[MF] MILF from the bar made me cum twice in my car

About a month after a breakup, my friends decided to take me out to a bar to cheer me up. We're all sitting around a table when my friend Shawn taps me on the shoulder and points out a woman waiting at the bar for a drink. She looked a bit older than us (I was 23 at the time), but was stunningly gorgeous. She was very short and petite, her skin was overly tanned, her hair was bleached blonde and viciously straightened and styled. Despite being very thin, she was wearing a grey long-sleeve shirt that was just a size too small for her, showing off the shape of her huge rack pushed up tightly under her chin. Below that, she had on thin black leggings that showed a subtle outline of her underwear, and below that, a pair of white sneakers. Everything about her screamed that she was a woman trying to maintain her beauty. I decided to approach her.

"How was your run?" I asked.

She looked up at me in confusion, "how'd you know?" I pointed down at her shoes, covered in dirt. "That could've been from yesterday."

"Well then how was your run yesterday?"

She gave me a half-laugh, then said, "sorry, I'm here with my coworkers or else I'd love to stay and chat."

"Understandable," I said, "I'm here with my friends, so I'll just give you my number. Text me if you get bored." I wrote my number down, passed it to her, and rejoined my table. The guys wanted desperately to know if I'd gotten her number, and I told them we'd have to just wait and see.

Our tables were on opposite ends of the bar, but still visible to each other. I caught myself peering over from time to time, and got caught looking once or twice. Eventually, I got a text:

"What are you looking at?"

"You"

"My coworker saw you and asked if I knew you"

"Did you tell her 'not yet'?"

"Lol well I'm bored now so entertain me"

"Bar across the street?"

"I can't just leave"

"Tell them something came up"

"Ok"

I watched as she slid her phone back into her purse and started apologizing to her coworkers. I told my friends what was going down, thanked them for picking up my drinks, and told them I'd keep them updated. We walked to the bar across the street and I ordered us another drink each. We talked about what brought each of us to where we were that night. I mentioned my breakup, and she gently rubbed my shoulder. She said she hadn't had much luck dating recently either, but that she was trying to get out more now that her son was old enough to take care of himself.

Wait, what?

Pregnant at 19, her boyfriend knocked her up and skipped town immediately after the baby was born. Now 35, her son was a teenager and finally mature enough to be left alone. It was a big shock to a younger me, who had lived a relatively sheltered life and never considered the possibility of having a child so young, so being in your early thirties with a teenager barely computed.

"I'm sorry if that's a mood-killer on this night," she said, "but I understand if you want to walk away."

"No, no. It's fine. I just want to be clear that I'm only 23 and not really looking to... get involved with..." I trailed off a bit, trying to find the words that wouldn't hurt her.

She laughed and said, "I know you're young. Maybe I'm crazy but I'm having fun tonight, and want to keep thinking about tonight, not tomorrow."

That was a hint even my dumb ass could pick up on. I reassured her that her being a mother and the age gap didn't bother me, in fact I kind of liked it. I leaned in and kissed her. We made out there in our little booth for a minute before realizing we were that gross couple making out in a bar. We laughed, and remained close to each other. My hand rubbed her thigh.

"It's been a long time since I've done anything crazy like this," she said, "in fact, I've been in a bit of a dry spell since my last breakup."

"That's okay, I can do the driving," I said.

She asked if I had my own place, and I apologized since I was still living at home at the time.

"We could take this to my car," I suggested.

She laughed, "now that's something I haven't done in a looong long time. You’re doing a great job making me feel young again."

We walked back to my car, which was located in the center of the parking lot. We got in and I reparked it somewhere more private around the corner. As soon as I put the car in park, she leaned over the center console and we started making out again. We could barely keep our hands off each other, and were getting really handsy. I reached my hands under her tight shirt and began lifting it. She took over, and lifted it all the way over her head to reveal her massive tits in a blue bra. Aside from that she was very skinny, maybe a little too skinny, but it didn't bother me since I was the same way at the time. She leaned over and started taking my pants off. My cock was oriented facing down my leg, so we had to pull my pants down quite far before it sprang out for her. She let out a subtle, "wow," then put her hands around it. Her hands were so small, it made my member look massive comparatively. She gave it a few strokes before leaning all the way over to suck on it. I could tell it had been a while since she'd done this, but once she got going, she was very skilled. My girlfriend before this prided herself on being "the best blowjob in town," but this woman gave her a run for her money. I actually had to stop her or else I knew I was going to cum fast.

"Crawl into the back seat and take your leggings down," I said. She smiled at me and obeyed. My cock throbbed as I watched her crawl over, her panties barely visible through her thin leggings. I was a bit too large to do the same, so I covered myself up and got out of the car to enter through the door. She was already there waiting for me with her legs wide open leading my eyes directly to her beautiful brown bush. I closed the door behind me, undressed myself again, and put on a condom. As soon as I was on top of her, I felt her reach down and grab my cock again. She guided it into her pussy, and wrapped her legs around me to bring me closer in. I kind of sat there in shock for a moment before I started fucking her. As soon as I got moving, she let out the loudest moan I'd ever heard.

"Ooh fuck yeah, own that pussy," she said with a growl, "I've been craving that young cock since you first approached me. I was at the table with my friends imagining you pounding me."

Wanting to live up to the hype, I fucked her harder and faster. She was an incredible dirty talker, and there was a lot of it.

"You're fucking huge. I want to make you cum. I want you to honor me with your big load."

She rubbed her clit with a fury only a woman could do after years of understanding her own body. She tensed her neck and threw her head back as I pushed myself into her again and again. She let out a loud screaming moan once more.

"You're so hard, I love the way it feels deep in my stomach," she said.

I kept pounding her with all I had in me, trying my best to cum for her.

“Oh fuck, you’re gonna make me cum,” I said. I kept fucking her as hard as I could, and she was screaming for me to cum. I made one last big stroke before my cock swelled up and started filling the condom with so much cum I thought it would overflow.

“Oh yeah that’s it, I fucking love that,” she said.

We laid there for a while with me resting on top of her. Our bodies were sweaty and sticky, we were both breathing heavily and the car windows were all fogged up.

I eventually slumped back in my seat and laughed. We sat in the backseat for a while talking about our sex lives. I told her about my limited experiences thus far in life, including some stories that I’ve definitely told here. She told me about the long string of lovers she’d gone through in the last few years, few sticking around longer than they can cum. All this discussion started to get me hard again, and she took notice. She reached over and started stroking me while we talked. The stroking eventually turned into sucking, then she asked if I had another condom.

I sat in the center of the backseat and she flipped her leg over to sit in my lap, facing away from me. She grabbed my cock in her hand and once again guided it into her with a deep moan. She rode me with passion, stopping occasionally to grind her pussy on my dick. Her bare ass flattened on my stomach as her hips moved back and forth. She stopped momentarily to catch her breath.

“I’m going to be honest, it’s been a long time since I’ve had a cock this thick,” she said. “So sorry if I’m not doing my best, it’s just a lot.”

I told her she was doing great, and I wasn’t lying. Even having just cum not long ago and wearing a condom, I was already getting close.

“Turn around, I wanna see your big tits while I fuck your tight pussy,” I said.

Again, she obeyed. She spun around and squatted on my cock again. Her huge tits were right in my face for me to kiss and suck, causing her to moan louder.

“Cum for me, baby. Cum for me,” she said while riding ferociously. I reached my arms around her and began thrusting into her with force until she was screaming.

"Your pussy is amazing," I said, "I've never felt anything like it. I wish we could go raw so I could fill you with my cum." That was stupid of me, I'll admit, but it was the heat of the moment.

"Will my mouth do?" She asked.

"Absolutely," I said.

She hopped off my cock and took the condom off. She knelt on the seat beside me and started sucking. With the way her mouth and hands were working, it didn't take me long.

"I'm cumming," I said. She held my cock in her mouth as I pumped my load down her throat. She was moaning the whole time. As soon as I finished she lifted her head and swallowed the whole load. She eventually got up and started to get redressed. I followed suit, and we got back in the front to wait for the windows to defog.

I drove her back to her car and we went our separate ways. I texted her the next day and we had a short exchange, but after a few texts she stopped and never talked to me again.