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The Motherless Members Hall of Fame is to honor those members who have significantly contributed to Motherless.com. These members have dedicated themselves to the advancement of the site and the site chat through their contributions in the form of pictures and videos, stories, friendship, advice or overall support for our endevors. These members may have joined at the inception, or later on in the history of the site, but continue to support our mission here and our community in providing user submitted legal content without judgement. Only five members will be chosen per year, and will be voted on by the senior leadership here at Motherless. Nominations will start in December from current members and the voting process will take place January.

Mature gilf and senior men

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This group is for mature gilfs and their senior men that still love to have sweet sex

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39
Anonymous
@confessions
05 Sep 2012 6:48PM
• 32,822 views • 0 attachments
[ − ] thread [ 49 replies ]

Here is how I got to mess around with two of my friends during our senior year of college. Names have been changed to protect identities. I will also warn you - this will probably end up long.

SO I knew Ashley and Sara since our freshman year. They had been roommates since the first semester, and we all had History together. We had been the best of friends throughout college, although none of us had done anything sexual together. My parents lived not too far from college, and they decided to take a winter vacation to a tropical The house was empty, which meant a perfect studying place for exams. I invited Ashley and Sara to join, since I knew all of us liked studying together, even if it was for different classes.

I should take a moment to describe Ashley and Sara. They are really polar opposites of each other. Sara is tall and slender, white complexion, with (I would estimate) B cups, a flat ass, and blonde hair. Ashley is 6'2", a little chunkier, is a little darker (basically looks like she has a natural tan), has huge tits (they look like fucking watermelons), a huge ass, and brown hair.

We ate dinner at college first then drove to my parents house. We decided that it was a little late to start studying, so we decided to drink in my parents half finished basement (half finished as in my dad started to finish it, but got distracted and never completed the project). We had an old couch and a bean-bag like chair with a mini-fridge stocked with some of my dads beer. We broke out the beer and start drinking while talking about random topics. Ashley and Sara were on the couch and I was on the chair. Ashley and I were three beers in, Sara was still milking her second. This was on-pace for us, and based on past experiences, I knew we were all buzzed. I got up and went upstairs to pee. As I got to the top of the stairs, I heard Sara say that she was going to go pee too.

Now, my parents house has two bathrooms somewhat close to each other on the first floor. I figured I would be polite and went to the further bathroom, leaving the closer one for Sara. I partially close the bathroom door and pulled out my dick when I hear the door open and Sara say "OH MY GOD." I look over, and she is staring at my dick. I close the door in her face and finish peeing. After I finished, I opened the door and she was still standing there. She said "I AM SO SORRY. I thought you were in the other one, that door was closed. And holy shit you have a big dick."

Let me stop again and explain. I hate to brag, but I will anyway. Yes, girls are routinely impressed by my dick. That is because it is huge and long while soft, but does not get that much longer hard. It mostly just gets thicker.

Anyway, I didnt say anything and went back downstairs. Sara came running down a minute later saying "Oh my god Ash, you have to see his dick. It is huge." Ashley smiled and said that she has seen plenty of huge dicks. Sara said "Yeah I know. I mean, not to sound like a slut but I have seen a ton of dicks too, but it was really big even soft".

So they start talking about guys and their dicks for a while. I was starting to think they forgot about me when Ashley turned to me and said "well, now I am curious. You willing to show me?"

Ok, sorry for the interruption again. There really was no good time to mention this before. Sara and Ashley had both been single for a couple of months, and I had been single for about 5. I was pretty certain neither of them had gotten laid in that time span, since I would usually hear about it.

I laughed and said that I would feel a little uncomfortable just randomly taking it out, and that Sara only saw it because she accidently walked in on me peeing. Ashley said "So what, I have to wait until you have to pee again?" It sounded like she was waiting for an answer, so I said "yeah, I guess." She countered with "What if I showed you my boobs?"

Well that took me by surprise. And I think Sara was surprised by it too. I thought Ashley was talking out of her ass and would never flash, so I said "sure, why not." In one move she sat up and grabbed her shirt and lifted it up, showing her bra. Then she lifted her bra up and her boobs flopped out. Holy shit, they were big and perfect. I should point out that the couch and chair were only a few inches apart..we were sitting really close to each other. So they were almost in my face. She shook her shoulders and her tits swayed back and forth, then she pulled her bra back down, fixed her boobs, and pulled her shirt back down. Sara looked shocked (almost a little horrified).

Ashley looked at me and said "Ok, it's your turn." I really didnt want to, but I pulled my dick out of my pants. By this point, the conversation and staring at her tits had made my dick semi hard. I shook it a brief second, and Ashley said "that doesn't count, it is hard!"

I laughed and said "Well yeah, boobs will do that." Ashley said that she wanted to see it soft, so I told them to change the subject. So Ashley turned to Sara and started talking to her about some on-campus event later that week. All while I sat there on the chair with my dick out. And it only took a minute until it was soft. I saw Sara glancing at it out of the corner of her eye, and she turned and said "oh, it is probably soft again."

I looked down and confirmed that yes, it was soft. Ashley said "bullshit" and leaned over and grabbed my dick with her hand. I heard Sara yell "ASH, WHAT ARE YOU DOING??" and Ashley laughed and said "oh man, that is large and soft. Jeez, how big does it get?" She then started stroking it.

I kinda gripped the sides of the chair, not too sure what to do. It got hard almost instantly, and Ashley said "oh, not that much longer, but pretty thick." She didnt stop stroking though, and only a few strokes after she said "Uhm, I dont know where I am going with this..." and then she laughed. I said "yeah, what are you doing?" and Sara yelled "ASH STOP THAT!!"

From someone standing in the room, it was probably a funny scene: Sara staring (with a horrified and uncomfortable look on her face) at Ashley's hand stroking my dick, Ashley staring at her hand stroking my dick, and me looking at my dick, then at Ashley, then at Sara, and then back at my dick, all in a loop.

Ashley then looked at Sara and said "here, feel this." Sara yelled "NO! It's Mark...I wont touch his dick! And you shouldn't be either." Ashley said "Shut up, just touch it." They bickered back and forth for a minute before Ashley grabbed Sara's hand and forced it on my dick. Either Sara was not expecting it and didnt have a chance to fight back, or she just didn't fight back at all.

So Sara's hand was on my dick. She squeezed it and the look on her face went from horrified to amazement. "Wow, that IS thick..." She then picked it up and gently started stroking. She took both hands and gently stroked with both hands for a few seconds, before going back to one hand. Meanwhile, Ashley was still staring at my dick. She pushed her hair to the side, and then leaned over and put her mouth around the top of my dick.

Sara pulled her hand back and said "Ash, what are you doing now???" Ashley took my dick out of her mouth and said "Shh, I am just doing this for a few seconds." She then proceeded to take my dick back in her mouth and bobbed her head up and down my shaft. She actually got it pretty far down her throat. She held her finger to the side of my dick to show how far it went. She turned to Sara and said "Ha, beat that."

Sara said "I probably could, but we shouldnt and your mouth was just all over his dick." Ashley said "who cares..bet you cant do it anyway." Sara looked at my dick for a few seconds, then leaned in and put her mouth around the head and slowly it went down her throat. And it went further than Ashley...it didnt seem like it wasnt even that difficult to her.

She pulled up, then sucked a few seconds, bobbing up and down, then took it out of her mouth and turned to Ashley and said "see, told ya."

Sara and I then realized that Ashley's hand was down her pants, playing with her pussy. Sara yelled "ASH! Really? Right here in front of us??" Ashley said "oh shut up, its not like we have not masturbated before when sharing a room." Sara said "YEAH, but we were each in our own beds, with the lights off." Meanwhile, without thinking, I was slowly stroking my dick. Sara sees me and says "MARK! Come on, we aren't supposed to be doing this stuff together.." I shrugged and said "Ash started it."

Ashley stood up and started to take off her pants. Sara started to say something, but Ashley said "Come on, we are all good friends, let's each just have a little fun." She took off all her clothes and sat back on the couch naked, with her finger in her pussy. Ashley could see that Sara looked uncomfortable, so Ashley said "It's not like we haven't seen each other naked. You can just close your eyes if you want." Ashley then fixated her eyes on my dick and continued to stroke her pussy. I stared at her pussy and tits, and glanced over to Sara from time to time. Sara sat on the couch, looking around the room and , from time to time, at Ashley and back over to me.

I saw she was looking at my dick a little longer, and slowly started to reach her hand down her pants. Ashley saw too, and said "you know Sara, it isnt really fair that you are still clothed."

Sara thought for a minute, then stood up and slid off her pants, but stopped and said "this stays a secret..." then continued to take off her underwear, shirt, and bra.

I should take a break here and say that this all happened within a few minutes, but it really seemed like much longer.

Anyway, Ashley is slouched spread eagle on the couch while Sara's legs are conservatively spread. Both are looking at my dick, but Ashley is also glancing over at Sara. I think Ashley was getting bored, because she whispered "you have a condom?" Sara's hands stopped moving, and she just stared at Ashley. I said "yeah, probably in my bag," and I reached over and looked through the front pocket. I had a few, and pulled one out. Ashley got up, snatched it from my hand and ripped the packaging open. Before I could even move, Ashley had the condom on my dick and she was standing over me, rubbing my dick on her pussy lips.

Sara started to get up and said "I should probably leave you guys down here..." Ashley said "No, just stay. I dont care," and I just shrugged my shoulders. Ashley's tits were swinging in my face, and I grabbed her boobs and sucked on her nipples. I looked up, and she started making out with me. I could see Sara out of the corner of my eye, and she was looking at us and masturbating slowly.

She got up off me, and I thought the fucking was over. But she turned around and sat on my dick backwards, facing the couch. I reached around and grabbed her tits as they bounced. She grabbed Sara's leg and pulled her closer. Before Sara could say anything, Ashley was bent over and her tongue was between Sara's legs. Sara's eyes closed, her mouth opened, and for once she looked like she was enjoying herself.

Holy fuck, this seems much longer written out. My fingers legit hurt. I will come back later to finish. If you have reached this far, CONGRATS. I doubt many will actually make it this far though.

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Anonymous
@confessions
30 Sep 2024 11:05AM
• 559 views • 2 attachments
[ − ] thread [ 5 replies ]

wat do yall think of my gf? we both seniors

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3
Anonymous
@chicks
28 Jan 2016 10:14AM
• 0 views • 7 attachments
[ − ] thread [ 22 replies ]

Friend of my sister named Kati. She is a grade A slut. Senior in HS, just turned 18 in November.

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6
dontaskmewhy1
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@confessions
19 Jan 2023 11:25PM
• 1,753 views • 1 attachment
[ − ] thread [ 3 replies ]

My Asian ex was a college RA. She was a virgin until senior year, when I broke her hymen and taught her how to take cock like a good girl. Do you think her residents could hear her moans?

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inabyss21
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@chicks
08 Apr 2025 7:15PM
• 663 views • 8 attachments
[ − ] thread [ 9 replies ]

My little asian college senior fuck hole graduates in a month. Here's a post in celebration of her grad pics being taken today

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Anonymous
@soapbox
20 Oct 2011 8:52PM
• 535 views • 1 attachment
[ − ] thread [ 15 replies ]

Even as p******** Obama declared that Moammar Khaddafy “is no more,” the circumstances of his death remained murky. Videos broadcast around the world showed a dazed Khaddafy being shoved by fighters and pulled to the ground. "They captured him alive and while he was being taken away, they beat him and then they killed him," a senior source in Libya's ruling National Transitional Council told Reuters. "He might have been resisting." Officially, the TLC said he died of a gunshot wound to the head in the crossfire between his captors and loyalists, the New York Times reported. The 69-year-old strongman was said to have been found hiding in a drainage tunnel - ironic, given that he called the insurgents who toppled him "rats," one fighter told Reuters.

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Anonymous
@confessions
01 Dec 2014 1:46AM
• 28 views • 0 attachments
[ − ] thread [ 3 replies ]

All I want right now is to be thrown in the mens shower room at a senior citizens center. I want to be groped and molested and taken and used and raped by old men.

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Anonymous
@confessions
11 Apr 2012 6:46PM
• 1,029 views • 2 attachments
[ − ] thread [ 8 replies ]

I confess that I want to take this sweet, naive little high school senior and violate her with a gang of men while she screams and begs us to stop.

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Anonymous
@confessions
21 Jun 2024 9:03PM
• 194 views • 2 attachments
[ − ] thread [ 8 replies ]

This is her old high school senior pic. She's fat, she's ugly, she has short hair, she wears glasses, she's a total nerd, she never got asked to prom. And I want to fuck the shit out of her.

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Anonymous
@confessions
17 Dec 2023 12:05PM
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I am a white American guy but grew up in Japan (long story as to why) and so I speak/read/write fluent Japanese, went to school with Japanese students, etc., and I have to say Japanese girls are the biggest fucking sluts on Earth, especially if you're a white guy WHO SPEAKS JAPANESE. I know many white guys who go to Japan to get girls and have no luck, but that is because they don't speak ANY Japanese and most Japanese people (guys or girls) don't speak English or other languages. In senior high school, I was able to fuck most of the girls in the school, take the virgnity of most of the girls I fucked, and had like 10 baby mommas. I had to leave the country to avoid getting in trouble and I'm back in America again, but damn I do not regret it at all, those were the best years of my life and I feel bad for guys who never had the chance to live like this.

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Anonymous
@confessions
30 Jul 2013 9:20PM
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[ − ] thread [ 7 replies ]

I have only ever creampied one girl. And it was someone else's girlfriend.

So here's the story: Back when I was a senior in high school, I played football with a guy that wanted to see his freshman girlfriend get fucked by another guy. I wasn't exactly "best buds" with the guy, but we had been teammates for the last 4 years and I guess that was enough to make him feel comfortable asking such a thing.

His girlfriend was the type of girl that was extremely sexy in an innocent, naive type of way. The type that would get hit on because of her sheer beauty (which I will get to in a minute), but the kind that guys wouldn't pursue too hard because her lack of overt sexuality made her seem like a prude, and a waste of time for those looking for a quick lay (which is most of us guys, especially at that age). In fact, you wouldn't even expect her to know the first thing about sex, which actually wasn't too far from the truth. According to her boyfriend, he had only just taken her virginity a few months before, and he was attracted to her for much the same reason as I was in the sense that he loved the idea of corrupting her innocence.

Now back then, this really wasn't something that was as appealing to me as you might think. I had only been with a few other women, none of them were ever that much younger than me, and I felt a little guilty about this plan to "corrupt" an innocent girl. This all changed, however, when he showed me the blurry camera phone picture of his girl sitting up naked, spread eagle on her pink bed sheets with the most embarrassed look on her face. I knew this girl was beautiful before, but considering she never went out of her way to look very sexual or wear anything revealing, I was stunned at the body she had been hiding all this time. The first thing that floored me was the sheer size of her tits. For a girl that hadn't even turned 15 yet, she was 5'2", no more than 115 lbs., and was sporting 34Cs that seemed to defy gravity. Couple that with a tight body; a nice plump, firm ass; and a gorgeous, shaved slit; and I was sold.

In the interest of keeping this from getting too long, I'll skip ahead a bit. But essentially I told him I couldn't do it with him watching, at least not the first time; it would be too weird. He agreed it was fine for us to be alone as long as we video taped the whole thing so he could watch it later. We ended up at her house after school, with the place to ourselves. She seemed very nervous, and started telling me how she hated that her boyfriend wanted her to do this. I immediately felt guilty and said we shouldn't. That I would never want to do anything she wasn't comfortable with. With that statement, she looked me deep in the eyes, jumped on me, and kissed me harder and more passionately than I had ever been kissed before. We made out for what felt like 20 minutes. The kiss itself was so sexual that it was almost satisfying by itself. She finally got up, turned the camera on, placed it on the dresser, and seductively walked back over to me.

"Take me. I wan't you. Right. Now," she said climbing onto my lap and getting closer to my ear in a whisper with each word. With that, I couldn't take it anymore and I ravaged her. Clothes were thrown about; I devoured her perfect, pink pussy; and she sucked my cock like a pro, never very deep, but putting in the effort to gag and continue to try for more. It was perfect. When it finally came time to fuck her, I reached for a condom and she stopped me. She told me to just fuck her without it, she wanted to feel me. I fucked her in every position imaginable and she seemed grateful for every thrust. I finally ended up on top of her, her legs wrapped tightly around my back, and my arm under her lower back and ass pulling her up into me. In turn she was pulling herself up into my cock with her hips and legs. She was working my dick and grinding into me just as much as I was fucking her back in return. I couldn't take it anymore and told her I had to pull out and cum. She clenched me tighter with her legs and begin to buck up into me harder. I thought maybe she didn't hear me and began to panic I wouldn't pull out in time. I reiterated that I was "GOING TO CUM!".

With that, she looked me directly in the eyes and responded, "So do it then." That was it. I began to cum like I had never cum before. Squirt, after squirt, after squirt; I filled her up while her body convulsed and we came in rhythm with each other. With her clinging to my body as hard as she could. Eventually we both collapsed onto each other and lay there motionless for at least ten minutes before either of us moved.

I remember finally sliding out of her and watching my cum pour out onto her pink bed sheets. I was a much better image than the blurry camera phone pic that didn't include my cum dripping out of her and pooling between her thighs. It was beautiful. We jumped in the shower, and cleaned off, and I headed out before her parents got home.

The next day, I got a call from her boyfriend. I expected it to be him telling me how insanely hot everything was and to thank me for helping out. Instead, he was furious, yelling something about how I was never supposed to cum in her, etc, etc. As I came to find out, she had apparently NEVER let him even fuck her without a condom, let alone cum in her. And apparently she wasn't big on sucking his dick either. Could have fooled me based on the exceptional head she gave me.

They ended up breaking up immediately after and she told me that was really her plan. That she was over him and she had fallen for me that night. The rest of the football season was a little tense to say the least, especially since I spent the rest of my senior year fucking and filling this girl with cum AT LEAST 5 times a week until I finally left for college.

We still keep in touch some 8 years later but no longer live near each other (multiple states away). I have seen her a few random times over the years here and there and fucked her, and she swears I am still the only guy that she has ever let cum inside her. Who knows if that's true or not, but what I do know is it is still the most passionate sex I have ever had in my life and she is still insanely beautiful and kept much of her reserved, innocent charm. If we lived closer, I'd probably make her my queen in heartbeat.

Sorry if that story got a little long. I've never retold that story before in such revealing detail, and I guess I got carried away in the memory. I hope you all found it enjoyable.

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