1 comments/ 53606 views/ 28 favorites Shemales on Vacation By: tawnysuede Shemales on Vacation or Fun in the Sun, When Boys Will Be Girls! ****** Chapter One - Cum Fly With Me! Teri Nolan and Brenda Vink giggled to each other as they whispered excitedly between them. It was hard to pay attention to the movie showing at the front of the cabin on their long flight across country to California. Their minds were on their sorority roommate, Dallas Green, who had just a few minutes earlier gone back to one of the washrooms at the back of the plane. The girls had noticed the handsome steward slip into the same washroom compartment as Dallas only a minute later and were wondering what kind of reaction he would have when Dallas revealed her little secret to him! Dallas wasn't saying anything at the moment since she was avidly slurping her tongue around the steward's stiff cock as her mouth bobbed up and down his slick shaft. Though fully twenty years old, Dallas was a short girl -- barely 4'6". But what she lacked in height she made up for in looks. She had a slim figure with flaring hips and very large breasts for her size -- breasts which currently flopped out of her blouse. She was kneeling on the floor of the compartment, eagerly sucking the steward's dick as he sat on the closed toilet seat while at the same time squeezing and mauling her sensitive nipples, working herself into a feverish state. Dallas' face was attractive as well -- big green sorrowful eyes, large red lips, delicate earlobes and short blonde hair cut in a page boy bob. Dallas loved sucking dick, particularly long ones -- and it hadn't taken long to notice the hardon that had swelled in the steward's pants when he had chatted to her while serving drinks in the cabin. As the steward grasped Dallas nipples and titillated them, Dallas used one hand to push his six inch rod up against his belly as her tongue lashed across his scrotal sac. Dallas briefly sucked on each of his balls before returning her attention to his dickhead -- her hand twisted his raging hardon as her teeth grated across the sensitive underside of his glans. Dallas' other hand, slid between her own thighs, gliding over herself, exciting herself. She felt the wetness dripping from herself -- she was eager -- she was ready to fuck! Dallas stood up and turned around, leaning over the small sink and counter. Her left hand held tightly to the front of her groin, Dallas raised the back of her skirt to expose her smooth rounded ass cheeks. The steward was surprised to see that the blonde sex kitten wore no panties (she had removed them while still in her seat). "Fuck me," purred Dallas, "Fuck me up the ass!" The steward smiled broadly. Very few women were experienced enough to know the true pleasure of being sodomized and the few women whom he had fucked anally had had to be primed with a full night of liquor first. If this bitch wanted it up the poop chute -- terrific! His pants around his ankles, he stood behind her and pressed the tip of his hard cock against her anus. His dick was well lubricated with her saliva and Dallas had long practised relaxing her anal muscle so the steward's glans plopped into her ass with little difficulty. He pressed forward and his entire six inches slid smoothly and deliciously up her anal shaft. The steward slowly pumped his hot meat stick deep into her ass and then back out so that only the bare tip remained embedded in her hot canal. He then thrust his shaft back into her, marvelling at her tightness -- much better than almost any pussy he had ever fucked! Dallas was in heaven, she loved the feel of a long hard cock slowly gliding up and down her poop chute, loving caressing her prostate, sending chills along her spine. But she was still attentive enough to guide the steward's probing hand to her hot eager nipples when he tried to instead reach around to her pussy, to stroke and caress it. Clutching one of Dallas large breasts in each hand, thumbing her nipples rapidly, the steward started to plough his cock along her love channel much more vigorously. His cum boiled in his balls, eager for release deep into the blonde vixen's bowels. Sensing that this was the best moment, Dallas reached down and undid her skirt at the side and lifted it off so that she was now naked from the waist down. Her left had moved away from her groin and what it hid and she bucked back eagerly into the steward, working in tandem with him, driving his cock further down her anal shaft than it had yet reached, sending ecstasy through her body. Releasing one of her tits so that it slapped madly against Dallas body as he fucked her, the steward reached down to stroke Dallas' clitty, to help her reach her orgasm. But instead of a furred pussy, his fingers encountered a rigid cock, as thick and as long as his own. "What the fuck!?" exclaimed the steward, suddenly pausing in his fucking, with just the tip of his cock in the short blonde's ass. "What is this!?" "What's the matter, honey? Never felt another cock before?" replied Dallas. "Fuck me, sugar! I want to cum!" So saying, she thrust her ass back, sending the steward's slick cock sliding back up the full length of her ass. "But I don't... how can... I mean, I don't understand." The steward just stood there, neither fucking her nor taking his cock out of her tight ass. "Shit," said Dallas, "I'll have to do this myself!" She pushed her ass backwards roughly, causing the steward to stumble against the toilet compartment and sit down heavily, his cock slipping out of Dallas' ass. Giving him no time to argue, Dallas straddled his cock, one foot on the floor and the other up beside the toilet seat. Steadying the steward's cock with one hand, she squatted down and slipped his still hard rod back into her anus. The earlier fucking had stretched her ass mouth wide so she easily slipped him back in. Dallas raised and lowered herself on the stiff member. Using her own weight and practically dropping herself on the hard dork she managed to thrust the steward's meaty dick deeper than it had yet travelled. As she fucked herself up and down the shaft, her own heavy ball sac slapped itself against the steward's balls. She had to steady herself with both hands against the walls of the narrow compartment and so her large boobs flapped freely against her heaving chest until the steward awakened from his shock. He couldn't believe it -- this beautiful bitch had a fucking cock! And bigger than his! But what the hell -- she had a sweet ass, he thought as he grasped her mighty boobs and began to pump his cock up into her as she in turn sank down on him. Dallas squeezed her ass muscles along the full length of the steward's dick. "Oh JEEEZZZUS! That's fucking fantastic! Oh... oh... I'm... I'm CUMMINGGGG!" cried the steward as his thick man scum erupted from the head of his cock, washing across Dallas' bowels. Dallas remained seated on the cock, but continued to squeezed her ass muscles, milking the organ of all of its delicious fuck juices. Dallas slowly fisted her own hard dick, eager to cum, but satisfied for the moment to let the steward glow in his own orgasm. She turned her head and the steward kissed her passionately, his tongue probing deep into her mouth. She sucked his tongue hungrily. Spent, the steward collapsed backwards, and Dallas too fell back against him. His half wilted dick still embedded in Dallas' ass, the steward ran his fingers teasingly across the large nipples of her breasts, causing them to rise to full rigidity. Dallas shivered and again kissed him. "What the hell are you, anyway?" he asked her. "You don't look like any transvestite I've ever seen!" "Transvestite? Is that what you take me for? Honey, I ain't no boy in a dress. Does this feel like a flat chest? Do these feel like rubber?" she said as she took both his hands and rubbed them across her titties. "Hell, I'm a normal healthy girl - I've just got a little something extra! You can call me a SHEMALE if you have to give me a name!" And so saying, reached down and languidly jerked on her cock which was still fully erect. Faster and faster she jerked on her cock. The steward looked in the mirror on the back of the washroom door and the vision there excited him tremendously. He saw himself with his cock jammed up the ass of a delicious young blonde tramp, her heavy tits heaving on her chest as she jerked off her large thick cock. The steward cupped and mauled Dallas' tits, squeezing and pinching the nipples as she frigged her cock harder and faster. Her manicured bright red nailed fingers flew along the length of her dick. Her hips bucked upwards, eager for her cum to fly. The steward's cock slowly rose again, filling her anal canal. Dallas' tongue flew across her lips as she panted in lust. It was coming, her orgasm, her blast, was building deep in her. And suddenly, indeed, her cock erupted sending a stream of jism fountaining across the washroom compartment to land, splat, right on the reflection of her gaping mouth. Dallas jerked and squeezed and fisted her cock, milking all of her shemale jism from her cock. Satisfied, she rested, but only for a moment. The steward heaved upwards, spilling her to her feet. He bent her over the counter and once again fucked her deep in the ass, his efforts made even easier by the lubrication of the jism from his previous ejaculation. In only a minute his cock erupted again. A minute later, his clothes straightened, he gave Dallas a quick peck on the cheek and somewhat ashamedly exited the washroom, to return to his duties. Dallas took a while longer to clean herself up and then returned to her seat where she recounted the whole episode to Teri and Brenda. Interlude Teri slowly rubbed the taut nipple of her tit as she listened to Dallas' blow by blow description of her sexcapade. How she wished she could be as bold as Dallas was -- just picking up any man when the urge hit her. How she wished she could be rubbing her cock instead of her tender nips, but it was held tight between her thighs by her cock harness -- after all, an unseemly bulge wouldn't have made the proper fashion statement with her tight black leather mini skirt. Dallas was wearing a loose skirt and so didn't have such a problem today. Yes, Teri was also a shemale, as was Brenda. Two years ago Terry Nolan would have never dreamed that within six months his sister Stacy would have put him into a situation where he would welcome being transformed into a near-girl, a SHEMALE. Gone was all of his former life. Now he lived at the Tau Iota Tau sorority house at Eastbrook College, his tuition and all living expenses fully paid for so long as he continued to take his hormones and undergo the operations that had been necessary to transform him into the beautiful creature that he now was. And he had had plenty of company. Almost all of the girls living at the sorority were actually shemales, living and being transformed at the expense of an elite club of rich men who lived out their secret fantasies a few times a year with their young charges, but otherwise left them to their own playful sex games so long as they didn't reveal themselves for what they were. Brenda and Dallas were Teri's roommates at the sorority house; Teri a sophomore at the college, Brenda a junior and Dallas a senior. At the end of the school year, Dallas would have a decision to make -- to remain a shemale or to have the final operation and become a full female, at least to all outward appearances. For the first while, Teri had rebelled against her transformation. But then she had welcomed it, finding that she had all the benefits of being a beautiful female and yet still having the stiff hard cock she had always possessed, and with plenty of sorority sisters willing to play sex games with her. It was now Thanksgiving break at the College and Brenda had invited Teri and Dallas to fly home with her to Santa Barbara and spend the holiday with her family. Teri had already met Brenda's father, Dr. Vink. He was one of the club's plastic surgeons, and a member himself. Though Teri's breasts had grown quite large from the hormone treatments, Teri had wanted still larger boobs and so Dr. Vink had performed the breast augmentation surgery. He had also performed minor cosmetic work on her face -- enlarging the upper lip, sculpting the nose, raising the cheek bones. In only a year and a half of treatment, Teri had become the most beautiful shemale that the sorority had ever produced. She was in top demand at the club's sex gatherings. Dallas, who had visited the Vinks several times in California as Brenda's guest, had also been physically enhanced by Dr. Vink. But strangely, Brenda herself had never had any surgery of any kind; her transformation so far had been totally the result of the hormones she had been taking for over three years now. Oh, well, thought Teri. She was looking forward to a fun week in the sun! Chapter Two - Feeling is Believing! A half hour later, Teri noticed the steward in animated conversation with a pretty dark haired stewardess at the front of the cabin. During the next fifteen minutes the stewardess, who's name tag said her name was Maria, walked past the girls' row several times and each time she stared at Dallas. Again, Teri noticed her talking to the steward, this time shaking her head as if in disbelief. Braving her own fear, Teri got up from her seat. As she scrunched past Dallas, the shorter girl grinned broadly at her and said "Go for it!" Teri walked slowly down the aisle towards the front of the cabin. As she did, every man's eyes were upon her. She was a knockout. Teri was not an especially tall girl either, standing just 5'2" flat but today she was wearing three inch heels which accented her long, shapely legs over which she wore black stockings, the very tips of which occasionally peaked out beneath her short black leather mini skirt. A bright green tube top barely covered her ample chest, the taut nipples of her 40D breasts quite evident. Her narrow waist gave way to solid hips lending her an exquisite 40D-26-36 figure. Her long straight blonde hair reached just below her shoulders. Two large hooped earrings, hung from her delicate ear lobes, two extra holes pierced in each ear currently held open by studs. Her face was exquisite -- any model would die for her pert nose and high cheekbones, her perfect blue eyes and long lashes, her just right lips. And through long practice, her makeup was impeccable -- the right amount of mascara, eye liner, eye shadow, blush and lipstick. At the front of the cabin she approached Maria and asked her for a couple of aspirin. The stewardess was nervous as she fumbled in a drawer for the pills. "I couldn't help noticing how you were staring at my friend, Dallas." Teri said to her. "She... she's quite pretty." "So are a lot of other women on this plane. Why her in particular?" "Joey... the steward... he, he told me something about her... your friend I mean..." stammered the pretty dark haired girl, "I couldn't believe him. I mean... I don't believe him." The stewardess lowered her head and blushed. As Maria handed her the aspirin, Teri grasped ahold of the stewardess' hand and tenderly caressed it. "Maybe you should be more trusting!" "You, you mean she really has a...?" Maria couldn't say the word. "Uh-huh!" "And... and you?" "Dallas hasn't got anything that I haven't got," said Teri as her hand patted the front of her skirt above the groin. Teri's tongue flicked across her lips, wetting them. "Would you like to see," invited Teri as she opened the door to a washroom compartment. "I... I don't know. I really shouldn't!" "Come on, it'll be fun!" said Teri as she pulled the Italian descended girl in after her. Teri immediately locked the door and then turned to face the nervous stewardess. Teri kissed Maria tenderly on the lips, but Maria pulled back. "I've... I've never kissed a girl before." "You've missed out on a lot of fun, then!" Teri pulled Maria's body to hers, their tits mashing together as she kissed the stewardess more aggressively. Maria quickly responded, her lips parting, allowing Teri's tongue to slide into her mouth, sucking on it hungrily. Maria's own tongue fought back and lanced into Teri's mouth, tasting the blonde shemale's oral juices. Maria was panting as Teri pushed her back. Teri drew down the top of her tubetop, exposing her firm proud breasts. They were large but not sagging -- bullets thrusting outward from her body. Her aureole were about the size of dollar coins and were set just atop the end her breasts. Her nipples were already a quarter inch erect -- as they always were. One of the reasons Teri was always sexually aroused was because, when Dr. Vink had last enlarged her boobs, he had shot a small amount of silicone in each nipple, so that they would never lay perfectly flat -- no matter what Teri wore across her breasts they were always teased and tormented by the material, keeping her in a constant, low-key state of arousal! "Oh, you have beautiful breasts," cried Maria. "Would you like to suck on them?," Teri asked teasingly as her fingers gently toyed with her own nipples? "I've never... yes, oh yes!" Maria eagerly wrapped her lips around Teri's left aureola. She sucked avidly, her tongue rasping across the nipple, then her tongue lightly biting at it. Maria knew how she liked her own tits sucked, and applied that knowledge well. Maria turned her attention to Teri's right titter, though one hand toyed with the saliva slicked nipple she had just abandoned. Her other hand ground against her own cunnie, through her skirt. Meanwhile, Teri was busy unbuttoning first Maria's uniform vest and then her blouse. Maria was surprised at how large Teri's nipples grew. She drew back in surprise, her fingers continuing to caress the blonde's nipples. She stared at Teri's nipples which were at least three- quarters of an inch long. "I have never seen such long nipples! They are wonderful!" Maria's bra fastened in back, so rather than fumble with the catch, Teri simply grasped it and pulled it down hard. Maria's breasts flopped out of their holder. Teri grasped each breast and pulled them firmly outward so that the still fastened bra and its straps now forced the dark haired girl's breasts to thrust forward in a confined space. Maria's breast were quite different from Teri's. They were smaller and less firm -- they would have sagged if not supported by the sling of the bra. But most noticeably she had what Teri called "apple" nipples -- large pinkish aureola as large as small saucers which covered the entire rounded ends of her boobs and small almost minuscule nipples. Teri flicked her nails across Maria's hardening nipples, eliciting a deep moan from the stewardess. Teri drew Maria to her and once again kissed her passionately, this time their bared breasts sliding across each other, their nipples fighting each other. But now was the time for Maria's treat. Teri undid her leather skirt and drew it off, exposing her long legs, sheathed in black stockings supported by a black garter belt around her waist. Maria was puzzled to find that Teri's panties were smooth and tight fitting to her groin -- no room for the promised penis! Teri undid her panties by the special snaps on the side so that she could draw them off while leaving her sexy stockings in place. It was then that Maria noticed the special strap that was tied around Teri's waist. Teri undid the string and then opened her thighs and from between her ass cheeks, drew forward her cock which had been imprisoned there. She undid the loop of the cockstrap from around the head of her penis and tossed the strap on the counter. Shemales on Vacation Maria gazed upon this vision before her -- a gorgeous blonde woman with a thick limp cock and large balls! And how much more perfect she would be when that cock was erect! Maria fell to her knees, unmindful of getting her skirt dirty and heedless of her heaving tits poking out from her blouse. She reached up to grasp Teri's cock, but Teri brushed her hand away. "Wha-" "Tell me what you want -- say the words!" "Oh, I want to suck your cock -- I want it in my mouth! Then I want you to fuck me!" Maria's eyes were wide with desire. Teri held her limp cock in one hand and wagged it in front of Maria's face. Finally she held it close to Maria's mouth and the Italian girl's tongue licked out and touched the dickhead. Teri was ready. Maria eagerly sucked the full length of Teri's cock into her mouth. As she ministered to the shemale's cock, it grew larger until Maria had a full eight inches to contend with. Teri had to admit that Maria was an expert cocksucker. Not once did Maria touch Teri's cock with her hands, rather she controlled the dick totally with her mouth, her tongue and her teeth, bobbing her head up and down vigorously on the stiff member. Maria attacked Teri's large balls, sucking first one and then the other fully into her mouth and chewing tenderly. Teri moaned. It was while she had one large cream filled egg in her mouth and Teri's erection draped across her nose and left eye that Maria realized that Teri was perfectly clean shaven. There wasn't a pubic hair anywhere on Teri's cock or balls. As she returned to sucking the cock, she did notice that Teri had a small patch of very short pubic hairs above her cock, perfectly trimmed into the shape of a heart. This woman was wild. But Maria was ready for more. She fisted the shemale's cock as from her kneeling position she looked upwards, past those magnificent tits, straight into Teri's eyes and said "Fuck me, oh please fuck me -- I need it so bad!" Teri lifted Maria up so that her ass rested on the counter by the sink -- Teri knelt on the floor in front of her. Maria rested her feet on Teri's shoulder as Teri tossed the hem of the stewardess' skirt over her knees, into her lap, exposing her crotch area to Teri's view. "Oh shit -- pantyhose! Good damn I hate these things! Don't you know enough not to wear these things if you're looking for a quick fuck!" "I'm sorry. I hadn't really expected..." "Never mind -- I'll take care of these!" The front of the pantyhose oozed pussy juices that had leaked copiously from Maria as she had sucked Teri's rampaging dick. Teri pressed her lips to the crotch of the pantyhose, partly to lick up these delicious juices but also to apply her own saliva, to wet them even further and therefore to weaken the fabric. Maria fingered her own nipples as Teri's worked on the pantyhose. When Teri had the nylon material good and wet, she pried at the material with her long hard fingernails, and finally bit at it with her teeth. Suddenly it ripped and she was able to grasp the edges and tear it back, exposing Maria's ripe plump pussy. Teri gasped at the sight of it. Teri had heard that some Italian women had such cunts, but had never seen such a sight before! Maria's cunt lips were big and meaty -- extremely fleshy -- both her inner and outer lips. The cunt and surrounding pubic area were covered in dense black bush -- thick coarse pubic hairs. As Teri watched, Maria's aroused pussy pulsated, the lips opening and closing, revealing their inner pinkness, beads of pussy juice pooling in the entrance. And at the top, protruding from its little cover was Maria's thick clitty, fully an inch long -- bigger than any that Teri had seen before. Teri dove her face into Maria's pussy, eagerly slurping up the pool of juices therein. She munched savagely on Maria's hairy cunt lips, sending sparks of pain along Maria's pubic bone. Maria lifted one heavy breast to her lips, attacking her own nipple with her teeth, something that Teri could never do -- her tits were much too firm! The blonde sex vixen spread the dark haired girl's outer cunt lips wide with tight clenched fingers and attacked the inner pussy lips, also sending her long tongue deep into Maria's fuck hole. Then she turned her attention to Maria's long clitoris, sucking on it avidly and at one point biting it so hard that Maria was afraid she'd lose it. Maria orgasmed as Teri sucked deeply on her clitty while driving two long fingers furiously in and out of her soppy cunnie. Barely giving Maria time to recover from her first cum, Teri stood upright, and fisting her cock, lay it across Maria's cunt lips, but not so that it would penetrate her. Teri slowly fucked her cock along the length of Maria's meaty cunt lips , teasing and tantalizing both of them. When Maria had her breath back, Teri did the deed -- she fed the entire length of her cock, through the black haired girl's portal and deep into her cunt. Maria wrapped her legs around Teri, drawing her ever deeper with each thrust of the shemale's hips. Teri in turn held onto Maria's breasts while her own bounced joyously in time to her vigorous fucking of the Italian trollop. Teri's ball sacs grew bigger as the cum boiled in them, ready to ejaculate. Teri's torrid pace of fucking increased -- her cock pistoned furiously in an out of Maria's cunnie. "Pinch my nipples. Squeezed them. Tear them off of me!" commanded Teri. Maria did as she was told, mauling the three-quarter inch tubes of dark flesh that she found so fascinating. Driven wild by the sensations running through her breasts, Teri came! She buried her cock deep inside the stewardess' pussy as her scalding scum cream shot from her piss hole. Multiple orgasms ripped through Maria as her insides were filled with the creamy jism. Finally, Teri's cock began to wilt and she drew back from Maria's hot cunnie. Teri grasped her dick and wiped it against Maria's thighs to clean off the mingled fuck juices. Maria lay back on the counter, content in her afterglow, as Teri began putting her clothes back on. When she was almost completely dressed, Maria was still lying there, one hand rolling around a nipple, the other frigging her clitty -- obviously she still wanted more! Suddenly the door to the washroom opened. A redheaded stewardess, using her special key, poked her head in. "Maria, are you all right? You've been in here so long and we are about to land... oh, I'm sorry," she blushed, "I didn't realize that you had company!" The redhead caught a glimpse of Teri's magnificent tits just before Teri drew the green tubetop back up and over to cover them. Teri excused herself and pushed past the stewardess. Only then did the redhead pay attention to Maria, lying on the counter, her tits hanging out, her legs splayed wide, her pantyhose torn and her cunt leaking juices onto the floor. "Oh, Maria, I never knew you liked girls! If you'd told me, we could have been having so much fun!" The redhead knelt between Maria's thighs and eagerly licked up the pussy juices. Chasing a trail of scum, she pushed Maria further backwards so that she could lick up the juices that had slickened Maria's asshole. Returning to Maria's cunnie, the redhead was puzzled to find herself slurping delicious musky man jism as well. How did that get there? As Teri closed the door behind her she caught a last glimpse of Maria jamming the redhead's face hard against her hairy cunt and heard her moaning "Eat me, Heidi. Eat my fucking cunt!" The remaining few minutes of the trip passed uneventfully. As the girls left the plane, Joey the steward stopped Dallas, whispered a few words in her ear and left a slip of paper in her hand. Maria stopped Teri, kissed her tenderly on the cheek and put something in her hand too. "What's that?" Brenda asked Dallas as they hurried to the baggage carousel. "His phone number. He wants me to call him in Los Angeles." said Dallas as she tore up the paper and tossed it in a waste bin. "He's got to be kidding!" "And that's the stewardess' number?" "Yeah, but she's based in Philadelphia." said Teri as she opened her purse. "You're going to keep it and call her sometime?" "Maybe -- who knows. After all it may be worth my while!" Teri opened the note to show Brenda and Dallas the hundred dollar bill that had been folded inside. The girls all laughed as they walked through the terminal arm-in-arm to pick up their rental car. FIN