I was especially satisfied by a handsome stud pilot who flew me over to Catalina for the weekend in his private plane, then treated me like his sex slave all weekend, even having me perform on two other men to increase his pleasure. I dressed up in a sexy stewardess outfit for the flight over, wearing a miniskirt and blouse with a sexy white lace panty and bra underneath. I wore sexy white fishnet stockings to draw attention to my hot legs men liked to rub so much. I added a pair of white stiletto high heels and I was ready to give my handsome pilot a good blow job all the way to Catalina like the slutty stewardess I was.
Stewardesses get to fuck a different man in a different city, every night. They get to fuck any man and make him a member of “the mile high club” while they work. And, as I was about to find out, they get to suck on the handsome pilot’s big hard cock in the cockpit while he flies the plane. I was going to love being a stewardess. They get as much dick as they possibly can want. That’s why I liked being a call boy so much, for all the dick I was getting, too.
Wearing sexy lace panties and little lace bras always gets me ready to suck men’s cocks. As soon as I put them on I’m ready to suck a big one, so by the time I arrived at the airport I was really horny for my stud pilot’s cock. A girl can get just as turned on thinking about a man’s big cock as he can thinking about her hot ass. This was the case when I arrived at the airport in Burbank for the flight to Catalina with my client the agency hooked me up with for the weekend. I was so horny for his cock I would have sucked it for free.
Far too many men don’t know how much their cocks are craved by women when they wear their sexy lingerie. These are the clothes we enjoy wearing when we suck cocks because it makes them bigger and harder for us. And the bigger and harder a man’s cock is, the more a woman can enjoy it. Being a twenty-year-old crossdresser who never turned down the opportunity to suck a man’s cock, I had gotten quite good at turning men on for me to suck by wearing sexy women’s clothing.
My plan was to strip out of my blouse and miniskirt as soon as I got on the plane. Then wearing just my sexy white lace panties, lace bra, white fishnet stockings and stilettos, I would go down on my client’s cock like a horny stewardess eating her in flight meal. It was what I was looking forward to all the way to the airport. Down in my lace panties, my clitty dick was so turned on thinking about all the hard cock I was going to get being a sexy stewardess, all weekend.
The pilot was a big, handsome, strong man, the kind I liked to let fuck me hard for hours. My ass can take a hard cock pounding it as much as any pussy can, so my plans for the weekend began to grow as soon as I saw my stud pilot. I’m sure there isn’t a stewardess in the world who wouldn’t want to be in his cockpit sucking on his cock. Sexy stewardesses are such horny, cock-loving sluts.
“Hi. I’m Courtney,” I said upon arriving.
“I’m Phillip,” he replied.
“Well, Phillip, I can’t wait for you to fill my lips with your big one,” I said smiling.
“Oh, babe, you sure are sexy,” he said.
He reached behind me and grabbed my ass cheeks with both hands and he pulled me up to him and kissed me full on the lips like a stud who meant business. When our lips parted, he held me in his arms like a sexy little girly boy. It was always special to me to be kissed by a man and held in his arms. I rubbed my hard clitty dick against his boner and felt it growing down in his pants. It wouldn’t be long and I’d be sucking it good for him.
I never planned on becoming a tranny call boy. It just kind of happened. I wore sexy girl hot pants and miniskirts to the adult bookstore near my house when I was sixteen years-old. And I learned the men coming out of the video booths there were glad to pay me to give them blow jobs. At first, I did it as a hobby just to give me extra money to buy sexy lingerie to wear. One thing led to another and, before I knew it, I was a full-fledged male prostitute sucking and fucking men for money every night of the week.
Now, I was twenty years-old and I had moved to L.A. where I was told a hot tranny call boy can make lots of money servicing big handsome studs who know how to treat a tranny. Although I was making more money in L.A., it was more expensive to live in California, so I was glad when I was hired by Phillip to be his stewardess for the weekend and service two pilot friends of his, too. It meant I was getting a thousand dollars each from them for a three thousand dollar weekend. I loved thinking like a whore about all the money I was making giving men pleasure with my lips and my body.
But being held by a handsome stud man who I would have sucked and fucked for free was such a turn-on for me. I couldn’t wait to unbutton his shirt and rub my fingers through his chest hair like a horny girl because that’s exactly what I felt like in my stud pilot’s arms, just a horny little slut who can’t get enough cock.
“Mmmm, you’re a good kisser, Phillip,” I said.
I reached down with my right hand and rubbed his hard cock still growing bigger down in his pants. It was a big fat cock that turned me on the second I touched it.
“Yeah, baby,” said Phillip. “That’s what you’re going to be taking care of for me, all weekend.”
“It feels so big. I love it, darling,” I replied.
He pulled me closer to him and kissed me again while I reached down and rubbed his stiff cock. I felt like a cum-loving slut who couldn’t wait to put her lips around the dick of this handsome man with brown hair and blue eyes whose lips felt so good pressed against mine. From my rubbing it for him, his cock was fully erect and ready to be sucked and I couldn’t wait to get on the plane and pull his zipper down and get at it. Finally, our lips parted.
“I can’t wait to suck this for you, baby,” I said.
“Well, let’s get onboard and you can get started,” he replied.
Phillip set me down and led the way as I entered the plane carrying my overnight bag. I was surprised when I entered and there were two handsome men already on the plane. Phillip introduced them to me as his co-pilots, Dick and Harry. I don’t know if those were their real names, but I like hairy dicks and I knew I would love Harry and Dick, too.
As soon as the introductions were complete, I unbuttoned my blouse and took off my miniskirt and stripped down to my white lace panties, bra, fishnet stockings and stilettos. Now, I felt like a total whoreboy ready to service these three big studs all weekend. Oh, how I loved wearing sexy things and turning men on with my sexy body.
When I was sixteen and I first started wearing female underwear, I thought maybe I just had a panty fetish. But after I wore panties for my first boyfriend and I saw how hard it made his cock, I became a cock-loving slutboy who can’t get enough of men’s big cocks. So, you can imagine how turned-on I was being with three big studs wearing my sexy little bra and panties and fishnet stockings and ready to take off for our weekend excursion to Catalina.
Phillip sat down in the pilot’s seat and motioned for me to sit in the co-pilot’s seat beside him. Harry and Dick were sitting in the passenger seats behind us. Knowing they were going to be watching me suck on Phillip’s big fat cock while we took off let me know their cocks were going to be hard for me to suck next when I finished Phillip. Oh, the pleasure of being a slutty stewardess and knowing I would have three men’s cocks to suck in the cockpit on every flight was a big turn-on for me.
“Mmmmm, you look hot, Courtney,” said Phillip. “Your titties fill out that bra nicely.”
“Thank you, Phillip,” I replied. “What you have down in those trousers looks good to me, too.”
There was a big bulge in his crotch that I gave him when he picked me up and I was rubbing his dick for him while we kissed. Phillip licked his lips.
“What you have in those sexy little panties looks good, too.”
He was staring down at my perfectly-shaped seven inch hard boner down in my little white lace panties. I smiled at him.
“Big boy,” I said. “I’ve been wanting to suck your cock on take-off, all week. So, you’re going to have to wait to have me when we’re in the air. I get to suck you, now.”
I reached over and loosened his belt and unbuckled it. It is a pleasure I really enjoy as a tranny call boy. Every sexual escapade usually starts with me pulling down a man’s pants and knowing I’m going to get his cock to enjoy. But on this flight, there were three men’s pants I would get to pull down and I couldn’t wait to get started. I knew seeing me sucking on Phillip would really turn on Dick and Harry, so their cocks would be good and ready for me when I finished Phillip.
As a tranny hooker and call boy, I learned that lots of men are into different kinky stuff. But sucking on a pilot’s cock during take-off was going to become one of my favorite kinky things to do. First of all, it’s illegal to do so I had to stay really low so the men in the control tower didn’t see me. And then there is the rush of speed of the plane going over a hundred miles per hour and the thrill of lift-off. I loved being about to do it for the first time.
When I got his pants and underwear down, I finally saw that hard cock I loved rubbing when I was in his arms a few minutes before. It was 8 inches cut and it was big and thick. It was at least 6 inches round. I realized, right away, what a tight fit it was going to be in my hot little ass. The reason Phillip brought along Harry and Dick was so he could fuck me in the ass for hours while he watched me suck both of them. Now, I was getting nervous like a girl wondering if she could handle all a man had to give her in her pussy. Although I had had lots of longer cocks than Phillip’s in my manpussy, I had never had one quite as thick as his.
I looked him in the eyes and said, “You have a nice one, captain.”
“I’m glad you like it,” he replied. “I’ve been wanting you to suck it, all week.”
“Well, now you’re going to get it, honey. I want your first blow job of the weekend to be really special, so why don’t you fire up those engines and we can take off with you cock in my mouth.”
That was all the encouragement he needed and he was ready. He started the plane and we started taxiing to the runway while I assumed my position to be able to suck his hard cock while he flew the plane. It was a little tricky, but it was a lot of fun. Down in my panties, my clitty dick was spewing out pre-cum as I took his big fat cock in my hand for the first time.
I paused to make a special memory of being a sexy, slutty stewardess sucking on her first handsome pilot’s cock during take-off. I smiled at Dick and Harry. Then I put my lips on Phillip’s cock for the first time. It was amazing. The girth on his cock was so large that I had to open my mouth wider than I had for any other man. My stud pilot was definitely a mouthful, but I got half of his cock in my mouth on the first try.
“Oh, yeah, baby,” he said. “Oh, yeah.”
I pulled his big fat boner from my mouth and said, “You have such a big one, you stud. It’s going to take me awhile to get used to sucking it.”
“You’re doing great,” he said.
I put it back in my mouth and tasted his sweet pre-cum when I did. It was delicious. And I couldn’t wait for him to shoot his big cumload in my mouth, so I could swallow it for him while Harry and Dick watched me. I would swallow their cum next like the slutty stewardess they wanted me to be.
As a call boy, it was rare for me to have more than one client at a time. Sometimes I had two men who wanted to tag-team me, but having three men to please all weekend was one of the most special dates I ever went on as a tranny call boy. And I love remembering it, now.
We reached the end of the runway and Phillip got permission for take-off. He revved the engines and we started down the runway and I got extremely excited. I had his big fat cock in my mouth and he had my life in his hands. It was a daring blow job to give my stud pilot, but one he requested as a fantasy fulfillment so I had to do it. I felt the speed of the plane rushing through my body as we sped down the runway and I started sucking him faster and faster, too. I finally was able to deep throat him as we lifted off the ground and I knew he was loving it by all the moaning he was doing.
“Oh, fuck, you are good,” he said. “Suck that cock like a dirty whoreboy. Oh, fuck, you are good.”
I love being encouraged to suck cock and I was really doing a good job on him, considering how big and fat his boner was. I was sure that Harry and Dick couldn’t wait their turns as I slurped on Phillip’s cock like it was an ice cream cone that was melting.I was licking every part of it that my tongue could reach, especially around the big fat head of it each time I came up.
His cock was good and wet now from all of my sucking and I started to increase his pleasure by jerking him off at the same time I sucked him off.
“Baby, I’m gonna come in your mouth.”
Moments later, loads of his sweet cum started gushing into my mouth and I tried to lick it all up with my tongue, giving him lots of pleasure while I did.
“Yeah, babe,” he said. “Lick all that cum off my dick. Yeah! You’re a good little cum-guzzler, Courtney. That agency was right when they referred you to me. You’re fucking amazing.”
I was proud of my handiwork but with a mouthful of cum I couldn’t smile up at him. First, I had to swallow it after I took his cock out of my mouth. Then I could smile for him. I finally pulled his cock from my mouth and licked all of the cum off of the head of it for him with my tongue. He shot a big wet load and I was trying to suck it all up for my stud pilot like a good slutty stewardess.
“Fuck, you’re good,” he said as I licked up the last bit of his cum.
I felt like a cum queen bowing before her king. This was the special treat of being a tranny call boy, knowing I had satisfied a man the way women are supposed to do. It was the feeling I got when I satisfied men in the front seat of their cars as a tranny hooker. Now, it was in the cockpit of a plane. I suddenly thought, “My lips are earning their wings on this flight.” I felt like getting a sex change operation and becoming a fulltime stewardess just so I could satisfy lots of horny pilots during flights.
I tilted my head back and sucked down the big gobs of his cum that were in my mouth. I saw Dick and Harry smiling as they watched me. They knew I was going to suck down their cum next. I had to. It’s what every stewardess has to do. They all have to say, “Do you want coffee, tea or me? “
I suddenly remembered that Phillip had said he wanted to suck what I had in my panties.And my clitty dick was definitely in need of some attention. A girl can only go so long before she has to be satisfied by a man, so I decided to hurry and suck Harry and Dick and then Phillip could suck me.
I wiped some of the sweet semen from my lips with the back of my hand as I rose up from Phillip’s cock which was now getting soft. Looking out the window, I could see we were nearing the coast and headed out over the ocean. The flight to Catalina from Burbank isn’t very long, but Phillip was going to prolong it by flying over the Pacific Ocean for awhile before landing in Catalina.
Whenever I’m working as a tranny call boy, I only drink wine since it is a more feminine drink than beer which I prefer. I had some white wine in my overnight bag and I moved to the back of the plane to get it out of my bag. As I passed Harry, I reached down and felt his stiff dick in his pants.
“You’re next, big boy,” I said.
He smiled widely, knowing what a good job I had just done on Phillip. I took the bottle of wine from my overnight bag and handed it to Dick to open. The plane was a six-seater and Dick had moved to the last row of seats so I could sit next to Harry who was sitting behind Phillip’s seat. After Dick opened the wine bottle, he handed it to me. I held up the bottle in a toast.
“Here’s to having a great weekend with my stud boy pilots in Catalina.”
They all said “hear, hear” as I drank down the wine straight from the bottle to wash down all the cum I had just swallowed. I preferred my wine chilled, but it tasted great anyway. Since I knew I had two more hard cocks waiting for me to suck, I was glad I bought a large bottle of wine so I could wash down their cum, too.
Harry’s was the smallest of the three cocks and the easiest for me to suck. It was just over 6 inches long, fully erect, and not fat at all. He was a middle-aged man, the oldest of the three. He seemed to like me like a lot. His hair was brown but graying and he had a goatee on his chin and some tattoos on his arms, including one with an anchor that said “U.S. Navy.”
That weekend, Harry told me how he had his first tranny hooker when he was overseas in the Navy and he couldn’t believe how good she was. He said in the dark he couldn’t tell the difference between a tranny and a female hooker. After returning to the states, he developed an obsession with tranny hookers that made him sort of a connoisseur of tranny hookers. So, I really enjoyed sucking on him. I wanted to be one of his favorites so he would take me on more fun weekends. I got a big surprise when I pulled down Harry’s pants and I saw he was wearing sexy panties, too.
I smiled at him. “You’re wearing panties.”
“Yeah. I go both ways,” he said. “I like to take it in my ass, too.”
He looked at Phillip who looked back at him and they smiled at each other. I suddenly realized I had competition with satisfying Phillip’s dick, this weekend. It seemed like Harry wanted to be fucked by Phillip as much as I did. Of course, I could understand why. Phillip was a handsome thirty-four year old man with his own airplane and lots of money. But Harry, with facial hair and manly tattoos and hairy legs, wanting cock in his ass like I did intrigued me.
I went down on his cock and licked every bit of it for him and I even licked his balls with his cock in my mouth. After sucking Phillip’s fat cock, Harry’s was extra easy to suck. I was giving him great oral while Dick watched from the back seat. He was rubbing his cock through his pants while he watched me perform on Harry. With each cock I sucked on the flight, I had men watching me and enjoying it. They were definitely voyeurs and I’m an exhibitionist so it was agreat match. My clitty dick was still hard and it was making my lace panties soaking wet with hot pre-cum.
While I sucked on his cock, Harry reached down and started playing with my titties through my sexy white lace bra. It felt wonderful to be treated like a real girl by a man. He was playing with my titties like they do theirs. It was making me even hornier. I had been taking hormones and my titties were growing to a C-cup. Now, to have them felt up by a horny, older man felt really great. A lot of men don’t pay enough attention to a girl’s tits and they miss out on the pleasure of feeling them.
“Do you mind if I take your bra off?” said Harry.
I pulled his dick from my mouth and said, “No, not at all.”
I turned around so he could unhook the straps in back and I felt so feminine as he pulled the sexy white lace bra down my arms. Turning back around, I showed him my nice C-cup titties and he smiled at them like they were two ice cream cones.
“I know you want to suck on them, don’t you?” I said.
“I sure do,” he said, smiling.
“Okay,” I said. “I’ll jerk you off while you suck on my titties for awhile. But let me know before you cum so I can swallow it like I was planning to.”
I leaned back in the seat, wearing just my white lace panties, white fishnet stockings, and white stiletto high heels. Harry leaned over from his seat and took my left nipple in his mouth. The warmth of his tongue on my nipple sent a pleasant sensation all over my body. I don’t know if women get the same pleasure, but my body was loving having my nipple sucked.
Harry reached up and started feeling my right tit while he sucked on my left one. And I reached over and took his cock in my hand. Since his cock wasn’t very big it didn’t turn me on like Phillip’s did, so my clitty dick started getting soft down in my panties. I couldn’t let that happen since my clitty dick is what gave me the motivation to be a slut, just like a girl’s clit does for her.
With my right hand, I reached up and took Harry’s hand from my right tit and moved it down to my panties. He took the hint and started to rub my clitty dick through my lace panties while he sucked on my left tit. This stud was definitely a lady pleaser and he would have been my favorite, except that Phillip was so much more handsome. Yes, boys, I’m a shallow bitch who likes handsome men to suck and fuck. So, sue me.
Harry’s hand feeling my clitty dick through the sexy lace panty was making me hard again. But I suddenly wished I would have told him no when he asked to suck my tits. Now, it was taking longer to get Harry to cum and I wanted to be done all three blow jobs so Phillip could suck on me like he told me wanted to.
“Oh fuck, babe!” I said. “You’re getting me too turned on, playing with my clitty and sucking on my titty. I can’t stand so much pleasure. I want to finish sucking you off, now.”
I really was a dirty little slut who couldn’t wait to have Phillip’s handsome face between my legs and have him pulling down my panties for me. I pushed Harry’s hands away and positioned myself so I could suck on his cock some more. Behind us, Dick was enjoying the show I was giving him. I love having a voyeur watching me suck a man’s cock. I looked back at him to let him know he was next and he smiled at me.
Taking Harry’s cock back in my mouth, I licked the full length of it and I tasted his sweet pre-cum when the tip of my tongue reached the pink head of it. He wasn’t offering me encouragement by moaning like Phillip had so it was harder for me to get into. But I finished him off with a flurry of head bobs that drew his hot cum straight up the full length of his cock and into my mouth. It wasn’t nearly as much cum as Phillip had shot in my mouth and I swallowed it quite easily. After I swallowed his cum, Harry leaned over and kissed me on the lips.
“You were great, doll,” he said.
I didn’t understand why he said I was great when I finished when he hadn’t said anything while I sucked him off really good. I learned later that it was so he could judge how good a cocksucker I was without making me work harder than I normally would. Like I said, he was a connoisseur of trannies and he later told me I was one of the best he ever had. That really makes a girl feel good, guys.
After putting my sexy little white lace bra back on, I was ready for Dick who was sitting in the back seat smiling at me when I turned around. He was a tall and stocky twenty-eight year old bisexual who was into group sex and liked sucking dick and being fucked in his ass, too. I would learn later that that was why Phillip brought Harry and Dick because they were both willing to be fucked in the ass and Phillip was an assman who couldn’t get enough ass to fuck. That’s why he hired me, so he could fuck my ass, too. He loved fucking men in the ass with his big fat cock and hurting them. It was his biggest turn-on.
I had one more man to suck off and then I would get to have my clitty dick sucked by my handsome pilot who was busy flying the plane over the Pacific Ocean on a circling route to Catalina. Now, Harry and Dick switched seats and I suddenly felt like a dainty little chick. Dick was the tallest of the three men, around 6 foot 2, and his broad shoulders were an absolute turn-on. He was the kind of man I really liked to be fucked by the most. I guess every girl has her favorites and tall men with broad shoulders are mine.
“Well, hello, handsome,” I said. “I guess you’re last but not least. I bet you have the biggest one for me.”
“I’m so fucking horny for you, right now, bitch,” he replied.
“I love a man who calls me bitch. It means he wants to get rough with me in bed.”
“I’ll get rough with you,” said Dick. “I do have the biggest cock here. And I have the biggest set of balls to slap your tight little ass with while I fuck you.”
“Oh, boy, I can’t wait,” I said smiling. “Let me see this big cock you’re talking about.”
I reached for Dick’s belt buckle and loosened it for him. He helped as I pulled his pants down, revealing a 10 inch cock and a massive set of balls that probably held a quart of hot cum in them. I felt like a girl who just opened a wonderful gift, all of the sudden. Here was a beautiful specimen of manhood and I asked him if I could take a picture of it with my cellphone. He laughed at the idea.
“Sure, why not?” he said.”You’re the one who made it that hard. Watching you suck on Harry and Phil was great entertainment.”
I got into my overnight bag and took out my cell phone and I took a picture of Dick’s big 10 incher. I wanted the picture so I could play with myself later while I looked at it. That’s the thing with me, I get turned on the most by men’s big boners and Dick definitely had a nice one to look at.
“Thanks,” I said.
“Anytime,” he said, smiling.
I put my cell phone away and sat back down next to Dick. Harry had moved to the co-pilots’ seat next to Phillip. That way they would both have a good view of me sucking on Dick’s gorgeous cock in the seat behind them. Oh, my gosh, it was like a rock star’s cock, the kind groupies go wild for. After Harry’s 6 incher, it was a real meal for this slutty stewardess to eat.
I had learned from a girl I knew that when a man’s cock is too big to fit it all in your mouth, the trick is to stroke the part you can’t fit in your mouth for him. That’s what I intended to do with Dick, suck him good while I stroked his big long 10 inch love tool. I wanted to be the best stewardess these pilots ever flew with. I had the lips to do it with and a nice long tongue they really liked, too.
To be continued…
