My family are mostly from backwards third-world countries with ingrained patriarchal societies and a mindset from the 1800s. Some family members believe that people who have ASD should be locked up in mental institutions for life. You get the idea.
An example is when aunts and uncles at get-togethers would ask me, "Hey, you still single, boy? How old are you now 26?!" or "Hey, boy, I never saw any of your girlfriends. You do not want one or what, boy?"
It may be the Asperger's, but I always have felt obliged to answer questions totally honestly, without questioning the person's intentions of why they are asking in the first place.
My mother is much more sympathetic to my case, herself having Asperger's and also berated by family as a child. She was not insulted really for being a virgin until 27, but she was and is constantly berated for getting pregnant with me from her first time, plus out of wedlock. So my nickname amongst some family members is "the bastard".
My mother was called retarded and a mute as a child for her abnormal mannerisms and inability to respond to people in conversation due to Asperger's and selective mute autism. So she knows how I feel.
You are correct, I have set some boundaries. Last week I had severed all ties with my extended family, and I no longer will meet with them during family get-togethers. No point in meeting them so that they have more material to gossip about.
That still does not help that here in this city, where many people whom I meet are judgemental about relationships and virginity. Both male acquaintances/friends and women who may be interested. I once met a 33 year old male virgin during a meetup, and he was very ashamed of it when he admitted it to other people. Some male acquaintances refuse to talk to him because they do not want virgins as part of their social group. That includes people like me.
The only solution is to leave the city (and country), which I am working on right now.
Thank you for taking time to explain. Your oversharing/family dynamic makes more sense now.
Answering questions honestly, I believe, is an Aspie trait as I'm the same; however, I have years on you and have learnt to answer questions which I deem 'none of your business' with a question.
For example 'do you enjoy sex' would be answered 'what do you want to know that for'. So, when you're asked again 'are you a virgin', work on answering with a question or just a simple statement that doesn't give a direct answer.
I'm English and live in England. We are, as a rule, more reserved. The only time I've heard people being teased about sex/virginity status was at school, ages 14-16, not adults.
I think it's a positive thing that you're not going to attend family gatherings, particularly when you're the source of gossip. Remove the source, they have to find something else to gossip about.
You sound as if you have loads of positive qualities, but your social groups are not conducive to meeting like minded women. I hope that you do meet someone, but please, if/when you do lose your virginity, refrain from over sharing as it's disrespectful.