The following story contains graphic sexual scenes between men. If material of this nature offends you then you should not read this story. Additionally, if you are under 18 years of age in most states you are not allowed to read this story by law.
This story is purely a work of fiction. Any resemblance to person's living or dead, or to events that may have occurred, is purely coincidental. Additionally, the actions of the characters in this story are in no way intended to show approval of, or give sanction to, their actions.
The author claims all copyrights to this story and no duplication or publication of this story is allowed, except by the web sites to which it has been posted, without the consent of the author.
Comments and story suggestions are always welcome and you may e-mail them to: lacieman@yahoo.com
The Proposal
Steve looked at his computer screen with tired eyes. It was late - past midnight in the middle of the week and he was still awake when his wife had decided to turn in over an hour earlier. He had recently found himself surfing the web in places that he was unfamiliar with. In particular, Steve was looking at sites that had strong sexual content. It started innocently enough, looking at some pictures of famous women wearing little to nothing. Then he would find web sites with women and men in all sorts of sexual situations. And now, Steve was surfing some bisexual sites with curiosity.
He had never really considered being with a man before he had discovered these sites on the web. It didn't help that Steve also found chat programs where he could speak to men and women who actively led bisexual lives. At least, they claimed to when he chatted with them. He had been faithful to his wife during their marriage, never doing anything with another woman or man for that matter.
Like a babe in the woods, Steve found himself being hit upon by men when he would join a chat room for men that were "curious". It surprised him how open men seemed to telling him what they were interested in doing sexually. Then again, he realized what being a woman must be like. Men are typically very straightforward and though he wasn't a romantic, Steve hoped to chat with someone who was similar to him with curiosity.
It seemed to happen one evening when he came across a person named Jerry. Jerry had told Steve much of his background and they chatted for well over an hour. What Steve learned made him hopeful that there were "normal" folks out there online. Jerry was more interested in talking to Steve about what he was curious about rather than find out how big his cock was and what Steve would do with his cock. Jerry also had something that so many others did not, he lived not very far from Steve.
Steve went to bed thinking more and more about bisexual fun. Jerry had somehow made him more interested than just curious, helping Steve lower his defenses and building trust with him to a degree that no one had ever tried before.
Over the next few nights Steve found himself going more and more to the web to chat. He found Jerry as a person who was very similar to him. Though Steve was 33 and Jerry was in his early 50's, they seemed to be comfortable when chatting together. Perhaps it felt more like a mentorship than some sort of romantic connection.
The first 'move' so to speak was made by Jerry. During a chat, Jerry asked Steve if he would ever carry through with meeting a man for a sexual encounter. It made him think long and hard about what he could do in secret without his wife finding out. He had to be very discreet if he were ever to try this. It was crazy, he couldn't do this to himself and to his family. But somehow, the excitement that he felt thinking about this was something that kept him from dismissing the possibility completely.
His sensible side made him think of a neutral meeting first time. Steve wasn't going to do something sexual the first time he meets a strange man. He chuckled to himself thinking of his role being reversed, how far was he to go on the first date - knowing full well that men want to get a home run the first time.
They met. At a coffee shop. Someplace public and innocent. Steve's practical side made sure that he wasn't going to do anything foolish. He couldn't believe he was doing this in the first place. When Jerry came in, it made him feel a chill of excitement. He was just as he had described - a decent looking, well kept masculine man who dressed in business casual similar to Steve's everyday clothes at work.
They talked and seemed to connect. Having many things in common both from experience and in general attitudes. Jerry told Steve he had been with a few men before and liked the experience. He went on to tell Steve that he was interested in getting to know Steve even better. But, he had one small request. Handing Steve a large, blank business envelope that was sealed he asked Steve to consider the proposal within. As he went to tear it open, Steve was stopped by Jerry who asked that it be done after they part. Jerry wanted Steve to take some time to consider what was inside and then act upon it after thinking about it for a week.
Steve's curiosity made him want to rip it open quickly but he respected Jerry and his request. They parted and went back to their lives for the day. In short order, Steve ripped open the envelope to find a hand written note and a page from a catalog. The note detailed how Jerry had been very happy in meeting Steve and hoped to find a way to meet in private. However, there was one request he had. The note went on to say that Jerry had been visiting various web sites as well and was interested in a fetish. He plainly asked Steve if he would consider wearing the item from the catalog. It was a color picture of a woman wearing panties.
This was a surprise for Steve. He had never thought of something such as this. Steve thought that any kind of bisexual encounter would be between him and a man. Something of this nature had never come across his mind. He shook his head, this wasn't right, he wouldn't do this. It was just plain strange to him. The note went on to say that Jerry offered what he had hoped would be a fair trade. For Steve getting and wearing the panties pictured, Jerry offered to perform oral sex on Steve. No strings attached, no reciprocation requested. Was this a steep price to ask for something that he had thought about for a while? The note ended with Jerry asking Steve to think about it for 5 days before making a decision.
Those 5 days occupied Steve's mind whenever he had a free moment. He tried to visualize the silly look of him in panties and nothing else. Then, he saw Jerry with him, trying to suck on his cock. It seemed strange each time he tried to beleive it was being offered to him. However, Steve always ended up rock hard when he thought about it.
The 5th day came and Steve found himself at a lingerie store, purchasing a pair of panties that matched the picture that was in the envelope. That night, Steve told Jerry that he couldn't beleive himself but he had bought panties and was willing to try Jerry's proposal. Jerry was naturally thrilled and then went about trying to set up a meeting. A motel was the likely place since they could go, pay cash and remain anonymous.
Using a round of golf as an excuse, Steve had clearance to be away from his wife for 5 hours on Saturday. Plenty of time to meet with Jerry. They met in the lobby and Jerry took Steve to his room he had rented. Nervous like he had been on his first date as a teenager, Steve's heart raced. It was totally unreal how this all felt, as if he was watching a story rather than living it.
They entered the room and an uneasy quiet filled the room. Jerry went to the little table in the room and sat in the chair. He told Steve he would very much like to see him in the panties. Blushing, Steve took the panties from the bag he kept them in. Pulling off the tags, he held them up for Jerry to see and saw a smile of content on Jerry's face. Steve stepped back around the corner to the sink and bathroom, just out of sight of Jerry. Jerry laughed that Steve was bashful and made a comment to him about how funny it was that Steve was suddenly modest.
Steve laughed as he stripped just out of Jerry's site. He slipped on the panties and was amazed at how hard he felt when he put them on. The sheer material of them managed to hold his cock inside but it was clear they were not constructed to hold a mans equipment. Steve stepped out and faced Jerry. Jerry was stunned by how turned on he was by the site of Steve. Jerry had long fantasized about a masculine man in lingerie and now, there was one standing before him.
Steve stepped closer to Jerry who looked not at Steve's face, but at his pantied crotch. Just as Steve went to ask what Jerry thought, Jerry slid forward on his chair onto his knees, his hands came up to hold Steve's thighs. Before Steve could say a word, Jerry moved his face in and was kissing Steve on his panties. The hot breath and pressure of his lips made Steve groan in pleasure. He looked down to see and feel this man kissing his soft panties hard. Instinctively, Steve placed a hand on Jerry's head to encourage him to continue his affection.
Jerry's hands moved up to grab Steve on his butt. Gripping it tight, he continued to kiss and lick the panties until they became soaked with a combination of saliva and pre-cum. Moaning encouragement, Steve felt so caught up in the moment. Wearing panties was a small price to play for what was going on. Steve felt Jerry slip a finger in the leg of the panties to tickle his balls, causing a series of groans as Jerry played.
It wasn't long before Jerry pulled Steves cock free of the panties out of the leg. That way, he was still wearing them while receiving oral pleasure from Jerry. Steve nearly fell over as Jerry sucked him into his hot mouth. Moaning loudly now, Steve felt pleasure that was intense. His cock was being worked by a man for the first time and he loved it. It didn't feel strange - it felt incredible. The panties made him conscious of his butt and cock and balls as they gripped him so much tighter than his normal underwear. The constant sucking on his dick created waves of pleasure as he was being given a blow job by Jerry. This proposal to wear was everything he had imagined and more. The head Jerry gave him was as good as any woman if not better, Jerry knew how sensitive the cockhead was and his tongue exploited this. Steve moaned as he neared orgasm.
As Steve's cock hardened to orgasm. Jerry pulled the young cock out of his mouth and stroked it quickly. Causing Steve to shoot, arching his back, his cum shot several feet across the room - powered by the lust he felt from the orgasm Jerry provided.
Crying out, Steve was emptied of cum by Jerry.
Catching his breath, Steve stepped back and sat on the bed in the room. Jerry rose to his feet and handed Steve the key to the room. With a questioned look on his face, Steve asked what was wrong. Jerry told Steve that he loved what had happened and was so glad Steve took his proposal. But that anything further would need a new proposal. Jerry winked as he went to the door and asked Steve to look for him online in 2 nights.
As the door closed, Steve looked in the mirror of the room. Sitting in a pair of panties, he had just been sucked off by a man. And it was incredible. He thought of what could possibly happen - and would there be another proposal?
End