Kinky Kruise

In celebration of the last day of summer, I wanted to get Jessie into some sexy beachwear, inspired by Overwatch's own Widowmaker and her Summer Games skin.
I asked for the help of to make this happen through the reward for supporting him on Patreon, and I'm very happy with the result. ^_^
If you like what you see, please visit 's DA gallery for more art like this and if you want to help support him, please be sure to visit his Patreon: www.patreon.com/sneakattack122…

The story goes, Jessie decided to take a vacation to finish off the end of summer by taking a cruise. Jessie had never been on a cruise and was always curious to try one out. He was so excited for the experience, he went through the trouble of making sure he had the perfect outfit, spending quite the pretty penny on designer beachwear, and even spent a bit of time working on his tan before hand. Once the ship had set sail for it's tropical destination, Jessie made the rounds to see what there was to offer. Along the way, Jessie was approached and ogled by some of the other pasengers, men and women alike. Most caught on he wasn't really a girl, though some were not as sharp to catch on, but they were all interested in spending time with him and even getting intimate. As flattered as he was, Jessie was more interested in just relaxing and enjoying the cruise, though he did keep track of a few he might want to have some fun with later. In fact, one such person was a woman who seemed to be stalking him the whole time as he noticed her hanging around everywhere he went. Granted it was likely just a coincidence given there was nowhere else to go even on a large cruise ship, but it did seem suspicious that she was always right where he was at the same time. Eventually, while sunbathing, the woman approached him again. She sat down next to him and confessed that she had been in fact following him, admitting that she was very attracted to him. She commented that his androgyny  intrigued her and sparked her curiosity for him, wanting to get to know him better. The spent a good portion of the day talking and experiencing the cruise together. As the hours passed, they grew closer physically, holding hands, sitting side by side together, even holding each other and snuggling on a beach chair together. Finally, the woman convinced Jessie to take her back to his cabin to get more intimate with each other. Sure enough, as soon as they were in the room and the door was shut, she practically jumped him and kissed him. Before Jessie could really react he was making out with her. It was very obvious she wanted to have sex with him, and Jessie wasn't about to argue with her, feeling the sensation of lust come over him as well. With the help of a few marital aids, the two had a very wild experience together. Exhausted, they opted to sleep together in Jessie's cabin for the night. The next morning, Jessie woke up to find the lovely lady digging through his things. At first he was upset, fearing she might be a thief, but seeing she had laid out some of the "toys" Jessie had packed stirred a bit of excitement in him. The woman confessed that she wanted to know more about him, but didn't want to wake him. She knew rummaging through his stuff was intrusive, but after experiencing a couple of his "toys" the night before she wanted to know what else he might be into. Stumbling across his collection ropes, leather restraints, and gags she was really eager to play with them and she had laid them all out on the floor for him to choose what she would use on him. Jessie was a bit miffed that she assumed he'd be okay with her tying him up, even though that's exactly what he wanted at that moment. Unable to resist his own urges he chose the bundles of rope and the ballgag. The woman was quick to get him tied up and helpless, having had much experience with the fetish and a lot of skill, to Jessie's surprise. She used as much of the rope as he could handle, without going too overboard with it, which was almost every single length. She then strapped the ballgag in nice and tight so he couldn't push it out. Jessie was at her mercy. She wasted no time in lying him on the bed and teasing him and playing with him. However, their fun was stopped short when there was a rumbling in both their stomachs. They both agreed that some breakfast was in order before they continued, but the lady opted to leave Jessie tied up, which he was happy to accept. Not that he actually had a choice. She left him with plug in his anus to keep him company while she went to the diner to get them some food. A couple hours passed and Jessie began to wonder what happened to her. He was worried she had played a prank on him and left him helpless for the remainder of his stay. Those fears were quickly absolved when he heard the sounds of screaming and shouting coming from outside his door. There was also loud banging and even the sound of gunshots. Jessie tensed up and was fearful of what was happening. His mind immediately went to a hijacking of the cruise by pirates. Sure enough when the door to his own room was knocked down, his fear was realized. Two thuggish looking guys in ragged clothes and guns in hand stood before him. They eyed him with surprise to see he was already tied up, though far more elaborately than they deemed necessary for any of the passengers or crew. It was obvious to them it was due to some kinky foreplay he was involved in. They were even more surprised when they realized the pretty girl before them was in fact a pretty guy. They just had to show Jessie off to their leader. They carried him out to the main deck by the pool where dozens of armed assailants had held the passengers hostage. Their leader had been speaking to the captain of the ship when his two subordinates presented Jessie to him. He was very amused with the pretty boy's state of willing captivity. Even more so that he was an openly feminine crossdresser. Seeing how helpless Jessie was, being bound so tightly, he decided to have a bit of fun as well as use the opportunity to make sure the passengers were kept in check out of fear of punishment for resisting. He carried Jessie to the diving board and stood him up on it. using an oar, he swatted Jessie in his butt and nudged him forward towards the edge of the board over the pool. Given his limited movement, Jessie didn't really have any ability to resist. All he could do was whine and plead into his gag for mercy. Seeing he was over the deep end of the pool, he would not be able to swim or keep his head above water if he was forced in. He also knew wouldn't be able to wriggle his way to the shallow end due to a net that blocked the deep end from the shallow end, with a steep 90 degree drop where the net ended. Ironic that a something used to protect kids from drowning might ultimately keep him from saving himself from drowning. With on last push and a cry of fear, Jessie fell into the pool and quickly sunk to the bottom. He frantically tried to struggle free, but the ropes were too well tied. It seemed like Jessie might have met his end, but suddenly felt himself being grabbed and then lifted up to the surface. The woman he become familiar with had come to his rescue. She had forced her way past the pirates and jumped in to save him. As soon as they reached the edge they were both pulled out by the pirates and held down. The leader commended her for her bravery, but regretted to inform her that she would be joining him in captivity. They were escorted back to Jessie's room where they knew he had more restraints, and tied her up in the leather straps and single glove from Jessie's collection and then gagged her with a muzzle gag. They then put them both into hogties and left them helpless, but not before taking all their valuables. Eventually hours later, the pirates had left, but no one really knew the fate of Jessie and his lady friend until the ship made an emergency stop 24 hours later. The two were finally discovered and set free. Despite the frightening experience and losing their valuables, the two did find a kinship and agreed to keep in touch for future get-togethers.



Jessie © Me ^_^

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