Olivias Stiletto Seduction

She was standing on the seawall, her blonde hair fighting the onshore breeze. Her profile depicted sorrow and a sense of loneliness as she stared into the setting sun. Something drew me towards her. Her short white denim skirt was slightly lopsided, her deeply tanned calves were pulled taut by her 4 inch white stilettos.  I stood next to her and caught the erotic scent of her perfume. I could see she had been crying as tears had carved gentle furrows through her foundation.

She sensed my presence and smiled briefly. I suddenly felt her overriding sadness and opened my mouth to say something but failed to find the words. She smiled again, and this pulled the words free. Are you ok? No, I'm not. The words almost shuddered out. What's wrong? I asked. For a moment,  I thought she was going to collapse to the ground, so I took her arm as I didn't fancy going into the cold glassy harbour after her. She simply said: He left me. Who did? I asked. My lover.  My soulmate. She tempted him away. Now I'm alone in this strange town with no one to love. I noticed she was once again looking unsteady and suggested we move to a small bench perched on a concrete plinth, surrounded by small shrubs, importantly, away from the harbour wall.

She moved towards the bench, her heels slipping out of her stilettos as she walked away from me. I was mesmerised.  I had no idea why, but I found this uncontrollably erotic. I followed her and sat down. She crossed her legs towards me, and her heel popped out of  her stiletto, dangling but held in place by her tanned curling foot. She was completely unaware of how sexy this was and what it was doing to me. She turned to me, brushing my leg with her high heel. I smiled and suggested we find somewhere for a drink. She looked like she needed one, and I did for sure. She simply said ok then when to stand, but as she uncrossed her leg, her shoe dropped to the floor at my feet. I instinctively picked it up, feeling the slight warmth from within. She pointed her foot towards me, and I took her heel and slipped it back on her silken foot. Her deep pink painted nails disappearing into the pointed toe. As her heel slipped into her stiletto, I noticed her perfect toe cleavage teasingly revealed. I stroked the top of her foot and ran my fingers down, sliding them between the side of her shoe and down into her arched instep. She responded, pushing down on the ball of her foot, arching and popping her heel out slightly.  I explored the underside of her exposed sole, gently stroking the soft, warm skin. Her heel fell away, exposing the ball of her sexy foot. I responded  by lightly scratching the exposed ball and felt her breath quicken. She pointed her toe, and the stiletto slipped off into my hand. The heel was thin, and it ended in a metal tip, which made a very erotic clicking sound when she walked across the concrete plinth that supported the bench we were perched on. I turned the shoe upside down and started gently scratching the underside of her exposed foot. I made my way up from those dainty painted toes, sliding the thin heel between each one and then moving onto the ball. Increasing the pressure slightly,  the end of the heel now grazing in a circular motion I felt her push down on the heel, so I increased the pressure slightly and expanded the circle towards her instep. She increased the pressure further, so I dragged the end of her stiletto to her heel and then back to the ball using a waving pattern. This continued for a few minutes with her breath quickening further and moving her other foot closer to mine,  teasing my exposed skin with her other heel.

She plunged her heel into my instep, pushing down and stroking the underside of my foot. The cold tip of her stiletto sent shivers through my whole body.  All this was now driving me wild with desire, and it took all my willpower not to lean over, kiss her gently, and start stroking her legs up towards her skirt and beyond. I could almost feel the heat pouring down from between them. I slowed the pace of the heel foot massage and gently twisted her shoe back onto her foot. Once again watching her deep pink painted toes slide out of sight as her heel slipped back into her sexy and slightly slutty white stiletto. She was still mesmerised.. her lips slightly parted and her eyes had that far away gaze. Her other heel was still working its magic in my shoe, still driving me to the edge. I gently suggested we go and find somewhere to have a drink and dinner. She nodded and pulled her heel slowly out of my shoe but it caught the side as it slid out. Her foot came out of the high heel, leaving it hanging out of my shoe. It quickly toppled to the floor and her foot slid around blindly trying to locate it and bury her foot back inside.  After a few seconds pushing it around,  her foot slid in and the scraping of the heel in the concrete advertising it had docked with her shoe.

We walked back towards the town,  heading in the general direction of the tourist area. She took my hand and held it tightly, turned to me and said, Hello,  I'm Olivia. I introduced myself as Tom and we continued into town. As we approached a small alleyway on the left, she guided me up it towards a small restaurant tucked away in a corner. She let go of my hand and walked in. A waitress met us and she asked for a table at the back of the restaurant,  away from the door and other tables. We weaved our way, following the waitress, to a sung table in the back corner of the restaurant.  It was tucked away behind a small, low partition, and very private.  Little did I know, this was her plan to continue her seduction.

We sat opposite each other. My back to the other tables whilst she faced into the main restaurant but partially hidden by that low partition. I was still dizzy with desire after all the erotic foot play. Cocktails were offered.  I requested a Gin Fizz and she followed suit.  A different waitress brought the cocktails.  She was tall but most of her height was due to her 5 inch peep toe platform stilettos.  They looked like Louboutin's but I couldn't be sure in the lowered light. Regardless they were very sexy and she knew it. I made a mental note to return here soon.

We thanked her and touched glasses then took a sip of the still fizzing cocktails. I started to speak but she placed her finger across her lips to silence me. She captured me with her intense gaze whilst taking another sip of her cocktail. I felt the toe of her stiletto slide up the side of my right calf. Slowly she slid it up then down, pausing occasionally to twist her foot so the heel end grazed down. This sent shivers through my whole body. The gin was beginning to hit my bloodstream, I took another sip as she lifted her foot above my knee and started  to caress the inside of my upper leg with the side of her shoe. She soon hit the end of my cock with her stiletto heel and sole. She pulled back a little and rubbed the side of my engorged member with her 4 inch heel. Twisting her foot forward,  her sole nestled between my legs, gently massaging my balls whilst rubbing my cock with the side of her shoe and I could see the pointed toe of her sexy white stilettos between my legs under the table. I gripped my glass as I almost could not control my urge to cum immediately, which would have been messy as I'm sure I would have shot my load out of the bottom of my shorts and onto her leg. I let the feeling subside and got my breathing under control.

A gulp of gin fizz cooled my hot flush. She slipped her stiletto clad foot back to the floor and I heard the distinctive noise of her foot slipping from her shoe. Before I could completely recover my composure,  her bear foot appeared between my legs... massaging my balls and quickly bringing me, once again, very close to an uncontrollable orgasm. She worked the head of my cock with her pretty little pink painted toes which I could see occasionally pop up between my legs. Just when I was about to let go and let my orgasm take over, she withdrew her foot and I heard it sliding back into her shoe. The sound alone peaked my arousal. At this point, we were both reaching for what  was left of the gin fizz. I drained my glass, she took a sip but still had a little left.

I was about to ask if she wanted another drink when she passed me her phone. It was unlocked and on the screen was the Lovense app. She leaned towards me and whispered.. tease me! I had never used the app before but could see that it worked by sliding the dot up and down which controlled the speed of the device she had inserted within her. I took her phone and started to play with the app. Slowly moving the control and watching her reaction. At first, she didn't react at all but as I continued slowly moving the dot around the screen, she became aroused. Biting her lip, gripping the edge of the table and her breath quickening.  Watching her become more aroused was driving me towards the edge again.  Just as I thought I had this under control,  she raised her left foot and pushed her stiletto between my legs again.  I increased the speed of the Lovense but she didn't react.  She tapped her smart watch as she dug her heel under my balls and rubbed my cock with the side of her high heel. The phone in my hand vibrated and I looked down to see what it was. There was a popup in the Lovense app that simply said : "Get your cock out of your shorts"

She gave me a very seductive smile. I was under her spell. I reached under the table with my right hand, unzipped my shorts and prised my cock out. It sprung free and before I could position it to avoid it being seen by anyone else, she popped her heel out of the stiletto between my legs and slid my precum covered cock inside her 4 inch white high heel. I could once again see the pointed end of her high heel and the tip of the heel between my legs and this turned me on even more.

I had neglected her Lovense toy with all these distractions so I quickly started the circular motion again. This jolted her upright and I could see she must be very close to orgasm.  She was pulling her heel onto my cock which was pushed hard against the ball of her foot and trapped in her stiletto by the weight of her leg.. pushing my shaft against the back of the shoe. The arching of her foot was squeezing my cock in and out and I was so close to exploding my hot seed deep into her shoe when the cocktail waitress came back to our table to see if we wanted another drink. I had the phone flat on the table, still running the Lovense dot in circles but Olivia showed little sign of further arousal.  I looked at the phone and it was a different model but still had the app showing. I circled the dot faster all the time looking across the table. She was still curling her foot to pump my cock that was pushed hard into her high heel. I almost lost control but remembered the waitress standing there.

Her name was Tanya, so her badge said. She was about 5 ft 8 in her 5 inch peep toe platform black patent stilettos which showed off her red painted toes to match her fingernails. Her top was slightly too small, pushing her pert boobs up and out to give a seductive plunging cleavage. Her tanned legs were bare and her waitresses skirt was short and tight with an apron round her waist. She had jet black hair, cut in a long bob, heavy black eye makeup and bright red lipstick.  She was very pretty, probably in her 40s. I was expecting her to say something but she was speechless and her eyes locked with mine, she gripped the table and seemed to be shuddering in time with the circular motion I was drawing on the phone screen.  Then it hit me.. I was controlling her Lovense! Hence the phone swap.. This pushed me over the edge.. I came hard into Olivia's white stiletto,  it didn't seem to stop and I could already feel my hot cum filling her shoe. Tanya also came at that moment, her whole body went ridged, her calves tensioned and she parted her legs slightly. I kept the Lovense going and I watched as Tanya popped her heel out of her right stiletto and rested her toes on the floor just as her cum juices flooded down her leg and dripped off the end of her red painted toes and onto the tiles.  It was all in vain as she was cumming so hard that her other leg was also flooding so her remaining stiletto filled with her cum juices. I looked over at Olivia who had brought me here. She was also cumming, controlling her own Lovense with the phone she had swapped out whilst I was distracted. Seeing Tanya cumming again and again and Olivia cumming in unison combined with the white stilettos being pulsated in time to Olivia's orgasm was enough to push me over the edge again and I dumped another load of hot cum in her already full stiletto. I eased off on the Lovense but Tanya was still flooding the floor and her left stiletto, so much so that I could see her juices dripping from her peep toe. Her other shoe was on its side and was also covered in cum juice as she had cum so much that anything within a 30cm radius of her legs was covered in her juices. My cock was starting to relax and Olivia relaxed the pressure which allowed her to pull her foot and high heel back and down to the floor.  As she pushed her heel back into her white stiletto,  I heard the squelch of my cum flood round her foot and  toes. I was looking forward to seeing her toe cleavage oozing with my seed.

Meanwhile Tanya had slipped her sodden right foot back into her black patent platforms. I still had control of her Lovense but for now, she was under control. She regained her composure, picked up her phone, mouthed thank you to me and asked us if we would like more cocktails.  We both ordered the same again and I asked Tanya if she would like a drink and join us later if she wanted to. She smiled and accepted the invitation. She walked away to get our drinks and I could see her legs still glistening from her cum juices as they evaporated.  There were multiple wet patches on the floor and I could clearly see the outline of her shoe and her scent lingered in the air.

I looked over at Olivia who had made me cum harder than I had ever cum in my life. She smiled and said, I need to dry off at some point as my skirt is soaking wet. Feeling you cum so hard in my stiletto and watching Tanya pour her juices all over the floor, under your control, sent me over the edge harder than I've ever cum before. My lovense was in automatic and I couldn't stop cumming even after I stopped it. Watching and feeling you both completely lose control was the most turned on I've ever been. I'm still feeling little waves even now!

Our 2nd round of cocktails arrived,  this time delivered by the other waitress as I suspected Tanya was drying herself down in the ladies room. I needed a pee so excused myself and found the toilets.

They were unisex and I spotted Tanya in the end cubicle as I could see the red soles and back of the heels of her stilettos under the door! It was as if she was kneeling down with her heels popped out of her shoes. I then heard a low groaning sound coming from the same cubicle.  I crept closer and slipped into the one next door. She was not alone. I stood on top of the toilet cistern and slowly peeped over the top of the partition.  I could hardly believe my eyes. There was Tanya, on her knees, giving this guy who I vaguely recognised,  the most sensual blow job!

He was sitting on the toilet seat and she, on her knees, heels popped out of her 5 inch stilettos, her pert boobs were free from her top as she bobbed up and down on his cock. I could still clearly see her cum juices inside her exposed stilettos from the massive orgasms I had given her not 10 minutes ago! I was getting very aroused again and I could see from the look on his face that he wasn't far from cumming.

He gently held the sides of Tanya's head to get her to speed up a little, which she did. She then drew back so the tip of his cock was just resting on her red lipstick covered lips and said to him.. Are you going to fill my slutty stilettos with your hot seed? Oh god yes he groaned. She took his full length into her mouth and massaged his balls. Her mouth was working up and down his cock, caressing the tip then taking his whole length again. His breath quickened and he murmured I going to cum!  She reached down for her left high heel. She let his cock slip out of her mouth, took it in her right hand and guided it into her stiletto, gently teasing the end in and out of the toe.

He was so close to cumming so she gently started moving her hand up and down his shaft. Suddenly he went rigid and started to cum, blowing his load deep into her stiletto. Tanya pulled his cock out of the toe and let his cum spray into and all down the back of the heel, dripping off the bottom of the stiletto. I could also see his cum running down inside Tanya's shoe and slowly out of the peep toe. She lifted his cock out of her now flooded show and wrapped her sultry red lips round his still dripping member and finished him off by once again taking his full length deep into her throat. He groaned again as the last bit of cum jetted into her mouth. I was now incredibly aroused and I noticed her other heel was still popping out of her stiletto and I found myself imagining I was pushing my cock in and out, pushing down to the ball of her foot and the back of her heel rubbing against my cock. I just stopped myself from cumming again as I knew I would not be able to keep silent if I did!

I stepped down to the floor as they were untangling themselves.  I  heard the door lock click open but only one set of footsteps leaving. Tanya was still next door. I waited until she left the cubicle, her heels clicked across the floor and I could see that there was still cum on the back of her left heel! She stood by the sink and started touching up her makeup and lipstick. I clicked open the lock and walked out. She smiled and said: Enjoy the show? Did you manage to keep yourself under control? Only just I said sheepishly...