My Mother’s Friend, the MILF, and the Night in the Car

This happened a few years ago, one July night, right on my mother’s birthday. I should clear up a couple of things so the rest makes sense. Back then I’d been training at the gym for months with a couple of friends and I was in the best shape of my life. I never lacked looks or flirtation, and every so often I’d take advantage of one when I felt like it.

To celebrate my mother’s fiftieth, we threw a dinner at home with the whole family and several of her friends. I stayed behind helping, welcoming guests, and carrying drinks back and forth. Uncles, cousins, women my mother’s age I’d known all my life, and others I’d never seen before kept arriving.

Among those last ones came one who, from the moment she crossed the threshold, took all my attention.

I opened the door myself, and when I did I came face to face with one of those mature women who look like they’ve stepped out of a movie. I admit that being with a milf was one of my unfinished fantasies, so I was already at a disadvantage. She introduced herself as Lorena. She was a little taller than my mother, wore pointed heels and a tight dress that outlined every curve: her firm breasts, an impossible waist, and rounded hips that looked hand-drawn.

She had a friendly face, a few discreet wrinkles that took nothing away from her, and straight hair falling to her shoulders. Apparently I wasn’t the only one who noticed: I caught one of my uncles staring dumbly, other guests turning their heads as she passed, and I saw how she was invited to dance over and over. But I also caught Lorena glancing at me more than once out of the corner of her eye.

That night I’d dressed formally, and since I trained, my T-shirt was tight, showing off my back and arms. The pants, which I didn’t like wearing so fitted, didn’t help to hide anything either. Every time I went over with a tray of wine or appetizers, I felt those women’s eyes sliding over me.

At one point, while uncorking a bottle, I looked up and there she was, openly watching me, giving me a slow smile. I got nervous, I won’t deny it, but it was an opportunity I wasn’t about to let slip. I kept doing my thing as if nothing were happening, and little by little I started flirting with her, subtle at first, bolder later, until I dared to ask her to dance. She accepted at once.

We danced for a good while. At first I laughed nervously because she grabbed my arms and squeezed them before letting out a laugh. But I relaxed more and more until we ended up pressed together, her breath on my neck, her laughter brushing my ear. And, as expected, I started getting hard.

I tried to pull away a little so it wouldn’t show, but she wouldn’t let me. She held me by the waist and pressed closer, until I felt my own erection rubbing against her through my pants. Lorena didn’t flinch. She kept dancing as if nothing were happening. Later she would confess that yes, she’d noticed it, and that she wasn’t about to pass up the chance to feel someone so young like that.

My mother interrupted us suddenly, and we separated. I was already rock hard. From then on we kept looking for each other across the room for the rest of the night, smiling at each other from a distance, although we didn’t dance again because her friends had her surrounded.

***

After two in the morning people started leaving, and then something happened that I’ll always be grateful for. My mother asked me to drive one of her friends home because she had no way back. And Lorena, quick as lightning, slipped in saying she might as well get a ride part of the way too.

So there I was, driving at night with two women in the car. Lorena sat in front, and I couldn’t stop looking at her legs out of the corner of my eye. That dress left nothing to the imagination. I couldn’t even talk to her because my mother’s other friend wouldn’t shut up for a second.

I put up with the silence the whole ride until the first one finally got out. Once I was alone with Lorena, nervous but thrilled, I started driving again and began talking to her. We talked about all sorts of things. I asked her age, she asked me how long I’d been going to the gym. It was all pure flirting. She even told me I was very handsome, that muscle suited me. I laughed, but I also noticed that her skirt had ridden higher than when she’d gotten into the car.

“So, are you single, kid?” she blurted out all of a sudden.

“Yeah. Why do you ask?”

“Because I caught you looking at me pretty hard at your house, and I was wondering if some girlfriend of yours was going to make a scene.”

“Not at all,” I laughed. “And hey, you were looking at me too.”

“Of course, handsome. Only when you were looking at me, you weren’t exactly looking at my eyes.”

“I was just appreciating how well you moved when you danced.”

“And did you like what you saw?”

“I can’t answer that.”

“Don’t be shy,” she insisted, amused. “Be honest. What do you think of my body at forty-seven?”

“That you look amazing.”

“Wow. You’re not bad at all yourself. And now that we’re being honest, tell me: have you ever been with a mature woman like me, or do you just like staring holes through me?”

“I wasn’t drilling any holes through you. I was paying attention to you, since I was the host.”

“Sure, sure. And when we danced, are you going to deny that part of you that got bigger too?”

I was already nervous and hard again, so I countered.

“You’re not going to tell me you didn’t like it, that you didn’t want to stay pressed against me.”

“Oh, kid. When a woman my age sees she can still turn on someone that young, it feels good. Very good.”

“So it’s not the first time that’s happened to you.”

“I wish it happened more often. But I hardly ever go out. My husband doesn’t like leaving the house, so I spend my time locked up.”

I saw her face tighten when she mentioned her husband. I didn’t wait any longer. I asked tactfully, and between one sentence and the next she told me her marriage was dead, that he was a bitter man, and that she’d cheated on him. She had a few drinks on board and she seemed fragile. I put a hand on her leg to comfort her, with no intention beyond that, and then she was the one who threw herself at me and kissed me.

I managed to pull over at the side of the street with her mouth already pressed to mine. Her kisses tasted like wine and she kissed damn well. I slid my hands down her back and suddenly she pulled away.

“No. I can’t do this.”

Hot from the whole night and with those kisses still on my lips, I started trying to convince her.

“Relax. Nobody will know about this. Nobody.”

I kept insisting gently until she gave in. We kissed again, this time with our hands free, exploring each other hungrily, until a police car slowly passed down the street and forced us to break apart and keep going.

***

Lorena stayed looking out the window, blushing, not meeting my gaze. We went on for a few minutes in silence until, without warning, she turned toward me and started unbuttoning my pants. I had to find a place to stop as fast as possible while she, impatient, struggled with the seat belt and the fabric of my pants, which, as I’ve already said, were tight on me.

As soon as I came to a full stop, the good part began. I held her face and kissed her again while I finished lowering my pants myself. I was rock hard. Without waiting, I ran my hand over the back of her neck and guided her downward.

Lorena bent down without saying a word. Her tongue focused first on the tip, licking slowly, before sliding all the way down and back up. She worked me like that for a few seconds, slowly, until she lifted her head.

“Jesus, what a cock you’ve got, kid.”

The truth is I’m not that big, more average really, but I am a bit thick, and that day I was nicely dressed. So I asked her:

“You like it?”

“I love it,” she replied with a smile before going back down.

She repeated it with more hunger. She took me deep, again and again, setting the pace herself. When she pulled back, instead of complaining, she looked at me with that mix of shamelessness and satisfaction, and then started over. She sucked me with an intensity that had me on the edge, then stopped on purpose, lowering her head slowly to drag it out.

Meanwhile I’d reclined the seat. I lifted her dress above her waist and stroked her hips, which were pushed out over the seat. I started exploring her, first gently, then with more eagerness, keeping one eye on the street so nobody would catch us.

It went on for a good while, though to me it felt endless. Lorena sucked my cock as if she’d wanted it for years, making sure I was enjoying it, while I caressed her back and neck. At one point I tugged at my shirt and took it off completely. That seemed to turn her on even more: she let go of what she had in her hands and licked me from bottom to top, slowly, all the way to my navel. My whole skin prickled.

“Fuck me,” she asked me suddenly, her voice hoarse.

I didn’t need to be told twice. I took a condom from the glove compartment while she slid the straps of her dress down. She put it on me herself, quickly, and pulling on her arms I lifted her on top of me. We fit together on the first try, and right away she started moving, leaning on my chest, repeating how good it felt as she went up and down.

Her movements became faster, harder. She grabbed my face and came close to mine.

“I want you to finish in my mouth. Give it to me in my mouth.”

She sped up so much I couldn’t take it anymore. When I felt myself about to cum, I warned her, and she awkwardly climbed off my legs, knelt as best she could in the little space there was, took off the condom, and finished me with her mouth. I came hard, and she took every drop without pulling away, laughing afterward with a grin from ear to ear.

I was left exhausted and satisfied. When she cleaned herself up, I kissed her again. She smelled like wine and night.

“Oh, kid,” she sighed. “It’s been years since someone gave me a night like this. I hope it’s not the last. But now take me home already.”

We laughed, got dressed, and I started the car again. On the way we exchanged numbers, in case we felt like it again. Her house was beautiful, and her husband was already waiting at the door, scowling, reproaching her for the hour. She didn’t even answer him. She just got out, gave me a knowing look of thanks, and went in.

That was the first of a series of nights we had after that. But that’s another story, and I don’t know whether they’d be as exciting as this one.