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.
"That's better. Whose bra and panties are those?" "My sisters." "Hmm," he said again "I think next time I'll have something sexier for you to wear." Alexa shuddered at the thought. "Now, panties to your knees but don't you dare let them hit the floor."
Alexa was confused but did as she was told, hooking the waistband of her panties and taking them down to her knees. Sir walked over to the table where the collar had come from and picked something else up.
Alexa couldn't tell what it was until Sir came up to him and grabbed Alexa's cock roughly, squeezing. It hurt. "What is this?" Alexa, whimpered, "My cock, Sir." Sir slapped Alexa across the face hard enough to sting but not do any real harm. " Do sissies have cocks?" Alexa answered in a whisper, "No Sir." "What was that slut?" Another slap this time to the other side of Alexa's face. "No Sir, Sissies don't have cocks." "What do you have?" "A Clitty sir. Sissies have clittys." Alexa gasped as Sir had not released her clitty yet. "Good girl." Sir replied. "Now what is this?" Sir asked again, squeezing. his large hand grabbing both thin shaft and balls. "My clitty sir.!" Alexa cried. Her eyes were tearing up.
"We have to do something about this. I can't have a sissy of mine with a hard clitty without permission." Then, Sir slapped Alexa's clitty hard. She screamed loudly. but couldn't go anywhere since Sir still held her clitty firmly at the base. Before Alexa could recover properly from the slap there was a rough feeling around the base and a sudden pressure. Another CLICK and Sir stepped back. "That's better. What do you think sissy?" Alexa looked down and saw a pink cock cage locked on her. Alexa had seen them in porn but never in real life. It looked right on her. Her clitty was straining against it but she was enjoying the feeling it gave her. " I love it Sir, thank you."
"Turn around and bend over the chair " Sir said this while pushing Alexa's arm. it was more difficult to do with her panties still at her knees. Sir forced her to reach out and grab the back of the chair. This pushed her bare ass out. Sir walked behind Alexa, running his hands over her back and down her smooth ass. Sir knelt behind her and spread her cheeks. Her little hole was exposed to someone else for the first time. Then a wet sensation made her jump. "Stop moving slut. You need to be nice and wet for this next part." Alexa felt the wet sensation and realized Sir was licking her hole. The new feeling sent jolts of pleasure pulsing through her body. It was so much better than her finger in the shower ever could be. After a time, Alexa had no idea how long, Sir stood up and went back to the table. The next sensation was a cold liquid being poured on her ass crack. Sir's fingers then rubbed it on her hole. One finger slide inside her, working back and forth. then a second finger joined the first. Alexa felt very full. She had listened to Sir when he told her to stretch her ass with whatever she could before coming over but she has still never had anything larger than a banana, and she had stopped quickly because it really hurt.
After Sir got 3 fingers inside he started to push them in and out. Alexa felt waves of pleasure. Then Sir stopped suddenly and the fingers were withdrawn. Alexa heard moving behind then a solid cold lump was pushing at her hole. "Relax your ass for me." Sir said. The pressure increased until whatever it was slipped past her ring. It burned like her ass was on fire. "OWWWWW OW take it out, take it out!" Alexa cried and she stood up. Sir was right there and grabbed her by the back of the neck and forced her down. "Get back down there slut. I didn't say stand up." SMACK a hand landed across her ass. "OW" she jumped. SMACK, SMACK! Sir was smacking her ass while holding her down across the chair. SMACK, one final spank before Sir let up. He pulled Alexa so her back was against Sir's front. one hand gripped Alexa around the throat. "Your ass is mine slut. It needed to be prepped. If you had listened, this hole would be ready for me. The pain is a lesson." Alexa realized that the object was still inside but the pain had faded.
Sir stepped away. "Panties up." Alexa complied. When she stood back up Sir attached a leash to the ring on her collar. He pulled her roughly towards the couch. She felt full with whatever Sir had put in her ass. When he got to the edge of the couch he took off his robe. Alexa was staring at the bulge in his boxers though.
Sir sat on the couch then YANKED the leash down. Alexa had no choice but to go to her knees in front of Sir. Her face mere inches from the bulge now. "Show me how grateful you are sissy. Take my cock out and suck it."
