Anxious around women or gay?

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I have a long-held conundrum that neither my (straight) psychiatrist or psychologist have been able to answer. In short, I have never spoken to a girl on a personal level let alone had any romantic interactions. I have had sex with around 50 or so guys and chatted with another 450 over the past 8 years (I developed a database to keep track).

Around 95% of the guys have dumped me within hours of sleeping with me claiming that I am "strange" and "weird" which has left me feeling rather unfulfilled. The remaining 5% continue to speak with me but they all have some form of severe mental illness - one is always negative about everything whilst the other is an aspie who stalks, stabs, and has been in jail multiple times for breaking into houses of those he thought "wronged" him. The negative one likes having purple hair and outlandish dress - I used to have a banking job and other staff once saw me on the weekend with him which led to the office gossip of me being gay. I was then asked at the Christmas party whether I am a "thrower" or a "catcher" by a drunken co-worker. It also makes it difficult during workplace catch-ups - "so do you have a girlfriend?" etc. If I had some sort of sane bf at least I could maybe consider being gay.

I put much effort into looking attractive - I am 27yo, white, on a constant diet (being 55kg / 125 pounds), always fully waxed including brazillian (painful, expensive), constant visits to dentists for perfect white teeth, constant visits to doctor for perfect skin, spending on tight fitting clothes, etc. This leads to them nearly always wanting to have sex with me but that’s all they seemingly want. I use sex to attract them to me so they at least spend 30 mins talking to me.

A couple of years ago I was with my female cousin at a local cafe, I was surprised by the different reaction I got from the cafe owner. The last time I visited, he completely refused to serve either me or the guy I was with. When I was with my female cousin, he was all "oh what a cute couple - you are so adorable!" and was bringing out free cake etc. Given I had never really been out with a woman in a personal setting - this made me wonder....has this discrimination kept occurring yet I have been oblivious the whole time since I had not known anything different?

I later one time had sex with a pre-op transsexual boy who had developed breasts. I found it somewhat enticing to suck on his breasts during sex. It made me wonder maybe I should try a girl?

I then tried online dating sites but no woman seems to want to do anything with me. I am not sure how to approach such things in person. With guys, it is like ordering pizza - I just open up Grindr, Gaydar, Manhunt and within 30 minutes I generally have 5 or so offers for immediate sex or meetups.

It then led me to think - do I get with guys because it is just easier since it is all electronic?

Do you have or want more of an emotional connection with men or women? I'm a lesbian and I can get along well with men but I wouldn't want to be in a relationship with one.

Based on your history I would guess you are gay because your post doesn't reveal any physical or emotional longing to be with a woman and it seems you must like sex with guys. As for the breasts thing, in my high school and college years, my gay male best friend and I loved each other so much we tried to be straight together multiple times (in between breakups) and he seemed to love my breasts whenever we made out. But he is totally gay and has never been with another woman in the 20ish years since. I have never been with another guy and have been with the same woman since not long after he and I decided we were just really good friends.

People do treat us like crap when they think we are gay, sometimes. But in the end if you are gay, I think you'll be happier being who and what you are.

I love how blunt these posts are sometimes..."I use sex to attract them to me so they at least spend 30 mins talking to me." I don't mean that in a negative way, of course. I also loved your description of "the remaining 5%." I was slowly nodding and smiling while reading that whole paragraph because I've been in similar situations.

I generally consider myself the "sane bf" type, and from that perspective I can tell you that neither me nor, as far as I can tell, the vast majority of other "sane bf" types that I've met are warm to the idea of promiscuous guys. I don't know when you started and I don't know what your habits are like now, but step 1 to finding a sane boyfriend would be to cut way back on the whole having-sex-with-many-different-guys thing.

I mean, think about it- if a guy wants someone he can be emotionally close to, he's not going to invest his emotions in a guy who seems to have no regard for them. In my experience, a lot of "sane bf" types tend to be monogamous types, and monogamous types usually don't approve of their partners having sex with anyone but them, let alone lots of people other than them.

You have to find ways other than sex to attract the monogamous guy, such as sharing common interests with them. If you're both (just for example) into chess, then find a chess enthusiast. If you have no interests other than sex, then you have to develop other interests.

And finally, just follow your heart. If your heart leads you to a guy, then date him and don't worry about whether or not you get classified as straight or gay.

Thanks for the responses InTheDeepEnd and Magdalena.

InTheDeepEnd: I am not sure. Women generally scare me as I think they are plotting against me or somehow otherwise judging me. My two key experiences are a girl saying she wanted tickets to a dance party - it later came to my attention that she only spoke to me because it was highly exclusive and I happened to be a handful of people authorised to buy tickets, she came along and promptly dumped me within minutes. The other time was after inviting a girl who was very eager to accompany me to a high profile cocktail party, I was promptly dumped after she spotted a TV celebrity in the crowd. A guy at high school started touching me in the library and I later became aroused by looking at gay porn. Given I was at an all boys school, I became more accustomed to being around boys. It just feels safer since I can find them so easily via Grindr, Gaydar, etc. I have no idea how to approach a girl or what appropriate protocol is. With Grindr, no introduction is nessesary since I have already spoken to them and come to some sort of arrangement.

Magdalena: Yes, it seems that guys dont like "promiscuous guys". I have never understood why. My thinking was that the guy becomes more valuable as a result of increased sexual practice with the value being tempered by the increased risk of STIs. My problem is that I tend to approach queeny 20yos but it seems I dont have much in common with them except us feeling a physical attraction. As a result of no conversation and being uncomfortable about going to some gay bar to dance - I realise the best way to fix this is just to have sex with them. That keeps them sleepy and then they hug, cuddle, and talk to me about stuff. Nowadays I make deals with them - if they want sex, they are required to spend the morning having breakfast with me. It reminded me of my contract law studies - one cannot add new conditions once a contract has been formed without both parties consent. As such, rather than sleeping with them and hoping they will have breakfast (adding in a clause without prior notice), I realised I needed to assert the clause before the transaction (sex) took place and make it a part of the contract. That said, your idea has merit - one of my prior psychologists had suggested attending gay activity groups.....for chess, etc.....it seemed to have nice boys there......dentists, doctors, etc.....they all seemed to enjoy my company and kept laughing at everything I said....that said, they were quite boring compared to the 20yo queeny boy who would say "lets go on a cruise!" and who would look like a replica of a boy in the porn movie I had watched the night before.....I felt as if I was setting for second best.....

I keep thinking that all this incremental investment (additional expense to attract the hot gay guys) over and above my sunk costs (what I would have otherwise spent) - e.g. the waxes at $250 x 12 = $3,000 plus hair at $100 x 8 = $800 plus fashion at $200 x 5 = $1000 plus associated going out expenses $50 x 10 = $500 - results in around $5,000 per year. If we then apportion that across the number of successful events (i.e. getting boy to talk and improve my self esteem and have sex) of 1 per quarter which is the run rate at the moment that means each event comes at a cost of $1,250.

If we compare the $1,250 to the cost of a prostitute it seems that the prostitute provides a better return on investment. The prostitutes charge around $180 per hour. The prostitute also comes with a better risk/return profile - a prostitute is relatively well practiced and only has say a 10% chance of offending or dumping me mid-meet up. The random Grindr guy has no obligation to make me happy or have sex, thus there is a 40% chance of being dumped.

I was discussing this with my psychiatrist who said "just jerk off to some porn, it is the same as having sex with a stranger and has less chance of you getting STIs"?