Anal Play is Pleasure

IF done correctly and carefully, anal training can turn into anal pleasure in no time at all.  There is this sweet spot in your anus called the prostate and if you rub it the right way, you can have a mind-blowing orgasm.  Start slow.  Perhaps you might experiment with a lubed finger and just see how far you can insert your finger.  If this makes you a little uncomfortable, it’s best to be aroused as you are doing this.  So, go ahead and stroke a bit, then explore!  We understand it can be scary but you can do it.

Three Rules of Beginning Anal Training

  1.  You can never have enough lube.  Seriously.  Never!  Go with a LOT.  The slicker everything is the better it will feel, I guarantee it.
  2. Relax and breathe.  Concentrate on taking it slow and letting things happen.  It will become more pleasurable, I promise.
  3. Have items on hand for clean up.  Towels, baby wipes, etc.  Also, a little pre-preparation is always good if you’re going to have a long session.

Anal Training With Two Mistresses

Mistress Delia and I have had the pleasure of slowly training a wonderful man while he explored the world of prostate play and anal penetration.  We had such a wonderful time with him.  Recently, he bought a wonderful new anal toy and decided to take it on a “Virgin” voyage.   

This is part of his email to myself and Mistress Delia.  You can read the first part here:

Our anal training sub went on to watching some European porn in his exploration with his new anal toy.

Well, watching the video I was slowly rocking front and back on the chair feeling the dildo slide up and down an inch or so rubbing against spots inside of me I never knew I had.  Needless to say, I was very aroused and very erect.  When it came to the part of the movie for the first sex scene it was a 3sum with Monica, another blonde woman, and a man.
The two ladies started out very sensually enjoying each other, my ass clenched with its own accord around the dildo and I started to rock front and back, leaning forward and backward.  I had a drop of pre-cum escape from the tip of my throbbing, yes throbbing, it rarely does that, penis, I felt it slowly ooze out as the ladies pleased each other orally.
When it came to the part where the ladies were giving the man a sensual blowjob, I put some lube on my fingers and I slowly started to stroke my penis in time with their tongues on his shaft and head of his penis.  When their tongues traveled the length of his penis my fingers mimicked their movement on mine.
When their tongues circled the head of his penis, with one finger I slid it over the head of my penis, and when they kissed and sucked on the head and down his shaft, I closed my hand around the head of my cock and slid it up and down, all the while the pre-cum mixing with the lube, almost a bubbly cream.
When the man started to fuck one of the ladies the other would position herself in front of the mouth so she can receive oral sex from the lady being fucked by the man.
That is when I moved forward on the chair making the chair seat slide forward and the penis dildo inside of me slid deep into my me  I gasped, then moaned in pleasure, then I slid backward, and the way the seat slides forward and backward, the penis slid deeper into me as I slid back.  It felt so incredible and filling, I unconsciously moaned in pleasure again.
I then slowly mimicked the man fucking the one lady in her vagina.  It was so intense I stopped stroking myself.  I could not keep up the rhythm on the screen of his penis sliding in and out of her pussy and my hand on me, as I slid the seat forward and backward.
Then the man positioned himself behind Monica Roccaforte and slid his penis inside her ass.  When he did this I moved suddenly forward and rocked forward at the same time, grabbing onto the handles in front of the chair, designed just for that purpose.  With both hands on the upright handles. I started to fuck myself anally as he fucked Monica anally.  I was moaning in time to her, without meaning to but I was.  As I was fucking myself with his rhythm, inside her I was also rocking as well on top of the sliding chair seat to get deeper penetration.
At a certain point as I gained rhythm in time with the man fucking Monica anally, while she was performing oral sex on the other woman, I let go of the handles let my thighs do the work as continued to fuck myself on the chair, my left hand slid back down to my cock and I was stroking in time to Monica’s tongue kissing, tugging and sliding in and around the pussy lips of the other lady.
I came so hard a stream of sperm squirted out of me and landed on my keyboard, the cum just coming out of me.  It has been such a long time for such a sexual release.  I actually grunted and moaned when this happened. Monica came at the same time, and the man quickly withdrew and came against her.  All this time the inside of my ass was clenching and releasing against the dildo, on its own accord, I guess trying to milk it.  But that just added to the intensity and joy of my orgasm.
I just sat there gently rocking back and forth in slow gentle movements, feeling my ass still involuntary clench and release, clench and release, clench and release, almost in time with my heartbeat, just enjoying the sensation, the feel of my penis slowly softening as the inside of my ass was softening with the clinches.
I felt like I shard my orgasm with Monica, and I felt the same pleasure of having being made anally loved to as she did, that it was intimate, sensual, consensual, erotic, and safe.  Feeling a dildo penis slide in and out of me where I control and be pleasured.  Even when I stopped the movie, and I slowly stood up, even the feel of the dildo that slid out of my now hot, wet sticky bottom felt good, and my penis in response twitched again.
Just enjoying the warmth of the full-body afterglow.
That was only the first sex scene within the first 10 – 15 minutes I think, the movie is at least an hour-long if not longer!
Mistresses Delia, and Tia it is through your words, encouragement, kindness, tenderness, and support that I was able to explore like this in a very safe, sexual adventure.
I felt like both of you were here with me watching and approving.  The both of you “de-virginiated” me anally, if that makes sense.
So in my thanks to both of you, I wanted to share my first experience with both of you as a humble form of gratitude for what your words shared with me.  This experience would never have happened if it was not for both of you.
 Anonymous Emoji
Isn’t that just the best email?  I am so pleased to be part of this man’s training and even more pleased to share this experience with Mistress Delia. So, if you think you might enjoy this type of training, you know what to do, right?  Yes, yes you do!