Willow Arrives Poolside

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Willow Becomes a Friend with Benefits.
1.7k words
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Willow Arrives Poolside is the third installment of Nikki's weekend in Scottsdale. Nikki or Jamie if you prefer, lead a double life. She is gainfully employed as Jamie, a male marketing executive in the airline industry. A very limited few of his colleagues know anything about his alter ego. Nikki, the alter ego emerges, almost daily outside of Jamie's work responsibilities. Nikki has been dressing as a femme since her college years. Most of her family and close friends, with the benefit of being able to comprehend and appreciate her exploits, are aware of and love her. In this chapter you will meet new and old friends of Nikki. You have already met Victoria, Emma, William, and now Willow. This story contains sexual activities and situations between consenting adults. All characters are above the age of 18. Your comments and feedback are greatly appreciated. So then the life story of Nikki Madison's Kinky Adventures continues by adding another chapter, at this point in her life's journey.

Emma, as all good flight attendants do, left for a few minutes, and brought back some cheese and cracker snacks, Italian Spritzers for each of us. She also laid a small light blue box on the table. It was an interesting scene on the deck. I was surrounded three gorgeous and sexy women. Two I know intimately and one I hope to one day.

Then there is William. He just gave me a wonderful full body orgasm. His juices are leaking out of my boi pussy. I am truly sitting in the wet spot. I am a very lucky girl. As we sipped our cocktails we engaged in a little small talk. Soft music was playing in the background. Willow broke the ice, "It's time Nikki." She grabbed my hand to walk me over a deck chair. On the way over, she brought the blue box that was on the table next to us. Willow turned to Victoria, asking her to "Select some new music on the sound system, Girls, Girls, Girls is appropriate!"

I was getting a lap dance. Willow started swaying her impressive barely booty into my face, then down my chest then into my lap. My sissy clitty started to harden, pushing against the thin bikini fabric. She turned and placed her hands on both shoulders pushing her large, tanned boobies into my face. I instinctively lick the little bit of material that covered her nipples. After a few twirls with my tongue, I could feel them harden. Her body is stunning.

Willow pushed her boobies into my face, then taking a dance step back, then crotched her lower torso on my lap, then simply saying unhook my bra top. I did so, and she twirled back to face slowly sliding the top off but hiding her nipples with her hands. She leans in again, placing her hands back on my shoulders. My face was full of her wonderful boobies. Her pink nipples harden and swell. They are perfectly sized filling her areolas.

My tongue was moving back and forth licking and sucking each nipple. She took her right hand to push my face further in to suck. I took several deep breaths to smell her scent. Willow stepped back again, holding my hands, then pulling me out of the chair. She gently pushed down on my shoulders forcing me to my knees. I came face to face with her jeweled bikini bottom.

She pushed the back of my head into her pussy. I was all tongue and lips kissing and licking her pussy through the jeweled butterfly. There was very little fabric between my tongue and vagina lips. Her erotic aroma was overcoming my senses. I could feel Willow move again. She was now sitting on the side of the lounger. The light blue box was next to her. She opened the lid, reached inside pulling out pearl sequined leash, that complimented my pearl choker. and in one full motion attached it to the clip of my collar. She then opened her thighs and yanked me by the collar nestling my face in between her thighs.

With my free hands, I slid the tiny stringed bikini bottom down her legs. I pushed my tongue between her gorgeous bare labia lips.

I was focusing on Willow, but overheard Victoria say, "Come with me William, the sissy slut will be busy for a while. I need a real man!" I can sense them leaving the pool deck. Victoria then said, to Emma, "Come with us, there is enough cock for both of us!" I heard Emma squeal. The sound of footsteps disappeared.

Willow gently tugged on the leash bringing my attention back to her pussy. My tongue found her inner thigh once again. I licked and tongued my way back towards her pussy lips. As I nibbled on her labia, I discovered a small ring extending out. My tongue licked the ring, getting a small whimper as I continued to explore Willow's sex.

Using the tip of my tongue, I widen her lips, feeling her juices on my face and chin. I push one finger inside Willow's vagina blindly looking for that special spot inside. I insert the second finger as she takes control of my hand pushing my fingers up the vagina's inner wall. Ah, I found I turning her whimpers into moans. The rhythm of her moans increases as I exert more pressure on the inside walls. I am guided by her sound, then the movement of her lower body. My head is buried in Willow's thighs, my tongue and fingers are pushing her sweet spot. My mouth is drinking her sweet juices. As I continue to put more pressure on that spot, it begins to puff. I feel her body tighten then slowly shakes.

Willow's shaking increases with the pressure. My face is getting wetter. Her thighs tighten around my head. I hear an intense scream in ecstasy, spurting more fluid in my face. My mouth is open, and I gag on the sudden spurt of juices. I can feel her body slowly relax. I reach down and feel my aroused sissy clitty. Suddenly, I felt a tug on the leash, pulling me up her torso. The head of my sissy clit easily finds the lips of Willow's aching pussy. I slowly push the tip of my shaft in her vagina. I feel another slight pull on the leash again, as if to guide my clit further inside her pussy. I push her back on the lounger, thrusting my shaft deeper inside a very tight vagina.

I feel Willow's body tighten one more time. I hear her slow whimpers, then faster and faster. More quivering, then low shuddering moans, tells me she has orgasmed once again. I push once more. I can feel my load fill her pussy. I fell on top of Willow. She pulls me in. We kiss and cuddle. I know I am exhausted, but very satisfied. It's been an exciting morning.

Willow slides off the lounger, picks up the blue box, then gently pulls on my leash. Willow smiles, as she gently tugs on the leash then says," Let's go find the others!" She points down to her swimsuit and my bikini bottom. I grab them off the deck as she drags me behind her. Following behind Willow enables me to admire her superb booty once again and her all over tanned body.

As we enter the game room, we find Victoria in one of the high back chairs, William is in the other. Emma is on her knees, sitting beside William's chair. She too has a sequined leash attached to her pearl choker. There is a pink box on the coffee table next to her. All are naked too.

Willow sits in a third chair that faces the other two. I try to sit in the fourth chair that makes up this conversation area, but she tugs on my leash, ordering me to my knees in front of her.

She tosses my blue box on the coffee table. I obey. Victoria speaks up, "Don't we all look freshly fucked?" We all smiled back in unison. Victoria, pointing to the two boxes, telling both Emma and me to open our boxes, then take out the contents. I flipped the top back. Inside my box, was a pink plug alongside a pink silicone chastity. Lo and behold it was the one I already owned. There was also a tube of lube. In Emma's box was one pink plug. She also had a lube tube.

Victoria spoke up again, "Ok girls its time. We are going to go shopping, and then I have a party planned for later, but before we do, looking first at Emma then to me, it's time for your holes to filled. Stand up!"

We both stood at attention, me next to Willow and Emma next to William. I handed Willow my lube. I turned around facing her. As I handed her the chastity, she smeared the lube all over my sissy clit, she slid my balls through the ring, then fitted the shaft tube, then sliding the lock through tightening it in place.

She tossed one key to Victoria and kept the second one. She pulled me around by the cage, telling me" Bend over and stick your perky booty in the air!" She was generous with the lube on my hole, pushing the pink plug in. I wiggled a little. I could see William smear the lube on her butt, pushing the pink plug into Emma's booty.

There was silence once again, only to be interrupted by a humming noise; I then fell to my knees as a jolting sensation engulfed my body. I then saw Emma bend over too.

Victoria giggled, "Yes, its remote-controlled anal plug from our cell phones. We each have the app on our phones. Your plugs are separate and independent but controlled by the same app. We don't have to near you to control the plug. There are several speeds!" She then sent a jolt through my remote again. This time it wasn't as harsh but nonetheless it was very startling as the sensation swept through my entire body.

Wiliam stood up. With him standing his manhood was bigger than I imagined. He said, "Ladies, I must excuse myself. I have a few business dealings this afternoon. I hope to join you either tonight or tomorrow." All eyes followed this hunk of a man to one of the spare bedrooms. Victoria broke the silence once again, "Let's get dressed girls, we have some shopping to do! They are expecting us. At the boutique!"

To be continued

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NikkijMaadisonNikkijMaadison5 months agoAuthor

Thank you for your comments. I sincerely appreciate the feedback.

I have four story lines for Jennifer Nicole’s journey. When I started out, I didn’t realize the importance of titles and the pre-set line limitations. I also tried adding a story that would help the readers but that didn’t work out as planned.

Going forward, Jennifer Nicole ‘s college years will be labelled as Jennifer Nicole. Her career years will be labelled as ‘Kinky’ followed by the intended story line. Scottsdale belongs to this series but it’s too late now. The storyline that involves Nikki’s married life with Ashley will always have Ashley in the title. Jennifer Nicole’s transition to full time will have Nikki or Nikki Madison in its title.

Within each story line, there will be chapters but may not always be date sequential. Within each chapter I will try to tie in previous installments.

Sorry for the confusion, I hope you enjoy Jennifer Nicole’s journey.

niosatniosat5 months ago

Wish I could figure out the reading order of your stories. They hold lots of promise!

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