A Weekend with Him

Another night with a buttplug in my ass, a thong barely covering my dick, and fishnet thigh highs pulled up my legs. I'm 24, always been about 20 pounds overweight, and a little over 6 feet tall. Not traditionally who you see as crossdressers and sissies in videos and stories.

I was spending the evening, as i do many evenings, perusing DirtyRoulette for any guy that wanted to dirty talk about fucking me silly. As is the same with many evenings, I was met with a bunch of guys who wanted someone with a bigger dick (mine is only about 4 or 5 inches), or wanted someone who was going to cum immediately, or had a fetish about my weight, which made me uncomfortable.

So, I ended up on Xvideos again, watching people hotter than me fuck like rabbits. Maybe a JOI or two thrown in here or there. I felt down about it cause i've always liked crossdressing and sissy stuff but could never find someone who wanted me to do that for them in a way I was comfortable with.

That was, until I met Charlie. Charlie is a coworker of mine. About 6 inches taller than me and very buff, and from what I could tell from the outline on his pants, very hung. He and I often worked together and had become friends over time, and hung out outside of work somewhat often. He was nice, and had dated a few people over that time but it had never seemed to work out.

One night as we were hanging out, he went to use the bathroom, just like any other night. This time, the toilet paper had run out. "Where do you keep your extra rolls, Tom?" Charlie asked from the bathroom.

"In the cabinet above the toilet," I responded, without thinking. I quickly remembered that that was also the cabinet where I usually kept my crossdressing stuff and jumped off of the couch, in anticipation of what was to come.

"Thanks," he said, and finished up in the bathroom quietly,

When he came back out, he sat back down and didn't say anything. "Phew," I thought. "The coast is clear."

After another couple of minutes with no other noise than the movie we were both only half watching, he said "Is that your stuff in that cabinet?"

I froze, and began stuttering trying to come up with a better lie than "No, some girl left it here."

He stopped me before i could say anything, "It's alright. I'm into that too."

I was still silent.

"Do you want to dress up for me?" He said, confidently.

"I... sure..."

"Good. I knew I had seen you checking out my package before," He said. "Do you want to see it in full?"

I could barely speak without feeling like I was about to squeal. He pulled out his flaccid dick, and even flaccid it was bigger than mine could ever be. I stared at it, drooling a little.

"Now, go put on one of those outfits and come back."

I had 5 outfits in the cabinet: a Schoolgirl, a Playboy Bunny, Velma from Scooby-Doo, a Maid, and some sexy red lingerie. A little cliche, I know, but it was what I knew I liked.

I decided to start with the playboy bunny, pulling the black costume up over my torso, pulling the fishnet thigh highs up and getting the ears on, after spending a couple minutes fixing my hair up a little sexier. I have long, naturally wavy brown hair, so usually it doesn't take much to make it look at least somewhat sexy. I put on a little makeup, basically just the dark red lipstick I have when I want to imagine someone was going to fuck me dressed as a girl. Now it was going to happen.

I walked back in, and as I did a little spin, I noticed his jaw drop a little when he saw how great my ass looked in the costume. While I was in there, it seems like he had also gotten himself at least half hard. It looked now that it could maybe be nine or ten inches, which I hadn't taken before, even with any of my dildos. I quivered excitedly at the thought.

"Here," he said, and pointed to the floor in front of him on the couch.

I made my way over and plopped myself down in front of his dick, and began to feel myself drooling again.

"I like this costume a lot Tom. Or should I call you Tomi now?"

"Should I call you daddy?" I asked, eagerly.

"Oh, I like that too," he said, and then motioned to his semi-hard dick. "Well, it's not gonna suck itself baby."

Without a second thought, I took it into my mouth, feeling the first couple inches I could fit in begin to stiffen as I worked his cock with my tongue. The musk of his big cock was so intoxicating, I began to feel my own dick stiffen up completely with his. "Do you like that daddy?" I asked, pulling my mouth away for a moment.

"You're really fucking good at that, Tomi. Fuck," he said. "I'm getting so hard!"

I worked my hands up and down, lubricated by my spit covering the top. "I've practiced it a lot... with dildos." I said.

"That's okay, baby. Your practice is showing well," He said.

I took him back into my mouth, working up and down the first four or five inches of his dick, lubricating it all over and feeling him quiver when I did something he liked. I then felt him grab the back of my head and say "Open up a little more, Tomi."

I did as I was told and then mumbled as best I could with a dick in my mouth, "Yes, Daddy." Although it certainly came out more like "Yesh Dadduh"

He began thrusting his cock in and out of my mouth more vigorously and deeply than before. The feeling of him having total control over me made me so excited, and I began to feel almost drunk with lust. I let him take me, use me, and I loved it. He suddenly stopped his thrusts and pulled away.

I looked up at him with my drunken doe eyes, asking him without words why he was stopping.

"I was coming too close, baby. I want you to get on the couch, with your back down."

My heart and dick both fluttered. He was going to fuck me now. "Yes Daddy!" I said excitedly and rolled onto my back on the couch. he pulled me to the edge of the couch and kneeled right by my hole. He put a finger up to my mouth and I began sucking it instinctively, which he smiled at. He then moved it down to my ass, moving the bottom of the costume out of the way, and began working my ass with his finger. Then, as he fingered me, he moved his face up next to mine and stared into my eyes. Without thought, I moved my head up and began kissing him and felt his tongue moving into my mouth and pulling me in. I moved one of my feet down to his dick and played with it to make sure it stayed hard. After a couple of minutes of this, he pulled away and moved the tip of his dick to my now somewhat opened asshole. "Are you ready, Tomi?" he asked.

"Yes daddy, please fuck me!"

"Good girl."

The tip entered with no problem, and I shuddered as it made it's way in, letting out an involuntary moan of pleasure. He began working himself deeper little by little, me moaning as his cock moved deep into me. He started going faster and deeper until suddenly, with a stop, he was all the way in. It hadn't hurt at all when he made it that far in and began touching my prostate all the way. I looked at him and bit my lip a bit before saying outright, "Please, Daddy, fuck me hard again."

He moaned and smiled. "Whatever you say, baby. I love watching your little clit dick flop around as your ass is filled with my cock."

He began thrusting again, this time all the way in. My little hard dick was bouncing against my stomach as he took my ass as his own and my legs curled over his shoulders. I pulled myself up to his face and began making out with him again as i felt my dick build up with cum. "Oh, fuck, Daddy, I'm gonna cum," I moaned into his ear.

"Me too, baby."

I kissed him again as my dick shot out a minuscule stream of cum, and a moment after, I felt Charlie's dick shudder inside me, and fill me up with his cum, blast after blast. We held each other there for a moment as we caught our breath. As he pulled his dick out of me, already beginning to shrink down (if you can call it that, with a huge dick like that), I pulled him on top of me to keep making out for another few minutes. "Okay. I have to go clean myself off a bit real quick in the shower," I said. "Do you wanna join me?"

"Yeah, yeah." he said.

I stripped down completely and our size difference once again became clear, which we both began to laugh at as I started the water. As we cleaned off, we began looking into each other's eyes, and i saw his dick start to become hard again. "Can he wait a few minutes for me to dry off and put on another costume?" I asked.

"Certainly," he said. "Just not too long."

I laughed flirtatiously at that and gave him a towel, moving myself over to the mirror to start thinking about which costume to try next. "Any recommendations?" I asked.

He looked for a moment and said, "Velma."

"Oh, sexy choice," I said, and pointed him to the bedroom.

I closed the door after he stepped out and began to prepare, making my hair look a little shorter with a half pony and putting on some glasses that came with the costume. I chose a pair of leopard print thong panties, and pulled the skirt, knee high socks, and cutout sweater on. I then pulled out the black 2-inch high heels that I barely fit into, and have barely practiced walking with out and put them on. I cleaned off and reapplied the lipstick and made my way, slowly, to my bedroom.

I leaned up against the doorframe, partially because I had to with the heels, and said "Oh no, daddy. I heard you've been having trouble with ghosts. I can help with that."

He lifted up and eyebrow and snickered at that.

"Alright, I'm not the best at role play dirty talk. Just come over here and let me see that dick," I said.

He moved over to me and took out his hard cock, from under the towel he had wrapped around himself. I kneeled down, slowly again, and took it in my hand first moving it up and down, making direct eye contact and biting my lip. "Oh fuck baby, give me that mouth again," he said.

I opened my mouth and began sucking his dick, feeling my own dick lift up hard again from the feeling of taking this huge cock in my mouth. I started sucking hard, never breaking eye contact, and taking it as far down as I possibly could. I continued with that for what felt like a full minute before taking it out of my mouth and placing my face right under it, still making eye contact. I started licking the part of the shaft that I couldn't take in, and jerking him off with my hand. I moved my mouth down and started taking his balls into my mouth and sucking on them one by one, until he pulled away again and said "Bend over. I'm gonna fuck you doggy this time, Tomi."

Obediently, I bent down on all fours and felt him pull up the skirt, pull down the panties and start fucking my eager hole again, lubricated from the remnants of the cum left in there from before. He started going faster and I began to moan alternating between his name and Daddy louder and louder feeling his hard nine inches fuck me deep once again and feeling my little dick flop around. Soon, I shivered, and came on the floor, and he said "I'm gonna cum too, move your face over here."

I did as I was told and took another huge warm load of his cum on my face, smiling as each stream hit me. "Oh fuck, daddy! Yes," I said, taking as much of the cum as I could gather and putting it in my mouth, swallowing every drop I could get from my face.

"I need to shower again," I laughed, and went back into the bathroom.

When I came out, after my shower, I saw Charlie putting on his clothes and getting ready to leave.

"You're leaving?" I asked, sounding as sad as I could.

"Yeah, I, uh, We," He stuttered.

"Look. Neither of us work the next couple days. Unless you have plans you didn't tell me about we have three more outfits to try and more cum to fill me with."

"I didn't think you'd want me to."

"What? You're the first person who seems to actually like who I am and how I want to live!"

"Well," he smiled at me. "I guess I could stay."

After I pulled on some sexy pajamas I had bought on a whim, he pulled off everything but his boxers and joined me in the bed. We didn't fuck again that night but we did make out for a couple hours.

In the morning, before he woke up, I went and fixed some coffee in the kitchen, then went to put on the maid costume and start to clean. After he was up, and we both had had some coffee, he fucked me every which way in the kitchen and living room and laundry room, at least five times during that day all in the maid costume. By dinner time i was full of cum both from my mouth and ass that I ended up just making him something to eat and sucking his dick under the table.

After taking another load in my mouth, I went to shower and change, back into the sexy pajamas. I poured a couple glasses of wine and we watched a movie for a while, curled up next to each other. About an hour into the movie and 3 glasses of wine later, I looked into his eyes and moved in to make out again. He moved his hand down and started fingering my asshole, while I took out his dick and began to give him a handjob. For about ten minutes, this is how we were, him with his tongue down my throat, hand deep between my big buttcheeks, middle finger moving in and out of my ass, and me letting him take me as I moved my hand up and down his long shaft. I moved my mouth over it when it seemed like he was going to cum and took it all down again. I shuddered, from the feeling of orgasm (although my little clit dick had no cum left in it.) and he moved his finger out of my ass. We fell asleep there, cuddling on the couch.

Sunday morning, we woke up and spent the day in the usual way again. This time, I was in the schoolgirl outfit and we tried a little more BDSM-type stuff. Nothing serious, mostly handcuffs, a ball gag, and a spanking paddle. I loved the feeling of riding him cowgirl with the gag and handcuffs, and we both came from that multiple times.

In the evening, we decided to have one last big fuck before he went back to his apartment and we went to work the next day. I pulled out the sexy red lingerie. It was a full ensemble: a red corset and bralette, a lacy red thong, and red thigh high pantyhose with a garter belt. It also had a sexy red silky robe on top of all that. I did my hair the nicest I had done it so far and once again applied the lipstick. I also put on the heels to finish out the look.

We had dinner first, and while we ate, I slid my foot out of my shoe and rubbed his dick with it. He smiled and leaned back to let me give him a full footjob in the tights. I took it and rubbed it hard and eventually he came all over my feet. I moved my hand down, took whatever hadn't absorbed in yet and put it in my mouth, swallowing his cum again. We finished eating and moved into the bedroom.

"I want you to give me the best blowjob you've given all weekend, Tomi," Charlie said.

"I want that too, Daddy."

He laid on the bed face up, and I crouched between his legs and started licking all over his balls, his whole shaft, taking it in my hand and stroking it as I moved my tongue all around. I took his balls in my mouth and played with them, then started taking his dick all the way down without his thrusting. Each inch filled my throat deeper and deeper until I was all the way down. I held there for a second, licking the base of his big shaft until I had to take it out. I then sucked for another few minutes and got all the way down a couple more times before he rolled me over to fuck missionary.

I stared into his eyes as he thrust into me, fucking me deeper and deeper and all the way. He was being rough, but not too rough, gentle, but not too gentle. He moved closer to my face and we started kissing again. I moved my mouth to his ear and nibbled on it before whispering "Fuck, Daddy, I love you,"

He stopped suddenly, staring into my eyes. He didn't say anything and neither did I.

Then he started fucking me hard again. We kissed again, him moving his tongue into my mouth and me loving him, and every second of this sex.

He came deep in me, what felt like the biggest load yet. As he rolled over next to me, he said, "I love you, too."