The Day You Discovered Things Up Your Ass Was Enjoyable!

OK, so it's doesn't rank up there with THE "first time" but for me it was a shock how good it felt when an older woman I was fucking in college introduced me to the joy of receving a prostate massage while being sucked off. Up until then that place had been a pure exit but she was looking right at me with my dick in her hand when her lubed middle finger centered on my ass and snaked inside. "Hope you like this better than my husband" she whipsered as it curled into my prostate. Needless to say, it was the start of a beautiful relationship.

Saw (and fucked) her thru graduation when her hubby took a teaching position at another college. She was kind enough to introduce me to vibes, bullets, plugs, dildos, strapons and even four of her fingers before I cried uncle.

When did you first find this an enjoyable activity? Presuming, of course, that you did!
Still waiting.......
Her name was Nicole and I was trying to get in her ass and she beat me to the punch! I cam so hard I thought I injured her! Oh to be a teen ager again, hard to believe it was 19 years ago and the path that it has allowed me to explore over the past 19 years!
cumalot's Avatar
It was Mid December of last year with Ms Athena.....she explained to me how she would do the Prostate Stimuli so that there wouldn't be any surprises and that I would be comfortable. She began with some lube and put a condom on her finger, lubed it up and ever so gently began the rub my ass hole, the whole time massaging my cock with the vibrator. I felt comfort knowing that she is a nurse by profession and felt at ease with her as well. As she found her way in and found the button she was seeking, she slowly but deliberately began massaging the prostate. I felt so many sensations that were new to me and felt sooo good. I wish I had tried this a long time ago. After trying to hold back as long as I could I let go with the most awesome and intense cum I ever had, cum went everywhere her chest, tits, face, hair, every where. Since then we have had more explorations of dildo's, dongs, vibrators, strapon, and plugs to name a few....It's all good and it has been well worth the exploration. I never thought I would ever allow this before, but I'm sure glad I did...and it only gets better.
Ms. Athena's Avatar
Yeap, nothing like have a good olo prostate massage between friends...................lol
jsparrow's Avatar
Any suggestions: books or websites, on how to do this reasonably well? I know a wonderful provider who has tried this with me twice but it hasn't done a thing for me...just makes me feel "stuffed." I don't have a hang-up about anal play (DATO, TUMA, TUHA are always on the menu) but this particular massage sensation has eluded me. Help?
Any suggestions: books or websites, on how to do this reasonably well? I know a wonderful provider who has tried this with me twice but it hasn't done a thing for me...just makes me feel "stuffed." I don't have a hang-up about anal play (DATO, TUMA, TUHA are always on the menu) but this particular massage sensation has eluded me. Help? Originally Posted by jsparrow
Check out Tristan Taormino's website www.Puckerup.com She's been one of the acknowledged leaders in writing about safe anal play for years.
DallasRain's Avatar
FishGuy13's Avatar
I had an ex about 10 + years ago lightly rub on the outside of my anus, with a wet finger and I'm pretty sure her tounge but she did not go inside. I think it was about 5 or 6 years ago that I had my first taste of the hobby land with a wonderfull now retired lady who only did FBSM. She was at the same time slow and careful but also quick enough not to give me much time to think about it until OMG That feels AMAZING! Since then I've had some providers do ok with it and a few do pretty good, and very few to blow my mind. Every time I think I am ready to try more (perhaps a strap-on) ... life happens.
Ms. Athena's Avatar
FishGuy Dallas Rain is headed your way............
shortblkguy's Avatar
In college at age 18, hot Asian name Jeni inserted a finger while performing oral and worked it good until I blow. Been a fan since and have advanced to having quite the toy collection.
DallasRain's Avatar
Ms Athena maybe you need to make a roadtrip!!!
houston_switch's Avatar
Have tried it couple of times, but has not yet "rocked my world"...
Maybe I have not been with the correct person...
DallasRain's Avatar
Have tried it couple of times, but has not yet "rocked my world"...
Maybe I have not been with the correct person... Originally Posted by houston_switch
You should see Ms Athena!!!!!!
SlowHand50's Avatar
Getting with a prostate massage expert provider is near the top of my list. Especially after reading the posts here so far.