Cassie Caught in the Middle


Caution: This Sex Story contains strong sexual content, including Ma/Fa, Romantic, Reluctant, Coercion, Hermaphrodite, First, Pregnancy, .

Desc: Sex Story: Cassie's oldest and best friend Mark sprang an unusual request on the startled young hermaphrodite. His fiancee Tracy had confessed to fantasizing about having a three way with a little double penetration action! Reluctant Cassie has no wish for her friend and roommate Tracy to also discover her secret, so a tricky plan is soon hatched. One question remains. Just who is tricking whom?

Cassie McCaffery nearly dropped her coffee cup when her best friend made his request. "Th-Three way?" She gasped, putting the cup down with a shaking hand. "You have got to be kidding!"

Mark Benson grinned wickedly at his childhood buddy. "Cass, I thought you'd be overjoyed!"

The busty redhead felt her face grow warm. "Overjoyed, he says?" She took a deep breath. "You can't be serious! Tracy is my friend too! She isn't just my roommate! She's also your fiancée! She'd hate us both!"

The handsome young man sighed. "Cassiopeia Cleo McCaffery, Tracy isn't going to hate anyone!" He glanced down at his friend's lap and grinned. "I think at least part of you likes the idea."

Cassie grabbed a sofa cushion and quickly covered her lap with it. "I am sure I don't know what you're talking about!"

"Oh no?" Mark grabbed the cushion and yanked it away. The front of Cassie's skirt rose at an alarming angle. "Jeez, I'm impressed. You still pop boners faster then I do!"

The redhead glared at him. "Leave my cock out of this! I was going to, uh, relieve stress when Tracy left, but oh no! You just had to come barging in!"

Mark just shook his head. "Look, I'm trying to help you. I'm certain Tracy will be into this!"

"Into what!" Cassie felt herself on the edge of tears. "Into finding out her roommate is a freak?"

With a sigh, Mark reached out and plinked Cassie's nose with his index finger. Hard! "What have I told you about that 'freak' talk?"

Startled, the young woman clamped a hand over her face. "Ow! What the hell was that for? We aren't eight years old on the playground any more! Men do not hit women!"

"I'm sorry. You're right." He smiled. "I did get you to admit you aren't a freak. You're a woman! You just were blessed with a couple extra parts."

"You jerk!" she punched his arm and started to giggle. "Okay, so I'm not a monstrosity. That doesn't mean Tracy would jump at the chance to screw a hermaphrodite!"

"Listen, dummy! I know what's on her laptop!" Mark laughed. "Tracy has no idea I figured out where she hid her porn on the hard drive. Did you know she has hundreds of Japanese hentai anime files? I recognized quite a few that feature hermaphrodites. I could actually be running the risk of losing her to you if she discovered your secret!"

"Oh shut up!" Suddenly Cassie looked interested. "Really? No! Forget it! Just because she watches something, doesn't mean she wants it to come true! I loved "I an Legend" but I don't want to be chased by vampire zombies!"

"I hardly think a horror story is a good analogy." He laughed. "Besides, Vincent Price did a much better job."

The redhead shook her head. "Don't try and change the subject! Why me? Why not invite some girl Tracy doesn't know? You could have a perfectly safe three-way that way!"

It was Mark's turn to blush. "When we talked about fantasies, Tracy mentioned the three way only to bring up one specific thing. She wants to experience a, well, a D-P."

Cassie was well versed with Internet porn stories. "Oh my gosh! She wants it up both holes, at once?"

"Yeah." He rubbed the back of his neck. "That's why I thought of you. It would be sort of gay if I had another guy in bed with us. What if he tried something funny with me? You're the only person with a dick I know I can trust!"

"Thank you, I think." She sighed. "I still think you're crazy! What if she freaks out and hates us both? No, I'll just stick with masturbation. Nobody will learn my secret that way."

"Tracy drunk, without her glasses, would never catch on that you're really packin' heat! She'll think it's a dildo or something."

"No, I can't risk it." She smiled sadly. "Thanks so much for thinking of me though."

"Are you stupid or something? Do you know just how horny Tracy gets after a couple drinks? I give you my word. You will lose your virginity tonight! All you have to do is get some body paint and put it on your dick. Don't look a gift fuck in the mouth, kiddo!"

"Sometimes I wish you never caught me writing my name in the snow when we were kids!" Cassie giggled. "I'm not saying yes mind you, but if this actually did work, would I be the one to do her, uh, pussy?"

Mark smiled knowingly and patted his buddy's arm. "Kiddo, what are friends for?"

Cassie thought for a minute, and a big grin lit up her face. "I bet you're right! It actually may work! I read this comic once. A hermaphrodite mouse named Squeak disguised her, uh, difference with body paint. Mrs. Bull thought she was wearing a strap-on dildo!"

Mark gave her an odd look. "You may not be a freak, but you sure are weird." He leaned forward. "Could it be you're a closet furry?"

"Hey! There's nothing wrong with furry artwork!" she giggled. "I should show you my Doug Winger collection!"

He laughed. "I was just kidding! I told you. Just paint your dick like a dildo, and all your dreams will come true. Tracy likes purple. I'd go for that."

"No, wait." Cassie looked crestfallen. "I can't do it. Not today. Tracy and I are on the same cycle. She's fertile today. I know I am. Putting a condom on a strap-on would look kind of suspicious. Just find a nice girl and have her wear a real strap-on."

Mark choked a bit on his own coffee. It took him a moment to catch his breath, but his eyes had an odd burning look to them. "Look kiddo. Tracy and I are getting married, but you're still my best friend. If something should happen, she'll never know." He blushed again. "After all, I plan on getting me some 'sloppy seconds' tonight. I'll accidentally forget to put on a condom myself. Since you were only sporting a strap-on, She'll just think I shot off a massive load in her. I'll be the one Tracy will be pissed at. She doesn't want to walk down the aisle with a big belly. Besides, it'll just be a fifty-fifty chance you'll knock her up. I bet I'll be a daddy after tonight."

Cassie giggled. "Don't be so sure of that, Mark!" The redhead sat up proudly. "I looked it up. I cum much more then what's average for normal males! I have an abnormally high sperm count too. I bet I'll have her pregnant before you even slip it in and get your sloppy seconds!"

"Well just brag about it, why don't you?" Mark couldn't help smiling. "Tracy does have a few Bukkake videos. Maybe you should go for that too. You know. Slop up her glasses. That sort of thing."

"No way! I don't want to ruin our friendship because I'm a hermaphrodite! I'll get some body paint this afternoon. That way I can keep my secret." she sighed. "Make sure she isn't wearing her glasses just to make sure, okay?"

"Not a problem." He got up and headed for the door. "I'll bring her back home around ten o'clock. Be ready for action!"

The hermaphrodite leaned against the door after Mark left. "I'll be so ready!" she looked down and giggled. "Heck, I'm ready now."

The redhead put the chain on the door and locked the deadbolt. "Can't have Tracy walking in and catching me now! I can't wait until tonight though." She gave her penis a little stroke through the material of her skirt. "It's okay my not so little friend. Let's have a special treat today."

Bypassing her own room, Cassie strode right into Tracy's. "What a slob, but it does come in handy!" she picked up a lovely pair of pink panties from the floor and held the delicate garment to her face. Inhaling deeply, the hermaphrodite let out a sigh. "Oh Tracy! Tonight I'll get to sample the real you!" She sniffed again. "It'll be like a dream losing my boy virginity to you!"

Stripping off her own clothes, Cassie made herself comfortable in her lovely friend's room. Taking a bottle of Tracy's expensive body lotion, she liberally applied the cool smooth cream to her massive organ. "I can't wait for tonight." She whispered as her hand began gently stroking her erect cock. "I've dreamed of making love with you ever since the day we met. Mark is so lucky he gets to fuck you!" she giggled. "He's such a good friend though! Who else would want to share his girlfriend with me?"

Settling on Tracy's unmade bed, Cassie laid back and moaned softly as her hand glided over her slippery erection. "Tracy dear. I hope you don't mind me getting a big dildo! I bet you'll go wild when I put my eleven inch 'toy' inside you!" she laughed joyfully as her slimy lotion covered hand caressed the length of her penis. "Mark's pretty big. I heard you talk about how good he feels inside you. Wait until you feel me! I'm bigger! I'll fill you up so good!"

She pulled the panties on over her head so the crotch covered her nose and breathed deeply of her roommate's essence. Tracy had been running this morning. Cassie didn't mind that at all! She gloried in the rich musk that filled her senses and thrilled her soul! "Oh, my beautiful Tracy! I'm so happy you're marrying Mark, but I wish you could be mine! Thank God in Heaven I get this wonderful chance! How will I ever be able to repay him?"

Her hand moved faster. The room was filled with the sloppy sounds of slippery lotion penis pulling. "Oh, oh God! It's gonna be a big one!" With a practiced move, Cassie threw her legs up over her head. Eager pursuit of this 'hobby' over the years had made her rather flexible. Back arching upward with her firm butt in the air, her toes rested nicely on Tracy's pillow. Moving the waistband of the panties aside, the redhead captured the head of her cock between her quivering lips. The lotion tasted terrible, but who cared? The feelings were exquisite!

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Story tagged with:
Ma/Fa / Romantic / Reluctant / Coercion / Hermaphrodite / First / Pregnancy /