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Need advice on an offline sex adventure!


Question Posted Wednesday October 12 2022, 6:20 pm

I need advice about meeting someone offline for the first time. I am also needing advice about what will be a first sexual encounter somewhat out of my comfort zone.
I am Linus 26M. I have been invited to an in person visit with a very fun and sexy 35F I have been flirting with online, by video, and by phone for the past 4 months. That does include some sexting and phone sex type stuff and some things she had me do for her on video. I am not going to be more specific. We are both single and just looking for a fun relationship with no preconceived idea about romance. This will be about a 3-hour drive for me so nothing too extreme or expensive as far as getting there and back. It would be for a 4-day weekend with me staying at her place.
It is maybe 20 percent social friend visit and 80 percent sexual adventure based on our shared fantasies. We have been driving ourselves crazy talking about all the hot things we want to do and there is no way we will be able to do it all but it is something we are both psyched about. It is mutual, but she seems on a mission to entice me and it is totally working.
I am stoked but I am also way nervous about expectations as she is into a lot of what I consider extreme kinky stuff and female dominating the male. I have mixed feelings but she insists it is not meant to be a demeaning thing for me but just a rush for her to be in charge. Her enthusiasm, positive feedback, and taunting my ego to prove my manhood blah blah is like overriding the fear factor at the moment. I am also very genuinely attracted to her and am eager to see if I can handle what she wants to try and impress her somehow. Again, I am not being super specific because I don’t think this is that kind of site.
I was so happy she agreed to video contact first because it confirmed (a) she is actually female, (b) she is the same person as her pics, (c) I am very much attracted to her (both on looks and attitude), and (d) she is attracted to me visually and otherwise. Part of the video was an inspection thing she wanted to do and I passed. I agreed to some temporary appearance changes. She definitely seems to like shy young guys eager to prove something. She keeps saying I would look good “all tied up.” LOL But at least there will be no catfish surprises.
She provided me a checklist of the kinky things she wants to try and let me mark them off as (a) eager to try, (b) willing to try but not so sure about it, and (c) no way in hell I am trying it. TBH, more than half the list was (c) and only about 10 items were (a) but she said that was plenty to have a lot of fun and she was not disappointed. She gave me a safe word and we set up a deal where I will call a friend every so many hours to confirm I am alive and not being tortured to death. Also, she suggested I set up my phone so I can be tracked by my safe person.
She also has some people who are checking on her during my visit to make sure I am not a freak turning the tables on her. We are literally meeting at a neutral place (Applebees) and she will decide if I seem safe enough to get to go home with her after dinner. Worst case, I buy her dinner, it is a busy, I stay in a hotel room by myself, and I drive home the next day. She has done this before with other guys so I am on notice this is not something exclusive. That is weird and exciting at the same time and part of me is wondering I will compare to other dudes she has dominated for sex.
So, am I like falling into some kind of horrible trap with a female Dahmer where I will never be heard from again? She has promised she is not a cannibal and will not do any “permanent damage.” I don’t get a scary vibe, but I also feel like I am in over my head in some ways. She says she loves the idea I am a “vanilla” guy and she gets to rock my world in new ways. So far I really enjoy earning her praise and even the affirmation “good boy.”
I know my critical thinking is being influenced by the sexy sales pitch I am getting and her positive comments on the body inspection. On the other hand, it seems to me like we are taking reasonable precautions. Should I just chill and enjoy whatever happens and do my best to meet her expectations? Or, is this the stupidest thing you ever heard about a desperately horny shy guy getting himself talked into doing? Feel free to take either side or just give advice. I want to do it but need genuine objective feedback.


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Dragonflymagic answered Saturday October 15 2022, 10:12 pm:
Not sure what you were trying to convey at the beginning when I read "a first sexual encounter somewhat out of my comfort zone" So I am not sure if you meant this is your first dom-sub encounter or your first time having sex. I ask because I know there are people who sometimes have not ever had sex for the first time til much much later, so my answer will vary a little if thats the case. If its your first time ever, then I feel it may be a case of you biting off more than you can chew so to speak. You did mention feeling in over your head and half the check list not sounding good to you at all. I can understand how this must be an enticing thing to consider if you are a male who hasn't done this kind of thing before. There is enough excitement in just having a new partner for many. They seek that excited feeling at the beginning of a relationship, which I call new relationship energy and have read about the situation and think it may apply here. NRE is the same thing you feel about anything new to you, especially like when you were a kid and made your wants known and were sure that you would get it for Christmas or your Birthday, and just waiting for the day to unwrap the gift was so exciting.
So when you got exactly what you thought you wanted, it was great at first and you wanted to play with it every day but as time went on, you played less, and even less until you totally ignored it. I experienced that with toys and know the same applies in relationships. If the toy was just right for me, then I never tired of it. If it wasn't right for me, then I was excited due to the new experience of playing with it but it soon lost it's appeal. The same can happen in human relationships. This is something new for you no matter which way your beginning statement goes. Since this is for sex and not for a relationship, then once or twice is fine but soon after you or her may want another some one new and it ends. The worst that can happen is if there is no chemistry. Chemistry that I speak of is romantic sexual chemistry, important for most to have sex with a person. A persons looks come into the picture, yes. But there is more to chemistry than just what you see. After a divorce, I joined two online dating sites. I was not after what you want but there are plenty on line who state they look for just sex. So I speak out of experience when I say that on line chatting and on the phone can be so widely different than meeting in person. You can meet some one who looks like a model that just walked off the page of a magazine. I once met a man like that. Wow! I thought at first but after the one date, neither of us wanted to go further as we just didn't feel drawn to each other. I spent time on line, falling for a guys mind, how he thought and so on. That is what you currently have with her. The worst was when I arrived first at a restaurant to meet a guy and was at the front waiting. I did not recognize him from his photo, although the photo was of him. Some people are not photogenic. He looked okay but immediately I felt a lack of chemistry which to me was a lack of excitement as in "Oh gosh, this is my date? I am so lucky" and the feeling of butterflies or a quickened heart beat. He asked if I was who I am and I said yes. Without missing a beat he says, "This is not going to work out, is it " spoken more like a statement than a question. I verbally agreed, glad he felt the same but we sat and had our dinner anyways and in talking, confirmed we had many times in common except that chemistry was lacking. Chemistry isn't something you can make happen. It is there or isn't. And with on line relationships, it is not something you can tell because you have to be in person, face to face for it to happen. Even if just for sex, I can't see anything happening if you or both of you feel that when you first meet. You really won't know until the day. I got so hopeful a handful of times but when I met the guys, no chemistry and I actually wished on two occasions that there was chemistry cus the guy had everything in common with me and was very nice. However, when I met my 2nd husband this way, there was chemistry. So I am merely telling you that if you get together and you do not feel the chemistry because it feels like you are kissing your Mom like a female lover and that image can't be gotten rid of, it may be there is no chemistry, even if forcing sex to happen by pushing yourself to do the next step. I have felt that like at the end of a date, kissing the guy and it felt gross like kissing a male relative, not because he was bad at it, simply due to lack of chemistry. Also, you may like being the sub and her the dom. But if this is all she wants every time, just different versions of the dom thing, always telling you what to do, getting treated like a lap dog. Anything in life usually has to be experienced before you know if you like it or not.
There are some things you will know for sure but some times, a vocation, career type sounds great until in it and then you quit to do something else. Or trying different foods until you know whether you like something like Sushi or not for example. Same with sex. It is nice to have a partner also willing to try new things but in this case, it sounds like it is all about her when I read "it is not meant to be a demeaning thing for me but just a rush for her to be in charge." If she is pressing this so hard with you, it would seem that this is what gets her off. Will she be able to have 'vanilla' sex without the kinky stuff. Or maybe this kinky stuff is a first for her and til now she's only studied it in books or online and wants to experience it for real. If I let my mind wander, I also wonder if she is married or ever was, and her husband didn't like it, maybe divorced her over it when the dom thing and kinky sex was all she wanted. People will sometimes just decide on a whim to do something new. There are limits always to what a partner may want or be in the mood for on a particular day. As long as you are comfortable. If you get into the middle of this and inside your spirit is screaming to escape this, then use your safe word, tell her you've discovered this is not for you and then get up and leave to your hotel room and chalk this up as just one thing you learned that you do not like.

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