Looking through my old diaries seeing this entry I relived how I felt, how I took special care to pick the right outfit, makeup, wig and every moment of it. Hope you like it. Kisses

OK, so I am fifteen got my driving permit (Hooray). Mom and Dad would help me get a used car when the time came but I had to save some $$$ for its purchase, insurance, upkeep. Back then no one would hire the local trans who wore dresses and was more fem then the girls so what to do.
The solution!!! For you that have not read my post and profile I was pimped out by my 6th grade teacher for years he would give me a few $$ each time but kept most for himself (not a bad deal for him). Anyway, one hot July afternoon sitting at home looking in the paper want ads for something I was good at hoping for an ad "looking for faggot sissy transgender to help around the house" knowing there would be no such luck I thought I would get paid for the thing I did best giving blow jobs and getting fucked.
As the sun set I cleaned up slipped on my cutest short pink pleated tennis skirt, white "hello Kitty" sneakers with pink lace top anklets, black ruffled panties, black under wire lace bra, little budding "A" cup falsies, a white low cut halter top (bra showing), shoulder length blond wig, full makeup and headed down the trail through the woods behind our house to a "pick up" spot (met the boys there after school many times).
Coming to a clearing off the trail where there is a picnic table I sat on it swinging my skinny fem legs. My skirt hiked up reviling my soft thighs and a little panty peak as well and my flat young midriff from my waist to my halter top in full view.
Hearing some rustling in the woods behind me I quietly went and peaked. Some old guy was getting a blow job. Oh well back to the picnic table I went.
15 minutes of so later an elderly man game into view walking up the trail. He stopped at the cleaning looking over at me. I smiled at him and swung my legs like a little girl. He approached me "Your adorable sweetie he said. I looked up at him giving him a smile with my cherry red glossed full lips. "Thank you mister" I said, teasing him a little I crossed my legs so my skirt would drape over them showing my black ruffled panties.
You could almost see him drooling. Nervously he said "you for hire cutie" biting my lower lips and trying not to show how fucking nervous I was "25.00 get you a blow job, $35.00 you can fuck me also" I said. MMM he moaned taking out $50.00 from his wallet. Holding the $$ he asked "you a boy" "no a girl in a boys body" I replied, Perfect he said and reaching out and pushing the $$ in my bra.
He held his hand out helping me off the table "let go in the woods a little" he said. He wrapped his arm round me rubbing my exposed midriff and cupping my hard false breast. Once we got to a clearing he asked "You are so cute you sure you're a boy" I stepped back, raised my skirt pulled my panties aside showing him my little clitlit OMG he muttered reaching out rubbing it. I stepped back letting my skirt fall down and reached out running my hand over his rock hard cock (it was so hard in one more minute it would have ripped his pants). He unzipped his pants and his old cock sprang out. I wrapped my soft fem hand around it took a step forward and kissed him.
I pulled away from the quick kiss sliding down to my knees as I stoked his member. Looking up at him I kissed the head flicked my tongue over it and took just the head in my mouth. "How old are you honey" he said. Pulling off his cock a little drool dripped from my lip "I'm fifteen" I said. "Oh my god blow me you little fucking whore" he said held the back of my head and drove his cock down my throat. I gagged pulled back and started sucking it with slow genital stokes. Saliva building up I let some drip out so he would see it run down my chin.
He was so excited he started wobbling back and forth trying to maintain his balance he took a few steps back and leaned on a tree and I took is cock deep in my mouth pressing my lips to his groin gagging as I did. I started sucking faster and harder.
Some pre-cum hit my tongue and he pulled out pre-cum hanging from the tip in a long strand. "Don't you make me cum I'm going to fuck you" he blurted out. Reaching down pulling me up pushing me to the tree he raised my skirt pulled my panties down around my ankles cupped my tight slender ass cheeks. "You can't be a boy no boy has an ass shaped like this" I turned saying "the only thing about me that is a boy is this little dick now fuck me"
I parted my legs and he pressed his cock to my fem pussy. Feeling the head I pushed back sinking it in me. He held my skinny hips tight he plowed that old meat deep in me and started fucking me.
Driving his cock in and out my hands on the tree trying to stabilize myself he was like a wild man trusting his cock in all the way them pulling out driving it back in over and over calling me names and drooling on my back.
A couple power thrust I'm going to cum he yelled and pulled out spun me around pushed me to my knees "open your mouth" he said before my mouth was fully open he let go with a sloppy gush of cum some hitting my nose, cheek a spray on my neck and chest. He rested the tip on my bottom lips his load pulsating in my mouth as I swallowed over and over.
OMG he said over and over as his orgasm subsided. His legs shaking his dick dripping cum as he pulled out. I looked up at him his eyes were closed I took his wilting cock in my hand and ran my tongue over it licking up the stands of cu dripping from its head.
He let out a WOOOOO you are incredible and your not a boy darling your all girl I don't care what is between you legs you're a girl.
Thick cum on my face, heated by the July evening smearing my makeup and running down and hanging from my chin in long sticky strands, Cum on my neck and chest seeping down into my exposed bra as he helped me to my feet. You little slut he said reaching out sliding his finger under my chin collecting the dripping cum. I parted my lips a little in anticipation of sucking his cum dripping fingers. He raised his hand passing my eager lips and slid them into his mouth MMMMM he moaned as he licked and savored the cum.
I pulled up my panties pulled down my skirt and ran my tongue over my lips "thank you" I said and took his hand in mine. He said"thank you". Back at the picnic table he took $20.00 out of his wallet pulled my cum wet halter top out and stuffed it in my bra along with the other.
Friday night same time okay he said. "Gladly it's a date" I replied. He continued "I'm partial to petticoats and black stocking" I smiled saying "and a garter belt and prom dress right daddy". YESSSS he moaned rubbing his cock and with his voice cracking "you have any young fem-boy or gay friends" "A few" I replied. He took a deep breath "big dicks" he blurted out. My eyes open wide "oh yea nice and hard and full of cum" another deep breath "I will pay you to bring one with you and pay them $50.00 to let me blow them"
I kissed his cheek "I'm sure I can help you with that see you Friday". He headed down the trail one way I the other. I stopped turned "Hey misters tell your friends" "nope you're all mine".
Holy crap I though as I counting the money 20 minutes for $75.00 to suck his cock and letting him fuck me no need to read the want ads anymore.
I met him almost 2 times a week for the rest of the summer he paid for most of a second hand convertible the others paid for the rest. True story.