By CB Achtland

This is a work of fiction.

The days after I fucked with Leona I spent alone. She has told me that she was going for shoot in the Bahamas for a week. I was a man who had everything in terms of material comforts, and there was not a girl I couldn’t pull in a bar. But I found that I could not stop thinking of Leona and that I stayed at home fretting and looking at shemales and ladyboys on the internet. I had Leona’s number but was terrified of calling her in case she was working and I disturbed her.

I just wanted her to be back and worried that she may not want to see me again. My cock was perpetually hard and leaking pre-cum. Luckily I run my own business and have an honest manager. I put him in charge of things and took the week off. After much introspection, I had the brilliant idea of visiting the bar where I had first met Leona. So one evening I got dressed and ready to go out, but as I was about to leave, a niggling thought that had been at the back of my head came up right in front of me. If it wasn’t Leona, it would not be the same. It had to be Leona, I wanted to re-create my first time with her.

I stayed home that night and hit the bottle, and once I was fairly drunk, I decided to throw caution to the wind and to call her. Her cell was ringing:
“Hello?”
“Um, baby, its Jake…”
“Jake! How sweet of you to call! How are you, lover?”
“Fine, how are you?”
“Baby, you’re slurring, have you been out partying, meeting lots of lovely girls?” Her voice was teasing me.
“Er … no… actually I’m at home..”
“Oh you darling boy! Say! Are you missing me?”
“Errrr… when are you coming back. I miss you.”
“Oh dear … my darling, I’m sorry. We’re going to stay two weeks more. It’s off-season and we’ve got the location cheap and the producer wants to finish off a few more movies …”
“Damn!”
“Poor baby…”
Silence from my side, I was crushed. TWO more weeks without Leona. I would prefer to castrate myself!
“Listen baby! I have a bright idea! Why don’t you come and visit me? The girls would love to meet you!”
“You mean I can visit you? Won’t anybody object?”
“Certainly not, as long as you don’t get in the way of my work or behave like a jealous husband.”
“I promise baby, I won’t. Can I come right away?”
“Oh yes!!!”

And so it came to pass. I handed over charge to my manager, Pete, got my agent to get the first available tickets to the Bahamas and was soon on my way. This was an opportunity of a lifetime, and I was not going to miss it.

I knew that Leona was a porn star, or adult entertainer if you will, and that they were in the Bahamas shooting porn. For instance, I knew that she would be fucking men and women, and perhaps other shemales in the Bahamas, but I was only interested about when she would be back and whether she would want to see me again. I did not feel any of the typical male jealousy. Meeting Leona had somehow liberated me from the uglier human emotions, that of possession and ownership. Or was it that a transsexual was herself not possessive and that liberated the partner? Perhaps this is why some men were drawn so inexorably to the third sex. And in any event, the human race is not biologically monogamous.

Several hours later I was at Nassau airport and once through immigration my eyes hungrily scanned the crowd for her, and there she was, as stunning as ever. She was dressed in a skirt that barely concealed that magnificent ass. We immediately wrapped our arms around each other. I had a raging hard-on and so did she, and our hips seemed to have forged themselves to each other. Only when I did see some people starting to stare did I disengage.

We were soon in a private cab heading to the secluded beach location hired by the production company and Leona was all over me. I frantically indicated the driver, but Leona said, “Relax honey, he’s worked with us many times.” We made out in the car massaging our cocks under our clothes and kissing deeply. I was in a state of schoolboy excitement and ready to explode when we thankfully pulled up at a very pretty colonial-style bungalow.

I was plied with fresh fruit juice and introduced to the cast, a bunch of gorgeous shemales. There was Hilda, who seemed Brazilian, Jamie, a black American with the cutest smile, a tall white American called Mandy, and another black American called Veronika. Each was more beautiful than the other. The only woman present was Lucia, the maid, and she was suspiciously beautiful; black, tall, slim, with long, straight black hair, and a drop-dead gorgeous face. The crew were at a hotel in Nassau.

I stood there, my tongue hanging out with ill-concealed lust when Leona cut in, “Honey, which of them do you like?” I turned bright-red with embarrassment as the girls tittered, and to add to my discomfiture Leona began caressing my cock. She then, thankfully, dragged me into our bedroom. Our clothes were off in a second and we were locked in a 69. I guess she has lusted for my cock almost as much as I had lusted for hers.

When we had come, we lay in each others arms just content to be there with each other.
“So tell me darling, which of them do you like?”
“I like you,” I mumbled.
“Oh darling, don’t be like that. I’m not sexually jealous, I want you to have fun. You’re not the possessive type are you?” She looked worried.
“Er no, it’s just that I’m new to this.”
“Don’t worry darling, so tell me who you liked?’ a mischevious grin on her face.
“I liked all of them,” I said, turning bright-red.
“You dirty boy, I bet you’ve been surfing shemale porn.”
Bright-red again.
“I knew it the moment I met you.”
“How?”
“Can’t say, just think of it as a special talent exclusive to shemales. Lust for shemale cock?” Again that playful smirk.
“Er, I guess you could call it that.” I was beginning to relax.
“Good, because I have something planned for you.”
“A shemale orgy?” I was only half-joking.
“Perhaps… if you are a good boy. And do you like Lucia?”
“Lucia? I sure do, but isn’t she the maid?”
“She is, but Richard and Lucia also double and the female and male roles for this shoot.”
“Richard?”
“Her husband, who drove us back.”
“Oh…” Richard was black, well over 6’ tall, and had an athletic build. I wondered if he had ‘acted’ with Leona.
“Are you wondering if Richard and I have done it?”
“Er … yes.”
“We have. You jealous?”
“No baby,” and I meant it, “actually it makes me feel horny for you.” I hugged her. “I know you’re a porn star and I don’t mind.”
“Do you want to see Richard and me?”
“What, like now?”
“No, on video.”
“Cool.”

I was soon watching Leona, the love of my life, getting fucked by Richard. “Like it?” she asked, and I nodded. I was getting so turned on. It was beautiful and it was liberating. And neither, certainly not Leona, looked like they were acting. They seemed to be having a great time enjoying each other’s bodies.

“Now be a good boy and get on your hands and knees,” and then with passion, “I want to fuck you Jake.” I got on my hands and knees and Leona fucked my ass with passion. And I enjoyed every thrust. Yes, this is what I wanted. It was sexually liberating, and spiritually and mentally liberating, because, pardon the pun, I gave a fuck what anybody thought about my attraction to Leona in particular and to shemales in general.

We fucked the night away, consumed in our lust and emerged for a late dinner. The girls were off today and the next, and had gone out for an night on the town in Nassau. Richard and Lucia had also gone and so we fixed dinner for ourselves. After dinner we grabbed a bottle of champagne and headed to the beach. It was a private beach and Leona and I fucked again. We swam, and later on the beach I marveled at the moonlight falling on Leona’s generous curves. She tasted of the sea and we made warm and tender love to each other.

The next morning we woke and Leona insisted that I wear only a pair of boxers to the breakfast table. Although we had sucked off each other as soon as we woke I was still petrified that I would get a raging hardon at the breakfast table. Leona came topless with a tiny red thong to cover her ass. We stepped out and I was partially relived to see the others wearing only bikini bottoms, Lucia included. Richard was wearing boxers.

“Oooooh, here come the lovers!” cried Hilda in a husky voice, and the others joined in a chorus of teasing. Before I knew if Hilda had come up to me and was running her fingernails over my nipples. My cock was growing hard and she made things worse by grabbing it through my boxers.

“Oh look girls,” she cried, “I think Jake likes me!”
“Hey Lucia,” yelled Leona, “Jake wants to fuck you good. You okay with that Richard?”
“So long as I get you baby,” and Leona and him were kissing passionately. I noticed Leona watching me closely, but I had other things on my mind as Veronika was feeling my butt.

Somehow I made it through breakfast without shooting a wad right there, with the girls teasing me all through. They took turns sitting next to me and running their hands over my body and through my hair. It was made all the worse by seeing Leona and Lucia rubbing their bodies against each other.

When we returned to the room, I grabbed Leona, but she was having none of it. “No you don’t you horn dog,” she said, “I have something special planned for you.”

By the time Leona and I went down to the beach the others were already there, the champagne was flowing, music was playing and the dancing had started. We were greeted with a cheer and Leona and Richard were soon flirting shamelessly. Lucia joined them, whereas I was, to put it mildly, attacked by Hilda, Mandy, Veronika and Jamie. Fresh meat, as Hilda put it, much to the amusement of the others.

We were soon dancing, whilst Leona, Richard, and Lucia were dancing separately. I watched as they sandwiched Lucia between them and ground their hips against each other. I so wanted Lucia as well! I wanted to enjoy her with Leona. But I was brought back to reality when Veronika slapped my ass hard.

“Leona’s your first shemale?” she asked, and I nodded.
“She tells us that you like us,” teased Mandy, “do you, Jake?”
“Yes,” I stammered.
“Do you want to fuck with us, Jake?” It was the incredibly cute Jamie.
“You like getting fucked up the ass Jake?” This was Hilda.
And then the chanting started, “Jake wants to fuck us, Jake wants to fuck us,” but the champagne and the atmosphere were getting to my head and I could not care. My hardon was clearly visible through my boxers and my body was shining with sweat. God, I wanted to fuck these babes now!

We were dancing hard, rubbing our sweaty bodies against each other, and I loved it when one of the girls rubbed their tits against my nipples whilst another rubbed their tits against my back. I loved their naked sexual aggression and as they pulled me to them for a kiss and ground their hips against mine, I could feel that their cocks were astir and ready for action.

We were dancing away like satyrs, when all of a sudden Hilda attempted to pull down my boxers. It snagged on my cock but the other three were on my case and I was down with my back on the sand, buck naked with a raging hardon. Before I knew what was happening Mandy’s lips were around my balls sucking hard, while Veronika slipped a cock ring onto me and began playing with my cock head.

I would have cried out with ecstasy but Hilda’s cock rammed down my throat and she told me to suck her. I sucked and she was tasty. But she soon pulled out and I saw Jamie’s cock above my face. Hilda’s cock was pretty much like Leona’s, both had smooth cocks that stood to the right and had large ball sacks. Jamie’s was different. Of course, it was black, smaller than Leona’s or Hilda’s, and had an extreme curve, almost a kink, to the left. Coupled with her angelic smile and voice, I think I was in love and eagerly took her into my mouth.

They took their turns with me, “A whore for shemales,” as Hilda put it. Veronika’s cock was a fat and uncut black beauty and I looked forward to taking it in my ass. Mandy was tall, slim and fair, and her cock resembled her except that it looked small until roused and then curved straight up and back leaving the head touching her body. I enjoyed her cock as well. While one would stuff her cock into my mouth the others would toy with my cock and balls. Soon they raised my legs and began to play with my ass as well. I had died and gone to heaven.

When the girls were ready to cum they surrounded me. Their rampant cocks were magnificent. Hilda asked me to keep my mouth open and I gladly did. They came, almost simultaneously into my mouth and onto my face and chest. The splatter of hot shemale sperm was divine. This is what I wanted. In effect it was an initiation into the third sex. And I knew that although Leona was fucking with Richard and Lucia, she would have seen my initiation.

The girls then fed me the cum which had not gone into my mouth. At this stage I could not tell the difference in taste between the four wads of shemale cum, but I resolved to find out before I left the Bahamas. All I knew for certain was that Leona’s tasted creamy sweet and was thick.

“Let the poor boy get off,” said Hilda and she removed my cock ring. “Jerk for us Jake,” she smirked. And I did. And when I came I shot high onto the girls’ hair, faces, and tits. They collapsed onto me taking up my cum with their fingers and feeding themselves, and we were a lust-soaked, sweaty, and happy fivesome. As we caught our breath our eyes naturally turned to the action going on close to us.

Richard, Lucia and Leona were going at it. Leona was fucking Lucia’s cunt doggy style, and Richard was deep inside Leona’s ass. Lucia looked divine. Her face was pressed into the sand and her hair was entangled in her mouth. Her slim frame bore the combined weight of Leona and Richard and she was moaning with pleasure. The primeval sound added to the lasciviousness of the tableau. My cock began to harden as I though of fucking Lucia’s mouth.

But Hilda had other plans and I was on my hands and knees waiting for her cock. She drove into me with a force that stunned me. Leona had always been gentle but Hilda was not, and I loved it. As she fucked me I watched Leona pull out of Lucia’s cunt and slam into her ass. Lucia screamed and then her moans became louder and more intense.

Hilda noticed that my mind was on the threesome and so she yanked my head back and Veronika’s cock was down my throat and she was giving me a throat fucking while Hilda intensified her pounding. The cock ring was slipped on and Mandy and Jamie were at my cock and balls. My mind was back here all right!

Hilda and Veronika coordinated their efforts and came simultaneously, flooding my ass and my mouth. Veronika’s cum tasted like Leona’s and I loved it. I had no respite and Jamie was next in my ass and Mandy in my mouth. But in that instant I caught a glimpse of the threesome. Leona was sitting on Lucia’s face and Lucia was eating Richard’s cum out of Leona’s ass. Richard was hard at work deepthroating Leona’s cock. The pounding from Jamie and Mandy was not as hard but pound they did. They soon shot their loads and I got to taste Mandy’s cum. It was not too thick, but there was a flood of slightly salty cum.

I desperately needed to cum and the cock ring was slipped off. I was made to sit on Jamie’s face and she began to eat the loads of cum out of my ass. Her tongue probed deep into my ass and when Mandy began sucking my cock I shot my load almost instantly crying out with relief. She drank my cum and her place was taken by Veronika. Meanwhile Hilda stuffed her cock down my throat and began fucking my face hard, her balls slapping against my chin. Veronika’s cock sucking skills, coupled with Jamie’s tongue up my ass, got me hard again and after a couple of minutes of intense sucking I shot into her mouth. But Hilda’s face fucking continued and I knew she would cum any instant now and braced myself for it. Cum she did, in floods, and her cum was bitter and I almost gagged on it, but she held my head in place until I had sucked down every drop. As we lay down exhausted I could see the threesome finishing off what they had started. Lucia’s was sandwiched, with Richard fucking her ass while Leona fucked her cunt. Her body was racked by loud sobs of pleasure as all three came together. We trooped back to the cottage an exhausted bunch and as Jamie walked in front of me I marveled at her black butt and wondered what her cum tasted like. I also realized that I had not fucked any of the girls.

The next day it was back to work for the cast, and the production crew arrived. They were mostly cameramen. The director liked natural light and they all used hi-definition prosumer video cameras. Several movies were too be shot for DVD sales and for downloads. There were also shorter clips which would be sold to shemale websites. Several combinations of individuals would also be shot, including solo masturbation scenes. There were also three photographers who would shoot stills. Although a keen photographer myself I had not carried my cameras and so would have to be a silent spectator. But I had already decided that I wanted to photograph shemales and publish a glossy coffee table book of shemale nudes.

The first day’s shoot was for a full movie, a ‘shemale island’ theme, and so Leona and the girls were busy. Richard had been dispatched to Nassau on errands and I went down to the beach to watch the filming. This is the first time I would see Leona play with the girls and predictably, Leona, Veronika, and Hilda were the more aggressive. Mandy and Jamie seemed to take the brunt of the assfucking. I watched these five beautiful shemales fuck and suck each other’s brains out. Naturally I had a raging and painful hardon. I desperately wanted to jerk off when I suddenly realized that Lucia would be in the cottage, alone.

And so I rushed back to the cottage. I was determined that I would give Lucia the fucking of her life. I wanted to pound her ass and maul her tits. I entered the cottage and dropped my boxers. I wanted her to know why I was there. I found her in the kitchen wearing a flowery white bikini which showed off nicely against her black body. The moment she saw me, rather than being surprised at the sudden intrusion of a nude man, she smiled, and it was the smile of a seductress.

“Hello Jake, I’ve been expecting you.”
“What?”
“I saw the way you were watching me yesterday. You wanted to be the one fucking my ass, right?”

I didn’t want to talk. I grabbed her, ripped the bikini top off and began chewing her breasts. She responded positively, grabbing at my cock and kissing me. I threw her down onto the floor and tore off her bikini bottoms. Without any further delay I began to press down on her asshole and pushed into her. The familiar cock-hardening moans began to escape her. I pushed down inch by inch and my cock felt like it was on fire. I fucked her hard, I wanted to make Lucia moan, and the harder I fucked the louder she moaned.

After I had finished we lay next to each other. I was satiated and my cock was limp. Lucia played with it while she gently nibbled at my nipples. She then took my cock into her mouth and I was soon hard again. She asked me to fuck her and I dutifully climbed over her. I wanted to fuck her missionary style. I wanted to pound her and make her moan. And I did. She moaned like a bitch, wrapped her legs around my ass, dug her nails into my back, and we came together. Lucia was a good fuck, and she had a lovely tight asshole, but this was my moment of epiphany. I missed the shecock and now realized why dear Leona had baited me with Lucia. From now on, it would only be shemales for me.

When Leona and I were in the room that night, she was the one who brought up the topic.
“You fucked Lucia today didn’t you?”
“Yes, I did.”
“And…?”
I looked deep into Leona’s lovely eyes, “I missed something?”
“What did you miss, baby?”
“I missed shecock.”
Leona just smiled, lay back, and opened her legs. I went down on her and I was a confirmed addict. I would never fuck a woman again.

The next day, Richard and Lucia were to play a hapless couple stranded on a shemale island, so all the cast was busy and I had time to myself. I was supposed to leave in a day but was loathe to do so. I spent my time watching some of Leona’s movies, jerking off, postponing my tickets, and putting more responsibilities on my clueless manager after promising him a bigger pay packet. I planned to leave with the cast, in a week’s time.

The next few days were taken up with a lot of shorter shoots. Thankfully, Lucia was always needed for shemale on girl scenes. I didn’t have the heart to tell her that I didn’t want to fuck her. But I would certainly love to tell old girlfriends back home who acted as if I still wanted them, to fuck off. However, all the girls were not busy all the time and that’s how I got to taste glossy black Jamie.

It was a given that we would fuck. We were the only one’s to remain in the cottage that day and she had spent her time at the breakfast table fluttering her lovely eyelashes at me. I so wanted to taste her cute cock and cum. As soon as the others left, we were at it right in the living room, licking, sucking, and nibbling at each other. But Jamie was innovative and dragged me into the shower.. We showered together and I enjoyed exploring every inch of that black body. I knelt down and probed her ass hole with my tongue as the water cascaded over us.

We left the shower without drying ourselves and Jamie presented her cute ass to me. After Leona it was going to be my first shemale ass and I wanted to put on a good show. I fucked her gently at first but when I realized that she could take me easily, I began to fuck harder and faster. Jamie enjoyed it, and after I had cum I made her sit on my face and ate my cum out of her wonderful ass. I then spent an age sucking on her cute balls and cock. I didn’t want her to cum soon as I liked the kink in her cock and also because it tasted so good. But she had to cum at some stage and when she did it was the sweetest cum I had ever tasted. It seemed to taste and smell of vanilla, and I loved it.

That evening Jamie spread the word that I was a good ass-fucker and Lucia immediately seconded her. So all the girls were now after me to fuck them as soon as they were free. There were no free days for the cast after that and so they just had to bide their time. The first to get lucky was the incredibly tall and leggy Mandy.

Mandy is tall, fair, with smallish breasts. She also looks incredibly cute and has a nice long cock which stands and curves straight up when hard. Her ass is slimish and I looked forward to fucking a different ass since all the other girls had generous butts. In some circles I guess Mandy would be called a femboy. But whatever she was called I found her lanky white body to be incredibly sexy and was soon lapping at her balls. We got into a 69 and spent a lot of time sucking at each other. Leona had told me that Mandy had done some BDSM work and I asked her about it. She responded by making me kneel and then cock slapping me. But it was soon time for business and she presented her cute ass to me. I played around a bit with my tongue and she loved it. I then fucked her ass good, and she loved it, yelling encouragement. When done I made her lie back and gave her a good cocksucking. It was a fun session and I was glad that all these girls also lived in NYC and that there were good times ahead.

Fucking Veronika was another great experience. I had to fuck really had since the girl had a generous ass. I enjoyed the feel of her voluptuous ebony body and her sultry ‘come fuck me’ looks.

However, all good things must come to an end. The movies were shot and the week was over too soon. It was time to get back to NYC, and to my usual boring life. But then I knew that all the girls lived in NYC, and most importantly Leona would be there, so perhaps my life would no longer be boring. I looked forward to making contact with her again. But that is a matter for another story. More so since I hadn’t fucked Hilda as yet.