Yes, Cheryl was my sorority sister and best friend at our all-women’s private college. Taking her boyfriend to bed was wrong. On the other hand, any boy who would go to bed with his girlfriend‘s best friend was a bad actor and did not deserve to have a sweet girlfriend like Cheryl.
So that is how I justified my inviting Cheryl’s boyfriend Carl, to walk me home from the bar in Georgetown. Carl and I had been out with a group of mutual friends on a Friday night in October of 1986. Cheryl had just returned to Charlottesville on Monday to complete her final semester for her Master's degree in Systems Engineering. I was working for my family’s office furniture business in DC and living with 2 college friends.
Of course, I invited Carl inside and sat next to him on the sofa while we shared a glass of wine. Carl was a 3rd-year Medical Student, 6 feet tall, maybe 160lbs. A rower in college, his back, torso and legs were solid and strong. I was a petite girl with a firm runner's butt and C-cup breasts, which appeared larger given my small frame. After a few minutes of small talk, it was impossible not to kiss him and to lead him by the hand upstairs to my bedroom.
Of course, it was late - almost 4 am. The bars had closed at 3 am, and it would have been unfair to send him back home so late. We were both tired and needed to sleep. Asking him to sleep on the sofa would have been unfair. Besides, my housemates would have been startled had they discovered a strange man on our sofa in the morning.
So we climbed the stairs to “just sleep.” I retreated to my bathroom to put on my nightgown. Carl disrobed down to his boxers. When I exited the bathroom, he was waiting for me under the covers of my single bed.
We exchanged our “goodnights” as we positioned ourselves in bed, my back to his front, his right arm under my pillow, his left arm encircling my waist, and, understandably, his sturdy, stiff cock pressed into the small of my back.
We were just going to sleep together. Well, I tried to sleep, luxuriating in the embrace of his muscular arms. Carl had a harder time falling asleep.
I guess I should have known that Carl would not fall asleep easily. Of course, I enjoyed the passionate attention he offered me. He started by repeatedly kissing my neck, his unyielding erection rubbing against my back. His hands reached my breasts and stroked my skin ever so delicately.
His passionate kisses combined with the grinding of his cock on my back and the massaging of my breasts were a sensual delight. I pretended to want to sleep, but I loved the power of having this boy doing his best to work his way into me.
Oh, it’s not like I was a virgin at the time. I had dated a boy from our “big brother” fraternity at the nearby all-mens college. We would get together every other weekend. He was my “first.” Before sex, our highly responsible, meticulous birth control ritual consisted of a diaphragm, condoms and spermicidal jelly.
Having said that, I was not dating anyone at the time, and I was not on birth control. Cheryl had informed me that Carl had excellent “pull out” skills, but I was not prepared for such risk, even as much as I wanted him “in me.”
His kissing, back massage, and breast stroking won me over. I rolled over to face him, and we shared deep, passionate kisses. His hard cock pressed against my lower abdomen as he held me in his strong arms. Trying to sleep was futile.
His kisses moved deliberately down from my mouth, to my neck, to my breasts, to my navel and the top of my pubis. With his hands on my firm little butt, he rubbed his face back and forth over my pubic hair.
I gasped and arched my back as his lips brushed my inner thighs and then my labia. So badly did I want his cock in me, but I knew I could not take that risk.
Now I felt his tongue, gently at first, licking my labia, then my clitoris, then my inner vaginal walls. It was heaven. I should have allowed myself to climax, but the combination of guilt and fear got the best of me. Today, I still masturbate thinking about the passionate attention he offered my young pussy that night.
Inevitably, he moved up on the bed and gently inserted his swollen cock in my soaking wet pussy. I was so lubricated that his length slid into me with no resistance.

I was in erotic heaven, but knew it had to stop. While I never uttered the word “no,” I twisted my body and pulled my vagina away from his cock. I turned my back on him as we had been before we began kissing.
I do not know who said it, but the words “we should just sleep” were uttered.
And we tried to sleep, but it was impossible. His cock refused to yield. It remained hard, pressing into my back. 10 minutes later, the deep kissing resumed, followed by the southward journey of kisses, followed by enthusiastic licking of my excited pussy followed by a brief insertion of his glorious cock followed by my twisting off of it, followed by another attempt at sleep.
This unrequited mating ritual continued all night. By perhaps 7 am, Carl admitted defeat and fell asleep for maybe half an hour.
Of course, his cock and balls did not get the memo. With a mind of its own, his cock continued to maintain turgor - hoping, hoping, hoping that my vagina would offer it a more permanent resting place for the night. His balls continued to churn, producing millions and millions of sperm desperately aspiring to swim their way to my womb and fertilize a waiting egg.
By 730 am, sunlight began to sneak around my bedroom blinds. Carl began to stir. His proud cock had remained hard all night, and his balls most certainly were at capacity. This time, after we kissed some more, rather than move southward, he straddled my body with his legs and presented me with his glorious phallus. It stood tall with its heavy balls dragging against my xiphoid.
Our hearts pounded with anticipation as we both realized what was to happen next. Without a word, Carl laid his towering penis on my chest as I pressed my breasts together around it. His engorged cock journeyed back and forth between my breasts as his balls dragged behind. I knew what was to follow. I turned my head to the right as I angled his cock to the left.
To this day, I am at a loss for words when I attempt to describe the intensity and volume of ejaculate that exploded from Carl’s penis. It could not be described as a “spurt.” It was a powerful firehose surge of semen that seemed to last two full seconds. The fragrant, viscous fluid hissed as it hit the pillow behind me and splattered back onto my neck and into my hair. The room instantly smelled of bleach. Carl roared with satisfaction. It took a full minute for him to catch his breath. I smiled, relishing the power I had to cause such an eruption.
Carl fell asleep, justifiably exhausted. I had a Saturday, 9 am Junior League meeting to attend. As I left, I kissed him and told him to keep sleeping and let himself out later. I looked back to see him sprawled out nude on his back; his now exhausted soft cock lay gently over his groin. It was a beautiful sight.
When I returned home that afternoon, I learned that it was a sight also appreciated by my housemate, Bella. Bella wandered into my room after I had left and discovered the naked Carl lying on his back.
When I returned home that afternoon, there was no use in lying about my little indiscretion. The girls demanded details. Ultimately, we all ended up inspecting the now dried, stained and crusty pillow, which had absorbed the famous “cum shot heard round the world.”
“Thank god he didn’t do that in you, or you would be sooooo pregnant,” announced Bella. We all laughed.
Carl and I went out with friends a few times, but never got naked again. As could be predicted, he and Bella dated for a few weeks until she returned home to New Orleans. At least they had the decency to spend their nights together at his place. Cheryl forgave me for my indulgence. We both served as maids of honor at each other’s weddings.
Carl has gone on a have a successful career as a cardiothoracic surgeon. He is currently married to his third wife, who is pregnant with their second child. He has five children by his first two wives. He has no plans to retire anytime soon.
Almost 40 years later, I have never seen such an ejaculation. How I wish I could relive that night again.
