Sissy training

Day 11

We send Elena off in the morning, having a little extra fun of course. I was a bit sad in the morning, I will miss her. Luckily today was a big day for me. Dahlia had to go to a formal event tonight and asked me to be her date. We spend most of the day in the spa, relaxing and getting ready for tonight. In the late afternoon, we started to get ready for the party. Honestly, gay or not, sissy or not, it was super fun to me getting ready with her, maybe because I didn’t have to do it every day. We were just walking around fully naked, cocks hanging freely. We were listening to music and dancing, fooling around while doing our makeup. Dahlia had this tight golden dress picked out, which made her breast and ass pop out. On the other hand, I always wanted to get into a little black dress, and this was my shot. Nails and toes were all bright red, and lipstick as well. I had picked this black long wig, straight black hair going down my shoulders. The outfit was all black, and this nice push-up bra, was super-hot, with lace straps I could cover under the straps of the dress. Black thong, but first I had to cage my cock, there was no way it was not going to show if I get even a little hard under that tight dress, Dahlia got hers tapped to the tight, but I decided I like the cage more. I had these 12 centimeters heels on classy black shoes, and stockings going all the way up my tights, just where my little black dress ended. I was feeling hot and ready for action. Or like a whore who is ready to get paid.

We had a car pick us up from the hotel and we were on our way to an evening Gala, my first one and I was going dressed like that. I always thought it will be in a suit, but I guess this is better. We arrived and it was a Gala for designers and a model show. We chatted for a while, Dahlia was introducing me to her friend Viki, who is just visiting her for a couple of days. We watch the model’s show, and then it was time for the cocktails. We were at the table, and I was a bit bored since I didn’t know anyone. Dahlia was walking around talking to different people. I stood up to go to the bathroom, but I had no idea where they are. I saw a girl walking into a door that looked like one and I followed her. When I opened the door, I could see it wasn’t a bathroom, the girl was down on her knees blowing some older gentleman off, they did seem to care that I was there at all, I walked out and walked into the room next to it. There I found one of the waiters, being fuck by this massive dude while sucking someone else’s cock. They just smiled at me when they saw me and kept fucking, again not carrying if I was watching or not. Finally, I found a bathroom and then got back to the table. Dahlia was there talking to one of the models who got up the moment I sat down. I asked her what is with this room that people are fucking and so on.

• “Well this is not an ordinary party. “- she replied. “People come here to loosen up and let’s be honest cheat and swing with no consequences.” “You wave several options, most of the models you saw are “for sale”, you can bid on a night with them if you want, and there are private rooms upstairs for you to spend the night, most of the money is for charity so it is nice. Also, people can rent a room and have private fun, there are a lot of older couples here who like to swing, or fuck with some younger people, just to have some fun. And there are these fuck rooms here. People are free to go fuck and come back to the party, they are not private and anyone is free to walk in and join them if they want to. Everything is allowed, and people end up trying new things like that. There is a story of a modest girl, which ended up on her knees all night, waiting for every guy to cum in her mouth one night, and another when a stand-up, straight-as-a-nail older gentleman, who spend his entire evening, in of these rooms, sucking cock and getting fucked all night long. He is right there with his wife now. He is still straight and loves his wife, but people have cravings at the time and here you can satisfy them all. Walk around I’m sure you will find someone to have fun with.”

A dude walked by us and whispered something into Dahlia’s ear, that made her giggle.

• “Well I’m going to go suck dick, I suggest you do the same.” – she said, before leaving with the guy.

I grabbed 1 more drink, before walking around the room for a bit. I could see people coming and going out of this room, all the time.

While watching, I young nice man walked near me. He was tall with a nice suit, which was a bit small for him, you could tell he was jacked since I was pretty sure he can tear his shirt right off. He stood next to me and asked me if I saw anything interesting. I told him I was just watching people go in and out of the room, wondering what they were doing. He grabbed me by the waist and while licking my ear he whispered to me, he can show me. Well, that’s what I was waiting for. He said me to follow him, and he took me into one of the rooms. There he didn’t take any time before grabbing me all over and starting to kiss my neck, I was unbuttoning his shirt when this huge hair chest popped out underneath. He was grabbing my ass and flipped me over, and I could feel his tongue right up my ass, eating it with such passion. Then he forced me down on my knees and started to remove his belt, and I helped him undo his pants. The first thing I notice was this manly muscular smell. He was super hairy down there, with 2 huge balls, and this massive thigh-circumcised cock right in my face. Well, I knew what I had to do, so I took that thing inside my mouth. I was holding it with my hand, moving it back and forth, while sucking his head off. I was looking upright into his eyes, not breaking eye contact for even a second. The guy grabbed my face and started to kiss me while I was standing up, then he flipped me, slammed me into the wall, and moved my thong aside. He spits on my ass and his cock, and started to adjust it in my hole. He had me pinned to the wall with his left hand while adjusting his dick inside of my hole. His head started to enter me slowly, and I gritted my teeth, I was used to it by now, but there was still a bit of pain at the start. He was gentle and going in slow, when his head was in he told it there for a second, then he grabbed my ass with his right hand to open it up a bit, and started to push in. I was still pinned to the wall, he was so strong I had no way to move when he began to slowly move back and forth. I could feel every inch of that dick going inside of me. As soon as I started to gasp, he started to pick up speed. I loved the way this guy moved, I loved there is no chance of escape, he was fucking me so gently, and still, with every thrust, I could feel my caged dick tingle.

He flipped me over again, and just lifted me off the floor, I was with my back against the wall, and he was holding me with one hand while trying to adjust his cock inside me once again. When he was in he grabbed me with both hands under my ass, and he began to fuck me aggressively. I had my hand around his neck, legs upright in the air. I was in his arm, at his mercy. I was just taking that cock in, moaning, screaming with pleasure, I was begging him for more:

• “Yea you like that you little slut, do you love daddy’s cock.” – he said.
• “Oh, yes daddy, I love your cock, fuck me, daddy, fuck me, please.”
• “You are a hungry little slut aren’t you. Where you a bad girl.”
• “Ah, yes daddy I was a bad girl, please daddy punish me. Ah fuck me, daddy, fuck me harder I need to be punished.”

I loved every second, every trust inside of me, I wanted to cum so bad. My cock was getting hard it was trying to break free of the cage. People came in and out of the room a few times, even maybe watching us for a bit, but I wasn’t sure. I didn’t know where I was even, I was in a trance and started getting fuck by daddy.

When he got tired he laid down on the ground and I mounted his on top. I was also tired, but there was no way I was stopping at that point, I wanted that inside of me. I grabbed his big hairy chest for support and started to fuck myself on top of him. Touching that chest and how solid it was gave me strength. I looked up at the door, and I saw Dahlia staring at me with a big smile. I didn’t say or did anything I just kept bouncing around and taking my time with it. I closed my eyes and when I opened them again she was gone. My fucker had rested for a few minutes since I could feel him grabbing my ass again. I could feel his legs lifting me, and him starting to take control again. He started to slap my ass again. Going full force with every stroke, I could hear my ass slapping over his thighs, it was going to be red tomorrow. I just could not keep it in anymore, my dick started to leak cum from all my panties and over him, thru the whole in the cage. He didn’t seem to care at all, as he still kept pounding my ass. I just lay on top of him, trying to catch my breath, and letting him do whatever he wants with me. He was about to finish and he asked me if I wanted inside or not. I told him I want to taste it. So he stood up, with me on the floor, and started to finish right on my sticking tongue, he covered my face with sperm, and it was leaking down my dress my legs, and down on the floor.

He sipped his pants, button his shirt and thanked me for the wonderful time, and left the room. I was still laying on the ground, covered in cum, just sitting on the cold, floor legs on the side, stockings down my legs, ripped in places. I probably laid there for at least 20 minutes before I got up and tried to get myself together. In all of these rooms, they were mirrors and sinks so I could, wash a bit, and fix my clothes and makeup. I could smell the sperm on me, and I could get it all out of my dress but it was good enough. I could feel my ass still pulsating from all the fucking it took. I walked out and went to find Dahlia.

I found her in one of the other rooms, she was down on her knees, 2 legs were showing under him, and she was bouncing her ass onto some guy’s dick. Her cock was moving up and down, hitting the floor every time she moved down. I could see on her lips and chin there was sperm dripping, she had her hand full with 2 cocks, sucking one or the other. She saw me walk in but didn’t say anything just kept fucking and sucking. I as the helpful friend walked at her. Grabbed her face, licked the sperm off, kissed her, and started to suck on the cock while she was working the other. In a few minutes, I left her to finish and went back to the table to sit down and rest.

She came back in 15 minutes; you could tell what she was doing a few minutes ago.

• “So what do you think you like here?” – she asked.
• “Nice party, I get why you attend them.”
• “Did you like what you saw just now.”
• “Yea, you looked so hot, serving these cocks at the same time.”
• “Good she said because that is a sneak peek of your last challenge.” “Now do you want to go home, or we can just spend the night here?”
• “How we will spend the night here?”
• “Well I have a date, and he has a booked room, I’m sure you will find someone dick to suck to get a place to sleep tonight as well. The car will be waiting for us at 8 tomorrow.”

She left me there and went with some dude upstairs. People started to leave, or move upstairs, I was wondering what to do when 2 older maybe 50 gentlemen walked by. They asked me if I want to join them in their room for the night, and I like that I had a place to sleep. Of course, I had to work for it a bit, but my ass was so stretched, that it was no trouble at all. We ended up having a nice evening of them fucking me on the bed, sucking one guy, the other fucking me, and so on. It was really slow and lovely, they were at all aggressive and they let me lay down most of the time, which is good since I was tired as hell. I spend most of my time on my back or my side, getting fucked and sucking a dick at the same time.

Day 12

In the morning the car picked us up, and we went back to the hotel. I spend most of my day laying down and resting, my ass was still on fire from the previous day and I had to rest and prepare for my final test, which was the next day. Dahlia didn’t seem that tired at all, but she let me rest all day, and just came back a few times to check on me. I left my ass to rest for the day, but I did jack off a few times, just for old times.

Day 13

The day of my final test of proving I have become a true sissy. Dahlia told me to not be scared, just do what feels natural, and to have fun. I washed, prepared my ass, put on a short curly wig, and a maid costume Dahlia gave me. She told me that it was nothing too complicated, she just told me some friends will come over later and that I’m supposed to greet them and do everything to make them feel comfortable and satisfied. She then left me to get dressed and told me to expect them around 2.

It was maybe 2:30 when I heard a knock on the door. I was dressed and ready, with no cock rings, no dildos, just a lube in my apron. I opened the door. 5 guys were standing there, they greeted me and entered the room. They all looked me over and smiled before passing by and going into the living room and sitting down. I wanted to be a good host so I asked them if they wanted something to drink, then started to get them beers and whatever else they wanted. Five large men were in the room with me, dressed like a sissy maid, I knew what was expected of me to do, but I was scared. Two of the dudes were black, and that didn’t mean anything, but you know the stereotype of a black man. In a few minutes, a heard another knock on the door, and I felt chills down my spine. Even more? What will happen to me today? I opened the door and a black dude was kissing Dahlia at the door. He entered and introduced himself as Mokombo, then walked to the other guys, they all seem to know each other.

• “Mokombo as in the dude from the bathroom?” – I asked Dahlia.
• “Yes, I told you I knew him.” – she replied.

I looked at her and noticed, she had her hair in 2 ponytails, with a white tank top, a short red skirt, and white panties. She was dressed like a schoolgirl.

• “What are you wearing?” – I asked.
• “What don’t I look nice? You didn’t think I will let you have all the fun alone did you? Come on now let’s treat our guests properly. O by the way, take 2 of these, they will give you energy for today.” – she said and handed me 2 pills.

I was relieved, I would have to take all of these 6 dudes alone at least. Also having Dahlia with me always made me calmer and I loved that she will be a part of it. I walked into the kitchen and saw her taking the same pills as well, so I followed her example. She was talking to the guys, sitting on someone’s lap, while I was still running around serving drinks.

• “So Dahlia let’s see your new protégé, Viki why don’t you come here.” – said one of the guys.

I walked over and they asked me to stand in front of them and spin a little so they can look me over. They ask me to lean over the glass windows we had, and shake my ass for them, which I did, but the moment I turned around I saw all 6 dicks out and Dahlia smiling at me.

• “So sissy, are you ready to prove yourself? Show us what Dahlia has thought of you.”

I didn’t need a second invitation I just walked over and kneeled.

Both me and Dahlia were down on the ground, the guys had us surrounded, and there was dick left and right. We both got to work, sucking one and masturbating the other, moving from one dick to the next. There was no time to waste and a lot of dicks to suck. We had removed most of our clothes already, just some laces and stockings remaining. Also, this dude didn’t have a small dick, they all had average size cock, and they were all rock-hard. I was enjoying the taste of one of the dick when I felt a hand lifting me over the ground. I was put on the couch on my hands and knees, my ass was getting lubed up, and Dahlia was next to me the same way. We started to kiss each other, and in the next moment, we both felt a dick penetrating our asses. They started to slowly fuck us, while the other dudes lined up in front, away to fuck us in the mouth.

• “Guys don’t be gentle; this is a proper sissy here. Show her what you got.” – said Dahlia, just before receiving a second cock inside her ass.

The dudes did what they were told, and started to fuck me more and more aggressively. I was still sucking a cock when I also felt it, 1 of the dudes was bending over me, and a second one was trying to penetrate at the same time. And they didn’t care that cock was going in and they didn’t want to slow down either, all I could do is relax, loosen up my ass and take it. Me and Dahlia’s cock were hanging softly under us, and we were moaning together while getting fuck by 2 cocks at the same time. They took them out and gave me a moment to rest, while we were still kissing each other. Then one of the guys grabbed my hand behind my back and pinned me down while starting to fuck me hard. Dahlia was also getting fucked and sucking cock at the same time. I was slapping my ass and begging for more, while the guys kept switching, one at the back and 2 at the front, switching between me and Dahlia, I could taste my ass, and I could taste hers, in time I didn’t know which it was and I didn’t care.

They turned me over, and I was riding one of the dudes while sucking another, Mokombo was approaching to penetrate me as well, while dahlia still on all fours next to me started to suck my still soft cock. I don’t know what these pills were, fuck I was craving dick like never before. They lifted my ass, so Dahlia can lick it, before placing me over a cock again. Her cold tongue felt amazing on my already red and hot ass. I was so horny I started to beg them to put 2 cock in my ass again. One wasn’t enough anymore. Dahlia was on her back on the side, getting fucked, while the other 5 guys were around me, I lifted myself, tried to stick my fist inside my ass, licked it, and sat back down again on 2 cock while trying to suck another. The party just started. In a few moments, the dudes were going back and forth, getting a drink, and coming back. When they ask us if we want a drink, they started to piss all over me and in my mouth, and I gladly drank it, I could see on the side doing the same. She was facing one of the guys, ridding him, while another was behind her fucking her as well, I stood up and went in front of her giving her my now hard cock to suck. One of the dudes climbed the sofa I also needed a dick in my mouth, while another was already behind me fucking my ass. I had a dick in each arm, one in my ass, and one in my mouth, while Dahlia was sucking mine, and taking the 2 others from behind. We switched up, it was my turn to ride and suck her cock. While doing so she started to piss, straight into my mouth, then kept fucking me in the mouth.

One of the guys that were fucking me started to cum on my asshole, Dahlia went straight away to lick the sperm off, and she shared some of it with me, before mounting on top of a dick again. I don’t know how much time it was, the guys kept fucking us, Cumming in our asses and mouths, we eat every drop of it, shared a lot, and spit into each other mouths. It wasn’t over they would sit down to rest, while the other kept going, and when they were ready they started to fuck us back again, I don’t know what they had taken, but these dick weren’t going soft any time soon. Two dudes sat on the ground facing each other dicks touching and I just had to sit on top of that, with another one I was sucking of course. I was jumping on and off of them. Sitting back on the couch lets up, next to my head, while one of the other dudes was tearing me open. I was checking how much bigger my whole was getting before going down back on the 2 dick again. I loved it, I loved those 2 juice dick inside of me, and I was screaming and moaning the same. After some time, I went back on the couch on all fours ass in the air to receive some love, Dahlia wanted to take my place and ride those juice dicks for a while. It was getting dark outside but we were not stopping. the dude we're laughing, throwing jokes and complimenting us, resting, and coming back in the orgy. They were taking pictures of our asses, how they looked with 2 dicks, or how stretched-out holes were.

We were screaming to them to fuck us harder, Dahlia was looking at me with this lovely look, and sticking her finger in my mouth, while moaning from the cocks at the same time. She was stroking hard on her cock, I saw her getting ready to cum so I took that dick in my mouth to lick every last drop of it. On the other hand, I came at some point but I didn’t care and just kept riding. I was with my ass up, filled with cum from how many loads I don’t know, how could they keep producing so much cum. One of the guys was fucking me, when suddenly he started to piss in my ass, filling it up, then told me to push and I let it out in a mug. He gave me to drink before the next guy did the same. I was drinking the piss pouring it all over my body, drinking a bit, and spitting it all over myself. Just a sissy slut, taking the master’s dick, doing everything she is told.

I was down on the ground on my shoulder, with legs up on the couch and one of the dudes was fucking me, I was playing with my cock when I started to cum right into my mouth. Even Dahlia came to fuck me for a bit, and she came right into my ass. Then she started to lick all the sperm coming out, not missing a drop. She was caressing my asshole, when I started to feel her nails and then my finger going in, in a matter of seconds she had her hand in me and was fucking me like that, my ass was wide open.

In the end, I was laying on the couch on my back, while the guys were fucking me, and Dahlia was right on top of my face. The guys were moving from me to her ass, fucking her for a minute or so, before Cumming right in her ass. She was pushing the sperm out, and it was dripping off her ass, going down her balls and right into my mouth. Then the next guy, I was Cumming it off her ass, licking her hole. I had sperm all over my face and my mouth was full. I was playing with it not swallowing it right away. When the last guy came, Dahlia turned around and licked the sperm off my face, cleaning me up, before kissing me. I still had a mouth full of sperm for us to share.

We were exhausted, all of us laying around where there was space, breathing and laughing. What an amazing sissy experience, I was such a good slut, and they all told me to. I was a proper sissy now and they told me to be proud.

It was already late and the guys left, we were still sticky and covered in sperm and piss, but we were lying in bed, holding each other. Dahlia told me, that I’m the first sissy to take so many cock at once. Normally she max out at 3 or 4, but I jumped straight to six. I told her we can try again for more:

• “It doesn’t matter we can take them all”.

She laughs and said:

• “Ok next time we go for 10.”

We felt a sleep like that in each other arms, covered in cum.

Day 14

Day 14, my last day with her, before I had to go back to my life and work. What an amazing experience this all was. We got up and the morning and it wasn’t so fun anymore to be all covered in stuff, so we took a shower tougher. Just helping to clean each other and making out under the hot water.

Today was a day for rest. We were just talking about the future and what I think will do from now on. I honestly could not answer her, but I knew 1 think I was going to miss her. But with a smile and I kiss, she told me we can see each other any time I want again, I was her best sissy, and this time I believed it. She told me we can hook up again and again, and that Elena and Diana were asking for me, hoping I can do it again sometime. This made me so happy. She also mentions if I wanted to I could help her train the new sissy since she still wants to keep doing that. But she told me to first go back and embrace my new life. Figure it out on my own, go see my friends and family, but keep it all a secret. Not that I’m a sissy now, I could tell the world that, just the 2 weeks we had together. Of course, I was going to keep her secret, I didn’t want to tell anyone about my old life anything anyways, to be honest. I planned to go back to being a normal guy for a while again, maybe have a few casual hookups. I asked her what if after going on my own and in a few months I realized this is the life I wanted. This was my place and I wanted to return to her, for this to be my real life. Well then, she said, I will welcome you with open arms, you can be my assistant with the training, or whatever else you want, I would love to have you back, and I’m sure there are a lot of other people here as well that would love that as well.

On my last night with her, we were still tired from before, but since it was our last night together for a while we had to make love. Just passionate love all night long. Two naked bodies enjoying each other, fucking each other, and loving every second of it.

In the morning I back all my stuff and all the gifts Dahlia gave me, and it is time for me to fly home. Planning to come back very soon, even if it’s only for a visit. But I had a feeling it will be more than that.

The End