As I recall, I first became aware of Ms DeMilo back in the days of backseam dot com, a forum for nylon enthusiasts. Later, we both had clip stores on the now defunct clippette dot com. My earliest recollections of Jenny was that she was a very sensual woman, classy, articulate, intelligent, creative, strong and compassionate.
I also knew she did erotic hypnosis and that she was, and still is, at the top of the craft.
I was recently given the opportunity to select anything from Ms DeMilo’s catalog for review. This is my review of her Ass Bitch hypnosis session, but first, a little background.
I have had no prior experience with hypnosis nor do I even understand the concepts totally but maybe this is a good thing. It helped me enter this new world with a totally open mind.
I was concerned that my headspace .. the tgirl thing .. would clash with what Ms DeMilo offers and I found that it did to some extent, but only in selecting an appropriate session. Looking through her catalog, there are a number of titles related to the “sissy” experience and, of course, dressing in women’s clothing has no humiliation factor for me. I also can’t relate to being a gay man or forced bisexuality. But it seemed that most everything else was something I could get into.
Most of her work is in mp3 form but there are also “assignment” files in text form and short videos too. A lot of her hypnosis offerings include a sample audio file. The samples give an opportunity to hear her voice, her inflections and the background sounds.
She and I both felt that I would enjoy reviewing an audio hypnosis session. So on to my experience.
I selected a session called Ass Bitch based on the following description:
Listen, learn, be trained and turned into an anal whore, a real ass bitch. Be programed to be aroused by being trained to give up your ass and take what ever is dished out. Dished out to your soon to be stretched out ass. You cant stop yourself from the desire to be a fully trained, greedy, reedy ass bitch. Go deep into a trance, hear the triggers, the deepers, the subliminal back tracks and be programed and trained by powerful femdom hypnosis to need, crave and want to be transformed into an ass bitch, under my control. You wont be able to resist my hypnotic voice and implanted triggers.

I waited for a time when I had a clear head and was certain I would not be interrupted during my 18 minute session. With glass of wine in hand, I turned the lights down, put my best headphones on and sat down to enjoy the experience.
I never touched the wine.
The first thing that struck me was her voice. Oh. My. God. Total perfection in this context. Firm, sexy, trustworthy and really just a beautiful voice on any level. And she was speaking to me! Not to just anyone who bought this session but to me .. personally. That’s how it seemed.
Inside my calm exterior is a person that’s always wound up and her voice quickly helped me to relax. And relaxing made it easy to put myself into the place I think I was supposed to be.
Hypnosis equals real relaxation. I wasn’t aware of this. But for the balance of the 18 minutes, I listened to her speak to me. A strong yet soothing voice in a soundtrack that contained pulsation, echo and comforting sounds I couldn’t identify. I embraced her suggestions; found myself nodding subconsciously as she told me I would crave the feelings of having my ass filled with larger and larger objects. That I would crave being stretched and filled by huge cock. Although there was suggestion that I would get a huge erection thinking of large things in my ass, huge didn’t happen for me physically (the tgirl affect, I assume), although I did find my hand in my panties and I was quite content to leave it there, stroking. I was wet and my state of arousal was quite high.
I listened to the suggestions that I would have cravings, and that they would come to me at any time or place, and this just seemed so “alright” to me. At one point, I became aware that I was clenching to the pulsating rhythm but I don’t know how long I had been doing this and if it persisted until the end.
At the end of the session, she gently brought me back from where I was relaxing and, to some degree, I felt refreshed.
Will I listen to the session again? Absolutely. Would I do anything different to prep for the session? I don’t think so. Will I be looking for lasting effects from it? Yes, and I welcome them.
Will this turn me into an “Ass Bitch”. Probably not. I’ve been halfway there for years.
I recommend this experience for my tgirl friends who have submissive leanings and are sexually attracted to women and are either into strapon play or are curious about play with men. And to the open-minded guys out there … particularly the guys who admire trans girls like myself .. take your openmindedness to the next level.
Experience this! You just might find the final piece to your own personal puzzle.
Thanks for following along with me on this new experience. I do hope you enjoyed the little change of pace.
Now I’m off to explore that special shelf in the toy cupboard that’s home to my collection of huge dildos and butt plugs. *winks*
Jenny DeMilo’s website can be found by clicking the banner below. There is also a banner and link to her site on my Links page.
Learn more about Miss Jenny
Blog: jennydemilo.com
Twitter: https://twitter.com/jennydemilo
Mistress: mistressdemilo.com
Studios: eroticfemdomhypnosis.com • clips4sale.com/39472 • http://www.niteflirt.com/jennydemilo#goodies
Hmmmm, interesting. There are few hypnosis samples on Youtube … I must say, I enjoyed your review. I also enjoyed the suggestive nature of the so called “hypnosis” as much as you did.
In my opinion, these recording are designed to put you in the right mood for sisification or ass play or whatever the subject suggest. It is the perfect tool for the men who wishes to explore a wider range of sexual practices.
Like you said, it is pleasant to use for the curious, novice and experienced person, but I also doubt that the hardcore straight, manly man would even stand a chance to be magically converted to the blissful lifestyle of anal play and feminization.
Oh well, their loss !!!
Liz love for all.