Back in late December of ’02 Roxy and I had been seeing each other for a few months. She lived in a studio apartment above a restaurant in the Hell’s Kitchen neighborhood of NYC. Roxy worked in corporate sales for a large hotel and originally came from Puerto Rico. At the time she had dyed blonde shoulder length straight hair and fair skin. People would often be surprised to hear that she’s from Puerto Rico by her appearance and that she spoke English without an accent typical of Spanish speakers. She grew up bilingual and spoke Spanish too (and French). She was one smart and ambitious girl. Charming too. She certainly had a personality perfect for a sales job. At 5’6” and around 125 lbs. she was fairly trim with brown eyes that seemed to protrude more than normal, a well-structured and proportioned nose, and pronounced curves more typical of Latin women. Her backside could probably be considered her best physical asset (no pun intended) though she did like her own nose. Her fingers and toes are on the longer side and she’d often paint them pink at the time. Her sized 9 feet were somewhat flat with slightly longer second toes and she’d take good care of them and often wear nice shoes to work. All things considered it was a little unlikely that she was dating someone like me at the time in the first place. I was relatively introverted and insecure. But I had my moments and we had a few things in common. And she thought I had an understated charm and wit.
Roxy wanted me to attend to a few things at her apartment while she was away in Puerto Rico to visit family until just before the New Year. She left me keys and had an early flight on a weekday morning. I hadn't seen her much that week prior and we didn’t get together the previous night before she left because, as she put it, she had plans that night and in so many words had made it clear that I wasn’t invited. She said something about meeting an old friend visiting the city who lived in Denver now and a few other people. I felt okay if not thrilled with not being included at the time. We’d been together for a few months by then and there were a few disagreements, awkward moments, and friction over where things may be going or perhaps not going in our relationship. It’s hard to say exactly but my moodiness, indecision, and discontent with some other things going on in my life at the time probably didn’t help matters. Therefore a few days apart didn’t seem like such a bad idea at the time, especially with Christmas coming.
Leading into her apartment was a stoop, a vestibule with an exterior door, a small interior space, and another secured door directly in front of the staircase leading up to the second floor. The building had no elevator, as is typical in many NYC pre war brownstone buildings of that era. The stairs leading up to the second floor were cold, a bit dingy, but well lit. After a turn to the right on the second floor to her apartment door I put the keys in the locks, both the regular lock and the deadbolt, opened the door, and stepped inside. I didn’t immediately see the thing that would alter my mind so completely. But after I went to the kitchen space to the right to deal with the stuff I needed to there I gazed back toward the living room area and the bedroom space beyond and there they were on the hardwood floor: a pair of sexy Anne Klein pointy toe strappy black high heeled sling back pumps. One was upright and the other lying on its side.
After what seemed like a long day of thinking often about the shoes on the floor and a good deal of fantasizing we finally talked on the phone a few hours later. I felt a bit hesitant to ask. What would she think about my asking about the shoes? Would she find it strange? After some pleasantries like asking about her trip and stuff like that I somewhat nervously jumped in:
“Ummm i noticed that you left a pair of shoes on the living room floor. Black heels.”
She paused a few seconds. “Oh yeah i forgot and didn’t have time to put those away. I was in such a hurry to get going this morning to the airport. Couldn’t wait to get out of those shoes last night.”
I got a bit aroused as I thought of Roxy coming back to her apartment after the night out with aching feet, unbuckling those straps, dropping the shoes on the floor, and walking barefoot or in pantyhose feet around the apartment with her pink nail polish on.
“Hmmm. What else did you wear with those?” I continued.
After another short pause she countered. “I wore those last night out to the bar with some black pants and a sweater. My friend Paul and a few others were there. We sat on some bar stools with rungs on the bottom so i could cross my legs and hook one of my heels around the rung with the other leg out in front where everyone could see the my leg and foot sticking out with those heels on. I actually got a few compliments on those shoes.”
After hearing that my mild arousal had turned into a full blown boner in just a few seconds. The thought of her ample round ass in tight black dress pants perched on a barstool and her heels on full display for all to see was just too much. Part of me was jealous and miffed that I couldn’t be there to see this in person and that she was out with at least another guy in their party. Who the fuck is this guy she was with last night? But I was getting so turned on all the same.
She continued. “I think those heels must enhance my figure in those pants because later that evening when I was standing having a drink some guy came up to me and put his hand on my ass and said ‘who are you going home with tonight?’ it was soooo annoying.”
Now I felt almost ready to explode with arousal. She was telling me how she was out getting hit on by some random guy. It was so teasing. I replied:
“Well I have to admit I’m getting turned on hearing about this. I wish I was there.”
She chuckled.
“Oh yeah? You like the thought of me in those heels and that outfit do you? When it was time to leave I was outside trying to hail a cab down on Bowery and it was starting to rain. Do you the thought of me out there on the sidewalk in that outfit?"
My next mental picture went to her holding an umbrella, her arm outstretched to hail a taxi, while raindrops sprinkled on the exposed tops of her delicate feet and lightly streaming down in between her toes inside those shoes. I admitted outright just how turned on I was by her words. That prompted a few more chuckles and a challenge from her.
“So what are you going to do about that?”
I knew I’d have to do something more than just jerk off until she came back to town. I had a plan. I got a Polaroid camera (this was the era before cell phones and pics were dominant) and went back to her apartment that night. I picked up one of her heels and sat on the couch. First I held it to my nose. I could detect a slight smell of her sweaty essence – the accumulation of her night out on the town. That and the satiny feel of the shoe in my hands got me super hard. I pulled out my cock and started to run the tip along the contours of the upper and then inside the shoe itself. As I was doing this I snapped some Polaroids. The images in my mind of her turning guys on with her charms…her ass…her eyes…her smile…her shoes had me right at the edge very quickly with hardly any stroking. I could have very easily come right inside the shoe. But soaking one of her precious Anne Kleins may have made her mad, even if she deserved it for teasing me. So I opted for a release onto my stomach with a picture to go along with it. I then left the handful of cock shots I took there on her coffee table as a surprise to see when she arrived.
After what seemed like a very long week she finally came back into town just before New Year. When she got back to her apartment she called almost immediately.
“So I see you left me a surprise…Well…I was going to try and see you tomorrow but I think you should come by tonight.”
And after what seemed like a long evening at work and a few other commitments, I finally got over to her place. After a hug and an “I missed you” from both of us we basically cut right to the chase. We started kissing hot and heavy. Her warm wet tongue probing the depths of my mouth and I doing the same for her. She then led me over to the couch and picked up the Polaroid camera that was still on the marble coffee table and handed it to me. Then she asked me to take a few photos as she was unzipping my pants and reaching in to pull out my cock. I snapped a few pictures per her order as she started first licking the tip of my cock and then taking it wholly in her wet and warm mouth. It was the same place I took the cock and shoe shots just a few days prior. I could have blasted right then and there but held it together because I wanted this to last. Instead she led me by the hand to her bed and a few minutes later we were lying there naked touching each other all over. I should say we were naked except for one thing. She put those now famous black shoes back on! I was returning her generous mouth work with some of my own and then we assumed our mutually favorite position – Roxy prone lying on her stomach and me on top of her working from behind, her legs inside of mine as I straddled her making for extra tightness between her things. I always like this position because, besides getting to look at her magnificent Latin curves from behind, I can so easily feel her feet rub against mine as I’m thrusting. When she’s barefoot I like to rub the tops of my feet against her soft soles almost in a tickling way. Tonight however it was the all about the lustrous feel of those shoes that I felt with my own feet. I knew that if I worked too fast I’d come very soon. I also knew this was going to be a big, juicy orgasm. I wanted her to come the same time as I did and hear her shout, as she tends to do when climaxing. So I first slid my cock along her ass crack and against her tailbone as she reached behind her back and played with it. At the same time I could feel her heels press against my feet. Then after penetrating I slowed it down and savored the feeling of full and slow strokes. I wanted it to last as long as possible and talk with her as we were fucking. I whispered in her ear that this is exactly what that guy at the bar who put his had on her ass wants to be doing to her right now.
“You bet!” she moaned. “But this ass is taken!” And after a few more thrusts she said:
“And the shoes on the floor,” she whispered. “I left them there on purpose for you to see.”
It took two, maybe three more strokes before I could no longer contain myself and came with such force that the jerk off on the couch a few days prior felt like a little warm up for this ‘main event’ we were both experiencing. Supposedly a male orgasm only lasts a few seconds. But this one seemed to go on much, much longer. And as I was unloading, she bent her knees and kicked me repeatedly with one foot and then the other as if she were splashing in a pool. I could feel those sharp heels against my butt and that sensation squeezed out more hot juice if that was even possible. Her moans and shouts of “Oh yeah” told me she was climaxing too.
I still think about those days in the city, and the shoes that still kindle flames. She still has those shoes and we're still together. I think it's time that she and her feet revisit them for old time's sake
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