Paradiso Ch. 05

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Sara and I go to the beach and meet some special girls.
3.1k words
4.64
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Part 5 of the 22 part series

Updated 06/07/2023
Created 07/04/2014
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SlyKink
SlyKink
278 Followers

Day 2 Continued

I didn't think I had been asleep long, maybe just a catnap, when the sound of the door opening stirred me awake. I sat up on the edge of the bed and smiled back at Sara's smiling face.

"So," she said with a smirk "did Danielle show you a good time."

"She was ok." After a pause Sara and I shared a laugh and then a kiss.

"Where's Lauren?" I asked when I noticed that our beautiful brown lover was nowhere to be seen.

"She met a man at the beach, a Spanish hottie named Juan. They really hit it off. She's still there with him."

"Good for her."

"I met someone too. Her name's Jessie. She's amazing. I want you to come and meet her. She's still at the beach too."

"Let's go."

We grabbed a couple of beach towels from the linen closet, Sara took my hand and we walked together toward the beach. Along the way we stopped a couple of times to enjoy the view of couples and groups fucking, though we never joined in, and I recounted to Sara the details of Danielle's extra special massage. Finally we climbed over a rise and I got my first glimpse of a beautiful white sand beach. The sun shined down on the sand and crystal blue water and hundreds of nude forms of all colors.

Sara led me down onto the beach. As we went we passed people sunbathing and playing, many were swimming on the sea and of course many were having every kind of sex imaginable. Finally Sara saw who she was looking for. She pointed her out and I saw her. Facing away from me was a woman. She was tall, maybe a hair over six feet. She had a voluptuous, hourglass figure and long blonde hair tied back in a ponytail. Her most striking feature, however, was a large tattoo that covered most of her back, the backs of her arms, her buttocks and hips. It was reddish brown and portrayed an intricate series of intertwining geometric patterns. It looked like a Hindu symbol I had seen before in one of Sara's Yoga books.

"Jessie!" Sara shouted and waved. The beautiful blonde turned at the sound of her name and I took in the sight of her. Her face was beautiful, with high cheekbones, and strikingly deep blue eyes. Her breasts were large and firm, at least a C-cup if not a D, with pointed pink nipples. Her flat stomach led down to a completely hairless crotch, out of which jutted the longest, thickest penis I had ever seen.

I was in utter shock. I knew from the orientation materials that there would be transsexuals here, but it was still a surprise. Here was this beautiful, feminine woman with a cock bigger than any I had ever seen, even in pornos. It was almost as thick around as Sara's wrist and must have been close to ten inches long. It hung flaccidly between her legs and was tipped with bulbous red head, like a plum. She began walking toward us and I couldn't help staring as it swung lewdly from side to side. Before I knew it she was right in front of me.

"They always stare." Jessie said. Her voice was strong, but feminine. "Gay, straight, man woman; it doesn't matter. Everyone loves a big cock." I didn't know how to respond so I just took a moment to compose myself, stuck out my hand and introduced myself. I noticed that Jessie wore no anklet.

"I feel like a swim." Jessie announced after the pleasantries. "Who wants to join me?"

"Sounds like a plan." Sara replied.

"Lead the way." I added.

The three of us headed in to the cool, clear blue water and spent the next thirty to forty minutes swimming and frolicking. Both Sara and Jessie made a point to brush past me, their skin gliding over mine. At one point Jessie swam up behind me and moved her body up against mine. I was keenly aware of her big, round tits with their stiffened nipples pressing into my back and her huge horse cock rubbing up against the back of my thigh.

After we were swimmed out we headed back to shore, laid out our towels and let the sun begin to dry our bodies.

"So Gary," Jessie began "I see you're only into women."

"I like women." I replied playfully.

"So you've never even tried a guy?"

"No, I haven't."

"That's too bad. I think straight guys could benefit from taking a cock in the ass. I think it would make them better lovers. It would give you perspective to know what it's like to be penetrated for someone else's pleasure."

I knew what she was getting at, and while the thought of that massive piece of meat tearing up my asshole was a bit frightening, I couldn't deny that her sexy looks and silky voice were getting me hot.

"It's not like I haven't had my ass played with, you know."

"Yeah, Sara mentioned that she used dildos on you, but it's not the same. She might enjoy it, but it's your pleasure that matters when she's fucking you with her toy. When it's a real cock up your ass it's the person fucking you whose pleasure matters. If men knew what it was like to be at another person's mercy like that, they'd probably be more conscientious to their girlfriends or wives."

I opened my eyes and turned my head toward Jessie. She was lying on her back, looking at me. Her cock was at full attention and I saw that she was a shower, not a grower. Her cock wasn't longer or thicker than it had been when limp, though it was still plenty big. Sara was lying on the opposite side of her. She was stroking Jessie's cock at the base with her hand and swirling her tongue around the thick, purple head.

The sight was so hot my cock immediately began to stiffen. Here was this beautiful woman; everything about her was feminine, except that an enormous column of meat jutted skyward from her groin. All this talk of sex had begun stirring me and seeing Sara idly pleasuring that massive cock was like the last little pebble that started the avalanche. In my mind I crossed over a line. I knew that on this trip I would try anything and everything Sara wanted, and I would be starting with this gorgeous T-girl.

"What do you think?" Sara asked. "Do you want to help me with this thing?"

I hesitated for a moment and then dove in. At first I reached out and wrapped my fingers around the thick shaft. My thumb and middle finger just barely touched on the other side. I started stroking up and down, mimicking the motions I liked whenever I jerked off. Her breathing quickened a little and a slight moan escaped her lips.

I looked up at Sara and our eyes met as her tongue gently probed the slit at the tip of her cock. Her eyes called me over and I felt myself drifting closer. A moment later I found myself face to face with this beautiful woman's giant penis. I steeled my nerves and then I stuck out my tongue and gave the blunt head a tentative lick. The salty skin was not revolting so I tried it again. With each lick I grew bolder and enjoyed it more. It was an exciting new experience, feeling the soft skin beneath my tongue and the texture beneath the skin of the thick ridges and veins. I moved my head up and Sara and I kissed with Jessie's cockhead between us, our lips and tongues caressing her sensitive flesh.

When Jessie moaned again I took the plunge. With all inhibitions gone I took her cockhead into my mouth. It was a stretch just to fit the whole thing in my mouth without scraping it with my teeth. I began to tongue her pee slit and then I felt her hand on the back of my head begin pulling me down and then one, two and then three inches of her girlcock disappeared into my warm mouth. After about five inches I couldn't take any more without her cockhead nudging my throat and making me gag. My eyes began to tear up a little but through them I could see Sara licking Jessie's hairless balls.

I pulled back a few inches and started to give Jessie a blowjob in earnest. I bobbed my head up and down and stroked the sensitive underside with my tongue. I tasted a salty drop of precum and it sent a shiver through my body. I was sucking a real penis. And not only that but I was doing it in public with people all around who could see. It was so dirty and thrilling. I just concentrated on the massive slab of hard flesh sawing in and out of my mouth and the beautiful woman it was attached to, now moaning loud enough for anyone nearby to hear and thrusting her hips along with my sucking. Her thrusts were driving her cock deeper into my mouth and I was getting more used to it. I was able to take six inches now before starting to gag and there was now a steady stream of precum oozing onto my mouth.

I knew when her cock started to jerk and jump in my mouth that Jessie was beginning to have an orgasm and I steadied myself to take her load in my mouth. I felt her hand at the back of my head again and she pulled me down until seven inches were in my mouth and her head was pressed right to the back of my throat when her balls finally boiled over and her cum came flooding into my mouth. I sputtered and coughed as the thick, salty semen sprayed into my mouth and down my throat at the same time. Jessie's cock was already taking up so much room in my mouth that what didn't slide down my throat began dripping out at the corners of my mouth. Finally, after seven or eight spurts the climax abated and Jessie released my head.

I rose off of Jessie's cock and took a moment to catch my breath. My jaw and throat were sore, but I was still delighted by what had just happened. It was a wonderful, sexy new experience and I loved it.

"Wow!" I heard a female voice say from behind me. "That looks like you had some fun, Jessie!"

I looked behind me and saw yet another t-girl. This one was the opposite of Jessie in every way. Where Jessie was tall and voluptuous, this one was a tiny little pixie. Where Jessie was a tanned blonde, this one was fair skinned and had jet black hair in little schoolgirl pigtails. Where Jessie's cock was this massive hunk of flesh, this other girl had a cute little girly cock.

"Gary, this is Riley. Riley, this is Gary." Jessie introduced us.

"It's nice to meet you Gary. I hope you don't mind me saying this, but you're really cute. If Jessie hasn't worn you out could I get some of that action?"

"Well, I guess so. Do you mind giving me a few minutes to let my jaw stop aching?"

"Oh, Riley doesn't want a blowjob." explained Jessie. "She's a total bottom."

"You mean..."

"Yeah!" giggled Riley. She got down on the towel next to Jessie, doubled her legs over her until her knees were close to her perky little tits and revealed a pink puckered asshole just under her balls.

"I want you to fuck my ass."

Holy shit I love this place. Not only am I getting all the sex I could ever want, but I'm getting the chance to live out every crazy fantasy, every hidden desire buried in the dark little corners of my mind. Sex with complete strangers, group sex and now these two incredibly hot t-girls. I grinned ear to ear as I knelt down between her legs. Sara stuck her head between us and engulfed my prick and began coating it with her saliva. After a few quick sucks Sara pulled back and turned her head to spit on Riley's winking anus. She then took hold of my cock by the base and guided it forward.

My blunt head pressed against her tight anal opening and I slowly applied pressure until the sphincter muscles yielded and her asshole opened up like a tiny flower and my swollen, sensitive head became lodged inside her. Riley moaned in delight and her body squirmed, begging me to keep going. I obliged her and slid another couple inches inside her tight passage. She obviously was well acquainted with taking cock in her ass. I sported seven inches of fairly thick cock and though Riley was tight she showed no signs of discomfort as they disappeared inside of her.

Once my cock finally bottomed out inside her ass I took a moment to savor the feeling. Her inner walls were warm and tight and her anal muscles rippled and squeezed. I leaned forward and slid my hands all over her adorable little body; her hips, her stomach and those pretty little tits topped by stiff, candy pink nipples. I slowly withdrew my cock until only the last two inches were inside and then began a slow, pistoning fuck.

I looked up at Sara and Jessie, both relaxing and enjoying the show, and then back down at the cute little minx I was fucking and I marveled at what I was in the middle of. I had just given my first blowjob and now I was fucking a shemale. It wasn't like it was gay, what I was doing. Jessie and Riley were both attractive women. That they had cocks didn't change that, not really. There was honestly nothing masculine about them. Everything, even their scent, was all woman. I picked up my pace in Riley's slippery rectum and reached down to fondle her little balls and soft cock. Her penis soon began to harden in my hand and, unlike her blonde companion, Riley was a grower. When her limp inch and a half was fully engorged it was a respectably thick five inches.

I picked up the pace of my fucking again and matched it, stroking Riley's penis. She purred like a kitten and her face was a mask of pure pleasure as my cock sawed in and out of her ass. I could only assume that my cockhead was doing a number on her prostate and precum began to ooze over my fingers. My own pleasure was building to a climax and I knew it wouldn't be much longer. Normally I had more control, more stamina than this but the situation was so erotic that I was having trouble. Sara decided that she wanted to be in on the action a little and began her expert dirty talk.

"I want to see you cum inside her, baby." she began. "I want you to stroke her cock until she cums all over your hand and when her tight asshole grips your cock I want you to pump your hot load inside her. I love watching your cock swell up and jerk when you're cumming and I want you to do it. Cum for me baby. Cum in Riley's tight asshole. Pump her ass full of your hot cum, Gary. Do it now!"

Riley batted my hand away from her dick and began stroking it furiously, her hand a blur. After ten or fifteen seconds of this she shut her eyes tight and groaned loudly as spurts of semen began erupting from the tip. The added sensation of her ass repeatedly gripping my cock as it pumped in and out was all it took to put me over the edge. I came, hard. Just like Sara commanded I shot my load against Riley's tender insides as the waves of pleasure washed over me. As the orgasm subsided I slowly stroked my cock in and out to milk the last few drops of semen, and the last few scraps of pleasure from Riley's asshole. Riley giggled in that girlish voice of hers and I pulled out my softening dick from her anus and my cum started dribbling from her loosened ass onto the beach towel.

"That was fucking hot." Sara cooed.

"It sure was." Riley agreed. Jessie bent down over her girlfriend and started licking the cum off of her belly and cock. Sara slid up next to me, hooked a hand around my waist and pulled me in for a kiss.

"So," she said, pulling our lips apart "you wanna go get some lunch?"

I had been so focused on the fucking that I didn't notice until that moment the rumbling in my stomach.

"Yeah, I'd love to." I looked over at Jessie and Riley. "Would you like to join us?" Jessie shook her head.

"We have plans of our own." The four of us stood up and brushed the sand from our skin but then Jessie strode toward me and took hold of my dick. She locked her eyes on mine and her face took on this forceful, determined look.

"But later, maybe tonight, I'm going to come and find you. And I am going to fuck your ass."

I was locked into place. The strength of both her grip and her gaze had me pinned.

"That's right, Gary. I am going to slide every inch of this cock into your asshole, and it's going to hurt, but it's also going to feel so good you'll never be the same."

I couldn't think of a thing to say. The thought of that enormous cock fucking me in the ass was scary, to be sure, but Sara had taught me that my anus can be a source of incredible pleasure at the hands of someone who knows what they're doing. I could only imagine how many people Jessie had fucked, the sexpot. Nervous as the thought made me, I knew that when the time came I was going to go along with it. I was going to let Jessie fuck me.

She saw in my eyes that she had me in the palm of her hand, so she planted a quick kiss on my lips, grinned at me and then she and Riley took their leave. I stood there for a moment watching their gorgeous naked asses retreating across the beach. Sara slipped up next to me.

"How about we go get some lunch? I'm hungry." I agreed and we headed back up to the resort.

SlyKink
SlyKink
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4 Comments
AnonymousAnonymousover 9 years ago
Love The New Cock

Nothing like fucking the ass pussy of a hottttt girl with a cock. Love sucking their cocks before they get behind me and start fucking me while they stroke my hard cock. Every guy should feel a beautiful girl's cock fucking them, it would turn most guys into cock sluts like me. oldvintner@msn.com

AnonymousAnonymousover 9 years ago
more

I love this series. Please keep them coming.....and me coming.

AnonymousAnonymousover 9 years ago

Hot t-girl sex! I now want to read more of this story!

ballznall60ballznall60over 9 years ago
Great tale!

Eagerly awaiting the next installment when...I hope...Gary finally turns the corner and admits to a strong bisexual leaning.

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