• Home
  • /
  • Stories Hub
  • /
  • Transgender & Crossdressers
  • /
  • How James and I Started Together Ch. 02

How James and I Started Together Ch. 02

The next morning I awoke to the smell of pancakes and bacon filling the air. It was glorious. And then I remembered where I was. I was still laying in James's bed. Only, these weren't the sheets that had been there when I fell asleep. Had he picked me up and moved me out of the bed and changed the sheets? Not that I didn't mind, I mean, the sheets were covered in cum and I probably would have been stuck to them if it had dried up. Then I remembered the tampon he had put in my ass the night before. I reached down to feel for it, but the only thing i felt, was almost like a diaper inside underwear. I pulled the blanket all the way off and looked down. To my shock, I was wearing panties! When I pulled them off, I saw that there was a cum soaked maxi pad attached to them. I brought it too my nose and sniffed it. It smelled of salty sweet delicious cum, and a little bit of the lube that James had used.

"Does that smell good?"

I looked up to see James standing at the door with breakfast on a platter. "You have no Idea!" I said. "I don't know which smells better, your cum or your cooking! I guess I'll just have to try both and see."

"I'm sorry I had to put those panties on you. It's the only thing I had that would hold the maxi pad close enough to absorb all the cum." He said.

"It's ok! I don't mind...really! They felt soft on my skin, I kinda liked it. I noticed you changed the sheets too. How'd you get me out of bed?"

"Well, after I left the room last night, got fresh sheets and came back in, you were already asleep. Sleeping pretty deeply too. So, I moved you to the sofa for a minute, changed the sheets and wiped all the cum off your legs. That's when I noticed that the tampon was leaking from all my cum in you, so I grabbed a maxi pad, put it in a pair of panties, pulled them up your legs, and carried you back in here."

"Wow, you did all that for me?" I asked.

"Yea, I kinda felt bad for taking you bare back without telling you. But like I said, We can go to the clinic and we'll both get tested. But I promise I'm clean! I got tested just last week. See! Here are my test

results."

I picked up the paper. After scanning it for a minute, I found what I was hoping to see. A list of tests done, all negative.

"James, I don't think we need to go the the clinic. This says your clean, and you were right about me. Up until last night, I was a virgin. I had never even been with a girl. I was just scared that you could have something."

"It's ok. I totally understand." He said. "Just eat your breakfast! I cleaned up your clothes for you. They're in the bathroom on the counter. Feel free to take a shower. There's fresh towels in there too."

"Thanks." I mumbled. "The breakfast does look really good."

"Well, eat up. I'll be in the living room whenever you're ready for a ride back."

I quickly ate the meal and then set the tray down on the night stand. I got up and went into the bathroom and sure enough. My clothes were there, all folded and everything. I thought to myself: "Wow, he really knows how to treat a lady right!"

Why would I think that though? What made me want to think of myself as a girl that he had slept with. I was just a normal gay guy, not a girl...right? I stepped into the shower and started to think about all that had happened. It was a refreshing shower. As I reached down to scrub my ass, I noticed that the tampon was still in. I stepped out of the shower for a minute and sat down on the toilet and pulled it out. As I pulled the tampon out, another steady drip of cum began to come out. I was in shock. He had injected so much cum in me! So much that it was still in me. I pushed the rest of it out, jumped back in the shower and finished scrubbing up nice and clean. When I shut the water off, I heard a knock on the door.

"Hey Alin, you ok in there?"

"Um, yeah... Why do you ask?

"Well, you've been in the shower for about 30 minutes. I was just coming in here to make sure that you were ok."

Had it really been half an hour? It couldn't be. Could it? "Um, yeah, I'm fine. I just lost track of time. I'll be out in just a minute."

"Ok. Well, I have to run over to my neighbors house for a minute. Will you be ok in here by yourself? I shouldn't be more than ten minutes, and I'll be right next door."

"Oh yeah, go ahead! I'll be fine. I'm just gonna dry off and I'll be out."

"Ok. I'll be right back then."

I heard James's footsteps going out of the room, and then a few seconds later, I heard the front door open, and then shut. I was alone in the house. Call me messed up, and maybe I am for doing this, but as soon as I heard his door close, I threw open the bathroom door, went out his room, and into the spare room across the hall. When I opened up the closet, I saw that it was filled with girly clothes, and all over the floor, were different sizes and styles of women's shoes.

"Oh my god!" I thought to myself. "I have to try some of these on!"

As I pulled out a pink skirt, and a white blouse, and selected a pair of black stilettos, I spun to see a short but long dresser. It was a nice looking white dresser with 9 drawers. I opened one of them, and found it was full of panties! Any color and combination I could think of! I quickly grabbed a black with white lace pair of boy short panties, and pulled them up my legs. It felt so good to have the material against my skin. I could feel my little girly penis getting hard. I opened the next drawer and found it was full of pantyhose and stocking. I grabbed a black pair and pulled them up to my thighs. I knew the next drawer had to be full of what I hoped for, and it was. I grabbed an amazingly light, cream colored bra, and laced it up on my chest. I completed the outfit and stood there looking in the mirror. MY hair wasn't particularly long, just about down to my shoulders, but I was surprised at how feminine I looked.

As I was admiring how I looked in the mirror, the reflection showed the door begin to open, and there stood the tall muscular figure of James.

"EEP!" I squeeked. "Oh my god! I'm so sorry! I had to see what was in this room, and I just couldn't help myself when I found out! Please, please, please, please, please don't be mad at me." I said as I hung my head.

James moved over and placed his hand on my shoulder, and one under my chin, bringing my gaze to meet his.

"Alin, it's ok. Honestly, I think you look great. Way better than my old roommate ever did. If you want, you're more than welcome to try as much on as you like. She left about 2 months ago, and I've been trying to get her to come back and get her stuff, but she insists that she doesn't need it because her new boy friend buys her anything she wants."

"Really? So she just left all her clothes? I asked in disbelief.

"Yeah! She just picked up one day, handed me a months share of the rent, and said goodbye and that I could keep her stuff. She left her makeup and all her feminine hygiene stuff too. It's under the sink in the main bathroom."

"Wow! So you really don't mind that I'm dressed up like this in her clothes?"

"Not at all." James said. "Personally, I think you look sexy as hell!"

"Well, I'm not gonna lie, I do feel really girly and pretty. Maybe I can try some of her makeup on for you!" I said.

" I have a better idea. How about we don't just use her, clothes. Lets see how soft her bed is."

At that, James began to slowly push me toward the bed. I felt my legs hit the bed, and I fell backwards onto it. James almost pounced on top of me when my back hit the white comforter. Our lips soon locked and we began to kiss deeply. I felt his tongue start to dance with mine as we locked lips once again. I felt my little cock getting hard in my panties, and I knew James had to be getting hard too. I tried to ease my way back onto the bed a little, and then I wrapped my legs around James' middle. His powerful midsection helped me up as we moved fully onto the queen sized bed.

Soon, we were kissing like passionate lovers and I felt his hand come up my skirt. He pulled at my panties, and slowly exposed my boy parts. I reached into his pants and grabbed his monster, and whispered in his ear as breathily as I could; "Why don't you treat me like a real girl and put this in me again?"

These must have been the words that he was waiting for, because he immediately stripped off all of his clothes. I saw the he was again not wearing any kind of underwear, because he's massive cock jumped right out of his sweat pants. His shirt was off in a flash, and I could see his massive chest muscles, veiny as they were, he was the definition of a real man. I looked down at my girlish figure, and felt inadequate. Almost as soon as I felt that though, James was back on the beed, kneeled down over me. He reached up my skirt again, grabbed the soft material of my panties and pulled them down and off my legs, and threw them on the floor.

"Are you ready baby?" He asked.

"Of course I am."

With that, he began to push at my boi pussy with the helmet of his big black cock. It was a little painful, but not quite as bad as then night before.

"Mmmmm, baby, fill me up! I need you inside me so bad!"

I felt him begin to push harder at my hole, and then pull back. Then forward, then back in again a little deeper each time. I could almost feel my hole getting moist from my juices. I knew it had to be some of his pre cum too. Soon, James was all the way inside me. Pounding me like we were the lovers we had always dreamt of being. I could feel him slide in and out of me, and I could feel how tight I still was. It felt amazing, we were in total sync with each other, I'd move down the bed, as he would thrust in, and then I'd move up, as he pulled back out. With each time his head neared leaving my ass, I'd start to feel a little empty, but then, the heavens would light up again as he rammed his cock back into my hole.

It must have went on like this for a very long time, because I noticed that James was getting sweaty. It was so hot to see him perspiring while fucking his bitch. I knew that I wanted to please this man. I wanted to drain him of his load all day, everyday.

"Baby, let me ride on top of you!" I said.

"What?"

"Let me ride it! I want to feel like a real sissy cock slave, and to do that, I have to ride your cock like a little bitch."

"Ok, lets do it." We moved to switch positions on the bed, but as we were both on our knees on, we brushed bodies and some of his sweat got soaked into my blouse. I could smell the sweet smell of manly musk on him, and as soon as he was laying down on his back, I jumped onto his cock, and began to ride it like a cowgirl. The first time I let myself completely come down on his love spear, it went deeper than it had ever gone before, and a girly moan escaped from the back of my throat.

"MMnnuuuggnaahhh!!" I moaned. Your cock is amazing in my ass hole! I have to have it!" I yelled.

"It's all yours baby!" He yelled back. "Take it all into your amazing pussy!"

He began to thrust up as my body would sink down onto his, making his dick go ever deeper inside me. Exploring depths that I had never gone to before. I leaned my body down, and I began to kiss James's chest, as his cock rammed in and out of my hole. Before long, I couldn't help myself, with the smell of his musk, his cock hitting my "g"spot, and the feel of the woman's clothing I was wearing.

"Oh god James! OH GOD I'M CUMMING!! MMMMMMM EEEEH AAHH!!"

I began to spurt little drops of cum out of my cock onto James's stomach. This must have send James over the edge too. I felt my ass hole get smaller, or his cock get bigger, as it filled up with semen. Suddenly, I felt him erupt like a volcano in my ass pussy. Just like the last time, it felt like a fire hose filling me up with sweet sticky seed. As it began to flow out of my hole, I quickly jumped up off of him. I stood up, moved back one quick step on the bed, I kneeled down and took his cock into my mouth. It was the first time I had ever tasted a real cock, and to have it still flowing over with cum, made it perfect. I quickly worked to swallow as much as I could. I felt the gooey load oozing down the back of my throat. When it finally stopped, I went to work gathering up all the cum that had leaked out between when it exploded in my backside, and when I devoured it like a hungry cum slut.

Before I could finish cleaning James's cock, balls, and the bit of cum that had run down his musky crack, I felt myself start to leak his precious seed out of my hole. I clenched up as much as I could, but there was just too much, and it ran down my leg anyway.

"Do you want me to go get you a tampon my slutty little girl?" James asked me.

Mmmmnn baby, please do. I don't want to loose all this. The thought of wasting your jiz is unbearable."

"Believe me, none of it is wasted if it goes in your pussy."

With that, James left the room for a minute, and came back with a box of tampons, and a package of maxi pads. I took out a tampon, and slid it inside me, pressed the plunger in, and felt the tampon slide out, and into my cum soaked colon. James picked up the pair of panties he had pulled off of me earlier, and handed them to me. I graciously accepted, slid them up my week legs, just far enough to put the extra absorbent maxi pad in them, and then slid them all the way up my legs. I felt like a used sissy cum slut, and it was the best feeling I had ever had. I looked up and James and smiled.

"I think we might have to stop calling you Alin my dear."

"Oh really?!" I asked in a flirty tone. "And what should my name be then?"

"Well, I was thinking... Alison. Yeah, I think I like the sound of that. James' cum slut, Alison."

"Hmmm, actually, I kinda like it too. It's girly, and pretty, and it fits me."

"Well then Alison, it's nice to meet you. What would you like to do today?"

"Oh, I don't know, but I'm sure we could think of some things!"

  • Index
  • /
  • Home
  • /
  • Stories Hub
  • /
  • Transgender & Crossdressers
  • /
  • How James and I Started Together Ch. 02

All contents © Copyright 1996-2023. Literotica is a registered trademark.

Desktop versionT.O.S.PrivacyReport a ProblemSupport

Version ⁨1.0.2+795cd7d.adb84bd⁩

We are testing a new version of this page. It was made in 539 milliseconds