A Journey of Self-Discovery

Starting out when I was 16 year old boy the first time I remember my desires of being a girl coming out. I was spending the night with my best friend. It started out a normal night of video games and movies when his sister left saying she was leaving for the night. After the door closed to the basement he leaned over and said "I have idea of what we can do to have fun tonight." I asked "what's your idea I'm game!" he then got a Hugh smile and began to explain what his idea was "we go into my sisters room and we find some of her panties I bet there cute." "Let's do it" I said I was really excited I never thought of this before so we got off the couch and began to walk to her room.
We got into her the door was unlocked. He walked straight to her dresser and opened the top drawer then pulled out a pair of hot pink undies. It was a g-string with a cute little black bow on the front and back. He then said "have you ever wondered what it would be like to wear these kind of underwear instead of what we wear." without much thought I then dropped my shorts whitey tighties I grab the thong and put them on. My friend had I shocked look on his "i didn't mean let's put then on" with a pause "but dang u would make a really cute little girl!" I said "they feel really nice." "Give me a little spin" he said with an open mouth from excitement. I gave him a spin and said "let's find more clothes for me to put on then we can play a game." he then asked "what kind of game?" "I'll tell you when I'm all dressed!"
We began our search we found a red plaid skirt a pink bra that matched the panties I was already wearing a red tank top for the shirt. He said "OK that should complete the outfit." "Something is missing" I explained "where are your sisters shoes?" he went to her clothset and opened. Inside was a shoe rack I picked out a cute pair of pink strappy sandal heels they had to be at least 5" tall. He then asked "OK what is the game we are going to play?" I told him "I'm going or put these all on then we are going to play boyfriend/girlfriend." with excitement "OK". So I began to get dressed.
After I was dressed I walked into the room where he was I said "OK let's play." he was full of joy "this was a great idea so how do we play?" I explained "first you treat me like I'm your girl then we have sex." he said "OK let's start" he took me by the hand and walked me over to the couch where he had a movie ready to play. He started the movie while holding me in his lap it had barely started when through his pants I started to feel his weenie start to pitch a tent. I asked "what's that is someone happy?" he just smiled so I wiggled around enough to start to pull his little pecker out and look at it. he asked me to suck on it if I wanted. I took real good look at bald penis then opened my mouth and began to suck it like a lollipop. I did that for a little bit then we both got really tired to avoid getting in trouble I put my boy clothes back on and put away her clothes. And we went to bed him spooning me like I was still his girlfriend.
That was my first cross dressing experience now that I'm 18 now I think of that moment a lot I realized that night I should have been a girl. it always stuck with me I would wear a thong and bra as much as I could one girlfriend I had broke up with me BC she went to give me a blow job and I forgot that I had a pair of her panties on. Things happen though she promised to stay quite about for my reputation at school. now that I'm graduated I had my plan and that was to go buy my first dildo so I can finally feel what it's like to have cock in my ass. I was so excited to walk into the adult arcade. it was really easy to find the dildos they covered a whole wall. Long ones fat ones black, white, a few hands for fisting practice vibrators. All sorts of toys I also saw the she male movie choices wow that looks awesome. So I hurried to pick out my dildo so I could find she male video to watch while I fucked myself with it. looking I found a 10" long 2 1/2 " thick black dong said that should be great to hold too to pound myself silly. I grab it and headed to the movies. I was bent over looking at the bottom shelf so excited about everything I didn't notice my pants were riding a little low just low enough to show off my panties. a gentlemen walked up behind leaned over and said "he sweet thing Ur panties are showing!" I jumped up with in empraessment. He told me "it's OK sweetheart I won't tell" he handed me a card "hats my address and number if want to be treated like my girl call me and oh you won't need that dong I got a big one in my pants." I hurried up pick my movie went to the cashiers and bought my dong and movie and went home.
When I got home I rushed to the TV unclothing the whole way put in my she male porn and put lotion on my dong. The movie had barely started playing by the time had the dildo in the ass and had that first time pain subside. In no time at all I was pounding my hole harder than the porn starts fucking on the TV. I could feel all sorts of great feelings I knew my colon was Cumming like a women's pussy does. plus I could see precum from at the head off hard on I barely touched my member and it started blowing load after load of semen my butt got extremely tight as I was still trying to slide in and out. My body was shaking cum was flying all the way to my face. it was by far the biggest orgasm I've ever had. When the orgasm subsided I was just laying there enjoying the little rushes of feelings going my body cover in my own cum and dildo still deep in my ass. I started to think if that was that good being with a guy must be ten times better. Being able to just lay there as a guy pounding my hole. I remembered that guy said he wanted to fuck me good. So I got to get his card out my pants.
I got the card out of pants. Call or text James for a good time was on the card. I sent a short message [hi it's the guy you ran into at the porn store] a little time pasted I was able to get cleaned up and my phone went off. [I don't remember meeting any guys at any porn stores] damn it's not even the right number that's upsetting. then my phone went off again [I did meet this sweet girl at the porn store she was trying to buy a black dildo] I giggled and replied back [I see I'm the girl you ran into] [OK so did you still buy the dong] I replied [yes it was amazing but I really would like to ride the big one u said u had] [OK I only do girls and girls with dicks] [so you want me dressed up] [you got it] [ I don't have a whole lot I only got a couple skirts and under wear sets] [ don't worry I got everything you need just head to that address on the card] [ OK on my way]
I got dressed really fast and headed to the address. When I got there I couldn't believe it was a pretty big house at 5 bedrooms. I rang the door bell and James came to let me in he said OK lets go upstairs get you all dressed up he had a Hugh selection of cloths I grab a pair 4 1/2'' pumps with a peep toe I skirt the barely cover my butt and a blouse with v-neck to show cleavage I didn't have. He came in and said that's cute get in the shower the hair won't do shave it all off I did as I was told when I got out he asked "do you know how to put on makeup" I replied " no but I'll try" " OK when you're done put some polish on your toes and fingers get dressed here's a few wigs then come get me" I walked to the mirror I tried my best to put on the makeup I thought I did a good for my first time I looked like a slut. I saw a blond wig it made me look sexy. I put on some hot pink nail polish on my toes and finger nails. Then I got the rest of the way dressed. I look in the full body mirror did a few spins and said damn I make a good slut. I began to make my way to James so he could fuck me good I've been bad.
When I found him he looked me up and down real good took my hand and took me to what he said was his sex room. When we got in there I dropped to my knees and started to unzip his pants. I pulled out his pecker it was soft and had to have been 7" long and the girth was Hugh I couldn't fit my hand around it. So started tug on it and suck on the head to begin getting it hard it didn't take long he grew to 11'' long and a whooping 4'' around. I started to think this is never going to fit in my one time fucked but a dildo hole. He picked me up off my knees then went to his to pull my panties down then took me to the table said bend over. I did he pulled my skirt up and started sticky his tongue in my hole licking and fingering my hole I started to moan. He said "you like my fingers you'll love my cock. "I can't wait for it" I said. Good roll over to your back I did then he put my feet around his neck I knew what was next. I knew that Hugh penis going into my anus. I felt the head pop in it stretch me so far I bit my bottom lip grabbed his wrists and squeezed to try and release the pain he then slid it in slowly till I felt him hit the farthest point my colon would let him go he then slid it back out to the head popping back out. he then said "that wasn't so bad was it" I shook my head no as I felt the monster cock start pressing to my hole wanting back in I relaxed as much as I could to let it have what it wanted. pop its back in sliding to in and out he slowly picked up pace the pain was subsiding to pure pleasure I heard him grunting "damn you got a tight pussy oh and you got a nice dick too" he grabbed my penis and started rubbing it. I started moaning harder harder harder. After a nice pounding he pulled out really fast pulled my head up and too his dick just fast I started sucking his dick wow my ass tasted great. He pushed me back down and right back into my ass. I was licking my lips hoping this never ended just then I felt my cock start pumping my love juice up and out load after load all over the blouse and my face. While continuing to fuck me he leaned in to lick my cum off my face right then he pulled out and put his dick in my mouth I felt loads of cum filling my mouth so I swallowed as fast as I could but it kept Cumming pump after pump it tasted so good it was sweeter than I thought it would be I wanted to keep some in my mouth but didn't know how much more was coming. Finally it came I had still had a mouth full of his spunk as he fell next to me. He said "wow you have a great ass."
We laid there for a few minutes he then looked at me and said "have you ever thought of being a call girl.""What do you mean by that?" I asked "you know getting breast implants going full female" he said. "don't know" I replied " that gets expensive and I don't know if I want to get rid of my penis but boobs that would be pretty awesome just a lot of money." he then explained " I know a doctor who would do breast a little facial work make you look the full part of a girl and you pay with money you get working for me." "how would I be working for exactly?" "will we get done we do porn videos and you also take in clients to have with you" "I don't know let think about it" "OK"