First Time Trying Cum from a Trans

Author's Note: All characters in this story are 18 years old or older.

By now, I've had my fair share of experiences with different guys most of which were either my mates from school or friends of friends. Although it was fun and exciting for me my first few times that I did it, after a while I was getting bored and it all led back to the reason that I was doing it with another man. Before I realized I was bi, I was straight as can be. I still had fun doing it with guys but I was still really attracted to girls and the female image, it didn't help that I was also always the top whenever I did it with other guys.

I was stuck, I wanted the intensity and rawness of gay sex but I also wanted to do it with someone with a feminine face and figure who would let me be a bottom for once. That's when I stumbled upon the world of transexuals.

From looking at random videos on porn sites, to finding myself transfixed on sissy trainers. I eventually found myself looking at different dating sites which led me to find a site for escorts which was a rabbit hole in itself, but long story short this is where I met the shemale who would eventually take my virginity, Sam.

Sam stood out to me from the rest because of how feminine she looked. She had pale white skin, long brown hair, and tall but slim figure to go with it all. Her face was also very feminine with these alluring eyes and a small pink set of lips perfect for kissing. Her profile helped since she wasn't asking for much compared to the others but also how well written and sincere her post was.

After weeks of surfing the site and always ending up going back to her profile before eventually backing out, I finally mustered the courage to get her number from the site and to message her directly. My hands were shaking when I first tried to chat with her and she didn't reply to me immediately since she said she was at work and that she only does these things at night.

When she did finally reply I tried to play it cool and I tried not to reply right away but my excitement got the better of me. We talked over the chat for a while discussing the details of what I wanted to do and happen, where we would do it and all these different details to setup the night. We agreed to meet the following night and upon my request, she would give me a massage to set the mood right before she teaches me how to be bottom as she tops me.

The following day went by like a breeze and before I knew it, it was already just a few hours before we would meet at my house. Once I got home, I started prepping myself by taking a shower and making sure that I was clean from head-to-toe, inside and out.

It was still a little while before we saw each other which made me a bit nervous now that everything was starting to sink in. Tonight was the night that I would spend with a shemale and this might also be the night that I lose my anal virginity. I almost backed out completely from the night when I remembered that I still have a joint that I haven't used so I lit it up and smoked weed which helped me calm my nerves a bit.

After slightly losing myself from the high, I didn't notice that she already sent me a message that she was already on her way to me. My nervous feelings earlier were soon changed with feelings of excitement and after about half an hour or more, she was finally here.

She was a bombshell to say the least. She was even more beautiful in person than what she showed with pictures on her profile. She had a very seductive but playful look to her eyes, her small lips arched into a grin, and the way she stood with her hands clasping her bag while waiting for me to take it all in.

As Cal Weaver from the movie Crazy, Stupid, Love once said, "She's the perfect combination of sexy and cute."

"Hi," she said with a girly voice, "can I come in?"

I must've just been standing there like an idiot so I replied, "Sure, sorry about that. I was just surprised."

She tilted her head to the side and asked, "What do you mean by that? Am I not what you were looking for?"

I waved my hands in defense and said, "No, no, it's not that. It's just that you look a lot prettier in person."

Her head tilted back to the right position and she gave me a beaming smile while saying, "Well I hope I can meet your expectations for tonight, sir."

I welcomed her to my home and replied, "You don't have to call me sir, after all I'll be the bottom for tonight if all goes according to plan."

With that, we made our way to the room where I sat down on my bed just observing Sam while she made herself comfortable in my room. She asked if I was ready for tonight and all I could do was nod my head. She asked me to stand from the bed as she laid down the towel, after which she helped me strip out of my clothes. She stood very close to me, enough that were eye to eye and our lips were almost touching. "

She took of my shirt, followed by my shorts, and when she was going to take off my underwear she said, "You won't be needing these tonight anyway."

Now I was fully naked with a shemale that still had her clothes on. My erection slowly came to life and was soon as stiff as a rock. Sam laughed when she saw this reaction and said, "Wow, someone's a little excited huh? Don't worry I'll take care of that later so for now let's focus on your massage."

She then told me to lay down flat on my stomach for the massage but before she started, she grabbed my head lightly and turned it to her direction. Behind her was a wall of mirrors so I had a good view of both her front and back side.

She first took of her shirt as well revealing a small set of boobs that would probably fit the smallest A cup available but I didn't really mind since I liked petite features with women. She then turned around and while staring at me from the mirror, she pulled her pants down slowly with her plump round ass making it a struggle for her pants to be pulled down.

When she pulled her pants all the way down, she was bent over forwards with her ass and crotch staring right at me. She was wearing a green lace panty that barely covered her pussy as she made it throb to tease me even more. But what I was more interested in was the bulge in front, she was already getting hard and she was a good 5 or 6 inches.

I tried to reach for her cock when she stopped me and said, "Ah, ah, ah. You'll have your time with my dick later, for now I want you to relax."

Now that she was half naked with only her panties on, she straddled me from behind and started pouring massage oil over my back. It wasn't really one of those massages that would try to alleviate the pain from my body, but it was more of a sensual massage where she would glide her hands and body all over mine with intentional motions.

She first started with my upper body. She would start with her hands rubbing and caressing me until she would change it up by using her entire forearm which also made her slide her boobs onto my back.

She continued with this motion before she moved up a bit so that she could get my shoulders but this also meant that her dick was right between my ass cheeks. This was intentional since she would match the movement she would do with my shoulders with her grinding in between my ass.

She later moved on to my legs, slightly rubbing each one with massage oil. She then moved in between my legs and pushed them apart. I was now lying face down and my legs spread apart and Sam between my legs rubbing my ass, it was such an unfamiliar but exciting feeling for me.

She did a circular pattern on each of my ass cheeks before pushing and pulling on them, stretching my ass out and exposing my limp penis.

After a while she told me to raise my ass a bit so I dug down on my knees which were now bent at an almost 90 degree angle and pushed my lower body up slightly. I haven't really done this position in any of my massages before so I didn't know the point of it until she started caressing my crotch.

She would this motions where she would start from my thighs and slowly move up and then she would almost reach for my abs from below which would make her hands and arms graze my slowly growing dick.

I thought I was already lost in ecstasy from what was happening until she made a long motion going past my abs and reaching for my nipples. She was now rubbing my nipples as she grazed my dick while massaging my lower body. I was squirming from the pleasure she was making me feel and I could've cum right then and there but she suddenly stopped.

I looked up with dazed eyes and I saw her make her way in front me. I raised my head a little and I could see her looking down on me with a smile on her face. She put my head down but turned it to one side so I could still see her without straining my neck too much. She started working on my shoulders again but this time giving more emphasis to my neck area as well.

As she was rubbing me, I looked up and saw that she was focused on what she was doing but what caught my attention was the head of penis sticking out at the top of her panties. She was still focused on her massaging when I put my arms around her legs and slowly tried to push her into me.

She picked up on what I was doing and helped me by lowering herself closer so that her crotch was now touching my face. She couldn't really rub it into me because she was still trying to massage my shoulders so I took it upon myself to started rubbing her pantied dick on my face.

This went on for a while until I noticed that there was something wet on my cheek, it turned out it was her precum rubbing on my face already. I took some of it on my fingers and placed it in my mouth, tasting how sweet she was without a hint of it being salty or bitter at all.

We didn't get to finish the massage anymore. She stood up and she took of her panties revealing her 5-6 inch penis. I didn't really know what she wanted me to do but I found out when she went behind me again and straddled my ass but this time without any panties on. I felt her dick poking at my entrance but before she pushed through with it. she shifted her position on top of me and now her face was right on my ass.

I couldn't really see what she was doing from behind me, but all I know is she had her face close to my ass and she just pulled my dick out from under me. I got caught off guard when I felt something wet hit my penis, that's when I realized that she just gave me a little lick on my cock which made me tingle with anticipation.

She licked my penis a few times before moving up and rimming my hole. It felt so different but in a good way, which made me moan whenever she would flick her tongue across my hole or when she would smother her face with my ass and eat me up like that. When she was finished, I could feel a cool wetness drooling from my ass to my dick which made me even more horny than ever.

"Turn around and lie down on your back." She told me as she was panting with a slightly red hue on her lips and chin. When I turned around, I saw her already rubbing herself while she was applying a condom on her dick.

"Are you ready for me to take your virginity?" she asked me while she opened the pack of lube which she rubbed all over her cock and my ass also.

All I could muster was a pathetic nod, like a slave who just wanted to please his master. Before she put her cock inside me though, she went close to me and gave me a kiss. It started out as these small pecks on each other's lips but later turned into an almost carnal make out session.

I didn't even notice it but Sam was actually playing with my nipples while we were making out and eventually one of her hands made its way down to my ass. She stopped our kiss and gave me her finger to lick which I slopped all over since I knew what she was asking for.

With her finger properly lubed up, we resumed making out and she slowly inserted one finger into me. I have to admit that it was definitely painful at first, like my body was trying to reject her fingers from going in but I just tried to remember that I needed to push out first to let her in. With that in mind, her finger slowly went deeper into me and the pain was soon turning into a pleasurable one.

Once I started moaning, she dug in even deeper into my hole and this followed it with another finger which stretched my hole even more. While she was doing this to me, I saw her penis bouncing along with her movements so I raised myself a bit and reached for her penis. She was stroking her fingers in and out of my hole while I was stroking her dick up and down before entering my hole.

"I think you're ready for me now." She told me as she slowly pulled her fingers out my hole and when she was out, there was an empty feeling that needed to be filled.

"I'm ready," I replied, "I'm ready to lose my virginity to you."

She didn't need much more motivation after that. She gave me a quick kiss before going to down to play with my nipples and slowly moving down all the way to my semi flaccid dick. She grabbed my penis and started stroking it until it was almost as hard as it can be.

Before taking it into her mouth she told me, "I won't make you cum right now because I want this to last for both of us."

After which she not only gave me a blowjob, but went straight for a deepthroat the moment she took my dick into her mouth. My body was reacting by having these mini spasms whenever she would bottom out on my dick to the point that my back was arching as my dick wanted to go deeper and deeper into her throat.

She was bobbing up and down on my dick when she suddenly stopped with my cock covered in her saliva.

With some of her saliva drooling down her chin she said, "This'll help when I stroke you while fucking you later."

This made me gulp in both nervousness and excitement since it really was going to happen. I was about to get fucked by shemale, I was about to fulfill my fantasy.

She propped herself up and this time lined her penis straight to my hole. She opened a pack of lube again to rub on her dick and my ass which made us well lubed for the night. She raised my legs up told me to keep them up so that she would have an easier time going in and out of me.

I could feel the pressure from the tip of the head of her dick trying to make it's way into me. With the memory of having to push back and being fingered a while ago, my pussy gave way a lot easier than it was with the fingers earlier. There was some pain especially when the whole head just popped in to my ass. It was a hot kind of pain, the kind of pain that's telling you that you shouldn't do this but it was also the kind of pain where I wanted to see what happened when the pain goes away.

Sam noticed I was having a hard time adjusting so she stopped where she was at which was about halfway already and leaned into me, planting a long hard kiss on my lips. She also squeezed and twisted my nipples from time to time which definitely made me relax. I hadn't even realized it yet but she was actually slowly moving inch by inch when she was kissing and caressing me to the point that she already bottomed out and I can feel her balls next to mine.

We both let out moans while we were making out when Sam started to slowly pull out of me and I could feel the walls of my ass gripping onto her dick, almost like it didn't want her to pull out anymore.

I don't know what face I was making but Sam raised herself up and said, "Fuck, you look so good when I fuck you."

As she pulled out, she stopped when only the head was inside me and with a devilish smile she pushed back in with one motion causing me to moan even louder this time. She bit her bottom lip from my reaction and started to pick up the pace.

I felt my eyebrows scrunch together as she fucked my pussy. In and out. In and out. The sounds of our bodies slapping together in tune with the moans that we would let out. After a while, she was looking at me intensely and I had an idea what was about to come; or should I say cum.

I was also almost at my limit when Sam pushed all the way in to the base of her dick and told me, "I'm almost gonna cum, where do you want it?"

Without hesitation I replied, "I want to feel your cum on my face."

As I said that, she pulled all the way out my pussy with an audible pop and I felt empty longing for her to go back inside me. But I didn't mind since in exchange for that, I was going to feel her cumming on my face.

She stood up and made her way around the bed until she was standing on the edge of the bed. She pulled me closer to the edge and after taking the condom off, she started jacking off furiously on top me.

I thought that was all she was going to do until she held my face and pushed her dick straight into my mouth. This took me by surprise as I started to gag at first but when she finally lined it up correctly, she was now going in and out of my mouth while constantly grazing the opening of my throat.

I don't know how long this went on but I do remember that I really enjoyed this feeling. Having a hard cock of a beautiful shemale slide into my mouth.

She then pulled out and started jacking off again, this time almost sitting on my face with her balls covering my eyes. All I could hear was that she was moaning loudly and I could also hear the sloppiness of the sound coming from her masturbating her cock with my saliva as lube.

"Oh fuck baby, I'm gonna cum. This is gonna be a lot. You ready for this?" Sam said while alternating between panting and moaning.

To which I replied with complete horniness taking over, "Yes, yes. I want all of your cum. Let me feel your hot cum all over my face. I want to taste you so bad baby."

Sam kept moaning until she exclaimed, "Here it comes, OH GOD!"

The first streak of semen hit my lower lip with some it falling down into my mouth, immediately tasting how sweet she is.

I let out a small moan as I tasted her, "Mmmmm."

Spurt after spurt came out of her, covering my entire face. From my mouth, to my nose, my eyes, and my forehead. I was plastered with her cum. I didn't even notice it but I was also furiously jacking of my dick and after getting hit with her cum on my face, my own cum started flying onto my chest and some even going as far as hitting my chin.

She was still moaning as she now slowly stroked her cock on top of me. Even with cum all over my face, I raised myself up and turned to her. I took her softening dick into my hand and started stroking her to let out the remainder of the cum followed by me giving her a blowjob to clean the rest of it off.

She gave me one of the towels for the massage to clean my face up but I wanted to see my face first before I cleaned myself up. I went to the bathroom with her and as she was cleaning, I looked at myself at the mirror.

So much cum. The off-white liquid sticking to my face, not liquid enough to start running off of it. The scent of her semen going straight to my nostrils with the drop of cum hanging just above me nose. I licked my lips and even got a finger to push in some of the cum that's out of the way into my mouth, tasting her even more.

I realized it and I knew it. That was the day I knew I was a slut for cum.

We took a shower and took a rest after. We made sure everything was in order before she left and I thanked her again and again for a wonderful night to which she replied, "I hope we can do it again someday. I really had fun with you and you're a nice guy."

I agreed with her and told her that I would setup another meet whenever I was free, and we said our goodbyes after that. That wasn't the last time I saw Sam, we met each other again at least twice after that and I'm still waiting for the time that I'll be free again so that I can feel her cum on my face again; or maybe I can feel her cum inside me the next time around.

Thanks for reading this story. This was a true story that happened just recently and I've only changed the names of the characters and some of the dialogue but everything other than that really happened. This is my first of probably many trans stories and I'll be posting them here soon.