Filthy Fourth Date [MF]

I couldn’t believe what I’d heard, did she really just say that?

It had been a month since our third date, and here we were now on our fourth. Our first three dates were casual affairs. 30 minutes at a low key coffee shop. The second, a simple walk around Cal Anderson park. For the third we walked from Ballard locks to the shore in Discovery park and sat as the sun set behind the Olympic mountains. With each date we’d gotten closer.

On our second date, we held hands as we walked and parted with a kiss that held all the charge of anticipation. As we watched the sun setting on our third date, we were in full contact. I held her tightly around her firm waist, to feel every breath. Our bodies pressed side by side, from shoulders to calves, while we talked.

It was a rare connection. We are both busy executives, constantly traveling to visit customers and offices until the pandemic lockdown kept us working from home. We talked about our favorite coffee shops in San Francisco, New York, and London, as if the world were our neighborhood. We shared a small sigh at how many people never seem to get to the point quickly enough and just vent at life rather than steer towards a better outcome.

We talked a little about our past relationships and how they there were fine but would fizzle. We both agree that this life is all that there is, and that we still want to commit all that we will ever get to someone else. But it’s not worth compromising on happiness. We won’t settle for anything but the best. And so here we were, both single in our late thirties. Great careers, nice houses, financially secure, but nothing else to show for it.

The conversations on our walks had been a mixture of the kind of trivial observations, deep and personal insights, and occasional innuendo that make a great date so fun. Our last date had ended with me saying “I’d really like to see a lot more of you”. “I bet you would” she replied with a slight giggle and a grin.

She’d worn yoga pants for our little trek to the water, and as she walked away, her perfectly toned body swung with the confidence that makes her so attractive. She’s 5” 3’ and at 120 pounds, and is somehow both tiny and toned but deliciously curvy from firm C cups and a butt built on daily squats, each all the more prominent because of her slight waist. Despite her stature, she can command a room and is an absolute force of nature. She is certain of every sentence that she utters and I’ve yet to hear her hesitate. Every nod and gesture brims with unfazed poise. It’s easy to see why she’s Vice President of marketing for a big tech company.

After that date, we both had to travel. With the lockdowns ending we had new hires to visit in other cities. People we’d worked with for almost a year, but never met in person. Customers we’d had difficulties with who needed some love. I was off to Boston, while she had to visit the Washington DC area. Same coast, same time-zone, but too far apart to go for any walks together.

We built a little routine of long rambling phone conversations from our hotel rooms, catching up on each other’s day. We learned about each other’s families and friends, college experiences, pet hates, favorite foods. All of the things. Our text messages were more racy. After one of our first long conversations, I sent her a simple message “I feel a little stiff after laying here with you so long”. Not exactly top innuendo, but it was late. Her reply was swift, a heart reaction on my message and “I feel touched myself”. We were on. The next hour was a back and forth of messages that certainly ended in mutual orgasms, without ever being quite so explicit about it. Her last message to me that night was “I bet you have a fine sense of taste.”

Three days later she called me at 3PM, which was a little unusual, we were both still working. I answered right away and she asked “It’s ok to say no, but I need a quick answer. DC is getting back into the swing of things and I’ve been invited to a comeback gala for a political group I’m involved in. Could you be in DC this weekend?” “Sounds great, what’s the group? What’s the dress-code?”, I asked. “A simple suit and tie would be great, not a tux, it’s a group for better gun safety laws. Thanks, I can look forward to it much more now. Have a great evening.” and that was that. In less than a minute and just three sentences we’d arranged our next date. While I started composing a message to my assistant “Can you get me to DC for the weekend please?”, another one came in. “Don’t book a room, I have space.”

As it happened, I had a dinner with clients in Boston on the Friday evening that I couldn’t get out of, but I flew to Dulles the next day at around 3 and made my way into the city. We were to meet at a bar at 7, before the function, because she’d be spending the day shopping for the right dress. I used the time to wander down the national mall. I’d never done it before, and it was a perfect day for it. Not too hot, not too cold, and if I’m honest, plenty of younger women in yoga pants to be a nice distraction. But whenever one would run by I couldn’t help but think of my date. I missed her, and I was anxious to meet up, and I was nervous about what the future could hold. Is she the one?

She is already perfect in so many ways, but I found myself wondering if we would be a good sexual match. I desperately hoped so. I’d made connections before only to be dashed and disappointed when it turned out they were terrible in the bedroom, no matter how patient I was. I enjoy sex a lot. I work hard, I work out, and I’ve spent a lot of time getting good at sex. A lot of reading, a lot of learning from good amateur and women-focused porn, and a lot of bringing enthusiasm and energy to the bedroom. I’ve fucked women hard until they were a ragged worn-out mess. I’ve had women look me in the eye and count every orgasm until they can barely say the words. I know exactly how to reach a woman’s g-spot, when to keep doing exactly what I’m doing, and when to throw in a surprise or a change of pace. I’ve had friends with benefits and exes who are happy to fuck any chance we get. It would be a real shame to be stuck in missionary.

Half-way through my walk down the mall I got a picture message of black lacy underwear. What a way to get started. I sent my own heart reaction back. “I can tell already it’ll be more like 7:30, but worth the wait” was the next message. She was running a bit behind. I started heading towards the bar anyway, but slowed by walk to take in the cherry trees and spectacles that lined the city streets. My walk took me past the Whitehouse, with its tourists and protests and secret service agents. When I got to the bar, I grabbed a booth by a window and ordered a Guinness. “It’s good here” the server said.

Just about 7:45 exactly my date walked in. She was wearing a short red evening dress. It was stunning, low cut but not slutty. The hem stopped in the middle of her thighs, but it was light and flowing, which suited the DC summer. I’d never seen her bare legs and wow they were incredible. She was also suddenly 4 inches taller in elegant silver heels and held her Louis Vuitton handbag by its edge, more like a weapon than apparel.

She sat down in the booth. Beside me rather than across. She effortlessly caught our server’s attention and ordered a Moscow mule. While he was still making his way from the table to the bar, she leaned in to me and quietly, but not so quietly that our server might not hear, said “When we’re done tonight I want your cum in my tummy”. I couldn’t believe what I’d heard, did she really just say that? She pulled back, took a sip of my Guinness and looked me right in eyes without saying any more.

Instantly, I was hard as a rock. I’m not used to dress pants. They are much lighter than the jeans I normally wear, and it definitely felt noticeable. I was not going to be getting up from this table any time soon. I felt out of control of my own dick, like a teenager in high-school. I was stunned. I hadn’t expected her to be this forward this quickly, but also at the word “tummy”. I’d never heard this woman speak in anything but the most mature ways, but this was very playful. Her words and her look were telling me in no uncertain terms that she could be submissive and that she’s looking forward to to swallowing my semen, a type of intimacy that not every woman is up for.

We chatted away innocuously while my hard-on subsided, and when we’d finished our drinks we went on to the function. It was in a marquee tent behind a hotel and the guests were a mix of high-spending donors, and DC staff who’d helped elect Mark Kelly as a new Senator for Arizona, and some DC Nasa staff who had worked with him from his time as an astronaut. This wasn’t an A-list function, neither the senator nor his wife was there. More like an appreciation event for the behind the scenes people.

It was a fun night and I had a great time talking to people, but I’d be lying if I said that I wasn’t constantly distracted by what my date had said earlier. All I could think about was what she was going to look like obediently on her knees. There’s nothing more gratifying in life than having a sexy woman, with her own power to exchange, sucking freely from you like a fountain of pleasure. Would we also get to fuck? Is she bare, trimmed, or natural? What kind of nipples does she have? My lust for her was all that I was on my mind.

Neither of us are big drinkers, after our drink at the bar, we stuck to virgin cocktails at the event. By midnight, when the crowd was starting to thin out, she asked if I wanted to go. I couldn’t have been keener. She’d parked at the hotel. We took her ticket to the valet, who came back driving a gleaming silver Tesla Model S. “I have a company car for the weekend, but in these heels I want you to drive” she explained. I got in the driver side while the valet held the door open for her. I could see the grin on the valet’s face as she got in to the passenger seat. I’m pretty sure he got a real show as bent down to get in.

Before I had a chance to ask, she typed in the destination address into the center console and hit the navigate button. So that’s where we’re going. She leaned her seat back and let out a relaxed exhalation. “Oh I really needed to sit down” , she’d been standing in her heels for most of the event, talking to acquaintances, making new contacts, and chatting me up.

About a minute into our drive she rustled in her seat, put her handbag on the ground between her feet, and she reached beneath her dress from below. With a little shimmy down her legs off came the same lacy black underwear I’d seen earlier. No words, her actions were explanation enough. She put the underwear in her handbag and she was now bottomless beneath a very short dress. As we drove for the next 10 minutes she opened her legs. Not enough for me to see anything, but enough to constantly distract me and remind me very directly that there was pussy to be had. I couldn’t smell it, but I could almost smell it.

“Tell me now if you’d rather not have get intimate, this is our consent conversation.” She was looking dead ahead while she said it. “And we might need a safe word. ‘Red’ will do just fine, or a ‘nuh-uh’ sound when talking isn’t an option. There’s no need to complicate it.”. I was rock hard again. “Yes, yes” I said while driving.

When we got to her hotel, we parked ourselves in the underground lot and headed directly up to her room holding hands. When we got to the room, I wasn’t sure how I was going to contain an explosion of sexual tension, but she skipped ahead of me. “I just have to freshen up, why don’t you sit here”. She placed me sitting on the edge of the bed. At my feet was a plush thick piled rug, maybe 6 feet square, half under the bed, half extending out. It almost seemed tailor made as a blowjob pedestal, and it made me wonder if she been planning. She seemed on a mission.

About five minutes went by and she returned, still dressed exactly as before in her red flowing dress and heels and she climbed up on the bed behind me. She put her hands on my shoulders and gave me a deep firm shoulder rub that was just perfect and said “I want you to relax, close your eyes.” She leaned me back into a lying position. “Just relax there. Keep your eyes closed.” I took a slow deep breath in. I really was perfectly relaxed at the end of a perfect evening, with an absolutely stunning woman, wondering what was next. For a few seconds I thought whether she was going to undress, or would she undress me. Was she going to blow me right now?

Before I had too long to wonder, she shifted in her position and I suddenly felt a warmth and pressure on face. My entire world was now the inside of her dress, her pussy pressed to my lips, with her clitoris just above my nose. I did not expect this, but if you put a pussy in my face, I am going to eat it. I started licking her labia and mound, to orient myself. She was smooth as silk. Either with wax or lasers I’m guessing. Not a stitch of hair or any hint of stubble.

I alternated unpredictably between the sides of her pussy, and placed small kisses on the insides of her thighs. I wanted her to know that every tiny piece of her privates tasted delicious as I worked my way slowly towards her clit. I reached up with my hands to her butt to reposition. I got a good feel, briefly, but she took my hands away and intertwined our fingers. She tensed and pressed down and made it clear that she was in charge.

I kept stroking with my tongue. “I have a rule in the bedroom” she said, leaving me with no choice but to listen. “I like to serve, I can be very submissive, but I also come first. And second. And third.” I responded by licking her clit, not too firmly for now, but just enough to let her know that I know exactly where it is, and then by extending my tongue as deep into her pussy as I could manage, before returning to what I’d been working on. “If you know what you’re doing, I can come easily enough from cunnilingus. Fucking is harder, I like to be taken hard, and I need to feel full and stretched. I don’t know how big you are yet, so I’m not taking any risk of being disappointed with your cock before I have some fun. And we won’t be fucking tonight anyway.”

My mind was working almost as hard as my tongue. Here I was with my head inside her dress, her hands clamping mine, as she casually emasculated me. I was to make her orgasm, three times, on her terms. I lay there thinking “Is my cock big enough? I know it’s a little bigger than average, I’ve looked up the stats, but it’s not massive. If she’s disappointed is she still going to blow me? Are we over after that? Before that? Is she just fucking with my head because she can?”

As my tongue started to stroke her clit in earnest, I could feel her breathing begin to speed up. Her fingers grew tighter. “Good boy. I’d hoped you could eat pussy like a pro. Keep at it, just like that. You’ll know when I come.” I did as instructed. Her breaths began to vocalize, a loud soothing series of “ah”s began to build up. She let go of my left hand and grabbed my hair tight, pulling me towards her pussy as hard as she could manage it. “Don’t stop. Do not stop” she hailed before a long pause in her breathing. I could feel the strength of her sweating thighs pressing on my head. Just as my ears popped from the pressure, my mouth was flooded. I felt a warm salty taste, like a mouthful of Mediterranean sea-water on a hot day. She let out a giant breath and started panting.

“That was good” she added, her hands still firmly in my hair. “You’re not done, that was one.” I had no other reaction to go by, still locked in her dress, seeing only a diffuse and dark red light everywhere. I started licking again, focusing on the clit from the beginning this time, but very lightly. Like barely flicking a pencil eraser. “Obviously, I squirt” she said without a hint of self-consciousness about it. I responded by pressing harder on her clit. “A little slower” she directed.

I went more slowly, but within two minutes or so she was riding my face. I kept rolling my tongue and centered it on her clit, but really I was a human tool for her humping. Again her breathing stopped, but not quite as long this time, before she tensed up, this time shaking, and she flooded my mouth again. Less fluid now, but still as warm and just as salty. I let out a sound of enormous satisfaction.

“Let’s get you out of there” she said before shifting off of me. I could now see her flushed face and sweaty skin. She had a gigantic grin, which was gratifying. I immediately kissed her, completely covered in her juices, and we held a passionate tongue twisting kiss while I loosened the back of her dress and got it off like a flustered wrestling match. I could finally see her perfect nude body. Her breasts were firm with delicate small nipples. Somehow better than I’d ever imagined.

I reached down to pinch a nipple and she let out a moan. I pinched harder and her moan got loader. “Are you good your hands?” she asked. I reached down a put a hand between her legs. She was soaking wet. We weren’t going to need lube. Still, even with just one finger in, she was tight. She was laying down now and while we kissed I held her right hand tightly with my left and then with my right hand I lightly massaged the inside of her pussy before working a second finger in. I have long sensitive strong fingers and perfect rhythm.

Before working in customer relations, I’d played piano professionally and still play at a professional level occasionally. I reached up until I could feel the slightly bumpier texture of the skin covering her g-spot, while pressing down from the other side with my thumb just above her clit. When worked up and fully lubed, her pussy could take quite a bit of pressure. She shuddered and grabbed my arm, her neck craned and her eyes rolled back into her head she just said “oh my holy fucking Jesus”. I took that as a sign to go on.

I flipped her over, to lie on her stomach, continuing to work my fingers but now I could press down on her g-spot from above and behind. Small but firm strokes, like scrolling on a trackpad. With my other hand I smacked her butt hard enough to leave a butt, and then grabbed her hair from behind. Now she was helpless. With her hair in my hand and my fingers in my pussy she just gave up and relented to my control. I worked her for maybe a minute before she exploded into a sweating whimpering mess. She curled up for a minute and shivered.

We just lay there for a few minutes to recover, and she simply said “amazing”. All this time I was still dressed, but decided it would be a good time to do something about that. I took off my shirt and pants while she lay there, but kept my boxers on, still a bit nervous about what she might think. At least I was rock hard, which would help. “Your turn now” she said with a smile, before reaching into a nightstand. I thought she might be reaching for a condom, but instead it was a hair tie and handcuffs. She put her hair up in the tie, and gave the handcuffs to me just before standing up, fully naked, and presenting herself to me hands behind her back. “Fair is fair. You didn’t get to use any hands.” Is all that she had to say. I cuffed her and she turned around to face me on her knees.

“Stand up please” she began, before she started put the waistband of my boxers between her teeth. She pulled them down to my feet and I stood out. “I always like to impress” she went on, before kissing my feet and very slowly working her way up my legs, planting small kisses as she went. By now my cock was standing very proud, as hard as it has ever been. If she’d seen it, or noticed, she’d made no comment. The nerves inside me jittered as she got closer.

By the time she was at my thighs I could see that her eyes were closed. She paused there for a while, allowing the anticipation to multiply. Finally, and without opening her eyes, she planted a kiss on each of my balls and sucked each in turn, to a satisfying “mmmmm” sound. She then slowly licked her way along the length of my shaft until her mouth was at the tip of my cock, again pausing. She kissed the tip a few times, her lipstick leaving an impression. At last she opened her eyes and looked directly at me. I expected her to say something, but instead she simply opened her mouth and slowly descended. Bit by bit she kept slowly going down, eyes locked with mine, until she her lips were firmly pressed against my abdomen.

She let out another satisfying “mmmmm” and winked at me. I had been Deep-throated before, a few women I’d slept with could pull it off, but never like this. This seemed effortless. Then I felt something I’d never felt before. Pressure around the head of my cock, coming and going, almost like a hand job. I could hear short quiet glug sounds. My god, she was using a swallowing motion to stimulate me. Not only had she no gag reflex but she could jerk me off with her throat. If I came like this, it would be the express route, directly into her stomach. She paused again to breath, and she made a show of it. She was still as deep as ever, but could breath in through her nose and I could feel the cool breath across the head of my dick.

This woman absolutely knows how to suck a dick at the highest of levels. I had no words. I just stood there and watched this woman perform and create the most amazing sensations in my body. After another slow round of this, she released herself slowly down my dick and looked at me. “You can sit down if you’d prefer”. I sat. “You can fuck my throat, and you can come on my face or body, but I’d rather have your cum in my tummy. I hope that’s ok”. My god, what do you say to that. “That sounds great” is what I could muster, before sitting down to enjoy the most hoped-for blowjob of my life.

She resumed and before too long I grabbed her hair and pushed her down. She let out another big moan. I held her there, firmly, until she started to wriggle. She wasn’t struggling too hard, it was playful and not panicked, so I held my grip. She suddenly shivered and I could see new juices dripping between her legs and leaving a damp spot on the rug. A woman who can orgasm just from sucking dick is a precious find.

I released her and let her at it. She looked at me and then ramped up the enthusiasm, sucking as hard as I have ever had and going up and down, faster and faster, harder and harder. I could feel an orgasm building in me. This absolutely filthy woman wanted every drop of my load and I had no second thoughts or hesitation, no hindrances or worries that I would offend her.

I let it build and build and asked her “are you ready?”. She looked right at me, deep throated me hard, and nodded with a begging look in her eyes until I couldn’t hold it any more. The room disappeared and pale while light took over my vision as the most euphoric senses pulsed through my body. Through my shoulder blades, down my spine, my butt tensed up and then boom, I shot huge loads of cum right into her waiting throat. Even with a dick in her mouth, she couldn’t hide the smile of accomplishment on her face.

Instead of being done, she just held me in her mouth until I was done pulsing and starting to soften. Only then did she release me, again slowly. She licked me completely clean and savored every drop that she found. She put her mouth on the very tip of my penis and by pressing down she created another drop, which she held on her tongue for me to see before she swallowed it in a show of appreciation.

“Oh, I’m going to keep you” were her last words before rising from her knees, still cuffed. “I didn’t disappoint?” , “Oh no, you’re just right”. I reached for the handcuff keys and she turned around to allow me to release her. Instead I pulled on her hair again and smacked her butt. “Oh thank you” she said. We climbed in to bed and turned off the lights. Both worn out, but both glad to be spending our first night together as a couple. Just as I started to think about the night and come to terms with all of this happening she leaned in and said quietly into my ear “You can take my ass in the morning.” Now I was wide awake again. Did she really just say that?

Source: reddit.com/r/Erotica/comments/oaux3s/filthy_fourth_date_mf