Cassie Caught in the Middle

by Honey Moon

Copyright© 2008 by Honey Moon

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?

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

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!

Moaning around the rigid erect cock, Cassie's hand went into overdrive! It was nearly a blur as it shimmied up and down the thick organ. Her free hand teased her other self. The redhead's cute little pussy nearly flowed with honey as talented fingers thrummed against her erect clitty.

With a grunt of pleasure, Cassie accepted more of her quivering penis into her mouth. Her body shook as the inevitable happened. She exploded! She felt the pulses deep inside as her body released it's offering. Cheeks puffing out, the redhead's mouth filled with thick hot semen! She gulped, and gulped again. Still her ejaculation just kept on going! It took quite an effort to keep up, but as usual, she managed to swallow every drop her throbbing organ produced.

"Whoa, I needed that." She said thickly after swallowing the last of her seminal lunch. "Now I can be calm while I go shopping!" Yanking the panties from her head, Cassie just casually tossed them back to the floor. Sloppy Tracy would never know the difference!

Later that evening, a very nervous Cassie stood before her mirror and stared at her erect penis. She had carefully washed her privates and even shaved away all her pubic hair for this auspicious event. "Here goes." She gulped as the cool liquid latex body paint touched the warm flesh of her cock. "Tracy isn't allergic to condoms, and neither am I. This should work great!"

The hermaphrodite carefully applied the latex evenly over the flesh of her cock. "This looks so weird!" Cassie giggled as she spread the shiny purple coating over herself. "I hope she doesn't notice this." She whispered as she carefully avoided the bulbous head. "I don't want to make him less sensitive. I want to feel everything!"

She worked swiftly and eyed the results critically. The outcome was quite pleasing. "Wow! It does look like a dildo! Hopefully she'll just think I found a super expensive one with a realistic head and foreskin!"

The next part was easy. Using theatrical spirit gum, Cassie carefully glued the strap from an old purse around her waist. Perfect! The ends just touched the base of her purple giant! "It's a masterpiece! I look like a normal girl with a toy fetish! If Tracy isn't wearing her glasses, she'll never suspect a thing!"

The temptation to jerk off her new 'dildo' was great, but Cassie managed to resist. This way she was able to sustain her boner until she heard a key in the door. "Oh Gosh! They're here!" The suddenly nervous redhead threw on her bathrobe and hurried into the living room.

"Cassie! You're a true friend!" the petite blonde giggled. "Markie told me you don't mind a little bit of fun with a couple of good friends. I'm so glad!" Tracy walked carefully over, as if fearing she would fall, and grabbed her roommate. "Gimmie a kiss, you sexy woman!"

Startled, Cassie let the tipsy woman pull her lower until their mouths met. They both moaned as their lips touched. "That was wonderful." The redhead sighed as they parted. Her first kiss! She had kissed Tracy! Glancing at Mark, she saw his gentle smile of approval. This was going to be the best day of her life!

"Course it was wonderful!" Tracy giggled. "Girls always kiss better then boys do!"

Mark laughed. "Hey! I haven't had any complaints!"

The blonde glared at her fiancé. "You're an exception! Oh, I know! Kiss Cassie! Go on! Kiss your buddy!"

Cassie felt her heart do a little flip. "Uh, no, that's alright." She felt her face growing warm again. "Give Tracy that kiss. I'll watch."

Mark stood behind his bride to be and gave his head a little shake. Humor her, he mouthed silently as he moved around the happily giggling blonde. "Just one kiss. I promise, no funny stuff."

"Well, okay." Cassie sighed. "It'll be like kissing my mom or daddy, but, alright."

Mark put his hands on her shoulders and leaned closer. "I'll try not to be too much like your father." Their lips met, and Cassie felt an almost electric shock. Kissing Tracy had been wonderful, but this? Mark's tongue eased passed her lips to tease her own. Fear and excitement raced through her as her tongue teased back. Was this possible? Was it really real what she was feeling? Could one kiss turn friendship into, love?

She gently pushed him away. "Th-That's enough of that. I thought Tracy was the star of the evening!" In an attempt to distract her fevered mind from these new and frightening feelings, Cassie untied the robe's sash and let the garment fall to the floor. "A little birdie told me someone wants to try a double penetration fucking! I wonder who that could be?"

Tracy jumped up and down and waved her hand. "Me! Me! It's me! I wanna get it both ways at once!" The blonde gasped. "Oh wow! You found a purple strap-on! Purple is my favorite color!"

"Yep! I found it just for you!" Cassie reached out and snatched the glasses off of the tipsy girl's nose just as she was leaning close for a good look. "Uh, you should get contacts Tracy. You're too lovely for glasses."

"Nope! No contacts for me!" Tracy giggled again. "Markie has a glasses fetish!" she went on in a stage whisper. "Markie likes to blow loads on my face, an watch me lick my glasses clean. He's such a dirty boy!"

Cassie gulped as the sudden images in her mind made her penis gave a happy little twitch. Had Tracy noticed, even without her glasses? "Well, um, that's probably hot. I bet he likes it."

Mark laughed at her discomfort. "I sure do! Too bad that thing isn't real." He pointed at Cassie's quivering purple erection. "We could give Tracy a Bukkake bath."

The redhead froze! "It's just a dildo! Why say stupid things like that?"

The blonde giggled. "Not stupid! Not stupid at all! You should see Bukkake! It's so disgusting and nasty! It's degrading and really super filthy too! I so get off watching it! I finger myself like a crazy woman seeing those pretty Japanese women get soaked in spunk!"

"I know, um, I mean I'll have to watch one sometime." She tried to get the night back on track. "Come on Tracy! I thought tonight was all about you getting some D-P action! Should I take this back and get a refund?"

"Don't you dare!" The blonde grabbed Cassie's hand. "Come on! I can't wait any more!" she squinted at Cassie's disguised penis. "No offence Markie, but you get my hiney. Cassie's monster dildo would kill me up there!"

The hermaphrodite felt proud. Tracy was impressed with her cock! Too bad she thought it was just a toy. "Yeah Markie" she teased. "I'm, uh, it's just too big for the back door! Hope you don't mind!"

"Are you kidding?" he rubbed his hands together eagerly. "I've been dying to plow the back forty! Tracy never let me try before! I've been waiting for this for ages!"

"You say the sweetest things, Markie!" Tracy laughed. "I was saving my hiney-hole for a wedding present, but this is just too exciting to wait! Thank you Cassie! You're a true friend!"

"You're welcome, Tracy!" Cassie couldn't help smiling. "It is exciting, isn't it?"

Mark's eyes nearly glowed. "You have no idea! This is going to be the best night of all our lives!"

The hermaphrodite shivered as Mark and Tracy each took a hand and led her to the bedroom. The petite blonde stumbled and Cassie helped her remain on her feet. "Somebody's drunk." She laughed. "Is it true you get horny when you drink?"

"I'm always horny! Isn't that right Markie?" Tracy giggled. "That's why he loves me. I'll fuck'um any time he wants!"

"Nope, it has nothing to do with her wonderful charming personality or adorable good looks. I never even thought about how much I really love her either." He laughed. "I'm marrying her so I can screw all the live long day!"

Cassie was happy for them, but her newfound feelings made her feel more then a little jealous. It wasn't fair! One of them should be marrying her! "Mark! Don't talk about her that way!" She looked around in surprise. "Hey, wait a minute. This is my room!"

"Cassie-doll, you're so sweet to worry about me." The blonde smiled sweetly. "I know Markie is just kiddin'! We love each other, so everything is fine!" The sweet smile turned to a wicked grin. "Your room is nicer. It's so girly-girl it looks like something from the nineteen fifties! Just look at all the pretty plushies you own too! It looks like a little kid's room!"

Mark looked around in pretend shock. "Holy crap! How many pink things do you own, Cass? I feel like I'm in Barbie hell or something!"

"Mark, can't you tell anything? This isn't Barbie pink! It's Hello Kitty pink! Jeez! Didn't you notice all the kitty faces?"

"I did!" Tracy picked up a large Hello Kitty plushy and gave it a big hug. "I love your room Cassie! It's as sweet as you are!"

"Oh hell. I was right." He leered at the redhead. "Somebody is a furry!"

Cassie put her hands on her hips and tried to look angry. It was impossible though, while naked and sporting an almost painful boner! "Yes! I am a furry! I don't dress up in cosplay though, but I love all my little friends!"

Tracy playfully slapped Mark's arm. "Don't tease my girlfriend! I think it's cute she likes Hello Kitty! Say you're sorry or you have to go home!"

The amused young man bowed deeply. "I apologize from the bottom of my heart! Hello Kitty is a wonder to behold!" He looked surprised. "Hey, the TV is even Hello Kitty! Now that's impressive!"

"That's better!" Tracy started unbuttoning her blouse. "Now get undressed! I can't wait any more for my double fun!"

"Nether can I!" Cassie sat on her pink bedspread and happily watched Tracy strip. "Hurry up Mark! I never saw you naked before! I'm curious!"

The young man in question grinned as he kicked off his shoes. "Who am I to argue with two lovely ladies?" His hands went to his belt buckle. He made short work of undoing his belt. The tight jeans dropped, shortly followed by his shorts. Muscles rippled as he pulled the shirt over his head. "What do you think?" he asked in a sultry voice as he slowly turned around.

The redhead stared with wide eyes at his firm toned body. "Wow!" she giggled. "You should take your Speedos off at the beach though. You have a pale butt!"

Tracy jumped in front of Mark. "Hey! Watch me now!" The blonde was down to bra and panties. "I'm sexier then Markie is!" She gracefully slipped out of her bra and tossed it to the spectator on the bed. "See? I tanned all over!" The panties followed the bra and draped lightly over Cassie's disguised phallus. "I'm way sexier then he is!"

Force of habit made the hermaphrodite grab the panties. She held them to her face and inhaled deeply. They were still nice and warm! "Tracy, you certainly are!" she whispered from behind the lacy little garment.

Hands on her shoulders forced Cassie to lay back. "I know I am." Tracy said with pride. "I may be short, but I got a body that don't quit!"

The hermaphrodite looked up and giggled. "That's true, tiny! How can you be so short, and still have titties that big?"

The blonde snorted. "Tiny! Four foot eleven and three quarters is not tiny! My tits aren't that big either! I just have good posture!"

Mark sat on the edge of the bed. "Four foot eleven even. Face it baby. You're a living doll!"

"Well, this tiny living doll is gonna ride her a pony!" She climbed on the bed and straddled her giggling roommate. "Damn girl! Did you buy the biggest thing in the store? If you, um it were one inch bigger I'd be scared to death of it!"

Cassie felt her grin widen. "I, its not so big! Look at Mark's! It's big too!"

He actually blushed. "It's not all that big. I'm only about nine inches."

Tracy giggled as she wriggled over Cassie. "It's exactly nine inches. I measured it once." She moaned as her labia glided over the purple shaft. "Oh Cassie! Thank you again for this! Mark is the only man who ever made love to me. I wanna do this so badly, but I didn't really want some guy stuffin' his cock into me!"

The redhead gasped at the delightful warmth caressing her latex encased shaft. "W-What are friends for?" she said huskily as the lovely blonde's movements tormented her in delightful ways.

"Cassie, you are my friend!" Tracy lifted up and let the head of Cassie's disguised cock center on her opening. "My dear special friend!" Gently guiding the purple penis with her fingers, she settled down again. That head eased open her inner lips and pushed it's way into her body!

The hermaphrodite couldn't help a low moan as warmth like she never dreamed of enveloped her hardness. "It feels, uh, it looks so wonderful!" she gasped as Tracy took her fully inside.

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