So much has happened in the last week that to try and blog about it right now is too much. Don't worry! I am fine and happy as are Jenny and Heather but our lives have changed a great deal in the last 24 hours so I just wanted to write about a fond memory...well, until the end of it.
My mother, bless her heart, didn't trust me to be alone in the house when my parents would go out for the evening. To tell the truth, I played it up some because I really had a crush on my babysitter, Karen. She'd babysat me from when she was 16 and I was 8 up until she was now 18 and getting ready to go to college. I was 10 and never thought of girls as "icky" so her long, light brown hair and emerald green eyes entranced me. She knew this as I told her often of my undying love and was very kind. She'd hug me hello but kiss me goodnight just like my mom would when she'd tuck me in.
She was always a very appropriate girl in what she wore except for wearing tight jeans usually but never showed too much skin or cleavage...much to my bitter disappointment. I never knew of any boyfriends she had but being 10 might mean I was out of the loop. She was very pretty to me and had freckles on her cheeks and dimples when she smiled. She also liked to spank little boys on their bare bottoms until they were very, very sorry.
I remember the first time she came over. I was always required to go around with Mom and the Sitter, the first time she ever came, to hear the rules. Mom would then tell every Sitter the same thing: "We believe in being very firm in our discipline. If Jesse gets in anyway out of line, feel free to up-end him and tan his behind. He understands that quite well, don't you, Jesse?" This is the part where I would blush, always, cast my eyes down and say, "Yes, Ma'am."
Early conditioning? Could've been...but anyway, it was a little different when Karen came. She perked up at that last part and smiled widely. When I was done with my acknowledgment, she lifted up my chin and smiled sweetly, "I will have no problem taking Jesse in hand, Ma'am. I am a firm believer in good spankings for naughty boys. Do you understand me, Jesse?" I stammered and began to nod but remembered my manners before my Mom made me remember them, "Yes, Ma'am."
"Oh, I am not married yet, Jesse. I am a Miss." She waited.
Oh. "Yes, Miss." I obliged and saw her carefully wink at me with the eye away from my mother. I knew then that this was a match made in Heaven. My Mom thought so too and never got another babysitter for the next two and a half years.
We had a routine. She'd make me dinner then we would play games or watch television then it was promptly off to bed by 9:00 PM. I learned quickly she meant it when she said to finish my plate. My first night with her I left a vegetable. She warned me to eat it or else. I wanted to watch a show so I bolted. Karen came calmly into the living room, grabbed me by the ear, led me into the kitchen, sat down in the chair I had been in, and told me to drop my pants and underwear or she'd do it for me.
I was not comfortable with her doing it and only hesitated a minute before I did as told. She guided me over her lap and introduced me to her routine of punishment. She'd spank me until the tears started to come then stop and ask if I was sorry. I would tell her I was but it was never good enough. I always wondered how good it would have to be. She'd stop after a few more minutes of spanking and I would be more sorry than ever but not good enough. When I was a limp, rag of a sobbing boy over her knee, she'd say I was very, very sorry now. As a Sub, I would say she knew how to take me just past my submission point and then stop. I would assure her I was very, very sorry because I really was and would do anything to please her. She feed me my vegetable between quieting sobs while still in position. She let me up off her knees and, as would always be the case, cuddled me and praised me for taking my punishment like a good boy should. I was in love.
She spanked well enough that I never wanted to be spanked more than once in a night. My mother even commented on how better behaved I was around home and how I always cleaned my plate. She asked if it had something to do with Karen. I remember mumbling something about it might be. She called Karen and spoke to her and her mother about how good she was for me. She made me thank her, too. Karen just giggled and my face felt very hot and sweaty. She replied I was a good boy at heart but needed some firm reminding of it once in a while.
In all the time she took care of me, she was never, ever angry at me. I was even brave enough to spank her on the bottom one night as we were putting away toys and things in my room. She was bent over just perfectly. I couldn't resist even if it meant a second spanking for the night. She turned her head at me and smiled widely. "Did you enjoy that?"
"Yes, Miss." I was taught to always refer to her this way.
She came over and hugged me. "You're too young to be spanking 17 year old bottoms, young man, just be patient." She didn't spank me but just kissed my head and made me feel all warm and liquidy inside. I would later recognize this as a sexual release or climax but was then too young to really experience it.
I will put in here the one night I will always remember, not because Karen was mean to me, but because of my little game backfired on me. I would always choose rule to break that got me the spanking I wanted but it was always a rule that had no evidence after it was over with; however, there was one night about a week from Halloween my parents went to an office party for my dad. It was a costume party. My mom went as a witch and my dad...I can't really remember.
Well, one of the hard, bedrock rules was I couldn't eat dry cereal in the living room because it would leave crumbs. My Mom was a neat freak. Soo...that was the rule I broke because I wanted to see if Karen would ever use something besides her hand. No, she didn't but she used a lot more wrist action and made me very, very, VERY sorry before spanking was over. She sent me to bed a half hour early, too and that stung almost worse than the spanking.
Little did I know, but fate decided I was going to be royally punished that night. I found out later that my dad spent most of the evening flirting with another witch whose costume was much smaller and more see-through than my mom's that was just a normal costume. She was fuming furious when she got home. Karen had not had time to clean up the crumbs but was sent home. I could hear her protesting that it wasn't all my fault. She could see what I had coming in my Mom's eyes and got rather teary-eyed protesting for my sake. It made me feel very good...until my mom came into my room.
I was taken into the kitchen, bent over the table, she dropped my jammies and underwear. She then used something she never had before: the flyswatter. It wasn't one of those plastic ones...this was back when they used a wire frame with a big, rubber pad for the swatting. She stood directly behind me and whipped left to right, right to left, with no mercy. My bottom was already a little sore still and this...I had never been whipped in my life before. I bellowed, begged, pleaded, promised everything. She never stopped. She went from the top of my bottom to the middle of my thighs. I was hopping and squealing until I just hung on to the table a sobbed like a little, lost lamb. When all I could do was sob, she then sent me to bed without my jammies or underwear. I cried myself to sleep on my stomach.
She came in and woke me a later as she stroked my hair and apologized for being so harsh but I knew better. "Yes, Maa...amm." I sniffled. She then did something she had never done before, she started to rub some very cold, first-aid cream all over my bottom and legs. It felt soooo good. She commented on seeing some of Karen's handiwork. I told her it was. She praised her for being so firm and also for trying to defend "her little boy." She then promised to never whip me in anger before but learned that she'd use the swatter again when I really needed it. She did, too, and I think that is one of the reasons I am so frightened of being switched. I thanked her and drifted off to sleep with her still softly rubbing the ointment into me. She left me bare to the open air that night. I was tender for a few days afterwards but it was ten times better than it would have been without her administrations.
The best part? Karen called me the next day to see how I was. I told her what had happened. She cried. Really! I could hear her sniffles on the phone. She told me she was so sorry for not cleaning up afterwards and part of the punishment should have come to her. I must admit I grinned at the picture of Karen being whipped with the flyswatter. I didn't say it though. I thanked her very much for caring so much about me. She told me I was silly and she loved me. I knew it was a "mom" sort of love but I didn't care. I told her I loved her, too.
She invited me to her wedding when I was twelve. She hadn't been my Sitter for over a year by then but she asked if I was being a good boy. I grinned and told her I was when I was firmly reminded to be. I kind of wanted her to take me to some room and spank me one last time. She hugged and kissed me on the lips! I was so elated that I warned her husband that he had better take good care of her or he'd answer to me. He was a bit taken-a-back but handled it well and didn't make me feel stupid. I saw a tear of pride in Karen's eye when I walked away. Yup, that was my Babysitter, Karen.
