Chapter 3

Enjoying another bite of Belgian waffle topped with whipped cream, Tim Loewen admired his sexy, naked family seated around the breakfast table. His tanned, smooth, bare-chested sons, Garrett and Nate, now adults, but just barely, were acting more like adolescents, giggling and tickling each other under the table. Both were broad-shouldered, with older son Nate’s pecs a little more developed than Garrett’s, but Garrett was holding his own. Their dark, walnut shaped nipples rested at a pleasing angle. Chrissy, a little perturbed at her brothers’ antics, was developing nicely, her nubile breasts looking more and more like her mother’s. Tim’s wife, Lizbeth, now in her 40s, had firm breasts rivaling her daughter’s.

Not thinking about the erection he’d grown looking around, Tim stood up for dramatic effect to make an announcement, his napkin sliding off his boner, which brought snorts and chortles from his three kids.

“Alright, alright, calm down. We all know what an erection looks like. I’m willing to bet you two guys have one now,” Tim chided his snickering sons. “Now that we’re finally all adults there’s no reason to have interior doors anymore. As each of us has more and more sex partners, it will be safer, and more natural since we have an open house policy for sex and nudity anyway. So, as soon as we wash the dishes, we’re going to go around and remove all the doors.” As cheers erupted from the three kids, Lizbeth looked admiringly at her husband. Looking down, she also admired his now semi-hard sex organ which had pleased her countless times. She knew they were raising the family right so their children could enjoy the same positive body image and sexual self-actualization she and her husband have.

Dishes done, Tim marched his three naked kids through the house. Nate carried the tools and Chrissy made a make-believe trumpet with her hands and hummed along to herald the removal of all the interior doors. Garrett and Tim put on shorts and loaded the last of the doors into the truck to take to the re-sell store, then collapsed on the couch. “Good job, bud,” Tim patted his son’s inner thigh in appreciation for helping with all the doors.

“Dad?”

“Yes, son”

“So ... I’ve been checking out this gay dating app that has a lot of older guys.”

“And?” Tim responded curiously.

“I think I’d like to try having sex with an older man. I found this one guy who’s 45 and seems pretty cool. He sure took an interest in me and I’m keen to meet him.”

“Well, that is quite a difference in age. And we’d need to meet him and learn about him first.”

Lizbeth joined in at this point in the conversation. “I don’t think the age difference is any problem. An adult is an adult and we get to choose whoever we want to have sex with as long as they’re adult age and safe.”

Tim and Garrett nodded in agreement.

“Alright then,” Tim said. Does this fellow have a name? And when do we get to meet him?”

“We’re just in the chatting stage,” Garrett answered. “But I’m super excited to date him. Can he come here? His name is Ford”

“Yes, we’d much prefer that,” Lizbeth interjected.

“Now that I know of your interest in older guys,” Tim added, “there might be some bi friends from our swingers group who would be interested in deflowering you, son.”

“That would be awesome, dad!” Garrett could hardly contain his excitement. “I want to bottom with an older dude. And maybe flip-fuck.”

“Where did you learn such terms, son?’ Lizbeth jokingly chided.

Tim just added, “OK, but hold on. There’s some work that goes into having good anal sex and you need to learn the ropes some. I know you had some good practice on Mark’s hole, but it’s a little different being the catcher than the pitcher, especially with an older and larger man.”

“Will you teach me, dad?” Garrett asked innocently.

“Sure son, let’s have an anal lesson later tonight if you like.”

“Yay!” Garrett shouted. “I can’t wait!”

“First, we have to go to the adult toy store and get you a few things, like a rectal cleansing bulb, lube and butt plugs in increasing sizes.”

As soon as the dishes were put away, father and son put on shorts and t-shirts for the ride to the sex shop. Garrett had never been to one and his eyes grew wide at the variety of gadgets and toys adults can use for sex. An attendant approached and asked if he could help.

“My son is preparing to bottom for his first time, and I told him I would help him get ready. We’re looking for a butt plug starter kit, some lube and rectal douche bulb,” Tim informed the attendant.

“Sure thing!” The attendant got a big smile on his face as he walked the two family members to the anal toys section.

“A common rookie error is getting a butt plug, or a dildo, that is too big. I would recommend starting with this kit that has graduating sizes. This way, your son can start with the smallest and work his way up based on what’s comfortable.”

Garrett looked a little dismissive at the smallest sized butt plug but his dad reassured him he can graduate pretty quicky as he’s able, and suggested following the attendant’s advice as the expert.

“OK, I believe in science,” Garrett jested. Everyone had a good laugh.

After packing up the butt plugs and other gear, Tim and Garrett drove home. The ride was quiet but both men had smiles on their faces. Finally, Tim placed his hand on Garrett’s bare knee and squeezed it. “You’re gonna like anal, son. I remember my first time. I want you to have a good experience.”

“Thanks, Dad.” Garret replied, smiling up at his father.

Upon arrival, dad and son got naked once inside the door.

“Success!” Tim announced to cheers from the other family members. Garrett excitedly showed his mom and older brother his purchases then ran to the bathroom to meet his dad.

Tim instructed Garrett in how to use the enema and demonstrated it on him, clearing out his anal cavity. Garret thought to himself that this wasn’t unpleasant at all. He enjoyed the insertion of the tube and the feeling of fullness as the liquid was squeezed inside his bowels. He didn’t even mind expelling the liquid mixed with fecal matter since he was raised to think positively about how the body functions.

Next, Tim lubricated the smallest size butt plug, had his son spread his legs propping one foot up on the toilet. His dad knelt behind him inspecting his virgin, pink hole then slowly worked the tapered end of the butt plug inside. Garrett winced at the insertion and his dad reminded him to relax and push outwards to allow the toy to go in. Once inside, the plug felt full but was once again pleasant as Garrett lowered his foot from the toilet seat.

“Dad,’ that’s actually a perfect fit. I feel stretched but too much so. Thanks for encouraging me to take the attendant’s advice.”

“Alright, son. That’s great. Now the task will be getting used to it as you just go about your night and next day.”

“Thanks, dad. You’re the best.”

“No problem. That’s what dads are for,” Tim said as he playfully fist bumped his naked son.

Father and son exited the bathroom with Garrett’s butt plug snugly in place to applause from the rest of the family. They knew Garrett had been plugged and this was his first step towards bottoming.

Lizbeth said to Tim, “You know that email you sent to the swingers’ group about any older bi guys wanting to initiate our son to man sex? Well, you got a reply. It was from Jared Mathers.

“Oh yeh?” Tim perked up as he padded over to the computer, his flaccid, long dick swinging between his legs.

Sure, enough, Jared had sent a reply saying not only that he was interested, but his son might be also, if Garrett would consider a threesome for his maiden anal encounter. Tim was still getting used to his youngest son being asked direct question about his sexual decisions rather than going through him as his father. He reminded himself though that this is what it’s about. His son is making decisions now about sex as an adult, and Tim just felt honored that he was still around and could speak into it.

Tim explained to Garrett that Jared is 52 and bi and he and his wife have a 32-year-old son, Scott, who is also bi and married. Jared and Scott play together a lot with various male and female sex partners and they’ve always wanted to do a much younger guy.

Garrett looked at their pictures which included photos of both men erect and almost trembled out of excitement and anticipation. Practically sputtering, Garrett asked, “Dad, when can they come over?”

The whole family laughed and Lizbeth said, “It take it that’s a yes,” More laughter, then Tim started typing a reply. Then he stopped, and said to Garrett, this is your reply to write. Just identify that it’s you using my email.”

Garrett proudly sat down and typed his reply, “Hi this is Garrett using my dad’s email. You guys both look awesome and I think it would be great to have a threesome for my first time. When are you free???” Then, taking a deep breath, he hit send.

“Son, when you hear back from them, I’d like to suggest that the four of us have a video conference first. We don’t have to wear clothes, and we can all be hard, but I want us to just go over the ground rules. You’ll take the lead.”

“O.K. Dad. I really appreciate both your wisdom and encouragement.”

Tim smiled and tussled his son’s unruly hair.

The next day after work, Tim fired up the computer. Garrett joined and sat next to him, both men naked. Tim opened the link and saw Jared and Scott, both naked and smiling.

“Hi guys, glad you could join us,” Tim started out. “I’m going to hand the mic over to Garrett who can discuss plans with you guys. I just want you to both know I’m really proud to be sharing my son with you both for his first time. I’ve had such great experiences with both of you, and so has Lizbeth, at our sex parties.”

Both Mather men nodded and smiled remembering the various combinations of sex they’d both had with Tim and his wife, and which was about to include Tim’s son.

“Hey, Garrett,” Jared said and waved. His son Scott gave a friendly wave also. Both men had started boning up at Tim’s words and Scott was casually playing with his hardening cock.

“Hey, thanks so much, both of you, for agreeing to help me explore gay sex more and try bottoming.”

Scott looked at his dad smiling at how polite and a bit formal Garrett was. “Well, truth be known, we’ve both wanted to tear up your ass for a while,” Scott jokingly said.

That last comment broke the ice as all four men laughed and had a good conversation about sexual likes and dislikes and any boundaries. The call was a success and before Tim logged off everyone agreed to set the play date for the upcoming Saturday morning at 10am which would give Tim and Garrett enough tie to help Garrett prepare.

On the days leading up to Saturday, Tim and Garrett spent several hours watching gay anal porn together, masturbating some, and going over the different techniques and positions displayed on the screen. Tim also included an anatomy lesson on the prostate and the role it plays for a man’s sexual pleasure. Both men discussed it and felt Garrett was well prepared to get fucked.

Friday night, Garrett slept with the next largest butt plug inside him. He slept like a baby but woke up the next morning anticipating Jared and Scott’s arrival like it was Christmas morning. The guests were punctual, ringing the doorbell right at 10. Looking at his parents, Tim and Lizbeth motioned for Garrett to get the door. Garrett wasted no time letting his new sex partners in, greeting each one with a naked hug, and getting a friendly butt cheek squeeze in return.

“Come on in and take your clothes off,” Garrett offered his guests. “You know my parents, of course.” Garrett led Jared and Scott to the sofa where they all sat down with Garrett’s parents in the living room. Knowing that Jared and Scott both enjoy adult beverages, Tim offered to make drinks and the guests accepted the kind offer. Looking quizzically at her husband, Lizbeth asked if it would be alright if Garrett has a drink too. “It might help him loosen up,” she innocently said, drawing snickers form the assembled men at her double entendre. Tim served the drinks which they all enjoyed and the couples caught up on life since their last swinging adventure. Garrett looked on, smiling, and appreciating the inside stories on the adult swinger parties he would soon be attending.