by trashcan44 02/24/10
My aunt Betty. She was a shining star in my life. She had been everywhere and done everything. She was my mothers baby sister and had been a stewardess, a nurse and even a Los Vegas show girl. Mostly what she was was a prostitute. You name it, she had done it; call girl, stripper, house whore even a street walker.
She was about five feet tall, raven black hair, green eyes and a nice rack. She resembled Bree Olsen, the porn star, in build. God she was hot and attracted men like a light bulb attracts insects on a hot Georgia night.
I was raised by my mother and even though I had an older half-brother and two younger half-sisters it was mostly just me and mom. The rest of the kids almost always living with their fathers family's. I never met my father so there was no one to pawn me off on.
We always lived in small apartments and usually of the studio kind. Mom was a looker herself, about 5' 4", brunette with a slender frame and A cup titties. I used to play with her "falsies" as a kid before I knew what they were. She had the morals of an alley cat. There was an endless parade of men at our door and, under the living arrangements, there were no secrets. I did not grow up with a strong male role-model.
Aunt Betty used to show up at our door unannounced. Sometime on top of the world, driving a new Cadillac Convertible, sometimes carrying a beat up suitcase from the city bus stop. No matter, I was always thrilled to see her. I knew that for the next week or so I would have two gorgeous women walking around in bras and panties and sometimes even less. It was Aunt Betty who taught me how to be a "personal maid", shaving her legs, washing her hair and lingerie and even helping apply makeup. Mom waited till I had perfected my talents but then she too took advantage of my "skills". They even used to dress me "up". I loved it all. It was a very unconventional childhood but I didn't know it at the time.
Things changed when I turned eighteen. I don't know if mom was tired of me living with her or if it was me rebelling but we started fighting, a lot. Finally when school was out she packed a bag for me, handed me fifty dollars and a bus ticket and kissed me good bye. I was on my way to live with Aunt Betty. I only hoped she would take me in.
Bright lights and big city! I showed up at her door after two days on the bus. She was shocked to see me but she didn't turn me away. After listening to my tale she agreed to let me stay until I could decide what I wanted to do with my life. At least I had a couch to sleep on.
I quickly fell under her spell and within a day or two I was again her personal maid. She agreed to pay me a small stipend along with room and board for my "personal" services. I was more than happy with that. She also explained to me for the first time what exactly she did for a living. I was a little dismayed at first but she just giggled at my blushing and teased me.
"Hadn't I ever paid for sex?" she asked.
I blushed even more, afraid to tell her I was a virgin.
My silence must have tipped her off. She quit laughing and got a funny look on her face, then she leaned over and kissed me on the lips. It was a tender kiss but not at all like she had ever kissed me before. It was my first boy/girl kiss and I knew I was in love.
"You're so cute!" she giggled. "now help me get ready, I have an appointment to keep."
She giggled some more when she saw the tent in my pants as I stood up to follow her into her bedroom. Stripping off her clothes she told me to get her bubble bath ready. I scampered away. For the next couple hours I was in a constant state of arousal as I bathed her, shaved her legs and, I don't know why, but I actually had an orgasm when she had me shave her underarms. She noticed and smiled. Shaking her head she said.
"I was going to have you give my little pussy a trim but I don't think you could handle the excitement!"
I blushed at her language and I'm sure my disappointment showed. I had disappointed her and I silently vowed to have more control in the future.
She laughed at my stern look. I will always believe she could read every thought I had.
"That's OK, you can help me with my body lotion" she said as she toweled off.
I was in heaven and after seeing how obviously excited I became she murmured something about teenage boys and sighed as I lovingly ran my hands over every inch of her body. I was too shy to linger at her breasts but I did get to touch them and I gave her ass extra attention. I got to do her thighs but she stopped me short of her "money maker", (wink, smile).
Next came her sexy underwear. She threw open her drawer and told me to pick out what she should wear. I was in awe. There were hundreds of panties and bras in all colors, a huge assortment of slips and camisoles and garter belts. There was a section of corsets and bustiers. Stockings and pantyhose filled another drawer. I finally chose a matching turquoise bra and pantie set. I was in danger of breaking my vow of self control as I helped her on with her sheer white stocking and rather awkwardly fastened them to her garter belt. She even allowed me to fasten her bra! YES! She finished with a flowered sun dress and white high heels. God she looked hot.
She headed for the door then turned back and said.
"I remember how you used to like to play dress-up. You can play with my things, just don't stretch anything out. OK? Maybe later we can buy you a few sexy outfits that fit you better. Would you like that?"
I was so thrilled I could only nod my head. I had the best aunt in the world.
She left me then and for the rest of the evening I played with her sexy underwear. I must have jerked off ten times, always careful not to get any on her things. My favorite pair was the ones she had been wearing just before her bath. They had a combination earthy and perfume fragrance that drove me wild. I fell asleep lying on a dozen pairs of her panties and holding her soiled ones to my nose.
I woke the next morning with her spooned naked against my back. I was a little embarrassed to see I still had the panties in my hand. I also had a raging hard on and an overwhelming need to pee. Those were both normal and I would usually have to jerk off before my cock would go soft enough to pee. I tried to move away from her without waking her but every time I moved she moaned and snuggled tighter. Thinking about what she had pressing against me was not helping my hard on situation I can tell you! Finally, moving only the hand holding her panties, I started to stroke my cock. I just couldn't help it. Just about the time my orgasm hit I realized I didn't have a plan on how to deal with all the cum. I couldn't let it get on all the panties I was still laying on so with more movement than was prudent I did my best to capture it with my other hand although some of it did get on the panties I was using to jerk off with. I started to spasm and I could feel her holding me tighter and moaning softly in protest of being awakened. Praying she wouldn't wake up I finished cumming in my palm. Oh shit! Now what. I could only think of one way to dispose of it. I brought my hand slowly up to my lips and as quietly as I could I slurped the spunk into my mouth. It wasn't bad tasting but not something an eighteen year old boy wants anyone to see.
"Mmm, that's naughty!"
I froze. Oh my god! She was awake and she had seen!
"I'm sorry Aunt Betty" I felt like crying.
She snuggled closer and caressed my still hard cock with one hand and then nibbled on my ear lobe.
"Play with that wonderful cock all you want Sweetie" she purred, "That's what its there for. And I love watching you be naughty!" "From the looks of things you were naughty a lot last night. Now go use the bathroom, I'm going to get some sleep."
She gave my dick a squeeze and a tug then pushed me out of bed.
From then on I always shared her bed and almost every morning she watched, and sometimes helped, me jerk off. I always swallowed my spunk, not so much because I liked the taste, as that she liked so much watching me be "naughty".
We settled into a routine. I tried my best to earn my way. I did all the cleaning and laundry and she was able to let go of her cleaning service and everything except the dry cleaning. She was also surprised at my cooking skills and would make a big deal over the most modest of dinners. Just to please her I even took some extension courses in "home economics". I was the only boy in the class. She would teases me and say she was afraid of "losing" me when the other girls found out what a good "maid" I was.
She was also true to her word and bought me my own panties and silky night gowns. It's a whole other story about how that evolved into almost weekly shopping trips and girls days out. Eventually I came to dress the part of her maid as well.
After a couple of weeks she told me that she needed to resume entertaining some of her regular "dates" in her apartment. At first I would go out to a movie or a night class or something. That was getting expensive though. Like in most things Aunt Betty found a solution, one uniquely her own.
I would "stay in the closet". She laughed hysterically at that, me being dressed in panties and a silky nightgown at the time. The idea was for me to sit quietly in her walk in closet while she entertained her dates in the living room and then the bedroom.
"And no peeking!" she giggled.
Even she knew she wasn't serious. The door was louvered and I had grown up watching my mother service countless men while she thought I was asleep. I took every opportunity to see my aunt naked and she never minded. Hell I shaved her legs and trimmed her pubic hair. I was dying to watch her have sex.
That evening after I had helped her get ready she had me set a small chair in the closet. Just before she put on her lipstick she called me into the closet and set me on the chair. We could both see that I would have a perfect view of the bed. I was so excited I was shaking. I thought I would cum in my pants. A not so rare occurrence.
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