I was well into my twenties before I had sex (PIV and oral) for the first time. I won’t go into the reasons here but basically it was a perfect storm of religious influence, a small town dating pool, a shy nature, a desire to be a good girl, and an early discovery of masturbation (if I could get myself off, I didn’t need a pimply-faced, mullet-haired boy to do it.
For Valentines Day, six months into our relationship, I wrapped a box of condoms neatly in pretty paper, gave it to my then-boyfriend. Then I quickly put my head under the covers in a mixture of embarrassment and delight that I’d finally decided. He got the message loud and clear. I was ready to do it! (Bless him for his patience).
He was worried and nervous and waited a few weeks to make sure I was sure. We’d already been doing things other than PIV. I learned how to give him a blowjob by firing up my little turquoise iMac, dialing into AOL, and searching “How to give a blow job” on the new search engine called “Google”. I learned that I really, really liked cunnilingus and his fingers in my cunt (a word I would NEVER have used then) and while I was a lifelong masturbator I’d never experienced anything quite like someone else making me come with their fingers and tongue.
When the day finally came, he was very careful, so careful, so worried about hurting me, that I finally had to firmly say, “Just do it!” He did, and it didn’t really hurt for more than a second, and he kept asking me if I was OK. Then it felt wonderful, and also disappointing. “Oh, this is sex?” I remember thinking. It was not that big of deal, or it didn’t seem like that big of deal.
While he was inside me, the phone rang. He looked at the caller ID and then answered, “Hi Mom!”.
“Oh, just hanging out with Maria.” I slapped him playfully and mouthed “you are so naughty!” He grinned, it was adorable.
I will always be grateful to him for doing that. It was so silly and ridiculous and naughty that it lightened the mood and made me giggle (giggling made me clench my pussy around him which got a reaction out of him, and made me all tingly and wet which taught me a new thing) and it turned what I had built up for so long as some momentous thing, into just a fun thing that we were doing together.
I was lucky in that “losing” my virginity was a fun experience. I know that isn’t the case for many. He was experienced enough (and patient enough) to teach me all the fun things we could enjoy besides intercourse so by the time we actually did it, I was well used to coming hard in his presence. With him it was safe and fun and quite a revelation.
Do I sometimes wish I had done it in high school or college? Yes, sometimes. I try not to think about the sexual adventures I would have had if I’d been more confident and more free when I was young, but I like who I am now and all those past pieces created the present person I am. She is doing just fine.