Sleepy Silly Boy

Sleepy Silly Boy


The sequel to my classic session Silly Boy has arrived! Enjoy this stroking, edging session while you rest against my huge, hypnotic breasts.

(3 customer reviews)
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Product Description

The sequel to my classic session Silly Boy has arrived! Enjoy this stroking, edging session while you rest against my huge, hypnotic breasts.

Once again, I use the power of my large breasts and the cliches of hypnosis to soothe you into gentle trance where you’ll find yourself mindlessly stroking and coming right to the edge for Tessa! come relax and be my sleepy, silly boy!


Release Date06/18/2014
Recording QualityStereo
Length in Minutes26:30
Background MusicYes
Subliminal LayeringNo
Post-Hypnotic SuggestionsYes
Topics/Fetishesedging, joi, guided masturbation, sleepy, breasts

3 reviews for Sleepy Silly Boy

  1. Matty

    The thing I liked most about Tessa’s prequel to this session, “Silly Boy”, was the imagery she created of resting my head against her enormous breasts. (Note: she may not have used the term “enormous” to describe them, but my psyche automatically inserts that word when Tessa’s breasts are mentioned) So you can imagine the delight I experienced when I saw she was releasing a follow-up session. Every time Tessa releases a new session I hope and pray that she will use her fabulous assets to take me deep into hypnosis for her. So of course I was hopeful for a full frontal assault from her in “Sleepy Silly Boy”. Instead, what I got was a lovely induction that had my head laying back onto her….you know….boobs at the very beginning of the induction. It was such a pleasant way to be led into trance. I won’t go into any more detail about what is included in this session because it has to be experienced first hand. I will say that if you want to feel good about being easily manipulated by Tessa, to be taken in by hypnotic cliches (in all of their most erotic glory), and to find yourself wanting to cum so badly, but only being able to stroke away mindlessly, then you will probably want to get your hands on “Sleepy Silly Boy”.

  2. sleepysillyboy

    like to listen a file several times before writing a review of it. Moreover, in this case, I wanted to be sure I loved it for the right reasons, and not only for the excellent taste of Tessa in the election of the titles of her files.
    And I do it.
    I love it because it maintains the charming of its prequel that calms my stress.
    I love it because Tessa´s breasts are the best place in the world to rest.
    I love it because I love to feel the contrast between my absolutely relaxed body and my aroused cock.
    I love it because I love to obey Tessa mindlessly.
    I love it because I love how Tessa plays with my desperation, denying me what I first want, to give me what I most want, pleasing her.
    I love it because I love to feel how much Tessa controls me.
    I love it because I love to feel how Tessa enjoys with my suffering.
    I love it because it´s Tessa. Soft and dominant. Wicked and caring.
    Thank you Tessa. Thank you, thank you, thank you.

  3. Andrew A. (verified owner)

    I just wanted to say that this session is one of the best things that’s ever happened to me in erotic hypnosis. Knowing how good this feels – to find that sweet ability to actually dive deeper and ‘stroke’ at the same time, but never get release – is frankly one of the truest moments for the body to find reconciliation with the mind. That submission that one feels in the mind is then one with the body – sleepy, silly and stroking for Tessa. This file, through it’s mode of ‘silliness’ teaches you how you want to embody this submission and always want Tessa’s influence and Tessa’s pleasure. Having tranced with this file several times now, I’m at a point where I so desperately find myself not wanting to get release, to feel this urge in between my legs even hurt a little, to feel that want, that transfluence of submission from mind to body – alive. Try putting this file in a Tessathon and see how this file will beautifully place you in complete submission. Love this session Tessa. Thank you so much.

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