My What If Guy free porn video

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I was over at his place during the summer, just hanging out. Both of us were miraculously, concurrently single, which had never happened in the time we’d known each other. I’ve always found Roland attractive, with his sandy blond hair, tempting muscle definition, and his physical presence. He’s not the tallest guy, but big enough to make me feel petite, which I often forget I am. I’m 5’2” and have always been athletic. As a result, I have rather nice ass and flat stomach, with c-cups to top it off.

Just a note: Roland has always been my “what if” guy. We've never had the chance to be together but he and I have this chemistry that I imagine would translate fantastically in the bedroom. However, I’ve also found him to be rather passive aggressive, or alternatively, smug, and there’s something about him that makes me just want to tie him to a bed, humiliate and have my way with him. I wanted to wipe that smug, know-it-all look from his face. You can believe that when I headed over to his place that day, I was rather happily anticipating what might happen.

Anyway, he asked for a back massage. He sat in front of me and we chatted as I rubbed his back and neck. We started talking about our exes and sex - nothing out of the ordinary since we’ve always been comfortable talking about that sort of thing with each other. Then I started rubbing down his arms and had to lean closer to him, with my breasts resting against his back and my head nearly touching his. Before I was finished, he moved back and grabbed my arms so that I was held against him. I moved my head away as he turned his and gave him a quizzical look.

“What?” I asked.

“You’ve always found me attractive right?” he countered.

“Yeah, what about it?

“Well, we’re both here and single. Would you, perhaps, want to, uummm, have a little fun?”

I just stared at him for a bit, not because I was considering it, but because I wanted him to feel uncomfortable. He stared back with those big, persuasive eyes he uses to charm people. Right as he was opening his mouth to talk again, I kissed him. God it felt good! After years of sexual tension, we were finally doing something besides making jokes or “accidentally” brushing against each other.

The first kiss was light, but they quickly deepened. He pulled me around to his front. I wrapped my hands around his neck and started threading my fingers through his hair, which I know he loves. Meanwhile, he was feeling along my back, getting lower and lower. He hesitated above my ass, and I finally grabbed his hands and pushed them down. I shifted so that I was straddling his legs. As he was kneading my ass, I moved my hands along his back and arms and finally the hard muscles of his chest.

At this point, I started getting impatient. It felt like I was in heat. I reached and started pulling up his shirt. He helped with getting it the rest of the way off. He started trying to grab my shirt, but before he could, I began kissing down his neck, licking his ear and down his pecs.

“Kaley, let me take your shirt off. I’ve wanted to feel your tits since that time at the beach when your top came off.”

I laughed. “I know. Let’s take this into your bedroom.”

I stand up and lead him by the hand into his bedroom. After the door is closed, I push him onto his bed, straddling him again, and pull my light tank top off to reveal my white lace bra. Roland hissed and reached up to grab my breasts, groping them.

“Take your bra off,” he commands. I comply, but laugh to myself that this may be one of the last exercises of free will he will be allowed for a while. My bra comes off.

“Mmm, seeing both is better than seeing just the one,” he comments.

“And for longer too,” I add. I push him out of the way and begin kissing his neck and chest again. His hands are moving all over my back as I work my way down toward his stomach and cock, which I can feel pressing into me. As I kiss him, I unbutton and unzip his shorts. I pull them off and move back up his body to kiss his mouth.

“Do you want me to suck your cock?” I ask him as I rub my tits against his chest and my hands through his hair.

“Oh god yes! Melanie (his ex) never did that.” I move lower again and slowly remove his boxers. His cock springs up, fully erect. It’s slightly larger than normal and looks delicious. I grasp the base of it with one hand and start licking around it, teasing him. I take his balls in my mouth one at a time and bath them with my tongue. I move to his shaft, slowly moving my mouth up it, not touching it, but letting my breath caress it. He’s groaning, but I want him to beg.

“Do you want to be in my mouth?”

“Yes! Please.”

“Wait just one second then.” I get off the bed and turn around so my back is facing him. I slip my shorts over my ass, revealing the thong underneath. I hear him gasp and I remove the thong as well. I spin around and kiss him, then grab his cock and lightly stroke it as I whisper in his ear,

“Do you trust me?” He doesn’t quite know what to make of this, but I have his cock in my hand, so he’s not in a distrustful mood.

“Sure,” he says. Quickly I reach into my backpack, which I placed at the side of his bed earlier. I grab out some ties and start to secure his hand to the bedpost.

“What are you doing?” he asks, alarmed, but doesn’t pull his hand away.

“Relax, baby. I won’t do anything you won’t like. Trust me.” I say this as I begin stroking his cock again. This calms him down and I secure his other hand. The ties I use for his feet are slightly longer and give him some room to move. Once I’m done tying him up, I sit on his legs and kiss his body and mouth again. I rub my tits against his chest and stomach and then along his cock.

“Oh god, why did I let you do this? I want to touch you so bad” he groans. I lean down, running my hands through his hair and along his chest.

I kiss his neck and whisper in his ear, “You can touch me, but only when I say so. You like this, don’t lie. I know you, Roland, and you’ve always wanted to let someone do this to you, to take control.” And with that I push my breasts into his face:

“Suck on them. Lick my nipples.”

He obliges. His touch is light, too light. I push them harder against his mouth and he gets the picture. He begins abusing what he can reach with his tongue. The heat of his mouth and then the cool wetness he leaves behind are exquisite sensations. I lift up a bit.

“Have you ever eaten pussy before, Rol?”

“…”

I situate myself so that we are in a 69 position and tell him that I’ll keep sucking as long as he keeps eating. With that, I take him into my mouth and begin running my tongue all over his hard head and shaft. He hisses and begins to lick my pussy. I’m surprised because it actually feels pretty good. I don’t usually get off when someone licks me, so this is new. As he licks faster, I suck harder. I’ve been keeping it light though and I reach my peak before he’s too close. Waves of pleasure wrack my body, leaving me gasping and quivering. I feel him moving under me, trying to wipe his face off on my ass and legs. The odd sensation makes me giggle.

“Damn woman, you came like a train. This isn’t working very well; can you clean my face off?”

I’ve recovered by then and instead of responding, I return my mouth to his cock.

“Kaley, wait, just get a towel real qui-"

He starts moaning as I reach down to caress his nuts. He forgets his face for a while as I’m sucking his cock down my throat (a useful trick I’d learned with my last boyfriend) and playing with his balls. They begin to clench up and suddenly I shift off of him and abandon his cock right before his orgasm.

“You bitch! I was right about to come!” he exclaims needlessly. I turn around and lay on top of him, running my hands along his body and through his hair, careful not to touch his sensitive member.

“Duh, silly. But I just didn’t feel like you should waste that lovely come in my mouth. Wouldn’t you rather have it in my pussy?”

“Oh god, yes, just fuck me til I come.”

“Hey now, you’re going to have to be a tad more polite if you want that sort of treatment.”

“Please. Please ride me. I want to come inside you!”

“Better. You’d better keep it that way too or else you won’t get to fill me up like you want to.”

I move my body down. My pussy is dripping at this point and I rub it all over his dick, using my juice and spit to lubricate it and my hand to set it at the entrance of my pussy. Slowly, I lower myself down his shaft, centimeters at a time. All the while he is groaning from my tightness, wetness and heat. He is large, and I can’t help but moan as well. I can feel the ridges of his hardness as they move within me. Finally, I bottom out, our hips meeting and my clit rubbing up against his pelvis. I stay there for several moments, getting used to the feeling as it has been a while. I also want him to start squirming. It takes less time than I imagined. He starts moving his hips, hoping to make me move in the process. I pull off and he stops.

“Do you want me to free your hands, Rol? Do you want to touch me… to fuck me?”

“Yes, please! Untie me so I can feel you.” He gasps, the idea of release has him captive now. I lean down, pressing body to his and kiss him passionately.

“You already can feel me. I know what you want though.”

I begin to raise and lower myself on his dick, squeezing my pussy muscles as I drop down. He watches me, fixating on my breasts. His head rolls back as he groans.

“You like watching my tits bounce?”

He doesn’t look at me or answer, just nods. I pull off him so that just the tip is touching me and stop. That gets his attention.

“Answer me bitch! If you want me to continue fucking you, you will answer my questions. Do you like watching me ride you?”

“Yes, your tits are amazing and you feel so good around me. Don’t stop!”

“Good.” I resume bouncing on him. With one hand, I reach back and gently grab his balls. He gasps and I start to move my hands lower til I’m touching his little hole. I feel it clench and his eyes open wide. Now he’s really begging.

“Not there. No, no, no, no. Kaley, please don’t do this.” I smile down at him and remove my hand back to his balls. He sighs in relief and I begin moving faster on his dick. His sigh quickly turns back into groaning and I know he won’t last long. I’d imagined numerous endings to this encounter, but ultimately left the ending unplanned. I know I want to keep having sex with Roland, because he’s always turned me on, and even with him helpless, this session has been hot. That’s why, right before he comes, I grab the ties holding his arms and use the tab I had left free to quickly undo the knots. It takes a second for him to realize he’s free, but when he does, he attacks me. He grabs my hips and bucks up into me. I play with my clit and lose myself in the pleasurable sensations. We are both gasping and shaking, rapidly approaching our climaxes. He thrusts up into me one last time and groans. His orgasm triggers mine and I begin convulsing, squeezing around him, crying out for what seems like five minutes.

Eventually, his hands on my hips loosen and I relax and settle down on top of him. My mouth finds his, gently kissing. His hands roam my back while mine explore his hair. He breaks off the kisses,

“You had me scared for a while, but that was incredible.”

I smile. “Exactly.”

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She started experimenting with them both. In the beginning Simon got to fuck the pool guy while he was fucking his friends mother then fuck her. One fucking her pussy while the other was fucking her anus. She had them fucking each other. She had double penetration of her pussy & anus. She couldn’t get enough cock.She organised these meetings when the husband was away on business trips or when the k**s were sleeping over at friends’ houses.Simon had sex with his friend’s mother for the next...

2 years ago
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A Great Trip With a Young Guy

It was a Sunday, I was on business travel in a medium size mid-west town. I was driving on the interstate, near the edge of town, had to go to pick up a couple of things that were waiting for me on-hold at a FedEx-Kinkos near the airport, but didn't have anything to do the rest of that afternoon. Just as I started over the overpass, I saw him -- young guy probably 20 to 22 or so with two backpacks and a bag. He had his thumb out, and I made a quick decision to pull over on the shoulder of the...

4 years ago
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My First Guy

It was one of those evenings that had been happening a lot, I had had analmighty argument with my (soon to be ex) girlfriend. Once again I found myselfwandering the streets trying to calm down. When my anger started to cool off Idecided that I may as well carry on onto town as I seemed to be already pointedthat way.Now up until this point I had a little game, almost a way of teasing myself, Iwould occasionally go into a gay bar in the hope that someone would pick me up.It never happened but it...

4 years ago
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Lonely Hottie Fucked By Food Delivery Guy

Hey folks!! Kamini is here to narrate one of the interesting sex stories of her life. Well, to describe me, I am a typical south Indian unmarried girl living alone in one of the cities. I have a perfect figure such that any guy would give me a second glance and I am literally proud of my boobs! They are similar to that of actress Ayesha Takia and I always flaunt them so much! So, coming to the story – It was a winter night. At around 11:30 pm and after a busy day at work, I was relaxing at my...

3 years ago
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Dirty old guy

My name is Michelle, I’m 35, and my husband would consider me prim and prudish and so would nearly everyone who knows me. I consider myself very conservative and a bit of a goody two shoes, when it comes to the opposite sex, very reserved and shy, but until recently, fairly innocent. Mike, my husband, had begun mentioning the idea of me having sex with another man, but it really wasn’t for me, I was much too proper for that sort of thing. But I would play along with him in bed,...

1 year ago
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Getting Slammed by the Married Guy

While I feel this is a stand alone sexual experience, there was a first chapter/phase/preface where the Married Guy met me at the local pool. If you haven’t read that part, I think you might enjoy it. You can find it on my blog or my main website. Where I left off was me walking out of the changing rooms at the local pool after the Married Guy ruined my ADIDAS 3-stripe speedos. He ruined them by jerking me off on the inside of those speedos and him cumming on the backside of those speedos. As...

4 years ago
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I Dared My Wife to Blow Another Guy

I Dared My WifeJust by a simple dare, my 41 year old Felicity became a hot wife before my very eyes. Felicity was the type of woman who would never NEVER participate in a sexual dares game. She kept our sex life private among her friends and even acted a little too conservative in front of me sometimes, but our sex life was good. Nothing spectacular, but average for a couple married for 20 years. Still, I wanted more.The dare? I dared her to suck off another guy. It could be any guy she wanted,...

2 years ago
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Discovered by a Black Guy

I should preface this story by saying I've never identified myself as homosexual, but sometimes after being locked up in chastity for a long time combined with crossdressing, I must admit to some fantasies involving other men.I never expected anything to ever actually happen, and it's my own fault really. I had been paying a beautiful, very sexually fetish driven woman for her chastity services online. She had a pretty good system. She had me mail her one of the keys to my lock and then she...

3 years ago
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MY GirlFriend Fucks Another Guy

I had been pursuing Noele for awhile. After several dates I had only gotten as far as a kiss. I decided to go for it one last time and asked her out to dinner on a Friday night. To my relief she said yes and sounded excited to go. So was I! I felt like it was finally going to be my night. I had already spent close to $1000 courting her but I decided to double down and take her to the nicest seafood place in town. I bought a new outfit from Hugo Boss, picked up some flowers and went to pick her...

4 years ago
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The nice Latin pool guy

I watched him from my bedroom’s window, as I slipped down my hand and my long fingers found my wet clit.While I circled and rubbed it slowly, I imagined that Latin pool guy on top of me, with his big bronze colored cock driving between the swollen lips of my very hungry wet pussy cunt…Hubby had been inattentive to my needs lately and I really needed a release as I watched Pablo from the window.My needs grew too strong to deny, so I finally removed the naughty finger from my now wet and hungry...

2 years ago
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seduced by gay guy

I was only a teenager still at school and had a part time job in a builders retail shop selling paint and screws and timber etc.I was the only one that the boss employed to take things in after school that he had displayed outside the front doors , ladders, buckets and such like. During the school summer holidays he would employ me full time to work serving the customers and to take customers to the rear of the shop if they needed timber and timber mouldings as it was too dangerous for...

2 years ago
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A young and handsome bisexual guy

Friday night after dinner, some Ana’s old friend called her, asking if we were in the mood to go to the club for some drinks and dancing.She looked excited, as she arranged to meet him around midnight.Ana had loved for years that dancing club, as it has a large dance floor that is kind of dark and they always play alternative music. She told me she would wear something that would turn heads and I just smiled…She wore a tight black dress that clung to her round boobs nicely and accentuated her...

2 years ago
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Gender wap Confessions The Bar Guy

Well where do I begin with my story. It all started when My girlfriend Beth wouldn't stop Nagging on me. Telling me I needed a better job to support her. I was always like This is an Equal World now. You make the Money. Well After Our big Arguement I left The house and Headed to The Bar. As I had a few Rounds. This Guy came up to me and was like whats the Problem Man. I felt Bad Because All I did was whine about How My girlfriend Treats me like shit. He smiled and said he could help with that....

3 years ago
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Dave The Elevator Guy

The summer I was eighteen, I visited the City Hall washroom once in a while. One Friday, about three in the afternoon, I am there and a guy is standing at the urinals. He looks about forty-years-old, is six feet tall and probably weighs about two hundred pounds. We are the only two guys in the washroom. I stand at the urinal next to him and ask, “How's it going?""Pretty good, you?" “Not too bad. It would be better if I could find a job.”When we both finish pissing, we continue to stand there...

Gay Male
2 years ago
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Ashley Blows the Pizza Guy

Ashley could feel her heart pounding in her chest as she hurriedly rushed toward the door. She took a deep breath, hoping that it would slow her heart rate just a little. Her palms were sweating, but not because of the heat of the warm spring evening.In the five days she had been living in her friend's apartment, she had ordered pizza from the same restaurant on a number of occasions. Each time, Hector would appear at her door wearing his baseball cap and a blue shirt emblazoned with the...

Oral Sex
3 years ago
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Ch12 Honey Caught with Pool Guy

Chapter 1 – Honey gets six weeks worth of cum in a day My boyfriend, Paul has been away for six weeks, consulting on an oil platform off the coast of Africa so I’m happy to get his e-mail instructing me to pick him up at Tampa International Airport this afternoon at 1400 hours. It’s not that he expects me to be celibate while he’s away, nor have I been, but I know that when he arrives, his big dangling ball sack will be pre-loaded with about a quart of cum under pressure, his amazing,...

3 years ago
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The mature divorcee and the pool guy

Saturday was a very nice warm day and I was home alone; sunning at the back yard by the pool. As I was there, I suddenly heard some gasps and moans coming from the next house.There lived just Susan, an old divorcee lady who I had fucked wildly two weeks ago. It sounded strange, since I had never heard her this way.So I looked over the fence and found a very nice sight.There was sexy Susan, laying on a big lounge chair, her nice toned legs spread wide and somebody was mounting her; obviously...

3 years ago
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The Hot Tub Guy

CHAPTER 1 On the eve of his thirty-second birthday Ginger Jones gave up his job as a steakhouse chef, sick of kitchen smells and working shifts and being bawled out by diners who believed coarse-ground peppercorns on their rare peppered steak were rodent droppings. Redheaded Michael, who’d been called Ginger from the time he entered Junior High, had purchased a one-man business from a crooked-nosed man who’d promoted himself as The Hot Tub Maintenance Man. The annual statement of accounts...

4 years ago
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Bangladeshi Wife oggled by Danish guy

We are a couple from Bangladesh. We are from Jessore and we arrived in Denmark recently. Its very cold in this country but it is very nice in the summertime. My wife is Nazma and she is 35 years old and has a voluptuous body, dark brown skin and, long black hair and full lips. She wears colorful shalwar kameez all the time and teases the danish men when we go out. I have seen Danish men follow her from behind when we are out and some of them walk behind her with a camera in their hand filming...

4 years ago
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True Story Of An Ugly Guy With The Hot Guy

Hi all, True story of an ugly guy with the hot guy I am Harish.. Till the day I had sex I did not know I am interested in guys too. This is the real incident which has happened in my life before a month. So I thought of sharing this to everyone, because I have read lot of stories here. I live in Chennai.. I do not look much good and not even average. But good by heart.. I have very less friends and I like like mingle with all the people but no one considers me as a friend due to I look ugly....

Gay Male
1 year ago
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Straight Party Guy

I'm not sure how old he is, but Straightboy is in early 20s... a gradstudent who goes to the same school. He's about my height (6'2"), builtlike a football player, medium tan, and he has a nice tattoo on his back.When I say football player I mean thick... not fat, but kind of muscular. Ithink you all can get the picture.I call him Straightboy because he still considers himself straight. WhenI'm not around, he's fucking girls. Now that he's had a taste of cock Idon't think he's as happy with...

4 years ago
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Becky has her first black guy

The second night of my trip to California was equally as nice as the first night! Becky and I spent the day catching up with the past few years we have not seen each other. We talked on the phone, but always kept those calls casual until I was ready and over the loss of Kelly. Becky sat me down and said she wanted me to know something. She said “If you want to invite a bunch of guys over and see me having sex with them, I will. I want to do whatever it takes to make you happy.” I...

4 years ago
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My Gay Experience With A Massage Guy

Hi everyone. Well this is a true incident and not at all something that has come out of my head. This is an incident which happened when I went to get massaged in a gym, also it is a reputed gym so can’t take the name. Hi I am 28yr old guy and a resident of Navi Mumbai. Well to start off I am 100% interested in girls and love to fuck them. I am interested in working out every day but had started working out after a gap of two yrs. unfortunately my gym did not have massage services. Due to just...

Gay Male

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