First Time Creampie from Trans

After my first time trying cum from a transexual (see my story titled, "First Time Trying Cum from a Trans" if you want some background), I developed a craving for it and it turned into a desire not just to feel the cum of a transexual on my face and mouth but to feel her cumming inside me raw. I looked through the different dating sites that I've been on and at first, there weren't many profiles that caught my attention since they all basically said the same thing. That was until I stumbled upon Daisy's profile.

What stood out for me with Daisy was that she was a professional masseuse, someone who actually went through the training to learn how to give a proper massage and that she likes to take care of her clients by helping them relax before actually doing the deed.

As we exchanged messages, I asked her, "By the way, would you be willing to cum inside me without a condom?"

It didn't take her long to reply saying, "Well, I can assure you that I'm clean but have you done it raw with other girls like me?"

I told her the truth, "I've done it with other girls like you before but they always wore a condom whenever the would top me."

Daisy seemed to like this and replied, "That's good, it's been a while since I've done it raw with someone. Plus you look cute so I bet you can make me cum a lot once we see each other."

This sent a tingle of electricity across my body as I imagined her unloading herself into me which got my really excited and nervous at the same time. We continued the conversation a little bit more and agreed that we would meet in a few days when we're both free from our schedules. The next few days went by like a breeze as I just went through the motions at work since all I had in my mind was Daisy and her hard cock filling me with her cum.

The night that we were supposed to meet, I had done all the preparations on my end but there was a sudden shift in me that made me nervous all of a sudden and I almost wanted to back out.

Almost as if she felt the change in me, she suddenly sent me a message saying, "Hey, I just want you to know that I haven't cum since the time that we talked to each other and I've been saving up so I can fill you up real good tonight. See you!"

This message was exactly what I needed as it sent a bolt through my body that made me instantly horny for her, I felt my ass throb at the thought of her saving up all that cum only to unload it all inside of me. There was no backing out now. I wanted this, I desired for this.

When she arrived to my room, I was taken aback because she was a bombshell. Her pictures on her profile didn't do her justice as she looked even more stunning in person. She had sultry eyes and luscious lips that matched with an almost hourglass figure with just the right amount of curves. I must've been staring at her for a while since she suddenly laughed, and a cute one at that, and made her way into the room.

We sat down on the bed and made a few small talk here and there about each other until she stood up and said, "Well, let's get you ready for that massage then."

I had already taken a shower before she arrived so she told me to strip down. Now the massages that I would usually have would have you strip down only up until your underwear but Daisy stripped me off of everything. I was now completely naked in front of her while she was still fully clothed herself. She then told me to lie down on my stomach while she did her own preparations. I heard her shuffle around a bit behind me and when I looked back, she was already down to her lace underwear with her semi-hard cock bulging in her panties.

She must've seen me staring at her dick because she said, "Don't worry baby, that'll be all yours later." She then followed it up with a wink.

Soon after, she straddled my back with her panties rubbing in between my ass cheeks and started rubbing the massage oil on my back. The massage itself was really good, not like one of those where the masseuse would lightly touch you almost like air. She knew what she was doing with the massage itself but the best part was about to come.

After finishing with my back and legs, she turned her attention towards my ass. I didn't notice it at first but she actually took of her panties at some point of the massage and I turned around to see her hard dick pointing at my hole as she straddled me again. I could feel the weight and pressure from her as she sat on me and how she teased my hole with the tip of her cock. I heard the click of the bottle of oil open and she let a few drops fall right between my ass cheeks before running a line on my back. This sent shivers across my body and I even had a slight moan into the bed as I was getting really excited for what's next.

She grabbed my ass and squeezed them together and followed by slowly gliding her dick in between my cheeks. At first it was only on the surface, but later she was digging down on me and I could now feel her dick slowly poking my hole almost trying to get inside. I arched my back a little bit more out of instinct that that's what I needed to do to get this dick inside me already, but she had other plans. She lowered her torso onto me so now she was hugging me while rubbing our oiled bodies together. The sensation was so erotic, her breasts and nipples tickling my back while her dick glided on my hole forward and back.

I was moaning a lot louder now, almost like a slut in heat. Daisy took this as a sign and suddenly stood up from her position and then rubbed my ass and penis with the towel beneath me to get rid of the oil.

I didn't know what was about to happen until Daisy said, "I want you to raise your ass up a little bit."

Like the good slut that I was, I raised it up and it turns she wanted to do this so she could give me a rimjob. Her first lick was like a taste but the ones that followed after that were more aggressive. I could feel my ass throb from the pleasure of her tongue swirling on my hole and even more so when she would push it in and lick me from inside. She would also give my dick a few strokes whenever she licked which made my cock slowly grow into its 7 inch hardness.

This took her by surprise because she knew I wanted to be a bottom so she said, "You didn't tell me you had a dick like this. You wanna fuck me first before I fuck and fill you up later?"

I was taken aback because I didn't really consider being a top tonight but with the arousal she was making me feel, I couldn't help but oblige. I simply nodded in agreement as she continually rimmed my ass and stroked my dick.

She then told me to stand up and lie down on my back and said, "I hope you don't mind but you've been so cute with how slutty your reactions are, can we shoot a video of this so I can post it on my channel?"

I wasn't really sure about this because I haven't really done anything like that before but the thought of being recorded and being part of a sex video made me more excited than nervous.

It took me a while to properly reply to her so she said, "Don't worry, I have a mask here and you don't have to show your face to the camera. No one on my channel will be able to download our video once I post it as well. You're safe with me."

To be honest I didn't really need her to say those things anymore but it did help calm me down more and become more open to the idea of it. I agreed to her proposal and she set up the camera to face us. The problem that I did have with the camera was that it was a bit distracting since I could see as the phone recorded us and there was a nagging thought that it was risky being recorded, which was made evident by my now softening dick.

Daisy noticed this and tried to stroke my dick a few times to no avail so she asked, "What can I do to help you relax and get hard again like last time?"

I thought about it and replied, "I have a fetish with nipple play so maybe you can do that to me?"

She gave a naughty smile and went up from stroking my dick to giving my nipples slight pecks that turned into kisses and soon after she was swirling her tongue inside of her mouth as she sucked on my nipples. In no time, my dick was harder than it was before and she stopped sucking on one nipple but continued to play with the other as she made her way down on me to give me a blowjob. The room was filled with my moans and the slurping sound she was making from my sucking my dick, I didn't even notice that she also stuck her finger inside of my ass already causing me to tense up and arch my back which made my dick go even deeper into her mouth.

This continued for a while until Daisy raised herself up from giving me a blowjob, a string of drool connected between my penis and her mouth. She then took me arms and raised me up as well while simultaneously lowering herself onto her back where we basically reversed our positions from earlier, my wet penis now poking at her hole.

But before I actually inserted myself into her, I returned the favor and did the things she did to me; I started from the top, making out with her and eventually moving down to her neck caressing it and giving it a few pecks. I moved down to her breasts and played with them, fondling one while I ravaged the other with tongue swirls and nibbles. She was now grinding into me at this point, rubbing her semi-hard 5 inch penis into me.

I couldn't help but notice her dick and I stared at her hole that leaking precum already and I gave it a few licks, the taste of her sticking to my lips. I then took her cock into my mouth with no hesitation and lowered myself until it hit the back of my throat. I've been practicing with 6 and 7 inch dildos so it wasn't hard to deepthroat her but it felt different as well from the toys that I would use. I felt her hand behind my head as she slowly pushed it down so I can take more of her in.

I was now bobbing on her dick at this point and this continued for a while until she pulled me off her dick and said, "I want to save my cum for you later baby, now I want you to fuck me with that big dick of yours."

I raised myself up from her dick, lucky that I had a mask on because I was sure my face was a mess already. I spit out some saliva onto my dick and started stroking it while she got the pack of condoms and opened up one of them. She later slid the condom onto me, replacing my hand with hers as she stroked me and led me to her waiting hole.

She told me, "It's been a while since the last time I had a dick like yours, so take it slowly."

I nodded in agreement and after rubbing some lube on the condom and her hole, I slowly pushed my way into her hole. The heat at the entrance of her hole was already overwhelming but once the head completely entered her, we both moaned into each other as she grabbed my head to make out with me. Inch by inch, my dick made its way inside of her and each time an inch would go in, her face would melt with the pleasure we were both feeling. As I bottomed out and our balls touched with each other, I could feel the walls of her ass clench on my dick almost like it was feeling it out.

This is when I remembered that we were recording a video of this and I looked at the camera showing us hugging together with her legs raised up and me in between her legs. This distraction made my dick go a little softer and Daisy noticed this. She then told me to raise myself up a bit as she bent forward a bit more so she can start playing with my nipples. When she did so, my dick not only got harder but it was like it had a mind of its own. Without thinking, I started pulling out of her about 3/4 of the way and pushed back in, picking up the pace as I did so. It was such an erotic scene, her moaning and licking my nipples while I was pounding away at her pussy with the sound of the lube and our skins making a lewd noise echoing in the room.

I didn't know for how long we went like this but Daisy suddenly grabbed my ass while I bottomed out and said, "Since we're doing it raw with you, do you want to take off the condom now and fuck me raw instead?"

I don't if I was just caught up in the moment or I was just completely horny at that point but I didn't even reply to her and instead I just pulled out and let her pull the condom off of me. She then got some more lube and rubbed it all over my dick while her hole was gaping, waiting for me to go back inside.

She led me back into her hole and without resistance, she opened up and let me in with ease. Now I could feel her raw insides, inch by inch coiling around my cock as it made its way inside of her. When I felt that I've penetrated her entirety, I grunted with an almost primal growl and I didn't hold back from there. With my right hand, I grabbed at her waist and with the other hand I grabbed her between her shoulders making sure that she was going to feel how much I wanted this.

We were now staring at each other like we were furiously horny as I went in and out of her with ease, our skin slapping against each other as she looked at me with pleading eyes to fuck her even harder. Daisy wasn't one to let go easily as well as she pulled me up a bit so she could reach my nipples and started playing with them again. With the tightness from her pussy clamping down on my dick that was a piston going in and out of her and the moans we shared while she licked my nipples, I was almost at my limit.

Daisy sensed this as I was now pounding on her harder and I kept grunting and moaning so she said, "Cum for me baby, cum inside me and fill me up and I'll do the same to you after."

This sent me over the edge and I thrust one last time making sure I was deep inside her when I started flooding her insides. I couldn't count how many spurts came out of me but I could tell by Daisy's moans as she moaned along with each throb and spurt from dick to the point that it was leaking out of her already. She moved by herself and started riding my dick while lying down, churning the semen inside of her even more.

When I finished and was finally soft that my penis popped out of her penis, I thought it was over since we just had such an intense session at least for me but I thought wrong. Daisy suddenly pushed me back down to the bed and now she was between my legs, her cock staring straight at me.

"I can still feel your cum wriggling its way inside me. I'm going to make you feel as good as you did for me." she suddenly exclaimed as she started lubing up her penis and it seemed that she didn't have any intention of putting a condom on anymore. Before she plunged into me, she took a glance at the camera again and made sure she was satisfied with the angle from the camera.

Daisy then lined herself up to my hole and started teasing it by rubbing her dick up and down, slightly entering my hole whenever she would push her penis down and making me moan every time she did so. She then raised my right leg with her left hand and led her cock into my hole with the other. I felt the pressure from her pushing against me and I pushed out as well to let her in a lot easier.

This made her dick slide into me almost halfway without any issue but I tensed up a little bit and she said, "Relax baby, this is going to feel real good when you do."

I took her advice and focused on my breathing and I felt her slowly inch her way even more until all of her 5 inches was inside me. She bottomed out on me which made me release a very slutty moan that I've never heard from myself. It was a mix of how good she felt filling me up with her dick and at the same time how I could feel her veins from the rawness of her dick inside me.

I must've been making the same pleading face that she made a while ago because she suddenly picked up the pace and said, "You like that baby? You like how a girl like me fucks your sweet pussy slut?"

I wasn't expecting that at all. I didn't know that she would talk dirty to me like that but what surprised me was how turned on I was because of it. It made me realize that I was under her control now and whatever she wanted to do to my pussy, she could do it because I would let her. All I could do in response was to nod my head and whimper like that little slut she said I was.

She upped the ante even more when she suddenly went closer to me and I thought she was going to make out with me but it seemed that she remembered my fetish for nipple play and started licking and sucking on my nipples. I felt the cum inside me building up again and I didn't know what to do because I knew I just came a while ago but it was something different. My dick was limp but precum kept oozing out of it.

I don't know if Daisy noticed it but she suddenly commanded me, "Turn around. I want you on your knees with your ass up. I want to fuck you hard from behind."

At this point, I didn't even care about the mask anymore and while I was turning around I took off the mask and placed my head unto the mattress. I could see myself on the recording, I assumed the position of a slut that was about be fucked doggy style something that I've always seen in sissy trainers. I felt horny already from the position I was in but to see it with my own eyes, I almost lost myself right then and there.

She took the phone from the stand and recorded her point of view as she slowly pushed herself back inside me saying, "Oh yeah look at that pussy, you want me back inside baby?"

I nodded on the bed and said to her in reply while panting, "Yes. Yes I want your dick back inside me. I want you to stir me up and make this hole into a pussy for dick!"

I couldn't believe the words that were coming out of my mouth but even more so, I couldn't believe how turned on I was for saying those things. I was now looking at the recording with my eyes half closed as she started ramming her cock in and out of me, seeing the outline of her dick disappear back into me with every thrust. The moans that were coming out of my mouth weren't the deep manly ones that I did earlier, they were more girly, a lot more slutty than before.

We talked back and forth with each other which went something like this:

Daisy: "Fuck your ass is so tight right now it really loves my dick huh?"

Me: "Yes I love your dick going in and out of me. Fuck me more pleaseee"

Daisy: "Yeah you like it baby, you like being my slut and you love it when I fuck your pussy like this!"

We kept talking dirty with each other for I don't know how long as she just went wild with my pussy. After a while, she took her phone from the stand again and recorded her point of view so I had an idea of what was to cum.

While she pounded away on my pussy, she was panting when she said, "I'm gonna cum baby, this is what you wanted right? I'm going to fill your pussy with girl-cum and you're gonna love every single drop of it."

The best reply I could come up with was, "Yes, yes, yes. Fill me up pleaseee."

Instead of bottoming out like I did and spewing all the cum inside, she just kept her pace as she exclaimed, "I'm cumming!! Ohhh fuck this is a lot, take it all baby."

I felt it all. At first it felt like something really hot hit the walls of my ass then it turned into an almost full feeling like I need to release whatever was inside. I could feel some of the semen drooping down my balls and my legs, she really filled me up good. Spurt after spurt, and now I understood why she moaned along with my dick throbbing inside her a while ago. It really is uncontrollable at that point as I felt all of the cum gushing inside of me, making moan like a sissy cum slut who just got what she's been dreaming of for the whole week, which I did. She still had her phone with her when she popped her dick out of me and I could the warmth of the semen flowing out of me, making popping sounds because of the bubbles that formed.

"Look at that pussy leaking out all my cum, keep as much of it as you can inside you baby." Daisy exclaimed as she recorded my pussy.