Do you want to watch?" Ashley is this very hot Cali girl, much younger than me and way out of my league. But we met on a porn site and hit it off, so we had become long distance FWB—phone sex, sexting, sharing experiences. We live across the country from each other, but someday we will be in the same city and it will be awesome.

Ashley is a cute little thing, with a lovely face, long flowing hair I want to wrap around my dick and a killer body. She can fuck any man she wants to, anytime. Guys fling themselves at her at work, on the street and online. She loves to flirt and blue ball the bros in town, but I know from hearing her exploits that the lucky guy who gets Ashley naked is going to have the fuck of his life.

But this was different. Ashley had never offered to let me watch her bang a guy, so this text came out of the blue one Friday night. I knew she got turned on by the thought of being watched, but from afar, so she shared my love of fucking in the hotel window and stroking her date’s cock or having her pussy fingered under the restaurant table. But, being a total gentleman, my response was obvious.

"Fuck yeah I want to watch!" Where are you?"

"In the club. He is in the Men’s Room. We are getting ready to head to my place."

"How’d you pick the lucky guy?"

"Duh. He’s hot, he’s ripped, and he put his hard dick against my stomach when we were dancing. It’s a nice dick. I decided I wanted it."

"So how we going to work this?"

"I’ll FaceTime you when we get home. You’ll have a good view. I’ve been fantasizing about fucking on cam for weeks. Two fantasies checked off in one night."

"Damn you're amazing."

"Lose your pants. You’re going to want to stroke it to this one. He’s coming now. Later."

Ashley needn’t have encouraged me. As soon as she told me her plan, I got my dick out. I opened a bottle of wine, took off my pants and waited for the show to start. After about 45 minutes my computer buzzed.

"You ready?" Ashley asked in a hushed voice. I tilted the screen down so she could see my hand stroking my hard cock. She laughed. "Looks like you started without me."

"Where is he? Does he know you're camming this?"

"In the shower. His name is Derek. At least that’s what he told me. He doesn’t know, so stop your video and mute your computer."

"Of course. Damn Ashley, you’ve got a hot naked man with a nice cock in your shower—go!" Ashley stood, showing me the view of the room where the deed would be done. I pushed "record" on my computer. Ashley smiled at the camera and undressed in front of me. Damn that girl has a killer body. Before heading to the shower she stuck her tongue out at me, bent over and flashed me her tight little asshole. I could have cum right then.

Ashley bounced off to the shower in the next room. I only heard muffled voices, some laughter, a bit of heavy breathing. Then Ashley’s voice came through louder than before, enthusiastic, but, well, pained.

"Ahhhh! Ahhhh! Shit…don’t…yeah…" Then Derek came into view, carrying Ashley, her legs wrapped around his hips. Their bodies were still wet from the shower. She was sliding slowly up and down on his shaft. His hands were on her ass, and I saw him slide a finger into Ashley’s asshole. She started fucking him by just rotating her hips. His cock glistened with her wetness.

"Yeah baby…fuck me…gimme that tight pussy." Derek murmured as he jammed his finger farther up Ashley’s ass. Ashley’s head was thrown back as she writhed on Derek’s dick. She opened her eyes and looked at the camera and mouthed "OMG" at me before she shifted her focus back to fucking Derek. Her hip thrusts were getting shorter and her breathing was getting heavier. I could tell she was angling to rub her g-spot against the head of his cock. One of her favorite moves. Her thrusts were shorter and faster and then she came hard on Derek’s dick, her pussy dripping wet as her body convulsed with pleasure.

"Uhhhh…uuhhh…uhhh…fuck…" Ashley doesn’t make a lot of noise when she cums. She kissed Derek hard as she lifted herself off his cock and slid down his sculpted body onto her knees. She turned him a little towards the camera, giving me my first real view of his rigid snake. Ashley had good taste in dicks, and Derek was no exception. Not monstrously long, maybe seven or eight inches, but very thick. Maybe the thickness of a beer can, probably somewhat less. Whatever the exact measurements, Ashley is a small muscular woman. I was impressed that she took the stretching that cock gave her pussy and came out smiling.

On her knees, Ashley stroked his dick with one hand and cupped his massive ball sack with the other. If his cock was not unusually large, his balls were the largest I’ve ever seen, and I watch a lot of porn. Ashley slowly licked his sack, stopping to suck each ball into her warm mouth.

"Oooooh…damn…do it girl…" Derek purred as Ashley worshipped his beautiful balls. She took the skin of his sack with her teeth and pulled hard.

"Ahh! Ahh! Ahh! Jesus fuck," Derek exclaimed, not in pain but in pleasure. Ashley got a second grip on his sack and pulled again, while stroking his cock a little harder. Derek had two handfuls of Ashley’s hair but wasn’t pulling it, just holding her head in place. Ashley turned and sat between his legs. Holding his balls and stroking his cock, she began teasing his taint with the tip of her tongue. She licked her way towards his ass crack, but his cheeks were muscular, and his butthole remained hidden.

"You’re so bad baby…" Ashley’s tongue ventured back to Derek’s balls, licking, biting sucking while she stroked his cock vigorously with both hands. She returned to her knees, face to face with Derek’s throbbing member, grabbed his balls and pulled hard.

"Damn, girl, what you do…" Derek grabbed his dick and began slapping Ashley’s face with it. Precum spattered on her cheeks in the dim light. "Think you can handle this big black cock little girl?" He kept slapping her face with his hard cock. There’s enough mass there, I thought to myself, that could hurt. But Ashley kept her eyes closed as each slap turned her head slightly. I saw the start of a smile. Suddenly her eyes opened and she grabbed Derek’s junk with both hands and pulled hard.

"Let’s find out. Only one way to tell." Derek reached down and grabbed Ashley under the arms. He picked her up like she weighed nothing and tossed her the short distance onto the bed. As she landed on the bed, Derek knelt on the bed, grabbed Ashley’s ankles and pulled her legs apart. Her legs were straight up in the air, toes pointing to the ceiling as Derek eased closer and placed the head of his cock between her pussy lips.

"Oooh, yeah…" Ashley moaned. Derek’s knob glistened with pussy juice as he rubbed the head of his dick along Ashley’s wet slit. "Keep doing that…that…just like…that." Ashley reached between her legs and grabbed Derek’s shaft, rubbing it more vigorously around her clit. "Fuck, I could cum just like this…but I want this inside me." Ashley placed Derek’s cock against the opening of her wet hole. He slowly leaned forward giving me a perfect view of his beautiful black cock disappearing inch by inch into Ashley’s pussy. "Ummph…yeah…shit…".

"Take it all baby girl…take it all." Even from my imperfect vantage point I could see Ashley’s pussy stretching wide to take his big dick. Ashley’s head was thrown back and her eyes were closed. She was biting her lower lip.

"Oooohhh…mmmmm…fuck me…hard…I want you to fuck me hard Derek." Holding Ashley’s legs straight in the air by the ankles, Derek started moving his hips, sliding in and out of Ashley’s tight pussy. Ashley was much smaller than Derek, but I could see Ashley took all of Derek’s cock inside her. "Harder! Fuck me with that thing!" Derek pushed Ashley’s legs a bit farther and began pounding her pussy harder. Her tits slid in rhythm with Derek’s pounding. Ashley opened her eyes, locked Derek in her gaze and began massaging her clit. "Choke me…a little…choke me, Derek." Derek’s fingers wrapped around Ashley’s lovely neck and he began to squeeze. Her eyes closed again and she rubbed her clit harder. As Derek’s grip tightened, Ashley’s eyes opened wide, panicked, and her mouth opened as she gasped for air. "Kaaahhh…kaaahhh!" Ashley gasped. She stopped rubbing her clit as her hands shot to Derek’s wrist to pull his hand away.

"Don’t worry baby. I got you, I won’t hurt you."

"Gaaaaaahhh! Gaaaaahhhh!" Ashley’s gasping became more desperate as her eyes bulged. I was about to unmute my audio and tell him to stop when Ashley’s body writhed with a powerful orgasm. Ashley couldn’t make a sound, I thought she was going to pass out.

"Fuck yeah…squeeze me with that pussy baby girl…Squeeze me…hard…and I’ll let you go." Ashley was thrashing and fucking Derek so hard I don’t know how he didn’t cum. I came all over my hand just watching. Derek released his grip on Ashley’s throat and she coughed and inhaled sharply several times.

"Asshole!" Ashley rasped. "I said gently! I almost passed out you fucker!" Derek was now holding her still vertical legs, keeping his monster buried in her pussy. I could see Ashley’s juices flowing around his still hard shaft.

As Ashley came to her senses, Derek slid out of her pussy, his cock shiny with Ashley’s pussy juice. He pushed Ashley’s legs to one side. "Roll over baby girl." Ashley turned onto her stomach. Derek grabbed her hips and pulled her onto her knees. Ashley was now on her elbows, ass in the air. His large hands still holding her hips, Derek spread her ass with his thumbs. His long thick tongue came out and pushed against Ashley’s tight asshole.

"Awwww fuck yeah," Ashley whispered as Derek slid two fingers into Ashley’s wet pussy. His fingers worked her pussy, fingers on her G-spot, thumb swirling around her clit. The tip of Derek’s tongue was pushing hard and wiggling against her tight anus. He wasn’t rimming her, he was forcing his tongue up Ashley’s tight little asshole. For her part, Ashley was pushing against the bed with her hands, trying to push her asshole onto Derek’s tongue. "Harder…push harder baby…get in there…". Aside from his other toned muscles, Derek’s tongue seemed similarly made of steel. It didn’t bend as he pushed hard against Ashley’s reluctant sphincter. "Mmmmm…damn…yeah…" Ashley moaned again as I could see her asshole starting to spread under the relentless pressure of Derek’s rigid tongue. "Oh fuck! Baby!" Ashley said sharply but quietly. Feeling Derek’s warm wet tongue violating her asshole was clearly a new sensation for Ashley. It was taking her a bit to process it. "Fuck…what are you…how are you…fuck. Uh-huh…yeah."

As someone who considers himself an expert at tonguefucking a woman’s asshole, I can tell you that what Derek was doing was not easy. If a woman hasn’t practiced gaping, it is tough to get your tongue up her asshole, at least not without stretching it and relaxing it a bit with your fingers. Derek’s head bobbed back and forth as he had managed to get half his tongue up Ashley’s asshole. And it was clear he was going to get his entire thick tongue into Ashley’s anus.

"Jesus…" Ashley murmured. Her eyes were closed and her body rocked back and forth a bit in rhythm with the thrusts of Derek’s powerful tongue. She gripped the sheets tighter in her hands as another orgasm built in her body. "Damn…that’s so…fuck…". Ashley was lost in the moment, her pussy and asshole being aroused at the same time. "Fuck…I’m gonna cum again…fuck that’s nasty…deeper…go deeper…". Derek’s lips were now up against Ashley’s ass as his tongue slithered in and out of her stretched asshole. "Oh fuck…dude…yeah…keep…yeah…fuck…yeah…FUCK FUCK FUCK!!!" Ashley’s eyes shot open and she gripped the sheets like she was holding on for dear life. She usually came fairly quietly, but not this time. "Holy fuck…FUCK!" She thrashed about, but Derek’s strong hands on her hips held her in place and he kept thrusting his tongue deep into her rectum. Ashley rose up on her hands and turned her head to watch Derek’s last few strokes with his tongue. "Shit that is so nasty…but so fucking hot. Keep going…"

Derek finally slid his tongue out of Ashley’s gaped asshole. "Oh I am not finished with this asshole little girl." He rose to his knees and slapped Ashley’s ass with his stiff dick. Damn, but that man was packing some heat. "You ready for this black dick little girl?"

Ashley squirmed to get away, but Derek held her in place by her hips, his cock resting in Ashley’s spread ass crack. "Ummm, nope. No. Nuh-uh. Too big. Not doing it. Let me go." Ashley protested. Ashley has a gorgeous tight asshole that just begs to be fucked, but Derek’s cock looked enormous by comparison. It looked ever bigger than before.

"I’m going to fuck you in the ass little girl," Derek said casually. "You told me in the car that you loved getting it in the ass."

Ashley continued to squirm. "Yeah, I like getting fucked, not split in two. It’s too big Derek. It won’t fit, let me go."

"All you ho’s say that, but after they take it, they want to do it again." Derek worked the massive head of his dick against Ashley’s tiny anus. At least she was gaping a bit from Derek’s tonguefucking, but I imagine her asshole was tightening up in fear. Derek started to push. Ashley’s already-stretched anus began to spread immediately.

"Ow! Damnit it’s too big! Stop! It’s going to hurt."

"Relax little girl, you know it only hurts until I get it in. Then you gonna love it."

"Fuck. Ow! Ow! Ow, that hurts! Okay, just go slow. SLOW…ow…ow...ow…" Ashley whimpered her last protest, her face locked in a grimace. I think she glanced at the camera a couple of times though, and kind of smiled, happy to know I was watching her take that big dick.

I could zoom in my view of the action and watched as the bulbous head of Derek’s cock disappeared into Ashley’s tiny butthole. A hard cock spreading and violating a tiny asshole is about the hottest thing in the world. I was stroking my cock furiously, hard again and still slick with my jizz from the last time this live porn made me cum. I have dreamed of fucking Ashley’s ass for years and watching her take Derek’s thick shaft was pushing me over the edge.

"I’m in little girl, just relax" Derek said reassuringly.

"It still fucking hurts, asshole! Give me a minute to relax…you are so fucking thick." Ashley still grimaced as Derek pushed about three inches of thick black cock into Ashley’s asshole. Then he paused and just moved back and forth an inch or two. Ashley reached behind her and tugged on her ass cheeks, urging her asshole to stretch. After a bit her expression relaxed a bit, her hips started sliding her asshole on Derek’s cock, her hand moved between her legs to massage her clit. Ashley moaned softly. "Mmmm…Derek?"

"What little girl?"

"Will you cum in my ass? Fuck me hard and cum in my ass?"

"Yes baby."

"And Derek?" Ashley was almost whispering now. "If I scream and tell you to stop…"

"…I’ll stop, I prom…"

"No! Don’t stop. Even if I beg. I want you to cum in my ass."

Derek needed no further encouragement. He grabbed a big handful of Ashley’s hair and pulled her head back hard, using it as leverage to ease the full length of his shaft into Ashley’s anus. I couldn’t believe her ass could take that whole thing. Neither could Ashley.

"FUCK! FUCK! It’s too big! Too big! AAAhhhh! Shit shit shit…". Derek held his cock all the way up Ashley’s ass, his pubes buried in her crack. Despite her protests, I saw Ashley’s hips gyrating, grinding slightly on Derek’s dick. Derek pulled his cock halfway out and slammed it back in, hard. His large ball sack slapped against Ashley’s wet pussy. "OW!!!" Ashley said sharply. She reached between her legs and grabbed Derek’s swinging balls. "Do it!" she said softly. "Fuck my ass hard, baby."

Still holding Ashley’s hair in one hand, Derek grabbed his cock with the other and pulled all the way out of Ashley’s asshole. I could see how stretched it was in the split second before Derek thrusted his cock back in her asshole, hard. Just watching that made my ass hurt.

"Uh! Uhh! Uhh! Shit! Shit!! Uhhh! Uhhhh!" Ashley grunted loudly each time Derek thrust inside her. She was gripping the sheet with both hands as Derek pounded her tiny ass. "Cum! For! Me! Baby! Please!" Ashley spat out each word softly each time Derek buried himself in her anus.

"Your ass is so tight little girl. You’re gonna make me cum…fuck yeah!" Suddenly Derek stopped pounding and held himself deep inside Ashley. His cock pulsed as he pumped his semen into Ashley’s abused ass. "Aaawwww…fuck yeah little girl. Damn! Fuck yeah!" Derek murmured, his head thrown back, eyes closed. I couldn’t see perfectly, but it looked like Derek’s cock had pulsed hard about ten times. It looked like he had dropped a pretty impressive load of cum in Ashley’s ass.

My guess was confirmed as Derek’s softened dick popped out of Ashley’s asshole. I spurt of cum erupted from Ashley’s ass as the pressure inside was relieved. Then, a steady stream of cum oozed from her pounded asshole and ran down her thighs. Derek collapsed onto his back, breathing heavily from the pounding he’d given Ashley’s holes. "Damn little girl! How are you doing?"

"I’m okay, but that hurt like Hell." Derek had gotten quiet, his deep breathing more steady. It seemed like he was falling asleep. "Oh hell no!" Ashley said loudly. "You don’t get to pound my ass and pussy and just go to sleep. She spun around and straddled Derek’s head. He awoke to his cum dripping from Ashley’s ass onto his face.

"Wha the…?" Derek sputtered as he awoke.

"My turn to take what I want. Now clean up your mess." With that Ashley squatted on Derek’s face, cum oozing freely from her asshole. "Start licking babe." Derek squirmed a bit and made muffled sounds of protest, then grabbed Ashley’s hips and began to do what he was told. Loud licking and slurping sounds came from derek. Ashley leaned her hands on his large pecs as she ground her ass into Derek’s face.

With Derek’s face hidden, Ashley began mouthing and gesturing in my direction. "Did you see that?" she pantomimed. She held her hands apart, giving me her estimate of the length of Derek’s member. "Ow!" she mouthed in my direction. Then she used both hands to make a circle that she peered through like a telescope. Derek’s girth, I surmised. She was riding Derek’s face hard, occasionally reaching behind her and pushing his head deeper into her ass. Derek made no noise except for the licking and swallowing of his own cum.

Ashley was satisfied with Derek’s work after a bit and slid off of his face. She knelt beside him and rubbed his ripped abs and pecs while he used the sheets to wipe the remnants of cum from his face. Ashley casually wiped Derek’s cock clean with the sheets, presumably to remove the taste or her ass from it. Then she leaned over, took his flaccid cock in her hand and gently began licking its large head.

"What are you doing little girl? You gonna mess around and get me hard again."

"Just playin’. We’ll see what you got."

"Oh fuck baby…". Derek leaned his head back and enjoyed the warm feeling of Ashley’s head on his cock. Ashley was bent over, her ass pointed towards me. Her normally tight pink asshole was red and inflamed. That had to hurt. Ashley was concentrating on Derek’s cock, swirling her tongue around the head. Licking the shaft like a little girl licking up a melting ice cream cone. That girl is so fucking hot.

Just watching Ashley lick and suck that dick got me hard again, so it was no wonder that Derek’s cock soon began to stiffen and lift off of his stomach as she stroked and flicked her tongue along the base the rapidly swelling head of his dick.

"Little girl, you gonna have to give me some more of that tight pussy now," Derek said as he lifted his head to watch Ashley at work on his cock. She raised her head to answer while continuing to stroke Derek’s cock with two hands.

"Ha! No. Nope. No way. My holes are already going to be sore for a week. I don’t want anymore pounding tonight." Derek’s cock was now fully erect, throbbing in rhythm with his pulse.

"C’mon little girl! You can’t send me home like this. I’d have to…"

"I’m not," Ashley interrupted. "I’m going to take care of you. Just doing it my way. Lay back and let me make you cum."

Derek stopped protesting as Ashley climbed on top of him, straddling his cock. She traced the outline of his six pack abs with her fingers. She reached between her legs and placed Derek’s throbbing dick between the lips of her dripping wet pussy. Derek’s cock glistened with her pussy juice as she ground her pussy onto his cock.

"You’re still getting my pussy, babe. Just my way. Now cum for me baby." Ashley braced herself with her hands against his pecs and leaned forward so her clit would rub against his throbbing cock. "Mmmmm…yeaah…fuck yeah…". Ashley was already breathing heavily, the way she does when she is building up to an orgasm. Derek was grinding back with his hips.

"Fuck little girl…you feel so good." Derek was now watching Ashley slide her pussy along his shaft. "Just like that little girl…just like that…you’re gonna make me cum again…damn." Ashley reached behind her and started fondling Derek’s balls.

"I love your fucking balls…so big." Both people were breathing heavier and heavier, Derek was moaning slightly. Ashley fingers were dancing across Derek’s sweaty taint. "Spread your legs baby." Ashley said softly. She probed his crack with two fingers. "Pull your knees up." Derek obliged. Ashley leaned back a bit so her fingers touched his asshole. "Fuck baby, I’m going to cum," Ashley moaned, rubbing her clit faster against his tool. "Fuck yeah…fuck yeah…cum with me Derek…cum with me. Ashley thrust a finger, maybe two into Derek’s asshole. She watched his face has her fingers explored his ass.

"What the…fuuucckkk! Jesus!" Derek’s eyes shot open as a jet of cum exploded from his cock. Ashley smiled as she worked her fingers inside Derek’s ass. "What are you…". He couldn’t even finish his sentence as his cock spewed stream after stream of cum across his chest and stomach. Some shots even hit his face.

"Mmmmm…that’s it baby, cum hard for baby girl," Ashley didn’t make a sound as she squirted on Derek’s cock as she came. She jammed her finger harder up Derek’s ass.

"Damn…yeah! Fuck…" Derek’s balls had emptied all over his sculpted chest and abs. Ashley managed to coax a couple final small squirts from his dick as she manipulated his asshole. Derek’s milky white cum stood out on his chocolate brown skin.

"Better baby?" Ashley purred as she climbed off of his cock.

"Jesus…yeah…how the…I never…". Derek was delirious and could not finish a sentence.

"You were pretty amazing," Ashley said, kneeling next to him and still stroking his cock. "I’m going to clean up this mess." Ashley flipped her hair onto her back, bent over and slowly started licking Derek’s cum from his dark skin. She giggled a bit as she lapped up the cum pooling in his ripped abs. Derek held her hair back as he watched her slowly lick up his load.

"Damn little girl, you are nasty as fuck."

"Good, that's exactly what I was aiming for." Ashley laughed as she dipped her finger in a drop of cum and licked it clean. "We gonna do this again someday?"

Hearing Ashley say that, my cock exploded across my computer screen. I had been watching so intently I didn’t notice I was stroking my dick furiously. Ashley made both Derek and me cum twice that evening. I left my computer recording as I went to clean up. I sent Ashley a message saying I had a recording of her if she wanted a copy. I so wanted to watch it along with her…

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