Gay First Anal porn videos, gay first Anal experience - Page 20 - ShaRinG

LMChallea · 07-08-2025, 06:08 PM

Boy For Sale - The Grooming - The Boy Jack Waters Renault

Release Year: 2025
Studio: Boy For Sale
Cast: Ace Banner, Jack Waters
Genres: anal, dildo, gay, masturbate, oral, porn
While flipping through community college brochures at a career fair one afternoon, Jack Waters let out a discouraged sigh. School was extremely expensive these days, and it was becoming clear that his series of odd jobs during the week was not going to cover the cost of tuition. Disheartened, young Jack was about to give up when he saw the glint of a golden ticket half covered up by a stack of sex education pamphlets. Jack was both puzzled and intrigued by the fact that the golden ticket only had an email address followed by a four digit number and a strange request to submit a picture in .jpg format. With nothing left to lose, Jack submitted the random four digit number with a random photo showing his face, then sent it to the email address. Almost immediately, an email message came back with an invitation to meet at an address uptown. Perplexed but also desperate, Jack decided to go with it. The nervous twink was met at the end of a dark alley at the edge of town by a tall, bald, handsome man in a perfectly tailored suit. It looked incredibly expensive. Jack recited the four digit secret code to the severe-looking gentleman, who nodded and then unlocked a gold-plated doorway that led into a dimly lit chamber. Jack was informed this was the ‘Vetting Chamber’. The young man gulped, but excitedly entered the room. The door was closed behind him. The older gentleman introduced himself as Master Banner. In a no-nonsense tone of voice, this man with ice-blue eyes instructed Jack to take a seat and remain silent until spoken to. A shiver pulsed up the young twink’s spine. It was both terrifying and exhilarating to be addressed in such a way. He kind of liked it, but kept a straight face as he had a feeling even a stray smile might fuck up his chances at the money. A pearl-white document was placed in front of Jack. Master Banner implored the youth to read every line. If Jack agreed to the contents of the contract, and he subsequently obeyed every command given to him going forward, the dollar amount stated at the bottom of the contract would be his afterwards. A few moments later, his veins pumping with adrenaline, the newly-renamed Boy Jack was guided into another room. Master Banner said this was the “Grooming Chamber.” In the center of the room was a large square platform. The newly signed Slaveboy was commanded to remove his clothing, hop up onto the platform, and place himself in the doggy position. The Boy Jack swallowed hard and hesitated for a moment. Master Banner snapped his fingers sharply and with a frigid, buzzer-like tone of voice, reminded the young Slaveboy that compliance was expected to be followed with haste and a sense of urgency. Anything less was unacceptable. The Boy took a shaky breath and nodded. He made a mental note and decided it would probably be wise to pick up the pace a little. Soon, Boy Jack was completely nude and on top of the grooming altar. The twink slave was quite the specimen long, tall, with flawless skin, and clearly into physical fitness as his body was well toned for one so young. Master Banner salaciously groped every inch of the Slaveboy’s beautiful body. Boy Jack moaned and sighed in response to the intimate touch. Master Banner’s duty this evening was to prepare the slave for future buyers. The Boy, as stated in the contract, must be ready for anything - any desire that a gentleman buyer might have must be granted. And seeing that The Boy Jack was a virgin, Master Banner was required to begin the momentous ritual of preparing a Slaveboy for his first anal penetration. The Boy Jack closed his eyes for a moment, enjoying the pleasant sensations of Master Banner’s touch all over his body. Those eyes immediately snapped back open when The Boy heard the sound of a cap popping open. The suited gentleman had a large bottle of what appeared to be oil and he began applying a very generous amount all over the boy’s chest and back. The proceeding was very sensual and arousing. Boy Jack immediately sported an erection and secretly hoped that the experienced Master might permit him to stroke his own cock using the oil. Even better, Master Banner proceeded to massage the warm, gentle lubrication not just along the slave’s swollen twink member, but his hairless scrotum as well. That’s when the gentle ministrations suddenly turned more aggressive. The suited dominator held The Boy’s ballsack by the base and squeezed - hard. The Slaveboy involuntarily emitted a hiss of surprise and fear. Master Banner pressed hard up against the Boy and shushed him. Boy Jack took a long, slow breath and held it while the merciless Master continued to test the submissive’s will. Other Masters would surely expect the Slaveboy to be eager and docile even in the face of somewhat harsh sensation. The Boy Jack thought about the money and soon, the intensity died down somewhat. Finally, Master Banner released the Slaveboy’s testes from his tight grip and commanded The Boy to lie on his back and pull his shapely legs towards his chest, exposing his precious pink virgin hole. As he did so, the twink noticed how Master’s eyes seemed to feast on his boy pucker. The Slaveboy wondered with a slight shiver what was going to happen next. Master Banner pulled out a long, curved glass dildo and The Boy Jack took another sharp breath. The sex toy was shiny like diamonds and had two cockhead-shaped bulbs on each end. Master Banner caught the Slaveboy’s glance. Here and now was the moment of truth. Master Banner would be gentle - at first. The Slaveboy gulped loudly and took another deep breath. Master Banner poured a generous amount of oil all over the twink’s pink pucker. Then, when the Master pressed one bulbous end of the glass dildo against the Slaveboy’s anus, the older gentleman found himself aroused by hearing The Boy’s initial whine, followed quickly by a deep, primal groan as the dildo very slowly buried half-inch by half-inch deeper and deeper inside of the insanely tight anus...
Format: mp4
Duration: 30:26
Video: 1920x1080, AVC (H.264), 7781kbps
Audio: 156kbps

File size: 1.7 GB

DOWNLOAD FROM FILESMONSTER: Boy For Sale - The Grooming - The Boy Jack Waters

LMChallea · 07-26-2025, 04:50 PM

Plowing Dylan Nuuk

Cast: Chris ,Dylan
Genres: Bareback , Gay Porn
Video language: English
Two things I don't think I could ever get tired off - seeing Chris rim, and seeing Dylan get rimmed. So seeing Dylan get rimmed by Chris?! Awesome! Chris just loves to eat ass! He showed up at CF loving eating ass. The first ass he had the chance to eat when he arrived here, he dove in to immediately. Dylan, on the other hand, hadn't yet gotten to experience how the ass could be a part of sex. He was ass unaware when he first arrived at CF, but he definitely knows full well what a source of pleasure it can be now! Teaming these two up with one another to let Chris go to town on Dylan's hole - and get his tongue and dick buried in it - is a total treat and now is certainly a third thing I could never get tired of seeing!
Format: mp4
Duration: 17:40
Video: 1920x1080, AVC (H.264), 5842kbps
Audio: 184kbps

File size: 783.2 MB

DOWNLOAD FROM FILESMONSTER: Plowing Dylan

LMChallea · 08-01-2025, 05:45 PM

First Anal Fuck San Pierre

Release Year: 2024
Genres: Asian, Twinks, Oral, Anal Sex, Rimming, Masturbation, Toy, Fingering, Cumshot
Video language: Japanese
ノンケの持つ『爽やかさ』と『男ら� �さ』と『エロさ』を追い求める！ス� ��ウトしたての新人ノンケたち五人の処女雄穴に即巨根チンポを挿入！苦� �に悶える！密かに芽生えた快楽に戸� ��い！
Format: avi
Duration: 2:42:45
Video: 720x416, XviD, 1393kbps
Audio: 125kbps

File size: 1.8 GB

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LMChallea · 08-11-2025, 05:00 PM

Plowing Dylan North Vernon

Cast: Chris ,Dylan
Genres: Bareback , Gay Porn
Video language: English
Two things I don't think I could ever get tired off - seeing Chris rim, and seeing Dylan get rimmed. So seeing Dylan get rimmed by Chris?! Awesome! Chris just loves to eat ass! He showed up at CF loving eating ass. The first ass he had the chance to eat when he arrived here, he dove in to immediately. Dylan, on the other hand, hadn't yet gotten to experience how the ass could be a part of sex. He was ass unaware when he first arrived at CF, but he definitely knows full well what a source of pleasure it can be now! Teaming these two up with one another to let Chris go to town on Dylan's hole - and get his tongue and dick buried in it - is a total treat and now is certainly a third thing I could never get tired of seeing!
Format: mp4
Duration: 17:40
Video: 1920x1080, AVC (H.264), 5842kbps
Audio: 184kbps

File size: 783.2 MB

DOWNLOAD FROM FILESMONSTER: Plowing Dylan

LMChallea · 08-28-2025, 07:14 PM

Straight College Boy First Anal - Ayumu Tsukamoto 19yo 416p Lucca

Video language: Japanese
1は、極タチ航と22達の248手集！には、人気2啓志や新人2太一が生掘りで男同士の濃厚SEX体位を披露！「締込み千� �」「虹の架け橋」など24手収録。
Format: avi
Duration: 2:12:40
Video: 720x416, XviD, 1924kbps
Audio: 125kbps

File size: 2.0 GB

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LMChallea · 09-02-2025, 05:50 PM

First Anal Fuck part 1 New Roads

Release Year: 2024
Genres: Asian, Anal, Oral Sex, Masturbation, Cumshots
Video language: Japanese
リアル＆エキサイトをコンセプトに� �メーカー誕生！
ノンケの持つ『爽やかさ』と『男ら� �さ』と『エロさ』を追い求める！
スカウトしたての新人ノンケたち五� �の処女雄穴に即巨根チンポを挿入！
苦痛に悶える！密かに芽生えた快楽� �戸惑い！
初めてのアナルに感じて掘られイキ� �でしてしまうエロノンケ！
Format: avi
Duration: 2:42:45
Video: 720x416, XviD, 1393kbps
Audio: 125kbps

File size: 1.8 GB

DOWNLOAD FROM FILESMONSTER: First Anal Fuck part 1

LMChallea · 09-05-2025, 06:56 PM

Plowing Dylan Radcliff

Cast: Chris ,Dylan
Genres: Bareback , Gay Porn
Video language: English
Two things I don't think I could ever get tired off - seeing Chris rim, and seeing Dylan get rimmed. So seeing Dylan get rimmed by Chris?! Awesome! Chris just loves to eat ass! He showed up at CF loving eating ass. The first ass he had the chance to eat when he arrived here, he dove in to immediately. Dylan, on the other hand, hadn't yet gotten to experience how the ass could be a part of sex. He was ass unaware when he first arrived at CF, but he definitely knows full well what a source of pleasure it can be now! Teaming these two up with one another to let Chris go to town on Dylan's hole - and get his tongue and dick buried in it - is a total treat and now is certainly a third thing I could never get tired of seeing!
Format: mp4
Duration: 17:40
Video: 1920x1080, AVC (H.264), 5842kbps
Audio: 184kbps

File size: 783.2 MB

DOWNLOAD FROM FILESMONSTER: Plowing Dylan

LMChallea · 09-06-2025, 06:55 PM

Coat - Yusei Sports Club Domination Hettinger

Studio: Coat
The main star of 'Active body 16,' the sculpted, macho water polo player 'Yusei, 22,' makes his stunning debut in 'Athletic Club Domination'!! A stunning physique, a brave, masculine expression, and a curved cock brimming with veins!The invincible athlete's passionate first anal fuck!!An East-West collaboration with Hongo from 'R-30'! A total of four parts, including some intense muscle-to-muscle sex!!
Format: mp4
Duration: 2:06:48
Video: 1920x1080, AVC (H.264), 3424kbps
Audio: 124kbps

File size: 3.2 GB

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LMChallea · 09-16-2025, 05:56 PM

Rookie Private's First Anal Probing and Facial 1080p Parachute

Genres: Anal Sex, Oral Sex, Condom
A military recruit visits the doctor for a slight tear of his foreskin due to excessive jerking off and appears nervous as he waits for his turn. During the examination, the doctor thinks the recruit tries to cook up an excuse to escape training and decides to teach him a lesson. The scene ends with the recruit visiting the doctor again, but this time, he looks sheepish and slightly hopeful. The doctor, from the look on his face, knows the best medicine to prescribe.
Format: mp4
Duration: 39:38
Video: 1920x1080, AVC (H.264), 2818kbps
Audio: 312kbps

File size: 910.9 MB

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LMChallea · 10-10-2025, 05:39 PM

First Anal Fuck part 1 Budapest

Release Year: 2024
Genres: Asian, Anal, Oral Sex, Masturbation, Cumshots
Video language: Japanese
リアル＆エキサイトをコンセプトに� �メーカー誕生！ノンケの持つ『爽や� ��さ』と『男らしさ』と『エロさ』を追い求める！スカウトしたての新人� �ンケたち五人の処女雄穴に即巨根チ� ��ポを挿入！苦痛に悶える！密かに芽生えた快楽に戸惑い！初めてのアナ� �に感じて掘られイキまでしてしまう� ��ロノンケ！
Format: avi
Duration: 2:42:45
Video: 720x416, XviD, 1393kbps
Audio: 125kbps

File size: 1.8 GB

DOWNLOAD FROM FILESMONSTER: First Anal Fuck part 1

07-08-2025, 06:08 PM	#191
LMChallea Join Date: Jan 2016 Posts: 714,686 Сказал(а) спасибо: 0 Поблагодарили 0 раз(а) в 0 сообщениях Rep Power: 1448	Boy For Sale - The Grooming - The Boy Jack Waters Renault Release Year: 2025 Studio: Boy For Sale Cast: Ace Banner, Jack Waters Genres: anal, dildo, gay, masturbate, oral, porn While flipping through community college brochures at a career fair one afternoon, Jack Waters let out a discouraged sigh. School was extremely expensive these days, and it was becoming clear that his series of odd jobs during the week was not going to cover the cost of tuition. Disheartened, young Jack was about to give up when he saw the glint of a golden ticket half covered up by a stack of sex education pamphlets. Jack was both puzzled and intrigued by the fact that the golden ticket only had an email address followed by a four digit number and a strange request to submit a picture in .jpg format. With nothing left to lose, Jack submitted the random four digit number with a random photo showing his face, then sent it to the email address. Almost immediately, an email message came back with an invitation to meet at an address uptown. Perplexed but also desperate, Jack decided to go with it. The nervous twink was met at the end of a dark alley at the edge of town by a tall, bald, handsome man in a perfectly tailored suit. It looked incredibly expensive. Jack recited the four digit secret code to the severe-looking gentleman, who nodded and then unlocked a gold-plated doorway that led into a dimly lit chamber. Jack was informed this was the ‘Vetting Chamber’. The young man gulped, but excitedly entered the room. The door was closed behind him. The older gentleman introduced himself as Master Banner. In a no-nonsense tone of voice, this man with ice-blue eyes instructed Jack to take a seat and remain silent until spoken to. A shiver pulsed up the young twink’s spine. It was both terrifying and exhilarating to be addressed in such a way. He kind of liked it, but kept a straight face as he had a feeling even a stray smile might fuck up his chances at the money. A pearl-white document was placed in front of Jack. Master Banner implored the youth to read every line. If Jack agreed to the contents of the contract, and he subsequently obeyed every command given to him going forward, the dollar amount stated at the bottom of the contract would be his afterwards. A few moments later, his veins pumping with adrenaline, the newly-renamed Boy Jack was guided into another room. Master Banner said this was the “Grooming Chamber.” In the center of the room was a large square platform. The newly signed Slaveboy was commanded to remove his clothing, hop up onto the platform, and place himself in the doggy position. The Boy Jack swallowed hard and hesitated for a moment. Master Banner snapped his fingers sharply and with a frigid, buzzer-like tone of voice, reminded the young Slaveboy that compliance was expected to be followed with haste and a sense of urgency. Anything less was unacceptable. The Boy took a shaky breath and nodded. He made a mental note and decided it would probably be wise to pick up the pace a little. Soon, Boy Jack was completely nude and on top of the grooming altar. The twink slave was quite the specimen long, tall, with flawless skin, and clearly into physical fitness as his body was well toned for one so young. Master Banner salaciously groped every inch of the Slaveboy’s beautiful body. Boy Jack moaned and sighed in response to the intimate touch. Master Banner’s duty this evening was to prepare the slave for future buyers. The Boy, as stated in the contract, must be ready for anything - any desire that a gentleman buyer might have must be granted. And seeing that The Boy Jack was a virgin, Master Banner was required to begin the momentous ritual of preparing a Slaveboy for his first anal penetration. The Boy Jack closed his eyes for a moment, enjoying the pleasant sensations of Master Banner’s touch all over his body. Those eyes immediately snapped back open when The Boy heard the sound of a cap popping open. The suited gentleman had a large bottle of what appeared to be oil and he began applying a very generous amount all over the boy’s chest and back. The proceeding was very sensual and arousing. Boy Jack immediately sported an erection and secretly hoped that the experienced Master might permit him to stroke his own cock using the oil. Even better, Master Banner proceeded to massage the warm, gentle lubrication not just along the slave’s swollen twink member, but his hairless scrotum as well. That’s when the gentle ministrations suddenly turned more aggressive. The suited dominator held The Boy’s ballsack by the base and squeezed - hard. The Slaveboy involuntarily emitted a hiss of surprise and fear. Master Banner pressed hard up against the Boy and shushed him. Boy Jack took a long, slow breath and held it while the merciless Master continued to test the submissive’s will. Other Masters would surely expect the Slaveboy to be eager and docile even in the face of somewhat harsh sensation. The Boy Jack thought about the money and soon, the intensity died down somewhat. Finally, Master Banner released the Slaveboy’s testes from his tight grip and commanded The Boy to lie on his back and pull his shapely legs towards his chest, exposing his precious pink virgin hole. As he did so, the twink noticed how Master’s eyes seemed to feast on his boy pucker. The Slaveboy wondered with a slight shiver what was going to happen next. Master Banner pulled out a long, curved glass dildo and The Boy Jack took another sharp breath. The sex toy was shiny like diamonds and had two cockhead-shaped bulbs on each end. Master Banner caught the Slaveboy’s glance. Here and now was the moment of truth. Master Banner would be gentle - at first. The Slaveboy gulped loudly and took another deep breath. Master Banner poured a generous amount of oil all over the twink’s pink pucker. Then, when the Master pressed one bulbous end of the glass dildo against the Slaveboy’s anus, the older gentleman found himself aroused by hearing The Boy’s initial whine, followed quickly by a deep, primal groan as the dildo very slowly buried half-inch by half-inch deeper and deeper inside of the insanely tight anus... Format: mp4 Duration: 30:26 Video: 1920x1080, AVC (H.264), 7781kbps Audio: 156kbps File size: 1.7 GB DOWNLOAD FROM FILESMONSTER: Boy For Sale - The Grooming - The Boy Jack Waters __________________

07-26-2025, 04:50 PM	#192
LMChallea Join Date: Jan 2016 Posts: 714,686 Сказал(а) спасибо: 0 Поблагодарили 0 раз(а) в 0 сообщениях Rep Power: 1448	Plowing Dylan Nuuk Cast: Chris ,Dylan Genres: Bareback , Gay Porn Video language: English Two things I don't think I could ever get tired off - seeing Chris rim, and seeing Dylan get rimmed. So seeing Dylan get rimmed by Chris?! Awesome! Chris just loves to eat ass! He showed up at CF loving eating ass. The first ass he had the chance to eat when he arrived here, he dove in to immediately. Dylan, on the other hand, hadn't yet gotten to experience how the ass could be a part of sex. He was ass unaware when he first arrived at CF, but he definitely knows full well what a source of pleasure it can be now! Teaming these two up with one another to let Chris go to town on Dylan's hole - and get his tongue and dick buried in it - is a total treat and now is certainly a third thing I could never get tired of seeing! Format: mp4 Duration: 17:40 Video: 1920x1080, AVC (H.264), 5842kbps Audio: 184kbps File size: 783.2 MB DOWNLOAD FROM FILESMONSTER: Plowing Dylan __________________

08-01-2025, 05:45 PM	#193
LMChallea Join Date: Jan 2016 Posts: 714,686 Сказал(а) спасибо: 0 Поблагодарили 0 раз(а) в 0 сообщениях Rep Power: 1448	First Anal Fuck San Pierre Release Year: 2024 Genres: Asian, Twinks, Oral, Anal Sex, Rimming, Masturbation, Toy, Fingering, Cumshot Video language: Japanese ノンケの持つ『爽やかさ』と『男ら� �さ』と『エロさ』を追い求める！ス� ��ウトしたての新人ノンケたち五人の処女雄穴に即巨根チンポを挿入！苦� �に悶える！密かに芽生えた快楽に戸� ��い！ Format: avi Duration: 2:42:45 Video: 720x416, XviD, 1393kbps Audio: 125kbps File size: 1.8 GB DOWNLOAD FROM FILESMONSTER: First Anal Fuck __________________

08-11-2025, 05:00 PM	#194
LMChallea Join Date: Jan 2016 Posts: 714,686 Сказал(а) спасибо: 0 Поблагодарили 0 раз(а) в 0 сообщениях Rep Power: 1448	Plowing Dylan North Vernon Cast: Chris ,Dylan Genres: Bareback , Gay Porn Video language: English Two things I don't think I could ever get tired off - seeing Chris rim, and seeing Dylan get rimmed. So seeing Dylan get rimmed by Chris?! Awesome! Chris just loves to eat ass! He showed up at CF loving eating ass. The first ass he had the chance to eat when he arrived here, he dove in to immediately. Dylan, on the other hand, hadn't yet gotten to experience how the ass could be a part of sex. He was ass unaware when he first arrived at CF, but he definitely knows full well what a source of pleasure it can be now! Teaming these two up with one another to let Chris go to town on Dylan's hole - and get his tongue and dick buried in it - is a total treat and now is certainly a third thing I could never get tired of seeing! Format: mp4 Duration: 17:40 Video: 1920x1080, AVC (H.264), 5842kbps Audio: 184kbps File size: 783.2 MB DOWNLOAD FROM FILESMONSTER: Plowing Dylan __________________

08-28-2025, 07:14 PM	#195
LMChallea Join Date: Jan 2016 Posts: 714,686 Сказал(а) спасибо: 0 Поблагодарили 0 раз(а) в 0 сообщениях Rep Power: 1448	Straight College Boy First Anal - Ayumu Tsukamoto 19yo 416p Lucca Video language: Japanese 1は、極タチ航と22達の248手集！には、人気2啓志や新人2太一が生掘りで男同士の濃厚SEX体位を披露！「締込み千� �」「虹の架け橋」など24手収録。 Format: avi Duration: 2:12:40 Video: 720x416, XviD, 1924kbps Audio: 125kbps File size: 2.0 GB DOWNLOAD FROM FILESMONSTER: Straight College Boy First Anal - Ayumu Tsukamoto 19yo 416p __________________