Ronnie's College Secrets - Part 5
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, Ronald or Ronnie, now 19 and 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.
Quick editorial disclaimer - my stories often contain references to the smoking fetish. This one is no different.
And I guess another warning is in order. There are scenes in this chapter that involve drug use.
Please skip this chapter if the above scenarios offend.
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.
For a few days after my encounter with Sam, I'd thought of little else but our "cosplay" fuck. Sam in the Supergirl costume had been so sexy. It had been the best sex I'd encountered since my first trans girlfriend, Simone and I had broken up.
The thing was, I hadn't taken Sam's contact details. I had left my own email and cellphone contacts when I'd left Sam's apartment, but for whatever reason, I foolishly hadn't thought to get Sam's number.
I wasn't even sure I could find Sam's apartment complex. I thought about taking a drive to Humph's, the gay hangout I'd met Sam at. I suppressed the urge.
However, Friday afternoon 8 days after we met I saw an email in my Inbox that had the subject line "Hi from Supergirl". I opened it eagerly.
"Hey Ronnie. Sunday night I have a meeting planned with my friend Sherry. Sherry is a mature tranny I've had a lot of fun with in the past. She has a great house and I am going up there Sunday. If you pick me up 7pm we can go together. I mentioned you to Sherry and she'd love to meet you. Ping me back with your answer by Sunday noon. X. Sam."
I was surprised that our next meeting would involve another party. I thought about it for an hour, then I made my mind up. If I was going to get to play with Sam again, I was up for it. I hit reply and emailed Sam back.
"OK, Sam, it's a date. Give me directions to your place again. Will pick you up around 7. You got any pics of your friend? R"
Half an hour later I got another email from Sam. Subject line, "Sherry". In the email body, after giving me directions for Sunday night's rendezvous Sam signed off with "pic attached".
I opened the attached jpeg.
The photo was good quality, high res.
Sam's friend Sherry looked older, 40s I'd say, a real tranny MILF. In the picture, she was standing facing the camera.
Sherry's body shape was slim, quite toned. From her belly button, which I could see was pierced, down to just above the knee, Sherry was wearing a tight dark red rubber skirt which curved up at the front to expose her knees while hanging further down at the back to cover the top of her tight calf muscles. Sherry's slightly tanned legs were bare, and I could see two tattoos, one above the knee on the inside of Sherry's left thigh, a dark blue shadowed circular star pattern, and one on the outside of Sherry's right lower leg, a Heart and Dagger type design, in color, mainly reds and blues. There was script, but I couldn't make it out. High heeled leather ankle boots of a darker red shade covered Sherry's ankles.
On her top half, Sherry wore a tight black corset made of a shiny slightly crinkled looking fabric which had a zipper that ran up the front which enclosed what looked like a very ample pair of tits. Sherry had tits?!?!? Finishing the outfit off, Sherry had what looked like a black faux fur scarf loosely draped over her shoulders.
Facially, Sherry didn't look too bad. In that obvious tranny way, I mean you might, in the right light confuse Sherry with a natural woman. But to me, knowing Sherry had a cock, it was obvious looking at the picture Sherry HAD a cock.
The make-up was maybe a little too heavy. Eyes shadowed in contrasting silver and black, with curved thin dark penciled brows above, and thick false lashes. Rouge applied more thickly than natural, offset by white underlying dashes on each cheek to highlight the pastel red. VERY bright red lipstick with a thin black line traced around the outside of Sherry's lips to make the shape seem more feminine. Sherry's chin and jawbone were quite feminine.
From the photo, I couldn't tell if Sherry's hair was natural or a wig. A short dark asymmetric bob with a single striking flash of bright red on the longer side which covered the right side of Sherry's face slightly. The hair looked real.
I liked what I saw. I'd seen worse in tranny porn movies online. A lot worse.
Finally, I could see why Sam had picked THIS picture specifically. Sherry held her hands close together in front of her waist. In her right hand, Sherry was holding a red and white pack of Marlboros and a thin silver cigarette lighter. In her left, Sherry held a half-smoked Marlboro, emitting a thin almost bright blue smoke trail which broke up in circular loops at the left-hand side of the photo.
Not bad, I thought. Not at all bad. I was glad I'd made my mind up to go.
I pulled up outside Sam's apartment at about a quarter after seven that Sunday. When he approached the car, I was kind of surprised that Sam hadn't a bag with him. He must have seen this in my facial expression.
"Hey. I've got clothes at Sherry's. We're kind of similar size. I thought you'd want to try something different than Supergirl", Sam giggled.
"Supergirl was hot", I replied, "But I guess variety is the spice of life".
"Spice. Yeah. Well you'll see. Sherry is chili hot!", Sam replied enthusiastically. "No limits", he added. Sam seemed to be buzzing.
The drive took about 25 minutes. On the way to Sherry's, Sam and I chatted, mainly about sexual stuff. Likes and dislikes. Turn ons and turn offs. I explained a little about my smoking fetish. But Sam seemed a little disappointed when I explained I was an ass virgin, and was "Active only" with no desire to have my anal cherry popped anytime soon.
Eventually we pulled up outside a very large detached house. Sam wasn't wrong when he'd said Sherry had a great house.
Sam saw me looking the house over.
"Believe it or not Sherry was once big in finance. Some people automatically think she was a TV super hooker, or a madam, running high class TV escorts. Nope, much more boring. Maybe explains why she's so outrageous these days".
Sam paused.
"This house is worth a couple mil, easy. There's a pool out in the back garden, but this time of year it's too cold to swim. Sherry has some great parties, you'll have to come to the next one. Assuming you and Sherry hit it off. They are strictly, and I mean STRICTLY, 'invitation only' and Sherry only allows guests she's met before".
Another pause.
"The mix is pretty eclectic, roughly 30% trans, 30% admirer, 30% gay, and a few women who like to get together with trannies and gay men. Two or three swinger couples usually. Big shots from the business World, musicians, artists. Trust me, you'll never forget a Sherry party. Jesus, last one we had a five-guy fuck train with Sherry on the end of the last guy".
Sam smiled.
"I was on the front. Toot toot! Wild!".
Sam seemed to be very hyper tonight.
I parked and we headed towards the house, up a wide curved path with plush lawns on each side. I was surprised when Sam opened the front door and walked in uninvited.
"She knows we're coming, come on in", Sam gestured as the door opened inwards.
When we entered, I stopped for a few seconds. We'd come straight into a welcome area that led into a large open plan living space. To our left was a wide curved stairway leading to the second story, and under the stairway there was an open entranceway to what looked like a large room through the back.
Sam reached back and locked the front door. The decor in the living area was fairly modern, slightly sterile. A lot of whites and grays, a very large dark leather L-shaped couch faced onto an open fireplace. The couch itself looked about 10 grands' worth, it would sit 9, 10 people, easy. A very large flatscreen was positioned in a corner to the right of the fireplace. There was a large black wooden table off to the right with 6 angular chairs arranged around it.
Sam broke up my chain of thinking, tapping me on the elbow. "Playroom's through the back, come on".
We walked through the entrance way under the stairway into the back of the house. The area was wide and open, and it looked like there was a kitchen to the left. On the back wall in front of us there were 3 doors, all open. One looked to lead into a very plush looking bathroom, I could see a lot of marble, the lights were on. The door in the center of the wall led into a sitting room that was lit in a less bright purple tinge. The one on our left looked like a smallish guest bedroom, again a lamp was on in the room.
Sam prompted me through the center door.
The room we entered was subtly lit by two very plush thick free standing lamps with translucent purple fabric spherical lampshades. Again, I automatically thought of how much these would have cost. The decor in the room could best be described as "bohemian". Dark walls, I guess a very dark shade of deep purple. On one of the walls was arranged a set of thick silver bordered mirrors almost covering the wall entirely, one mirror full length, floor to ceiling, the others a variety of slightly different sized rectangles, arranged so that if you sat or stood opposite the wall you could see yourself in at least one, if not more, of the mirrors. There were a couple of plush fabric couches, what looked like an antique richly upholstered armchair, and, scattered around, at least four of those cushion type seats you sunk into. These were encased in rich wine-colored dark leather, not your cheap student beanbag type shit. The room had a strong middle-orient, Kasbah type feel, various multi-colored rugs scattered on the floor accentuating the look.
In a large crystal ashtray on a table by one of the couches I could see a smoldering Marlboro, and it was only then that I noticed Sherry to the left of the room.
"Hi boys!" Sherry exclaimed, "Glad you could make it."
"Sherry!", Sam instantly replied, "This is Ronnie".
Sherry glanced over at me, then Sam walked over to Sherry and they started a deep passionate kiss that went on for about 30 or 40 seconds.
Breaking the clinch, Sam signaled to me to come over. "Ronnie, come on over, meet Sherry".
Sherry. She was dressed differently to the photo I'd seen on my laptop.
Latex one piece bustier under which what looked like a decent pair of tits were being constricted. Sherry's shoulders and arms were fully exposed and I saw she sported another large tattoo on her upper right arm, a portrait of a naked dark-haired woman looking over her shoulder, done in a dark blue shaded style. The bustier had long rubber garter straps which were attached to a black pair of rubber stockings. Black rubber thong, tight, encasing a decent if not spectacular bulge. Patent leather black high-heel pumps.
Facially, her thick make-up look was mainly purple based. Deep purple and shiny gray eye shadow combo, light purple blusher, very dark purple lipstick with a shiny almost glitterish tinge. It was like Sherry had made herself up to fit the decor of the room.
The biggest difference from the photo Sam had sent me was Sherry's hair. Sherry was wearing a roughly cut short bleached blonde do, shaved in closely at the sides, with a longish gelled spiky top. I could see that it was Sherry's own hair, not a wig. Black quartz earrings completed Sherry's look.
Sensual. A little bit scary, but sensual. I wondered for a few seconds if I was out of my depth.
"Hi Ronnie", Sherry said with a voice rich with innuendo, "I've heard a lot about you".
This did nothing to alleviate my nervousness.
Before I could reply, Sherry gently but firmly pulled the back of my head towards her mouth and started to kiss me. Running her tongue over my lips, Sherry followed up by sliding her tongue forcefully into my mouth. I felt I had no resistance and responded wildly.
Fuck, this was some introduction.
"Ronnie, take a seat with me over here, while Sammy here gets ready. Sammy, you know where everything is next door, you choose an outfit. I got a few new wigs as well, take your time, Ronnie and I will get comfortable".
Sam smiled at me, exited via the doorway and swung right. The third room was the dressing room then.
Sherry and I sat down on one of the couches.
"OK, Ronnie. I take it you like the way I look?"
I wasn't going to split hairs. To me the look was a touch obvious, but as my stiffening dick told me, it worked. I quickly replied in the affirmative.
"Yes, I'm not bad for 45, am I?", Sherry giggled, as she ran her fingers over the inside of my thigh.
Sherry reached over and stubbed out the Marlboro in the ashtray. Picking her pack from the table along with her lighter, Sherry proffered me a smoke, which I declined, then slowly and sensuously lit another cigarette.
"I guess you have other vices", Sherry smiled. "Let's have a drink".
Sherry walked over to a small cabinet and poured 3 measures of something amber out of a decanter into 3 crystal glasses. The glasses chinked as she added ice, then she brought the glasses and put them on a table at the side of the couch we were sitting on. Sherry handed me a glass. I sniffed.
"Scotch. Johnnie Walker Blue Label", Sherry informed me.
I was thinking, I drink this and I'm going to risk a DUI. Sherry seemed to read my mind.
"Ronnie, I've got 8 bedrooms here. You can stay the night, OK?".
I don't know if it was the age difference, but I found myself reactively agreeing before I'd had a chance to think it through. I took a sip of the Scotch, felt a burn as I swallowed, slightly offset by the coolness of the ice. I could get used to this.
Taking a sip of her Scotch, Sherry eyed me intently. "So, Ronnie, you like girls with cock?".
Maybe the sip of Scotch had relaxed me a little and I found myself answering quickly.
"I guess I do. Have done since I was 16. I guess that's my thing".
"But you still see real girls, right?", Sherry continued.
I took another sip of the Scotch, a bigger sip. Less rough on the swallow this time.
"Yes, I still date. I think people expect me to. Had a girlfriend there for a couple of months, but we've kind of split up. Haven't seen her in a few weeks".
"OK. You come to my next party and I'll make sure I've got a couple of girls your age on the guest-list. You and Sammy can have fun with them, maybe. If you want".
Sherry suddenly looked up behind me over my shoulder.
"Ah, Sammy! Niiiicccce!".
I turned to see Sam walk back into the room. I immediately thought "cool" when I saw how Sam was dressed.
"Ta dah! Teen vixen!", Sam exclaimed.
Sherry purred, "Sammy, you do know I like the teen tramp look. And you've got one of the new wigs!".
Sherry switched her gaze to me, "Ronnie, Sammy's OK for you? I fucking hope she is, I'm hard, and I've been waiting all day for your cocks in my ass. Don't make Sammy get changed!"
I told Sherry and Sam the look was definitely OK for me.
Sam wore a torn football type jersey, blue, looked like an old Colts jersey. I could see number 69 on the sleeves; the area just below the chest had been cut off all the way round for a crop top effect. A bright red thong covered Sam's bulging cock and balls, and red nylon hold up stockings covered his smooth shaved legs. He was wearing the high tops he'd come in on his feet, white and red Nike's. Contrasting with the red on his bottom half, Sam wore a short cut shaggy dark and light blue tinted wig. Make-up wise, it was perfection. Light foundation, blue eye shadow, a blue / violet lipstick. Just the right side of trashy, like an inexperienced teen girl dressing up for a cock hunt in some seedy bar on her first night out. I could almost smell pussy in my mind. What I could actually smell was the smoke coming from the Camel Sam had lit in the dressing room and was now smoking.
"Let's get started", Sherry said, placing her cigarette in the ashtray as she re-arranged two of the cushion type seats so they were next to each other.
With a slightly awkward set of movements Sherry removed her rubber thong, which she literally snapped off with a twang of rubber onto the floor. I could now see Sherry's cock. Medium length, fairly fat, uncut, foreskin still covering the head. Semi hard. I guess with your tool constricted in rubber panties, getting a hard-on is not the easiest thing in the World.
"Ronnie, me and Sammy have a routine to get me warmed up. Please be patient, in a few minutes we're taking you to heaven and back. But right now, it's warm up time".
Sherry carefully reclined on her back on one of the large leather cushions.
Sammy stubbed out his cigarette in the crystal ashtray, then picked the ashtray up and placed on the floor it by Sherry's cushion chair. Sam then moved in close to Sherry, peeling his red silk thong away to reveal a very stiff thin 6-incher.
I just sat on the couch watching, mouth agape. I was getting really turned on. My cock was almost ready to burst out of my pants.
Sam glanced over. "Ronnie, get undressed. You need to be ready when we need you".
Sherry confirmed. "Take all your clothes off, Ronnie. We won't be too long".
I started to undress. I looked over at Sam and Sherry and got a surprise. A big surprise.
Sherry had taken a smallish slip of folded paper and was sprinkling a white powder on the front of her black rubber bustier, underneath her titty bulge. Sam stuck his face against the rubber surface and sniffed most of the powder in, taking two deep snorts. Sherry was sniffing whatever was left in the paper slip. She crumpled the paper up and tossed it in the ashtray near the cushion. Both Sam and Sherry looked over at me. Sherry flashed me a long smile.
"Got more if we need it, Ronnie. Poppers too".
Sam then positioned himself facing me, looking over so I could see his eyes, then bent forward and swallowed Sherry's cock. Twisting his waist to give Sherry access to his own cock, he gave out a long "Mmmmmhh" through his full mouth, as Sherry completed the 69. This was really turning me on now. Both Sherry and Sam were thrusting from their waists, fucking each other's mouth.
After about two minutes, which seemed longer, Sam and Sherry broke off. Sherry lit a Marlboro, blowing a plume of smoke in my direction. Sam seemed to know what Sherry wanted. He crawled to the edge of the couch where I sat naked and without asking wrapped his lips around the edge of my aching cock. He started moving his head up and down in a divine rhythm. Once again when Sam felt me stiffen slightly he seemed to clamp his throat muscles around the tip of my cock making me temporarily lose all sense of feeling. Sam withdrew his mouth from my cock when Sherry told him to stop.
"OK boys. Time for me to have my fun. Ronnie, I want you in my ass. Sammy, mouth duty. Chop, chop!"
Sherry turned over onto all fours, her taut ass pointing upwards at me. For her age, it seemed Sherry kept herself in shape. Sam crawled over to her, and from a small tube that was by the side of one of the leather cushions he spread a decent amount of lube onto Sherry's asshole, then slipped what looked like two fingers in. Sherry seemed to shiver slightly, and let out a soft "Ooooooh" sound.
Sam looked back at me, nodded in Sherry's direction and said, "Let's go, Ronnie".
As I positioned myself behind Sherry, I heard a muffled moan from the direction of Sherry's head. Sam had beaten me to it and he was already slowly starting to ride Sherry's mouth. My cock was still hard from Sam giving me head. I put two fingers on top of my shaft to push my hard-on away from my body slightly, then I placed the tip of my cock directly onto the well lubricated entrance to Sherry's poop tube. I moved my pelvis forward slowly and slid my cock in one long movement all the way into Sherry's ass.
I felt Sherry tense, so I initially kept my cock still, planted deeply in Sherry's hole. A louder muffled moan slipped from the area of Sam's cock in Sherry's mouth so I took that as my signal to start riding Sherry's ass. I kept it slow, deep, deliberate. Sherry seemed to be able to control her ass muscles and I felt the tight love tube which was swallowing my cock repeatedly constrict then relax.
Sherry reached forward and tapped Sam on the waist, and immediately Sam pulled his cock out of Sherry's mouth. I had kept my eyes open so saw Sam signal to me to stop pumping. I stopped on the in-stroke, so my cock was still planted deeply in Sherry's ass.
Sam told me what was next on the menu.
"Ronnie, you need to get yourself comfortable on the cushion here, Sherry likes a special kind of ass-fucking".
Sherry continued, "Ronnie, you and I are going to get romantic. Sammy here is going to get the both of us off. Just relax, I'll show you what to do".
Sam moved over to a shelf behind the couches and picked up another of the paper wraps. He headed over to where I had lain down on my back on the cushion seat. He opened the wrap and sprinkled the powder on my waist. It tickled slightly, but nothing compared to when Sherry put her face to my waist and sniffed in the white powder. Sherry finished off what remained of the powder with a deliberate slow lick, then repositioned her head down slightly and took my cock tightly in her mouth. I shuddered as she sucked on my cock HARD.
Pulling her head up, Sherry then explained what she wanted Sam and I to do.
"Ronnie, you and me are going to start off nice and slow, like boyfriend and girlfriend. I'll tell you when to slip your cock in my ass. Sammy here is then going to double up. I just LOVE two horny boy cocks in my asshole. When Sammy's in, let him take the lead. If he does this as good as he usually does he'll milk your cock with his slippery dick and you'll both fill my ass with your juicy come. You ready for this?"
I nodded I was. "Sure", I breathed.
Sherry leaned over me and started to kiss me. I threw myself fully into our passionate kissing, lifting my lips and tongue upwards, as Sherry rubbed her fat cock over mine.
Sherry bit my ear lightly, "Time for you to get back into momma's ass".
She moved up so her cock was actually pressed against my chest. Sam grabbed the base of my shaft, and took a few fast deep sucks of his own.
"Hhhhmmm" I heard Sam say from my groin, "Pre-cum. You're excited Ronnie. I can't wait to make you come".
Sherry slowly slid back down my body. The feel of her cock, her skin and then the rubber slipping down my midriff almost blew my mind. Sam gripped my cock even tighter, then Sherry presented herself at the tip. With a slight tug, Sam pulled my cock upwards and Sherry sat back. I blissfully slid back into Sherry's ass.
I let out a deep moan. How the fuck I was going to last for any length of time beat me.
Sherry edged up and down on my cock 3 or 4 times, then held herself still and leaned the top of her body forward onto me. My dick was now only half way in Sherry's hole.
"OK, Sammy, do your thing!", Sherry breathlessly commanded, her mouth so close to mine she finished off her sentence by giving me a deep tongued kiss.
"Ooooohh", Sherry groaned as she pulled her lips off of mine for a few seconds.
All I could feel was the base of my shaft being compressed as Sam slid his thin rod above mine at the entrance to Sherry's asshole. With a soft plop, Sam entered Sherry.
We were now both in Sherry's ass. Fuck, this felt amazing! Sam's penis rubbing forcefully on the underside of the head of my cock. I started to gasp and moan uncontrollably. Sherry holding her body still started to kiss and lightly bite my neck.
I kept still. Then Sam started moving slowly in and out of Sherry's ass, every stroke sending agonizing bolts of pleasure through my cock trapped in the same tight tunnel of love. I couldn't hang on. Blam! I started to spray my seed deep into Sherry's gut. I screamed in pleasure and Sherry stifled my cries by mashing her lips onto mine and forcefully thrusting her tongue into my mouth. As my orgasm subsided, I felt Sam's cock twitch and then start to pulse as several spurts of his jism joined mine in Sherry's ass.
I snapped out of my post-orgasm haze as a drop of sweat dripped from Sherry's forehead onto my cheek pulling me back into the here and now.
Sam withdrew from Sherry's asshole first, then Sherry rolled onto the leather cushion at the right of mine expelling my softening dick.
"Boys, that was delicious", gasped Sherry.
With a demure smile, Sherry continued, "But could you two be absolute darlings, and suck me off?"
Both Sam and I sidled in on each side of Sherry's cock. We took turns licking the length of Sherry's shaft, then tongued the bulging end of Sherry's cock together before I took the lead and started to up the pace with swift sucks, mouth fucking Sherry's fat cock as best I could. As I felt her stiffen I got ready to take Sherry's load.
Sam urged, "Save some for me, Ronnie".
Sherry's prick tensed then shot out a large pool of come which I struggled to hold in my mouth rather than swallowing.
As Sherry's low moans subsided, I slowly lent over to Sam, opened my mouth and we French kissed and shared all of Sherry's love juice. I swallowed what was left of Sherry's warm salty come.
Sherry was first to speak.
"Boys, two weeks on Saturday I've got my next soiree. Ronnie, you just earned yourself an invite".
Sam lit a Camel, passed the silver lighter to Sherry who sparked up a Marlboro. Sam then headed out of the room. Two minutes later I heard a toilet flush, then Sam returned carrying two damp towels.
"For you two, time to clean yourself up".
I took one of the towels and rubbed my groin clean. Sherry carefully and extensively cleaned herself up, taking extra time on her cum-soaked ass.
Sam passed Sherry and me two more drinks.
I guess I was staying the night. I was going to miss class in the morning, but at that exact point in time I didn't think too hard about it. But it was something I would soon realize I needed to fix. My Sherry situation really had the potential to spiral out of control.
To be continued.