Most of my stores are about past exploits. This one happened a few weeks ago.
Prior to this incident I’m about to tell you about, I hadn’t been with a man in 3 years, but the stories I’ve been writing, and the feedback I’ve received have inspired me to get back out and find some cock. There’s only so far you can go with vibrators, dildos, and memories, and at this point, I have definitely taken that road as far as it can go. I figured it was time to make some new memories, and so here we are.
Most stories I’ve written on here have been about my exploits when I was much younger, and figuring out that I was a sissy, or describing encounters that shaped me into the sissy I am today. This particular story is about something that happened just a few weeks ago. I’m in my mid 40’s now, which means a few things when it comes to sexual encounters.
For starters, I’m unable to spend a lot of time looking around for fun like I once could. My days are busy, and despite what you might think about the supposed “ease” of internet hookups, actually meeting someone who is real, sincere, and serious about hooking up is very hard to do. Following through seems to be the biggest online issue. Someone almost always flakes out, and I would be lying if I said that I had never done so myself. I absolutely have flaked out on guys who weren’t as advertised, or who said or did things that made me uneasy about a situation.
Another thing is my age. Let’s face it, hookups are more for younger people looking to explore their sexuality. Those people are almost always looking to and have fun with other younger people, so an amateur sissy in her mid 40’s isn’t going to be appealing to a guy in his 20’s.
Sissies that are in their 20’s have been working full time at being a thirst trap for men since they were teenagers, and they are usually almost always out of the closet, so their families and friends know about them, and they’ve been living their lives as girls full time for a while.
I’m none of that stuff. I still have a regular job, and still haven’t revealed myself to anyone outside of the men that I’ve been with. I’m only a lingerie obsessed cum guzzling whore behind closed doors, so I’m never going to win any sissy beauty pageant online. The other girls are far more beautiful, and will almost always outshine me in a lineup.
It takes a special daddy to see the potential in me, especially if the daddies online are all 20 and 30 something years old. I don’t get offended if they’re not into me. I’m an amateur, and for all intents and purposes, I’m a crossdresser, no matter how I feel on the inside about my sexuality.
I fully understand that these guys are looking for something far more advanced than me when it comes to stages of sissyhood. As I mentioned earlier, some of these younger sissies have had electrolysis, breast and/or butt enhancements, and are on hormones, etc. They’ve been wearing bras and panties and dresses since they were 13 and 14, all with the support of their families and friends. They are girls at this point. I’m happy for them, and totally jealous, but that’s not my reality.
Every so often, that special someone comes along, and those parameters all get thrown out of the window. Such was the case with Larry. I was looking around on a hookup site, when Larry popped into my DM’s. He wasn’t a wordsmith, and he had never been to charm school, but he was a 24 year old young black man who was at least willing to say hello to me, which immediately got my attention.
He had no picture in his profile, and I usually don’t reply to people who don’t show pictures. He also had little to no info in his profile, which is another red flag when searching for men to fuck me online. Out of about 20 profile questions, he had answered about 5. He was 24, 250 pounds, black, he was a top, he drank occasionally, and he couldn’t host. While looking around, I noticed that my DM box started blinking. The message was from “Larry24Top.”
“Sup” was all he typed into the message box. Again, that’s another red flag that I’m probably having a conversation with a bot. I’ll usually give them a one or two word reply then wait. A bot will usually immediately send you a picture of a drop dead gorgeous guy with a raging 9” cock and 8-pack abs. No supermodel man is looking to hook up with me. I’m an attractive person, don’t get me wrong, but I’m also not naïve enough to think that a young Greek god type guy is seeking me out when they could have their choice of people to fuck.
I replied, “Not much, what about you? I’m Katie, btw.”
I fully expected that I would soon be sent pictures of guys that look like male models, but nothing of the sort happened.
“Lookin 4 sissy pussy. U?
I wasn’t about to get caught up in some bullshit back and forth, so I said, “Need a face pic, body pic, and cock pic, or I’m going to block you.”
He replied, “K,” and within a minute or two, I had everything I had asked for. He even sent 2 cock pics. He had the face of a baby, the body of a lineman, and a really thick 7 or 8” cock. The cock pics he sent were one where he was holding it from the base, letting me see how thick and long it was, and the other was a similar pic with cum spurting out of the tip of his cock.
This really turned me on, as you could imagine. The pics were all amateur, and it was easy to see that he had recently taken them with his phone. My heart started fluttering, so I waited for a second to gain my composure, and replied, “Very nice, you like older sissies?”
“Yup, lookin’ to fuck now,” he said, “you host?”
Now the ball was in my court. I talk a big game sometimes, because I’ve been stood up a lot, but this seemed different, and it actually made me nervous. For as much as I’ve been stood up, when it comes time for me to actually commit, I’ll end up chickening out. I figured I would ask a few more questions before telling him where to find me.
“You play safe?” I asked and he replied, “Yup.”
“You clean and discreet?” I said, and he said, “Yup.”
“What do you want to do to me?” I said, and he said, “Fuck you, make you feel good, nut in you.”
My heart started racing, and before I could talk myself out of it, I said, “We have to be really quiet, I have neighbors on either side of my apartment, and they know nothing about this, understand?”
He replied, “Won’t make a sound. You might, I won’t.”
So I replied, “Come get this pussy. How long will it take you to get here?”
He replied, “This app say I’m 743 feet from you, I’m walking, leave now, see you in 5 min. Maybe less.”
Holy shit! This guy is in my apartment complex! My heart was pumping furiously, I ran into the laundry room and grabbed a sheet to lay over the bed, lit some candles, pulled out my rubbers, lube, poppers, and a dildo and put them all on a nightstand. I went to go make a drink, when I saw I had a message.
“Here”
I walked to the door, opened it, and there he was. Larry was a brutish man. Blunt features, thick, but not fat, and said nothing, just smiled and walked in. I told him to make himself at home in the bedroom, that I had to freshen up, and asked him if he wanted a drink.
“Water,” was all he said, and started walking towards the bedroom, “Thanks.”
I scurried off to the kitchen and made myself a vodka & tonic, and grabbed a bottle of water for him. I stopped off in the bathroom to fix my makeup and strip out of my clothes. I put a babydoll nightie on over my bra and panties, freshened up my lipstick, took a series of deep breaths, and headed to my room to go see Larry.
I had a small Bluetooth speaker on the nightstand, and shuffled my “Sissy Bitch” playlist, (which by now, if you’ve read my other stories, know the list consists of Britney, Rihanna, Iggy Azalea, Nicki Minaj, Madonna, etc. Various slutty girly pop). Larry was laying on the bed, totally flaccid, completely naked, and holding my dildo. I started to try and make small talk.
“So, Larry, I’m Katie, how are ya?” I said, as I pranced daintily to the other side of the bed and laid down next to him.
He didn’t say anything, he just motioned for me to come closer, and as I did, he wrapped his big arm around me and pulled me close. He put my head on his chest. I could feel his heart beating hard, and hear him breathing nervously. From my vantage point, I could see his soft cock in a nest of public hair. Cocks are amazing, in the sense that as I looked at his, it was nothing to be intimidated by. The head of his cock was well defined, but it was essentially deflated. I tried to talk to him some more.
“So, you’re doing alright tonight, daddy?” I whispered, and he murmured something that sounded like, “mhmm,” then reached down to his cock with his other hand and started pulling on it. It remained relatively small looking, as he flopped it around from the base. I reached down with one of my hands to grab it as well, and he made a motion with the arm he had around me that I took as a signal to start working on it, and I obliged.
I started kissing my way down his chest and belly, then got to his cock. I licked the head with my tongue, and gave it a suction cup style kiss. He grunted, and his cock began to slowly inflate. I could tell that he liked that, so I did it again, then took it between my lips and started running my tongue all around the head, burying my nose into his pubes and taking the whole thing in my mouth.
As I did that, his cock started thickening and widening, so I did it a few more times in a row, and it continued getting thicker and longer. It was big enough to suck at this point, so I began sucking on his cock, and as I did so, it began getting even bigger and harder. He was moaning and told me to suck his balls, which I did, and that made his cock even bigger. When he told me to go back to sucking his cock, I was looking at a full, thick, 8-inch BBC on a 24 year old black man.
It was a beautiful sight to behold, and I was excited to suck and lick and kiss all over it. As I did so, he started pulling at my nightie with one of his hands, then grabbed my legs and motioned for me to lay on top of him.
“Take off them panties,” he said, and I did so, pulling them down and positioning my pussy right in front of his face. My panties were wrapped around one of my ankles, and he grabbed me by the waist, pulled my babydoll up, and then pulled my pussy to his lips. He repeatedly stuck his tongue in and out of me, and I intensified sucking his cock on my end.
He grabbed my ass cheeks with his hands and spread them apart as far as he could, then buried his nose, lips, and mouth as far between my legs as he could.
I can’t describe how good it feels to have your sissy pussy eaten out by a man. He had large facial features, his lips were thick and luscious, and he was slurping at my pussy, which made me suck his cock with so much more lust. I started moving my pussy around on his face, and he started moaning more, as he licked, slurped, and kissed all over my pussy as I throttled his cock into my throat as far as it could go. We were both moaning and making each other feel good, and it was nice.
“I got to fuck you now,” he said, “get off that dick, and lay on your stomach. Put your legs together close.”
I did what I was told. He was breathing heavy as he got up on his knees. I grabbed my poppers and went to hand him a rubber and the lube when he said, “Not yet, I’m sticking that tip in first raw.”
I began to object to his plan and he said, “Trust me, I ain’t gonna nut in you. I need to stick it in raw first.”
At this point, I was hotter than Georgia asphalt, and agreed with and let him do as he wanted. He told me again to push my legs together, and I did what I was told. I felt him mount me, and after running the tip of his cock up and down my ass crack several times, he spit, and I felt it hit in between my legs. I took a hit of poppers and held it as long as I could.
I felt the tip penetrate my hole, and then plunge fully inside of me. I exhaled the poppers, and the room spun in a circle. He was exhaling in pleasure, my pussy was welcoming his cock, and gripping it with everything she had in an effort to keep him inside of her. The waves of euphoria, the rush of sheer size and force that his thick, hard, and veiny cock utilized as it pinned me into the mattress was all encompassing.
I groaned loudly and he quickly reminded me to shut up.
“I thought you ain’t want your neighbors to hear you, bitch. Shut the fuck up, and take this dick.”
He continued to thrust, and I caught my breath long enough to tell him to pull it out and wrap it, which he did. I took 2 big hits of poppers and held it as he reentered me, and I began to squirm. He put his entire body on mine, and brought his lips right up to my ear and started whisper talking dirty as he began thrusting powerfully inside of me.
“This my pussy, you get it? My pussy, bitch. Don’t squirm, girl. This my pussy. This yo dick, take that dick, slut. Take that fucking dick. Enjoy that dick. Get to know that dick, trick. You love that dick. That dick own you, bitch.”
I was replying to him in gibberish, and could feel my pussy being blown apart by his fat, young cock. All I was trying to do was release whatever tension that remained down there, so that he could do as he pleased with my quivering hole.
There was no slap as his balls hit between my legs, it was more like a thud. He was barely pulling back, he would just inch backwards then thrust forward hard inside of me.
“Tell me it’s my pussy, bitch.”
I couldn’t catch my breath, I would start to reply, and he would ram it harder inside of me.
“Tell me it’s my pussy, bitch. Say it, bitch.”
Finally, I said, “It’s your pussy, daddy.”
“You goddamn right it’s my pussy. What would your daddy think of you if he saw you right now, little sissy cunt? You his shame. I’m yo daddy now, bitch ass sissy.”
With that, he backed out. I scrambled for the poppers bottle, and tried to catch my breath, when he started talking to me again. Everything he said was in a low, deep tone. He was being quiet, and it was somewhat scary.
“Get up on your knees, arch that back, sissy.”
I did as I was told. I was still struggling to catch my breath, but managed to get up on my knees and arch my back. I took 3 big hits off the popper bottle before he plopped his dick right back into my pussy, then grabbed my hips with his fat hands and started thrusting. I held my breath for as long as I could, then released.
Upon release, all pain dissipated. I was in a complete state of numbed out bliss. He was breathing like a bull as he hammered me over and over again as fast as he could. He grabbed my hair with one hand and pulled my head back, and resumed barreling into my fuck hole. I started bouncing back on it. I wanted it harder. This confused him.
“That’s my dick, motherfucker,” I said, “that’s my motherfucking dick, give me that dick, motherfucker.”
He slowed his pound down, then started responding.
“You goddamn right that’s your dick. I own your sissy cunt, faggot. Take that big black cock, sissy cunt faggot!”
I was numb by now, he was raging, and there was sweat and fluids all over both of us. He thrust into me about 10 more times, then pulled out, ripped the rubber off, and ordered me to turn around. I did as I was told. As soon I did, he stuck his cock right up to my mouth, and said,
“Drink my seed, sissy cunt! Drink that big black cock seed, slut cunt!”
I rifled his cock into my lips and he began erupting. His cum was hot, thick, and voluminous. He was grunting and his hips were fully flexed as he expelled his load all over my face and down my throat. I was moaning, covered in sweat, his cum and my own cum, but I didn’t stop drinking.
He pulled out of my mouth and was slapping his cock violently across my face. Each slap would produce more steaming fluids. My eyes were burning, and my entire face was covered in cum and streaking makeup.
I fell over on the bed after he turned away from me. My panties were still dangling around my right ankle. My legs were shaking uncontrollably, as I reached down and pulled my panties up and put them into place. Larry had walked into the bathroom and I could hear him washing up in the sink.
I closed my eyes and tried to regain my composure. “Raining Men” by Rihanna was playing on the Bluetooth, and I just laid there and attempted to recover.
After a few minutes, I realized that I hadn’t seen or heard from Larry, so I called out to him, but there was no answer. I got up and walked to the bathroom, but he was gone. I checked the website we had been talking on.
“Did you just leave without saying anything?” I asked.
He replied, “Yup. That sissy pussy was fire. HMU if you need daddy to come set you straight again.”
I slinked back to bed, grabbed my dildo, and fucked myself to sleep.