The Stewardess Re imagined and Expanded
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Shemale Stewardess Seduction free porn video
Please note that this story is not written by me! It was stored in my computer for a long time now and decided to share it with you. The author's name as well as the site I found the story are not known...
My introduction into the sultry, steamy world of shemales came (and I mean came!) at 35,000 feet, on a plane flight to the Northwest.
I had been working myself to the bone, staying until ten or eleven at night, coming back in at six o'clock in the morning, and I guess the stress was visible. My boss, Terry, a very pretty, sexy lady (who I later found out was a hot-bod tranny too!) called me into her office.
"Nick, you need to get away, and I know just the place," she said, handing me a set of keys. "I own a cabin in Northern Washington. There's no phone, no television, no radio. Just you and the Great Outdoors."
"But it's out busiest two weeks!" I protested, imaging the whole mail order lingerie house would collapse if I was gone for a minute, let alone two weeks.
"It's an order, Nicholas!" Terry said. "Alan and Denise can fill in for you. You're under too much stress. You need to unwind. Then you can come back refreshed and ready for the fall inventory."
I argued, but to no avail. I never could win an argument from the tall, willowy brunette. She called and made the plane reservations for the following week.
Terry had booked me in the First Class cabin on a small, charter airline. She'd given me maps to the cabin, and arranged for a rental car at the airport. I threw together some of my old camping gear. Maybe she was right. Maybe I needed to away from people, constantly ringing telephones and the Internet for a while. By the time I'd boarded the plane, I was beginning to look forward to two weeks of solitude.
First Class was very comfortable. I'd never traveled that way before, and there were lots of little perks, like comfy, overstuffed seats with arm rests, personal VCR's, and of course, the service…which is where my wild sexcapades started. Our stewardess was real knock out. She was tall, leggy strawberry blonde with sparkling blue eyes and a very tight blue uniform. Her figure would have given a super model a run for her money.
"Hi, I'm Sherry," she said, smiling broadly. "If there's anything you need to make your flight more enjoyable, just let me know."
She said the same thing to the ten other First Class passengers, so I figured it was a standard, prepared speech. But as the long, eight hour flight continued, she seemed to be paying more attention to me than the other passengers. When my water glass was empty, she'd swoop down and fill it up, giving me a mouth-watering eyeful of cleavage. She brought my meal before anyone else's, and kept fluffing my pillows and pouring me champagne. She gave me a whole series of sly winks and smiles I was sure was a prelude to seduction.
About halfway through the flight, most of the other First Class passengers fell asleep, except for an old man who'd never taken his eyes from his lap top computer the whole trip. Sherry sauntered into the isle and whispered,
"Follow me if you want to join the "Mile High Club," Nick!"
Wow! What a trip this was going to be! Not even four hours away from the office, and I was about to get laid by a hot blonde!
I carefully followed her up to the front of the plane, to a spacious, empty lavatory. She locked the door behind her and grabbed me, planting a hot, wet kiss on my lips which I eagerly returned. I held her tight and caressed her round ass and upper thighs as we continued our lip lock, tongues probing like wild a****ls. She pulled off her top and undid her sheer, black lace bra, then brought my mouth down to lave her tits with kisses. They were big and full and beautiful, with red nipples like pencil erasers which jumped to erection under my sucking and nipping. I kissed her long, flat stomach down to her navel, where I could just make out the golden shimmer of her pubic hair.
"Just as second, honey," she whispered. "I'll make it easier for you."
She started to slide out of her mini-skirt, then smiled and said "Turn around and don't peek, bad boy!"
I laughed and faced the wall. I heard the silken swoosh of her tight dress hitting the floor.
"Close your eyes and follow me," she said, taking my arms. "Keep them closed!"
She led me over to a little padded shelf next to the toilet and sat down. She told me to kneel down in front of her. I could smell the musky perfume of her pussy wafting up to my face. I could hardly contain my excitement at the thought of plunging my hungry lips and tongue into that blonde bush.
"O.K.," she said with a slight giggle. "You can open your eyes now."
When I did, I nearly fainted. She did indeed have a healthy patch of golden pubic hair, but rising up from that furry forest was a huge, pink cock!
I was stunned speechless. How could this lovely creature have a penis? It seemed impossible. I wanted to run. I wanted to jump off the airplane. I wanted—to suck her cock. The sight of it poking up from those milky upper thighs, between those sheer blue stockings made me so hot, I just couldn't resist. I dropped my mouth down and began to shower her six inch "surprise" with kisses. I tasted hot and spicy as I took her dripping glans into my mouth and sucked gently. She took my head in her hands and slid me down the luscious length of her stiff shaft, until my face was nestled up against her pubic hair. I sucked and gulped for all I was worth. It was a strange sensation, like putting a sausage into your mouth, but not swallowing it. This was my first blow job, and I hoped it was giving her pleasure.
She began to gyrate her hips, drawing my head back towards the top of her rod, "mouth fucking" me in series of hot thrusts and bucking motions. Suddenly, she gave a little moan and pulled her dick out of my mouth. It glistened hard, powerful and gorgeous in front of my face.
"That's not where I want to come," she cooed in a seductive voice. My face went white with both fear and anticipation. I had a hunch I knew where she wanted to shoot her load.
"You don't mean?" I started.
"Oh, yes I do!" the sultry shemale purred. "Don't worry. I know you're an ass virgin, so I'll be gentle. Now come on. You'll love it, I promise!"
I don't know what amazed me more, the fact that I didn't run screaming from that lavatory, or the fact that she was right about being ass-fucked!
She had me strip and lean against the stall door, facing away from her. Then she lubed my asshole with KY Jelly and slid a long slim finger up my anus. I'd had girlfriends do that, so it didn't really feel bad, just a bit uncomfortable as she spread the cold gel around my asshole. After about two minutes, she pushed as second finger in and began to wriggle them around, spreading my butt cheeks with her hands. At first it burned, but soon it started to feel very erotic, and I felt myself getting a huge boner.
"Mmm," Sherry said. "Looks like you're ready for the ride, big boy!"
She gave my cock a firm yank, and positioned herself behind me. I felt a tremendous pressure as she shoved her hot, wet glans up past my asshole. She left it there for a few minutes, allowing me to "loosen up" and adjust to the feeling. Then she rotated her hot hips and sent another inch up my virgin ass. I screamed. It felt like my ass was on fire, but each time she pushed more of her big bone into me, my own dick got harder and wetter. Finally, she had all six inches up me, and then she began to fuck me in earnest, thrashing and bucking wildly. I moaned in both pain and pleasure as she gave me an expert reaming. She pulled my pelvis close and thrust deeper, making me squeal with delight. Sweat poured off my back as she continued her hot, rhythmic thrusts. Suddenly, she gasped, shoved me flat against the door and really jammed her whole six inches up me. I cried out as I felt her engorged cock head pulsate and her steaming come shot up my rectum. I'd never felt anything that sexy in my whole life! I came a few seconds after she did.
Her cock was still rock hard up my ass, and despite the burning, screaming pain in my rear, I asked her, almost begged her, to fuck me again, which she did happily, lowering me to the floor to take me "doggy style." She didn't come a second time, but her dick was still erect, so she left it in. It was starting to feel like it belonged in there. Finally, after about an hour had passed, we cleaned each other up, got dressed and went back to the cabin. I slept, exhausted and sore, the rest of the flight.
"Have a nice vacation, Nick," Sherry said, winking at me as I left the plane and headed for the rental car agency.
We weren't alone, so I couldn't thank her, or kiss her, for the marvelous new experience she'd given me. I figured I'd never see the tall, leggy strawberry blonde shemale again. It took me ten hours of driving to discover how wrong I was!
When I got to the rental counter, I discovered that I'd forgotten to take the most important thing—the map to Terry's cabin! I could have sworn it was in my left jacket pocket, but it wasn't there. I called her up on my cell phone and she gave me the instructions. I didn't tell her about my bizarre, amazing entry into the "Mile High Club."
Because I'd have to drive on tiny, winding dirt roads, I'd rented a 4 X 4, sports utility vehicle. I began to regret that decision as soon as the highway ended, because every bump (and there were about ten miles of nothing BUT bumps!) made my recently reamed rectum scream with renewed pain and soreness. I wasn't going to be in any shape to go hiking!
It was dark when I finally saw the tiny cabin at the end of a long, lonely road surrounded by tall Douglas firs. There was a lake on the other side of the cabin, but I didn't see any signs that there were other cabins. Terry said the lights were on a timer switch, so I wasn't surprised to see lights coming from the windows. But I was surprised to find that the door was open! I hesitated. Was there a burglar in there, possibly armed? Should I drive the fifteen miles to the nearest town and call the cops (my cell phone wouldn't work this deep into the woods)? I fished around on my key ring and found that the key was missing! That was impossible! I'd only put it on this morning! I was beginning to feel a bit spooked, when I saw a figure limned in the doorway, and a flash of golden hair.
"What took you so long?" Sherry teased. She was dressed in a tight, black lace catsuit, and she handed me a perfectly mixed martini, no olive, just like I liked them.[ILL. # 3-Insert of Sherry in door frame, dressed in lace catsuit, outline of her cock just visible beneath the material, holding out Martini, looking very "Lauren Bacall"-i.e., seductive, eyes flashing, ultra-sexy.]
"How did you get here?" I gasped. It seemed impossible that she'd gotten to the secluded cabin before me.
"I fly charter, remember?" she said. "I'm not just a stewardess. I've got a private jet license. There's a hanger just across the lake, and I rented a row boat. That one, down there."
I saw the row boat tied to the small pier on the lake.
"That still doesn't tell me how you knew I was coming here," I said, lugging my bags into the cabin.
Sherry laughed and held up my map, the one that had gone missing from my pocket, and the key Terry had given me. I knew it was the same key because it had a blue key-guard around the top.
"Guilty!" the statuesque strawberry blonde smiled. "I took them when you were—busy."
"Why did you follow me?" I asked. "I mean—other than what happened on the plane, what's so interesting about me?"
"I like you," she said in a tone of voice that made my toes tingle. Boy, was she sexy! Even her voice was a sex organ! As she posed languorously on the sofa bed I could see just the barest outline of her powerful prick in the black lace around her "bush". That made me hot, and I knew before the night was through, I'd have to taste its exotic musks again.
"Why?" I continued, curious. A girl that good looking could have had anyone, and I wasn't exactly a hunk.
"You're fun to fuck," she admitted. "You didn't cry and moan like most of my men, and you didn't run screaming when you saw my—big clit. The last guy who let me do him that easily was a movie star. You'd faint if I told you who. He always plays such macho, straight roles."
She told me his name, and I was stunned.
"He employs a shemale maid at his house in Beverly Hills," she added. "And he told me whenever his wife's away on a picture shoot, she screws his ass all night long."
All this talk of sex was making me hot, but I was really too exhausted from that long, draining drive to do anything about it.
"Well, I guess two is better than one," I said. "Though I was supposed to be coming here to get away from people."
"I'm not people," she smiled enigmatically. "I'm your mistress, and you will obey me. Now come here and give me a hello kiss."
Who was I to argue with a woman that gorgeous? A kiss was about all I could manage, though.
"Oh, poor boy," Sherry said. "Tired from your drive, huh? Next time we come up here, you can fly with me. Since today was your first time, I'll let you rest and rebuild your strength. But I've got a lot of activities planned for tomorrow, so get a good night's sleep!"
"I can guarantee that!" I said, kissing her again, and giving her cock a clandestine caress beneath that sexy cat suit.
"Here," she said, fishing a small plastic tube from her purse. "This will help loosen you up for me, and get rid of the soreness at the same time."
"What is it?" I inquired, squeezing out a dab of oily, green stuff which looked like toothpaste.
"My special recipe," she explained. "Aloe vera, plus a muscle relaxant. Here, bend over and let me apply it."
The touch of her velvety soft hands on my ass sent erotic shivers up my spine as she smoothed the cooling ointment around my sore asshole. I kissed her one more time, then I had to go to bed. We unfolded the sofa bed, and I collapsed beside my strawberry blonde goddess, and was asleep in minutes.
The next morning, we took a sexy shower, soaping each other's slick, wet bodies up and down. I gave her another blow job, then she gave me one that made my hair stand on end! Her lips and tongue were so skilled that I came in about two minutes. Then she did something both sexy and a bit disgusting. She didn't swallow my hot semen, instead she straightened up and kissed me, spill my own cum into my mouth! Wow, did that feel weird—but it tasted pretty good. I kissed her back, and we shared the cum between us, licking each other's lips until it was all gone.
"Now that you've had your nutritious breakfast drink," the tall blonde smiled playfully. "I'd like to go on a hike around the lake. It's about ten miles, so that should get us back here in time for lunch. After lunch, I want to fuck you on that picnic table. Then we can go for a row on the lake. When we get back, we can have dinner, take a twilight walk, and then I want to fuck you in the woods, right on the ground with the leaves and the stars above us. How does that sound?"
"Sounds amazing!" I admitted, pulling on my shorts and hiking boots. I was astounded to find that Sherry had planned not only activities for each day, but sex times, places and positions as well.
"One question," I asked, practically drooling as I watched her pull a pair of red, crotch-less panties over her magnificent ass. "When do I get to return the favor, if you know what I mean?"
Sherry glared at me in a very sexy, dominant way.
"When I think you're ready, and not one moment before," she replied. "If you serve your mistress well, maybe on the last day of our vacation, I'll let you fuck my pussy."
"I promise I'll serve you well, Mistress Sherry," I said, kissing her feet. That was the beginning of a long, hot week of wild, passionate sex the likes of which I'd never even dreamed possible!
It had been a long time since I'd done a ten mile hike, and Sherry lapped me the whole way.
"How do you think I keep these legs in such great shape?" she laughed, watching me pant and puff like an old man. I was ravished, but we ate only a small lunch of fruits and vegetables.
"Gives you stamina for sex," Sherry explained, sucking a carrot provocatively between her beautiful, full lips. "Which reminds me—clear off the dishes, it's party time, baby!"
She had me spread a thick blanket across the table top and told me to lie on my back, with my legs open, to the side. This position was awkward, but fairly comfortable. Then she whipped her six inch "clit" out from her shorts and slid it in. It still hurt, and took about a minute for me to relax my sphincter enough for her to penetrate, but once she did, it felt very good. I liked this position, because I could see her face and her tits and cock all at once. She pounded away, really reaming me good.
"Oh, yeah, Mistress!" I moaned under the powerful thrust of her moist, white thighs. "Fuck me!"
She went in "balls deep" and I could feel myself cuming, too. Her glans pulsated wildly, but instead of cuming up my butt, she quickly withdrew and squatted over my mouth, plunging her wet, hard rod between my lips, making me eat every drop of her luscious love lotion. When I'd drained the last drop, she withdrew.
"Time for our boat ride!" she said. Well, she fucked me in the boat, too, while I sat on her lap. That was very sexy, too, but we almost capsized! She didn't shoot again, and said she'd have to wait until tonight to build up some more of what she called "pussy juice." My ass ached less than yesterday, and she gave me some more of her aloe gel to cool down the burning. We rowed and stayed out on the lake until dinner time, watching the stars come out. It was very romantic, and I kissed her and sucked her big, sexy tits as we watched the star light twinkle. Then we rowed back for the shore.
Fortunately for my aching asshole, my stunning stewardess/mistress was too tired for the "after dinner fuck" she'd planned earlier that day. Instead, we just sat around and talked, which was nice and intimate. When I told her I worked for a mail-order lingerie catalog, she gave me a wry, knowing smile which I wouldn't understand until three weeks later.
The rest of the week we divided our time between leisure activities, like fishing, hiking, jogging and rowing, and sexual adventures. Her knowledge of positions seemed limitless, and I was more and more amazed by how good it felt when she reamed me deep and hard. Once, she had me lean up against a tree and literally hug it while she did me standing up. The bark dug into my skin as she drove her dick up my yielding rectum, and I had a little scar on my stomach for a few days, but it was an astounding combination of pleasure and pain.
On the fifth day of the second week, Sherry sprung another surprise on me. When we got back from another combination row boat trip and on the water fuck session, there was a white Ferrari parked in the dirt driveway outside the cabin. When we got inside, there was a beautiful, buxom redhead in a lovely, crinoline dress, white stocking and boots sitting on the sofa, sipping a glass of our champagne.
"Monique!" Sherry cried, rushing in to hug the woman. They shared a very passionate, wet kiss. I remembered wondering if Sherry was bisexual, but didn't I found out soon that this woman was "special" like my blonde mistress.
"This is Nick," Sherry said. Monique held out her hand for me to kiss, then simply stood up and thrust my head under her skirts. Nestled between her fleshy, stockinged gams was the biggest cock I'd ever seen! I'd read magazine "true stories" where the guys claimed to have nine inches, but this torrid transsexual really was packing a nine-inch rod in between her luscious thighs. I got to work on that huge horse fucker right away, sucking and lapping it like a huge popsicle. Meanwhile, Sherry got me up on all fours and began ass fucking me doggy style. Her thrusts forced me further and further down Monique's long, tasty tool. I didn't think I could take all nine inches into my mouth without gagging, but I managed somehow. Then, just as both of my shemale mistresses were about to come, they changed places!
Sherry's throbbing tool in my mouth kept me from screaming as Monique forced her huge fuck stick up my asshole. It felt like she was going to split me in half with that monstrous dick. She straddled me with those stocking-clad legs and pumped hard, driving more and more of her pulsating, probing prick up me. I almost fainted as Sherry came in my mouth and Monique came in my ass simultaneously. Sherry was exhausted, and withdrew her "clit" from my mouth, but Monique was just getting started. Her gigantic rod was still impaling my ass, and she led me over to the bed and initiated the longest, wildest night of solid fucking I'd ever experienced. We did it in every position, and she never seemed to run out of jism, coming gallons up my butt and into my eager mouth. She even fucked me awake the next day. Then all three of us went into the shower, where Monique screwed Sherry's pretty little ass while Sherry mounted me. Then they switched. We did that all day, never leaving the cabin. By that night, we were all so drained and sore, we could hardly move!
The next two days were a wild, non-stop fuck fest. I got to fuck Monique's hot, tight butthole, which felt incredibly deep, satiny and sexy, but Sherry never did let me enter her "pussy" as she called her great, round little ass. Monique also let me "tit-fuck" her, wrapping her huge, soft breasts around my cock while I pistoned in and out. That felt great. She also let me fuck her ass cheeks without penetration, and do "femoral" intercourse between her gorgeous gams, both naked and in silky, sexy stockings. She even let me screw her armpit once! Finally, it was time to leave, and we said our sad goodbyes. Sherry gave me one last blistering anal session in the backseat of the 4 X 4, then she and Monique left together.
When I got back to California, I could hardly sit down for a month! Things got hectic at work pretty fast. I thanked Terry for the cabin, and said I'd had a good time, never letting on to the crazy, wild week I'd had. But one night, when the others had gone home, Terry called me into her office, and locked the door!
"So," she said in a very sultry tone of voice. "How did you like my little friends Sherry and Monique?"
I gasped for air. How could my boss have known about what had happened on my vacation?
"How did you know?" I asked, shocked.
Terry laughed. As she sat on the edge of the desk, she kept crossing and uncrossing her legs. She was wearing a pair of our green, sheer stockings. I'd always thought Terry had beautiful legs, and now I was getting glimpses of her upper thighs, which were just as nice. Was she trying to seduce me?
"I lied a bit," she admitted, laughing again. "It's really Sherry's cabin. I just happen to have a key. You see, I really needed you to meet Sherry and Monique."
"Needed?" I asked, confused. "Why?"
Without answering, she stood up and whipped off her skirt, and then did a slow, sexy striptease out of her panties. I saw a normal looking patch of brown pussy hair between her slender, curvy thighs. Then she laughed again, and opened her legs, revealing another shemale surprise! Even with Sherry and Monique, there were slight, very subtle manly things about their figures or faces that might give them away to someone who knew transsexuals, but Terry was 100 percent feminine. I'd never have guessed in a million years that my beautiful boss had a "boy toy" between her legs!
"I've been attracted to you for years," the sultry shemale admitted, stroking her cock to full erection. "But I didn't know how to approach you. Now that I know you like my kind of woman, why don't we stay late and have some fun?" I dropped to my knees and took her long, lovely cock into my mouth.
Five minutes later, Terry had me bent over her desk and was jamming her seven-inch shaft up my eager, accepting asshole. She was every inch as talented at anal love-making as sexy, stewardess Sherry, but not as painfully large as Monique, making her dick feel just right as it worked its way deep inside me.
"Oh, yes!" I screamed as I felt her engorged glans pulsate and cum in me. "Terry, I love you! Fuck me again!"
She was happy to comply, and later that year, we got married—by Monique! It was a hell of a honeymoon, and I'm sure glad I found a whole new world at 35,000 feet!
My introduction into the sultry, steamy world of shemales came (and I mean came!) at 35,000 feet, on a plane flight to the Northwest.
I had been working myself to the bone, staying until ten or eleven at night, coming back in at six o'clock in the morning, and I guess the stress was visible. My boss, Terry, a very pretty, sexy lady (who I later found out was a hot-bod tranny too!) called me into her office.
"Nick, you need to get away, and I know just the place," she said, handing me a set of keys. "I own a cabin in Northern Washington. There's no phone, no television, no radio. Just you and the Great Outdoors."
"But it's out busiest two weeks!" I protested, imaging the whole mail order lingerie house would collapse if I was gone for a minute, let alone two weeks.
"It's an order, Nicholas!" Terry said. "Alan and Denise can fill in for you. You're under too much stress. You need to unwind. Then you can come back refreshed and ready for the fall inventory."
I argued, but to no avail. I never could win an argument from the tall, willowy brunette. She called and made the plane reservations for the following week.
Terry had booked me in the First Class cabin on a small, charter airline. She'd given me maps to the cabin, and arranged for a rental car at the airport. I threw together some of my old camping gear. Maybe she was right. Maybe I needed to away from people, constantly ringing telephones and the Internet for a while. By the time I'd boarded the plane, I was beginning to look forward to two weeks of solitude.
First Class was very comfortable. I'd never traveled that way before, and there were lots of little perks, like comfy, overstuffed seats with arm rests, personal VCR's, and of course, the service…which is where my wild sexcapades started. Our stewardess was real knock out. She was tall, leggy strawberry blonde with sparkling blue eyes and a very tight blue uniform. Her figure would have given a super model a run for her money.
"Hi, I'm Sherry," she said, smiling broadly. "If there's anything you need to make your flight more enjoyable, just let me know."
She said the same thing to the ten other First Class passengers, so I figured it was a standard, prepared speech. But as the long, eight hour flight continued, she seemed to be paying more attention to me than the other passengers. When my water glass was empty, she'd swoop down and fill it up, giving me a mouth-watering eyeful of cleavage. She brought my meal before anyone else's, and kept fluffing my pillows and pouring me champagne. She gave me a whole series of sly winks and smiles I was sure was a prelude to seduction.
About halfway through the flight, most of the other First Class passengers fell asleep, except for an old man who'd never taken his eyes from his lap top computer the whole trip. Sherry sauntered into the isle and whispered,
"Follow me if you want to join the "Mile High Club," Nick!"
Wow! What a trip this was going to be! Not even four hours away from the office, and I was about to get laid by a hot blonde!
I carefully followed her up to the front of the plane, to a spacious, empty lavatory. She locked the door behind her and grabbed me, planting a hot, wet kiss on my lips which I eagerly returned. I held her tight and caressed her round ass and upper thighs as we continued our lip lock, tongues probing like wild a****ls. She pulled off her top and undid her sheer, black lace bra, then brought my mouth down to lave her tits with kisses. They were big and full and beautiful, with red nipples like pencil erasers which jumped to erection under my sucking and nipping. I kissed her long, flat stomach down to her navel, where I could just make out the golden shimmer of her pubic hair.
"Just as second, honey," she whispered. "I'll make it easier for you."
She started to slide out of her mini-skirt, then smiled and said "Turn around and don't peek, bad boy!"
I laughed and faced the wall. I heard the silken swoosh of her tight dress hitting the floor.
"Close your eyes and follow me," she said, taking my arms. "Keep them closed!"
She led me over to a little padded shelf next to the toilet and sat down. She told me to kneel down in front of her. I could smell the musky perfume of her pussy wafting up to my face. I could hardly contain my excitement at the thought of plunging my hungry lips and tongue into that blonde bush.
"O.K.," she said with a slight giggle. "You can open your eyes now."
When I did, I nearly fainted. She did indeed have a healthy patch of golden pubic hair, but rising up from that furry forest was a huge, pink cock!
I was stunned speechless. How could this lovely creature have a penis? It seemed impossible. I wanted to run. I wanted to jump off the airplane. I wanted—to suck her cock. The sight of it poking up from those milky upper thighs, between those sheer blue stockings made me so hot, I just couldn't resist. I dropped my mouth down and began to shower her six inch "surprise" with kisses. I tasted hot and spicy as I took her dripping glans into my mouth and sucked gently. She took my head in her hands and slid me down the luscious length of her stiff shaft, until my face was nestled up against her pubic hair. I sucked and gulped for all I was worth. It was a strange sensation, like putting a sausage into your mouth, but not swallowing it. This was my first blow job, and I hoped it was giving her pleasure.
She began to gyrate her hips, drawing my head back towards the top of her rod, "mouth fucking" me in series of hot thrusts and bucking motions. Suddenly, she gave a little moan and pulled her dick out of my mouth. It glistened hard, powerful and gorgeous in front of my face.
"That's not where I want to come," she cooed in a seductive voice. My face went white with both fear and anticipation. I had a hunch I knew where she wanted to shoot her load.
"You don't mean?" I started.
"Oh, yes I do!" the sultry shemale purred. "Don't worry. I know you're an ass virgin, so I'll be gentle. Now come on. You'll love it, I promise!"
I don't know what amazed me more, the fact that I didn't run screaming from that lavatory, or the fact that she was right about being ass-fucked!
She had me strip and lean against the stall door, facing away from her. Then she lubed my asshole with KY Jelly and slid a long slim finger up my anus. I'd had girlfriends do that, so it didn't really feel bad, just a bit uncomfortable as she spread the cold gel around my asshole. After about two minutes, she pushed as second finger in and began to wriggle them around, spreading my butt cheeks with her hands. At first it burned, but soon it started to feel very erotic, and I felt myself getting a huge boner.
"Mmm," Sherry said. "Looks like you're ready for the ride, big boy!"
She gave my cock a firm yank, and positioned herself behind me. I felt a tremendous pressure as she shoved her hot, wet glans up past my asshole. She left it there for a few minutes, allowing me to "loosen up" and adjust to the feeling. Then she rotated her hot hips and sent another inch up my virgin ass. I screamed. It felt like my ass was on fire, but each time she pushed more of her big bone into me, my own dick got harder and wetter. Finally, she had all six inches up me, and then she began to fuck me in earnest, thrashing and bucking wildly. I moaned in both pain and pleasure as she gave me an expert reaming. She pulled my pelvis close and thrust deeper, making me squeal with delight. Sweat poured off my back as she continued her hot, rhythmic thrusts. Suddenly, she gasped, shoved me flat against the door and really jammed her whole six inches up me. I cried out as I felt her engorged cock head pulsate and her steaming come shot up my rectum. I'd never felt anything that sexy in my whole life! I came a few seconds after she did.
Her cock was still rock hard up my ass, and despite the burning, screaming pain in my rear, I asked her, almost begged her, to fuck me again, which she did happily, lowering me to the floor to take me "doggy style." She didn't come a second time, but her dick was still erect, so she left it in. It was starting to feel like it belonged in there. Finally, after about an hour had passed, we cleaned each other up, got dressed and went back to the cabin. I slept, exhausted and sore, the rest of the flight.
"Have a nice vacation, Nick," Sherry said, winking at me as I left the plane and headed for the rental car agency.
We weren't alone, so I couldn't thank her, or kiss her, for the marvelous new experience she'd given me. I figured I'd never see the tall, leggy strawberry blonde shemale again. It took me ten hours of driving to discover how wrong I was!
When I got to the rental counter, I discovered that I'd forgotten to take the most important thing—the map to Terry's cabin! I could have sworn it was in my left jacket pocket, but it wasn't there. I called her up on my cell phone and she gave me the instructions. I didn't tell her about my bizarre, amazing entry into the "Mile High Club."
Because I'd have to drive on tiny, winding dirt roads, I'd rented a 4 X 4, sports utility vehicle. I began to regret that decision as soon as the highway ended, because every bump (and there were about ten miles of nothing BUT bumps!) made my recently reamed rectum scream with renewed pain and soreness. I wasn't going to be in any shape to go hiking!
It was dark when I finally saw the tiny cabin at the end of a long, lonely road surrounded by tall Douglas firs. There was a lake on the other side of the cabin, but I didn't see any signs that there were other cabins. Terry said the lights were on a timer switch, so I wasn't surprised to see lights coming from the windows. But I was surprised to find that the door was open! I hesitated. Was there a burglar in there, possibly armed? Should I drive the fifteen miles to the nearest town and call the cops (my cell phone wouldn't work this deep into the woods)? I fished around on my key ring and found that the key was missing! That was impossible! I'd only put it on this morning! I was beginning to feel a bit spooked, when I saw a figure limned in the doorway, and a flash of golden hair.
"What took you so long?" Sherry teased. She was dressed in a tight, black lace catsuit, and she handed me a perfectly mixed martini, no olive, just like I liked them.[ILL. # 3-Insert of Sherry in door frame, dressed in lace catsuit, outline of her cock just visible beneath the material, holding out Martini, looking very "Lauren Bacall"-i.e., seductive, eyes flashing, ultra-sexy.]
"How did you get here?" I gasped. It seemed impossible that she'd gotten to the secluded cabin before me.
"I fly charter, remember?" she said. "I'm not just a stewardess. I've got a private jet license. There's a hanger just across the lake, and I rented a row boat. That one, down there."
I saw the row boat tied to the small pier on the lake.
"That still doesn't tell me how you knew I was coming here," I said, lugging my bags into the cabin.
Sherry laughed and held up my map, the one that had gone missing from my pocket, and the key Terry had given me. I knew it was the same key because it had a blue key-guard around the top.
"Guilty!" the statuesque strawberry blonde smiled. "I took them when you were—busy."
"Why did you follow me?" I asked. "I mean—other than what happened on the plane, what's so interesting about me?"
"I like you," she said in a tone of voice that made my toes tingle. Boy, was she sexy! Even her voice was a sex organ! As she posed languorously on the sofa bed I could see just the barest outline of her powerful prick in the black lace around her "bush". That made me hot, and I knew before the night was through, I'd have to taste its exotic musks again.
"Why?" I continued, curious. A girl that good looking could have had anyone, and I wasn't exactly a hunk.
"You're fun to fuck," she admitted. "You didn't cry and moan like most of my men, and you didn't run screaming when you saw my—big clit. The last guy who let me do him that easily was a movie star. You'd faint if I told you who. He always plays such macho, straight roles."
She told me his name, and I was stunned.
"He employs a shemale maid at his house in Beverly Hills," she added. "And he told me whenever his wife's away on a picture shoot, she screws his ass all night long."
All this talk of sex was making me hot, but I was really too exhausted from that long, draining drive to do anything about it.
"Well, I guess two is better than one," I said. "Though I was supposed to be coming here to get away from people."
"I'm not people," she smiled enigmatically. "I'm your mistress, and you will obey me. Now come here and give me a hello kiss."
Who was I to argue with a woman that gorgeous? A kiss was about all I could manage, though.
"Oh, poor boy," Sherry said. "Tired from your drive, huh? Next time we come up here, you can fly with me. Since today was your first time, I'll let you rest and rebuild your strength. But I've got a lot of activities planned for tomorrow, so get a good night's sleep!"
"I can guarantee that!" I said, kissing her again, and giving her cock a clandestine caress beneath that sexy cat suit.
"Here," she said, fishing a small plastic tube from her purse. "This will help loosen you up for me, and get rid of the soreness at the same time."
"What is it?" I inquired, squeezing out a dab of oily, green stuff which looked like toothpaste.
"My special recipe," she explained. "Aloe vera, plus a muscle relaxant. Here, bend over and let me apply it."
The touch of her velvety soft hands on my ass sent erotic shivers up my spine as she smoothed the cooling ointment around my sore asshole. I kissed her one more time, then I had to go to bed. We unfolded the sofa bed, and I collapsed beside my strawberry blonde goddess, and was asleep in minutes.
The next morning, we took a sexy shower, soaping each other's slick, wet bodies up and down. I gave her another blow job, then she gave me one that made my hair stand on end! Her lips and tongue were so skilled that I came in about two minutes. Then she did something both sexy and a bit disgusting. She didn't swallow my hot semen, instead she straightened up and kissed me, spill my own cum into my mouth! Wow, did that feel weird—but it tasted pretty good. I kissed her back, and we shared the cum between us, licking each other's lips until it was all gone.
"Now that you've had your nutritious breakfast drink," the tall blonde smiled playfully. "I'd like to go on a hike around the lake. It's about ten miles, so that should get us back here in time for lunch. After lunch, I want to fuck you on that picnic table. Then we can go for a row on the lake. When we get back, we can have dinner, take a twilight walk, and then I want to fuck you in the woods, right on the ground with the leaves and the stars above us. How does that sound?"
"Sounds amazing!" I admitted, pulling on my shorts and hiking boots. I was astounded to find that Sherry had planned not only activities for each day, but sex times, places and positions as well.
"One question," I asked, practically drooling as I watched her pull a pair of red, crotch-less panties over her magnificent ass. "When do I get to return the favor, if you know what I mean?"
Sherry glared at me in a very sexy, dominant way.
"When I think you're ready, and not one moment before," she replied. "If you serve your mistress well, maybe on the last day of our vacation, I'll let you fuck my pussy."
"I promise I'll serve you well, Mistress Sherry," I said, kissing her feet. That was the beginning of a long, hot week of wild, passionate sex the likes of which I'd never even dreamed possible!
It had been a long time since I'd done a ten mile hike, and Sherry lapped me the whole way.
"How do you think I keep these legs in such great shape?" she laughed, watching me pant and puff like an old man. I was ravished, but we ate only a small lunch of fruits and vegetables.
"Gives you stamina for sex," Sherry explained, sucking a carrot provocatively between her beautiful, full lips. "Which reminds me—clear off the dishes, it's party time, baby!"
She had me spread a thick blanket across the table top and told me to lie on my back, with my legs open, to the side. This position was awkward, but fairly comfortable. Then she whipped her six inch "clit" out from her shorts and slid it in. It still hurt, and took about a minute for me to relax my sphincter enough for her to penetrate, but once she did, it felt very good. I liked this position, because I could see her face and her tits and cock all at once. She pounded away, really reaming me good.
"Oh, yeah, Mistress!" I moaned under the powerful thrust of her moist, white thighs. "Fuck me!"
She went in "balls deep" and I could feel myself cuming, too. Her glans pulsated wildly, but instead of cuming up my butt, she quickly withdrew and squatted over my mouth, plunging her wet, hard rod between my lips, making me eat every drop of her luscious love lotion. When I'd drained the last drop, she withdrew.
"Time for our boat ride!" she said. Well, she fucked me in the boat, too, while I sat on her lap. That was very sexy, too, but we almost capsized! She didn't shoot again, and said she'd have to wait until tonight to build up some more of what she called "pussy juice." My ass ached less than yesterday, and she gave me some more of her aloe gel to cool down the burning. We rowed and stayed out on the lake until dinner time, watching the stars come out. It was very romantic, and I kissed her and sucked her big, sexy tits as we watched the star light twinkle. Then we rowed back for the shore.
Fortunately for my aching asshole, my stunning stewardess/mistress was too tired for the "after dinner fuck" she'd planned earlier that day. Instead, we just sat around and talked, which was nice and intimate. When I told her I worked for a mail-order lingerie catalog, she gave me a wry, knowing smile which I wouldn't understand until three weeks later.
The rest of the week we divided our time between leisure activities, like fishing, hiking, jogging and rowing, and sexual adventures. Her knowledge of positions seemed limitless, and I was more and more amazed by how good it felt when she reamed me deep and hard. Once, she had me lean up against a tree and literally hug it while she did me standing up. The bark dug into my skin as she drove her dick up my yielding rectum, and I had a little scar on my stomach for a few days, but it was an astounding combination of pleasure and pain.
On the fifth day of the second week, Sherry sprung another surprise on me. When we got back from another combination row boat trip and on the water fuck session, there was a white Ferrari parked in the dirt driveway outside the cabin. When we got inside, there was a beautiful, buxom redhead in a lovely, crinoline dress, white stocking and boots sitting on the sofa, sipping a glass of our champagne.
"Monique!" Sherry cried, rushing in to hug the woman. They shared a very passionate, wet kiss. I remembered wondering if Sherry was bisexual, but didn't I found out soon that this woman was "special" like my blonde mistress.
"This is Nick," Sherry said. Monique held out her hand for me to kiss, then simply stood up and thrust my head under her skirts. Nestled between her fleshy, stockinged gams was the biggest cock I'd ever seen! I'd read magazine "true stories" where the guys claimed to have nine inches, but this torrid transsexual really was packing a nine-inch rod in between her luscious thighs. I got to work on that huge horse fucker right away, sucking and lapping it like a huge popsicle. Meanwhile, Sherry got me up on all fours and began ass fucking me doggy style. Her thrusts forced me further and further down Monique's long, tasty tool. I didn't think I could take all nine inches into my mouth without gagging, but I managed somehow. Then, just as both of my shemale mistresses were about to come, they changed places!
Sherry's throbbing tool in my mouth kept me from screaming as Monique forced her huge fuck stick up my asshole. It felt like she was going to split me in half with that monstrous dick. She straddled me with those stocking-clad legs and pumped hard, driving more and more of her pulsating, probing prick up me. I almost fainted as Sherry came in my mouth and Monique came in my ass simultaneously. Sherry was exhausted, and withdrew her "clit" from my mouth, but Monique was just getting started. Her gigantic rod was still impaling my ass, and she led me over to the bed and initiated the longest, wildest night of solid fucking I'd ever experienced. We did it in every position, and she never seemed to run out of jism, coming gallons up my butt and into my eager mouth. She even fucked me awake the next day. Then all three of us went into the shower, where Monique screwed Sherry's pretty little ass while Sherry mounted me. Then they switched. We did that all day, never leaving the cabin. By that night, we were all so drained and sore, we could hardly move!
The next two days were a wild, non-stop fuck fest. I got to fuck Monique's hot, tight butthole, which felt incredibly deep, satiny and sexy, but Sherry never did let me enter her "pussy" as she called her great, round little ass. Monique also let me "tit-fuck" her, wrapping her huge, soft breasts around my cock while I pistoned in and out. That felt great. She also let me fuck her ass cheeks without penetration, and do "femoral" intercourse between her gorgeous gams, both naked and in silky, sexy stockings. She even let me screw her armpit once! Finally, it was time to leave, and we said our sad goodbyes. Sherry gave me one last blistering anal session in the backseat of the 4 X 4, then she and Monique left together.
When I got back to California, I could hardly sit down for a month! Things got hectic at work pretty fast. I thanked Terry for the cabin, and said I'd had a good time, never letting on to the crazy, wild week I'd had. But one night, when the others had gone home, Terry called me into her office, and locked the door!
"So," she said in a very sultry tone of voice. "How did you like my little friends Sherry and Monique?"
I gasped for air. How could my boss have known about what had happened on my vacation?
"How did you know?" I asked, shocked.
Terry laughed. As she sat on the edge of the desk, she kept crossing and uncrossing her legs. She was wearing a pair of our green, sheer stockings. I'd always thought Terry had beautiful legs, and now I was getting glimpses of her upper thighs, which were just as nice. Was she trying to seduce me?
"I lied a bit," she admitted, laughing again. "It's really Sherry's cabin. I just happen to have a key. You see, I really needed you to meet Sherry and Monique."
"Needed?" I asked, confused. "Why?"
Without answering, she stood up and whipped off her skirt, and then did a slow, sexy striptease out of her panties. I saw a normal looking patch of brown pussy hair between her slender, curvy thighs. Then she laughed again, and opened her legs, revealing another shemale surprise! Even with Sherry and Monique, there were slight, very subtle manly things about their figures or faces that might give them away to someone who knew transsexuals, but Terry was 100 percent feminine. I'd never have guessed in a million years that my beautiful boss had a "boy toy" between her legs!
"I've been attracted to you for years," the sultry shemale admitted, stroking her cock to full erection. "But I didn't know how to approach you. Now that I know you like my kind of woman, why don't we stay late and have some fun?" I dropped to my knees and took her long, lovely cock into my mouth.
Five minutes later, Terry had me bent over her desk and was jamming her seven-inch shaft up my eager, accepting asshole. She was every inch as talented at anal love-making as sexy, stewardess Sherry, but not as painfully large as Monique, making her dick feel just right as it worked its way deep inside me.
"Oh, yes!" I screamed as I felt her engorged glans pulsate and cum in me. "Terry, I love you! Fuck me again!"
She was happy to comply, and later that year, we got married—by Monique! It was a hell of a honeymoon, and I'm sure glad I found a whole new world at 35,000 feet!
Mei
- 02.05.2022
- 40
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Sexy Stewardess on a Hot Flight Part One
- 2 years ago
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The Stewardess
- 4 years ago
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