During university, I used to work on the western coast of the United States. I had an internship with an accounting house based out of Washington state. I used to occasionally visit a locally owned restaurant due to its close proximity to my work location. I grew acquainted with the staff there and knew most of them on a first name basis. That is why I was quick to notice a new worker that was hired for the evening shift.
This worker was very young (early twenties), no facial hair, blond, skinny, and about five feet and five inches tall with buzzed hair. He was an archetypical twink with a relatively high pitched voice.
“H-Hello sir, that’ll be nine dollars and twenty-three cents,” he said with a shy smile after my order was ready. I was well dressed and somewhat out-of-place at this establishment but I was hungry as fuck (in more ways than one). I asked for a copy of my receipt and saw that his name was Sam. I also tipped him with a two dollars that contained a special handwritten note in between the notes. After sitting down to finish my meal, I saw him glancing sheepishly at me. All I had to do was wait to see if he took up my offer.
…
I had already booked the hotel room for the night for Sam and I had all of the materials ready. I was dressed in a dress shirt and tie. For added appeal, I was sure to wear tight leather driving gloves so I could make the best of the following situation. At around nine p.m., I heard a knock at the door. I opened the door to find Sam dressed in a dark tank top and tight ass-hugging denim shorts.
“Hi Allen!”, said Sam. “Hey Sam. Are you ready to get dressed?”, I said as I slapped his ass. A few minutes later when I saw Sam, I was impressed. He was a perfect representation of a sissy. He had on a blonde women’s wig and women’s knee high leather boots that showed off his nearly hairless pale legs. “Remember, your name is Samantha now…”, I said as I handcuffed Sam’s hands behind him as he sat on the bed. As he just squeaked out something in the affirmative, I went to retrieve my the beverage I bought a few hours earlier.
“Remember this Samantha?”, I said as I shook the milkshake in front of her face. “I never finished the vanilla milkshake I bought. That’s gonna be your job. Understand?”, I said. Samantha said yes quickly. I unzipped Samantha’s jeans to reveal that she was wearing nothing underneath as indicated on my note. As I gently pressed my fingers against Samantha’s neck, I felt her pulse pounding against my fingers. My cock began to throb as I began to stroke Samantha’s penis with my right hand. “You’re not man enough to be a man in my opinion. You’re too weak and diffident. It doesn’t help that your dick is barely three inches hard…”, I said gruffly. With my left hand, I held the uncovered partially consumed and melted milkshake in front of Samantha’s dick.
“Cum, sissy. Your face is flushed red. Cum for me now!”, I said as I felt my Samantha’s cock throb in the my right hand. She made a pathetic gasping noise as if someone knocked the breath out of as she came into the milkshake.
“Good girl. You don’t disappoint…”, I said as I kissed Samantha’s cheek lightly. “T-thanks”, she whispered. I undid my silk tie and dropped my pants. I took the milkshake, grabbed my now pulsating cock with my right hand, and came into the milkshake. Samantha quivered and bit her lip in anticipation. The outside of my right leather gloves now contained both my own and Samantha’s cum. I extended my right hand and Samantha extended her tongue to lick up our combined cum. I undid her handcuffs and she thanked me.
I then grabbed the old and liquified milkshake and sat behind Samantha so she could rest against my torso. “Drink it sissy. Drink it for your master”, I said as I held the milkshake in my right hand. I gently pressed Samantha’s ear against my chest with my left hand. I wanted her to hear how she made my heart pound as she slipped down all of the milk, sugar, and semen. “I did it master”, she said with a smirk. As I lay there with newly sissified Samantha, I was satisfied and looking forward to future encounters together.
Source: reddit.com/r/sexystories/comments/g6yths/creation_of_a_sissy_the_milkshake_part_i_mtmm_gay