Is there something sex-related that you have not done in real life, that you would like to do?

Get paid to have sex.
I actually did get paid once. In a video booth and just dropped my coins in. Unzipped and an older man, I was 16, entered. He pulled my cock out, took it deep in his mouth and sucked until I ejaculated. He stood up wiped his lips with a handkerchief, handed me a $20, said thanks and left.
 
Buy a neighbor a vibe, she looks so depressed and forlorn. 🌭

Carly, just do it..... or have her over for coffee and bring it up...... post divorce I waited about five years to put myself out there, I joined a dating site (meet some lovely people, all a thousand miles away sadly) but there was an older local widow who wanted a relationship. I really had no interest, too dissimilar, but I gave her my number and she called to chat about who she was connecting with or more like who she was potentially connecting with and I was seeing all kinds of red flags with some of these guys. I told she didn't need to rush into things but then she started to mention that she had 'needs' that weren't being addressed..... I asked her if she had any toys to help with that situation. She said no, and that she would be too embarrassed to purchase one. I told her I would buy her some, asked her to look on a site and send to my phone approximately what she had in mind. She did. I went and bought them and delivered them to her door. She was thankful.

Yes she could have ordered them herself on line and they would have arrived discreetly. But I was really game, as she was I think, to purchase them...... intimacy without contact.

So yeah, not as good as a partner, but no man is better than the wrong man. And let's face it, multiple orgasms can be guaranteed.
 
My biggest, and theoretically easiest one to do, would be anal. Both women I have been with were/are a hard pass; ex just was just a no, wife had tried it and had a bad experience with an ex so isn't keen, but said there's no way she could take my girth anyway. So, it shall remain a pipedream.

My realistic one is to have sex on a balcony, outdoors, at a hotel. Not super public, maybe just a private balcony overlooking something. But I've never had sex outside a bedroom/living room. Super vanilla, I know.
DP, fisting, tranny
 
I'm curious to have sex with a woman who's much younger than me, by between 30 to 40 years. I'm also curious to try anal sex with a man, but I want to be the bottom. He needs to have five inches.
 
Chastity. Finding a cage that is comfortable enough to wear long term and having a keyholder who enjoyed the power it gives her. Unfortunately wife is way to vanilla to even consider suggesting it.
 
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