This is a long story. My apologies If it is to much. I had to get this down and with a lot of detail. Not a unique story but definitely a hot one. Got very excited while writing it. Will check out comments.
I do not know what I was thinking. There was this nagging itch that I needed scratched. Not the first time for an itch, however this was one never scratched before. Why in the hell was I thinking about being with a Trans woman. Never have I ever done this or been with a man before. This wanton desire just would not go away.
Here I was thinking “I think she may be the one.” When I saw her online I could not stop researching and watching her videos. She was an amateur porn actress I found while searching the web. This was before the good websites were taken offline for hiring SWr’s. For some reason I found myself down the rabbit hole of pages that went from my usual to “Other Interests”. Probably spending a couple hours browsing until I landed on her.
She was very attractive for a trans woman. Honestly this entire encounter would not be happening if I wasn’t attracted to her. Being the research freak I am, there was little left to chance for our encounter. She seemed fun, forceful, entirely capable and of course sexy sexy sexy.
After a bit of messaging and back and forth I was in the parking lot of where she was staying. She told me her room number. Now my heart started to beat a little faster as I approached the door. I went up and knocked on her door. After what felt like a half hour she opened the door but stayed behind the door to obscure the view from the hallway.
As I stepped in I felt a calmness kind of take over me. The energy in the room was peaceful and quiet. Not what I expected. Although truth be told I did not know what to expect.
We stood near the entrance and she allowed me to drink her in. I was very happy with my choice. She had long dark hair that went past her shoulders. A purple negligee over a very nice lace bra and tiny panties with matching thigh high stockings. She wore the outfit beautifully and carried herself with confidence and grace. Also not what I expected.
I laid the money on the counter and walked over to the couch sitting next to her. “What would you like to do?” She said in a sweet voice. “What did you have in mind for us?” “I know you have dealt with men like me before, but I have never done this.” I said while looking at the floor. Her perfume was floating in the air. You can feel the energy shift. Shifting to a more anticipatory vibe exciting and sexual. I liked that it did.
The whole reason I went through all of this was to explore more sexuality and tastes. To open the door to more of my sexuality. Fulfill my desires and fantasy. She asked “I am here for this baby. What do I need to do to fulfill your desire and fantasies.” I looked up at her face and into her eyes. She was so pretty, a rare find that made me feel very lucky to have this opportunity.
“I have never been with anyone else but a biological female. Don’t misunderstand. When it comes to the women I have been with. They are always attractive to me. I love to please them. I love to eat them out. To lick their asses. To kiss them endlessly. To suck on their breasts. Basically to put any part of their body into my mouth. And most of all. I love to fuck them. I love to fuck them hard and make them cum. Make them squirt. Make them shake from the cock pounding I lay on them. To fuck their mouths. To fuck their pussies . To fuck their assholes. All or one. There has never been a problem for my hetero side. ” I could see her visibly swallow while staring straight into my eyes.
“I wanted to start with exploring your body. Then see where it leads.” I said with a little hesitation. She said “alright, I would love to be your first.” I could see a devious little smile come across her face. Which made me smile as well. I knew exactly what I wanted. What I really wanted was to suck on her cock. Just to be blunt and honest here. Lets face it, you can get sex just about anywhere and with what ever your looking for. So this was a practice in realm that I have never ever played in. Of course I wanted to explore her entirely, that was for sure. But the other stuff was secondary. There is no rush because this guy is going to enjoy every second of this.
I stood up to move in front of her. She was sitting on the bed with her feet on the ground and her hands propping her up so she could watch me. This is exactly how I would sit if a hetero man was about to have his first shemale cock. Or any cock for that matter. Perfect view allowing for instructions or better yet approval.
Her negligee was draped over her shoulders. Her breasts were sticking out nicely. I kneeled down in between her legs. Touching her knees lightly and stroking the smoothness of her thigh high stockings. She was built for this. Beautiful and built. I was kinda dizzy with the hormones in the air and the anticipation. The energy was intoxicating and it was exactly as I had hoped for. The couple of puffs on my vape certainly helped with the dizzy anticipation.
I looked at her face and then into her eyes. She smiled and did not say a word.
Reaching up I touched her cheek and lightly ran my fingers over her ear to push her hair back. With a slight touch I ran my fingers down her face to her neck and further down to her shoulders. She involuntarily shuttered. Slowly softly touching, I traced her skin around her bra and tickled her ample cleavage. Like a kid in the candy store it was difficult to contain myself and not tear Into her. One of the tricks I taught myself was how to get a bra off of a woman quickly. That was exactly what I did. With my other hand I reached around her gently and flicked the hasp on her bra and poof. Everything let loose. I reached up and pulled the nightie down and off her arms followed by her bra.
She leaned back and let me admire her beautiful tits. I used both hands. Lightly at first I traced around the soft globes. Putting one breast in each hand I could feel the weight and heft of them. Whoever did the work on her chest did a great job. Her nipples were tiny and hard. Running my fingers around her nipples which forced a slight gasp from her. I leaned in and sucked on one them while holding the other with more pressure. She liked them being flicked and traced around the areola. Not that much different from the women I have been with. I went back and forth between them for a bit. She held my head while I did so. Stroking my head and hair and telling me how good I was doing. That she liked it.
She was starting to squirm and move her pelvis around from the attention. Admittedly I was super turned on as well. But now I want what I came for. I sat back on my heels and looked at her on the bed. No bra. Breasts hanging high in the sky. Smile on her face. And just a tiny pair of panties at the end of her long legs. Legs that were covered by purple thigh high stockings trying to contain her dick In its confines. It was a sexy site that I had been waiting for.
I reached up and stroked her thighs with my hands. Her purple panties were struggling to keep her cock inside. She said “I am big.” “Well I saw online and I think I can handle it.” I said confidently. She reached up and touched my face “baby I have been told I am nice and big” “It looks like you may be right. Thank you for the warning.” I quipped back at her while we locked eyes for a moment.
It is real now. I’m in a hotel with a gorgeous Trans woman who I am super hot for. How did this happen???? Here she is with her tits out, legs spread with a huge bulge in her panties and me kneeling between her knees.
FIRST TIME FOR EVERYTHING.
I looked up and down her body. Admiring every inch. Sitting back on my heels I stared at her panties. Breathing in and out trying to hold onto this moment. Her cock was semi hard held in the confines of her skimpy panties. Her cock was kind of draped towards the left along her crotch. She wasn’t kidding, it looked like a nice size already. I reached up to touch her panty covered dick. Tracing my fingers along the length of her panties from the tip of her cock to her balls. Feeling her cock over the top of her panties felt nice and soft and smooth. I saw her wiggle her pelvis when I did this and heard a “mmmmm.” escape from her mouth.
I wrapped my hand around her cock and squeezed a little. Then I slid my hand down to her balls and felt them on top of her panties. This is the part that always gets me hard. I reached up and tucked my fingers into her waist band. She sensed what I was doing and lifted up her pelvis a little. It was them I tugged her panties down. Her cock flopped out and landed on her thigh. Now it’s on baby. I reached up and ran my fingers over her cock. Lightly touching it without any encumbrance. Just the feel of soft skin and pulsating. Gripping it firmly I was feeling my first cock besides my own. At least for sexual purposes. Being in the medical field I have seen and had to move many penis’s in so many years. But this was for my pleasure and enjoyment.
She felt soft and smooth and hard at the same time. I could tell she wasn’t fully hard yet and I wanted to change that. I gripped her cock at the base and pointed in towards my face. It wasn’t hard to admire her size. Her cock looked a little thicker in the middle then mine, and less so at the tjp and base. She had a small amount of foreskin, which was new for me as well. And unexpected. I guess I didnt research this enough I thought. But this isnt a problem because I am going to make her feel like the queen she is with my mouth.
With a firm grip on her dick I checked all sides and base admiring It pointing in back and forth. Hers was darker than mine and longer and thicker. This was a turn on. I licked my lips and started moving my mouth to her dick.
Her dick was getting harder from my hand and my breath. With a small motion I opened my mouth, stuck out my tongue and licked her cock head. Then I opened my mouth and took her dick in until I was past the ring of pleasure. You know. The ring of skin just below her cock head. Letting my lips squeeze her cock I savored the feeling of it. In my mouth it was soft and spongy. She let out a little moan when I ran my tongue under her head. Letting her cock pop out of my mouth, then let it slide back in. Every time I went down her shaft I tried to take more and more of her dick into my mouth.
After a couple attempts I was working her cock like a champ. She reached up and grabbed the back of my head. With some assertiveness she pushed my head down while I was sucking. She wanted me to take her cock. You want to suck your first dick, well let’s see how much you really want it. I let her push my head. With a little effort I tried to take her cock into my throat. Believe it or not it wasn’t that difficult.
She kept my head in her hands and I took a lot of her cock in my mouth and throat. This went on for a couple minutes. I wanted to savor the feeling of it more. So I let my tongue wash her dick. I loved how it felt in my mouth. The slick softness was addictive. I’ve always had this oral fixation. Hell I loved eating pussy too. My girlfriend’s pussy especially. Her lips were always loose enough to suck on. And her cock in my mouth was so slick It let me run my tongue around very easily.
She stroked my hair and said you are doing so well. With her encouragement I shoved her dick in as far as it would go. I think I took about 90% into my mouth and throat.
I had done it…I have a cock in my mouth. And I love it. It was so intoxicating. So much anticipatory sexual tension. It was all coming to life. What does this say about me? Well we are not done yet I said to myself.
The thing about oral sex is the intimacy. Some people have argued with me but I still to this day believe that oral sex can and should be more intimate than intercourse. When you have someone who is into doing it. Or you yourself are into doing it. There is no denying the feeling and satisfaction of it. For me I can tell you that there is nothing I enjoy more then putting my girlfriends legs up and supported on say the living room chair arms. Taking a seat and having her pussy at the perfect level. Having all access to her makes dive in and suck her lips and clit and stick my tongue into her pussy hole. Never forgetting to run my tongue down to her taint and asshole and tease that a little. God I really love it. The way it feels in my mouth is addictive. Well the same goes for this. Her cock was so silky and soft in my mouth I loved how it slid around like it was butter on a hot frying pan.
What I wanted and needed to hear was the sounds of her enjoyment. Everybody wants to do a good job. Well this was no exception. So I tried different things to see if I can get that from her. Pulling on her cock to make the skin taught and then slowly taking her length in my mouth. Letting my tongue glide along the underside of her dickhead to the ring and then shaft of her cock. Well that one she loved. So I did that a few more times. Pulling it out of my mouth and admiring her size and hardness.
I told her to stand up. Now I was on my knees in front of her and cupped her balls and softly tickled them while I guided her cock back into my mouth. I would occasionally look up at her while she was still inside of my mouth and check to see where her attention was. To my pleasant surprise she was looking at my and smiling and had to close her eyes occasionally from the pleasure. She grabbed my head and told me to take my hands away. I did what she asked and knew what was next. WIth a strong force she pulled her hips back so her cockhead was just inside of my mouth. Then with a good bit of force she pushed her hips forward and my head towards her pelvis. I felt her cock hit the back of my throat and start to tip downwards. She pulled me back an inch or two and then pushed my head again. This time her cock got past my throat and down into it. Now she was there it wasn’t coming out right away. So I let her push with tiny thrusts into my throat. Never did I think i would be making those throat fuck noises but her I was. Eventually I pulled back and had to breath. She said baby you took that like a champ. I almost came in your mouth.
Now that was what I wanted to hear. Also what I wanted to happen. All I wanted now was for her to cum in my mouth from my blowjob. That is an experience however, that would have to wait until another day. Today I wanted to keep feeling that smooth cock in my mouth.
So now I got up and stood next to her. She was totally naked except for those hot stockings. I unbuckled my belt and started to unbutton my pants when she grabbed my hands. She reached for the pants button and quickly unzipped them. I watched her as she knelt down in front of me and pulled down my pants until they were on the floor. Stepping out of them I was left with my boxer briefs on. There was a pronounced bulge from my cock being nearly fully erect. I could feel the wetness of my pre cum from being so turned on for so long.
She stayed on her knees and ran her palm over my boner and slipped her fingers into the waistband. With a quick jerk my underwear was off and my cock sprang out and up. It was instantly hard now that it was out of the cage. The temperature in the room was perfect and that made my balls nice and loose. Hers by the way were smaller than mine. But like me her balls were loose and dangling. This if you cant tell, is how I love my balls to be when I am having sex. They look better and slap my girlfriend’s chin or clit depending on where my cock is inside of her.
She then proceeded to inspect my cock. I was not as long as her. My cock is white and pink colored while hers was darker toned. Her cock was thicker in the middle than mine. My cock is the same thickness expcept for the base which is larger for sure. My cockhead was a little bigger than my shaft and hers was smaller than her shaft. You know guys have to compare everything. This was no exception. Albeit this was my first time and I really wanted to remember every detail for future spank thoughts.
She squeezed my cock in just the right spot. Having about 13 of my cock in her hand the pressure was perfect and caused my cockhead to swell. A little more precum came out and glistened in the light. She stuck her tongue out and licked the cum. Just a little. Swirling it around my cockhead making it very slick. Then she licked the underside of my dick from the base to the head. God that felt like heaven. Without fanfare I was inside her mouth almost 70 %. She started to work on my cock for a bit. Obviously this woman knew how to suck a man’s dick right. Good God it was so good. Just enough pressure. Just enough depth. One of the best I ever had.
It wasnt long. Maybe 5 minutes and I said hey. Pulling myself out of her mouth I was like “I dont want to cum yet. You are blowing my fucking mind right now. Thank the heavens that your skills are legendary. But now I want another position.
I stood up and went to her. Just because I was dieing to do it, I grabbed her cock and mine. I put her cock alongside mine and squeezed them together. Not knowing exactly what I was doing or going for I had them touching and rubbing together. She took the hint and we stood facing each other. She had my cock in her hands and hers in mine. Now we got a good look at our cocks side by side. It was a moment I wish I had asked her to film. Our dicks were both equally hard. Now we both had precum dripping and both pulsed almost in unison. I get so hard that my cock jumps from the contractions of my horniness.
WIth that I went onto the bed. Being totally naked I laid on my back with the pillows propping up the left side of my body. I told her to put her pelvis over my head. She understood and knelt on the bad with her cock dangling over my face. Now her balls were hanging down nicely and her cock swayed back and forth. She also would occasionally make her dick jump. It was universal I see.
I reached up and lightly touched her ran my fingers from balls to tip. Then I gripped her cock and pointed it towards my mouth. She dipped her hips a little and that was perfect to get a huge amount of it in my mouth. I loved this angle. She could push into my face or me raise my head to take her in. I stroked her dick while sucking on the head. With some more force I got her balls to slap my hand and she let out a couple “of my gods.” She would also let out those moans of pleasure I am addicted to. This went on for a bit. I had spent so much time on her I think she forgot about me.
Well she must have sensed my disapproval and I felt her hands on my balls. She was squeezing them and tickling them at the same time. This was nice. Note to everyone. Don’t neglect those bastards. Men have sensitive skin in the scrotum. You are just adding to the surface area you can pleasure a man when you play with them. Sorry that was my public service announcement. I felt her wet mouth on my cock now. The first couple of seconds are usually so intense. That is why you start with a softer suction and get it nice and wet. She did that. Super wet and soft suction. Then she took me entirely into her mouth and down her throat. That was so fucking sexy and hot. I started to buck under her. She kept throating herself on my cock. It was like a couple minutes and I said “i am going to cum”. Without telling her that I really do cum. I cum alot.
She let me out of her mouth with a pop. I felt her hand start to jerk my dick nicely. With it being so wet she got a perfect motion going. Then I tensed up and squeezed her dick in my hand. She was still inside my mouth when I started to cum. I am not bragging but to say I shot my load is an understatement. This was so hot and so much time before I came the first blast went right at her face and shoulder. The second shot hit her in the chest with a splash that landed on me. I can feel my cum splash on my chest and then the third blast came out. This time it didn’t go as far but was more cum than the previous two shots. I almost laughed when I heard her say “wow, now that is a good boy. You shoot like a fucking water pistol. God that is sexy”
I was so happy right then and there. This could not go any better. But now we have one last thing to finish. She needed to cum and I wanted to make sure it happened. I asked her if she could cum from my blowjob. She said “not usually baby.” “Most of the time I need to fuck to cum” she said.
Now to be honest this was the part of the experiment that I was unsure how I would handle. Blowjobs were what I was after. I was after oral sex in the biggest way possible. But I had this feeling that right then and there I wanted her to cum. I want this women to cum so much that I am going to give up my ass. This would be the first time anyone was inside my asshole. I have spent many many times with fingers up there or tickled with a tongue or even small dildos. But this was the actual cherry I am giving her. So I said “baby you can have my ass. I want to thank you and reward you for something special to me. If that is how you like to cum then you fuck me good.”
She was happy and could not contain her smile. I said “you put me how you want me baby.” She had me lay on my belly with my legs scissored. I heard her with the condom wrapper. It took a couple seconds and I felt her hands on my ass cheeks. She was pushing my ass apart when I felt her cock head touch my asshole. With some pressure she pushed until her cockhead just got past my asshole. I heard her let out a sign like she enjoyed that. It felt good actually. Then she started to push in and out and got all the lube to cover her cock and my entrance.
It was a strange experience to say the least. She was balls deep in my ass. I felt her balls rest on my ass cheeks. That was sexy. I let out a moan of myself and wiggled a little to get her in deeper. She took the cue, grabbed my hip and started to pump her cock into me. At first slowly and within a few minutes she was going from tip to base and balls slapping my ass with a lot of vigore. I let her fuck the hell out of me. If this is what she wanted and needed then I am gonna give her the farm. Now she was pounding me so hard that her hips were smashing my ass cheeks. I remember having my eyes closed and letting out soft moans and groans of pleasure. When she had the right angle and depth she hit my prostate perfectly. This went on for a couple minutes. I was being pushed further on the bed from her pounding my ass. It wasn’t uncomfortable at all. I knew I had to relax and she would be able to do whatever she wanted without any discomfort.
I could tell she was close because she was saying “fuck yeah. This is one nice asshole to fuck.” I moaned and rode the energy wave she was giving me. She grunted and kept fucking me. “Fuck baby I just came”. With that she kissed me passionately on the shoulder while her cock was still inside me. I felt her lay her body on me and kept kissing my back and shoulders. Eventually she popped out of my ass and stood up. I rolled over to see her limp cock hanging down and the condom full of cum. “Baby do you think I was a good cock whore tonight?” I asked her. “Did I suck your cock well? Did I give you my virgin asshole right?” She smiled and said that she loved taking virgin assholes and throats. I felt my cock twitch when I heard that.
I knew this was a common thing. Not that it wasn’t important and special. She just happens to fulfill my need and biology to allow my darkest sexual desire to be a reality. I got up and walked to her standing over me. This needed a hug or some other contact before we end it. I remember feeling our cocks touching and how I liked her hugs. She was genuine and it showed in her energy and actions.
After I was dressed I asked her ”how many men has she taken like this? Her response was a smirk and eyelash fluttering. Never got my answer but I always imagined it must have been so many.
I went home and had nobody to tell it to. So I did write a comment on Whisper to say how confused and satisfied I was. Some people commented that it was normal and hot. To this day not a single person in my life knows I was a cock sucking fuck toy for a night. It may happen again because I refuse to corner myself in life again. If it is meant to happen it will. Or I just get another craving to suck on some cock and break down for another go.
Sorry this was so long. The writing of this was to get as much detail out there so I never lose or forget it. Thank you for reading it.
Source: reddit.com/r/gonewildstories/comments/pit0p2/never_thought_i_would_have_done_this_trans_mf
Sexy story! Enjoyed reading your adventures. Xx