Aunt Sherry Takes It

In one way this made me feel better. In another I wondered if she wanted me to give her oral sex. This was request made me nervous. I was never with a woman before and I certainly didn't know how to give a woman oral. I believed I would have disappointed her. The least thing I wanted was to disappoint my Aunt Sherry. I wanted to prove I was a man.

She very gently lifted me up. We walked together to a living room love seat. It felt like the times she would assist me when I first moved back home. After sitting me down she pressed her breasts together teasing me. I suddenly felt guilty. I didn't want to have sex with my Aunt. I felt the way to escape this was by jacking off.

She became angry when I reached for it.

She snipped, "This isn't the time for that."

I was unsure of what to do.

She stepped up to me and gently touched me face.

She whispered, "We are a special family. You are my special nephew. We have a family others would be jealous off. We should consider ourselves silent passionate lovers."

In my mind I questioned if an Aunt and Nephew should be lovers. We were crossing boundaries I felt were wrong to cross. I did love her. She was so beautiful. I adored her bra and pantie set. She was wearing nylons. I often imagined sneaking into the laundry room and exploring her intimates. I never did because I knew she would be disappointed in me. I never wanted to cause my Aunt any trouble. She was sacrificing so much for me. The least thing I wanted was for her to think I didn't love her.

She laid down on the couch. The love seat was in a direct line of sight of the couch.

She gave me a seductive look, "Have you imagined me in lingerie? I know you have a thing for lingerie."

I tried to look away but she forcefully told me to look at her.

"I nodded my head."

She asked, "I bet you like me in these nylons. I love it when you glance at my petite legs."

I nodded my head.

"Isn't this better than those fake women in those magazines? Or in those catalogs? I'm a real woman. I know I'm better than those immature college girls at your school."

I looked at her.

"Or some of my friends who you stare at."

I blushed.

"Look at that."

She winked at me.

"Look at it stand at attention. See. You like it too. I felt this was the day.

She teased me by asking me if I liked a pose or not. It was as if I was a photographer and she was a model. Then she teasingly sat sideways at end of the couch and placed the right side of her body on the arm of the couch. IShe pulled down one of her bra straps.

"Should I remove this?"

I wanted to see but then I didn't.

"Look at your throbbing cock. See you want this just as much as I do."

I was unsure about all of this. But it was true it was at attention.

As she sat up she slipped her bra down. For the first time in my life I saw the tops of a real woman's nipples.

My cock throbbed.

"Remember what I taught you. You need to have control." She winked, "But this is the first time you've ever seen a real woman nude. I guess it shows how attractive I am."

If I was able to run I would have ran to my room locked the door and jacked off. Then again I could have told her no.

She gave me a look, "Don't touch it until I say. If you jerk it now it will ruin it for us."

She turned and knelt on the couch. I could see her rear end. I adored her beautiful purple panties. She reached behind and undid her bra. She let it fall. She turned slightly so I could see the side of her breasts. I loved how large they were and I could see her nipple pointing to the wall.

My cock throbbed. I was trying to have control. She told me a good man has control. She seductively turned to face me. Still kneeling on the couch she teased me by dropping her bra. My Aunt was topless. She knelt there letting me study them. I was feeling waves of guilt. I shouldn't have these desires but she was so beautiful. The real thing was in front of me. She started to play with her nipples. I watched her nipples harden. She rolled her tongue on her lips. Out of excitement, nerves, guilt, anticipation, and a thousand other conflicting emotions. I shot all over the my chest and onto the chair.

With a mix of emotions and I started to cry.

I started to say, "I made a mess."

She quickly jumped off the couch and aggressively rushed me, "A real man doesn't cry over this. You need to learn control!"

She grabbed my face.

"This is the first time you've ever seen a real woman. This happens. But don't be some sort of pussy. Be a man."

"Your my Aunt?"

Soft but stern said, "Yes. But we are passionate lovers too. You want it just as much as I do."

She took my hand and placed them on her breasts, "You like how this feels?"

I was afraid to caress them.

Like she did with other things she placed her hand over my hand and we caressed her breasts.

She smiled, "Lets go to my room."

"What about the mess?"

She touched my chin, "You will one day make a wife so happy."

She went into the bathroom grabbed cleaning supplies, soap, and paper towels. She first made me clean off my chest. She helped me up. By leaning on the chair I helped clean off the chair.

*** Entering Her Room ***

After she led me to the elevator. We went up to the third floor and to her master bedroom. It once was my parents room. I felt guilty when she opened the door. I resisted.

While supporting my waist and leaning up against my body she whispered, "This is my room now."

She kissed me. I found myself kissing her back. She gently led me into her room. There she laid me down on the bed. She seductively removed her nylons and her panties. She was telling me how wonderful I was. How I would one day make a great husband. She told me how she was glad she moved in with me. How we were a special family. How all of the sacrifices she made were worth it. How I gave her purpose.

She took my hand and again placed them on her breasts.

"It would mean so much to me if you touched them."

I fumbled for a bit.

Sternly she said, "Be gentle. Start on the outside and work your way in. Tease my nipples. If you feel up to it lick them. I guarantee a wife will like it."

I did as I was instructed. She moaned and her breasts became erect. She laid down next to me and spread her legs.

She instructed, "Don't be in a rush. Women need to be prepped. I need you to touch me. If you are ready you could use your tongue."

I was unsure of what to do. She sat up took my hand and led it down to her spot. While looking at me she named her female parts. She placed my fingers on what she called her button.

She whispered, "Twirl it."

I looked at her awkward. Everything was so overwhelming to me. I wanted to please her. Wanted her to find me special. I wanted to be a man.

"I should have let you watch me. Make round circles."

She showed me.

I felt her get wet. Her sent filled the room. I was again hard. My mind was telling me I should leave. I should move out of the house. Tell someone what she was doing. Yet, I wanted to put my cock into her.

"We are a special family. I'm making you into a man. It's a privilege for me to do so. I hope you know that."

She said in between her panting, "You can't tell anyone about this. They would wreck our family. You don't want that?"

I shook my head. I didn't want to loose another family.

She panted.

I was feeling a woman's pussy for the first time. The conflicting thought was it's my Aunt's pussy. I questioned if this was a good idea. She was moaning because of what I was doing. I felt guilty I was the one causing it.

She said in a seductive voice, "I've been imagining this for a long time."

She let out a shout. She shook, shivered, made frightening noises, and convulsed.

I thought I hurt her.

I panicked, "I better call an ambulance."

She stopped me from grabbing the phone next to her bed, "Sweetie. It's how a woman orgasms. You did great."

"What?"

"You were wonderful."

She reached up and kissed me. We cuddled for a while.

I tried to look around the bedroom but she would grab my face and say, "Look at me."

I listened.

In a serious whisper she said, "You were wonderful but you are not a man yet."

I nodded.

She asked, "You know what a condom is?"

"It was in the book you gave me."

She smiled, "Oh yeah. I'll show you how one works for real."

She reached over and opened the drawer of her night stand. She took out a brand new box of condoms. She gave me one and she took one. She took out a dildo from the same night stand and used it to show me how to put one on. I knew what this meant. I was so nervous I never asked about the dildo. When she tried to put one on me I went limp.

"Oops. We can't have that."

I was surprised when wrapped her mouth around my cock. It felt amazing. Once I was at attention. She slipped the condom on me and quickly mounted me. This stopped me from questing if we should continue.

She started to aggressively rock back and forth. I watched her boobs bounce. She placed her hands on the head board. Even with the condom on this was the most amazing thing I ever felt. She kept rocking back and forth. I was so hard. I was surprised when she took her hand and aggressively attacked her button.

She screamed, "HOLD IT!"

I tried. I really tried. I didn't want to disappoint my Aunt Sherry.

It felt amazing. I was seeing her boobs move back and forth. She even allowed me to touch them. I could see her body become flush. She was becoming more aggressive touching her button.

Her voice frightened me, "HOLD IT!"

I tried.

I just about lost consciences when I filled the condom.

Just when I started she made the most frustrating noise.

I barely heard it.

Angry she said, "You need to do better!"

I was crushed.

She lifted herself off me, she yanked the condom off, grabbed tissues next to the bed, she threw me a few, mumbling, she stepped into the bathroom, mumbled in the bathroom, I assume chucked the condom into the a garbage can, mumbled some more, and started to wash her hands.

I started to sit up. My goal was to get my crutches and leave.

She quickly turned, jumped in front of me, pointed, and demanded in a stern tone, "Don't you leave!"

I shook. I felt so terrible. I let her down. I disappointed her. I was a disappointing man. I couldn't please a woman. I came to fast. I just couldn't hold it.

She hugged me.

She looked into my eyes, "You are a man now."

Meekly, "I am."

"Because of what I'm teaching you. You will make a woman very happy."

*** Again; reluctantly ***

She laid down next to me and we intertwined. She caressed my hair, gently touched my skin, and was telling me how lucky she was to have a nephew like me. At some point she reached down and touched me. I didn't want to do it again. I was worried I would let her down for a second time. I wanted to take a shower. Read a book. I wanted everything to go back to the way it was before. But this was impossible. We crossed boundaries we weren't suppose too.

I wanted to please my Aunt. She was my guardian but I had always wanted to be the man of the house. After all she was helping me. She was teaching me how to treat a woman. Like she said I must have liked it. This was much better than jacking off.

She slipped another condom on me. I was trying to avoid the dark feelings that seemed to be surrounding me. She was over me. She separated my legs, she closed her legs, she secured her feet on top of my legs, and slid herself onto my cock. Her pussy now felt tight on my cock. She started by slowly grinding her body. She started to whisper in my ear sexual things. I was shocked my Aunt would say these things. She was being slower and more sensual than the first time. She was telling me how I was helping her feel like a woman. She shifted her pelvis and made an awful noise. She said I was hitting her spot. I could feel her wetness and the room filled with an odd smell. I loved how it felt as she was slowly grinding. An added bonus was how her breasts were shifting on my chest. She then kissed me. This lasted only for a few moments. She screamed again,.She started to move faster and all at once she shook, panted, and shuddered. She collapsed on top of me. She mumbled something about all her planning was worth it. I was still rock hard. I didn't know what to do. She noticed how stiff I was. She told me to wait a second. She removed the condom and wrapped it in tissue. She again threw me some tissues. She took the condom into the bathroom. I looked at my wiped off hard cock. I wanted to just jack it off. I knew this would anger her. She stepped out of the bathroom holding onto an old towel. She approached the bed. She opened a drawer of her nightstand, took out some lube, rubbed it on my cock; it felt so hot. She wrapped her hand around my cock and twisted and turned it. She took her other hand and played with my head. Soon I was squirting all over her hands and my chest. She handed me the towel and stepped into the bathroom.

I waited for her.

*** Aftermath ***

We ended up taking a bath together. Nothing overtly sexual happened. She was playful. She pored me a glass of wine on account I was a man now.

After the bath we drove to a local grocery store where we rented a movie and bought a couple frozen pizza's. With how frugal and health conscious she was this was a treat. While watching the movie we cuddled on the couch.

I was unable to articulate it but I wanted to reach out and fix all of the boundaries we broke. I was unable to touch them; much less fix them. I knew we would never be the same. I would never be the same.

I felt guilty for wanting it again.