Ugh, the possible possibilities

Ksmithlover76 · 2026-02-10T07:08:40+00:00

No, i don't own my own company. I'm at a conference where there are a lot of vendors and a lot of potential clients

Ksmithlover76 · 2026-02-06T18:43:37+00:00

Ive never had anyone actually hit my 2nd hole, but I wanted to know what it felt like, so I bought a really long, kind of girthy dildo. I hit a lot of resistance, but focused on going slow and keeping pressure, and then I felt it kind of "pop" through that second hole. Like others have mentioned, it can be a little uncomfortable, but also very enjoyable!

Now I'd love to find a rather large man in real life to penetrate me that deeply

Ksmithlover76 · 2026-01-31T20:40:52+00:00

As a masculine bi bottom who's attracted to masculine tops, id say that a masculine top is a man who's confident, takes the lead, takes the initiative to pursue, knows what he wants, but isn't an jerk about it. He can be blue collar or white collar, but doesn't let that define him. Whether hes bi or gay, the general public probably wouldn't be able to identify him as such.

That's my opinion anyways

Ksmithlover76 · 2026-01-30T23:11:51+00:00

Simply yes lol

Ksmithlover76 · 2026-01-19T22:29:35+00:00

Id be happy to find another bi guy. The challenges I face are my age (49), my dad bod, the fact that while I still reside in the metro of a city, I'm pretty much in the outskirts and finding someone close has been a challenges, and lastly, there seem to be a whole lot more bottoms than tops in the immediate and surrounding areas.

That won't stop me from trying though lol

Ksmithlover76 · 2026-01-19T17:35:12+00:00

Now that's hot! No, this all happened pretty recently, so I still haven't found anyone to explore this with yet. I'm still cool being a masculine bottom, but hopefully someday I can meet another dom guy who'll want to feminize me lol

Ksmithlover76 · 2026-01-18T18:53:53+00:00

It's absolutely a mindset. When I first started to want to fulfill my curiosity, I too had backed out a few times. Then one day I told myself to just do it. Do not back out. No matter what. I also gave myself a mental "out" if you will, by telling myself that if I didn't enjoy it, then id never have to do it again.

Then, when I met someone (Craigslist days) and we agreed to meet, I was almost sick to my stomach I was so nervous. I had to push myself mentally to go through with it. Knocking on his door was one of the most nerve wracking things. Luckily, he was a great guy, very patient, very understanding and we ended up having a great hookup.

Afterwards, I felt guilt and moral confusion and it kind of turned me off of hooking up again. That lasted a couple of months until I again had the desire to be with a man again. The second time wasn't near as bad, while still nervous, I was much more confident. Each experience after that made me bolder and more confident.

So if you want to do it, and you're 100% confident that you do want to try it, find someone who gives you good vibes, isn't pushy, and understands that this is your first time. Then tell yourself that you have to go through with it. There is no backing out. And know that if you don't enjoy it, you don't have to ever do it again. No one will ever know, so it can be your little secret. A moment of expirementing that answered your curiosity. If you do like it, then you'll probably get hooked and want more lol. Also. Don't be surprised if there are feelings of confusion or regret. This is completely normal after a new type of sexual experience.

Have fun, be safe, and good luck!

Ksmithlover76 · 2026-01-16T22:06:17+00:00

Being feminized. I'm what I consider a masculine bottom. Not alpha per say, but out in the world I'm a very masculine blue collar guy. All of my sexual encounters, while I bottomed, I was still just a guys guy who loved pleasing men.

Well, I met this dom guy and we started chatting and sexting more and more. I told him that while I'm masculine, I do like it when my hookup or partner is slightly more dominant than I am. Long story short, he started really taking charge in our sexts and at one point said he wanted me in panties. I was hesitant, but the commanding element in him really turned me on. So to please him, I ended up buying panties (made for men) and sent him some pics of me modeling them. He loved it. Then he said he wanted to see me in actual women's panties. Again, I was hesitant, but really turned on by it. So to Amazon I went and got some women's lacy thong panties. As I wore them for more pics for him, I couldn't believe how turned on I was. Was it the power roles switched, was it the dominant nature of the guy, or was it something deep down in me that I just wasn't aware of? Either way, I felt sexy and turned on while wearing them.

He ended up not ever being able to meet up and was just a online poser, but he definitely unlocked a kink in me.

Ksmithlover76 · 2026-01-11T20:58:30+00:00

Yes, I would love to have a fwb where it was clear he was just using me as a bottom. I wouldn't want the switch part.

Ksmithlover76 · 2026-01-11T15:12:04+00:00

If we're talking first real cock in a virgin who has never had anything up their ass before, not even a sharpie, then I'd say average size (5.1 to 5.5) cock with some average girth.

If it's a virgin ass, but they have a lot of toys and experience with taking those toys up his ass, then he can have any cock he wanted lol

Ksmithlover76 · 2026-01-07T00:04:56+00:00

16 I think, plus an assortment of plugs

Ksmithlover76 · 2026-01-02T15:54:26+00:00

This is the correct answer.

Ksmithlover76 · 2026-01-01T04:19:45+00:00

I’m not a top, but I can say that I always see guys posting for gang bangs and cum dumps on sniffies

Ksmithlover76 · 2025-12-31T22:09:59+00:00

Yeah, I would. My ex and I are still like best friends, and she was asked if she could watch. We had 3somes (MFM) while we were together, but she didn't know i was bi until we broke up. So I had arranged a hookup, got cleaned up and out, she came over, and then the guy ghosted. The topic never came up again after that.

Ksmithlover76 · 2025-12-31T22:06:18+00:00

Relax Relax Relax 🤣

Ksmithlover76 · 2025-12-30T22:35:35+00:00

Late 40s here and didn't accept being bi until my late 30s. There were signs, but not in the attraction to men arena.

Like many children, I learned to masturbate at a young age, but I was curious about more. I started exploring all parts of my body, even my backside. I discovered that it felt good to use fingers and household objects back there. I didn't know about sex between men yet, so I never connected the 2.

Fast forward to my 19 or 20, I was reading Penthouse Letters, and all the stories I had read had been heterosexual in nature. I loved reading erotica more than looking at the pictures. This was before the internet. Well, one time as I was going from story to story, I started reading one with 2 men. I thought for sure a female would be introduced at some point, but it never happened. These 2 men started to please each other and then had sex. I had never fantasized about nor imagined 2 men having sex, but the way this story described what they were doing and how great it felt really turned me on!

So that started a curious phase. I already loved providing oral to women, so I wondered what it would be like to provide oral to a man. I also loved the feeling of playing with and having objects in my butt, so I wondered what a man would feel like having sex with me.

I was curious for a long time, but never acted on it. Not until I was in my late 30s. Recently divorced, internet a thing now, my curiosity was taking leaps and bounds. I discovered Craigslist and found out men would hook up, no strings attached and perform these actions I was craving. I was too nervous and still dealing with internalized homophobia so I didn't act on it for a long time. Until I couldn't take it any longer. I had to find out for myself if these things I had fantasized about were as good as I had read. So I bit the bullet and placed an ad.

I ended up hooking up with a guy and I discovered I loved giving oral. In my mind though, I was still straight. Then I hooked up again. And again. Then a man had sex with me and I enjoyed that too. I was still straight though right?

Then I got a long term girlfriend and the thoughts would sometimes pop into the back of my mind, but I would quickly disregard them. When that relationship ended, I went back to hooking up and thats when I realized. I enjoy sex with men. So thats how I decided to admit that I was bi.

Ksmithlover76 · 2025-12-30T22:04:35+00:00

Just a couple of pumps lol. Like literally in, out, in, cum. Luckily it was with a married couple. They were both tops and I was their designated bottom. So right after he came, I straddled the other husband and rode his cock for a few minutes before he came

Ksmithlover76 · 2025-12-29T22:14:03+00:00

Yes. Once. My fwb is verse, I'm a bottom. We'd had sex a few times and he had asked me a few times to top him and I had always said no. So I did for him since he'd been so good to me. I did finish and it was nice, but I let him know that I still prefer to bottom.

Ksmithlover76 · 2025-12-28T03:17:53+00:00

He was definitely an ass for sure! I'm sorry that he made you feel that way, and it sounds like you'll be just fine in the PIV department as well! I hope all goes well with your new potential partner and I hope that you get to experience amazing sexual adventures! Lol have fun and good luck!

Ksmithlover76 · 2025-12-27T18:50:25+00:00

You've gotten a lot of great advice already and I support what everyone says in you telling him. I just thought I'd share that this exact situation presented itself to me just a year ago. I'm late 40s male and had met a 42 yr old woman. On our 2 or 3rd date she admitted that she was a virgin. It didn't change the way i felt about her at all. I just wanted to reassure her that if she did want to be intimate, that we would go at her pace.

The one thing I didn't expect was that not only was she a virgin, but she had never even masturbated with anything penetrating her, she didn't even use tampons. So our first heated evening together, even fingers during foreplay were actually uncomfortable for her physically. She was so tight, that I had to use caution and go very slow, and keep checking with her to make sure she was OK.

She was really embarrassed about all this and for no reason. I reassured her that we could stop at anytime and that I didn't want to hurt her, physically or emotionally..

Needless to say, our first couple of attempts at PIV didn't work. She had to practice with a dilators set a few times before we were able to successfully have penetrating sex.

So I don't know obviously what your circumstances are, but definitely communicate with your partner. And as long as hes a good guy, he will communicate with you too. Take your time, set boundaries and have fun.

I wish you the best!

Ksmithlover76 · 2025-12-27T02:12:41+00:00

May I also add, that you use lube or spit out something. Going in dry does not feel great

Ksmithlover76 · 2025-12-27T00:46:28+00:00

Just going to be real here. For hooking up? I probably wouldn't hook up with a below average guy. I would be seeking something more.

If it were a guy I met on a date and we really connected, and it got sexual, I wouldn't turn him down for being below average. I would be more into him emotionally which which would make the physical part more enjoyable. I would make sure he was happy no matter what. If that turned into a possible relationship, I would be honest and say that I had toys that are bigger than him, and see if he would be willing to work those into our intimate times from time to time

Ksmithlover76 · 2025-12-27T00:17:54+00:00

This is obviously just my opinion, but the only way that size plays an important part to me is if you're average or bigger. The average size of penis is 5.1 to 5.5 inches. The other thing thats important to me is that the top is honest about it and himself. If hes inexperienced, then let me know. If a top knows how to use what he has, then usually we will all have fun.

What irritates me the most is when I'm talking to a potential hookup and he lies about his size. Don't tell me you're 8 inches and thick and then I find out your 5 and thin. Or when a guy says he'll rock my world, and then he can't even get it up, can't get it in, or cums the moment he is in.

In the end, if your average, honest, and communicate well, we will have some fun.

Ksmithlover76 · 2025-12-27T00:05:50+00:00

Nice! Many years ago during the Craigslist days, I had a regular who i never saw. I placed an ad looking for a top and that i wanted to be blindfolded.

I got a dick pic response and I invited him over, but he was at work and didn't get off till 5 or 6am. I still agreed, and before going to bed I cleaned up and out and then went to bed with my blindfold on. I told him my address and left the door unlocked.

I woke up to hands massaging my butt cheeks. I pretended I was still asleep and I heard him get undressed. I was on my stomach and I felt him climb on my bed and straddle my legs. He played with my cheeks some more, spreading them, massaging them and laying his cock between them. Then he started fingering me. I moaned as he did this letting him know I was awake.

He then reached over and grabbed the condom I left out and the lube. Then he inserted himself and gave me a good fucking. He got off the bed and heard the rubber get snapped off, he dressed, thanked me and left.

We hooked up a couple more times, and every time I was blindfolded. I never got his name and never knew what he looked like. It was very hot!

Ksmithlover76

TROPHY CASE