A true and original story from my crazy life;
My friend Billy did not have any interest in sports or other things that boys do but we got along just fine. I would go off to play little league or catch with the other guys but Billy and I would watch TV, go to movies, or just goof around doing other things. Looking back Billy was a little effeminate and the other guys thought he was nerdy but I guess since he didn't have many friends I maybe felt sorry for him. A few times when we had a sleep over he would crawl into my bed with a flashlight and would ask if I wanted to show him my pee-pee and he would show me his. I assumed this was just part of growing up and didn't really think much about it.
On day however, when we were about 15 I went over Billy's house to see if he wanted to do something. I was greeted by him mom at the back door. She said Billy was upstairs in his room and to go ahead and go up there and surprise him. I thought this was a funny choice of words, but quickly dismissed it from my head as I went up the stairs. His bedroom door was closed and without knocking I barged right in. Standing at the mirror above his dresser was Billy.all dressed up like a girl! He was wearing mascara eye make-up and lipstick with a blue and pink sundress and he had his hair styled in a girlish way. I was shocked to say the least. I didn't know what to say and was embarrassed, so I turned to leave.
"Please don't go Jimmy" he said. "Come on back and let's talk." I, ah, don't know what to say Billy, I had no idea" "Well, I am glad you caught me Jimmy because I don't want to hide it any longer" he said. "Well I must say you do make a better looking girl than a boy" "Wow thank you" Billy said and he hugged me. "This is just too strange for me Billy. I don't think I really like it" "It was strange for me too at first but I really do feel so much more comfortable as a girl and I hope you will understand. In time I am hoping you will accept me this way." He said. "I guess I can try" I said reluctantly. "Great" Billy said then he leaned into me and kissed me on the lips. "Whoa, wait a minute here, I didn't say anything about kissing me" I said as I pushed him away. "Well you are my best friend, and you're a boy, so.that makes you my boyfriend" "Look Billy, I really need to think about this whole thing. I'll talk to you later" "OK, call me tonight, OK?" he said. "OK, maybe" I replied then I left.
As I was walking out Billy's mom must have noticed the strange look on my face and she asked if everything was OK. I said yes it was, and as I walked out the door she said Billy is really much better this way. Wow, she knew all about this and evidently was fine with it.
I was in shock all afternoon and just sat in my room thinking about Billy, my best friend, as a girl. I was really confused but now I was remembering subtle clues and mannerisms and things Billy said since puberty that all of a sudden made a lot of sense to me. I also had a sexual thought or two pop into my head, after all, I was a 15 year old boy, but I did my best to not go there.
That night I called Billy and I told him I was willing to give it a try as long as he didn't try to kiss me again. He said he would try not to do that again too but sounded disappointed. He said that he would finish the school year as a boy since we only had a few weeks to go, then reenroll in the fall as the girl "Billie" He said that he was seeing a doctor that started him on hormones, and was seeing a psychologist. Guess this thing was serious and not a passing phase as I had hoped.
Over the last few weeks of school I avoided him as much as I could. I wasn't sure how to act around him and I think I was a little embarrassed by the whole thing. Billy called often but I always had an excuse as to why I couldn't come over, but we did have some good talks on the phone. When we got out of school for the summer Billy, or I guess I should say Billie, went to stay with her aunt in California for most of the summer as she always had. She.I suppose I began calling her she over the summer. called a couple of times a week and it was obvious that she was well on her way to becoming a full fledged girl and I was accepting her that way.
Near the end of August she returned back to Texas and she called me and asked me to come over to her house. She said she was real happy to be back home and excited to see me. I rode my bike over to her place and I was a bit nervous but I admit I was excited to see her too. Coincidently was my 16th birthday and she said she had a present for me.
I rang the bell and the door opened just an inch or two. "Are you ready for a surprise? She said "I think so"
And the door opened the rest of the way..
I don't think I will ever forget the first time I saw her. There was no doubt this was a girl I was looking at. Billies body changed dramatically and she had curves she never had before, and titties too. She was wearing a denim mini shirt and a white tank top. Her hair was longer and blonde and really looked cute. She had make-up on, mascara and lipstick. Maybe a little too much make-up but she was far cuter that most of the girls at school. She hugged me and I noticed she smelled real great too. I remember just saying wow a lot because I couldn't get over how great she looked.
We grabbed a couple of cokes and went out to the patio to talk. Billie told me all about her summer in California. Her Aunt helped her a lot in her "transition", teaching her to act and talk like a girl, and she told me about the whole new closet full of clothes she had.
I saw Billie in a whole different way now. Being a 16 year old my mind wandered to those thoughts that boys my age have about every 45 seconds. Billie noticed how I was looking at her titties a lot. "Don't they look nice? She said. "Uh, what looks nice" "My boobs you silly boy" "Um well I guess so" I stammered. "The feel even better than they look" "Oh" "So?" She said "So what?" I replied "So why don't you feel them" she said "Billie I.." With that Billie got up and kneeled in front of me and looked me right in the eye. "I really want you to touch them Randy" she said. "Please" she said. "But you Mom." "My Mom is at work and she wont be home for hours..After you feel up my boobies I will give you your birthday present" she said.
I dint know if I should get up and run or feel her boobies, but I guess I had a hormone rush so I put one hand over her tit. "Feel under my shirt, Jimmy" I slipped my hand under the tank top and she was right, they did feel nice.
Billie closed her eyes and softly moaned. "I lay in bed at night thinking of this all summer Jimmy" Billie leaned forward and kissed me full on the lips and I kissed her back.
My dick was now hard and it was creating quite a tent in my shorts. When Billie pulled back from kissing me she rubbed it and asked if I wanted my 16th birthday present now. "Um, I think so Billie" I said. "Here, lift up a bit" said Billie as she pulled my shorts down. Billie stroked me a few times then put my dick in her mouth. I had never had a blow job before, heck I never even had sex before except the kind we have alone in the bathroom. It only took about a minute.OK probably only 30 seconds and that feeling started at my toes and spread through my body. Billie sucked away and I shot. She gagged a little at first than swallowed it all down her throat, than kissed my dick and balls real gently until our breathing slowed back down to normal. "How did you learn to do that?" I asked. "I guess it just something a girl knows silly boy. And besides Aunt Margie show me some videos on how a girl acts in the bedroom" "Was I the first?" "The one and only" she said.
Fortunately we heard her Mom pull in the driveway so we sat up quickly and I pulled up my pants and Billie quickly pulled her top up. Her mom came out back to the patio to say hi and I am sure we looked guilty of something because I sure felt guilty. I am pretty sure her mom suspected something was going on but she didn't say anything about it.
It was dinner time so I said bye and headed home. It's funny how after your first blow job felt I felt like I was suddenly not a boy anymore but a man. For the first time in my life I felt like it was childish to be riding my kid bike home.
By the time I got back home I was hard again thinking of my first blow job. Before dinner I jacked off because my hard on just wouldn't go down any other way. That night about 9:00 Billie called me and said she cant wait to do it again. We both snuck out of the house and met half way. Billie sucked me off behind the bushes in front of the Spencer's house.
Over the next few weeks before school started Billie would suck me at least once a day and sometimes more. I was now lasting several minutes longer and she wasn't gagging at that first squirt anymore.
One memorable day I went over her place about 10 in the morning while her mom was at work. Billy greeted me in some things she had "borrowed" from her mom's closet. She was wearing a sheer black nightie, black stockings and very high heels. She had her hair pinned up in a grown up style and she was wearing real heavy eye make-up and red lipstick. Billie looked like she was at least 25 years old, and very sexy. We got drunk on wine coolers and had sex all day. I think I came at least 6 or 7 times. I came in her mouth mostly but one time I was on my back and she made me cum all over my chest and stomach and she licked it all up. We even tried the anal thing but she said it hurt too much. This whole time by the way, Billie never wanted me to touch her penis. Since hormones it stayed small and she kept it pretty much tucked away and she didn't like being reminded of it.
Billies mom had decided that she should start over at a different school where no one knew her as a boy. So when school started her mom drove her across town everyday until they found a house. The once daily blow jobs became once or twice a week during this time. By November they moved and we were only able to see each other every few weeks. Even the phone calls between us tapered off then stopped altogether.
I moved on with my life and had and dated some girls but hadn't had much success finding any that were as motivated to give blow jobs as Billie was. About two years later I was playing baseball on that side of town and one of the guys said there was this chick in the boys' bathroom at the park giving blow jobs to any guy that wanted one. Of course I headed over there and saw about 5 or 6 guys hanging out outside the bathroom. I peeked in and saw three guys with their pants down and the girl on her knees. She had one dick in her mouth and one in each hand. I wasn't at all surprised that it was my old friend Billie.
I smiled and headed back to the ballpark.