How I Met Your Milf

When I got my first job in the tech industry it was right after the big dot com boom. The team I worked with was made up entirely of girls, most of whom were Asian. When we went out to lunch together as a team, one waiter once said I was a really lucky guy. I would say for the most part I have been pretty lucky. I wasn't like some playboy fucking all of them, but I did get to know some of them very well.

One of my coworkers was a tall older Korean mother. Most the Asian girls I've known tend to be really short, so when I meet a tall one they always catch my eye. Even though she was a fair bit older than me and a mommy, we still got along really well, working together on several projects but the most physical we'd ever gotten was one of us leaning over the other shoulder to see a computer screen better. That happened a lot, but I have always been hoping for something much more.

Then there was the big end-of-year company holiday party. A nice open bar meant everyone had their guard down a bit. All the girls were fun and flirty, but I spent most of the night with the Korean MILF. She was wearing a stunning pink dress with thin transparent straps on her mostly bare shoulders. It had a small V cut down the middle showing off some of her cleavage that I'd never gotten a really good look at before. It took a lot of willpower to not get caught just blatantly staring at that cleavage all night.

She was really cutting loose that night because her daughter was staying with her father for the night so she could stay out as long as she wanted. I caught her on the dance floor and I wouldn't say she's a great dancer, especially in heels but her clumsy movements got her rubbing against me and even falling onto me at some point. All the girls being a little tipsy were bumping into each other a bit, but when smaller girls run into you, it's easy to not pay much attention, but when a really tall one is falling into your arms, you just have to catch her.

I ended up being her designated walking assistant towards the end of the night. She was staggering around a fair bit. The company made an announcement reminding us that if we had too much to drink we could get a room at the hotel where the event was being hosted and then we could expense the cost of the room to the company. My tall staggering coworker seemed like she needed to take advantage of that offer, but she was hesitant because she'd never done the whole expensing process at work. As I'd had some experience with it from a company trip I went on, I offered to get a room and handle the expensing so she wouldn't have to. She loved that idea, so I got us a room.

It was pretty late when we got to the room and we were both pretty tired. With the lights turned off, we both undressed out of our fancy clothes down to our underwear, and got into bed together without really peeking too much. And even then being mostly naked in bed together we still were talking to each other like normal about who we saw at the party and what was the best food. Eventually, she stopped responding though. I told her good night without a reply and fell asleep myself as well.

In the middle of the night, I woke up with her arm and leg wrapped around me. I thought to myself, "oh okay, we're hugging now" and went ahead and put my arm around her as well. Once I was touching her bare back I couldn't help but feel up and down along her body. Instinctively she started doing the same feeling around my body with her hands. She would occasionally hug me tighter, pulling me close against her body and then releasing me so she could continue exploring my body with her fingertips. I ran my own fingers through her long dark hair and then down her back to her bra.

I tugged at the back of her bra teasingly and to my surprise it came undone very easily. When she felt it come loose she gasped a bit and turned away. From behind her, I rubbed her shoulders a bit and then started reaching down the front of her more and more until I was touching the inside of her loosened bra, cupping her breasts. I gently squeezed her tits a bit and playfully rubbed her hard nipples some with my fingers. She must have enjoyed my touch because she slipped out of her bra completely and then turned around to hug me again, this time pressing her bare chest against mine.

We started rubbing our bodies against each other. All of our skin sliding against each other felt incredible. I kind of awkwardly pulled her underwear down her long legs and off her feet and quickly got out of mine as well. With nothing between us anymore, I got on top of her, between her moderately spread legs. I rubbed my hard cock through her hairy pussy as we continued rubbing against each other. I reached down with my hand between her legs and felt her pussy. I slipped a finger slightly inside her a found her pussy to be extremely warm and wet. She let out a gasp when I did so. I froze for a moment.

"It's okay." she finally whispered.

I started moving my finger in and out of her a little and her whole body started moving. She was so sexy. I could not wait any longer. I pulled my finger out of her and grabbed my hard cock and guided it into her pussy rather forcefully. She let out a yelp as I did so, but I was so horny I pushed all the way inside her and started fucking her.

More sounds came from her mouth. It was a combination of whimpers and moans. They got louder as I started fucking her harder and faster. Her hands reached around and grabbed my ass, digging her nails into each cheek as I continued moving in and out of her.

After a few minutes, I felt my cum building up in my balls. I slowed down a little, enjoying the feeling of her pussy wrapped around my cock. I fucked her right to the edge of cumming and then held still inside her, still holding myself up over her with my face just an inch or so from hers.

She suddenly moved upward and kissed me. It was a long and unbreaking kiss. After a few seconds, her tongue invaded my mouth and slid alongside my tongue which was happy to dance around with hers. As she continued kissing me, she started moving her own hips up and down, sliding my cock part way out and back in repeatedly. The feeling was amazing. I knew I couldn't hold back from cumming anymore.

I started to pull away to tell her, but she grabbed the back of my head and held me close so our mouths stayed sealed together. I attempted to mumble "I'm gonna cum" directly into her mouth, but she still did not seem concerned and continued her movement. Sure enough, a moment later I moaned loudly into her mouth as gobs of my cum started erupting from my cock inside her pussy. She continued moving her hips up and down, milking every last drop of cum from me with her pussy.

Finally, I collapsed next to her. We continued holding each other and stroking every part of each other's bodies for a few minutes. Then she slid under the sheets and put my wet cock in her mouth and started sucking it. It felt incredible since I had just cum and it was so sensitive at that point. After a bit it was actually feeling so strong that I couldn't take it. I pulled her back up from under the sheets.

"What? Is it not good?!" she asked worriedly.

I laughed a bit and told her, "It's TOO good."

She giggled as well with relief. Then I disappeared under the sheets. I started moving down her body but paused at her tits and began sucking on them for a little bit. She moaned and kicked at the blankets a bit. I rubbed her wet pussy at the same time which made her grab onto the bed with both hands as she continued semi-thrashing about with her legs. I took turns sucking one nipple and then over the other, back and forth for a bit.

Then I slid further down past some thick bushy hair and then tasted her pussy. It was salty and sweet and sopping wet. I could taste a bit of my own cum in her which I generally am not too fond of, but I still ate it all up. I took turns diving my tongue as deep into her as it would go and then when I pulled back gasping for air, I immediately slipped in two of my fingers. I alternated back and forth like this until she scream with pleasure and a gush of wetness filled my mouth, drowning me in her pleasure.

Making her cum had turned me on so much that I was hard again. I slid back up on top of her and started fucking her a second time. She didn't cling to me like she did the first time but mostly just lay there, as though her body had been defeated. She still moaned though each time I pushed my cock into her. I held myself up with one arm and played with her boobs with my free hand. They were quite big for an Asian girl. I figured it must have been because she was a mommy. I continued fucking her like that for a few more minutes and I felt my next orgasm building inside me.

When I got close to the climax, I pulled out quickly and straddled her stomach, placing my wet cock between her big boobs. I squeezed her boobs together and started fucking them. She started to ask what I was doing but before I could really reply, I suddenly groaned out loud and start shooting cum through the dark all over her neck and face. She squirmed a bit under me to attempt to dodge the streams of cum, but with me straddling on top of her, she couldn't really escape it.

When I finished cumming I got up off of her and stood next to the bed. I turned on the lamp on the side of the bed and saw where my cum had landed (all over her face and neck with small drops of it on her upper chest. She had her eyes clenched shut to keep the cum from dripping into them. I apologized and grabbed a couple of towels from the bathroom. I gave one to her which she immediately used to start wiping her face off. I used the other one to help clean her up as well. Then just stood then admiring her naked body which I was now seeing more clearly for the first time. Despite her age she was fit and fairly slender without any wrinkly skin that I could notice. When she saw that I was staring, she immediately turned off the light and turned away from me.

I got back in the bed behind her and spooned with her, holding her close to my body.

"You're amazing," I told her.

"I'm old," she countered.

"You sure don't look like you're old," I argued. Then cupping her boob in my hand I continued, "And you sure don't feel like you are old."

She ceased her argument, I looked at her and I thought she was smiling, but since the light had been on my eyes were still adjusting back to the dark and it was really hard to tell. I just lay there quietly with her, still riding down the euphoria from having cum a second time with her, and eventually drifted off to sleep.

When I woke up in the morning, I was still spooning with her. Sunlight was starting to peek through the edges of the curtains on the windows. She moved a little bit, snuggling close to me. I think it was her movement that woke me up. My morning wood was pressed tightly against her ass. I gave a little push against her ass and it felt pretty good, not even being inside her. I started a little dry humping of her like that, getting hornier and hornier.

Then I reached down and guided it into her pussy. Her pussy was still warm and a little wet but not as much as the previous night. Once inside her, I continued my humping, enjoying her pussy yet again. I looked around her long dark messy hair and her eyes were still closed. I was enjoying every bit of her pussy, pulling my cock almost completely out before pushing all the way deep inside her. Her pussy wasn't the tightest I had felt but it still felt pretty great. All the way in and all the way out was making every inch of my cock feel pleasure. One of the times I was pulling out it slipped out completely.

My hands were busy playing with her tits, and my cock was so hard I tried to just push it back in without guiding it with my hand. I tried pushing in her a few times but it wasn't sliding in. So I attempted to clench, making my cock stand out a bit straighter and it felt like I had found the entrance that was wrapping around the head of my wet cock. I started pushing it in, but it felt a lot tighter as if she was clenching her pussy hard to keep me from going back in. Slow and steady I kept pushing until it was about halfway inside her, but I was a bit confused.

Usually, when there's resistance, it's only as I'm first trying to push inside. Once I have the head, in the rest goes in pretty easily, but at that moment it seemed to be giving me resistance even with my cock halfway in. Also it didn't feel as wet as it did a moment ago. I let go of her boob that I had been fondling and reached down to her pussy and found that I wasn't in it!

I had my cock half inside her ass instead. I look at her face again and her eyes were still closed. A million things raced through my mind. Most of my girlfriends never let me fuck their ass, so this seemed like a prime opportunity but I also didn't want to ruin this thing I had just started with her. All the while, as this debate was going on in my head, my body was instinctively pushing slowly deeper into her ass. Eventually, I decided it wasn't worth the risk of upsetting her, but it was still feeling so good and tight.

Even though I wasn't moving much I felt like I was really close to cumming. So I pulled out of her ass a little, but with about half of my cock still inside her ass, I started stroking it and sure enough in less than a minute I started cumming inside her ass. Oh man, it felt so good. What a way to wake up in the morning. I slowly pulled my cock out of her butt and to my surprise there wasn't much of a mess. Just a little bit of my cum leaked out of her but she must have kept the rest inside her.

I went back to spooning with her for a bit but I was too excited, I couldn't fall back asleep, so I got up. With the room brightening up more, I got another good look at her naked body. She really was sexy. I couldn't believe how lucky I had been. I used the towel from the night before to clean up some of my cum dripping out of her ass and then tucked her back in under the sheets. I went to the bathroom and took a hot shower and came back out of the bathroom expecting her to be awake, but she was still sleeping. I lay next to her and started checking messages on my phone.

The room kept getting brighter. I had been awake so long I was starting to get hungry. I thought that it would make a nice surprise to order breakfast to be ready for her when she woke up but then wasn't entirely sure what she normally ate for breakfast as this was our first morning together. The naughty side of me also fantasized, what if I gave the room service guy a good look at her naked body or even better, let him fuck her. My top fetish is sharing my girls with other guys. So thinking about the room service guy earning his tip by kissing every inch of her body and servicing her pussy got me more than a little excited.

All of my thinking ended up not mattering because there was suddenly a loud knock on the door. It was housekeeping. It turned out that checkout was at 11 am and it was 11:43 am. I talked to the cleaning ladies through the door and told them we'd be out as soon as we could. My coworker was finally awake with all the noise and scrambling to get dressed when I turned around. She already had her underwear on and was trying to get her bra on. I went over and helped her out with her bra and started getting dressed too.

"Good morning." I hurriedly told her.

"Uh yeah, good morning," she replied while trying to get her dress on as she disappeared into the bathroom.

We did get out of the room not that much later and went to a restaurant at the hotel for breakfast. She kept apologizing that when she drinks she tends to oversleep the next day. I told her it was perfectly alright and that I had a great time with her. We ate breakfast kind of quickly without saying much of anything to each other. Then she broke the silence.

"How was it?" she asked.

"I wish there was more cheese in the eggs and I tend to prefer sausage patties over the sausage links they served but overall it was pretty tasty. The orange juice was definitely the best part." I delivered as a mini-review of breakfast.

"No, I meant, last night. How was it?" she clarified shyly.

I felt a wave of embarrassment sweep over my face.

"OH! How was that! Well, that was simply amazing!" I exclaimed and I reached across the table and held her hand for the first time in public. She looked at our hands with a smile and visible excitement on her face.

"I'm glad." she managed to say in return.

We made idle small talk for a bit after that. I did confess that I had a concern about the first time we did it when I finished inside her. She told me not to worry and explained that she had no longer been getting her period anymore and could no longer get pregnant. So I could cum inside her as much as I wanted without worry. She saw me get very happy with that news and then clarified just not right at that moment because she had to go pick up her daughter from her ex-husband's house.

Later on, I found out she hadn't really dated much since her divorce. The next week, she started inviting me to spend the night at her place. I was happy that we ended up not being just a one-night stand. She had lots of sexy lingerie and silky nightgowns that she loved teasing me with. We quickly learned what kinds of things we could do to turn each other on. It was also kind of kinky making her moan every night knowing that her teen daughter could hear from across the hall. But that's another story.