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I have been thinking about trying to bottom, but the only things I've had in there are fingers and didoes. I wanted to know if it is really pleasurable or a mixture of pain and pleasure. Please be honest.
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Curious1972 Amateur Jackinchatter

155 posts since 2017-05-13
62 year old bisexual male from Southern Colorado
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It's really all about preparation. I clean myself out with a warm enema beforehand. Then foreplay with lubricated fingers and toys. This gently loosens your sphincter muscles and prepares you for more vigorous penetration. I find that if my partners well lubricated cock is inserted slowly, allowing the anal muscles to relax, there is almost never any pain. And if there is, it's minor and quickly morphs into pleasure. I love being a bottom and getting fucked! Just make sure your partner is in tune with your needs and goes slowly ... at first. Once mine gets me going I love a long hard fucking with him plunging into me balls deep and then almost all the way back out ... over and over and over. Your partner can/could hurt you ... especially if he has a very large cock, but not if you proceed at your own pace. My first couple of times were not completely enjoyable, but I soon learned to relax and enjoy it!
It's all good!
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jjonn3 Professional Jackinchatter

1053 posts since 2015-04-23
bisexual male from California
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Don't try with anyone with a thick cock.
Take it slow.
Lots of lube.
Make sure he knows it is your first time and to take it easy.

There will be some pain - but once you are past that...
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Thank you.
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Thank you.
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slow steady as you go!ass
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BarbieBoy Novice Jackinchatter

13 posts since 2023-07-30
39 year old
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First Anal at 13, hurt like hell but after was very proud I got through it. After that I wanted it once a week.
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jackbird Skilled Jackinchatter

686 posts since 2017-09-21
66 year old bisexual male from Dover /Rochester New Hampshire
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66 years old here my first time was a couple of years ago and loved it right away. Been a cocksucker since I was 14. I have used lots of things over the years to fuck my self. Mostly used cucumbers and still do. It was like a game to see how big I could take. Had some big ones up there. Met a guy we were sucking each other for a few months. One day made sure I was well cleaned out handed him a tube of lube asked him to fuck me he got on my back slide right no pain. He started out slow as I jerked my cock. I then told him oh yes fuck me. He gave me a couple playful smacks on the ass. I told him oh I love it. He grabbed my hips and fucked me hard. I said that?s it harder oh fuck yea. He tensed up I felt a warm feeling inside me and his cum was leaking out as he pulled out.
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TommiBiGuy Amateur Jackinchatter

139 posts since 2023-05-15
20 year old bisexual male from Ohio
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For me it was painful at first.
I was so nervous I couldn't relax.
It did get more pleasurable the more we did it.
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ILickDick

ILickDick said:
Hit me up via PM for trading young boy <16 pics. Session available for trading.
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wankcum Novice Jackinchatter

59 posts since 2020-05-26
47 year old bisexual male from sussexish
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Hi i like being a bttm 1st time i tried it i went to an older guys house he kept talking about poppers he was much more experienced than me; i turned up and he had some hot polish porn on i remember seeing a fat guy fucking a slim guy hard;he gave me some wine then told me to strip before i knew what was going on i was naked and on my knees sucking him off; i was like wow this is really hot he told me to bend over and to stay like that; he went into his bedroom and came back redfaced and a bit wild then just stuck his cock in me it hurt so much i jumped out of my skin thaen he just wanked over me. The 2nd time i tried it was with a lovely kind guy who had a really small cock but took his time a fucked me good; you need to be opened up 1st to enjoy it but when you do its sooo good
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jjonn3 Professional Jackinchatter

1053 posts since 2015-04-23
bisexual male from California
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My first time wasn't great - we were teens and he came before he got all the way in.

The real key is lube - lube and more lube.
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