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New2Bttm's Avatar
New2Bttm Novice Jackinchatter

8 posts since 2013-12-21
44 year old curious male from Terre Haute, Indiana
Just recently discovered this new excitement. I'm looking to learn all that I can, i.e. Different methods, tips & tricks, multiple orgasms, advice etc. it would be great to find a local guy that is into this and we could have regular buddy milking sessions

What's your thoughts?
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grunt3661 Amateur Jackinchatter

227 posts since 2012-10-05
40 year old bisexual male
I'm 39 and been getting milked since 18. The mature 50 something woman that took my virginity introduced this to me. I've been milked by my gf, men massage therapists. Love it. I tried to milk myself on cam for a guy but it didn't really work out.
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oldercuriousguy Novice Jackinchatter

56 posts since 2009-09-04
61 year old from western Pa
I sometimes use a 1 inch diameter candle with a rounded end to insert and then massage my prostate. It will often make cum dribble out. It can feel exhilarating and is a special sensation. I have also made other items for that purpose, such as a rounded end hot glue stick, a formed piece of soft plastic, etc. It can be especially awesome if your bladder is full and you have a raging hardon.
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anon4074 Novice Jackinchatter

57 posts since 2013-04-14
52 year old curious male from Nebraska
I have a small dildo, about 3/4" around, that is ribbed and especially made for prostate massage. Bought it at my local adult store and absolutely love it. It's flared at the base so no losing it up there. I would be cautious improvising with things like candles that can quickly slip up into you. That would be an embarrassing trip to the ER.
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I too just started into prostate milking started with just a vibrator and my wife bought me a Anrous prostate massager feels really good when getting head or cowgirl style sex
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jjerismo Novice Jackinchatter

30 posts since 2013-10-21
66 year old curious male from USA
I've loved anal play, solo of course for years!
I finally made my own prostate massager from the handle of a shovel.
Yes you heard me right. I made it long with a hinge in the middle of it for flexibility.
For me at my age I love slow play lying on my back and then some deep stroking.
I use both feet, left foot can either hold it still while I rock my body on it, or to push it deeper. Then use my right foot to push down in the center which makes the end of my shovel handle push up against my prostate.
BANG goes my orgasm!
Love cumming like this, just don't have enough quite time being married and all.
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alrightee_then Novice Jackinchatter

4 posts since 2009-11-30
40 year old curious male from arlington, TX
My gf uses an angled dildo with one of those bulbs on the end and it's amazing how much she milks me with it
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wgm00 Amateur Jackinchatter

435 posts since 2012-04-12
53 year old curious male from Central Cali
Hope you don't mind the long post....

I hadn't tried it up until a couple of years ago. I was a bit reluctant to try but this particular woman I went to (massage 'therapist') specialized in prostate massages.

She was very gentle, slow and explained everything before she did it. After a nice full body massage, on the flip I had a raging hard on, of course. She took her time, oiling me up (cock and balls) and then applying KY lube in my ass and her finger. She stroked my cock slowly as she gently pushed her finger in, very slowly. Then she held it there for a bit until she felt me relax. Then she started the actual prostate massage, she pointed her finger up and started stroking and rolling the prostate around. I was about to pop so I told her so, then she stopped stroking my cock, but continued with the prostate massage. Just having her finger wiggling in my ass was pleasurable alone, but working the prostate was intense.

After a bit, liquid just started oozing then flowing out of the tip of my cock, which she said was normal. At this point I was going insane with pleasure. Basically I couldn't hold back any more and I exploded. I was bucking around like a bronco, and when I started to cum she grabbed my cock again and stroked and fingered me until I was empty. She is really good love

As budget allows, I visit her every few months and it's sensual and mind blowing as ever each time.

Find someone who knows what they are doing. You won't regret it!

Note, I had visited other "therapist" prior to the lady mentioned above, who said they offered prostate massages but they had no clue. They think that by simply sticking a finger up your ass qualifies as a prostate massage. Obviously not so.

Do some googling, you'll see a lot of topics and discussions about prostate massages, some good, some bad experiences.

Let your cum fly!
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justanxious Novice Jackinchatter

22 posts since 2010-12-05
62 year old curious male from St. Louis MO US
The massaging of the prostate is like a gift to men in that you can get a lot of the sensations and juices of cumming and still retain the load for the big final orgasm. I prefer to use a chrome cigar tube larger may not be better in this case since the object is to get enough force on the prostate to get it to release its gold. Larger is always fun once you get past the pain of entry. As long as things are smooth with no edges or rubbery surfaces there is little worry. Nothing is not as good as two skilled fingers. Glass dildos and NJoy brand toys are also awesome, knobs and curves can be fun.
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SloStroker Enlightened Jackinchatter

3756 posts since 2006-08-21
42 year old bisexual male from Nashville, TN
I had a GF who would finger my ass while she blew me. Then she got a 7" dildo and fucked me with it while she sucked me. I would get me dribbling in no time and she was really good at controlling my orgasm. Some days when we had nothing to do, we would fuck and play all day but she would not let me cum. She'd spank my balls and tell me if I came she was going to hurt them bad. It made me so horny. Gosh, I miss sex with her, but she was bat shit crazy. Don't miss the drama.
If it feels good....it's good.
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plush Professional Jackinchatter

1388 posts since 2010-02-06
heterosexual male from USA
Not for me had more pain than pleasure. I still try from time to time with negative results.
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Smoothy Amateur Jackinchatter

248 posts since 2006-01-10
48 year old bisexual male
I use a basic Aneros massager and with patience, time and concentration can ejaculate whilst flaccid by just tightening and releasing my sphincter muscles. The feelings I get are incredible - better than a normal orgasm, and whats more after I've cum I can carry on wanking as normal! Double the fun!!strokestrokestroke
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jackwguyz Skilled Jackinchatter

838 posts since 2013-03-16
45 year old heterosexual male from New Hampshire USA
wow! so many innovative and dangerous tools to jam in your ass and possibly hurt yourself for the sake of cumming. nice! I was also thinking an old, splintery shovel handle would be good. I was thinking of dipping it in glue then a vat of broken glass for a real "kick" of pleasure. of course I would put a condom over it to be safe, I'm not fucking crazy! hopefully I won't bleed too much but as long as it feels good for a few minutes its worth it, right? I can't wait to start this project. so anyway, I'm in the market for a shovel from like 1930 if anyone has one. thanks. grin
A guy who loves to stroke!
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Smoothy Amateur Jackinchatter

248 posts since 2006-01-10
48 year old bisexual male
Now that would be silly.wink
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betterthisway Novice Jackinchatter

1 posts since 2014-03-04
58 year old bisexual male from Dallas
Just keep having sex in the missionary position and continue sticking just your head up your ass for the best results!
I wish I had a group to meet with nightly
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Index » Sexuality » Rainbow Room » Anyone else enjoy milking their prostate? Have some good stories to tell?