I would say the lack of positions available is the first problem, doggy is next to pointless, you will slip out more often than not, even more so when spooning. My wife needs to keep her hand over her pussy to stop me from slipping out or to guide me back in when I do... so we rarely bother. Missionary is 50/50, if she's wet and i try to fuck hard, it will slip out as well, so going slow is ok. The only one that sort of works is cowgirl with her on top, that way she'll just grind her pussy rather than bounce, plus she can play with herself at the same time.
Other than that, before the internet came along, trying to find or purchase small condoms was next to impossible, regular ones would just slip off, which made it next to impossible when trying to date women, especially in the mid 80's when HIV hit, so guys like me just had to go without.
Even ****** wouldn't fuck without condoms, so there were no options... for me anyway.
And lastly, dating itself, was/ is *******, trying to meet women. Wanting a second date, and knowing the whole time you were going to have 'have the conversation'... either knowing, they wouldn't ring you back after that... or if they did see it/ experience it, if you didn't get a third date, you'd be certain, all her friends would be told/ laughing about your size, once they ask what happened to that nice guy you were dating? Then fearing they may know mutual friends/ colleagues and 'your dirty little secret' being spread even further.
