My First Time with a Woman

I still remember my first time with a woman. I was nineteen and had been recalled from college by my Aunt Wilhelmina. Father and Mum had run off with the family fortune and I was officially without means. Aunt Wilhelmina gave me options.

“Listen, kid,” Willie said, lighting her umpteenth cigarette of the day. Willie is one of those tall, stout women one suspects was born with a white blanket. Willie sported a loose fitting man’s suit and sprawled into one of the large, overstuffed chairs. “You are a beautiful girl. You could get married to any number of men and live an extremely comfortable life. For that matter, you could accept gifts from any number of men and keep yourself quite comfortable while maintaining your freedom.”

Willie inhaled deeply on her cigarette. Her eyes narrowed as she studied me. “However, if you decide to date women,” Willie continued, punching out her cigarette and moving to stand behind me, her large, mannish hands cupping my ass gently before alternately squeezing each cheek. I remember leaning my head back against her shoulder and pushing my ass into her hands. “With women, there is no risk of pregnancy. The risk of disease is greatly decreased. And,” she continued, one of her hands bunching my skirt between my legs while her hand found my pussy and began to rub it down, “secretive as we are, you will be more than welcome to have both a private life and a public life without any fear of the two lives meeting.”

I turned into Willie arms, and with a move I had perfected during my dating life, I had her single breasted jacket unbuttoned and shucked with my hands gliding inside her shirt. I knew the rules of the game. Women, men, senator or gas jockey. It was the same rule whomever you fucked. Make sure they got theirs and then you would get yours.

My Aunt Wilhelmina stands 5’10” and weighed around 200 lbs. She was a tall woman, both broad of shoulder and broad of ass. I, however, was a taller woman, standing 6’3” and weighing about 145 lbs. I am long, lean, with the best, all natural rack. I am sure Willie felt petite for the first time in a number of years. Yeah, she out weighed me, but she got to look up for a kiss.

My hands were pleasantly surprised to find two hard grapefruit sized breasts with the absolutely stiffest nipples ever. I slowly pulsed them in my hands while my mouth found hers in a long, passionate kiss. I increased the pressure on her breasts and began rolling her nipples in my palm, making Willie moan deep in her throat. Willie kept trying to lead me to the davenport, but I bullied her body to the glass doors opening into her private garden. Once I had Willie pressed up against the doors, I began to grind my hips into hers.

Shocked, I pulled away from Willie to look into her eyes, a huge smile lighting up my face. “Why, Willie,” I exclaimed in mock consternation, “are you holding out on me?” I threw my head back and laughed as I watched the blush redden that old battle axes complexion. In a flash, I had Willie’s pants yanked down to her ankles. There stood Willie, in her open oxford, socks and wingtips, and a huge, black phallus pushing its head out of her briefs with little lipstick kisses all over them.

I grabbed the back of Willie’s head and kissed her long and hard. Willie returned my kisses with equal passion, her hand jacking her big, black phallus. “Strip!” Willie ordered, her voice hoarse. Slowly, I stripped off piece by piece, until I stood in nothing more than my heels and stockings. Falling to my hands and knees, I crawled back to Willie, my eyes never leaving hers. Sitting up on my knees, I rested Willie’s ass in my hands before my mouth made love to her thighs. Up and down and back again I kissed and licked each thigh while I massaged her ass. Slowly, I began pushing her legs apart, and inch every couple of minutes.

I grabbed Willie’s wrists, held them firm against the window, and began the head bob game. Taking a little bit now, and then a little bit more, I had all 10” of her sliding down my throat, the speed slowly increasing.

Before I knew it, Willie had ripped her hands out of their imprisonment. She gripped my shoulders as her hips began to buck wildly against my mouth. When the bucking stopped, I caught Willie’s weight as her knees began to give and brought her down to the floor.

With my back to her, I sat down on Willie’s cock, starting my pelvic figure eights. It was exquisite. All that lovely, hard cock pressing against the walls of my cunt. As I continued to pleasure myself, I did not forget about my benefactress. Leaning over, I brought her foot to me and began a firm, sensuous massage, occasionally taking a toe into my mouth, or making love to one of her arches.

An hour later, we were both replete, dressed and Aunt Wilhelmina handed me a check for ten thousand dollars. That was my first time with a woman. It was the start of my long and prosperous career as a female’s prostitute.