Brad’s Search : Part 37

We finally reach the end of the work day. I pack up all my things and begin driving home.

James texts on the way. I have my phone read it out loud to me. “Hey, cutie. I just got done with work and don’t feel like cooking tonight. Want to head out for dinner?”

I call him back. “Hey, I’m just getting off, too. Going out sounds good. Where to?”

He gives me directions to a place close to the law firm. I tell him I’ll meet him there shortly.

I drive to the restaurant and meet him outside. We head in together and get a table.

“Brad, can you drive me home tonight and drop me off at work in the morning? I might need a drink or two.”

I place my hand on his. “That bad?”

“No, not bad; just a bit overwhelming.”

Our server approaches our table. We order food and James orders a drink.

“Did you have a talk with your dad?”

James takes a deep breath. “Yeah. I didn’t really feel like talking, but Paul called the office again and Dad came to me right when he got off the phone.”

“What did he say?”

“Dad’s just getting more and more tired of this sibling rivalry with each passing day. He’s not taking sides; he knows it was wrong how Paul treated me years ago, but he thinks I should be over it by now and that it shouldn’t stop me from having a relationship with Paul.”

“And what do you think?”

He pauses for a moment. “If it’s starting to affect him this much, I think it’s worth it to talk to Paul.”

I caress his arm. “Good. Honestly, I’m glad to hear that. I never really like it when conflicts remain unresolved for so long.”

“Me neither. I just know it’s going to be a painful process.”

“Sometimes we need to go through the pain in order to heal and grow stronger.”

He sighs. “Yeah.”

Our server returns with James’s drink and our appetizer.

I turn back to James. “So when are you going to talk to him?”

“Probably on the way to Portland.”

“In the car?”

“Yeah. I don’t think I can muster the energy to talk to him after I’m done with work, and I certainly can’t talk to him at length during work. I want to spend my free time this weekend with you. The only other time is when we’re driving down to Portland.”

“But you won’t mind me being in the car, listening to your conversation?”

“Brad, you and I have no secrets. Even if you weren’t present during my phone call with Paul, you’d still hear about it from me. I’m not really worried about what he’ll say. I have no shame about the decisions I’ve made in the past.”

“All right, as long as you’re OK with it.”

We relax and wind down as we eat dinner. We’ve both been pretty taxed mentally and emotionally. And it’s only Tuesday.

We finish dinner and I drive us home. On the way, James places his hand on my thigh. “Dad also said he’s sorry for how he acted last night. He wants to take us out to dinner on Friday to make it up to us. I told him I’d ask you.”

“That very nice of him. I know he’s a good man - there was probably just a lot on his mind last night. I’d like to see him again on Friday, though.”

“Great. He feels so bad about it, and says he’ll try to be a little more on his best behavior.”

I continue driving as the sky grows darker and darker. We arrive home and I park along the street. We step inside and head to the kitchen.

“Brad, can you make me one of your world-famous lemon drops?”


He lightly pinches my cheek. “Thanks, cutie.”

I gather the ingredients, shake them up, and pour them into two martini glasses. I hand one to James and we toast to our new relationship.

“Did you have a good run this morning?”

“It was OK. It’s great being near the water, but it’s kind of spooky at night with no one around. I kept waiting for the boogeyman to jump out and kidnap me.”

James chuckles. “I know what you mean. I’ve gone there late at night once or twice and felt the same way.”

We take sips of our drinks. James continues, “Speaking of running, you looked so god damned sexy this morning in that jockstrap.”

I’m a little shocked and surprised. “Really?”

“Yeah. Can I see you in it again?”

“You mean, like right now?”

James gets a dreamy look in his eyes. “Yeah.”

Weirder things have been asked of me. “Sure.”

James downs the rest of his drink, and I follow suit. We walk upstairs to the bedroom. He sits on the bed while I grab a random jock from the dresser.

“Can you put on a black one like you had on this morning?”

“Yeah, I think I have a clean one in here somewhere.”

I search through the underwear drawer until I find a black jock. I set it on top of the dresser, then I undo my belt, unbutton and unzip my pants, then push my pants and underwear off my body and onto the floor. I place one leg, and then the other, into the jock and pull it up to my waist.

James stands up and walks over to me. He runs his hands over the waistband, pouch, and leg straps. “The jockstrap is such an interesting piece of underwear.”

“It sure is. Don’t you like how it feels when you put it on?”

“I don’t know; I’ve never tried one.”

I gasp. “Really? You never had to wear one in gym class?”

“I never had to take gym.”

I stand there, stunned, for a few seconds. “Wow. I guess Denver and Seattle are more different than I thought.”

“I’ve always wanted to try one on, though. Do you mind?”

“I’ve already had your dick in my mouth. Why would I care if you wore my underwear?”

He chuckles. “Never thought about it that way.”

I hand him the first jock I had pulled out - a white one. He bends down and struggles with putting his legs in, but eventually gets it on the right way. He pulls it up and snaps the waistband against his body. “You’re right; it does feel kinda weird at first, but I love how it lifts everything up. I wonder how it feels underneath jeans.” He grabs a pair of jeans, puts them on, and zips them up. “Yeah, I think it would take some getting used to, but I kinda like it.”

“Well, they’re really meant for when you’re doing lots of physical activity, because they keep everything from flopping around everywhere.”

He moves his legs around, attempting to get a more comfortable fit. “Can I borrow one when we go play Frisbee on Saturday?”

“Sure. I’ll probably have to do laundry a day earlier, but I don’t mind.”

He thinks for a few seconds. “You know what else I’d like to do in a jock?”

I have no idea. “What?”

“Get fucked while wearing one.”

“Uh-, I-, ah-” I’m at a loss for words.

“Care to help me out with that fantasy?”

I slowly regain my composure. “Like, tonight?”

“Yes, tonight. If you’re ready to.”

“I wasn’t quite expecting that so soon, but I’m not going to say no.”


He wraps his hands around my hips and cups my bare ass. The warmth of his hands feels wonderful. I reach my hands between his arms, unbutton and unzip his jeans, and slide them to the floor. I take his ass in my hands and massage it. He begins walking backwards toward the bed and pulls me with him. He reaches the bed and lies down on his back, pulling me on top of him. Our cocks rub against one another through the pouches of our jocks. I lie flat on his chest and torso, our cocks pressing against each other. We make out for a while, and then I pull away.

“Are you sure you want to do this tonight?”

“Yes. I’m more than sure.”

He grabs the back of my head and pulls me into another kiss. We break contact and I get up and walk to the dresser to grab the lube. I walk back to the bed, place the lube on the nightstand, and begin to take off my jock.

“No, leave it on. I want you to fuck me with it on.”

I pull the jock back up and lie on the bed beside him. He sticks his knees in the air and spreads his legs, giving me easy access. I squirt some lube on my fingers and move them in a circular motion around his asshole. I lean into him until our lips meet and we kiss. We keep kissing as I gently push my finger further and further inside him until my knuckles meet his perineum. I slowly pull out and insert two fingers this time until they’re all the way inside. I lightly massage his prostate, and he softly moans in pleasure.

I whisper in his ear, “Are you ready?”

He nods. “Go for it.”

I pull my fingers out and get back on my knees as he pulls his knees to his shoulders, leaving his ass wide open. I pull the pouch of my jock to the side to expose my now-hard cock. I squirt some lube on my hand and begin to work it on my cock. I position the head at the opening of his ass, slide it up and down a few times, then push it against him. His hole gives way easily and quickly swallows the first few inches of my cock. The sensation almost pushes me all the way over the edge. It has been a long time since I’ve felt this sensation - that I can remember.

I gently push my cock the rest of the way inside him until I can go no further. I lie flat on top of him and we kiss for a few seconds, then I hoist myself back up to my knees, grab his ankles, and start thrusting. I start off slowly, but the sensation feels so amazing that I quicken my pace.

I look straight into his eyes. “How’s that feel?”

“Oh, God, it’s wonderful. Keep going, Brad, keep going.”

I keep thrusting at my new, quicker pace. His eyes roll to the back of his head and his mouth hangs open and his breathing gets faster. I lie down against his chest so that our faces are just inches apart. We gaze into each other’s eyes as I keep thrusting.

“Fuck, James, this feels so good. I’m getting close.”

“You feel like you’re gonna cum soon?”

“Yeah,” I gasp.

“Me too.”

He slides his hand between us and grabs his cock from underneath the jock and begins jerking off. I get back upright on my knees to give him more freedom to move.

I start thrusting faster and faster. “James, I’m getting really close. Want me to cum?”

James is breathing so rapidly he can hardly get the words out. “Yeah. Cum. Inside. Me.”

“You sure?”

“Yeah. Do it.”

I lean forward and support myself with my hands. I pound deep into his ass a few more times and feel myself going over the edge. I moan very loudly as I feel my balls preparing to empty their load.

“God, Brad, I’m gonna cum!”

His balls tense up as he starts shooting his load. The first few spurts of cum fly right past his head onto the pillow behind him.

“I’m cumming, too! Augh!”

My own orgasm starts. I maintain my motions as I shoot rope after rope of cum inside his ass. Believe it or not, this is the first time I’ve ever done something like this.

Our orgasms subside and I collapse on top of him. He wraps his arms around me and we hug each other tightly.

“I love you, Brad,” he whispers in my ear.

“I love you, too,” I whisper back.

I lift my head up to kiss him, then hoist myself back up. I slowly pull all the way out of him and walk to the bathroom to get a washcloth. I wipe off my cock and then clean up around his ass and all the cum on his chest and torso. I toss the washcloth onto the bathroom floor. I then grab the waistband of his jock and pull it off of him. I do the same to mine. I hop into bed and we crawl underneath the sheets.

“Brad, that felt absolutely amazing. Thank you for indulging in my fantasy.”

“Fuck, I’d be happy to, anytime.”

“I do have one more thing to ask of you.”

I patiently await his request.

“Do you think you can get hard again and stick your cock inside me and we can fall asleep like that?”

“Wow, that’s kinky!”

“Not really; I just want to have my boyfriend inside me as I drift off to sleep.”

“Sure thing.”


He kisses me, then rolls over and turns his back to me. I reach my hand under the covers and jerk myself off so I get good and hard again. I feel around for his hole and then position my cock and gently push until I’m balls deep inside him.

“Like that?”

“Yeah, just like that.”

He turns his head and we kiss. “Good night.”

“Good night.”

I normally sleep with someone else holding me, so it’s a bit of a different feeling holding him - not to mention having my cock inside him as well - but it’s a pleasurable sensation nonetheless. And I’ve never felt closer to anyone else in my whole life.