Steve's Last One Night Stand

"Good morning LOVER!" came the voice, the screen still unclear.

"Who is this? Look, I will pay whatever ransom you want, you just have to let me go" Steve desperately pleaded with the faceless voice on the TV. The voice, obviously female, sounded vaguely familiar but Steve's mind was racing so fast he could not concentrate.

"Come on over and sit down in front of the TV sweetie so I can get a GOOD LOOK at you" the voice commanded.

Realizing he had no choice and accepting the fact that whoever owned the voice was obviously the one in charge, he reluctantly sat in the chair but covered himself with his hands, shamefully aware of his nudity (well semi-nudity if you count the cage).

"No no baby, let me see ALL of you. Now spread those legs nice and wide, let's see how you look in your new uniform."

Steve blushed, both out of embarrassment but also out of anger. He knew better than to mouth off, as he was certain he was in the clutches of some kind of sick psycho so, he sat in the chair and reluctantly spread his legs, letting it all hang out. He tried hard to look nonchalant, but obviously he was not successful.

"Oh Stevie, why so mad?" The voice playfully cooed. "You look so unhappy, and look at little Stevie, he looks very cramped too. Turn that frown upside down sweetcheeks."

Steve said nothing but finally the TV picture came on and his captor was revealed.

"GLORIA!" he screamed when he saw her face. "What are you doing to me?"

"Miss me baby?" Gloria laughed.

Steve, now terrified by knowing he was imprisoned by a former conquest, tried his best to put on his charming face.

"Well Stevie, things are a going to be a lot different for you now. I think your love em and leave em days are over. "

"Come on Gloria, Jokes over!" Steve yelled at the screen. "You can't really think you can keep me here forever do you? People eventually will come looking for me and I am sure you don't want to go to prison, so look, just let me go and we will just forget the whole thing."

Gloria laughed long and deep and the way she laughed really worried him.

"Steve, you don't really know who I am do you?" When he said he didn't, Gloria explained who she was and even better who her father was.

The look on his face as he realized he had fucked the Don's daughter was a classic and Gloria made sure she took a screenshot of it to keep as a remembrance.

"Listen Steve, I don't want to cut you off short here, but you REALLY won't be missed. My dad has friends that are very good at making people disappear, and you my dear have been THOROUGHLY disappeared. After a few months no one will really look for you anymore. But cheer up, things aren't too bad now are they? I am sure you will like living your new beachcomber lifestyle."

Steve gulped hard when she said months and he was rapidly beginning to panic, his hand reflexively fondling the lock on his chastity cage.

"Ah, and now we come right to the point. I am sure little Stevie is wondering when (or if) he will ever get out again. Well it is all up to BIG Stevie. Now as I am sure you have noticed, there are cameras all over this house as well as the rest of the island. They are on a private satellite channel that only has ONE viewer, he he, ME! I must admit Steve, you are one hunk of good looking man-meat, even if you are (or should I say WERE) a total player. Well, all that spunk that is building up in your balls, all those raging hormones and desperation to spew your seed all over everything with a skirt will now have only one outlet, servicing my needs. And if I were you Stevie, I would make sure my needs are serviced well."

Steve knew he was trapped, so he did not argue. He figured it best to go along with whatever this crazy woman said until he could find an opportunity to escape, which hopefully would be soon. Silently he nodded his head.

Gloria then explained what her expectations were. As he was constantly monitored by video, his options for escape were pretty limited and any attempt would be detected and severely punished.

On the other hand, if he was good, and did as he was instructed each day, she promised to come visit him on the weekends. This island it turns out had been in her possession for quite some time and is extremely secluded, being approximately 90 miles off the east coast of Florida, and because of its size, it did not appear on any of the standard maps.

She is the sole owner and has the whole thing programmed to her exact specifications. Each morning she would check in with him and give him his tasks for the day. If he pleased her during the week, she would visit, if not, she would not.

She informed him that he had enough supplies for a month and would be instructed on what to do when he was to be re-supplied. She then asked a question that really puzzled him.

"Did you ever work Construction Steve?"

He indicated that he had, back when he worked his way through college to which she giggled that it showed in his shoulders and would come in handy now.

Nodding, she informed him that his task was to rebuild the wall around the back patio. The stones he was to use were on the other side of the island, so it might get a little tiring, but, she added for emphasis and with a hint of malicious glee in her voice, it certainly would keep that fine muscular body of his in shape for her.

As he started to ask her more questions, which he of course had plenty of, the TV suddenly shut off. In frustration he pounded the bare table in a fury. He wanted to know answers and most importantly to him that minute, he wanted to know how long he was going to have to wear this goddamn cage!!

After finding food for breakfast, Steve went out exploring the Island again, looking for the patio and of course the supplies. When he found the patio his heart sank. It was going to be a hell of a job as it was 50 x 50 and no foundation even existed.

As he walked to the other side of the island his heart sank even further when he discovered just a big pile of bricks and a small metal drum with some 100 lb bags of mortar mix. Realizing he better do as instructed until another plan arose, he struggled to pull the supplies over to the patio.

All day he struggled, muscles straining, sweat pouring off in buckets as the Tropical sun beat down on his naked ass.

Ninety miles away, Gloria, sitting at her desk flipped on the feed to her computer and watched the display and luxuriated in air conditioned comfort.

She was getting incredibly turned on watching him heave, sweat and struggle with the stones and unconsciously she reached down and felt her pussy through her panties, and as she suspected, they were drenched. The thought that she was sitting in her air conditioned comfortable office slowly frigging away while watching her "slave" toil in the sun, completely naked and cock all bound and controlled made her hornier than she had ever been in her life.

That evening, as Steve showered, she watched him again on her computer, pushing herself over the edge as he desperately tried to rub himself to an orgasm through his cage. After 45 minutes, he gave up in frustration and dropped to his knees almost weeping, pounding the floor of the shower and cursing up a storm. As he screamed in impotent, desperate and throbbing rage, Gloria once again brought herself to a screaming orgasm watching his performance as she rubbed and teased herself with her vibrator.

She shuddered and moaned as her fluids rushed over her hands, and she spread herself naked before the screen, imagining his frustration and desperation throbbing in his cage. She loved this so much, and it awoke in her dark desires she never knew she had. She couldn't wait until the weekend.

Steve was sleeping very fitfully, tossing and turning, dripping in sweat. Flipping over onto his stomach he moaned lightly as he rubbed his cock, still in its cage, helplessly on the bare mattress.

He was still asleep, and having a wonderful, and at the same time terrible dream. In his dream he was chained to a bed in a strange house, and all around him were women, all beautiful and all incredibly horny.

They each took turns riding his face while one or two sucked his cock which, as you would expect, was unbelievably hard. In the dream he kept getting closer and closer to cumming, but at the last minute they would stop stimulating him and he would just throb, desperately hanging on the edge as they all pointed and laughed at his desperate gyrations but then began sucking him again.

Even his dreams were tormenting him now as his lack of sexual release was affecting him an all levels. As he became more desperate, the part of his body that was still conscious tried desperately to get some friction to release the cum that was boiling in his balls. Right as he was approaching blastoff in his dream, the TV set turned on he woke up.

"DAMN IT!!" Steve screamed as he realized his dream had been cut short right at the last moment. He looked down at himself, face down on his bed, dry humping the mattress like crazy and he was humiliated as his face filled with shame. He knew Gloria was watching all of this, and as her voice filled the room from the TV, she was laughing at him. His tortured and denied lust obviously was very amusing for her.

Shaking the cobwebs out of his head he sat up quickly and tried to cover himself. Knowing the drill, he sat in the chair and awaited his instructions for the day, taking care to be as charming as possible, hoping he could still weasel out of his situation somehow.

"My, My, My Steve" Gloria started. "You sure do know how to put on a show."

Her grinning face filled the screen, but today was different. He noticed she was dressed very provocatively; leather teddy, long black stockings, push up bra, and as she came into focus his eyes greedily devoured her incredibly sexy image. The past few days had been the longest he had gone without getting off since he could remember, and he was climbing the walls.

Steve winced as he felt his cock try to burst out of its cage, growing hard at the sight of her, but denied room to expand to the fullest.

Even though Gloria was his tormentor, she was still a very beautiful woman, and with him lost in a haze of denied lust, as well as being denied ANY other female company or even image on this island, his bulging balls were happy to see her.

Steve forced a grin onto his face and then noticed that on a chain, hanging between her glorious breasts and nestled in her cleavage was a gold chain, and on it, a key.

"Ah, I see you spotted the most important object in your sad little world" Gloria continued as she picked the chain up in her fingers and began to swing it back and forth. "Yes, this little piece of metal is now the center of your whole universe. This is the key to your cage and whether you earn the right to have me use it is really up to you. Today is Tuesday and I already am planning a getaway for this weekend. Now, if you keep being good I may decide to come to the Island Friday Night instead of flying up to New York."

Steve smiled. Although he was incredibly angry obviously at his situation, this was the first time in days that even the HINT of possible relief for his aching balls was suggested. He again decided that the best policy was to play along with whatever Gloria suggested and hope for an opportunity for escape presenting itself at the right time.

For now however, he only had one thought and one thought only, and that was getting out of this cage and blowing his load as soon as possible.

"So here is the deal. IF I decide to visit, don't think you can overpower me or pull some other stunt. As you know, this whole island is being monitored by video, so ANY funny business and some of my "friends" will come and teach you a lesson you won't forget."

Steve nodded in agreement, and added that even though he is most distressed about his situation, he could never hurt a woman. This wasn't idle talk and Gloria sensed he was telling the truth.

Steve, although a dog in his former life, was not a monster and the idea of ever striking a woman was an impossibility to him no matter what might provoke him. No, she would be safe with him, although she knew she would have to be careful.

What also was dawning to Steve was how, even though this whole situation was completely intolerable, and he should be absolutely furious at Gloria, he found her incredibly exciting and in some weird, dark, and until now unknown kinky side of him thought he might be oddly enjoying his treatment. Part of his brain was really getting off on being so completely dominated by this woman and it both intrigued and shamed him to realize it.

"I am glad you agree Steve, as I would hate to see anything "bad" happen to you if you were to try something stupid. Now, Today I have a special assignment for you, but it is different than yesterday. I have some workman coming to the Island to make a few "modifications" for me, so when you hear the horn on the boat as it moors at the dock, you are to lay down on the bed, and attach those manacles to your feet and wrists. The workman will go about their business and will make sure you can get out before they leave. Do NOT speak to them or make any attempt to escape. They have all been informed of your situation and work for ME, so they will NOT speak to you in any way unless they need your cooperation. Understand?"

Steve gulped as he realized his shame would now be broadcast to others as up to now he had not seen another soul on the island other than Gloria. He was also not hopeful that this was a method for possible escape, as he was worried about what these "workman" might do to him when he was naked and helpless.

Even on a more practical note he also worried about how they would all think him a giant fool, letting himself get caught into this situation. When Gloria mentioned that, as a special treat for him, and realizing he might be craving a bit of female companionship, she went to the trouble of contracting with a firm that had hot girls as workers and she giggled at his response as his face turned red.

Steve blushed even harder as he thought about these hot girls looking at him chained to the bed, naked and his cock encased in it's little plastic prison and obviously laughing their asses off at his predicament. Hearing her speak he knew that this was going to be the most humiliating day of his life.

Gloria explained that he was to do whatever the girls asked him to do and since she would be watching via closed circuit, any failure to comply with their wishes would be punished. He was not to speak to them at all, but only answer questions they might ask. Steve listened intently to her instructions and again, more questions arose in his head. Who were these girls? What sort of modifications were they making? As he opened his mouth to ask, once again the TV suddenly went black, and Steve was sitting alone in silence.

As he did the day before, he had his breakfast and went down to resume his work on the patio wall. It was backbreaking work, and after just a few minutes he was already drenched in sweat but kept an ear out for the boat, not knowing when it would come. He figured he should continue this project and guessed, and he was correct, that the more he "obeyed" Gloria, the better his treatment would be.

As she had the day before, throughout the day Gloria switched on her live video stream from the Island and lost herself in lusty thoughts watching Steve sweat and struggle. The perspiration running down his back and the fact that his man-fur glistened in sweat caused her to squirm in her seat as her juices were running down her inner thigh. Steve's slavery touched her in ways she could never have imagined.

She was obsessed, and reveled in the fact that whenever she wanted, she could "tune in" to her own little private porn channel, made JUST for her. As she lightly rubbed her clit through her panties, watching Steve lifting the heavy stones up onto the wall, she noticed him stop and look at something on the ground. As he looked around suspiciously, trying to spot the camera outside he picked it up.

Steve knew about the cameras inside the house, but still was unaware that he could be seen EVERYWHERE on the Island, as hidden cameras were dotted all over the island, covering every inch in their scope. Disguised in the trees as coconuts, or on the beach as a rock formation, there was no place he could go where he was unobserved. Gloria knew this, but of course, Steve did not, and when she saw the object in his hand she wondered what he was planning.

The object was a long white feather that must have fallen from a seagull or some other bird. She giggled as she saw Steve run down the path leading to the beach and into a little cove he obviously thought was hidden from her view. Thinking he was out of sight, he started to desperately manipulate the feather under his cock cage.

Gloria gasped as the scene of Steve trying so desperately to pleasure himself made her wetter than she had ever been in her life. That boy was so desperate for release he would do almost anything she thought to herself, and as she watched his display she finally could not control herself or her arousal anymore. As she watched the display intensely she stripped off completely naked and spread her legs wide, putting each foot up on her desk.

Her right hand rubbed light little circles over her nipple while her left slowly curled up into her pussy, using her own fluids to wet the end of her pleasure bud.

Watching Steve's desperate thrashing in an attempt to get off made her beyond hot and her mind imagined that instead of her hand teasing her clit, it was Steve's tongue instead. And that tongue was attached to his glorious body, bound, desperate and throbbing; willing to do anything on earth to please her. Reveling in her imagination and frigging furiously, she climaxed almost instantly, the first of many she would enjoy that afternoon.

This show went on for hours and to Steve's great disappointment the feather did provide a little stimulation, which his cock sorely needed, but it was not enough to get bring him to orgasm. Sweat pouring off of him for hours, he attempted to stroke himself with the feather through the opening in the cage, but all he ended up doing was making himself more desperate and frustrated than before. Finally disgusted and furious he threw the feather to the ground and pounded it with his fist, tears flowing from his eyes as he grabbed his tortured caged cock and rocked back and forth moaning. He ached so bad he could not stand much more and feared if he didn't get relief soon his sanity would be a casualty.

As he panted and gasped in his horny haze, he heard the horn of the boat as it approached the dock. Jumping up quickly he feared he would be caught outside, and therefore disobeying his instructions, so he ran like a bat out of hell back to the house and quickly shackled himself to the bed. Gloria adjusted some controls on her computer and the camera in his bedroom focused tightly on his balls as she saw him run inside. Grinning she admired the delightful shade of violet they had turned, and wondered to herself what they would look like on Friday.

At the dock four stunning girls got out of the boat all with slightly nervous expressions on their faces. Their boss had explained this unusual assignment to them, and they all wondered what it was all about.

Being the only females at the company, it was odd that they all be sent on the same job together and even odder when it was explained to them how they were to be dressed. All were wearing cutoff jeans and T-Shirts, as directed, and they looked more like they were about to film some sort of beer commercial rather than work on a contracting job.

They had balked at first at the weird requests, as they were contractors not strippers, and were a little worried about what sort of pervert was setting this whole thing up. Once the bonus they were to be paid was explained to them ($5,000) each their worries did not totally dissipate, but their enthusiasm certainly increased.