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Prostate milking prostate-O toys&advice

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Dedicated to info on milking and P spot-O's, particularly urethral prostate massage and urethral prostate fucking and milking for straight, gay men, femdoms. Share techniques, devices, tools, toys and their sources. How to for milking, full, large load cum harvesting with or without orgasm, full body prostate orgasms, training your self or a sub, savoring the product. Share pics and vids. Contact members through inter mail for private conversation or hook up.

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2
Anonymous
@random
09 May 2012 1:16AM
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i am gay i know and i walk around with some kind of butt plug up my ass everywhere i go. i have been running a fevor for 2 weeks now so i decided to go to the doctor. he told me he wanted to check my prostate. fuck i was in trouble i had a 4 1/2 wide butt plug 9 1/2 long up my ass. (he knows i'm gay). i told him i had it in and he acted like it was nothing and told me to stand up and drop them and bend over.

i did and i heard him gasp and pulled it out. he told me there not much of a reason to check. but he stuck a finger up my ass anyway. he said he cant even feel it so i told him to put his fist in its ok. thinking he would say na thats ok. but i was wrong he put his fist in my ass. and started fist fucking me. i looked back and told him to get more lube and he can go to his elbow and he did. then he started rubbing my balls and stroking my dick. he was suprised that i could get hard while being fisted. he didn't stop untill i came all over the table.

it was 4 days later he showed up at my house. he told me he wanted to do a follow up on me. i was like ok and we went into the house and he told me to bend over and pulled my butt plug out.my boyfriend was there and he said he might need to check him too.
hell the next thing i knew is he ws fisting both of us elbow deep. and now it seems he comes by on fridays to check us over. and hes learning to take a fist hiself. it took me over 2 years to take my first fist and my b/f took over 1 1/2 years.
but the doctor is only been doing it 4 months and can damn near take one.

oh test show i have aids and i said no meds. just going to live untill i die and i hope they put the biggest butt plug up my ass they can find when they put me in the ground.

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Anonymous
@confessions
10 Mar 2012 10:30PM
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25 year old male. Hi, my name is Brandon. First of all let me start by saying I have certain interest in penis. This is not a joke, ever since i was a child when my weird uncle first touched me, i knew since that day i like the soft touch of penis against my lips. what im looking for in a mate is either a gay man, cross dresser, or legit trans sexual. i cant resist penis popping off the inside of my cheeks, and no, i dont mean my ass cheeks, i mean the popping sound off my mouth cheeks when i finally let the air escape from my mouth.... the point is im ready for any sort of cock intercourse... but please let me continue (dont worry ill post my phone number) ... other than my mouth i also enjoy a firm hard cock in my tight asshole.. there is nothing like the feeling of hard grim cock hitting the sweet spot of my prostate gland.. theres nothing better than receiving a reach around while being pork fucked in my tight asshole... it makes my orgasms that much more intense.. listen boys, i could go on and on and on........... but heres my phone number please give me a call if youre in the new england area.... im waiting... im waiting .. impatiently i might add... waiting for your cock... in my ass. good night and sweet cum dreams to all and to all a good night

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Anonymous
@confessions
02 May 2022 2:55PM
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I've just turned 50 and with that age bracket - there comes problems, the main ones being an enlarged prostate and erectile disfunction. I've got some Cialis and sometimes I wonder if a lot of the ED isn't psychological. My wife and I have been in an open marriage for a few years, she's bisexual and I love the fringe benefits of it. One night she went to a bar and brought back a very attractive female, who was about 45 years old (same age as my wife).
They were both tipsy, and my wife introduced me to Jessie, raven haired, medium sized tits and a nice tight body. They sat down on the couch and invited me over. Small chit chat ensued. My wife poured her some wine, and she drank some too - I refused because I knew that just in case I was going to get lucky, drinking wine would screw with my ED. I stepped away for a minute and went into the bedroom and took a Cialis, got a drink of water and chugged it. I went back into the living room where they were sitting and they were making out. Jessie noticed me, and stopped kissing my wife.
"Oh, I'm sorry I thought you were going into the other room to give us privacy..."
My heart sunk, looks like I wasn't going to be sticking my dick into Jessie tonight.
"My bad," I said, looking down - defeated.
My wife saw that I was a bit hurt and explained, "Jessie is a lesbian, she isn't into men... she doesn't mean any disrespect..."
I should really give them their privacy, I thought...
"Ok, cool - I'm going out."
So I got in my car and drove around, no destination - but then I thought about it, I just took a Cialis. Pretty soon my cock would be begging for some wet hole to fuck. I guess I could get sloppy seconds once my wife is done with Jessie... but that could be a while, so I decided to go to an adult bookstore a few miles from my house. Weird shit popped into my mind, "Maybe there's a hot chick I could fuck in a glory hole, I've never done that... or maybe I can get an escort or hooker..."
All kinds of shit was going through my mind. This bookstore is a 24 hour store, so I went in and it was busy as fuck. All I wanted to do was ask the guy behind the counter where to find a lady of the evening, but too many people were around him. I noticed two women looking at toys and giggling, the looked like they were in their mid 20s, so I tried to blend in and started looking at masturbators. The small version of the Fleshlight was 79$?! I was taken aback and shaking my head. I was trying to maintain the "no eye contact" creed while I browsed all kinds of toys. I stopped in front of the 'prostate massager' section, all shapes and sizes - I never had a massager or anything anal but I heard of the wonders of prostate massages. Too bad my wife and her new friend were fucking around or I'd definitely try to experience something like that. I heard a little whisper behind me, something like "you ask him..."
I turned around and it was the giggling ladies. One was a brunette with very dark brown eyes, the other woman had purple and white streaks in her hair, but had cool blue eyes. Both were very attractive.
"Hmm? What's up ladies? I asked.
They blushed, "ummm, are you gay? No offense if you are... we're just wondering about the prostate massagers..."
I blushed, "OH, NO NO! I'm not gay, I'm straight..." so I did something that I never did with a stranger, I opened up, "I have ED, and I've done some reading and some people say these things help. I just turned 50 a few days ago, and my wife is at home banging her girlfriend and I'm just here... browsing because - well I just took a damn Cialis and ... well that's that. Sorry if it's too much information... I'm not a creep or anything."
The brunette smirked, "You don't look 50 at all, I thought you were about 35 or 40 at most."
Purple haired girl nudged her friend, "he's cute for a 50 year old..."
They both giggled and blushed. I didn't know what to say, this was odd because I've never talked to anyone in any adult bookstore given the exception of the checkout clerk. They saw I was struggling too, and the purple haired one spoke up.
"So you let your wife bang other women? That's kinda hot... I just broke up with my boyfriend, and Amanda just doesn't like dating at all so we're both kinda of single but we keep each other company if you know what I mean?"
My dick twitched.
"I'm Mike," I said, extending a hand out to the purple haired girl. She took it, and replied, "I'm Mary and this is Amanda, nice to meet you Mike."
Amanda's face was turning a bit red, "Mike, since you don't have anything else to do, you want to join us for some coffee? There is a cafe just down the street!"
I agreed, and started walking towards the door when Mary said, "Mike, aren't you forgetting something?" while pointing to the prostate massager.
I picked up the smaller one, $45... and headed for the check out. I paid for it and the clerk put it in a black bag. I turned around and Amanda and Mary were gone. Well there goes that. I left the store and walked to my car.
"Mike!" I heard a call from a distance, it was Amanda waving from across the parking lot.
"Oh I thought you both bugged out," I laughed.
She took me by the arm, "oh hell no, and miss the chance to hang out with a sexy 50 year old with ED??"
We both laughed. Mary, Amanda and me walked down the street arm in arm to a cafe. We sat down and talked for what seemed to be hours. These two women were not only attractive, but smart as hell too. I asked how old they were.
Amanda spoke first, "I'm 23, just turned 23 in January."
"I'm 26," Mary said sipping her coffee.
I laughed, "you're both half my age!"
"Older men are sexy, our generation likes older men. You guys know what you want and you're not complete idiots, or assholes," Amanda said.
Again, my dick twitched.
Mary looked me in the eyes, "we're freaks in the sheets, Mike."
I couldn't help myself, "is that an invitation?"
Amanda put her hand on my knee, "why would two girls in their 20's be hanging out at a bookstore at night unless they had an agenda? You were the first decent guy that came in there and we were in there for a while..."
My heart started racing.
"We're gonna put your little toy to the test, if you let us..."
I was in for an adventure of a lifetime.
We went back and got in my car, I drove them to Mary's apartment, and we all went inside. There really wasn't any wasting time. They stripped me down as soon as the door was shut. My cock was in Amanda's mouth as Mary's tongue probed my throat. My hands wandered from Mary's sexy tits, down to her dripping wet pussy. My cock was rock hard as Amanda shoved it all the way in her mouth to the hilt. I'll admit, I don't have a huge cock, I'm just normal - but the way she was sucking my dick put me on top of the world. They led me to the bedroom and Amanda pushed me down on the bed. Mary unwrapped the prostate massager and started playing with it using her pussy. She let it slip inside her.
I got kind of worried, I never had anything going up my ass before... so my erection started going down.
"Oh, baby - nothing to worry about - just relax..." Mary said.
Amanda climbed on top of my face and I started licking her pussy, she smelled really good, and her pussy tasted sweet. Amanda started moaning and I grabbed on to her nice soft ass to steady her.
I felt Mary playing with my cock, pumping it with her hand, then I felt her mouth around it and I was hard again. As Amanda rod my face, Mary mounted my hard dick and I felt how tight she was. I moaned as her pussy stroked me up and down.
Amanda came hard on my face, squirting a little - but I didn't mind at all. I held her against my mouth until she almost passed out.
Amanda crawled off to the side, and shivered. I could see Mary in all of her glory, bouncing on my cock, smiling. Her nails sunk into my chest as she rode me, moaning. Amanda got up and started fingering Mary's clit and licking her tits as she rode me. Soon Mary came hard, and I could feel her warm pussy juices dripping onto my balls.
"Your turn," Amanda said to me as she grabbed the prostate massager and rubbed it on her pussy.
"We gotta get it nice and wet Mr. Mike..."
Mary spit on her fingers and started rubbing my asshole and Amanda slowly pushed the pussy juice soaked massager in. I moaned in pain, that shit hurt...
"It's ok Mike, we're going to go slow..." and they did.
Mary started sucking on my cock as Amanda slowly used the toy on me. I tried my best to relax. I was trying to focus past the pain... it took a while but Amanda started hitting something that felt so good.
"That's it Mike, relax... we're going to drain those balls..." Amanda said, pushing the toy in, and pulling it slightly out. She started going faster, and then faster as Mary moved her mouth up and down on my pulsating cock.
"Give us all that cum babe, come on..."
I had these two young women fucking the shit out of me... and I felt this weird feeling starting to erupt around my entire body, like all of my nerves were electrified (but in a good way). Suddenly my cock erupted as Mary stopped sucking both of them literally started making out as cum exploded on their tongues and faces. They moaned, they licked my cock and more cum sprayed out. Mary deep throated me, then Amanda did. Then they kissed deeply. I was on the verge of passing out.
"Did you like that, Mike?"
"HOLY FUCK LADIES" I gasped.
They both laughed. They took the massager out of me and put it in a bag.
"I'm going to give you my number, I really hope you call me... I wouldn't mind having more adventures with you..."
"Did you think this was a one time deal old man??" Mary joked.
"You can spend the night with us if you want... no strings, just chill and cuddle and sleep..."
Amanda lit a joint and took a small hit, passing it to me. I took a hit, held it in and let it go as I passed the joint to Mary.
"I'd love to spend the night," I said as we all laid in the bed together.
When I woke up in the morning, both of these babes were cuddled into me. I woke them up and told them I had to go home. They both kissed me goodbye, we exchanged information and they promised me that there were a lot more adventures to come.
When I got home, my wife was passed out in bed with Jessie. Both were naked. Jessie had a tit hanging out of the covers, it was a little saggy compared to the ladies I just spent the evening with.
I started cooking some eggs, but couldn't help of thinking of Amanda and Mary.
I have to confess, I think I am falling in love with two women I just met at an adult bookstore... I've never been treated like that in my life, I felt like a king. Not only was everyone sexually satisfied, we all got along great. Maybe I'm just too deep into a fantasy with two young ladies... but honestly I want more of them. Not even concerned with fucking my wife at this point.

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Anonymous
@random
06 Sep 2013 5:27PM
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True Story From The Annals Of Newport Beach:
Around 6pm, I went over to my favorite bar, JoJo’s, in Newport Beach for a beer and to find a pool game. The bar has a nautical motif, lots of fish nets, stuffed fish, pictures of big surf…that sort of stuff. The bar’s in front and there’s tables behind. It’s a cool little place pretty much locals only, the tourists don’t know the place even exists.
I’m 25, work in Irvine just up the street inland but I live in Newport Beach. I love the beach, love the town and am very happy with my life.
Sitting at the bar was this luscious little babe who looked vivacious, young and eager, with white short shorts, golden legs all the way up to her waist, really cute face, lips, eyes and nice natural tits…a handful at the most but very attractive. She looked at me and I looked at her and it was love t first sight. She was sooooo fucking cute! I wanted to fuck her right there but….and she knew it!
I sat down next to her and went through the preliminaries: Her name was Cindy, she was from Whittier but someone told her about Jo Jo’s and she thought she’d try it out. I thought it was unusual for a girl by herself to have come all the way down from Whittier just to try the place out. I was wondering what she was up to. She said, ”oh no, I’m not alone, my friends are sitting at the table back there,” pointing to the back where the pool tables are and the eating tables. “I’m just getting the beers.”
Yep…there were three girls sitting back there, all by themselves. She got the beers and invited me back to join them, and I went.
As it turned out, there were two really cute girls and one guy. He is rather effeminate but actually a guy. It turns out he was Cindy’s brother--so I could see a bit of a problem of her going with me to my place later.
We all chatted and laughed, chugged several beers and were all feeling quite good. I was flirting heavily with Cindy and she knew what I wanted—her, all of her, and she was ready for it.
Then Cindy came clean: “Jeremy is looking to try something he’s never done before. He isn’t sure about who he really is and wants to experiment. He wants to see what it’s like to be with a guy”. I said, “HUH?” “WTF”? I asked if he is gay and the three girls all screeched and giggled looking first at him then me. Cindy said that Jeremy would like to, “you know”. I said, “no, I don’t know, what the hell are you talking about?”
Monica whispered, “Jeremy wants to see what it’s like to suck a guy’s, you know. You know what he wants to do…he wants to suck a…GUY”! All the girls screamed in their Valley Girl accent. Cindy said, ”he is wondering if you would let him suck you off.” The girls screamed again laughing and giggling and having a great time. Cindy said, “I’ve been trying to find him a guy who would let him do it. Would YOU let him?”
I’m looking at her and I can see the ultimatum on her face--let him suck my dick or she won’t go with me tonight. “So, does he swallow?” The girls screamed with delight crossing and uncrossing their legs.
So far, no one had even spoken to Jeremy to ask him anything. The conversation was between me and the girls. Monica said, “if he has to I guess he probably would.” I replied directly to Cindy, “how about this; I’ll let him suck my cock [the girls screeched in laughter] if you’ll go with me tonight out on a date.” Cindy knew what I wanted. She said, “YES, let’s do it”.
”Ok girls…put some lipstick on him first, make it real nice…I want a red ring on it when I’m finished.” The girls knew exactly what I meant and set to work doing preparing him for his first submission to a guy.
All three girls whipped out their lip color, outline pencils and started in. They were chattering like a bunch of parrots in a tree, telling Jeremy about how he was going to like his first oral experience with a horny guy, who by now, needed his dick sucked. They were primping and painting his lips. When they finished, he did look like a girl: small, submissive and ready to suck! My dick started swelling at the thought of a virgin mouth around my demanding pole. I made a mental picture of how he would look after I had fucked his mouth…ejaculated in it…and then made him swallow all the sticky fluid.
When he was ready to go, I got up and looked at Jeremy’s face. He looked flustered by all the activity but ready to take his first step to see if he was gay. Cindy looked up at him and said, “just relax Jeremy, this is what you wanted. Just do whatever he wants you to do. Don’t say “no” to anything--just do it--that’s what guys like.” “When it comes to sex, guys like to be obeyed,” Hearing that made my dick swell more.
OH BABY…THIS IS GOING TO BE FUN. A BLOWJOB FROM JEREMY AND THEN….FUCKING HER ALL NIGHT LONG….ALL NIGHT LONG!!!
Jeremy sheepishly followed me out to my car…as SUV….blacked out windows. I got in the front and started it then turned on the AC. Then I got in the back and had him sit in the back too. I had on rather tight slacks…good fabric..thin, flexible and tailored. He could clearly see my excitement AND my boner lifting up those thin slacks. I was enjoying this especially since he had never had a cock in his mouth and mine would be the first oozing erection he had ever tasted!
Then he asked…”what do you want me to do”? I asked if this was his first time and he said “yes”. I almost ejaculated right them. I told him to lean over and kiss my hard on. He was kind of slow so I put one hand on his head and guided his mouth to my crotch. I held him there while he kissed and nibbled my dick through my slacks. I was so hard now that my dick hurt. I told him to unzip my slacks while I undid the belt.
His hands were literally shaking with excitement. I pulled my slacks down shorts with them. My boner sprang up right in his face. I laughed and said, “well…there he is…in all his glory”. By now, he was leaking cum…I pushed Jeremy’s mouth down on the tip so he could suckle the slimy liquid oozing out of my urethra. I had him lick it off. He pulled long stringers of cum back with his tongue as he began exploring my erection, the head, shaft and testicles.
I was ready so I pushed his head down until penis met teeth. “Open your mouth Jeremy…he wants to come in and get sucked”. Jeremy opened his mouth and in he went. Tongue met glans…glans met back of throat. Jeremy gagged, further exciting me. I pulled back to let him suck the head then we’d go slow while he got used to having a demanding penis in his mouth. Jeremy looked up almost pleading…torn between desire and revulsion. I had to laugh because I knew he had no option, his brain would force him to suck my dick and drink my cream even if he consciously didn’t want to. He was a twink and he had no choice but to pleasure me…with his mouth!
A few years back, I had let a friend suck me off one time in high school. He had literally begged me. When it came time to do it he told me he didn’t want to put my dirty cock in his mouth and suck it. But…he had no choice…he had to do it. He was being made to do it by something he didn’t know what. That was what was happening here. Jeremy’s mind was making him carry out his fantasy of submitting to a horny male who would make him go all the way…including swallowing semen.
I had my hand on Jeremy’s head and I pushed and pulled his head [and mouth] up and down my cock. I was determined to make it last so I pushed him off and them made him lick my balls. I wanted him to worship the source of the testosterone and sperm that he was about to eat. He actually sucked them, one at a time, while I humped his face telling him what a good job he was doing.
OMG…I was HOT, HOT, HOT! I could hardly wait to see how he handled a load of my sticky cum in his mouth…LOL!
Then, back to my totally stiff erection. I pushed his head down on it again and, this time, began in earnest to fuck his mouth. Not deep but just enough to make him choke on it now and then. In and out. In and out. In and out. In and out. I let him suckle and lick the head…. In and out….until I was ready.
I held his head tight and began spurting. I was grunting and swearing and pushing his head down on it…I was making him eat my entire masculine issue. My prostate, testicles and other glands emptied their rich cream in Jeremy’s mouth. He was green..lol! All that sticky, gooey slime in his mouth at one time…straight from between my legs. His stomach was wretching. His eyes were literally bulging out…LOL! He had a mouthful of my cum and I really wanted to watch him swallow it..
“Just hold it in your mouth and just let it trickle down your throat”. He held it but motioned that it wasn’t going anywhere. I told him to open his mouth and show it to me. It was a big pool of sticky white cream that filled his mouth. I loved it! Then, looking very brave, he took a big gulp and swallowed. Then he took another gulp and swallowed again. He coughed and choked but it was down. He started telling me how rough I was on him but he liked it. He sounded like a girl. His mouth was sticky with cum and he was lisping. I laughed and patted him on the head. “You did a good job for your first time”.
We went back in to the bar and sat with the very excited girls. They could see just by looking at him that he had done it! His lips were glossy with semen and his mouth was sticky and gooey. They all questioned me at once: “How was it? Did you…you know…in his mouth? Did he swallow? Did he like it? Did YOU like it?
I told them “I liked it”, “he did a decent job for his first time” AND---here it comes---“HE SWALLOWED”. They screamed with laughter at the picture of him with a mouthful of cock and creamy cum, unable to take it all at once. They all at once started telling him, “you see, I told you there is a lot to learn about how to give a guy a bj”. “It’s not that easy. You have to find out how each guy likes it…then do It for him”. “Now you know what he likes”, they all sang in unison.
Cindy and I eventually took off for my place. By now, she was horny as a hoot owl after seeing her brother with cum in his lips and the smell of my semen on his breath. They could all smell it wafting around the table as Jeremy began to explained it…and how much he had liked it. He said he was hooked. Monica asked, “would you do it again”? Jeremy answered, “OH YEAH…I’D DO IT AGAIN….AND AGAIN”, again to the screaming laughter of the girls.
When we were alone, the first thing Cindy said was, “OK, show me what you made my brother do for you. I said, “OK but I’ll have to pull over so we can get in the back seat”. She was eager and I was erect again. I could hardly wait to teach her the meaning of respect and she was licking her lips in anticipation of her lesson in obedience. This One loves being a GIRL…and all the things that go with it. Hey…so does her brother….LOL!

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Anonymous
@confessions
19 Jul 2014 11:00AM
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Since my fiance and I broke up, I got really into prostate massage and got some toys to help out. I would sit for hours and watch porn and just slowly milk myself before letting my self cum. I got into a lot of shemale and ladyboy porn in the process and eventually started jerking off to femme bois and some crossdressers as well. I even mail ordered some lingerie to wear while I do it and started to shave my legs since I have a stocking and garter belt fetish. After a while more I wanted more than just toys in my ass. I wanted to have a real life encounter but didn't know how to do it but figured a gay bar was the best bet because I could likely find someone for a casual hook up who I could let fuck me in the ass. But without the lingerie I'm just not as into it and I wasn't sure if I could really do it. I put on a pair of panties, a garterbelt and some stockings under my jeans and went to a gay bar last weekend, but chickened out because I don't know much about gay culture and don't know what they think about crossdressing. I looked at a few guys and wondered what it would be like to suck their dicks but got scared, went home and jerked one out instead. Last night I tried it again and hooked up someone. He didn't seem to mind my stockings. We sucked each others dicks for a little bit, and then I let him fuck me in the ass. It was different than milking myself, but I really liked it. Now I want to do it again, but this time I want to suck more cock and actually swallow someone's load. Some people on here will call me a fag, but whatever, I bet they'd still let me suck their cocks too.

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Anonymous
@confessions
21 Feb 2014 2:02AM
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Later tonight I have a woman coming over to my place. I met her on craigslist. We've been texting over the last week about everything we want to do to each other and tonight's the first night for us to finally get together. I'm 29, white, tall and athletic, and she's 38, white, short and a bit thick with huge tits. And I have a 22 y/o tiny hot asian girlfriend already, but she doesn't know how kinky I can be.

This is how it all began. I started watching interracial porn years ago, then eventually cuckold porn before about a year ago going on to sissy/tranny porn. Soon I started watching the "hypno" videos and started getting really turned on by them. After a while of watching them I went and got a little beginner buttplug and started using it myself. That wasn't enough and eventually I was looking for guys on craigslist to hookup with. I was always telling my girlfriends how to suck my cock, so I wondered if I was any good at it. I found a guy and he said he loved the oral then fucked me pretty good ... after that I was looking for a guy online about once every few months. I had sex with my girlfriend all the time but also liked getting fucked. Meeting online took too much time and eventually I went and got a bigger and better dildo to use myself.

I've had the dildo now for about 6 months and can use it pretty well learning how to cum on it from prostate stimulation. So I don't have any physical attraction to guys, don't like to kiss or anything else intimate, but my fantasy of a bisexual MFM 3sum with a down woman has grown. In hopes of finding a woman I made a post on craigslist. That post was much longer than this is but it basically said how much I liked both sex with woman and getting fucked, but not the actual intimate gay sex stuff.

This lady replied to me about how much she's been getting off on gay porn lately. We started emailing, then texting. It was all sorts of dirty stuff about what we liked. And now she's coming over tonight for hours of fun and sex. What she's really excited and looking forward to is getting to rim me and play with my cock at the same time. Then she wants me on my hands and knees while we 69 so she can also fuck me with my dildo while sucking me and I'm eating her out. HOT! I told her she'd probably make me cum so quickly like that and that I'll even cum twice. Then she really wants to get fucked in the ass too.

Best part is I'm setting up my camera hidden away to record the first part of however much it can get tonight. And if tonight goes well, she wants to consider watching me get fucked and have a 3sum. Then, she's also mentioning she likes women in bed, so maybe someday we'll have a MFF 3sum. She gets very turned on by the idea of 3 people all into each other and what we can do.

Last, a warning: Don't watch those sissy hypno trainers unless you really want to do that! I'm tall, masculine, hung, never left a woman unhappy in bed, but now I also shave my ass to get fucked.

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@confessions
13 Mar 2014 8:25PM
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Some time ago, I met a guy online through sheer chance on Omegle, and we hit it off. We lived far apart (different countries, I in the US, he in Canada) but we still talked lots and grew together.
Recently I had the opportunity to stay in Canada for a while, so I chose his hometown. Needless to say, we hooked up, majorly.

That first night, our first date, I went from a champion virgin to 3rd base in the space of a couple hours. He couldn't get me off - I'm just lacking the libido and sensitivity, I guess - but we took turns sucking each other and exploring bodies, then settled in for the night.
The next morning, I sucked him again, but this time I was determined to make him cum. He eventually finished himself off with the help of my mouth on his balls, but I'm glad to say as soon as I saw his first drop of cum I immediately starting sucking out the rest right into my mouth. I suckled him and fondled his balls while he came until my mouth felt full of cum and drool. I moved up him and shared his cum with him in the most passionate kiss yet.
Showered, played with his ass, fingered a bit. I was afraid I was going too fast, so to speak, but man, he's sexy-fine with the most beautiful ass, I just couldn't help myself.

Just last night we finally had another real date - schedules and work kept us apart - and it was awesome. Cut to the bed again where we're teasing each other and stroking and just getting naughty, then we went to sleep.
We woke up and started messing around again, when I decided to do something I never thought I'd do: rimjob. That's right, I licked, sucked and kissed his hot little ass, and tried my best to get my tongue inside him. I'm here to tell you that a clean ass tastes... alright. It tasted like the rest of his body, I guess. I tried to finger his wet asshole again but he was just too tight, so I backed off. I guess if my fingers were a bit longer, or if his ass was a little more relaxed I could've hit his prostate, but as it was it was just a new sensation for him, one that wasn't terrible, but also not gloriously erotic.
More shower, he tried to suck me again with mixed results. Mixed, because while it felt good enough, I just couldn't cum like that. I love that he likes to tease and pleasure me and try to swallow my less-than impressive 5 inches, but I guess I just can't get off that easily. Ohhhh welllll. At least I taste alright.

I guess there should be a confession or two in here, so here it is:
First, he's turned me mostly gay, with his beautiful body and dick and amazingly delicious cum. I'm not full gay, I still like boobs and the female form, but I think I'm more likely to suck a cock than eat a pussy.
Second, I encourage everyone to at least try to rim someone they love. The sounds he was making, the whole "you're so dirty!" talk the whole time, the taste of his anus... I don't think he was super turned on by it, but I know I'll be doing it more in the future, so he can get used to it. Also, it's a great way to help relax the anus for more ass play. And if you're curious, I didn't get sick or anything like that from it. If the ass is clean, it's safe for a spit-shine!

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Anonymous
@confessions
18 Aug 2023 6:06PM
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so this happen the other day my wife gay friend stop by to hangout. my wife has been in Germany on business' for the last two weeks and he figured I could use some company. We went out to dinner and started hitting our usually hangouts. I knew it was time to go home I started feeling no pain. I got us a uber I was no where near able to drive. We got back to the house I said I was hitting the sack and he could sleep in the spare room. He said he was going to shower first. He was in the shower and I needed to piss so I knocked and ask if it was ok. He says sure, I go in and he opens the curtain and I see he was fully erect. He says I was going to jerkoff and would you like to join in. I said never done anything like that and I give it a try. We go into the bedroom I get naked and we start playing with our cocks while watching gay porn all of a sudden I am hard as rock and he starts playing with my cock and and then he starts to lick and suck my cock and next thing I know he has a finger in my ass and then two and he is massaging my prostate. I told him I was going to cum and I exploded and filled his throat and he swallowed every drop. He says to me now it is your turn to make me cum. He flips me over and starts licking my hole and tonguing me deep and I am moaning and my cock is getting hard again. all of a sudden I feel something pushing against my hole I think it is his finger. I can feel it spreading me open and next thing I know he is balls deep in my ass. He starts out slow in and out and my cock is dripping cum not precum cum I mean cum. He picks up the pace and all of sudden I am shooting streams onto the bed and I him he say I am cumming I can feel him shooting streams of cum in me and it is warm and now I am really lubed up and he just keeps fucking and I am dripping cum again and he keeps fucking for another twenty minutes which seem forever and I start shooting cum again and fives minutes later my ass is filled again and it is just pouring. My ass was sore but the next morning he fucked me again and we fucked each other all day I sucked his cock and swallowed every drop. I hope the wife stays another week. he took a picture of my asshole I posted it!

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@random
19 Dec 2016 9:49PM
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Wanna know how us gay guys have rock hard abs along with a rock hard cock?

Get yourself an Aneros prostate massager, strip naked, and stick it in your arse. Feels good right? Don't get carried away yet though.

Now get out the yoga mat and lay on your back and start doing crunches. After about 200 or so straight crunches -- no stopping for breaks, your body will reward you with a massive eruption of cum all over your body and face, leaving you groaning and shuddering uncontrollably in ecstasy.

Do this a few times a week for a few month, and you'll be ripped!

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Anonymous
@confessions
24 Aug 2018 3:02PM
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One day I came home from work, there was a small box on my porch. My wife orders far too much shit online. I brought the box in, it was addressed to me, not the wife. I opened the box and there was a note in the packing "surprise babe!" signed by my wife. I pulled it out an it was a prostate massager. First off, I was like hell no - nothing is going up my ass. There was some lube in box too. I put everything back in the box and texted my wife "that isn't going to happen." All I get back from her is a smilie face winking emoji. She comes home from work later on, I'm chilling on the couch and she starts getting frisky, touching my balls, stroking my shaft through my shorts. I get hard and she unzips my pants and starts going to town on my cock, first slow and then faster and faster - I can feel the back of her throat! My cock swells in her mouth - but I have some weird hang up with BJs, I can never ever cum! I get to the edge always, but it never happens. She pulls my shorts all the way off and I feel her finger starting to probe my ass. She has never done that, I was a bit freaked out. She takes my cock out of her mouth...
"Just lay back and relax, I read on a website guys have the best orgasms if the prostate is massaged. Just let me do this."
"I'm not gay babe..."
"shut up and relax," she said putting my dick back in her mouth, sucking up and down as her finger eased in to my ass... It felt uncomfortable as fuck, not going to lie. My erection started going down and she noticed.
She stopped sucking, "I'll be right back."
She comes back naked, with the lube and the prostate massager, takes my dick in her hand and gives me a full deep kiss - her tongue is all the way in my mouth. She slowly works her way down to my cock, again - starts sucking on my balls and then I feel her tongue probing my asshole. That felt really good, then her mouth wrapped around my cock and I felt her lubed finger start poking inside me. The prostate massager was next. It took a while to get in, I was too tight - never ever did that before. It was very uncomfortable! But then she started to hit a spot that made me feel... warm at first. I started to quiver, an after a while I blew the biggest load I've ever blown.... My entire body shook! I couldn't stop cumming! My wife couldn't hold all of the cum in he mouth!!!! She was choking on my cum!!! IT came out through her nose!!! I'm telling you, if you haven't tried to find your male G spot, do that shit guys. I confess - I LOVE IT.

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Anonymous
@confessions
03 Jul 2014 3:53PM
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Omegle is awesome! A quick side note: I'm in my late 20's, straight, and an ex gf got me into like prostate play, but I have NO interest in men. If you haven't tried it, you don't know what you're missing. And I don't want to hear anything about gay here. I just don't care. Just like there will be no pictures here.

So just a few nights ago I decided to go on omegle and play with some of my toys. I usually do unmonitored video section and hope a girl pops up. I usually have a bigger dildo out and girls always do a double take when seeing it. Then about two thirds of the girls usually want to see me play with the dildo and get fucked by it. It's fun having a young girl watch and be amazed at it. But eventually it get old with 99% of the others just guys with dicks out. So that's when I start going to the texting section where you can pick topics.

For a while at first I started using the topics bi and lesbian, but I found most girls in the lesbian section have no interest in a guy with toys. That's when I started doing just bi/bisexual topics. The first thing I'd say to every match was "I'm over here playing with my toys (;" and ask for their asl. If it's a guy, on to the next, but if its a girl the fun begins again. Usually I say I'm 18-21.

There's a lot of younger girls there, but this is about a girl I found who's 18. She told me her asl and she ended up being in the same state as me. We narrowed it down closer and closer, until turned out she lives in the same city, about 20 minutes away! I kept an image of the chat record and will post a copy of the conversation, but to summarize it, I told her I was 21 and she really liked the idea of me playing with my toys, and that even she'd like to ride the the long 12" double dildo with me. I tried to get her to text me but she didn't want to give her number out to a stranger. So after we talked a bit more, I asked if she had a toe we could talk on later. That's when omegle crapped out on us with "technical difficulties"!

I was a bit pissed at omegle there but hoped something would happen. I kept scrolling through new partners, pasting my "playing with toys" line, and after a few minutes, I found her again!

Our second conversation went very differently. I found out she has a beautiful name, and from there it went from talking about her little vibrator, to anime, and 50 Shades of Grey. And by the end of a much longer conversation, she decided she was pleasantly surprised and that I wasn't a stranger anymore. She decided she wanted to text now.

That was three nights ago I believe (it's hard to tell because we've been staying up texting til 3-5am each night) and we've been getting very sweet and flirting with each other. Then last night, when she had a sleep over with her cousin, little sister, and a friend all in her bed, our texts started turning into heavy sexting. But she couldn't do anything for being squished between two girls in bed. By the end of the night she was telling me how wet her pussy was for me, that she was in agony not being able to relieve herself, and when she knew how excited she was getting me, she begged me to cumm for her. I did, and after some more flirting, she wanted me to cum again for her, telling me how much she wants to help take care of me and clean me off with her mouth and that I can only imagine what she's going to do when she finally gets real a taste. After she made me cum twice last night, she starts talking about how turned on she got me by thinking about "taking and spanking her naughty ass" (her words) and now I can't wait to find out what's going to happen next.

Now we've been flirting more and more heavily over the days and building up to getting together. She really wanted to see fireworks together and get a fourth of July kiss but we're both too busy that night, so instead now she can't wait for what I told her would be our own personal private fireworks that we could make. But I still have to tell her I'm ten years older than her, not three, and I'm still wondering if she'll love it or hate it. But from our texts, I think it's going to be a good surprise for her.

I'm going to go through the two logs of our chat next and edit out a few details. Then I'll post them for you guys to enjoy too.

But first, just how awesome omegle is... Another girl I met that same day there, that I won't go into much detail about, told me she was a virgin and a bit young, and she was very curious to see what dildos looked like. I toe'd her some pics and videos, telling her how good it feels when she finally get to stretch that pussy and ass to take something. At first she was curious, then said it looked kind of gross and dirty seeing anal for the first time, but shortly after she's asking me to teach her where her clit is and show her more of my toys... now that's a awesome toe log that I'm saving with pics that motherless won't approve of. d:

And that's it for now!

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Anonymous
@confessions
31 Mar 2010 1:22AM
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Just got my first blowjob from a man tonight.

The worst part is it was entirely due to boredom on my part.

Work was unusually slow tonight. My main obligation was basically to sit around for the last half of the night, just in case something happened. Got bored as Hell and started reading STUFF magazine. The pics gave me some ideas, but there was no way I was going to score pussy at work, that wouldn't cost me my job. Then to Craig's list personals, which got me more excited. I can't believe some of the shit that gets posted there. Eventually I got myself rather excited.

Then this fat little gay guy from another department comes wondering in. He always hits on me. He's creepy and even if I was gay I wouldn't be attracted to him. Of course he notices the hard on I have, and immediately goes into how he would suck every last drop of cum out of my balls. So I'm like "You talk alot of shit. Prove it"

5 minutes later were locked in a conference room, where no one should go anywhere near at night. I'm sitting on the table with this guy sitting between my legs. Staring this dude in the face I started losing my erection. Men don't do anything for me, and this fat little dude is no poster child for porn. I'm starting to have second thoughts and he's not so eager to let me leave, unitll he's given it his best shot. I lay back and start imagining one of the hot secretaries we work with and he starts working his tounge up and down my shaft.

I get hard and he starts giving me some pretty good head. He keeps changing his technique but he seems fond of ticking the tip of my cock with his tongue. As long as I don't look at him I can enjoy myself. He keeps playing with my balls. I don't think I've ever had any woman pay so much attention to my balls. It was weird, but it didn't hurt, so I let him do his buissiness. Then he started tounging my ass hole. I got a little worried what he was planning when he started tounging my asshole, and I think he sensed it so he went back to sucking my cock.

He stopped fucking around at this point and started taking it deep. I started thrusting and getting loud and he ontop of it. He had one arm across my stomach, one hand cupping my balls, and his head bobbing up and down on my cock like his life depended on it. I tell him I'm getting close, and he takes that as his cue to start twisting my nipple with his left hand and slide one of his fingers up my saliva soaked asshole. I would have hopped off the table if he weren't holding me down. I like a little bit of pain. The nipple thing worked. He hit my prostate with his finger and I cummed and twitched like I was having seizures. He sucked me off for a few more minutes after that untill I got paged.

While I was getting dressed, he asked me what were the odds of me returning the favor and I told him slim to none. After that I gave him a pat on the head and went off to answer the page.

When I got back he was gone. Which was a shame, since I was eager for some more head.

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