5 Funniest Sexual Bloopers (Relationship Humor)

I spotted the girl I’d taken to our prom. She looked as gorgeous as she did that night 30 years ago! From the moment our eyes met, the same old sparks started to fly. We caught up over a few glasses of champagne, and I was thrilled to learn that she was divorced and unattached as well.

As we slow danced, she put her mouth to my ear and whispered, "How would you like to drive me home right now and relive prom night?" We raced like hell to get back to her house. I pulled into her drive way and we started making out like two teenagers in heat. The car windows fogged up as I lowered the leather seats and climbed onto her. I worked her dress up as eagerly as she worked my pants down.

She really started to get going, so I picked up the pace and rode her even harder. That’s when I felt something pop in my lower back. My entire body seized up in one excruciating spasm. I had just re-injured my newly healed slipped disc! There was no way I could move –let alone finish the job of satisfying this incredibly hot woman. It would be at least an hour before I could get her out from under me. I couldn’t even raise my sorry, middle-aged ass up enough to get my now limp self out of her. With no hope of having an orgasm, she said, "What do we do now?" obviously unfamiliar with this type of injury.

Feeling like the biggest loser in the world, I said, "We have to wait until the spasms subside enough for me to move. It could be a while." She just smiled and said, "Well I suppose that’ll give us plenty of time to reminisce about what it was like when you were 18 and could do this without paralyzing yourself in the process."

3. International Arrivals: United States of Erotica

I’m a call girl with wealthy gentlemen clients who often require me to travel to discreet locations of their choice. A few years back, I was invited to join a client on a weeklong business trip to the French Riviera, where I would spend my nights pleasing him and my days basking in the Mediterranean sun.

Because he’d been a regular of mine, I knew exactly what kind of sex he liked, and took extra care to fill one entire suitcase with a wide array of S&M paraphernalia. Since he also liked to watch me masturbate while I pretended to be a parochial school student, I packed my schoolgirl uniform and favorite vibrator.

A deliciously devilish week later, we ended our trip a friendly kiss and boarded our separate planes back to the states. The flight home was one of the smoothest I’ve ever had –it was only after we had landed that I hit turbulence of my own. The line through customs was moving at a snails pace so I start up a friendly conversation with the three nuns behind me. I smiled smugly as they told me they were returning home from a spiritual retreat and going back to their parochial-school classrooms.

Suddenly, my vibrator went off inside my luggage (I’m sure it was God’s way of getting back at me for playing with his three girls)! The buzzing raised suspicion and a large, no-nonsense female customs agent demanded that I place my suitcase on the counter for inspection. With the three nuns looking curiously on, I reluctantly opened my suitcase. There in the pocket of my neatly folded parochial school blazer was my pulsating vibrator!

The nuns recoiled in unison. The agent remained stone-faced as she removed the batteries and proceeded to go through the risque contents of my suitcase. With each item she pulled out, the nuns blessed themselves. Carefully comparing my face to my passport photo, the agent asked the nature of my travel…

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Dan and Jennifer are the Founders and Senior Editors of AskDanAndJennifer.com, which has been called "the best and most popular Love and Sex advice column on the Internet today". Their videos are some of the most popular videos on YouTube. Don't forget to ask your dating, love, and sex questions in the Ask Dan and Jennifer - Love, & Sex Forums. You should Fan Dan & Jennifer on Facebook and Follow them on Twitter!

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