Ronnie's College Secrets - Part 9
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, or 21, depending on where you are, please close this page now.
This tale takes place in a Universe where the main protagonist in this story, Ronnie, now a 19-year-old male at college, first found his love for "chicks with dicks" as a 16-year-old. Check out the teen section of nifty / transgendered if you would like to read Ronald's back-story.
Warning - my stories more often than not contain references to the smoking fetish.
If you enjoy accessing erotic literature on nifty, please donate to nifty at http://donate.nifty.org/donate.html. Nifty is run for us all 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.
After leaving Sherry's party, Gina and I were driven to Gina's apartment. When we got in I was too fucked to do anything. I had developed a splitting headache. I guess Coke and Champagne didn't agree with me. So, after sitting on Gina's couch while she smoked a couple of Marlboro Lights, we went to bed. And slept.
When we woke in the morning, well early afternoon, my headache if anything was worse. I noticed in the daylight in my sober state that it was clear that Gina was a good deal older than me. She had told me that she was 30 in a month's time, and minus her make-up, it may sound very shallow on my part, but Gina didn't look that great. I noticed dark showing in the roots of her blonde hair. I really tried to picture Gina as she had been at the party. Natural, feminine, sexy, but it simply wasn't working for me and I eventually got Gina to call me a cab without even fucking or sucking her. Luckily, I had my envelope full of cash. Gina's place was 45 miles north of my college rooms. It was an expensive ride home.
The Gina thing fizzled out before it really started. Like earlier with Simone, I had trouble admitting to myself that trans girls were what I wanted. Committing to a long-term "normal" relationship in what society felt was an "abnormal" situation was not something I could cope with at that age. Casual sex I could handle. A "proper" relationship with a trans girl I couldn't.
I got the emails from Sofia about signing up for "Delight Productions", and Gina sent me an email saying she was going to take the work and prompting me to do it too. But I thought at 19 I wasn't in the right place mentally to start working in the porn industry so even after Gina and Sofia pressed me, I stuck to my guns and said no. Plus Sofia offered a two-grand sign-on fee. It wasn't going to change my life exactly. I'd made more at Sherry's party. And given a lot of the pitches Sofia was making, almost exclusively guy-guy scenarios with me as the twink in a young/old situation, or just twink-on-twink action, I wasn't interested anyway. The last email I got suggested MILF TV / son / neighbor situations, "more to my taste" was how Sofia pitched it. But I'd realized my studies were suffering and I'd already been pulled up about non-attendance of classes, so I slammed the door shut with a final and emphatic "no". I didn't even open the "You'll regret it" email I got from Sofia.
I stopped seeing Sam after that crazy night at the party as well. I got a few obviously Coke-induced text messages and emails from him. Sam also got on my case about the porn work opportunity. It was pissing me off majorly, so I told him to stop bothering me. It struck me maybe the invite to Sherry's party had only ever been about getting me onto Sofia's roster.
I guess you could say in this case that I was actually able to show some maturity. I decided to take a break from this wild life I'd somehow fallen into, and to concentrate on my studies. I never received an invite to a Sherry party again, anyway.
I got back into the normal college way of life. I occasionally smoked some pot, very occasionally, if there was peer pressure at a party. I started dating another girl, Mandy. Things seemed to be back on the straight and narrow. But there was still one more bump in the road.
After class one Friday I was called to the College Judicial Officer's office. I was told to be there at 8pm, which I thought was late, but if you got a call to the Judicial Officer's office, you went. Regardless of the time.
Our Judicial Officer, Mr. Jackson, was a college alumnus who had starred for the swim team during our college swim team's "Golden Years" when two of our swimmers had made the Olympic Team for the LA and Seoul games. He hadn't been as good as the Olympians, but he had been All-State and still kept himself very fit. He had a thin body, it was obvious he'd been a good athlete.
Mr. Jackson had worked briefly in law enforcement, and had done some time as a paralegal before ending up back at our College about 4 years before I enrolled. He was in his 40s, tall, very athletic, shoulder length dark blonde hair, always clean shaven. A lot of the girl students had the hots for him. He looked a lot younger than he was. Mr. Jackson had married a former student who was 10 years his junior.
I wasn't too worried about the call to the office. I'd been keeping myself out of any trouble, I hadn't even driven out to Humph's for months. Sam and the people he'd introduced me to were out of my life. I'd told myself I was never ever doing Coke again, and I steered well clear of any hard drugs.
But I was curious. The only thing I could think of was that there'd been a fight at an on-campus party I'd attended the prior Saturday. Well, all it had been was some pushing and shoving, and I'd helped separate the two "combatants". Somebody got elbowed accidentally breaking it up and had broken a crown.
I went to the library to complete some assignment work as it was only 2 minutes from Mr. Jackson's offices. Eventually, glancing at my watch I noticed it was a minute to 8pm, so I gathered my stuff up and walked across the courtyard to the office.
I knocked on the door and heard Mr. Jackson's voice say "Come!".
I opened the door. Then I got a shock.
Mr. Jackson had a large office. Towards the back wall there was a large desk behind which there was an open door to what looked like his personal bathroom.
Mr. Jackson was standing, leaning slightly on the front of the desk. He faced three chairs, two of which were empty. On the chair on the left of the three sat Dominic. Fuck! What was happening?
"Sit down next to Mr. Vincent please, Mr. Shearing" said Mr. Jackson pointing to the middle of the three chairs.
Now, I was nervous. FUCK! I thought again. What was this about? Nothing good, I thought.
I walked over and sat down on the chair Mr. Jackson was indicating with the palm of his right hand.
Dominic leaned slightly towards me, "Sorry man, I dropped us in the shit, but I didn't mean ..."
Mr. Jackson interrupted, "Quiet please Mr. Vincent. Dominic. I wish to speak first to Mr. Shearing. Ronald."
I noticed Dominic's rucksack on the desk. I gulped as I also saw Dominic's laptop.
"OK. Dominic, let's put Mr. Shearing, sorry, Ronald, a little in the picture. Then we'll discuss next steps"
I was nearly hyperventilating. Fuck, I knew this was going to be bad.
"At 11am this morning a female student in the library saw Dominic watching hard-core porn on his laptop. Of course, using the college network in such an unauthorized manner is a serious offence. When word reached me I immediately requested Dominic's presence in my office. Now, when I spoke to Dominic about this, he made the case that he wasn't actually using the college network, he was playing a 'home movie'. So technically, he wasn't breaking THAT particular rule. I obtained Dominic's password from him, the threat of instant expulsion opens a few doors, and I myself viewed the offending material. Here, let me show you"
Mr. Jackson logged onto Dominic's laptop. He had a movie-player window open, nearly full-screen. He clicked on ">Play".
As I suspected. Me clearly nude on the couch, Dominic joining me dressed as Dominique, me fucking Dominique in the ass, both of us cumming. The movie stopped.
I couldn't stop myself from speaking, "Dominic you deleted it, I saw you!"
"Sorry", Dominic replied, "I got it back from my email sent-items attachment. I didn't ..."
Mr. Jackson interrupted again. "Quiet please, Dominic. I've not finished fully explaining the situation to Ronald"
I gulped. What now?
"These days it helps a lot in my position to be computer literate. Anyway, I found some other movies, I don't know why boys these days feel the need to masturbate and film themselves, it really beats me. And I found a number of what the tabloids would call 'compromising photos'. Apart from seeing that Dominic has an extensive wardrobe of women's clothes and lingerie, I found three photos in particular that I can't ignore. It's a conundrum really. And I'm afraid the three of us together must work out the best way in which we deal with the situation. Without ruining young lives. Specifically, your young lives gentlemen. And without damaging the college, and an icon of its sports program"
I knew what was coming. Mr. Jackson flicked through the Coach Enderle photos. Coach Enderle, the power behind the college swim program. Coach Enderle, who early in his career had trained swimmers to be good enough to swim in the Olympics.
Coach Enderle sucking Dominic's monster cock. Coach Enderle spilling Dominic's come out of his mouth. Coach Enderle squeezing come out of the end of his cock that Dominic was about to eat on camera.
Mr. Jackson turned to Dominic and me. Then he reached into Dominic's rucksack. It was a large rucksack, light brown fabric, had "50L" and the maker logo in black on it. Mr. Jackson started pulling the contents out.
A make-up bag. A long blonde wig. A long bright red wig. Two packs of unopened hold-up stockings. A red bra and panties. Two pairs of black lace panties, loose. A black garter belt. Two packs of Winstons, one open, and a lighter. A dildo. A pack of condoms, unopened. Some lube. The tube wasn't new. A pair of high heeled black patent leather platforms. A pair of women's black leather gloves. A loose pink latex play-dress. It looked very short. And finally, still in its pack, what looked like a lacy black bustier.
Fuck, what had Dominic been planning? Where the fuck did he carry his books?
Mr. Jackson coughed slightly, and turned back round to face Dominic and me.
"OK. Coach Enderle is a college legend. Dominic, have you ever posted these photos online?"
"N-n-n, no", Dominic replied.
"Emailed them?"
Dominic nodded his head, "No".
"Are there copies on any other devices? A zip-drive, a portable HD?"
"No"
"OK. One minute." Mr. Jackson went back to the front of his desk, retrieved something from a drawer, then turned the laptop away from us. He inserted what looked like a pen-drive, then pushed some keys on the keyboard that was obscured from us. He removed the device from the USB, turned the laptop back towards us.
He walked back round to the front of his desk, leaned back.
"OK. The FBI could get those pictures. Probably. But no-one outside of law enforcement could. No kid hacker for example"
Mr. Jackson unbuttoned his jacket.
"Gentlemen. There have of course been rumors over the years about Coach Enderle's 'particular tastes'. But the college has ways of keeping this type of thing quiet. Now, let me make the situation clear. I've made copies of your movies and pictures, Dominic. And of course Ronald, with your starring role, you may wish to ask yourself how would your mother find it if she was to watch the movie you made with Dominic?"
Before I could answer, Mr. Jackson's phone buzzed. He looked at the screen, then glanced back up at us.
"Text from my wife. She's just arrived at her mother's down in Trenton. It's a long drive, I always ask her to check in when she arrives. Two weeks free for me. Thank God. I can relax a little"
Mr. Jackson let out a little laugh to himself.
"Right. I'll sum up the situation for you. You both could cause a lot of unnecessary pain and suffering for a college institution. A college legend. But, now I've erased the pictures, it would come down to your word against a college legend's. And the college would fully support that college legend. Certainly against a couple of deviants. Likely to lie to justify their own perverted behavior. So, let's be clear, this is one thing that does not leave this room. Got it?"
I nodded. Dominic muttered, "Yes".
Mr. Jackson continued.
"You get another chance. Assuming you don't fuck up again, you finish college, you get a job, you get married, or whatever the fuck you want to do. But what happens tonight has to stay in this room. Or you are finished. Got it?"
Dominic again muttered, "Yes".
I was confused. "What happens tonight". What did Mr. Jackson mean?
"Ronald?"
I nodded.
Mr. Jackson then pointed at Dominic.
"Dominic, gather up your stuff. Quick, pick your shit up, I'll help you"
When Dominic had got most of his tranny gear picked up, Mr. Jackson walked over to the main door of his office, and turned the lock, pocketing the key.
Oh oh! What was he up to?
Mr. Jackson walked back to his desk, picked up the blonde wig and some of the remaining lingerie then motioned with his head towards his bathroom door.
"Dominic, through there. Now"
Dominic looked slightly bemused.
"Go! Now!"
Dominic went through the door.
Mr. Jackson turned to me.
"You. Stay there. Don't move from that seat"
Mr. Jackson entered the bathroom behind Dominic, then closed the door behind him. I heard the lock click shut.
I was thinking to myself, what is going on? Did Mr. Jackson have a large trash can in the bathroom? Why did he lock the door?
I really started to worry when I checked my watch and saw that Mr. Jackson and Dominic had been in the bathroom for 15 minutes. But I didn't know what I could do. Once again, my dick had gotten me into trouble. Real trouble.
20 minutes. Still in the bathroom. Were they fucking? I didn't hear any noise that suggested there was sexual activity in the bathroom. 25 minutes, I checked my watch again. No movement. Then I heard the lock click, and the door opened.
Fuck. What was this?
Dominic, now dressed as Dominique was first out.
I'd forgotten how good Dominic could look as Dominique. The blonde wig looked totally natural. The long shiny blonde hair was parted in the middle, on Dominique's left, thick long strands flowed downwards, about halfway between Dominique's chest and waist. It was clear in the months since we'd gone our separate ways, Dominique had learned the art of applying make-up. Dominique's eyebrows were thin and sleek, accentuated by eye make-up. A silver eye shadow underlay was graduated to a deep pink nearer the eye, and Dominque's eyelids were perfectly shaped underneath with a deep purple eye pencil. Dominique's eyelashes were deeply mascaraed giving a rich massively feminine look.
Dominique wore the pink latex play dress, tight round the chest flaring out slightly at the waist. Actually, the bottom part of the dress barely covered Dominique's waist, and I could see Dominique's monster cock straining against the black panties.
Finishing the look off, Dominique's smooth legs were covered to mid-thigh by a pair of black nylon hold-up stockings. I also noticed that Dominque wasn't wearing any shoes.
As Dominique stood in front of the desk where Mr. Jackson had been standing, I noticed she held an unlit Winston in her right hand, and a pink lighter in her right. She smiled at me, and blew me a mock kiss with her pouted glossed full pink lips.
What happened next was so totally unexpected I almost pissed my pants.
Mr. Jackson entered the office. For a second I thought no, there must have been a third person in the bathroom. It just didn't compute.
Mr. Jackson had transformed. He'd tucked his hair under the long curly red wig which now curled over the front of his neck and collar bone. His face looked totally different. Dominique had applied gold and green eye shadow, dark eyeliner and mascara. On Mr. Jackson's face Dominique had put on a thick tan foundation with a slightly darker shade blended in at the sides accentuating Mr. Jackson's cheek bones. Dominique had also applied a dark red lipstick to Mr. Jackson's lips, making them look fuller, more sensual. The look was provocative, not quite drag queen, but definitely more hooker than girl-next-door.
Mr. Jackson was wearing the body hugging bustier, the garter belt wrapped around his slim waist attached to the second pair of Dominique's black stockings. A smaller tighter pair of black panties enclosed a decent looking bulge between Mr. Jackson's legs. Mr. Jackson was wearing the shiny black platform shoes, which made him look about 7-feet tall.
Mr. Jackson bent down and opened one of his desk drawers, pulled something out and placed it on the front of his desk with a metallic clang. I looked over and saw an engraved gunmetal ashtray.
Mr. Jackson walked round the desk and stood next to Dominique. To my great surprise, Mr. Jackson put a cigarette to his lips. Dominique clicked his lighter, Mr. Jackson inhaled, then Dominique lit her own cigarette.
I was astonished when Mr. Jackson leaned closely towards Dominique's face and they started a slow passionate tongue kiss. I felt my cock starting to stir.
Flicking ash from the tip of his cigarette into the ashtray, Mr. Jackson turned to face me.
"So, Ronald. Dominic here says this turns you on. The sluttiness of it all. Right?" Mr. Jackson took a deep drag on his cigarette.
"Y, y, y, yes", I managed to reply.
"Good. Take your clothes off. All of them. Now. Then sit back down in the chair"
I started to peel my clothes off, and once more had trouble stripping off my boxer shorts due to my rapidly stiffening pole getting caught up in them. I laid my clothes in a pile by the side of my chair, then I sat down.
Mr. Jackson gently ran his left hand over the massive bulge in the front of Dominic's panties. Dominic almost purred. They started to kiss again, passionately. I was getting really hard.
Mr. Jackson stopped, then turned to me again.
"Ronald. Nothing leaves this room. No word about Coach Enderle, no innuendo, no tittle tattle, no anonymous letters, internet postings, nothing. Dominic, as we discussed"
Dominique moved forward, pulled the front of his panties down, as his massive cock sprung free.
"Suck it, Ronald", Mr. Jackson commanded.
I wrapped my lips round the end of Dominique's giant weapon, then totally enclosed his glans in my mouth.
Mr. Jackson approached us.
"Ronald, hold it, hold it ... ... there".
I glanced round as Mr. Jackson shot 2 or 3 photos on his iPhone.
"OK. Dominic - your turn, suck Ronald's cock. Actually, just put his cock so it's touching your lips. That's it, good"
Dominic, sorry Dominique, did what she was told. Mr. Jackson took 3 more snaps with his iPhone.
He leant back to his desk, stubbed out his cigarette, then walked round the side of his desk and locked his iPhone in a desk drawer. I couldn't see which one.
"Gentlemen", Mr. Jackson said looking at both of us.
"Before the real fun starts tonight, I want to make sure we are all clear on this. Anything to do with Coach Enderle's past. Anything that happens in this room tonight. If any of it gets out, then the photos I've just taken will find their way into my official Inbox. Probably an anonymous third party who you coerced into breaking into my office with you as part of a perverted sex game started to feel guilty and sent me the pictures. I'll rustle up this fictitious third party easily, I can think of 2 or 3 troubled students who need to keep on my good side. I'll also get the real police involved, I mean technically it's breaking and entering. Don't doubt I have the contacts. However, I think I can count on you to KEEP YOUR FUCKING MOUTHS SHUT on these matters. So, I suggest you get your mouths OPEN, and start sucking my cock. NOW".
Mr. Jackson lit another Winston, exhaled towards the ceiling, and pushed his legs and thighs forward while digging his ass onto the edge of his desk. He roughly pulled his black panties to the side to reveal a decent sized cut cock, maybe 7-and-a-half inches. I almost felt disgust at myself at how hot I thought Mr. Jackson looked. The thick make-up, the fiery red hair, the stockings, the lipstick covered cigarette, I just couldn't resist the MILF slut look.
I actually moved in quicker than Dominique, grabbed Mr. Jackson's shaft and started sucking his cock rapidly. Mr. Jackson let out a long moan. Dominique knelt down beside me, edged me to the side. I removed my hand from Mr. Jackson's cock, popped my mouth off his cock head, and put my hand on his stocking top, which turned me on massively. Dominique kissed the side of Mr. Jackson's knob with her shiny pink lips, then flicked out her tongue to lick the side of Mr. Jackson's glans. Dominique signaled to me with her eyes to do the same, so I lightly kissed the opposite side of Mr. Jackson's head and started licking. Mr. Jackson immediately tensed and started making a breathless "Aaah-ooh" sound repeatedly as Dominique and I worked our tongues on his cock, licking each side of his shaft from top to bottom.
Dominique next directed the head of Mr. Jackson's cock away from me with her index finger, and started sucking sloppily. Without thinking I started tonguing Mr. Jackson's ball sack. After about half a dozen sucks, Dominique pushed Mr. Jackson's dick towards my mouth and I took over, swallowing nearly all of Mr. Jackson's cock. I was now massively turned on.
I felt Mr. Jackson's hand lightly push me away.
"Hhhhhmmm, you definitely know how to suck cock you two. But now it's time for something different".
Mr. Jackson told Dominique to lay down on a patterned rug that covered the main space near the office door.
"Lie like you did in the movie with Ronald!", Mr. Jackson ordered Dominique.
Dominique propped herself up on her side, fidgeted slightly until her asshole was exposed. Mr. Jackson then lay down behind Dominique, then carefully moved until the tip of his cock was at the entrance to Dominique's asshole.
"Ronald, my desk, get the lube!"
I scampered over to the desk, got the tube, which was about half-full. I then got down on my hands and knees in front of both Dominique and Mr. Jackson's groins.
"A squirt in Dominic's ass, Ronald, then get my dick well lubricated too. After that, lube yourself up. We're all taking the train to the Hershey Highway together. I'll fuck Dominic. You'll fuck me. You're a better size. It's been over 20-years since I've had a cock in my ass. Dominic, you're just too big. Ronald, your cock looks a perfect fit for my hole. Quick!"
I put a blob of lube on my middle finger, and gently slipped it into Dominic's ass. Dominic shook briefly, letting out an "Ooooh". I then squirted a larger amount of lube onto my hand and gripped Mr. Jackson's hard-on, sliding my hand up and down his shaft 3 times to get it fully lubricated. Mr. Jackson also moaned quietly as I did this.
"Ronald, put the rest on your cock, hurry"
I lubed myself up then Mr. Jackson grabbed the tube out of my hands and threw it across the room.
"Ronald, I'm going to stick my cock into Dominic's ass. I'm going to hold my position until you've got behind me and penetrated me. Then when I say go, you fuck me for all you are worth. Got it?"
I said I'd "Got it".
I lay down on my side, then lifted Mr. Jackson's left leg up until the tip of my cock was at the entrance to his asshole. Feeling the smooth sexiness of the stocking top again sent shivers down my spine.
I felt Mr. Jackson push his cock forward into Dominique's asshole. Dominique let out a sudden squeal. I leaned forward, as I was about to grip the base of my shaft, my well-lubed cock just slid of its own accord into Mr. Jackson's ass. It was his turn to squeal.
We lay still for about 5 seconds, then Mr. Jackson grunted the command.
"Fuck me, Ronald. Start pumping. NOW!"
I started pumping, just as Mr. Jackson had demanded. My slippery cock was gripped tightly inside Mr. Jackson's rectum. He started to groan loudly as I slid in and out. Dominique had started a high pitched almost whining sound, broken by a short "Uh!" after each thrust from Mr. Jackson's dick.
The daisy chain fuck was going much better than I thought. We avoided any ass-cock ejections, Mr. Jackson's toned muscles keeping me tightly inside him even though my generously lubed cock was very slippery. Mr. Jackson was relying on my thrusts so he could match my rhythm. After a few minutes I felt Mr. Jackson's anal muscles start to quiver and he yelled incoherently as he dumped his seed into Dominic's gut. A few seconds later I erupted in Mr. Jackson's asshole and I also started to groan loudly, the sound driven by my orgasm all the way from the core of my body.
Mr. Jackson was the first to move.
"Ronald. Off me. Stand up."
I pulled my still twitching cock out of Mr. Jackson's ass. Then I pushed myself off the floor with my right hand, and stood up gingerly. I noticed I had a slight friction burn from the rug down my right leg.
Mr. Jackson's softening cum-drained cock had already slipped out of Dominique's anus. Mr. Jackson awkwardly tried to get up, he was having problems with the platform heels, so I reached out my right hand and helped him get back on his feet. Mr. Jackson managed to get up.
"Thank you, Ronald", Mr. Jackson taking me by surprise as he put his shiny red lips to mine and started tongue kissing me.
Dominique was last to get up. By that time, Mr. Jackson had gone back to his desk, and had lit up one of Dominique's Winstons. He exhaled then looked at the cigarette in his fingers.
"I had genuinely forgotten how much I enjoyed smoking. Coach Enderle caught me smoking once. He explained to me how bad it was for an athlete to smoke. In his bedroom one night"
He passed the lit cigarette to Dominique, then lit another for himself.
"Ronald, I'd also forgotten how joyous a cock in the ass could feel. Dominic, I need you to help get us cleaned up. If you do a good job I'll let you shoot your load down my throat before we leave. In fact, on second thoughts, with my wife out of town, you can come over to my place".
Putting his cigarette in his mouth, Mr. Jackson opened his desk drawer, and picked up the door key. Walking to the door he looked at me.
"Ronald, you can go. I expect not to see you in my office again. If I do, it will be very bad news for you. Keep your nose very clean on campus from now on"
As I walked across the courtyard outside Mr. Jackson's office building, I looked at my watch. Fuck! 10pm. And I'd been meeting Mandy at 9! I found out the next day that Mandy and I were no longer an item. She dumped me by text.
To be continued