When my old college roommate Patrick texted me to tell me he was engaged to his long-time girlfriend Ashley, I was overjoyed. He and Ashley had been together for five years and were the perfect couple - socially awkward nerds whose weirdness perfectly complemented one another.
Patrick and I first met in freshman year when we were randomly assigned to be roommates. We bonded quickly over our love of pranks, both on each other and working together to prank our dormmates.
After college we had gone our separate ways, each moving back to our hometowns. With our busy lives, we texted occasionally but hadn't seen each other in several years. His engagement was the perfect excuse to plan a guy's trip - so we booked flights back to our college town to visit campus and spend the weekend catching up.
It was only right that I send him a prank gift to celebrate his engagement. After looking online for a while, I settled on a novelty tuxedo thong. Black and white with a little bowtie and buttons in the front. With it I sent a note that said "to wear for your wedding."
I didn't know at the time what that dumb prank would lead to.
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The weekend arrived and my flight got delayed for several hours. So I didn't get to the hotel until late in the evening, and I met Patrick in our hotel room. I was absolutely exhausted, and I couldn't wait for a shower and a good night of sleep. When I arrived though, I was surprised to see that there was only one bed! There must have been a mixup or something, and instead of two twins we just had one queen bed. No problem though, we had shared a bed on a couple occasions in college.
Patrick greeted me with an enormous hug. I noticed the last several years had been good to Patrick. Although he had always been a tall guy, 6'2", in college he was lanky and underfed. He had clearly hit the gym, and he now filled out his frame with muscular shoulders under his typical AC/DC t-shirt.
Patrick wasted no time in thanking me for my gift. He blushed a little and dug in his suitcase to pull out a wrapped box, which he handed me.
While I opened it he said, "It's so good to see you again! I'm glad we finally made time. I wanted to ask you, though... would you be a groomsman for the wedding? I got you a little something. I guess I sort of assumed you would say yes."
Inside was a nearly identical black-and-white tuxedo thong, but this one had the word "Groomsman" embroidered on the triangular back.
Embarrassed and a little bit aroused, I managed an "Of course I will!" then mumbled something about being tired and absent-mindedly carried the package with me to the bathroom where I ran the hot water and took a much-needed shower. Under the water my mind kept coming back to the tiny tuxedo Patrick had gotten me. Surely he understood that my gift to him was a joke, right? He wasn't really meant to wear it... I was just trying to razz him... and I probably wasn't really meant to wear mine... unless...
I decided to take a chance. I toweled off and changed into the little embroidered thong, feeling for the first time the arousing and surprisingly-not-so-uncomfortable sensation of the string between my cheeks. I discovered I liked the pressure against my virgin butthole. In a moment of either bravery or stupidity I re-emerged into the room to show off my gift.
