I was busy with the family mostly with Thanksgiving being this week. Also on Sunday I was planning to meet someone from Grindr just for a casual hello, but I got very sick. And I’m still sick!

• J and I continue to text back and forth, twice I guided him through jacking off, sending new pics back and forth but also recounting how we spent our time together, and all the thoughts sensations and emotions we packed into those few sessions. He might be coming into NYC in a few weeks. He really wants to spend another week together. We discussed that while he wants me to be his top, that he’s open to flipping sometimes and breeding me, too. I like him, and I think I’d like that. He is about as well hung as me, so it will be a fun challenge!
• New experience: flipping! I really wanted some action this week, but here on Long Island not many people can host since they’re living with (or visiting) their parents. There’s a local top who really wanted me to top him, and I couldn’t pass that up.
  • He leaked precum like a dripping faucet it was fun! His penis is significantly shorter than mine but also much much thicker. He took a lot of time to open up, and at one point he fell asleep while I had a finger inside him. That was weird! I asked him if he was on anything, but he said nothing other than the poppers I saw him using.
  • He was a great fuck once we got going. We both found it all very pleasurable. He came when I told him to, and I came inside him just moments later. I gave him a kiss and said “Happy Thankgiving!” and he said, “Am I the turkey?” 😂
  • Once we both relaxed and were ready to go again, he suggested I fuck him again, but on a whim I suggested that we change positions. And y’all, I enjoyed the experience! I don’t know if it was because I topped him first or I just felt more connected, but I even stayed nice and hard while he was fucking me. He finished in an unusual position, with me on my back and him on his side, locking his one arm with my one leg. I’ll have to try it.
• omg it’s a small town wtf I get a message from an adorable side on Grindr, and we realize he’s a few years younger but went to the same high school. Oh his brother is the same year as me, oh also in the band, same instrument, oh dang: his older brother is my high school friend! And when I went to his birthday party, and the younger brother was there 20 years ago! We decided that’s fine with us, and still plan to meet up. He’s such a sweet guy, and we’re both still into each other. 🙈

Tuesday was my birthday, and my sister and my girlfriend surprised me by taking me out for a fun night with a couple of my close friends! We met up for drinks and went to this Pho place for dinner, then we did an escape room, it was a really fun time! It was so cool to be able to hang out and have a good time with everyone and be open about things, everyone really liked my girlfriend and told me we were cute together!

Afterward, she took me back home just the two of us and treated me to some spa type pampering, complete with a full body massage that felt amazing and became more and more sexy until we couldn’t take it anymore. She insisted on focusing on me the entire night, I normally try to give as good as I get (although she has more experience so that’s sometimes hit or miss) but she wouldn’t budge and I didn’t try to fight too hard lol. And she was definitely thorough, by the time we collapsed to go to sleep I was basically a quivering puddle and was so hyper sensitive to touch I don’t think I could’ve survived coming even one more time.

On Thanksgiving with my family I did tell my parents about being in a relationship with a woman. Overall it went better than I expected, my dad just gave me a hug and told me he didn’t care who I loved as long as I was happy. My mom was more reserved, she doesn’t really understand and I’m pretty sure she thinks it’s like a phase or me trying to be trendy or whatever. She’s always been more conservative about things, but she didn’t freak out or shun me or anything, and she did ultimately tell me that she also just wants me to be happy.

My girlfriend was out of town visiting family for Thanksgiving so we weren’t able to meet up for the weekend like normal. But it did give us the perfect chance to use the birthday present she got me, it’s this vibrator toy that she can control from her end. We called over video and did a long distance thing, it was sexy but a bit awkward since I’m not really experienced with that stuff. It definitely made me realize I need to up my dirty talk game! Fortunately her’s is really good and we got there in the end! No substitute for the real thing but overall it was really nice!

I actually went to a real-life sex shop for the first time in my life.

I was nervous out of my mind and I was doing this weird fidgeting thing where I rub the inside edge of my eyelids with my hands over my nose and mouth, and the woman who runs the place asked if I was having an allergic reaction to the air freshener. That’s the humorous bit I think about to stop dwelling on how intense it was for me. It broke nearly every rule and norm I’ve ever lived by. I’ve had about ten distinct “I can’t believe I’m doing this” moments just in the last month.

The owner of the store was very polite, and spoke plainly about sexuality and masturbation so far as it was relevant to my business there. It was as if none of it were ever taboo to begin with, and that kind of approach was just what I needed to not have a heart attack right there. I got a mid-size metal plug and a small thing of lube and I’ve been casually exploring with it since then.

In other news, I learned that I’ve made enough progress restoring my foreskin that artificial lube doesn’t do much for me, and a lot of the time my glans looks like I’m uncut. Nature is healing

I spent the week visiting family, so I didn’t have much privacy. By Thursday, I was so horny, my horny brain decided to wear a buttplug to Thanksgiving dinner, which of course made me even hornier. I ended up fingering myself in the bathroom half way through dinner with my whole family in the next room over. Then again later in the night while everyone else was cleaning up and relaxing.

We had our first date with another couple. We already knew that we were not going to end up in the sack, but a four-way flirt was exciting. It took a little bit of liquid courage, but all went well. The other couple were very engaging, the female half obviously was interested in my girlfriend, and we ended up staying five hours in a bar. Nice! We plan on visiting a swinger club with them next time.

Besides this, lots of sex at the moment, from cuddly loving one to bondage sessions. :)