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SqueezeWax

Someone has offered to 'hookup' with me for the first time and I'm not 100% sure I should

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Posted (edited)

At 31 years old, I've never had a sexual experience. I placed an ad online a few days ago asking if there were any men in my area interested in 'meeting up' with an 'inexperienced' individual. I've received at least 15 responses since then, to my surprise. I figured they would draw the worst possible conclusion about a 31 year old virgin.

There is one guy who responded I've taken an interest in, and who wants to meet up at a hotel. He is 41. I asked specifically for older men. 

I've never even been on a date before, never been close to having a boyfriend, and here I may be on the verge of meeting this stranger for sex. 

I talked to my therapist about it today, and unsurprisingly he has some reservations about this, to say the least. I was afraid he would immediately speak to my parents, but he didn't. He understands I'm of age, and it's normal for a 31 year old to be sexually active. He acknowledged that 'hooking up' isn't exactly unusual or taboo, but he's worried about my safety. He suggested I text him where I would be if I went through with this. 

Before I talked to my therapist, this guy suggested I meet with him tomorrow. I told my therapist it would be at least a week until this could happen. He wants me to give this more thought, and to be as sure as possible I won't be endangering myself, but I don't want to put this guy off. 

He's the only one I've talked to at any length who isn't suggesting a 'friendship', and that we 'get to know one another'. This is something I found off-putting from others who have responded. One guy even asked if I would consider going camping and traveling with him. Another guy sounded like a cult leader. Another one suggested doing it in the woods.

Edited by SqueezeWax

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safety first... i don't judge people if they want to have hookups or just casual sex...i dont see anything wrong with it .. but just be careful i think that's what your therapist is worried of ..

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Would I do it probably.  You have to be prepared for anything or anyone to come through that hotel room door though.  If things are exactly what they're supposed to be great have fun but just be prepared for anything.

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Posted (edited)

This guy says he must ejaculate inside me. No dice otherwise.

I don't know if I should have been surprised a guy looking for anonymous sex online would suggest such a thing, but I was.

Is this normal? I've been reading online about how often gay guys risk this, and lot of act as if it isn't any big deal.

He says he's clean, but how would I know?

 

Edited by SqueezeWax

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I agree with the others that safety is important. I would talk to my doctor about PrEP (Pre-exposure prophylaxis). It's a medication that can be taken either continuously or around the time of the sexual intercourse, depending how sexually active one is. It greatly reduces the chances of getting infected with hiv. It doesn't prevent infection from other diseases, so using a condom is still advised.

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I'm not sure how all of this happened but I will say when you placed your ad you got 15 responses in a few days.  You can probably always have someone in your life if that's what makes you happy and that's what you want.  

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4 hours ago, sober4life said:

I'm not sure how all of this happened but I will say when you placed your ad you got 15 responses in a few days.  You can probably always have someone in your life if that's what makes you happy and that's what you want.  

I'm not ready for a relationship. I never really cared about romantic relationships. All I want is casual sex with clean, disease-free, easy-going, responsible people.

I have gotten over thirty responses by now. I figured older men would find it a turn on to deflower a younger, boyish looking guy. Yet they have continually expressed doubt that I could possibly be a virgin at my age. It's unheard of to them. They've apparently never heard of all these 'incels' online.

The issue is how I'm going to keep this a secret from my parents. My father still protects me like a bloodhound at my age.

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Posted (edited)

I'm trying to be careful by limiting this to this one guy. I'm more afraid of catching an STD and having no choice but to tell my parents what's been going on than I am of being raped.

It wasn't the guy who wanted the unprotected sex I met, by the way.

I like the guy I did meet because he was cautious himself, as far as who he was getting involved with. He gave me a little lecture about safety in regards to doing this kind of thing, which I appreciated. It felt like an honest, simple, clean transaction. I'm sure I'm making myself sound like a complete idiot, though. I feel like I'm in a TV movie.

I'm also afraid that now that I've had my first taste of this, I'm going to be more preoccupied and in need of sex than I even was before. I can feel it starting already. I'm afraid nothing else is going to have any value to me at all.

 

Edited by SqueezeWax

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So I met up with this other guy at the park yesterday. He has this women's lingerie fetish that I don't understand at all, but he's really handsome and sexy.

Unfortunately, I'm having an STD scare (possibly gonorrhea or chlamydia) from the first guy I met, and this guy is under the impression I am still a virgin. I don't want to give this guy an STD. We obviously can't do much if I don't want to possibly infect him.

I also told him a few lies about where I live, and about my family, and my job situation. I spoke to him extensively online and was truthful about everything. Once I saw him face to face, I got a little scared and threw in some things that weren't exactly true. Including the fact that my former psychologist is my father, and I live in a fairly upscale neighborhood. This guy wants my address and phone number.

He's also into me spending the night at his house, and going camping and boating with him. Am I a fool to believe he is very lonely, and to feel a little sorry for him?

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This is a terrible idea. 

You're both needy right now;  yours is sexual, his is emotional.  It sounds as if you know what you want, and it doesn't seem to be compatible with what this guy wants.

Your instinct is telling you to maintain boundaries.  So do that.  Listen to that voice inside you that says "no," or at best, "not now." 

When I was in high school, I had a teacher who had a very helpful approach to making a difficult decision.  She said that If ANY part of you says "no," then "no" is the best answer.  That advice has been proven to me to be correct.  When I got into a relationship with the last man I was involved with, I was emotionally needy and physically h o r n y, and I ignored that doubting voice.  I should have listened.

My best wishes to you, whatever you decide.

 

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