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Confessions of men: first anal experience.
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Perhaps a cheeky finger up the bum when the wife was giving you a blow job. Maybe safely in the privacy of your own bedroom all alone. Possibly a strap on or for the more sexually adventurous an actual cock….
How were you introduced to the pleasures of anal and where has it taken you. Time to confess  |
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By *omRachCouple
over a year ago
Wirral |
Rach was the 1st to ever visit my bum hole many many years ago and since then it has been on the receiving end of tongues and toys also.
It has also been introduced to a couple of guys too and both got to get their cocks inside it. |
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By *lexV16Man
over a year ago
Welling |
Got along with a couple where wife after few meets wanted me to fuck her hubby. Through few meets when they become bi mmf I don’t remember how but I end up rimmed and fingered by her and eventually with her hubby cock up my bum  |
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By (user no longer on site)
over a year ago
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Started as a teen with whatever was safe to stick up there. Coincidentally this was the time I started dressing too.
Progressed from there to actual guys and girls fingers at uni and then a cock (and never looked back).
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Other than normal experimenting as a youngster, at age 19, an 18 year old best friend asked if he could blow me and that then led to us fucking each other.
Was an amazing experience even if he was huge.!
Been bi ever since.
It’s just sex and sexual attraction. I don’t get hung up on it. |
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Initially wasn’t sure what the fuss was about until I had a ex gf who was wild about all things anal. I was hopeful that I may be introduced slowly to it, my first experience happened on my birthday where I was cuffed, blindfolded and put on all fours. I kept feeling the slightest of touches hit below my balls and cock making me drip until I felt something I’ve never felt before.. two hands spreading my at the time tight ass making it open, she was very vocal and exclaimed that it was a lovely tight smooth hole before slowly licking around the area causing me to twitch and throb. It continued with a slow but sensual tonguing, which was incredible.
It’s safe to say our anal play escalated, and now I am a huge fan of it all  |
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First time was receiving oral from this girl. Saw her put her finger in her mouth and felt it on my bum hole.
Then felt it go in must have had it in up to here knuckle lol. She just fingered it along with the motion of the blow job it was really nice explosive orhasm
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"First time was receiving oral from this girl. Saw her put her finger in her mouth and felt it on my bum hole.
Then felt it go in must have had it in up to here knuckle lol. She just fingered it along with the motion of the blow job it was really nice explosive orhasm
"
Orgasm |
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By (user no longer on site)
over a year ago
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For guys that don't feel anything do you get any feeling of anykind of pleasure when you are full and it feels good to be empty?
Toilet wise that feeling.
It's a similar feeling.
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Can't remember the first time a woman fingered me during a bj but I love it. Various butt plugs are nice and I've got two awesome prostate vibrators. Rimming is nice occasionally too.
Taken a cock a few times - I like it because it's transgressive, but tbh the actual sensation is a bit dull. If anyone has a cock that vibrates, please message!
Love giving women anal but never really fancied buggering a bloke. I've inserted a cheeky finger in a fella whilst other hot stuff was happening, to see if I fancied it, and will probably do that again. |
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It's not a confession in the slightest, as it's no different to anything else.
Started exactly as you say, with a finger. Has been two fingers when the woman was a little tipsy (and me too!). That was great, but not something I'm rushing to do.
Now, I'm happy for a guy to fuck me, if he's got the patience to go in slowly.
And Alice gets VERY turned-on watching me with her vibrator up there. |
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"For guys that don't feel anything do you get any feeling of anykind of pleasure when you are full and it feels good to be empty?
Toilet wise that feeling.
It's a similar feeling.
"
I get the feeling of something in there, but zero pleasure from the feeling, its just like "OK now what" |
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Many years ago I was enjoying a 3 some with a married couple where I was balls deep in the wife in the missionary position...... felt my bum being lubed followed by the hubbys cock entering me, not painful at all and thoroughly enjoyed it...... Not looked back since!  |
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By (user no longer on site)
over a year ago
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"Perhaps a cheeky finger up the bum when the wife was giving you a blow job. Maybe safely in the privacy of your own bedroom all alone. Possibly a strap on or for the more sexually adventurous an actual cock….
How were you introduced to the pleasures of anal and where has it taken you. Time to confess "
Mr had a cheeky finger from an ex while she sucked him, he's always enjoyed anal since, despite being straight, then about 6 years ago despite not being turned on by anything mm based, he started living big cock / cuck porn which developed an interest in bi fun, which he has enjoyed ever since. But not kissing, caressing etc. Just wanking sucking and fucking. |
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Away on business in a hotel. I was cross dressing and feeling sexy in my lingerie.
Organised a meet with a guy. He came over. A BJ start went further and he gently took my virginity. Lots of lube eased his BBC inside me.
Loved it. Quickly organised another meet on my next business trip |
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By *iM4kinkMan
over a year ago
San Antonio |
My first time was outside in me and my friends elaborate for. We really did get extremely filthy for young boys experimenting. i was only a little older when i took my first adult cock in my ass. And by that time i had fantasized about it so much i had crazed desires to used and fucked. |
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By *zlakMan
over a year ago
Lowestoft |
When i was in my 20's a mate after a few beers told me he was bi, i told him i had thought about it and it turned me on. We want to his and after some play he asked if he could try it on me.
Lets just say i have not looking back since.
Even better if a wife is watching  |
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Confession submitted by DM:
My first anal experience was being told that a finger in your arse makes wanks better and so I tried it the next day told my mate he was so right! First rim job was as a laugh from a mate as a forfeit n first time being nailed was when me n a mate were messing about n he showed me a video of a lass taking a huge cock in her n said bet you couldn’t do that n so to prove him wrong I took his huge dick. |
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By (user no longer on site) 45 weeks ago
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Had a finger in the arse a few times likes it n ever the same if you do it to yourself, tried being pegged this year and not looked back what an experience
Would recommend to anyone |
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Confession submitted via DM:
Me and the Mrs saw a MMF threesome at a club night last month. At one point one fella was fucking the other as he was busy with his tongue on the lass. Me and the Mrs both found it a huge turn on watching. We talked about it a few times over the next few days and she decided it was her mission to get me ready for our next visit where she wanted to see me get fucked. We’ve used her toys to help me explore and get used to it (with plenty of lube!). I came home from work one day a couple of weeks ago and she was looking very naughty. When she came into the bedroom wearing a strap on that night I knew why. To be honest I’ve been loving it all. I’m nervous about our next club night but get super hard thinking about being in my back, a guy between my legs fucking me as my lass is sat on my face. I hope the fantasy lives up to the reality. |
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Hah. I knew that if I wanted to have pornographic sex, and realised that I wanted to be the one being fucked. So I practised with a dildo until I met a guy and... I realised that the psychological thrill of *being* fucked is something special. |
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By (user no longer on site) 45 weeks ago
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I was getting a fantastic blow job from a good friend of mine when I felt her finger making its way up my bum. She was a touch too foreceful and I asked her to take it out. I recently bought her a surprise Christmas gift--a medium size clear glass dildo. She was very happy with the results she got fucking my ass with it and so was I. We are on a journey and we will finally get to the point where she and I will be riding a double-sided didlo stuck up our asses while her pussy is impaled on my cock. |
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Self exploration.
Saw it in porn and wanted to try it so tried a finger.
Then have explored with plugs and other butt toys.
Now it's more when we decide to play together, either with a prostate vibe or plug.
Sometimes Mrs will slip a finger in, and has used the strap on (though that is rare)
I would do it more, but more than anything I can't be bothered with the prep
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First anal experience was first year of being cuckold and had just got used to being in chastity full time my gf inserted a plug and stated this is part of your uniform you'll be wearing this whenever my bulls visit from now on |
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Mine was a meet via Craigslist, met an older guy when I was maybe 19 and he was 50’s.
Had nowhere to meet so met outdoors, it was really underwhelming lol
I got him hard and rolled on the condom, lent against a tree and he slide in. It felt amazing if a little sore, he started to fuck me and after maybe 3-4 pumps he was groaning and cumming.  |
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Older guy, met online and agreed to meet. He was very forward and had me naked in about 5 mins from arriving. Thrown on the bed legs spread and being sucked I just let him do his thing. He very quietly slipped on a condom which I noticed when he walked to the bedside table and got lube. Daft at the time I didn’t put the dots together what he was doing as a bj from another man was pretty new to me. He then teased it around my hole and started pushing in. Really fucking hurt then eased of massively. He came in about a minute. |
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Confession submitted via DM:
My first time was with my army buddy I had seen he was close on fab and he had winked at me, i recognised his tattoos, dropped him a message and he said to come over to his room which was on the other side of camp, (I was a little d*unk and honry) I let myself into his room and he was there bent over jockstrap on lubed up, he said he had already been taking loads all night, dunno why but the thought of him being used and full of cum just sent me crazy I dropped to my knees and rimmed him he was cleaned shaved and I could see the cum start to drip out of him and on to lips and tongue, I then slid my cock deep into him and fucked like crazy I had never had my cock in a guys ass before it felt amazing, I came so hard and deep inside of him. He told me later that time he took 3 more guys cock that night. All army! |
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By (user no longer on site) 11 weeks ago
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Fingered by a fwb about 2 years ago whilst being given a BJ. Thought that was the hardest I'd ever cum but......then trained myself with butt plugs and she pegged me a few weeks later...then it was the hardest I'd ever cum when being wanked off at the same time |
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It started with a finger as you described whilst getting head from an ex many years ago, from that it led to a d*unken night where she ended up using her dildo on me.
From then on i openly state to future partners i enjoy anal play, rimming, fingering, toys etc.
The next move would be to be full on pegged |
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I was at university and had managed to pull a girl on a night out, I was fucking her missionary and she just licked her finger and slid it in my ass. At first I was unsure, but she started making loader moaning noises and telling me to fuck her harder as she was going to cum. Made me shoot so fast
I think I fucked her another 3 times that night and she loved fingering me |
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My first time was while serving a Domme. I was in stirrups and she slid a vibrator into me the first time, I absolutely loved it. This progressed in time to being pegged and I have never looked back  |
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First time giving was with my wife a few years ago, was horny and she was hungover and i was trying to have some fun and at first she wasn’t into it as she was hungover. I jokingly said if you do I’ll bum you and she just said go on then.
My first time with me bottom was years ago, Cannt say what age lol and how |
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"First anal experience was first year of being cuckold and had just got used to being in chastity full time my gf inserted a plug and stated this is part of your uniform you'll be wearing this whenever my bulls visit from now on "
was your prepare bottom available to her bulls ?did any take advantage, even briefly to demonstrate their dominance of you both |
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met a couple who i explained quite new to bi play but very open. as i was fucking her he was rubbing his cock on my arse hole fuck o was rick had and blew so hard now wanna find a lovely couple to take this further. |
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Confession submitted via DM:
My first anal experience was with a tv who just so happened to be someone who had made plenty of porn. I used to wank to her vids a lot so when she responded to a social media message and was keen to meet I had to visit her.
Upon arrival I was asked if I wanted to dress up and so I was dressed in stockings panties skirt and blouse high heels wig and make up which was an amazing experience in itself, I felt like such a slut.
She was all dressed up and looked and smelt amazing. She asked if I wanted to kiss like lesbians and watch in the mirror so our tongues entwined and it made me so horny watching us kiss. I couldn’t help but move my hand up her skirt and couldn’t believe how rock hard she was in her satin panties. It felt massive and as she pushed me down to my knees and pulled it out the sight of her huge cock was so arousing. It looked just as it had in the pornos id wanked to. Huge bell I could barely fit in my mouth.
She moved me to the hall way where there was a long mirror so I could watch myself sucking her. I pulled out my cock at this point and I was covered in pre cum looking at myself sucking this gorgeous porn stars cock. I looked up at her and asked if she would fuck me so she took me to the bedroom and told me to get on all 4s. The bedroom was a turn on too as I had seen vids of her in the very same room.
I wasn’t sure what to expect as I had never taken cock before and hers was 8 inches and so thick.
I asked her to be gentle and she was. She lubed me up and slowly eased her bell into me. She was very good, I didn’t feel any pain it was just pure pleasure as she now started to fuck me nice and slow at first but then she was banging it into me. I was moaning like a slut and could feel the pleasure right through my balls and cock as she pounded me. After a few minutes of fucking me she told me to cum for her as she grabbed my cock wanking me fast as she continued to fuck me it wasn’t long before my spunk was shooting all over the bed, was such an intense orgasm.
Afterwards she thanked me and said that I took her cock well. |
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Recently on a night out with a few guys and one started talking this girl who had pegged him and he loved ass play. Never really tired apart from on myself in the shower a few times ages ago and didn’t really do much for me. Anyway, back to the night out and managed to pull a girl and went back to hers, while she was sucking me off she sucked my balls, spat in my gooch and stuck two fingers into my ass, loved it. |
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This is an interesting strand.
My first was a woman I was seeing. She slipped a finger up it - it felt amazing. She must have initially used spit, but moved onto lube. She said we should try toys but never did, unfortunately.
She must have sensed something about me as she said she know I would be into it and that she thought I would enjoy guys doing that to me too. |
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By *ikilovesCCouple 10 weeks ago
village life, closest main town inverness |
"Started with finger then on to toys and strap on with the Mrs but only tried the real thing once but wasn’t very successful but really want to try it "
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Yup, started with finger, toy and then strapon with us too lol
Not tried the real thing yet though |
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Confession submitted via DM:
Anal play started with my ex. She was much more kinky and experienced than me when we met. Started with some rimming, then fingering me while she gave me a blowjob. I loved it. One day she pulled out a small dildo and persuaded me to try it. Again I fucking loved it and she loved pushing me to try new things. She broached the subject of going to a club and convinced me it would be fun. It really was. After a few months of going and having a lot of fun playing with others we found ourselves playing with this lad. Out of nowhere she said she wanted to see this lad suck my cock. He was game and to be honest she was definitely in charge so I went with it. This lad had skills and I was loving it. She was kissing me as this lad sucked my cock and I was teasing her down below. Then she looks down and tells him I love to be rimmed, and tells me to turn around. Obediently I did and bent over the bench I’d been leaning on. He wasted no time and got right in there. It was much more forceful and eager than when she rimmed me. She squeezed in front of me, her back to me and reached down to slide my cock into her and started rocking up and down my length as this guy kept teasing my arse with his tongue. I was in heaven. “He likes a finger in there too” she told him. Next I feel this guy sliding a finger into my wet hole. He fingered me a bit then went back in with his tongue. Then two fingers which felt great. “He likes bigger things in there too” she said with a laugh. “Put a condom on and tease his hole with your cock”. I was on the verge of saying no way to this but then she started really working my cock and turned her head round and whispered that she was so turned on. Next I feel his cock teasing my arse crack and I just go with it. I reached back and felt his cock. A decent size but probably not much bigger than the dildo we’d used. He’d slipped on a condom and lubed it up. I was too far in now so I just went with it. I felt him guide his cock head to my hole and just let out a long “fucccckkkk” as he teased my hole. She stopped riding me and turned to look at me, a very mischievous twinkle in her eye as she watched my reactions. Slowly he kept pushing in a tiny bit until I pushed back a little and his cock head slipped into me. I couldn’t believe I was doing this and just froze. Then she started riding me again as this lad slowly slid his cock into me and started fucking me. A couple of minutes later they were the ones frozen in place as I pushed back and forwards. Back to ride his cock and forward to fuck into my lass. Absolutely incredible. I shot my load a couple of minutes later and pulled off him. He whipped on a new condom and slid into my lass when she invited him in to churn up my load inside her. An incredible night that was definitely a turning point in my sex life. I’m not with her any more but I’ll always owe her for opening my eyes and expanding my horizons. |
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Until i met my Domme, anyone who tried, even the narrowest of pinkies, couldn't get me beyond the feeling of needing to poo.
One day, while i was tied and gagged, She was engaging in some psychological play and scaring me with a butt plug, and it slipped out Her hand, going most of the way in. Wasn't allowed it as a limit after that because i could handle it  |
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A partner suggested trying it so I gave it a go. She wanked and sucked me while inserting a well lubed finger. It was very uncomfortable and I thought she had a whole finger up there but turns out it was up go the first knuckle of her little finger.
Didn't bother again. |
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Bi night in a club I was bonking the wife in a hot tub when I felt someone touching my bum hole next thing he slipped his finger in as I bonked her.
My wife loved me telling her what he was doing. |
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I was 26, gf was 46. We were out shopping in Lakeside, she told me she had special plans when we got back to her flat. Nothing was said but I knew what she intended to do.
She tied my wrists to the bedhead with scarves, got out the lube and a vibratory and proceeded to give me a bj while using the toy.
A mind blowing orgasm followed that I've never got close to again. I felt like what I presume a woman feels like after a real bone shaker orgasm. |
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By (user no longer on site) 2 weeks ago
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It was a long time ago when I had my first anal experience I was still a teenager. I was with my best mate at the time naked swimming in a creek then we started fooling about and it happened and I’ve never looked back. |
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A Fabster friend asked me if I’d ever been ‘milked’ before? I said I hadn’t, then on our next play date she introduced me to her 7” vibrator and told me to get on all fours, and just ‘relax’ lol. She definitely knew what she was doing, using lube, fingers then the vibrator (which slipped up there rather more easily than I imagined), and a short while later, omg! The most intense orgasm I’ve ever had, like a ‘whole body’ orgasm, and the biggest pool of my cum ever…..  |
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