A woman has shared the painfully awkward story of a one-night stand that went hilariously wrong, revealing a fundamental lack of sexual experience on her date's part.
The Promise of a Passionate Night
In 2018, fresh out of a serious relationship, the anonymous woman turned to dating apps like Hinge for comfort and intimacy. She matched with a man named Tom, who was 28 and seemed like a good option for a casual encounter. After minimal chat, they arranged to meet for drinks at a pub near her flat, with the unspoken understanding it would lead to a one-night stand.
The date started well. They bonded over a shared love of the TV show Spaced, shared a kiss against the pub wall, and giggled their way back to her flat. The expectation was clear: a night of fun, no-strings-attached sex.
The Bedroom Blunders Begin
The first red flag appeared when it was time to put on a condom. Tom fumbled clumsily, dropping it and examining it with confusion before finally managing to get one on. The woman's hopes for the night began to dwindle.
Things took a far more awkward turn when they began having sex. Multiple times, Tom accidentally attempted to insert his penis into her anus. "'Oop!' I feel him go towards the wrong hole," she recalled. After several failed attempts, she sat up to see his face full of confusion and embarrassment.
She suggested switching to the missionary position to eliminate any further mistakes. The sex that followed was quick and unsatisfying for her, after which Tom fell asleep snoring, leaving her bewildered in bed.
The Shocking Revelation Weeks Later
The mystery was solved a few weeks later when, while scrolling through dating apps, she received a message from Tom. He confessed: "I didn't tell you because I was scared, but I was a virgin when I met you."
The woman was not shocked by his virginity at age 28, understanding that people wait for various personal, cultural, or religious reasons. What upset her was his failure to communicate this crucial fact beforehand. She reflected that had she known, she would have been gentler, moved more slowly, and actively guided him to ensure a better first experience.
She politely declined a second meeting but expressed hope he would have great sex in the future. The encounter left her with a poignant lesson about bedroom communication.
"If men communicated in bed, I truly believe they would have a better sexual experience every time," she concluded. She lamented that Tom's primary memory of losing his virginity would likely be the repeated mishap of aiming for the wrong hole, a situation that could have been avoided with simple, honest conversation.
