My First Threesome

NOTE: A slightly edited version of this originally appeared anonymously in The Celestial Teapot Magazine in 2013. Here is the version that was sent to them before their editing.

This is a true story. Names have been changed.

It was toward the end of the school year in 1988, and I had already turned 17. We would spend several weekends at our friend Tina’s house. Tina was a lesbian and in 1988 living in Southern California: no one gave a shit that she was. Tina’s parents were cool with it and let boys spend the night because they knew nothing was going to happen. Of course, they let girls spend the night, too… and surely they knew something was happening there?

Whenever I would crash at Tina’s, I would sleep on the floor at the foot of her bed. One weekend was pretty crazy and several friends were crashing at Tina’s house: including Anna. Anna was bisexual, and again, living in Southern California, no one cared. I think it’s safe to say that most teenage boys adored the fact that she was bisexual because they all secretly hoped that if she were their girlfriend that they could share the bed with another woman. What can you do about raging hormones and puberty? Oh yeah… that fantasy continues on into adulthood, doesn’t it?

Something woke me up during the night. I’m not sure what time it was, but I guessed around two in the morning. I opened my eyes and listened to figure out what woke me up. What I heard was the moans and groans of pleasure coming from two distinct female voices. They were close. They were behind me.

I slowly picked my head up and peered over the foot of the bed. There before me were two writhing bodies: Tina & Anna. I’ll avoid referring to them from here on out as “T&A.” They were way past heavy petting and practically sliding into home base by the time I was put into the awkward position of being an indoor version of a Peeping Tom. It should go without saying that the erection was instantaneous. You know, raging hormones and puberty and such.

I’m not even sure how much time passed when Anna noticed me at the foot of the bed. She looked at Tina and waved her head in my direction, letting Tina know I was there. Tina looked down at me and I could see the sigh in her face. I felt instant guilt for being there, guilt for staring (even though it could have only been seconds or as long as an hour), and even guilt for having an erection. Before Tina could cover up or protest, Anna said, “You know, you’ve always said that if you were going to try, you wanted it to be with someone you knew and trusted.” Anna peered down the bed and gave me a wink, and I assumed that “going to try” meant sex with a boy. I nodded back letting her know that no one would know about this. Ever. Not even when I write about it as an adult for a magazine.

Tina thought about it for a second… or a minute… or a decade… I couldn’t tell. She then said softly, “Okay.” I think I did a good job of hiding my exhilaration at that single word, but I probably didn’t. The guilt I was feeling went away instantly.

I moved up onto the bed and Anna helped me get undressed while I kissed her and caressed her already naked body. Tina was watching, curious and suspicious at the same time, but she did not flinch when I caressed her leg and inner thigh. When I was fully undressed I moved between both of them. I had seen some porn and thought for sure that I’d know what to do in this situation: how to divide my time equally, how to not pay too much attention to one woman over the other, how to not orgasm too quickly, and most importantly how to please two women at once with only one penis: how to use all my other body parts to accomplish that and compensate for my singular penis.

In my mind as I fantasized about this moment, pretty much from the appearance of my first pubic hair, the video that played in my mind was smooth and seamless with eloquent and fluid motions and rhythms. But we all know reality is different. It was slightly awkward and there were a few giggles as we tried to figure out what to do and transition from one position to another.

I’ll spare you the details of the actual sex. It was fun and sweaty and loud at times. Mostly it was clumsy. All three of us had orgasms (some more than others) and all three of us ended up lying on the bed with limbs intertwined when it was all over. I had just had the most amazing night of my seventeen years. Years waiting for what I saw on porn videos of my friend’s father’s hidden VHS stash, to happen to me. Long years. I found myself lying there thinking, “Now what?” My inner voice told me, “Don’t say a word and just lay there and enjoy it.”

Finally Anna leaned over to Tina and asked, “Well?”

Tina replied, “Meh, it was okay, but I think I’ll stick to vaginas.”

That was the answer to my “Now what?” question. It was my queue to go back to the sleeping bag at the foot of the bed. Tina and Anna continued on for another thirty minutes while I stared at the ceiling listening: wishing I was Tina.