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Jennifer's Birthday Paddling

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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?"

I breathed a sigh of frustration inside. Linda would need a ride home afterwards, and it could mess up the whole evening. However, it was my sweetie's Birthday...

"Sounds super. I love you, and I'll see you in a bit..."

I hung up the phone and headed for the shower.

I left the house about half past six, rolled the windows down, and started driving over to Linda's place. It was a warm August night, and the trees were full and dappled with bits of late afternoon sunlight. I could hear lawn mowers and crickets faintly in the breeze, as I wound through the suburban streets.

I had a smoke on the way, to quell my jitters.

Linda looked just beautiful when I picked her up. She was freshly scrubbed, and her long black hair simply glowed. She was wearing a white knee length summer dress, white matching sandals, and just a touch of lipstick. A faint smell of ChanelNumber 5 wafted in the air - it was heady and romantic. I hugged her from across the seat, and gave her a small kiss on the cheek. We started to drive...

I had placed Jennifer's presents in a bag on the back seat, and Linda put heir's back there as well - a large box. We chitchatted with each other during the 15 minute long drive. Finally at one stop light I pulled up a bit short, and my special box containing the paddle slid out from under the passenger's seat, and bumped Linda's heels. She reached down...

"Hey, what's this? Another secret present?"

She smiled and wiggled her eyebrows up and down at me.

"Oh nothing" I said. I playfully tried to grab the box away from her, but couldn't while I drove.

"Besides, it's none of your business Linda"...

"Uh-Oh" Linda gleefully shook the box and said "Gee, sounds like something illicit in there". She clutched the box to her chest...

"I'm going to tell Jennifer - ohhhhhh".

"Common, knock it off silly" I replied, and snatched the box from her grasp. She smiled again, and tried to make another grab for it, but I had reached around and thrown the box into the hatchback section way in the rear. The car careened wildly down the street.

"Mmmmm...Sounds like a hot night for Jen tonight!" she giggled.

I had no idea how much Jen shared about our sex life with Linda, but seeing as how they were so close, I assumed it was everything. The three of us joked around all the time, and there was no way could even kiss Jen in front of Linda, without her making some sort of cute little remark or teasing us.

Finally we got to Jen's, and she was sitting on the front porch waiting for us. I hopped out and gave her a warm hug, and long kiss on the lips. She smelled wonderful, and also had on a pretty summer dress. Sort of a light and gauzy thing, with a plunging neckline. It had a small print pattern of flowers on it. Jennifer liked wearing a bra much, and her breasts filled the dress nicely. I could see the faint outline of her nipples peeping through the thin material.

"Happy Birthday Sweetie"

"Mmmmmm" Jen held me tightly, and kissed me on the lips again. I could feel my prick stirring faintly in my jeans.

"Hey, am I gonna have to call the Vice Squad?" Linda chimed out from the car.

"All right, all right - we're coming" I replied.

Dinner was great. Jennifer had a favorite Italian restaurant right in her neighborhood that we had been going to for months. We got there around 7:30 - and enjoyed a bottle of wine while we sat in the cafe's garden patio.

Dinner seemed to slide right by, and by the time we left at 10:00we had consumed 2 whole bottles of fine French wine, and Irish coffee during the dessert course. The girls were rather tipsy, and I was as well.

All through dinner I kept thinking of the paddle, and how satisfying it would be to hear it crack against Jen's ass. How she would love it...my cock kept springing to attention, and I was glad the tablecloth concealed my condition.

We all walked back to the car (swayed), and I had my arm around Jen's waist, and Linda's hand in mine.

Finally we got back to the house, and Jennifer poured us each an after dinner liqueur, while she opened her presents. Linda had given her a wonderful ceramic bowl, and I had given her two books, a new blouse, and finally a set of pearl earrings.

"Oh Claude they are wonderful".

Both girls cooed over the earrings and Jen tried them on right away. They looked beautiful with her outfit I thought. She plopped down on the couch next to me, and gave me long wet kiss on the lips. She was rather bombed, and started rubbing my thigh in circular motions, moving up my leg towards the bulge in my jeans.

"Hey shall I get a bucket of cold water for you two?" Linda teased from the other end of the couch.

"Besides, Jennifer has one more present to open" she added.

Jennifer stopped kissing me, and looked at Linda.

"Another present?" - "where?". The bag I had brought up was empty, so I Jennifer started looking around the room. Here eyes were glassy, and she was in an obvious state of lust.

"Oh just a little something Claude has stashed down in the car for you my dear". Her voice was mocking, and she did that silly little eyebrow wiggle of hers, that she did when she teasing us about sex.

Jennifer got that impish grin of hers. "Oh goody, another present!"

"Now wait a minute!"

Jen had sprung up from the chair and already had my car keys in hand from the small table near the door.

"Ah, sweetie - that's something you should open LATER...when we're alone, ahem."

She was swaying back and forth from all the wine. "Sorry" she giggled, "I want my present now". And with that the clomped down the wooden stairs outside and made a bee-line for the car.

I was too buzzed to really be upset and leaned back lighting up a cigarette. Still, I couldn't let Linda get away with this...

"That's just great Linda. Thanks for nothing" I said sarcastically.

Linda grinned that silly grin of hers, and I could tell she was really feeling the effect of the wine too. Moments later, Jennifer came bouncing back into the living room with my special present in her hand. She literally flew into in to the empty spot next to me on the couch.

"Ahh, Jen - why don't we open this a little later, after I take Linda home?" My voice was soft but serious. She could tell I meant business...

"No! I want to open it now!" She was playing the part of the spoiled brat, and loving it. I sighed...

Slowly she tore open the paper to reveal the Victoria' Secret box inside, and she let out a gasp of excitement. This was my last chance...

"Ah, Hon - well it's not really what you think it might be". I gulped. "Are you sure we can't open it later?"

"Open it now! Open it now! Open it now!" Linda chanted. My arguments fell on deaf ears, as Jennifer opened the lid of the box and undid the tissue paper inside. There lay the paddle, gleaming in the soft light of the living room. Linda grabbed my shoulder and craned across me to get a better look. Jen lifted the paddle from the box...

I think both girls had really expected it to be some sort of G-String, or short nightie - anything but a paddle. Jennifer grinned hugely, and showcased the paddle to Linda; especially the side with the heart and "Jennifer" painted across it.

"I love it!" she squealed.

I have to admit, Linda looked a bit shocked at this point and a blush had come to her cheeks.

"God, I just Love it!"

Jennifer leaned over and gave me another wet kiss, and then jumped to attention.

"I've just got to see how it feels!"

And with that, she tuned her back away from us - facing us, bent over, and slammed the paddle against her backside, right through the dress. She proceeded to give herself two more swats.

"Ok" I said - feeling a bit embarrassed at her tipsy condition, "Time to take Linda home".

"No no no" Jen responded, "I want my spanking now!" She followed this up with by wiggling her hips around like a Hula dancer.

"Not only that" she added, "I want Linda to watch me get my Birthday spanking".

I looked over at Linda, who seemed sort of dazed at the whole event.

"Linda, do you want me to take you home?" I asked?

She shook her head back and forth.

"Are you sure?"

"Yes" she whispered.

"Ok Linda, you better knows what you are getting yourself into here. Jennifer has asked me for a birthday spanking, and I aim to give her one. Once we get started. There no turning back, is that understood?"

Linda nodded, her cheeks were flushed, and I could tell she really wanted to watch. My heart felt a new burst of courage, I was in command here, and these two women were my charges.

Linda nodded again.

I stood up, grabbed Jennifer's wrist and stated to lead her to the bedroom. Linda just sat there, smiling.

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