Girlfriend's Challenge by AnonUser
To Begin with, I live in a small town in Florida, of course i love it down here the sunshine all day, and the total absense of winter climate. There are some things down here that are out of the usual, as in my life and an Abstract Gamer, tend to play too many video games...other than that and school I carry a job at a local fast food resteraunt, thus where this story picks up.
WARNING This story contains some content in which some people(s) might not be content of, such as thoughts on crossdressing and related topics, <If you do not like that such of thing, please return to a more friendly story/website> This story does not contain any sexual acts, so if thats what your looking for, im sure theres other stories that do
Chapter 1: The Question
One day at work, I was just minding my own business, while a co-worker started to get a bit flirty, talking about how she thought that she wished she could have my ass behind my back, I'm 17, about 6 ', brown hair, about 175lbs, decent build, to be honest with you, most of the weight is in the backside, gathered around the ass area. She was a beautiful girl, about 17 years of age, about 5 ' 5'', long brown hair, brown eyes, She came of Latin Decent, and was very gorgeous. Her breasts were about a C-cup. She had a very firm ass, in which she would tend to show off with pride. Of course; being a normal straight male I responded. This continued for over 2 weeks, finnally on a decent Friday, i got the balls to ask her out. Only to find that I was not the only man who she was "interested" in, so i asked, "Why so many men?", only to get the reply "I have fun in it." At this point i was somewhat crushed, but i was determined, that Saturday I asked again "Is there anything that I could do to get her to go out with me?" Knowing her, previously we talked about how she felt like she was always being looked at as a toy, men were using her, or just seeing her as a whore. No love was involved in any of the relationships she had before this time. So I pleaded to her "I'll do just about anything to go out with you!" Later that day, I had recieved an Email from her, here as it read
"Dear Kyle,
I took your offer into consideration, while thinking about things i could do to that would be considered as romantic, i could find none, so i found a certain task that you would find very embarassing if confronted, this would be the ultimate test to see if you really are willing to anything for me. Meet me at my house, Tuesday at 7:00 AM. Bring no one else, dont be late, and make sure that your ready for a interesting time.
Love, Iris"
Chapter 2: Iris' House
After reading the letter she had sent me, i found it intreaging, though i had aggreed mentally to go to her house and go through anything she asked me to. I traveled to her house, pulled up, got out of my car and proceeded to go up the stairs and knocked on her door, where she answered. I was shocked to find that she was wearing a pair of skin tight pants, with a cute top which tended to really show some cleavage. Very hot looking, she pulled me inside, and told me "Ready for some fun?" I followed her, where she took me to her room, which was mainly a pink pastel color, really girly. Full walk in closet, a giant bed covered with pillows, a dresser full of perfumes, make-up and such. She sat me down on her bed, then asked me, "How bad do you want me?" I answered "I have feeling for you that i havnt shared with anyone before" She seemed puzzled, how a guy that was seeming to be on his way to a very successful life, who could have any woman he really tried, would be falling in love with a Latin Vixen. She knew that there were many other women out there better than her...but she proceded to make sure that his love was real. To make sure she wasnt dissapointed again. She called me, i looked at her, she then sat down on the bed next to me. She spoke in a very honest and sexy tone, "In order to make sure that you are really willing to make this relationship work, i have to do somthing to make sure that no matter what happens, we can remain together, even if it makes me do things to do you that any normal man would die over." This is when she proceeded to walk over to her dresser, she opened the top drawer, and pulled out a pair of black thong panties. She once more asked "Are you sure about this?" I replied "Yes..." She put the panties back into the drawer, then sat down next to me again. "In order to see who you really are, you must find out what it's like to be me."
Chapter 3: The Challenge Begins
She told me to stand up, then she took me into the Bathroom, in which was very nicely decorated, told me to sit down on the tiolet. In which she then tried to rummage through the cubbards, she eventually pulled out a pink bottle, in which had no lable. She told me to take this and spread the lotion all over my body, except for my pubic area, which i did. She then told me to take a shower...Which i did, to find out. The lotion that i had spread over my body, was hair removal lotion, my legs/arms/chest and all were completely smooth, it felt kinda good when i ran my hand up my leg, which i never felt this way before. As the mist cleared within the bathroom, i found a pink towel on the sink counter. with a little note, which read "If you really love me, come to my room, i have the challenge already ready, just follow my orders, and I'll will know that you are truly in love with me" I then wrapped my now smooth body in the towel and went back to her room, i found her sitting on the bed, wearing nothing but a pink nighty that she gotten from her closet, she stroked my now smooth leg. suddenly i found my self partially aroused, seeing her tight, luscious body in that tight silk nighty. If felt myself shudder with thoughts of lust.
She got up, which made her breasts sway. She then proceeded to move over to the dresser where she had pulled out the thong panty before, this time she got more than that, she pulled out a matching Thong/Bra set, royal blue in color. This is where i remembered from before "Are you sure about this?" Jesus!, she planned to make me into some kind of faggot sissy boy! She moved toward me, with the underware in her hands, She placed them upon the spot next to me on the bed. Panic set in, she told me in a very commanding voice "Put these on...you will find them a bit more comfortable than you think." Once again i moved towards the bathroom, where i took off my pants, then my boxers, then looked at my now smooth body in the mirror, just felt alien while i stood there, never felt like that before. I then picked up the thong, thinking of that being the easier of the two objects. I slid one leg into one side, then the other. carefully i slid it up my legs, which sent a tingle down my spine as the silk material had caressed my thighs. I pulled it up towards my ass, in which it seems odd. I had to position it to fit properly, never had somthing as such slide up my asscrack before, felt very unconfertable at first, after a while I got used to it, then it felt as if it wasnt there, After adjusting my member to actually fit within the pants, carefully positioned within the little area which covered my crotch. The silk material felt good, as a felt pre-cum start to form at the tip of my now semi-erect penis. After figuring out that part of clothing, I took off my shirt. Picked up the bra, in which was marked as B-Cup, which was odd, seeing how Iris was a C-cup. She must had found a bra that she wore earlier. I possitioned my Pecs within the cups, it felt odd...I never had anything to support my chest area before, it lifted my chest into what represented small breasts, with a bit of cleavage in the middle. Still i didnt fill out the cups. It seemed very odd, the straps seemed to keep sliding down my shoulders. Which was very tedious to attempt to fix every 30 seconds. After figuring out this, I walked out from the bathroom, after putting my pants and my shirt back on, The thong kept on slipping out of the pants that i had, and tended to show when i walked, when i got back to Iris' room, she looked at me, asked if i had put on the clothes, told her yes. Then she told me to take off my pants and shirt, which is did cautiously. She then looked at me, giggled a bit, then simply smiled. She told me that i looked "cute", then she moved to her closet. took out a very skimpy shirt and a pair of jeans that looked to be bleached in some spots.
"This is the next part of your challenge and test" She told me, she handed me the clothes, told me to to put them on, in which i felt no need to go to the bathroom and do so, sinse ive already lost all dignity here in front of what i hope would be my future girlfriend. I put on the pants first, hoping to be able to hide my nakedness and the half erect bulge in my panties. The pants seemed to go OK, but near the butt region is where i had a minor problem, seeing they were womans pants, they were tight, but after some negotiation, they fit. I looked around to see my now very tight looking ass, in which was very round, the pants helped. A lot, but Iris giggled seeing how she liked what you saw. I blushed a little bit. After that difficult adventure, she told me to take a shot at the shirt, in which was grey. But had the words "Linkin Park" written on the front, she thought it was cute. I had no problem with putting that on, but the sleeves were very, very short. barely covered the ending of my shoulder blade. When that ended, she told me to spin around, she admired the way my body filled out almost everything, she told me that she had one more thing that could help. She reached under her bed, and pulled out a box, which she opened and pulled out a pair what looked like breasts, in which she told me that they were Silicone Breast Forms, in which was to increase your cup size by at least 1 letter size, She walking up to me, with the breast forms in hand, then took off my shirt, then proceeded to pit the breasts inside the bra that i was wearing, this filled the cups to a max capacity. It felt odd, cause of the fact that i now was staring down at a pair of tits that looked and felt real... She simply told me I looked good, then sat me down at a vanity in the corner, then started to apply make-up upon my face...This took several minutes, she applied almost everything that she could find, eyeliner/lipstick/foundation. This only made my appearence be more consealing, Trust me, at times i almost thought that i wasnt myself. All this time Iris was having a ball too, every minute she was looking and talking like it was another woman in the room. This freaked me out a little bit. She then proceeded to find a wig that she had within her closet, it was blonde in color, and was very finely detailed. Looked almost like real hair. She placed it upon my head, hid my hair from view, and took me over to a mirror. I was shocked that within 2 hours, i would go from looking like a good looking man, to a complete knockout of a woman, She simply looked in disbelief.
Later that day, after she had told me to take off the clothes, but she told me to take them home, she had no need for them, so i did...dont know why, just did. She agreed to out with me, she stood up to her word, just that we have a "special" relationship. We are like a normal couple, just every now and then, we have a "bonding session".
Thank you much, Send comments/compliments/suggestions for later stories and such to AnonUser2k4@yahoo.com
I hope to be able to create such stories in the future. Look out and keep checking this site for updates.
Thanks, AnonUser