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  • Asking for casual sex to women as a shy guy

    After years of wandering, I'm considering to have sex only recently given a number of long lasting and various reasons I can list quickly before going into the topic.

    The first reason is that I originally have a fetish for big breasts, coupled to an addiction to masturbation, which took over the need for making out. The second is that I have difficult ideals, as I've always been attracted by older / taller girls / women only, which is linked to the third about having a certain personnality / psychological profile.

    I've always been sickly shy (and clumsy) to begin with (which can lead to small problematic situations at the occasion) and I realized it's a little more than that when it comes to male / female relationships, and I pointed this out for myself also only recently.

    I just dislike the idea of being or feeling superior in male / female contact - in other words, the reverse of the typical relationships between opposite sexes. I think there is a well hidden part of my psychology which is like the one of a stereotypical, intellectual school girl doing things on her side but seeking for recognition - I don't know how to explain that - mixed with my androgynous and adolescent-looking aspect as I'm 30 but still looking in my 20's and easily younger compared to guys of my age.

    With that in mind, I just don't really know where to search, for a certain type of women I'll describe below, and how to express this need, other than in the form of letters where to express this "weak point" of mine and this desire to offer myself to some women. I think I just need to be more focused / confident about myself and my desires, but I get depressed easily upon the idea of being ignored or refused, in any circumstances.

    When it comes to the types of women I like, it's generally very slim or tall women, depending of the style, blonde / blue eyed at best, and I like asians too, generally between 35 and 65. Also, tall athletes / muscular women, and it's a special thing or kink I don't know what to make of since I never went to a gym (I like sports but I'm asthmatic sadly). In fact I dream of getting "f**ked" by one of these but I don't know where to do my research on the internet or irl to reach this goal, what communities to target.

    I would detail more about my situation after getting some replies since I think the introduction is long enough already.

  • #2
    I don’t think it’s entirely clear what this post is asking… are you wondering if asking for casual sex (for the reasons listed) is morally acceptable? Or asking if your reasons seem sound? Whether or not it’s morally acceptable to hand yourself out in return for sexual tokens of validation of worth, that is something that only you can evaluate for yourself.
    Your physical ideals alone will be hard met by nature. Depending on how tall you are talking, that alone isn’t too hard to find among women. And tall+skinny typically goes together since they have a higher metabolic demand to maintain, especially if they are athletic or exercise on a regular basis. However, tall+skinny+big breasts could be much harder to find since being skinny and having a higher metabolism to start with inclines them towards smaller breasts since they’re predominately made up of body fat, again especially if they are athletic. Adding the Asian requirement or hair/eye color on top of all that could only narrow down your options further.
    I myself have always preferred tall girls (over 6’), but I learned over time that there are much more important things in a relationship than whether or not they meet every single one of your physical ideals. Currently I’m with a girl who is only 5’5-6” so she wouldn’t meet that ideal, but she makes me much happier than I’ve been in other relationships for other reasons (which in my opinion outweighs the ideal physical condition). There is of course always a chance of finding someone who is close to meeting the majority of your ideals, and if you can part with an ideal or two here and there to give someone a shot, you might find that particular ideal to not have been as detrimental to the overall picture as you once thought.
    As for being shy and submissive in a relationship, that comes down to the woman on whether or not their personality type meshes with that and how open the communication is between you two. An older woman might have more maturity/understanding of the matter, but even someone on the younger end of the spectrum you’re looking at could mesh with that just as well. There are plenty of strong personality types that wouldn't have a problem taking over the dominant role in a relationship. The biggest thing imo is open communication with your partner on how you feel and what you think your comfortable role in a relationship needs to be.
    As for where to find such women, I’d imagine that dating sites or apps would be the best way for a shy guy to filter through a large enough population to have a chance at finding some close matches to your very specific ideals. I’ve been out of the dating scene for a while now though so maybe someone else could shine some light on the best places to look.
    Hope you can find what you’re looking for
    Just an average guy, with a not so average package.
    Starting: 33.3cm NBPEL, 23.5cm MEG
    Goal: 34.3cm NBPEL, ~23.5cm MEG w/consistently strong EQ

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    • #3
      You need to open yourself up to others in possible relationships. Yes, you have your ideal candidate and I hope you find that. But honestly, a relationship is so much more than what you physically see. You need to deeply connect with someone mentally as well as physically. Truth is, if everyone held to ideals, most would never find a partner. The fat ugly guy would never find love, the chubby gal either. Yet, take a moment next time you are out and about and look. You see overweight guys with attractive females and vice versa all the time. It should tell you that there is something deeper you need to be looking for. Someone that makes you laugh, someone that makes you feel special, someone that fills your heart with warmth. Someone that fills you with want when they are not around. That person can come in any shape or size, but when you find it you will know. Expand your playing field my friend, she is our there. And when you find her you will look back on this thread and think - Why was I so narrow minded back then. Good luck in your journeys and I look forward to your future post telling us all about who you found and how they have changed your world.
      Last edited by TheZZMan; 2 weeks ago.
      “You can make more friends in two months by becoming interested in other people than you can in two years by trying to get other people interested in you.”
      — Dale Carnegie

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      • #4
        Thanks for the first replies guys.

        So I think I was suggesting 2 or 3 things at once and you encompased them into 1 (single relationship), but nevermind...

        At the moment I'm just seeking sex-friends for one night or two, as the casual sex topic suggests. Getting in couple is another thing I'm not sure to consider any time soon for more intimate reasons - unless I happen to find someone single meeting most of my demands, I could change my mind, or not, it's hard to tell... I don't have a good opinion about dating websites otherwise - I think some (most ?) of them are scams with fake profiles used to make money with paid subscribtions from credulous and desperate people bank accounts. I'd much rather do my research on social networks or even IRL if I really wanted to be with someone by chance at some point.

        I guess my questionnings were about finding new things or way of thinking to be more confident and uninhibited when it comes to asking for casual sex to strangers. For example, I think my serotonin levels are low and it makes me unwilling to do things and feel positive and creative in general. There's also this loss of interest for sex after masturbating at night that makes me uncertain, and this feeling is more or less pronounced each night. So it's like I'm not sure about how much I dramatize the idea of having sex with someone, but I wish it would be as simple as a sport or well-being activity for example... which it kind of is, but it may not be seen or felt like this so easily. I've never tried aphrodisiacs as a side note, only maca but I don't recall if it had any positive effects about being uninhibited.

        I also have to take care of me physically, I don't have a bad alimentary discipline, I try to eat less than 1k calories per day in fact - I eat seasoned rice and try to drink more than I eat. I'm 164cm (5,4 ft) for less than 60kg actually, and I only feel at my best close to 50kg. It may seem very low but keep in mind I still have an adolescent structure despite my age. I wish I could start musculation a little but it's like the desire to do things in general, but I can do that, I'd just wait to be dry enough.


        In my surroundings at the moment, there's a skinny girl a little smaller than me but older (~35) with a hot voice (she wore a YouPorn logoed sweat one day... weird) that I can see saturday nights at a pizza truck ; an asian cashier, also skinny (~40) but probably married ; and a taller and older girl (~35) with a punk-ish style and a gorgeous butt seeming to be single in my village (she was nice to me once).

        I've written different messages for each where I try to stay simple, using the right words and ideas like the one of my submissive complex and the other about offering myself. In fact I'd invite them to come at my home freely at night to find myself in a bed (I live in an old 3 floors inn with many bedrooms) where they could enjoy me like in a dream if they find me. I like the scenario and I think it's the best approach as it's giving the sense of two free choices instead of one : contacting me via e-mail and enjoying myself at night after that. I'd also like to propose to make massages to some of them, I'm used to beauty institutes and I buy cosmetic products all the time, so I'm curious about making a back modeling myself.

        About my writing technique, I start telling them why I find them attractive physically in one sentence, I make sure to use the forbidden word "sex" only once or twice (asking them if they'd like to have sex with someone younger like me, or if they want to become sex-friends) to try to spark sexual desire and let it take or not, then I explain my position about enjoying some older women and my idea of offering myself at night, ending with my e-mail adress ; and I think I would add the sport / well-being activity aspect somewhere too. I try to put myself in the skin of the ones I want to contact when I write these letters, but the sex part is difficult to imagine, it's either hit or miss in my mind and I'm always concerned about leaving some bad memory after all - it's something quite constant in my ideas of relationships in fact. I limit myself to half a page or a page of text to stay simple and effective, and I set the font small in size 11 or 10 to increase the secret aspect of the letter.

        I vaguely thought about letting some piece of paper with only my e-mail adress written to get in contact instead, but I think it wouldn't be as inticing as sharing some thoughts "in person" through a "love letter" ; in fact it would make myself look suspicious, not communicative at least and not making known what it's all about before contacting me, so I fear it would only lessen the chance to look clean or interesting and get contacted in return. Also it would be nicer on my side to get directly contacted about something expressed in secret as if my mind was red and my desires considered from afar.


        About the tall athletic / muscular girls, I'm wondering how I can get in contact with some of them through internet as it's unlikely I happen to go to or find a gym where to meet them. I don't care what part of the world they are as long as my wish could be fulfilled as long as I'm young enough.

        I'll give news about how things go in my current surroundings... I just have to print my letters and break my mental ice to give them.
        Last edited by Crystal; 2 weeks ago.

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        • #5
          I think these letters sound incredibly creepy. My advice would be not to do this to strangers.

          Since my mid teens, boys and men have approached me for sex. Not once with a letter like that. Thank goodness.

          You call them 'love' letters at one point in your post. Well I have had love letters and there nothing like that.

          Go out in the real world, strike up conversations and ask people back to your place etc. Or go on tinder etc online and state you want no strings attached sex.

          Many women want the same. if they find you attractive, it will happen.

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          • #6
            Originally thought you were looking for a relationship, I see differently after your last post. I agree with Tara123 in the fact that you have run into a fantasy realm of your desires. Nice to have wants, but you seem to have specifics to your fantasies that most likely are hard to achieve. Work on your shyness and just approach women and ask. Might have more success if you go the date route first, always nice to get to know someone first before doing the deed. But in all honesty, you are out there my friend, casual sex doesn't involve any type of stalking, which you seem to be leaning toward.
            “You can make more friends in two months by becoming interested in other people than you can in two years by trying to get other people interested in you.”
            — Dale Carnegie

            Comment


            • #7
              Okay, your last replies are not reasuring to say the least...

              I make sure it's not to be felt like stalking of course, I hardly look I can even stalk someone anyway, I explained long enough my singular point of view of relationships between male and female too, but I understand it's not easy to imagine my life setup so to speak as an anonymous guy on the internet (who's well-known to be the somber coward of another here and there). Dating just as to "go out" with someone is just not my spirit also (unless I'm the one being targeted, who knows, but I've always been solitary). I may be shy but I like to be transparent rather than manipulate through flirting, which I'm unable to do at all.

              I think I'll try another approach nevertheless, maybe I'm just projecting too much for now. I'd keep my messages very short, hand-written, but explicit enough about my affinity, so the contact via e-mail would be more interesting and fertile hopefully. I just don't know how direct I should be from there, but maybe I'd be of interest instead if I made known my own interest through the letter and if the archetypes are matching in the moment. We'll see.
              Last edited by Crystal; 2 weeks ago.

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              • #8
                You don't think it's a bit odd to ask women just to have sex for a night or two and then bye? Sex is the most personal act 2 people share and to make it lke it's just a nothing thing but a thing you want with no commitment, no love no nothing, well I don't think you'll get many takers on that approach.
                The world's still a toy if you just stay a boy!

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                • #9
                  I have a couple younger guys in their early 30's I golf with. They seem to have no problems with hooking up for casual sex with skanks online.
                  -Foldus,
                  L.G. Hanger,-
                  Owner/Licensed Master Machinist
                  www.lghangerllc.com
                  PEGym members get $10 off! Coupon Code PEGYM

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                  • #10
                    I think you should talk to a psych that has experience with relationships for multiple reasons.

                    your question has a superficial answer but also raises questions which will probably lead you to deeper answers.

                    One answer is actually in your question. You are asking how a shy guy can ask for casual sex. Not if a guy can ask for casual sex. Your problem isn’t with asking for casual sex it’s that you don’t see yourself as the type of guy that can communicate like that. Figuring out why is the real first step towards being able to do that. And you’ll also learn if that’s REALLY what you want as well.

                    Edit - to be clear. The process for figuring out why should be done with a professional (in almost all cases imo). Doing it by yourself, trying to fix it yourself can have bad unintentional consequences
                    Last edited by Kickstand42; 1 week ago.
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                    • #11
                      Originally posted by Crystal View Post
                      After years of wandering, I'm considering to have sex only recently given a number of long lasting and various reasons I can list quickly before going into the topic.

                      The first reason is that I originally have a fetish for big breasts, coupled to an addiction to masturbation, which took over the need for making out. The second is that I have difficult ideals, as I've always been attracted by older / taller girls / women only, which is linked to the third about having a certain personnality / psychological profile.

                      I've always been sickly shy (and clumsy) to begin with (which can lead to small problematic situations at the occasion) and I realized it's a little more than that when it comes to male / female relationships, and I pointed this out for myself also only recently.

                      I just dislike the idea of being or feeling superior in male / female contact - in other words, the reverse of the typical relationships between opposite sexes. I think there is a well hidden part of my psychology which is like the one of a stereotypical, intellectual school girl doing things on her side but seeking for recognition - I don't know how to explain that - mixed with my androgynous and adolescent-looking aspect as I'm 30 but still looking in my 20's and easily younger compared to guys of my age.

                      With that in mind, I just don't really know where to search, for a certain type of women I'll describe below, and how to express this need, other than in the form of letters where to express this "weak point" of mine and this desire to offer myself to some women. I think I just need to be more focused / confident about myself and my desires, but I get depressed easily upon the idea of being ignored or refused, in any circumstances.

                      When it comes to the types of women I like, it's generally very slim or tall women, depending of the style, blonde / blue eyed at best, and I like asians too, generally between 35 and 65. Also, tall athletes / muscular women, and it's a special thing or kink I don't know what to make of since I never went to a gym (I like sports but I'm asthmatic sadly). In fact I dream of getting "f**ked" by one of these but I don't know where to do my research on the internet or irl to reach this goal, what communities to target.

                      I would detail more about my situation after getting some replies since I think the introduction is long enough already.
                      First, this is kind of unhealthy as you really shouldn't have anything in sex you obsess over. It sort of sounds like that your interests sexually are so profound that you might have them impacting your life. If that is the case, you need to work on that, possibly with a psychologist. If these are just sexual interests, that is a different story.

                      The other thing is that no average woman is going to be into these things. I've dated a huge amount of women. Sometimes I go on 5-8 dates per week. During this time, I've gotten to see a lot of similarities with women. I'm looking for something else, but I have come across several women who do have fetishes. So one date was enough for me to move on.

                      People who have these fetishes do not have them in a bubble, meaning that they tend to have other circumstances in their life that are unhealthy and need to be dealt with. In my experience, women have been severely emotionally damaged. One woman I knew who liked this is unable to have a normal relationship with the opposite sex. She is single, still has her fetish, but wants a partner. There are lots and lots of life problems these people have. I understand you are looking for fun, but by inviting these people into your life, you are inviting in their problems as well. Some of these people are emotionally unstable due to the trauma they've experienced.

                      As far as sex goes, really you should get to know the person. Regardless of the sexual act, it requires trust to some extent. I realize probably that is what you are trying to avoid, but the FACT is that women feel vulnerable with men regardless of fetish because they know that men are capable of overpowering them if they wanted to. So women are very careful and cautious regardless of fetish. In fact, women with fetishes are probably more cautious because they've had more negative experiences with men who have issues.

                      So knowing all of this, you should probably not be into women in this way. It isn't really going to turn out all that well in the long run for either of you.

                      But that being said, there are websites that cater to these sorts of things. Be direct about what you are asking for because being indirect about this won't work. If you were willing to have a typical sexual encounter with a woman, you could be indirect and seduce her in a positive way, provided it is the right woman. I've met a few dom women and all of them want to own a man for some time and those that don't expect you to pay. Being direct and open about who you are is pretty much the only way... But most women are naturally into the opposite dynamic, so you are ruling out a good 90% of women, at least. Then with some sort of compatibility, you are looking at really a very low amount of possible women who MIGHT be willing to do this.

                      I am a former athlete and I still train. I like feminine women. All of the female athletes I know are kind of like guys. We hit the weights together. Some of them have deep voices, broad shoulders, etc. Definitely not my type. Yet, they are still women and they tend to want a guy who is bigger, stronger, more dominant than they are (not necessarily sexually).

                      You are going to have a very tough time meeting a woman who is going to fit your fetish.

                      I'd suggest working with a psychologist to figure out why you have this fetish, cleanup your diet, hit the gym 3-4 times per week, and build some career goals. If you work your ass off for a year on that, then also work on how you dress and how to clean up your physical appearance. Meanwhile, get out and socialize with people and build some social skills. After that year, 10% of chicks you meet will do almost anything you want once they trust you. That is the most direct way.

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                      • #12
                        Originally posted by Kickstand42 View Post
                        I think you should talk to a psych that has experience with relationships for multiple reasons.

                        your question has a superficial answer but also raises questions which will probably lead you to deeper answers.

                        One answer is actually in your question. You are asking how a shy guy can ask for casual sex. Not if a guy can ask for casual sex. Your problem isn’t with asking for casual sex it’s that you don’t see yourself as the type of guy that can communicate like that. Figuring out why is the real first step towards being able to do that. And you’ll also learn if that’s REALLY what you want as well.

                        Edit - to be clear. The process for figuring out why should be done with a professional (in almost all cases imo). Doing it by yourself, trying to fix it yourself can have bad unintentional consequences
                        I think you are absolutely right.

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                        • #13
                          You know, being single and looking for casual sex is not that bad. Of course, everyone has their own ideals that's why I look for single ladies near me free on 100hookup website. By the way, I am sure you will find this service awesome too so just give it a try and enjoy. Hope it helps.
                          Last edited by Cavel; 8 hours ago.

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