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An Original Story By:
Take Those Panties Down
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Synopsis: Very Long story. Jennifer and her friend Linda get a paddling, and Jennifer gets her rectum pleasured by her friend.
(c) Copyright 2012
All Rights Reserved.
Tags: spanking, anal, first time, M/FF, F/F, sex, bisexual
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Jennifer's Birthday Paddling
Jennifer was really a sweet catch, and an older woman to boot. I had been working a Real Estate office for 2 years in sales, and she joined the company in May of 89'.
I immediately liked Jennifer a lot, not only because she was older but had a very sweet and kind air about her. I was 27 at the time, and Jennifer was a bit older than me (closer to 40 I guessed). I have always enjoyed the company of older women since my mid twenties. The have their acts together, know what they want, and are at their sexual peak.
The other thing I liked about her was that she was rather plain looking, but had a big heart. Most of the other sales guys I worked with were too busy screwing 20 year old coeds from the surrounding colleges, or swilling beer and generally lying about their conquests. They wouldn't have touched Jennifer with a ten foot pole, and that was fine by me.
Personally, I thought Jennifer was great. She was about 5'4 - slim figure, and beautiful wavy hair cascading over her shoulders. She never liked to wear makeup, and I think that's why she looked rather plain. However, looking plain myself - I figured we might get along famously, and we did! She also had the most smoldering green eyes I have ever seen, and they sometimes glinted with mischief when you would talk to her. She also likes to touch you when she spoke. Sometimes softly on the arm, or the hand.
Our courtship was a wonderful experience - intimate, romantic, and filled with expectation. She was absolutely a great lover, and could get me up and running sometimes four or five times in one night. During that summer, we had gotten into some light spanking during our lovemaking sessions. Nothing too serious, 20 or 30 light swats to warm her bottom and then a long night of lovemaking. She was always alluding to getting spanked, and would find all sorts of ways to work it into the conversation.
After a while, we tried to get the spanking routine into almost every Saturday's lovemaking. Jennifer has a strong will (stubborn), so even then I found that the spankings were more her idea than mine, with her asking for it, and me responding...
This was soon to change....
We'd been together for about nine months, and I realized Jennifer's Birthday was less than a week away. One night on the phone, I started asking her what she'd like. It was to be her fortieth birthday (a biggie as they say), and I really wanted to treat her to something special. A nice dinner, some presents, a hug and a kiss, whatever she wanted...
"So Jen, what would you like for your B-day?"... This was after ten minutes of prying and prodding.
"Well, what can you get for the woman who has everything?"
I joking said (knowing she'd like this), "How about a Birthday spanking you'll never forget?"
She paused for a moment...there was silence on the line.
"That sounds wonderful...I want a birthday spanking like I've never had, I want my ass so red and stinging I can't sit down for a week".
I laughed.
"Are you really serious?"
"Yes sweetie, this time instead of those mild spankings you always give me in bed, I want a real spanking. A spanking for a woman, not a girl - something that will really mark my fortieth birthday".
I thought this was great, but I had to view it with a certain amount of skepticism. Jennifer liked lovemaking like no other woman I've known, but she had a tender heart. And for that reason, I really never let her have a good one. I always kept them mild, a nice mixture between pleasure and pain as a good lover would.
"Are you serious Jen?"
"As a Church Warden!" she replied.
"OK, enough said".... I took a moment here to collect my thoughts...
"On Saturday night, I am going to give you a spanking you will never forget ".
My boldness quickened....
"I am going to sting your ass like you've never felt before, and take you to new heights. Don't ask me what's going to happen, just think about it. Think about how it's going to feel sweetie. You want a real birthday swatting; you are going to get one. If you want to back out now, this is your chance... once you say yes, that's it, No turning back".
My voice had grown hoarse. There was silence on the other end of the line... Then:
"Yes. I want my Birthday ass swatted. Hard!"
I boldly added..."OK, no masturbating until Saturday is that understood? You aren't to touch yourself for the next four days...You are to remain pristine and virtuous until then" I added...
"All right"... Jennifer's voice was more timid than I had ever heard it before. She was enjoying this, and I was aiming to please her.
We hung up.
Since Jennifer's birthday was the following Saturday, (just 4 days away) I figured I had better get things prepared. Wednesday night after work, I went to a local lumber yard, and started casting around for the right materials. I wanted to fashion a truly unique and deadly paddle to warm her ass with. I wanted something light, not one of those paddles you see in frat houses. Those were too coarse and blunt for my Jennifer's bottom. I wanted to hand craft and sculpt a weapon that could sting her ass most delicately and precisely - something hand built that would last for many a good spanking to come.
A scalpel for ass blistering, as it were....
After looking at all sorts of planks and larger boards, I finally spied a bin of "leftovers". These were pieces of board that had been cut from larger sheets and planks and then tossed aside as scrap. Sticking out from the top of this barrel of discards was the piece I had been looking for. A thin strip of paneling about 2 feet long, and seven inches wide was there for the taking. It was made of cedar, a quarter of an inch thick (thinner than a ping-pong paddle), and perfectly unblemished on both sides. This handy scrap cost less than a dollar, and I was on my way home.
I spent the next 2 nights down in my woodshop fashioning a tool to warm Jennifer's ass. Sometimes it was difficult to concentrate with my cock springing to stiffness at what was to come - but I would shake these thoughts from my mind and concentrate at the task that was at hand. I had shortened the thin piece of board down to a little over a foot long, narrowed it a by an inch, and had formed the whole affair into a rather nice teardrop shape. It reminded me of one of those paddleball toys I had owned as a kid, you know - the kind with the elastic string and the rubber ball. After cutting the basic shape, I had rounded off the sharp edges with a sander, and then finally hand sanded it with finer and finer grades of paper. By the end, I had a perfect paddle, and the wood was as smooth as a baby's skin.
I then carefully painted a nice red heart in the middle of the paddle, with the word "Jennifer" emblazoned across it in light blue. Perfect. Two coats of shellac, with sanding in between...and time to let it dry. By Thursday night, I had the supreme paddle. It was very light, and could be wielded quickly and with precision to the exact spots I wanted on Jennifer's backside.
After work on Friday, I came home and finished the paddle with a final coat of butcher's wax, and a fierce buffing. I decided to give it a test.
The paddle was so glossy now; you could hold it up and see a perfect reflection of your face in it. I had a raging harden in my pants by this time, so after the last coat of wax, I dropped my trousers and bent over my tool bench, I held the paddle up, and it shined wickedly - reflecting the overhead florescent into my face. I quickly reached back, grabbed my underpants and jerked them down as my cock sprang free. Before I could talk myself out of it, I brought the paddle up and back behind me, and delivered three stinging swats to myself.
SNAP! SNAP! SNAP!
Tremendous! Superb speed and balance. I looked back to admire my own handiwork, and there were 3 perfect red ovals forming on my right ass cheek.
My cock was a flagpole, and my ass was on fire, and it took all the restraint in the world not to touch myself. I was saving myself for Saturday night. I could barely contain my fantasies at this point, just the thought of Jen's bottom twisting and undulating under this tool made my head swim.
I spent the rest of the night wrapping her other presents, and then packaged the paddle in an old Victoria's Secret Box. I then wrapped the box in some handsome paper I had picked up at the mall. The box seemed like a great touch, especially knowing she'd undo the wrapping and see the Victoria's Secret Box, and think: "Oh wonderful, lingerie!", and instead find a present that would sting her derriere red. I decided not to put a card on it.
Finally Saturday afternoon came, and I was about to hop into the shower. The phone rang....
"Hello"...
"Hey sweetie, it's me! How are you?"
"Great" I said, thinking of the box of with its deadly contents.
"So what's up?"
Jennifer said, "Well hon. I hope it's ok, but I asked Linda if she would come out a celebrate my big Four-Oh with us tonight. Is that going to be ok?"I hesitated for a moment as this might change things a bit. Jennifer had been friends with Linda now for five years, and they were practically soul mates. They did everything together, told everything to each other. They shared everything, and at times I had suspected that they also shared a physical relationship.
The three of us had done things together hundreds of times too, and I loved Linda as well, though Linda's relationship was platonic with me in a physical sense. The three of us had even gone on vacation together once. She was a sweet woman, about Jennifer's age - with long black hair that hung half way down her back. She was slim, and actually better looking than Jennifer in some ways. I have to admit there were times when I would fantasize about Linda, or even how great it would be if all three of us went to bed together.
Linda however was bit timid and shy. She didn't say much sometimes, but when she did - it really came from the heart. In some ways she reminded me of a woman from the Victorian ages. Very pale, milky white skin and fine features. A professional business woman like Jennifer, and the same age...
I decided between diplomacy and compromise - then finally love won out..
"OK, That sounds good... are we still going to the same restaurant?"
I thought about the paddle, and how I'd have to stash it away until after Linda left. I also thought about how restrained I'd have to be during dinner, thinking about anything but swatting Jennifer's white ass, and to keep from getting a hardon.
"Sure, it's my favorite restaurant"
"Terrific, I'll see you at 8:00?"
"Yes".
"OK sweetie, I'll be there - shall I pick Linda up?"
"Yes could you?"
