Jim
Jim first time was with a girl he meet in the pub, he was sixteen and drunk. She was kind and kisses his scars, bones and stretch marks, told him his was beautiful. He didn't believe it at the time.
Spock
His first was with Nyota, it was sweet but awkward. It was a month before their on year anniversary.
Leonard
With a boy called Brandon, in Brandon parents bed it was the last year of high school. They almost got caught.
Nyota
With her boyfriend Justin, she regrets that too.
Hikaru
With a boy at the adacamy who was training in security. He was cheated on by him. He meet Ben a week after.
Pavel
Was with Gaila, it was after Khan, they got drunk at a pub and it just happened. They parted as friends.
Scotty
His high school sweetheart a boy called Nick, he often let him stay on his crouch after his Nan died. They never spoke after he left for star fleet.
Carol
Was with at a party mostly because everyone else was doing she did it with a boy call Harry. She lasted about 30 seconds.
Christine
Was with Lillian they won first prize together as a duet, they celebrated together.
Gaila
Was with Joel her boyfriend who later gave her a STI, he told her he loved her.