Three guys meet at a bar. One is a devilishly handsome young bachelor who normally shoots par. Another is a middle aged, average looking, divorced man with an eleven handicap. The third is filthy rich and never mentions his golf scores. Of course, they are having a drink at their country club.
Most of the conversation revolves around golf and sports until Guy, the middle aged man, says, “I’ve come up with a cool idea for the Internet. Tell me what you think.”
“Go on,” Bernie, the older man said.
“I was watching one of those reality shows like ‘Bachelor’ or ‘Bachelorette’. I can’t remember which. Well, I got thinking about producing an online reality game?”
Randy, sitting across from Guy asked, “Does this somehow involve us?”
“It could,” replied Guy.
“Count me out,” Randy said rather emphatically. “We’ve heard your crazy schemes before.”
“Wait,” Guy responded. “Hear me out.”
“Okay, what’s the idea, Mr. Producer?” Bernie inquired.
“Look, there are a couple of parts to it. First, all three of us are different ages and have different lifestyles, but we’re all single. I got to wondering which of us would get the most hits from women if we put our profiles together on a blog, something like a dating site. Who would they choose to date?
“The reality part is that women will respond to one of our links with their profile. Each of us chooses the best profile from our site and arranges a date with her. She will be one of three semi-finalists.
“After having a date with the lady, we compare notes. The woman providing the best experience wins an all expense paid cruise with the man of her dreams.”
“So what do we tell them about us?” Bernie asked.
“Okay, Bernie, you are a multi-millionaire and a widower. We tell them no more, not your age or include a picture. Randy, you are a young, single, ruggedly handsome guy with ‘to-die-for’ abs. I am the compassionate recently divorced middle aged family man with a killer sense of humor. The idea here is have them choose superficially. We don’t want them checking off their bucket list for the ideal man. By the way, only women between thirty and thirty-five are allowed to play.”
“Why that age” Bernie asked.
“That’s the age when women are still young enough, but experienced, and have an interesting history. It’s a stage when they have become dissatisfied with their life, and looking for more. It’s a little like a mid-life crises, and they might be more vulnerable.”
“That makes sense, Guy, but I don’t think this is going to work,” Bernie, the voice of reason said.
“Me neither,” added Randy, the pessimist. “Anyway, women aren’t gonna fall for it. They’re not that gullible. They’ll think it’s a scam.”
Guy replied with a high degree of optimism, “Some will think it’s a scam, but they go for it on the ‘Bachelor’, don’t they? Look, I really think we can pull this off. When a woman sees something she wants, there’s no stopping them. That’s what the cruise is all about. Hey fellas, we have nothing to lose. Come on, let’s give it a try. I’ll set it all up.”
With a few more beers and a little more persuasion, they all shook hands in agreement.
Guy, as a computer programmer, had little trouble merchandising and commercializing the venture. He had links all over the Internet. The blog was professionally designed and read:
LADIES: A TRIP OF A LIFETIME!
Here’s your chance to win a free ten day cruise with the man of your dreams.
Play the new, Bachelor4U online game. Date the bachelor of your choice!
It pictured a cruise ship along with the rules. They included:
1. Women 30 to 35 are eligible.
2. Choose one (1) and only one of the three men below, and send him your profile.
A. Young, single and ruggedly handsome with “to-die-for abs.
B. Compassionate divorced family man with a wicked sense of humor.
C. Retired multi-millionaire and widower.
3. Tell him about yourself in detail. Pictures are preferred.
4. Send your information to the following site: and click on the link to your favorite bachelor.
5. The three finalist will be notified by e-mail. A time and place for your date will be by mutual agreement.
6. A winner for the cruise will be declared following the completion of all three dates.
For the three men involved, all that was needed was lots of patience. The responses creeped in slowly at first, then all at once after Guy posted it on Craig’s List.
The contest ended six weeks later. The results were a bit of a surprise since Bernie received the greatest majority of the responses. No one was really surprised when Randy was next, then Guy..
Narrowing down the three finalists was a challenge. Some entries were long essays. Others were more concise like a Reader’s Digest version of their life. Pictures varied from facial to whole bodies. Some were even topless and several were completely nude. Women were willing to drive or fly from out of state. Many were mothers seeking fathers for their kids. Those were always deal breakers. Most suggested friendships with benefits. Those offers were definitely welcome.
Randy selected Samantha or “Sam” who had just turned thirty and had big tits. Guy chose Betty who was honest about her divorce, was not pretentious, and didn’t seem to take herself too seriously. She said if it hadn’t been for her getting caught shacking up with her husband’s brother, she probably would still be married. Finally, Bernie chose Gail who read the same books and listened to the same music as him. Gail said she had a father fetish and liked older men. Gail added that she hoped she hadn’t offended him by assuming he was older.
Guy and Betty were the first to hookup. She drove five hours to meet him on the edge of town for dinner. He recognized her immediately from the picture she had sent. At least she hadn’t sent a Photoshopped airbrushed photo. Betty was a pretty woman with a nice body, curvy, but not over-weight. She ordered a glass of Chardonnay. He had a Manhattan with a twist. They talked for a half hour before ordering dinner.
“What got you interested in our game, Betty?” Guy asked.
“Oh, it sounded exciting and to be honest, I need a little more excitement in my life.”
“You said you are a nurse. That’s pretty exciting, right?”
“Yeah, but it isn’t the kind of excitement I was referring to. Since getting divorced, I haven’t dated except for occasionally screwing my brother-in-law. After his wife found out about our affair, we haven’t gotten together very often.”
“How did that affair get started?”
“I was madly in love with him when were were both teenagers. Then he went off and married my girlfriend. To make him jealous, I impulsively married his brother. I really didn’t like the guy that much but all my friends were getting married, so I wanted a ring too. Ring-a-ding-ding, I got the ring,” and she showed it to Guy.
“That’s a nice ring, but you didn’t explain about the affair.”
Betty took a sip of wine and said, “Well, I wanted to get back at my girlfriend for taking my boyfriend.”
“How has that worked out?” Guy asked.
“Not well, so here I am. I really need to get away and the cruise sounded perfect.”
“Where are you staying?”
Betty looked a little surprised when she said, “I thought we were staying together at your place.”
“Did I say that?”
“Not really.
“It is, Betty, as long as you are okay with it.”
“I didn’t drive five hours to get a pedicure. Look, Guy, I’m past the age of playing hard to get.”
“Apparently,” Guy answered with a grin. “Let’s order dinner.”
During dinner, the two found many things in common. She was easy to talk to. In addition to being a great dinner companion, Betty intensified his sexual appetite as the meal progressed. They didn’t finish dinner until after ten that evening.
Guy’s excitement only doubled driving to his home. Betty followed in her car close behind. He was thrilled with his choice. Betty was perfect only he was unsure about taking the next step.
He didn’t have to worry. Betty knew how to proceed, perhaps from her sexual escapades with the brother-in-law. “Can you fix me a vodka martini?” she asked once they settled in Guy’s apartment.
“Sounds great. I’ll have one too,” he said nervously.
“How do you like it?” she asked.
“On the rocks, and you?”
“I didn’t mean the martini.”
“Well, what did you mean?”
“What are we here for, Guy, a home improvement inspection?”
“Okay, you mean how do I like sex?” he asked rhetorically.
“You got it my gallant lord and master.”
“My wife wasn’t into it much, so there wasn’t much experimenting. It’s one reason we divorced.”
“How about if I become you sex slave?”
“I don’t know. I don’t know much about that.”
“Oh good. Then I can show you. I brought along some toys that might help us, say, experiment.”
“Like what?”
“Like restraints, clamps, plugs, dildos and my favorite, an Hitachi magic wand.”
“My god, you really came prepared. It’s going to take some time for me to get up to speed with all of that.”
“Have you used a cock ring?”
“Nope.”
“We’ll start with that after I bring in my luggage.”
Guy helped her park her baggage in the bedroom.
“Okay,” she said. Get undressed, and I’ll fit this around your cock and balls. It’s easier to get it on if you are soft. So don’t get too excited.”
Betty took out a collection of three silver rings and said, “I didn’t know what size you were, so we have a few to choose from. Later, we can use the smaller ring at the base of your cock. It helps a guy from coming too quickly. Oops, sorry for the pun.”
Guy laughed while he kicked off his shoes. The rest of his clothing tumbled to the floor like snow in a blizzard.
“Alright, you’re about the same size as my ex. This middle ring will be perfect,” and she pressed his cock and balls into it. With that, his excitement began to show.
“Help me out of this dress,” Betty purred. She wore no bra or panties to expedite the situation. She said, “I really don’t like the constraints of underwear. I feel sexier without it.”
This was Guy’s first view of her naked body. Betty’s breasts were large but not huge. Age had not caught up with them, so there was no sagging. Her nipples were large and a healthy pink. She was shaved except for a small fluff of pubic hair above her slit.
“You are beautiful, Betty.”
“Thanks, I appreciate that. How about clamping these onto my tits. It really turns me on.”
She showed him how to clip them on after tweaking her nipples to make them erect. It had a chain connecting the two ends.
“God, you are so sexy wearing those clamps. My heart is exploding,” Guy admitted.
“Glad to hear it. Now take my wand and massage my clit. I’ll give you a blowjob after you get me sopping wet.”
Betty spread her legs lying on the bed, and showed him what she meant. He quickly got the picture. It didn’t take long before Betty’s juices were flowing and was on her knees with Guy’s cock down her throat.
“Hmmm, I love the taste of precum. You are so hard and big, Guy. Let’s try it in my pussy.”
He didn’t have to be asked twice. He rubbed her slit up and down with his prick then plunged into her hot slippery cunt. It felt so fantastic, especially after not having sex with a woman since his divorce. He had almost forgotten the sensations. Thankfully, the cock ring helped, otherwise he would have exploded after a couple of strokes.
Even then he didn’t last long. He was blasting load after load of cum into her accommodating tunnel. Sweating profusely and trying to catch his breath, he collapsed on the bed,.
“Wow, that was a quickie,” Betty gasped. “Maybe you haven’t been with a woman in awhile. It’s okay. I liked the feeling of you squirting inside me. Thanks for that, Guy. I think with my toys, next time we’ll manage a longer playtime.”
“Maybe in the morning, Betty. I’m wasted.”
In the morning, Guy was nearly back to normal when Betty said, “Tie me up, Master.”
“Really?”
“Look in my toy chest and take out the cuffs. There is a set for my ankles and another for my wrists. Put them on me, then tie the ropes to the opposite sides of the bed.” She laughed and said, “I’ll look like an ‘X’.
“There’s an orange ball that goes in my mouth. You hook it up behind my head. Be sure to use my nipple and clit pumps when you play with me. I’m your sex slave now. You can do anything you want, but don’t forget the wand. Oh, one last thing, I see you left your cock ring on from last night. I suggest you add the smaller one at the base of your cock when you fuck me this morning.”
A long period of submissive foreplay followed. Guy tried out all of her glorious tools of torment. For Betty, they were the implements of pleasure.
Guy pumped her nipples to a swollen erection. He loved the look, then applied the vibrating wand to them. He did the same on her clit. Betty’s eyes rolled back in her head in dreamy passionate contentment.
Betty’s excitement could only be surpassed by his. Guy’s cock was throbbing and needed relief. He slipped on the second cock ring as Betty had suggested and plowed into her defenseless cunt.
This time Guy responded with an Olympic gold medal performance. Betty cried out with burning desire. Her orgasms came early and often. Her face turned a blushing pink and her pussy flowed with passion.
Guy’s thrusts accelerated and he bore deeply into her inflamed juicy hole. He was intoxicated by the frantic undulation of her hips meeting his, each time as if begging for more. He gave it everything he had.
His hard throbbing staff began to pulse, and he shot wad after wad of his creamy sperm inside her pleasure cave filling her time and time again. He didn’t waste a drop. Guy squeezed out every last thick glob of his seed before pulling out.
“My god, Guy, what a guy!” and she giggled. Betty wrapped her arms around him and gave him a deep passionate kiss before saying, “That’s what I meant last night about needing more excitement in my life. You gave me what I needed just now,” and she gave him another passionate kiss and hug. “I can’t wait to do it again.”
They did an encore but not that morning or afternoon. In the afternoon, Guy showed her the city. They went for an early dinner and resumed their debauchery after dark. Both parties had completely fulfilled their lurid expectations.
The next morning, Betty left for home saying, “I enjoyed your company, Guy. Keep me in mind for the cruise.”
“Definitely!” he responded and waved to her goodbye.
NOTE: Next up, follow Bernie on his date!
