Where it happened: In a college dorm
This isn’t a story about letting a boy’s penis in my mouth for the first time (that happened when I was fourteen), nor is it about letting a boy’s penis inside my vagina for the first time (that happened when I was sixteen). Instead, this is about the first time I let my boyfriend enter my anus. It happened only a few months ago at age nineteen, during my first year of college.
The boyfriend that I had in Grade 12 didn’t get admitted to the same college that I wished to attend, and we knew that it was over. I met my current boyfriend Bill in September of my freshman year, and our relationship quickly turned sexual.
We had oral and vaginal sex every time we met, but Bill increasingly introduced anal sex play. At first, it was one finger well-lubed with K-Y Jelly. This was all he did for the next several times. We started to make love doggy style with Bill’s penis in my vagina, and his finger in my anus. When I came I could feel my anus throbbing against his finger, which heightened my pleasure.
One day as I was about to come he withdrew his finger, and then put two fingers in. When his fingers went in all the way I came wonderfully. Still with his penis inside my vagina, he put a third finger up my bottom. His three fingers increased their speed as Bill’s release approached. Now he was using four fingers, two from each hand. The two fingers from his right hand pulled to the right, and the two fingers from his left hand pulled to the left, stretching my anus. “I’m fucking cumming, Brittany”, Bill shouted as he ejaculated deep inside my vagina. Still with his fingers stretching my anus, I came when I felt Bill come inside me.
I knew that we would soon progress to anal sex. I had always thought that anal sex was something to be tolerated by women who didn’t want to lose their boyfriends. I was beginning to discover that women could obtain sexual pleasure this way too.
The next day I began our foreplay by lubricating one of my fingers and shoving it up Bill’s bottom. Bill got hard instantly. I progressed to two, then three, then four fingers just as Bill had done to me. Bill was stroking himself as I played with this bottom. Then I got on my knees with my bottom high in the air and said, “Now it’s your turn.”
Bill lubricated his cock and my anus with K-Y Jelly. He then put his penis into my vagina, and put two fingers in my bottom. After fingering my rectum for a minute, he put three fingers in. I could feel the tips of his fingers touching the insides of my rectum. Bill knew the pleasure that I was having, because I shook with a very intense orgasm. Bill then began using four fingers as he had done the previous evening. I was in both pain and pleasure as Bill stretched my anus further than he had done the previous evening. My body seemed to release some painkillers and all I could feel now was pleasure.
Bill then pulled his penis out of my vagina and put the tip of it at the entrance to my anus. “Yes”, was all I said, and his member, well-lubricated with my vaginal juices and the K-Y jelly, entered my anus. Bill’s penis isn’t much bigger than the size of four of his fingers, so I had no problem receiving him. He began pounding, and within a minute his hot ejaculate filled my rectum. I came for a second time, as Bill continued to shoot spurts inside my rectum.
About three days later, my period began. Up till now, my periods were a time of sexual abstinence. Now, with anal sex available to us, we can make love every day of the month.