College Sissy's First Time

******Hey guys, this is my first story I've written so I hope you enjoy. I'd really love any feedback because I'd like to continue writing, maybe. Anyways, this is a story that is based off of me taking my first BBC. I've just added a few embellishments to make it slightly more interesting*****

"These look pretty good right? I think so. Fuck it, yolo" I hit the post button and leaned back in my uncomfortable dorm chair. 19 years old and in my first semester of college I could finally explore my bi side and some of my kinks. I had heard of FetLife before but didn't make an account until now. Staring at the photos I posted, I wondered which would be the favorite; the gym bunny, the schoolgirl or the bikini in my profile pic. I was on my 4th white claw before I started fleshing out my new account, "Tags? Things I like? Uh, ok; BBC, big black cock, chastity, being a sissy, anal play..."

I typed out all the short tags as they popped into my head. I'm an aspiring sissy crossdresser who thinks about pleasing cocks, like, all day. I haven't been with a guy yet, but I've got a few toys and I'm no stranger to anal play, sucking cock or chastity. I've been practicing and I'm finally ready. "...crossdressing, cum, piss play, uncut cocks, older daddies. Ok, I think that's all I can think of right now. Fuck, I'm getting a little dizzy. This fucking website is hurting my eyes." I shut my laptop and collapse onto my bed. This is why I don't like to drink often; dizzy, about to pass out at 9:45. Besides the Fetlife account, this was a pretty normal Friday night for me. I don't like going out a whole lot and I can't keep up with my roomie and his frat bros partying all weekend.

Saturday morning came and I the first thing I do before I get out of bed is check my phone. you know, the normal shit; check the news, weather, email, bank. Just take care it all before I'm even up. That's what normally happens. This morning the first thing I see is 57 Fetlife notifications! My eyes bug out of my head. I'm as introverted as it gets so this is pretty much the most I've ever seen at once. I log in to take a look. Lots of likes on my photos, a few friends requests and even a few messages. I mean, I'm not particularly fem, mostly androgynous I guess? I'm not on HRT or anything. Just a twinky boy but I'm small and have long hair. I get lots people thinking I'm a girl at first glance. I'm 5'6" and about 145 pounds, blue eyes. Long blonde metalhead hair that goes almost touches my ass. I ran track in high school and I've become a squat-fanatic in my 2 months at college. I've got a nice sissy figure going with my flat chest tapering into a thicc booty. I've also been wearing my pink glitter Holytrainer chastity cage almost every day. I fucking love college.

Anyways, even I didn't expect this kind of response. I ran a bath and hopped in while I looked at things a bit more. First I check my real texts, "Staying at the frat until sunday. You missed out last night, bro" from my roomie. Hell yes. Perfect. Then I moved on to the Fetlife stuff. All the guys who sent me friend requests looked like creeps but there was a message that caught my eye. Sent from a MikeD100, it said "Yo what up babygirl. I want that ass on my BBC right now. You go to state? I'm a senior."

I instantly clicked his profile to check it out and he was HOT. His profile pic was a shirtless selfie in a football locker room with a huge bulge in his pants. I practically started drooling. My anxiety skyrocketed and I got super nervous thinking about a reply. This only happened last night because of alcohol. But here I was, my dream BBC telling me he wanted a fuck, and I might chicken out? I've had my cock locked up for a week now and I resolved, drunk or not, I wasn't cumming until it was with a black cock in one of my holes. "Yes sir, I'm a freshman. I'd love to take care of your big black cock." I didn't really know what else to say. I was a sissy slut presented with a BBC. I needed to finally have it.

I didn't hear back until later in the evening. I got another message on my last homework assignment, "I'm almost 9 inches. You think you can handle that, sissy boi?". I instantly respond, "Yes sir! I've done lots of practice! I've only used toys but I know I can handle you! I'll be a good girl! My roommate is actually gone all weekend, do you want to come over tomorrow around lunch and feed me your cum?" Asking an upperclassman to come to my dorm and fuck my ass? I've never been this bold sober before. I'm being driven more by horniness than courage. He responds quickly too, "alright I'll be by lunch time for that ass." I giggled with excitement as I sent him a message with my dorm and number.

It's getting late but I still get my favorite 7" pink jelly dildo and matching buttplug from my dresser. I take my toys into the bathroom and smack the suction cup of my dildo at perfect ass-level on the shower tile. I squirt some lube into my hand from a bottle on the counter and get my plug ready next. I start with a slippery middle finger, just to get the inside of my pink hole lubed as well. This is my daily plug, so my ass swallows it up as I firmly press it between my cheeks. The familiar feeling of being filled makes me smile as I turn and step into the tub. Kneeling down, the pink dong hangs even with my mouth. A good sissy trains every day. It takes about 10 minutes of blowjob practice before I'm satisfied. Satisfied that my ass is warmed up and the dildo is lubed. I stand and remove my plug to replace it with the dildo. This is also my daily dildo, and the significant volume of spit on the toy helps it glide past my ring. I gasp as my butt bumps into the shower wall and feel the toy inside me, balls deep in the initial thrust. I'm an absolute leaking mess at the end of the 15 minute training session. I refuse to cum. I was waiting for the real thing. I hopped into the shower and got everything cleaned up. I needed beauty sleep for my lunch date in the morning.

I wake up on Sunday, around 10:00, absolutely wired with excitement and immediately get my dorm cleaned up and start to get ready. I go to the bathroom and do my routine; wash hair, shave everything below the eyebrows, lots of lotion and moisturizer, makeup. He didn't say anything about what to wear, so I picked out another gym bunny outfit. a matching Pink thong and sports bra with black yoga pants. Getting dressed, I brush my hair and it goes into a messy pony tail. The last thing I need to complete my outfit is the pink butt plug. Finally dressed and ready, I check my phone, it's 11;30, and Mike had just sent me a message that says his ETA is 11;45. My anxiety jumps through the roof. I sort of panic but I take a hit off of a blunt I have stashed away and it helps me calm down. I go to the entrance living room area and start doing some yoga poses and breathing exercises. I'm dressed the part and stretching never hurts. I'm finally pretty relaxed again when I hear the *knock* *knock* *knock*.

I answer the door and immediately have to look up at the taller black man in front of me. Hes about 6'3", lean and muscular, probably about 210 pounds with his hair in a short fade. He's wearing his football sweatpants in our school colors and I swear I can see the bulge already. He's like twice my size and his dick is even more than that. Needless to say, he is just my type. "Hey Mike, come on in. Take a seat on the couch if you want." I motion towards the couch and shut the door behind him, "Do you want some water or something? I just started a blunt, do you smoke?" As he sits down on the couch he says, "While I'm here, you call me daddy. Ok, sissy boi? A blunt and some water sounds great."

"Yes daddy!" It feels weird to hear myself say it out loud but I swear I felt a drop of pre-cum leak out in sissy bliss. I fetched both and sat down next to him. I think he could tell how nervous I was, because while we smoked it was just normal conversation. How do you like the school? What's your major? Do you like any of your classes so far? Normal stuff. After about 15 minutes, daddy got serious, "Ok sissy, I think that's enough chit chat. Lose those pants and take my cock out."

I squeaked out a "Yes daddy" as I stood and took off my yoga pants. He looked me up and down a couple seconds. I noticed his eyes stopped on my groin for a split second longer. My caged package was small but my tiny thong was even smaller and it didn't hide any details. He grinned as he saw the difference in our sizes, "Goddamn. Even hotter in person. Get to work, girl."

I kneel down and place my hand on the bulge that has been stuck in my mind for the past 20 hours. My first time touching a real cock. It wasn't fully hard yet but I could feel his how thick he was. I started to rub gently and just feel the outline of it through his pants. Feeling his excitement got me even more excited, and for the first time I was aware of my own tiny penis pushing the limits of my chastity cage. Knowing that I was making him hard made me swell with sissy pride. As I reached into his sweatpants he told me, "That's it, sissy, take it out. Daddy wants to see you with his cock."

I pull it out and holy fuck. This beautiful, uncircumsized, black slab of man meat springs out and points straight at my face. I have a toy about the same size but an imitation is not the real thing. I reach out to feel it and the first thing I notice is how it dwarfs my hands. Then I notice everything else. The warmth. The smell. The thickness and how I can feel it pulsate in my grip. I slowly pump up and down, and the sight of his glistening glans emerging from his foreskin is what finally breaks my trance. I open my mouth and force the behemoth down my throat as far as I can. I gag almost instantly and pull myself off to tell him, "Your big black cock is so huge, daddy, I'll try my best!" Time for some sissy deepthroat training. After about 10 minutes of choking myself my jaw starts to tire out. For such a short practice, I can definitely fit more of his length down my throat.

Swapping from fast-paced blowjobbing to slower and more delicate ministrations, I realize that my panties are pretty much soaked through. But good sissies know not to focus on their own cocks. Worshipping the BBC the BBC that dominated my senses is my goal. I start at his tip. taking the whole thing into my mouth, I slide my tongue underneath his foreskin and swirl it around. I have a thing for foreskin, so I focused on this for a few minutes by itself. I could tell I was doing a good job while I sucked and slurped because he was letting out long growling moans.

I reach up with one hand and cup his balls. They are enormous compared to my own tiny pair. Feeling the weight of them in my hand mentally reinforced my sissy status. "This is a real man" I thought to myself. Moving on from the tip, my tongue dances across every square inch of the beast with small kisses and licks until I reach his balls. I don't hesitate and dive in. I take one dark orb into my mouth as I moan with sissy satisfaction. Big black cock is all I can see. All I can taste. All I can smell. I imagine this is what sissy heaven is like. Except with more cocks.

Once I'm satisfied with giving his balls a thorough tongue bath, I finally lean back on my knees and give myself a quick break. He uses the pause to tell me, "Bedroom. Now, sissy. I'm not ready to cum yet."

"Yes daddy! Follow me!" My eyes light up and I jump up off the floor. He gives my ass a smack as I pass, and I dance down the hallway, trying to give him a show. I get to my bed and I fall forward into doggy style, showing him my plugged hole for the first time. I hear him growl his approval as he gives each cheek a few more slaps and starts pressing onto my plug. I give a small purr back as I adjust to the sensation of another person playing with my asshole. I feel him grasp the base of my plug as he tells me, "Daddy needs a taste first, baby." I try to relax my hole and my plug comes out with a *pop*.

A taste? I wasn't sure what he meant until I felt warm breath on my slightly-gaping hole. This was certainly a new sensation. His tongue felt heavenly as he ate my ass. he licked and kissed my hole with the same care I gave his cock. I throbbed in my cage the whole time. I felt him pull back and got 2 spanks on either side of my ass, "You ready for this cock, sissy boi?"

"Yes daddy! Please! I need to feel your cock! please!" I look over my shoulder and watch him pull out a condom before he undresses. He grabs the bottle of lube off my dresser and squirts some onto his fingers, "One last thing, sissy." He said, as his middle finger slid into my ass. The lube was startlingly cool and I gave a hybrid gasp-moan at the intrusion. It only took him a few moments before he was satisfied because he stepped closer and I felt some thing that was NOT a finger bump into my hole.

"You ready, sissy? You ready for this big black cock?" I paused. This was the moment I had been waiting for, "Yes daddy!" I felt him press the head of his cock against my ass. I try to relax and breathe out as he pushed more firmly. His monster slipped past my well-stretched ring and I gasped again. With only a couple inches inside he paused, "I'm gonna start off slow, but I know you're a good girl. You'll be getting fucked hard real soon." I gave a low moan. It was partly hearing that and partly pain. It isn't too bad but I need some time to adjust. I take deep breaths and grip my bed sheets while he starts rocking, slowly, out and in. There is plenty of lube and my hole quickly opens up to accommodate him. 3 inches turns into 5, into 7. We both moan as his hips bump against my ass. His is more of a growl and than my significantly higher pitched moan.

9 inches of big black cock in my ass. He pulls back and continues to fuck me slowly. Getting me used to his full length, "Fuck yes, there we go. That's it, sissy boi, I knew this ass could take it. You're fucking tight." I only give him a moan in response as he starts to speed up. The slow fucking turns into him pistoning my ass. Face down in my sheets, I'm a drooling mess. There are strings of pre-cum leaking from my cage and I'm too cock-drunk to speak, just moan. The pain disappears and it feels fucking amazing but its only after about 10 minutes I manage to get my hips in the perfect position; every thrust starts slamming directly into my prostate. I haven't cum in a week and this just sends me over the edge. I do manage to say something, though, "Daddy! I'm fucking cumming!" I've been steadily leaking out of my cage but once I cum it explodes out. I shoot cum across my bed, each thrust from his cock sends another spurt. His grip on my hips tighten and I hear him grunting as my asshole clenches down on him through my whole orgasm. I send him over the edge. He cums aggressively and slams into my ass. He spanks me a few times while he is balls deep and he rides out his orgasm, my conquered hole trying to milk every drop.

He pulls out and I manage to turn around on the bed and face him. My eyes go straight to his cock. Still mostly erect, half of his dark shaft is obscured by the milky condom, "Daddy, I don't want to waste that. Can I have your cum please?" I don't know where that came from, but he grins, nods and says "Of course, slut, come here. I forgot this was your lunch."

I drop to my knees in front of him and stick out my tongue as much as possible. He pulls the condom off and grabs my pony tail with his free hand. Tilting my head back, he upturns the condom over my waiting mouth. His cum drips out all over my tongue and face. I'm the happiest slut in the world. He squeezes the last few drops out and tosses it in the trash. I swallow everything and I'm still kind of out of it when he grabs my pony tail again and pulls my face into his groin. "Clean it up, slut, there's a little more cum for you to get up." I hungrily suck his cock clean. He starts getting dressed again while I sit on my bed. He finishes putting on his shoes and says, "I'll see you around, sissy boi, I might bring a friend next time. I'll hit you up soon."

He lets himself out while I'm still sitting in a daze on my bed. I look down and realize I sat in the cum puddle I made all over the bed. Fuck, I've got to do laundry.