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All Forums > The Porn Pool > The Porn Pool Forum Page 6 > Scenes where a Milf or Gilf struggle with big ock

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Opal2001 Member 73 Posts 2/24	Posted - Jun 7 2024 : 8:06PM Any scenes where a Milf or Gilf struggle with the young guys cock being to big or going too deep? Thanks for helping out [Link]
Opal2001 Member 73 Posts 2/24	Posted - Jul 6 2025 : 7:14PM I guess I asked for something impossible to find :-( [Link]
ssimfa Member 226 Posts 6/25	Posted - Jul 6 2025 : 9:13PM Opal2001 wrote: Any scenes where a Milf or Gilf struggle with the young guys cock being to big or going too deep? Thanks for helping out Click to expand Not sure if you are looking for the usual rough kind of scenes. I can think of one if you like the more intimate stuff. Zoey Holloway in My Daughter's Boyfriend 2. She doesn't necessarily struggle with the cock but the dynamic between her and the guy is quite special. There is a big age gap between the two and it genuinely feels like Zoey is very vulnerable/self conscious (in a good way) in the scene, so more than a couple of times during the scene, Zoey's expressions while having the guy inside her indicate that the guy is in pretty deep. Attaching some shots. [Link]
Opal2001 Member 73 Posts 2/24	Posted - Jul 7 2025 : 3:29PM ssimfa wrote: Opal2001 wrote: Any scenes where a Milf or Gilf struggle with the young guys cock being to big or going too deep? Thanks for helping out Click to expand Not sure if you are looking for the usual rough kind of scenes. I can think of one if you like the more intimate stuff. Zoey Holloway in My Daughter's Boyfriend 2. She doesn't necessarily struggle with the cock but the dynamic between her and the guy is quite special. There is a big age gap between the two and it genuinely feels like Zoey is very vulnerable/self conscious (in a good way) in the scene, so more than a couple of times during the scene, Zoey's expressions while having the guy inside her indicate that the guy is in pretty deep. Attaching some shots. Click to expand Biggest of thanks! Great scene! [Link]
Opal2001 Member 73 Posts 2/24	Posted - Jul 9 2025 : 7:00PM ssimfa wrote: Opal2001 wrote: Any scenes where a Milf or Gilf struggle with the young guys cock being to big or going too deep? Thanks for helping out Click to expand Not sure if you are looking for the usual rough kind of scenes. I can think of one if you like the more intimate stuff. Zoey Holloway in My Daughter's Boyfriend 2. She doesn't necessarily struggle with the cock but the dynamic between her and the guy is quite special. There is a big age gap between the two and it genuinely feels like Zoey is very vulnerable/self conscious (in a good way) in the scene, so more than a couple of times during the scene, Zoey's expressions while having the guy inside her indicate that the guy is in pretty deep. Attaching some shots. Click to expand I would also like to recommend Erica Lauren - BlacksOnCougars. Here Boz knows he can cause discomfort if he goes too deep and sometimes he succeeds and she has to push him back. It is very rare to see milfs or gilfs struggling with depth. Enjoy and please share more. [Link]

Opal2001 Member 73 Posts 2/24	Posted - Aug 4 2025 : 10:09AM Opal2001 wrote: ssimfa wrote: Opal2001 wrote: Any scenes where a Milf or Gilf struggle with the young guys cock being to big or going too deep? Thanks for helping out Click to expand Not sure if you are looking for the usual rough kind of scenes. I can think of one if you like the more intimate stuff. Zoey Holloway in My Daughter's Boyfriend 2. She doesn't necessarily struggle with the cock but the dynamic between her and the guy is quite special. There is a big age gap between the two and it genuinely feels like Zoey is very vulnerable/self conscious (in a good way) in the scene, so more than a couple of times during the scene, Zoey's expressions while having the guy inside her indicate that the guy is in pretty deep. Attaching some shots. Click to expand I would also like to recommend Erica Lauren - BlacksOnCougars. Here Boz knows he can cause discomfort if he goes too deep and sometimes he succeeds and she has to push him back. It is very rare to see milfs or gilfs struggling with depth. Enjoy and please share more. Click to expand Do you guys have any other scenes to recommend? Thanks [Link]
RitaDismyqueen Member 169 Posts 11/23	Posted - Aug 4 2025 : 1:58PM I remember a hardcore Brazzers scene entitled "Bed Ridden" where legendary gilf Rita Daniels repeatedly struggles to deepthroat Keiran Lee's monster cock. She is also seen struggling to take his big dick deep in her pussy in some instances in this scene. Edited by - RitaDismyqueen on 8/4/2025 1:59:13 PM [Link]
Opal2001 Member 73 Posts 2/24	Posted - Aug 12 2025 : 6:40PM RitaDismyqueen wrote: I remember a hardcore Brazzers scene entitled "Bed Ridden" where legendary gilf Rita Daniels repeatedly struggles to deepthroat Keiran Lee's monster cock. She is also seen struggling to take his big dick deep in her pussy in some instances in this scene. Edited by - RitaDismyqueen on 8/4/2025 1:59:13 PM Click to expand Thanks! Such scenes are very rare! [Link]
leatherface Senior Member 1258 Posts 7/07	Posted - Aug 12 2025 : 7:01PM I remember a scene at 50 plus milfs with this 20 year old guy with a 50 something lady, and this guy had a very large girth, so especially during the bj she was struggling to even take it in her mouth. I can't remember her name at the moment, I have to look. [Link]
biggins Member 657 Posts 5/09	Posted - Aug 14 2025 : 11:57AM leatherface wrote: I remember a scene at 50 plus milfs with this 20 year old guy with a 50 something lady, and this guy had a very large girth, so especially during the bj she was struggling to even take it in her mouth. I can't remember her name at the moment, I have to look. Click to expand please do ! [Link]
Opal2001 Member 73 Posts 2/24	Posted - Aug 15 2025 : 6:51PM leatherface wrote: I remember a scene at 50 plus milfs with this 20 year old guy with a 50 something lady, and this guy had a very large girth, so especially during the bj she was struggling to even take it in her mouth. I can't remember her name at the moment, I have to look. Click to expand Sounds hot! Would love to know more. [Link]
RitaDismyqueen Member 169 Posts 11/23	Posted - Aug 16 2025 : 10:40AM I also remember a hardcore interracial scene where milf Melissa Monet, acting as a stepmom, struggles to take Rico Strong's huge cock in repeated instances. It's a very old scene. Rico, sure was at his early years of his porn career, given his shyness and very young looks. [Link]
yosemitejack664 Member 482 Posts 4/25	Posted - Aug 16 2025 : 11:48AM Reagan Foxx seemed to be struggling with Isiah Maxwell's BBC during her first interracial scene. [Link]
Opal2001 Member 73 Posts 2/24	Posted - Aug 17 2025 : 8:00PM yosemitejack664 wrote: Reagan Foxx seemed to be struggling with Isiah Maxwell's BBC during her first interracial scene. Click to expand Great recommendation. [Link]
Opal2001 Member 73 Posts 2/24	Posted - Aug 17 2025 : 8:02PM RitaDismyqueen wrote: I also remember a hardcore interracial scene where milf Melissa Monet, acting as a stepmom, struggles to take Rico Strong's huge cock in repeated instances. It's a very old scene. Rico, sure was at his early years of his porn career, given his shyness and very young looks. Click to expand Thanks! I do however wonder how much she faked it since she is playing the role of a nervous wife with a small sized husband. [Link]

alex9 Member 26 Posts 8/25	Posted - Aug 17 2025 : 8:17PM Opal2001 wrote: Any scenes where a Milf or Gilf struggle with the young guys cock being to big or going too deep? This Mexican MILF was a real school teacher and is a school teacher to this day ( how she has been able to keep this scene a secret is a miracle ) but in the scene you can tell she is not use to being Fucked like that. It was pretty hot and intense. I'm not sure if we're allowed to say the name of the site, it has gone out of business because of their affiliation with another website. But this site was full of first time MILFS who were not use to being F()^& by guys who have sex for a living. Thanks for helping out Click to expand [Link]
alex9 Member 26 Posts 8/25	Posted - Aug 17 2025 : 8:18PM alex9 wrote: Opal2001 wrote: Any scenes where a Milf or Gilf struggle with the young guys cock being to big or going too deep? This Mexican MILF was a real school teacher and is a school teacher to this day ( how she has been able to keep this scene a secret is a miracle ) but in the scene you can tell she is not use to being Fucked like that. It was pretty hot and intense. I'm not sure if we're allowed to say the name of the site, it has gone out of business because of their affiliation with another website. But this site was full of first time MILFS who were not use to being F()^& by guys who have sex for a living. Thanks for helping out Click to expand Click to expand [Link]
Opal2001 Member 73 Posts 2/24	Posted - Aug 17 2025 : 8:32PM alex9 wrote: Opal2001 wrote: Any scenes where a Milf or Gilf struggle with the young guys cock being to big or going too deep? This Mexican MILF was a real school teacher and is a school teacher to this day ( how she has been able to keep this scene a secret is a miracle ) but in the scene you can tell she is not use to being Fucked like that. It was pretty hot and intense. I'm not sure if we're allowed to say the name of the site, it has gone out of business because of their affiliation with another website. But this site was full of first time MILFS who were not use to being F()^& by guys who have sex for a living. Thanks for helping out Click to expand Wow! Any studio name? Edited by - Opal2001 on 8/17/2025 8:32:42 PM [Link]
Opal2001 Member 73 Posts 2/24	Posted - Aug 17 2025 : 8:33PM Any studio name? [Link]
alex9 Member 26 Posts 8/25	Posted - Aug 17 2025 : 8:44PM Opal2001 wrote: alex9 wrote: Opal2001 wrote: Any scenes where a Milf or Gilf struggle with the young guys cock being to big or going too deep? This Mexican MILF was a real school teacher and is a school teacher to this day ( how she has been able to keep this scene a secret is a miracle ) but in the scene you can tell she is not use to being Fucked like that. It was pretty hot and intense. I'm not sure if we're allowed to say the name of the site, it has gone out of business because of their affiliation with another website. But this site was full of first time MILFS who were not use to being F()^& by guys who have sex for a living. Thanks for helping out Click to expand Wow! Any studio name? DM me, I'm not sure if we're allowed to share the name of the site on the forum. They were a sister site to that one site that got into all that trouble for coercing models. Edited by - Opal2001 on 8/17/2025 8:32:42 PM Click to expand [Link]
alex9 Member 26 Posts 8/25	Posted - Aug 17 2025 : 8:45PM w [Link]
Opal2001 Member 73 Posts 2/24	Posted - Aug 17 2025 : 8:57PM alex9 wrote: w Click to expand You got a message now😊 [Link]
ninja1 Senior Member 2939 Posts 1/08	Posted - Aug 18 2025 : 9:35PM Rubee Tuesday struggles with Wesley Pipes in an Exploited Moms scene. [Link]
leatherface Senior Member 1258 Posts 7/07	Posted - Aug 19 2025 : 12:43PM biggins wrote: leatherface wrote: I remember a scene at 50 plus milfs with this 20 year old guy with a 50 something lady, and this guy had a very large girth, so especially during the bj she was struggling to even take it in her mouth. I can't remember her name at the moment, I have to look. Click to expand please do ! Click to expand it was Sindi Star with Matt Sloane [Link]
Opal2001 Member 73 Posts 2/24	Posted - Aug 21 2025 : 6:54PM leatherface wrote: biggins wrote: leatherface wrote: I remember a scene at 50 plus milfs with this 20 year old guy with a 50 something lady, and this guy had a very large girth, so especially during the bj she was struggling to even take it in her mouth. I can't remember her name at the moment, I have to look. Click to expand please do ! Click to expand it was Sindi Star with Matt Sloane Click to expand Thanks! It is rare to see Gilf / Matures struggle with cocks. [Link]

Opal2001 Member 73 Posts 2/24	Posted - Aug 22 2025 : 5:38PM ninja1 wrote: Rubee Tuesday struggles with Wesley Pipes in an Exploited Moms scene. Click to expand Great scene! Thanks [Link]
Opal2001 Member 73 Posts 2/24	Posted - Aug 26 2025 : 11:18PM Opal2001 wrote: ssimfa wrote: Opal2001 wrote: Any scenes where a Milf or Gilf struggle with the young guys cock being to big or going too deep? Thanks for helping out Click to expand Not sure if you are looking for the usual rough kind of scenes. I can think of one if you like the more intimate stuff. Zoey Holloway in My Daughter's Boyfriend 2. She doesn't necessarily struggle with the cock but the dynamic between her and the guy is quite special. There is a big age gap between the two and it genuinely feels like Zoey is very vulnerable/self conscious (in a good way) in the scene, so more than a couple of times during the scene, Zoey's expressions while having the guy inside her indicate that the guy is in pretty deep. Attaching some shots. Click to expand I would also like to recommend Erica Lauren - BlacksOnCougars. Here Boz knows he can cause discomfort if he goes too deep and sometimes he succeeds and she has to push him back. It is very rare to see milfs or gilfs struggling with depth. Enjoy and please share more. Click to expand Erica Lauren was outmatched by Boz. Any other scenes you guys can recommend on this topic? [Link]
RitaDismyqueen Member 169 Posts 11/23	Posted - Aug 29 2025 : 5:40AM I forgot the title of the scene; A very hardcore threesome with milf Mikki Lynn, acting as mom, Wesley Pipes and Maia Davies (daughter). Dirty talking Mikki is repeatedly seen struggling to take Wesley's long monster dick in its entirety, in various positions, no matter how she tried hard. [Link]
RitaDismyqueen Member 169 Posts 11/23	Posted - Aug 29 2025 : 5:51AM Another such scene that comes to my mind is a rough and hardcore Dog Fart scene between horny milf Mikki Lynn and Rob Piper. Mikki seems to be a real sub who passionately needs a true slut treatment. Though she manages to take Rob's huge dick in her pussy deep down, during the whole scene, she repeatedly struggles to deepthroat his monster cock in her mouth, in which she failed several times. [Link]
killbillvol69 All-Star Member ^Lucy Pinder 18634 Posts 4/08	Posted - Aug 29 2025 : 11:33AM RitaDismyqueen wrote: I forgot the title of the scene; A very hardcore threesome with milf Mikki Lynn, acting as mom, Wesley Pipes and Maia Davies (daughter). Dirty talking Mikki is repeatedly seen struggling to take Wesley's long monster dick in its entirety, in various positions, no matter how she tried hard. Click to expand That's scene 4 from Mommy, Me, And A Gangster 3 [Link]
RitaDismyqueen Member 169 Posts 11/23	Posted - Aug 29 2025 : 5:03PM That's right. That's the exact title. What a brilliant editor!!! [Link]
Opal2001 Member 73 Posts 2/24	Posted - Aug 29 2025 : 7:34PM killbillvol69 wrote: RitaDismyqueen wrote: I forgot the title of the scene; A very hardcore threesome with milf Mikki Lynn, acting as mom, Wesley Pipes and Maia Davies (daughter). Dirty talking Mikki is repeatedly seen struggling to take Wesley's long monster dick in its entirety, in various positions, no matter how she tried hard. Click to expand That's scene 4 from Mommy, Me, And A Gangster 3 Click to expand Thanks!!! [Link]
RitaDismyqueen Member 169 Posts 11/23	Posted - Sep 1 2025 : 8:41AM Legendary New Zealand milf Lake Russell repeatedly struggles to take young JMac's huge dick full-length in an old hardcore scene. JMac wasn't bald back then. He was very young and energetic. I think it was in his early years of his porn career. [Link]
Opal2001 Member 73 Posts 2/24	Posted - Sep 1 2025 : 7:47PM RitaDismyqueen wrote: Legendary New Zealand milf Lake Russell repeatedly struggles to take young JMac's huge dick full-length in an old hardcore scene. JMac wasn't bald back then. He was very young and energetic. I think it was in his early years of his porn career. Click to expand Thanks bro! Great scene. I'll match you. Forgot the name of the vid but here are the scenes: Janine Lindemulder vs Sean Michaels Janine Lindemulder vs Mandingo Janine struggles badly from depth 👍 [Link]
RitaDismyqueen Member 169 Posts 11/23	Posted - Sep 2 2025 : 1:31PM Though elegant milf Rachael Cavalli has several scenes (most of them on OnlyFans) with the very young Damion Dayski, one hour-long scene stands out. Rachael finds it hard to take Dayski's black monster dick full-length in various few positions and instances. However, she was able to take him deep-down in almost the entirety of this hardcore scene. Both had awesome chemistry. [Link]

Opal2001 Member 73 Posts 2/24	Posted - Sep 2 2025 : 6:32PM RitaDismyqueen wrote: Though elegant milf Rachael Cavalli has several scenes (most of them on OnlyFans) with the very young Damion Dayski, one hour-long scene stands out. Rachael finds it hard to take Dayski's black monster dick full-length in various few positions and instances. However, she was able to take him deep-down in almost the entirety of this hardcore scene. Both had awesome chemistry. Click to expand Just watched it. Did not see any struggle? Which positions are you refering too? [Link]
Opal2001 Member 73 Posts 2/24	Posted - Sep 5 2025 : 12:21PM Opal2001 wrote: RitaDismyqueen wrote: Legendary New Zealand milf Lake Russell repeatedly struggles to take young JMac's huge dick full-length in an old hardcore scene. JMac wasn't bald back then. He was very young and energetic. I think it was in his early years of his porn career. Click to expand Thanks bro! Great scene. I'll match you. Forgot the name of the vid but here are the scenes: Janine Lindemulder vs Sean Michaels Janine Lindemulder vs Mandingo Janine struggles badly from depth 👍 Click to expand I think the first one might be a movie called Janine has been blackmauled or something. [Link]
RitaDismyqueen Member 169 Posts 11/23	Posted - Sep 5 2025 : 5:40PM I remember watching a handful of Janine's scenes in the mid 90's. But, I never watched her scenes with those two. I've seen some milfs struggling to take Mandingo's long monster dick full-length. I can mention Jillian Foxx and Brandi Love. Both had hard times trying to take his dong deep down in various instances of their respective scenes. [Link]
Opal2001 Member 73 Posts 2/24	Posted - Sep 6 2025 : 10:38AM RitaDismyqueen wrote: I remember watching a handful of Janine's scenes in the mid 90's. But, I never watched her scenes with those two. I've seen some milfs struggling to take Mandingo's long monster dick full-length. I can mention Jillian Foxx and Brandi Love. Both had hard times trying to take his dong deep down in various instances of their respective scenes. Click to expand Check the Janines been blackmauled scene👏 [Link]
RitaDismyqueen Member 169 Posts 11/23	Posted - Sep 6 2025 : 4:52PM Okay I will. Do you have any other recommendations of such scenes? Edited by - RitaDismyqueen on 9/6/2025 4:53:34 PM [Link]
Opal2001 Member 73 Posts 2/24	Posted - Sep 6 2025 : 8:02PM RitaDismyqueen wrote: Okay I will. Do you have any other recommendations of such scenes? Edited by - RitaDismyqueen on 9/6/2025 4:53:34 PM Click to expand Shorty vs Lisa Ann I believe had one moment. [Link]
Opal2001 Member 73 Posts 2/24	Posted - Sep 7 2025 : 7:18AM Opal2001 wrote: ssimfa wrote: Opal2001 wrote: Any scenes where a Milf or Gilf struggle with the young guys cock being to big or going too deep? Thanks for helping out Click to expand Not sure if you are looking for the usual rough kind of scenes. I can think of one if you like the more intimate stuff. Zoey Holloway in My Daughter's Boyfriend 2. She doesn't necessarily struggle with the cock but the dynamic between her and the guy is quite special. There is a big age gap between the two and it genuinely feels like Zoey is very vulnerable/self conscious (in a good way) in the scene, so more than a couple of times during the scene, Zoey's expressions while having the guy inside her indicate that the guy is in pretty deep. Attaching some shots. Click to expand I would also like to recommend Erica Lauren - BlacksOnCougars. Here Boz knows he can cause discomfort if he goes too deep and sometimes he succeeds and she has to push him back. It is very rare to see milfs or gilfs struggling with depth. Enjoy and please share more. Click to expand Is this the best scene of this topic or do you have some other scenes to compare to? 😁 [Link]
RitaDismyqueen Member 169 Posts 11/23	Posted - Sep 7 2025 : 1:46PM My most favorite such scene so far is Lady Sonia's. It's an old scene from her official site several years back. A very rough & hardcore scene with young masked black man- Shaft UK. At one instance during the blowjob session, Lady Sonia puts Shaft's long monster dick in the middle of her face and remarks, "Your cock is bigger than my face." Later, she repeatedly struggles to take him deep-down and full-length in missionary, cowgirl and reverse cowgirl positions. [Link]
Opal2001 Member 73 Posts 2/24	Posted - Sep 8 2025 : 9:25AM RitaDismyqueen wrote: My most favorite such scene so far is Lady Sonia's. It's an old scene from her official site several years back. A very rough & hardcore scene with young masked black man- Shaft UK. At one instance during the blowjob session, Lady Sonia puts Shaft's long monster dick in the middle of her face and remarks, "Your cock is bigger than my face." Later, she repeatedly struggles to take him deep-down and full-length in missionary, cowgirl and reverse cowgirl positions. Click to expand Wow! Lady Sonia seems invincible so it would be great if you could find the name of the scene? [Link]
RitaDismyqueen Member 169 Posts 11/23	Posted - Sep 8 2025 : 11:14AM I don't remember the exact title. This British milf had several such hardcore scenes, with lots of dirty talk and name calling with this same young masked black man-Shaft UK back then. As far as I know, he is the only alpha male who totally dominated Lady Sonia in most of their scenes.He truly knows how to treat horny, slutty milfs. Edited by - RitaDismyqueen on 9/8/2025 12:57:41 PM [Link]
Opal2001 Member 73 Posts 2/24	Posted - Sep 9 2025 : 10:52PM RitaDismyqueen wrote: I don't remember the exact title. This British milf had several such hardcore scenes, with lots of dirty talk and name calling with this same young masked black man-Shaft UK back then. As far as I know, he is the only alpha male who totally dominated Lady Sonia in most of their scenes.He truly knows how to treat horny, slutty milfs. Edited by - RitaDismyqueen on 9/8/2025 12:57:41 PM Click to expand Thanks for trying to find it [Link]
Opal2001 Member 73 Posts 2/24	Posted - Sep 13 2025 : 6:41PM Any more scenes where a Milf or Gilf struggle with the young guys cock being to big or going too deep? Thanks for helping out [Link]
Opal2001 Member 73 Posts 2/24	Posted - Sep 18 2025 : 8:18PM Opal2001 wrote: Any more scenes where a Milf or Gilf struggle with the young guys cock being to big or going too deep? Thanks for helping out Click to expand I guess these type of scenes are very rare. [Link]
mkurat Senior Member 1450 Posts 1/15	Posted - Sep 21 2025 : 3:48AM i like the three scenes below where the milfs are feeling the dp: kat (AKA sydney vicious) dp in blacks on blondes (her one and only dp) veronica rayne for asstitans lizzy licious (believe its her one and only dp) for maturenl [Link]
Opal2001 Member 73 Posts 2/24	Posted - Sep 23 2025 : 7:47PM mkurat wrote: i like the three scenes below where the milfs are feeling the dp: kat (AKA sydney vicious) dp in blacks on blondes (her one and only dp) veronica rayne for asstitans lizzy licious (believe its her one and only dp) for maturenl Click to expand Any where the milf / gilf show struggle? [Link]
mkurat Senior Member 1450 Posts 1/15	Posted - Sep 24 2025 : 3:42AM Opal2001 wrote: mkurat wrote: i like the three scenes below where the milfs are feeling the dp: kat (AKA sydney vicious) dp in blacks on blondes (her one and only dp) veronica rayne for asstitans lizzy licious (believe its her one and only dp) for maturenl Click to expand Any where the milf / gilf show struggle? Click to expand like I said its where they feel the dp. not necessarily would be any sign of struggle... i only state what i like and am sure the scenes may be preferable to certain ppl... respect all sorts of opinions as mine should be too... [Link]

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