Got picked up by a [M]IL[F] in the pool | 2016

I was on vacation last week. We'll say it was Cuba, but it was a different island. I had two amazing experiences. I already wrote about the first one, but here's the second story.

It was my last day at the resort, and her first. I had spent the morning in the ocean and was now camped out in the pool reading and drinking. I stayed in there for hours, churning through my book.

At some point during the afternoon, this woman came to the pool with a few friends. It was impossible not to notice her. First, her and her friends were pretty loud. Not overly obnoxious, but they had definitely had a few drinks. Second, she had on a tiny bikini and enormous fake tits.

I'd find out later that she was from Florida. She was 44 years old, but was in great shape. Very fit body, blonde hair, and a dark tan. And again, huge fake breast. Her bikini top was almost comically insufficient to contain them.

This isn't here, obviously, but it's a pretty accurate reference photo.

Nothing about her was my "type". I don't really care about breast size normally, but I've actually never been with someone with fake breasts before. So she had my attention.

She passed by me a few times on her way to get a drink. She clearly caught me staring at her tits, but her smile told me that it didn't bother her at all. Besides, you don't wear a bikini top like that if you don't want some stares. On the third trip by me, she made eye contact and she said hi. Nothing more, but I was please.

A bit later, some of her friends had left. She came by me again, but this time she stopped and asked me how my book was.

Guys, read books. I can't tell you how many times a girl has approached me to ask about my book. It's an easy opener for them and reading is sexy.

We started talking and she was definitely tipsy. She seemed a bit desperate to prove that she wasn't a bimbo. I guess, since I was reading, she just wanted to make sure I thought she was smart. But she was also hinting at sex too.

So she'd tell me how she had her PhD and the stuff she likes to read, but she kept telling me that everyone thinks she's just a barbie type and that nobody takes her seriously. We'd get on the subject of something serious and she'd give an opinion, but then say "Am I making any sense, or am I just some drunk lady with big boobs." As she said that, she ran her hand down her chest, forcing me to look at her tits and then looking for my reaction.

I told her I was leaving in a few hours. She put on a pouty face and said, "That's disappointing." But then she leaned over so that her tits were pressed against my arm and added, "I guess we'd better not waste any time then."

I smiled and asked her what room she was in. She started to get out of the pool and just said "I'll show you."

I followed behind her as she led me to her room. I was trying not to get too hard already, walking through the resort in just my bathing suit. But I was walking behind her and watching her ass in that little bikini, imagining all the things I was about to do to her.

We got to her room and she opened up the door and went in, me still trailing behind her. She walked over to the bed and with her back still turned to me she said, "I saw you staring at my tits all day." Now she turned to face me. "Is this what you wanted?" As she said that, she reached behind her back and untied her top. She took off her bikini top in a way so that hands were still covering her nipples, teasing me. She took a few steps towards me, stopping a foot from me, and then dropped her hands.

God, those tits.

I stepped forward and kissed her, my hands moving up to caress her chest. They were so big. So firm. Her nipples were rock hard and now so was my dick.

We kissed deeply and almost frantically. And then she quickly dropped to her knees. She looked up at me with a huge smile on her face and began pulling down my suit. Her eyes were full of anticipation and excitement; it was as if she were opening a christmas gift.

My dick sprang out of my shorts, obviously rock hard. She took it in her hand, still smiling and said, "Oooohh, I knew you were going to be a big boy."

With my dick in her hand, she traced her tongue the length of me. Starting at my balls, she slowly licked all the way to the head of my dick, never breaking eye contact.

She stroked it a few times, now just looking at it. I let out a loud moan as she finally took it in her mouth. She immediately tried to take as much as she could, forcing my cock down her throat.

She wasn't sucking my dick so much as she was fucking me with her head. Hard and deep, she'd move her mouth up and down on my cock. When she needed a break, she'd back off my cock, stroking it in her hand, and say dirty things to me like "Do you like that?" "God your dick feels huge in my mouth."

Then she'd return to fucking me with her mouth. I started to reach down and play with her tits as best as I could from my standing position. She had her one free hand down her bikini bottoms and was working her clit furiously.

She tried to take me deep in her throat again. This time, I grabbed her head with both hands and forced her down farther. It was my turn to talk dirty. "Do you like that big cock, baby?" She looked up at me, my dick still deep down her throat, and tried to nod. I still had her by the head and was holding her down on my cock. "Are you ready to get fucked?" With that, she let out a big moan. She tried to nod again, looking up at me still, her eyes now watering.

I let go of her head and she came up gasping for air. I told her to get up on the bed. I climbed up after her and we kissed while pawing at each other. I broke the kiss, and pulled off her bikini bottom, revealing a little landing strip of hair above her little pussy.

I positioned myself between her legs and held my dick over her pussy. I slowly stroked my dick with my right hand. My left hand moved down to her pussy and I circled her clit with my thumb. I just sat there for 30 seconds, slowly stroking my dick and staring at her body. She was laid out on display for me and I wanted to take it all in. I wanted to remember the picture of this woman I just met and was going to fuck.

Her hips were rocking up and down, begging for my dick. She was playing with her tits. Eventually, I had teased enough and asked her, "Do you want me to fuck you?"

She nodded with a pleading look on her face.

I pulled her close by her leg, bringing our hips together. I took my dick and slapped it against her pussy. Once. Twice. A third time.

"Are you ready for my dick, baby?"

"Oh god, yes" she replied. "Oh please fuck me."

That was the magic word, so I went inside. Not slowly or gently. She was soaking wet as I pushed the length of my dick deep inside her. She let out a cry as I hit bottom. I just left it deep inside her. She started to try to fuck me, but I was still holding her firmly by her leg, so she just writhed on my dick.

I started to fuck her with long, slow strokes. She was loud. She was gripping the sheets with both hands as I built up a rhythm and continued to fuck her warm pussy. She asked me "Fuck me harder. Please fuck me hard." And I was happy to comply.

I started to fuck her with sharp, angry, deep thrusts. Building speed and always hard. Soon she was practically screaming and then I felt her pussy tighten, her back arched right off the bed, she tore the fitted sheet loose, and literally screamed in orgasm.

It was one of the most intense orgasms I've ever witnessed. She collapsed afterwards, my dick still deep inside her. I gave her some time to recover, just slowly moving my dick back and forth inside her while she came back down to earth. But her orgasm had me on edge. I wanted to cum so badly.

This whole time, I had been over top of her fucking her. Now I brought my body down and kissed her. Still barely moving inside her. I started to play with her tits. Her fabulous tits. I kissed them. Fondled them. Sucked on her nipples. And tried to take as much in my mouth as possible. I needed to cum so badly.

I had one of her tits in both of my hands, the nipple in my mouth, when she said "Do you want to fuck them?"

Normally tit fucking doesn't do anything for me. But yes, I wanted to fuck these tits.

I positioned myself on top of her. I leaned forward and she took my dick in her mouth. "That's it," I said. "Get it nice and wet."

And then I repositioned myself and slid my dick between her two enormous tits. I had a hand on each, holding them together as I started to fuck her big titties. I stopped for a second, moved my dick back out, leaned down and spit on her tits. I wondered how she'd react, but she moaned in pleasure. I moved my dick back in place and started thrusting again.

She was looking up at me smiling. A pleased, satisfied smile. "That's it, baby. Fuck my tits."

I warned her I was going to cum. "Yes," she replied. "Give me your cum."

I moved up slightly, taking my dick in my hand, and I let loose. She opened her mouth, but the first rope hit her right on the nose. Rope after rope of cum shot out of me. It was in her mouth, on her cheeks, even over her eyes. I came and came until she was covered. And then put my cock back into her mouth so she could suck me clean.

It was an incredible way to end my vacation.