Welcome to the 4th and final installment of "Chastized Until He Became a Sissy". Sorry for the delay! My life has been crazy... in fact I think I may start a new series about what has been going on! For those of you following along, you already know that this is based on my real life. If you haven't read parts 1–3, you may want to go back and read those teases... the story will make a lot more sense.
For this tease you will need your sissy items... you all know what they are!
The best way to start this tease if you haven't been in chastity long-term is to stroke to the edge 10 times... ice yourself down and then lock that clitty away. At the point of the story we are at, I had been in real life chastity to an online mistress for weeks!
So get horny and lock it away if you want to truly experience my story... if not, you may stroke but don't cum until I am allowed – if I am ever allowed.
So, I was really in chastity and had my first analgasm... sissygasm! OMG it felt amazing... it was truly a full-body pleasure! Mistress had commanded me to practice... she wanted me to learn how to sissygasm in 7 minutes or less!
She sent me messages every other day... asking how long. I tried to make conversation, but she only responded to my number. I would say "10 min"… she would say "Not good enough... If you ever want to free your cocklet you will work harder."
This went on for weeks... and then one night I found the trick.
You see... I was doing it because I had to! One night I just said, "I'm going to love this," and made love to my dildo.
Shake that cage and feel your horniness... get your dildo out and start kissing and sucking it with love. Be gentle and let your mouth receive and give pleasure... you may want to softly moan as you suck... let the horniness fill your body.
On this particular night, my sissy self took over! I got so horny sucking that dildo... I put in my anal plug... and made love to that cock with my mouth! I started to drip... I was moaning and contracting!
After about 10 minutes... I took that dildo and slid it into my well-lubed boy pussy... I bounced and bounced and in about 5 minutes... I continuously leaked! I remember moaning, just like Mistress liked: "I am a sissy... I love cock." I just kept saying it over and over. It was amazing!!!
Make love to your dildo and put that anal plug in... at this stage, focus on the pleasure of being a sensual sissy and let that cock please you. Then slide it in and ride it... you may have to shake your cage! You may drip as much as you like...
`If you aren't in a cage, just edge 2–3 times! Remember to moan like a sissy! Say it over and over at least 5 times: "I'm a sissy." Mmmmmm feels good, right?
It took me about 60 minutes to recover... but then I immediately texted Mistress to let her know of my progress! She laughed and said "Good sissy!" She then said we are going shopping... you need to save $300 and get your time down to 6 minutes with oral and anal combined.
Look into Mistress’s eyes and shake that cage! Feel your submission... Cageless subs — edge for Mistress!
She then said, "Oh yea... two more things, sissy... I want you to stay full-body shaved, buy a wig... or two... and check your email. I’m sending you 8 shemale pics to become your idols!"
I was so humiliated and horny all at the same time! I checked my email and loved all of the pics!
Which is your favorite? Shake that cage and imagine sucking each one... cageless sissies, edge to your top 4.
I eventually chose girl number 8... do you agree?
I called Mistress the next day to let her know of my choice! She said that she would send me pics of her to sissy masturbate to. I was happy! I thought I had earned the key... I asked Mistress when the key would get to my house...
She laughed and said, "No silly... anal masturbate... that is what you love now, right?"
I confessed my love and agreed to continue self-fucking with my dildo. She said, "You will have plenty of time to earn your key... don't be in a rush!"
She then said, "Let me know when you can cum in 5 minutes to pictures of your TS girlfriend idol. I want to see pictures of you all dressed up while practicing!"
You know what to do... shake that cage and/or edge to my idol!
I found myself loving my TS idol more and more! Some days I even cheated to get a big release... I bought a vibrating wand and used it on my cage to cum. I never did tell Mistress about this!
If you have your vibrator, you may use it... but don’t overdo it!
Stare at her body. She is perfect! Say it aloud as you stroke or vibrate: "Mmmm, she is perfect."
About a week later, I got online to let Mistress know that I had saved up the money and got my time down to 5 minutes. She asked about my progress, and I told her I was in love with this TS and that I had sissy masturbation time with her every night.
She laughed, "Hahahaha... you are turning into a fag even faster than I thought."
I distinctly remember her saying that, because at that moment I realized I really enjoyed being a sissy and looked forward to my nighttime release.
Mistress said she would call me back — she had a treat for me. I was so excited! I thought we were going to go to the store and get a new toy, or maybe... I might even get my key back.
Pleasure that sissy cock in anticipation of Mistress’s surprise.
A few hours later, Mistress called — we were on a 3-way conference call. I heard the phone ringing. Mistress Cheryl said, "Hi slave, we are gonna have some fun. I am calling a friend. Check your email, and don’t speak unless you are spoken to."
I got so excited! It all seemed like an out-of-body experience. I was so horny and wanted relief — however I could get it.
Get to the edge as you anticipate the email and phone call. Don’t overdo it!
I checked my email and saw a message from Mistress Cheryl. I opened it, and it was a link to a Backpage.com ad. I clicked on it... and saw my TS idol. My cock jumped in the cage.
I started to read the ad, and then I heard a voice on the phone... "Hello". Mistress Cheryl responded, "Hi Alexa… it’s Mistress Cheryl again... I have a sissy slave boy all ready to come see you."
I heard Alexa respond, "Oh great... I’m pretty fucking horny... I need to shoot a few loads into a willing mouth... hahahah." Mistress laughed with her and said, "I have him on the phone now, he is dying to meet you… say hi, slave."
I was so horny hearing her actual voice. It was soft like a woman’s, with just a hint of male on some of her words. Her voice was sexier than I had imagined. I couldn’t believe it — I had imagined her voice a thousand times and actually hearing it drove me crazy.
I said, "hh hh hi Alexa." She said, "Hi slave, are you coming to see me?"
I froze. Mistress jumped in and said, "Yes. In about two hours. He needs to prep."
Alexa moaned and said, "Mmmmmm now that’s a good sissy! I’ll be waiting. Give me a call when you leave so I can let you know where I’m staying."
I was in a fog just thinking about what was getting ready to happen.
Stroke or vibe yourself in preparation! Don’t edge.
"Ok slave, today is a big day! You will have your skills tested. If you ever want the key to your clitty back, you will do everything in your power to impress me."
"Yes Mistress," I responded.
Mistress Cheryl said, "Take a shower, shave, and put on your sexiest bra, panties, and stockings; I want you looking hot for Alexa. And you better not forget to take your computer — I want to watch the whole thing!"
I said, "Mistress, is this really happening?" She laughed and said, "You are my fucking slave. What did you think was going to happen?"
I got ready. It took me about an hour. The entire time my clitty filled my cage. I put boy clothes over my sissy clothes and called Mistress back, "I am ready."
She said, "Ok, one sec." Then I heard the phone ringing. After a few rings I heard Alexa’s voice again, "Hello."
Mistress said, "Hi Alexa, my slave is ready to come see you."
Alexa told us the hotel and room number and said, "Knock 3 times and I will answer."
I felt my sissy cock shrivel — I was so anxious, but I was so horny at the same time. It was a feeling like no other.
Just as I was walking out the door, Mistress said, "Don’t forget your computer!"
The entire drive, Mistress stayed with me, reminding me of my training. She said, "I want you to enjoy this. You worked hard for it!"
Get to the edge as you prepare to meet Alexa! That’s how I felt the entire ride!
I got to the hotel. Mistress said, "Get out and go to her room."
I began to make my way to her room. To this day, I don’t remember walking into the building — I was in a fog, almost like a dream.
I got to the door, knocked three times. Alexa opened the door and said, "Come in and strip down to those sissy clothes."
I told Mistress I was there and that I was commanded to strip. Mistress laughed and said, "Well... do as she fucking says! When you are done, ask to set your computer up so I can watch."
After stripping down, I asked Alexa if I could set up my computer. She laughed and said, "Hurry... I’m fucking horny, sissy."
I quickly got onto the network and logged into Yahoo Chat to invite Mistress Cheryl to my cam. She got on. Alexa looked into the cam and said, "I am in charge now."
Mistress Cheryl said, "Lovely."
I said, "Yes Alexa."
She grabbed my face and said, "It’s Goddess Alexa to you."
Stroke/vibe that clitty! You may edge again!
She began rubbing me... It felt so good... I was moaning in pleasure, until she got to my cage and then she laughed!
She said, "This is pathetic. Haven't even met Mistress Cheryl and she owns your small ass cock."
I said, "Yes Goddess."
She sat on the bed and said, "It's time for you to please a real cock."
Stroke and rub as you prepare to suck Goddess Alexa. Get your dildo out to suck while you read, sissy!
Goddess Alexa took her clothes off and said, "Look at me! Do you want to suck my cock?"
At this point I had cum thinking of that countless times. I said, "Yes Goddess, I do, so badly!"
She said, "Good, now beg me for it!"
Beg for Goddess's cock. Say it: "Goddess please please please may I suck your cock in my mouth!"
Mmmm say it and stroke as many times as you need until you are on the edge! Look right at your dildo as you say it!
When you are on the edge, click continue!
As I begged Goddess, she just stroked her cock! I must have said "Can I have your cock?" 30 times! I was so horny!
Goddess finally said, "Yes! Get over here and make love to my cock!"
Suck on that cock, do it gently! Make love with it in your mouth and then press continue!
I gently put her in my mouth and began sucking and kissing on it! I heard Mistress Cheryl in the background say "that's a good sissy."
Goddess Alexa grabbed my head and face-humped me as I sucked her... she reminded me, "Make love to it, sissy!" I was so gentle as I sucked and rubbed on her balls...
I slowly took it deep in my throat... she moaned, "Yes!!!!!!! Deeper..." I kept going until I could tongue her balls with her cock deep in my mouth!
She belted out, "You're making me want to fuck you, sissy!" I came up for air and then slowly went back down and tongued her even more! My face and her cock were getting so sloppy with spit and pre-cum.
She pulled my head up and said, "Lick my ass, sissy." I did as commanded while I gently stroked her. I was drunk with lust! She said, "I'm going to fuck you silly, baby!"
Suck on that cock and tease that clitty! Then press continue.
After licking her ass and stroking her for about 10 minutes, she stood up and said, "It's time for me to fuck you, sissy boy." I couldn't believe this was happening — this was the moment I trained for.
Countless days and hours watching sissy porn, hypnos, and reading sissy memes. I was in femme clothing, face covered in saliva, ass juice, and precum. As I laid on my back, I thought of all the times I practiced getting fucked.
I heard Mistress Cheryl say from the computer, "Remember your training sissy, you better cum quickly."
Goddess Alexa said, "Oh don't worry, he will... I’m going to fuck him silly!" She put a pillow underneath my lower back and ass, and I felt her start to finger and lube my sissy hole.
At that moment, I didn’t care about chastity or anything else in the world. I was a complete sissy and just wanted to get fucked.
Prep that sissy pussy as you prepare to insert that dildo in your ass!
I began to leak, it was amazing! Goddess Alexa moaned, "Ummmm that's right, cum like the little sissy bitch that you are!" I kept on flowing as she took long, hard pumps deep inside me! Each pump pushed out more sissy juice.
Mistress Cheryl yelled, "You fucking faggot, I created the perfect sissy whore... you love cock."
Goddess Alexa began shaking my cage—my dribble went all over the cage! I was in euphoric bliss! I responded, "Yes, I love cock."
Goddess Alexa said, "Good. Lay on the bed, time for me to feed you!"
I laid on my back with my head by Goddess Alexa’s knees. She began to stroke her cock and said, "Open up, faggot, I’m gonna cum in your mouth." I wanted it so bad! I reached up and began rubbing her legs and begged, "Please Goddess Alexa, cum in my mouth!"
She let out a moan and said, "Oh my god, you are such a fucking sissy faggot, ohhhh mmmmmmm," and then shot her load in my mouth and all over my face.
Get on your back and get into that sissy position with your legs over your head! You know the position—use the wall if you have to, but get that cock right in your face for the rest of this story. Any leakage needs to go on your face.
I was still incredibly horny and in bliss. Mistress Cheryl was laughing in the background. She then said, "Do you want to earn your key back? Do you want to cum?" I said, "Yes, Mistress."
She said, "Then there is one way that you can do it!" I begged for release and asked how. She said, "Wait a few minutes. I am gonna send the key up."
Goddess Alexa began to laugh and said, "You are in trouble now."
About 15 minutes later, there was a knock on the door—I couldn't believe it, Mistress Cheryl was here?
Keep edging that clitty as you anticipate release!
From the bed I couldn't see who it was, but I heard a voice—Goddess Alexa said, "Come on in, sexy!" I moaned and called out, "Mistress Cheryl, is that you?"
Keep playing with that cocklett, you know what's coming!
I looked up and saw a skinny black male. He looked at me and said, "I was sent here by Mistress Cheryl! I paid good money for this key of yours!" I asked, "Who are you?" He laughed and said, "I am your God, your master, your new owner."
I heard Mistress Cheryl's voice from the computer, "Sorry slave... I sold your key to Sean. I'm sure you won’t have to do much to earn it back." She laughed and said, "Good luck... It’s been fun, but I like real life in-person slaves and this online stuff is boring me. I took you as far as I could go! Take care slave, it’s been fun turning you into a sissy bitch!"
I was sure this was just part of some game, so I played along. I said, "Sean, what do I have to do to get my key back?" He slapped me right across my face. Goddess Alexa, now sitting in a chair in front of the desk, burst out laughing. I was in shock. He said, "Don’t you ever call me that again. Who did I tell you I was?" I repeated, "My God, master, and new owner?" He said, "That’s right, bitch." I was not ready for this type of aggressive play! He began taking his clothes off!
Edge that sissy cock! Deep down, you know you want this day to come!
He said, "Look at my body! If you want this key, you will drop to a knee and suck my D..." Goddess Alexa started laughing again! She said, "You will be sucking me again too, this is turning me on."
I saw my key on his keys... I was horny... I figured... I just sucked a tranny, why not a male... it would be worth it. So, I did as I was trained to do. I dropped down, and slid him into my mouth. From that moment I knew I was really a sissy fag. I took a few licks and soft kisses and I was so fucking horny! My body liked it!
Get to the edge while thinking about big man cock sissy!
I kept on sucking! I found myself getting so turned on! I kinda don't remember it all! I do know that Master was grabbing my head and Goddess Alexa was coaching me and calling me names... "Sissy slut fag! Suck deeper, that's right... Earn that key."
I heard Master say something... I couldn't make it... Goddess Alexa then slid her cock into my mouth. She grabbed the back of my head and pulled me in! She said, "I'm gonna cum in your mouth again sissy!"
She slid her cock into my throat... And then I felt it! Hard cock begin to pulsate and shoot another heavy load in my mouth. Master was moaning, Goddess Alexa was yelling "Don't swallow!"
I couldn't believe how horny I was... Master said "To earn that key... You have to take one in your sissy ass too." Mistress Alexa put her fingers in my mouth to play with the cum... She made me suck it off her fingers and swallow.
You are so close to freedom and coming! Stay right on the edge and hold it!
And then it happened! Fate... My fate, your fate, the fate of every sissy! He entered me and slammed me over and over! My ass was still lubed from Goddess Alexa! His cock was bigger than Goddess Alexa's and felt much harder. I moaned as I felt him deep inside me over and over!
I didn't leak, I kinda wanted it to stop but at the same time I wanted more and more! And then his pumps got slower and harder... Each one made me belt out a tender moan! He pulled me in tight and came; all in my ass! I felt the cum inside me!
At that moment I remembered every picture and video I saw that led to this moment! The truth started settling in as I reached back and felt the cum dribbling out of me! He laughed, Mistress Alexa started laughing also! I looked down and my clitty was pulsating in my cage!
Mistress Alexa said... "I think he likes it!" And then finally... Master reached down and unlocked me... I was free!
He looked at Mistress Alexa and said watch this... He looked at me and said "Sissy lick my dick... Get your ass juice and the rest of that cum off my cock."
I could have said no... I could have taken my freedom and run... but I didn't want to... I wanted another taste! I crawled over and did as he said. I was now a Sissy! I was always a sissy! I wasn't chastised into becoming a sissy fem fag... I was just led into the path that I always wanted!
Reach down and finish yourself! Oozz all that cum into your mouth! This is your fate also! It's only a matter of time until you will be finishing a hung stud! Trust me, if it can happen to me, it can happen to any late night stroking closet sissy fag!
To this day I haven't talked to Mistress Cheryl, Goddess Alexa, or Master Sean. I've reached out to Mistress Cheryl several times, but I never heard back. As of late, I've been serving a Fin Domme online and in person... In fact that's what has had me so busy! I've been keeping a sissy journal, I think my current experiences will make another hot series! You see, being a sissy is an addiction, you are forever a cock addict!
Congratulations, you’ve completed the webtease!