Right before I left for my Christmas break, I had the pleasure of meeting Mr. Submissive. We were talking back and forth and I was able to squeeze him in a few days before I scheduled my leave. He said he really enjoyed my blog but in particular this one and he wanted to try pegging. However, for first encounters (especially with those who haven’t tried pegging before) I always suggest we start out with a prostate massage so that you are relaxed, the situation has more control (my hand versus a dildo without any feeling) and I can also make suggestions as to the type of toy I’d recommend for our next visit. He agreed with my suggestion and recommendation of a neo-tantric experience with a prostate massage.
When he walked through the door, I could tell her was nervous. I pulled him in and hugged him until I could feel his heart rate slow down and his trembling dissipate. I showed him around my condo, and lead him to my massage room. He was excited but still fairly nervous. We chatted a bit and he took a look around my condo, imagining where I’ve taken certain pictures that he found particularly appealing and turned him on. I asked him if he wanted to remove all his clothing. I could tell he was shy but he also told me he wanted me to take control and so at this point I told him that choosing to not remove his clothing was no longer an option. “Take everything off and lay facedown on my table” I instructed him. He complied.
I started massaging him and he told me that he has been following my posts on social media (X and Instagram) for at least 6 months. I told him that many people will follow me for months until they work up the courage (and trust for me) to finally reach out. He told me that he feels like he already knows me through my posts and blogs, which was something I hear a lot (but also aim to convey through my writing - and have been told that I do a great job of it).
Mr. Submissive shared that he loves the way that I write and that, to him, it feels like he is actually there in the room with me. He mentioned that one of his favourite blogs was the last one I posted, which could be found here, and that he wanted to replicate this experience where he will sit on my cock and ride me while I sat in my white chair. I promised him that we can try the next time.
After massaging his right side and moving to his left side, I removed my dress without his detection. I slid my bare breasts on his back, kissing his neck and blowing into his ears while I used my hands to lightly stimulate his balls, perineum, up between his butt cheeks and gently around his asshole. “I cum very quickly” he informed me. “I’m not worried - I’m going to keep stimulating you until I allow you to cum” I told him.
I pulled myself up on the table, kneeling in between his thighs and continuing to stimulate all of my favourite parts. His hips were rising with each gentle stroke, moaning with pleasure and begging for more. He told me that he was my slave and I told him that his body is all mine to do whatever I want to it. Not too long afterwards, he was face down, ass up in the air trembling from the edging and begging for me to enter inside of him. I ignored his pleas and kept teasing him and gently touching him making his body respond to my teasing, watching him move and moan when and in the ways that I wanted him to. Each time I would build him up, I would give him a slap on his asscheeks to take him back down a little bit before building him up again.
I finally told him to turn over, facing up the ceiling, feeling his hard throbbing cock and continuing to drive him crazy with my sensual touch. I used one hand to stimulate his cock (with very gentle touch) while I continued teasing his ass. I started putting a little more pressure on his asshole, entering half a millimeter and taking my finger out only to slide it in a little more upon each entry. He was really tight on the outside but open and ready as soon as I was fully in. He was ready to receive me but I think we need to do a little more training with a beginner dildo before I give him a full cock.
He was moaning loudly with pleasure and he knew that I was ready to let him cum. He blurted out loud “punish me, I’m cumming” and so I kept stroking, not too fast or aggressive, but keeping the same pace as he was climaxing. I will talk about this experience in a future blog, which has been reported to be an extremely pleasurable experience with training and persistence.
He was spent. He enjoyed every moment. It’s not just the climax that took everything out of him, it’s the anticipation, the teasing, the edging and the idea of surrendering. I asked him if he’d like a shower and he took me up on my offer. Right before he left, I told him to reach out to me anytime if he would like me to give him some recommendations for strap ons. I’m sure he will be back soon, ready for me to take his pegging virginity in 2025.
Do you have any goals or desires for novel experiences for 2025?
