Study Break Surprise
Introduction:
My girlfriend and I take a study break and find my roommate and a friend in a compromising position
I think I hit all the themes so, if you don’t like any of them, don’t read this and don’t flame me. Keep your negative comments to yourselves, please.
My girlfriend, Cathy, and I had been studying hard in the library of our small, Midwestern college when we decided it was time for a study break. Little did we know, as we headed back to my dorm for some privacy, my roommate Jason had the same idea – with his hot friend Mark.
I’d met Cathy, a petite, 17-year-old freshman with fiery red hair, during an orientation mixer the month before. We’d hit it off right away, her tight, tiny body with amazing b-cup tits and a tight ass to die for drawing my interest from the first time I saw her. She admitted her surprise that a senior was interested in a freshman.
We’d fooled around some, but I had yet to bury my rock-hard 7-inch cock in her tight, tiny pussy. She was a virgin when we met (I know, surprising at 17 in this day and age) and wanted to wait for the “right guy.”
Laughing, we entered my dormitory and headed up the stairs with Cathy in the lead, me playing with her ass and tickling her as we went. Out of breath, we stopped at the door to my room, panting as I fumbled with the key and opened the door.
Cathy was already pulling her shirt off as we burst into the room. She stopped suddenly, shirt in hand and beautiful, firm tits glowing in the half light of the room. Her mouth fell open as I rounded the corner, hearing a gasp and an “Oh, shit!” coming from the bed against the far wall.
There, on the bed, was Jason. He was buck naked, his 6-inch cock rock hard and buried inside what at first appeared to be a hot, young girl wearing what could only be described as a slutty Catholic school girl outfit – tiny plaid skirt, white blouse and matching plaid necktie. As Cathy and I watched, the “girl” rolled off to the side, letting Jason’s cock slip from “her” ass and revealing the face – and a rock-hard 5-inch cock and tiny, tight nut sack.
Shit, I thought. That’s Mark.
“Um, hey, dude,” I said. “Sorry.”
Cathy, meanwhile, had a look on her face which was difficult to describe. It was definitely part shock but, if pressed, I’d have to say there was more than a little bit of arousal in there, too. Glancing down at her still-naked breasts capped with rock-hard nipples only added to the feeling she liked what she was seeing.
“That’s really hot,” she whispered.
She dropped her shirt on the floor, leaving her in just her tiny black miniskirt and low heels, and reached out for my hand. Her eyes never left the two boys on the bed as she pulled my hand up, around her body, and placed it over her right tit. Instinct took over and I squeezed her tit and pinched her nipple. Cathy moaned and leaned back into my body.
“Dude!” Jason said. “What are you doing home? I thought you’d be in the library for hours yet.”
“We thought it was time for a study break,” I said, as I brought my other hand up to cup and fondle Cathy’s starboard tit. “Looks like you, um, guys had the same idea.”
“You’re not going to tell anyone,” Mark said. He sounded close to tears at getting caught out.
“No, dude,” I said. “I don’t care what you guys do. More power to ya.”
Mark visibly relaxed. It was quiet in the room for a second. Then Cathy shocked us by asking the question which would drastically change all our relationships.
“You guys like girls, too?” she said.
Mark’s and Jason’s mouths both dropped open. I looked down at her, my hands still cupping her b-cups, my eyebrows raised in a silent question.
“What?” she said, looking up at me. “You’re still going to get my cherry tonight. I’ve just always thought guys doing guys was really hot.”
Little did she know, I did, too. I’m very strongly – and very secretly – bisexual. I’d shared oral pleasure with a number of friends back home, beginning in about sixth grade. Most boys that age experiment with some form of homo-erotic pleasure, I believe. Most also leave it behind as they graduate to girls. I didn’t.
Nothing had ever happened with Jason in the two years we’d been roommates. I didn’t even know he rolled that way. If I had, honestly, something definitely would have. Jason is just good looking, there’s no two ways about it. Hell, in two years, we’d seen each other naked more times than I could count. I’d always thought he had a cute ass and really tight upper body.
Jason replied in the affirmative. Mark, though, admitted he was fully gay, had never been with a girl and wasn’t really interested in being with one. Then his eyes lit up.
“Jason, you still got the thing?” he asked.
Jason just grinned and climbed off the bed. He started rummaging through the closet and emerged in a few moments with his lock box. Cathy, meanwhile, worked my jeans open and dropped them to the floor, followed shortly by my boxers. My thick, throbbing cock sprung free to bob in time with the beat of my heart. Her eyes – and Mark’s – grew wide at the sight.
“Damn,” they said in unison, then looked at each other and laughed.
“Mine first,” Cathy said as she dropped to her knees.
“Bitch,” Mark replied, his grin taking the sting out of the word.
“Share?” she said.
Mark walked over, knelt beside Cathy and cupped my balls as she took the head into her mouth. Jason, meanwhile, had found the key to the lock box. He opened the lid and, with a grin on his face, pulled a strap-on from inside.
“It belonged to Jill,” he said. “She loved to shove this thing up my ass and fuck me good.”
Jill was his ex-girlfriend from last year. She’d transferred to another school at the beginning of this year. I remembered her as a hot little black-haired beauty with disproportionally-large, 36D tits which almost look out of place on her 5-foot-1 frame. I pictured her naked, the strap-on in place, ploughing Jason’s hot ass with those big puppies flopping in the breeze.
“My turn,” Mark said.
Cathy relinquished my cock and Mark, to my surprise and pleasure, swallowed me to the root on one go. My brain – and my balls – almost exploded at the sensation.
“Show-off,” Cathy said.
She stood and stripped off her few remaining clothes and pulled my t-shirt over my head. I ran my hand down and cupped her lightly-furred pussy, enjoying the feel of her ginger pubes and shaved lips on my fingertips, as Mark continued to work on my cock.
“Mmmm, baby,” she moaned as I leaned down and drove my tongue into her mouth.
Cathy maneuvered me back toward the bed with Mark following on his knees. Jason moved in behind him, dropped the strap-on on the bed and guided the head of his cock back into Mark’s upturned ass. He moaned around my cock as Cathy straddled my shoulders and presented her dripping pussy to my questing tongue.
What a pictured we’d have made – me, lying back on the bed with Cathy grinding her snatch into my mouth, Mark deep-throated my cock while getting plowed doggy-style by Jason. The only sounds in the room were lustful moans and wet slurping punctuated by the rhythmic slap of thighs on ass cheeks.
Cathy suddenly cried out, “God, I’m Cumming!” She grabbed my head and ground her pussy harder on my tongue as she shuddered through her first orgasm of the night.
Mark released my cock, glistening with his saliva and my precum, and pulled Cathy back off my mouth. She groaned in frustration until he slotted the head of my cock into the entrance to her pussy. He pulled her hips back and down, forcing the head inside.
“Wait!” Cathy cried. “I’ve never . . .”
“I know, girlfriend,” Mark said. “Just relax.”
He started slowly pumping her hips back and forth slightly, moving just the head of my cock in and out of her dripping honeypot. The stimulation continued and intensified her orgasm. Cathy groaned aloud as she came, crying out toward the ceiling, as Mark continued to fuck her up and down on my cock.
He slowly increased the depth of the strokes, eyes locked on her crotch. I don’t know what he saw but, at some point, he decided she was ready and pulled her down, tearing through her hymen and burying my cock fully in her snatch.
“Oh, shit!” Cathy moaned out, part pleasure and part pain. “Oh, FUCK!”
“Relax, girlfriend,” Mark repeated as he stood and made his way around toward my head. “It only hurts for a little while.”
That said, he grinned at me, then at Jason, and brought the head of his cock toward my lips. I looked briefly at Cathy. She just smiled and nodded.
I opened my mouth, accepting the head of Mark’s thin, 5-inch cock. He immediately pushed forward, obviously attempting to choke me. But, as I said, I was no novice at sucking cock. I simply opened my throat and allowed his shaft to slip fully into my gullet.
It honestly wasn’t that much of a chore. I’d sucked, and swallowed, bigger cocks than his before I was a sophomore in high school.
Cathy started slowly rotating her hips while Mark slid his cock in and out of my mouth. Jason, meanwhile, was busy somewhere behind Mark. I couldn’t see what he was doing until he stepped into position behind Mark, his cock hard in his hand, shining with lube in the dim light.
He gently pressed Mark’s legs further apart and bent him forward. Jason guided the head of his prick to Mark’s rosebud and, slowly, pressed it in. Mark groaned as Jason’s shaft split him open.
“Oh, yeah, daddy,” he said. “Fuck me good. Fill me up with your cock.”
Cathy, meanwhile, was riding my cock faster. She’d lift up until just the head remained inside then slam her hips down. She grunted each time she bottomed out, the head of my cock slamming into her cervix, filling her to the brim.
We were fucking up the proverbial storm. Cathy was riding my cock like a cowgirl on a bucking bronco while Mark stroked my mouth and Jason pounded Mark, each thrust pushing his cock deeper and deeper into my throat.
Cathy slammed down hard on my groin and froze, screaming through her second orgasm of the night. To my surprise, she climbed off me, my cock popping from her oozing snatch with a wet “plop.”
She rolled to the side and onto her stomach before arching her back and raising her ass in the air. She begged me to fuck her doggy style, just like Jason was fucking Mark.
I was quick to oblige, letting Mark’s cock slip from my mouth and sliding in behind her, slipping my cock back into her pussy. Mark looked at me for a second, then down at Cathy and, without missing a beat, slipped the head of his cock into her mouth.
“Damn, I guess girls are as good at this as boys,” he said after a moment, feeling Cathy’s hot mouth and slipper tongue glide around his cock shaft.
Jason just laughed and said, “I told you so,” giving Mark a sharp slap on his ass.
My roommate slipped his greasy, shiny cock from Mark’s ass and looked me in the eye.
“You wanna try this?” he asked.
“Get over here,” I said, spreading my legs further apart. “Give me that cock.”
Mark grinned as Jason stepped in front of Cathy and fed her his cock. Mark grabbed the bottle of lube, greased up his fingers and pushed one, then two into my ass. I groaned at the sensation, relishing the feeling of a hard, live cock filling my bowels. It had been a long time since I’d had more than a girlfriend’s finger up my ass and I’d forgotten how much I enjoyed it.
“Oh, that feels good,” I moaned. “Oh, yeah.”
“God, your ass is tight,” Mark groaned. “Is this the first time you’ve been fucked?”
“No-oooo,” I moaned back. “But it’s been a while.”
Once Mark was settled into place, his slender 5-inches felt amazing buried in my ass. It wasn’t so large as to be painful. But it was just long enough to tickle my prostate and wide enough to stretch me just right.
I’d buried my cock again in Cathy’s pussy, battering the top of her womb, the slide out onto Mark’s cock. I developed a good rhythm, fucking myself and my girlfriend at the same time, driving Jason’s cock into her mouth for good measure.
The moaning, groaning and slaps of flesh-on-flesh filled the room. The smell of sex permeated the air. I don’t know about the other three, but my mind was going into sensory overload at the wild, impromptu orgy we’d stumbled in to.
Jason suddenly moaned out an “Oh, FUCK!” He gripped Cathy’s shoulder-length red hair in both hands, threw his hips forward and buried his cock deeply in her throat. She gagged as he shuddered, obviously filling her gullet with a massive load of cum.
When he finally released her head, she collapsed forward, letting my cock fall free from her pussy. She rolled onto her side, on top of the still-unused strap-on, which she pulled out from under her back. She looked at me, still being fucked my Mark, and got a wild grin on her face.
Even though he’d just cum bucket loads down my girlfriend’s throat, Jason was obviously still horned up. Almost immediately, he took Cathy’s place in front of me, on his knees with his ass in the air. He backed into position and reached around to set the head of my cock in place against his ass.
With just Cathy’s pussy juice as lube, Jason speared himself backward onto my cock. It was his turn to groan as I bottomed out in his ass.
“Fuck, that’s thick,” he moaned. “Damn, you’re tearing me open!”
I slapped his upturned ass hard enough to raise a red hand print on his right cheek.
“Hey, it was your idea,” I said. “Now, man up and take it.”
Cathy had rolled off the bed and stood on somewhat shaky legs with the large strap-on in her hand. She studied it for a moment as we three boys banged away in front of her. Then a light seemed to dawn on her face and she stepped into the harness. She pulled it up and cinched it tight around her waist.
The dildo appeared to have two ends, the obvious one protruding to the front and a second, smaller cock-shaped appendage. Cathy fit the smaller end into her pussy then grinned.
“Who wants it?” she said.
We all laughed. Here was this tiny, 17-year-old redhead with perky, b-cup tits and a massive, jet-black cock sticking out of her crotch. Jason reached out, grabbed her by the shaft of “her” cock, and pulled her toward his side of the bed.
He wrapped his lips around the head and pulled her by her tight little ass until the faux phallus was buried in his throat. He gagged slightly, then relaxed into it as Cathy began to fuck his throat.
“Hey, what about me?” Mark asked, his cock still buried in my ass as I fucked back and forth between him and Jason.
“He’s a bit of a whiner,” Cathy said. “Isn’t he?”
“Mmmm-humph,” Jason moaned in agreement.
“Guess I’d better fuck him to shut him up,” she said.
She popped “her” cock out of Jason’s throat with a groan, stepped into place behind Mark and, just using Jason’s spit as lube, pushed it hard into his ass. He groaned as Cathy’s momentum pushed his cock fully into my ass and my cock hard into Jason’s.
“Shit!” Mark moaned. “God, that’s huge! Oh, yeah! Fuck me!”
Cathy ended up doing most of the work, fucking into Mark, who fucked into me and me into Jason. It was an insane, four-way ass fuck, the likes of which I’d never heard of before or since. The slapping of flesh on flesh was punctuated by moans and groans of “Oh, yeah!” and “Fuck me!”
“God, this is sooo hot!” Cathy groaned before she screamed and came. Jason, who was madly jerking his cock, shuddered and coated his hand and the bed with jizz. His ass clenched as he came, rippled over the full length of my cock and milked my cum next. Finally, with a loud groan, Mark convulsed as my ass gripped his thrusting cock and filled my ass with his juice.
We rolled apart, panting, and collapsed into a sweaty, satiated heap on the bed. As we caught our breath, Jason and I looked at each other and started laughing. Mark and Cathy looked at us for a moment like we were nuts, then joined in. Soon we were rolling around on the bed, kissing and laughing like the fuck-out bunch of kids we were.
Cathy and Mark soon dressed, kissed each of us goodbye and headed for the door, both walking a big gingerly. Jason and I remained naked and went about straightening up our room before we collapsed into our separate beds, exhausted from the marathon session.
I dreamed about having hot sex with my girlfriend, roommate and a friend. I woke sometime in the wee hours of the morning with a hot mouth wrapped around my rock-hard cock.
