He Understood the Mission at Hand
By Katie Johnny

Posted With Permission from Katie Johnny

I am writing this to you less than 24 hours after having the best sex that I’ve had in decades, and perhaps in my life.

I’ve had a lot of sexual encounters over the years. I’ve had mostly good ones, and a few bad ones, but out of all of the experiences I’ve had, there are only 3 or 4 that I can look back on and immediately get horny and tingly from just reliving them in my mind. The one that I had yesterday quickly moved into that rarified air.

I’m in my mid 40’s, so getting laid with any regularity isn’t nearly as routine as it was in my late teens, and 20’s and 30’s. 20 years ago, I could post a single pic and get 3 or 4 inquiries right away from people who wanted to devour me. These days, everybody has multiple pics and various other forms of media, and after chatting/flirting with people on the site, they will often just ghost you out of nowhere, and half of those guys are probably bots.

I was all alone in a hotel room, so I had a few drinks, had a few puffs, listened to my slut pop playlist on the Bluetooth as I bathed and shaved my body to be as smooth as a baby’s ass. I brought my vibrator and my dildo with a suction cup at the base. I plunked it against the back wall of the bath, and would take a sniff of poppers, then work this large silicone cock into my pussy. I did this for about an hour, just leisurely toying with my pussy and stretching it out.

Once I was out of the bath, I threw a long t-shirt over my bra and panties and began looking around online for some dick. I logged on to one of the gay dating sites, and within a minute of logging on, my mailbox started flashing with a new message. The message was from username, “hickorytree,” and he asked me what I was into and if I was looking for right now.

For those who might not be familiar with the “online hookup” process, I’ll give a quick explanation: 9 out of 10 interactions on these sites end up falling apart, or after chatting with someone and making plans, they will hit you up for money, or after revealing that you’re a panty wearing sissy, they’ll insult you, then ghost you.

It’s for these reasons that I will sometimes hide the fact that I like wearing girls clothes and being treated like a girl in bed. So many macho shitheads on these sites go out of their way to overstate just how masculine they are, and how that’s all they are interested in, and blah blah blah. I’ve yet to find a cool website dedicated to amateur sissy, crossdressing, trans girls, and their admirers. If anyone reading this knows of one, please leave in the comments…

So when “hickorytree” asked what I was into, I didn’t tell him that I’ve spent the bulk of my life feeling like I’m trapped in the wrong body, I just told him that I derive sexual pleasure from pleasing a man, and that I love to suck cock and bottom if it got there. He immediately responded and told me that he was a top, loved a good blow job, and could travel to me right away.

This threw me for a loop, because most guys on these sites will hem and haw and waste so much time volleying 2 and 3 word responses back and forth to each other until someone can no longer hook up. My man was so quick and concise with his response to me that I immediately went to review his profile again, and noticed that he had joined the site just 1 day ago, which typically means the person isn’t even a person, and are a bot that will soon solicit you for “gas money” to come see you.

I sent a message saying, “That’s great, head this way if you’re even a real person,” and he immediately replied that he was, and asked me why I would say something like that.

I responded, “I’ve just noticed that almost anyone who sounds too good to be true has usually been on the site for a day or two, and in most of those instances, they end up asking for money, or try to lure people into going to another site to chat, or whatever. In other words, they’re not real.”

“LOL, let’s swap pics then quit talking and start having fun,” was his response, and he immediately followed that with a face pic, full body pic, and another full body pic that focused mainly on his cock. He was really handsome, had a salt & pepper beard and hair, and a million dollar smile. His cock was uncut, thick, and was about 7 inches flaccid.

I quickly sent him a face pic, a body shot, and a shot of me pulling my panties to the side and showing off my tight hole. He sent back a row of about 30 exclamation points and said he was leaving and would be at my hotel in 20 min. I got really excited, but metered my excitement based on previous experiences of guys saying things like this and never showing up.

It was for this reason that I just spoke from the heart, and told him what I was hoping to get out of this hookup.

“I’m really excited to see you,” I said, “and my deepest fantasy is to basically be made love to as if I were a girl. Does that make sense?”

A few minutes went by, and he replied, “Yup! I’m 10 minutes away!”

The way he casually and excitedly answered my request with multiple exclamation points and said he was getting closer got me really excited. I was both really excited, and really nervous. It’s a pretty vulnerable feeling to be standing in a hotel room in satin bra and panties, and awaiting a strong and capable man’s arrival. Not just a man, but a man who has told you that he’s going to treat you like a girl, at your request, no less.

I brushed my teeth and made a drink, then put poppers, condoms, lube, and my Bluetooth speaker on a nightstand. I went extra subtle on my makeup, in case it wasn’t something that he liked, and took my bra off, since he had mentioned more than once that he loved being naked with his lovers. I was playing with my hair in the bathroom mirror when I heard a knock at the door. Not only did this man not flake out, he was downright punctual in his arrival. My heart was beating out of my chest as I turned to walk towards the door.

I took a deep breath, removed the bolt lock, and let him in. He walked in with a giant smile on his face, and stopped just inside the door. So many people will misrepresent themselves online with doctored photos, or pics of them from 15 years ago, etc., but not my man. He was exactly as advertised. I was taken aback by his good looks.

I was smiling in silence, and devouring him with my eyes. He looked around the room, then looked at me, and inched closer while smiling. I went to say something, and he made a “shhhhh” sound, then went in for a kiss. I went towards him as well, and the minute our lips met, I began breathing very heavily. He could tell I was really turned on, and incredibly nervous, which gave him even more confidence and made him kiss me even deeper.

As he did so, I wrapped my arms around him and began kissing him back as enthusiastically as he was kissing me. I ran my hands up and down his back, and into his hair, pushing his face closer to mine. He French kissed me that entire time, and anytime he would stick his tongue down my throat, I would wrap my lips around his tongue and begin sucking it like a dick. He took off his shirt to reveal that his entire body was covered from head to toe in curly, manly hair. I began caressing the back of his head with one hand, while running my other hand up and down his back.

I began trying to take off his shorts, but I couldn’t get the right angle on his belt, and my hands were visibly shaking from nervous excitement. As I struggled with it, he grabbed my hands and put them down at my side. He undid his belt, dropped his shorts and undies, and pulled gently on his cock to let the foreskin roll back. I swear I think his cock head was also smiling.

At that point, he just looked at me and nodded towards the ground. He didn’t have to say a fucking word. I immediately fell to my knees, grabbed the base of his cock with one hand, then sort of pulled back the foreskin and licked the head like a lollipop while looking up at him. I was on my knees, ready to serve, when he smiled and nodded at me, signaling that it was officially time for me to suck his dick.

I immediately put the head in my mouth, then inched my way down the entire shaft, moaning the entire way. He exhaled in delight, and put one hand behind my head, pushing my head into his crotch. I was so fucking turned on by the scenario and his throbbing cock in my mouth, that I gleefully let him force me down until I started making a mild gagging sound.

He let me go up and down his shaft two or three more times, then pulled me back up, and stuck his tongue all the way down my throat. We were hugging tightly, and making out intensely. Both of us were breathing heavy. He pushed me back down gently, then took my tank top off with one hand as I was descending to my knees, and threw it to the ground.

“Are those bra marks on your skin?” he asked, and I got really nervous. I didn’t know what to say, but bra strap and band marks on a body are unmistakable indentions, especially on my pale, soft, milky skin.

“Yes,” I replied, as I gazed up at him with his cock in my mouth. I pulled it out and said, “I didn’t know how you would react to me wearing a bra, so I took it off right before you arrived. I’m sorry if this ruins the vibe for you,” and began sucking his cock again right away.

He smirked and said, “That was a kind thought, but if you took it off for me and me only, then I’m going to have to insist that you put it back on right now.”

I peered up at him again with my best baby doll eyes, and with his cock in my mouth. He gently pulled it back and said we could continue once I put my bra back on. I got up and walked to the drawer where I had stashed my bra, and clumsily put it back on in front of him as he calmly stroked his cock, never taking his eyes off of me. I was struggling to get the straps flat and correctly on my shoulders, which made him chuckle, but I finally worked it out.

There I was, clad only in a black satin bra and panties, which is pretty much as vulnerable a situation that a sissy girl can find herself in, and walking back towards my man. He smiled and welcomed me back with a deep embrace and a big kiss. I immediately began breathing heavier again, and after a single kiss, he gently pushed me back down to my knees, and nodded for me to pick up where I left off. I rifled his stiff cock back into my mouth as fast as I could. He let me continue for a minute or so, then pulled back and pulled his cock out of my mouth.

He pulled me up, kissed me even deeper for a second, then pulled back, smiled, and nodded towards the bed. I told him that I was self-conscious of my body as I was walking over to get the poppers and other party favors, and he told me not to be.

“Why would you feel like that?” he said, “You see how hard my dick is right now, don’t you?”

I glanced down at it and he wasn’t lying. That dick was at full mast and throbbing.

“Don’t worry about the poppers and stuff,” he said, “just come back over here to me right now, baby.”

I did what I was told. I was totally under his control. I was putty in his very strong and capable hands. As I approached him, he came forward and wrapped me back up into his arms and began kissing me again. Then he sort of nudged me backwards onto the bed, and I fell on my back, facing him. He held my legs in his hands by the ankles, and pulled me forward to exactly where he wanted me to be. He told me to take my panties off, and I tried but couldn’t really pull them out from under my ass, so he reached down with one hand and pulled them off for me.

He held both of my legs up with one hand, and began kissing them all over. The panties were still hanging on one of my ankles, and he ripped those off and threw them to the ground. He spit on his free hand, and gently inserted two fingers into my pussy. I began grinding on them, and they were knuckle deep in no time. He let my legs go, and they fell to either side of him. My legs were spread wide open. He kept fingering me as he planted himself firmly on top of me, kissing me. He pushed my bra up and started sucking on my rock hard nipples.

I was in total ecstasy, and kept whispering things like, “oh my fucking god, oh my fucking god, you can’t be real, this can’t be real, oh my fucking god you absolute fucking stud,” and so on. He smiled at me and began kissing me, and as he did so, I ran my hands through his hair, down his back, then all over his chest. I kept trying to reach his dick, but it was just out of my reach.

He could sense that my being unable to reach his dick was frustrating me, and apparently he thought that was cute and funny. He kept kissing me, and telling me to relax, and rest assured, his dick was definitely going to reach me in due time. I was breathing so heavy, and was so fucking turned on by his seductive actions.

He kissed for a few more minutes while grinding on my body, then pulled back to where he was hovering over me. He kept eye contact with me as he did so, then he smiled, put some spit on his fingers, and put his hand right around my hole. He ran his fingers around the outside of my hole, then gently stuck one in, and quickly followed with another finger. I was moaning like a sissy bitch when he did so, and he worked them back and forth gently as he leaned forward to kiss me more.

I was breathing heavy, and gyrating my hips and ass as much as possible as he kissed and fingered me. After a few minutes of that, he smiled at me and asked me if I was ready. I told him yes as I was runningmy hands over his hairy pecs and trying to catch my breath. He smiled wider and began kissing my neck and my shoulders, then finally arriving back to my lips, where he buried his tongue down my throat.

As we kissed, my mind kept racing, and at this point, it was racing as fast as my heart was. I could not believe that such a prince of a man had arrived in my life, and that he was making deep, passionate love to me like I was not just a woman, but he was about to fuck me like I was HIS woman. Anyone who has ever hooked up online knows that the odds of actually having a great experience with someone on any of these adult sites are low. For every good experience I’ve had, I’ve had at least 10 bad ones, but this good experience was shaping up to perhaps be the best of my entire sissy life.

He pulled his fingers out of me, and stopped kissing me long enough to spit onto his hand, then quickly but gently reinserted his fingers inside of me. He pulled them out again and spit on them again, and began stroking his cock to lube it up as well.

I pointed to the lube and rubbers laying on the nightstand. He smiled, leaned in to kiss me deeply, and as he was doing so, he stuck his rock hard and raw cock inside of me. I don’t ever allow bareback, and this would have been no exception, except in this particular instance, I was in such a euphoric state, my entire body was tingling, and I had been seduced so badly that I felt like he might actually end up being “the one” for me. That’s when you know the cock is good. I take every precaution, but once he plopped his rod inside of me, I wasn’t fighting it.

On top of all of that, his raw cock felt so amazing inside of my tight sissy pussy that I temporarily lost the ability to speak. I opened my mouth to tell him wrap it, and before I could speak, he started kissing me and ramming his tongue down my throat. I was going to get fucked exactly how he wanted to fuck me. I felt droplets of sissy cum lightly spurting out of my shriveled dick as he fucked my mouth with his tongue, and fucked my ass with his beautiful cock.

He laid down on top of me and pumped away at me furiously, then stood up on the floor, and pulled my body to the edge of the bed. I was grabbing for his body, so that he would be able to smother me with hugs and kisses as he methodically fucked me. He remained inside of me the entire time that he pulled me to the edge, and never stopped smiling or making constant eye contact. He knew that I was basically speechless and under his complete control.

Once he got me into the position that he wanted, he pinned my legs back over my head, and collapsed on top of me, taking turns between sucking my nipples and French kissing me, all the while he was steadily pumping his cock inside of my now fully flowered out pussy. My hands ran up and down his back and his head, and I couldn’t effectively speak, thanks to the mind rotting dicking down that my man was giving to me.

I assumed that the level of intensity that he was fucking me at could have been maintained for at least another half hour, which was totally fine with me, but I was wrong. As I was rubbing him all over his body and moaning in ecstasy, I felt his body tensing up, and before I could request that he pull out and let me drink his cum, he began grunting and thrusting, and I felt his warm seed filling up inside of me.

He began kissing me intensely as he was spurting inside of me. All of this scorching hot activity triggered gushes of my sissy cum to start shooting out of my flaccid, floppy, useless sissy hose. I was moaning quietly and gripping him as if I wanted him to stay inside of me forever. His sweat was dripping all overme as we made out and groaned and grunted in each other’s ears until he stopped pumping, and just let it stay inside of me as we continued to make out.

He smiled at me, kissed my forehead, and withdrew his pistol from my stamen. When he got fully out of my pussy, he got up and laid next to me on the bed.

“You naughty thing,” he said, “look at what you did to my belly!”

I glanced over and saw my sissy cummies matting the hair on his belly and giggled, which triggered him to reach over and kiss me. I laid there gazing up at him, and was subconsciously sticking my fingers into my sissy pussy, running them around the edges, and feeling the load of baby batter that he had deposited inside of me. I could feel it slowly escaping from me and dribbling down my quivering thighs. I can’t explain it, but it was one of the hottest fucking feelings I’ve ever experienced.

We made small talk while we made out for the next 10-15 minutes, then he got dressed, and kissed me goodbye as he was walking out the door. As he looked back at me upon leaving the room, I just melted into the bed and began playing with my dripping wet pussy and clitty until I came all over myself and the bed again. I want to see him again soon. Wait, I take that back. I NEED to see him again soon.

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