Turned into a Sissy Pt. 03

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My journey continues with first humilation and more.
2.4k words
4.59
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Part 3 of the 18 part series

Updated 12/25/2023
Created 02/20/2022
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cd_luna
cd_luna
195 Followers

After we had decided to freshen up and get something for dinner outside, not too much actually happened that day. She let me dress normal guy clothes, just panty as underwear and as mentioned in the last part, she did not unlock the cage. After dinner, both of us were actually tired and a bit tipsy, since we had a few drinks as well. Since we had to work the next day, nothing happened, we just fell asleep, me still with the cage on. I unsuccessfully tried to convince her to take it off.

The next morning we both had to rush to work, to my surprise, she offered to release me, but I had to promise not to touch myself. Of course, I promised that. She opened the cage, sat down and kissed my little one gently, licking the tip, and the shaft, taking it in her mouth. Just when it started to get hard, she stopped and slapped it gently.

"You should focus a bit. Remember, don't touch yourself, don't relief yourself."

She stood up and we kissed, my little one now got really hard.

"Please, can you help me with that?"

"No, my bitch, I won't do it now. But if you keep your promise, it will be very rewarding for you."

She kissed me, turned around and got dressed for work. I went to get a really (really, really) cold shower, then was also heading to the office.

The week actually passed fast and boring, long hours work, dinners with clients and my girlfriend had some days a late shift. So we only talked a lot on the phone, but she slept at her place and I in mine. Whenever we talked, she checked on me, if I still did not touch myself. It was getting really difficult, but I stayed strong the whole week.

Finally it was Friday and we agreed that I pick her up after work at her place, that day she was able to finish work earlier. In the morning she sent me a message,

"How about you wear stockings and garter belt today, panty and bra. And don't forget to bring your cage tonight."

So I put on white stockings with matching garter belt, white panty and a white bra. Above that I was wearing my normal suit to work. I can tell you, my little one was leaking that day a lot, just from the thought of meeting her tonight.

Once I got off work, I grabbed a cab and drove to her place, went upstairs. She had already packed a few suitcases to bring to my place, stood at her doorstep and looked just amazing. Black high heels, black leather miniskirt and a black and silver top. I could not take my eyes off her, kissed her, and my little one wanted to get attention.

"Before we go downstairs with the luggage, there is one more thing to do."

She said and directed me inside. She opened my trouser and pulled it down. "Sexy white lingerie set, I love it!"

She smiled. Then she pulled down my panty, my small cock popping out. She massaged my balls.

"You really are fully loaded, as it feels." She giggled.

"Of course I am, how could I break my promise?"

"Give me the cage! "

"Really? Can we not leave it off tonight?"

A look in her eyes gave me the answer, so I gave it to her. She put on the base ring, pinched my little one as last time, and it worked again. The cage was on in no time.

"I promise, if you keep it on for a bit longer, you will see that it is worth it."

She stood up and kissed me. And in hindsight, she was completely right.

I carried her bags downstairs and we got in the cab. She had her hand on my crotch area and moved close to me, put her head on my shoulder.

"You really are my bitch, aren't you? You did not come even once, since we first met."

I was quite embarrassed, since a lot taxi drivers here speak a bit English. She continued.

"I really love that. I know you expected different, but I hope you like it, too."

"I do, it was hard to stay strong, but I feel good that I did it for you."

We kissed, then she rested her head again on my shoulder.

"You know, I also did not come since last weekend, I have saved a lot for you." Hearing this made me feel again embarrassed in the cab, but at the same time also very happy.

Once we arrived at the serviced apartment building, we went inside and I carried her bags to the apartment. We ordered some dinner upstairs and while waiting she asked me to take off my suit. Again she said that she thinks my lingerie choice is very sexy.

"Do you have a matching dress here?"

"Unfortunately nothing white, but how about light blue? I will show you, wait a second."

I went to the wardrobe, picked a light blue short dress. It has long and wide sleeves, tight around my waist and a wide skirt part, reaching around middle of my upper thighs, so that you could just see the start of the top part of the stockings.

I went back to the living room. She came closer, went around me and looked at me from all angles.

"Do you have matching shoes?"

"No, sorry, nothing that would work with this outfit."

"You have a good sense of style. But how about we go for a girls shopping spree tomorrow?"

That of course sounded awesome to me. We kissed, hugged and she played with my nipples through the dress and bra. This always makes me instantly horny, of course the cage didn't allow for any hard on. I returned the favour and played also with her nipples through her top, close as we stood, I felt that her cock was starting to get hard.

"I told you, I saved a lot for you."

Suddenly the doorbell rang.

"Why don't you go and open?"

I hesitated.

"Dressed like this? Without wig or make up?"

"You look perfect to me, I don't see an issue."

I still hesitated. She stepped back and walked to the dining table, sat down.

"I am really hungry."

The bell rang again. I had no other choice, I walked to the door and opened, my heart beating like hell. The guy from the restaurant downstairs bringing our food just handed me the bag with our order. I knew him, since I ordered a few times before from the place. To my surprise he did not show any reaction or make any comment. I closed the door, leaned against it and took a deep breath. Then I walked to the living room, she looked at me and smiled.

"You are blushing, that's really cute, I love it. Thanks that you did this for me."

I went to the kitchen, arranged the food on plates and served it on the table.

Then I poured two glasses of wine and went back. When I came back, she had pulled her skirt up and panty aside, her cock was hard and she stroked it.

"You make me really hard, seeing you like this, my little bitch."

Of course, I knew what to do. I placed the glasses on the table and kneeled down in front of her.

"Please do a good job, the food should not get cold!"

She laughed, "but don't immediately swallow."

She leaned down and kissed me. Then I lowered my head, started to lick the tip of her cock, kiss it, then licked along her shaft. Suddenly she held my head and just pushed me down on her cock, I gagged a bit then started to suck hard, moved my head up and down, played with my tongue around her shaft, I just loved it, and judging from her moans, I did a good job again. I moved my head all the way down, and massaged her balls, then I started to move up and down faster, until she suddenly shot a big load in my mouth. I stopped, sucked to get every drop.

Then I lifted my head, of course I did not swallow, I played with the cum in my mouth, it was really tasty and a huge load. She held a wine glass close to my mouth, so I spit the cum in it. She handed it to me and took the second glass.

"Thank you baby, cheers!"

And I took a sip of the wine with her cum in it. I can tell you, that combination tastes really good.

I sat down as well and we started dinner. Just chatting about the past work week and our plans for the weekend.

She also asked me about details of my previous experience with girls and guys (I had sex only with two guys on short hook ups, other than that had only sex with my ex-girlfriends).

And at some point she asked:

"How did you feel in the taxi and with the delivery guy?"

"It felt strange and embarrassing at first, but seeing that both really did not care, makes me feel better about it."

"You tell me, if I go too far. I just wanted to try, what you would do for me. And I love the result."

Hearing this made me unbelievably happy and just this feeling made my little one want to get hard.

"You are blushing again, little cutie."

She smiled, stood up and walked over.

She kissed me, raised my dress and looked at my cage.

"Looks like you got a bit wet down there."

"Can we take it off, please?"

"You know the answer, don't you, bitch? But I promise, you will get the reward this weekend. Although it might be different to what you think. So long you should try to stop always thinking about the cage and your little cock."

She giggled, and I just loved her like this, she looked so cute and sexy at the same time, playing with me like this.

Afterwards we refilled our glasses and sat outside on the balcony, chatting more. The light and warm breeze felt great under my short dress.

"Did you also bring a plug?"

She asked at some point. I nodded.

"Just one."

"Show me."

I went inside (made a detour to the bathroom to quickly clean myself. Fortunately the toilet had a hose next to it, like many in South East Asia have) and grabbed my plug, it was a silver metal plug, just 3.5cm diameter, with a black jewel at the end. I showed it to her.

"We should not only buy some clothes for us tomorrow, but also some toys. One with a pink jewel would be better, don't you think?"

Then she looked in my eyes with a look only girls have, when they ask a favor (if you know, you know, what I mean ) and continued.

"Can I see, how it looks in your hole?"

I turned around and leaned on the railing of the balcony (the railing was made of concrete, not a glass one). She lifted my dress, lowered my panty and spit on my hole, then she came closer and started licking it, it felt unbelievably good. Then she took the plug and slowly pushed it inside, until it was in place.

"Still looks pretty cute there."

She slapped my butt gently. From the rimming and the plug, my little one wanted to grow again and got wet. She noticed of course, massaged my balls a bit.

"Patience, my little bitch."

Then she turned around, went inside, I followed her to the bedroom. I was incredibly horny, I just wanted her, although I knew, I cannot fuck her, the stupid cage was still there, I thought. But at the same time, I also really wanted to taste her cock again.

We started to make out, I took her top off and her bra, played with her nipples, kissed every inch of her body. Then i opened the strap of her high heel sandals, and kissed her legs upwards, opened the zipper of her skirt and took it off. I wanted to take my dress off, but she stopped me. She lay down on the bed, opened her legs. I stood up and just watched her lying there.

"Do you know that this is the sexiest view, I have ever seen?"

She grabbed her cock, which already got hard and started to stroke it, looking at me.

"Are you jealous that you cannot touch your cock?"

"Indeed, I would love to. And I would love to take you, sexy."

She had this special smile again.

"Tonight, you definitely won't. And my cock doesn't suck itself."

She giggled again. I understood the assignment.

I got on the bed, kissing her legs again all the way to her cock, which she was still stroking. I looked in her eyes, she took her hand off and I immediately took her in my mouth all the way. This time, I wanted to be in control, I sucked her and licked her and whenever I felt her cock stiffen more, I stopped, held the base of her cock tight. Then I continued. She was moving her hips, obviously she liked it. When I stopped the next time, she said,

"You really are a bad bitch do you know?"

"Only the best for you!"

I smiled and continued. This time I did not stop and it took not long that she shot another big load in my mouth. It tasted delicious again. (did I mention, I really am a cum addict nowadays?) I swallowed it all, then licked her cock clean. Moved up next to her, we hugged right, she said

"I love you my bitch!"

"I love you too."

I guess that was the official start of our relationship. that night we just fell asleep as we were,me still dressed and plugged, she just naked. She wanted to be the little spoon, wanted to be hugged. So I ded and we fell asleep. It was a weird situation, being the big spoon, but having my cage on. Nevertheless, I felt content, I was happy. I forgot that I did not come for a really long time.

-- Sorry that this got a bit longer. Next part will be about our shopping spree (fun part, I can tell you) and how I got closer to my reward. Hope you liked this part, please let me know in the comments.

cd_luna
cd_luna
195 Followers
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AnonymousAnonymous5 months ago
New Sissy

I love dressing in womens things.I love the silk next to my body.And the stockings on my leggs.give me a over the top feeling.Now that i dress and do my make up i have taken to having sex as a woman.I in joy a hard cock in my ass and mouth some time at the same time.

MichaelfantasiesMichaelfantasiesover 1 year ago

I may have to save this series to my favorites! I'm becoming more interested in the dom gurl! "She" seems to LOVE being the dom in the relationship, and loves getting HER cock sucked! The chastiy thing would be a very difficult thing for me to commit or submit to though (just being honest). I'm definitely wondering where this story is leading too!

tvlove007tvlove007almost 2 years ago

I couldn't resist. I put my plug in after part 1.

ChrisissyChrisissyabout 2 years ago

Love the teasing and denial! That always drives me crazy!

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