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"Four! I'm going to kick your ass!" I said very confidently. "I don't think so," said Jen. "You are all talk and no action." "You want to make it interesting," I replied. Jen had been a friend of mine for a year. She was cute. Very cute. Not a bombshell. Jen was about 5'3". Maybe 100 lbs. She had a wonderful smile. Very charismatic. Lots of freckles. And big breasts. Jen wasn't like most other girls I new. She liked to golf, to drink, and to hand out. She liked a lot of the same movies as me. Same music. Like everyone, I liked a mix - alternative, techno, singer-songwriters (particularly the girls), and the occasional popular song you people don't admit to liking. Jen wasn't dating anyone. I was new in town. She won me over with a smile and a beer. We became good friends. Buds. Although I had a little crush on her, I wasn't all in. I still had reservations. I couldn't quite put my finger on it, but there was something that held me back. I liked being single. She clearly liked being single. But we were good together. We both had other friends, and other social lives. But we were together a lot, and it was become more like all the time. We went to lunch together most days. Went out to bars at least two nights a week. We golfed together almost every week. And, we would go to concerts together. Most were at small bars listening to up-and- coming artists. Particularly the female singer-songwriters. They seemed to be playing the local bars a lot. And, Jen and I both liked that sort of thing. Can girls and guys be friends? I wasn't convinced. In those situations, one of the two liked the other. They just didn't admit it or act on it. I'd seen a lot of "friends" in my day, and that was always the story. So far we had been doing the friends thing pretty well. We had some moments that there had been some tension. Watching movies late into the night sitting on the couch together. I could tell there were times she'd look at me and there was some thought of "maybe..." I know I had considered it some times. She's cute. We're good friends. Why not? Did I mention Jen was gay? She was the head of the LBGA in college. She just told me last week. But, I had figured it out a few weeks earlier. There had been sings. But, she seemed like she could be straight too. At least I got the vibe that she liked me, and considered "us" hooking up a couple of times. "Interesting... What are you thinking?" Jen asked. "How confident are you that your going to win," I replied. "Today.. Very!" "Alright then. If you don't think I stand a chance to kick your ass, then let's make it interesting." Jen asked, "First tell me what you mean by 'kick my ass'. Are we talking win by one stroke, or do you plan to give me a buffer?" "Well, you are already hitting from the women's tees, and I have to hit from the men's. What else do you want?" "How about you hit from the pro's tees?" Both Jen and I were average golfers. She had been playing since childhood. Both her dad and brother loved golf. They played all the time. Even with all that experience, she was OK for a girl. I'd only picked up golf in college. I wasn't very good. We were pretty evenly matched. But I usually won. We both loved to play. We managed to get out about once every week. This time we were playing on a new course that had just opened. In fact, we had strayed off the first 18, and were playing a part of the course that wasn't open yet. We had the whole second 18 to ourselves. It was nice. No one rushing us. Occasionally, we took liberties with second drives. I paid. It cost me $100 bucks, on a Saturday, and we were walking. We abandoned our golf cart in attempt to remain incognito. "The pro tees? I'm not that good. I might as well spot you two strokes each hole." "I guess you just a girlie man then". Jen liked to taunt me. She was tough. And accusing a guy of being girlie, or a sissy, is about as damaging as you can get. "Take off your skirt little girl." "Ouch! Dem's fighting words." "Comon' I want to see what you got. You are already ahead by four, with nine holes to play. If you want to make it a bet you gotta tee up from the pro's. Take off your skirt. Don't be such a little girl," she said. I thought about it. I've been playing really good today. That was one of the best front nines I've ever shot. She really thinks if I tee from the pro's, she'll win. If I'm going to give her that kind of advantage, I bet I can really make it interesting. This may be the ice breaker I'm looking for. What do you think she will go for? Maybe I should make her go on a real date with me? No, I'm not sure I really want a real date. Maybe a blow job? Yeah, that would be great. I haven't had sex in at least a year. There's been a few times when I thought she might be game. Maybe this is the sort of thing let will let us do what we really want to do. A little sex. No commitment. Still friends. Besides, she challenged my man-hood. "OK, I'll hit from the pro's. But you know that puts me at a HUGE disadvantage. So, this is going to have to be worth my while," I said. "Hey, if your hitting from the pro's, then you can name your poison, because you are going to loose anyway." "Bullshit. I'm going to kick your ass." "What'll it be?" Jen asked. I hesitated. But she got my adrenaline up with all the insults and challenges. So I said it. "If I win, you gotta blow me." Silence... I couldn't read her. She looked stoic. I didn't know what she was thinking. I was nervous. One of those moments where everything froze for a minute. Shit, what did I do? She was definitely thinking. Was she thinking, 'how the fuck did I get into this'? Or, was she considering it? "ok" "Really," I said in complete disbelief. "Yes! OK!" Wow. I really didn't consider she'd say yes. I thought she'd laugh it off, there'd be some awkwardness, and we bet dinner, or the cost of the next round. But she said yes. "OK, but your not going to win," she replied. "Get on with it. You won the last hole, so it is your turn to go first. Tee it up big man," She grinned. Now, I have been on my game with driving today. My drives have been straight and long. For some reason my typical slice hasn't been bugging me today. And I was in the lead. So I had only reasons to be confident. But, for some reason, now my nerves were bothering me for the first time today. There was no pressure. No one is playing behind us. The golf pro hasn't been driving by in his cart pushing us to go faster. But, now I was feeling pressure. I walked up to the black tees, teed up my ball, took a couple of practice swings, and then.... SHIT! I flubbed. I caught the ball with the top of my club, and the ball bounced straight up, and landed a few yards in front of me. "Wow, that was really bad," Jen taunted. "Shit, shit, shit!" I yelled. "Hey, and it appears that your ball didn't even make it to the women's tees. You know what that means sista? You gotta wip it out and play like that for the rest of the hole." "Fuck! No. Really? Your not going to make me" "Yup! You didn't reach the women's tees. You know the rules," Jen said. "Besides, I want to know what I'm in for when I loose." "Fuck!" I yelled again. "Comon' take it out, girlie man," Jen taunted again. I did. It was humiliating. I had never thought I'd be in this situation. I'd fucked up some drives before, but I was never in danger of not reaching the women's tee box. Then again, I'd never played from the pro's tee box either. And, I'd never had so much riding on a game before. "Shit! Are you happy? Take a good look!" "Hmmmm... I can now see why you didn't hit the ball very far. You ain't much of a man, now are you? What is that, about four inches erect?" "Fuck you! More like six. It is your turn. Let's get this over with," I replied. "On a good day, maybe," said Jen. We both finally reach the green. And there I am, putting with my dick hanging out. Embarrassing. I ended up hitting a ten. Jen hit eight. My lead was down to two. But, for the next few holes I got my groove back. I began to hit the ball well. Particularly on the drives. But, hitting from the pros set me back, and Jen and I were even with three holes to go. "Hey, we never decided what happens if I loose," I said. "I didn't think we had to since you weren't going to loose," said Jen. "Well, what is it. How about I clean your house for a month," I suggested. "In a French maid's skirt, maybe," offered Jen. "OK," I replied. I wanted to make sure what I had to do wasn't too bad. And, although Jen's offer was humiliating, it seemed like she could have said worse, so I jumped to say yes. "No, that wasn't really my offer. You want me to suck you dick, and all your going to do for me is wash my kitchen floor in a maid's outfit? That's not fair enough. You know, Halloween is a week away. We were already going to two parties, may be three. How about you have to dress in whatever costume I pick for you. And, you gotta pay for it? And, you gotta be a good looser, I mean good sport, and play along." "What do you have in mind?" I asked. "I don't know yet. But you seemed to jump at the chance to wear a French maid's uniform. Maybe something like that," Jen grinned. "I don't think so," I said. "OK, the bet is off," Jen said. "Wait, not so fast." I wasn't giving up my blow job so easily. Heck, I'm ahead by two, there is only three holes left, and other than that one flubbed drive, I'm back to playing well. "Which party? I will go dressed in drag to your friend's party, but not to our work party." "No. You don't get to make the deal. I took your offer as is. You have to take my offer, as is," said Jen. "OK," I said. "You're on. But if I win, it is going to be more than just one blow job. I get to tie you up, and we're going to have some fun." Jen's eyes lit up. "Deal," she said. From that point on, it was all downhill for me. Jen not only beat me. She kicked my ass. I hit into the woods, into the tall grass, into sand traps. And, I lost 3 balls. She ended up beating me by 4 strokes. I was not happy and wondering how I could back out. *** "Hi sissy," Jen's new greeting for me. "Cut it out. I lost the bet, but I'm not a sissy." "I think it fits. Besides I've gotta come up with a name for you. For the party that is," she said so sadistically. "The party isn't until the weekend," I said. "Oh, but the preparation, and my fun, both start now," she replied. "We gotta get started. There is so much to do. If we are going to do this we are going to do this right. And, remember, the deal was that you had to do what I say, and really get into it." "So what is it going to be?" I asked. "I'll tell you some, but not all of it. I'm definitely going to need your measurements. And, you and me have some shopping to do. Don't think that you are going to put on some tights and go like that. We're going for a total transformation. You are going to fake everyone out. The real thing. We're going to start by telling work you are not going to the office Halloween party." I felt a huge sigh of relief. I was worried Jen was going to make me wear a dress to the office party. "That's a relief," I said. "Not so fast. Your going. Your going to the office party as my cross- dressed baby doll....Sally! But, if you want to save face, what you gotta do is be so believable that no one recognizes you. That is your out. Get it? You are going to the office party, but if you pull it off right, no one will know it was you. And, that way you stick to the bet and save a lot of embarrassment. Good thing the office party is Saturday, but my friend's party is Friday. That'll give you time to practice. So, are you ready to get started?" "Alright, alright, alright," I replied. "I'll do what you ask. But, I can't guarantee anything. So, more about me. I'm about 5'10," and between 150 and 155 lbs. I almost have that swimmers build, but too many slight features. I'm straight. At least I think so anyway. I've cross-dressed before. Not in public. But, when I was 14-15, I would wear my older sister's stuff. She was a cheerleader. Those were some of my favorite outfits. The short pleated skirts made me look very cutesy. The shimmering spandex tights made my legs pass for hot. She had some lingerie too, that I'd wear. She had this lacey corset and garter. With some silky black stocking, I felt like a real whore. When no one was around, I'd dress in these things. Spend hours in front of the mirror. Sometimes, I'd get brave enough to try on her makeup. Eye liner, shadow, mascara, lip stick, and even nail polish. The nail polish was really hot. That was when I had a lot of time and was feeling really brave. Because you need enough time to get everything on, 'enjoy it', and clean up. I liked the look of my colored nails on my hand when I'd hold my dick. Sometimes I thought of it as if some girl was touching me. Other times I thought of it as it was - me, wearing really sexy girls clothes, and touching myself. And, sometimes I went further than that. My sister had this a dildo. It wasn't hers. Well, it was hers. But it was given to her as a joke. It was a crude gift given by a friend of hers as a joke. She put it in her closet. I don't think she ever used it. But I did... It took lots of time, lots of Vaseline, and lots of painful trials. But eventually I could get it to slide in and out without much problem. And, sometimes, I'd try my mouth. I had this notion of "deep throat" from the Kielbasa Queen on some late night show. I figured if some girls can get a kielbasa down that deep, I must be able to get the smaller dildo down. I never did, but I tried a lot. I was definitely not gay. I didn't want to be gay. I didn't like men. I still don't. At least not in person. In my mind I could get hot and bothered about some young cut guy. I definitely imagined different scenarios with underwear models. But, I never had those thoughts or feelings standing next to a real guy. But, then again, I had the same fantasy relationship with girls. And only had a few girlfriends. And, right now I'm single. So, it is all very confusing. Well no one know about that. And, certainly not Jen. There was a very tiny part of me that was willing to do this. Looking forward to it, maybe. But, most of my senses were telling me to forget the whole thing. "First, you are going to move in with me for a while. I don't want any excuses. I want all the time I can get. Second, you are going to take the week off from work. You need to tell everyone your going someplace far away. New Zeeland, Tibet, or someplace. That way people will be more likely to dismiss the idea that Sally could really be you. And, it gives us some time to prep. So go home and get some of your things. But, not too much. You won't be needing much of your stuff at all. Oh, and leave me with your credit card. This is on you." *** Jen was so excited. I think she was surprised I decided to live up to the bet. I got my things and moved in for the month. "OK, let me have all of your stuff," Jen said. "I will decide what you can have and when. I will decide what you will wear and what you will do." I reluctantly gave her my stuff. I'm starting to wonder if I agreed to this. I'm not sure this is what I bargained for. "And, what you are wearing..." Jen said with a demanding tone. "You can go into the bathroom, but I want all your clothes out here. Including your tightie-whities." I hesitated and gave her a look. But, then did what she asked. "OK, Step 1, turn on the shower and cover your body with the stuff in the pink bottle." "I know what hair remover is," I shouted. "I had sisters you know." "Step two," she said. "when your done with the hair remover, take a hot shower, and go back over everything with a razor and some shaving cream." "Is this really necessary," I shouted out. "I don't think I signed up for this." "You did, and you lost. So shut up and get to it." I did. I felt ridiculous with a shaven body. My nuts burned when I applied the hair remover. I don't think I was supposed to put it there. After the hair remover and the shaving, my whole body felt electric. It was the weirdest sensation. I felt cold. I felt smooth. And, part of it was an outer body experience. My skin felt alive. I liked it. It felt really awesome. I was hard. The feel of my skin and the thoughts running through my head were making my blood hot. And, my dick was showing it. "I'm coming in, so if you want to, you better put on a towel now." Then Jen walked right in before I could do anything. I grabbed the towel as fast as I could and wrapped it around me. It was pink, of course. "Nice," exclaimed Jen. "Very nice. I'd say more like four and a half inches." "It is six!" I insisted. "Whatever you say, sissy. Let's get started. Sit down in front of the mirror. I'm going to pluck your eyebrow, and I want you to watch me." We must have spent hours in the bathroom. She plucked my eyebrows, played with my hair, and put makeup on me. She applied false eyelashes, false nails and painted them pink. Then she sent me into her room (she rents a two bedroom apartment), to put on some clothes. On the bed were some of the sexiest, sluttiest, outfits I've ever seen. But, why were there many outfits? And, did I pay for all this? WTF? "I couldn't make up my mind," she said. "Should you go as your typical whore, or French maid, or cheerleader, or frilly sissy, or ... as a rubber gimp? I couldn't make up my mind, so I bought them all. Let's try the typical slut first." I put on the clothes. The feel of the silk stockings sliding over the top of my foot and rolling over my calves and up my thigh was better than sex. It was the best feeling I've ever had. Then we placed the lacey corset over my waste. Jen told me to hold onto her bed as well as I could. Then she shoved her foot into the small of my back and pulled. It hurt. It was tight. But, the effect was altering. My waist looked smaller and curved. It gave me a girlish figure. The corset even pushed my slightly built chest up to give the impression of perky little breasts. Looking in the mirror at this point was the first time I thought I might be able to pull this off at the office party. I was starting to look like someone else. No one had to know it was me. Jen showed me how to snap the stockings into the garter. When I moved the garter tugged at my stockings. The feeling on my legs with every movement sent shivers up my spine. My head was already feeling light and my breath felt short from the rush of blood and excitement. I pulled a very small and very tight skirt up my legs and over my waist. It was so tight I had to maneuver and wiggle my legs to get the skirt up. And, it was so small I think the head of my penis and the bottom of my bum cheeks were slightly visible. I kept tugging at the edges of the skirt. But no matter how much I tried, it didn't cover me any better. And, let's not forget my silky little thong. How good did that feel over my shorn scrotum? I put on a pair of shiny high heeled boots. Even though I'd tried on my sister's clothes before, it was never like this. The clothes were never my size. I'd never shaven my body hair before. I'd never plucked my eye brows, or put on false eye lashes, or put on false nails. And, I'd never worn heels before. This was fucked up. The boots just covered my ankles. The heels where tall. I've only heard of 6-inch heels before. I think these were them. They instantly accentuated my calves and upper legs. My calves were bulging and the stress of balancing kept my leg muscles tight. "Wholly shit!" cried Jen with a gasp followed by some giggling. "You are so fucking hot. Dude, I'm a lesbian, and all I've got to say is right now I would do you. Oh my god. You look like a super-model. All we need to do is figure out the hair and the voice. Damn! You are hot!" *** This went on all week. Jen made me walk around the apartment, playing the part the whole time. I was to talk girlie and walk girlie. I wore girlie clothes the entire week. What was striking to me was that as the week went on, not only did I feel more comfortable as a girl, some of it felt more natural. My girlie voice became more and more effortless. I sounded smoky and sultry. In fact I must have practiced so much that I had to really try to make my voice sound as it always had before. I had lost weight. She wasn't feeding me well at all. And, yes, Jen determined what I ate all week. I thought I lost 5 pounds. But, when she finally had me step on the scale, I weighed in at 141 pounds, with two days to go. And, although I found being shaven and wearing the clothes just as exciting as on day one, my dick wasn't getting stiff over it any more. It was content to hand out in my silky thong. My chest felt sore. Most likely from wearing all of these different things. Some were lacey and a little scratchy. Some pushed at my chest and rubbed as I walked. So it was no wonder my chest hurt a little and my nipples were red and swollen. When I wore a t-shirt or satin nightie, I looked like I was nippin' out. I had the part down. Jen said so. But, more to the matter, I really felt it. It had been days of complete immersion practice. And, I was sure I had it down. Jen set up hidden camera in the apartment to tape everything. She would download the video, and we'd watch it. Me sitting on the couch watching TV. Me in the bathroom, getting ready. Me in the kitchen, making us something to eat or cleaning. We'd watch the film and she'd critique me. Give me pointers. And, I took it in. I was living up to my end of the deal. In fact, my reluctance was gone. I wouldn't say so much, but I was enjoying my temporary conversion. It must have been obvious to Jen, because I simply stopped questioning her and stopped putting up a fight. I was eager to make myself more believable and took in all the suggestions and practiced all day. *** "Rise and shine, sunshine," Jen said as she drew open the curtains. "Today is the big day. My friend's party is today. Come one sweet heart. Get up and get to it." I was feeling a bit weak. Maybe it was the diet I was on and all of the weight I lost. Or maybe it was the lack of sleep. Or, maybe it was all of the exercise I was getting from walking around hours at a time on heels. Jen also had me cleaning her apartment (hey, wasn't that my original bet) and working out. I was not feeling very strong the last few days. "I have a surprise for you," Jen said excitedly. "You're not going to the party as a slut tonight. I decided that would be too clich?'. Lots of guys and girls do that on Halloween. Every chick wants to be a sex kitten for the day, and every guy a closet transvestite. No, I laid out a different outfit for you." I was shocked and disappointed. I had grown accustomed to my outfit. I had practiced all week. I was prepared to do the slut thing, and get it over with. Why now a change. I didn't want change. "OK, I've decided you are going as a sissy. I have many reasons for changing my mind. Not the least of which is that I think this is more humiliating, and therefore, a better fulfillment of our bet. Take a look. What do you think? Isn't it all so pink and soooo pretty?" "No," I replied. "I was already comfortable with the costume I had." "So, you were starting to like being a little slut" "No. Yes. I mean, no.," I stammered. "That's enough. This isn't up for debate. I won, you lost. Tonight, you're my little sissy. And, if you're a good little sissy, maybe I'll let you go as a slut to the office party. After all, you don't want to be out of character and be discovered." I don't know what I was thinking anymore. My head sunk down and I pouted. I had given in again. I was unhappy, but not up for a fight. I did as I was told and put on the pink frilly outfit. It started with a pair of pink satin panties. On the back was the word "cunt". The panties were super silky and double think. Then there were the bright white stockings. They pulled up to mid thigh. They were super silky and super tight. They gripped my legs without any garter, and never felt like they might creep down. The white stocking really accentuated my pink toenails, which had grown longer by now. You could see the little pink digits through the tights. I was told to put my heels on next, because I wasn't going to be able to bend over. The heels where a shiny pink strap shoe with very high heels. There was very little to them. The looked delicate, but felt rigid. I don't think the boots were six inches after all, unless they make heels bigger. Because these were definitely taller. What they did to the look of my legs was only equaled to how much they messed with my balance. With an additional strap that wrapped around my ankle the shoe seemed to lock in, forming to my foot perfectly. Next I put on a white corset. This one was different then the last. I had worn the slutty one all week, and was getting comfortable with it. This one was stiffer and Jen was able to draw it much tighter. I felt my stomach and everything squished. My lower chest was drawn in. My breathing was difficult. I had to work at it. I looked like a very sexy, yet cute, virgin on her wedding day. Jen then pulled the pink dress with white frills over my head. It was tight, but once it was over my shoulders my corset had cleared the rest of the way. The layers of frills stuck out what seemed like a foot, but the dress didn't come down very far. At least not as far as I had assumed or wanted. The fronts of my panties were slightly exposed. The rear was too. Jen tied a pink bow around my waist to cinch the dress and add to the girlie-ness. I couldn't believe this. I was a straight guy, who had the week to get used to playing a convincing slut, who now looked like a silly childish little girl. I didn't notice at the time, but now that I think back on it, despite the new feels and new look my dick didn't budge. It sat quite and small, as it had been for the last few days. I must say, before the panties and the dress, it looked smaller than I'd ever seen it. My penis had shrunken and pulled in so much, it stuck out of my groin area as a very straight and small and fat little nub. There was no hang to it and there wasn't any movement to it. I didn't notice it growing and shrinking throughout the day anymore. I could see the bulge of the nub in my panties when I looked in the mirror. I could also see the word "cunt" in the mirror when I spun around. I felt helpless and vulnerable. My eyes began to water. Jen came over with some tissues and handed them to me. I started to ball. I don't know what came over me. I was sad. I was emotional. I couldn't help myself. It wasn't like I didn't want to do it. That was there in the back of my mind. I wasn't a slut. I wasn't a sissy. I wasn't even gay. But, part of me had given in. I felt weak. Physically and emotionally. I cried on Jen's should for a bit. Then as the tears slowed, she reassured me everything was going to be ok. I was going to be ok. We were going to have fun the next two nights. We were going to fool her friends (most of whom didn't know me, and many of whom where gay). And, then we were going to fool everyone at work. It was going to be fun. I stopped crying and cheered up a bit. "We're not done," Jen said. "There is more. It is almost time to go. Let's put on the final touches." She had my interest peaked. I looked in the mirror and saw this perfect little sissy girl. What else was there. Then Jen brought over a pair of long pink silky gloves. "Put these on," she said. I did. They were soft and silky and tight. Jen had to help me with them. And the most interesting feature, there were no fingers. These gloves were sorta like mittens. They forced my hand into a little tight space and shaped my hands like that of a beauty queen waving from her float. There were really weird, and really tight. My hands were useless, and I figured I couldn't take them off if I tried. They were too long and too tight, I was too weak, and I hand no hands to grab with. Then Jen brought over this thing that looked like a fat and red little penis with a strap on either side. "What is that" I said effortlessly in my most feminine voice. "Oh, sweat heart, this is your nuk. Your going to wear this tonight." "Nuk, what is a nuk?" I asked. "I'll show you," Jen said. "Close your eyes and hold still. Don't move unless I tell you." She walked behind me and I closed my eyes. I felt my long eye lashes settle lightly on my cheeks. It seemed like minutes went by. What was she waiting for I wondered. What is a nuk I thought. Then, in a quick motion, I felt something thrust into my mouth, and straps tightened around my head. I jumped and shook my head around. But it was too late. The damn thing was lodged in my mouth and fixed to my head. My reaction was to turn around and take some swings at Jen. But she just flinched a little and deflected my blows. She finally grabbed my arms and bid me to calm down. She explained that I was supposed to go along with whatever she asked. And she was asking me to wear this thing. She was particularly concerned that since I hadn't practiced being a sissy, she was worried I wouldn't pull it off tonight. So, the nuk was for my own good. I sulked, and if my mouth wasn't full, would have pouted too. I guess I understood what she was doing. I did agree to it. And, I did want to pull it off. I wanted people to believe I was someone else. I didn't want to get caught. Tears welled up in my eyes again. Then Jen put on the final tough. It was a little pink leather choker. The choker straightened my neck and hid my Adam's apple. And, it had some writing on it. The writing was a fancy cursive script. It looked like it said, "Little Sissy". Jen then attached a leash to the choker - and attached the leash to the bed post. She asked me to wait as she got her costume on. What was Jen? A dominatrix, of course. She wore a tight black rubber cat suit. Lots of leather - belts and gloves and high heeled boots and a collar and a whip. And, she wore a leather mask that covered her eyes, much like cat woman or robin. Jen grabbed her whip, grabbed my leash, and we were off. *** Jen walked high through the front door of the party. The home was a huge mansion. And, seeing Jen, I had never saw her look so tall before. Between the very high heels and the corset that seemed to straighten her mid-section and her collar that seemed to elongate her neck. She seemed confident and imposing. I skittered along as best as I could on my dainty little heels as she pulled me behind her on the leash. A couple of times I tried resisting, but I just could get a grip on anything. And with my heels I hould get a purchase. I felt weak too. Jen just pulled me along, and I started to do my best to keep up. I was embarrassed. We were in public for the first time. Jen seemed like she walked me all around the place. It was the biggest home I'd ever been in. we walked from room to room, up and down staircases. It was exhausting just to do that. Jen knew a lot of people. But she was sociable, and talked to everyone she saw. And, she put a plug in for me for everyone she saw. "Please vote for my little sissy hear as the best costume. You know he's straight? He's never done this before. No really he's straight. He's a friend of mine from work. He lost a bet. What a good sport, huh? You have to vote for him." She offered several people to have my leash for a while. She whispered in my ear to cooperate. She thought they needed to see how committed I was to this sissy thing so they would vote for me. First prize is a $1,000 cash and a trip to Cancun during spring break. You know I want that. So don't let me down. Usually when people I didn't know had my leash, guys and girls would come up to me and give me the once over. They would feel up my legs, check out my long useless gloved hands, and lift my dress (as if it needed any lifting to see me). Some would tickle my nub. One guy, dressed as Robin (in a tight red shirt, stretchy gold briefs, and white nylons) played with it for a while. I guess he was hoping to make it hard, for further embarrassment. But once he determined that nothing was going to happen, he moved on. There were a lot of 'good' costumes. Most everyone was dressed in something that was very tight or very revealing. But, as I was walked around the party, I didn't see anyone who had gone to the extremes as I had. Although I was drooling. Probably the only one at the party that was drooling uncontrollably. I couldn't help it. It was the fat red penis gag stretching open my mouth. My jaw hurt. My tongues was lost. It couldn't find it's home to settle into, and just kept wandering around the fat implement in my mouth. My feet were killing. My legs were shaking. I was working on the adrenaline energy that came from my nervous yet excited situation. I noticed Jen talking with this really big black guy. He looked like a football player or something. Maybe a linebacker or safety. The dude must have been 6'2," maybe 195 - 200 pounds. He was ripped. And he was hung. I knew this because his costume was that of a varsity swimmer. His stomach was washboard. His legs were ripped. Every part of his arm had muscles. He reminded me of a dark race horse. He was like the underwear models I fantasized about, only bigger, blacker, and right here. He and Jen were talking a lot. Occasionally she, and sometimes he, would look my way. Finally he walked off and Jen came over and retook my leash. My legs were so tired. I needed to sit. They were quivering occasionally. But Jen wouldn't let me. "Did you see that guy I was just talking too?" Jen asked. I nodded. "He is so fucking hot, isn't he?" She looked at me as if expecting a response. I justed stared at her in disbelief. "Well, you don't have to answer that. I put a plug in for your for the contest. He is one of the judges. I really, really, really want to win. He liked what he say. I mean you by that, not me. He wasn't sure if he would vote for you though. He said there were some other people who might beat you. So, I told him to take your leash and give you a spin around the block. He is busy right now, but I think he is going to take me up on the offer later." I continued to stare at her. I must have looked blank, or maybe I looked distracted. I couldn't concentrate on what she was saying because I was so uncomfortable. My legs burned. And I felt dizzy or light headed or something. I think I now know what extraordinary rendition techniques are. I was humiliated, starved, needing sleep, and I was over worked. I was exposed and helpless. Is this what Gitmo feels like to those guys? Is this the humiliation the prisoners in that one prison in Iraq felt? Did they break as easily as I had? No, they were real bad and real tough guys. I simply lost a bet to a friend over golf. But I felt so much more committed. Something wasn't right. Ever since I moved in with Jen I felt different - as if something was slipping away. I was less resistant. More compliant. Jen was in control and I wasn't sure why I acquiesced so much over a bet. But I couldn't help it. I felt different inside. I was more vulnerable. More emotional. And physically I was skinnier and weaker. I felt an attraction to the clothes. I actually wanted to wear them. I wanted to feel the compression of my waist and the slide of stockings on my legs. I wanted to try to pass as a girl. As a whore. And now, as a sissy on a leash. "Do you understand me? When he takes your leash I want you to go with him as if he were me. Don't resists. Follow where he leads, do as he says, and be the most convincing little sissy you can be." I hung my head and nodded a bit. "Oh, and there is this girl over there that I'm totally in love with. She is incredibly hot and I think she is digging me in this outfit. She the really pretty girl dressed as a princess? I told her that I might lock her in my tower and put my chains and whip to use. That seemed to turn her on. I think I'm going to get laid tonight. So as soon as Apollo take you away, I'm going to be gone for a while. In fact, you might want to stay here, or convince someone to take you back to my place. OK. And, don't disappoint me. I expect a $1,000 cash and a plane ticket to Cancun - one way or the other. Oh, here he comes. Don't disappoint me." Zeus, or Apollo, or whatever his name was - the big black god, came over and Jen handed him my leash. He looked at me a gave me a charming but devilish grin. Jen took off over to the princess, and Apollo lead me away. *** So I guess I was Apollo's now. My eyes were trained on his backside. He had muscles in places I didn't know there were muscles. His lower back and upper back had all these tight contours. You could see veins, too. And his ass was packed in a tight red Speedo. From the front it barely could contain his manhood. From the rear it hugged is butt, revealing muscles there too I didn't know existed. His legs looked long and lean and muscular. He was barefoot. A Nubian god. I hated some of the thoughts I was having. I was checking him out, in an interested way. Like my fantasy guys. But, I'd never once looked at a real guy that way before. I was disgusted with myself for actually entertaining lustful thoughts for a real guy. This is screwed up. I need to get out of this situation. But how. Was I going to backhand him with my dainty little paws? I couldn't fight of Jen, never mind this brick wall. For hours he lead me around the party. I was his. He didn't talk to me much. Occasionally he gave me one word commands in his deep booming voice (e.g. "Wait here!"). When we walked he wanted me at the end of my leash. At least my high heels and tired legs could barely keep up. After a while, when we stopped he wanted me close. He would position me so one gloved hand was on his chest and the other was on his bulge. Sometimes he would put both of my hands on his chest and make me rub. Or, he'd have me tenderly caress up and down his arm while I kneeled at his side. I'd never touched a man before. This was weird. I handshake was a close as I'd ever get. Now, I was made to feel his muscles and gently fondle his cock. There were all kinds of cameras at the party too. People were constantly taking pictures of me. I was a hit. The potential Best in Show. People were interested in taking a look. First, at the sissy with the dominatrix. Then at the boy toy with the Nubian god. Several times people took videos of me be lead by and touching Apollo. It was embarrassing and humiliating. The only saving grace was that no one really new me hear. A few of Jen's friends new me, but only through Jen. They didn't know anything else about me. The pictures and videos may go past this room, but not to anyone I knew. Once I was finally getting settled into the routine of being paraded around, I was lead out of the house and into the back yard. It was a cool evening. I was cold. I was not dressed for a stroll in the cool night air. But, neither was Apollo. The cold air brought my nipple to attention, as well as goose bumps all over. It reminded my how naked I was. No hair. And it reminded me of my recently swollen nipples. I remember looking in the mirror yesterday and thinking how unusually large they were, and guessing as to why. "The judging is going to start soon," Apollo said to me. "Your Mistress tells me that you really want to win. Is that right? Do YOU really want to win?" I nodded my head yes. Jen warned me about how important it was to her. This is what she wanted and I was to deliver. And, yes, I wanted to win. Part of me wanted out -wanted to leave and go home. But something in me wanted to take advantage of the moment. I'd gone really far this week. I'd challenged my friend to have sex with me. Then I actually let her put me in make up and girls clothes. I practiced at passing as a real girl in a slutty Halloween costume. Or at least a boy no one knows in a slutty Halloween costume. I dieted, exercised, watched pornos practicing the girl parts. I made my whole identity as a girl for one week. And, somehow, I gave over part of me. I allowed part of me to be a cross dresser, or a queer, or a submissive little sissy girl. I allowed my brain to go for it, to believe it. And I allowed my body to follow somehow. How did that happen. How did I loose so much weight and so much strength? How did my mind determine to like, crave things in a way I never did before? Right now, I didn't want to run. Instead, I wanted the hottest guy I ever met to take me. To make me his little bitch. This might never happen again. It is Halloween. I'm dressed as a girl. And, there is no one around me that I know. 'Fuck it!', I thought. 'Go for it!' Apollo removed my gag, but told me not to say a thing. The relief I felt when the gag was removed. My jay hurt. I couldn't even close I right away. He touched my face with his strong hand, and made me look up at him. He drew me in and put his tongue down my throat. Shivers ran up and down my spine, and I melted in his arms. He was so big, so strong, I naturally felt like a girl in his embrace. It felt natural. My gloves caressed up and down his body. My left hand finally reached into his Speedo, and his cock sprang out of its cage. One of his hands pulled me in close while the other rubbed my little nub. Unlike with the gay little Robin, I actually felt myself getting excited. Blood started to flow. My penis swelled, but didn't grow. I didn't know why, but it didn't matter because it still felt good. I touched and rubbed him all over. Until he finally pushed my head past his ripped abs and down to his pulsing giant black dick. I was doing it. I was really doing it. I still didn't feel gay. Whatever was happening didn't feel totally good and or entirely right. I put my mouth on his cock. It was definitely too big to put much of it in my mouth. But I was going to try. I licked and sucked and ran my tongue back and forth. I licked his balls and put them in my mouth. They were large and heavy. Eventually he began to strengthen his grip on the back of my head and take some control. My hands were on his butt now and I could feel the muscles tighten. He began with short quick little strokes into my mouth. Then he started increasing the pace and increasing the depth. I started to gag and tried to get away. But I couldn't. His hands held my little head and neck in place. He was revved up now and began to pound my throat. Every couple of pushes and I would gag either making a girlie regurgitating sound ("bleaht") or a blow out sound ("pthhhhhwt") with my cheeks blowing out like a blow fish. I was trapped. I was panicked for air. I wanted to swallow. I wanted his dick out of my mouth. But there was nothing I could do. Pthhhhhwt, mmm, pthhhhhwt, mmm, bleaht, hu, pthhhhhwt, it went over and over. My bright pink lips were glowing in the dark, stretched around a thick black cock. Drool and vomit leaked from my mouth. And, all I could do is try to catch my breath and hold on until he was done. Something in me was enjoying being his little sissy bitch. Although uncomfortable and torn, part of me was relishing the fact I finally jumped in. I made a life long fantasy become real. Or maybe Jen made it become real. But I took advantage and did it. Then it happened. He had begun to rub my little clitty. As he pumped my mouth faster and harder, the clitty rubbing because faster and harder. All I wanted was for Apollo to finish. But instead, I blew my load. Thick yellow and thin white semen dripped from my nub. I could feel it jerking as it always had when I cum. But this time the jerking felt different because the size and shape of my penis was different. It didn't jut out six inches long. No it stood straight out of my crotch about one-half an inch. And is spasmed, over and over again. Then it hit me like a brick wall - Shame. I was embarrassed again. I was done with the idea of this fantasy. This wasn't me. This has never been me. I'm straight. Just because I had some fantasies when I jerked off. That didn't make me gay. Just because I had cross dressed when I was a skinny awkward teenager, didn't mean I wanted any of this. I began to panic. I was trapped. I felt like my mouth was being rapped - like I was being rapped. But, how can that be when I started this willingly? Why did I do such a stupid thing? Why did I allow Jen to dress me up? Why did I put on the clothes, the make and practice? WTF? Pthhhhhwt, mmm, pthhhhhwt, mmm, bleaht, hu, pthhhhhwt... I was a weak little man dressed in a little girls dress being pumped by the biggest black guy I'd ever met. Somehow I'd started off excited. And now I was hating every second of it. And, there was nothing I could do about it. Pthhhhhwt, mmm, pthhhhhwt, mmm, bleaht, hu, pthhhhhwt... I knew when it was coming. I felt a change in the rhythm and a new tension in his muscles. Finally he slowed down and pushed his dick deeper than it had gone before. I thought I was going to choke. I thought he was going to suffocate me. I pushed at his leg muscles with my silky little gloved hands. It was like pushing again an immovable object. I tried to wiggle my head free. MMMMM, mmmmmm, MMMM.... Nothing. I felt his balls rest against my chin. I felt his thick curly pubic hairs fill my nose and rub against my face. I felt his cock force past the inner workings of my throat. And he wiggled as his spunk shot into and down my esophagus. It was hot. It made my throat feel dry. I thought for a minute I could die like this. Then, pthhhwwwttttttt. He pulled out, sending saliva, air, and cum flying out of my mouth onto his dick and all over my face. I was in a frantic state. Breathing was my only goal. I inhaled and exhaled over and over. Drool and juices dripped from my lips and ran down my chin. Fuck! Inhale. Shit! Exhale. I held onto his legs for support, crouched on the ground, breathing again. I was so ashamed. What had I done. I felt like a person who had been drugged, only to come to in the midst of something he'd never do. Only I wasn't drugged. And, I wanted to do it. Now I didn't. I couldn't even identify with the person who did this. I was a straight guy with a disgusted conscience, holding onto muscular black legs with my forehead resting against a big black dick, panting for air, dripping cum from my mouth. I'm straight. WTF? WTF? WTF? I look over to my left and saw Jen in her crazy rubber and leather outfit. As I gathered myself I looked over at her and noticed she was holding a camera. She was filming this. Jen grinned at me in a twisted devilish way. "Hi roomie," she said to me. "I think I got just about the whole thing. At least the juicy parts, anyway." I felt Apollo push the red penis gag back into my mouth and strap it on. Jen said, "Tomorrow night is going to be more interesting now. Unless of course you want this video to get out to people you know. Let's not forget all of our training video too. And, I think we're going to have many fun and interesting weekends ahead of us with my new roommate. Don't you agree sweetie?" Jen giggled. It went straight to my core. I was angry and ashamed and frightened and helpless... Apollo tugged on my leash and demanded, "Come!" as he lead me back into the party. I looked up at him for the first time since I came. He looked very satisfyingly at me.