Back to Back Sissy Slut Sessions

I know there’s some of you out there who aren’t interested in sissy play and some of you that are interested in play with sissies. I had the amazing opportunities to have two back to back sissy sessions last week.

My first sissy, who I will keep an anonymous for now as she hasn’t picked out her official feminine name, was meeting me for the first time. She wasn’t dressed up, but I could tell her feminine side was present psychologically.

She was a beautiful slut who told me she has been with many DOMS before, but never experienced a sensual session. She requested for me to wear the shirt in my photo (below), and I surprised her when she walked through my condo door.

She told me a little bit about her life, and she was very open about her feminine side. I totally loved her confidence and trust that she had already placed in me, even though we had only known each other for a total of 5 to 10 minutes.

She laid on my massage table allowing me to work my magic hands all over her feminine body.

As per my usual routine, especially with first timers, I started it with a firm and light gentle play, here and there. As her feminine side was coming out, I could see her responding to my touch even more intensely. The more response I got, the more teasing she received. Even though there was no physical domination (and punishment) in this time together (as she shared with me), I certainly took control with my touch and verbal commands.

Her bum was up in the air, begging me to play with her boy pussy. I continued to tease around the area, ignoring her non verbal cues on purpose. I knew she was craving for me to be inside of her, but this is something that she had to wait for.

I directed her to flip over, and I can tell that her clitty was excited and dripping wet. I continue to tease her girly erogenous zones: boy pussy and clitty simultaneously.

I positioned myself between her thighs, straddling the massage table having her legs on top of my legs. She was moaning and squirming with every touch, again begging for that G spot stimulation. I didn’t want her to get what she wanted right away, she had some more waiting to do to earn that orgasm.

I started to tell her about my other sissy, Alexa who knew that this sissy was visiting me that day. Alexa was begging me to play but I told her that my newbie wasn’t ready yet. I shared this with my newbie during our session and she said this is certainly something that could be in the cards for future exploration. After all, it would be the first time that she sucked a real cock for a woman.

After some tickling and brushing outside her external boy pussy, I filled her up with my finger allowing her to feel every centimetre and every inch of my penetration. Her clitty was dripping wet at this time and I was playing with it just as a girl needs it played with.

I could feel her G spot enlarging and getting close with every touch. I wanted her to feel the full release of her orgasm, so I started stroking her faster and faster giving her permission to fully release.

As she was catching her breath, she shared that this experience was different than what she’s experienced with previous dominatrixes. Obviously there was less punishment and more sensuality. She shared that she was very calm and felt an intense level of pleasure and relaxation.

After she departed, I surprised my next sissy Alexa by greeting her with this same t shirt at the door, and she surprised me by walking into my condo, fully dressed head to toe, looking like a slut she was born to be.

We went into the bathroom together to get some photos done before we started our session. Of course she allowed me to post these photos. After all, she’s more than just a cock sucking sissy slut. She’s liberated sexual being who wants the world to see her while maintaining full discretion.

She wanted some more photos of her, and so I found the best positions to take them in. Here are some of them below.

She wanted her pussy to be nice and wet, a reflection of her dripping wet desire for me to give it to her.

Alexa pulled out her cock and she wanted me to fuck her. It’s been a while. She was feeling extra slutty today and she was ready to suck a real cock for me if I had one waiting for her.

At first, I gave her a nice massage, teasing her and slowing opening up her pussy with my fingers. She pushed her bum back so I can go deeper as she wasn’t waiting for me to tease her any longer. She was now in the doggy style position. She asked me to take a video of my finger going in and out of her pussy so she can have some masturbation incentives for later to relive this experience. As I was fucking her, her clitty cock was bouncing back and forth as I was moving in and out.

She wanted to switch positions and so I grabbed my wedge and encouraged her to lay face up on my couch. “Fuck me just like this” she begged.

I slipped on her harness with her purple cock, and it fit with a glove. I put my cock inside of her and fucked her slowly and sensually, exactly as she likes. She can be freaky but she needs a good slow entry.

After sometime, she wanted to ride me. I retrieved my white chair and magic wand. She straddled me, still wearing her heels and rode me like a cowgirl. I took out the magic want and put it on her clitty. She was ready to cum. As she approached orgasm, I removed the wand and started stroking so she can enjoy the orgasm all the way through without overstimulation. It lasted for a good minute.

Next week, we are setting up a Gloryhole session with another favourite of mine. Alexa may or may not bring her girlfriend with her to suck his cock together under the table.

We will see what future endeavours bring.

Posted from my X account

I have the pleasure of meeting a lot of sissies and sometimes back to back sessions aren’t as common. I decided to share an experience through this blog. Although the sessions look very different on the outside, the impact, desires and fantasizes overlap and, in some cases, can be very much the same. Perhaps I’ll talk more about this topic someday.