Growing in confidence: Planning header image, Black and white photograph of two kneeling naked ladies, one arm each wrapped around the other with the outer arms reaching over to touch hands.

Growing In Confidence: Planning.

Growing in confidence: Planning header image, Black and white photograph of two kneeling naked ladies, one arm each wrapped around the other with the outer arms reaching over to touch hands.
Photographer: Dark Lion. Model: Dr Lovelace and Me

Following my first trip to the boudoir, Sir enjoyed my tales of the fucking machine and doxy wands. He is always very careful not to objectify me out of context, so we didn’t discuss his sexual gratification at my pleasure that evening. However, he has always taken great joy in celebrating my growth. In this situation I was growing in confidence, planning future play dates, starting to understand and relax into my enjoyment of women. By shedding the labels and embracing the hedonism I had made a huge leap forward and he was thrilled to see this.

He has never been one to rest on his laurels, rather choosing to maintain momentum. Although he was due to be out of touch for a few weeks he had something for me to work on in his absence.

Task confidence – N will let men worship her

You with one other woman are to safely arrange a Bukkake. This must involves numerous men who will cum on you and the other woman.

A big task, one that would prove challenging on many levels. The difficulty for me was seeing myself as exciting and attractive, two words he wanted me to relate to. He also wanted me to be centre stage, which is tricky for a woman who has always been happy for others to shine brightly from their pedestals while I dance discretely in the shadows. My growing in confidence came from his meticulous planning!

Whatever the problems I faced with this task, ultimately it was one that ticked a hell of a lot of my boxes for all sorts of reasons. During the early days of our dynamic he had asked me what I would be willing to do for him.

As I hadn’t mentioned it he asked me about “Bukkake”.

I must admit needing to google the word, but the search engine told me it matched a long held desire! In case you don’t know, here is a brief introduction:

Bukkake is a sex act in which one participant is ejaculated on by multiple participants. It is often portrayed in pornographic films.


I had six weeks to complete this task. To find a woman, a space and enough safe and respectful men to make it worth our while. He wanted me to be centre stage, covered in cum because they found me exciting and attractive. If I could see that too then I would gain confidence at a time when this area was somewhat lacking.

But where does one start when it comes to planning this kind of adventure?

And did I know any ladies that would be keen to join me for the ride?

I’d had a couple of meets with the red shoes by this point, and my task came up in conversation one evening. He said she could join me, but she said she wasn’t ready. As she was very new to swinging and kink I wasn’t surprised. Perhaps, due to my own nerves, I was relieved not to have to provide hefty emotional support while planning my biggest task to date. A time when I would likely need to be able to show my nervous excitement to whoever joined me.

Scratching my head I kept mulling it over, until the solution presented itself at a munch.

CC and I were chattering away over dinner while the munch buzzed around us. She had an important birthday that year and we discussed her plans for a “year of celebrations”. It turned out she had a bucket list, and this included bukkake. Welllll… she and I had been friends for quite some time. I knew she had been swinging a long time before arriving at kink, and in that moment I knew she was the woman to join me.

Laying out my task, Sirs instructions and my timeline, I asked if she would like that as a birthday present? She didn’t take much convincing, and together we checked our diaries for dates that would work for us both, within the time frame.

But where would I find a safe place?

I wanted to be able to share the experience with Sir, so the ability to record bits and have photos taken was imperative. And I knew I needed to be safe, which kind of ruled out a hotel room. If I was going to be responsible for CC and myself, I would rather have a male figure around just in case male ego took over. Yes, for this task I was allowed to let them fuck me. But only if I wanted them to. And I wanted to explore bukkake without penetration. And so, if any of the men decided that they wanted to fuck us it was important to have a presence.

Perhaps the obvious option for me was to ask Pie.

He has a gang bang group, his lads aren’t people I want to fuck but if they were safe then I wouldn’t mind being on display for them, in exchange for getting covered in spunk. I trust Pie in many ways, and his home is set up as a sex palace. I know, he had overstepped some boundaries, but open and honest communication is my forte and we had moved on nicely. As he had often offered me the use of his house for Sir and myself, or if I needed somewhere safe for solo meets, I knew he wouldn’t mind my request.

What I hadn’t expected though was him to decide exactly how the party would go. In the blink of an eye (well, the time it took him to respond to my text) he had taken my task, set by my Sir, and come up with a scenario of his own to kind of fit the brief. His reply was clear… Me and CC at his house. His fucking machine, his gang bang group. I’d be DP’d by them all and by the fucking machine.

Errrrr… NO!

This was my task. If I was going to be growing in confidence, the planning would be done by me. For me! The first thing I did was mark his response unread. That gave me some breathing space to contact Sir. I was cross with Pie for muscling in on Sirs ideas, and my task. All I’d asked was if I could borrow his house and him to be on hand, just in case. Sir’s response was simple.

“Familiarity breeds contempt. You still have plenty of time to look elsewhere”


He always knows just how to talk to me, ease the puzzled frowns and make me chuckle my way out of troubling thoughts. In this case he cleared the way for me to reply with clear boundaries firmly in place.

I explained to Pie that his idea wasn’t in line with my plans.

While he was happy for me to use the space, I wasn’t comfortable with his input (I couldn’t risk that male ego rearing it’s head from the man who was supposed to be on hand to support) and said I would find somewhere else. If the task was to help improve my confidence I was already achieving his goal!

Back to the drawing board, but not for long! An event notification on Fetlife gave me an idea. And I kicked myself for not thinking of it sooner…

However, you’ll have to wait until next time to find out where I was thinking…



Did you enjoy “Growing in Confidence: Planning” so much you can’t wait to read more? Perhaps you’ll enjoy this post while I write the next part of this story: Personal Growth Is About Unlearning Old Limits.


  1. I think you should become an events manager! u really had your work cut out here – fascinating post – and I would rather have spunk on me than in me 😉
    The image is amazing!
    May x

  2. I look forward to reading your finale. It’s unfortunate that the situation with Pie took the turn it did, but your Sir was correct in his reply. I hope the confidence is still growing.

  3. I love it when I come to the points where our moments are shared , makes me reflect on what wonderful times we have had .

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