Roommates in the Real World (Part One)
Ft. Sydney Sweeney & Madelyn Cline
Tags: M/F/F, cons, oral, big tits, blonde, titfuck
*This story is entirely fictional and did not happen in real life or between any real people. Characters are consenting adults and this is written for 18+ adults only. The fictional writing is mine, the photos are not.* This is an AU where Sydney and Madelyn are not famous.
A light knock on Sydney's door made me jump back from her lips. It wasn't the first time her roommate Madelyn came to her door while I was over. It also wasn't the first time Sydney nudged me into hiding in the attached bathroom while she talked to the other woman.
We were a secret, Sydney and me. The university held an iron-tight policy against any interactions between students and staff. Didn’t matter if you were the school’s president or in the custodial department—no personal relationships with students. Syd also kept those pretty lips sealed about us, not willing to risk disciplinary action for coming on to a guy almost double her age.
But she and I had a spark from the first day we met on campus. It didn’t take long for me to be breaking every rule I knew, and we were secretly fucking for three months already.
“What’s up, Maddie?” Sydney asked, adjusting her shirt that I was just beginning to slip my hands beneath.
Madelyn entered the room slowly, looking at Sydney sitting against a row of pillows on her bed. “Hey, Syd.” Her somber tone was undeniable. I watched them while concealed in the bathroom, the cracked door and darkness serving as the perfect secret vantage point. Madelyn’s cropped white shirt and shorts left very little to the imagination and I let myself take full advantage of eyeing her fit body.
“I can’t believe we turn in our keys tomorrow.” Madelyn’s plump lips turned into a frown, and she dropped onto the foot of Sydney’s plushy bed. "It's our last night in this apartment and living together."
Sydney moved closer to her friend, draping an arm over the other girl’s shoulder. “Aw, Maddie. Me too. But it’s a new chapter, right? We’re graduating college and it’s about to be us versus the real world.”
“I don’t feel ready. I feel like I wasted all my time here studying and staying in.”
I was well aware that Sydney and Madelyn were very close friends. Sydney loved living with her and raved about the fun they had in the two years they had together. It never dawned on me that their graduation also meant their friendship was on the line.
“Don’t even—” Sydney scoffed. “You really let loose at that bar crawl over spring break.”
Madelyn stood up and I promptly noticed the bottom of her ass cheeks spilling from her shorts. She paced the room. “One time. One crazy night that only resulted in me waking up while hugging the toilet. It’s not like what you had. You got to experience a lot—with guys. All I got was mediocre dick from my ex. And that was almost two years ago!”
“Well, we both know you could get any guy you wanted. On or off campus, for that matter. I told you to get out there and give people chances!”
Sydney was right, Madelyn could have anybody she wanted. She was gorgeous with her naturally sun-kissed skin and long, firm legs. I was shocked to know she kept to herself so much.
Madelyn stayed quiet, still pacing the bedroom until Sydney spoke again. “Who’s saying we can’t have one last holy-fuck of a time?”
The other woman giggled and shook off Sydney’s suggestion. “We move out tomorrow. Our apartment is loaded with boxes. I wouldn’t even know where to find a nice cocktail dress to wear out.”
Sydney eyed the bathroom and I locked eyes with her in the darkness. My body stiffened over what she might be getting at. She then pulled Madelyn onto the bed with her. “I know a very easy way to make you feel better. You just have to trust me.”
“Really?”
Sydney’s voice was so confident, and when she looked towards my hiding spot again, I knew what she was about to do. I was about to become part of the solution to this problem.
“Come here,” Sydney said to me. I didn’t waste any time overthinking it. Of course I was worried it was too much. Maybe Madelyn would be the one to spill the secret or be weirded out by her best friend's idea. I’m not sure what Sydney would do if this tarnished their friendship.
I entered the bedroom, clearing my throat a little as I looked at the two young women on the bed. Madelyn jumped, her eyes flickering with confusion as she looked at me. “Who’s that?!"
I looked at Sydney to provide an answer because my hands were tied on giving that up. But all she did was snicker.
"How often are you hiding men in your room?!” Madelyn asked.
Sydney wrapped her arms around her and pulled her into a hug. “More often than you’d think.”
A smile grew along Madelyn’s lips. “You’re bad, Sydney.”
Little did her roommate know that our sexual relationship was even more forbidden than she thought.
“I’ve heard a lot about you from Syd,” I said.
Her eyes wandered up and down my body, then she looked at Sydney. “What’s your plan with all of this?”
Sydney’s eyes pierced through mine even though she was speaking to her roommate. “He’s going to fuck you. I mean, if you really want one last round of fun before we close this chapter.”
Madelyn’s teeth sank into her bottom lip. Her eyes kept landing on the crotch of my pants, and that alone was making me hard. She nodded quickly, looking back and forth at the two of us.
“I want it.”
Sydney giggled and squeezed her roommate again. This time, she kissed her on the cheek, moving down her jawline and neck. “It’s good dick, I promise. He’ll fuck you right.”
Damn. Hearing Sydney gloat about our sex was quite a highlight. I knew we had mind-numbing sex, but I wasn’t sure how much of that was just the fact I was fucking her, and how every bit of what we did was a risk. Still, I couldn’t be sure what this meant. Was Sydney going to lock me in her room while I fucked her friend in her bed? Was she going to send us out somewhere, or even join in the process?
She reached forward and stroked me through my pants. “You need to suck his cock first.”
Madelyn bit on her lip again, and then her hand met Sydney’s. I smiled down at both women, admiring their conjoined touch on my straining cock. Madelyn unzipped my pants while Sydney pulled out my shaft and balls, giving me a few strokes as she did so.
Madelyn was eager to take me into her mouth. Her warm lips sealed around my tip and she flickered her tongue along the bottom ridge of my length. A moan vibrated around me, making my eyes close for a second.
“Feels good,” I groaned.
Sydney moved her roommate’s hair out of her face and watched closely as she sucked me off. “You’re doing really well, Maddie.” She ran her hands along the other woman’s body and even dipped her hands in front of Madelyn to unbutton her shorts. “Go deeper.”
Madelyn let out a little gag as she pressed me deeper into her throat. Sydney giggled, then secured her fist around the base of me. She pumped it up and down, meeting Madelyn’s tightly sealed lips and spreading her spit further along me.
My toes curled against the floor and a few sighs slipped out of my chest. One woman stroked the one half of my cock, while the other sucked the rest. Was I dreaming?
I reached over to run my hand across Sydney’s chest, and she quickly took off her shirt. Her tits sat perched in her bra, and I took turns squeezing each side of her cleavage. Sydney cupped my balls, fingers still wet with Madelyn’s spit and gave each side a light suck.
“Does he ever?” Madelyn looked at my length, then down at Sydney’s cleavage.
Sydney narrowed her eyes at Madelyn. She knew what her friend was asking, but she wasn’t going to let her get away with not saying the words.
“Does he…?”
Madelyn fought a smile. “Does he use your? Does he fuck your boobs ever? I know it’s a porn thing, but is it real?”
Heat traveled to my face. It was as if Madelyn somehow knew one of my favorite things to do with her friend.
“Mhm.” Sydney nodded and put Madelyn’s hand on her back, centered on the bra clasp. She took the hint and pulled it, setting Sydney’s tits free from the lace constraint.
“Jeez,” Madelyn said, swallowing hard.
“You’ve never seen her tits before? I thought you two were close,” I teased her.
“Not that close. I knew I was envious of her, but…fuck, Sydney.”
Sydney’s eyes sparkled over the adoration she got from both me and her best friend. She moved forward and encompassed my length between her breasts. Buried in the warm soft skin, I ached for more.
“Spit right here,” she told Madelyn, who happily did so. I bit down hard, fighting the overwhelming sensation of Sydney’s tits suffocating my cock while Madelyn’s spit ran between them and allowed me to slip around. Madelyn looked in awe over the combination my cock lost between her best friend's tits.
If I thought about it too much, I knew I’d come, and fulfilling Madelyn’s wishes would become a bit more difficult.
“Can I…?” Madelyn asked and pushed one hand into Sydney’s right breast.
Fuck. Fuck. Fuck.
She wanted to be the one to jerk me off with Sydney’s tits. I almost couldn’t look as she took over, but I had to. I had to see her petite hands pressing into Sydney’s best assets, working them up and down and around my cock and even delivering more spit between her soft breasts.
I shook away the creeping sensation of an orgasm and noticed how unsteady my breathing was when I spoke again. “You two are…” My molars pressed together. Hard.
“Amazing? Perfect?” Sydney fluttered her eyelashes as she spoke.
My jaw ticked and I managed to say, “all the above.”
I was relieved when Sydney pulled back and released my throbbing cock from between her tits. It was so she could finally kiss Madelyn on the lips. They looked gorgeous as they kissed, with their mouths eventually parting to allow their tongues to clash. I drew in a deep breath as Madelyn’s hands settled on Sydney’s chest, holding the weight of them in her palms.
“You ready to fuck Maddie?” Sydney asked me when they parted.
I nodded eagerly, scanning her body even though she was still dressed. I was still standing at the side of Sydney’s bed as Madelyn leaned back and opened her legs. Sydney’s hand darted between them and gave her a pussy a few quick circles with her fingertips.
“Aw, she’s already so wet for you. I can feel it through her shorts.”
END OF PART ONE