Fall 1997 – 18 yrs old
After I’d given my self to my best friend Dave, I lived in my “Angie” persona whenever I was around him. I was still in my cross-dressing phase, not yet realizing I would evolve and grow into a transgendered woman. I didn’t believe my parents would approve of my new behaviors. I would change at a gas station before I went to Dave’s house.
His parents allowed him to live in an apartment over their garage. I could come and go unseen. As my hair grew longer, I quit wearing a wig. I had a couple of skirt and blouse combinations, but Dave bought me my first sundress. He also bought a couple of tank tops and some short denim skirts for me. I looked like a late-blooming teenage girl.
I would get to his place about mid-afternoon. Dave would fuck me once or twice during my visit, but he preferred I suck his cock. I didn’t mind, so much, since I REALLY enjoy cock sucking. I can’t get enough! I did wish he’d fuck me more.
Usually, I would kneel before him and take him into my mouth while he watched Porn on his TV. He might fondle my nipples and suck them, but mostly, he wanted blowjobs. I might remove my top and pull up my skirt, but Dave didn’t seem to want to see me naked. I thought it strange, since I was his girlfriend. He called me his girlfriend and would take me to movies, or to get a pizza. It never occurred to me to wonder why we only went to dark places He never took me
We’d been seeing each other for several months. I was on my knees (as usual!) hungrily sucking his cock. He’d already come twice. My top was on the floor beside me, my skirt pulled up to my waist. He’d been caressing my bottom and I was hoping he might fuck me soon.
“So this is Andrew!” I heard a female voice speak. “He makes a very pretty girl, doesn’t he?”
I turned around and saw Dave’s older sister, Janet. Janet isa heavy girl with an attractive face. She was staring at me, sneering with contempt!
“I wonder what your parents would think? I wonder if they know their little boy was a cross-dressing, cock sucking slut?”
“Please, don’t tell them!” I begged, tears running down my face.
“And why shouldn’t I?” She asked, arms crossed.
“Please…..I’ll do anything! Just….don’t tell!”
Janet walked to Dave’s bedroom, then returned shortly, wearing only her high heels. She walked over and sat on the edge of his sofa,s preading her legs wide and exposing her hairy pussy. She crooked her finger and motioned me over.
“Lick my pussy good enough, and I might not tell.” She commanded.
I’d never eaten pussy before, but I’d seen it done enough in the porn videos to know how to do it. I knelt before her and buried my face in that hair! I ran my tongue all over her opening. She smelled terrible and tasted worse! ( I found out afterwards she was in the middle of her period!)
She directed me in what to do to please her and after a few minutes, she squeezed my head with her legs and came very loudly. She grabbed my head and held me tight against her pussy.
“Again!” she commanded.
I continued to lick and suck her, licking her clit and running my tongue deep inside. I must have licked for another half hour. Dave caressed my bottom. I hoped he would fuck me, but he only played with my ass.
Janet came again and released me. She and Dave laughed as Iran to his bathroom and threw up. I cleaned up and returned to the living area.
Janet stood up and sauntered over to the bar, sitting with her back to me and her very full ass hanging over the back.
“Lick my asshole!” she commanded.
I sat on the floor behind her and forced my tongue into her crack, lapping her like an ice cream cone. Dave grabbed my hips pulling me to all fours. My head was at a difficult and painful angle as I struggled to reach her asshole with my tongue. Only the tip was flickering across her pucker.
Dave grabbed my hips and forced his rock hard cock all the way into my ass. I yelped in pain: he hadn’t bothered lubing first. Since he’d already came twice, I hoped he‘d fuck me awhile.
Dave fucked me about a couple of minutes then pulled out and pushed me aside. He then rammed his cock into his sister’s ass.
“Yeesss!...” she moaned as he cupped one of her full breasts and held her close.
I could only watch in stunned silence as he pounded her for another thirty minutes. He came, then pushed me back to her cum-filled ass and ordered me to lick her clean. He rammed his still erect cock into my ass and roughly pounded me.
Janet reached between her legs, fingering herself to a couple of orgasms before Dave came in my ass.
They sat on the sofa, me sucking Dave’s cock while he fondled her heavy breast. After a few moments, she left and returned wearing a strap-on cock and harness. She knelt behind me and rammed the dildo into my ass while I sucked Dave.
It felt like an eternity before Dave came on last time, and she withdrew from my ass. I was very tired and sore. I cleaned up and left. I snuck into my room and changed before my parents came home.
This became a frequent routine with them. I soon learned to like eating pussy and ass. I just didn’t feel very much like I was someone’s girlfriend.
places when It was light outside!