Merry Cocktober 🍆 and Happy Hallo-Weiner 🎃 (Part 1)

I met with a person last week, who we shall call Mr. NTL (Never Too Late). I’ve had the pleasure of knowing him for quite some time now. Winter is coming, and there are many trips to be planned, so therefore a visit was executed before it was time to escape the cold - and luckily we both had the time to accommodate.

When he first reached out to me several months ago, he shared that the blog I wrote many months ago “It’s Never Too Late” resonated with where he was at in life. He has the privilege of living a long and very full life with many years of wisdom on this earth but, from what he shared, he felt like he held back from experiencing the spectrum of what sexuality and exploration had to offer. He has shared one story several times of an experience with a couple, and he has relived this throughout his life, but he wanted more than just this one time. He wanted the space to explore further, to discover parts of himself that he may not ever had been aware of or perhaps parts of himself that he knew were always there but never had the pleasure of meeting beyond that one experience many years ago.

The first time we met, he shared his desire for a bi experience. Sure, he could’ve met with another man one on one, but it’s not the same as being directed and told what to do by a strong yet caring woman, such as myself. I believe I fit the description of what he needed and fantasized about to take the steps for further exploration.

After our first visit, he shared that he was ready for the bi experience for next time but I always give others some time to reflect. Taking this step can be daunting, and choices can be made minute to minutes, which I can appreciate. Our second visit came around, and I asked him if he was still open to the idea. He said it was up to me, but I truly didn’t feel like the time was right. I didn’t think that this was a decision I could make too far in advance, this soon in our meetings without it feeling organic.

We had several visits filled with several hours that lead up to the big Cocktober celebration last week. He trusted me fully, and I feel gracious when I’ve earned that trust. I never feel like others saying it right away is enough for me. I feel like I need to do more to earn it - and that I could never do enough no matter how well I know a person.

He arrived a little early and I was running behind - as always - but he patiently waited for me with kindness and grace - which I always appreciate and reward with more attentiveness and time. When I gave him the green light, he buzzed me and walked in without knocking as instructed. He walked in wearing his immaculate clothes and shoes with not a speck of dirt on him - as per his usual. I brought him in for a hug and he shared the positive feelings he experiences when he is walking down my hallway and first walks through my door. It is a familiar feeling that many people have shared - my place is the representation of non-judgment, sexual liberation and an opportunity to drop the masks we are required to wear in our day-to-day life and breaking down gender norms and expectations society places on men. Perhaps it’s the lighting, perhaps it’s the music, perhaps it’s the smell of cleanliness, purity and femininity. Perhaps it’s my presence or all of the above. Whatever it is, I’ve created a world that I’ve envisioned and I’ve never felt so successful to give this to people who I believe have earned it in a world that can feel so cold sometimes.

He made his way over to the coach and started to get undressed as per our usual. He shared with me the last time that we met I mentioned I would want to make him wear my panties, so I dug a beautiful white pair out of my closet that I knew would fit him - which I wanted to wear first. As athletic as I look, you’d be surprised how many of my clothes I can share with anyone - male or female. My goal is comfy, stretchy clothes with a little bit (or ‘a lotta bit’) of allure.

After he was fully undressed, we started embracing. I removed my dress wearing nothing but the white panties, marinating them to whatever we decide to do with them in the next moment when the time is right. Little did I know what was to come and that they would end up on the floor with no physical use during this session, but rather a psychological representation of what lead us to my next idea of what was to come during this time spent together. I felt like the time was right and I wasn’t out of line to bring this up. I believed I earned my trust with Mr. NTL and my thought would not be misconstrued as any ulterior motives.

Alexa is my favorite duo partner for bi curious and “forced bi” sessions (not forced but you can imagine what I mean). I’ve taught her well to be my sissy - to be submissive, to be sensual, to be feminine and yet bossy at my direction. When we have our victim on the table, everyone in the room knows who is in charge and who is running this tight ship. It’s always helpful for me to get acquainted with new personalities to understand what limitations and fantasies exist so that I may direct the session appropriately. Everything that I instruct is done with consent and pleasure.

I chat with Alexa almost on a daily basis so therefore, I knew there may be a chance I could invite her into our session last minute. Before I reached for my phone, I told Mr. NTL that I believe today was the day that he needs to meet Alexa. He agreed with excitement and giddiness, like a “kid in a candy store” as he said several times, knowing that today was the first day of pushing more limits. “I fully trust you” he said. “I am grateful for your trust and I would never betray that” I replied.

I sent Alexa a text and ask her if she could head over. I know sometimes she finds herself close-by so these last-minute requests are not unreasonable or unfeasible. She texted me back within five minutes. I saw the blue dots come up as she was typing to reply. “I’ll need 30” she said. “I’m canceling my appointment, getting ready and I’ll head over”. I shared the good news with him “she’s cumming” I said. “Oh boy!” he exclaimed with excitement, overlapping with nervousness. We had almost 3 hours left at this point so we had time to wait.

He asked me to purchase a sex toy for our session previous to this. I recommended a butt plug. During our last session, we had shared four hours over pizza, chats and sensual touch. He asked me to keep the toy at my place and I made sure I had it charged for our next visit.

I came up with a plan in the moment. I told him I wanted to make sure the butt plug was inside of him before Alexa arrived. This the plug also has a vibrator so we could play with the remote while we had him wait. Since this butt plug was a little on the bigger side at the largest point (quite small at the initial opening), we could take advantage of taking our time to successfully have it inserted slowly and sensually. Mr. NTL complied with my request to have him lay face down on my massage table.

I was tickling him and teasing him. For a man of many years of wisdom and experience on this earth, he is an excellent shape. I was admiring his strong legs and his cute butt. I was still wearing the white panties, and we looked so good in the mirror. I asked if I could snap a photo and he apprehensively agreed. I took photos from above his butt crack down his legs and ensured that I was in the photo from my neck down. There were no discerning features in the photo. He looked like he could be anybody in this world, which is always my goal. No faces, no tattoos, no birth marks and no scars.

I showed him the three photos I took, scrolling all the way to the left to show him there were no additional photos and then scrolling to the right, showi g him some of my personal photos to ensure that he knew I wasn’t snapping anything else without consent. I asked him if he would be comfortable with me posting them with this blog, but he told me he wasn’t sure. I told him he’s allowed to say no to me at any point and that I don’t find myself offended over anything.

To Mr. NTL: I will not follow up and ask you whether I can post the photos. I could tell that this was not a question you were ready to answer and asking you the same question may put unnecessary pressure on you even though I gave you permission to speak your mind. I will delete the photos at your request. If you want the photos or if you want me to post them to this blog, I will leave it to you to mention to me.

I had prepared a soapy bowl of warm water with a hot towel. I wanted to give him the experience of a body scrub without the commitment of a shower. I notice the pattern that he chooses never to shower, which is never a problem because he doesn’t have an issue with hygiene. I think it’s correlational with many anniversaries on this earth. One person I know hypothesized it could be challenging physically as our mobility changes over our lifetime. I’m worried about falls. Maybe it’s something else. But, as Mr. NTL shared of his new-found mentality in our new-found friendship, we had built a trust where he was open to me doing anything to him. He just wanted to give up control for once in his life.

I squeezed out the washcloth that I had prepared in the warm water and ran it across his back down his body. I had a second towel in my hand to dry him with each swipe so that he didn’t freeze. I repeated the pattern over and over while he shivered with pleasure, incorporating my light touch periodically and without warning. I brought the butt plug to the massage table with the castor oil I had warmed up. I needed something more viscous than my massage oil as we had less than 20 minutes to get this butt plug in at this point. I didn’t communicate this countdown with him so no pressure was involved - except the pressure I would put between his cheeks as I was inserting this soft, squishy and well-circumferenced butt plug.

I slowly started to slide it inside, ensuring there was enough lubrication around the odor edge of his hole and lubrication on the toy as I slowly opened him up. I always recommend toys that are soft and squishy with a large base and a generous girth (if you can handle it). The width and length are different fits for different people, and because I knew his anatomy and his desire to be pushed, I found a toy that could vibrate, that was a good quality, squishy to touch, but not to thin and too short given that he’s a very tall person.

From my experience, the prostate, tends to be a little higher on those with more height although I can’t verify that this information is scientifically accurate at this point.

I worked the toy in, moving it in deeper, periodically pulling it out and lubricating the outside before inserting it again. I was opening him up slowly and, even though he told me I already earned his trust, I am conscientious enough to make sure that he remembers the way that I touch him to help him relax further. I’m not forceful. My goal is pleasure with the perfect balance of pain - not in the traditional sense, but rather the pain of shock experienced from achieving certain goals. Almost the same electricity we feel when we receive a spank on the bottom. We have used this book plugged before so I knew that with the right touch, patience and enough lubrication, we could successfully have it inserted.

We were at the largest point and I could feel the resistance. I turned the vibration to the lowest setting to increase the pleasure. “We’re almost there. Should I push it in?” “YES! I’m ready!” He said. And with a little extra pressure, it popped right in, creating a sense of relaxation once the external pressure was transferred internally and the butt plug touching his ‘P’ spot with the extra length earned through successful insertion.

I saw the familiar blue dots come up as Alexa was typing - “I have arrived”…

To be continued… stay tuned

(Which I will pair with a photo of my Halloween costume for your viewing pleasure)