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Real 18 Year Old Sister's Anal Assault

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2
Anonymous
@chicks
23 Nov 2024 1:43AM
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42 y/o Vietnamese MILF hotel room selfie

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Anonymous
@random
16 Jul 2024 5:23PM
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Met this MILF on the beach after she got in argument with her husband. She said she wants to hang out in my hotel room for a little..

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Anonymous
@random
01 Jun 2024 7:56PM
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Drunk milf in hotel room.. WWYD?

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Anonymous
@random
21 Apr 2024 11:29AM
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Anybody want to comment on these clips?? Just a quick jerk at the hotel. Couldn't resist after scrolling the boards.

I need to find a milf or cougar to suck it outta me.

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Anonymous
@random
16 Apr 2024 2:14AM
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Met this MILF bitch taking a walk from my hotel.. she was getting some space from her boyfriend so I invited her to my room for fun

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Anonymous
@random
31 May 2023 3:53PM
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Hey y'all. Working today in a building alone with an older milf. She's in her mid 40s, huge rack with long blonde hair. We work in a hotel that's currently out of season (ski resort). I'm 28 and a cougar hunter.  

Anyways I think she has a thing for younger men as shes always looking to talk to me and I've noticed she's come to work all done up randomly when she knows we are working together. The way I see it we have an entire building to ourselves complete with beds, showers etc, and I really want to go to town on this lady, maybe even hide a camera somewhere and make a little incognito porno. 

I just need some advice on how to break the ice. She's European and I've heard they tend to be a lot more open to sex so part of me is considering just asking her if she wants to relax in one of the bedrooms...this is kind of risky though as I don't want to end up getting in trouble for harrassment if she's not down.

Here are some other things I've considered.

1. Jerking off so I'm half hard and somehow drawing attention to my bulge
2. Starting up a conversation and steering it towards sex, seeing if we can get into it and see if it gets her horny
3. "Accidently" bumping into her with a hard on. 

Any advice on how to proceed would be appreciated. We've got everything we need to have a fun time I just got to break the ice on this. 

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Anonymous
@random
22 May 2023 1:12AM
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I’ve started to meet younger men in hotels while my hubby is away on business. I’m addicted to it. I love  dominant young men and submitting to and them and pleasuring them. How would y ou use this milf? Two lucky guYs got to meet me by writing dirty things on\e\ this forum…. I’m horny For more….

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Anonymous
@random
30 Sep 2021 8:49PM
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Slut milf dressing after taking cock in hotel on the beach

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Anonymous
@confessions
27 Mar 2019 3:15AM
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My mom sat on my lap as we posed for the camera, this went perfect with the shot of her big round ass in her mini skirt. We had some pics of her spread eagle in a g-string on the hotel bed and one of her grinding on my dick from my pov. The online ad was almost complete and I got ready to fill in the description. The description read: Mom and son looking for straight dick to give mommy her first mmf fucking! Call us for hotel room number and be prepared to sand which this petite, thicc, white, brunette, 38-year-old milf; with her 21 year old son. I was trembling and my heart raced as I entered the ad, mom was going to be a true slut after this.

The guy knocked on the door, I greeted him as we waited for my mom. Mom came out of the restroom in a robe and wasted no time stripping for us. Mom loved the attention especially when we started to grope her up and down. Mom got on her knees and undid our pants, before you knew it two dicks were at her face. Mom sucked us up with so much passion, her curly jet black hair was already smeared with saliva and pre-cum. Mom ate us up sloppy and wet, she was so cock hungry, this was her biggest fantasy.

Mom got on the bed and spread her pussy out for us, we started to suck on each of her nipples and fingering her pussy and asshole. Mom got on her knees in the spit roast position with me behind her and her head buried in the strangers crotch. Mom became our fuck toy as we took turns on her ends, feeling mother's raw pussy as her mouth moaned on dick was mind blowing. Mom got fucked by her son and a stranger in a mmf threesome for about 2 hours. I will try to get her to go for about 6 hours when I take her to have a train ran on her.

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Anonymous
@random
15 Dec 2017 1:19PM
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So all this nonstop media coverage of all these people coming forward about sexual harassment, etc, along with being the Christmas season, reminded me of when I was "sexually harassed" by my first boss at my first job out of college. I apologize in advance since this will probably be a long story, but I like to always be as complete as possible when I tell about something that happened to me. Feel free to bug out now if you don't want to read it.

At the time, I was a cocky, full of myself, 22 year old guy and a recent graduate. I landed a good entry level analyst job making what seemed like insane money to me at the time (kind of ironic 20 years later that I thought it was a lot of money). My boss was a married female, in her late 30's, & a mother of two. She seemed so mature and experienced in work and life. I wouldn't say she was hot, but she was attractive and always dressed impeccably.

As I got to know her, I learned that she married her college boyfriend within 3 months of graduating and had her 2 kids by the time she was 25. The "harassment" started with her always telling me that I should make sure not to make the same mistake she did and to live my life a little before settling down. That a person's 20's are meant to be spent fucking as many people as possible and partying like crazy, not raising a family. When my college girlfriend and I broke up about 6 months after I started working there, my boss looked overjoyed and told me "now that you wised up, it's time you started living life. you should go out this weekend and fuck some random girl." Being that I was a very flirtatious, social, and a pretty good looking guy, I actually ended up doing just that. Monday morning she called me into her office and asked how my weekend was. I gave a standard mundane, "it was fine" answer and she said, "bullshit, let me hear it. did you get laid or not?". When I probably turned bright red and was being coy, she said, "ha, I knew it. a good looking young stud like yourself would have no problems getting laid. now tell me all about it",

This sort of minor banter would continue for a while, her always asking me about my conquests and making sure I wasn't falling into the same settling down trap she did. Then she stepped it up a bit and with some of my stories of my exploits with girls she told me she wished she had known me when she was young and how she would have been all over me, but now she's just a "old lady" that nobody finds attractive anymore. "Day Old Bread" is what she would always refer to herself as. I'm sure she was fishing for me to say I thought she was attractive or whatever. She told me how she basically had no sex life anymore. That 99% of the sex in her life consisted of a warm bubble bath, soft music, burning candles, and masturbating to the thoughts of the young guys that she wished she had fucked. She told me that she went to college a virgin, met her now husband at a party the first weekend, and had stayed 100% faithful their entire time together. Yup, she had only been with one guy her entire life. Even with suspecting her husband had strayed plenty, she still never did. "More regrets in life" she would tell me. For my birthday she gave me a present. She said open it when I get home. So I waited and that evening I opened it up. It was a DVD copy of The Graduate and with it a card that she signed "Laura. aka "Mrs. Robinson"" with a smiley face and a heart next to it.

Time continued to go by with much of the same types of conversations, but nothing more. I had been at the job for about a year and a half and for my continuing career growth had decided it was time to move on from the entry level position. I accepted a new job at a different company and gave my notice the first week of December. I was starting the new job the day after New Years and agreed to stay on at my old job for 3 weeks leading up to the vacation I had already planned for Christmas week. Laura said she was disappointed to see me go, but knew I had outgrown the entry level role and she had no opportunity to offer me a higher level job. And even though it was technically going to be held after my last official day, she said I better still get my "cute little ass" to the company Christmas party. I told her I would absolutely be there.

I went to the party which was being held at a hotel ballroom near our office. Was a pretty sweet affair with great food and open bar and a well known band from the local bar scene. The owner of our company definitely didn't seem to skimp on this annual party. Everyone was invited to bring their significant others, though I went solo since I wasn't dating anyone seriously. I finally after a year and a half met my boss's husband and all I could think was what a douchebag he seemed like. Just gave off a slimy, sales guy vibe. I overheard his conversation with one of the other younger analyst girls on my team, Sarah, and he was blatantly hitting on her with his wife within earshot. I totally now understood why Laura assumed he had been cheating on her for years since it seemed obvious to me that he would have no issues doing so and seemingly not caring if she knew. Laura was feeling good with some cocktails in her by the time we got to talking. I will admit, done up in a formal dress, full make-up and hair, she actually looked really good and the dress was very flattering to her figure versus the normal business suits she would wear in the office. She made a point of repeatedly saying she was surprised I didn't bring a date, but glad I didn't so my attention wasn't occupied with someone else being this could be one of the last times we saw each other. Then she started joking and saying was I going to "make a run at a going away fuck with Sarah" now that you didn't work together anymore. Her and I talked about Sarah a few times over the previous year and I said I lived by the "don't shit where you eat" mantra. I laughed and said, "No, I don't think so. Looks like she is occupied." nodding in the direction of her own husband still flirting with the much younger girl. She let out a sigh and mumbled under her breath, "what an asshole."

The night went on and plenty more drinks flowed. I went over to Laura to tell her I was getting ready to head out as I had an early morning the next day. She right away blurted out, "oh I forgot, I have a going away present for you out in my car. Come with me.". We went out to the parking lot and walked to her car. As she walked up to the back door of the car with me following behind her admiring her MILF ass, she quickly spun around and just grabbed my cock with one hand and pulled my head into her with the other and planted a huge kiss on me. I just went with it and started kissing her back. She stopped and said that she had wanted to do that for a year and a half and judging from the growing bulge in my pants I didn't mind it. It was a dark parking lot, but clearly if someone walked near us we would have been in plain view, but Laura clearly didn't care...thank you alcohol! I said what else had she wanted to do, and she just gave a look of pure lust and dropped to her knees without saying a word, unbuckled my belt and pants, which fell to the ground. She pulled my boxers down, unleashing my now fully hard cock and began to perform an expert level blow job on me. For having only been with one guy her whole life, she could suck a cock like a pro! After about 2 minutes of getting head from her, I pulled her up, kissed her and spun her around so her hands were planted on the door frame of her car at the roof and her body slightly bent at the waist with her ass pushed out towards me. I lift her dress up around her waist, dropped to a squatting position and proceeded to eat her pussy and asshole with a wild abandon. She was so wet and tasted amazing. To this day I still remember vividly the taste and no girl since has tasted as sweet. She started moaning and moving her hips like crazy as I was grinding my face into her ass and when she said "holy fuck, that feels amazing" I took it as my queue to rise up and slide my cock into her pussy. I slipped right in and began pounding her hard as I could with her bucking back against me in unison. I could already feel my load building up and I knew I wouldn't last long. She started moaning that she was cumming and that is all it took as I unleashed rope after rope of my hot sticky cum deep inside her pussy. Her legs sort of buckled and I caught her with my arm and held her from behind close to my body. We stayed like that for a short minute to catch our breaths. Then I let go and reach down to pull her dress back down and my boxers and pants back up. She turned and kissed me again and then kind of adjusted her dress back into the proper placement. She just looked at me and said "Thanks for everything you did for me the last year and a half and in particular the last 10 minutes...you've changed my life." All I could muster to say was "No problem. It was my pleasure." And she walked back towards the party and me to my car.

We stayed in casual contact over email and in recent years over social media and I have used her multiple times for glowing references with each new job I have taken over the years. Whether sadly or not, I saw that her husband passed away a while back and she did remarry. For her sake I hope she finally lived a little in between those events. We ran into each other a few times over the years as well but no reliving of that night or anything. It was a total one shot deal never to be spoken about again between us.

So that was my workplace "sexual harassment" story. I never complained to HR or anything else, well because, I am not a pussy, candyassed, snowflake like most people are today. But I guess I can join all the people out there that starve and crave for attention and say.....

#metoo

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Anonymous
@random
17 Sep 2017 10:40AM
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Anjaa GF of asian milf mature Valerija is dreaming at the hotel pool about fucking the
the young hotel guests

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FrumhornyJew
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@confessions
23 Sep 2016 1:30PM
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About 3 or so years back I found this Jewish chat. There was this one couple who claimed to be the main people in group. I traded pics of the wife with husband and was amazed how sexy she was. Also keep in mind that in the Jewish religious world this is beyond taboo. Anyway a couple of weeks passed and I had built up the courage to ask the husband if I could talk directly to his wife and trade pics with her. She had agreed to do so and gave me her email. We started trading pics directly and slowly started chatting as well. I got her number after about a month, unknown to her husband of course, and the chats became more intimate and more than just sexting. Well she came in to NY to visit family and we had agreed to meet. First time we met she had a family affair to go to and looked so gorgeous. I had driven to the location where the family was having their celebration and picked her up. Now keep in mind this was the first I had ever met a married woman and was pretty nervous. We spoke a little about regular things and she then said don't be nervous you can touch me. I touched her leg and went up her skirt to her pussy and rubbed it through her panythose and was so turned on. Unfortunately we had to cut the first meeting short because she had to get back to the affair. We had agreed to meet again a few days later. We met and this time parked in my car about three blocks from her sister in laws house and fooled around in my car for about 3 hours. I ate her pussy made her cum about 5 times. She sucked my cock and made me cum 4 times. She had decided that staying in the car was best because a hotel would be too far away. We met about 2 nights later in a shopping center parking lot and while fooled around outside her van. She was really into exhibitionist stuff. She pulled my pants down and sucked my cock all while pulling her skirt up and taking her tits out. We then went shopping and fooled around in the dressing room of the target I believe. We videochatted a couple time while over the remainder of her stay. She returned home and out relationship become stronger. We had told each other that we love one another. Continued chatting, videochatting and sexting everyday until I had business and had to travel out to her part of the country. We met a couple of times over my 5 day stay. We met at the hotel I was staying in. Never did we have full out intercourse as this would be grounds for an immediate divorce according to Jewish law. (Thats what she told me. Later researched it and found it to be true). Not to make it sound that its ok for extra marital relations in the religion. I returned home and continued the same relationship with her. She had again come to visit family and we met a few times. Again in my car but first time of this trip a guy was standing on his porch watching us fool around. She loved it. Each time we met she had given me her panties to keep as a memento from each night. This trip of hers was a lot shorter so we had time to fit in only 2 meets. Few months later she had to come back to my part of country for a family thing and we met 4 times over her 1 week stay. Most memorable time was while she was staying at her brother and SIL house. I think they were renting out the basement to young college age jewish girls. We had gotten naked and fooled around in the entire downstairs. Started in living room eating her pussy, then moved to dining room where I laid her down on table abd fingered her cunt and ate her again until she had her second and third orgasms then moved into kitchen where she sucked my cock until I came twice. We cuddled on this little leather sofa they had in the corner on the kitchen and I ate and fingered her Frum MILF pussy again to the point where she had an additional 2 orgasms. The entire time I was nervous the girls from downstairs would come up becasuse apparently they had that freeness of the owners to do so. The wife lets call her "Aliza" was hoping they would. We sat naked on the couch she sitting on my lap grinding my cock I played with her tits and we just spoke. We had a little bite of food to eat and then called it a night. I believe it was this trip where we met again by her other relatives house and fooled around in her minivan by the target again. All the same stuff but this time she took my hard throbbing dick and started sliding it in her tight pussy. Now of course I wanted to fuck her but asked her about the law she told me about and said she couldn't fully go through with it. I completely understood but enjoyed the six orgasms we shared that night anyway. Main reason I am sharing this story is for the most recent events. Aliza and I continue to chat everyday and videochatting and all. I recently created a tumblr and found pictures of Aliza on it. I like and commented on a couple of them and next thing I know a man claiming to be Aliza's husband messages me. We trade pics all the while he has no idea that I have met his wife numerous times and has no idea that we fucked a ton as well. Recently while she was at work she had to excuse herself to go to the bathroom. In the past I had joked if I could join her and watch. Yeah I enjoy that. She said yes and actually recorded it for me and sent via imessage. I was shocked as she said she never did that for her husband. Well I introduced that into our sexting where I like her pee drenched cunt clean. She loves it. Also I had requested she finger her sexy pink asshole for me. Again another thing she wasn't into prior to me asking her to do so. In my most recent chat with her husband I had asked if his wife was into anal play or pee play and he said only rubbing her ass and pee would "disgust" her. The entire time I was holding myself back and ecstatic to know that she tries more with me than with her husband. He said he was with another woman but that his wife Aliza, the woman I had met several times and made cum more times than I can count, was never with another man. He shared that they both want her to be with another man but that it is still in discussion.
This might be a pointless story to some but the fact that Aliza tried so many things with me for me and not her husband is so hot. She also once said while I was tongue deep in her cunt that I eat her pussy so much better than husband. I once included her husband in one of our sexting chats. He was watching us and she was telling him how I fuck her so much better. Who knows maybe one day I will fuck her in front of him.

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