Exploring Fantasies In Key West free porn video

Hello. My name is Megan. I’m 26, I live on Miami Beach, I have an MBA and I’m doing very well in the business world. I’m a blue-eyed brunette, tall and athletic and considered attractive, although with a youthful face, made more so with my dark brown ponytail. I have kind of a girl-next- door look about me. I’m positive and enthusiastic by nature and I’m well liked but underneath I’m an aggressive sexual adventuress, using my youthful, innocent appearance to help me get what I want. I’ve had sex with many different people, in all kinds of configurations, on 4 different continents. This is a true story and happened last year, much closer to home.

I’d just broken up with my boyfriend (I was getting bored ... sorry) and decided to treat myself to a 3 day weekend of sun, fun, tennis and maybe some action at a hi end resort I’m familiar with in Key West. It’s a pleasant drive from Miami, especially in the early morning, in my red Boxter 718 convertible. (Showing off. Again, sorry.) I got there early on Friday, as I wanted to get in some morning tennis. It’s almost summer here and it’s just too hot to play in the afternoons. After checking in, I dropped off my clothes bag in my room (I was already dressed in my tennis clothes) and went to the courts to work out with the teaching pro for an hour.

While we were playing I was aware of two guys several courts away playing a game. They weren’t especially good but they were having fun and they were in-shape, attractive men, in their, umm ... early 50s, I think. They had a healthy, money look about them. After I finished drilling I watched them for a bit as I toweled off, making sure they noticed me and when I turned to leave one of them calls out:

“Excuse me, miss.” And here was his line: “We were watching you playing and saw that you were pretty good and we were wondering if you would hit with us and maybe give us a few pointers.” Pawn takes Rook. (I like to use chess metaphors.)

This was so obvious, part of me wanted to laugh but I figured wtf ... because I’d already decided I was going to have sex with at least one of them ... maybe both. Intros were made (I’ll call them Allen and Bill, to keep it simple) and I drilled with them a while, me on one side and them on the other. We finished, sat in the shade, toweled off and ordered some cool drinks from the bar. Now here’s the thing: I know many men are put off by an aggressive woman, so the way I play it, I let them think this is all their idea. When I do that it requires a little more skill and patience on my part but that’s OK. If it’s too easy, it’s not as much fun ... you know what I mean? After all ... like tennis, this is sport.

We ended up having lunch together and we hung out at poolside, talking for a while. I actually enjoyed their company. They were both well tanned and handsome in a rugged sort of way, which I like, as I don’t care for pretty boys. They had good manners, were bright and well spoken and I happen to like older men anyway. I had a massage appointment and I knew I wanted to take a nap after that, so I excused myself but before I left they invited me for dinner and after stalling a bit I accepted. Rook takes Knight.

We met for dinner. I wore a cute yellow sun dress. I let them pick the wine. They explained that they were partners in real estate development in the Boston area. They must have felt a little guilty, because they revealed that they were both married and their wives were on separate vacations. Ordinarily I wouldn’t mess with a married person ... man or woman but under the circumstances, I wasn’t fazed and I told them so.

After dinner we moved to the pool bar and we had a few more drinks. You should have seen their faces when I ordered Macallan, neat. We were having fun and there was a lot of laughing but I’d had enough and I wasn’t fucking them that quickly. After all, I wanted them to work for me. I know, I’m bad but like I said, it’s sport. It’s all a game. Just call me Megan, the baby-faced predator.

I let them walk me to my room and then I let them both kiss me good night (no tongues) and give me a sexy hug, although after letting him cop a quick feel of my ass, I pushed Allen’s hand away with a little righteous indignation and I sent them on their way. They’ll jerk off. They’ll get over it. We promised we’d meet up the next day ... Saturday, although no specific plans were made. Night takes Bishop.

When I walked into the room the message light on the phone was lit. The pro had arranged a match for me in the morning. Cool.

It was a great match, even though the guy beat me 2 straight sets. I played well but he played better. And being the exhibitionist that I am, I enjoyed that we drew a lot of spectators, who applauded after a terrific rally or a great shot. I don’t obsess about winning and while winning beats the hell out of losing, there’s always someone better. It turned out he was a former pro player, who was now the instructor at another club. It’s no wonder I lost. Man, what a serve!

When I got back to my room there was another message. It was from the guys, inviting me to meet them for lunch at poolside, which I did.

I wore a pair of white shorts and a white tank top. The guys looked great. These are two very healthy looking, apparently successful business men. (Even off season, this place isn’t cheap.) While we were eating a light lunch and having a couple of drinks they made a few off-color jokes, which I laughed at. They also took opportunities to compliment me and I certainly let them do that as well. The truth is, I was really enjoying their company and I felt very comfortable with them. Lunch was over and I was curious what their next move would be and how they would make their play ... when they made their play. They invited me to join them for the afternoon at the pool. It was tempting, as I could have teased them by wearing a skimpy two-piece (I don’t wear thongs, as I consider them slutty) but I wanted some alone time and I was going into town to do a little shopping. However I did agree to meet them for dinner. Bishop takes Queen.

While shopping, I purchased a black sundress with built in cups, so I wouldn’t need a bra and a pair of white see-through panties. I wore them to dinner. It was time.

The poor guys almost tripped over themselves, as they both rushed to pull out my chair for me. I stifled a giggle but I do appreciate good manners. I let them buy me lobster but this time, after coquettishly asking if they didn’t mind, I ordered the wine, as I knew the wine list and in this case, I chose a 2013 Grgich Hills Cabernet. (God, I’m an incorrigible showoff.) Eventually we ordered a 2nd bottle and by the time dinner was over we were having a great old time. After paying what had to be an absurdly large check they looked at each other, cleared their throats and invited me to their room for a nightcap.

“Wellll, I dunno, guys. OK but just one.” Queen takes King. Check mate!

Their room was a suite as it turned out, with bedrooms on opposite sides of the living room. They offered me a Macallan, which impressed the hell out of me, as they’d gone to the trouble of buying a bottle, hoping I would visit them. They put on some music and we went out to the balcony, which was well furnished and we brought the bottle with us. These guys could hold their booze as well as I; also impressive. After a bit, there was slow music playing and Allen asked me to dance, so here it comes.

We went back into the living room ... the floor was Spanish tile, so we could dance some and we started to slow dance. I have to tell you, I felt very comfortable in his arms. Or maybe it was all the booze. It didn’t matter, the result was the same. Bill slithered up behind me and joined us and this part of the experience was very erotic and very sensual.

Allen started kissing me and I kissed him back; first tenderly, then passionately, with my hand on the back of his head, pulling him into me. He had a hard-on that he was pressing into my lower belly. Bill was kissing my neck and his hard-on was pushing into my ass. I’m tall, remember. Umm, cocks on both sides and it felt so good. Allen reached down and put his hand between my legs, pushing into my pussy through the thin material of the dress and stroked me. Then, while he was humping my ass, Bill reached around, slipped his hands inside the top of my dress and cupped both my breasts, fondling my nipples, which were hard. I reached down and fondled Allen’s cock through his shorts and then I reached behind and fondled Bill, as best I could. Then I turned and kissed him; long and passionately.

We kept this up for a while, me alternately kissing Allen, then Bill. Them touching me everywhere. They pulled down my top, fondling, caressing and sucking my breasts and my nipples, both men at the same time. I caressed the backs of their heads as they did this. They reached down and put their hands under my dress, pushing it up and caressed and fondled my pussy and my ass through my panties. They pushed the panties aside and put their hands inside, feeling my wet pussy, playing with it, messaging it and also the crack of my ass, including my anus. I couldn’t stop kissing them while they were at me. I wanted more.

But I had trouble getting to their cocks and there was something I wanted to do but not on tile. I asked them if their bedrooms were carpeted. They were and we went into one of them. I had them stand next to one another, I backed away a few feet and slipped off my dress, standing there in just my see-through panties and my still high and firm breasts. I did a slow turn, letting them take it all in. OK, I know I’m hot, in that girl-next-door sort of way I told you about but don’t hate me ‘cause I’m beautiful. I guess I should mention that I trim and mow my bush, as I feel that’s sexier than the full shave all the girls are doing now. I figure if the reader is getting into a visual, I think that counts.

“God, you are so beautiful, Megan.”

“Why thank you, sir. And so are both of you. Now would you be so kind as to take your clothes off? I wanna look at you and please don’t rush it.”

They both had beautiful hard-ons that stood out like fat, flesh-colored bananas. I stood in between them. I closed my eyes as they caressed my breasts, my nipples, my pussy and my ass. I heard myself purring. They put their hands inside my panties again and felt my pussy and my ass at the same time. Bill snaked my panties down and off and we were all naked.

Allen put his finger in my mouth and I sucked on it. I knelt down on my knees and fondled their cocks and their balls. I took Bill in my mouth, sucked on him and then Allen and switched back and forth, sucking one and fondling the other, then switching again. I lathered up their cocks with my saliva and while I was sucking on the head of one, I was pleasuring the other by sliding my hand over the head of his cock and back again. I loved the feeling of their cock knobs sliding in and out of my mouth. Their cocks were a nice healthy size and would feel so good inside me. One of them, I don’t remember which, was stroking my hair, which I love while I’m giving head. I made love to their cocks, bringing moans of pleasure to both of them but I didn’t want them cumming yet, so I stopped and we moved to the bed ... king-sized, of course.

The guys were gentle and tender with me. Some men are sexually rough (expressions of hostility towards women, I think) and I won’t put up with that but their tenderness increased my pleasure a whole bunch.

I lay down on my back, in between them and spread my knees, making sure to give them a nice open view. Allen lay on his stomach, his head facing my feet and began stroking my pussy, which was already soaking with my juices. Bill was kneeling next to the bed, behind me, reaching down and feeling my breasts. I put my hands on top of Bill’s while he felt me up and at the same time I pushed my pussy hard into Allen’s hand. I was really moaning. He rubbed my clit so hard and so fast he almost got me off right then and there, so I slowed him down a little. Then he inserted his finger into my pussy and fingered me, while Bill leaned over to suck my breasts, first one, then the other. Allen took his finger out of my pussy and put it in my mouth and I sucked it clean, while Bill took his mouth off my breasts, kissed my neck and caressed my head.

Bill climbed onto the bed, got on his knees and put his cock near my face. I held it, stroked it, put my mouth around it and sucked it. He got his hips moving and started fucking my mouth. At the same time, Allen put his head between my thighs and began licking my pussy. He came up for air long enough to tell me he liked my trimmed pussy hair. He stuck his tongue deep into my pussy as far as he could and wiggled it around, which felt great. Bill pulled his cock out of my mouth and leaned into me and kissed me very deeply. He put two fingers in my mouth and kind of fucked my mouth with them.

I turned over onto my knees and elbows, making my ass higher. Allen got on his knees in front of me and I took his cock into my mouth. Jesus, I love giving head! This opened up my ass for Bill. He got down behind me, put his face into my crack and buried his tongue in my ass, then my pussy, then my ass. I had a cock in my mouth and a tongue in my ass. Holy shit, this was fun!

I stroked Allen’s cock while I sucked on it (the secret to a great blow job is a lubricated hand) and he nearly shot his load, so I backed off. I didn’t want him cumming yet. Then Bill took his tongue out of my ass and put his finger in and rotated it. Holy fuck!

I deep throated Allen’s cock and got most of it in. I loved that he was stroking my hair while I did this and I looked up at him. Christ, did I say I love sucking a big, hard cock? Meanwhile, Bill was alternating fingering my ass and then burying his face in my pussy. I had so much going on at once, it was driving me insane with pleasure.

I wanted both their cocks some more, so I got up on my knees and took Allen in my mouth, then Bill, then back to Allen. While I was sucking one, I was stroking the other. I had two nice cocks fucking my mouth. I rubbed their cocks over my face. I loved making them groan. I felt sooo slutty.

They were both enjoying getting blow jobs but Bill, who was on my right, seemed to be enjoying it more, so I focused on him. He had a big cock and it filled my mouth. I sucked it, pulled my mouth off and stroked it. Sucked it, pulled off and stroked it. I licked his balls and put them carefully in my mouth and tickled them with my tongue, while he jerked himself, almost getting off. Allen put his hand under me and played with my pussy while his friend fucked my face. I reached under Bill and stuck my finger a little ways into his ass and at that point he couldn’t hold back any longer and exploded into my open mouth. I swallowed it, all of it, like the slut I am.

I turned back to Allen.

“Lie down for me, Allen”, which he did, although he wasn’t sure what I wanted.

I got on my stomach and put my face in his ass. He saw what I was doing and pulled his legs back, giving me access to his anus. I stuck my tongue in his ass as far as I could reach, massaging his balls and his cock at the same time. I love rimming people ... men or women, I love it. I love the musky odor and I love how people love getting rimmed.

This went on for a while. Allen was really, really enjoying it.

“Oh my God, a young girl has her tongue in my ass!”

‘A young girl’, I thought. He said ‘A young girl, didn’t he?’ Hmm.

He was ready but wanted my cunt, so he gently urged me down on the bed. I was on my side and he got behind me, kind of in a spoon position. I could feel his cock against my ass. Finally, I was going to get some of what I needed and wanted so badly, as he slipped into my wet cunt, completely filling me up. “Oh shit!” He began. I was getting fucked and fucked hard from behind.

“Oh God, this is good!”, I heard myself saying. “Oh fuck, yeah! Come on, Allen ... fuck me. Fuck me some more!”

He picked my leg up, spreading me wide, allowing him to get into me deeper. He was fucking me so good when out of the blue, he shoots his fucking God damned load! What?

“Whoa, Allen ... WTF, man? Too soon. Too soon.”

“No worries, girl.” I turn around and it’s Bill and he’s getting hard again. These guys were full of surprises. He lays down and I climb on top him, so I can straddle him and fuck him and I fucked him good. Our hips found a rhythm and, oh man, what a ride! And then I look up and Allen is on his feet, standing on the bed and he’s stroking his cock and wants my mouth. Damn, these guys were fun!

As Bill fucked my cunt and Allen fucked my face I could feel my orgasm building. I could hear myself making girl sex sounds, while the guys were building their own crescendos and just as we were all getting close (just like a young girl?),

“Make me cum, daddy. Please make me cum.”

“WHAT!?”

That set them both off and everyone exploded in a huge group orgasm. Bill into my cunt, Allen into my mouth and me ... well ... where girls cum. But I wasn’t done.

“Bill. Don’t pull out ... not yet.”

I kept fucking him, riding him hard, rubbing my clit against his rapidly shrinking dick and in another heart-pounding explosion, I came again, even stronger than the first time.

“Holy shit!”

King had taken Queen and taken her good.

“Fuck, yeah!!! And we all collapsed, breathing heavily, gradually slowing down to contented sighs and then the damnedest thing happened ... totally unexpected ... I guess from all the booze and the great sex, we all three fell asleep, with me, in the middle, not a slut but daddy’s good girl. Daddy’s good girl. Daddy’s good girl.

That was Saturday night. Sunday’s experience was very different. Our sex play was far more cerebral, visual and verbal, as we explored my new friends’ deepest fantasies. There was a lot more talking and I’ve done my best to recreate our dialogue from that day.

I woke early, as I usually do. The guys were sound asleep, on either side of me. Careful not to wake them, I climbed over them, gathered up my clothes, put them on and made my way out of their room, back to my own. The way they responded when I said “Make me cum, daddy”? Well, I had an idea and there was no way we were finished.

There are certain clothes I always pack when I travel for fun, just in case; a role play I’ve always enjoyed and always been good at, although it might be a little tricky under the circumstances. After showering I put the clothes on and made my way back to them, pretty certain they would be appreciated. I knocked on the door. Allen peeked out and stood there with his mouth open. I was wearing a blue pleated school girl skirt, a white short-sleeve shirt with buttons down the front, white sweat sox and sneakers. My hair was in it’s usual ponytail.

“Hi daddy. I just got home from shopping after school. Would you and uncle Bill like to see the white cotton panties and bra that I just bought?”

This is the role play I’ve been doing with older men since I was a girl. It’s fun for me and it turns older guys on like crazy, especially since I’m so young looking. And it’s very verbal. I’m guessing the reader understands what I mean.

After he got over his surprise, a big smile spread across Allen’s face.

“Come in sweetheart. Uncle Bill and I were just talking about how mature you were getting, now that you’re uhh, 15.” Fuck yeah, he was into it.

“Hey Bill”, he called to his friend’s side of the suite. “Got a surprise for you, as soon as you’re finished in there.”

Bill came out and “Holy crap!”, which made me giggle.

“Hi, Uncle Bill.”

“Your 15 year old niece here went shopping after school and bought some white cotton underwear”, Allen said to his friend. “She asked me if we’d like to see it. What do you think?”

“What do I think? Are you kidding? I’m already turned on, seeing her in these clothes. Sweetheart, would you like a drink?”

“Maybe some OJ, Uncle Bill. I’m too young to be drinking alcohol, right?”

“Sure, sweetie. Of course.”

I sensed they weren’t certain how to proceed, so I took charge.

“Look, I’ll tell ya what. We’re gonna have some fun here, so why don’t you guys pop some more viagra and I’ll have myself some breakfast. An hour should do it, right?”

“Hey. What makes you think we take or need viagra?”

“Seriously? Come on. You guys are in great shape but you’re not 20 and last night you fucked me like a couple of young stallions. Nothing to be embarrassed about. I think of viagra as a sex toy for women.”

They looked at one another and laughed.

“You sure speak your mind, Megan. Yeah, we each popped one last night and because we thought ... hoped ... you’d be back today we wanted to be prepared, so we already popped some more. Yeah, we’re set ... ha, ha.”

“This place pipes in both Sirius and Pandora. Can you find us some reggae? Or maybe some surfer music? I’ve been getting into that lately.”

They fell all over themselves getting to the music system. Ya gotta love their enthusiasm. They found some Bob Marley. Yeah, that’ll work.

They looked at me expectantly. Yeah, they were into it. But this is going to be different from last night. Last night was pure physical sex. This morning, I knew, was going to be something else. Sex, sure but something else.

“Why don’t we all sit down, fellas. There’s something I’d like to ask you.”

I sat down across from them in an arm chair, with my OJ and my school skirt hiked up well above my knees. I opened my legs a little more so they could see my inner thighs. Their eyes went right in between my legs. I opened them a little further, so they’d catch some white panties crotch.

See here’s the thing: Even though they both saw every inch of my body last night, this is today and I’m wearing clothes ... schoolgirl clothes ... and that’s different, so the game changes. I’m dressed and that’s sexy too and now they want to watch me undress and see my teener underwear, which now becomes much more important. I’ve just become a15 year old school girl to the guys. Does that make sense?

“This is going to be very direct, fellas and I’m hoping we’ll all be honest here, OK?” Here goes nothing...

“Is this going to be truth or dare or something?”

“Na. No dare. Just truth. So, fellas ... you have daughters? How old? Allen?”

“Two girls. A 14 year old and a 17.”

“Bill?”

“One, Kiley, 16.”

Perfect. I’ve never met a father, who, when given motivation, safety and opportunity to explore his imagination and fantasies, didn’t admit to having sexual thoughts about his teenage daughter.

“Do you get off on them?”

“What?”

“Come on, no one’s being recorded and we’re friends here. Do you get off on them?”

They looked at one another. Bill spoke. My Uncle Bill. Such an uncle.

“Yeah, I do. Kiley has always walked around the house in her underwear and the older she’s gotten, the more it turns me on.”

“Jeeze, Bill”, Allen said to his friend.

“Come on, Allen”, I said. “No judging here. We’re just three happy pervs on holiday. You’re looking forward to watching this 15 year old girl undress and then yer gonna fuck me. So let’s have a little sexy fun here.”

“Do you jerk off thinking about her, Bill? Do you sniff her soiled panties? Do you think about her when you fuck your wife? Assuming you still fuck your wife, that is.”

“Yeah, I do. Yes to all. I’ve been in her underwear drawer many times, playing with her bras and panties. I like rubbing my daughter’s underwear on my cock and balls. I’ve seen her tits on several occasions. She’s gorgeous.”

I ground my thighs and spread my legs wider. I was already lubricating. This was turning me on and once the guys let go, I knew it would turn them on, too. Mr. Marley played on.

“Holy shit, Bill!”

“Yeah and you know what? This is turning me on to talk about her” he confessed.”

“Cool. Me too. Now you, Allen.”

“Now me, what?”

I just looked at him, hiked up my skirt up almost to my panties, spread my legs a little wider and ran my fingers across my inner thigh.

“Come on, daddy.”

“OK, yeah. I find myself getting aroused. They’re teenagers, for Christ’s sake. Beauties at that.”

“They take after their daddy”, I said.

“They dress in next to nothing these days. Even the 14 year old. I’ve spied on them from our upstairs bedroom ... Jeeze, this is difficult for me ... when they were sunbathing, naked, at our pool, when they didn’t realize I was home.”

“Did you jerk off, Allen? Did you play with your cock while you spied on your naked teenage daughters?”

He looked at his friend, then back to me.

“Yeah, I jerked off. God, they’re sexy!”

“They sure are”, said his friend. Both of them. It’s hard not to look at them when I visit your house.”

“Since we’re being honest, Bill ... I feel the same about Kiley. She is gorgeous.”

“Do you guys fantasize about the other’s daughter or daughters?”

I was getting very turned on listening to my new friends talk about their daughters. I slithered my fingers across the cotton crotch of my panties. They looked between my legs, then looked at one another a little sheepishly.

“Yeah, I do”, said Bill. “And by the way, Megan ... it’s very sexy looking between your teenage legs and seeing your white panties.” He rubbed himself.

“I’ve seen your girl’s underwear like this, Allen. The kids aren’t modest anymore. They don’t seem to care.”

“Yeah, me too”, said Allen. “And to be honest, one day when I was at your house, Kiley was wearing a short school skirt ... like you have on, Megan ... plopped herself down in a chair and accidentally flashed the crotch of her panties. I think they were pink. I got so turned on I hurried to your bathroom to jerk off. But what about you, missy? Any dark secrets you’d like to share? Hmm?”

“Yeah, a couple but let’s do this”, I said mischievously, as I spread my legs over the arms of the chair, exposing the full crotch of my white panties for their viewing pleasure. “I see you both have hard ons. Why don’t you take your shorts off but not your underwear. Not yet.”

I could see they didn’t know where I was going with this but at this point, I don’t think they cared and off came their shorts.

“Love your tighty-whities, fellas. Shows off your bulges. And you do have very nice bulges, which are poking out of your underwear, naughty, naughty. I guess talking about your daughters is turning you on as much as it does me to listen. Now your shirts, please. Ahh, very nice. Very masculine gentlemen.”

“So?”, asked Allen?

“When I was young my father and I used to watch each other masturbate. He would strip and start playing with himself, then I would undress ... he loved when I was wearing pretty much what I’m wearing now ... and then I’d start playing with myself.

Guys, your mouths are open. Come on, breathe. No, really we used to do this. It went on for about a year. No, it was fun. I loved it. He would tell me how much he loved watching his little school girl undress ... he would describe every item of clothing ... how he wanted to do things with my body and he would jerk off while he did that and I would say things like how much I wanted to suck his cock ... my daddy’s cock. The whole thing was very verbal and looking back on it, very surreal.”

“And you liked it? What about your mother?”

“Only when my mother was out, silly. And yes, absolutely, I loved it. Then one day we were in the living room. I was on the couch, wearing my school clothes and thinking we were going to do our usual strip and jerk. He stripped, as usual but then he got on his knees in front of me, jerked on his cock a few times, pushed my skirt up and my legs back, put his head between my legs, pushed his face in between my legs, into the crotch of my panties. I thought that was pretty funny at first but then I got into how sexy it felt and he got me off with his lips and his tongue.”

They started stroking themselves furiously through their underwear.

“This is incredible.”, said Bill. “I never heard anything like this. How long did this go on?”

“Yeah”, said his friend, as he pounded his cock through his cotton underwear. “How long?”

“Not long. The next time we were doing it my mother caught us and there was all kinds of shit went down, which was the last time my father and I went near one another. But I told you there were several things. Would you like to hear the other?”

“Please!”

“After that, starting I guess when I was 14, I used to pick up older men and let them watch me undress while they jerked off. I always wore a white bra and white cotton panties for these things. And I would play daddy’s little schoolgirl and even if they didn’t have daughters or granddaughters, the fantasy would drive them nutty.”

The guys had their hands inside their underwear and were pulling on themselves even harder.

“Did you have sex with them?”

“Naa ... I just let them watch. It was like a sexy hobby. They also gave me money. Sometimes a lot of money.”

There was a lot more crazy shit when I was a teenager but this wasn’t true confessions ... they were ready. So was I, as I massaged my pussy through the soft cotton fabric. I closed my legs and stood up. I walked over to the couch, leaned over and massaged their cocks through their underwear, feeling their cock knobs as they poked out.