Jenny DeMilo’s Erotic Femdom Hypnosis

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.

SeleenaK_6532sI 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.

Includes: subliminal triggers, back tracks, anal servitude, oral servitude, cock control, anal stretching, ass obsession, heightened arousal, brain washing
This one seemed to suit me quite well since I already lean in this direction.  Anal sex and large, no  .. make that huge .. insertables, fisting, strapon play and a well-hung gentleman or two already have a revered place in my life.  I’d never turn down a size challenge and love that brink of orgasm for a long period of time feeling that only someone with a prostrate gland can totally understand.

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 seswebsite samplesion, 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.





Gal’s Spring Fling

an early morning walkWhat is it?

Gal’s Spring Fling is the premier transgender event  in Canada.  It’s primarily a Gender Mosaic (Ottawa ON) event, with assistance from Xpressions (Toronto ON).  I’m a member of the latter.  It’s more of a social event and less about support and education (which is perfect for this girl) than some of the other events.

When is it?

It’s an annual event held late in May.

Where is it?

Gananoque (pronounced gan-a-NOK-way) Ontario, or “Gan” to the locals, is the host city for this event.  Gan is known as the Canadian Gateway to the Thousand Islands, a scenic area where the Great Lakes, and more specifically Lake Ontario, empties into the St Lawrence River, which connects the lakes to the Atlantic Ocean.

sitting outside my room

My Thoughts

Although this is closest trans event to where I live, the timing has always been difficult for me.  But this year, the planets aligned and I was able to attend.  And what a pleasant surprise it was!

What really set this one apart for me were the people .. the attendees.  Around 60 of us were in attendance including a relatively large number of significant others.  Friendly?  Yes!  This was, by far, the most approachable group I’ve encountered at a trans event.

Of those in attendance, a couple were friends, I had met a couple more and had chatted online with another two so it wasn’t like I was among strangers, even on the first day.

The town is just starting it’s tourist season so it was pretty quiet.  I sensed almost everyone we encountered were locals, and they were quite welcoming.  A couple of the girls mentioned hearing comments they didn’t exactly appreciate but none were humiliating or confrontational.

The Ramada Provincial Inn was quaint.  Motor Inn style.  Park outside the room; enter the room directly from outside.  The rooms were on the small side of average size but were comfortable and clean.  Not exactly SCC-luxurious outside restaurant at the hotel but they were fine.  The room rate was very good and a full breakfast was included.  Grouping of fifteen or twenty attached rooms were scattered around the rather large property so depending where your room was, the walk to the restaurant or bar  could be substantial, especially in heels and bad weather, but it certainly was not a problem for this girl.

The weather this year included mostly sunny, mild days with rain showers late in the afternoon or evening.

I arrived the day before the event started, got checked in, unpacked and met a small group of girls in the lobby area.  We all went to dinner at an Italian restaurant in town called Riva.    Although dinners were included in with the conference registration, Tuesday night’s dinner at Riva was not but it was fabulous!  In my opinion, the nicest dinner I had all week.  Classy, a wonderful menu with fabulous food and top notch service (although a gentleman a few tables from us suffered some type of medical emergency during dinner and required EMT’s and transport to the hospital.  Hope he’s okay!)

The other (included) dinners were good too, but the service wasn’t exactly impressive at either the Glen House or Ivy Lea Club.

The 1000 Islands boat tour was awesome.  Dinner on the boat while traveling around a gorgeous part of Canada was great fun andtook up most of a sunny and warm afternoon.  Just perfect!

Although I didn’t attend, the free makeup sessions in the cosmetic department at Shoppers Drug Mart were well received.   And the fashion show girls had a great time selecting clothes and getting fitted at Sear in Kingston ON.

Side note about the fashion show;  the organizers like to get first time attendees to participate in the fashion show.  I was to be one of the eight but while talking with a girl I had just met, I sensed that, although she was on standby (the 9th girl in an 8 girl show), she seemed more keen than me to get involved.  So I spoke to Amanda, the organizer, and opted out so the other girl could jump in.  And it worked fantastically well.  She did a great job and had a lot of fun.

Besides .. the event I really wanted to participate in was the Best Legs Contest.  And guess what?  I won!  Quite an honor considering thegetting the Best Legs trophy from Samantha other leggy entrants but my leather short shorts, Wolford hosiery and Santana stilettos surely helped.  I get to keep the trophy at home until next year’s even when I’ll get my name engraved on it for posterity.

The other conference event that always gets a lot of attention is the evening at the Legion.  Royal Canadian Legion Branch 92 puts on a big dinner and dancing evening for us every year.   It’s our best opportunity to mingle with the locals.  Dinner was good and so was the band but honestly, I can’t really get into an evening of dancing and drinking.  And having to drive back to the hotel afterwards adds another challenge.

Finally, the Gala.  The big dinner dance on the final night.  This one was held at the host hotel and is was wonderful!  Food was great and a wonderful slide show during dinner reminded us of the fun we had all week.  And I was able to have a whole lot of adult beverages but again, didn’t dance much.    And, of course, dance music makes it difficult to chat (Listen to me?  Do I sound like an old lady?  haha!)

But honestly, playing footsy under the table in a dark piano bar is more my speed these days.  Did enough dancing when I was young and even survived the disco years so Iwith my friend Pauline‘m just not interested in that anymore.

To this event, I wore my long black skirt that’s “slit up to here”; a sheer black turtleneck under a purple satin bolero jacket  and black sheer to waist pantyhose from  I know .. stockings and a garter belt are my usual legware but there would have been no way to hide my stocking tops with the rather extreme slit skirt and it just didn’t seem like the slutty look was right for this one.

In Summary

GSF is a fun event!  Relatively inexpensive; extremely friendly people, a nice laid back feel, a good motel and held in a beautiful little town.  I came away from this event with more new friends than I ever have at any event in the past.  Did I mention friendly people?

early arrivals group photo after the boat rideYes, if transportation between events was provided I could have hit the wine a little harder.  Yes, registration was a little confusing.  And yes, me and a small handful of others would have preferred a little less dancing but, all in all, this event is a great time.  Although attendance growth is usually a sign of success, I hope this one continues forever and never grows.  This size was just perfect.

My spouse accompanied me to this event and she had a wonderful time too!  So if you’re thinking of attending, and have a supportive spouse, please bring her or him along.

A Special Thank You

It appears that circumstances this year left a single girl with the responsibility of organizing and planning the entire show.  Amanda Ryan, your selflessness and organizational skills were greatly appreciated.   Not only did you do so much yourself, you were totally sweet during the whole event.  I’ve never come away from an event in the past where I felt like I needed to hug an organizer (and never let go) but I did this time.  You’re a special lady and I hope you have the energy to continue to do this forever.

And to my non-Canadian friends, come to Canada!  You’ll have a great time.