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I have put a finger or small object up my arse before when wanking but today I used a soft dildo (floppy not rigid) with a condom and plenty of lube. WOW i hit my spot and can honestly say it blew my mind.

I didn't actually cum but the feeling was so intense, it felt like i was cumming when i wasn't, I can now see why guys like anal. Its not something I will do regularly, but when I am alone and have time to enjoy without rushing I will defiantly be exploring again.

I now have a bit of a tender feeling but expect that is just either air inside where I went in and out, or just a bit sore as nothing has been that far up before.
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Mmftaster69 Novice Jackinchatter

35 posts since 2020-12-15
bisexual male from Maryland
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Sounds hot
Makes me wanna try it
Mmftaster69
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jjosh Amateur Jackinchatter

311 posts since 2020-11-23
64 year old from florida
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yes.. anal play does spice it up for sure.. i started with a small prostate toy.. then i moved up to we vibe vector... really luv the vibe.. for sure.. intense orgasms
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Workoutbud Novice Jackinchatter

82 posts since 2016-12-02
69 year old bisexual male from Florida
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dmtove..... you stopped too soon. Next time, keep up the pressure and see if you can milk a prostate orgasm from that dildo doig its job, massaging that prostate. It will be very intense....a hands free orgasm.
Enjoy yourself...life is too short. Cum often.
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TwoBiFour Novice Jackinchatter

75 posts since 2020-01-02
56 year old bisexual male from MI and IN
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dmtove said:

I now have a bit of a tender feeling but expect that is just either air inside where I went in and out, or just a bit sore as nothing has been that far up before.


Most likely your prostrate is a bit swollen - it will (should) go away. It will happen until you get more use to it. Just wait until you can cum without touching your cock. It's about as close to a female organism you can get.
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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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Yep discovered anal play as a teen at age 14. Tried mom's dildo at first it hurt trying to get it in but can't explain why keep trying till it popped in.
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InPanties Amateur Jackinchatter

420 posts since 2018-06-24
43 year old bisexual male from London
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love anal play, first thing for me was finger, then best buds cock i just love it, all ex gf's & current have a dildo selection i have bought them ;-) , then no problem around having them at home
A lover of used Panties, tiny TITS & Taboo
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Dan_Glebitz Skilled Jackinchatter

668 posts since 2009-10-03
73 year old curious male from UK South
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It's a nice enhancement to a good wank. Snag these days, not a thing I want to be caught doing and thanks to Covid restrictions I no longer get the place to myself

I started by feeling around the hole with a lubed finger before taking the plunge. I progressed to using a lubed vinyl glove and can ease two fingers just about. Upgraded to a sharpie in the glove and that to me is dead right, not too intrusive and gets to where it needs to be.

Great thing with the glove is having something to hold onto so nothing disappears.
If God created anything better than wanking - he kept it to himself.
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Bateman Novice Jackinchatter

7 posts since 2021-04-21
62 year old bisexual male from Canada
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I worked my prostate at times but unfortunately, couldn't get any pleasure from it (only got the feeling of peeing).

From what I have read, it's the most intense and long lasting orgasm a man can get. I wish I could reach to that stage.
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philinlondon Amateur Jackinchatter

204 posts since 2011-03-31
66 year old bisexual male from London / East Herts
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During lockdown I bought an Aneros Helix Trident and have been enjoying this. I then added a WeVibe Vector (which is a vibrator).

Both are not too big and with a bit of water based lube slip in pretty easily and target the prostate.

I had never had any anal experience before this (and am 62 and only discovered bi bud cock fun about six years ago - via this site!), so it was a totally new ball game for me.

I have enjoyed reading up and learning about the joys of Prostate massage. While I have not experienced long dry orgasms yet, I have had hour long sessions where my cock has been leaking pre-cum and I have been shaking with some great feelings. I have finished my sessions with a hand job and the power of those orgasms and the amount of cum that is generated has been fantastic. The pressure of the toy when you cum seems to help pump up the volume.

As a novice, I would recommend having a go at prostate play as great extension of your jacking fun.

If you want to chat about it PM me.
Phil in London
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Dan_Glebitz Skilled Jackinchatter

668 posts since 2009-10-03
73 year old curious male from UK South
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Bateman said:
I worked my prostate at times but unfortunately, couldn't get any pleasure from it (only got the feeling of peeing).

From what I have read, it's the most intense and long lasting orgasm a man can get. I wish I could reach to that stage.


The trick is not to use anal play as part of your orgasm, your cock will lose some sensation and the cum load might not be that intense as the pleasure from within takes over - well it does for me.

So I play with my cock with lube then add some to the rear entrance before slipping something up there, then I just squeeze the end by the glans and concentrate on the anal play. When I'm ready I remove whatever I'm using, run more lube onto my shaft then have a slow gentle wank and enjoy the spunk.
If God created anything better than wanking - he kept it to himself.
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Oh yes having no alone time is the greatest challenge at the moment. I will try the sharpie and glove, as those won't look out of place and raise any questions!
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firecrotch55 Amateur Jackinchatter

343 posts since 2011-12-25
72 year old curious male from nys
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Have been into my anal entrance since late teens. Have only had a couple of prostate stimulation orgasms but the overall sensation of massaging my walnut while having a wank makes the orgasm so intense that I loose my breath.
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mikewesten39 Amateur Jackinchatter

319 posts since 2021-04-17
63 year old bisexual male from New Hampshire
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I have used a finger and a few objects. Really enjoy the feeling and stimulation. Now looking for a JO buddy that will put the real thing in me!!!
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keithgnabor Amateur Jackinchatter

399 posts since 2013-12-07
65 year old curious male from south carolina
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yeah such toys can be addiction they're so pleasurable.
now i need to get another one after hearing these stories.
stick to seat and ride!
keithnabor usually
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