Manolo Makes a MILF

I was a young man of twenty-two when I fucked an older woman of fifty-two, a woman better described as someone's mom than someone's daughter.

I met her at the mall.

I was shopping for clothes when she approached me.

"Have you been helped?" she asked.

It was one of those stores whose cashiers were also floor attendants and so they excelled at customer service.

"Not yet," I told her.

I was by some fitting rooms, picking out clothes, and I was about to go in there to try them out, when she said, "There's some fitting rooms over there, why don't you try them out there?"

"There's this one here, too," I told her, pointing to the one right in front of me.

"Yeah, but that one isn't mine. Come to mine."

It dawned on me that they probably work on commission, so I did the lady the favor and went to her fitting rooms.

"Let me know if you need anything," she offered.

"Yes, ma'am."

I stripped down to my underwear and I was about to reach for the new pants when the door swooped open. The attendant had opened the door while looking behind her so she didn't realize I was in there, and when she looked straight ahead and saw me semi-naked, she stopped, and then time stopped as her gaze fell upon my bare skin.

Her eyes traveled all over my body, slowly from below at first and even slower as her eyes traced the curves around my thighs and up towards the bulging print that left little to the imagination, and although time had stopped, her eyes didn't, and her lips quivered as she continued her journey up my body, hiking through my happy trail, over my belly button and up the soft stiffness of my abs and up again towards the lightly bulging pecs I had so diligently been working on, and when her eyes met mine, they widened, and she took one last glimpse down between my legs before quickly slipping an, "I'm so sorry," and before I could tell her, "No worries," she closed the door and shuffled away.

I stood still for a moment processing what had just happened because it happened so fast, and I looked down at myself because I could feel an all-too familiar heat, and sure enough, my cock was swelling behind my briefs, growing bigger and thicker as I remembered, as I relived, how the lady had been looking at me.

I'm not sure how long I stood there but soon enough a knock brought me back to reality.

It was the lady.

I was surprised she was back. I was surprised she wasn't staying away like most ladies would, feeling embarrassed and ashamed of having seen a much younger man practically naked.

"How did it fit? Do you need anything else?" she asked in a calm and quiet voice.

Caught unaware and without having even tried on the pants, I muttered an "umm," just to give myself more time to think, and when I thought it through, I told her that they didn't fit, and I asked if she could bring me a size up, and she said, "Sure," but then I said, "Wait, you can take these?" and I opened the door slowly in the same semi-nakedess she had just seen me in, except this time, I was rock hard, and for the tiniest of seconds, I noticed her eyes checking me out down there before darting her eyes back up to mine.

I smiled at her, maintaining eye contact, and then I gave her the pants.

"I found these just outside the dressing room, in the corner," I told her nonchalantly as I handed them to her, and she said, "Of course, let me go look," and she took off.

I was the only one there, so I left the dressing room door wide open and I looked at myself in the mirror as I waited for her to return, looking at myself through her eyes, wondering what she could possibly be thinking.

I heard her coming back and I decided to flex in front of the mirror so that she could "catch me" checking myself out, but also to show off because it was becoming increasingly clear that this lady liked what she was seeing.

If it wasn't clear then, it was immediately clear when she brought back the pants and said, "Here, try these on and see how they fit," because when she handed me the pants, she didn't move. In fact, the only thing moving was her eyes as she once again scanned me up and down and sideways.

I took the hint and I put on the pants right there in front of her, and I did it slowly, for both of us, and as they came up and covered my legs, my bulge, somehow harder and stiffer, refused to cooperate so I grabbed my cock from outside my briefs and rearranged myself so that I could button up the pants.

Shirtless and only in pants, I asked her, "What do you think?"

She smiled, crossed her arms, then said, "I don't know, why don't you turn around?"

I did, and she was about to make a comment, but through the mirror I saw her face dropped, and she quickly closed the door and walked away as another customer was heard coming into the dressing rooms.

I waited for the customer to leave, and then I waited to see if the lady would return, but she didn't.

The pants fit me just okay, I was between sizes, so I got dressed and took them over to the lady who was standing by the cash register.

"Did they fit okay?" she asked without looking me in the eye.

I looked around and since there was no one, I said, "You were supposed to tell me."

She finally looked me in the eye.

"You looked great," she said, and I had a feeling she was holding back so much.

So I probed.

"Did you like what you saw?"

She smiled, and then she also looked around to make sure we were alone.

"Yes, you're a very sexy young man," she said. "Your girlfriend is a very lucky woman."

"I don't have a girlfriend," I told her.

"Oh, well you should go find one. I'm sure it's not hard for you."

"What do you think I'm trying to do?"

She laughed a little too loud, then almost whispered, "Young man, I'm married."

"Doesn't mean we can't have some fun," I said.

She was about to say something, but then she stopped herself, and I could tell she was thinking it through, there was a devious little smirk on her lips, but she must've shook the thought away because she said instead, "I could be your mother."

"But you're not."

"How old are you?" she asked.

"I'm twenty-two."

"And I am thirty years older than you, young man, you don't--"

"Manolo," I interrupted.

"Huh?"

"Call me Manolo. That's my name."

She composed herself.

"Manolo, I'm sorry for looking at you that way back there, and I'm sorry if you got the wrong impression. I shouldn't have done that, it was not right. I hope you have a great rest of your day," she said with finality, then handed me the receipt and my new pants.

I didn't press any further. I had shot my shot, and the game was over, but it was a good game, and I had sportsmanship, so I thanked her and I told her, "You're a very beautiful woman, and your husband is a very lucky man," and once again she was taken aback, and I walked away as she considered what to say.

I came back to the mall a month later, and there she was. We made eye contact, and she smiled, and I smiled, but I kept walking because that's all I thought it was: a friendly smile.

She found me at a coffee shop about fifteen minutes later. Had she followed me?

"Did you follow me?" I asked her with a sly smile.

"I'm on my break, and I was going to come here either way," she said with an even slyer smile of her own. "Mind if I sit?"

"Go ahead, please, umm," I paused. "I never got your name."

"Maria," she said as she sat down in front of me with her hot caramel macchiato steaming between us. She took a delicate sip with her tender lips.

"Do you really think I'm beautiful?" she asked me.

"Of course," I almost yelled, "and you're not just beautiful, you're sexy as fuck."

I apologized for my crassness, and I told her I wanted her to know that I truly meant it, and sometimes fancy words just don't cut it.

A shade of red, just the smallest of hints, spread across her cheeks and down and around her neck.

She didn't say anything for a moment, she just smiled sheepishly at me, until she said, "Thank you. I haven't been called that in a long time."

"That's a shame," I said. "If I was your husband, I would remind you of your beauty every day."

She chuckled.

"You're young, you haven't been married and been with the same person for decades, so it's easy for you to say that. My husband did remind me of that for many years, but as the years went by, it was less and less, and now it's probably been, what, five, maybe ten years. Time flies, young man, and it takes everything with it. You should enjoy every moment."

"Manolo," I reminded her.

She smiled.

"Yes, Manolo," she repeated.

"I want you to know I am very much enjoying this moment with you, Maria. It came out of nowhere."

"I am, too, Manolo," and she took another long, delicate sip with those tender lips, then she added, "but I will confess that this moment didn't come out of nowhere. I've been thinking about what you said, and I've been wondering if you truly meant it, and I've been thinking about what it means for me moving forward. I've been thinking a lot lately."

"I knew it. You did follow me," I teased.

"Can't something be two things?" she asked, and I nodded touché because I knew exactly what she meant.

She continued.

"I know I'm older now, but I miss being young, and I miss being flirty, and I miss having sex and I wish I hadn't gotten married so early in my life. I was so young and I didn't even know it, and now I'm here wondering out loud in front of a sexy young man of what my life could have been had I done things differently. It's maddening, Manolo."

Like I said, sometimes fancy words just don't cut it, so I asked, "When's the last time you were fucked?"

She spat her coffee and drenched my face with warmth and wetness, and with my mouth gaping at the shock, I could taste her as she slid down into my mouth and down onto my tongue.

"I am so sorry," she said, and she rushed for paper napkins and she stood in front of me, grabbing hold of my face with one hand and caressing the napkin across my face with the other, and I just let myself.

"Thank you," I told her when she finished, "for the mess and the cleanup," and I bit my lip.

"It's on you, really," she defended herself. "You can't just ask an older woman when's the last time she had sex. Put it up there with not asking her age."

"So when was it?" I teased.

She sighed but she played along, and it made me smile because I could tell she was slowly loosening up. "It's been a while. Gosh, is that what you wanted to hear?"

"No, I was hoping to hear about your favorite ways to have sex."

She laughed.

"Why are you laughing?"

"I just remembered something, that's all."

"Tell me."

She thought about it for a moment, I could tell she was trying to resist, but then she shrugged in submission.

"Back in the day, before I met my husband, I used to keep a little black book, and I used to sketch all the different positions I wanted to try fucking in. There were hundreds of doodles I had sketched over the span of a few years and many of them had names and descriptions, and I used to fantasize a lot about being in a gangbang where man after man would use me in the ways I had drawn up, page after page, one sketch after another, and it had to be a gangbang because one man alone would never have the endurance to get past a handful of pages, and I was right because then I met my husband and I showed him my sketches, and he tried with all his heart and all his might to get me to the end of my little black book but he never once could and he never once did, and now, many years later, I just lay on my back when he enters me, the few times a year that he does, and I try not to think about it too hard because if I do, I start to feel resentment about my boring ass sex life."

"Damn." I didn't know what else to say.

"Damn is exactly right," she said, sipping at her coffee once again, but then she continued.

"That day I first saw you, when you called me beautiful, I went back to my husband, and I tried to have sex with him. I even brought out my little black book after so many years, and we tried but I could tell there was something on his mind, so I asked him, straight up, and he broke down and he confessed that he had been cheating on me."

"Fuck."

"Fuck is exactly right, Manolo. Like, what the fuck? What the fucking fuck? I do everything right and shit still goes wrong. Like, what the fuck? So I ran. I left for the weekend because I needed to be alone, and I was looking at myself in the mirror at the hotel I was staying at, and I thought about what you said, that I was beautiful, and I looked at myself, but really looked at myself like I hadn't in years, and I started to wonder if young men like you actually thought I was beautiful, and then," and here she paused, looked around, leaned closer, and continued with a lower voice, "and then I started to touch myself, and I thought about you, Manolo, back in that dressing room where I first saw you standing there practically naked, and I thought about how I had wanted to let go, how I had wanted to pounce on you, how I had wanted to kneel and rip off your underwear and take you into my mouth, and I know you would have loved it, I saw how receptive you were, but no, it was wrong, I told myself, and I held back like I've always held back, and here I am now, not even sure of what I'm doing or why I'm doing this right now."

She sighed a deep sigh, and before I could say anything, she continued.

"Actually, Manolo, I do know what I'm doing, and I know why I'm doing this, and if you're okay with it, I want you to fuck me, back there, in that same dressing room. All you have to do is go back there and wait for me and just be ready because we won't have much time, and then you'll leave and we'll pretend none of this ever happened, but only if you're okay with it because I don't think I could do this with anyone else, and as I say this I'm starting to realize how silly this is and how silly I--"

"Let's go," I said before she could change her mind, and I got up, and she just sat there, perplexed, wondering if this was really happening.

"Let's go," I repeated, and then she followed.

I went straight into the dressing rooms as directed, and I stripped, and there I waited, hard as a rock for who knows how long, but she eventually came in, and she came in with a rush of energy.

She stripped herself quicker than I had, and I admired her body, and I wanted to slow down, to touch her slowly first, but when I told her this she said, "No, baby, I'm sorry, but we don't have much time," and she threw herself at me and my naked body.

We began to kiss, and I sensed her urgency, and she pushed me down to sit on the bench while never letting go of my lips, and she rested her knees to my right and to my left and the warmth between her legs radiated down to where my cock stood at attention waiting to be called into action.

She lowered herself into me, and she pulled on my hair and bit on my lip as my big, bulging head spread her open, and the wetness was an unexpected welcome, and she let herself fall deep into me.

Her body was gripping mine, from head to cock, and we both began to moan as she rhythmically slid up and down my cock, and I scratched her back as the rush of pleasure threatened to explode out of me, and I held back for dear life, and then she tensed up around my cock and around my entire body, she tensed and began to shake.

Was she coming?

She was coming!

Yes, the spasms soon came, and they were unmistakeable. As her pussy contracted around my cock, aching for me, I could no longer hold back because her pussy was now milking me so hard that my own spasms around my legs forced me upwards, and I lifted her, and still inside of her, I came, hard, shooting load after load of cum into her, filling her up, and I held her against me, no I pressed her against me, and all her weight came down to her pussy and into my cock as we both came as one, a veritable beast with two backs.

She moaned into my mouth and pulled the hair on the back of my head and even took a few bites of my neck towards the end of her climax, and then she relaxed, and a long-awaited sigh of relief left her.

We regained our breath for a few seconds though they felt like infinite minutes to our bodies still stuck as one, but then she grabbed my face and looked me straight in the eye and said, "It's been years since I've come like that," and she kissed me, then climbed off of me, dressed herself, thanked me, and walked out of the dressing room as fast as she had come in.

I left soon after, and although I looked, I found no glimpse of her at all.

I came back to the mall a few months later. It was closing time, and as per usual, business was slow with scarcely a customer to be seen. As I went to pay for my items, I saw Maria coming out of the dressing rooms, and when she saw me, she beamed me a smile and came over to ring me up.

Behind her, a young man, about my age, came out with a shirt on a hanger and he hung it up on the nearest rack and sped out of the store, and then, just a few seconds later, another young man followed the first, doing the exact same thing, and I looked at Maria with wondering yet accusatory eyes, and then a third young man left the dressing room in exactly the same fashion as the other two before him.

My mouth dropped and Maria smiled deviously.

"Will that be all?" she asked.

"I mean, I wouldn't mind some of that," I told her, nodding towards the dressing room. "Seems like you're finally making your fantasy a reality."

"You have no idea," she said, then added, "and you're a little too late," she told me as she wrote down her number on my receipt, "but text me, and I'll let you know when you can come over. I hope you don't mind sharing me with a few other guys."

"Not at all, maybe we can get you through your entire little black book."

"Perfect," she said. "Then bring a friend."

Just then, a man called out to Maria from afar.

"That's my husband," she whispered, "we're going on a date," and she gave me the receipt. "Things are looking up again, Manolo, so thank you."

"Thank you," I said, courteously. "Have a good night."

I turned to leave, and as I passed Maria's husband, he stared at me and I stared at him, and we said nothing because I knew the man, and he knew me, and we knew each other well, maybe even more than I now knew Maria, but I kept walking because that is a story for another time, in another place, in another little black book.