Caught Skinny-Dipping

Too bad for you but I am still in a memoirs-type mood, I had intended this next memory to be in a list of the top five humiliating experiences in my life but I kind of ruined that when I told you about Teri the R.N. Did it sound too tame? You wait until you are getting your temperature taken that way every four hours with a few, well-places swats, being baby-powdered and forced to open your mouth for a baby pacifier while an extremely attractive woman coos about you like you are an infant, then tell me how humiliating it is...anyway. This one is in the top five...although it has a happy ending of sorts.

We got a swimming pool in our backyard around the time I turned 11 years old. It was great because we lived where it got very, very hot and it felt so good to jump into the pool and the water was sooo cold. Well, little pervert that I have always been, I soon learned the joys of skinny-dipping. I was very careful about it because I KNEW what would happen to my already naked behind if my mom ever caught me, that was part of the fun. I always waited until my parents were gone and no one was home but me. I'd make sure the front and side door were locked and then I was safe.

It was an early summer morning so the water was still icy cold. My mom was gone for at least an hour so I had time for a quick "dip." I always went out in my swimsuit and would dive in...then I would shuck the suit to the side of the pool. I had tried just letting it stay in the pool but if I ever had to make a quick change back into them it was harder to find them. I stripped my suit off and started to swim around. There is no sweeter feeling than having that water whoosh past your privates. I had a great time going underwater and splashing around. I figured I had about ten more minutes before I was taking too much of a chance so I was going back and forth under the water the whole length of the pool.

"Well, helllooo, Jesse."

My heart froze. I had just come up for air on the wrong side of the pool and there was my sister-in-law to be, Colette.

She was just plain hot at 19. She wore a bikini. She was the first "woman" I had ever been around while she was wearing a bikini. It had a daisy flower print. She was strawberry-blonde, green-eyes, and had a very nice body. She knew it but was always very sweet to me and my invariable crush on her. I'd seen her in the bikini, a tennis skirt, and tight jeans. She taught me a great deal...even besides this incident.

One my first afternoons with her by the pool, she had taught me the art of how to rub a woman's back. I could hardly breath for being so turned-on. Yes, lower back but not buttocks. She said I was very good at it and let me practice on her several times until my brother tattled to my mom and I got banned from the pool for two days. Neither my brother or I had mentioned the message lessons or I would have been spanked and then banned.

Anyway, there she was by the pool in her sandals and bikini. She was smiling wickedly as she made eyes at me in the pool. I had never felt so naked in my life up to then. I was going to dash to my suit but she stopped me with the words I will never forget. They were so classic!

"Looking for this?" She had already gotten my suit and was dangling in from her finger tips with her eyebrows arched.

I couldn't speak I was so embarrassed. I had forgot she had a key to come to the pool whenever she wanted. My mom was getting home any minute. "Puh-Pleeze...may I have my suit, Colette?"

She took my suit over by one of the pool chairs and laid it on the table. She bent over and undid her saltwater sandals and placed them to the right of the chair closest to the pool. "Don't you dare make a move until you have my permission." Without a word, she dove into the pool - where I was NAKED! I couldn't help it - I moved my hands to cover myself as she swam past to the deep-end and then with quick thrusts of her legs came back to the shallow end. She glanced over her shoulder to make sure I had obeyed and went up to the chair and sat down.

The water dripped from her skin as she moved her long hair out off her face and back over her shoulders. "Come here and get it, Jesse." Her eyes narrowed. Remember that look #2 (your seconds are numbered)? I was getting it but not my suit.

I made a decision. If I hurried up there then I would retain some dignity and hopefully have this over with before my mom came home and I really got it. With head hanging low, I came up out of the pool. I didn't even reach for my suit. I just stood on her right side. I knew she was right-handed because of seeing her play with that tight butt swaying under a little skirt. Why was I always ending up over the lap of a tennis player with their excellent backhands?!!

She lifted my chin. "What would your mother do to you if she'd caught you right now?"

My voice quivered. "Pretty much what I think you are going to do to me right now."

She caressed my face. "You know you deserve it, so lets get this over with."

And so I found myself being placed over the naked thighs of my hot sister-in-law-to-be. I knew my whole body was blushing. My only consolation was a spanking was a lot nicer than what my mom would have given to me. She lowered her left knee so I was properly displayed and I felt a very stinging and loud THWACK! HER SANDAL!

This was my first and not last taste of a saltwater sandal on my naked bottom. They sting like a thousand bees biting your rear end. I was a howling mess after only five or six swats. She was just warming up. She quickened the pace and soon had to hold my middle down with her left hand as I was bucking as I was sobbing how sorry I was. I was just about to break completely when she stared on my upper thighs. I would later realize she knew how well to do this from having four younger brothers. I just went limp and waited for her mercy as I whimpered, "I'm sorry, Miss!" over and over again. Karen's good teaching showing through.

It took me a few seconds to realize it was over with. I waited for her to let me up and once I was standing I made a move for my suit. My feelings of embarrassment were long "behind" me as I could feel the heat and throbbing from my much abused bottom. I was still sniffling as I almost reached the suit.

"Not so fast, Jesse, I am really sorry but I heard your mother get home."

I groaned and nearly fainted. Colette grabbed me by the arm and with suit in one hand and my arm and then ear in the other hand. My mother came into the backyard and took it all in at a heartbeat. "Thank you, Colette, for teaching Jesse some manners. I knew you were a good daughter-in-law. Would you be so kind as to bend him over the ping-pong table on the porch there? I need to put down my groceries and bring out the swatter."

I thought about fighting Colette on it but just meekly bent over the table. She did thoughtfully put a towel over the edge so I have something soft to rub against. I just kept crying as she softly said she was sorry but had no choice. I told her it was okay but I felt betrayed. She and I had a history. She should have just handed me the suit in the beginning. My poor 11 year old heart was breaking as well as my bottom was soon on fire.

Mom came out and inspected Colette's handiwork. She was impressed and I think my whipping was somewhat shortened from her original plan since I had been punished well already. Still, I was a howling, hopping, naughty boy with her left to right and back motion of the swatter. It really hurt on a very tender area plus there were parts of my thighs that were still virgin. It was probably only 30 seconds but it seemed an eternity. I was then led to my room and smacked on the butt into bed. I was grounded to my room except for potty breaks and I had to wait until someone took me there and back. I was allowed to put on my jammies but I didn't do that until much later in the evening.

My sort of happy ending? Well, much later that night after I got a dinner of water and crackers while everyone else was having bbq burgers outside. I could hear all the splashing and laughing. I heard my mother loudly telling what happened to me complete with kudos to Colette and her sandals. I was mortified all over again. My brother was loving it and asked Colette to tell it again but she refused. I went to sleep, crying softly into my pillow as I was laying down on my stomach and would be for 3-4 nights.

I was awakened much later by a loud yelling sound. It was 3AM! What was going on? It was something loud and angry...it was my mom! My butt clenched in automatic reaction which produced a groan from me as it was very sore. I got out of bed and started to go to the window but heard someone coming down the hall. It was my father. You may notice I don't tell any stories about him punishing me. With him there was only one answer: the belt. I was considered to young still to get the belt but my brother wasn't. My father was leading a my very wet brother down the hallway. My father was muttering, "You are not too old for this if you do things like that under my roof. Mother is taking care of your Colette. You worry about yourself." He took him into my parents bedroom.

I had a very tough decision. My room didn't face the pool but my brother's window had a great view of the pool area. If I got caught doing this...I couldn't even think about it but as the sounds a belt smacking into my brother came down the hall. I couldn't resist. I just couldn't. I scooted around to my brother's room and peeked out the window. It seems my brother and his fiance had decided to skinny-dip themselves. Somehow, my mother had caught them because there was Colette by the pool very naked and shivering but not with cold. My mother had the swatter in her hands.

She made Colette bend over and grab the edge of the table by the pool. She then made her part her legs so it was a V up to her bottom. Hot Colette, naked, wet, bent over...and about to get the whipping of a lifetime. My mother was ruthless. She covered ever inch of bare skin from the top of the buttocks to the top of the ankles. Colette tried to dance a bit but just got it worse for it. She cried, then she wailed, then she sobbed, and finally just begged for mercy. My father had let up before my mother did because I could hear them coming! I hid under my brother's bed but Dad took him past it and thrust him out the front door and locked it behind him. He'd thrown him out...without clothes. I went back to the window to see Mom leading a very sorry but still naked Colette by the window. Ooo, she wouldn't be sitting or playing tennis or wearing anything revealing for at least a week.

I ran back to my bed and just savored the scene over and over and over again. Colette asked me a year or so later if I had seen what happened. I smiled widely and nodded. She blushed. "I got what I deserved, too, didn't I?" She said with her head down. Without thinking, I blurted, "Yes, but I wish I had been the one to give to you." She'd blushed an even deeper scarlet and gasped. She looked up slowly with a small smile I didn't understand then. "I kind of wish you did, too, Jesse." Ever since then she would make excuses for me to smack her on the butt; as she went by or she'd bend over for something right in my line of fire and pause, or a number of things. It did great things for my sexual confidence. We were discrete about it...no one else ever knew. I sure never did it in front of my mom but I spent lots of time over at their house after they were married...when my brother was at work. Yeah, Colette was something else.

They ended up getting a divorce. My brother was not the attentive, loving type and she was rather needy in a passionate sort of way. I have no idea if she ever let him spank her or told him she enjoyed spanking and being spanked. She always spanked me for my birthday but never again on the bare. What was interesting to me was something my brother said after the divorce was all over with...he said, "It was the strangest thing. She seemed more worried about how disappointed you would be than anyone else in the family. She kept asking if she could see you."

I considered seeing her. I was over 18 then and debatably an adult but loyalty to my brother and parents kept me from it. I saw her again 5 years later. She'd remarried and seemed happy. We were in public so couldn't say much. I finally asked her if he treated her the way she wanted. She caught my attempt at subtlety and gave me a sad grin. "No, Jesse. No one has ever treated me that way for a long time." Her eyes left little misunderstanding. I felt sad for her but that's sometimes how fate deals it for us. I hope she finally got the spanking she wanted. I certainly have again and again.

*sigh*