I was lying atop fresh sheets and blankets, my cock as hard as ever, thinking about the day and the amazing blowjob I had gotten from my mom. My mind in a whirl, skipped to the amazing way that I masturbated with my sister as well. My cock head, though technically we hadn’t fucked, had slipped between her sweet pussy lips. I came instantly and like a horse, spewing more cum than I ever had.
‘If it felt that good just from the way we had done it,’ I thought, ‘Real fucking is going to be unbelievable.’
I wondered if she would ever let me. I could only imagine, never having fucked a girl, how amazing it would be. I also wondered if my mother would repeat our earlier fun. She had sent many videos to my phone. I watched them all, stroking my dick as I did. For the last three hours I stroked, bringing myself just to the edge of orgasm then stopping until the feeling passed.
One video showed her sucking the UPS driver. His black cock, though not as big as my own, was impressive. He was circumcised and the head and last few inches of his cock was pink rather than black. It was a curious thing to see. I wondered if he tasted different to her than I did. His cum was not thick like mine but more liquid. I wondered if she liked it more.
Mom sucked like a Hoover vacuum taking his hard, black cock deep into her throat.
Opening her mouth wide, she looked at her phone when his cock began to pump cum onto her tongue. Just like a porn star, she showed the camera a mouthful of white cum just before swallowing it in one big gulp. Squeezing his cock, she licked the last bit of cum from the tip.
I nearly jumped from my bed when my phone began to ring. It was James Craft. You remember, the guy I ran into during my jog earlier in the day. I could only imagine what that horny fucker wanted. I let it go to voice mail the first time but he called again without leaving a message. I figured that I might as well answer. He would continue to call until I did.
“Hey, James.” I greeted, “What’s up man?”
“My dick,” he answered with a chuckle. “How’s it going with your sister’s friend?”
“You wouldn’t believe me if I told you.”
“You gotta tell me, Terry.”
“No shit, James,” I warned him, “You can’t repeat any of this.”
“I swear, but not on the phone,” he said, the excitement in his voice was obvious, “I’m coming over.”
“What? It’s ten o’clock at night.”
“So what, I’m on my way. I’ll be there in five minutes.”
“Okay, okay. You just hafta leave before my mom gets home.”
“Deal,” he agreed, “I’ll be there in five minutes.”
“Okay, but come to my window. Don’t knock on the door.”
“Whatever you say. Seeya in five.”
I hung up the phone and found a pair of basketball shorts to cover my dick that just would not wilt. It didn’t really matter. He saw my bulge this morning and didn’t even try to hide his. It would have been very embarrassing had anyone seen the both of us standing there with our boners on display. It wouldn't surprise me, however, if someone had. What my mom said about Mrs. Wheatley, next door was true. She had called about two hours ago and left a message for me on our machine.
The tapping on my window pulled my mind away from my Mrs. Wheatley fantasy. James wasn't lying when he said five minutes. Opening the curtain, I unlocked my window and let him in. He was winded and sweating from his run but when he stepped through the opening, his dick was obviously erect.
“Damn, James,” I joked, “Put that thing away before you hurt yourself.”
With a laugh, my friend replied, “After you. You're as hard as I am.”
“I've been hard all fucking day. That girl is hot as fuck.”
“Did you have any fun with her after I saw you on the street?” James asked.
I told him the story of what my sister and I had done, changing the names of course. You know, to protect the innocent. I couldn't tell him that my sister was the one I was masturbating with. Although he said earlier that he had fucked his mother. I wondered if that was true or just a joke.
“Is she here?” he asked, “I gotta see her.”
Thinking fast, I answered, “No. She had to leave an hour or so ago. Some family emergency.”
“That sucks but at least you got to have some fun with her.”
“I’ll be jacking my dick for days thinking about her. I really wanted to fuck her but she said my dick was too big.”
“Bull shit,” James laughed, It’s not as big as mine. Girls like them big anyway.”
“She is very petite,” I told him, “And my dick is way bigger than your little Vienna weenie.”
“Whip it out,” he challenged, thinking I wouldn’t.
“You want me to show you?”
Put your money where your mouth is, Bud,” he goaded.
“So, we’re betting on this?” I asked, “How much?”
“I ain’t got no money,” James said, “We can bet something else.”
“Like what?” I asked sourly, “And I already told you, you ain’t fucking my sister.”
“Fuck, man,” he laughed, “The friend is gone. Your sister is off limits, your mom is at work. That just leaves you and your dad.”
“Okay. If you want to bet your cock is bigger than mine, then let’s bet blowjobs,” I challenged.
“Woah,” he said, eyebrows raised, “If mine is bigger then you’re going to suck me?”
“And if mine is bigger, then you’re going to suck me,” I said, offering to seal it with a handshake.
I already knew mine was bigger, having seen him in the boy's showers after football practice. I knew I had at least two more inches than him. Surprisingly, James took my offered handshake and said, “Whip it out, big boy.”
With a tilt of my head and an eye roll, I pushed my shorts to my knees, my rigid cock slapping my belly after springing from the elastic waistband. Hands on my hips I wagged my cock back and forth in front of my friend, “Your turn dickhead.”
His eyes closed in defeat and I saw the life drain out of his soul. He knew the second he saw my hard dick that he had lost. Shaking his head in disbelief, he just stood there staring at my cock.
“Whip it out, asshole,” I laughed.
“You keep that thing away from my asshole,” he laughed, pushing his shorts down. His cock was as hard as mine and his balls hung low. He was impressively thick but his length just didn’t match my own. Still, he didn’t concede defeat.
“We need to measure them,” he suggested.
“What for?” I grumbled, “I’m definitely longer. Besides, I don’t have anything to measure with.”
“Well, I’m not going to lose without some kind of measurement.”
I looked at his cock, his balls shaved like mine, hard and with an upward curve. Just the opposite of mine. He knew as well as I did that he had lost. He was trying to get out of paying up. I wasn’t about to let that happen.
“Look, asshole,” I began, my tone a tad sharper, “You can see that I’m bigger. But if we have to do it, come here.”
James just stood there looking at my cock, knowing he had lost. Shaking my head, I reached for him, taking his bent cock in hand and pulling him to me, I put his shaft next to mine to compare. Both our cocks in my right hand, I let him see that mine, even with the more pronounced downward bend, was touching his thigh while his was a good inch away from mine. Surprised as he was that I was holding his dick, he made no effort to pull away. I noticed his heart beating very quickly and his breathing was slow and very deep.
Thinking that he was about to come, I released him from my grip. James, apparently didn’t expect me to touch him like that and I could tell that he swooned nervously.
“You alright?” I asked.
After a few seconds, his eyes a bit glazed but still fixed on my cock, he answered, “Uh, yeah.”
“Time to pay up, bud.”
“Wait,” he balked, “You don’t really expect me to do it, do you?”
“A bet is a bet and we shook on it.” I answered, “If you back out, then you’re a fucking coward.”
“I’m not a coward, but.”
“But nothing,” I demanded, maybe a bit too loudly, “You need to pay up.”
I noticed his dick beginning to wilt but he was still standing there, shorts around his ankles, staring at my dick, “Look, I’ve never um. I ain’t never done this so you probably won’t like it.”
“Nothing to it,” I said before thinking.
“You’ve done it?” he asked in surprise.
Thinking back to my sister’s advice, “Own it.” I answered honestly, “Yes. Once.”
“Who?”
“I don’t know if I should say. I mean I don’t want it to get out.”
“You think I want this getting out?” James asked, “I promise not to tell.”
“Okay,” I conceded, “But only after you pay up. Then I know you aren’t going to tell.”
“What should I do first?” He asked.
“Uhm, let’s see,” I said, trying to make up my mind where to let him do it. Call me lazy but I wanted to lay on my bed. Kicking my shorts to the side, I told him to get on the bed. I laid back with my legs apart, my cock stiff and throbbing, “Now get between my legs and stroke it for me.”
“That wasn’t part of the deal,” He protested.
“Look, asshole,” I hissed, “You need to try and get used to the idea of what you’re fixin’ to do, okay? Just do like I say and you will be able to do it without being nervous.”
“Yeah, I guess you’re right. So whose dick did you suck?” He asked after slowly and nervously taking hold of my shaft.
“Not so tight. Damn.”
“Sorry.”
“Just go easy. Stroke it slow and get used to it.”
Looking up at me after a few seconds, James asked, “Is that better?”
“Yeah,” I moaned, eliciting an odd smile of achievement from my new best friend, “Pull my foreskin back and lick the head.”
His smile melted, replaced with a serious and determined expression. I could tell that he had committed himself to this. Gripping my shaft further up by the head, he slid my foreskin back, revealing my wide cock head. It glistened with pre cum that began to slowly ooze down my shaft. James cocked his head, watching intently, the steady leak of clear fluid from my pee hole.
“Don’t think about it, bud,” I encouraged with a whisper, “Just do it.”
His eyes glanced up at mine with a nod of his head, he flattened his tongue and licked it like an ice cream cone.
“Salty,” he whispered.
“Yeah, I know,” I smirked, “I guess yours tastes like vanilla.”
“No, it’s salty too.”
James continued to lick my cock head tentatively. I snuck a short video of him on my phone, just for insurance. He never suspected.
“So how did you end up sucking a cock?” he asked, “Are you gay or did you lose a bet too?”
“No, I’m not gay. We were drinking and it was a dare,” I answered. “I guess I always wanted to know what it would be like.”
“Did you like it?” James asked, then continued to lick the clear liquid that oozed from my dick.
I was looking at the ceiling when I answered, “I don’t know, really. I was a little drunk and very horny. We were talking about Miss. McKenzie from English.”
My eyes closed, I was enjoying the feeling of a tongue on my dick. I felt his lips on my tip. Looking down at him, I saw him taking my cock head into his warm mouth. A soft moan escaped my lips.
Taking my cock from his mouth, James said, “It’s not as bad as I thought. At least so far.”
“Well, you are doing good so far,” I told him, “Just be careful of those teeth.”
With a playful growl, James, not so playfully, bit the head of my dick. It didn’t hurt but it surprised the hell out of me. With a start, I pulled away and my dick came out of his mouth but not his hand. Taking a tight grip, he held me, saying, “Bring that back. I’m not finished with it yet.”
“You starting to like it?”
“I like the clear stuff,” he admitted. “You should try this while you aren’t drunk. You might like it too.”
“Do a good enough job and I might return the favor,” I said, encouraging him to continue. It was my intention from the get-go to do it anyway. But I wanted to make sure it would be our secret. I even wondered if I could talk David into it again. Maybe even a threesome with my mom. I knew he had already gotten a blowjob from her just like I did. Mom would be willing I was sure.
Turning my attention away from my thoughts and back to the guy sucking my dick, I saw that he had my cock head in his mouth, swirling his tongue. He was taking it slow but learning quickly.
“That feels good,” I whispered.
“I figured,” he said, “You were moaning. You make a lot of the clear stuff.”
“You like it?”
“Just between us? Yeah.”
“You take your time then. Just be ready when the white stuff comes.”
“Oh,” James, “Yeah, I wasn’t even thinking about that part. Are you going to warn me.”
“That depends.”
“On what?” he asked, looking at me over the exposed head of my cock.
“Whether or not you plan to swallow it or spit it out.”
“I dunno,” he mumbled, his hand slowly stroking my cock.
“If you’re going to spit, I’m not going to warn you,” I told him. “I swallowed the whole load when I did it.”
“Okay,” he began, “If I do a good job and swallow, are you going to do me?”
“I was thinking about it. I was drunk last time and I think I want to try it again. But you gotta let me cum while you’re sucking me.”
“Deal,” he said, shaking my dick instead of my hand.
“I bet you can’t take it all,” I told him.
“I’ll try but you’re probably right.”
“You never know. You might even like it,” I encouraged, “Only one way to find out.”
With a nod, James took my cock back into his mouth, slowly working up and down my throbbing shaft. He was making an effort to take it all but I was sure he wouldn’t be able. If he was honest, and I’m not saying he was, this was his first time. It just seemed like he was taking to it quickly.
I let my head fall back into my pillow and just enjoyed the pleasure he gave. It was almost a loving experience, the way he fondled my scrotum. Pulling my cock from his mouth, he stroked my spit-slick shaft. I thought he was giving himself a breather but was surprised when he began to suck one of my balls. The feeling was almost indescribable.
His tongue played over and between my testicles, while his hand slid up and down my dick. With every passing minute, my doubts grew that I was his first. That doubt was confirmed when he took my dick in his mouth again, swallowing my shaft until his nose touched my closely trimmed pubic hair. His eyes looked directly into mine as he held my cock deep in his throat for as long as he could hold his breath. I wanted to come right then.
