Author's Notes:
This is a work of fiction - just a story from my addled imagination. If you are sexually active, please be safe and use protection.
This story takes place in the 1990s. While the 'when' really isn't important, you will likely notice the absence of smartphones and the internet. Such were the breaks of growing up Gen X.
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Donny and Friends Chapter 8
We went straight to Toby's house after school the following Friday. It was a distant away game that night, so we didn't go. Toby, Marcus, and I went to every home football game, and nearby away games, to support Cullen and Hank, but the school we were playing that night was way the other side of Fort Worth, so Cullen told us not to bother, especially since as second string they seldom got to play.
It was a short walk from the bus stop in Toby's neighborhood to his house, so we were there in short order. We raced up to Toby's room since his parents weren't home yet. We threw down our backpacks and I flopped down on his bed. Toby immediately began taking his clothes off.
"Toby," I said, "maybe you shouldn't get naked."
He looked at me confused, "That was the deal, wasn't it? The 'condition' that you set?"
I chuckled when he air quoted condition with his fingers, but he continued to strip.
"Yeah, I know," I said, "but with your dad coming up here at some point to have his 'word' with us, maybe you should keep your clothes on."
This time he chuckled at me as I air quoted 'word' back at him.
"Besides," I continued, "I'm kinda thinking now that it's not fair to require something extra from just you. So we can forget that part. I'm still gonna let you fuck me whenever you want, so it doesn't matter."
Toby put on a pouty face as he pulled off his jeans. He now stood in the middle of the bedroom in just his boxers. "But what if I LIKE being naked for you? What if seeing you ogling my sexy body makes me happy?"
I threw up my hands in defeat. "Well, fine," I said. "But as long as it's something you want to do, and not something I'm making you do."
Toby got this really mischievous expression that I'd seen many times, and said, "Okay, buddy. I'll make a deal with you. I'll keep my underwear on, unless we're actively partaking in 'club business,' provided you join me in only wearing underwear."
"I'm not wearing just underwear in front of your mother!" I declared.
"Fine," he relented. "You can put on shorts or sweats or whatever when you go downstairs."
I thought it over, watching him stand there with that pleading - yet a touch mischievous - expression. How had it just gone from something he had to do to something I had to? He could always get me to agree to anything and he knew it. I knew it.
He whooped in victory when I relented and agreed to wear just my underwear while upstairs. But I insisted on wearing shorts or something and at least a tank top when downstairs. He reluctantly agreed to my stipulations.
Then he just stood there in his boxers, looking at me. "Well?" he finally asked.
"Well, what?"
"Your clothes, dip shit! Lose 'em!" he exclaimed, waving a hand at me.
"Gagh! Toby!" I complained, but I complied and stripped until I was standing there in just my baggy boxers.
"Ok," Toby began, excitedly. "I acknowledge you just released me from the requirement, but I've found that I kinda like being naked or almost naked. I've been wearing nothing but boxers around the house for the last two weeks!"
"What have your parents had to say about that?" I asked.
"Nothing!" he declared. "Isn't that weird? But I'm not looking a gift horse in the mouth!" He turned and went over to his dresser. "And actually," he continued, "I got some new underwear I plan to wear from now on. But I was saving them so you could see them first."
He opened a dresser drawer then told me to turn around.
"Why?" I protested.
"Because," he said, "I don't want you to see them until they're on. Turn around."
Dubiously, I did as he asked. After a moment of faint rustling, Toby said, "Okay, turn back around." And as he said that the wadded up boxers he'd been wearing struck me in the back of the head. I caught them behind my back as they fell.
When I turned back around perhaps the most glorious sight in all of creation greeted me. Toby stood there, hands on his hips, shit-eating grin on his face, clad only in the tightest pair of fire-engine red boxer briefs I'd ever seen. The material actually stretched from his waist to upper thigh, but the cloth hugged his body so tightly he might as well not have been wearing anything!
"Holy fuck!" I exclaimed, my jaw dropping and his boxers falling from my hand.
"I know, right?" he said, grinning and popping a few poses. "They look good on me, don't they?" He turned to the side showing me his perfect bubble-butt. "How's my ass look?" he asked.
"Does this answer your question?" I asked, pointing at my now erect cock poking out the fly of my boxers.
Toby swaggered up to me - yes, swaggered! It was the most sexy, masculine, professional athlete type walk I've ever seen him pull off, and he most certainly pulled it off! He took my swollen cock in his hand, and cupping the back of my head with the other, he pulled me into a kiss. It was so gentle at first, feathers brushing against my lips. Then it slowly grew in intensity, increasing in pressure until his tongue slid between my lips and danced around inside my mouth. I moaned in pure pleasure and bliss. Then it all instantly stopped. He pulled back and turned away from me.
"Nope, nope, nope," he said, frustrated.
I was standing there, eyes half closed, mouth slightly open, cock drooling pre-cum when he turned to look back at me.
"Snap out of it, Donny," he said from across the bedroom. "If we start fooling around now, we'll be all sweaty and smell like cum when Dad gets up here, and I don't think either one of us really wants that."
It was like being hit with a bucket of ice water.
"No... no... you're right," I stammered, regaining some control. I looked down at my shrinking hard on still peeking out through my boxer's fly, then over at Toby and his erect cock deftly outlined in the skin-tight material of his boxer-briefs. "Maybe we should put some pants on," I whispered hoarsely.
"Yeah... yeah," Toby managed to get out. "Just this once... since, you know... Dad," he said, his voice trailing off.
We slipped our jeans back on. I sat on the bed again and Toby sat at his desk across the room. It seemed like a good idea to stay out of reach of each other for a bit. Finally, we started talking about something other than sex, his hot body, or those goddamned red boxer briefs! I found out at some point later on that while he had purchased several pairs in different colors, he'd chosen the red ones to show me first as an homage to that gag pair of bikini briefs I dared him to wear that first night we'd ever fooled around. If we'd been lovers rather than best friends I would have thought of that as a bit romantic... but maybe I did anyway.
We got ourselves under control and our erections down. Toby turned on the little 12-inch TV he had in his room and found a game show or something. I did some homework. We talked, Toby was quite a chatterbox, you know. Time started to pass quickly and before we knew it his parents began arriving home from work.
From Toby's bedroom we could hear the rumble when the garage door opened and closed. I suddenly felt like I was on pins and needles. I glanced over at Toby who was looking at his alarm clock.
"That'll be Mom," he announced. "She always gets home first. Dad'll be along in another 30-45 minutes or so." But suddenly we heard the garage door opening again. Toby jumped up and ran to his window that overlooked the driveway.
"Shit!" he exclaimed, "Dad's home early!"
My stomach suddenly twisted into a knot. Why was he home early? Did it have something to do with us? Since the day Toby had told me Mr. C. wanted to 'have a word' with us, both together, we'd been trying to reassure ourselves that it couldn't be anything too bad since he didn't seem to be in any kind of hurry. Still, I couldn't help but feel guilty even not knowing what might be wrong.
Toby turned the TV off and I cracked the bedroom door slightly. Toby stood right behind me listening. We could hear their voices drifting up from downstairs but couldn't make out what they were saying.
"Wait a minute," Toby whispered, "Mom sounds... excited. What the fuck is going on?"
We didn't have much longer to stew, though, as we suddenly heard Mr. C.'s footsteps coming up the stairs. I dove back onto the bed and Toby quickly turned the TV back on and sat down at his desk. We did our best to give the impression that we hadn't just been standing at the door listening for... anything. Mr. C. rapped his knuckles twice on the slightly ajar door and then came on into the room.
"Good afternoon, boys," he said with a smile. His eyes flitted back and forth between us. Both Toby and I were shirtless and barefoot, but our jeans were on. "I gotta say," he continued looking at Toby, "I'm surprised you're wearing pants. You know, considering your wardrobe has pretty much been just boxers the last couple weeks."
Toby and I just stared back at him.
"Mind if I sit down," he asked and stepped over to the bed. I pulled my feet up and sat crossed legged at the head of the bed and Mr. C. sat on the foot of the bed. He kicked his shoes off and loosened his tie, then unbuttoned the top two buttons of his shirt getting comfortable.
"Donny," he said, looking at me. I literally jumped at the sound of my name. "I hope you know," he continued, "that I consider you to be one of my sons. You practically live here, and I wouldn't mind if you did. Carol feels the same way." Carol being Mrs. C., of course.
My heart swelled and I got a little teary-eyed. Part of me had long sensed this but hearing it out loud was a whole new dimension. Seeing my reaction, Mr. C. scooted over and gave me a hug. He patted me on the back then released me and moved back to the foot of the bed.
"Toby," he said. This time Toby jumped. "I think you must have had some kind of party here that weekend we were gone."
"Just the guys," Toby said and he tensed.
"I thought so," Mr. C. said with a grin and he winked at me. "If you think you're in trouble, son," he said refocusing on Toby, "you're not. So relax."
He heard the words, but Toby didn't appear to me to relax. Mr. C. seemed to take a moment to collect his thoughts before he started talking again.
"Sex is a wonderful thing, and something to be enjoyed to the fullest," he said. "Whether that's between a couple in a romantic relationship, or just between friends who like to help each other out."
I glanced at Toby and his eyes had gotten huge, as did mine, I'm sure.
"Look," Mr. C. continued, "this house is a safe space. I've been saying that for years, haven't I? Even if you didn't really comprehend all I meant by that." He began shifting his gaze back and forth between Toby and me as he spoke. "If you want to have sex with your friends here, that's fine. If you want to bring home someone you're romantically involved with for some love making, that's fine. If you want to bring over someone new just for a taste of something different, that's fine, too. Sex is awesome and always welcome here provided it's consensual."
He let all that sink in for a couple minutes. Toby and I just kind of sat there looking at each other. His parents knew we'd been having sex! And they were okay with it. What the ever-lovin' fuck!
"Now," Mr. C. finally said, "having said all that, we have to have some rules, don't you think? Call them House Rules, if you like. First, no sex in the living room or kitchen. Nudity is fine, but no sex. That's where we entertain guests and prepare food; it's a personal thing for me, so humor me. Plus, cum stains are a bitch to get out of a sofa."
"Holy shit!" I exclaimed, then quickly covered my mouth with a hand.
"That's why Mom was mad," Toby said, realization setting in.
"Yep," Mr. C. said with a chuckle. "But I smoothed it over by promising her a new couch. But I can't keep doing that!" he exclaimed, shaking a finger at each of us in turn.
"Lastly," he said, and he took on a more serious tone to his voice, "I'm never going to tell you not to hook with someone as long as it's consensual, but," and he pointed a finger at each of us in turn, "you two are still under age and I'm legally responsible for anything that goes on in this house. If you start having partners who are over 18, I need to know about it. I will not judge, but I need to know so I can take precautions to keep us safe. Okay?"
Toby and I were both completely dumbfounded but we managed to say, "Yes, sir."
"Great!" he exclaimed, a big grin on his face. "If you two ever have any questions about anything - and I do mean anything - you can ask Mom or me. The only reason she isn't up here right now is she thought her presence might be too awkward for you."
"Oh, God! It would have been!" I declared. They both laughed.
"Okay," Mr. C. said, "now that that's out of the way, there are going to be some changes around here."
He went on to explain how he was converting the third upstairs bedroom, previously the guest room, into what he called a play space for us. Now, I know how you guys think, so no, it wasn't a sex dungeon - although we kinda used it like one. It was really more of a game room. Mr. C. put in a huge vinyl sectional that he said was "cum stain proof," a 30-inch TV (huge for the time!) with cable hookup, a new game console, plush rug, pillows everywhere, and a mini-fridge! It was really something when he was finally through with it - and he didn't even use it! It was all for us! We began calling it our 'club house' to go along with our 'club business' code word!
"Finally," Mr. C. said with a big sigh, "your mother and I are going to start having guests over once in a while. Probably not anybody you guys know, and if you're here at the same time they are you do not have to interact with them, I want to make that clear." He hesitated, as if searching for the right words. "When we were much younger, before Jack came along, we used to be very active members of... let's call it a club. We pulled back significantly when Jack was born and completely when you came along, Toby."
My eyes widened as I started to imagine where this was going.
"Now that you're old enough to make your own decisions regarding sex and sexuality," he continued, "we want to become active again while we're still young enough to really enjoy it."
I was floored.
"Oh, my God, Dad!" Toby exclaimed. "Are you saying you and Mom are... swingers?!"
"Something like that," he said and shrugged. "What can I say? I like what I like."
I suppressed a chuckle. Toby had uttered those exact words to me just recently.
With that Mr. C. rose from where he was seated. He grabbed his discarded shoes and said, "Now, you'll have to excuse me, boys. Mom and I are going out tonight and I need to get ready." He started unbuttoning his shirt before he was even out of the room. He stopped at the door and looking back he said, "You guys are on your own for dinner. Oh, and Jack's on his way home for the weekend. He already knows all this, well, except for my plans for the guestroom. You can fill him in on that if you like. And... you left his bed worse off than the living room couch. It'd be nice if you changed his sheets before he gets home." And with that, he was gone, closing the door behind him.
Toby and I just sat there looking at each other. What the absolute fuck?! We were speechless. Even chatty Toby. Every now and then he'd open his mouth like he was going to say something, then just not, and close it again. Finally he got up and I followed him over to Jack's room. We changed the sheets and put the cummy ones in the dirty laundry. When we were done we heard Mrs. C. calling to us from downstairs. We went to the top of the stairs to say goodbye and when I looked down at them my jaw dropped. Mrs. C. was wearing this skimpy, tight black dress that showed off her toned arms, cleavage, and long legs. Mr. C. was wearing a satiny blue shirt open halfway down his abdomen showing off his muscular and hairy chest. His black slacks were so tight they looked painted on and the outline of his ample cock could easily be seen.
"We're leaving," she called up to us. "Y'all have fun! Don't wait up for us! We'll see you in the morning!" And with that they headed into the kitchen and out through the door to the garage.
"They're going to their fuck club," Toby whispered, his eyes wide.
"Safe bet," replied.
I stepped up beside him and put my hand on his strong bare shoulder as he stared off the way they had gone. "Are you okay?" I asked.
After a couple minutes he turned to look at me and just seemed to stare into my brown eyes. I stared back into his hazel eyes with their flecks of green. I loved those eyes.
"I will be," he said. "I think... I think I just realized that my childhood is over. I mean... I'm glad. But things are different now, aren't they?"
I wrapped my arms around him in a gentle hug. "I came to the same conclusion two weeks ago as my four best friends in the whole world gangbanged me on your living room couch," I said with a little smile.
"Our childhood is indeed over, but I think our future looks bright," I said, "and I can't wait to spend as much of it with you as you'll let me."
He hugged me back and pressed his forehead to mine. "Do you think your mom would let you live here?"
I thought about it for a moment before answering. "I don't know," I said, stroking his cheek. "But even if not, I'm sure I can be here a lot more than I have been."
"I'd like that," he whispered, then he kissed me - the gentlest, sweetest kiss imaginable. When he ended the kiss he looked me in the eye and had that mischievous glint again. "Game of Street Fighter?" he asked.
"Loser sucks my dick."
"What if I win?" I huffed.
"You won't," he said. Planted another peck on my lips and headed for his bedroom.
When we got to his bedroom he shucked his jeans and just the sight of him in those goddamned red boxer-briefs had my dick getting hard.
"Lose the jeans," he said, and went over to his dresser and opened his underwear drawer. I complied and stood there in my baggy boxers. He then pulled out a bright yellow pair of the boxer briefs and held them out to me. "Would... would you wear these for me? Please?"
Fuck. It wasn't a command, which I might have objected to, and he knew it. It wasn't a trick or a bet payoff, which I would have complied with, and he knew that too. It was just a request, and one hesitantly expressed, like it was something he really wanted but... he wanted me to want it too. He seemed so vulnerable to me at that moment. How could I refuse?
I nodded and took the soft cottony material into my hand. I removed my boxers and slid on the boxer-briefs. They were tight, but so comfortable! They pulled my balls out in front of me, my half-hard dick sticking off to one side.
"Holy fuck!" Toby exclaimed. "They make your ass look ten times better than mine!"
"Not possible, but thank you, sir!" I said chuckling, and wiggling my ass in his direction. "Maybe I can distract you enough to beat you at the game."
We settled down to a game of Street Fighter. I almost won, but no dice. Toby sprang to his feet and did a little victory dance in those boxer-briefs - shit! I was sitting cross-legged on the floor and just leaned back on my hands enjoying the show. He danced over to me and his crotch was suddenly in my face. I reached up prepared to deliver on the bet.
"Anybody home?" a voice came echoing up the stairway from the front door. Jack was here!
Disappointment flitted across Toby's face, but it was fleeting. He was happy to see his brother. He bolted for the stairs, and I jumped up to follow. I started to grab my jeans, but then I thought, 'Fuck it!' and I followed Toby out the door and down the stairs in just my bright yellow boxer briefs.
Jack was all smiles and hugs, happy to see us, too. If he thought it odd we were both dressed only in those brightly-colored boxer briefs that hid absolutely nothing, he didn't let on. Typical college kid, he had a huge duffel bag over his shoulder full of dirty laundry. We followed him into the garage chatting as he got his first load going in the washer.
Jack said he wanted to take us out for dinner since Mr. and Mrs. C. were out for the night. So Toby and I got dressed and Jack took us to a sports grill in town. There was a high school football game on the TVs but not our school. We were too small to get any coverage like that. But we had a good time and just enjoyed being with Jack.
It was after dark by the time we got back to the house. Jack said he had some things to do so we split off with him heading to the garage to tend to his laundry and Toby and I heading upstairs to Toby's room. Toby had started stripping before we were even inside the front door. He'd pulled his t-shirt off as soon as he got out of the car and kicked his shoes off at the foot of the stairs. He picked them up and darted upstairs and I followed. Jack was behind us as we made our way from his car to the house so he saw, but made no comment. Once up in his room, Toby shucked his jeans again and I followed suit without waiting to be asked. Once again we were in those goddamned, skin tight boxer briefs. Just seeing the way they hugged Toby's ass made me start to chub up.
Toby turned on his little TV and made some comment about how great it would be once the guestroom conversion was done so there'd be a big TV up here. I agreed, grabbed a sci-fi magazine and flopped down on Toby's bed to read it. Toby put the TV on some cop show then settled down next to me on the bed to watch it.
I was laying on my stomach sideways across the bed, my legs bent at the knees with my bare feet up in the air and propped up on my elbows flipping through the mag. Toby was sitting cross-legged beside me with his back against the wall. After a few minutes I felt his hand come down on the back of my ass and just rest there. A couple of minutes later his hand started to caress my butt-cheek through the stretched cotton fabric. Toby's bedroom door was not shut all the way and I could hear Jack moving about in his room across the hall and in the hallway.
I pushed Toby's hand off me, and turning back to look at him over my shoulder I mouthed, "Jack's right there."
"So?" Toby whispered, and put his hand back on my ass. This time he began to run a finger up and down my cotton-clad ass crack. I was about to protest again when the door swung fully open and Jack came into the room. He was carrying a brown paper bag that looked like it held a few magazines, but that's not what I noticed at first. Rather, the first thing that caught my eye was that Jack was now wearing an orange pair of the exact same type of boxer-briefs as Toby and me and nothing else!
Jack walked across the room, sat his bag down on Toby's desk, then turned the chair around to face us and sat down in it with his legs spread wide apart. I almost died! His body was basically an older version of Toby's - a little more muscularly developed, a little more hair on his chest, same rounded shoulders, defined pecs, and ripped abdomen... just more of it. And the bulge in front of his boxer briefs was a lot bigger! I was so glad I was laying on my stomach because my cock was instantly hard!
I felt movement behind me and realized Toby's hand was still caressing my ass - IN FRONT OF HIS BROTHER!
"Earth to Donny!" Jack said, and I suddenly realized that he'd been talking since he entered the room but I'd missed all of it, mesmerized as I was by this golden Adonis!
"Wha... wha...?" I managed.
"I said, do you want to see what I brought you?" Jack said, apparently for at least the second time.
"Brought me...?" I stammered.
Toby chuckled and swatted my ass, but his hand stayed there. "I think he's a little distracted, Jack," Toby said. "Cut him some slack."
Jack laughed. It was light yet manly. How could a laugh make my dick twitch like that?
He picked up the sack and said, "I brought you some new porn mags for your stash. Well, for both of you," he said, then set them back down.
"I brought you something else too, Donny, if you want it," he said, his tone hinting at a chink in his armor of self-confidence.
"What else?" I asked.
Jack leaned forward in the chair placing his elbows on his knees. His face took on a serious, almost pleading expression. "Me. I'd like to join your little club... if you'll have me, that is. I realize I'm a bit older - I'm halfway to 19. And I'll be away at school a lot, but, you know, I was hoping... that when I come home for visits, that, um..."
"Jack," Toby said, "take a breath." Then to me, "He wants to be your friend, Donny."
I cocked an eyebrow and glanced at Toby then back at Jack. Was he really saying what I thought he was saying? "You are my friend, Jack," I said.
"No," Toby replied. "He means he wants to be your friend like me and the guys are. You know, 'friends with benefits.' He wants to fuck you."
"You don't have to put it so crudely," Jack complained and sat back nervously.
My heart was all aflutter. I sat up on the edge of the bed, my erect cock now on full display within the confines of my tight underwear.
Turning to Toby, I began speaking as if Jack wasn't right there in front of us, "He IS fuckin' hot. I've always wanted a piece of that just like I always wanted a piece of you. But he's your brother."
Toby smiled and winked at me. "He is."
"And you're okay with it?" I asked Toby, but glanced back at Jack.
"I don't own you," Toby said. "But he wouldn't be in here if I wasn't okay with it. You know Jack's a real stand up kind of guy. He's a hero-type, just like me and the guys. He and I already talked about it and I told him the decision was yours."
I kept glancing back and forth between Toby and Jack. "You obviously expect me to say yes. What if I say no?" I asked.
Alarm and disappointment flashed across Jack's face. "If the answer is no," he said, "then I'll go back to my room. No harm, no foul... and no judgement. Hopefully, we go on like we always have up to this point, and I hope you don't hold it against me. You'll still be my little brother's best friend and very special to me, even if your opinion of me changes for the worse."
I sat there for a few moments just watching him, his brow above those bright green eyes netted in worry. There was never any doubt in my mind, but it was nice to hear him say it. I stood up and crossed the room to him. Kneeling between his legs, I ran my hands up his thighs, enjoying the feel of his muscles and leg hair. I leaned in and kissed the outline of his cock in his boxer briefs, which was now growing rapidly.
"I'd love for you to fuck me, Jack," I said, and then nibbled on the head of his cloth covered cock. I pulled him to his feet then, and grabbing his boxer briefs by the waistband I pulled them down and off. The circumcised monster that jumped out at me took my breath away! His now fully erect cock was huge! It was longer than Marcus, who I knew to be seven inches exactly (we had measured everybody's dick that first sexy weekend) but it didn't seem to be as thick around. That was good - I knew I could handle his girth, but nobody had yet been as deep as he would be going. But I felt up to the challenge!
I took that monster in my hand, wrapped my fingers around the base and cupped his low hanging balls with my other hand. A pearl of pre-cum materialized at the slit and I caught it with my tongue. He tasted just like Toby! I ran my tongue up the underside of his shaft and swirled it around the glans, eliciting a moan from the god before me. I looked up at his face to see him watching me, eyes wide. I maintained eye contact as I opened my mouth and took him inside.
"Aw, fuck!" he yelled and threw his head back. I heard Toby chuckle behind me from the bed.
I worked that massive cock over good. When he hit the back of my throat I struggled to suppress my gag reflex but I was determined. I had to pull off a couple times to regain control of it, my saliva was streaming down his cock and my arm. Long strings of the stuff would connect my lips to his cock each time I pulled off to breathe. Finally, after several attempts he hit the back of my throat one more time and I swallowed hard. And with what felt like a pop, I felt his cock head enter my throat!
"Oh, Donny!" Jack moaned. He grabbed two fistfuls of my long wavy brown hair and began to fuck my mouth. He pounded me hard, his cock entering my throat at the end of each thrust now. I was grunting and moaning from the abuse.
"Don't hurt him!" I heard Toby cry out, his voice full of concern.
Jack immediately released me from his grip and I fell back onto the floor. He was instantly kneeling by my side, regret all over his face.
"Donny, I'm sorry! I..."
I grabbed him by the back of the neck and growled at him, "Jack, don't you ever stop fucking me!" And I pulled him into a passionate kiss, viciously attacking his tongue with mine.
I felt the relief wash over Jack as he kissed back and behind me I heard Toby scoff under his breath, "Jesus, Donny."
Jack then scooped me up in his strong college baseball player arms and stood, holding me like I weighed nothing. He held the kiss for a few more seconds then broke it to say, "Toby, there's lube in my nightstand. Would you get it, please?"
"Oh, that's all used up," Toby said proudly. "But I have some here."
And he got up to retrieve a new tube of KY from his dresser.
Jack laid me down on my back, ever so gently, sideways across Toby's bed, so that my ass was right at the edge. He pulled my underwear off and tossed it over his shoulder. Spreading my legs wide, he knelt between them and gazed down at my 16-year-old's five-inch circumcised dick and smiled. "That's the prettiest cock I've ever seen," he declared and then dove down on it taking the entire length into his mouth.
Lightning danced through my entire body! My senses exploded in total overload! "OH, MY FUCKING GOD!!!!" I yelled so loudly if anybody else had been in the house they certainly would have come running! I grabbed Jack's sandy-blond hair in fistfuls of my own and pulled his face tight against my pubic bone. I wrapped my legs around his neck and squeezed just as tightly. I didn't fuck his face, I just held him there as his tongue and mouth suction did all the work. Within moments I was shaking violently in orgasm as my spunk shot across his tongue and down his throat over and over and over!
"Wow," I heard Toby comment.
When it was finally over, I released Jack, my arms and legs falling away completely limp. I was in ecstasy.
Pulling off my still hard cock, Jack turned to Toby who was back on the bed near us and asked, "Jesus, Toby, have none of you given him head yet?"
"Um... no," Toby mumbled sheepishly. "He usually just cums on his own."
Jack rolled his eyes at his brother, then placing his hands behind my knees he pushed my legs back until they were high in the air and my ass was on full display for him. He dove back down, nuzzling my ball sack with his face then licking and kissing my taint. These were completely new sensations to me since, no, the boys hadn't really done anything to me other than fondle and caress me with their hands. Well, and of course with their dicks. For the straight boy I always thought he was, Jack sure knew how to please a man. We would have to have a talk about that.
"OH MY GOD!!!" I screamed again as Jack's tongue found my anus and attacked it. His tongue swirled round and round then tried to enter. I flexed my sphincter for him, and in it went. I was in Heaven! I was moaning and cooing and telling Jack how wonderful he was. I kept reaching down to feel the top of his head as he worked over my hole, as if I didn't really believe he was there or something.
Finally, after several minutes of this, Jack pulled off and I heard him ask Toby to hold my legs up for him. He took the KY and squeezed some out onto his fingers and slowly began inserting them into my hole. He started with two fingers! Swirling them around, sliding them in and out opening me up. Then three. Then four!
"Donny," he whispered, "do you think you're ready for me?"
"Oh, God! Yes, Jack!" I yelled back at him. "Stick that monster in me! I need it so bad!"
Jack and Toby both chuckled a little at that, but fuck, I didn't care. Jack took some more of the KY and generously slathered it on his hard cock and then brought it to my hole.
"Here it comes, buddy," Jack muttered and began to push.
There I was, flat on my back on my best friend's bed, legs in the air, held in place by my best friend, while his brother penetrated my ass with the largest cock I'd ever seen in real life. Fire shot through my ring as Jack's big head slipped in. He paused for a moment maintaining eye contact with me as he let me adjust to him. Like I said, he wasn't as thick as Marcus, but it had been a while since Marcus and I'd had any time together, so it took me a minute. But the pain soon faded to pleasure and I nodded at Jack. He pushed and went in another inch or two. He paused again to let me adjust. This went on for at least 10 minutes before he was all the way in, but all the way in he finally was, and I felt his pubes tickling my taint and his ball sack came to rest on my ass.
"Fuck me, Jack," I said.
"You got it, Donny," he answered me and began to pull out and thrust back in.
Long slow strokes at first, giving me more time to get comfortable. Nobody had ever been this deep before. But it wasn't long before it felt good... really good. Toby released my legs and I wrapped them around Jack's mid-section. He was leaning over me supporting himself with his arms on either side of me. I began to caress his hard, muscular chest and tweak his nipples.
"This is good, Jack," I cooed at him. "You're so good!"
He picked up the pace, but very, very slowly. I loved everything my friends had done to and with me up to that point. It had been wonderful, they had been wonderful. But I realized at that very moment staring up into Jack's rugged, handsome 18-year-old face, that Toby, Marcus, Cullen, Hank, and I were still boys and had so much to learn. Jack was a man. And he was fucking me like a man. He had experience and knew things that my friends and I didn't. But he was going to teach us. He was going to teach me.
Jack fucked me right there on Toby's bed for over half an hour. He kept varying his speed and changing positions, edging himself. I was in total awe. I came twice more just from him hitting my prostate.
Finally, just as I thought I would give out, Jack, the sweat from his exertions dripping down onto me, said, "Here it comes, little buddy! Take my load!" And I felt a warmth flood my insides as rope after rope of his spunk rocketed into me. He moaned loudly and every muscle in his body stiffened. Then he collapsed on top of me shaking. I wrapped my arms around him and kissed his ear and cheek as he nuzzled my shoulder.
"Fuck, Jack," I said. "You completely wore me out. But, like, in the best possible way ever!"
I felt more than heard him chuckle. Then he lifted his head and looked at me, "That was... the best orgasm... I've ever had," he whispered.
"I told you he was a good fuck," I heard Toby say. I glanced over at my best friend and saw that he was leaning against the headboard, naked and covered in his own cum. He'd jerked himself off watching us.
"You're the best, Donny," Jack whispered, and kissed me ever so gently.
--=TO BE CONTINUED=--