I had worked for Andy for almost two years as his assistant – or secretary if you like. I was nineteen and he was forty-six. Our relation went from strictly professional to extremely sexual only two weeks after I started my internship when I was seventeen. More about that some other time. Today I want to tell you about a business trip to New York City six months before the pandemic struck.
NYC was pretty overwhelming and exotic for a Norwegian teenager like myself and I could hardly wait to suck in the atmosphere of this massive city. I also expected to suck something else while I was there.
Andy wasn’t the classic handsome guy I had always dreamed about, but he had tons of charisma, a tight butt and an absolutely massive cock. I’ve had my fair share of dicks but absolutely no one could compare to Andy’s huge member. It is truly one of a kind..
On every single business trip we’re on we play the same game. I slip him a blue pill just before the first meeting of the day and watch him try to hide his brutal erection as the hours and meetings pass. As the effects of the pill wears off, it’s my job to try and maintain his erection until we get to a place where we can get down to business.
After three meetings on day one in NYC we hurried back to the hotel. Our room was on the 34th floor and we started making out in the elevator as soon as the doors closed. Andy’s cock was already dripping with pre-cum and a small stain was showing through his grey trousers. On the tenth floor another guy entered the elevator. He was in his mid-thirties, black, with a chiseled gorgeous face and a twinkle in his eyes. He understood the situation immediately and said to Andy: “Lucky guy!” and laughed a big and warm laugh.
The elevator suddenly stopped between two floors. The lights went out for ten seconds before they came back on.
“Don’t worry” said our new, black friend. “This happens all the time in this hotel. It’ll take15-20 minutes and we’ll be on our way up again. I’m Darren, by the way.”
“Nice to meet you, Darren,” Andy said and shook his hand.
Darren tried to shake my hand as well. He looked me in the eye and said with a big smile, “I guess your hands are too busy holding something else?” That’s when I noticed I was holding my hand firmly on Andy’s pre-cum-stained crotch.
“Oh, I’m sorry,” I said and removed my sticky hand from his crotch and shook Darren’s hand. “I’m Jen.”
“Nice to meet you, Jen,” he smiled. “You’re a lucky, lucky man, Andy.”
A voice started talking over the speaker next to the buttons in the elevator: “Hi. We’re aware of the problem with the elevator and we are on our way. There is quite a lot of traffic so it might take 20-30 minutes. Hang in there!”
I pressed the button with the picture of a microphone on and said: “I think we’ll be absolutely fine!”
I didn’t think Andy was able to get any harder but at this point his cock was practically forcing its way out of his pants. The vein in his forehead was pumping and I noticed his pulse was racing. He was beyond ready for an orgasm.
I could feel my pussy starting to drip as I was trapped in this elevator with Andy and Darren. My pussy juices were running down the insides of my thighs and I felt an intense urge to rip Andy’s clothes off. Andy looked at Darren and said: “Do you mind? The whole day has been building up to this and we were supposed to be in our room right now, so…”
Darren smiled his big beautiful smile and said, “You guys go ahead, but I ain’t going nowhere!”
Andy whipped out his beautiful cock and I could see in the corner of my eye Darren’s jaw dropping, accompanied by a small gasp. “Fucking hell, that’s a big one,” he whispered.
I let my finger catch some of the warm pre-cum and put it in my mouth. It was salty and delicious. I pulled down Andy’s pants and threw them across the elevator. I got down on my knees, lifted his cock and started sucking his balls. I could hear Darren’s whisper, “Oh fuck…”
Andy did his signature move and lifted his right leg up against the wall and asked me to lick his ass while I was down there. I loved licking his ass. It was smooth, clean and turned me on beyond belief. While I was eating Andy’s ass I caught a glimpse of Darren’s crotch. He was struggling with a raging erection while stuttering, once again “A-A-Andy… you’re so lucky…”
Andy looked at Darren and then looked at me. “Babe…shall we…?”
I knew immediately what he meant and my answer was of course a big, “YES!”
Andy looked at Darren and said, “Get undressed, Darren. Marie will make you a very happy man!”
I don’t think I’ve ever seen a man undress as quickly as Darren. It was really impressive. But not as impressive as his cock! It was way above average in length, but the thickness was unbelievable! It was as thick as a can of beer and absolutely dripping with pre-cum!
All I could think was, “How the fuck can I fit that in any of my holes?” And “I need to start trying as fast as I can because the elevator guys are on their way!”
Andy always wanted me to have sex with others. He loved both watching and of course joining in. He even liked being cuckolded if the other guy was hot enough. Darren was definitely hot enough and the setting was super sexy and felt a bit dangerous and illegal as well. But we didn’t have too much time, unless we were going to get caught!
“Go ahead babe, I know you want to. But don’t forget about me…” Andy whispered.
I took Darren’s cock in my hand. It was even heavier and thicker than I thought. I lifted his cock the same way as I did with Andy’s and started sucking his balls. Darren couldn’t believe his luck. “Fucking hell! This is so hot!”
He lifted his leg the same way as Andy and I started licking his ass as well. It was perfect! After licking his ass for about thirty seconds Andy said to Darren, “Would you like her to put a finger up there? She’s a magician with her fingers.”
Darren moaned, “Yes, please.” I slowly slid my index finger up Darren’s ass while I sucked on his balls. He was shivering. I pulled my finger out, licked it and slowly shoved two fingers up Darren’s willing ass. As I slowly fingered him I started licking the tip of his cock..
While I was doing this, Andy was stroking his gigantic dick, sitting in the corner of the elevator. “Don’t forget me,” he whispered.
I pulled my two fingers out of Darren, sucked on them for a second and gave Andy the wettest kiss I possibly could.
“Fucking hell, you guys are something special!” Darren almost shouted.
Andy looked Darren straight in the eyes and said, “I want you to fuck her. In the ass.”
I couldn’t believe my own ears. How the fuck would I be able to fit that monster cock up my ass? In an elevator? And to be honest, an elevator that might start again any minute now?
Andy pulled me close to him by pinching my nipples. “We’ll do it like we did when you were seventeen. That time in Venice…”
Darren looked puzzled but before he could ask, Andy took the command. “Just do as I tell you and you’ll experience a new level of ectasy.”
Darren nodded while stroking his thick, black, delicious cock.
“Get down on your knees and lick her asshole while you pull her ass cheeks apart. Get your tongue in there and make her really wet.”
Darren gladly obliged. It was the craziest situation. I was on all fours with my ass in the air in a New York elevator. In the corner my boss was stroking his cock and with his face buried in my ass was this beautiful stranger. At the same time, someone was on their way to try and get this elevator going again.
“Now slide one finger from each hand up her ass and slowly start stretching her ass open.”
Darren did as he was told. Little did he know that my nickname had been “The Anal Princess” so he was really impressed by the way my asshole opened up so easily. He stretched, licked and gaped me almost to orgasm. He knew his way around a girl’s ass!
I could feel my ass gape from the stretching by Darren’s fingers. “Now spit into her ass. Lube her up really good!” Darren spat and stretched, spat and stretched. I knew what was coming. Cock.
“Keep stretching, but move your head. Keep those fingers deep in her ass!” Darren did as he was told, made room for Andy. Andy shoved his cock in between Darren’s fingers and up my gaping hole.
“Do you like that honey?” he asked.
“Mmmhmmmm,” I moaned.
“How ’bout you, Darren? You like what you see?”
Darren was still fingering me and had his face three inches from Andy’s cock filling up my ass. “It’s incredible,” he moaned. “You’re so big and she’s so hot!”
“Keep stretching, Darren!” Andy commanded. His cock was touching Darren’s fingers and my asshole as he went balls deep in my nineteen-year-old ass.
Andy was pumping faster and faster. Suddenly his dick slipped out and smacked Darren straight in the face! Darren grabbed Andy’s cock and guided it back in as if it was the most natural thing to do! Andy pumped harder and harder and suddenly I felt the warm sensation of his huge load filling me up. I could feel the cum drip from my ass and onto Darren’s hands.
“Now, your turn,” Andy commanded. “I’ll give you a hand.”
Andy and Darren switched places. At this point my ass was gaping open wide. Andy used his own cum as lube when using two fingers from each hand to stretch me as open wide as possible.
“Do it!” he almost shouted at Darren. Darren guided the tip of his beer can cock towards my ass and Andy’s fingers. I could feel him fill my gaping ass to the brim. It was fucking unbelievable!
Andy said from his front-row seat to Darren’s cock, “Fucking hell, that’s massive! I’ll help you!” Andy spat at Darren’s cock to lube it even more than what Andy’s cum did. “Go on! Just push it in!”
Suddenly all of Darren’s cock went up my ass. Really deep, all the way up, balls deep. I could hear Andy gasp impressed. Both by my ass, but also by Darren’s incredible cock.
Darren didn’t last long and came in my ass after just a minute. But the amount of cum was incredible! It felt like a never-ending stream of jizz filling me up.
Both of the guys had their orgasms, but I needed mine! I commanded Darren to stick his huge cock in my mouth and told Andy to make me cum. Darren pulled out and I could hear a stream of cum hit the floor of the elevator. My ass was wide open and I needed more.
Darren’s cock tasted a mix of his and Andy’s cum combined with the taste of my own ass. I loved it! As I sucked the remaining cum from the black monster cock I felt Andy’s tongue licking my gaping asshole. After licking a cocktail of cum from my butt he slid four fingers up my gaping ass and started sucking my clit. His hand was fucking my ass really hard and suddenly I had an orgasm for the fucking history books. My body was convulsing and all I could do was scream, “FUUUUUUUCK!! from the top of my lungs. I almost passed out.
A voice came out of the speaker: “We’re here and ready to get the elevator going.”
We got dressed as fast as we could. The mirrors in the elevator were covered in steam and the air was thick with the smell of jizz, pussy and ass. Hopefully no one was coming into the elevator in the next ten minutes!
The elevator made a small jump and continued upwards. We made it without getting caught!
And then the voice came back on the speaker: “Luckily there are two cameras in the elevator… Enjoy your stay!”