Aunt Sherry Takes It

She handed it to me, "I suggest you start here."

I looked at the page and blushed.

She touched my chin.

"Why should you be embarrassed about masturbation? It's normal."

I asked, "It is?"

"You don't feel guilty when you do it? Do you?"

"I try not too."

She rolled her eyes.

"You have to be kidding me?"

"No."

"That explains a lot."

I wondered what that meant.

"Go and enjoy yourself. I never want you to feel guilty for getting yourself off."

She turned and headed to the kitchen.

She yelled in frustration, "What eighteen year old man doesn't get off? My sister was such a prude."

I took the reading materials into my bedroom.

*** Going Deeper ***

During Spring Break of my Senior year of high school Sherry took on the project of changing the basement living room. She often changed the theme of this room but she was doing a complete makeover. There were three ways I could reach the basement. The one way was to wheel myself out of the front of the house and to the back sliding doors. I could wheel myself to the small elevator which slowly took me up and down the three floors. Or I could hobble down the stairs while holding onto the railing. At this point I was able to walk in short bursts and I had just started using crutches. The goal was to move beyond the crutches and walk on my own. Because it was a spring day and it was faster I wheeled around the house.

When I reached the sliding doors of the basement I observed my Aunt hang the last of three mermaid prints. She had changed this whole living room into a nautical theme. She hung these prints above the new L shaped sectional couch. She was overjoyed she found one on clearance. I never believed mermaids could look like this. All five seemed sinister; yet they were beautiful. When I looked into their eyes they seemed to want me. I could easily imagine these magical creatures teaching me the wiles of sex. So far sex had been book knowledge and my own self exploration. Since my Aunt gave me permission to masturbate I was masturbating at least once a day.

The middle print was of three mermaids sitting on a huge rock. In the background sailing under the moon was a pirate ship. These three mermaids were blond, brunette, and redhead. Their hair covered just the front of their breasts. The mermaid print on the left was a blond mermaid pushing herself up on a shallow beach, the moon was behind her, her tail went up behind her back, and the side of her tiny breast were exposed. The painting teased me because it never showed the details. The painting on the right was of a large breasted brunette facing right on a rock with skulls floating on the water. In the background was a pirate ship. Her hair covered the front of her large breasts.

Sherry turned when I opened the sliding door. She watched me open and close the sliding doors and approach her in my wheelchair.

Sherry leaned down and asked me, "Why do you like them?"

I was honest, "They are beautiful."

"Which one do you like best?"

"The one with the red hair."

Teasing she asked, "Would you want me to dye my hair red?"

I shook my head.

"Why?"

"You are beautiful the way you are."

She smiled, "You are so sweet. Girls will love you."

"Why would they like me?"

She answered with a tone, "Because they are foolish. Trust your Aunt. More important. You don't want to date a woman who can't look past some of your difficulties. A good woman will see your determination and your heart."

"I'm not sure."

She gave me a look.

She said, "Once you've become a man. They'll know."

Before I could ask a question she stated, "I was feeling we should add a fish tank."

I eagerly agreed. We immediately left to purchase one. We went to a variety of stores. Like always she wrote down the prices of each store and we asked many questions.

For lunch she treated me to a 1950's style restaurant. The waitresses were wearing fifties style outfits. They were sexy and classy at the same time. She surprised me when she pointed out a waitress she was attracted too. She asked me which ones I liked and if I wanted to have sex with any of them. I was surprised by this. She reminded me we were adults. She felt we should start being more "open" about sex. This led to a very candid sexual talk covering a wide range of sexual topics. Topics she never discussed with me before.

In the afternoon we purchased: a hundred gallon fish tank, the stand, and everything to keep the tank healthy. After we went shopping for the decorations. We hit all of the thrift stores and checked out many yard sales. She always had patience getting in and out of the van. A few times she helped me hobble around. She said she was proud of me for using my crutches. We were able to find many nautical and mermaid trinkets to go into the tank and to decorate the living room. We were overjoyed to find a bin of rocks and shells at a yard sale (she boiled all of the items we intended to place in the tank). Before buying the fish we went home and assembled the stand and set up the tank. While doing so she: made sure to touch my hands, hovered over me, often times her breasts brushed up against my body, she went out of her way to tell me how strong my arms were, complimented me on how much I was accomplishing, and repeatedly mentioned how proud of me she was. This was the first time she ever touched me this way. I felt awkward when her large breasts would rub against me. After we headed back to our favorite tropical fish store and purchased: a few hardy fish, a selection of plastic plants, and a draw bridge bubble castle. She again completed me for using my crutches. She believed there would be a time when I wouldn't even need them. I wanted this to be true.

We placed the fish into the water and observed them swim in the tank. After a short while led me to the couch. She said it would be better to watch them from the couch. At first we were sitting an arms length away. Soon my Aunt placed her head against my arm and snuggled up against my body.

This is when she changed her voice into one I never heard before. She complimented me on the job I did on the fish stand. She was proud of me for using my crutches in public. She believed we were special and she was lucky to have me as a nephew. She mentioned how special our family of two was.

She pointed to one of the mermaid trinkets we placed into the fish tank. She told me I should imagine me being a strong sailor of the sea. How the mermaid wanted to be with me. She knelt down in front of me. She shocked me when she started to undue my belt. I tried to stop her. She stood up and touched my chin and told me how disappointing I was being. I immediately became passive. She: unhooked my belt, undid my pants, and tried to slide them down. I again tried to protest and hide myself. She reacted angrily and accused me of being childish. This again caused me to be submissive; she slid down my pants and underwear. She reassured me this was natural and I should appreciate what she was doing. My family would have been horrified to know my Aunt was stroking my cock. I strongly believe if I told any of my other Aunts and Uncles they would have removed Sherry from the house and figured out different arrangements.

This was the first time anyone other than myself ever touched my cock. Even though I felt terribly guilty. It could not be denied her hand was much better than my own hand. But this was my Aunt. She insisted she was blessing me. She felt I deserved it after using the crutches and shopping without complaint. She said a future girlfriend would appreciate it if she taught me self control. She again made a point to tell me it was natural for two people to want to touch one another. She told me if I learned self control and how to use my tongue my size wouldn't be an issue. She promised she would teach me how to use it. She started to kiss my neck and nibble on my ears.

I was unsure of what I should feel. Part of me knew we were crossing boundaries we shouldn't. What she was saying was a huge turn on for me but it was haunting at the same time. I felt guilty. I asked myself why this was normal. Still having a different persons hand on my cock was thrilling.

She removed her shirt.

I became harder seeing my Aunts tits. The only thing covering them up was a red bra. She moved forward and directed my cock toward her breasts.

She instructed, "I want you to cum all over my bra and tits. Just let me know when it's about to happen."

"Okay."

I warned her when the feeling was there.

She yelled, "That's it! It's cumming!"

The cum went all over her chest and on her hand.

Her eyes became wide, "Wasn't that better than your own hand? Isn't this better than anyone in the lingerie catalogs you like looking at."

I was exhausted.

This is when she calmed down. She stood up and casually walked to the bathroom just off of the basement living room. She washed her hands and removed her bra. When she stepped out she had a towel wrapped around her top and handed me a paper towel.

"Clean up and button up."

I did.

She said, "You need practice."

"Huh."

"You need to last longer."

"Okay."

"A new rule. I consider the whole house private. You may masturbate whenever and wherever you want. Excluding my bedroom and my bathroom."

"Even if you are in the room?"

"Especially if I'm in the room."

I gave her a shocked look.

"I need to teach you how to last."

I blushed.

She touched me on the chin. "One day a women will appreciate what I'll teach you."

Sheepishly I answered, "But your my Aunt?"

"I bet you think I'm ugly? Am I getting fat?."

"No."

"Why wouldn't you want me to teach you? Do you love me?"

"I do."

"Why is there a problem?"

"There isn't any?"

With a tone, "You should like me teaching you. You should feel privileged. Plus. Haven't I provided for you? Haven't I taught you other things? Don't we love each other?"

"Yeah."

She became stern, "You can't tell anyone about this. People wouldn't understand how special our family is."

"I won't."

She gently touched my chin and leaned in, "Don't fret."

She leaned down and tried to kiss me.

I freaked out and flinched.

She became angry, "Don't be like that."

She angrily turned and marched upstairs.

I was crushed. I disappointed my Aunt Sherry.

***The New Rule **

The next day she sat me down and declared we were more liberated than other people; this included our families. She felt masturbation was natural and people shouldn't feel the need to hide it in their own homes. She declared the whole house to be private. The exceptions being: we should be careful of windows, I was banned from entering my Aunt's bedroom or bathroom without her, I was always to clean up any mess I made, I was to take a shower after, and most important I was never to tell anyone about our masturbation rules. I was smart enough to understand this openness to masturbation was unusual.

Twice on the first day when she noticed I was excited I was to pull it out and "get off." I listened. After a while I started to pull it out whenever and wherever I wanted. If my Aunt was in the room she would instruct me on how to stroke myself. She would get irritated if I came to fast and would praise me if the longer I lasted. Many times I would jack off to the catalogs and fashion magazines she subscribed too. We'd often discuss the articles in these magazines and she'd want to know what models I liked.

A few weeks after implementing this masturbation rule adult reading material started to appear on the kitchen table and on the coffee table. These included: Playboy, Playboy Lingerie, Penthouse Letters, Penthouse Forum, Gallery, little erotic paperback books, and a few Playgirl magazines. Half were brand new, a quarter were in wrapped in clear shrink wrap with a large black square on the front, and the rest were obviously paged through before. We often discussed what models we liked and why. She never needed to tell me she was bisexual but it was obvious she was. This was a big deal back then. I believe my family would have removed me from the house if they knew she was bisexual. My Aunts would have removed me if they knew she purchased me pornographic magazines.

My favorite pictorials were the ones where women wore lingerie or were in skirts. As a straight male I was never turned on by pictures of nude men. Often times, I felt an inadequacy looking at these pictures because my cock was never as big as the models were. She would often tell me a women appreciated a good tongue over a big dick. She would often say, "A small dick is no excuse to be a bad lover. Just as a big dick was no excuse to be a lazy lover." No mater my size I was to treat a woman correctly.

These sexual conversation would immediately change if I asked her a personal question. A personal question would change her from being receptive to being indifferent and often times angry. One time, she became so angry at a question, she stopped touching me and told me to finish in my room. I felt so rejected. I felt guilty I asked a question that made her angry.

*** Full on seduction ***

Six months into the open masturbation rule. I remember arriving home after the first day attending University. I was attending the same university my Aunt was a professor. I heard her shout to me from the living room. I used my crutches to enter the room. I spotted her laying on the couch wearing a very tight v-neck yellow dress. I immediately recognized the dress. It was on a model in a women's magazine. A model I often masturbated too. When I finished Sherry asked me why I liked the model. I told her I liked the tight dress, the model reminded me of a friend of hers, and I liked the nylons the model wore. Thinking back on it, this friend and my Aunt were both; petite, had larger breasts, were outgoing, were artistic, had long brunette hair, and were in their early thirties. After this my Aunt became jealous of this friend and they had a falling out. There was no way my Aunt would let anyone know she was jealous of anything. This yellow dress stuck to her body. It highlighted her very large breasts and it hugged her hips. I loved how how her short irresistible legs were wearing nylons.

When she spotted me she smiled and asked, "You like what you see?"

I was tongued tied.

She purposely played with her tongue,"Cat got your tongue?"

I stared at her.

She asked, "Am I as attractive as Ms. Sass?"

This was a teacher I often mentioned. I nodded my head.

"Am I as pretty as the women in the magazines?"

I nodded my head.

"Do I look better than the women in those catalogs?"

I meekly said, "Yes."

She looked hurt and said, "You don't sound to sure. I guess I'm getting old."

I quickly answered, "Your beautiful. My friends think your hot."

"They do?"

She asked in sly voice, "How does that make you feel?"

"I don't like it."

"That's wonderful. Your the type of man who will be loyal to a woman. Women like that."

She seductively sat up.

"When you masturbate do you think of me?"

I blushed.

She stood up and said, "I think of you when I touch myself."

She stepped up to me and gently kissed me on the lips. I pulled away.

She became assertive and asked, "Why don't you like me kissing you? You must not love me? After all this time? Maybe if you weren't a virgin you'd have more confidence."

I blushed.

"It's okay. It's not your fault women your age don't see you the way I do. There isn't any reason to feel nervous. Fate brought us together. Fate has allowed me the privilege to watch over you. You've been through so much. It's a shame you don't know what it feels like to be with a woman. I want to make love to you."

She paused.

She asked, "You love me don't you?"

I honestly did love her. I just never thought this meant I'd have an erotic relationship with my Aunt. I felt terribly guilty for my desires. Since living with my Aunt I often fantasied about being seduced by an older woman. I often fantasized about my teachers. I'd dream of having sex with my nurses. I had the vision of seducing my physical therapist. I wanted my first time to be with an older woman. I was ill prepared for this to be my Aunt. It wasn't until I was older struggling with the consequences of this did I realize my Aunt had prepared me for this moment.

Still stern, "It's different when an older woman teaches a younger man. I'm going to teach you how to make love to a woman. I know you want to treat a women well?"

I nodded my head.

"Do you love me?"

I answered, "Yeah."

"Why fret?"

She again stepped up to me and kissed me.

She reached down and in a seductive voice said, "See you like it."

I did but then I didn't. I felt just as much shame as I was excited. She was my guardian. I knew my parents would have never approved. But they were no longer alive. I knew my Aunts and Uncles would have freaked out but they were not involved in my day to day life. She gently took my crutches and set them on the floor. She held me up and led me to a chair she had set out in the living room. This reminded me of the first few months after the accident. She stepped away and started the CD player. It played an odd dance song with a heavy beat. While the music played she started to seductively dance. She slipped the dress passed her large breasts. I'll never forget the light purple bra she wore. I was transfixed on her breasts. I wanted to turn away but it was impossible for me to do so. While the song played she slipped the yellow dress below her panties and she stepped out of the dress. She was standing in front of me in a brand new purple colored feminine looking bra and pantie set. Over her panties she was wearing see through nylons.

I suddenly felt guilty. This was wrong. She was my aunt. She had been my guardian. This didn't feel right. I wanted to reach down and grab my crutches and tell her to stop. I didn't because I would have felt horrible if I disappointed her. I didn't want her to think I didn't love her. Truth be told I was tired of being a virgin. I wanted to suggest a few of my Aunt's friends I would have slept with. Then again, if I mentioned any of them, or they should me interest; they would have never been invited back to the house.

She casually stepped over to me, bent down, and whispered in my ear. She told me how attractive I was. How she had imagined this day. Because we loved one another every thing we were about to do was all right. She whispered it was natural for a man to be attracted to a more mature woman. She told me how she wanted to make love to me because I deserved to become a man. She said women my age were foolish to ignore me. She told me she adored my cock. This gave me confidence because I was smaller. Based upon the showers I took at school (there was a modified gym class I took my senior year) and at the Y; more guys were larger than me than smaller than me. There were guys at school who were teased for having smaller cocks than me. There was no way a girl would specifically choose me because of the size of my cock.

*** Doubt and crossing boundaries ***

In my mind I wondered if I should be having these feelings. She seductively started to dance to the music. I was memorized. I loved seeing my Aunt in the lingerie two piece and it was exciting to see her in nylons. Temporarily I buried the guilt I was feeling. She suddenly leaned down and passionately kissed me. I wanted to pull back but I found myself kissing her back. I felt guilty because I embraced the feeling of her lips. She responded with small moans of pleasure. She gave me instructions on how to gently kiss a woman. I pulled back when she placed her tongue in my mouth.

She chuckled, "I guess you aren't ready for that."

I was unsure I was ready for any of this.

This is when: she slowly unbuttoned my shirt and removed it, she unbuckled my belt, she unzipped my pants, undid the button, carefully slipped off my pants, and she slipped off my underwear. She commented on how much she liked my cock. She told me no matter what its size it I should be confident. She went behind me and whispered in my ear. Before she moved into the house she had been with big cocks, small cocks, and average sized cocks. She reassured me both small and large cocks had their pluses and minuses. She mentioned how one of her favorite male lovers had a small cock because he was an attentive lover. She made sure to tell me how much she loved his tongue.