Not sure of what type of disclaimer to put here, so I'll do a generic. This is a fictional story. The author does not recommend unprotected sex in any cirucmstances. Remember, it's a cess pool out there.
Jake paused for a minute to consider the possible outcomes, good and bad, of replying to the message. There was so much to think about. Urging him to press “Enter” were the thoughts of sexual excitement and fulfillment of fantasies that he'd been having for decades. All the positives for replying were easy to appreciate. It was the potential downside concerns that made him cautious. Safety issues and the possibility of being exposed were top of the list. He did live in a relatively small city and he couldn't afford to be “outed” in this way. But in the end, he pushed the key to send his reply on it's way. No turning back now.
At 56, Jake still considered himself young, at least in his mind. Yes, his body was old, and he had to slow down, but it was hard to do. He still had the desire to do things people half his age were doing. He was married, for just over 30 years now, and he loved his wife. She did everything for him. Everything, except the one thing. Over the past 10 years, their sex life had slowly but surely come to a screeching halt. Part of that was his fault. He did have some health issues. But still, it didn't slow down his masturbation activity in the least. If anything, he had become even more regular. And his video stimulation during the jack-off sessions had become more and more extreme. Everything from group sex to trans-girls; bestiality to bi and gay videos. There was little that was not on the menu.
So a few years ago, it wasn't really that great of a leap for him to try out an escort. He had been away on a business trip and planned out the encounter for months, being sure to do everything he could to keep all the risks low. Perhaps because he still loved his wife and had a desire to keep from hurting her, he had decided to retain the services of a trans-girl escort, or T-girl. In his mind, it was the best of both worlds. Since she was not a genetic female, he wasn't actually cheating on his wife. But by the same token, here was a person who was trying her best to be the perfect woman.
It had been better than he had imagined it could be. So much so that he repeatedly saw the escort several times, going out of his way to make sure his business trips included travel to the same city. It wasn't more often than every six months to a year, but he found himself looking forward to the next visit shortly after he returned home.
One of the many things he enjoyed during these encounters was the oral sex. Like so many married men, his wife had long ago stopped pleasing him in this way, even though he made it clear that it was something he wanted. The escort, being a genetic male with a penis, inherently knew how to please a man orally. At least this one did. And Jake found it thrilling, even fulfilling to bring her to orgasm orally. To have her spill her semen into his mouth was the highlight of their sessions. He savored the thick gooey cum, rolling it around in his mouth. He knew it would be months before he would have another opportunity and wanted it to last as long as possible.
Perhaps it was his fascination with blow jobs, both giving and receiving, that eventually led Jake to search for interaction sites for gay men. A quick Google search had revealed many such sites that facilitated gay men meeting others for all imaginable encounters. Everything from quickie one-night stand meet-ups to long term relationships. But it was clear that all the sites he visited were predominately younger men. The profiles were actually quite aggressive, so much so that he never went through with any meetings. Yes, he responded a few times to contacts, but the replies seem to always have a hint of danger.
Then one evening, in the random way that the internet seems to work, he stumbled on another gay meet-up site. This one was called Silver Daddies. The site was dedicated to meeting up with older, mature men. The idea was intriguing to Jake. He perused the site, and liked what he saw. Sure, there were the usual pictures of guys holding their dicks in various states of hardness, some with gobs of cum dripping down the shaft. But he saw captions that were less aggressive than what he'd seen at other sites.
He entered one of his typical aliases as a username, StuP, and profile ID, selected a password, and signed up for the site. The site had two different levels of users – free and subscribers. Since he believed he would most likely be a light user, or possibly even delete his profile soon, he didn't sign up for the fee-based subscriber membership. Plus, he thought that the features of the free membership would be enough for him.
He took the time to create a profile that was inviting, yet not too revealing. It was linked to one of his alias email accounts. Of course, the site requested his actual age by way of having to enter a birth date. He indicated he was into both giving and receiving oral, but left the boxes for top/bottom anal sex unchecked. Jake selected a zip code of a location near to his actual address, but different from his own. He chose that he was interested in “sex partners” and/or a “date,” but not long term relationships. Finally, there was a box for a message. He read the suggestions, and settled on the following: “MWM loves oral sex, both giving and receiving. No strings, just hoping to share some time and excitement. So send a message -- let's see if we can have some fun.”
As usual, responses didn't come as fast as he hoped. He did get a few, but nothing became of them, or at least, nothing that he was comfortable with. He had decided he was going to put it out there up front that discretion was of prime importance. He was going to have to take things slow and careful. It was one thing to visit an escort out of town where it was virtually impossible for him to run into someone he knew. It was another to engage in this type of activity in one's own hometown area. He understood the risks, and was going to do everything in his power to mitigate them.
After inquiries slowed, he did a search of profiles in his area. This yielded a couple of possibles, so he sent messages. Still, he got the same “danger” vibe from the replies. Jake eventually quit checking everyday.
Then one day, he got a message that was different. Odd, but different. It was someone named Andy6969. It read: “Hello, How are you? I would like to find out more about you and if we can get together. I realize you can not host and neither can I, but maybe we could meet and then work out something. If you have read my profile, you know that I like the same types of things that you do; of course the only thing you said that I really love is giving and getting oral sex. I also, like to watch porn of any kind, jacking off, especially with another man, rubbing together, I love having a cock rubbing against me, there are a lot of things that I really love, but anal sex is not one of them. Let me know if you would like to meet, and play together.”
Jake looked up the sender's profile. It said the the member was 70-years-old. He was looking for oral sex, and was interested in sex partners and dates. His profile message was truly bizarre. “LOVE TO SUCK AND BE SUCKED, LOVE PORN, AND JACKING OFF. LOVE PRE CUM AND CUM. LIKE TO RUB TOGETHER. LOVE SEEING AND/OR PLAYING WITH ANOTHER MAN IN PANTIES. LOVE THE FEMS. I AM PARTIAL TO THE OLDER, OVER 55 AGE GROUP, SEVENTIES OR EVEN OLDER. I LOVE A SMALL, LIMPISH COCK JUST AS MUCH or more AS A LONG, HARD ONE. I ALSO LIKE THE HEAVIER, CHUBBY, FATTER GUYS. WILL SUCK YOUNGER COCK ALSO. I'm looking for a feeder that is close to me. Even better if you can host. Looking to suck a younger man. Would love to have a lot of cum shooting off on me. Looking for a top that likes and wants his cock sucked. And now, I would like to suck a young cock, or a older cock would be really nice too. There are only certain times that I could look for someone that is farther away. And if you are close to me, please let me know and let's see if we are compatible. I'm very easy to get to know and I like a lot of different things. I just need you to contact me and let's chat.”
Jake wondered what was it with people and the all-caps thing. He noticed all the grammatical mistakes in the profile message – it was a curse he endured. Still, this guy was putting it out there in the open. Saying exactly, if not over stating such, what he wanted or was looking for. What was clear is that he wanted oral fun, but was going to be open to all types of partners. He decided to wait a bit before responding.
By the next morning, he knew he was going to reply. He thought carefully about his message, and finally decided to send: “ Andy, Wow, between your message and profile info, it's clear you don't like to beat around the bush ;-) Still, there's a lot to be said for putting things right out there, and reading your message and profile gave me a bit of a chubby.
“I am into the oral stuff as well. Genuinely want to give and receive. Doing that is among my frequent fantasies. However, this online thing is new to me, and I've not met with anyone like this before. That's not to say I haven't had gay experiences, but it has been a long, long time (decades).
“So have you met up with anyone here before? The reason I ask is both to maybe get some ideas of how to get things rolling, and there is the hosting issue. Like you surmised, I cannot host either. But maybe if you are friends with another, there's the possibility of a threesome thing at their place. I guess that could be fairly exciting.
“I'm very much closeted, so discretion and safety are important to me. Look forward to hearing from you.”
That was the message he struggled with sending, but eventually hit the “return” key. It was sent, and nothing could change what he said now. But Jake was fairly pleased with his response, and he couldn't wait to hear back.
It took three days. In the past, the delay would have drove Jake crazy, but he had learned that not everyone checks their computer everyday. He was retired, and had settled into a routine of checking things every morning, then in the afternoon, as well as in the evening, if wasn't busy doing something else. But at least once a day was the norm.
On the third day, in the afternoon, he got a response. “Stu, thanks for answering. Don't know about the hosting thing – we'll have to see. Anyway, I would like to meet you. Contact me at ...” He gave an e-mail address. That was it. Again, straight to the point. How can you not like that?
Jake logged into his alias e-mail account and sent Andy an email. “Andy, let's do this. I'm retired so my schedule is wide open. We could meet for lunch or a drink in the afternoon. Sometimes I have evening commitments, so for the first time, lunch or afternoon is best. We could meet up anywhere in town, I'm not that picky. Just choose a date and time and send it to me; I'll let you know. Looking forward to this!”
The next day, Jake checked the site. Andy had read the message. He quickly logged onto his e-mail account, and there was a message from someone new. It was from Andy. “Stu, how about meeting face to face this Thursday at 1:00 in the afternoon?” Andy indicated a restaurant that Jake was familiar with.
Jake thought about it. Here was the moment. All in or fold. He had invested some time and effort into looking into things. Was he ready to go through with it? Without hesitation, he quickly typed a response. “Andy, sounds good. I'll be there at 1:00. I'll be wearing a dark purple polo shirt and jeans. See you then.”
That was two days away. He couldn't wait. Over the next couple of days, Jake found himself thinking about the meeting all the time. It was hard to conceal his excitement. Even his wife asked if there was something bothering him. Jake manufactured an excuse for getting out the day of the meeting.
Thursday came. Jake showered, put on the purple shirt he'd mentioned, and got ready to leave. Just in case things progressed, he got a condom from his stash, and got a dose of sildenafil. Better to be prepared than not. He left home in time to get to the restaurant exactly at 1:00.
Traffic was kind, and Jake got there right at 1:00. He walked in, and looked around the restaurant. There were only about 10 people there – the lunch rush had concluded. There were only two single men seated at tables, and only one was older. He raised his hand to subtly waive at the one. The man nodded, and motioned for him to come on over. Jake made his way to the table.
Of course, butterflies were churning in his stomach. Andy was a fairly typical older gentleman. He didn't really look 70, maybe more like 60, but Jake was terrible at estimating ages. He was a little chunky, but not bad. He was clean shaven, and had a somewhat friendly face.
As Jake approached the table, Andy motioned for him to seat next to him.
“I ordered a beer,” Andy said. “You want anything?”
“A beer sounds great,” replied Jake. He looked around, and a waiter caught his eye. He made his way to their table, and Jake ordered a beer. Jake extended his hand towards Andy. “Nice to meet you face to face.”
Andy took his hand and shook it hard. Not the wimpy, soft handshake often associated with a gay man, but the typical firm handshake one would expect from a real man. “I'm a bit nervous about all of this,” said Jake.
“I know what you're saying,” said Andy. “I've only done this a couple of times. But it's good to meet you face to face. How are you doing?”
“I'm good,” replied Jake. “You're much younger-looking than I expected. You look good for your age.”
The waiter brought Jake's beer, and he took a long draw from the frosty beverage. There was a slightly uncomfortable moment of silence. “Listen,” said Jake, “I like what you said in you profile. Do you mind if I ask about your experience?”
“No, not at all,” replied Andy. He took a drink from his beer. After a moment, he leaned back. “I've met only two guys through silver daddies. One was obviously not going to work. I did meet him face to face, but he was a bit more aggressive than I was looking for. It scared me a bit.” He stopped to take another sip. “The second guy was nice. We ended up going back to his place and I had a good time. That was only a couple of weeks ago, and I haven't heard back from him. On the other hand, I haven't tried to contact him, so I guess it's up in the air at this point in time.”
Jake took a drink. He wanted to let Andy expand on what he said, without giving the impression of pressing him for details.
“Other than that, I've had no other encounters. I guess you can say I'm a newbie. What about you?” asked Andy.
Jake looked directly into Andy's eyes. It seemed that he was genuinely interested. Jake decided to open up. Hell, he'd gone this far, so why not go all in? “I've not had any encounters through silver daddies. Or any other gay-based web-site.” He paused. The next bit of information was a bit private. But he felt he had to be honest at this point in time. “When I was a teenager, around 14 or so, I had a few gay experiences. Mostly with one friend. I enjoyed it, but it was short-lived, and I have experienced nothing over the years.”
Jake looked at Andy, who seemed to take it the information in stride. “Recently, I've had the opportunity to travel out of town, and I've seen a TS escort a few times over the past couple of years.”
“You mean a she-male?” Andy asked.
“Yes. Although they don't like that term. I will say that it has been some of the best sex I've ever had. I can't say that I love her, and I do purposefully say 'her', but I do enjoy my time with her, and it seems like the feeling is mutual. I can honestly say I've never been with someone who is more of a woman. Of course, that's her job to make me feel that way. Still, there seems to be something there. Maybe it's just mutual respect. I don't know,” Jake said. “Other than that, I've had no recent gay encounters. Hell, I don't even consider that gay.”
Andy nodded. “You seem like a nice guy. I think I'd like to take this to the next level, if that's OK with you,” said Andy. He paused, looking for some indication of Jake's agreement.
“I agree totally,” said Jake. “So, how can we do this. I am uncomfortable with giving you a cell phone number, so it looks like e-mail is the only way we can proceed. Do you think that'll work?” he asked.
“Well, the problem is where to meet up,” said Andy. “You got any ideas?” he asked.
“Not off hand,” said Jake. “I do have a cabin up by the lakes, but that's a two hour drive. It may be more economical just to split a hotel room. Nothing fancy, but nothing cheap either. What do you think? He asked.
“I think that'll work,” replied Andy. “I know you mentioned a threesome, but I'm not sure that'll work yet. Let's do the hotel thing and go from there.”
“I'm salivating already,” said Jake. He put his hand on Andy's knee and squeezed. “So when do you think?”
Andy took another drink from his beer, and it was a minute before he spoke again. “Let's shoot for next Tuesday afternoon,” he said. They agreed to all the specifics. Time and place, as well as how to communicate the information. Andy said he'd take care of the room.
“I'm looking forward to it,” said Jake.
“Me too,” said Andy. “See you then.” He got up.
Jake got up as well, and shook Andy's hand. He looked him hard in the eyes, then winked. Andy smiled, and then headed for the door.
Jake sat back down to finish his drink. He thought about how it had gone. He tried to imagine how things would work out at their rendezvous. He lowered his empty glass to the table, thinking about how five days would take forever.
Actually, Tuesday rolled around quicker than expected. Jake cleaned up real good that morning, and told his wife he had to meet one of his friends that afternoon. The story was a good cover. Jake made his way to the agreed-upon hotel. When he got to the parking lot, he checked his phone for an e-mail message to see what was up.
There was an email from Andy. He indicated he had already rented the room, and gave the number.
It was the point of no return. Jake sat in his truck, thinking about the pros and cons of getting out and making his way to the room. It didn't take long. His desires weighed heavy against any possible problems, and walked toward the room. It was a ground level room. When he got there, he noticed that the door's bar guard lock or latch had been placed such that the door was held slightly ajar. Still, he knocked. He heard Andy say “Come on in.”
Jake pushed the door open, and entered the room. It was your typical low-rent hotel room. Two double beds against one wall, a dresser and TV against the other, with a bathroom towards the back. The TV was on, and Jake saw Andy reclined against the headboard of one of the beds, dressed only in his underwear. Andy was looking directly into Jake's eyes. There was a devilish grin on his face. He had a moderate amount of gray hair on his chest. A bit of a belly.
As Jake's eyes lowered to Andy's underwear, he notice a sizable bulge. It was hard to tell actually how large Andy was, but it was encouraging that he was at least partially hard.
Jake turned to shut the door, turned the deadbolt, and closed the bar guard lock. He walked across the room towards the foot of the bed. “Hi Andy, you look great,” he said. He lowered his hands to Andy's leg and started to caress his inner thigh, up and down, being careful not to get too close to his genitals.
“Oh, yes, that feels good. Why don't you get undressed?” asked Andy.
Jake unbuckled his belt, unbuttoned his pants, and let them drop to the floor. He had been going commando, and his erection was immediately apparent to Andy. He had taken a dose of Viagra just before arriving, so there was no doubt he would be hard. Not waiting for any comment, Jake pulled his shirt up and off. He stood completely naked in front of Andy, with his boner angling upward to the ceiling. He didn't have a huge penis, probably average at best, but it worked.
“Take my underwear off,” said Andy.
Jake reached out and grabbed the waistband of Andy's briefs. He pulled downward, and Andy lifted his ass off the bed to allow the underwear to slip down around his thighs. At this point, Jake stopped and admired the penis now exposed. It wasn't huge by any means. In fact, it was relatively thin, but of good length. And for a guy of almost 70, it was nicely erect. No, a more accurate description would be that it was rock hard.
Jake continued to pull the underwear down, then off of Andy's legs. They were both naked.
It was tempting for Jake to bend over and take Andy in his mouth, but before he could, Andy said, “Come here, come up here.”
Jake shuffled up to the head of the bed, his dick was pointing outward and upward across the mattress towards Andy's lips. Andy raised his head and licked the tip of Jake's dick. It felt great. He couldn't control himself. He lowered himself down on the bed, and began to kiss Andy's nipples. He had always enjoyed it when anyone had played with his nips, and he was sure that Andy was getting off on this. He licked, nibbled, kissed, and sucked one nipple, then the other. Back and forth, as Andy moaned with pleasure.
He wanted to spend eternity there, given the oral feedback he was getting. But he knew his destiny was lower down, so he left the nipples, and kissed his way down Andy's chest and abdomen towards his penis. He felt Andy grab his cock and start to stroke it. Gently and softly. Like a guy would do himself.
Jake was now down at Andy's groin. He smelled the musky scent of Andy's genitals. He skipped over them and began to kiss his inner thighs, first one, then the other. At the same time, he used his right hand to grasp Andy's hard cock, and slowly caressed it the shaft up and down, taking care to avoid stimulating the head.
Soon, Jake made his way up to Andy's scrotum. He licked it, gently jostling the testicles. At the same time, he continued to run his fingers up and down the shaft of Andy's magnificent erect penis.
Andy could be heard to be softly moaning. The pleasure was something he had never experienced before. “Suck me,” he said to Jake.
That was all Jake needed, if anything. He raised his head up and took Andy's cock into his mouth. At first he just moved softly up and down, rolling his tongue on the underside of Andy's cock head. But soon he began to apply suction, and bobbed his head up and down on the beautifully hard dick. Jake could taste the salty pre-cum that was exuding from Andy's meatus. It only served to make him hungrier for the prize that was sure to follow.
“Oh, yes, suck me, suck my dick,” said Andy.
Jake needed no encouragement. His mind was already set on accomplishing the goal of filling his mouth with Andy's bitter-sweet cum. Just as Jake had experienced as a teenager, he wanted to have Andy's gooey prize shoot into his mouth. He wanted to have it there, to savor and play with.
So Jake continued to bob up and down Andy's cock. Every so often, Jake would take a deep breath in, then lower his head all the way down to Andy's pubes. Doing so, he would feel Andy's cock head press against the back of his throat, then turn downwards, truly deep-throating Andy's dick. Sometimes, he would drive downward, and hold his position with Andy's dick deep in his throat, making swallowing motions to encourage Andy to explode.
Jake opened his eyes and admired the mixture of grey and dark pubic hair around the base of Andy's cock. He began to focus his efforts to make Andy cum, spending more time on the head of Andy's penis. Up and down, around, and using his tongue to caress the sensitive area at the junction of the head and shaft.
Andy began to thrust his hips back and forth, unable to control his actions. Still, Jake took it all in stride. In fact, he was enjoying the pure sexuality of what was going on. Jake grabbed the base of Andy's cock to provide some sort of stability to the movements, then started stroking his cock.
Andy's breathing quickened, and the moans became regular. Jake could feel Andy's cock expand. Suddenly, his cock head twitched, and pulses of sperm made their way into Jake's mouth. He then made his bobbing motions coordinate with the spurting of semen he felt, and the explosions continued. Soon, they subsided, and he lowered his mouth over Andy's cock head, and held it there, gently sucking out any remaining cum.
Jake slipped his mouth and lips off of Andy's dick. He looked up at Andy, who was obviously in a state of great pleasure. His eyes were half closed, but the still made eye contact.
Jake swirled the fresh semen around in his mouth, savoring the consistency and flavor, then made his way up to Andy's head. He swallowed about half of the protein-laden goo, then lowered his lips to Andy's, and let the remainder drip into Andy's mouth.
Andy realized what was happening, and sucked his own semen into his mouth. He flicked the substance around, then happily swallowed. It was Nirvana. Sperm Nirvana.
Jake drew back, then laid back on the bed to recover. It had been exciting, but exhausting. He was almost ready to fall asleep, when he felt Andy's hand caress his still semi-hard cock. The up and down motions of Andy's hand quickly brought Jake to full erection.
Jake looked down at Andy, who was returning the gaze. “Suck my nipples while you that,” he said.
Andy moved his head up to Jake's chest and began to suck and nibble on Jake's nipples; first one then the other. It was driving Jake insane. He had always had a thing about having his nipples played with, especially orally.
Then Andy moved his way down towards Jake's dick. He trailed his tongue across Jake's abdomen, skipping over his rock hard penis, then began to tongue Jake's scrotum. All the while, he grasped Jake's cock in his hand and stroked him, up and down. Next, Andy stopped at the top of Jake's dick with his hand. He licked up and down the shaft. Andy spent time up near the head, licking and flicking his tongue against the frenulum. It was intense for Jake.
Andy continued his tongue play, but began to move his lips more frequently towards the tip of Jake's cock. Suddenly, he sucked the head of Jake's dick into his mouth, and drove his lips down his shaft.
Jake felt his cock head press against the back of Andy's mouth. The sensations were so intense, and he felt he was close to orgasm.
Andy began to bob up and down in earnest, and about every third time, he pushed Jake's cock into the back of his mouth, letting it make the turn down his throat. He'd hold it there, and make swallowing motions, essentially milking Jake's cock.
A few more times was all Jake could take, and he erupted into Andy's mouth. At that instant, Andy stopped, and sucked all of Jake's cum out of his penis. He waited until there was no more. Remembering what Jake had done for him, he lifted his lips slowly off of Jake's cock, then moved up to Jake's mouth.
Jake opened his eyes, and then his mouth, to give his agreement to receiving the load in Andy's mouth. The goo dripped past his lips, and for the first time ever, Jake tasted his own jism. It was so erotic. He relished both the thickness and taste of it for a few moments, then swallowed it down. He looked up at Andy and smiled.
“That was unbelievable, Andy. Thank you.”
“No, thank you. I couldn't think of anything more erotic than what we've done today. I can't wait for the next time.
They both laid back and relaxed for a few minutes. Soon, Jake got up and said, “We better get going.”
Andy agreed, but added, “But we've got to do this again. Stay in touch?” he asked.
“Absolutely,” said Jake, as he made his way to the bathroom to clean up, although there was little need for it.
When he came out of the bathroom, Andy was already dressed. “I'll shoot you an e-mail. I hope to see you again,” Jake said.
“It would be my pleasure,” Andy said with a huge grin. They made their way out of the hotel room to their respective vehicles. It had been a good day, and they both would see better days in the near future.