Paradiso Ch. 15

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Jessie and friends put me through my paces.
6k words
4.66
36.8k
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Part 15 of the 22 part series

Updated 06/07/2023
Created 07/04/2014
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SlyKink
SlyKink
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Day 4

Sunlight streamed through the windows and I woke to the sound of conversation and the smell of cooking eggs. I felt sticky and gross from the night before; badly in need of a shower and toothbrush. The price of sexual gratification, I thought with a chuckle. I staggered into the kitchen to see Liam and Devi chatting away happily and cooking a nice breakfast.

"Good morning." They both said as one.

"Jinx!" squeaked Devi as she playfully punched Liam's arm.

I looked with a mix of admiration and disbelief at the sexy couple standing before me. I had made love to the beautiful Devi, which was quite enjoyable but not out of the ordinary, given how often Sara and I invited other women into our bed. But I had also had sex with Liam. More accurately I had sucked him off then let him fuck me in the ass, and I had enjoyed it.

"Where's Sara?" I asked.

"In the bathroom, getting ready." Devi replied.

I went looking and found her at the sink brushing her teeth. I sidled up next to her and began brushing my teeth as well. After we finished with our teeth we stepped into a hot shower and took turns washing each other. We made out a bit as we did and she paid special attention to my ass, working a soapy finger in and out of my well worked anus.

At one point Sara looked me in the eye and asked,

"So, really, did you like last night?"

"Yes." I said honestly. "I liked it all."

Soon we joined our lovers from the previous night for eggs, toast, coffee and fruit. The morning conversation gravitated toward last night's activities. Liam seemed interested in getting some feedback. I explained that while I didn't feel the same kind of attraction toward men that I felt for women, I had to admit the sex was really hot.

"Just because you occasionally eat Mexican food," Liam said in a way that gave me the impression he had said this before, "doesn't make you Mexican. But just because you aren't Mexican, that doesn't mean you can't enjoy some really great Mexican food every now and then." He flashed a smile that I returned and I couldn't deny his logic. I wondered how many times he'd said that very thing to men who'd had their first gay experience with him.

Just as we were ending our breakfast there was a knock at the door. Sara rose to answer it and a few moments later she returned with a familiar face. Well, a familiar face, and tits, and hair, and hips and legs with a massive, meaty dick swinging between them.

"Jessie!" I exclaimed.

"Hey Gary. Nice to see you again."

I turned to our other guests and made introductions all around.

"Jessie?" Liam asked. "Is this the Jessie? The one who..."

"That's right?" she said proudly. "I'm the one who took this boy's little anal cherry."

I felt myself blushing a little at that.

"So he told you all about that?" Jessie continued.

"Yeah. So you're the one I have to thank for breaking in his little asshole for me." Now I really blushed. Jessie turned to me, wide eyed.

"Naughty boy." She cooed.

"I think he's actually kinda nice." said Devi, sliding up next to me and taking hold of my prick which had begun to stiffen.

"Would you like to join us for some breakfast? There's some toast and fruit left." Sara offered.

"Thanks, I already ate. I was actually hoping I might borrow Gary for a while. I have some people I'd love him to meet."

Jessie had told me that she had some friends in Paradiso the wanted to introduce me to. My girlfriend and guests all looked at me to see if I was interested, so I looked over to Jessie. Our first encounter on the beach had been a lot of fun. I sucked her colossal column of girl cock right there for all to see, and then I fucked her little t-girl buddy Riley in the ass. Then that night she had come to our room and gave me an ass fucking unlike anything I had ever experienced before.

"I'm game."

Sara told me she would have no trouble entertaining herself so Jessie took me by the hand and led me into the crisp morning air. The sun was bright and the sky was a clear blue with just a few wispy clouds. The air held the faint salty smell of the sea and Jessie was leading me toward it.

"The first time I saw you, you were wearing a pink anklet. I had no idea I'd given you such a taste for cock."

"I still like tits and pussies." I joked.

"Well if you like tits then I have someone for you to meet."

As we made our way across the grounds there were couples and small groups here and there engaged in sexual play. I could hear the sound of waves off in the distance but before cresting a last rise that would have led to the beach we turned left and passed by a café. When we turned the corner we came upon an outdoor terrace and a group of perhaps forty people gathered around watching something.

Jessie smiled at me and pulled me by the hand over to the crowd. We found a gap and worked out way in. The people formed a ring and in the center was one of the more remarkable people I'd seen since arriving here. She was maybe five feet two inches tall with raven black hair to her shoulders with pink highlights. She had an hourglass figure with wide hips, a slim waist and firm D-cup tits tipped with pointed pink nipples.

The most impressive thing about her was the truly enormous penis jutting out from a few inches below her navel. It was actually just a little bit bigger than Jessie's; eleven or so inches and a hair thicker with a gentle upward curve to it and a red-purple head that was leaking pre-cum. Her entire length glistened with oil and she was pumping away at the shaft with both hands.

The assembled audience watched the show with rapt attention. As she stroked herself off she thrusted with her hips as though she were fucking someone. She moaned and sighed with pleasure as she stroked away. She was completely hairless from the neck down so her oily hands glided easily over her smooth skin.

Her stroking and thrusting grew faster and faster and her moans turned into a half scream as her ass and groin tightened her cock began pumping cum. The beautiful t-girl cupped her hand in front of the bulbous head and caught the spurts of creamy spunk. When she had finished cumming she lifted her hand to her lips and proceeded to drink her own load.

A spontaneous round of applause erupted from all around us and both Jessie and I joined in. She smiled and took a bow before her appreciative audience. The crowd soon began to disperse and the mysterious t-girl began walking toward us. Her tits and cock were both large to begin with, but on her small frame they looked obscenely large. Her enormous, still erect girl dick swayed back and forth as she strode toward us. She flashed a beautiful, white toothed smile.

"Hey Jessie!"

"I never get tired of that show, girl."

The two t-girls embraced warmly and kissed. When they broke apart they turned to me.

"So who's the new talent?"

"This," Jessie laughed "is Gary. Gary, this is my friend Leah."

When offered her my hand she walked right past it, wrapped her arms around my neck and pulled me down into a soft, sweet kiss. The faint, salty taste of her own cum was still on her lips. It was a warm, pleasant greeting and I was keenly aware of her tits pressing into my chest and her cock, now finally beginning to soften, rubbing against my thigh. She finally pulled back and smiled.

"Nice to meet you, Gary."

"Nice to meet you, too." I replied. "That was quite a show you just put on."

"I've always been something of an exhibitionist." She said with a wink. She then turned to Jessie. "So are we bringing him to see the others?"

Jessie nodded and then looked back to me.

"One of our friends has a place nearby. They'll be waiting for us there."

The two sexy women took me by the arms and the three of us headed back toward the beach. My heart fluttered with anticipation at what was to come. Jessie alone had worn me out the other night. I could only imagine what she and several of her friends together might do. I felt a similar sense of intimidation and desire to the one the night Jessie fucked me when I considered Leah's mammoth member forcing its way into my asshole. The only thing I can compare it to is eating an incredibly, painfully spicy dish at my favorite Indian restaurant. It hurts, but it's so fucking good.

A short walk later we arrived at one of the apartments overlooking the beach. It was of similar size and design to mine and a few moments after Jessie knocked on the door it swung open to reveal a beautiful Latin transsexual. She had light brown hair with blonde streaks through it, flawless light caramel skin, perky tits that were a large B or a small C, and a flaccid cock that was of average size, at least for now.

"Hey, Girls!" she said with a smile. "Come on in. We've been waiting." As we walked inside I saw her looking me up and down out of the corner of my eye.

When we arrived in the living room I saw two other sexy t-girls waiting. The first was Riley, the fair-skinned little pixie from the beach who I ass fucked. When she was me she smiled and squeaked with excitement then jumped up off the couch and ran into my arms, wrapping her own arms around my neck and pressing her lips to mine. We were getting off to a flying start.

The other one was tall and slender with nut brown skin, curly brown hair, B-cup tits and a thick, dangling, uncircumcised cock. Once Riley released me Jessie started the introductions.

"Ladies, this is Gary. Gary, this is Marina." She said motioning to the one who opened the door. Marina reached for me as if to shake my hand, but before I could take her hand she took hold of my limp cock and began stroking it until it began to stiffen. When she let go the black t-girl stepped up.

"And this is Sierra." She wasn't quite as forward as Marina and shook my hand.

"So, Jessie told us all about how much fun you had with her and Riley at the beach and then again with her later at your place." Marina said. She had a sultry voice with a sexy Spanish accent.

"Yeah," I confessed, "we had a hell of a time."

"Well," Leah began, "how would you feel about having some more fun with us?"

I took a moment to look around at these five hot transsexual babes. They were watching me with a look in their eyes like a group of cats watching a mouse they had surrounded. After all I had been through so far this week I didn't have enough inhibitions left in me to say no to virtually anything.

"I'm up for it."

"You sure are." Riley giggled, motioning to my groin. I looked down and saw that I was fully erect. I looked back up at the ladies, stood still for a beat, and then the six of us just laughed.

"Well," said Jessie "I could use a drink first."

I inwardly sighed with relief, thankful that we were going to ease into it rather than the five of them just ripping me apart like a ragdoll. I knew Riley was a bottom, but for all I knew the other four were all planning to get well acquainted with my mouth and asshole.

Sierra, whose room it was apparently, led us to the kitchen and from the refrigerator produced a large bottle of vodka and a jug of orange juice. Shortly thereafter each of us was sipping screwdrivers and chatting about our time in Paradiso. Jessie, it turned out, was the only one of them who was strictly a top while Riley was the only pure bottom. Leah, Marina and Sierra liked to give as good as they got.

I told them all of how my girlfriend Sara had been buttering me up for quite some time to try to get me to broaden my sexual horizons. By then end of day three I had both given and received anal sex from transsexuals and had both my mouth and ass fucked by a man. Apparently these five t-girls were all friends and each day one of them got to bring a favorite lover back to one of their rooms for the rest to enjoy.

I was half way through my third screwdriver, and feeling nice and mellow, when Riley couldn't take it any longer. She gently took the glass from my hand and put it down on the counter before taking my now empty hand. Her eyes were wild with excitement and she grinned from ear to ear.

"I just can't wait any longer, Gary." She pulled me into the next room and laid me down on the freshly made bed. It was big and soft, like the one in my own room. She had me lie in the center of the bed and I watched her slowly crawl toward me with a look in her eye like a lion stalking prey. When she reached me she began caressing my thighs and stomach. Once again I began to rise and stiffen.

When I was fully aroused she took hold of me with her delicate fingers and began stroking up and down my seven inches. She snuggled up next to me and when I turned my head she began kissing me with soft, full lips. My eyes were closed but I could hear the soft footsteps of the others crossing the bedroom floor. Riley's tongue and my own danced sensuously in each other's mouths. A minute later she pulled back and I saw the other hot t-girls all stroking themselves to full hardness while looking at my prone, aroused form.

Riley ducked her head down over my hips, stuck out her tongue and softly licked a drop of pre-cum from the head of my stiff prick.

"Mmmmm... so tasty!" she cooed.

A moment later she lowered her head again and took almost my entire length into her mouth in a single gulp. Her lips and tongue were warm and wet and they moved over my stiffness, swirling and sucking with the expertise of much practice.

As Riley sucked my penis, Sierra crawled onto the bed and knelt next to my head, inching her way closer and closer. At full hardness her penis was roughly the same length and thickness of my own, though it looked quite different. It was seven inches of smooth flesh the color of milk chocolate with the head still mostly covered with a sheath of skin. I had seen a number of uncircumcised cocks since being here but this is the closest look I had ever gotten at one.

Without having to be asked I leaned in closer and began to lick the bit of the tip not still covered by the foreskin. I was growing more adept and less hesitant when it came to sucking cock and I enjoyed the taste and feel of her as I took about half of her between my lips.

"You're an enthusiastic little cocksucker, aren't you Gary." Sierra purred.

A week ago calling me a cocksucker might have gotten someone anything from a dirty look to a punch in the head. But today it was an accurate description, and besides I was too aroused to care. I took another inch into my mouth and began sucking and licking with passion. I liked the way the extra skin slid between my tongue and her swollen cockhead.

We lay there for a few minutes, pleasuring each other with our mouths. Sierra's salty pre-cum was coating my mouth with its faint, salty flavor and I know I must have been doing the same with Riley. Sierra was the first to cum. She began to moan and thrust her hips, driving more of her cock into my mouth. I felt it flare and swell up and a moment later was treated to five good spurts of hot semen.

Unlike the night before with Liam I let the cum pool in my mouth until she was finished. It was a healthy mouthful but before I could swallow Marina appeared above me and pressed her mouth down over mine. When her tongue parted my lips I returned the gesture and Sierra's cum flowed freely between us. She took about half of it and when she pulled away we looked in to one another's eyes and swallowed in unison.

"That looked tasty." said Riley, taking a momentary respite from blowing me. She went back to work with greater energy and in less than a minute I squeezed my eyes shut as the cum rose up from my balls and flowed out through my shaft. Riley sucked and swallowed greedily as my salty seed shot into her expert mouth.

"Alright," Leah announced. "Enough with the appetizers. Let's get to the main course."

She knelt between my legs and took hold of my ankles. Then with a strength surprising in someone so small she lifted them up and pushed them toward me until my knees nearly touched my chest. I looked down to see her enormous erection straining and prepared myself to be impaled, but instead she lowered her head and began teasing my asshole with her tongue.

I just laid there for a time and enjoyed the dirty, sexy feeling of an expert rimming. Her tongue stimulated the sensitive flesh and then dipped inside, pushing past the tight ring of muscle to stroke my tender passage. As my ass was being tongue fucked I looked over to see Jessie reclining across the bed with Sierra between her legs stroking and sucking her massive hard-on.

When she judged me to be warmed up and relaxed, Marina gently pushed Leah aside and positioned herself between my ankles. Riley appeared next to her and began applying lube to her erect penis. It was, perhaps, a little larger than my own but not by any means as big as Jessie's or Leah's. I would be able to take it as easily as I had taken Liam's the night before.

"Do it." I told her. "Fuck my ass."

With a grin, Marina leaned in and, guiding it with her hand, pressed the head to my warmed up asshole. My experiences with Sara had taught me how to physically handle taking considerably sized dildo's in my ass, and my experiences with Jessie and Liam had dispelled all the fear I'd had about taking a real cock.

It only took a bit of pressure before my asshole yielded and sucked the head of Marina's cock inside. I was now relishing the feeling of real flesh penetrating me. Inch after inch it began sliding up into me. When at last her hips met my upturned cheeks her face and body contorted in pleasure, like the way a cat looks when it's stretching. She pressed her hips into me as hard as she could and rotated them around, as if to penetrate me as deeply as possible.

"Oh, Gary. Your ass is yummy." She groaned, enjoying the feel of my asshole gripping her sensitive length.

My asshole was hot with sensation as Marina's lovely girl dick sawed in and out of me, stimulating my prostate with each thrust. Even though I had just cum I was hardening again after just a couple of minutes. It was such a huge turn-on to look up and see such a beautiful woman; her smooth skin and feminine features, her shapely tits jiggling and bouncing, and knowing that her big, hard dick was up my ass.

Even though I still preferred women, their soft looks and gently curving figures, over men, I had to admit that I was developing quite a taste, for lack of a better word, for cock. Jessie and Leah crawled toward me from opposite sides of the bed and knelt next to my head. When they brought their knees as close to me as they could and thrust their hips outward the tips of their immense girl cocks touched just in front of my face.

I lifted my head, opened my lips, stuck out my tongue and began servicing the feast of girl meat spread out before me. Seeing them there in front of me and up close I saw that Leah's was just a hair bigger both in length and girth. I licked all along the length of their touching cocks and ticked the sensitive ridges under the heads. I took Leah's plum sized head into my mouth and eagerly sucked the first few inches for a minute, then released it only to turn and do the same for Jessie.

"You were right, Jessie." Leah enthused. "He is a keeper."

I responded to her praise by turning back and sucking her cock some more. After a few minutes I heard Marina cry out and her cock leapt inside of me, swelling and jerking until liquid warmth began to fill my bowels. Jessie reached over and grabbed Leah by the head, pulling her in for a kiss. This drove Leah's dick deeper into my mouth and I started to gag and sputter. Mercifully, Leah drew back and I gulped air before resuming my oral pleasuring. Marina pulled out of me and rolled onto her side with a sly, cat-that-ate-the-canary grin.

SlyKink
SlyKink
277 Followers
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