Chris was spending three weeks out-of-town training for a new job.
Chris was a middle-aged man known to be a "social butterfly." He would often be the ring leader for nights out after training each day. As the ring leader for the parties, he would help other middle-aged men in the group relax and socialize with women at the hotel bar.
After the last night of training, Chris ensured each guy was having fun at a party. Scott was in his early 40s and had the quintessential "dad bod". About six feet tall, still well-built and fun as hell to go along with it. Scott's wife left him 20 years ago after the birth of their only child. Scott had not been with any human being since.
Chris made a promise to Scott that if he didn't go home with a chick, that Chris would give up his ass in return. At around 1 am, Scott was empty-handed. Chris himself spent the last three hours trying to help him, but was unsuccessful.
As the group of guys staggered back drunk to the hotel, Chris announced to the group that he would be "paying up" in room 317 later if anyone wanted to come and help.
Chris himself was happily married and had no issue with getting an ass. He was six feet two and kept himself in great shape. He shaved his head, but grew a great beard.
As Chris reached the room, he thought about how he always wondered what it would be like to have a hard cock in his mouth. While the thought made him curious, he just considered tonight to be more transactional than erotic.
When they got to the room, Chris grabbed Scott and himself a beer from his fridge. The rooms had an open floor concept with a kitchen, couch, desk, and bed with a traditional bathroom.
Scott sat on the couch, and Chris sat on the edge of the bed. "So, how are we going to do this?" Scott asked with a slight tone of anxiety. "Dude, it's pretty simple. You take off your pants and I will blow you." Chris replied, as he took a big drink of his beer.
Chris started to feel butterflies, but didn't want to show them to Scott.
But like, do you want to? Because you don't have to. " Scott still kept talking. "Let's do this, Scott. You sit on the couch, take off your pants, finish your beer, and we'll just leave it at that," Chris replied.
Chris himself was now nervous. He wanted to help his friend have an orgasm, but didn't know if he could live up to the expectations. He had never sucked a cock and was not one hundred percent sure what to do.
After the beer, Scott stood up and announced, "Here goes nothing," attempting to ease his nerves. Scott pulled down his jeans and white underwear to his ankles. Scott was still wearing his white t-shirt and button-up dress shirt. Scott then sat back down on the couch.
Chris chugged his beer and stood up to stagger over. After the five steps from the bed, Chris got down on his knees in front of his friend. Scott and Chris made eye contact and didn't say a word. Chris moved his hands slowly up his exposed and hairy thighs.
As Chris's hands reached his inner thighs, he watched his growing cock twitch. "Make sure you tell me what you like AND when you're about to cum," Chris said. Scott just nodded his head. He was so hungry to have his dick sucked after all these years.
Chris grabbed his still growing cock with his right hand. He started to use his thumb to rub the underside of the shaft near the head. As he did, Scott let out an audible sigh. Chris continued to rub his shaft while touching his balls with his left fingers.
At this point, Scott grew to his max size of seven inches. Chris watched in excitement and fear. How was he going to suck all of it up? At this point, he made a deal and had to pay up.
Chris leaned in and simply opened wide. He let Scott's cock penetrate his nervous mouth all the way to his tonsils. Chris quickly gagged at his overeager attempt. Chris quickly recovered and simply did what he liked.
He ensured his teeth were buried behind his gums and let his tongue do the work. As Chris sucked Scott's cock, he started to close his eyes. He wanted to do the best job he could and didn't realize his own cock was stiffening in his jeans.
Scott reached down to rub his shoulders and head in appreciation of the blow his friend was giving him. As the two men started to get a good pace going, they were interrupted by a knock on the door.
Another trainee came to "help". Tom was also a middle-aged father, but was clean-shaven and of average build and shape. "Did you guys start yet?" He started to ask and abruptly stopped once he got two steps into the room and saw Scott on the couch with his cock at full staff.
"Wow, you guys are really doing it?" he asked, but was pleasantly surprised. Tom, too, had never been with a man and was always curious.
Like Chris and Scott, Tom was also drunk and very horny. "Well... don't let me stop you two," Tom stated as he sat down next to Scott on a three-cushioned couch. Chris got back on his knees and started sucking on his new best friend. This time he watched Tom out of the corner of his eye. It didn't take long for him to take off his pants.
Incredibly, he got totally naked in minutes. Chris noticed his cock was still large, but looked bigger since he had no pubic hair.
After a few more minutes with Scott, he turned to Tom. "well mean, if I am helping him, I should help you too," he stated in an attempt to validate his actions, but deep down he loved sucking cock. The warmth of the flesh, the pulsing of the veins, the mushroom head that was soft vs the hardness of the shaft. Sucking a cock did not directly compare to licking the pussy. Half the time, Chris was guessing what to do, but with a clue, he knew.
Chris and Tom quickly matched motions. "Damn, you are a good cock sucker," Tom complimented him. Chris worked his shaft and brought his hand to match. Chris started to taste the salty precum coming out of Tom's cock head.
Tom stood quickly. Chris, thinking he was about to blow his load, arched his back and opened his mouth like a cum whore.
"Not yet, pal," Tom chuckled. Tom pulled Chris up and did something totally unexpected: he kissed him. Chris was taken back at first, but matched his tongue. Chris and Tom felt each other's arms and chest as they explored each other's mouths with their masculine tongues. The kisses were not gentle like a woman, but more savage and aggressive.
Tom quickly dropped to his knees and fumbled with Chris' belt. Tom had never sucked a cock, but he was very competitive and had to see if he was as good as Chris.
As he finally unleashed Chris's six-inch cock, he went right to work. Bobbing up and down while thrusting Chris into his clean-shaven mouth by grabbing Chris' ass.
Scott sat down behind Chris and parted his ass cheeks.Scott buried his tongue deep into his ass and lapped his virgin asshole while Tom engulfed his cock. Chris would reach back to rub Scott's head buried in his ass, then use his left hand to comb Tom's hair while he slobbered on his dick.
The three men were way past pleasantries and deep into exploring each other's bodies. Scott would reach under Chris and fondle his balls or reach for Toms, still leaking cock.
"You guys better pick a new position or Tom is going to be wearing a pearl necklace." Chris panted.
Tom stood up and asked, "What do you have in mind?" Before Chris could talk, Scott started to kiss him now. Watching Tom and Chris make out turned him on even more, and he just had to try it. The two made out deviously, and Scott got on top of Chris. There were two bodies grinding ed as they explored each other's "dad bods".
"You want to fuck me now, don't you?" Chris panted as Scott sucked on his neck, Tom watching and slowly jacking his cock, trying not to cum.
"Do you have lube or what?" Scott sat up and asked. Chris had lube and condoms just in case he was able to get lucky. even though he never thought the lube he bought would be used on him.
Scott fumbled with the boxes and put on a condom. Chris arched his back and let Scott apply the lube while Tom leaned down and started making out with Chris again. While the two tongues wrestled, Scott prepared to take Chris's anal virginity.
Scott placed the head of his cock towards Chris's lubed up asshole. He inched his cock in, giving time for Chris to relax his asshole and welcome this intrusion. After about two inches, Scott hiked Chris's left leg over his shoulder. This gave him a better angle.
