Ronnie's College Secrets - Part 1
Nifty / transgender / college
Legal stuff.
This story is fiction and is intended for mature readers only. If it is not legal to read this story in your jurisdiction, or if you are not over the age of 18, please close this page now.
This tale takes place in a Universe where the main protagonist in this story, Ronald or Ronnie, first found his love for "chicks with dicks" as a 16-year-old. Check out the teen section if you would like to read Ronald's back-story.
Quick editorial disclaimer - my stories often contain references to the smoking fetish. This one is no different.
If you enjoy accessing erotic literature on nifty, please donate to nifty at http://donate.nifty.org/donate.html. Nifty is run for us by volunteer(s) whose dedication is admirable and should be supported by all our community.
Finally, I love feedback. Feel free to email me at Ronald DOT Shearing AT yahoo DOT com.
I'd reached college off the back of the break-up of a long-term relationship with my girlfriend, Marie. I wasn't too heartbroken if truth be told. Prior to Marie, I'd had an explosive relationship with another girlfriend, Simone. Well I felt Simone was my girlfriend, but in fact Simone was actually my dorky school mate, Simon. Dressed as a girl. A very hot girl. The seed had been sown. I liked girls. But I LOVED girls with cocks.
I was confused at that time. As a 16-year-old, I had been unable to come to terms with my feelings for a girl who was not really a girl. To some extent I was ashamed. And the pressures of regular teenage life and keeping an affair of that type secret killed the relationship before it was meant to end, I think.
But I could not get rid of my desires, and towards the end of my relationship with Marie, my natural female girlfriend, I'd found myself fantasizing about girls with cocks as we fucked. Marie couldn't be persuaded to try anal. So, I was quietly relieved when Marie headed off on a European trip prior to college, and we'd agreed to split. By agreed, I mean she suggested it, and I agreed. Sounds better than being dumped.
My first Romantic experiences at college were with natural girls. But the feeling that something was missing kept gnawing away at me, and I found in my spare time I was diving deeper and deeper into tranny/shemale porn. And I would visit gay contact sites which had CD/TV/TS/TG rooms. Although I never quite gathered up the courage to meet. I knew of a gay bar nearby, where it was rumored cross dressers would show up on certain nights, but again I lacked the courage to actually go there.
It ended up being my penchant for shemale porn that led to my first person- to-person trans encounter at college.
One Saturday morning I'd been browsing some shemale porn in my room before I remembered I'd arranged to meet a soccer fan friend at a local hangout that showed English Premier League soccer games live on Satellite TV. I grabbed up my laptop and headed over. I got to the place first before my friend Dominic showed up. Dominic was a massive soccer fan coming from an Italian family and we'd often watched games together. I'd been on the soccer team at High School and had gotten massively into the game. I had sat at a table and opened my laptop, then when Dominic arrived I realized I needed to piss quickly before the game on TV kicked off, so without thinking I headed to the bathroom. When I got back to the table, Dominic gave me a strange smile. My screensaver had kicked in, and I hadn't really looked at my laptop before Dominic arrived so I suspected nothing.
After the soccer match had finished, I'd expected Dominic to head straight home as he usually did, but he suggested we hang out further that day so we walked a little then sat down on a park bench.
In the afternoon sunshine in the park, Dominic came straight out with it.
"So, Ronnie, you're into shemales?"
I was shocked. I didn't know what to say. My computer. Fuck! Before I could respond, Dominic continued.
"Trannies?"
I still could only stare blankly at Dominic, my mouth slightly open.
"It's OK. I am too. I like to dress. Are you a dresser or an admirer?"
I couldn't respond, I started to speak but the words won't come out.
"I'm hoping you're more of an admirer. I wouldn't mind a dress-up friend, but I'd REALLY prefer a cute guy like you who might want to fuck me in the ass. And if you like to suck cock, that's a big bonus. For both of us".
I eventually managed to speak.
"Dominic, no you've got me wrong..."
Before I could finish, Dominic turned and looked me straight in the eye.
"Ronnie, if I've got you wrong, I've got you wrong. But I kind of expect you to visit me in my room tonight. 7pm sharp. I'm thinking you're going to show. Bailey and Gregg are away on swim team duty. I'm on my own in the house".
And with that Dominic stood up and headed out of the park.
First a little about Dominic. He was taller than me I'd say around 5' 11". Very slim, weighing about 140 lbs. He was half Italian, his mom was from Sicily, so he had a slightly darker complexion, with striking blue eyes. Very short cropped black hair. Cute face, but more masculine than I personally would have liked in a "girl". Dominic had been on the swim team, but had fallen out with the coach and was taking a break from competitive swimming. I hadn't seen Dominic without a shirt on, but it was obvious he had a thin muscular frame. Dominic also had long thin legs.
After Dominic walked off, I sat in the park stunned. I opened my backpack and took out my laptop, which I hadn't touched since putting the lid down earlier and stowing it away. Logging in I was greeted by an open but disconnected browser session. On the front of me on the main tab a hookup site, the link ending "/transgendered", on the other tabs, various links to porn, most tabs showing the word "shemale". I had been well and truly busted.
I nervously walked back to my room and wondered what to do.
At around 6:30pm I finished dressing after a long shower. I'd made up my mind to go see Dominic. I was half-kidding myself it was only to talk this situation through, but in the shower my own body had given me away as I'd fully stiffened imagining the possibilities. Resisting the urge to jerk off also reinforced my hidden desire. I wanted something to happen that night. So, I headed out fully in expectation of something happening. I really hoped so.
When I got to the place Dominic shared with his fellow swimmers, Dominic buzzed me in. As I walked upstairs I was nervous and excited at the same time. Would Dominic be dressed, or was he going to dress up while I was there? Did Dominic only wear girls' clothes, or did he wear make-up, a wig? What kind of clothes? I approached Dominic's room not knowing what to expect.
A shout emanated from an open door on my left.
"Over here, come on through!" I heard Dominic beckon me towards his voice.
I walked through the door.
First question answered, Dominic was dressed. And how.
Second question answered, Dominic was wearing make-up and a wig.
Bonus question, I hadn't even considered asking myself on the way over. I'd never seen Dominic smoking, but here Dominic was lighting a Winston from the smoky remains of one he'd smoked nearly all the way down. You see, smoking, well "girls" smoking, really turned me on. I felt it in my loins as Dominic took several short puffs to get his new Winston going.
"H. H. Hi" I stuttered.
"What do you think?" Dominic shot back at me, opening his arms and doing a slight twirl.
Where do I start? I wouldn't describe the look as natural. But it was definitely feminine, albeit a touch obvious. Tonight, I didn't give a shit. Obvious was good when you've gone as long without girl cock as I had at that point in time.
Dominic obviously knew the web address of Victoria's Secret online store.
Black lingerie. A thin satin garter belt held up a sheer pair of shiny classic black stockings. Dominic's legs showed through, and it was clear he'd shaved them, they looked completely smooth, as did the rest of Dominic's exposed tanned flesh (I found out later shaving body hair was something serious male swimmers did routinely). I could see the garter belt and straps were threaded inside a shiny black v-shaped thong that encased a large bulge. And I mean a LARGE bulge. It also seemed that Dominic had shaved his pubes smooth. A matching shiny black padded bra completed Dominic's outfit, the padding actually giving the impression of small girlish breasts even though I knew Dominic's chest was flat. I noticed there was a small dark red bow between the cups of the bra, and glancing down once more at the bulge below, I could see a matching bow at the top of Dominic's thong.
I have to say, Dominic had surprised me with his choice of wig. I'd assumed given his complexion if he'd worn a wig he'd have elected to go brunette, but, no, here was Dominic rocking a blonde longish wig, the left-hand strands of blonde hair tumbling over the front top of Dominic's left bra- strap. Dominic's make-up wasn't too heavy, maybe only his lips. Red shiny lipstick and blue eye shadow applied gently to each eyelid. No obvious mascara or false lashes. A very faint tint of rouge, but with Dominic's skin color he hadn't had to apply any foundation.
I sucked in a deep breath. Dominic had surprised me. The look was not as natural as my previous tranny girlfriend, Simone, true, but there was no mistaking it, Dominic looked good. Very good. Very fucking sexy. I felt myself starting to get stiff.
"Dominic, you look fantastic", I eventually managed to say.
Dominic took a deep inhale on his cigarette, and exhaled happily with a beaming smile, "Why thank you Ronnie".
Smiling at me, Dominic pointed to his small couch, which I could see he'd thrown a blanket over.
"Let's sit down and have a talk".
As I sat down Dominic offered me a cigarette from his blue pack of Winstons, which I declined.
"I didn't know you even smoked, Dominic", I said, sounding quite surprised.
"Oh, Dominic doesn't", Dominic answered. "But when I become a girl, I do. Maybe I smoke too much when I'm a girl. I just find it a total turn on, so slutty even. Before dad sent me to boarding school, all the slutty girls at my High School smoked. I used to use it as an indicator of the likelihood of a blow-job or a fuck when I'd hit on girls. Sounds silly, but it usually worked out that I was right. Teenage girl smokers love cock".
I was still a little nervous. Dominic was beside me on the couch, the small size of which meant we were close, but not too close. Yet.
I guess I wanted to know more, so I asked Dominic when he'd started dressing.
"Only a couple of months ago actually. I've been into Tranny porn since I was around 14, 15. I'd occasionally tried on my younger sister's panties and jerked off in them. I'd also experimented with make-up. Hell, one day it took me ages to clean up my eyes, I had to wear shades for 3 days. I was pretty sure mom knew that I'd been experimenting, but she didn't say anything so I toned down the make-up routines. When I boarded, there wasn't any opportunity to carry it on. But to this day I rarely wear eye-liner, I struggle to get it off. I did love smearing lipstick all over my cock. Still do. I used to shoplift lipsticks, the samples, and that got me through boarding school, kind of".
Dominic flicked the ash from the end of his cigarette into an ashtray on the table near the couch. Then took another pull on his Winston.
"Have to say it. Halloween is my favorite night of the year", Dominic continued. "Like, I can make myself up and pretend I'm a vampire or something from American Horror Story. I'm really making myself up as a girl facially, but telling people you're a vampire or a freak works. In fact, last Halloween was my first time with a guy when I was dressed up. Rocky Horror Picture Show".
Dominic giggled.
"Fuck that got them going, the Basque, the fishnet stockings, the trashy make-up. I was fighting them off with a stick. I ended up sucking three guys off in about 30 minutes. If I told you the name of one of them, you'd be REALLY surprised. I had to jerk myself off though, seemed these guys only liked receiving. I did see one of them afterwards, it was embarrassing, maybe I'll tell you about it one day".
So maybe there were other admirers at our college? Student? Staff???
Dominic stubbed out his cigarette, immediately lighting another.
"See? I smoke too much when I'm a girl".
Dominic laughed, and I let out a laugh as well. I was starting to relax a little.
"I get turned on by girls smoking", I confessed.
"I get turned on turning on boys who like girls smoking", Dominic cheekily responded with another big smile.
I glanced down at where the bulge was in Dominic's panties. My breath stopped momentarily.
Now clearly poking out of the top of Dominic's panties was the biggest cock I'd ever seen outside of internet porn. It had to be 10, maybe 11 inches long. And the uncut foreskin covering the head of Dominic's cock hadn't even fully exposed the purple wet glans I could see straining to get out.
"See what I mean? I bet you like to suck on a nice cock, Ronnie, right?", Dominic added with a glint in his eye.
Holding the cigarette in his lips, Dominic reached over and gently touched the back of my head, slowly directing me to where his gorgeous cock had started to visibly twitch. I didn't resist, and I let my mouth drift to Dominic's waist.
My first reaction was whether I'd be able to handle such a big cock. I gently touched each side of the bulbous head in front of me with my thumb and forefinger and fully exposed the purple glans by sliding Dominic's foreskin fully downward. Dominic let out a slight hiss through his lips as I squeezed a little bit more tightly.
I started by licking the underside of Dominic's cock head, the ran my tongue over the back of his beautiful purple helmet. Another hiss, as Dominic seemed to clench his butt checks together. Then I opened wide and took the whole of Dominic's giant shiny purple head into my mouth. Dominic let out a sudden staccato "Ah!"
This was bliss. Such a big beautiful cock in my mouth. The likes I'd never seen before in real life. I had a 7-inch cut cock I thought was OK. Which itself was now stiffening inside my jogging pants. But Dominic's uncut monster cock was something else.
Dominic grasped my head lightly. All I could smell from the side of my face was the strong smoke drifting from the side of his lit Winston he held in his fingers. This made my own hard-on start to ache even more, I was so fucking turned on, I could feel a slick wetness oozing out of the tip of my cock into my underpants.
Holding my head Dominic started to ease himself up and down in a slow rhythm, with each move I took a little bit more of Dominic's tool deeper into my mouth. I myself had started moaning in pleasure, the sound coming more from my stomach rather than my full mouth.
When Dominic's cock hit the back of my throat I gagged slightly. Fuck, he wasn't all the way in, I still seemed to be 2 or 3 inches from the base of his shaven shaft.
Dominic shafted my mouth and throat slowly. His own grunts and moans filling my ears. After a few minutes, Dominic lifted my head from his groin.
"Ronnie, let me up, I want to come on your face".
I slid down onto my knees on the carpet in front of the couch, as Dominic stood up off the couch at the same moment, and positioned himself in front of me. I noticed Dominic's shoes for the first time, black patent leather heels.
With the extra height the shoes gave to Dominic, I had to arch my neck and head upwards. The sight in front of me was making more pre-cum seep out of my cock into the inside of my jogging pants. The beautiful massive cock in front of me would flop sideways every time Dominic pulled his hand back down to the base of his shaft. He was stroking frantically with his right hand, and was cupping his own balls in his left. I suddenly saw Dominic's left hand tighten, gripping his ball sack more tightly and I knew what was coming.
"Oooooooohhhhhh FUCK!", Dominic nearly screamed, the Winston now tightly gripped between his teeth.
The first spurt of come hit my left cheek and splashed my left eye slightly, causing me to blink. Then a bigger flood of come hit the area around my mouth and chin. I'd had my mouth closed, but rapidly opened it to receive the final two warm salty spurts of Dominic's jizz. I kept my mouth wide open as Dominic squeezed the remaining milk out of his still throbbing dick onto my eager tongue.
"Ronnie, that was soooooohhh fuccckiiing good", Dominic panted. "I can't wait for part two. Tell me you didn't come in your pants?"
"No" I confirmed, "But I can't wait to come in your ass".
Dominic smiled at me. "Ronnie, I like you when you're nasty."
Dominic crushed out what remained of his Winston in an ashtray on the table near the couch. "Go and clean up, when you fuck me I need to be hard. Let's take a 15-minute smoke break".
Dominic showed me where the bathroom was. The setup of the house made it clear if anyone else was home there'd be no fucking way we'd be able to get it on like we had. Like we were about to again in a few minutes which seemed to drag as I fervently anticipated what was coming next.
In the bathroom, I licked most of Dominic's come off of my face getting the goo that my tongue couldn't reach onto my fingers so I wouldn't waste a drop of Dominic's semen. I cleaned my face up and checked myself in the mirror. Nothing had landed on my T-shirt thankfully. My cock had deflated somewhat which gave me the opportunity to piss. I flushed the toilet, washed my hands again, and headed back into Dominic's room.
Dominic was laying back on the sofa, smoking. He hadn't replaced his panties. Even soft his cock was impressive. It dangled between his legs, it looked about 6 or 7 inches soft.
On a table in front of the couch, Dominic's laptop was open, and I heard the sounds of what was obviously porn. I sat down beside Dominic and joined him in watching a Pornhub short. Large black shemale fucking a twinky guy in the ass. The tranny on the screen switched from ass to mouth, erupting soon after onto the lucky twink's face.
"You suck cock great, Ronnie" Dominic said, while we were both still watching the denouement of the movie on the laptop screen. "But you're such a cute guy, and I really wanted to see my come on your face. I really had to see that. Get undressed, I haven't even seen your hunky body yet". Dominic gave me a wink. "Go on, I've shown you mine".
I had come dressed prepared I thought. Loose grey sweat T with ripped off sleeves at the shoulder, black loose jogging pants, my best Calvin Klein boxers underneath, and trainers with no socks. I untangled myself from the T, and quickly discarded my jogging pants, boxers, and trainers. I was fully naked when I sat down.
"Let me get you ready Ronnie", Dominic said. "I need you good and hard for me. I've had a few cocks up me before, I guess it's a boarding school thing".
Dominic had gone to a boarding school for 2 years preparing for college. I'd heard the rumors about the gay sex there, and this was a confirmation.
Dominic pulled me out of my thoughts.
"Ronnie, this is a special occasion. You are going to be the first boy to fuck me as a girl".
My eyes widened in disbelief.
"No, Ronnie, it's the truth. I've blown a couple other guys since my Halloween cock binge, but I've not done the deed. Been done, I mean, when I feel like I'm a girl. I don't know why, I guess liaisons in parking lots and mens' rooms don't really make the act easy to pull off. Today's accident, me seeing your browser when you went to the bathroom before kickoff, it seems so serendipitous. I have to say, you're my type of guy. I decided right away I wanted you inside me, and I took the risk. I was pretty sure you'd say yes. And here we are. I was right".
I saw Dominic reach down to the floor and pick up his discarded thong. He straightened it out with his Winston once again dangling from his shiny red lips, then stretched the black shiny thong over the fingers of his right hand. Fuck! This was going to be good.
"Let me get you ready with these Ronnie", Dominic smiled, as he wrapped the hand enclosed in the panties around my hard-again cock, and started to slowly slide his fingers up and down my shaft.
"Don't come baby, I need all of your hot cum in my asshole".
I could only grunt and nod, and I wasn't sure I could keep my end of the deal. The soft material sliding over my circumcised cock head was like nothing I had felt before. Slightly milky pre-cum soon appeared from the tip of my rod.
"Looks like it's time, Ronnie".
Dominic removed the panties from my cock, and again stretched downwards. I could see that Dominic's monster was fully awake again. Dominic splashed lube from a small plastic bottle onto my cock (now I realized why he'd covered the couch in a blanket) taking great care to smear it on gently in case he triggered a premature ejaculation on my part. I started slightly when Dominic applied lube to his own cock. No way was I ready to take that thing in my ass, I hadn't had so much more than a tongue slipped into my anus so far during my sexual lifetime.
Dominic saw my look.
"Don't be worried Ronnie, I'm going to jerk myself off as you're fucking me. Who knows, my cock, your ass, maybe some other time?", Dominic added with a hint of excitement in his voice.
Dominic then squeezed another healthy portion of lube onto his fingers, edged his body upwards slightly and pushed three fingers under his ball sack and into his ass, swiftly frigging his own asshole with four or five jolts of his wrist.
"Ready now".
Dominic edged off of the couch then told me what he wanted.
"Ronnie, lie back slightly with your back on the back of the couch, slightly sideways like you're watching TV leaning on your elbow. In fact, look at my laptop".
I did as Dominic suggested.
"I'm going to snuggle into you facing away from you. When my asshole is close to your gorgeous dick, pinch it tightly and squeeze it into me. OK?"
I grunted a yes. I'd seen the position before in porn, but I'd never tried it.
"The way we'll do it, I can lean back and kiss you while you're fucking me. If you'd like to kiss me that is?"
At that point, I would have done almost anything Dominic suggested. "OK" I agreed.
As Dominic got ready, I felt the back clasp of Dominic's bra scrape my chest softly, then his ass cheeks rubbed against my slippery cock. Slightly arching himself up a little, Dominic made his asshole available to me. I pushed my cock forward with my fingers, Dominic then suddenly rammed his ass back into me.
"FUCK!" I screamed as in one swift movement my dick slid all the way inside Dominic's heavily lubed asshole. I was jammed against the back of the couch, but it didn't matter, Dominic started grinding his ass up and down on my penis. Up down, slight twists side to side. I started to let out low moans with each move, and Dominic had started to grunt in time with our coital rhythm. I could feel a slight shaking as Dominic pulled on his cock, then a slight pause as Dominic twisted his neck slightly and presented his tongue for me to lick. I mashed my lips onto Dominic's as we started to kiss passionately.
After about a dozen or so more thrusts, Dominic suddenly detached his mouth from mine, and leaned away slightly with a massive groan.
"Again! I'm cumming again. Arrgh! Fuck! Ronnie, keep on going, fuck me, don't stop. Aaaaahhhhhhhhhhh!".
Dominic's asshole spasmodically tightened and loosened on my cock, in time with his spurts.
My own floodgates opened.
Spurt after spurt of my come flowed into Dominic's insides.
I was moaning uncontrollably, the sounds I was making sounded barely human.
As we became still, I glanced at the laptop opposite us. Fuck. I suddenly noticed the green webcam light at the top of the lid was brightly lit.
Dominic slipped off of me.
"Dominic", I asked seriously. "Did you just fucking film this?"
Dominic just smiled. "We can delete it after we've watched it if we don't like it. Or if we decide just not to keep it. Or maybe we keep it as a souvenir of our first time together".
It wasn't my first time in the movies, so to speak. I sighed in a mood of half acceptance.
"OK, but if I say to delete it, we delete it, OK?"
"Sure Ronnie", Dominic replied. "Anything you say".
Dominic once more gave me a sexy stare.
"Let's get cleaned up. I've got another outfit I'd like to try on for you. How about we chill for a couple of hours? I've got some cold cuts in the fridge, and some cans of Coors. You up for it? Little late night action after we browse some interesting places on the web together?"
I smiled half nervously, but after no more than a few seconds thought, I replied, "OK Dominic, sounds good".
"See, I knew I could count on you, Ronnie. And when we're cleaned up there's something else I need help with"
I once more looked at Dominic with a slight frown.
"Ronnie, I need you to help me find a girl's name. Maybe something exotic, 'Ayeesha' or something like that, or ...".
I interrupted Dominic's flow.
"Fuck sake Dominic, it's obvious. Didn't you do French in High School?"
Dominic looked puzzled.
"Dominique", I said, "Dominique. D. O. M. I. N. I. Q. U. E. It's French. Dom-inn-eeeek"
Dominic smiled at me.
"Ronnie, you clever bastard! You sexy clever bastard!".
"Dominique" then moved close to me, gave me a long slow kiss, broke off slowly, and headed to the bathroom.
To be continued.