Tom was 16 when his parents told him they were going on a 10 day summer cruise. His joy was quickly dampened when they also announced he would be minded by Sandi, a neighbour's daughter from down the street.
Sandi was six years older than Tom and had just returned from college. She was about 5’ 10" with dark hair and a killer body that had been toned by two years on her college rowing team. She had grown up in a strict home where corporal punishment was not spared and she in fact had helped raised her younger brother. On numerous occasions she had administered a bare bottom OTK spanking or used her Dad’s strap when the offense was more serious. ______________
Sandi baby sat me a number of before she went to college before and I had a huge crush on her. Although my parents had often told her she could spank me if I acted up she had never done more that give me a smack on my pajama clad bottom.
Sandi had moved into our house for the 10 days and I was in my room where I was supposed to be working on a summer term paper. She appeared at my door wearing a white bikini which hugged her body and displayed her perfect tits and ass. Breathtaking.
“Tom” she said as she leaned against the door frame. “I am going to tan by the pool for a bit. Put a dent in that term paper or I will dent your butt. As far as I am concerned I still have permission to spank you.” She chuckled and walked down the hall. My heart raced as I imagined being spanked by Sandi and by cock started to swell.
I has recently purchased a new SLR with a zoom lens and rushed to my parents room which overlooked the pool. I hid behind the curtain and stared out the window at the most incredible sight I had ever seen. Sandi lay on one of the lounge chairs reading a magazine. She was way better that a 10.
I poked the lens from behind the curtain and zoomed in on her breasts and pressed the shutter. The high speed motor drive took 4 pictures in a little over a second. I quickly moved the zoom to the small triangle piece of swimsuit covering her snatch and once again pressed he shutter. I saw Sandi start to lower her magazine and I ducked behind the curtain once again. I feared she may have heard the motor drive and I rushed back to my room.
About 10 minutes later Sandi opened my door. “How’s it going Tom?” she asked as she strolled into my room and over to my desk.
Sandi walked over to me and stared at the computer screen. “Does not look like you have made any progress on your paper.” Before I could answer she continued “Nice camera, it’s the same one my boyfriend has,” she said as she picked it up. I froze as she turned it on and pressed the picture preview button.
“Nice pictures creep” Sandi said, “Tom, I know what a motor drive sounds like. What the hell did you think you were doing?”
“I’m sorry Sandi” I whimpered “You’re so beautiful and I just wanted a few pictures”
“Nice try Tom, a full body picture would have been one thing but you zoomed in on my tits and pussy. That’s disgusting. You obviously have no respect for privacy. I am going to call you parents..or”
“NOOOO. Please don’t. What’s the or?”
“I know this is the first trip alone your parents have had in over five years and they should not have it ruined by your creepy actions. Do exactly what I say and accept my punishment and I won’t call them”
“If I tell your Dad, I know he will blister your butt. I intend to do the same.”
I could tell from her tone and body language that she was not about to change her mind.
“Ok. Just don’t tell my parents.”
“Tom, what does your Dad punish you with?”
“A Scottish tawse.”
“Go and get it.”
I went to my Dad’s office and returned a few minutes later with a tawse that had been in the family for multiple generations. It was made of heavy leather hide and was about 18” long including the handle , 2’ wide and ¼ inch thick. It had obviously see a lot of use. I handed it to Sandi who swished it in the air a number of times and said “This should work nicely.”
“How many strokes do you usually get with this?” Sandi asked
“If he’s really pissed, about 10,” I answered.
Sandi nodded as she answered “Well, your Dad is much stronger than I am, so I am going to start off with an over the knee spanking.”
She walked over and sat on the bed and gestured for me to come over. She lay the strap beside her and pulling me closer quickly unbuckled my shorts and pulled them down to my ankles. My ample cock sprang to life and made a tent in my underwear.
“Is that because of me?” Sandi asked, as she stared at the bulge. “ Normally, I would be flattered but lets see if he still feels that way in a few minutes.” She pulled down my underwear and had me leave them in a pile on the ground along with my shorts.
Sandi placed me across her lap and stared to deliver crisp spanks to my bottom. From the start I realized that this was not going to be a few love taps! She was an experienced spanker and she increased the tempo as she moved from check to check. I started to wiggle to which only caused her to spank harder and warned me to stay stay still. If Sandi had thought a hard spanking would cause me to loose my erection she was sadly mistaken. Being naked across the knee of a beautiful woman, with my cock inches from her pussy had a different effect and if anything my cock got harder. I lost count of how many spanks she had delivered at around forty and yet she kept up her pace and I was started to cry and beg her to stop.
Sandi stopped spanking and said “Your tiny little brain is obviously overly stimulated and the message of the spanking is not getting through to you.. get up.”
I slowly got up from her lap and tried to hide my erection with my hands. “Put your hands by you side.”
Grabbing my cock she led me into the bathroom and turned on the shower. Turning to face me she said “Get in and jerk off.”
“WHAT,” I yelled.
She was still holding onto me and she squeezed me hard causing me to cringe.
“I heard that naught boys like you feel a spanking more after being milked. We are going to test that theory. Get in the shower and jerk off, NOW,” Sandi exclaimed as she released my cock and gave me a hard swat on the ass.
I entered the shower stall and adjusted the water temperature. Grabbing the soap I lathered up my still erect cock and started to stroke its long shaft. I had been at it for less than a minute when she smiled said “I can tell you have done this before. Faster Tom, I don’t have all day.”
I increased the speed and it took about another minute before I felt my climax approaching. I squatted and exploded into the stream of warm water. I squeezed the last drops of cum from the now limp cock and washed him off again.
Sandi handed me a towel as I emerged from the stall and I quickly dried myself.
She led me back to the bedroom and picking up the tawse told me to bend over the bed.
“Put your hands on the bed, Tom. I want your ass nice and high and don’t even think about moving.”
Sandi stepped back and raising it brought it done hard on my already sore bottom.
CRACK. CRACK. “OMG - That really hurts,” I cried.
“That’s the intent, Tom,” Sandi said. “Are you learning from the experience?”
“Yes. Pleaseeee no more. ”
CRACK. CRACK. My knees buckled and I fell on the bed. “OWWWWW.”
“Back in position or I will add strokes. Five to go”
I was already sobbing as the next two landed and Sandi was not letting up. She used the tips of her fingers to inspect my bottom. “You are going to be sore for a few days. Three more Tom.”
The last three were delivered slowly but with no less intensity. Sandi dropped the strap on the bed and told me me to stand up. I struggled to do so and was now crying with tears streaming down my face. “I hope you learned a lesson about respect for privacy today,” Sandi said as she pulled me closer. Sandi hugged me for over a minute until my crying had slowed. She released me and looking down, noticed my cock was once again starting to swell.
Sandi looked up at me and smiled as she cupped my cock in her hand, “Maybe, he needs to be taught a lesson of a different type...”
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