She was disappointed I didn’t wear my work boots [MF]

Joan and I began bantering immediately after meeting on ‘one of those apps’. Unlike most women whose repeated half sentence answers indicated a desire to either play hard to get or simply a lack of interest, she was easy to talk to and was fully involved from the start. Her first message was long and to the point, I responded in kind, and within a day, we were both interested in meeting.

Within another day, she suggested a phone call, again, being direct and to the point. She wasn’t wasting any energy in determining if I was worth her time. I suggested we meet up that night, as she was on the road and I knew she would be available that night. She agreed, with the warning that her time was a little up in the air. We settled on a place, and the waiting until 6 pm began.

I was at the office, the usual ‘business casual’, but not really right for a first meet, I would have preferred to have upped it just a notch. So in order to set expectations right, I would have hated for her to have gotten dressed up and find me in sneakers, I teased her about the dress code for our first date.

I messaged her “So, I’m in work clothes. if you picture my job as being similar to working on an oil rig, complete with beat up work boots, sweat-stained wife-beater, hard hat, and together with a faint scent of fish, I mean, the ocean, then that would be setting the bar sufficiently low that you’re bound to be pleased in with the real thing. Oh, and I started No-shave November a few days late. I look like I should be walking around with a coffee cup asking for spare change.”

She was enthralled with my sense of humor and detailed description. She joked back, “No flip flops today?” in reference to my insisting that I wore sandals until the first snow.

We now were more than ever looking forward to meeting.

Deciding to up the game a level, I stopped at a goodwill store on the way, and found a pair of flip flops. Then I searched and chose the nastiest pair of work boots in the store. They didn’t really fit, but I didn’t need to wear them for long.

Unfortunately, I couldn’t find a parking spot very close to the restaurant, but then she texted me that she was already inside. So I decided to walk up to the entrance, where they had a couple of tables on a patio, and quickly changed into one flip flop and one work boot. I walked in, and whispered to the hostess, “I’m playing a joke on a friend, can you hold on to these for just a couple of minutes?” holding out my regular shoes. She looked down, and with a puzzled, yet conspiratorial look, stuffed my shoes behind the podium and led me to the table.

I stopped a couple feet away, so that she would notice, but she didn’t at first. However, she did stand up to greet me, and as she took a step toward to hug me, she saw my footwear.

She burst out laughing, couldn’t stop, gave me a big hug, basically collapsing into me while she was laughing.

We sat down and immediately continued our banter.

“Just ONE work boot? I’m a little disappointed.” she said, still chuckling.

“Merely the first in a long series of disappointments I’m going to provide you.” I paused. “So does that mean you’re not going to surrender the pink tonight?”

She looked at me wide-eyed, “You’re NAUGHTY!”

I pretended to back-pedal. “Did I just say that? I’m SO sorry!”

She laughed at my fake apology. “Yes you did, and no, I’m not. Not anymore. Two work boots, and I would have been all over you, but now, you’re out of luck. You need to up your game.”

Our banter got interrupted by the server. She ordered wine and I asked for a cocktail befitting a loser. She laughed while the server looked at us curiously. “I played in the Senior World Championship Tiddlywinks last weekend, and I didn’t even make it out of the first round. She…” I motioned to Joan, “agreed to have dinner with me out of pity. So what would a pitiful loser drink?”

We both laughed, and the server became even more confused. “I don’t really know, I only started here last week. I can ask the bartender…”

“No, no, really, I’ll just have this” I pointed to a local on tap.

The server quickly disappeared, and I suspected we wouldn’t see her much.

Joan continued her explanation.

“She was clueless!” referring to the server. “That was funny! Keep it up, play your cards right for the rest of the evening, maybe you’ll get a shot at a blow job. I mean, you did make the effort, that sounds fair, right?” She joked, laughing. Except for a hello hug, we really hadn’t any sexual flirting, so I was a little taken aback by the directness, but since I had started it with a very obviously inappropriate suggestion, she was just firing back in kind.

“Would that be a real blow job, or a pity blow job?” I smirked. “Just trying to set expectations. Because matching expectations are the key to a successful relationship.”

“Or if he’s rich, that would work just as well.” She dished it back to me again.

The server arrived with our drinks, and I asked, “Can I get my real shoes? My foot is FREEZING.” “REALLY? You’re not going to wear that one work boot all night? Go ahead, but you’re going to lose points. I think you’re down to a handjob now.”

“Hey, I wasn’t expecting you to even show up, so by my scorecard, I’m already counting this as a win.” I stood up and went to the hostess, asking for my shoes. She followed me back, saying, “I have to hear the story behind this.”

As I switched shoes, Joan relayed the clean part of the story, satisfying the hostess. “I wonder if I’ll remember to bring these”, pointing to the lone flip flop and boot, ” or if the next people at this table will wonder why there’s a flip flop and boot on the chair.”

Our evening continued to be so much fun, joking back and forth. She was flirty and a little touchy, at the same time, we had backed off from the explicit sex talk earlier, which had served to break the ice and make it clear that we were both sexual people. But we were truly interested in each other, this wasn’t just a hook-up. Conversation flowed easily and deeply. Suddenly we realized that the staff was starting to put chairs up on the tables.

I walked her to her car, and conversation slowed a bit, getting to that ‘first kiss’ nervousness. At her car door, she turned to hug me, and then I decided to go for it, kissing her firmly. She responded the same way, then we kissed again, deeply, pressing our bodies together. She felt really good, just the right height, an inch or so shorter, maybe. Her hands on my shoulders, pulling me to her. We kissed several times, hard, but it was cold, and she couldn’t help but shiver.

I’d love to stand here some more, but I’m sorry, it’s just too cold. Where are you parked? I pointed behind her car, “around the corner and down at the end of the block.”

“You walked all the way in a flip flop?” She laughed. “Uh, I have to come clean, I changed on the patio right outside the front door. “Good thinking! You get points for having common sense.”

“Oh shit!” I interrupted. “Guess what I don’t have?” I held up my hands. “Your footwear!” she exclaimed. We went back to the front door, and it was already locked. “No points for me!” I mimicked the Soup Nazi.

“No points for you!” she joined in. “Now, seriously, can I give you a ride? Too cold to walk that far, even with covered feet.”

It wasn’t really that cold, but never turn down a woman who offers you a ride. I hopped in and instead of turning around, she went around the block, and ended up having to go a second block due to a one-way street. Finally she got to the street I was on, and I pointed out the dark shape behind an imposing truck. “I’m right there, the dark blue one”

She pulled in behind, under a tree’s shadow, mid-way between two street lights at either end of the block. She put her car in park and turned to me. We chatted idly for a moment, then I leaned in and kissed her again. She responded instantly, and we made out for a couple of minutes.

As we tried to navigate the hump between us, she put her hand on my thigh above me knee to gain purchase to pull herself closer to me, and slipped my hand behind her ear, pulled her head to mine.

“mmmm, you have muscular thighs!” she purred. I feel all sorts of legs (she was a physical therapist) and you have great ones, I can tell!”

We made out for another minute, the heat in the car rising. She moved her to my back, by my shoulder blade, to pull me in closer, then to my neck, and in return I slipped my hand under her arm, to her shoulder blade, conscious to not inadvertently cop a feel, but aware that her breast was brushing aginst my forearm as I pulled her to me. And she didn’t resist the light touch.

We kissed again, harder, then I cocked my head and nibbled on her ear, then the side of her neck, and felt her shudder a bit. I continued a little more and felt her relax, shudder again, and sigh happily.

She reached under my arm, and found my thigh again, and began massaging it. I was pretty worked up, and felt myself begin to grow. I squirmed in response to her touch, spreading my legs apart a bit, to signal that I was interested in her continuing to touch me.

We kissed again, her hand moved up my thigh, and I instinctively flexed.

“So…. ” she whispered. “About that blow job…..”

I couldn’t believe she was bringing it up. Our joking in the restaurant was absolutely just teasing and banter, but now, in the privacy of her car on a dark street, touching each other, ‘shit just got real’.

“Yes?” I offered, wondering where she would go with it. “I thought I was limited to a half-hearted handjob after changing out of my work boot. Make that an incomplete one!” I added, reminding her that I did indeed forget the flip-flop and boot back at the restaurant.

“I really like you. And I’m really having a good time. This is so not me, but I told you about my cousin dying, and we were really close, and I’m suddenly aware that it’s true, you only live once.”

She continued. “I don’t want you to think I’m a slut or anything, but you’re so easy to be with, and I really want to touch you.”

Her hand crept further north, until she was almost at my balls, and I spread my legs further apart. “I really want you to touch me too. If you’re ok with it.”

I was now completely hard, my cock pointing up toward my hip. She began teasing my balls, very lightly, and then looked up at me. “Is this ok? Are you sure?” I leaned back and spread my legs further apart. “Yes, it’s absolutely ok! That’s sooooo good!”

She kept teasing, making little circles around each with her fingertip, one, then the other, and back and forth, until she could see me throb inside my jeans. “Oooo, look at what’s happening there!” She ran her finger up the ridge, and back down, lightly, just barely touching me. I wanted to thrust my hips up to cause her to press harder, but patience was going to be a virtue, I was certain of that.

I let her dance her fingertips up and down the ridge, then back around my balls for a bit, then back up the ridge. I was in heaven. She was enjoying my reaction, too, and so continued. Running her fingertips around the knob, the ridge around it was visible through my jeans, I’m not sure how, but she knew exactly where it was, and how to touch it. I thought to myself, if she keeps this up much longer, I’ll come even without her handling or sucking me. We’d had hours of ‘foreplay’ during dinner, I was definitely primed.

She must have been aware of my state, because she started stroking me through my pants, gently but firmly, then squeezing the knob, like you would the tip of a banana. “You are really ready, aren’t you? Feels like you could come right now!” she said.

“Pretty close, I can’t believe it!” I whispered.

“How about if we unzip you for me?” She moved toward the zipper pull, and I pulled my belt up, to make my zipper taut. As she slid it down, I undid my buckle, so that my fly opened up. She pushed both sides apart, exposing the contours of my cock showing through my grey boxers.

“I’d like to play with you like this,” she said, running her fingers along the ridge. “But I don’t know how long you’d last. And I kind of don’t want to wait either.” She tried tugging my pants down a bit, and I raised off the car seat a bit to help her. Then she tugged the waistband down, exposing my cock, now standing straight up, and gently throbbing by itself. She pushed the waistband down underneath my balls, and held it there with her hand.

“I just want to look at you for a minute!” she cooed. “Guys are always slobbering over boobs, well most girls love a really hard cock just as much. But we hardly ever get to see them in real life. And porn just isn’t very good.” She looked down my cock again. “Ooooo, that’s so nice. A good hard cock is a work of art! Can I touch it? Here, hold your underwear down for me, ok?” I did as she asked, so her hand was free, and she began teasing me again, like she had over my jeans, but this time, bare skin.

She played and watched it react to her touch, running a finger up and down, then around the knob, then without warning, grabbed the shaft with her fist and began pumping. “mmmm this feels so good.” “You have no idea,” I murmered back. “No idea at all!”

She looked back up at me as she stroked me, watching my reaction carefully. “I want to keep doing this!” she purred, “but you’re not going to last. Or be able to drive home!” she giggled. Then, pushing her hand down to the base of the shaft, she leaned over and I felt her warm, wet mouth on top of me.

My legs straightened out and stiffened, and I started shaking. “Now, now, can’t have that quite yet!” she said as she pulled off. She gripped me firmly again, like the handle of a beer stein, and then began kissing the tip, licking it clean of the drops that had formed again.

She looked around outside the car. “Hmmm, I forgot where we were!” She leaned over again, and began pumping with her hand and twirling her tongue around the knob, then swallowed me again, bobbing up and down, over and over. “Mmmmmm. Come on, come for me!” she tried to say, her mouth full.

I’ve always wanted to be courteous, not assuming that a woman is OK with me cumming in her mouth, just because she’s blowing me. So I like to ask at some point before the moment. But Joan sure seemed like she was ready and interested in a mouth full, so I tried to give her a warning in case she wanted to change positions. “Oh my god, you’re making it happen! I’m going to cum! Are you ready? Want me to come now?”

I was still almost completely in her mouth, and she kept pumping and sucking, so I relaxed, she clearly wanted it, so I relaxed and then let out a loud groan as I felt myself gather and get ready to shoot. “Fuuuuuucccckkkkk” and then I shuddered as I started to ejaculate.

As the first shot filled her mouth I heard her murmur, “Mmmmmmmmm…” and kept sucking. With that confidence I felt free to completely enjoy my orgasm, knowing that she was completely into it as well. It didn’t take long, but it seemed like eons, until I was done orgasming, but she kept me in her mouth until I started to shrink. She pulled off and I heard a big smack of her lips. Her hand didn’t leave me, though, she kept stroking as I continued to shrink.

She looked up at me and smiled, then back down, and quickly leaned down again to lick a couple of drops that had escaped. “Oh my that was unexpected. I had such a good time tonight, I wanted you so badly. I haven’t been this turned on in a long time,” she said quietly. “I hope you don’t think less of me,” with a touch of sudden remorse.

“Oh, goodness, no, not at all. I am so glad you made the first move. I wanted to kiss you all through dinner.” I pulled her face toward me, aware of the awkwardness of my holding my underwear down while she had her hand wrapped around my balls and cock, and kissed her again. Her wet lips and eager tongue met mine willingly. I could taste a slight hint of my semen on her, and she kissed me harder when she realized it wasn’t a turn-off for me.

As we kissed, she played with me a bit more, and then broke off, saying, “I think we need to get you zipped back up, before someone comes along…” We put me back together, and then she kissed me again. “Thank you so much for dinner, and everything else. I’ll call the restaurant tomorrow about your footwear. I’m sure they won’t get thrown out randomly.”

And now we wait, will she want to see me again?

(Messages and DMs welcome. I enjoy hearing from you guys and girls.)

Source: reddit.com/r/gonewildstories/comments/qp4c45/she_was_disappointed_i_didnt_wear_my_work_boots_mf