I watched as two beautiful women waddled their asses past me as I sat at the bar. One of them was in her forties, but she was still good-looking for her age. I was about to start my junior year of college as a Hospitality major. The thought of taking a few years off before I started searching for jobs in my field did cross my mind. I thought about being one of those cute girls in the tight dresses. I’d fill it out pretty well. I was still a student-athlete.
“Damn. That ass,” a man said near me.
“Which one?” another asked.
“Both!” the first man laughed.
I turned to look. Our eyes met when they realized I overheard their crude comments. They were both pilots. The first man was older. Maybe fifty years old. He had a clean haircut with dark and gray hair. He was very handsome, and he nearly melted me with those piercing blue eyes. His name tag said, “Wade.”
The second man, Cunningham, looked to be in his early forties. He only had a few grays, and his light brown hair was bigger, if that makes any sense. It’s funny that the younger guy had an older man’s hairstyle. But he had a handsome gaze, with his dark brown eyes. Despite his last name, I suspected he was biracial. Either Indigenous or Asian. I won’t lie. Wade definitely had more confidence. His shoulder things were more decorated. The Captain, I guessed. Despite my looks, I never attracted the attention of the star quarterback. The way he looked at me, that teenage girl deep inside of me wanted that.
“I apologize,” Wade said. “I know we’re falling into that stereotype.”
“We don’t actually have sex with each other often,” Cunningham added. “With the flight attendants, I mean. With a few exceptions, most of them are older than TV shows, married, and tired all the time.”
I smiled at them, not really offended at all. Then I admitted, “Honestly, I was kind of gawking at them, too. I’m Brianna, by the way.”
I told them a bit about my story: school and my thoughts about maybe becoming a flight attendant. Matthew Wade, as I learned his full name, went into an ad spiel about how amazing it is, and listed several benefits. All of which I was already aware of. But it was nice hearing him be enthusiastic.
After a while, I said, “Well, I guess the only thing that’s still making me hesitate is the lack of social life. So, really? You don’t have a lot of sex?”
Brandon Cunningham stuttered something, but Matthew Wade totally got my hints. He cut Brandon off. “What time do we need to be in the cabin?”
Brandon answered, and then my eyes went wide. I finally noticed their jackets had the logo of my airline. “Flight 1635?” I asked. Then I grabbed his phone that was sitting on the bar counter.
A surprised look came across their faces, and a little smirk from Matt Wade. “We have a twenty-six-hour layover before our next flight when we land.”
I finished putting in my phone number and slid it back to him. “Let me know where to meet you.”
“Which one of us?” Brandon asked.
“Both of you.”
The sound of his voice saying, “This is your captain speaking,” nearly set me off. I was wet the entire flight. After a few hours, we landed. The doors weren’t even open yet when I received the text to meet them in Terminal A. I don’t think they wanted to be seen walking with me. But I told Matt that I’ll be waiting by the nearest bathrooms after we exit. He sent a smiling emoji and agreed. Honestly, I wanted people to see us, and I wanted them to know exactly what was about to happen.
They both stood by the cockpit door to thank every passenger for flying with them. They both gave me knowing smiles. The moment I was out, my cool-girl act went away and I ugly ran to the bathroom. Not only did I need to go really bad, but I wanted to change. I was afraid it was in my checked bag, but I was happy to find my little black dress in my carry-on. I last wore it when I broke up with my boyfriend a few months ago.
I composed myself so that I didn’t look like I was just scrambling, and gracefully walked out of the bathroom in time to catch Matt and Brandon. Then they escorted me, and I took the walk of pride all the way to bag pickup.
They were gentlemen and let me rinse off first. I took my dress off in front of them, left the door open, and then showered in front of their lusting eyes.
“Holy shit,” Brandon gasped upon seeing my unhindered body. I was pretty proud of my body. I worked hard for it. As a lacrosse player, I ran a lot, so I had toned legs and the kind of ass men sought. I wasn’t a bodybuilder, exactly, but my shoulders were defined. I had a lot of core strength. I wasn’t ripped with a six-pack, but I had creases near my obliques and a beautiful line that traveled from just below my breasts to my belly button.
It was good to know they were comfortable around each other. Actually, Brandon showed signs of being bisexual, and Matt seemed unbothered by it. Brandon had a slight tint to his body and a good-sized penis. Matt was a bit on the pale side, but despite his age, he was still athletic, like an action movie star in his early fifties. And then there was his cock. It was veiny, and quite long. I couldn’t wait for that to be inside of me.
After our respective rinse-offs, we stood naked by the bed together. It was a tiny bit awkward. I was so confident until this point. I just didn’t know how to get a three-way started. Matt, the leader that he was, walked up to me and grabbed my waist. Then he spun me around, presenting me to Brandon. It’s funny that I say Brandon was the younger man when he was still more than twice my age. But he became braver and touched my breasts. Then he reached down and pressed a few fingers into me.
“Oh,” I moaned at his touch. Matt stepped aside, and with his fingers still lodged in me, Brandon guided me onto the bed. I fell back. It hurt a little, but it was exciting to get tossed around with fingers inside. He started to lick my clit. Matt sat next to me. He leaned over, and I just melted the moment our tongues met. I think it took me a few years to admit it to myself, but I was actually in love with him. Don’t worry, I’m not stupid. I knew he wasn’t in love with me, but I did appreciate that he at least acted like he cared. I was about to have two cocks in me, and he was still being romantic.
As Brandon continued to work on my pussy, Matt explored my body with his tongue, his lips, and his hands. “I don’t think I’ve ever been with a woman as beautiful as you,” Matt said.
“Bullshit,” I laughed. “You were probably the Shit when you were in school.”
“I was,” Matt admitted. “But I got married too young. I should have waited for someone like you.” In that moment, I realized he was divorced. There was a subtle pale line on his finger. “I want you to suck Brandon’s dick, now.”
Brandon was on the bed, but close to one side. I was on all fours, head between his thighs, then I dove in. I licked the head of his cock, then I took him deep in one motion, nearly choking myself. Matt stood by the side of the bed. His hands slowly explored my back and my tush. Fingers entered me, and I moaned.
Then I climbed over Brandon, mounting him. I meant to take it slower and take in the moment, but the moment I had his head positioned, Matt put one hand on my outside shoulder, and his other massive hand grabbed my waist. He pulled me down.
“Oh, shit!” I whimpered. With Matt guiding me, I started rocking on Brandon’s cock. God, he felt good. I always wanted to have a threesome, but I had a steady boyfriend through most of my time in college. Everything just felt so hot. “Holy… your cock feels so good.”
I think Matt really liked just watching me. He liked watching my incredible ass jump and fall onto his first officer’s cock. My labia gripped Brandon as I pulled up. With Matt’s help, I slammed back down.
“Matthew, I need your cock, too!” I begged.
Matt got behind me. Brandon reluctantly pulled his cock out of me. I felt one of Matt’s hands on my ass. He tightly grabbed where my butt met my back, squeezed, and then the biggest cock I’ve ever had pounded into me in its entirety. The shock sent a shiver through my entire body, and I’m pretty sure I vibrated for a bit there. “Fuck!” I hollered. He didn’t fuck me fast. But when he pounded into me, it was like a slingshot. He slowly pulled out, rested with just the head inside, then BAM! He hit me so hard my ass made a smacking sound. But holy fuck, did that feel great.
Brandon scooted up, putting his cock right below my face. I sucked his cock, grunted with him inside me as Matt pounded me. Matt then started fucking me with a normal rhythm. I was in a different world now. I was happy.
“No, no, no!” I begged when I eventually felt him pull out. “I want you. I want you to keep fucking me!” Matt laughed. I felt his penis against me again, but this time at my ass. “Oh, fuck…”
But I didn’t resist. Brandon knew better than to have me suck him more at this point. We were all just waiting for—
“FUCKING CHRIST!” I shouted. Matt only fucked me with half his cock. It hurt, but then my body relaxed. He slowly pushed more inside of me. It felt amazing. I was getting ass fucked. His second stroke was slow, and he only pushed about two-thirds in before he pulled out. “No. I want you to do that thing you did to me, again. Fuck me. All of you at once. I want you to just pound it all—MOTHER FUCKER!!!”
Well, I asked for it. And then Matt fucked me hard in the ass. Literally, like no one ever has. After a bit, Brandon had his turn. I adjusted to him easier, and it felt fantastic.
“Oh, my god, Brandon! Yes. Fuck. What is… Oh! Oh. Ooohh! FUCK! Aaahhh!” I squealed during my first anal orgasm. “Don’t stop fucking me! Keep! FUCK! Arrgh!”
My body tensed. I stopped sucking Matt at this point, obviously. I just fell face-first onto the bedding. I stuffed some blanket in my mouth and bit down. I yelled muffled profanity.
“Oh…fuck…” I gasped after my orgasm passed. Brandon relented at just the right moment, paying close attention to my reactions.
“No!” I shouted suddenly. “I didn’t get you guys to cum, yet!”
“I told you she blacked out,” Matt laughed.
“You were only out for like thirty seconds,” Brandon said. “But holy fuck. I’ve never done that to a woman before. That was awesome.”
I was splayed out belly-down on the bed. My body went numb. I wasn’t sure if he was talking about anal or making a girl cum so hard she blacked out.
After a good laugh, I started sucking their cocks again, and then straddled Matt. I nearly came just feeling him inside me again. I rode him for a few moments, enjoying every inch of him. Then I felt Brandon poke his cock around my ass again. I turned, and he smiled at me. I turned back to Matt with a shocked face.
“We’ll stop this if you want,” Brandon said behind me.
“No,” I said. I smiled wide. “I mean, yes. I want you both in me. Holy shit. I can’t believe this is happening. This is amazing.”
“We haven’t double-fucked you yet,” Matt laughed. “Hold your praise until you actually feel it.”
Matt was about halfway through his sentence when Brandon started pushing his cock into my ass. Now that I knew I could cum from anal sex, I was excited at the prospect of having a cock in my pussy and my ass at the same time. With Matt’s lovely cock in my cunt, I reveled in every millimeter that Brandon progressed inside my ass. Then he was fully in me. Matt remained still as I got used to two cocks.
“Come on,” I said. “Fuck me.”
I started swaying my hips forward and back, releasing the cocks and then pushing them back in me. FUCK! That felt good. I grunted with pleasure. Two sets of hands grabbed my hips. Matt tilted his head to look past me. They never actually fucked a girl together until me, but their chemistry flying together was apparent. I matched their energy. Pulling up and pushing back was easy when we synchronized.
“Holy FUCK!” I shouted as we got into rhythm. It was slow at first, but the feeling of two cocks in me was absolutely incredible. My holes felt so tight with two cocks competing for space. Then we quickened our pace, and I got properly fucked. “Motherfucking god! Fuck! Ahhh—ahhh! Aaarrhaaah!”
I knew my screams escaped our room and into the hall. I knew both sets of neighbors could probably hear us. I didn’t care. I wanted the whole world to know that I was getting the best fuck I ever had. Brandon grabbed a breast and pulled me back. Both cocks were pounding into me hard and fast. Fuck. It felt so fucking good. I felt my pelvis getting hot. I knew something was gathering. Even before my orgasm, I knew that I would be chasing after this feeling again and again.
Here I was, getting double penetrated by two men who were both twice my age and more. But I was confident that even just one of them was better than any partner I’ve had up to this point.
Then it came. I was silent at first, almost in disbelief. My eyes went to the back of my head, then I squeezed my lids and hollered. “OH MY FUCKING GOD! OH GOD! YES!”
“Oh, god, yes!” Brandon matched me. I felt warm liquids hit me. YES! He’s cumming, too. He’s cumming in my ass! Matt groaned beneath me, and I felt his semen fill my pussy. Oh, my god. They were both cumming in me!
Even as I earned my first anal creampie, I screamed as I enjoyed my first double orgasm. Is that a thing? I’m calling it that. Orgasm by pussy and ass. Holy shit. My sounds became guttural at this point. I doubt it was sexy. I sounded like a dying zombie. And then I passed out.
I woke up two hours later. Both men were collapsed on either side of me. I couldn’t help myself, and I started sucking Matt’s cock some more. All of the slurping stirred Brandon awake.
“Round two?” he asked.
“Round two.” I smiled.
Three Years Later…
“Mandy just called in sick,” the head flight attendant said. “We have someone on standby. New girl. She’s running here now.”
We still had a few minutes left before she was considered late. Not that it would be her fault. “She doesn’t need to run,” I said.
“She’s pretty dedicated. Good kid,” Rebecca said. Then she gave me a look. “Don’t be a walking stereotype, Captain Wade.”
I laughed. “What? Hey, I don’t do that all the time. Only the hot ones.” Rebecca gave me a look. “Oh, she’s hot? How hot?”
“She’s right there,” Rebecca said.
“Mega hot,” Casey said. He was my first officer for the flight.
My eyes went wide the moment I saw her. She was even more beautiful than I remembered.
“Matthew,” Rebecca warned. “Walking stereotype.”
The new girl hopped and mockingly stood at attention, giving an equally mocking salute. “Good to see you again, Captain Wade!”
Rebecca’s eyes rolled. But Brianna and Wade’s eyes locked in.
Brianna smiled. “I’m looking forward to fucking… I mean. Working with you.”
