The Shoe Dates

Kinky for me might be rather tame for some. I'm sort of a hot vanilla guy, you know, pretty conventional sex done with extra heat and production values, music, loud dirty talk, candles, outside, in a parking garage, in the hot tubs, maybe a little role-playing dialogue. I've had women watch me masturbate, and I've used toys on girls before, but really, nothing you can't find in any porn magazine for sale in any respectable bookstore in America.

The kinkiest it's ever gotten for me was about four years ago, and involved no sexual contact at all. Well, no penetration. My supervisor at work was a smartly dressed older woman, Tonia, and Tonia had great taste in shoes and boots. I definitely have a shoe fetish, and Tonia caught my eye from the first day. One evening while out for drinks, she was a little drunk and I had more courage than normal, and so I propositioned her. Tonia was flattered but mentioned she had a very serious boyfriend and, plus, the working situation made a relationship of anything beyond friendship unwise. 'Fuck,' I said, 'because I really love your shoes.' She gave a flattered laugh and we discussed them and then I had an idea.

'If I can't date you, maybe I could date your shoes?' I said, and she laughed. She was wearing a pair of 3 inch, pointy slingbacks this time, but I had seen her in other styles, strappy buckled pumps, high-heeled slides, stilettos when she was really daring, and boots galore, including a pair we called the 'slutty boots.' Tonia laughed. 'I don't know if I can trust you with my girls,' she purred. 'I know what boys like you want to do with shoes like these .'

'I just want to get your shoes in bed, baby,' I said, mostly serious, and, curious, Tonia asked me if I have a shoe fetish. That began a round of incredibly dirty talk, with me describing how I loved to fuck shoes and stockinged feet. She asked me what it felt like and if it was enough to make me cum, and I said of course. 'And do you shoot your cum all over her shoes too?' Tonia asked. I described in lurid detail all the thick whips of cum I've pumped on shoes, with or without their owners present or knowing, and I was hard as a rock.

So Tonia then said, 'Well, I have a few old friends that haven't gotten any in a while, would you like me to fix you up with a pair?' At first I didn't get what she was talking about, and then I realized, she was proposing a shoe date. So we worked out the particulars, what night (the coming Friday), where to meet (my place) and then when I'd have them home (by midnight). The next day at work I laughingly reminded her of the date, and she sent me an Outlook invitation to make sure it was on my calendar. But I was still surprised when, at 7:30, Tonia rang my doorbell.

'Hi! Here are the girls, and they're very excited to meet you!' Tonia cooed. She held up a pair I'd seen her wear frequently, black patent, scalloped heel, modest spike (maybe 3.5 inches). 'Really, Tonia, you know what I'm going to do with these, right,' and Tonia shrugged and smiled, she was very sexually confident and passed no judgment on others. 'Have fun with them sweetie,' Tonia said. 'I want them back at midnight.'

As soon as the door closed, I was tearing off my clothes, sitting down with some wine and looking at porn pictures that reminded me of Tonia, I'd fantasized about her alot while rubbing her shoes all over my rock-hard cock. I wanted to make sure my velvety cockhead touched every inch of these so when Tonia slipped them on, she knew I was fucking her feet in my mind. I fucked the insides, worked the heel around my shaft, then fit both over my hands, pressed them together and worked my dick between the soft ankles. Tonia said to have fun and I did, and I blew cum all over her shoes, inside them, wiping off the final pearls on their toes and right where her toes would touch.

About 10 I got a call, 'Just checking up on you!' Tonia sang. I was almost exhausted. 'We're having a great time,' I said. 'OK, just so long as you don't do anything the girls don't want to do,' she replied.

At midnight, I showed up at Tonia's door, wearing a shirt unbuttoned and wrinkled and my tie loosed and askew, looking like the picture of a wild date. I handed Tonia the cum-stained pumps. 'Look at you!' she said in a scolding voice. 'I don't care! Get upstairs and get in the shower, we're going to have a long talk afterwards!' We chatted and joked and I thanked her for the release.

On Monday, Tonia was wearing the exact same pair, and it got me instantly hard. I had to go to the bathroom and jerk off just to release all my excitement.

Our shoe and boot dates continued with some frequency, and with Tonia inquiries into my masturbation becoming more assertive and explicit. She was wearing her shoes now without wiping them off, and depending on the material or the pattern, the cloudy streak of cum could be quite obvious if you were looking directly at them. We were finally in a no-holds barred discussion, cum this, cock that, confessing I jacked off thinking about her, god I'm wet right now when Tonia suggested she 'chaperone' the next date. 'I want to see what it looks like,' she said. 'I want to watch you.'

Tonia showed up at my door, per the norm, but this time was wearing a pair of unmistakable Fuck-Me-Boots, thigh-high lace ups with a 5-inch stiletto and pointed toes. She took off her overcoat to show a simple brown miniskirt and white t-shirt. I'd never seen strippers wearing these. She handed me a pair of cheetah-patterned slingback pumps that were similarly unladylike.

'You like?' Tonia said, modeling the boots. I moaned my approval and moved in for a short kiss. She came inside, poured a cocktail and proceeded to model the boots for me while I masturbated with the pumps. She sat down across from me, crossing and uncrossing her legs, and in less than two minutes I was groaning that I was about to cum. 'Show me what it looks like,' she said, 'Talk the way you talk when you spunk, baby, do it, don't hold back!'

'Oh, Tonia, honey, god dammit I want to fuck you, shoot it all over your shoes and tits, pussy goddess YEAH! and out it shot, warm gooey tendrils that draped the toes and landed on the insoles, globs spraying on the leather cushions of my couch.

'Did you call me a Pussy Goddess?' Tonia asked. She was really turned on. I sat there, naked, drinking from her gin and tonic while I told her all about my fantasies and what I did to myself when I imagined them. Tonia told me about her masturbation rituals, a rabbit device, some wine, a pillow under her back, the dirty parts of a trashy novel. At this point, fucking her would have been anticlimactic, and I felt it was going to happen soon enough anyway, so why rush it.

Tonia and I kissed and groped each other for a long few moments. 'Tell me all those words you use when you fantasize again,' she said. I clumsily worked my fingers around her panties to finger her, called her my Pussy Goddess, my sex kitten, my Triple Sexxx-rated totally tarty fuck fantasy, how I wanted to kiss, lick, suck, fuck, and cum all over her big bouncy tits.

She lay back and lifted up her legs. 'Fuck my boots, baby,' she said. And I traced my hard cock up and down the insides of her thighs and calves, then along the outer, lace-up edge, making sure to dab my pre-cum on her exposed skin. Tonia played with her pussy through her panties, then finally paused, unzipped her miniskirt and slid it off so she could spread her legs wider and play with her pussy more. I stood on the couch with her legs fully extended, pressing her feet together and fucking the gap between her insteps-it wasn't the best shoejob, as the stiff leather was wrinkled up where the boot met the hard sole, but my purple cockhead flared and bulged as it emerged from between her shoes. 'Look at it!' Tonia cooed. 'Look at your cock! Show me your cock baby!' She was moaning incoherently, eyes fixed on my dick. I fucked her boots for 10 minutes, but it seemed forever, and I was looking for a graceful way to make myself cum, because the boots were very erotic but just not providing a good enough feel for my sensitive, swollen dick. 'I want to cum on your boots,' I said, 'but I can't standing up like this.' Tonia said her legs and ass were getting tired too. So I got down and, with one knee on the couch and the other on the floor, straddled her booted legs and started stroking. This really aroused Tonia. She told me she loved watching me stroke my cock, and was this what it looked like when I fantasized about her? My breathing was ragged, and I croaked 'Yes,'

'I want to see what it looks like when you cum again,' Tonia said, and that was enough to do it. My second load spurted out, not as much as the first, but I was pumping my dick so hard I flung a short burst right into Tonia's curly hair, which was bunched over her face and puddling by her shoulders. She laughed as I worked the remaining drops out, smearing them all over her boots, then collapsing on the floor, lungs burning, exhausted.

Sex with her was, bar none, the kinkiest and most erotic I have ever had, it's where I picked up most of the hot in my hot vanilla repertoire. And it was kinky and hot simply because we did everything, or close to it, before I ever got my cock inside her pussy, or her mouth. And that made our actual fucking and sucking even hotter, not anticlimactic.