As the star running back of my high school football team, I get more than my share of attention - girls who want to be my girlfriend, girls who'll beg to give me a quick blow job. And the boys give me plenty of attention too - from the other jocks who want to be my buds (some of them have full-blown crushes on me and don't realize it) to the less popular guys who treat me with a mixture of envy and awe. And I've had my share of fun and wild sex, but in my senior year of high school, I knew I wanted to focus on my real desires that none of my high school friends know anything about - my growing, desire to dress and live as a very sexual, independent woman.
Don't get me wrong - I've got no desire to have the full operation. I enjoy my penis but I've come to enjoy more and more dressing and passing as a woman and I knew in my senior year it was time for me to start living out some of my desires. As a seventeen year old with almost no family, I've lived full-time (since I was ten years old) with my "Aunt Jackie", my mom's best friend. My Aunt Jackie was always the primary adult in my life because my mother was always starting a new relationship with a man and either didn't want her new man to know she had a son or just found it inconvenient. My Aunt Jackie has always been supportive of me in every way and when she discovered my interest in cross-dressing. She taught me how to walk, sit, and put on make up. Later she even taught me how to flirt and tease a man - "Aunt Jackie's Finishing School" we called it. But she made it clear that it was all strictly our secret and let me know how taboo it was all considered especially in the black community.
Aunt Jackie has been a flight attendant for many years, as I got older she has felt free to go on longer flights and spend more and more time away from home. She gives me plenty of love and plenty of freedom. She even helped me come up with my "fem" name, "DeShawna" and on a couple of special occasions has taken me out in public as "DeShawna". Once when she had a date with a particularly lecherous pilot, a married white man named Brock, she took me along and we played a fantastic game of teasing Brock into thinking he'd be lucky enough to have a hot threesome with us. Brock was ordering very expensive bottles of wine and then Champaign - you could see he was visualizing himself in bed with the two of us. At the end of the evening, Brock was really drunk and Aunt Jackie left me alone with him in the living room for about an hour while I teased the man unmercifully. He started by putting his hand on my thigh and then working it up my skirt - he started kissing me and I was really enjoying it. Brock was very rugged, very handsome, and he was a great kisser. I kept his hands from traveling too close to my taped down private parts - though he likely would never have suspected even if I'd let him fondled me there.
Eventually he lay on top of me kissing me passionately, telling he wanted to fuck me, and grinding his huge, hard penis against me. I asked him innocently if I could touch it - he had his pants down around his ankles so fast I nearly laughed. I made a big deal about how huge his penis was (and it was). I stroked it masterfully with my well-manicured acrylic nails. By the time I leaned over to put my mouth on his penis, I thought he was going to shoot his wad like an inexperienced teenager but he barely managed to contain himself while I sucked and licked his huge dick. Brock was becoming more and more verbal, "Oh God, yeah, baby suck my big cock?you love my big dick, huh? Bet you wanna eat a big load of my sweet cum, don't you baby?"
He took his cock into his own hand and was masturbating furiously when I moved my mouth down to his hairy balls and the hairy mound between his balls and his asshole. I don't know if any girl had ever sucked Brock's balls and licked his asshole before, but Brock blew his load with so much enthusiasm, I thought the neighbors might call the police.
Instead Aunt Jackie, popped back into the living room and flipped on the lights with a scream of indignation, "What in the hell do you think you're doing with my 17 year-old niece? You freak - I'm going to call the police." Aunt Jackie did a brilliant acting job and poor Brock was in shock. He tried to get to his feet but got tangled in his pants and fell forward across the coffee table, landing in a jumbled mess on the floor, his huge red cock still throbbing and the air heavy with the smell of his cum.
Aunt Jackie kicked him out into the hallway with his pants still around his ankles. And if he hadn't been so drunk and scared, he probably would have heard us shrieking with laughter as she slammed the door.
(To be continued)