Nifty Archivist, Please add this to my series "Son of an American Housewife" under the gay celebrity section.
Son of American Housewife part 6
Usual disclaimers apply. I don't own these characters. This is total fiction. I welcome your comments. chubbyboyinbama@yahoo.com
Once again, Cooper found himself riding along as Oliver drove. This was a perfect analogy for their relationship. No matter what they did, Oliver drove. Oliver was always in control. Cooper was just along for the ride. At first, Cooper had thought maybe they were going to back to Trip's house and his cock twinged in his khakis. But as they drove out of Westport, Cooper's interest was peaked. They drove for a long time, all while talking and laughing, but Oliver wouldn't give Cooper even a hint as to their final destination. They drove into a city that Cooper didn't recognize and into a neighborhood that Cooper thought looked sketchy at best. But then again, Cooper probably thought the Otto house looked sketchy compared to any of the mansions and summer homes that he had grown up in. Finally, Oliver pulled into a space in front of a store called "Cherry." and Cooper could tell instantly the kind of place it was.
Cherry was a huge store front with big glass windows. But the windows were all covered in black paper to obscure the contents of the store from the casual passer by. Instead, the posters in the windows listed items for purchase inside. One side simply said, "toys", which even Cooper knew didn't mean hula hoops. "What are we doing here?" Cooper said in a confused tone. Cooper was frequently confused. He wasn't that smart of quick on the uptake. This was one of the reasons that Oliver was able to get him to do so much.
"Well," Oliver said as he locked the car with the fob and walked around the fender to meet Cooper at the curb. "We are underwear shopping." Cooper looked dubious. "You are always saying that a real man shouldn't wear underwear from a Target. And you are right of course." Oliver smiled, like always, to disarm Cooper. "But if you need underwear, why didn't we just go to that boutique in Westport? They have what you need. Nothing there is less than $100."
Oliver smiled again and touched Cooper on the shoulder. Inside, Cooper shook with delight every time Oliver touched him. "Yeah, but I thought this place might have more selection. I've been here before and it is kind of wild."
Cooper shrugged, happy as always to defer to Oliver's judgment. They went inside and Cooper's suspicions were affirmed. This wasn't really an underwear store, but a sex shop. One side of the store was shelves lined with DVDs. The other was shelving and racks filled with bizarre clothes. Oliver stopped in front of the counter and made eye contact with the tall, burly biker type behind the counter. "Hey Henry." Oliver said. "Henry came over and spoke with a jovial tone that belied his appearance. "Hey Ollie! Is this your friend you were telling me about?" Henry nodded up and down Cooper, which made him feel a little uneasy. A million questions went through his head. He called him Ollie? They knew each other? They had talked about him? Instead of asking any of these questions, Cooper nervously shook his head to say, "Hi." Henry laughter and clapped the boys on a shoulder each with both his hands as he walked them toward a section of men's underwear.
Cooper was uncomfortable to say the least. He had done a lot with Oliver, and while he hand't put it into words for himself, he was beginning to realize that he was likely gay and in love with Oliver. Oliver had done unspeakable things to Cooper. He had been in his every hole. Almost every night he fell asleep with Oliver's load inside him. He had even done the same for Trip and Oliver's dad at Oliver's urging. But they never spoke about these things. They never talked about the things they did or what it meant. And here they were surrounded by sex toys and dirty underwear and bikers named Henry? It was all too weird. But Cooper was also afraid to say anything. Henry showed them to a fitting room and said, "I picked out some things you might like, just let me know if you have any questions." How much thought and planning had gone into this little outing? Cooper was more and more confused.
Henry closed the curtain in the tiny fitting room (a booth really with three mirrored walls and a curtain. Now hidden behind the curtain, Cooper confronted Oliver. "What are we doing here? You know that guy? What is going on?" Cooper whispered, but there was almost a sense of panic. Once again, Oliver put his hand on Cooper's shoulder to calm him. And it worked. "Everything is fine Cooper. Henry has sold me stuff before. He and I go way back. He knows what he is doing. You are just gonna try some things on."
"What do you mean I am going to try some things on?" Cooper said. "I thought we were here for you, not me."
"I'm gonna get some stuff too. But I asked Henry to pick out some things for you." Oliver stepped closer, his face inches from Cooper's. Cooper instantly felt the temperature in the room change. "Stuff you can wear....for me." Oliver had never said anything like this before. They never alluded to what they did at night in the dark or in Trip's bedroom, or the time when he had pushed Cooper's ass down on Mr. Otto's monster dick. But the idea that Oliver wanted Cooper to dress up for him. To be sexy for him, this excited Cooper. Cooper looked down and said, "Ok." Oliver gently put his hand on Cooper's chin and pushed his face up so that they were looking into each other's eyes. "Ok?" Oliver said sweetly. When Oliver expressed genuine interest in Cooper's feelings, it made his dick hard. Cooper smiled a little and once again said, "ok." This time sounding more convinced.
The first two items were standard underwear. Oliver tried these on. Oliver looked particularly good in a pair of red briefs, very tight, with a white piping that showed off the "y" shaped opening in the front. Cooper relished watching Oliver get undressed and dressed again. Oliver's dick was soft for a change, and so impressive on the boy's slender frame. Cooper had a nice dick, but he wasn't hung like Oliver or Mr. Otto. Sometimes he worried that he wasn't big enough, but just as he had this thought, Oliver, almost as if reading Cooper's mind, said, "try this one on. I think it will really make your package look great." Cooper smiled as Oliver held out a large spandex blue thing on a hanger. It was tangled a little, so Cooper couldn't tell what it was at first.
Oliver leaned back against the wall of the stall and crossed his arms. He was a vision. His shaggy brown hair always almost in his eyes. His toned chest and arms. His striking red briefs. His full cock and balls bulging beneath the bright red fabric. Oliver watched Cooper as he said, "put it on".
Cooper obeyed, quickly stripping off the yellow briefs he had been trying and as he unfolded and untangled the blue garment, he realized it wasn't underwear at all, but a kind of singlet like a high school wrestler would wear. It was blue with white striping, and as Cooper figured out what it was, he looked up at Oliver and smiled with a laugh. Oliver smiled, but didn't laugh. "Go on." Oliver said softly.
Cooper figured out the legs, and as he was stepping into it, he realized that this singlet wasn't like one a high school wrestler would wear, because there was an opening in the ass. As he put the straps over his arm and stretched it out to a proper fit, he looked in the mirror his ass, partially exposed by the opening. Cooper laughed and said, "what do you think?"
"I like it, "Oliver said quietly. "But we need another opinion." Just then, Henry peaked in through the curtain before stepping into the now crowded booth with the boys and pulling the curtain behind him. Cooper flinched and sought to cover himself, facing his bare ass toward the wall and cupping his hands over his crotch.
Oliver, gently placed his hand on Cooper's forearm and pulled his hands away from his crotch. Henry, with a sly smile said, "I like it. Especially the ass."
Henry was tall, taller than both he boys, and of a husky build. His arms were muscular, but he appeared to have a little bit of a gut. He wore black jeans and a sleeveless black shirt and silver chains. His bald head make him look a little older than his 40 years. Had Cooper been forced to give his honest assessment, he would have said that Henry was attractive, but not his type. Cooper honestly only had eyes for Oliver. So if you weren't a skinny, pale, narcissist with a giant cock, Cooper probably wasn't going to be into you.
Still surprised at Henry's presence in the booth, Cooper knew what was going on. Even Cooper could figure out that Oliver had planned this. And that at the right time, he had either singled to Henry to come in or maybe Henry had been listening for the right time. But either way, as Henry spoke, he pointed to the mirror behind Cooper where his bare ass was reflected. Cooper was confused for a second more. But then perhaps he not only understood, but decided to go along. Obviously this is what Oliver wanted. And Oliver always got what he wanted. And the fact that this would please Oliver, kind of made it please Cooper. Kind of.
Cooper turned to face Henry. His previously shocked and confused face was now more one of seduction. "This hole." Cooper said softly. "What's it for?"
Henry smiled and was about to speak when he Oliver chimed in. "You know what it's for."
Cooper smiled innocently. "Turn around." Oliver said. Cooper looked at Oliver, then at Henry, then slowly turned to face the mirrored wall behind him. Cooper closed his eyes and felt Henry step closer behind him. Henry pressed Cooper up against the mirror, which was cold on his exposed skin. Cooper wasn't exactly sure what was about to happen, but the list of possibilities was short. He heard the jingle of a belt, a zipper, a rust of fabric. Then he felt a hot pressure on his ass. Then a searing pain as Henry pushed himself into Cooper's hole. With Oliver, there were two types of encounters. Either he gently rimmed or lubed Cooper first, or (more commonly these days), Oliver would penetrate him with no lube or loosening first. It didn't hurt like it did at first, but it still hurt. Cooper still had his eyes closed as Henry began to pump in and out of him. Even if they were open, he wouldn't have been able to see Henry's dick. He knew it was big, but smaller than Oliver's. As it slid in and out, the pained lessened and Cooper began to enjoy it a little. He found that no one satisfied him inside like Oliver. But Mr. Otto had felt good after a while. And now Henry did too. It was like he had an itch that only a big dick could scratch.
"Open your eyes." Oliver said flatly from behind. Cooper opened them and immediately focused on Oliver's reflection in the mirror. Oliver was standing in the same spot, behind and to the left of Henry's shoulder. As Henry quietly jammed his dick into Cooper's ass, Oliver had pulled down the front of the tight red briefs and was slowly stroking his enormous boner. Cooper had seen Oliver's dick now countless times. But something about this stance, or lighting, or something, make it look even bigger. Oliver smirked at Cooper, which made his dick twinge again. It was only now that Cooper realized that his dick was oozing pre-cum inside the spandex of the singlet. And while Cooper was starting to enjoy the slightly rough pounding he was getting from this stranger, he secretly wished that Henry would pull out so that Oliver could jam himself inside and fill up Cooper's guts.
Henry lasted a while. So much so that Cooper's legs began to cramp from the semi-crouching stance he was forced into. But Cooper was playing through the pain. Finally, just as Cooper thought his knees might give way, he heard Henry grunt. This was followed quickly by the now familiar sensation that Cooper felt whenever a man ejaculated inside of him. Henry gave Cooper a bristly kiss on the back of his neck as he pulled out. As Henry's dick slipped out, his cum flowed out too, dripping onto the undercarriage of the singlet and the floor of the changing room. Henry, breathing hard, stepped back and leaned against the mirror and Oliver stepped up. Cooper held his breath expecting to feel Oliver slip inside him, but instead, he heard Oliver grunt softly before he felt Oliver's hot, sticky load shooting onto his back. Some hit his exposed back, but most hit the fabric of the singlet. Cooper wasn't exactly sure why Oliver had chosen to cum on him and not in him. For a second, he wondered if Oliver could read his mind and was purposely denying him what he wanted.
Henry quickly put his dick away as Cooper leaned against the mirrored wall, trying to recover. Henry, now having dressed and righted himself, leaned over and put Oliver's cock in his mouth long enough to lick away the last remnant of jizz before standing, saying, "mmm" and turning to leave. Once the curtain was closed, Henry called back from the other side, "Oh, um, keep the singlet, I can't sell it now anyway! On the house."
Cooper looked down at his crotch to realize what Henry meant. The blue singlet was dark at the crotch, where Cooper had pre cum (or had he just cum and not realized it?). Cooper couldn't see the back where Oliver's cum stained the back and Henry's stained the undercarriage. Cooper recovered enough to step out of the singlet, which Oliver then used to wipe away the extra cum. Oliver laughed a little, and Cooper, still not believing the encounter they had just had, smiled. But when they left the changing room, Cooper was instantly embarrassed and red faced when they saw Henry at the counter. Cooper tried to avoid eye contact. Oliver laughed and joked with Henry (though not about what had just happened) as Oliver used Cooper's Dad's credit card to pay for the red briefs and a few other pair that Oliver had picked out. True to his word, Henry did not charge them for the singlet. As they left, Henry shouted after them, "Please come again!"