The Eager Fool free porn video

I was one of the smart ones. School was easy without effort. I barely spent time on homework, never studied, kept straight A’s. Lacrosse and martial arts kept me in great athletic shape despite my utter lack of talent for the former, it allowed me to cross social groups between the nerds and jocks easily. My first girlfriend for 2 years had never let me past 2nd base, and maybe I overcorrected by losing my virginity after my first date with the second girlfriend. We had a short but passionate relationship and I discovered the immense joy of sex! Not simply the carnal physical pleasure, or the feeling of control that came with being the alpha partner. What I enjoyed most was the opportunity to send someone into orgamic bliss. To me, giving pleasure was the reward, and watching a woman lose control of her body overwhelmed with stimuli was the ultimate trophy. Learning came naturally to me and soon I wanted to explore the boundaries beyond vanilla sex. I studied knots for bondage, massage techniques, and researched various kinks that piqued my interest. Thank Science for the internet!

Single again in my final year of high school I turned to a dating website specifically for hookups. This was before smart phones and apps, but the idea was similar. My site of choice attracted a lot of swingers. Mostly I met women, but eventually the idea of joining a couple intrigued me. I had always considered myself straight, but as I explored kinks like BDSM, mature women, and groups, I developed the motto ‘try everything three times: once to see what it's like, again since you probably did it wrong the first time, and once more later, in case you've changed your mind.’

After several successful hookups with women from the site, I set my mind to finding the right couple. I chatted for a few weeks with multiple pairs, but one stood out. About 15 years older than me, Eva the wife had a voluptuous full figure, well-endowed with large naturally perky breasts, hourglass hips, dark wavy hair that flowed to the curve or her tight round ass, captivating eyes, and an Eastern European accent. She was the ideal cougar, and I would have done anything she’d asked for the chance to watch her thrash in orgasm. She was a flight attendant and they regularly played with young men in hotels so she could stay close to the airport.

Mark, her husband, was a good looking guy. Taller and broader than I, though we had similar sized members. He agreed that our encounter should be about pleasing Eva. That if I wanted to experiment with male-male contact it would be fine, he was bisexual, but that it wasn't necessary. I could stay within my comfort zone as much or as little as I wanted, as long as Eva got what she needed. We set a date and place to meet, and I was extremely excited to see this cougar vixen squirm by our collective effort. Perhaps that very excitement lead me to look past the red flags.

We had planned to meet at a coffee shop, somewhere public, before going to the hotel, as is typical when meeting strangers from the internet. Mark texted me a few hours before.

“Hey Mike, Eva and I are running late. Her flight has been delayed and I had a meeting run long. Can we meet a little later, how's 8PM?”

“No problem, I'll see you both at 8. I can't wait!” I replied.

“Thanks! Me neither.”

As I arrived at the coffee shop:

“Would you mind coming straight to the hotel? I'm still behind, just getting in the shower now.”

Huh, that's not what we agreed to but fine, whatever gets my face between those big beautiful titties the fastest.

“Sure, I guess, where are you at?”

“The Marriott on Spring St, room 566. Come up and knock.”

At least they’re close I thought as I drove the few minutes down the road. Once parked I collected my bag, took a few deep breaths to calm my nerves, and started for the lobby. Past the clerk with an impossibly suspicious gaze, up the elevator, to room 566. I knocked a little too hesitantly.

The door swung in to reveal a barrel chested man in nothing but a towel. Mark was strikingly handsome, better looking than his pictures had conveyed. I hoped a similar surprise was in store when I met Eva. It turned out that I was in for a surprise, but not the one I expected.

He stepped back and out of the way, extending his left hand inward to lead me. I stepped in and he reached for a handshake with his right, which had been holding up his towel, it fell as the door closed.

“Nice to finally meet you Mike.” He offered, standing naked and imposing before me.

“Likewise, Mark I presume?” I tried to sound collected. He could see the hesitation in me.

“The one and only.” He smiled, enjoying my discomfort “Don't mind me, I'm just getting comfortable.” He strode to the bed and I looked around for the first time as he reclined onto a stack of pillows, pressing play to restart the porno on the TV. Soft moans and wet sounds filled the room.

“No problem. Looks like you've started without me, I hope I haven't missed the show” I joked, smiling timidly. I wasn't usually this demure. A combination of this large naked man and the unexpected way our encounter had unfolded so far was throwing me off. “Where is Eva? In the bathroom?”

Was that sincere confusion on his face, or an act? “I told you, her flight was delayed.” She was still in New York an hour ago.”

“Oh…” I started. “I misunderstood…”

“Get comfortable, we can watch this for a while until we hear from her.” He gestured at the blonde getting double teamed on the TV.

“Yeah, sure.” That didn't sound too bad. He did have a bit of a suspicious glint in his eyes, though. “The drive was a little long. I'll rinse off while we wait.”

“Help yourself.”

I left my bag near the door, undressed in the bathroom, and got in the shower. The warm water allowed me some reprieve from my anxiety. What had I gotten myself into? Was he up to something or am I paranoid. I really want to fuck Eva, so far this is definitely worth the trouble, but how long will she be? Well, I can always leave if things get weird.

I turned off the shower and grabbed a towel to dry off. Suddenly the door opened and Mark, still naked, stepped through handing me a phone.

“It's Eva.”

I took it. “Hello?”

“Hi Mike? It's Eva.” Her voice was like silk. I so wanted to hear her cum.

“Eva! It's so good to hear from you! How are you?”

“Not great, I'm sorry Mike, my flight was cancelled. I'm spending the night in New York. I won't be able to make it to our date tonight.” She did sound genuinely sad.

“I'm sorry to hear that…” my heart sunk. Damn. I wasted all this time for blue balls.

“I was really looking forward to it. We should reschedule.”

“Oh definitely. Mark told me how sexy you are! I can't wait, but I don't know what my schedule will be like yet, we'll have to get back to you.” She purred.

“Of course.”

“Great, well it's been a long day. I'll leave you in Mark’s more than capable hands.”

What did that mean? “Ok Eva. Get some rest and dream of me!” I quipped. She giggled as she hung up.

That had turned around quickly. I handed the phone back to Mark.

“Damn. What a disappointment. She sounds amazing, Mark, I wish she could have made it.” I turned, looking around for my clothes. They weren't on the vanity where I had left them.

“She is.” He grinned wide “But it doesn't mean the fun has to be over.”

“I appreciate the offer, but like I said I'm not sure about being with another guy. If I'm going to experiment I'd rather have a woman present. It would just make everything more comfortable.” we’d been over this, but I felt the need to reiterate. “Do you see my clothes? I could have sworn I left them here.”

“What happened to ‘try anything three times’? I thought you were adventurous.” He shifted, placing a hand on my shoulder. As he moved I glanced behind him. My bag was not at the door anymore.

“Well usually I am, but this all changed so suddenly, it's just not what I was expecting.” I was backpedaling and he knew it. He put pressure on my shoulder, leading me out if the bathroom.

“Just give it a chance. I promise you'll have fun.” He said, guiding me into the main room. The blankets were off the bed and the massage oils I had brought were arranged on the nightstand.

What’s happening, I thought, fighting the urge to panic and run out the door. If I held my composure I might actually be able to face him again and meet the sweet goddess I was promised. But what does he mean, I'll have fun?

“Mark, did you go through my bag? Where are my clothes?” I asked trying to sound like it wasn't a big deal.

“You said you would bring toys!” he defended, “I got curious. I could really use those massage skills you bragged about. My back is really tight.” He ignored my second question, laying face down on the bed, head towards the TV. “Help me out. It would go a long way towards convincing me that you're the right guy to fuck Eva with me.”

What?! I thought he had already decided that! Shit! Was I being extorted? I paused, unsure of what to do.

He grabbed one of the bottles of oil, extending it out to me as if I had already agreed. Grinning still, knowing his leverage was working.

I reasoned that a massage was nothing I couldn't handle, and I really did want to get on his good side. This was my chance to steer the encounter to safer waters.

Taking the oil I said “Yeah, of course. I might as well put this to use if I'm here anyways.” I tried to play it cool, rubbing the bottle between my hands, warming it.

“Where does it hurt?” I resolved to do a good job.

“Where doesn't It?” he joked “Mostly my legs, lower back, and upper shoulders.”

I poured a large dollop of oil onto one hand, transferring to the other, and lifted one calf, starting on his legs. I slowly, firmly massaged into the muscles, stretching the fibers and working out any knots I found. Up the back of one leg, then the other.

“How’s that? Good pressure?” I inquired.

“Mmmmm" was all he could manage.

Mark was moderately hairy on his legs, arms and chest. His pubic hair was trimmed short. He was quite muscular. Despite my fighting experience, i thought, he might be able to beat me if he knew what he was doing. He probably had 40 pounds on me. His cock lay semi-erect pointed down between his legs. I made a point to avoid it as I worked up the back of his thighs. I brushed it once with my fingertips on the way by and his exaggerated sigh told me he wanted more.

I worked up to his defined ass muscles. He didn’t tense up like most people do as I reached to smooth oil over the firm globes. I pressed the palm of my hand deep into the muscle, smoothing out the knots. He wiggled his ass on the way by, causing my thumb to tickle his asshole. He was suggesting more, but I wouldn't have it.

I changed positions to start on his shoulders. I knelt on the bed beside him, leaning over, gripping his strong neck and shoulders.

“That's not enough pressure, you don't have the right leverage. Sit on my legs so you can use your weight.” He knew why I had avoided that. Giving a massage is a sensual act whether or not it's sexual. While I may not be attracted to him, between the intimacy and the big titted bimbo slobbering over a black dick on the TV, I was rock hard. I swung one leg over him still massaging his shoulders, and knelt straddling his upper legs. Predictably my erection nestled between his now slippery ass cheeks. Each time I pushed forward to put pressure on him, my erection glided along his crack.

“Mmmmm that feels good.” he groaned as I loosened his shoulder blades.

“Right there?” I pushed into a knot.

“Everywhere.” I could see him smiling as he rotated his hips, stimulating my cock. “So you've never been with a guy before?”

“No, never. You're the first guy I've seen naked outside of the locker room.”

“Do you like seeing the guys in the locker room? Checking out what everyone’s packing?” he chuckled. He seemed to enjoy making me uncomfortable.

“I've never really been attracted to guys.” I replied.

“But you like sex?”

“Well yeah, I'm here aren't I?” It was my turn for a laugh.

“Would you fuck a girl you weren't attracted to if it meant no strings?”

“Maybe…” I thought for a moment. “If we had a good platonic relationship and we both knew we could enjoy it without getting emotionally attached.”

“Hmmmm…” he started. “Sounds to me like you would have sex with a guy as long as they were a friend.”

“I don't know whether I would enjoy sex with a guy, I haven't tried it.”

“Well, you know how to fix that.” He cornered me. I chuckled awkwardly, not wanting to get myself in more trouble, and worked my way down to his lower back. In this position, at least my cock wasn't between his cheeks. Maybe he would get the message.

“Oh my god. That feels amazing!” I blushed a little “I haven't felt this limber in years, you have talented hands Mike.” He complimented. “My thighs and groin are hurting pretty bad now by comparison.” He rolled unexpectedly, effortlessly taking me off balance. Demonstrating a clear physical advantage while repositioning himself face up again, seated against the stack of pillows. I was left kneeling beside him. “Would you mind?” His now full erection stood at attention, his legs splayed. He looked directly into my eyes, willing me to comply. Was this still just a massage? I wondered. He took both my hands and pulled them to his thighs, eyes still fixed to mine.

I caved. Without a word I continued, kneeling in front of him on the bed. Pressing deep into the tissue of his thigh muscles, working slowly, reluctantly towards their apex.

He shifted his gaze to the TV behind me. Two young brunettes were fondling each other and kissing. With my hands on his thighs he started to slowly stroke his erection. With the rigid member less than a foot from my face I couldn't help but take in the sight. He was a similar length as me, about 7", but with much more girth. The perfectly straight shaft was wrapped in bulging veins. He was circumcised with a large dark mushroom head that glistened with pre-cum.

I moved my hands as high as I dared. Gripping his groin muscles and kneading the tension away. If I could get this over with maybe he'd let me fuck Eva. I could surely manage being face to face with a big cock for that.

He made his move. He reached for his drink on the nightstand but came away with a pair of handcuffs, evidently from the drawer below. Before I knew what he was doing they were secured to my wrists. I spoke up to protest as his hands wrapped behind my head, only serving to open my mouth as he forced me down.

“Hey- hmmmph" his bulbous mushroom head passed my lips and he let out a long gasp.

“Ahhhhh that's more like it.” I pushed against his thighs with no effect. One of his legs wrapped behind his hands, around my head, he trapped that foot in the crook of the opposite knee, capturing my head in his lap with a figure four lock. I struggled and sputtered in a moment of panic. I breathed through my nose as the salty taste of his pre-cum sank into my taste buds.

“That's enough pussy footing Mike.” He spoke while gyrating his hips, gently fucking my mouth. “You came here tonight for a new experience and I'm going to make sure you get it.”

I shook my head as best I could, trying to protest, but that only served to drag my tongue back and forth across his shaft.

“Mmmm that's a good boy, now you're getting the hang of it.”

He was clearly much stronger than me. Maybe I could make a play. Hit his nuts, eyes, throat, and run. No way to know if it would work for sure. And I could just make him angry. What would he do then? Even if i made it out of the room I was naked with no idea where my clothes were, where would I go? Part of me wanted this over as soon as possible, maybe if I just played along he would take it easy on me. Maybe he'd be satisfied once he came. My neck and arms grew tired of pushing back against him. I resigned to do my best. Apparently I was going to learn how to give a blowjob, I might as well make it a good one. If I get a chance to fuck Eva out of it, maybe it would be worth it.

I stopped struggling, relaxing my arms, bringing my hands to the base of his cock. I pushed my head forward a little, restricted by his tight grip. He sensed the change in me, releasing the lock with his legs but keeping his hands on my head just in case. At this point I could get a little more than half of his cock in my mouth. My jaw hurt from opening so wide, and I was humiliated by his forcefulness, but I didn't hate the taste. I explored the texture of his manhood with my tongue, almost finding enjoyment in the silky softness of the skin over his rigid pole. He pushed deeper into me and I felt his tip nudging at my throat. I suppressed the urge to gag, having taught a few girls along the way about the trick of squeezing your thumb to distract. Pleased with my compliance he loosened his grip on my head. I bobbed a few times, just as deep, to indicate my intent, then removed his shaft from my lips with a slurp and started licking the entire length.

“I knew you'd like it.” His voice dared me to resist again. “Fuck that feels great. You're a natural.”

I felt crushed. Humiliated. He was going to get his way with me and he would not allow me to object.

“Look at me boy.” He commanded. I couldn’t. Pretending this was still hypothetical, maybe happening to someone else, somewhere else. He pulled my chin up as I rounded his shaft with my tongue. My eyes pled for him to stop, I didn't want this. Not this way.

He grinned that smirking grin. No sympathy for me in his gaze. He grabbed his dick and guided my tongue to his balls. At least he’s clean I thought, tonguing his scrotum as he jerked next to my face. One last lick around his balls then I placed the flat of my tongue below his balls and dragged it slowly up to the tip of his cock, swallowing as deep as I could. He roared with appreciation, bucking his hips to meet my face. I grabbed his shaft with both hands, twisting and jerking his shaft between downstrokes. I pushed him further and further into my mouth, against my throat. After a few minutes my throat relaxed enough to squeeze his wide mushroom head past. I buried my nose against his pelvis. My throat flexed involuntarily against the intrusion, massaging him further.

Hmmmm. Fifteen minutes into my first blowjob and I've already taught myself to deepthroat. Maybe he was right after all. I looked up at him as he withdrew his shaft from my throat. He grinned down knowingly. I coughed, sputtered, and drooled.

“You're doing great, get on your back.” He commanded. He rolled off the bed. I hesitated and he grabbed the handcuffs, pulling me by my arms so that my head leaned off the edge of the bed. He straddled my arms and pointed his slick cock back at my mouth. Unable to push away I watched as the glistening rod probed at my lips, slid slowly and steadily across my tongue and down my throat propelled by his weight. He stood at the side of the bed feeding his engorged cock into me, giving me just enough time to gasp a breath with each withdraw.

“Oh yes, your throat’s squeezing me perfectly!” He sighed. “You were made for my cock, boy, and I can tell you like it.” he reached down to fondle my cock. Only then did I realize how hard I was. He gave me a few quick strokes as he drove his steely rod into me again. I shivered from the unexpected pleasure. As much as I hated what he was doing to me, the part of me that needed to please was being fulfilled. He grabbed my pelvis and used it as leverage to grind his hips deeper into me. He withdrew, wiped a big glob of my spit and mucus from his cock onto his finger, and plunged back into my throat with a grunt. Mark leaned over my prone body, impaling my throat, his balls dangling and swinging into my closed eyes, he reached past my cock and felt around for my virgin asshole. As he swirled a lubed digit around my tender hole I made the first sound of protest since he first forced his way into me. Humming a “no, please!” into his shaft, I tried to clench my legs.

“Don't struggle boy, or I won't bother with the lube.” His warning scared me sufficiently. As long as it was just a finger. I had let a girl milk my prostate before, it couldn't be too bad. His finger was thick but well lubricated. I unclenched and he plunged into me from both ends, bottoming out on my face and pressing his fist against my ass, his middle finger deep as he could go from that angle. He curled the finger like a hook, again using the leverage to fuck deep into my throat.

“Mmmm!” he groaned. “You're such a good fuck toy!” he degraded me further. “Come here.” He leaned forward, grabbed me by the waste and picked me up, upside down. It was a good thing I hadn't tried to run, I was like a rag doll to him. I was still attached by the lips to his cock as he knelt on the bed, crawling forward until I was pinned between him and the wall at the head of the bed. He eased me down so my weight rested on my shoulders. From this angle he couldn't penetrate my throat, but he continued to piston in and out of my mouth. He eased his torso backwards, trapping my left leg under his left armpit so that i was bent against the wall with my cock pointed straight down towards my face. His knees kept my head in place. He reached under my leg with his left hand and stroked my cock. He spit on my exposed asshole and teased it with two fingers. Slowly he inched them inside me. One finger had felt OK. Two fingers stretched me to the point of hurting, but the sensation of fullness was unexpectedly welcome. He used more spit as he inched deeper, until both index and middle finger penetrated me fully. He curled his fingers toward himself, this time dragging them across my prostate. I moaned involuntarily. That felt great. Despite my immense discomfort at the situation, I couldn't ignore my biological needs. He gradually increased his rhythm, drawing his fingers out as he thrust into my lips then pressing hard against my prostate as he pulled out of my mouth, eliciting a soft yelp from me each time, all the while jerking my cock. My mouth and jaw were numb from effort. My back ached from the contortion and my mind clouded as the blood pooled in my head. The urgent pleasure from his prostate massage was building. I forgot momentarily that I had been taken against my will.

As my orgasm boiled over I lost control of my body. Mark pulled his cock from my mouth, leaving my face exposed to the imminent gush. My mouth, still expecting to be impaled again, remained open. He aimed my cock straight at it. Bullseye. My orgasm erupted, shooting steaming jets of cum directly into my mouth. Pinned as I was against the bed and wall I couldn't object or evade. He pulled me down, closer to my mouth as I folded, dribbling the last drops of salty ejaculate into my still open mouth.

Mark released my leg and I crumpled to a heap on the bed. He clapped a hand over my mouth. “Swallow.” I obeyed. The truth was that I liked the taste of my own brew. Sometimes sampling it after I jerked off. But not like this. Not this much, not this way. It didn't taste bad, but the action still caused me to gag.

I laid crumpled on the bed, exhausted and bewildered. I couldn’t look at him. He had used me badly and against my will, but I had cum.

“Rest boy, it's my turn next.” He grinned again. That grin began to terrify me.

“No... “ I pleaded, softly. “This isn't what I wanted. I didn't want to do that. You forced me.”

“At first, maybe. I didn't force you to cum. That was you. I didn't force you to deepthroat me. Like I said, you're a natural.” I shuddered at his words. “I'm just helping you along the path to self discovery.” Now he was mocking me.

“This isn't who I am…” I objected.

“Prove it.” He returned. He stepped toward me and I recoiled.

“Ah, ah…” He cautioned. “No tricks this time, just sit up.” I sat on the edge of the bed. I couldn't look at him, so I just stared through him, eyes slanted down. He approached slowly, his large erection bobbing as he walked, at face level. He moved right up against me, his dick still slimy from my earlier ministrations, poked me in the upper lip. He stopped. Leaning forward just slightly. I didn't choose to open my mouth, it certainly wasn't a conscious effort. My lips parted automatically. A response cultivated by the onslaught i had just been subject to. As he leaned I stayed put and let his warm slippery cock slide over my lips once again. He held there, gently rocking his tip along the surface of my tongue.

“See boy. You like it. You want it.” No, I thought, I just can't bring myself to defy you. I pulled back enough to speak.

“All I wanted was for us to have fun with Eva.”

“Good, that's exactly what's happening.” He said, gesturing to a laptop on the desk nearby. “She's watching everything.”

Oh god no. It was one thing to be humiliated like this in private. To have the object of my desires be the only observer to my failure crushed me.

“Turn it off, please.” I begged

“I will…” That grin flashed again “when we’re done. Now lay on the bed, face down, put your hands underneath you.”

“What? Aren't you listening? No. I don't want to!” I pleaded, hoping blindly for some compassion.

“You don't want to YET. Just go along with it boy, you do want lube don't you?”

Lube for what? My mind raced. He pushed my shoulder, I fell backwards. He grabbed me by the hips, spun me around and up onto the bed, placing me just as he had commanded.

Mark moved to the nightstand and took something out. He climbed onto the bed and straddled my legs. I heard him take a lid off whatever was in his hand. Then a cool shock to my anus. Petroleum jelly. This was it, he was definitely going to fuck me.

“Please don't do this.” I begged. With my handcuffed hands pinned under me and Mark on top I could barely struggle. “I've never been fucked! You're too big!” I tried to roll beneath him.

“That's ENOUGH!” he struck me hard in the back, knocking the wind out of me. In a flash he had another pair of handcuffs from the night stand. He grabbed my hips and lifted, bringing my knees up almost to my shoulders. He cuffed one wrist to an ankle, uncuffed the original set, and did the same on the opposite side. I was face down on the bed with a freshly lubed asshole thrust high in the air, gasping for breath. He lined up behind me and shoved. My first breath was a scream. He managed to get the thick head into my sphincter on the first push. I felt like I was being torn in two from the inside. I grunted and moaned painfully. He eased back a bit and his head caught on my anal ring. It felt like having my guts yanked out and I hollered. He pushed in a bit further, inching his way into my ass, relishing the sounds of struggle and pain that he was causing. He gained more ground with each repetition until I felt his balls swing and hit mine. He hilted in my ass, pausing to let out a triumphant growl.

“Holy fucking shit this is even tighter than your throat.” He withdrew steadily until his head snagged on my sphincter again. I discovered that despite the burning pain of penetration I found the emptiness left behind uncomfortable.

He was right all along. I did enjoy getting fucked.

His next thrust was brutal. As fast and hard as possible into my rectum no pause for adjustment. “Ahh!” I cried. He set a dizzying pace, driving deep until his thighs slapped my ass and pulling out to the tip, almost pulling my sphincter out of my body. Each time it felt as if I would prolapse. Each time he would drive back in at the moment I thought I could take no more. I cried out with each thrust. It felt like hours of fucking and he still hadn't cum. His breathing became ragged. His assault on my hole more urgent and less controlled. As my muscles and resolve weakened my moans of pain became less strained and more effeminate. The pain was fading, replaced instead by a wet pistoning fullness. He leaned forward to thrust deeper and his head began to graze my prostate. My squeeks became squeals, and I felt my orgasm rising. Oh no, not again, I thought. He grunted loudly, slammed hard into my ass, and stayed there. I felt his cock swell in my ass as he came. A pleasant warmth flooded my insides as he coated my rectum with his juice.

He stayed behind me, flagging erection sheathed in my anus, rubbing my sides and slapping my ass, panting heavily as he recovered. When he did withdraw there was a distinct pop as his head separated from my anal ring. He left me handcuffed on the bed, grabbed the laptop, and moved the camera in for a close-up. I heard a giggle. It was real, she had been watching. I turned my head face down and wept. He had humiliated me, degraded me, dominated me, all while the goddess Eva watched. They had probably planned this from the beginning. Maybe it was a regular ruse and I was only their latest target. I could feel his cum, probably mixed with my blood, drip from my asshole over my balls.

Mark didn't say anything, he knew I was broken. He removed the cuffs, sat on the bed in front of me, legs splayed around my head, he set the laptop on the nightstand facing towards us. “Clean me off, boy.”

“Yes, sir.” I said. And set to work on my task.

I never heard from them again after that night.

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