2 comments/ 14871 views/ 3 favorites How James and I Started Together By: CrossdresserAlison77 It was a Friday night in southern California. I had been checking the Craigslist.com M4M section recently and found someone to respond too. After a long back and forth conversation, and a nervous wait, we finally met up. All he wanted to do was give me a blow job, but our night ended up going a little different. My name is Alin, and this was the first time I met James. After a semi awkward ride from the McDonald's we met at, back to his house, I finally sat down on James's couch and we began to make out. It felt kinda weird to be going so fast, but as nervous as I was, I knew it would be better to just go with the flow. James was using his tongue and also feeling me up at the same time. I started to feel him up too. I could feel him getting harder in his gym shorts, and I knew I was getting hard too. Soon I felt my hands going under his shorts and grabbing his massive cock. I opened my eyes wide and looked into his. My look of shock at how big he was, was met with a smile from James. "You want to take this back to my room?" he asked. "Oh my god, yes!" I replied. On the way back to his room, we held hands. As soon as we got in, he pushed me onto his bed and began to kiss me anew as I laid back. I reached my hand down to his crotch and began to feel his massive dick again. It had to be at least 8 inches. I had never had sex with another man before, and needless to say, I was wrapped up in the heat of the moment. I pulled his gym shorts down and realized he wasn't wearing underwear. He was ready for the night. After a bit more kissing, I asked "Do you want to fuck me? "What?" "Do you want to fuck me?" I repeated. A little louder this time. The look on his face said that he wanted to, but our arrangement was just for him to give me a BJ. But I wanted more now. I needed more now. "Um... yeah, but I'm just supposed to suck you off. Are you sure this is what you want?" "If you want to fuck me, and you have a condom, then fuck me." "Ok, give me a second." He went to his night stand and took out a tube of anal lube and a condom. I quickly stripped out of all my clothes and laid there on his bed looking at him. He stripped out of his clothes too, and I realized that I was wrong about 8 inches. It had to be at least 10, and it was thick too. This was going to hurt. He climbed on to the bed and spread my legs with his knees. He leaned down and I felt something squeeze past my tight hole. It had to be the lube. Suddenly I felt his lips around my hard 5 inch cock and he began to suck me off slightly. It was amazing. It felt so good that I almost came. "Baby, no!" I said. "Ok, I just thought it would help you relax. You are super tight down there." "I know. I've never been with a man before so its going to be a little tight." "Alright, I'll be gentle... at first." Soon I felt his massive head pressing at my tight hole. He pushed a little and the head started to penetrate me. He did go slowly at first. But as he worked his way in, and went deeper and deeper, he began to go faster. I was in a lot of pain. I reached back and grabbed his pillow and put it over my face. I bit into it to try and take my mind off of it. Bright lights of pain erupted in my vision as my tiny hole strained to take his gigantic cock. But soon, my pain turned to pleasure as my hole stretched out. I placed the pillow back under my head and began to moan like a little bitch. He sensed my pleasure and began to pound me. Harder, faster, harder, faster. I soon felt that he was up to the hilt. I couldn't believe that I was taking the whole thing. He pounded in and out of me for a good long time. It felt so good, I could feel my dick slapping back against my stomach with each thrust from James. "Mmmmm baby! you feel so good!" I screamed "Oh baby so do you! your boy pussy is so tight! I wish I didn't have this rubber on!" "I know babi, I'm sorry, but we just can't be too careful." I knew about the risks, and trust me, I wanted it bareback, but I was afraid that I'd get a disease. The pounding continued as I heard the raw sounds of man meat slamming into boi pussy. I could hear the juices sluicing in and out as his hard cock penetrated me over and over again. Suddenly, I felt James pull out and I feel a sudden sense of emptiness. I heard him say to me, " Roll over, I'm gonna take your ass pussy from behind." I complied with what he said, and flipped over to my knees. As soon as I put my face down into the pillow, and put my ass back into the air, I felt his strong hands grab my hips. In one swift motion, he pulled my face off the pillow, my hips and legs back, and his cock right into my slippery wet ass hole. Soaked in lube, he didn't have any trouble slipping back in. It felt a little different than before, but I could't quite figure out why. I didn't care though. I was in heaven. I felt like such a little sissy boy. Here I was, a skinny little white boy, getting absolutely railed in the ass by a big black man with a ten inch cock. "OH MY GOD!" I cried out. "Your cock is amazing! You have to let me suck it before you blow your load! If you can't cum in my ass, I want you to pull your condom off, and let me suck the cum out of it! "Ok slut. I'll let you know when I'm about to cum." James said in between thrusts. What happened next I did not see coming. Literally, and figuratively. Just a few short minutes after he began taking me from behind, and I had told him what I wanted to do, and where I wanted him to cum, I felt James' cock begin to swell. " OH babi! Your about to cum! Quick, pull out and let me suck it!" I said. I was so excited, having a man about to cum in my mouth after fucking me, that I felt my own little dick shoot off and spray a little bit of jiz onto his sheets. "Hurry babe! Let me suck it!" "Na, we're gonna do it how I want! MMnnnggghhhh!! AAHHHHH!!" I hear James start to climax, and I try to pull away, but James has such a strong grip on me, I couldn't get off of his massive cock. "Babi! I want your cum in me! Let me suck it quick!" I shouted. "Oh you're going to get my cum in you. You just ain't gonna swallow it!" Suddenly, I realized why it felt different doing it doggy style, rather than missionary. When he had pulled his cock out, he had pulled his condom off. I was being fucked raw dog, by a man, who I had just met. And then I felt it. His massive cock erupted in my smashed asshole. I felt the warmth of it surging up into my bowels. After it went as far in my guts as it could, the pressurized seed began to flow around his cock and out my ruined hole, dripping down my legs and his. James leaned forward and pinned me to the bed, and kept pumping his seed in me. If i had been a girl, I'd be pregnant, with or without birth control, there was so much cum. After he stopped spurting semen into me, he pulled out with a loud slurping sound. I felt the weight of his softening cock drag against my leg and smear cum and other body fluids all over it. He stood up and looked at me. "I'm sorry I did that to you. But you should know that you'll be fine. I don't have any diseases, and I could tell from the moment we met, that you were a virgin. Then, when I felt how tight your hole was I was almost positive. But when you told me you had never been with another man, I know for sure that you were a virgin" "I don't know if you're clean or not!" I said angrily. "You could have just given me AIDS! And I could have given you something from all the girls I've been with!" "Ha! You with a girl! You're more likely to Be a girl, than be WITH a girl. And trust me, you didn't get anything from me. If you want, we can go get you tested in the morning. I'll pay for it too. But if you're clean, we come back here for a little bit more fun. Deal?" "NO! No deal! I am going to go get tested, but I am going right NOW!" I shouted. I moved to the edge of the bed. I could still feel the gaping hole of an ass I had, dripping with manly seed. I moved my legs off of the side of the bed and moved to stand up. My legs quickly dropped out from underneath me. I couldn't stand up. As a lay there on the carpet, semen seeping out of me, I felt James put something in my ass. "What is that?" I asked, still angry, but starting to realize just how amazing his cock was. "I know you might not think you need it, but it's a tampon. It'll help keep all the cum that's still inside you from leaking out. If you want, I can get you to my truck and we can go to the clinic right now." "No..." I said, sounding forlorn and feeling like a jerk. "It's ok. We can go in the morning. Can you just get me back into the bed? I'm really worn out, and I don't think I can make it up there myself." "Sure" he said. "Gimme your hand." I was soon back into James' bed. I could feel the tampon slowly soaking up all the cum. It felt good. It felt girly. It was a feeling I had never had before, but I really liked it. As I lay in his bed, I started to drift off to sleep, and I had the most wonderful dreams... 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!"