I am a bisexual guy who around this time last year, began dating men or more accurately, hooking up with men and my experiences taught me SO much about women and helped me have more empathy for the opposite sex. I have always had these bisexual feelings but never acted on them until last year.
Two things changed. I was single and just out of a LTR and I got a job that required relocating to a new city every few months. I decided that this was the time to find out what guys were like. Full disclaimer, I wasn’t really looking to date guys, I never really felt romantically that way for a guy. I was open to it but it just never happened and I just never felt the urge. So I basically started looking for hookups. I also quickly realized that I did not like the gay scene, either in bars or with OLD (Online Dating). I was open to it, it just wasn’t working out. Maybe it was too much radical change, too fast. This was a whole community and a whole lifestyle I guess, that I knew nothing about and honestly many were not that accepting of bisexuals!
I realized that I pretty much prefer sex with guys in the “female” role I guess, receiving, not pitching so I was actually able to hook up with guys who considered themselves straight but would fuck a guy on occasion, if they were horny and it wasn’t reciprocal. This was the majority of my experiences. So.. as such, I was hooking up with many of the same guys that women hook up with or date and I learned a lot about women and what they experience that was very, eye-opening to me! It helped me understand and empathize with them and I HOPE it makes me a better boyfriend or husband in the future!
First observation. It is REALLY a vulnerable feeling to be on the receiving end of sex! I had strap-on sex with a girlfriend before but she was about 5’2, petite and was very tentative and cautious. A real penis with a real guy attached, who is in many cases bigger and stronger is a whole different world! I never really associated intimidation and even fear with sex before. I’m placing myself in this very vulnerable position, mentally and psychologically and when the guy is in the middle of the act, in the throes of sex… I’m not quite sure if he’d slow down or stop if I wanted him to at that point. Some guys get really aggressive during sex, not abusive but more dominant and physical. I never had an issue but it was a big difference between what sex with women is like and I now understand why women might not be as eager to jump into the sack as quickly as guys. They have more to consider.
I had at least one experience that surprised me and taught me something I never knew about myself and still don’t really understand. I met a guy who was basically an ass. Rude, complete narcissist, basically a person you would seek to avoid in any other circumstance. Anyway, I nearly called off the encounter but decided to stick it out because a female friend warned me he was an ass but was also great in bed and I had a previous series of duds sooo… We did it.
I basically realized that I was just being used like a sex toy after awhile, like a means for him to get off without any consideration or really even acknowledgement of me. What surprised me is that this was turning me ON! I was being moved into different positions by him like he was giving his penis a workout and I was just a means to that end. He’d do things no one else ever did like sit on my face and have me kiss his butt while he called me a good little slut and again, I was turned on. So that was strange because I never thought I’d be turned on by being dominated like that or playing the role of a slut who is just there to please him. Before this, I’ve always wondered why otherwise normal women would be turned on by things like Fifty Shades of Grey or be sexually attracted to “bad boys” or jerks who treat them with no respect. Now that I’ve experienced it.. I don’t totally understand it but I can be more empathetic.
There was lots of bad sex too. Most of it was bad, honestly. Maybe that’s part of why I was so obsessed with the asshole guy I just mentioned, because he was actually really good at sex, had a beautiful penis that worked well, and knew how to use it. He was clean, smelled good, had a nice body and was well groomed. Basically what 80% of the other guys failed to be able to do. Poor hygiene, bad breath, wearing socks while having sex, finishing far too quickly or unable to finish at all. Many guys just were not that good at it would end up being a disappointment. Even one guy with a huge cock! It was fun to see the thing up close at first but sucking it just makes your jaw hurt quickly and there is really no way I’d have something that big inside me so I basically gave him a handjob.
During this time, I also began lightly experimenting with makeup. Not to look like Caitlyn Jenner or some guy in drag but to even out my complexion and just look better. No one knew I was wearing anything, it was really subtle. Well… no GUYS ever picked up on it, a few women did but they are more
attuned to it and every one of them complemented me on it. I had a very minor regimen but even at that, I was surprised at how expensive it could be an how much time it could take to properly clean your skin, exfoliate and then apply the product. I’d do a fraction of what most girls do so I can really
appreciate the time and effort now!! I also started doing things like getting mani-pedis, occasional facials and buying more stylish clothes. Again….Time and Money!! As a guy who used to use a combo bodywash/shampoo and wear jeans and Tshirts. This was a brave new world!
Another experience that I had was for a period of about a month, I actually had a male/male sugar daddy relationship with an older businessman. I did not go looking for this nor did I expect that it was something I’d ever do, I just fell into it and was surprised at how easy it was and I got a taste of how much power there is when you are on the side of the sexual dynamic that is offering sex to an eager party. I was utterly amazed at how opportunities would open up and entire lifestyles and social circles that were unreachable before could become accessible simply with the promise of sex. Again.. I was just an average guy and I had a mind blowing experience. I can only IMAGINE what opportunities there are for a young woman in her sexual prime with most of the male population vying for her attention! Even if you could not bring yourself to do this sort of thing (and honestly, I never thought I would) the temptation must be huge! So.. I was basically sitting at a bar one night playing with a hookup app when an older businessman strikes up a conversation and eventually buys me a drink. He eventually offers to show me around the city and I agree.
Long story short, we ended up in bed in his amazing suite overlooking the city after an amazing meal. I realize that he basically kept getting me to agree a drink first, then a walk, then a meal and before I knew it, he had me! You keep tasting more and more of that world and you don’t want it to stop. He was charming as well and made it seem like nothing, which it was to him because he was so rich. So pretty soon I am hooked and I keep telling myself I’ll end it soon, just one more time! I had vacation time from work and got to go on a trip to another city with him, all high end hotels, restaurants, shopping. He was easy to please sexually too, was never abusive. I found out he was married but that his wife totally approved of this so long as the guys were not exclusive. Meaning he could not see any guy longer than a month. I was relieved and also a bit disappointed and I flirted with finding someone else to do this with but never did. I actually got to meet his wife too! Very pretty woman! She said that she lets him do this and feels better about him seeing guys instead of girls. She took me out to lunch and she told me that she liked me more than any of the other guys he’s seen but their rule was that it could not continue endlessly. I told her I understood and was both relieved but disappointed too.
Another revelation was simply having female friends that I was not looking at as sexual possibilities! I met a very attractive woman who in the past, I’d be thinking constantly about how I could impress her or get into her pants and instead we bonded over makeup! She saw me fumbling around in Sephora in the mall like I was completely lost and we struck up a friendship. It was refreshing that I could see this person as more than just a hot girl! I noticed for the first time how so many men would openly gape, gawk and say the stupidest things to get her attention. I got to learn that she was had lots of interests and was studying to be a graphic designer in her spare time. She only managed to attract a series of losers and players or guys she’d intimidate too much with her beauty and they’d walk on eggshells around her.
So basically, I am winding this life experience down a bit and thinking of dating women again. It’s been really eye opening what women experience when dealing with men, with the sexual power that comes from offering sex and with the amount of time, money and effort that goes into looking good.
I’m not going to insult your intelligence and pretend that I have some amazing insight into femininity now. This was all very superficial and on the periphery but even at that it showed me that women’s experiences are very, different from guys and guys could do well to walk a mile in a woman’s shoes, even as just a simple mental exercise.