This is a fictional account with minor inspiration from real life and fantasies.
After a recently being fired and then ironically a fire burned down my house I had to go live with a friend out of state. All I had to my name was a few hundred dollars and my college degree, in history. I slowly made my way across the state when I finally caught my final bus and good thing cause I was down to just about twenty dollars.
It was already five o'clock at night when I managed to walk up to the door of Christy's house. I knocked 3 times before the door swung open. Christy jumped out and gave me a huge hug and she said "Oh I am so sorry to hear what happened... Come on in I have a guest room ready for you. Don't you have some bags or something?" I shake my head and explain everything that happened as we headed to the guest room. Once she let me into the light pink room and I sat down she spoke once more. "I guess you can borrow some of my pants and shirts if you want, some of them should fit you."
I smiled "Thanks for understanding." For once my slender form was actually a benefit and not just being made fun of by my friends. I had a similar build to Christy although I was alittle bit taller.
It had been a few weeks since I arrived at Christy's and I had not gotten a single job or any way of making money and I couldn't afford anything so I had not had a chance to get a hair cut. I also had to kinda get use to wearing Christy's boyish looking clothes but when I got up this morning and looked through the guest room wardrobe after my shower I realized there were no pants left. I walked downstairs to the kitchen where I heard Christy humming while making some breakfast. "Hey Christy do you have any more pants? I could not find any?"
She rather dismissively said "No they are in my dirty laundry pile. Why don't you just wear a skirt or dress today? I mean it isn't like you go out very often anyway." I was shocked at what she said but realized she was right. I headed upstairs and grabbed a pure white skirt and a light blue V Neck she had. I had been looking through the underwear drawer but all that were left were very frilly panties or some thongs.
After slipping on a pair of frilly black panties I looked at myself and realized that I actually looked a little bit like a girl and I felt a twitch of pleasure as my cock grew hard in the black panties. I actually liked how I looked in these clothes. However as I let my hand wander under my skirt and began rubbing my cock I got embarrassed. I could barely believe that I actually liked wearing girlish clothing.
After a few moments I headed downstairs extremely self conscious about myself. When I walked into the kitchen Christy looked at me and she smiled. "You know, you don't look half bad in a skirt. Now sit down and lets have some food." I blushed at her comment but did as she asked. Christy served me some pancakes and she sat down with some as well. We ate there in silence and ate. After several moments she broke the silence "So what do you plan on doing today? Still looking for jobs or you finally give up?"
I was getting kinda discouraged and I doubted I would get any good jobs until I could maybe get a teaching job come the fall. "Ya maybe... after all I can't really go out like this... maybe I will resume my search tomorrow."
Christy laughed. "Aww but come on you look cute, surely you could get a job in a getup like that." She winked and made me feel incredibly uncomfortable but also slightly flattered. "Come on I can make it so you actually don't look like a guy if it would make you more comfortable. After all you don't seem to mind wearing that skirt." She had a huge grin on her face as she then pulled me out of the kitchen and to the bathroom. "Come on it will only take a few moments." She then sat me down on the seat of the toilet.
I tried to protest for a few minutes but she then told me. "Just shut up and let me try, after all you owe me." I sighed and sat there as I saw her pull out a razor and some makeup. She immediately began to shave my legs and arms completely clean and then without missing a beat she pulled the panties down and said "Might as well go full shave, you wanna get your balls or should I?" As she let them fall to the floor my cock got very hard very fast. It was unbelievable, I thought she was hot and all but this had never happened to me before. I took the razor and said that I would do it as I reached up under the skirt and began to shave my balls. It felt very weird to be completely shaven and she then let me pull my underwear back up.
She looked me over then lightly applied makeup to my face to make some of my less feminine features much more feminine. Christy turned me to face the mirror and I was utterly surprised. I... I... I looked good. I grew hard from looking at myself in the mirror and I could not believe it. Christy then said "Damn you clean up nice, if I didn't know better I would think you are a girl." She laughed and then said "Alright now go on do whatever you want today, I had my fun."
After she left I looked at myself and I began to rub my cock slightly. I could barely believe it was me in the mirror as I felt myself stroking my cock and felt myself nearing climax when I realized what I was doing. I stopped and relaxed then decided I was going to head out and try to clear my head.
I walked all the way to the nearby mall trying to clear my head, after walking around the mall for abit a guy walked over to me and started to hit on me. I then realized he thought I was a girl. I blushed and spoke "Hi... I um... Hi." I could barely believe that I was convincing enough to fool this handsome guy. After a few moments I said I had to go but he invited me to a party later that night. I agreed for some stupid reason.
I headed back to Christy's house and when I got there I was glad she was still at work. I laid down on the bed and tried to relax. I was turned on and needed to just masturbate. I pulled my skirt up and my panties down and began to stroke my cock. It was so hard and I was thinking about how that guy had been hitting on me and I quickly felt myself overcome with pleasure as I begin to climax. I cum onto my bed and relax. It was amazing. I drifted off to sleep and relaxed.
I woke up to the sound of a door closing. Christy must have just arrived home and I quickly got up pulling my panties up and headed out to greet her. "Hey Christy was work good?"
"Kinda after all how was your day?" She said slightly exhausted.
"Well um I went to a mall and kinda got hit on by a guy."
Christy almost burst out laughing and tried to contain herself. "Oh wow, that is really too much. Did you get a number or anything?"
I glared at her and slightly annoyed I said "I got invited to a party but I can't really go... after all I am a guy not a girl... he is expecting a girl." Christy then got this very devious smile on her face and I was worried. "What are you smiling about?" She then declared that we both would be going to the party whether I liked it or not. I protested but she was having none of it.
She took me to her room and stripped me down. "Now we need to find something good for you to wear and here is a padded bra to give you some tits." I looked at the pink bra she handed me and she then glared at me with cold unforgiving eyes "Put it on." I was scared and slipped it on and surprisingly it did look like I maybe had B cups. She then stripped down to her bra and panties herself and she said "Now don't we both look nice, oh and so this does not cause a problem..." She said motioning to my dick she pulled out a couple of pieces of tape and my rather hard cock was pulled up and taped tight against my skin. "That is so you don't get no awkward boners at the party."
She then pulled my panties back up and they held everything in place fairly well. She then pulled out a black leather miniskirt which she slid on and she also slid on a very tight blue top without sleeves. She then handed me a little black dress which would barely fit me let alone be very long. I managed to squeeze into the little black dress and it hugged my waist tight and showed off what tiny tits this bra gave me. She then handed me a pair of 2 inch black heels and said that I needed to wear them or I would just look ridiculous. After I slipped them on she smiled and looked me over. She slipped on her own pair of black thigh high boots and she turned me to the mirror and made me look at myself. I was extremely convincing as a girl and with her standing right behind me I could barely help but get turned on. She then whispered into my ear. "You like this don't you?" I froze at the thought. I actually kinda did like this. She then began to let her hand play with my ass and I blushed. "Tell you what if you don't like it tonight then I will stop this but if you like it then I just might have a better present for you tonight."
Several hours later we were sitting in her car outside the party. I was absolutely terrified of being found out but the terror was actually turning me on a lot. I was hard despite my cock being restrained. I walked fairly well in heels surprisingly and the level ground definitely helped. I stepped into the home where the party was and Christy was right behind me. The party was in full swing already. The boy who hit on me earlier saw me enter the house and waved me down. I came over to him and he offered me a drink. I nodded and gladly took the drink. He seemed like a really nice person and it was actually really nice to talk with him especially since he seemed very interested in me.
I slowly drank more and more drinks and at points I almost forgot I was dressed as a girl, but right as I was starting to forget the guy I was talking to let his hand slip onto my side and down my back onto my butt. The feeling of a guy's hand on my butt was weird but slightly enjoyable. As the party progressed I realized his hand had wandered under my skirt right before he asked me if I wanted to go into a bedroom. Luckily right as he asked me Christy came to my rescue and said we needed to get going.
When we got back into the car I let out a huge sigh of relief and before I could say anything she smiled and said "You loved it and you know it. You were chatting up that boy like none other. Honestly I think you might have gone back there with him if it were not for me."
I shook my head "No way I wouldn't have..."
"Have what?" She interrupted "Fucked him? At least it proves it went through your mind so I get to give you a little present tonight."
I was afraid of what this 'present' she was referring to would be especially after things so forceful as before. Something about her demeanor seemed different from college but it actually made me attracted to her. "Alright." I said conceding that I did infact enjoy the party.
"Good then when we get home you are to go to my room and strip everything except the panties and bra."
I nodded to her order and mentally prepared myself for whatever might come.
When I arrived back at her house she sent me to her room and I did as she said. I stripped off the dress and slipped the heels off. I sat on her bed slightly afraid of what would happen but also turned on from what might happen. Soon she came up and smirked as she looked me over. "From here on out you don't wear any pants except when I directly tell you it is okay, right?!" She spoke in such a demanding voice that the question came across as an order and I simply nodded. "Here take this." she held out a pure white lacy nightie which was partially see through. "Sleep in this and the bra only, and I don't want you cumming on it so if you do then I will make it bad for you." She seemed serious and I was terrified of incurring her wrath.
Thus ended my first real expedition into my new life.
If you want more or have feedback please comment.