Insightful breakdown of First Time:

First time being squirted on?
How did you react the first time your SO squirted?

First Time Dildo Use
My partner suggested anal play. What do you suggest we start with? He's interested in a toy he can use on himself but that would be fun to also use...

The first time this happened to me...
I just had a date last night and we started kissing and whatnot. I realized that even though this girl is ridiculously hot I am just not attracted to.

First Time Vibe
I want to buy my best friend her first vibrator. In your opinion, what's the best kind (or even specific vibrator) or function to buy a newbie to...

Is this first time ?
Hi I was wondering if this woukd be to big of a change from reg size vibe 1.25. Thanks

I was 18 and he was 19. We were in a serious relationship and I'm glad that I waited til I found someone I had feelings for - it's a much better experience! I think it went as well as a first time could.
Poor guy must have been eager cause we slept in the same bed for 3 weeks before I was completely ready.

We were both 18 and secretly in love but dating other people. We would met at a soccer complex to talk and found a spot to be alone. Awwww, sweet memories. I married him 6 years later and we've been married for 15 years

I was 14 and he was 16. I was sooo enamored with him. He came and knocked on my window at 2am to come see me and that's when it happened. We had a bit of a falling out after that because I got a call from his girlfriend the next day. We ended up dating seriously a while after that, though.

Even though it wasn't "ideal", I don't regret it.

I waited until I was in high school. We dated for almost 2 years and one day we were laying on the couch watching movies and I kissed him. It was a completely different kind of kiss, and it just happened. We dated for a long time after that, however, we drifted apart when college started and figured out where our goals were taking us. We are still good friends, but I don't regret it at all.

I was 16 and my boyfriend was 20. Even for a 20 year old, it was obvious that wasn't very sexually experienced. His bedroom was in the basement of his mom's house, and we had the house to ourselves. We were listening to music and fooling around as usual. We had attempted to have sex a couple of times previously, but he had trouble penetrating me those times. This time again, he was having trouble, and I did something I hadn't thought to do before: I took initiative and used my hand to guide his penis into the right spot. I may have been a virgin, but I knew how to insert something into myself. It wasn't super painful. I felt something like a rubber band being snapped against my skin for like a second. After that, it felt pretty good, but it didn't last long! I was bleeding a tiny bit afterward, but no biggie. I actually bled the next couple of times we had sex. I think I still had some intact hymen that was getting gradually torn with each successive encounter.

Bf and I were 16 he had stayed over at my house and we were up late talking and fooling around. It started to rain and for some reason we decided to spread some blankets and pillows on the floor one thing led to another and we had sex for the first time. It was really nice and kinda of romantic.

I was 15, he was 17, we were in a serious relationship and had been fooling around in his parent's basement for a while at that point. One day I brought a condom with me and told him that that night, I wanted to try it out. It was on a pull out sofa bed. Maybe not ideal, but certainly wasn't horrible.

Lasted 5 minutes and was terribly boring.

I was 18. He was 20.
We were dating for 5 months, and it was the Thursday before Valentine's Day. He was joking around and said if I kissed him we were going to have sex, so I kissed him. A lot. And that night he asked what I wanted to do, and I said sex. We were both pretty nervous and awkward. He was super sweet though.

I was 17, he was 19. We'd been dating for a year and 3 months. He was pitifully small, it didn't hurt, but it didn't feel good either. He was really nice, and looking back, even though I'm no longer with him, I'm kinda glad he was my first. He was gentle and loved cuddling and it was his first time too so there wasn't a lot of pressure.
Since then, things have gotten more interesting, but I'm glad I had a 'soft opening' rather than a 'grand opening'.

i was 15 and he was 16 and it was just terribly, horribly embarrassing for both of us lol