The Filipina MILF

A few years back, I felt really alone. I hadn’t had a serious relationship since college, I was bummed out about my job and I spent all my free time watching porn or getting blindingly drunk with one of the two friends I had in town. Not more than a week prior to the day I write about here, I had rediscovered how magnificent MILF porn was.

One day, with my dick in my hand, watching a laptop screen mid-way through a scene of Lisa-Ann getting fucked on a kitchen island, I dropped my dick, and said “I want the real thing.” I closed my Firefox browser tab, deleted my history, cleared my cache and closed my laptop, took a shower, dried off and sat back down on my living room couch. Placing the laptop on my lap, I slowly opened it up.

I started browsing different dating sites. I didn’t join one site because it wanted me to answer too many questions, I didn’t like another’s UI, and I thought it would be strange to start messaging random girls on Facebook (this was back in the day when you could without having your witty, wonderfully concocted message end up in her ‘Other’ folder). I came across a simple site and this was by far the easiest to use. I signed up with my spam e-mail, and started browsing it.

I wanted a MILF. I wanted a piece of ass over 40 years old. I was in my early twenties and I had only slept with my college girlfriend and this Indian girl after the ‘Big Break Up.’ The Indian chick gave amazing head and her handjobs were as perfect as you could have them. She’d lick and tickle the head of my cock with her tongue and lips. It was sublime. I would have stayed with her just to keep seeing her head bounce up and down on my dick while she worked her skills on my shaft, but I moved across the country for work and we knew long distance wouldn’t work. We just wanted to fuck one another.

Anyways, I’d only had been with a couple girls, both college-aged, and it was time for some older pussy. I wanted a woman who knew what she was doing. I wanted a woman who had been fucking for years and knew exactly what got her off. I set the minimum age of my search to 40, set the distance to ‘within 5 miles,’ briefly debating to only see profiles with pictures but decided against it and hit ‘search.’ There were less than a hundred results and only a handful that were online at that moment. I wrote up a generic hello message and sent it to all of them.

At this time of the site’s life, it let you to chat with other people real-time. I noticed one username named after a character in a Victor Hugo novel which had a chat button next to it. The user hadn’t posted her picture so I looked at her age. 48. Nice. This was exactly what I was looking for. I scanned the rest of her profile. She was Asian and liked to dance, cook, and read. Oh, she had a PhD too. And she lived in the same town as me. I wondered what she looked like. I clicked the chat button next to her username.

I tried thinking of all kinds of witty and original things to say, but I had nothing to go on, so I just said “Hey, how’s it going?”

A minute or two passed and I figured she was ignoring me, so I kept looking through the other profiles. There was a blonde 55 year old who had a profile picture of herself in a low cut top with a cigarette in her mouth and a drink in her hand. She wasn’t that hot, but she oozed sex. I just kept picturing my dick in her mouth. She probably knew how to suck cock and from the looks of it she definitely knew how to fuck. In the middle of this quasi-fantasy, I heard back from the Victor Hugo loving Asian.

“I am doing well, how are you?”

Shit. I immediately got hard. My heart was pounding as I wrote her back. We exchanged some pleasantries and learned a little about one another. Her name was Darla, she was Filippino, divorced and had two kids. They were staying at their dad’s and she lived literally three blocks from me. After she told me that, my dick was harder than it would be if I watched an Erica Lauren vid. Darla did something in education and really did love to dance because she kept asking me if I wanted to dance sometime. Honestly, I really didn’t, and I thought the conversation was getting boring so I decided to be a little forwards.

“Why don’t you come over? I have some wine and we can order dinner.”

A pause before she responded.

“Oh, I don’t drink.”

Well, fuck. I took that as a no, but to my surprise she kept writing.

“But I am hungry. Maybe I can pick up something for us and come over?”

Woah. Really? My dick was just ready to break through my boxer-briefs at this point.

“That sounds great, when do you think you’ll be here?”

We exchanged phone numbers and she said she’d be by in an hour. I ran around my apartment with a raging boner trying to clean up and arrange. I didn’t want my complete mess of an apartment to turn her off. I put on some jeans and a maroon button down shirt rolled up to my sleeves. I had a glass of red and smoked a clove on my balcony to calm my nerves. I was nervous as hell.

My phone started ringing. It was her. I picked up and said “Hello?”

She had a Philippino accent. It was medium to mild but definitely noticeable. It sounded like a mix of a Chinese and Spanish accent. It was cute. I sighed in relief that the person on the other end was a woman, and this whole thing wasn’t going to turn out to be a joke. She told me she was downstairs.

I gulped down the rest of my wine, put out my clove, sprayed on some cologne and headed down to get her. I opened the door and she was standing in front of me.

She was pretty. If I didn’t know she was Filippino, I would have guessed she was a darker skinned Chinese or Korean woman. She had shoulder length black hair and when she smiled, I could tell that it reached her eyes. She looked prettier with her smile. She was wearing a jacket so I couldn’t tell what her body looked like, but I could tell it wouldn’t be a bad one. I took the Indian food she was holding and welcomed her in. She walked past me and I followed her upstairs.

She walked in front of me so I had a perfect view of her ass. She was wearing black yoga pants and her ass was round and straight up fuck-worthy. All that dancing must have been working. Ever looked at an ass and thought, ‘Wow, that thing was made to get fucked’? Well her ass was just that. I watched her walk upstairs and I followed slowly, both of us just talking about the weather and how it was unseasonably cold.

She handed me her jacket and my eyes went directly to her chest. She didn’t have huge tits. They were probably a B cup but I saw them outlined over her tight white shirt. I wanted them right there. I felt my dick starting to get hard so I hung up her jacket and started opening up our dinner.

We continued chatting about nothing, and I was devouring her with my eyes. I’d scan her legs, take a few looks at her tits and watch her lips move. I probably heard about 80% of what she was saying while imagining my dick in her mouth and pussy the rest of the time. When we finished dinner, she asked if she could see the rest of my place. I showed her around the kitchen and she got excited by a painting I had. It was a stupid thing — maybe I paid $10 for it in Chinatown — but she loved it and wanted to analyze it. I played along, all the while brushing my body against hers while she commented on the painting of a lotus flower. I stood behind her and stared at her lovely ass again. I wanted to give it a grab, and squeeze it while I drove my hard shaft into her. It really was a perfect little ass.

I was close enough to smell the light scent of citrus coming from her hair. I decided to be forward and run my hand over her back while telling her what I thought about the painting. She paused for a second as I did this and then looked up at me and smiled. The she licked her lips. Score, I thought.

At this point I knew we’d fuck, but I was still nervous and I wanted to play the game we were going at a little longer. I told her I was going to have a glass of red and thought we could chat more on the couch. To my surprise she told me to pour her one too.

“But I thought you don’t drink?”

“Tonight’s a night for new experiences.”

Score.

Our conversation on the couch got more comfortable. She swung her legs over my lap, drank her wine and told me more about herself. At this point I became more interested in what she had to say more than just wanting to fuck her. She had traveled the world, spent time in refugee camps working with the poor and doing some generally interesting things. She got her PhD, had a couple kids, watched her ex-husband become an alcoholic and eventually left him.

We were about done with the bottle of wine when I asked her if she’d mind if I had a clove while we talked. I lit one up after she said it was fine and though at this point my nerves were relaxed, it still felt nice. Then she asked me a question that led me on a path to become utterly addicted to her tight little perfect pussy.

“You know what else would go well with that clove?”

“What’s that?”

She gulped down the last bit of her wine, placed the glass on the table and moved closer to me. She ran her hands over my legs and settled both of them on my crotch. She answered, “This.”

She unbuckled my belt and unzipped my jeans. She reached into my jeans and began rubbing my cock over my boxer-briefs. I took another drag of my clove and she smiled. “Am I not right?” All I could do was exhale and smile back.

After she was satisfied that she had completely hardened my cock, she reached under my boxer-briefs and took it out. I felt a chill run through my body. Her small hands wrapped around it. “I love how thick you are,” she said as she caressed my manhood.

I told her to take off her shirt and that I wanted to see her breasts. She leaned back and pulled off her white T. Unclasping her bra, she chucked it on the ground and went back to work on my cock. She was straddling my legs at this point. I reached out and grasped one of her tits. She let out a gasp and a sigh. She had wonderful creamy breasts. They were a perfect size for her body, and I couldn’t believe a nearly 50 year old woman would have tits like that. I was getting hornier and hornier and my cock was ready to get wet.

As if to answer my desire, she licked the head of my shaft. With my jeans down to my ankles, her hands had moved freely around to my ass. She grasped my butt firmly, squeezing it while she licked and kissed my thickly veined cock. Then she squeezed my ass hard and took the entire length of my cock into her mouth. It was incredible and insane. It put that Indian girl in college to shame. What Darla was doing to my cock was a literal work of art. My eyes were rolling in the back of my head as she teased, licked, and sucked me. She swirled her tongue over my shaft’s head while she used her lips to suck it. I told her it felt incredible and she told me to enjoy it. At some point during all this my shirt came off and her yoga pants were on the floor. She guided my hand to between her legs. She was wet.

I needed her pussy. I needed to fuck her hard. I needed to fuck her on her back. I needed to turn her over and fuck her from behind. I needed for her to sit on top of me and ride me. I needed to fuck her in every which way possible. I needed to fuck her until I came inside her. I told her she hadn’t seen my bedroom yet. She laughed.

I took her hand as she walked in front of me to my bedroom. She was wearing a green thong and her ass was as perfect as I had expected. I grabbed it and slapped it on the way to the bedroom and she laughed again. She was excited. So was I.

I realized I was the only one completely naked and I told her this. She sat on my bed, her weight on her elbows as some of her hair drifted playfully over her face. She lifted her legs up and spread them open for me to have a clear view of the diamond between her legs and said,

“Then do something about it.” Damn, this woman was hot.

I knelt near her legs and slipped off her thong. I wrapped my hands around her hips and slid them over her ass and her legs. She loved it. There was an electricity in the air when we touched one another. I looked down at my cock which was throbbing at this point. Then I looked at her pussy which was pink and wet, just waiting for me. It was covered with just a bit of hair, like she never expected to have sex so she left it natural. I looked at her face and she was biting her lip. She nodded.

I grabbed her hips hard and forcefully thrusted inside her. She moaned. I grunted and thrusted again. I briefly wondered how a woman with two kids was still so tight. Her pussy was tighter than the two college virgins I fucked. I thrusted harder again, this time while holding her wrists down. She wrapped her legs around me. Between feeling her warm, silky thighs brush against my back and hearing her moan, I couldn’t take it anymore. I thrusted again, hard, and exploded inside her. I dug deeper into her as my cum coursed out of my shaft and into her pussy. My head dropped next to hers and I whispered in her ear that her pussy was perfect. She wrapped her arms around my back, squeezed her legs tighter, gyrated her hips and milked the rest of my cock until I was drained.

“So is your cock,” she whispered back.

I kissed her. Her lips tasted of wine and sweat. I pulled out of her, spooned her while holding breasts in my hands. We laid there for a few minutes, the only sounds of our heavy breathing beginning to taper. Then she began to sob.

I shifted over and looked at her. I asked her what was wrong.

“The only man I had ever been with before you was my ex-husband,” she said.

I had no idea what to say. In my head I thought she sucked dick and fucked like a pro. Had she really been only with one other man? “Are you ok?” I replied.

“Is there something wrong with me? Look at me, I’m almost 50 and I just slept with someone young enough to be my son,” she answered while sobbing.

I just said what was on my mind. “You’re the hottest woman I have ever fucked.”

She looked up at me and stopped sobbing. “Really?”

“Yes, really.” I was emphatic. It was true.

She wiped her face and told me to lie down. Her hands went to my ass again as her head moved to my crotch. Her mouth enveloped my dick and she played with my soft member in her mouth. It felt amazing. Before I knew it, I was getting hard again. She jerked me for a little bit telling me how thick and veiny my cock was and how incredible it felt insider her. She wanted more. She sat down on my cock as it slid in slowly. She began to gyrate her hips again before bouncing up and down on my now incredibly hard cock. Her moans were loud now and I didn’t give a fuck if they woke the neighbors. I caressed her tits and she pushed my hands away, holding my wrists down while she fucked me, just like I fucked her. Her movement became frantic and she fucked me harder than anyone else had ever ridden me. She said she was going to cum. Her loud moans turned to whimpers as she came, and her body fell over onto me as her hips kept gyrating, albeit very slowly. She kissed me and we laid there, me inside her, and her completely spent on top of me.

At some point, we went to sleep and woke up an hour or two before sunrise and fucked again before falling back asleep. When the morning finally arrived, it was bright and I looked over at her, her curves accentuated by the morning light. She woke up soon after and smiled. We chatted in bed for a bit and she told me she had to run to go to a recital for her son’s later that morning. But before she left, she went down on me again. She stopped before we both knew it would turn into full blown fucking. Then she got dressed and left.

I texted her later thanking her for a wonderful night. I added that I wanted her to cook dinner for me in lingerie and heels, and that I would provide the wine. I didn’t hear back for a few hours. When she responded, I got hard. She said she was free that night and for the rest of the weekend, and that she would provide the lingerie and the blowjobs.

I hope you enjoyed this. It brought back a lot of memories for me. It was my first interaction with Darla in what became a fling that lasted for a few years. She taught me about the details of sex and I think I helped her get her confidence back. She got hotter and crazier over time. We would fuck everywhere: indoors, outdoors, in parks, on hiking trails, in theaters, and museum bathrooms. We couldn’t keep our hands off one another. She needed my dick and I needed her tight little pussy.