HOMEMADE PORN MILF VOYEUR. UPDATED DAILY FREE

TITLE: I Cheated With A MILF
STORY:
LOCATION: Medical-Yamz-4-u - USA
AGE: 22 - 30
VOTES: 2,457
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I'm 28, my wife is 27. We've been together since we were in college, almost 10 years, and married about 3.

We've started going to this weekly community event in our local downtown every weekend. It's part craft fair, part local entertainment, party community building. A few blocks of downtown are closed to cars and people set up booths and there are food trucks and live music. You get the idea.

Well there's one food truck in particular that we both really like. Let's call it Grace's Grill. We started getting Grace's every week, to the point where the woman running the truck, Grace (who would have guessed) started to recognize us.

We got to talking with Grace every time we ordered from her and got to know her a bit. Her nephew helps her in the truck on busy days, she took over her dad's restaurant then sold it to start the food truck, and she has a couple of rescue dogs at home. Real small-town, friendly-neighbor type chat.

Now, my wife is, in my opinion, gorgeous. She's got that lean, muscular build of a lesbian woodcutter and it really works for me. However, she's always had the same, rough-and-tumble, outdoorsy, function-over-style look. She wears only a bit of makeup every now and then and dresses in comfortable clothes. I've never had a problem with it, and I really do think she's gorgeous.

But. I've always had a thing for moms. Call it my fucked up childhood. Call it an unresolved crush on my 11th grade history teacher. Call it exposure to an unsupervised, unregulated internet growing up. But god damn do moms make me weak in the knees. Casual moms, moms in mom jeans and slightly wrinkled tee shirts, moms in last year's athleisure, mom's with hair that hasn't seen real care other than the stylist at Great Clips in four years. Thick moms. Thin moms. Moms with mom bods and moms who work out to keep the baby fat away. Moms with big sagging tits.

Let me tell you: Grace is a mom. Her kid is off at graduate school and her husband died a couple of years ago. She's a bonafide mom. She's got platinum blonde hair that's slowly fading to gray. She's maybe 5'2", is somewhat heavy set, and, as far as I can tell, always wears whatever is the most practical for working the food truck. She even treats my wife and I like her kids. She gives us little extras on our plates and asks about our weeks. It checks a lot of boxes.

One day, while I was picking up food from the truck, I mentioned to Grace that I am an insurance rep. I do coverage for mostly small businesses, but also auto and home of friends and family. I told her I'd be happy to get her a good deal given we know each other now. She said that sounded interesting and said she'd give me a call. I didn't really think anything would come of it, and I was actually interested in getting her a good deal, but I'd be lying if I said there wasn't some small part of me that was hoping for a bit more.

A few days later, Grace called me. We set up a meeting and I offered to meet her for a coffee on a Thursday morning so she didn't have to come all the way out to my office then turn around to get back in time to take the truck out. It would just be a basic info-gathering meeting anyway, so there's no need for a bunch of formality in the office either.

We met and it went great. Grace was easygoing, friendly, and, as usual, a total bombshell of a mom. The meeting felt flirty, but I put that down to me reading into things. Near the end she put her hand on mine and looked into my eyes and said, "thank you, you're really sweet to help me," and I nearly passed out. We wrapped up and we walked to our cars and she gave me a hug. A big, soft, warm, hug.

I spent the next dozen nights trying to convince myself the meeting was normal and she wasn't really flirting while simultaneously stroking myself to the thought of her.

When all the paperwork was ready to sign, I gave her a call to arrange the meeting. She said she had a busy week for the food truck and asked if I could come by her place. "No problem," I told her, ideas and images swirling in my head.

I got to her place and knocked on the door. I'd done plenty of client signings at plenty of places. But I was nervous as hell. I'd put on a suit and planned a lame excuse like having a big meeting later in the day to justify having dressed up.

Grace answered the door wearing a blue floor-length dress. Her platinum blonde hair slightly curly, locks just touching her shoulders. The dress's neckline dropped between her breasts and showed serious cleavage. She had subtle makeup on, a little eyeliner and some burgundy lipstick. No shoes, just house sandals. She smelled like flowers. I could hear the rescues dogs in a back room somewhere.

We said our good mornings and hellos. She paused, "everything okay?"

I must have been staring. I was still standing in the doorway, taking her in.

"Yeah, definitely, just haven't had my coffee." It was 10AM and I'd had two already.

Grace said she could fix that and led me to her kitchen. I gave her the usual round of compliments about the house and the decorations. She made me coffee and I explained the docs and spread them out on her dining table. We talked through the different agreements, coverage, all of it. I know that you really wanted to hear about the insurance element of this sex story, so I'm really going to get into the details here. Jk.

She signed and that should have been that. But she was kind of lingering. And I wasn't in a rush to leave either.

"Do you have any other questions?" I asked.

"No, this all makes sense," she said.

I got the sense she wasn't happy ending the meeting, and I assumed it was about the documents. "Do you not like the coverage? We could find something else." I said.

"Everything is great," she said, "I was just admiring how professional of a young man you are." My heart raced. She put her hand on mine again. Reflexively I rolled my hand over and held hers.

I'll be honest here. I don't know exactly what happened next. We said some stuff to each other, justified this behavior, asked if the other was into it, and then started touching one another. Before I knew it, she was pressed into me, kissing me, grabbing my back. She stripped my jacket off and started unbuttoning my shirt. I could taste her mouthwash and the coffee and her little bit of sweat on her lip. We made out at the table for what felt like 20 minutes. Her panting getting heavier, my grip around her getting tighter. We pulled back from each other and laughed at the awkward position we’d worked ourselves into. I looked around and she got my intention.

She led me to the couch where she sat me down, hiked up her dress, and straddled me. I felt the intense heat from her thighs and crotch through my pants. I'm sure she felt my boner. At some point between the table and the couch my shirt and belt had come off. My pants’ single button was putting in overtime to hold together. She leaned down and pressed her body into mine and we kept kissing.

My hands found her legs under her dress, then found skin through the folds of fabric and chased up her legs to her hips. I felt the sheer fabric of lace underwear. Her hips started grinding, both to rub herself on me and to naturally guide my fingers to her underwear’s hem.

“Is this okay?” I asked.

“Yes, do you want to keep going?” She whispered in my ear.

“Yeah.”

“Then take them off.”

I didn’t need a second invitation and hooked my thumbs over the top and tugged down. She shifted and arched to get them around her substantial ass, and then laid back between my legs onto the other end of the couch, her legs up by my face now, as I pulled them toward me and off her legs. They were black lace, but in an old fashioned way. She probably bought these 10 years ago, but they looked unworn. She’d never had the opportunity to put them to any real use.

Then I felt her hand on my cock. While I’d been busy with her underwear she’d been busy with mine. Her hand was hot and slick against me and I couldn't tell if that was her spit or my precum coating the shaft. I tossed her underwear aside and ran my hands up her thighs. Then I think we both had the same thought. I slowed down and she stopped stroking me.

I jokingly told her I don’t normally bring condoms to client meets. She bounced up, tangled in her dress, ran off down the hall. She came back in a few seconds with a condom. She thought of everything.

She sat next to me on the couch and opened the wrapper. I was slowly stroking myself to stay hard as she fumbled with the little plastic packet. In the lengthening time I took my pants off and stripped out of my shirt. Still no progress from Grace. She gave me a sheepish look.

“It’s been literally more than a decade since I’ve put one of these on someone. Maybe 2 decades,” she said.

I laughed and traded her the condom for my cock. She started stroking and spit onto the head and wiped her saliva around with her fingers. The condom she got was one of the cheapest, most bulk buy condoms I have ever seen. Off, off brand type thing. I fumbled and was starting to lose hope. Then I finally got it. I rolled it down onto my cock and she eagerly stepped over my waist and started to sit herself down on my cock.

Grace is, to describe it kindly, a full-figured woman. She has thick, weighty thighs, a thick ass, a few rolls around her middle, and heavy, but not huge, breasts. Her figure, the seemingly bottomless cushions on the couch, and her long dress meant she spent a few moments trying to arrange herself on top of me. All the while I’m trying to keep hold of my softening member and not dry out the two microdrops of lube that came with the cheap condom. The only redeeming feature here was watching this ungodly sexy mom trying to get on my cock (mine! A dream come true!) and feeling the heat coming off of her vagina. But that wouldn’t keep me going for long.

I could tell her legs were tiring as she tried to straddle and sit and fit things in the right place. By the time she was close to ready, I was desperately trying to get hard again. She tried to slide me in a couple of times with no success. She half laughed, half sighed.

“That’s okay,” I said and started to climb my way out from under her.

“I’m sorry,” she said and sat back on the couch.

“Not your fault, just a gotta find the right position. Can I go down on you?” I asked. I love oral and to taste Grace would be even better than her cooking. At the same time, it would hopefully give me enough time to get out of my head and get hard again.

"Okay," she said. I helped her out of her dress and she laid back on the couch. She cupped her breasts in her hands, almost embarrassed of them. I kissed down her neck and to her breasts and sucked on her nipples. Grace's long nipples made them easy to suck hard and she moaned as I did. She tentatively put a hand on the back of my head and pressed me into her. I let out a moan to let her know I liked that.

I worked my way down and found her throbbing, wet pussy. She'd trimmed her bush, too. Nothing fancy, but definitely more thought put into it than what I suspect was usually there. I dove in. Her thighs crushed my head together as I licked at her clit. I tried to work an arm in to finger her at the same time, but her legs kept me locked in, smothered in dripping goodness. I can't really remember how long I was down there, but it only felt like a few minutes. Sucking, licking, exploring with my tongue, feeling her moans as vibrations through her body into my skull. After a few moments she shuddered hard and pressed my head in with a hand. Her hips rolled up into my face and I could hardly breathe. What a way to go, right? It'd be worth it.

Her thighs released me and I came up for air and made eye contact with her. She was sweating and pinching her nipples. But I still wasn't hard. Fuck. Usually going down on someone gets me really going, but this dry, rubber boot of a condom wasn't working for me. Double fuck. I sat up between her legs and scooted my hips towards hers. Her pussy was begging for me, and so were her eyes. I looked up at her and she was nodding at me, telling me to get in there. Time to shine, buddy. This is it! The big show. I looked down at my soft cock. Fuck fuck fuck.

"All good?" She asked.

I stammered my way to a yeah and she could tell what was going on. She pushed her hips closer and slowly rubbed her wetness onto my cock. Still nothing. I rubbed her thighs gently, trying to be cool and reassuring but losing my shit internally. She moved her hands from her nipples to my cock, and slowly tugged up on the condom. My hands started to grip her thighs tight. She wasn't about to do what I thought she was about to do, right? The condom snapped off with a dry thwap that would have hurt more if I cared more. My nails dug into her thighs. I was already harder, the tip of my cock wet with her juices and my saliva from rubbing her clit. In the couple of moments my heart could pump the blood needed, my cock was throbbing and ready.

"Are you clean?" She asked.

"Yeah, you?" I asked. I'd only been with my wife since my last test, so that was true. But how could I have unprotected sex with this person who was basically a stranger? And that didn't stop the pregnancy concern, I thought. Then it clicked that this woman's kid was in grad school and she apparently hadn't used condoms in decades, so she was likely well beyond the point of needing them for birth control. And, if as I suspected, she came once already from me licking her clit for all of two minutes, she hadn't been intimate with anything other than her 1980s vibrator in some time. Any viruses probably packed up and left out of boredom.

"Yeah," she said, "I want you." And in one motion she held my now throbbing cock in one hand and guided it into her with the other between her thighs.

She was tight and wet and warm and heavenly. Immediately she shivered and I felt the pulse up and down my shaft. All I can remember muttering is "oh fuck" for the next 30 seconds as I pumped in and out of her. I leaned over her and we kissed as I slide all seven inches as deep as I could and then back as far as I could without popping out. We fucked like that for maybe two or three more minutes and it felt incredible. So incredible, in fact, that I felt like I might cum. I slowed down and she pulled me tighter. I had to figure out some way to prolong the experience.

"Can I fuck you from behind?" I asked and pulled all the way out.

She nodded and rolled over and got up on her knees on the couch. It was an awkward position, I was half on, half off the couch and trying to angle my cock right to get into her while balancing on this god awful couch. The cushions had zero support and only made me strain more. Had I been wearing a leotard I could have been auditioning for a circus contortionist. Frankly, it was gonna make me last longer and that's what I needed.

I pushed my cock up into her and again felt the immediate tight hold of her pussy. As I went as deep as I could, I felt her dripping onto my balls. She let out a long, low "oh my god" and pressed herself back into me. It felt absolutely incredible, but given the sharp pain and burning sensation from half of my muscles keeping me upright I managed to occupy my mind adequately.

I stood steady as she rocked her whole body back into me in rhythmic pulses. With each slide back her entire ass would press against my hips in a warm embrace. With each pull forward I felt her entire pussy grip and slide along my cock. My hands gripped her hips and I added a slight bounce of energy to each end of the slide to maximize the impact for each of us.

She bent farther forward and I felt one of her hands go underneath her, reach up for her clit, and start rubbing vigorously. Her back was now covered in a fine dew of sweat and her platinum curls matted against her neck. I leaned over her and pressed as much of my body against hers as possible, my cock absolutely throbbing inside of her.

"Will you spank me?" She asked between breathless panting.

I slapped her right cheek. Not to hard, and not with any weight behind it. I am never quite sure how hard someone likes to spanked or pinched, so I start near the bottom of the spectrum and work up from there to find their limit.

"I'm a big girl, I can take it harder," she said. Well, that as a pretty good indicator I was off the mark somewhat. I slapped hard and put the weight of my arm into, right as she rocked back and slammed her body into the base of my cock. "Yes," she moaned into the cushions. The slap smashed her ass against my hips, sending vibrations through her thighs and causing her pussy to tighten and convulse around my cock.

Her right arm extended under her, worked furiously against her clit, her nails occasionally catching the skin of my balls with a sharp flick. Her other hand pinched her left nipple. Her head and shoulders pressed into the cushions, her face turned to the left to breathe and pant. Her drool and sweat making bubbles at the corner of her mouth.

I could feel my cock pulsing toward an orgasm. She slid back and forth with heavy, rhythmic slams. I was riding that fine thread between orgasm and edging. Had she been going any faster or breathing any harder I would cum. I could feel my balls tightening up and had the hyper-sensation of feeling every millimeter of her body gripping mine.

"Spank me again as hard as you can and I'll cum," she said. And then her ass slammed into me again.

"If I spank you again I'm going to cum," I said. Another slide back and forth. Closer and closer to pumping my cum into her.

"Good," she said and tried to look back at me. Another full body slam. I swear this one was harder. We'd only been fucking for five or six minutes at this point. There was no way this was all I could last. I usually went twenty minutes easy, thirty or so if I was working hard like right now. But how could I resist?

"Where?" I asked. Trying to delay the inevitable. Slam. I felt it on the horizon.

"Wherever you want, I'm so close," she said.

She rocked forward and started back with an intensity not yet felt. Her whole body tensed up to slam into me. I slapped her ass, hard. The sweat that had built up on her right cheek sprayed outward. I felt her whole ass and pussy clench and pulse. She moaned, nearly screaming, and tugged on her nipple. Her legs shook and she looked like she was having a seizure. My cock was on fire and about to explode.

For the life of me, I don't know why I did what I did next: I pulled out. I slipped my cock out of her, a bit of her juices splashing out onto the couch as I did, and I did one half stroke and shot a hot rope of cum right at her asshole, splattering across her ass. The second and third ropes shot up the entirety of her back and into her hair. I kept stroking and shooting smaller and smaller ropes across her ass and thighs. '

Why, god, why did I pull out? She said wherever and I could have finished inside of the best pussy I'd had in years.

After a few moments of panting we collapsed onto each other on the couch. I kissed her neck and her lips and licked at the sweat on her shoulders. She just breathed heavy and pressed my body into hers. We laid like that for a few minutes, probably longer than I'd lasted.

We got up, just making small talk about where our various pieces of clothing were, and made our way to her shower. We rinsed off and made out in the shower and I tried rubbing her clit a bit more, but she told she'd cum twice already and probably couldn't again for a little while.

I tiptoed around it a bit and then told her I was sorry I didn't last very long. I just found her so attractive and the whole encounter so exciting that I popped fast. As soon as I said "popped" to her I cringed inwardly. She laughed it off and told me not to worry about it. She came, I came, we had fun, who cares about lasting longer? She continued to tick the mom boxes.

While we were drying off she asked why I pulled out.

"Habit, I guess," I said and laughed a bit.

"Next time, you can cum in me."

I was astonished, not just at the invitation, but at the thought of next time.

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