After reading, 'Spanking with Karen', I realized my own experience might not be so strange after all!
My parents used to send us kids to Grandma's and Grandpa's during the summer. I used to think it was because it was fun for us, but now I suspect, it was to get a break from us!
One year, when I was 14, we couldn't go to Grandma's and Grandpa's so we split up; my sisters going to one Aunt & Uncle and I going to Aunt Keri's.
Aunt Keri was 31 the summer I went to stay with her and was a widow who lived alone. She was very pretty and I was totally enamoured by her. We had fun at night but she was at work all day and I thought I would die from boredom after the first week...and I still had five weeks to go!
Then things got interesting. One night, I woke around midnight and couldn't go back to sleep. I slipped out of my room and headed toward the kitchen. I helped myself to some cookies and decided to try to peek in her bedroom. I tip-toed to the door, which was partially open, and her light was still on. When I peered through the crack, I saw what was to be stamped on my mind for the rest of my life. She was naked, spread eagle on the bed, her hand moving furiously over her pussy and with her face buried in a pillow to stifle her moaning.
Instantly, I had a full hard-on and I watched in fascination for what seemed like an hour. I had already become somewhat proficient in auto-erotic stimulation and slipped my hand into my pajamas. Five seconds later, I had a big wet spot in the front. When she finished, I slowly crept back to my room and masterbated again. I threw the pj bottoms in the laundry.
The next few nights, I would lie awake, then creep to her door for an encore, and finally, I lucked out. This time, she was on all fours working a vibrator in and out with her ass and pussy in plain view. I instantly got hard and began masterbating, but didn't realize that my pajama bottoms had fallen to the floor. When I came, I shot right through the crack of the door and onto the floor in the middle of her room! The floor was wood so the little puddles glistened in plain view! Horrified, I picked up the pjs and snuck back to my room. I waited in the dark, wondering what might happen, but finally fell asleep.
The next morning, there was a note from Aunt Keri that read she had to leave early and would be home late. I went to her room to see what had become of the evidence and saw that it was cleaned up. I thought she must know what had happened, and I dreaded her coming home.
Finally, my boredom and foolish curiosity overrode my embarassment and found myself exploring the strange wonderment of an adult woman's bedroom.
I went in to snoop a few times that day and must have lost track of time. I kept retuning to the beckoning of her underwear drawer, running my hands through the shimmery silky panties and lace. I thought it would feel good on my penis and dropped my shorts. I started to rub the smooth panties all over my cock and balls (which felt especially good) and butt. I was lost for a moment in the feeling of the panties on my hard-on and was startled by my Aunt's cry of, 'Brian! What do you think youre doing?!'
I froze. I couldn't look at her. My erection quickly faded. She entered the room, yanked the panties out of my hands and said, 'Go to your room.'
I went to my room, having no idea what she was going to do. Within a few minutes, she came in and shut the door. Standing with her arms crossed, she demanded I look at her. She said, 'I found your cum all over my floor last night. And I found your cum soaked pajamas in the laundry. How many times have you spied on me?' Her face was flushed; she was embarrassed and furious.
I didn't answer, and she yelled, 'How many times?'
'Two!' I croaked.
She then gave me a speech about privacy and gave me a choice; either she punish me herself or she would call my mom, send me home the next day, and have my mom punish me. I couldn't imagine what my mom would do. I didn't want her to know what happened, so I chose to be punished by Aunt Keri.
She said, 'Wait here'. She left, and when she returned had changed out of the business suit she wore to work into a short black satin nightie. I was too confused to be aroused by it, and she asked, 'Your mother doesn't spank you, does she?'
I said, 'No!' suddenly scared.
She said, 'Well, she should, and I'm going to...now get undressed!'
She sat on the bed and when I was naked she said, 'Get over my knee.'
I got over her knee and started to get aroused by the silky fabric of her nightie. She started to lightly rub my butt in fast little circles. As my skin warmed, I felt my penis getting hard, and wondered how she would react. She reached around and grabbed it, and said, 'You won't be hard for long.' Then she said 'Your punishment is going to last the rest of your stay. I am going to spank you whenever I think you need it; you are going to obey me, and you are absolutely forbidden to masterbate unless I tell you to. Do you understand?' I didn't really, but I said, 'Yes'.
Then she started to spank me. At first it wasn't too hard and I thought it wasn't going to hurt, but she had just gotten started. She spanked me harder and harder, pausing a few times to lightly stroke my butt and legs and back, before spanking me again. Soon my butt was bright red and stinging terribly, and I was crying like a baby. When she was done, she told me to stand in the middle of the room with my hands on my head. She left, and after a long time came back with a feather duster. She lightly stroked my whole body with the duster, paying special attention to my cock and balls, and soon I was very hard. She stood in front of me and said, 'You got to watch me, now I get to watch you.'
I was shocked, and I didn't react. She said, 'Go on, get started.' I reached down and started to masturbate, my face bright red from embarrassment, and Aunt Keri watching with a weird satisfied look on her face. I was very close to cumming and she said, 'Stop.' I didn't want to; I was going to cum, so she grabbed my hand and pulled it off my cock. She looked at me and said, 'I thought you were going to obey me. Put your hands on your head.' I did, and she grabbed the base of my cock and my balls in one hand and started to spank me again with the other. I lost my erection and when she was done spanking me, she played with me until I was hard again.
She said, 'Ok, let me watch you again. When I say stop, put your hands on your head.' I started again, and just before I came she said, 'Stop!' She did this at least five times until I was aching to cum. She took the hem of her nighty and rubbed it lightly on my genitals. She looked me in the eye and said, 'You are not allowed to cum tonite. And you better not let me catch you masterbating, or you will be sorry. Don't try to lie to me, because I always can tell when someone's lying. Now go to bed!' She left, my cock still hard, but I didnt dare touch it.
The next morning was Saturday, so she didn't go to work. When I came out of my room, she was cheerful and smiling; still wearing her nightie. For the next two days, she teased me incessantly, wearing very sexy clothes, 'accidentally' letting me see her naked after a shower, wearing sexy lingere at night, and watching me masturbate but not letting me cum.
She went to work Monday, and when she returned home that night, she looked me in the eye and asked if I had masturbated while she was gone. I said, 'No', and she said, 'I will let you cum tonite but you must be spanked.' I agreed, and after dinner, she told me to go to my room and get undressed.
I undressed and when she finally came into my room, she was wearing a tiny bikini panty and a bra. She stood in front of me, reached around and grabbed my butt. She said, 'Put your arms around my neck!' As we embraced, she started to spank me and our bodies rubbing together and her grunting in my ear when she spanked me got me extremely excited!
I got a huge erection, but my butt was stinging from the spanking I was getting, and I eventually went limp. When she was done, she reached down and played with me until I was hard again. Then she stepped back and said, 'Ok, you can jerk off now.'
I started to stroke my cock as fast as I could and was soon moaning, which freaked me out cuz I never moaned like that before. It must have turned her on, because she put her hand in her panties and began masturbating, too! She turned me around to face the bed and she laid down, pulling off her panties. We watched each other masturbate until I shot three long streams of cum on her.
For the rest of my stay, she tried various forms of teasing and spanking, (maybe I should do installments!) and the next summer I begged my mom to let me go back to Aunt Keri's. She agreed, and I spent another six weeks with her. After that, she met some guy and remarried, and we have never mentioned it since, although sometimes when I see her, I get a wink and a knowing smile!