over one of my heels in the three steps between the car and the pump. I caught myself and looked up to see a teenage boy in the next isle staring at me. He quickly turned away, obviously embarrassed. I slid my credit card and noticed my hand was shaking when I tried to place the nozzle into the tank. A few beads of cold sweat rolled down my body. The boy made quick glances in my direction. I saw him staring at my ass. I finished up, hopped back into the car, and squealed the tires on the way out. "So how was that?" Karen asked. "I thought I was going to have a heart attack! That was awesome." We both started giggling, and Karen held my hand the rest of the way into town. The sun had gone down, and I felt a little less conspicuous in the dim lighting. We stopped in a commercial district where all the offices had closed, and Karen had me hop out. She drove a few blocks a head and parked, and I walked up to meet her. There were a few people on the side streets but no one seemed to notice me. It was the first time I'd heard the click-click sound of high heels on concrete coming from beneath my feet. We drove out to what Karen described as a gay-friendly shopping district, and just walked around holding each other's hand. Karen ran into a local Greek restaurant and grabbed us dinner while I waited out on the patio. It was nice, and no one from high school showed up. On Wednesday, when I went to see my client, Maxie went in full makeup and a dress. Karen went with me to the building and walked me to the office door, but she waited outside until I was done. No one but I knew she was there. The client complimented me on the dress, and asked why I'd gotten myself all dolled up. When, I told her I was having dinner with my girlfriend that night, I didn't even think about the gay implication. It caught the woman off guard. She was surprised and embarrassed, but we got back to work, and things settled out. After that, Karen started taking Maxie out at least twice a week. It was a nice change from being couped up at home whenever I was dressing. *** The next few months were easy, Karen gave me simple things to do like watching some women's TV and learning to sew. It was easier than I thought to swap out clients, and by week 32 they all knew my as "Ms. Maxie." To my horror, a few of them realized I wasn't a woman, but the few who asked me about it shared their support in the same breath. One evening, I was in a silent mood, and Karen snuggled in next to me on the couch. I got up to go to the bathroom, and when I sat back down, I guess I wasn't sitting close enough. "Why are you sitting all the way over there Maxie?" "I'm sorry. I'm guess I'm just not in the mood to snuggle. I'm thinking." "You always were the more serious one. What'cha thinking about?" "What do you think?" I said pushing up my boobs. "You want bigger boobs or something? Fine with me." She looked confused. "No, it's just that you know, this started out as a bet, a game. And now it's not, but we keep treating it like it is... Sometimes." "You mean I keep giving you girlie stuff to do?" "Yeah. We're not really taking this seriously." "I thought you enjoyed the game?" "Not if I'm being forced into it." "Maxie... You can stop anytime you want. It's always been just a game." "But I don't know if I can go back. I feel painted in a corner." "You really do take this seriously. You know what? You don't have to go back, and you don't have to go forward. It's all been about nudging you forward, but only to a place we both want you to go. I care more about you then that bet thing." "Oh no, you're not going to tell me that your tranny kink is over are you?" "God no, I think that's lifelong," she winked at me. "So where do we go now?" "Where do you want to go with it? I mean I think you like being a woman." "Yes, I guess I do. I do. Funny how it just started out as a kink." "So what's next? Do you want to have a sex change?" "Sort of. I mean more socially. I like the female side of things. It's just that the thought of losing my special... my penis, is a bit shocking." "The rules are only here to help you do something you want to do anyway." "So you think I really want to lose my penis?" "You wouldn't be losing it. You'd be transforming it. Look at you, I haven't lost you, you're just different now. Let me ask you something, does your penis really want to be a vagina?" "I don't know." "Did it get hard when I asked it that?" I blushed, my penis was trying to force its way out of my panties. "Look, you don't have to go through with it, not if you don't want to. But let's see how far you really want to go." "What do you want?" "Honestly Sweetie, I still get a rush whenever I think about what we've done to you. I love the idea that you're becoming this feminine being. I kind of like wearing the pants in the relationship." "So you want to become a man?" "No... just the butch lesbian in the relationship. Somehow the idea makes you seem sexier. You know the next steps, unless you back out, are going to be pretty dramatic. How do you look at yourself, what you've become?" "I look in the mirror, and I see the girl of my dreams. Only when I move, she moves. When I look in her face I think she's the sweetest thing ever." By the time I finished this sentence, I noticed I was smiling. Karen moved in close and twirled my hair behind my ear. "I think so too." *** Over the next week, I noticed she started wearing bits of my old male wardrobe. She'd never dress like she was a man, but she'd work in different masculine elements. She seemed to give up wearing dresses and skirts completely. She didn't look butch, more like a tomboy. A few weeks later, she popped something on me. "This is one of those big weeks Sweetie. We're taking a trip." "We're not going to Thailand yet are we?" "No, not yet. But we are going to Canada, and Maxie is having some work done." She huddled in next to me and held my hand. "What are we going to have done?" I was breathing heavily, my eyes were wide open. She began rubbing my chest "Just a few alterations, just a few improvements." Her cheek glided against mine. "It'll be fun. It's a French speaking clinic. I'll have to translate, and I was thinking..." "What were you thinking?" "I was thinking, that if you wanted to, I wouldn't tell you exactly what was going to happen beforehand... Are you scared?" I felt my heart pounding "Yes." "Are you excited?" "Yes." She held my breast and leaned in to kiss the back of my neck. "Do you want to go through with it?" "Oh, God yes!" We flew up the next day. The clinic was clean and very professional, but they spoke in French and Karen did most of the talking. I'd just smile and nod my head. After the surgery, we spent a week in Quebec to recover, so I wouldn't have to travel. Karen rented house near Montreal. Part of the game, part of the fun, was that I shouldn't see myself in a mirror until the swelling had gone down. I wasn't surprised by the swelling in my chest as much as by the swelling in my face, so much so that I didn't even notice my ass until the bandages came off. There was bruising, and my eyes were blood shot. The changes were subtle, but noticeable. My nose, was smaller, slimmer. I didn't think it had been masculine before, but now it was something you'd never see on a man. My jaw was slimmer too. The face starring back at me looked delicate. "Don't put makeup on just yet, Sweetie. We still need to let it rest a bit. But I have another surprise for you. Here try these on." I was puzzled, as Karen had handed me a shirt and pants from my old men's clothes. But when I went to put them on, they no longer fit right. They had been skinny fit before, not loose at all, and now they wouldn't quite close. My breasts kept the shirt from buttoning, and the jeans couldn't get around my ass. "Okay, now try this on." Karen handed me a red silk baby doll nightie. It cupped my breasts together to from cleavage. And the skirt blossomed out around my ass. "How does it feel to be voluptuous?" "I think my breasts are bigger than yours." I still had my penis; it had just gotten hard. "I know. You're more of a girlie girl, than I ever was." "No one's ever going to take me seriously again. They're all going to be staring at my boobs." "...what were you saying? Just kidding." She glanced at my breasts and licked her lips. " So what do you think?" "I can hardly believe it's me, it's like a different person. I really want to go shopping and try dressing her up." "Well, tell you what. You rest up for a few more days, and then let's go out and get our new dress up doll here a bunch of slutty little outfits to wear for us." "Mmmm, I can't wait." *** A week later, Karen told me she had something special in mind, something exciting. We found a salon and had my hair dyed a deep auburn color, and added extensions so that it fell past my shoulders. I got long maroon finger nails, and matching lipstick with dark eye shadow. That evening, we went down to one of the seedier areas with a shopping area near some of the strip clubs that specialized in fetish wear. Karen bought me a shiny red metallic pvc romper (a sort of unitard that zips up the front), a pair of black fishnets, and black five inch heels. She collected all of my other belongings, my purse, my money, and my phone; and dropped me off on a street corner. She said she was only going to go just out of sight, but I didn't see her anywhere. A few cars slowed down near me, and I tried to my best to ignore them. I think about an hour passed, and more cars came by. I still tried to ignore them, but one stopped next to me. "Hey Sweet thing. Want to go on a date?" I was surprised the driver spoke English. "No sorry. I'm not working right now." "Could have fooled me. I'll give you ten bucks if you just come over so I can have a look at you." I didn't have any money, and Karen was nowhere to be seen. But with ten bucks I might at least be able to make a phone call. "Come on, I won't bite. I promise." I nervously edged toward the car. And even that close, recognition took a while. She'd gotten her hair cut short, it was man's style, but it wasn't too short, not butch, it looked okay on her. She was wearing some of my old clothes, the very ones in fact I tried a week before, and couldn't wear anymore. And she was wearing aviator sunglasses, at night. The car she was driving was different from the one she dropped me off in. She handed me a ten dollar bill. "Come on, bend over for me. Baby." I leaned in so my forearms were resting on her window sill. "Give me my money's worth. Unzip a little." "Out here?" "Sure Sweet thing. You owe me." I looked around to make sure no one was looking. A block away, I saw a group of men leaving a strip club. "You want to wait and give them a show?" It took longer than I expected to grasp the zipper, my fingernails kept getting in the way. I tried to do it slowly. When the zipper opened past he bottom of my breasts, I felt them separate. I pulled the romper open so that my nipples were exposed. Karen was squirming in her seat; she was having a hard time staying still. "How much do charge for me to spank you?" "You want to spank me?" "Yes, you've been a very naughty girl." "Two hundred." "Get in." *** She was lacing up a bow on my pink satin teddy. "One thing that'll be nice, if we do go through with it, is that your clothes will look a lot nicer." "Is that a good reason?" I caught a glimpse of myself in the bedroom mirror. I was arching one of my eyebrows. They had been darkened with a pencil and looked almost like a comic book drawing. The shiny lined lips underneath looked sultry. If I'd make this face as Max it would have been friendly in an almost comical way. Now it looked pouty. "I guess not. But I keep thinking about how you could look 'sleeker'." I was sideways to the mirror. She reached under my teddy and pulled my penis over to the other side so that we could see a clean arc, from the bottom of my breasts to the tip of my torso, reflected in the mirror. "It's not like you'd be losing it. It would just be inside you." "That'd make sex a bit tricky don't you think?" "We could get creative. Use our fingers, our tongues. If you want, I'll buy a strap-on." "Wouldn't that be a waste? Why not just leave the real one." "Well..." She blushed. "I was thinking I could wear it... most of the time." She ran her finger over my inner thigh. "I'd like to fuck you. I want to see what it does to you. I think it will change you, once you're used to having me inside you. It'll ease you up a bit. You're living like a woman right now anyway. Why do you want to be a man?" "It's just have you ever had a penis? It's been one of the most important things in my life for such a long time. I remember when I was a boy, being horrified at the prospect of losing it." "Maybe that's just because you never got to be a little girl. I wonder if it would help if you tried dressing like one for a while." I felt my penis start to squirm in Karen's fingers. "I could get you a teddy bear, and some lollipops." "That's... that's okay. I guess it would be inside me. But what about my balls?" "Just imagine, instead of feeling them swing when you walk, all you'd feel is a light breeze against your pussy. You could go anywhere, do anything, strip down naked in public, and everyone would know are a woman. All you'd feel from this teddy would be the light slap of satin against your body. Not the tug of that other thing." "Whenever I think about it, I get hard." "It wants to change. You've enjoyed the other changes." "I used to think of myself as a tough guy, if I needed to be. Now, I'm turning into a bimbo," I joked. "I still have a hard time believing it's me in the mirror. It's like a dream." "Merrily, merrily, merrily..." "Huh?" "Would that be so bad? If life were a dream?" *** A few weeks later, I found myself walking along a beach with Karen. I wasn't wearing a bathing suit, rather a long skirt, and I felt the wind circling around my legs, tickling the slit in between my legs. We stopped for a drink at an outdoor bar. While she ordered, I looked through my purse. I had to remember to get my passport updated. The men in customs asked quite a few questions. At first, they didn't believe it was me, but Karen had brought along a few pictures of me over the last year, so we could explain. I couldn't wait to cut the damn thing up, and my old driver's license. It wasn't really me anymore. Karen had changed too. I think she got a thrill whenever she opened the door for me, and now whenever she shopped for lingerie, it would be for me. I'd find something new layed out for me almost every weekend. It had changed me in other ways at well. Occasionally, I'd find myself staring at guys, wondering... That made her jealous, and put a look of determination into her eyes that wouldn't go away until she'd thrown me down on our bed and had her way with me. Sometimes I'd look at guys just to get her going. Originally Posted on Fictionmania (Review it if you like it. It makes me happy.) [email protected] This was very minimalistic compared to my other stories. I tried to distill it down to two characters, and focus on their relationship and the transformation. That's why there aren't many hard details. (We don't know their ages, exact professions, etc...)