Alex becomes Alexa Ch. 01

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."

Alexa reached up tentatively and pulled Sir's boxers down. He lifted his hips so she could pull them off. Then Alexa was staring at the first real cock she had ever seen in person. It wasn't porn star big but it looked like a log from where she knelt.

Alexa gently grasped the base and marveled how it could be hard and soft at the same time. Sir pulled the leash again and Alexa's face was now inches from the head. "Don't just stare at it sissy, suck it." She opened her mouth and her tongue just grazed the head. Sir pulled again. Her mouth opened in surprise and the head was in her mouth. "Good sissy. Now get sucking you have a lot to learn."

Alexa tried to remember everything she had read about sucking a dick. no teeth, then use your tongue and gently suck the head. Then Sir's hand came down and pushed her head as far down as it would go. Alexa gagged at the sudden intrusion in the back of her throat, She came up coughing, a trail of spit trailing from Sir's cock to her mouth. Sir laughed. "You have to work up to that but soon you'll be all the way down on my cock." He pulled the leash. "Get back down there and SUCK, don't you dare come off of it until I let you. Do you understand sissy?" Alexa nodded.

She enthusiastically went back to sucking Sir's cock. She really liked the feeling in her mouth. Her clitty strained at its cage and her ass was still full. Alexa realized as she took as much of Sir's cock that she felt like she belonged right where she was.

Sir put his hand on the back of her head gently pushing down. "That's it sissy, are you sure this is your first time?" Alexa tried to respond but her mouth was full at the moment. "MMMMHMMM " was all she could manage. "Good girl, use extra spit get it nice and lubed up." Alexa tried to add more spit. The sucking sounds she made around Sir's cock seemed to make it harder. She moaned into it. She was enjoying this. She stroked and sucked for a while until Sir stopped her. "Good sissy but since this is your first time, my load is going to go somewhere special. Stand up."

Alexa stood up. She wiped her mouth with her hand. Sir pointed to the chair. "Now bend over the chair again. l'm going to make you mine now." Sir puller her panties down. This time they were all the way off. He nudged her legs open wider.

SMACK! she cried out. "Is this what you want slut?" He pressed his hard cock against her ass. "Is it?" Alexa moaned. "Yes sir, I want it so bad." SMACK. "What do you want?" You have to use your words to get what you want." Sir was still pressing against Alexa's smooth ass. working the base of the butt plug around and around.

"I want you to fuck my ass sir. Please take me and make me yours." "MMMM good sissy, see what happens when you use your words?" Smack, a gentler smack this time. "Now relax your ass for me. That's it, good girl." Alexa felt the plug be removed. It felt weird coming out, once it was out she felt empty. She was surprised how fast she had gotten used to it and how much she now missed the full feeling.

Alexa felt more cold liquid being poured on her ass and Sir's fingers pushed more inside her. She heard more stroking and saw Sir lubing up his cock in the mirror.

Sir came up behind Alexa, he rubbed his hard, wet cock up and down her crack. he positioned the tip right at her entrance. Before he pushed in he watched her face in the mirror. As he knew she would she bent her head down in anticipation.

Sir grabbed Alexa's hair and pulled her hair up so she could look at herself in the mirror. "Look at yourself sissy. I want you to see the instant I own you. " Alexa looked at herself in the mirror, spit and precum all over her face, a collar around her neck and a man about to take her virgin ass for his own.

"Now, you belong to me sissy," Sir pushed forward. Alexa's mouth opened in a silent O as Sir, slid the head past he opening. He stopped pushing, letting Alexa get used to the feeling of a real live cock inside her. a little a a time he pushed until she felt his hips bump into her ass. "See Sissy? Feels good doesn't it? This is what you were meant for."

Alexa could only moan. She watched her face in the mirror, she saw the look of ecstasy on her face and the matching one on Sir's face. She quickly moved past that thought because her next thought was that Sir's cock felt amazing. He pulled out a bit and pushed back in. Going farther and farther each time. Then he pulled all the way out and pushed back in. Her hole was still sensitive. This hurt. She cried out again but as soon as the tip of his cock brushed a certain spot it felt amazing again.

Soon Sir got into a rhythm long deep strokes. Her clitty felt like it was going to explode despite the cage. She was delirious as he fucked her tight hole. Sir sped up thrusting harder and harder until he slammed into her. She felt a hot liquid erupt into her hole as he came. "UNG! OH GOD YES!" "He just came in me." Thought Alexa feeling blissful. He slammed into her a few more times making sure to fill her up completely. After Sir had filled her to the brim with his hot cum he slowly withdrew. Her hole felt empty again. She felt his load drip down her crack. She looked up just in time for Sir to place the plug at her hole and push it in. It went in easier this time with a soft POP. halting the flood of cum from flowing from her. Sir pulled her up by the leash. She fell back against him. Her legs were a little wobbly from the pounding she just took. Sir pulled them over to the couch she felt his wet softening cock under her as they both sat down.

Sir produced a key and unlocked her clitty. "Now cum little one. Cum for me." Alexa touched her clit, it was still recovering from the cage. Soon it was standing tall. She stroked it until she exploded all over her chest with a loud moan from her. The release felt so good. Sir then spread her cum around and then fed every drop to her. She licked his fingers clean. They both relaxed into the couch feeling spent.

After a while Alexa realized she had dozed off. She sat up, the collar was gone but the cage was back and the plug as was still inside. Alexa had become Alex again.

Sir walked in, dressed in his robe again. "Oh good you're awake. How are you feeling?"

Alex sat up, confused but content for the moment. "I'm ok, why do I still have the cage on?"

"That and your plug are presents. Whenever we play you will arrive plugged and caged. For the time being and until you want to do anything differently you will ask my permission whenever you want to cum. Even at home. Do you understand?"

"Yes sir." Alex answered. "Good. Now put your clothes back on. You laying there like that is bound to get my worked up again and its late enough as it is. "

Alex got off the couch and found the bra and panties and put them back on. Sir approved not many would have bothered with the bra. It seemed this new sissy was very diligent. He was staring the whole time. When Alex finished dressing with his boy clothes over his bra and panties, Sir walked Alex to the door. Before he opened it he kissed Alex again passionately. "You did great for your first time. I cant wait till next time."

Alex smiled. Happy to have finally done something. This had been a great experience. He walked out to his car and waved to Sir. As he drove home, the plug still holding Sir's cum inside him, Alex couldn't wait to be Alexa again.

Epilogue-As his new sissy drove away, Sir, whose name was actually Mike, was scrolling his phone looking for something. He went back into his sex room and put the file he wanted on the TV in the corner.

The picture showed the room he was in, it was wired for full video on 3 cameras. A young woman stood in frame wearing a matching pink bra and panty set. He looked at the time stamp. It was two years ago but the she was wearing the exact same set and bore a striking resemblance to his new sissy. "Well this just got more interesting..."