Dave and I worked at a midwest tool and die company and hung out sometimes with overlapping mutual friends. We both play baseball and hockey, although Dave is probably 6'2" and build like a running back or power forward in hockey. I'm 5'8", lean and athletic, a lifetime runner and keep myself in pretty good shape. I'm 25, he's maybe 38 give or take a few. We are both small town guys - nothing too complicated.



I wouldn't say Dave and I were natural friends. He's more of a guy's guy; doesn't say a lot and mostly talks about sports and keeps his emotions on a short leash like most dudes. I am way more social, don't mind talking sports, but get bored with that after a while and wander into other topics like people, politics (less and less a good idea...), history, or whatever is interesting.



Truthfully, I get along fine with guys, but I often have better conversations with chicks. Besides, there is always the outside chance of getting laid, right?



It was after a hockey game last winter that Dave and I discovered we both were facing relationship changes; me - I'd split with Heather after two years and was looking for a place to rent, although money was tight since the recession hit and I was trying to figure out something cheap. Dave's girlfriend Rebecca was deciding to give their relationship a break, and was traveling for a year through Asia and Europe. Anyway, one thing led to another, and Dave offered to rent me a room in his place while Rebecca was away, which worked out perfectly for me.



For the first few months everything was fine. He was a bit of a slob by my standards, leaving small messes all around the place that I found myself cleaning up. He is a handsome guy and takes care of himself though. Dresses sharp, especially for a small town guy.



In October, I lost my job at the factory. Dave had more seniority as he is a skilled machinist, but I was apprenticing and lower on the totem pole, so when the economy turned south, I was one of the first to go. I scrambled to get some odd jobs, but there was not much going on in our little town. As November rent came due, I had to fess up that I couldn't pay the rent. Dave was cool about it, and said not to worry, I could owe it to him. Relieved, I did extra work around his place while he was at work, which seemed to be ok. I have to admit, the guilt was building though, as I had missed another rent and Dave was getting a bit edgier. I built up the courage for a difficult conversation with him as he got home from work on a Friday night:



"Hey Dave, how was work?"



"Alright I guess. Mark was being an asshole again. They should fire him. It's not like he's that good a machinist but just because he has a couple of years seniority, he likes to throw his weight around."



"Oh, sorry to hear that."



"How's the job search going?", Dave asked.



"Um, well, not that great. I did get a small job helping with setting up Christmas decorations, but it's tough."



Tom popped the cap on a bud from the fridge and sat down to watch some football. "So are you going to be able to pay rent this month?"



"Dave, I'm really sorry, but I can barely make my car loan and credit card interest. Can you float me for one more month? Things should look up here, they have to."



Dave sat staring at the TV, and took a slug of his beer. "Ya know, I've been thinking about this recently, and I don't think I can do this much longer. With Rebecca gone, I could be renting out that room for $400 a month and you are now in the hole for $800 with no prospects of a job. You are going to have to find somewhere else to stay after the end of the month, bud. I can't keep carrying you."



"Listen Dave, I know you've been really great and put up with me. I just don't have anywhere else to go right now and it's the middle of winter. Is there anything I can do to make this work?"



Dave sat staring at the TV.



"I'm just going to be straight with you Brian. I've been thinking about this a lot cause I figured you weren't going to be able to pay rent again. I miss having Rebecca around; she made my place cozy in a way that only a girl can do, and she was sweet with me, if you know what I mean."



I had no idea where Dave was going with this, but I assume he meant he wanted to get rid of me and rent the room to a girl. I'm pretty sure Rebecca would be pissed if she found out about that.



"I know I can't rent the room to a girl with Rebecca travelling, but I'm looking for some feminine company around here. Someone to come home to who looks cute, makes dinner, takes care of me after a long day, like girls do right?"



"Sure Dave, I get that." I didn't know what to say, but I could see that I was about to get kicked out and was desperate to find a way to not end up in a shelter in the middle of winter.



After a brief silence, Dave said: "Ya know, you and Rebecca have a similar build. How tall are you and what do you weigh anyway?"



I paused, confused, ""I'm about 5'8" I guess, maybe 150 lbs, something like that. Hey, how about I offer to cook all the meals and keep the house super neat and clean like Rebecca did for you? I could do your laundry and shopping and shit like that."



"Yeah, that could work, but I need something more than that from you..." Another long silence while we both slugged beer and watched the Rangers - Wild game.



"Rebecca's clothes are all in my room; lots of nice stuff too - sexy lingerie, pumps, tight jeans, lots of very hot dresses. I could move some of those clothes into your room."



I was totally confused, and didn't understand what he was getting at.



"Um, sure Dave, if that frees up some cupboard space for you, that's not a problem, I can store her stuff in my room, sure."



"Well, I'm thinking more than that Brian. You know, you're kind of a smaller guy, you could look pretty nice in some of Rebecca's clothes; it would give me something to look at when I come home from work and compensate for the rent you owe me."



I sat in stunned silence for a minute. "Um, what are you...what are you saying Dave. You mean you want... you want me to wear Rebecca's clothes...like dresses and shit?! Like actually put on her clothes, like a girl? You've got to be kidding, right; I'm not going to fucking do that!"



"Suit yourself man. Like you said, you asked me what you could do to not get thrown out in the cold, and I gave you an option. Either way, rent is due on Friday, so you have a couple of days to think about it. If not, you're going to have to pack your bags and be ready to go on Saturday morning."



I sat in stunned silence staring at the TV, my face flushed red and acutely embarrassed. Did this conversation really just happen? Is Dave really asking me to dress up in Rebecca's clothes, for fucks sake. Does he think I'm gay or what? Now that I think about, she and I are the same height and build in many ways. Has he always had fantasies about me being cross dressed? Fucking asshole. Is that why he offered to rent a room! Fuck me, I have to get out of here!!



We didn't talk much more that evening amid the awkward silence, although he seemed completely nonplussed by the conversation, like a guy telling his mate that he should wear his girlfriends clothes was an everyday thing. As he got up to go to bed, he put his hand on my shoulder, sending shivers down my spine, 'Think about it...it's really not that big a deal" and walked off to bed.



I got myself another beer and sat contemplating my situation. I can't believe that just happened. What a freak. I'll call around tomorrow and see if I can get another friend to rent me a place, but shit, I have no money to pay them.



Sick fucker, that is so fucked up that he said what he said. What does that mean anyway? I imagined myself dressed as Rebecca; what kind of clothes did she have anyway? Surely they wouldn't fit me. Fuck, what I am I doing even thinking about this.



The next morning Dave left early for a 7 am shift. I had a sick feeling in my stomach remembering the last night's conversation. After coffee, I started texting my mates, to see if I could drum up a place. By noon, Jerry, Nate and Bill had all gotten back to me saying no, they didn't have any room. That left only Jeff. By 2 pm, he had also responded - negative. I checked my bank balance; not more than $200 left, and no job prospects.



It was Thursday night and Dave was late getting home from work and had clearly had a few brews.



"So, how did it go?" he said. "Did you find another place, or have you decided to play along."



To play along, I thought, fuck you.



"This is some sick shit man. I don't know why you want me to do this," I said despondently.



Dave walked over to me; I had noticed how much bigger he is than me, and how physically intimidating he can come across sometimes, especially with alcohol on his breath.



"Why don't you head upstairs. Rebecca's stuff is in the dresser on the right side of the bed, and she has a lot of clothes in the closet too. She is a very sexy dresser, so I'm sure you'll have no trouble finding a cute little outfit. Like I said, you and her could have been twins."



Holy shit, this is creepy. I couldn't even make eye contact while he was talking, and just took a deep slug of my beer. God, I didn't say I was going to do it.



"By the way, you can't be hairy wearing women's clothes, that's nasty, so have a shower and shave, and I mean all of you, legs, arms, crotch, everywhere. That might take you a while, so hop in the shower and I'll lay out some clothes for you."



"Jesus man, this is really fucking weird."



"Like I said, it's no big deal and better than being tossed out in the cold. We're going to get a big storm tonight... Hop to it."



I felt like me ego was being crushed before my eyes. Here was a guy telling me to go have a shower and shave my whole body, and that he was going to lay out girly clothes for me to wear. How is that possible that I am letting this happen?



But I had no choice. I slugged a couple of beers hurriedly and went upstairs, gathered up my shaving stuff and stepped into the shower. I guess I can put up with his little kinky game for a bit, while I sort myself out. What a knob.



I am not a hairy guy, but It took a couple of razors and it seemed like forever to remove all the hair from my legs and arms. By the time I was done, my legs and arms were all tingly. I was shocked to see how feminine my body actually appeared without body hair. When I stepped out of the shower, and looked down at myself, I shuddered involuntarily and felt a cool breeze on my skin that was light and sensual in a bizarre way that I hadn't experience before.



"Hey, I laid out some of Rebecca's clothes on the bed for you", I heard Dave say from the other room, " One of my favorite outfits of hers. When you get dressed, come on down and fix us some supper."



I waited for him to leave and looked around the corner with dread. I stared at the clothes on the bed. A pair of white lace panties and a bra were placed neatly on top of a sheer pair of black nylons. A black skirt and white blouse lay to one side, a grey sweater next to it. On the floor, a pair of 2 inch black pumps were placed next to the bed.



I stared at the pile of clothes in disbelief, and then down at my freshly shaved body. I felt like I was in a dream; this can't be real, I can't actually be doing this. I reached over and picked up the delicate white panties, almost afraid to touch them like I was some kind of pervert stealing women's underwear. Did Rebecca actually wear these? It made my cock stiff thinking about it; suddenly I felt flushed and embarrassed like I had sneaked into a girl's bedroom to see her lingerie like some pervert, except this was laid out for me, and I had to put them on.



At first I hesitated, but then I opened the lace panties which seemed tiny and frilly and slid my foot through each side. I pulled them onto my legs and up to my waist. The G string filled my crack and settled into place. So that is what a G string feels like, I thought. My cock was fully erect and barely held into the panties. Next I picked up the matching bra. It was an underwire and I fumbled with the clasp. Fuck, how do you do these up when you can't see what you are doing? How do chicks do this anyway? In the end I had to roll it around in front of me to get it clasped and then rolled it back around. Is that what girls do, I thought? The panties and bra fit me perfectly, too perfectly, fuck, I really was similar to Rebecca's build now that I think about it.



I then reached for the nylons. I didn't know how to put them on and fumbled with getting them started on my legs. Once I had both feet in, I stared in disbelief at my own feet and ankles, which seemed alarmingly feminine and petite in sheer black nylons. I was getting a raging hard on which was confusing and disturbing, as I pulled up the sheer black nylons up my over my thighs. I couldn't help but feel intensely erotic as the sheer nylons slid up my freshly shaved legs and over my ass. Fuck, I thought, I look like a hot chick staring down at myself...I would nail her if I got her naked...shit, this is just so fucked up.



I reached for the skirt and pulled it up over my waist. I remember seeing Rebecca in this classy skirt at a dinner party one time and sure noticed her tight ass and curvy hips. Dave is a lucky guy. I slid the skirt up over the nylons, and sure enough it did the same to me, as I glanced over my shoulder at myself in the mirror at the cute little ass and nice legs framed in the full length mirror.. Jesus, how is it possible that a guy can so easily look like a hot chic. That's just fucked up, I thought, no wonder women obsess over clothes - they are just fucking powerful when they are dolled up in sexy outfits like this.



I pulled on the white fitted blouse, which showed the lace underwire bra underneath, and then pulled on the light grey sweater and did up one button just underneath the bra, giving me the affect of having actual cleavage. I stepped into the black pumps, which felt very strange and uncomfortable to wear, but I could see why guys like them on chicks - they force you to arch your back and lift and accentuate your ass. You also feel vulnerable, like prey, unable to run, which I suppose is exactly what guys want women to feel.



I turned and looked at myself in the mirror. From the neck down, I looked like a pretty fine looking woman; like an office girl you'd see downtown, or the chicks you see in Banana Republic ads, which was kinda Rebecca's look. I'd fuck her. Alarming to say the least.



"What's taking so long!", I heard Dave yell from downstairs. My heart jumped into my throat. Oh my god, am I actually going to go downstairs looking like this, and be seen dressed like a woman? After a few minutes hesitation and another yell from Dave, I forced myself to the door of the bedroom. I heart was pumping out of my chest as I gingerly made my way down the stairs, afraid I was going to tumble headfirst down the flight from these awkward pumps, in disbelief that I was actually doing this. It was shocking that being in this getup forced to move down the stairs exactly like a woman in a tight skirt and pumps would do.



As I reached the door to the living room and kitchen, my heart was pounding so hard, I could feel my temples bulging and could barely breathe. Am I really going to do this? One more step and Dave would see me; there would be no turning back. I just can't do it. If I make my way back upstairs, I can change back before it's too late.



"Just get in here" I heard Dave say, in a calm but assertive voice.



I stepped into the kitchen, trying not to look at him. Fortunately, the lights were dimmed and Dave had his back to me watching the ball game.



"Grab me a beer, would ya."



He sounded so matter of fact, I couldn't believe it. Was I supposed to bring him a beer, looking like this?



I grabbed a budweiser from the fridge, and saw him put his hand out, but with his back turned to me.



I walked toward him, my throat so dry I couldn't speak.



As I approached him, he turned and looked at me. I was frozen in the spot.



He had a sly look on his face, like a man in charge. "See, you look great, just like I thought you would. You fit that outfit perfectly, which means all of Rebecca's clothes are going to fit you and she has a lot...nice."



I couldn't make eye contact, just blushed and looked at the floor as I handed him his beer. It occurred to me alarmingly, that all those gestures and my inability to talk were entirely feminine and submissive, and I was playing into Dave's power dynamic, but how could I help it, dressed like this, as vulnerable as I am standing here.



'Come sit beside me" Dave said, gesturing to a pillow beside his chair. With the tight skirt and pumps, I couldn't help but move like a girl, the clothes made me do it. I squatted next to him trying desperately not to make eye contact. This was all intentional I thought; he used to get Rebecca to sit like this too. I suddenly realized that everything about this dynamic was a set up of him as dominant and me as the female submissive. I surrendered to the horrible reality of this evening, and my predicament. At least I am not packing my bags right now, and heading out into the freezing cold winter in the morning.



This will buy me a little time to sort things out, find another place to live.



I felt Dave's hand on my back, resting gently right at the bra strap. I shivered. I could feel him rubbing lightly, confirming for himself that I was wearing the lingerie he laid out for me.



"Packers are taking it to them tonight. Should be a great game" he said, like this was any ordinary day with a guy unwinding after work with his girlfriend.



At half time, Dave said: "Why don't you fix us up some dinner", commanding me to do his bidding, exactly as he used to do with Rebecca. What could I do? It was awkward getting up in a tight skirt, nylons and high heels. We made eye contact as I made my way to the kitchen. I wasn't quite sure what to make of his look - he looked calm and in charge, like he knew what he was doing, and that I was going to go along with his wishes, whether I liked it or not.



Standing in the kitchen making spaghetti and salad was a surreal experience. A couple of time I forget I was dressed like Rebecca, and it was only when I looked down and saw the hem of the skirt, the sheer nylons over my knees and slim calves, and the pointy toes of the pumps, that I would look up in alarm and realize this was real, Dave was really there watching television 10 feet away while I cooked him dinner dressed in a skirt and pumps. Fuck.



I brought him his plate. "Thanks darlin'" he said without looking at me.



I flashed red and fought back: "Fuck this man, I'm not going to be treated this way. I went along with this fantasy or whatever this is, but this is fucked up. I'm going to get out of this stuff, and won't be doing this again."



Dave turned to me, a hard stare on his face: "Listen, you can do what you want. But if you expect to be here when I get home from work tomorrow, you better be dressed properly. As soon as you can pay your rent - including the last 3 months you owe me - you don't have to wear girls clothes. But until that time, let me be perfectly clear: when I get home from work everyday, I want the house clean, the laundry done, dinner on the way, and I expect you to meet me at the door with a cold beer in hand, and you had better be dressed like a good girl or I will throw you out the minute I come in the door. Your choice. You can hang out all day, but if I am carrying your sorry ass, you had better bring something to this that meets my needs."



We both stood there in silence. "Besides, it's not much to ask. A few hours a day, dressed and acting like a proper lady, taking care of her man, is really not much to ask. Women have been doing it forever. You can too. It's entirely up to you. I have an early shift tomorrow, so make your decision for when I get home tomorrow."

