This weekend, I went to my fourth overall con with S, and my second Fetish Flea (technically third, but I didn’t get to experience it the way it was intended). We attended some interesting classes, two of which were presented by Midori. She was entertaining and educational, I really enjoyed her, as I think everyone else did. Her interrogation and humiliation demos were fantastic!
The tying your man down class was fun, as it always is. I love being tied up. I also believe the instructor really likes us. The hypnosis classes were good too. I feel like doing the demonstrations in the class can’t work as well compared to doing it privately. I found it hard to focus. I also think the hand gestures used to put me under made it hard to keep a straight face. Both classes were informative as well. The bastinado class was incredibly short, and the instructor reminded me a lot of Amy Poehler. The chastity class was great. There wasn’t much that she taught that I hadn’t seen, read, or heard of online, but I enjoyed the class greatly. I’ve enjoyed the chastity experience I’ve been having, and I think the course increased my desire to be caged. The Chakra class was a tough one. The breathing exercises were moving too fast, and it was incredibly hard to focus when you are in a room next door to Rocky Horror. I had a hard time keeping up with the instructor’s pace, but it did help with relaxation and replenishing/increasing energy.
I got to meet S’ friend J, who she’s known for a long time. He’s cute, very sweet. We got to meet his Domme and Her husband and a few of their friends/partners(?) over dinner at a Thai restaurant. It was my first time wearing my kilt outside of a kink event, so I was a bit nervous, self-conscious at first. But nobody gave any judgmental looks or stares.
We had a scene later on that night. I was feeling slutty and got on all fours, almost into a yoga pose. She gently touched my back with Her right hand, gliding down to my ass. With Her left hand, She teased my nipples. Breathing heavy and softly moaning, She teased my asshole with Her finger. I could feel the excitement in my cock as it began to drip and harden slightly. She stopped for a moment to get a towel to put under me. She also grabbed some lube, a glove, and Her cock (I believe). She put the lube on my ass, massaged and inserted a finger, which turned into two, and I could feel Her rubbing my prostate as She teased my nipples, cock, and balls with her other hand. I could feel the in and out action increase a bit, and I think She had started to insert a third finger. That’s when my heavy breathing and moaning turned into screaming. The pleasure of Her hitting my prostate was increasing, but I was starting to feel some pain as I hadn’t stretched my ass like that in a while- I hadn’t been plugged or fucked with a dildo in quite a while, so it hurt a bit. She knew she may have gone too far because of my strange sounds, so She asked if She should stop. I said yes, because I was close to saying the safe word anyway. When we stopped, I told Her I love Her, and She lay down and then I kissed Her, licked and suckled on Her nipples, working my way down. I licked, kissed Her inner thighs, and sucked on Her labia, kissed and licked Her clit, breathing in Her natural scent, taking Her all in, and licking Her to satisfy our hunger. She needed and deserved an orgasm, much more than I did. I played with Her nipples, tasted Her pussy, and moaned into her as I licked up her juices. I could feel Her thighs squeeze my head, and afterward She pushed me away, which I’m guessing She climaxed.
We talked more about safe words, when to say them, why I haven’t said any yet, and how it doesn’t help with trust. Honestly, I have been wanting to say it, but I keep wanting to test my limits, which I don’t know if we have reached them yet, with the exception of the ass play that night. I feel like I have a high tolerance for pain and punishment, and perhaps I haven’t been truly broken yet. We might have to push me further.
One of the things S purchased was a leather harness. She told me if I hit the gym and got in better shape, She would buy me one. I was surprised to learn with the weight/fat loss/muscle gain, I fit into a small harness instead of a medium. I love the harness, and I almost want to wear it every night when I get home, along with my collar. Speaking of collars, She also purchased a leather bow tie, and we had my collar cleaned at the bootblacking station. She also picked up a few other sticks to add to Her arsenal.
Monday, we slept in for quite a while. It eventually turned into me licking Her yummy pussy while She encouraged me with her feet to move my ass in the air, telling me to get ready for his cock to fuck me right. She then had me lay on my back, positioned Her pussy over my face so I could lick it some more, but more so She could tease my perineum. After some caressing, rubbing down there, She got me hard enough to get on top and said “show me you want it” and I began to thrust my hips. I think something must have driven me over the edge because I felt myself cum after a few thrusts, I barely lasted thirty seconds, if that even. After all that, S didn’t cum. I felt guilty not giving Her what She deserved.
Later that night, I asked if I could wear my harness. She said “only if you’re plugged” which I gladly made sure I was. My ass felt better by then. I was ordered to insert the plug in front of Her, so She could watch it go in, and hear me moan as it made its way inside me. We watched two episodes of Altered Carbon before I was allowed to take out the plug. My ass needs more training.
Overall, it was a fun weekend. I can’t wait for BiB next month.