Sissy training

Day 8

I was sleeping fully naked as usual, but today I woke up with a surprise. I don’t know how Dahlia managed to lube my ass and penetrate me, but I woke up on my back, legs up with a cock in my ass. She was going slow in and out and, and greeted me with a kiss. We kept making love, I wrapped my arm around her neck, and we were kissing. With my hand wrapped around her neck, legs wrapped around her waist, her cock going in and out of me, and her lips on my neck, I felt in heaven, everything was perfect at that moment. She could feel my cock getting under her, so she took hers out of my ass, put some lube on my dick, and mounted me. I was fucking her, while she was leaning back cock pointed at my face and masturbating. In a few minutes, she started to cum right at my face, hitting me in the eye and some of the landing in my mouth. She kept riding me, till I came in her, her semi-hard dick slapping around. When we were done I asked her:

• “What was that for?”
• “I wanted to wake you up in a nice way.” – then she kissed me.

We had coffee on the terrace, fully naked not caring for anyone seeing us like that. The feeling of the warm sun on my dick and naked ass was pretty nice.

• “So did you complete your task.”
• “I did, but no pictures or video, the guy wasn’t really happy, when he realized I had a dick.”
• “Haha, but he still fucked you right?”
• “Yea, you can’t escape this ass that easily.”
• “Yea I agree.” – she replied with a smile.

We spend the morning talking about my day, I told her how I was scared at first, but overcome it, about the blowjob in the elevator, and everything with the random dude from the pool.

• “Well another task complete, you are doing great so far.”
• “I don’t feel them like a task anymore, just having fun and obeying my Mistress.”
• “Good, that’s how you know it’s working, well then let’s have some more fun, I have a lot planned for the next days.” “And no more tasks, except your finals tasks, but we will get to that another day.” “So how do you feel, want to go out dressed like a sissy?”
• “Hell yea, I embraced it, and I do like it now.”
• “Great let’s get ready.”

Today I was feeling it. So before I got dressed I caged my cock and put a plug out back, just for fun, when Dahlia so me, she decided to joy and did the same. She was wearing a business suit today, a black short skirt, dark panties, a white tank top, the jacked of the suit, and red high heels. I decided to match her, I got a gray suit, with a short skirt as well, a blue tank top, colorless panties, a suit jacket, and black heels. I also put on a dark red wig to match her hair color. We were 2 business ladies going out, with caged dicks and plugged asses.

We were wondering truly the stores, trying clothes and other stuff. We were like “sisters”, always in the same dresser, watching each other change, giving opinions on the outfits, occasional slap on the ass, or grabbing and kissing, pulling the plug out just to put it back in a moment later, or to see how it look like without it when measuring underwear. We had a lot of fun, I have never before had so much fun shopping. We were thinking of going to a restaurant. We were looking thru some bathing suits when I caught one of the guys working there checking us out. Dahlia remember something she forgot to buy and told me she will be back in 15 minutes. I told her ok and kept looking thru the store. I caught the guy checking me out again, he was arranging clothes next to the dressers. I picked something up and went to “try it on”, and when I was inside I pulled the curtain slightly, showing only my head, and asked him if he can come to help me for a moment. He asked if I want him to get some of the girls to help, but I told him that is ok and that I want a guy’s opinion. He approached me, and I grabbed him by the shirt and pulled him inside, directly unzipping his jeans, and started to suck his cock. He was surprised but didn’t mind at all. The dude came in less than 5 minutes, but that was ok, I just wanted a quick taste anyway. I left him their pants down and went on the way for Dahlia.

In the restaurant, we picked a table and I went to the bathroom to freshen up, and clean my lips from the blowjob. When I came back to the table Dahlia was sitting with 2 dudes, they locked pretty cutely, both wearing suits, she said that the place is full and she invited them to have lunch with us if I don’t mind. We were laughing and having fun, and they were touchy. When we finished with lunch, one of the guys whispered something in Dahlia’s ear, she then leans over to me and said:

• “He asked me if we want to go to the bathroom for a quickie, what do you think?”
• “Fuck it let’s go.”

I know Dahlia fucked me a lot, but turns out she loved to take cock up the ass a lot, maybe more than me, such a slut.

We went to the man’s bathroom om, and one of the dudes put an off-limits sign outside, no idea where he found it. In the bathroom, it didn’t take us long to push them to the wall and start sucking them off. We each had chosen a dude we liked, and we were sucking them off like the professionals we are. The guys pinned us on the fall, and lifted our skirts, they pulled our pantyhose down and moved our panties to the side. Remember we both still had plugs inside, but the dudes didn’t seem to care they just took them out, they them on the floor, and started to fuck us. They had a pretty big dick and were fucking us pretty hard, you could hear the echo of their tight slapping against our asses, and the sounds we were all making. They swapped, and I had the other guy’s cock inside me now and Dahlia my guy’s cock in her. We were facing each other and we were watching each other in the eyes, while both of us were taking cocks inside. I reach and grabbed her hand, so we are holding hands while the guys are rapping us. They put us on sick, and we were back with our original dudes, legs up and spread, pantyhose hanging from one leg, panties still on covering the cage dick, not that this dude cared. They wanted to fuck us, and they did. We finished, with me and Dahlia on the floor faces touching, makeup going down our faces, and these dudes masturbating and getting ready to cum all over us. Sperm was everywhere, we were licking it off each other and kissing to share the taste, and the guys were happy to watch us. They said goodbye and left us to clean up before we left as well.

Dahlia did say what she forgot, or what she was carrying in the bags when she came back, before the restaurant, she told me it was a surprise. Well, tonight I was going to find out. We were talking in the evening, about her previous experiences, other sissies she trained, and so on. I learned so much about her and what she loves, she also told me how much fun we are going to have the next few days, in preparation for my “final test”. She told me to go to the bedroom and wait for her. She had a surprise for me since I was doing so well. I lay in bed waiting for my Mistress.

Well, I got a Mistress tonight. She showed up all dressed up in leather. Black and red were the colors. She had long red boots, with big pointy heels. She had fishnet stockings, and red gloves on. Her hair was dead in a ponytail and wet. She had a black corset on, but her boobs were out, the corset just cupping them underneath, she also had nipple clamps on her tits. Her already hard cock was also out; she was wearing some kind of crotchless leather panties. Holding a whip in one hand. I was just stunned.

• “Are you ready for me bitch, are you going to serve your Mistress.”
• “Yes Mistress Dahlia, command me.”
• “Get over hear slut, my boots need cleaning.”

I jumped off the bed and ran toward her, going down on the floor and licking her boots. She started to slap my ass with the whip while I was down there, she didn’t hit me hard, but at this point, I didn’t care it was all so hot, and I didn’t expect I was going to be into this stuff, but seeing her like that, I just wanted her so bad. She told me to lay on my back and started to run the whip up and down my body, slightly spinning it and hitting me at times. She then stepped on me, she was playing with my balls with her feet, hitting me, and asking me to suck her heels. She then sat on my face and told me to eat that ass up. I was licking it, fucking her with my tongue, my hand was pinned down, so I had my tongue to use only, and I was even struggling for breath a bit. She lifted herself, and the moment I open my mouth to take a bit of air in, she stuck her dick inside and started to fuck me in my mouth. She was holding my head and just fucking me aggressively, my only choice was to take it, I even started to choke a bit.

She told me to get up, and slowly remove her nipple claps, then she grabbed them and place them on me. They were connected with a chain. She then pushed my face down, and ass up, and started to lick me, the next moment I felt something penetrating me, but It wasn’t a dick. I could see her fucking me with her heel in the mirror. It was pointy and I could feel it pocking me inside, I was afraid it could damage me, but she was so careful. While pinned down, she also handcuffed me and told me to turn around on my knees. She then started to fuck my face again, and I could feel her foot playing with my balls and dick. She grabbed the chain connecting the nipple clams and pulled me to follow her. She led me to the balcony and put me on the sofa we had there. Then she stood behind me and penetrated me, pushing it hard inside and fucking me at full speed. I was pretty sure my scream was heard by the neighbors, but I didn’t care. I was a proper sissy slut at that time, taking dick and begging for more, for her not to stop, out in the open. The handcuff was broken, they were cheap anyways, but I was holding the rail on the balcony while she was fucking me from behind while choking me with the whip. I had tears going down my eyes, from both pain and pleasure.

We moved back inside the bedroom, and she was laying on the bed, legs spread, heels touching and I was on top of her riding that dick. The pleasures I felt at that point were too much again, my dick started to leak, and I started to cum on her leather corset. I was feeling so much pleasure I didn’t even care I just came, but she did. She got mad I came without permission, and also on the cloth, she told me I better clean this shit up fast. I licked every last drop of her and started to kiss her breast and purr like a cat.

• “Oo you are sorry for the mess you made, now you want forgiveness don’t you pussy?” “Well you better get that dick hard fast then, I want you inside me”

That was all I waited for, I lifted her legs and penetrated that ass.

• “Yes baby, fuck you, Mistress, that it fuck me hard, fuck me.”

Dahlia was creaming, and that was making me even hornier. I flipped her on her chest and started to fuck her pinned down on the bed, holding her hand behind in a tight grip. I put her on her back again, and lifted one leg, fucking her like that, while keeping eye contact with her. I could see how much she was enjoying every second of it, but I still could make her cum, to experience the same prostate orgasm she gave me. The roles reversed again, I was on my back legs up, and she was laying on her side fucking me like that, I didn’t know what I like more fucking her or getting fucked by her, but at this point, I didn’t care. She had me pinned on the backboard of the bed, and I could feel my dicking hanging under me slapping around. I loved the feeling of that dick going inside of me in this position, I was biting a pillow I had under me to keep myself screaming like crazy. I came for the second time tonight like that, what did she take how did she keep going for so long? I ended up on top of her, legs in the air, she was holding my waist and fucking me like that when I felt my ass finally getting filled with warm goodness. We just felt sleep like that, I was once again sleeping with a dick in my ass.

Day 9

The next day we spend most of it just resting and relaxing. We went to the pool, got some drinks, and flirted with the waiters. In the afternoon we just cuddled and watch a movie like any normal couple it was nice. But I still had a mission in mind.

After dinner, Dahlia took a long bath and I prepared myself mentally and physically. I picked up vibrators I liked, spread some roses on the bed, lit up some candles, and put on some romantic music. When she got out of the bathroom she asked me what is all this.

• “This is all for you babe, I wanted to make you something special.”
• “Aaaaa, so nice of you.”

Then I walked toward her and I whispered in her ear:

• “That’s not all, tonight I’m going to make you cum, I fill you fuck you as long and hard as I need and you will cum hand free. You are my lady tonight and I do what it takes to make my lady happy.”

She could not say anything, she just had her mount open in shock. I kissed her and lifted her, letting her down on the bed. I poured hot chocolate all over her still-wet body, which I ordered earlier, and started to lick it up, she was so excited. I started to play with her cock a little, and while she had her eyes closed enjoying it, I lubed up a vibrator and put it in her. She was happily surprised by that. I then laid on my back, and sprayed some whipped cream on my dick, she didn’t need a second invite to start licking it off. I took my time to enjoy her lovely lips around my cock. The vibrator was still working inside of her ass. She took it out and mounted me, and so my task begins. I was fucking her for 30-40 minutes, stopping to rest but using the vibrator while was not inside of her. I even had her on the ground, legs up on the side of the bed, and fucking her like that, switching between my dick and the vibrator. When I had her on all fours, they told me to stick the vibrator in as well, she was begging me to do it. She had both me and the vibrators inside of her, which made her go crazy, and she started to slap her ass at my legs. I had already cum inside of her tonight, but I kept going, my dick was working perfectly tonight, it didn’t matter I was rock hard. Finally, while I was on top of her, fucking her in the missionary position, holding her thighs. She started to moan hard, her legs were lifting her, and her ass was moving up, but I kept fucking her. Her ass and waits getting lifted by her legs, and with her head leaning backward, and closed eyes, she started to scream, and her dick started to spill sperm all over her sweaty torso, and over her belly, breast, and even face. I was so happy, a minute later I started to spray my seed on top of her as well. Laying in each other arms.

• “Thanks babe, that was amazing, I came so hard.”
• “You can say I completed my task then.”
• “Yea you were the man tonight, but tomorrow back to being a sissy slut.”
• “Yes, Mam.”
• “O feel free to call me what you want from now on. I would say we are just 2 basic whores now.”

Day 10

Tonight we will have guess told me, Dahlia, in the morning. But she didn’t say anything else. We were wondering what to do today when Dahlia remember something.

• “I didn’t even show you the second part of the gift from the other day.”

She grabbed a bag and pulled out 2 vibrating plugs. She told me we should put them in, and we can control them from our phones. It should be a lot of fun. We had to go out to pick up dresses since we had an event we needed to go to tomorrow, so I proposed we used them in public to have more fun. Since I was picking a dress for myself as well, so I dressed like a girl again and we left. We also put in the toys and we decided it will be more fun to have each other control over the vibrations. The vibrations were stronger than I expected. We were walking and since one of us open the up and started to play with it, the other one started to walk funny right away. I was going to cum due to this toy. In the shop, we were trying on dresses in different dressing rooms this time, and from time to time you can hear someone moaning or gasping, I will let you guess why. I loved this app.

I guess Dahlia was done since I didn’t hear her anymore, I was trying a blue dress, but could not get her to fit, I called Dahlia and ask her if she can get another one for me. I have just removed her, and I was in my panties only, which we white and soaked with pre-cum already, my door opened, and I girl showed up with a dress. She looked at me and smiled, she walked in, left the dress on the hanger, and started to touch my cock and started to kiss me. I don’t know if Dahlia knew her or if she just send her and this girl is thirsty, but I felt a bit set up, since the moment she fell to suck me, I started to feel the vibrator going on like crazy. This girl was having fun, but it was hard for me to last long with this thing inside my ass, making me go crazy. Still, I came in the chick mount, and they took it happily, she kissed me with cum filled mouth, to share a bit of the taste, then told me to let her know if I need any other help and left. We picked up our dresses and left the store to go to a restaurant. I had pulled out my plug, but Dahlia still had hers inside, it was time for some revenge.

We sat down and started to look at the menu, the moment the waitress came, I started to pump that app. Dahlia was having difficulty ordering at that point. She told me to stop, but it was too much fun. Every time she was trying to eat or drink, I will increase the speed. I could see her sweating. She tried to grab the phone but no chance. I started to play with it, going up and down, on the speed, and program settings. I could see her getting hot in front of me. I could see her dick, it was rock-hard under her dress. She was trying to hide it under the table. She started to rub her boobs, and her nipples, and even took one out for a second before someone walked by. I could see how horny she was getting from it, so finally when no one was looking, I snuck under the table, and helped her release the pressure. That way I also got my dessert. Such a fun toy there was. We got home and rested, preparing for the guest tonight.

Well, the guess tonight was a coworker of Dahlia. They were longtime friends. Her name was Elena and she was also a trans woman. They talked about work for a while, while I was just listening. I was washing some dishes when Elena walked behind me and grab my ass.

• “I can see why you like him so much Dahlia, that’s a nice ass.” – she said.
• “That’s not all that nice.” – Dahlia replied.
• “So what do you think Viki, you ready to have some fun.” – Elena asked me.

Well, I didn’t expect it but I wasn’t surprised either by it. Of course, we will fuck, Dahlia never disappoints.

We all went into the bedroom and started to make out. I don’t know what their plan was, but my first action was to bend over and suck these 2 cock together. Elena’s dick was 6.7 inches, it was curved to the side a bit, and it was the prettiest dick I had seen. She also had a hard tattoo right above it. I started to lick both of those tranny cocks at the same time, while the 2 ladies were making out and sticking fingers into each other asses.

While I was still sucking, Elena didn’t care much and just mounted me from the top, penetrating me straight up. My ass was pretty used by now so I didn’t have any problem anymore. I was sucking while gasping from the cock in my ass at the same time. Then they switch me around and I was getting Dahlia’s cock from behind and sucking Elena’s. But that was not all, the 2 ladies pushed me down on my back and started to lick my cock together. They were laughing and smiling, the whole playing with my cock and kissing each other.

• “Well are you going to try it on?’ – Dahlia asked Elena.

She just put some lube on her ass and sat on top of me. This ass was a hard-working one, she just took it in with no problem, and started to fuck herself. I could see her dick going up and down while bouncing on top of me. After some time, Dahlia was behind her, pushing her to lean forward. She did by making an incredible sound and flipping he hair back at Dahlia with lust in her eyes. Dahlia covered her cock with lube, get in position, and started to push her dick inside Elena’s ass, right next to mine. We were fucking her together at the same time, and Elena was loving it. She was screaming and squirming right on top of me from the pleasure. They swapped, and Dahlia laid on top of me, with her back facing me, and front-facing Elena. She mounted me with no problem, and waited for Elena to penetrate her as well, we were double penetrating Dahlia now, and she was screaming and squirming as well.

• “So what do you think you want to try?” – asked me, Elena.
• “Hell yes.”

They said facing each other, cock touching, told me to lube up good and try to sit on them, it was easier that way for the first time. I did what I was told, trying to take those 2 beautiful cocks inside at the same time. It was painful but I didn’t care, I was going to take them. I sat there for a minute and then something happened. They were fucking me together, but not only that, the tips were in all the time, but when one was going deeper inside, the other was coming out, and they had a perfect sync. And the feeling inside of me was amazing, I just started to leak cum. But I didn’t care and told them to keep going, which they did while laughing at me. This kept going all night long. I was fucking them both together, stacking them on top of each other and swapping between one ass to another. They were fucking me as well, and each other, it wasn’t the first time for those 2, and they looked cute together. They knew what they liked and how to get it. All I know is I fell asleep, between 2 trans women, and I had 3 dicks between my legs that night.