Note: All characters in this story are over eighteen years of age.
It was a long week of anticipation for Jack. He had made love with his wife, Beth, on three occasions. It was purely "vanilla" sex: She was only willing to fuck in missionary position, with limited foreplay, no oral - neither giving it to him nor wanting it from him.
The incentive was not the "act" with her; but, rather it was the thought of his upcoming game day date with Chris. Although Beth was a fairly attractive lady, Jack could not finish without some other fantasy assisting. The boredom of repetition was just too much. When he flooded her hairy cunt with his load, it was Chris, panties and porn that drove him over the edge.
Of course, Beth was curious about Jack's suddenly increased libido. He responded by telling her, "Getting out more, as you have encouraged, seems to be helping!" She accepted his explanation and was happy to get the increased frequency.
"I am going to visit sis tomorrow. I will be staying over until Sunday night. If you want, you can invite Chris over to watch the games."
"Sounds good to me, Beth. I hope that you have a good time with Jill!" He quickly texted Chris, inviting him to his home turf.
That night, Jack snuggled lovingly with his wife and he drifted off, thinking of his meet-up the next day with his new intimate acquaintance.
Chris also spent the week in great anticipation of the upcoming weekend's activities with Jack. He did not have another sex partner, but did regularly use his expensive sex toy. Her name was "Anastasia": A very realistic doll, with soft, elastic TPE material, perky B cup tits, and a lifelike "cyberskin" vagina. He also opted for the "shemale kit", which turned the young female doll into a nicely-dicked trans female.
Months after losing his wife, Chris found many advantages of a love doll: She was always ready; she didn't complain; and, after the initial investment, she was much cheaper to maintain. Most times he used the doll's female features, preferring her tight vagina. Unloading inside her sweet asshole or nice mouth were also hot for him. He had experimented with the insertable penis a few times, but never took it inside - that is, until the past week.
Since last weekend, Chris had fantasized about having Jack's sizable cock buried deep inside his tight ass. The thought of that possibility was too much for him, and, on Thursday night, he felt like he had to have Anastasia's trans cock inside him. With the aid of plenty of lube, he managed to get the doll dick inside, "reverse cowboy" style. After getting used to the feeling, he squatted down more. He rode the rod for quite some time, while stroking his hardness.
With his prostate being assaulted, he could not hold back any longer. He spurted a massive load across the bed and on the doll's sexy black stockings. Chris fell back atop Anastasia, balls entirely drained.
The next night was more of the same, but he also dressed in a thong, garter belt and stockings. After getting a good ass fucking from the doll, he assaulted her tight asshole, ultimately filling her rear cavity with his hot semen. As he laid beside his fuck mate, Chris got Jack's text. He responded, "I'll be there by noon." As he pressed "send", his heart raced, thinking about all of the possibilities for the following day.
The sun was shining brightly on Saturday morning. Beth kissed her husband and headed east, about 300 miles away, to visit her sister. Jack was straightening up the living room, and later, preparing guacamole, salsa and chicken wings.
It was already 11 a.m. and it occurred to him that he had not even picked out his panties yet. He had several options laid out neatly across the king bed: a solid light blue thong; a transparent black bikini; a red silk, lace trimmed pair of "sissy" panties (open back); and a bright orange pair of lace cheeky panties.
Jack enjoyed trying on all of them, before deciding on the transparent bikini. He had gotten quite an erection and his shaft was well defined in that pair. He really wanted the "sissy" as first choice. However, he was not sure about the message that it would send to Chris. He feared that the open rear might be an invitation for rear entry - something that he was not quite ready to do. He admired his panty-covered boner in the mirror one last time, before donning his jeans and T-shirt.
The doorbell was chiming as Jack finished dressing. Even though he wanted to hurry, he was very careful zipping up, lest he snag his pretty undies. He greeted his new playmate at the door, and invited him inside, smiling widely. "Chris, an overnight bag? I didn't know that you were planning to sleep over here tonight, but it's OK, if you would like."
Chris walked over to the plush sofa, dropping his bag on the floor. "Actually I hadn't thought of that, but would be happy to stay over! I have a surprise for later in this bag."
Jack responded, "I hope that later comes soon! Gotta be a hot surprise!" He walked into the kitchen, retrieving the food. When he returned, Chris was on the sofa, taking off his shirt. "Damn, Chris, I thought we would wait until at least halftime. The kickoff is still fifteen minutes away!"
"There's no rule about getting comfortable first, is there?" Chris joked.
"Nah, I guess not!" Jack answered. He put the food tray on the ottoman and stripped off his T-shirt. "At least we won't have to worry about wing sauce on our shirts, Chris!"
"Well, Jack, I know you have pretty good sauce!"
"As do you, my friend!"
Both men chuckled as Jack sat close to Chris on the sofa. The jean-clad pair began to devour the chips, dip and wings as the game started. The two were quite a contrast physically: Chris' smoothly waxed hairless chest and Jack's hairy upper body; Chris' beautiful darker skin and Jack's pale skin, which was rarely exposed to sunlight.
They watched the game intently, happy to be beside each other, nibbling on the snacks and making comments about the game and the pretty cheerleaders. The two-minute warning came and Chris began to unzip his jeans. Jack glanced over. "You are a horny fucker! We still have a couple of minutes!"
