Alex was gay, he'd known that, it seemed like forever. He didn't try and hide it, he accepted who he was. What he couldn't accept was the fact that he was still a virgin. He'd tried talking to a couple boys in high school but nothing ever happened. Much to his disappointment.
After he turned 18 he started exploring porn, he stumbled into sissy and cross dressing porn pretty quickly and never looked back. Alex ached to be a sissy for a daddy Dom type that he read about all the time. One of the best days of his life was the day his older sister finally finished college and moved away to the city for her new job, and threw away all her old clothes. That night Alex helped himself to as much of her underwear as there was and some other things. He would wear it every chance he got at home but he hadn't worked up the courage to go out wearing anything, even under his clothes. He'd even stolen some of his mom's makeup and tried it out when his parents were on a weeklong vacation. He got to spend an entire week in the house by himself. He wore his girl clothes the entire week and had never felt happier.
When he was finally tired of just looking at porn he decided to do something about it. He made a profile online and started looking. He spelled out what he was looking for. He wanted an older Dom top to take him and show him his place. It didn't take long to get tons of responses, all the older horny types trying to entice him with off angle dick pics and making demands of him in their first messages to him. After several days he found one profile that piqued his interest. A man that lived fairly close and offered to take it slow with him and to fulfill his every fantasy. They talked for several days, Alex explaining that he wanted to be a submissive but was very inexperienced. The man who he called Sir, was very patient and explained everything from certain terms to Alex, to how sex between men actually worked and not just what he watched in porn. He set ground rules for their meetups and what Alex should be on the lookout for with other partners. In between the friendly advice, he teased Alex mercilessly but one of Sir's rules was that Alex wasn't allowed to cum for 1 week before they met up. Sir passed along some of his other rules and tasks for Alex to make sure he was properly prepared. Finally the day came. Alex prepared himself, accomplished his tasks and drove over to Sir's house.
He was slim, 5'5, and only 120lbs. He had shaggy blonde hair and dark blue eyes. His body was almost entirely hairless, and what he did have was now going down the drain back at his parents house on orders from his host.
He breathed deeply and then knocked on the door. It was opened quickly by a man that stood about 5'9, average build of about 30, dressed loosely in a robe and shorts, a few days of stubble on his chin. Alex could see a medium amount of hair on his chest. He paused, looked Alex up and down. "Come in." He motioned Alex in.
"Hmmm." The man looked down at him like a predator and Alex was a juicy bit of prey. "You're even cuter in person." The man lifted Alex's chin and looked right into his eyes. While still holding his chin he leaned down and kissed Alex. His rough chin stubble felt good on Alex's bare cheeks. Their mouths opened and their tongues danced. For Alex it was the most erotic kiss of his young life. Considering it was also the second kiss of his life wasn't important.
When the kiss ended the man turned and walked deeper into the house. "Leave your shoes by the door and follow me." Alex quickly complied, following the man to a back room. Inside there was a couch at the back of the room. Hanging on one wall was a selection of sex toys, along with a small table covered in more. The wall opposite the toys was one giant mirror. In the middle of the room sat a wooden chair.
The room was lit but only by several recessed lights that shone into cones on different objects in the room. One was right over the chair, another concentrated on one side of the couch, a third in the middle of the room.
The man held the door for Alex and closed it behind them. Alex heard a lock click. "Stand over there." He pointed to the side of the room by the chair and the sex toys.
The man approached from behind. He started to rub his hands down Alex's back, then down to his round ass. "Do you remember what we talked about?"
Alex's mind flashed back to their conversations on the app. Where Alex had told him how desperate he was to be fucked and that he wanted to be used by a man. turned into his slave, his play toy, his sissy. "Yes, sir I remember." he said.
He remembered the man tell him what he wanted Alex to wear, how to prepare his body for today, and what would be expected of him. They also went over any limits that Alex had and what safe words to use. "Good." The man stepped away and picked something up from the table. it was a black leather collar with a metal closure and a big ring in the front. "Now what happens when I put this on?" he asked Alex.
Alex answered, "My name becomes Alexa, I become a sissy girl and become your property until you take the collar off. I will do whatever you say and you can do whatever you want to me unless I use the Safeword, in which case we stop playing immediately and I leave."
"Good, now do you consent to that?" Alex gulped. He was almost shaking from the anticipation. Here was his chance to back out, he could walk out right now and forget this happened. But his cock was as hard as steel and he WANTED this. he had been craving this. "Yes, Sir, I want this." CLICK a lock was fastened to the collar and with that Alex became Alexa. "What's your name?" Sir asked sternly. "Alexa." "And what are you?" "I'm a sissy Sir."
Sir stepped away and stepped in front of Alexa, "That is not appropriate attire for one of my sissies. Take those boy clothes off right now. You are a sissy now and sissies wear girl clothes. Lets see if you followed your first task." Alexa reached down and pulled the black oversized t shirt off revealing a simple pink cotton bra underneath. Alexa was staring at the ground as she started to lower his tight jeans. "Faster sissy," the man barked. Alexa fumbled at waist of the jeans undoing the belt and sliding them down. Alex stepped out of them, revealing a matching pair of plain pink panties. The front was bulged out by her thin 5" cock. A small wet spot was staining the front. Alexa stared at the floor still hoping that Sir would be pleased by what he saw.
