I Finally Become A Sissy Gurl free porn video

This is a FigCaption - special HTML5 tag for Image (like short description, you can remove it)
When I travel for work, I have often fantasized about meeting another sissy or a daddy from the internet. But I am usually so busy that I don’t have the time or the nerve. Time can be worked around, but I worry that they may have an STD and don’t disclose it. You can get herpes from sucking cock.

Some back story – For years I have been a sissy. I sucked the cocks of a core group of three friends in high school. I got really good at it. But none of them would ever agree to top me. Also, they let me wear panties and sometimes some lingerie, but going full fem-sissy was never on the menu.
As I got older I tried anal with a few guys. But no one ever taught me how to do it properly. I didn’t even know that there should be prep work involved and I knew very little about lube. Needless to say that my experience was very painful and left me wanting it only in the realm of fantasy.
When I started traveling for work, I didn’t bring any panties or anything fem with me for years. I always feared that I might somehow get a random bag check in the security line and be mortified. Many times I traveled with coworkers and would have to open my carryon.
Now I travel alone and check my bag every time. Most times I don’t bring anything with me. But when I get to a city, I will find a department store or boutique and pick up something new and cute to wear while sleeping in the hotel. This time however, I had packed two pairs of panties, a bra, and a nighty.

Now to how it happened.
My job is a corporate trainer. I travel around the country pretending I know how to teach people to run their business.
There was one guy who came to my trainings and was always very friendly. We will call him Terry. I assumed that Terry was friendly with everyone, and I never thought much about it. In the last 12 months he had been in 2 other trainings and I saw him briefly at an industry meeting in Texas.
This third training with Terry, was three days long, and I was just observing another trainer.
I spent most of the day on my phone in the back of the room. The courses are usually held at nicer hotels but this one was in a conference room of a $200 a night business hotel. The kind that gives you free breakfast with each stay.
The first training day was a normal day. Flew in the night before. Woke up, did the job. Had drinks with the students at the lobby bar and went back to my room to dress up and masturbate.
I would fantasized about the guy who I talked to online. Him coming to my room and using his cock to make me into a woman for the night. It’s a pretty standard fantasy when I travel. Sometimes I will even text pics of me dressed to guys I’m trying to meet online. But at that point, I had never actually tried to schedule a meet-up.
On day two, I woke up 10 minutes before the class was to start. I raced to get dressed and forgot that I had left on my panties from the night before. I was clearly hung-over. I got to the conference room, barley on-time. About an hour into the class I dropped a pen from my table and reached over to pick it up. It was then I realized I had accidentally been wearing panties and maybe, maybe, maybe for a brief second exposed a small shot of them to the only person sitting behind me.

They weren’t 100% fem panties. The were from a plus size retailer. Cheetah bikinis with a black nylon hip. Very French cut and very see-thru. The kind of panties women wear when they know they are putting out. But if someone got a glimpse of just the back they might have been taken for mens underwear.

Most of the time I sit in the very back and check out online personals on my phone. Trying to get the nerve to write someone and ask them to come to my hotel room and make love to me as a woman. But I am not at all passable and I usually lose the nerve.

At the end of the day everyone left the class. Most would rush to get 2-3 drinks in them at the lobby bar, before going out to eat at some insanely expensive steak house. Some of them would also wind up going to strip clubs with the other students. I guess it was the only time they were away from their wives long enough to get away with it.
I was alone in the room to clean up a few things. Pack up my laptop and head back to my room for a quick sissy-session before going to dinner.
I leaned down to unplug my laptop from the powerstrip on the floor when I heard him say “I always wondered but now I know.” I jumped up surprised to find Terry standing very close behind me. Terry was a CEO of a family business. Very smart, very accomplished and had a presence to him sometimes. Like he had a commanding personality if he ever had to turn it on.
I stood up and looked at him. Smiled and said “I thought I was alone.” I continued to gather my things and he came very close to me. Terry stood about 4-6 inches taller than me and he was close enough to touch me.
“I say to him, I hope that you enjoyed to course. You’re becoming a regular here.”
Then he says to me “The courses are helpful but the surprise view this time was better than anything I could have planned.”

“What view is that?”
“Oh each time you lean forward today I could see something poking up from your waistline. It was the same thing I just saw again, but maybe I shouldn’t call it a waistline maybe I should call it your panty line.”
He didn’t back up or move forward. Terry just looked at me. He was probably focusing on how quickly the color drained from my face and I began to start shaking.
I began to mumble and stammer “my I guess I” I tried to think of a spin to his comment but nothing was coming. I knew now that I had flashed him earlier in the day when I dropped my pen and I flashed him again when I thought I was alone in the room. If I had taken the time to get ready I would have had a shirt long enough to tuck in and probably not worn panties. Something I had only done once before.
What made it even more difficult to deny is that that tag on these panties suck out the back like a giant sissy flag screaming “this guy is wearing CACIQUE PANTIES!!!”
Before I could get a thought together Terry stepped close enough to me that I could feel his breath. “I have suspected you were a sissy since the first time I saw you. But I wasn’t sure. There could have been an explanation for your shopping, I’ve bought lingerie for my wife before. But I don’t wear her panties to work.”
When Terry said that he slightly motioned his right had towards my waistline.
My mind had come to me by now and I responded “I think your confused and probably have a mistaken something for…”
Terry interrupted “I saw you back in January I saw you shopping in Atlanta. I was almost sure you were a sissy then. Buying panties and makeup. But it could have been for your wife. But now I know that isn’t the case. The question is how far are you looking to take it.”

When I have gone shopping while at a training, I try to go to place I wont run into anyone. I take a taxi at least 10 miles away, I wear clothes that don’t call any attention, and I try to go before anyone gets into town, or after everyone has flown home. But this time I was dumb enough to go to a mall. Something I had wanted to do so many times before but lost the nerve. Fuck I was stupid.

I backed up and put on a masculine attitude. “Dude I think you have me confused with someone else and I am not comfortable with…”

He came right back into my personal space, and then like a cheesy rom-com, puts his finger over my lips and said “Shhhh. I saw you, and I knew it was you. I’ve been looking at your ass all day and I knew I had to try.”
Then without warning he took his long arm reached around my body and stuck his hand down my pants. Rubbing my panties and pinching my ass. Surprised I didn’t jump away. After all this is something I wanted right?
Terry then says to me “you may not look like a sissy, but I’m sure you act like one. Now lets just see if your playing sissy or if you really are one.” Then he grabbed my hand and pressed it against his crotch. He was big and hard. I knew instantly that he must be dripping precum from how warm it felt. If my hand stayed there it would probably soak through his jeans. My cock was also starting to get hard. Terry’s hand kept rubbing and pinching my ass, while his other hand forced my hand to rub his cock.

As you can guess, I had no idea what to do. My mind began racing with questions. Do I give in? What is he going to do next? Was he going to just take me right there? Was he going to kiss me? What should I do with my hands?
Terry had instantly taken control of the room and the situation. I was in a complete submissive role. At the same time, my adrenaline was pumping like it had never before. My hands shook, my mouth was instantly dry, and I felt like my eyes were losing focus.

Terry just stood there. Rubbing my ass with one hand, using his other hand to force me to massage his cock. I didn’t realize it instantly, but we were no longer face-to-face, he had pivoted to my side and I had started to close my eyes. I could feel my shoulder almost touching his chest. He started to push his finger into my bottom a little more and a little more, to he was almost massaging then entrance to my hole.

When my adrenaline had rushed I lost track of time. All I knew when I got my head back was that I had not said no, I didn’t say to stop. I had my one hand rubbing his jeans and what did happen was that far too much time had pasted for me to protest.
Terry then said “I don’t need a yes, I just need you to meet me in 304 in 30 minutes. I need to let them men know I wont be joining them for dinner. My dinner is already served.” And with that, Terry pinched my ass as hard as he possible could. It hurt so much I thought that he was going to rip part of my cheek off. And he walked away.

I stood there like a c***d “what the fuck just happened?”

I grabbed my bag and almost ran back to my room. As I walked to the elevator I saw Terry talking to some of the other people in the training at the lobby bar. He didn’t even act like he saw me. He played it very cool.
I got back to my room and at that point I was furious, “dinner is served”. Fuck you Terry. You can eat my ass if you think I am doing anything with you. I took off my pants. I wanted to get out of those panties as quickly as possible. I was embarrassed and kind of scared and a whole lot of other feelings.

As I went to throw my panties away, I grabbed my nighty and my bra, then I saw the second pair of panties I brought. They were a pair I had bought with one intention. I told myself “you only wear these when you decide you are going to give into a real man.” They were powder blue flower print, satin, with purple lace trim around the waist, and purple lace ruffles around the legs. They were the sexist panties I had ever bought. They were the panties that tell a man, if you are seeing these, my pussy is already wet.

I looked at them and for a brief second I thought why the fuck not? This is someone who isn’t going to have a disease. He is probably safe. He is always nice. But I was also scared. He had a big cock. What if I wanted to stop and he didn’t? What if he told people? How far did he want to go?
I thought about getting on the bra, nighty, and panties, going to his room and trying to figure out what happened. I would only suck his cock. I wouldn’t do anything more. But what if he says he wants more and doesn’t take no???

With in a few minutes it was time to meet him and I found myself knocking on his door. Instead of wearing anything other than jeans and a t-shirt, I opted to put my sissy clothes in a runners bag. In case for whatever reason he was able to settle me down enough to get into character.

Terry answered the door to his room. But it wasn’t predator Terry, it was nice friendly Terry. He invited me. It wasn’t a suite, this hotel didn’t have them, but it was probably the largest room they had. “Do you want a drink to loosen up?”

I said “we need to talk.” Terry responded rather quickly “I hope the subject isn’t how we aren’t going to do this thing, cuz you wouldn’t be here if it were.”
Terry had a bottle of Johnny Walker, he pour a drink and handed it to me and topped off his glass.
At that moment my guy brain kicked in, I was as clear thinking as I had been since his hand grabbed my ass in the room downstairs. So I began “Terry, I am not going to try and pretend that I don’t wear womens clothes. I do. And lets be honest you had me pegged when you called me a sissy, I am. But what that means to you, and what it means to me might be very different.” He interrupted “tell me what it means to you and I will tell you what it means to me.”

“You go first” I responded. But that was a mistake. I gave him the chance to take control of the conversation, and while he didn’t become a predator, he didn’t answer the question either.
What Terry did say was “I am glad you came, and so please drink up and relax. I’m happily married, but I have always wanted to experiment. I love my family I discretion is a must. I used to let my roommate in collage blow me. He gave the best head. He was probably bi or some shit like that. But in collage…look he used to get drunk and put on panties and blow me. You reminded me of him from the second I met you. I know you want this too. So lets just get to it.”
He was sitting on the edge of the bed drinking his scotch and I sat in a chair across from him. Normally I might have thought that he only wanted head. I could blow him and leave. But finding a dick to suck is never a challenge. I was clear in my head and I wanted more. I wanted someone to make me their wife for the night.
I then said to him, “Terry I am going to be really honest here, if all you want is for me to suck your dick, probably not gonna happen. I am not saying yes, I am not saying no. But what I came here for is more. If I am going to do this, then we need to have a conversation. You may just want to cum and send me on my way, but that isn’t what I want.” He interrupted “then say what you want. Stop being a pussy, let me see those panties and the back of your head in my crotch. If you want something more then you need to ask me for it.”
Annoyed I finally blurted out at a place that was far longer than I ever should have “I want a daddy! I can suck a random cock every day of the week. I want someone to make love to me like their wife. For fuck sakes, I don’t want to just be a cock sucking whore. I want someone to make me open up. I want someone who will entice and seduce me to the point where I want them in my pussy. Yes that’s what I call! I am a fucking sissy and I want someone to make me give them my pussy. To cuddle me and do it slow and help me. I don’t want my pussy ripped open. I want sex. I want it the way that a man gives it to a woman. I want to be treated like a woman. If that is what you want then fine lets get to it. If you just want to shoot a load because you want a better blow job than your wife then this is a fucking waste of my time.”

Terry responds “We both know you didn’t come here to leave. You want to show me your panties, you want my cock. We both know it.”

I interrupt him “I don’t want your cock Terry, I want a daddy. I want to be someone’s sissy for real. Not for a quick BJ and high five.”
He then gets up from the end of the bed. I thought he was going to hit me. He came over towards my chair, but then stopped short and grabbed the whiskey bottle. Filled his glass again. He takes a drink and doesn’t say anything for a second.
Then he says “do you want more?” Motions with the bottle. I lift my glass to him and realize that I had finished off my glass of scotch. He fills my glass and then goes back to the end of the bed. “I told you that my roommate wore panties. But that was only the beginning. We were roommates for 2 ½ years. I expected there to be more on the menu, and that’s why I prepared.” He then got up and walked over to me, lean down. Terry ran his giant hand through my hair, then he kissed me long and slow. We kissed long enough that it was like making out.
Daddy bought you a gift and its in the bathroom. But first daddy wants to know your name. “You know my name” I replied. “No baby girl I want your sissy name, if you want a daddy then you already have one, and daddy wants to know what’s in your bag there, I bet you brought something you want daddy to see. Go into the bathroom and see what daddy bought you, then come out and show daddy what you brought for him.” He then kissed me again, took the glass from my hand. He took my by the hand and led me to the bathroom.
He opened the door, turned on the bathroom light and gently pushed me into it by the small of my back. I walked into the bathroom. Then said that my gift was in the box.

Sitting on the floor was three large boxes, from….. lets just call it the most famous online retailer. I could hear Terry from the other side of the door say, I ordered them yesterday while we were in training. I guessed that they would fit. Inside was a bright white cocktail dress, black heels, a wig, several different kinds of makeup. There was some trashy cheap lingerie, a black bra, a black thong, and some cheap costume jewelry, and an enema kit. My cock went insta hard.

Now if you have read the story to this point you may be thinking “GET TO THE SEX ALREADY.” Well I am getting there and trust me it happened.

I wont go into detail about getting dressed. Suffice to say I put everything he bought on. I didn’t think to put on anything that I wore. When I came out Terry handed me a glass of vodka in a martini glass. I said asked him what it was and he said “scotch it for the boys, vodka is for the girls.”
I sat down on the bed. I was in full female mode at this point. Terry came over and sat down next to me. He leaned in and kissed me. Then said “I hope you like it, I cant wait to see your present for me.” I responded “later.” Then we started making out.
I reached down and rubbed his hard cock while he kissed me. Then he slide his hand up my thigh. Eventually he pushed his hand in between my legs to my extremely hard cock. “Oh feels like someone is ready.”
“Yes I am Daddy, and it feels like your ready as well.” I moved down from the bed to get on my knees in front of him, he then made me stand up and pull up my dress and show him the thong. As I kind of twirled around he pulled my onto his lap and positioned me to face away from him and kissed my neck. At the same time I could feel him grinding against my pussy. He pulled my dress up enough to get his hand onto my panty-covered cock. He jerked me a little and then said, daddy wants to taste you.

Like a good gurl, I wanted him to suck me. But I also didn’t want to cum and then lose my nerve. I said to him, no daddy, not yet. Later. I want to thank you for the generous gift first.
I laid him down on the bed and unzipped his pants. After a little maneuvering I had Terry’s pants around his knees. To my surprise Terry had on a pair of Vanity Fair full cut briefs. Which are one of my favorites. I looked at him and said, “these are so sexy”, as I rubbed and stroked his cock through them. They were absolutely drenched in precum, which I liked from them. Then I pulled his cock free and began sucking his cock. Like a good sissy, I showed my gratitude for him by kissing the tip of his cock first. His precum lined my lips and stuck my tongue out and licked it off my lips. After that I ran my tongue up the shaft of his cock, got to the top then went down and licked his balls. I worked on them briefly before hungrily devouring his cock. He was much larger than I was able to take in. He began breathing heavy and rubbing the hair of my wig.

I stopped for a second and said, “Daddy, your far too big for me to take all of this.” I reached up and took his hand into mine. I then lowered my head and began sucking him again. At the same time, I placed his hand on the back of my head. His hand sandwiched between the back of my head and his cock, I pushed my head down onto him crotch. Instructing him to force me down. Terry knew what I wanted took both of his hands onto the back of my head and began pushing his cock into my mouth while pushing my head. He was gentle as I gagged on his cock. My eyes watered. I then stopped looked at him and said, “Daddy push me all the way.”
I went back down on his cock and Terry gagged his entire cock into the back of my throat. He kept my head pressed into his crotch and let me gag for a second. Then he realized his pressure and I came up for air.
I looked at him, wiped the tears from my eyes and then said “Again.” This time Terry pushed his cock even harder into my mouth. Relaxed his pressure I came up and the second I motioned back down, he thrust his cock into my mouth. He did this five or six more times. Then I said Daddy, I want to feel you inside me.

I realized I just offered to let this giant cock inside me, and I never thought about lube or anything else. I was a submissive woman and I didn’t want the moment to pass. But I had not brought protection or lube.

Terry leaned over to the bedside table. Opened the top drawer and pulled out lube and condoms. I had planned on coloring his cock the same color as my lipstick but I was too into it now.
Terry got up, pulled his pants all the way off. Took off all his clothes except for his panties and put on a condom. Then put a ton of lube in his hand. I was now on my knees on the bed. I wanted him to lay down and I was going to go cowgirl.
He walked behind me, climbed onto the bed and spooned me. He rubbed his hands together. Then with one hand rubbed my lil sissy clit and the other he moved his fingers around then entrance to my pussy. The more how was stroking the further his fingers went.
I was growing closer and closer or orgasm. At the same time I was pushing against his fingers more and more. Terry reached down and picked up the lube, put more on his fingers and then began probing me with them. It wasn’t long before I found myself bending over a little with each push. I felt on finger go in all the way, then two. He fingered me and I was really losing up and getting into it.

I was bent over and I assumed Terry put lube on his cock. Then I felt him start to rub his cock up and down inside the entrance to my pussy. I responded instantly by pushing back into him. We tried for a few minutes to get inside me without it hurting. Each time I tried and tried. I wanted to be the kind of gurl that he could just jam his massive cock into and start pounding me. I was spirited in my effort but it hurt. Each time he would pull out, he would say something reassuring. The first time, he said “don’t worry baby girl.” The next time “Relax, your pussy for me.” Again he said “It hurts every woman the first time, I am patient, take as long as you need.” But I wanted it and it was hurting a lot.
After several attempts I asked him to lay down. His cock was so hard it stood up from him like a flag pole. Maybe he was too big for me to take. Maybe I should have tried other guys first. I applied more lube to my pussy.
Then I startled him and lowered my pussy onto him. At first the tip went in easily. But this time, I had flashes of all the tranny porn I had watched. I was finally that gurl. I pushed on. It hurt. But it is something I had to know about. With in a few minutes I lowered myself all the way on to him. Retreated my pussy back up to his tip and went all the way down again. I then relaxed myself and laid my head down to his chest. This last time he went into my pussy much easier and it actually felt really good.
I then quietly whispered to him “its finally happening, I have been dreaming about this moment for a long time.” Terry ran his fingers through the hair of my wig, and then started rocking his hips. He did it slowly and with minor strokes at first. There was still some residual pain, but I composed myself and propped myself up and started to ride him.
At first Terry was pushing into me, but as it got better I began to lift up and down on him. Eventually, I was doing all the work and it felt amazing. I had his cock inside me, fucking me. I don’t know when it happened, but I realized that I was no longer wearing my dress. I was there with my thong pulled to the side. Rubbing my tits and bouncing on this mans cock.
After a little while of enjoying this ride I needed to catch my breath and I slowed then stopped. Terry told me to lay down on my back and I did as I was told. Then he took off his condom. I freaked out. At first I thought that he was going to bareback me. I didn’t protest, just looked at him. But he reached down and put on another condom and more lube. I could see that then condom he was wearing was leaking a lot of precum out of it as he dropped it onto the floor.

Then he came to me and pushed my legs apart. He then put his cock inside me and fucked me missionary style for a few minutes. I kept arching my back into his thrusts and before long I was moaning and then I found myself saying things like “oh fuck me daddy, please use my pussy, I belong to you, this feels so amazing. I moaned and thrust. After what felt like ages he quickened his pace then said “ I want you in so many different ways.” I was confused but then realized his statement was an apology, because then he thrust harder than before, and then harder again, and then he started to shake. I had made my daddy cum. He was cuming in my pussy. He let out a huge breath when it was done and then laid down next to me.
I could feel the lube around me and what felt like it was inside me.

He laid there looking at the ceiling and rolled over and placed my head on his chest laying next to him. After a few minutes, he asked me, if I wanted him to finish me.
I was not going to let this night end with a cheap hand job. I thought we had been fucking for hours, but in reality it had not even been 30 minutes. I laid there, told him no and then I reached down and started caressing his balls.
What I had hoped for was for him to get his second wind. I was going to start sucking him again and then get one more good fuck from him. But eventually he got up, went to the bathroom and cleaned himself off.

He came back and asked me if I wanted another drink. He had taken off his panties and clearly he acted like it was time for me to go.

I had to figure out how to be enough of a woman to get him back in bed. I began rubbing my balls like they were labia of a vagina. I liked my fingers and then went back to rubbing them more. I said to him, I would love another drink. He poured one and handed it to him, I drank it all down in one swift swig. Handed him the glass. I liked my fingers and went back to rubbing my balls. As I handed him the glass, I said “another please.” Then I folded my balls to look like a vagina. I did that while he poured another glass.

He hands me the glass and asks if I want to take a shower. I said, I can shower in the morning. But first I want to finish. I sipped the drink laying on the bed. Eventually he came back into bed. He said “its clear you are not letting me call it a night.”
“Do you want to call it a night?”
“I’m exhausted and unless you are planning on sleeping here so should you.”
“I don’t thin we will get much sleep if I stay, but I don’t want to be alone.”
“Do you want to stay here? You can, but you will have to leave early so no one sees you.”

“Then get up form the bed, I walk/prance to the bathroom. And say “fine by me.” I went into the bathroom and cleaned myself up. I didn’t notice it the first time, but inside the box was a small sampler of some cheap knock-off version of perfume. After I cleaned up, I sprayed it all over me. I put on the panties I brought, the bra I brought, and the nighty.”
I came out of the bathroom. He had already dimmed the lights and was in bed in a bathrobe. He was on one side of the bed, on the other was a full glass of vodka waiting for me. His lamp and my lamp were the only lights in the room. I walked a feminine as I could muster over to my side of the bed, pulled back the sheets, and said to him “this is daddies present.” I then got into bed.

Terry and I cuddled for a bit. But I could tell that my body was done. I was exhausted, he was yawning and I could feel the anal pain in my pussy and stomach. It was probably good that we didn’t go for round 2.

The next thing I knew, I could feel a hand rubbing on my soft clitty. I had fallen asleep at some point and the clock on the table said 1:37am. Was it correct? Had I been asleep that long. It was dark, but it’s a hotel. Do people actually set them?
As Terry rubbed me I came to life. I could feel him in a more subdued mood, but also like he was hungry. He stroked my cock and rubbed my ass with slow, but purposeful motions. It didn’t take long and I went right back down to his cock. No longer wearing a wig, he pushed my head down, but didn’t choke or gag me this time. It didn’t take long before he was pulling me up to his massive chest. I reached around and started stroking his cock. He let out precum the more I was able to move my hands. I was laying on his belt line now. Rubbing his cock against my pussy. The only thing that separated us was my panties and parts of my nighty as it fell up and down. Eventually he said to me, take your panties off.
I rolled over, and got up. I stood on the floor of the hotel room and as I took them off I bent straight over. Basically acting like some cheap version of a whore or a stripper. But Terry didn’t notice. He had already rolled over and was getting lube from the nightstand. Neither of us could see well as none of the lights were on. I could hear him lubing up, then he mounted me again and put his fingers inside me missionary style. I relaxed and forced myself against them. I could feel some residual pain from earlier, but I wanted to loosen up faster. Terry then leaned down and put my cock in his mouth. He fingered me while he applied several different doses of lube.
I was getting close to Cumming for the first time that night, when terry said roll over. He puller his fingers out of my and positioned me on my knees bent over. I fingered my a few more times, then I felt him enter into me.

It only took a few thrusts and he was inside me. I could feel him pushing and fucking me. After only a few thrusts, I relaxed my head down onto the mattress. There I was wear a bra and nighty. A man was pushing his cock into me. I was for the first time, face down, ass up and I felt like a woman. My nighty slipped down my down with each thrust till it was almost bunched up on my head.

He fucked my like that then stopped. Pushed me onto my back again. In the missionary position he put my legs above his head and started fucking me again. This time he was really fucking me. He pushed my legs almost above my head and slammed his cock into me. A few times it hurt, but it also felt so amazing. I was feeling like a used woman having her pussy enjoyed by a man.
Daddy got much more verbal this time, he was saying things like oh sissy, your pussy is so tight and feels amazing. I would respond saying things like, daddy you own this pussy. Its yours.

“Take it all sissy, take everything I have”

“Oh daddy, don’t ever stop. This pussy belongs to your cock. You own this pussy.”

Then it happened. He sped up his strokes and began to climax. It wasn’t until that moment I realized, it felt like something more was happening. I knew he was about to cum so I reached down and started stoking my cock. I wanted for us to cum at the same time. But if not the same time, then I wanted to cum with him still inside me and hard. Daddy began to cum just a few seconds before I did. I could feel him pushing and I couldn’t tell if that was his cock throbbing or my prostate. I cam all over my stomach. I was amazing. Daddy also cam. When he was done he stayed inside me. On his knees. Staying upright. He stayed in longer than last time. At first I thought it was because I had covered my belly in cum. But that wasn’t it. It felt different this time. Then he said to me “i'm sorry.”
That was the moment I realized he forgot to put on a condom. He had cum inside me. I didn’t know what to do. I panicked for a second. But it had happened. I have always wanted a daddy to take me. In my fantasies, he doesn’t wear a condom. I would never in a million years let him do it. But it was done. I had let my daddy breed me. His cum was inside me and I wanted it there.

After a few minutes, he moved to go clean up. I grabbed his hand. I didn’t want anything to be weird between us. My cum had begun to drip off my stomach. I took his hand and laid in on my stomach. I then moved it around and used his hand to rub my cum all over me. Eventually when it was sufficiently cleaned, I liked one of his fingers. He stopped me and then he proceeded to lick the others. I could tell it was not a flavor he was accustom to and he didn’t like it. I rolled over. Got out of bed and put my panties back on. I had to keep my behind tight. I didn’t know if his cum would leak out of me, but I didn’t want him to see that. I jumped back into to bed. I tried to act normal and I set my phone alarm for 4am.

When my alarm did go off, I got up. Put on my jeans and left his room without saying anything. I walked back to my room. His cum had gone somewhere in the time I slept. But all I could focus on was not accidentally running into any students. Because I still had one more day of training with Terry and the rest of the class. And as you can imagine, it was not the last interaction I had with Terry or have had with Terry.

Same as I finally become a sissy gurl Videos

3 years ago
  • 0
  • 33
  • 0

Raised as a gurl

“Here, Slut Puppy! Here, girl!” Gina called from the living room, and I dutifully crawled in from the bathroom where I had just finished using the litter box. My little cockette dangled between my legs, the lock on my chastity cage clicking and the little bell on the end of it tinkling with each sway of my hips. My breasts hung down and swayed slightly as well. Gina liked me to crawl when I was being her Slut Puppy. She liked the collar around my neck and the little tail attached above the butt...

2 years ago
  • 0
  • 35
  • 0

My Wife Teachs me to be a Gurl

There was a note and a small box on his desk when he arrived home. The note said, "A gift for you, do not open until I arrive home, Mistress Victoria." As was Her wishes he sat naked except for his collar, ready for anything Mistress wished. Shortly after She arrived and entered the den, carrying a bottle of lube and a small towel.She grinned and said, "I see you saw My gift and like a good slut you did not touch it until I arrived."She knelt in front of him and poured some of the lube into her...

3 years ago
  • 1
  • 31
  • 0

The White Sissy Slave Society A Walk into Sissyhood

The White Sissy Slave Society: Sold into Sissyhood By Meeah Soo They were standing in a small group, drinking beer, smoking, and laughing. I could hear the rap music thumping aggressively from their boom-box. I could see them watching our car. It was late, well after midnight, and this particular park was no place for a white sissy to be at this hour. I've never been a physically or mentally strong person. I'm very easily intimidated. And there I was in a tiny plaid mini and white...

4 years ago
  • 0
  • 36
  • 0

Mattie Gurl

MattieShemale, Micro Cock, Lactation, Role Play, Flashing, Kinky A Fiction requested by a Contact.Waking to find Mattie not in bed, Jacob went to check on her. His eyes saw her still sitting on their couch with Jim and Jack beside her. He could see her arms over their shoulders, her head thrown back, eyes closed. Quietly he moved closer and almost gasp out loud, the boy's were nursing on her breast! Having heard their floor creak, Mattie opened an eye, raised a finger to her lips and motioned...

4 years ago
  • 0
  • 20
  • 0

made to be his gurl

After waiting tables for a good 6 months, I had finally got myself clear and could maybe get myself back to California. But I wanted to get there with some money in hand, so to save the air fair I thought it would be fun to share an the ride with someone or ones. I put an ad on Craig’s list for a ride share.I got about 4 responses and thought I had better meet with um to see if I could deal with a 4 day trip. The second guy that rumbled up was a long haul trucker, with a sleeper cab. He...

2 years ago
  • 0
  • 22
  • 0

MEETING THE NEW GURL

Well this happened to me about 10 years ago i was still dressing when ever i could you know shaved body no hair anywhere i'd put on a waist cincher (tie-up corset) gave more hips and smaller waist also added to my tits with inserts and pushup bra with nude stockings, tong, micro mini skirt, with a loose silk blouse and 4 inch heels i was almost passable add make-up and you couldn't tell me from a tall girl anyway i went off to one of our many locations for gays, t/v, t/s, c/d and lesbian bars...

2 years ago
  • 0
  • 32
  • 0

That Gurl

That Gurl Monica was a little nervous as she rode the elevator up to the 45th floor. It was the Executive Floor, influential money makers. She worked in the interoffice mail room for the whole building and had never hand delivered to “45”. Monica checked herself out in the mirror like walls of the elevator. Hand brushing her hair, she was satisfied that her cowl neck sweater with her pleated skirt were OK. The elevator stopped on floor 20 and a tall lady stepped in. They exchanged glances...

3 years ago
  • 0
  • 55
  • 0

Would she be a gurl

I was spending my third night out of town, supporting a very bad stressing business trip. Worst of all, I was horny as hell, since I had not fucked my sensual Ana in those days.On the other hand, I was pretty sure that my sexy babe would be now in her Black Master’s bed, being fucked in a very wild way.That bastard nigger would also fuck her in that nice tight ass…After having some light meal for dinner, I went back to my hotel. I was really tired and just wanted a relaxing warm shower and some...

2 years ago
  • 0
  • 26
  • 0

Working Gurl

Working GurlMy name is Danielle and I’m a working gurl . I started working in 1991 at the age of 20, my first job as a hooker was working out of an Adult Book Store North of Ft. Worth, Texas on I-35W South of the airport My boss was an older tranny named Jannice she ran the book store. On nights when she would call me in she would set me up in a booth in the video room. I never knew who or how many would come in to my booth. I was to service all that came to see me. Was I doing this for the...

3 years ago
  • 0
  • 46
  • 0

BiBoy turned to SubGurl

When I was young, my friend & I started to play the "I dare you" game which quickly evolved from looking at each others privates, to touching, to licking, to sucking. We would take turns sitting in a swivel chair in the middle of the room while the other sucked our cock for one minute intervals. Surprisingly I enjoyed sucking his cock just as much & if not even more than having mine sucked! And I could tell he didn't because he was just doing it so I would do it back, plus I would go...

4 years ago
  • 0
  • 22
  • 0

Me dressed as a Gurl

this happened about 25 years ago when i could half way pass i went to this night club for crossdresser, transexuals and transvestites west of balboa park one thursday night it wasn't has busy has on a friday or week end but there was a nice crowd mustly crossdressers a few trannys it was not to late about 8:30pm the company was fine mainly playing pool and looking around some good conversation us gurls we in back the guys were in front at the bar checking us out i was dressed to kill had on...

3 years ago
  • 0
  • 21
  • 0

Chrissie Becomes a Sissy Chapter 2

Chapter 2 Chrissie becomes a sissy It was Friday morning and I was sitting in the doctor's surgery waiting to be administered my weekly dose of oestrogen and my three month shot of Depo-Provera, which is the drug which chemically castrates me. I have been on Depo-Provera for the last three years and I could tell the last dose was wearing off as my mind was increasingly focused on submissive sexual fantasies. Nevertheless, Friday is my favourite day because I have begun to view the...

4 years ago
  • 0
  • 64
  • 0

stepson becomes moms sissy

Mark Peters let out a low moan that couldn’t be heard above the organ as it played "Here Comes the Bride." Although every other head in the church turned to glimpse the tall, dark-haired beauty imperiously making her way down the aisle, Mark kept his eyes fixed on his feet. Had anyone been paying attention, they would have seen a small tear escape Mark’s eye.It seemed like only yesterday that Mark’s mother and father had split up. Mark’s dad, Mark Senior, was a partner in one of the city’s...

2 years ago
  • 0
  • 28
  • 0

White gurl

Well this is something I never expected. Here I am in a gay resort in the Canary Islands, can't remember what it's called, with a man, a black man.I am effectively his woman and my raison d'etre is to pleasure him. Well, he has paid to bring me here and bought me clothes to wear, not that he asked or that they were anything I would have chosen for myself but I seemed to have any choice.He is black, 6ft, muscled and hung, a good 8 inches I'd say. I am a 5'6" straight man not getting any luck...

4 years ago
  • 0
  • 25
  • 0

The New Cheer Gurl

The new cheer gurl By Debry White This is a work of fiction. Names, characters, places and incidents either are products of the author's imagination or are used fictitiously. Any resemblance to actual events or locales or persons, living or dead, is entirely coincidental. It was the last year of high school for most of my so called "friends" but not for me. Even I am not in sports nor I am popular, I hang out with the football and cheer teams because I am the one that makes their...

3 years ago
  • 0
  • 49
  • 0

How to become a SissyCuckold

This is a How To Guide for Sissies and Cuckolds.Please do not read this guide if you have no interest in the cuckold/sissy lifestyle. Like most couples these days both partners will be doing demanding full time jobs. Traditionally husbands have done gardening, cleaning the car, putting out the trash, performing do it yourself jobs around the house, driving the car if you are going out in it together and anything that might come under the heading of 'physically demanding' work. It's true that...

2 years ago
  • 0
  • 30
  • 0

Moms teaches son to become a sissy sperma slut

I never knew my dad.That's not an excuse for what I've become – and that's not to say I need an excuse – it's just a simple fact that some people find relevant when trying to examine what I've become.Anyway, he was killed in a plane crash before I was born. Technically, he was killed in a plane crash while I was being born, but he died without knowing that. He'd been overseas at a business conference when my mom called to tell him she was going into labor, and had boarded the first plane he...

3 years ago
  • 0
  • 35
  • 0

Sissy Becomes a Slut

So by this time I was a sissy with two lovers Peter and David the brothers next door. They were quiet different from each other, Peter tended to be the gentler of the two. When he fucked me, he would carress my sissy body, lick my nipples and toy with my boi clitty. When we had the house to ourselves we would make a date out of it. We would kiss on the couch and explore each others bodies, he would take me upstairs to the bedroom, I wouold suck his fabulous cock and he would then hike my legs...

2 years ago
  • 0
  • 23
  • 0

White Boy Becomes a BBC Sissy Chapter Two

Chapter Two - Dominick's Plan I lay there on all fours, butt still gaped open, staring at its picture on his phone. I was getting used to this feeling of shame, embarrassment, and arousal at his objectification and domination of me with each humiliating thing he subjected me to. I didn't know it, but my soft, bare dick was beginning to leak pre-cum. "Here's what's going to happen today, sissy boy. I know you have more girly clothing and shit like that at home. You don't just show up at...

3 years ago
  • 0
  • 24
  • 0

Meeting an Old Buddy After Becoming a Gurl

When I arrived at his house, he was waiting for me in the front yard. I was nice seeing Victor after all these years. His once huge afro is now gone, replaced with a glistening shaved head. His 6’6” frame is still in excellent shape plus a few pounds. Then I remembered how much I used to tease him because his was so dark, I called him “blue-black” but he looked good. Vic welcomed me in the house, and told me how embracing being a gurl suits me. Victor complimented me on my dress, my new...

3 years ago
  • 0
  • 24
  • 0

Meeting an Old Buddy After Becoming a Gurl

When I arrived at his house, he was waiting for me in the front yard. I was nice seeing Victor after all these years. His once huge afro is now gone, replaced with a glistening shaved head. His 6’6” frame is still in excellent shape plus a few pounds. Then I remembered how much I used to tease him because his was so dark, I called him “blue-black” but he looked good. Vic welcomed me in the house, and told me how embracing being a gurl suits me. Victor complimented me on my dress, my new...

2 years ago
  • 0
  • 47
  • 0

Becoming a Sissy

Previously published, but in separate parts, this one is the whole story start to finish.This is the story about how I went from being an inadequate husband to being a porn addicted goon and finally in the past year fulfilling my sissy ambition to worship a big cock and balls. They belong to my best friend Tom who I have known for 20 years. It was a journey that took a few years but if I had been brave enough when I was younger would have taken no time at all and spared me lots of humiliation...

4 years ago
  • 0
  • 21
  • 0

Becoming a Sissy Part 8

Tom makes a decision. It lists Mandy's help. And Sissy proves herself.Tom had already made his decision concerning Peter. He had thoroughly enjoyed his role-play with Mandy, but knew that having his best friend as his sissy would be even better. He trusted that what Peter wanted was to service his Daddy, and he knew from the way Peter (Sissy from now on) had serviced him on that evening, that he would do anything for his Daddy.He too had explored X hamster and was aware of the degree of...

3 years ago
  • 0
  • 30
  • 0

Becoming a Sissy Maid for Mark and Rebecca Part Three Ms Rebecca Shares Her Sexual Research of Sissies

Becoming a Sissy Maid for Mark & Rebecca, Part Three - Ms. Rebecca Begins Sharing Her Sexual Research NOTE to Review Writers: Thank you so much for the incredibly positive feedback. It is definitely motivating me to write more and write faster. Now to part three of our story. "Tell me what you know about males who are feminized so completely they are transformed into a sissy, changed from the less than manly person she had been before coming under the control of a strict...

2 years ago
  • 0
  • 29
  • 0

Becoming a Sissy Part 10

Apologies for the delay. This is the final part of "becoming a sissy". Obviously, I have packed a lot more into this story, and I apologise if it got complicated with too many characters. I'm thinking of writing another story which will take up from where we are now, but I will make it more focused on one or two characters. It's my first story, so I guess lessons.Over the next five days a plan formulated in Tom's mind. As he thought about it he would have three submissive sluts vying for his...

4 years ago
  • 0
  • 50
  • 0

Becoming A Sissy Slut part 2

I awoke Sunday morning alone in Kassy’s bed, still in the tight mini skirt, my ass was deliciously sore bringing back a flood of memories from last night. I had spent the evening in full drag dressed as a slut and serving my mistress’s rubber cock followed by swallowing my own cum. It was hands down the best night of my life, I had never came so hard, and the rush I felt while serving her was a high that I’d never known. I rolled out of bed and stood up, my wig had fallen off in the night...

3 years ago
  • 0
  • 24
  • 0

Becoming a Sissy Part 6

The story returns to find Peter in the aftermath of his mind blowing night with Tom, how would he react?When Tom walked out the door and left me on my knees with my own cum stain on the floor, the taste of his arse, cock, balls and cum in my mouth I was stunned. The whole night was like a dream. Earlier in the day I considered myself to be a porn addict who would goon and wank for hours. Now? Well I had answered one question, this was more than a fantasy, the satisfaction I felt for giving such...

4 years ago
  • 0
  • 31
  • 0

Becoming a Sissy Maid for Mark and Rebecca Part Four Ms Rebecca Shares More About Meeting Stephanie

Becoming a Sissy Maid for Mark & Rebecca, Part Four - Ms. Rebecca Continues to Share the Events Surrounding Her Meeting and Getting to Know Stephanie NOTE to Review Writers: Thank you so much for the incredibly positive feedback. It is definitely motivating me to write more and write faster. Now to part four of our story. If you have specific suggests or would be willing to proofread the story before I publish it as an eBook, please write me at [email protected]. Thanks so...

3 years ago
  • 0
  • 44
  • 0

Danny Becomes a Sissy part 1

Daniel realized he had been spacing out again. Well, not really spacing out - staring at Dr. Brooks' pretty face. Daniel had never seen a doctor as beautiful as Dr. Brooks. She was young, maybe thirty, but she looked younger. She was pale and tall, as tall as Dan and even taller in heels. She had high, round cheeks, emerald eyes and the straightest, blackest hair you can imagine, flat bangs cut across her brow and the rest pulled back in a high ponytail. She was in a tight blue skirt that...

4 years ago
  • 0
  • 29
  • 0

Becoming a Sissy Maid for Mark 5

Becoming a Sissy Maid for Mark & Rebecca, Part Five - Ms. Rebecca Tells Mark About Meeting Stephanie and More I continued telling Stevie about Stephanie and how I got to know her and her sissy, picking up from where I had left off with my having just finished sucking Mark to a climax and being told to share the news of my good fortune performing the research he had assigned me to complete for him. "Good girl, Rebecca," he said smiling. "I'm glad you still like sucking your...

4 years ago
  • 0
  • 30
  • 0

He knew how to treat a Gurl

So, as all you cum sluts like me know when you are sucking a guy off and he is ready to cum they pull out tell you to open your mouth then jerk off and shoot their load mostly on your face (which is fine with me) as you try to get as much of it in your mouth to swallow. We work so hard sucking, licking, kissing a cock only to get some of what we worked so hard for. I could never understand it. Finally last night while I was trolling my favorite truck stop (looking so cute I must say) parked my...

3 years ago
  • 0
  • 28
  • 0

A GOOD GURL

Awhile back I ran into a guy online in one of the dating sites that was a TG. I was always turned on by a gurl with a boner so I chatted with “her” for a bit. She was married to a bi man. I quickly offered to join them both in bed as that would have been great fun! She told me he doesn't like to share but she did get horny when he wasn't in the mood. We quickly made a date to meet at one of the local waterside parks. She described her car to me and I told her what I would be in. At the...

4 years ago
  • 0
  • 40
  • 0

Hotel Gurl

I had posted an ad on Backpage and received the standard amount of online responses from the mouth breathers or the spammers. One response was very nice that read “nice pic! I’ll be getting into Tampa on the night of the 14th, staying for a few days. MWM, 6’ 3”, 250 pounds, DDF, late 50s, safe, clean, discreet. I’ll be staying the Hilton downtown and would love to get together.” We started texting back and forth and he seemed pretty sincere. He told me his name was Alan and that he is in town...

3 years ago
  • 0
  • 24
  • 0

September Gurl

September Gurl Belladonna [Author's Note: With Apologies to Big Star for the Title] Davis Perry rubbed his fingers across his forehead before he looked down at his son and said, "Are you sure you can handle it?" "Mom's asking me to watch Susanna for a few days, not go to the moon," Peter retorted, shaking his head. Susanna was four years younger than him and just entering high school. Peter had graduated the June before, but he had decided to take a year off before going to...

3 years ago
  • 0
  • 34
  • 0

Wolf Mountain Found Gurl

Wolf Mountain, Found Gurl By: Melody Anne Layla Pearson hadn't seen home in years, not since that summer day at thirteen when she was taken away to the private school. Or rather when Lyle had been banished because he wasn't what his father expected of his son. They called it a private school, in reality it was a mental hospital where rich parents sent their children when they didn't want to deal with their problems. The Wilder Institute had...

2 years ago
  • 0
  • 45
  • 0

Becoming A Sissy Slut Part 1

It was a Friday evening in late January as I walked through the lounge in the back of a bar in downtown Spokane Washington. A friend from work named Mark had invited me to come to his wife’s 30th birthday party and even though I didn’t know her, it was a good excuse to get out of my apartment. I had just moved to Spokane the previous fall, taking a job as an engineer for large road building company. At 21 years old and just out of college, I was pretty proud to start out with a $60,000 a...

4 years ago
  • 0
  • 63
  • 0

2088 Its a Sissy World

2088: It's a Sissy World Charles Pauline - Data Processor Cindy Pauline - Charles' wife Ms. Miriam Jensdotter - Charles' Boss James Marie - Charles' work friend Ms. Marysdau - James' boss Creampuff - A Sissy Store Worker Babykins - A Sissy Store Worker Suzi - The Sissy Store Owner Butterscotch - Creampuff's Roommate Supervisor Gabriellez - Creampuff's Apartment Supervisor Janice and Roger - Passengers on the Looper Ms. Hardcastle - Milking Salon Director Nurse Hamilton - Milking...

2 years ago
  • 0
  • 40
  • 0

Becoming my friends sissy

I was standing in the pub toilet having a piss. I had been in the pub for a couple of hours and had had a few pints with my mate Roger. I had tried to slip off for a piss by myself while Roger was up getting another pint. As I stood really close to the trough my little cock was dribbling, when Roger came bounding in. There you are Tom, I thought you had done a runner, he laughed. He stood beside me and fished out his enormous cock from his trousers. Unlike me he stood about a foot from the...

3 years ago
  • 0
  • 22
  • 0

Becoming a Sissy Part 4

Toms voice"Fuck me daddy, fuck me daddy, use me like the Sissy that I am, FUCK MY BOY CUNT, Give me your cock Daddy" I had my hands around the sissies hips as I fucked her doggy style pulling her pussy onto my hard cock, pounding and pounding. "Please daddy cum on me, paint my Sissy face, I want your cum on me, fuck me harder, I've been a bad boy"I loved the power Sissy submission gave me. I was a fucking sex god getting the respect I deserved. As I looked down at her back I could see the butt...

3 years ago
  • 0
  • 46
  • 0

Meinen Mann zur Sissy erzogen

Achtung diese Geschichte ist noch voller Rechtschreib- und Gramatikfehler. Jeder der m?chte kann diese Geschichte als Vorlage nehmen und sie verbessern. Jetzt reicht es mir. Ich hatte die Internet Seiten meines Freundes gefunden. Er surft also st?ndig auf Adult Baby Sissy Seiten. Ich hatte mich schon l?nger gefragt warum er im Bett nichts zu Stande bringt. Das kann er haben, ich werde ihn einfach in ein kleines Babym?dchen behandeln bzw im Grunde verwandeln. Er war eine Woche zu einem al...

1 year ago
  • 0
  • 54
  • 0

Chrissie The Saga of a Lovestruck Sissy Maid

Chrissie by c.w. cobblestone BOOK ONE "Mrs. Martin" Part I My right leg had a mind of its own. Rebecca frowned. "Why you keep bouncing like that? What's wrong with you?" "Um, I ... I ... nothing." "Bullshit, nothing. Something's up; you been acting weird ever since we got back from Paris. What the hell's going on, Chris?" I balled my fists. Clenched my jaw. Closed my eyes. Drew a breath. Took the plunge. "Okay. Okay. It's just ... well, now that we're...

2 years ago
  • 0
  • 44
  • 0

Sissy spit roast sleep over

Pt 1: Long black limoSissy Saraya was very excited because her new mistress had told her they were going to continue with her corset training tonight, she had been wearing her waist trainer and inflatable plug all day along with her favourite pink maids outfit and cute sissy 6" white heels and stockings with pretty pink bows, She had been watching BBC porn all day and was dreaming of cock while she finished her chores, Mistress text to say her driver would be arriving at 6pm sharp, Mistress...

2 years ago
  • 0
  • 43
  • 0

The SissyMaster

THE SISSY-MASTER CHAPTER 1 I have read many tales and stories on this site over the years; some of them 'autobiographical' and some of them complete fantasy. It strikes me that most of the stories have been written by the, either real or wannabe sissy girl and therefore is 'her' fantasy from a sissy's perspective. So I have written my stories of my experiences, beliefs and methods from the perspective of the male. This is for the REAL MEN that read this site, a guide to the...

3 years ago
  • 0
  • 25
  • 0

The Sissy App

The Sissy App 1. Setup "This is the longest user agreement I've ever read!" thought Rick as he scrolled and scrolled through the hundreds of pages of legalese on his recently-downloaded smartphone app. The "Sissy App" User License Agreement was indeed voluminous, containing numerous sections detailing the GRA Software Corporation's exemption from penalties, payments or legal requirements, granted by authorities or statutes, for any harm that may come to a user when using the Sissy...

4 years ago
  • 0
  • 30
  • 0

Subgoal sissy Desperate streamer slowly becomes a girl pt2

[heyyyy, I'm really really sorry this took so long, but wow here it is. I didn't expect so many nice reviews on the first part, thank you, it means a lot. And I'm really glad that we're going to be able to have so much fun on this journey together. I promise I'll do my best to keep this story coming but this is way more exhausting than I thought it would be. Please let me know if this length is okay. I'd be able to send them out more often if you prefer them shorter. I wish I had more...

4 years ago
  • 0
  • 34
  • 0

A Sissy called Jezebel Part VIII

A Sissy called Jezebel Part VIII - Jezebel has returned to hir classes at Templeton Academy: where young womyn become dominatrixes and sissies are crushed into submission. We are all getting an education on the Matriarchy in hir sissy life skills class. (Authors note: We are definitely at that world building point, where I really let my imagination fly off the hook. I am throwing out a lot of ideas, but hopefully in...

2 years ago
  • 0
  • 31
  • 0

Adult Sissy Little Girl World

Journey Into A Special World My name is Hannah Stone. I've been a reporter for a newspaper for years. A couple of days ago I ran into an old sorority sister and good friend Linda Hart. It's been a few years since we last saw each other and we decided to do lunch together. At the beginning of lunch we had the usual light chat. Then we sort of got on the serious side of chat, when I asked Linda how her marriage to Bob was going. "Oh, Hannah I divorced that bastard years ago. He was...

4 years ago
  • 0
  • 28
  • 0

Forever Her Sissy Chapter 6

This is a work of fiction for your enjoyment and all the characters are fictional. Please practice safe sex, respect others limits and know that bondage and discipline can be dangerous if done to extremes. None of the scenes in this literature are meant to be reproduced in real life. Be respectful to all women and to local ordinances and laws. I Absolutely love reading the reviews that you wonderful readers have been leaving, please, please, please continue to write and post...

4 years ago
  • 0
  • 23
  • 0

Becoming a Sissy Part 3

Third instalment. Apologies it has been slow until now, but things progress a lot. In part three. We start with Tom, getting some of his background and thoughts on Peter and then back to Peter's voice.Tom's story.Myself and Peter had been friends since we were in school together were we had an interest in supporting common which really kept us as friends for years and years. We finished school, went to college got our first jobs and settled down all the time being in touch with each other,...

2 years ago
  • 0
  • 34
  • 0

Training Sissy Michelle

I first became aware of "Sissy Michelle" back in the old Craigslist days. She would pop up in the T4M section, advertising herself as an older but very horny sissy looking to serve a group of kinky guys. She said she was interested in all sorts of kinky stuff, everything from group sex to watersports to hypnosis and lots and lots of bondage. She practically begged to be photographed and blackmailed into doing all of this. Here's an example of one of her ads that piqued my...

4 years ago
  • 0
  • 44
  • 0

Tweak Chapter Four Whats A Sissy To Do

What makes a sissy happy? What makes a sissy's Mistresses happy? It's complicated. Author's note: Although I'm posting this in serial form, I assure you, dear reader, this humble offering consisting of eight chapters, is complete. "Tweak" By: Simonne Danielle © 2008 - 2010 All Rights Reserved Chapter Four - What's A Sissy To Do "You have made your Mistress very happy, sissy Simonne. Let's see if we can't make you just as happy." She led him to the bedroom...

3 years ago
  • 0
  • 33
  • 0

Cocky Weewee Peepee Sissy Slut Training The Bladder Test

This is one of the sets of stories I am currently writing. The set is called Cocky, Weewee and Peepee Sissy Slut Training. These sissies are in the hands of Mistress Katrina, Mistress Heather and Mistress Satin. Sometimes Master John and Master Rick are involved in their training. Many situations await them. MANY! If these stories succeed I will add some prequels and sequels. Hope you enjoy it! English is not my native language! I will do my best! Sissy Joan Cocky Weewee and...

3 years ago
  • 0
  • 24
  • 0

Good Sissy Girl

Good Sissy Girl. I kept pressing myself backwards. Not much further to go now, I could feel the flare really stretching my lips now and that meant I was almost there. As the plug's biggest width popped past my sphincter and went all the way in I shuddered all over. It felt so full. It felt so good. "That's a good girl. Allll the way in..." my Mistress purred at me. I loved seeing her this excited. I loved turning her on. I loved that transforming myself for her turned her...

4 years ago
  • 0
  • 37
  • 0

Sissy School Part 3

SISSY SCHOOL - PART 3 By Missy Crystal After Sissy Heather had swished and drooled a couple of more times, she began to give me gentle nibbles and licks to clean the cummy residue on my lips and chin. After the kitty bath, she stood up. Since her crotch was now at my eye level and since her short skirt exposed her frilly panties, it was obvious that I wasn't the only one that got turned on by her sucking my dick. She must have been aware of it too, because she pulled her panties down...

2 years ago
  • 0
  • 40
  • 0

Sissy tasks

Your First Sissy AssignmentThis is your first step on your journey into femininity. A journey that will change your life. You will be humiliated and embarrassed. Most of all, you will be feminised. If you don’t intend to follow all of these assignments to the letter, then turn away now.Your first assignment is to buy yourself a pair of panties. Be sure to measure your hips before you set off. You will go to a smart department store or, better still, a specialist lingerie shop. How exciting – a...

4 years ago
  • 0
  • 42
  • 0

She Found a Sissy

She Found a Sissy ? by: Donna Sash She had been working at Bardwell's for the last 10 years. Five years ago she Had moved to the scarf counter and had been there ever since. Sales had gone up because she really likes it here. From the time she was a little girl she always loved wearing a scarf with her outfits. Now every day she wore a different one on the job and it helped sales. Women reacted well to someone who believed in their product. Some women just wore a scarf...

4 years ago
  • 0
  • 31
  • 0

100 Sissy Points

Author's note. This is a work of erotic fiction, so if this offends you, please stop reading. Also, most of what's described in this story wouldn't be ethical or legal, but again, I remind you that it's fiction! I hope it's good-and-kinky fiction, and while I wish something like this had happened to me, once again, it's only fiction. Some readers think that my stories are autobiographical. I wish! Also, a fan of my work suggested this story concept. Feel free to message me if you have...

4 years ago
  • 0
  • 45
  • 0

Welcome Your Now a Sissy

Are you ready?Are you ready, princess?It's finally time. It's finally time, princess. It's time to begin. Are you ready? I think you are, princess. I think you're ready. I think you've been ready for so long.You've been ready for your whole life princess.It's time to drop the mask and be who you are. Who you really are. What you really are. No more lies, princess. No more games. It's finally time to reveal everything.It's time to reveal the sissy.That's right, princess. You are a sissy. Say it...

Porn Trends