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I am a 31 year old bicurious male. I love to wear women's thongs and stockings. Recently I have started exploring more. It started with chat lines, but last night my wife's best friend and her husband came over and he must have noticed the thong sticking out of the back of my pants. Because he came up behind me while the girls were talking and whispered in my ear that he would like to see more of what I had on underneath my pants.. we excused ourselves and acted like we were going to get a beer then slipped down the hallway to the bedroom and closed the door.
I slipped off my jeans and bent over for him. I explained that this had been a fetish of mine since I was 11. He asked if I had ever been with another man, I told him no, but my fantasy was to be a submissive bottom. He told me he was obsessed with anal but his wife thought it was gross. I suggested that we could turn on a porno and he could treat me like he wanted to treat his wife..
I took his pants off and got on my hands and knees on the bed. I grabbed the bottlebof lube from beside the bed and pulls my g string aside. Come make me your butt slut I told him. With that he mounted me from behind and began to work his cock into my ass.
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Anal sex as a punishment, well I'm a man, age 40 now, we moved in with my stepdad we he was 42 and I was 8, I wanted a dad so bad back then, and I was finally getting one. He was so nice and generous at first, then he was always angry, at me usually. I had never been spanked before, and I don't recall hearing I was so bad before him either, but suddenly every thing I did was bad, and He said he was sorry but he had to spank me or I'd never learn. I didn't know what a spanking was, and he said don't worry he'll show me. I asked If he was gonna tell mom, and he made a deal with me. He would spank me and mom never had to know about any of it. Then he took me to my room and I got totally naked and he assfucked me with only spit for lube and no sphincter dilation, and I puckered up my ass trying to keep him out every time so it was never relaxed, and it hurt like hell and made me cry every time from age 8 to 11, and to this day no one in my family believes me, and they've all cut me off for saying what he did a year before he died. No one would even ask him if he did it, I was just blocked and deleted by everyone and he didn't even know what I had accused him of. I turned 41 yesterday, he died at end of August from Colon cancer, how fitting. He was 76. Kept his fucking secret and only ever exposed it so he could confess his sins. I was not allowed to attend the funeral. I was "spanked" for calling my sister fat, putting my socks in the wrong drawer - every drawer was the wrong drawer, for playing too loudly all alone in my room on a Saturday morning, anything that happened was my fault. The teachers called in the police because they knew I was being abused, I lied to protect him, and then he fucked me after they left. Twice the same day. I was 8, he was 45. Everything I did was an excuse to fuck me. Got a bad grade, told a lie, told the truth, tattled on someone, got a detention, forgot to bring my lunch to school, stole an apple out of the fridge, didn't do my homework, laughed at him, called my mother she, not home straight from school, anything and everything. If I got jumped and Beatup on the way home from school, I was raped walking in the door. I thought I was the most horrible child who ever lived and when my teacher asked me what I wanted to be when I grow up, I said I want to be good so no one will ever hurt me everyday - I was 8 years old, and nobody understood or believed me. She told me that was the wrong answer and I should think of an occupation. I always thought I was a bad person my whole life until two years ago, when I realized every single time I was ever called bad it was because somebody bad was doing something bad to me and it was never my fault. I am not a bad man and I never was but i didn't know that until I was 40 years old, they just told me i have had PTSD and I'm dissociative, and I discovered alcohol on my 18th bday, and every time I got drunk or high I would look for some man to fuck me up the ass and i never knew why until I was 27 and all my memories came back. I am only now finding out what's wrong with me and getting therapy for it. I have nothing to show for my life, no family, never married, no kids, no debt, but no property or career either. I'm all alone, I owe no one, and I own nothing, but no one ones me anymore either. I'm very misunderstood and I seem to get along with no one for very long because I am not motivated by the same things they are. I want nothing of this world more than the desire to leave it, and every night for more than 30 years, I go to sleep asking God not to wake me up again, but here I am. God only knows why
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I applied for work at a gay adult novelty and video store on Davies street in Vancouver when I was 21 and I'm not gay. That was even one of the questions on the app and the manager immediately flags it and asks If I checked that right. I say yes and he takes me to the back and says you're a real young and beautiful pretty boy type, do you live around here or just need a job or what. I said I don't really know. I mean I need a job, but I kinda want to know what gay is all about. I guess I have a fantasy kinda maybe sorta... I had a female boss I didn't really care for hit on me and stuff and a played along for a bit until I realized I was gonna lose my job cuz there is no way I'd want anything like that with her. I have this fantasy of having a male boss after me tho. My exgf worked at a store where they fired her and she made good money there and didn't want to leave, so the manager turns it over to the store supervisor and he says are you begging to keep this job? She thinks for a second and gets on her knees and when she looked up she saw his dick. Suddenly she's very arroused and wants this dick in her mouth and she's sucking it as deep as she can and it's taking a while when she feels hands on her head and knows what's coming (cumming) and he thrusts his cock all the way in her mouth and holds is as hard as he can. She feels his dick swelling and then explodig into her throat and she choked and gagged and swallowed his whole load and gasps for air. He laughs, she asks if she still has a job and says he doesn't know, and it sure isn't up to him, but he will float memo asking that any junior staff slated for dismissal who are wanting to perform random and reoccurring oral sex on senior staff be considered for promotion since a hottie just gobbled my cock for no reason lol. At some point I know she didn't stay at that job, but I loved the story y'know? Anyways this guy at the gay video store says they ain't hiring but he may know of some work for a guy like me. How'd I like to make an easy $50? I say sure, he tells me to get naked and bend over his desk, I hesitate, but decide to do it, as awkward as it was, and he lubed up and asks if I've ever done anal and I kinda just shake my head, he slides in somewhat painfully but not deliberate and then starts fucking, slowly at first, and then hard and fast, he doesn't cum yet, but pulls out and tells me to suck him off and I took his dirty dick in my mouth and he clenched my head and holds as he groans and shoot, I swallow his load, stand up to see he opened the blinds and the whole can see me. Some clapping from staff with a few disgusted faces. I could totally taste ass and cum and rushed to get dressed and headed out before remembering the money. The manager is smiling and says it really wasn't about money at all, was it? If you still want a job you're hired. But consider it first. I found a better closer job which paid the same and took it. I realized I didn't want to be a gay guy tho, I wanted to experience the feel of being dehumanized sexually by a man, and I was. And it wasn't the last time. I let a man who happened to be a boss over me at a new job I started in Winnipeg gain power over me intentionally, I dunno why. It was my first Friday on the job, we all went to the bar after work and I was told by a dozen people that the super nice leadhand was a shark out to conquer men sexually, maybe not even gay or bi, just wanting to dominate. I went right up to him and asked of there was any money riding on him taking me home. Just pride mostly, why do you ask? Well, lots of bullshit and rumors, but if there was money to be had I would do it to split it with ya... Do it anyways and see what happens... You're not in any danger here. After a few more drinks and warnings a few cars go to his place, like me and 3 or 4 guys, not sure now, but we went and had some drinks, and watched porn and I started feeling funny, realizing the drink was spiked I asked what was in it, someone laughs and says a little speed to give ya a boost, so you don't pass out. Watching the porn I was getting way too horny and they started getting undressed and jerking off, and I was starting to sweat, so i undressed too. Suddenly I'm flashing and all over the place And my boss in the middle of the big couch tells me I'm safe if I get in front of him. And so I do, now I'm watching porn and getting pulled towards a cock and then it's in my mouth and I'm sucking my boss's cock in front of coworkers and then getting fucked up the ass at the same time. It's all a blur but somehow the whole weekend goes by and all I'm doing is sucking dick and getting used and abused and then we go get all my stuff at the rooming house and I'm tied down to a bed getting my ass torn all the shit, and then swallowing all this cum from somewhere and tasting ass drinking piss and it just keeps going and going. He untied me and turns me around and reties me. Starts beating on my face and such, tells me I can't look like a total sellout when they see I'm his bitch and I don't believe it. But he makes me shave my whole body and writes things on my I forget are there later, like "man cunt" with an arrow to my ass, or "Billy's bitch", or "fucked by 4 guys all weekend". I end up going into work with him and a black eye and shit. I realize my ass feels held open and sloppy lose and when I bend down I fart cum into my uniform, and I think everyone must know I'm gay or some shit, and one guy asks if I woke up with a condom up my ass and I say ya at least he used protection and he says billy and his friends don't play safe. You prolly drank a gallon of goop and tasted ass all weekend, and he leaves me alone. Getting up dressed to get in the shower is a mistake and I suit up when I notice people reading my body. I tell bill I need to go home and he agrees to take me at lunch - and. I still haven't eaten or slept yet. Anyways, story is long enough, but I was a live in sex slave for a man who wasn't nice at all and always fucked my ass as hard deep and fast as possible while I begged him to slow down and. Stop, yet I always defended him and told people they were all wrong about him while getting. Fucked and swallowing cum every day. Getting out became the only option and I did. I won't forget any of it tho. Got high and fucked like every day for months makes one a little crazy for sure.
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I retired young and got bored. Decided I would pas along my experience in chemical engineering to the next generation and so received my teacher's certificate. Applied to several positions and after some rather lame interviews selected a position in the science department at the local high-school.

While it is a public school it is located in a very upper-crust suburb of Charlotte. Most parents, and some of their kids, drive BMW, Audi, and Lexus; belong to the country club, and live in exclusive neighborhood on a lake. Just the kind of girls that turned up their noses and ignored me when I was in high school. Now I drive a Corvette and live on the lake among their parents, sit on several boards, and am hired as a consultant to tell them how to improve their businesses.

Although school here has only been in session for ~2-months I've already gotten multiple blowjobs from 3 separate girls, and fucked another in her tight (but definitely NOT cherry) ass. They're all the same - never had to work hard for anything in their lives, they snap their fingers and daddy comes running with anything they want. Each of them needs a passing grade from my class in order to graduation. None of them do their homework, participate in class, or could tell the difference between an electron and a homing pigeon.

Because I live in their neighborhood I've offered to tutor several of them. For $90/hr they can come to my house on Saturday or Sunday and learn how to pass my class. The fastest way, of course, is on their knees or back. So far 4 of the girls have given in. Stripped naked, taken my load, and then been sent home.

Yes, I'm running a risk - I do, of course, leave behind plenty of DNA - but in reality it's minimal. As long as they keep putting out I'll keep the grades in the system at a 90-95 and they'll pass their end of grade tests. Their fathers use me for my education, experience and brains. I use their daughters for their bodies. I think it's a good trade.
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My ex girlfriend and I were very open with sex of all kinds when we were talking. We spoke about anal sex and she told me she would like to try it some day and entirely separately she told me she would like to be fucked while asleep(she was curious as to whether she would have an amazing wet dream). One morning when I woke up and she was still sleeping(she always slept much longer than me and she was a deep sleeper) I carefully moved her onto her so she was sleeping on her stomach. I straddled her and used my saliva to lube my dick and her ass and then gently had anal sex with her. I came inside her asshole. When she woke up she spoke about a dream she had about us having sex(she didn't specify anal or vaginal). I was too embarrassed after she started speaking about it to tell her what i had done. Even when she came back from the toilet with a puzzled look on her face.
If you want real sex, send me message here:) https://ujeb.se/9GiSY
If you want to see me naughty... Im Wait YOU HERE >>> verrywet.com (My Nick Grace2002)
She had to have been passed out or drugged to have not been awakened from having a cock put up in her ass. Don’t lie about your confession
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First-time-anal Confessions
First-time-anal confession stories and sins

Confession Stories
Confessions Current: first-time-anal

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I am a 46 year old woman, divorced twice, kids are grown. I have had 12 boyfriends and 2 husbands who have had sex with me in my life. I've always kept myself in shape and as thin as I could after 3 kids. My legs and ass have always stayed in good shape. I will let me cum in me in front, only my husbands and 2 others came in my mouth and I steadfastly refuse to have anyone in my butt.
I was on a date with a very wealthy super-handsome guy who is only 38 and divorced. After a very good and very expensive dinner and a trip to the theater, we were picked up by his limo. He raised the privacy window, and pulled out his cock and told me he wanted me to suck him. I don't know why but I just did it. I wasn't even appalled by his actions. I just started sucking his cock. As I did he pulled my 36C boobs out of my dress top and proceeded to stroke them and pinch my nipples. He came in my mouth and I swallowed it all and he deeply kissed my jizzed mouth moving his tongue around to get what remained. He pulled me over his knee, raised my dress and ripped off my panties and proceeded to spank me soundly. He said it was for being such a cum whore and an easy slut. After he was done we were at my place and he told his driver not to wait to get a change of clothes and meet him for the office at 7 in the morning.
Without being asked he came up to my place, the doorman could easily tell my hair was mussed, my lipstick messed up, and my boobs weren't placed back in my dress very well. I looked and my date hadn't bothered to zip up his pants. In my place I tried to recover and ask if he wanted a drink, when I turned back for an answer he was totally stripped and opening the drapes to the balcony so we could be seen. He told me to take off my clothes right there and I did it without question hoping I was going to get at least one orgasm out of the evening. I confess I'd planned on sex yet since it was our first time out together, so I was in full growth between my legs. It wasn't pretty. He asked if I had lube and I said I only had Vaseline, no vaginal lube, but I was wet enough. He went and got the Vaseline, and rubbed it on his cock. I told him he wouldn't need it. He replied that it was for me not for him.
"I made up my mind I'm fucking that ass tonight slut" he said
"No, I've never done that, and I don't do that, won't happen" I retorted
"Fuck you" was his answer.
With that he bent me over the back of my couch and I started screaming, he stuffed his socks in my mouth and said that he want' fucking that forest of a pussy but he was going to fuck me. He pushed it into my backdoor and it was hot and searing. After he was done he made me stand there even wiped up a bit of blood from my anus and showed it to me. Then took his belt to me. I was crying, my ass was red and swollen and I noticed he was hard again. He forced me on the floor face down, and fucked me again.
I came, not only did I get the biggest O I've had in my life, I had 3 of them while he banged me in my backside.
Now I beg him for it in my butt, suck him in public when he wants, let him fuck me in the front door anytime, anywhere, and beg him for anal sex.
He gives it to me but not enough. I now have two other guys who will do it to me that way, and I have several orgasms everytime I get a cock pistoning in and out of my butthole. I think back that I started letting the first boy fuck me at 14, and I've missed out on 31 years of sheer bliss.
I'm a buttwhore now totally, unwavering, submissively, giving my butt to any cock I can. I even went back to one of my ex husbands and let him do it to me.
too bad I missed out for soooooo long.
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I met this Korean woman who was in her early 30's. Good looking, tight body, great legs and ass, and huge tits. She was very chatty, and eventually after becoming a bit of a regular asked me to come back at closing time. I came back and helped her close up and as we were turning the lights off she opened her blouse and kissed me. I grabbed those huge tits over her bra kissing her as I worked my hand under it to push the bra up over her tits. DD size tits that were very firm, with very little sagging and the most perfect dark brown areolae and nipples. Her areolae were about an in
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