What (naughty) fun have you been up to this week? (from 5th February to 11th February)

I'm not a great story teller. Please remember that and don't judge me to poorly for the telling

First ever Tinder date last night. I'm not completely inexperienced but it's been more than 10 years. (I'm middle aged now)

We both decided we liked each other enough to smoke some weed together and just see what happens.

Was great to hang out to have someone to chill with and we got along well enough. Not sure if I'm just too old now, the weed or if it has just been too long but i didn't have much in the way of arousal. Unfortunately it turns out shes is a very horny lady and got very aroused chilling with me. I love cuddling so i was very okay with that. I felt really awkward though having to tell her I'm not going to try and force myself to have sex if im not feeling it but that I'm having fun just hanging out if still into hanging out. And she was very understanding not wanting to pressure me into something if I'm uncomfortable with.

We talk about it for a bit and decide that she can be as frisky as she wants as long as she stops when i say stop. I want her to have as good a time together as she can i just dont want to get her hopes up because i am comfortable speaking up if i dont want to do something but that theres a lot im still willing to do.

A lot of hands roaming, cuddling and some heavy breathing later and the couch is not very comfortable. So we talk about expectations again before moving things to her room so we do. Shes very vocal, but quiet and hard to hear but shes telling me how turned on she is and i want her to enjoy this as much as possible so i have an idea. Maybe im not going to finish her but i like to make people happy so maybe we could use those to help her get off.

Now im not sure here, but i think she was shocked i suggested it. Like in a really? You would be okay with that? Because it took her a second but she immediately grabbed a few toys and put them to use.

So here we are, me first time getting stoned with someone who is very horny and now theres a very happy sounding person in my arms twitching a very good twitch from how she feels against me. Somewhere over the next 20 minutes she begs for me to play with her nipples. I am okay with this and she feels great in my hands by the way.

She is grinding hard into me and she goes completely silent multiple times before turning off the toys and then cuddling up to me. She quietly admits she made a mess and is apologizing for getting me wet. She was very very wet but that just makes me think she must have enjoyed herself. Which was really fucking cool to be a part of that even if i didnt do much but be there and encourage it. Ive never felt someone squirt so much it was a lot of fun being a part of it.

We ended up using her toys on her 5 or 6 times over the next 3 hours or so in her bed. I can no longer say i havent spanked anyone.

I forgot how much i enjoy just being naked and comfortable holding someone is. Highly encourage everyone include their favourite toys and put them to good use. I really like to help other people feel good

Fuuuck that's so hot. Good for you! A lot of guys hesitate to use toys on their partner because "what if they get used to the toy, then they won't need me" lol. If a vibrating piece of silicone could replace you, you're not bringing much to the bedroom 😅.

So it's awesome that you showed her how flexible you are in how you can be intimate. Frankly, toys free up your mind and body to do a lot more to please your partner and flex your erotic imagination. You sound like a good lover. I hope you and this lady see each other again 🙂
- Interestingly enough you mention it, i really don't think i do bring much to the bedroom. I'm pretty simple, i dont need much from other people other than to enjoy them and im often confused about why people enjoy urges they have. The ones that involve other people are especially hard for me because if i havent had them or even cant relate a little bit. I just don't want to cause anyone harm.
  
  And thanks. Me too. And thanks for the kind words, im glad you asked to share it. I can't across your post at an opportune time. I was like hey! I have something to share! Lol
That sounds so hot, and definitely agree using toys on each other is fun!
- Im very much keen on repeating the experience sometime

My FWB brought over his fleshlight, I showed him my toy collection. We spent all Saturday together completely naked. He used a vibrator on me for several hours over multiple session, I came sooo much. I edged him all day with his fleshlight, it was so fun making him squirm, until he finally came inside it.

Sunday night we watched the superbowl with some other friends, and went to his place to fuck afterwards. I wore some red lingerie under my clothes to watch the game and surprised him with it, he asked me to keep it on while we fucked.

We had agreed to only do the benefits thing on weekends but we're making an exception for valentine's day.

Eee this is sexy and adorable! Both using your toys on each other, and you edging him with it. It's great to see that much communication and experimentation in a hetero pairing. And I totally get it. Sometimes sex partially clothed is even hotter than being totally naked, I totally get where's he's coming from with fucking you in you lingerie ♥️

Enjoy V-Day. Just remember if you're also doing to have dinner, have dinner after you fuck! You'll enjoy it more. That's some sage wisdom from Dan Savage, himself!
- Thanks! I've been having so much amazing fun with him!
  
  I'll definitely take your advice on that. I hope you're spending V-day with someone as well! ❤️

Still on Long Island, still no job, so things have been weird.

Friday, however, while out to run some errands, I met up with a guy on Grindr who lived near the hardware store. He wanted to take care of my cock, and I wanted that, too.
- Fun guy, very chill, played music on his PS5/Spotify. Spent so much time sucking me off, about an hour the first time. He was somehow squeezing his throat tightly around my cock while fitting most of me in his mouth -- I have no idea how it was amazinig. I was rimming him for so long, too, and I loved how much he loved it. I'm starting to get pretty good at slapping a nice big booty while chowing down. Sounds good, and feels good in the hand.
- Slowed him down a couple of times so we could keep going. Finally, I let him swallow my load and we had some nice chatting and goofing around.
- I had him cum while I was rimming him, which was enough to drive me to cum a second time. He was a good boy and ate it all up again.
- Some fun embarrassing stuff with his roommate coming home early and me mostly naked cleaning up in the bathroom. Good chat about the anime we like. He also had an adorable and chill cat that played with me for a little bit :-)

Not bad! Isn't that two weekends in a row of sexy times?

I've always been a bit apprehensive of the Grindr crowd. The weekly flings with different partners are not for me. I'd like to find one or two kinky people who would stay with me for a couple of years and keep the intensity up on weekdays as well. It won't happen in the pueblo I'm stuck in now, and I think I give off loser vibes because I can't dig myself out. At least people are giving candid accounts of the fun they're having so we can all join in the discussion.
- Yeah it is. While I'm looking for that more regular partner I figure I may as well have some fun. Most of the guys I meet are well-educated professionals and we often have lovely chats before, during, and after our time together.
  
  From what I've seen, Grindr is very very different in different towns. A few months ago I was in Pasadena and it was terrible, then I was in Beverly Hills and it was dope. So I'm not surprised if you have a very different experience.
  
  Not everyone is fwb/relationship material, but y'know if someone cute wants to SMD, who am I to refuse? 😉 Even a little casual fun can help you get out of a rut - in some ways the pressure is off if you're never going to see them again. My first Grindr hookup was just last year: a tourist who was staying in a nearby hotel. Kind of helped me flex some muscles I hadn't used in a while (literally) 😏
Oh man I had no idea you've lost your job too! So sorry to hear - I hope you get a job soon!

Friday guy wanted to take your cock off??!?! 😱 I hope your cock has recovered!

Jokes aside, the dude sounds like a real winner! As always, super impressive all the mad sex you get on a weekly basis!
- Thanks. I'm taking my time to find the right next thing.
  
  Good catch. I edited to correct the missing word.
  
  Good guy. But for me weekly is so much less than I want it ;-)

I matched with this girl on Bumble, and the conversation went from "lets meet up in London" to "lets meet up at your town".

We met up, had coffee, went back to my place, made out and had some filthy sex!

Sad news is that I thought this was going to lead to a capital R relationship, but I think she just wanted to have a cheeky shag. Nothing wrong in it, but I wish she hadn't strung me along.

Doesn't Matter: Had Sex.

EDIT: Completely forgot two things:

She said I had a big cock! Anyone who knows my past knows I had some insecurities around this area, so I was so chuffed to hear that!
She said I was the first person to have made her cum through penetrative sex alone!!

My friends, I think I deserve a trophy 😎 😎 😎

Great to hear from you. Yes 🏆 for you! Been a while, right? Getting a woman to reach orgasm from penetration alone is quite an accomplishment. You're clearly a good lover, with good attitude, good equipment, and good technique!

Edit: other than "good" how are you feeling, champ?
- Man, I had like a whole paragraph typed up and it got lost! I wonder if this has been happening for some time!
  
  I'll keep this one short in case it reappears:
  
  Thank you! I gracefully accept my prize!
  
  It has been a while, things have been up and down. Work sucks. Applying for jobs sucks. Family have been awesome throughout the whole ordeal.
  
  I've matched with another woman, although she hasn't given selfies when I asked (despite asking me and I gave selfies - in my PJs no less!!) so I think that's a red flag tbh.

I was invited over to cuddle with a guy I know. It immediately escalated and he was slapping my balls hard while I sucked his nipples. He had his finger in my ass begging him to let me cum when he said no. Then we fell asleep lol. He Dommed me so well I'll be going back lol

Hot. Love when there's a delayed gratification component. Did you know that's how he likes to play?
- We had talked before and he said he just liked to be what his play partner wants him to be. So when we started I told him I liked orgasm control and CBT and he did a great job of it. The only bummer is he didn't let me get him off either.
  
  Things got cut short though cuz I wasn't feeling well.

... I guess that makes sense..

Thanks

Had a long discussion about sexuality with my neighbor/coworker/roommate. (it's complicated). Also, he has a new headmate who calls me mommy/sis (it's also complicated) in a sexual manner. Which is neat.

What's a headmate? Like he has multiple personalities? That's fascinating.
- Essentially? But unlike a dissociative type, he's the core about which other personalities /people revolve and he has a bit of control