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Several months ago I met this guy online. We are both males, both married and in our late 40's. He put feelers out there as a feminine guy, wanted someone to meet while crossdressed and he wanted to be sub to a dom man. I'd not had any strange pussy or ass in over 20 years but was interested. We talked exchanged pictures and he started showing me pictures of his fat wife with huge titties and ass. He would even write my name on her while she was nude and take pictures to send me. I had some old pics of my wife and showed them to him.
We met, and started a fem/masculine get together in which he would dress and I would fuck him and dom him. He wouldn't suck cock though. I finally made him do it and he got mad and I finally got him back to meeting me. He had been fucked by 4 guys before me, I'd parade him around and call him slut, cunt, and other names. I would even open the drapes in the hotel/motel rooms so that people would see this chubby older woman getting banged in her butt through the window. They didn't know I was fucking a guys ass. I always started the session by making him stand up and stick my finger up his butt and make him walk around the suite, opening drapes, windows anything I wanted. He got really sub and I even more dom and I would make him do things to his wife, and take pictures to send me. She dommed him in real life (not sex life) even making him wear cotton panties all the time usually in pink, pastels, and white. So he wouldn't mess them up she made him wear a panty liner or a full pad, just as she did everyday. Sometimes she would make him wear a bra as he had cubby manboobs. Even when they first started fucking she refused to let him stick his cock in her mouth, or in her ass. So I told him he should take his wife and force the bitch to take cum up her ass or mouth. His cock had gotten to where he could barely get it up (usually with injections) so I wrote a story about her being passed out and my fucking her.
He started experimenting with her drinking and slipping in a sleeping pill. She would pass out and he took pics of him dildoing her cunt and sticking his limp cock on her lips. At his suggestion I waited till I got word from him that she was passed out and went to his house. I played with her for a while, ate her pussy out, let him play with my nipples, then I laid on top of her and she automatically spread her legs. Instead of fucking her then I just put my cock into her sopping pussy and got it really wet, then laid him down in his girly clothes next to his wife and fucked him right next to her, in the bed the two of them shared.
After that I made him do some kinky shit, and got my cock hard again, then fucked his wife while he placed my cock at her entrance. I shot a load up her slit all the while sucking, mashing and bruising her tits. I kissed hickies on her neck, and stuck the business end of a wine bottle up her loose cunt after I was done. I made him make me dinner, while dressed in his nightie with stockings and heels. Then told him it was time her virgin asshole got fucked by a real man. We went up to the bedroom and rolled her fat ass over, I made him grease her up with some lube she had and I got on top of her while she was lying face down on the bed. I put my cock into her, and reminded him that this was the position in which I first fucked him. After having shot two loads already, it took me about 45 minutes to cum up her virgin ass. It was certainly tight, I think she was indeed a virgin, but after a 45 minute reaming with a pretty thick 7 inch cock, and her being passed out, it was gaping open bigger than a quarter.
He started to panic wondering how he was going to explain the cum in her cunt and ass. I didn't give a shit and instead jacked him off all over her face and tits. I then told him that her cunt was way too loose for her to only be fucked by his scrawny little cock. She was having an affair. I then told him the best way for him to not be accused of fucking her while she was asleep would be to suck all my cum from her cunt and her ass, and lick his off her face and tits. Then I left. I don't know what he did, but it worked out.
I fucked her about 12 times that way, and finally he told her that he liked being fucked and dressing up and she liked the idea of him being a "woman" too. So he had permission to get dressed and fucked in front of her. I went and fucked him several times, then going off with her to the store, or out to eat (using his credit card each time) then I'd go back and get off again. She made him start sucking my cock to orgasm many times, and eventually she let me fuck her in front of him. She took my cock up her cunt, her mouth, her ass, she even did ass2mouth in front of her husband. I even made him clean my shitty cock with his mouth after it was in his wifes ass.
It's a very rewarding relationship, but we still like to get her drunk and passed out so I can abuse her cunt and ass and bruise those big tits of hers. She just laughs about it now.
This goes back 30 years. I went to New York City in Manhattan for business. I was stressed and tired and a little buzzed and drunk. I went to an oriental massage parlor that was located in one of the lesser hotels that populated Times Square at that time. There was a cute Japanese girl giving me a massage, I was totally naked. She started rubbing my balls and cock and I got hard. She asked if I wanted a happy ending and I said yes, and gave her the required $20 extra. Then I asked her to get naked and gave her $40 more. She did it. I was fondling this skinny Japanese girl with horizontal pussy hair, and for being so thin, she had at least D cup tits with dark nipples. I tried to stick my finger in her pussy and she backed up very quickly. We started talking more, I offered her $ 150 if I could fuck her. She said no and eventually said she was a virgin. I questioned her because she was jacking guys off for a living. But she insisted. I told her I'd give her $ 100 to look at her hymen. To this day it's the only hymen I've ever seen. Then she wanted to go back to my happy ending. While she was jacking me we talked a lot, I was trying to convince her to go out with me. Finally I had a date for the next evening, and for $1000 right then I fucked her virgin cunt. To this day I have the white panties I used to wipe her blood and some of my cum off her pussy and ass cheeks. We went on the date and I fucked her again for free. Each time I came in her super tight pussy. That date night before we went out I got her to suck me off, then went on the date and could spend plenty of time when it came to her pussy fucking.
I went back 6 months later and went to get a massage. She was working the counter instead of the back. She stood up and was pregnant. I told her I guessed she'd let other clients do it to her for money. She said no, she'd only had sex twice between her legs, and once in her mouth.
I made her book me with a really young girl, fucked that girl and let her know about it before I left.
Never saw her again.
#virgin #oral #sex #prostitution #massage
It was my first time at a gay bar. My wife is a real bitch sometimes, and she dared me to go that night. I'd never been with a man, but she was a little more liberal than me and said I might enjoy it. I thought, "What the fuck. Why not?" I arrived about 8:30 and ordered a drink. Within five minutes a large man walked over to me and offered me another drink. He was about 10 inches taller than me and had a huge belly. "I like the way you look," he said. "I want to fuck you." I stammered and didn't know what to say. He just grabbed my hand and started walking away.
We walked outside to his van. He had all the back seats removed, and when he closed the door he told me to strip. I dutifully took my clothes off. He did the same. He had a rather large cock and was uncircumcised. "When's the last time you got fucked?" "Never," I said. I was a little nervous. "Then, here's how this goes. You suck my cock until I'm hard, then I flip you over and fuck you until you cry." I tried to protest as he pushed my shoulders down and forced me to my knees. I really didn't want to put his cock in my mouth, but he was much stronger than me and pulled my head toward him. His cock pushed past my lips and I gave in. I couldn't fight him. I started to suck him, rubbing his hood back and forth over the head. "Fuck, dude. You suck cock better than your wife does." About that time the door opened and my wife was standing there. She quickly got in and closed the door, sitting on the floor to watch the show. I didn't know what to do, but she said nothing, just stared at me sucking this guy's cock.
She wanted this, and I love her to death, so I decided not to fight it. It took a few minutes, but he got hard as a fucking pole. He pushed me off and told me to turn around and get on all fours. I noticed my own cock was hard and nobody had even touched it. As soon as I was in position I felt a wet finger enter my asshole. It hurt quite a bit but I held my tongue. After a minute he pulled his finger out and I felt him shove his cock all the way in my asshole. I yelped. "Oh, yeah," he said. "Not only do you suck cock better than your wife, your cunt is tighter than hers, too." I was shocked. That's right," my wife said. "I've been getting Tom's dick for months." She turned to him, "Now fuck him until he's your bitch." He started to fuck me and it hurt a lot. Within two minutes my asshole was on fire and I felt the first tears stream down my face. He fucked me even harder and each thrust brought new pain. Within another three minutes I was weeping openly, begging him to stop. "Shut up you little pussy," she said.
He fucked me for nearly a half hour. The tears had stopped and his thrusts were brushing against my prostate. My own cock had gone soft through the pain, but now was hard again as the feeling had changed from pain to ecstasy. It wasn't long and I was telling him to fuck me harder and deeper. He asked her, "Where do you want it, ass or mouth?" "How about both?" she said. He pulled my hips back and said he was cumming. I felt his cum hit the inside of my ass, then he pulled out and told me to turn around quick. When I did I saw he had pinched the base of his cock. As I turned he shoved his cock into my mouth. He let go of his cock and resumed cumming. He filled my mouth and she told me to swallow it all. I tried. A little came out of my mouth. Even after he was done cumming she had him mouth fuck me until he got hard and came a second time.
She drove me home, my ass and mouth sore from the pounding. She said that was the sexiest thing she had ever seen. We're more in love than ever and I really did become his bitch and let him fuck me anytime he wants.
I´m really worried about her the addictions gotten really bad and she dumped me because i wouldnt let her call the dealer for more rocks and pills so now the last person i had left just got taken away from me by drugs.
#goddamnit #nobodyleft #alone #lonelyfuck #fuckass #shesgone
I am embarrassed that at every summer bbq & gathering of family & neighbors at my parents house my Mom makes reference to our neighbor "Frank" helping to assemble our bikes for me and my 3 siblings on Christmas Eve in 1985 and thanks him in front of everyone. My parents are in their late 60's now.
Why am I so embarrassed?
Because I was 11 that year and, during the night, I heard noises from our den around 2 a.m.
As I approached the den, I could hear voices and groans, it was obvious that someone was in there.
When I got to the entryway I saw my Mom on all fours with Frank on his knees behind her, holding onto her hips, banging the shit out of her. My Mom was clearly loving it. I heard several "Oooooh yeah!!!!" remarks out of her. At one point "Frank" turned his head and saw me staring at them and just smiled and caressed my Mom's ass and asked if she was enjoying herself. I will remember him saying "I've wanted this for a long time" to her and my Mom replying that she had too. I watched for several minutes until they finished and began kissing.
My Dad was a cop and was working overnights at the time. I never saw my Mom in such a good mood as she was that Christmas Day in 1985.
Every time she tells the story of "Frank helping me out so much that night!" and smiles at him, "Frank" almost always glances at me and smiles as if to thank me for keeping my mouth shut.
I am 33 year old bachelor from India, I recently went to thailand solo trip , it was my first ever international trip and I was very excited .
I would like to share 2 stories in this confession. Both are a little embarassing. Its a true story so just enjoy and let me know in comments if u enjoyed .
I am a hairy guy so I decided to get my body waxing done while I was at thailand . I opted for full body waxing and they charged me 1800baht . I paid the amount beforehand and then entered the spa. The lady who was appointed to me was quite old (maybe 50yrs ) . She told me to get naked and lay on the table .
She started my waxing from the neck below then chest . It was hurting a little but slowly she reached till my crotch area . She held my dick in one hand and began waxing with the other hand . My dick became so hard within a few minutes and a few minutes later the inevitable happened. Even though I tried to control myself and stop myself a sudden pressure started building up inside my dick n crotch area I began spurting out loads of cum in front of her
#naked #beach #embarassing #neighbours #nude #shy #shame
I mixed up my depressants with my laxative and I now have to go to the toilet every few minutes, it's terrible! :(
Please release me from this! :(
#depressants #laxative #toilet #terrible #confession #embarrassing
I work construction and this highschool senior named Alissa, came to me looking for part time work. It’s rare that someone younger, comes to me looking for hard work, especially a young lady. I gave her hours that suited her school schedule. She’s pretty tough, built for work. Strong legs, thick butt. I’ll admit a major part of me giving her work was so me and my guys can have a good piece of ass to stare at while we’re working in the sun. We all talk about her and what we’d do to her. It doesn’t help that her butt is so big and she wears tight jeans. I’m 35 and my guys are all over 30, so I know nothing romantic will happen with this girl. She’s just a temporary hire until she graduates. But if I somehow could convince her to fuck even for some cash I would love that. But that’s just unrealistic thinking. I’m satisfied just staring at her ass from a distance while she’s all sweaty working for me. I’m really sulking it in while it lasts. This is the only time I’ve ever had a young lady work with me, especially with an ass like hers.
I was trying to flirt with this guy on a chatroom, and he did this action which made our characters have a sexy hug, and I thought that I'd try something like that, so I clicked on the one that said "KissButt", and I thought it sounded like it could work, so I clicked it... The characters then moved to a position where I bent over and pointed to my butt, and this guy was forced to kiss it, So embarrassing.
I knew theres space to see through in the washroom door, so i kept my big butt towards the space. My colleague pushed the door creating more space and kept it that way for some time getting a good look of my ass. He thinks i dont know about it.
I would like to make amends and confess. It happened many years ago back in school and in retrospect I feel terrible about it.
There was this one kid in our year and he was kind of unpopular. Maybe not unpopular, but he ran in another circle of friends and was rather shy. So we made fun of him, but really harmless banter mostly.
One day we had this huge event at our school that took place in our gym. A lot of people came... I think round 3,000 people watching the festivites on the ranks around the gym, parents, teacher from other schools, principles,.. so many people....
My year and me had to take part in a rely race, so we had to get in a row and in front of me was that kid. He was a bit on the chubby side and really un-sporty. He wore very worn out pants and that is when I go the idea.
Just seconds before it was his turn to start running I pansed him. (I have no idea how that is spelled... well, I pulled his shorts down all the way). And I not only pulled down his shorts, but also his boxershorts underneath. As he was about to start running, he tripped BUTT NAKED and fell face first to the ground. He had a really small penis.
The whole gym, everyone!! was laughing and pointing. Some where even crying with laughter and I think some took pictures. He was the joke of the whole school for the rest of our time there.
Now I feel rather embarrased for what I have put him through.
#school #pants #sport #chubby #bullying #embarrassing #laughing
My 6th grade grammar teacher was literally sexist. she would give no work to the girls and all the work to the boys. she hated my guts so i hated hers. not much else to say.
I'm 16 and young for 3rd year in college. I'm attending summer sessions to advance further. There was a wild party, and this very pretty girl of 21 passed out drunk. Some girls asked me to lift her and take her into the bedroom and lay her down. I did, she was totally out of it. While in there I pulled her blouse and bra up played with and sucked her tits. Then I lifted her skirt to see her pantie-less pussy and ass. She had brown pussy hair trimmed so it was about 2 inches wide and went straight up from the start of her pussy lips about 3 inches or more. She had light and soft hair on her pussy lips. I softly licked on her pussy, she moaned, I panicked, but she was out, just having a reaction. I licked some more, fingered her with two fingers, and walked over and quietly locked the door.
I raped her pussy. I then pulled her clothes back, covered her up and went to the party. It all sounds like I was gone a while, but it was my first time. . . it was all over in about 4 minutes, I'm ashamed to say.
That was Saturday, today; Monday I just finished a 2 hour class with her sitting next to me. I'd really like to date her but I'm so much younger and she knows it. It's that way with almost all the girls. I guess I'll have to wait for another party.
I am a bisexual queer woman. Instead of openly coming out to the community around me, i picked a convenient target, a nerdy quiet girl and harassed her to no end. [email protected]
My crazy girlfriends dragged me out of the shower to embarrass me in front of boys. I know we were all friends and it was just a friendly joke, but watching boys looking at me naked and hearing them saying "nice pussy" turned the joke into a very humiliating one. My worst nightmare of being seen naked had come true. I got forced to show everything that day and I'm sure those boys loved it. The stupid part was, as embarrassed as I felt, had to laugh right along with all of them. I guess it was all teenage fun.
I used to be obessed with my crush in 7th grade and then he movied and unfollowed me from instagram..
A young man was showing off his new sports car to his girlfriend. She was thrilled at the speed.
"If I do 200mph, will you take off your clothes?" he asked.
"Yes!" said his adventurous girlfriend.
And as he gets up to 200, she peeled off all her clothes.
Unable to keep his eyes on the road, the car skidded onto some gravel and flipped over. The naked girl was thrown clear, but he was jammed beneath the steering wheel.
"Go and get help!" he cried.
"But I can't. I'm naked and my clothes are gone!"
"Take my shoe", he said, "and cover yourself."
Holding the shoe over her pubes, the girl ran down the road and found a service station. Still holding the shoe between her legs, she pleaded to the service station proprietor, "Please help me! My boyfriend's stuck!"
The proprietor looked at the shoe and said, "There's nothing I can do...he's in too far."
#embarrassment #shoe #car #crash #boyfriend
Hi, I'm 49 yo woman. I live with my daughter, my son and my daughter-in-law. I always had disagreements with my daughter, and we tried to be calmed since my son married, but unsuccessful.
My daughter is very impulsive and shameless. She became a very good friend with my daughter-in-law. On the other hand, I keep a distance with my daughter-in-law, just to have some normal relationship.
One night, when my son was at work (he works as a security), my daughter and my daughter-in-law were out. They came home late at 2.30 a.m. .
I didn't sleep when they arrived, so I needed an explanation why they came so late, and where they were. My daughter got crazy when I asked them, she started offending me and called me useless.
I was mad at her and I slapped her. On my biggest surprise, my daughter-in-law interfered, protecting my daughter and she stood on her side.
My daughter just said to me: "you're lucky that you are my mother, but let's see if you can beat your daughter-in-law". I was stunned. My daughter-in-law pushed me on the couch and got on top of me.
I was afraid and confused. I tried to fight her, but I couldn't, she caught my arms under her knees. They were both laughing at me, as my daughter-in-law slapped my face.
She started slapping me with her feet, while my daughter watched and reminded me how miserable I am.
That night I was embarrassed like never, by my daughter-in-law and my daughter. My son never knew what happened, cause I don't want to ruin his marriage.
#fight #daughter #slapping #feet #embarrassed
Ok I know this is terrible but, I admit it.
when I make cereal...
....I pour the milk and then add Cereal.🤦🏾♀️
and on top of that I put the finished milk back in the fridge. please forgive me.
#laziness #milk #cereal #embarrassing #fridge
I was attacked in an outdoor rock concert by bunch of rowdy guys tearing off my clothes and groping me. I remember my tits hanging out, the sound my skirt and panties ripped off and panicking about being naked in a public place. Felt hands grabbing my tits, legs being forced apart. and sodomized with a beer bottle. I remember flashing lights, loud music and hearing guys saying '" fuck that pussy" Don't know how I managed to get away from them. I remember pushing through the crowd, covering myself with a piece of skirt I had picked off the ground and running into portable bathroom. If it wouldn't have been for the girls that were in there that rushed my into their car, I would most probably gotten gang rapped in some dark corner with people not even noticing it. I was so scared and upset I was way past feeling humiliated.
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