First Time

I just did a blog entry detailing the time I lost my virginity, so I was wondering:

What was your "first time" like? Was it awkward or amazing? Was it with someone you were dating or just some random chosen for that particular purpose? Did you start off in Kink or was it vanilla?

My first time was my wedding night in our new apartment. So new that we only had a bed and little else. It was sweet, awkward, nerve racking, painful, absolutely amazing, and totally vanilla. Lol.

I read your blog post for this! Awesome!!

Figured I'll share a bit about my first time... Might as well.

It was vanilla. Spare of the moment with a boy I had the biggest crush on at the time..? lol.

It happened at my house while my parents was gone one Saturday evening. All in all, it was kosher. Later in life found out it could've been better had I taken the lead haha.

Crazy thing though, this all happened 14 years ago, and he's still here!!! ???

My first time was also my first experience with any type of kink and they talked me through the correct way in choking beforehand and it was great although I was quite nervous. It was a girl I met at a bar but she helped guide me with her limited knowledge of kink for a while afterwards.

I don't remember, I was drunk and can only recall flashes.

so many jokes....So your partner still has the box your virginity came in ...Ducks the flying coffee cups!
joking aside, that was beautiful to read

My first and only new years resolution I kept lol. To lose my virginity before I turned 16! Was eh he was my bf a year old then me. Found out the next day he also slept with a so called friend of mine. I dumped his lunch tray and chocolate milk on his head. Lol we are friends till this day!

I chose someone for that particular experience. The first time was painful. I halted the whole proceedings and went home. I went back the next weekend to finish what we had started. The next few weeks was the best sex I have ever had. Definitely on the kinkier side ?... Sometimes I wonder if I should have chosen someone less experienced. Lol.

My first time was so horrible its a danged wonder I didn't become a nun like my mother wanted. LOL I had graduated high school and moved into my own place I was 17. I had been dating the guy about 8 months or so and figure why not? I have my own place. He was a fumbling idiot, not sure he was large enough the break my hymen and I just found it all disgusting, messy and gross. LOL It was very Vanilla. I threw him out afterwards, drove to my parents and woke my father up for a "talk". We went to the kitchen table over glasses of Spumanti and I told him everything. Told him I never wanted to do it again as long as I lived. He laughed and told me I would change my mind later and not to worry about it until then. He was right, as always, and he still teased me about that night until the day he passed away. Even after having two children and becoming a grandmother he teased me. I miss the teasing actually.

I was 29 yrs old (as I mentioned in another topic before, I had run away from a couple of girls years before who were in pursuit of me, but I didn't feel I had enough to offer in the way of personal comforts and was more focused upon building my career). So anyway, by now I was moving along nicely and had a girlfreind (my first, whom I was serious about) that I had been seeing for several months. I remember more about events before and after our encounter than I do about the encounter itself, but it was good and satisfactory to her as well. It happened at her apartment. We woke up next morning and she was refreshed and happy. I kissed her and rushed back to my house to get ready for work.
She had two boys, the elder was 15 and he was a juvenile delinquent and had a bad attitude about any man in his mother's life that wasn't his own father. The younger boy was totally accepting and didn't take after his older brother. I liked him and we talked often. I believed he had a bright future ahead. The older boy was possessive of his mother and wanted his own father back rather than anyone else. At some point I can remember sitting with her in my car someplace and asking if she could steer him to accept that his father was not coming back to live with the family, and that he wouldn't always get his way in life. She explained she knew all to well that her son would never give up trying to get his dad back. I recall that the boy did somehow sabotage our relationship, so I walked away, wishing her best of luck.
It wasn't to be for about another decade that the chance to have another girl in my life happened.
But hey, no complaints here. Life happens and sometimes it ain't pretty.