Discussion in ' Oral and Anal Sex ' started by gboudMay 11, Log in or Sign up. I pratically begged my highschool girlfriend to let me cum in her mouth but she didn't let me in the 2 years letting a guy cum in your mouth where together. So my first time was my first year of college. I went back to the dormroom of a girl i met at the bar and we slept together. The next mourning she was giving me a blowjob and I asked her if I could cum.