The Society Boys By Connor Matthews
Chapter 35 -- Preparing Kyle
The next day the event planner came by to ask for the cheque from Colin, but since he had left early, I needed to call him.
"Shit, I forgot." He said. "Just use that account I gave you and grab some cash to give them. I totally forgot about a cheque and I have the credit cards with me. I'll have to make sure to get one for you when I get home."
"No problem, babe. Have a good trip." I turned to the planner and asked if he had a few minutes to go with me to the bank so I could withdraw the money. He handed me the bill and I almost choked at it. It was a little over $30,000. Holy shit, I had no fucking idea. I guess I wouldn't be using the banking machine. Thankfully the TD bank was open on a Sunday, so it wouldn't be a problem. I headed down and got the money for the guy. The teller asked me if I would like my balance, so I figured I should keep a record for Colin. With bills like that it wouldn't take long to run out of cash. She handed me my printout and I stared at it in disbelief.
"Are you sure this is right?" I asked cautiously. She looked it up again and assured me it was. The balance was $4,975,000. Colin's idea of leaving me some money was $5 million bucks. I wonder if he had actually meant to do that. But regardless, I was keeping the statement to frame on my wall, so I could look back at it one day to remind myself that for a few brief moments, I was a millionaire! I paid the bill and headed home, almost giddy with excitement. I wanted to go out and spend some, but figured Colin might not appreciate that, although it was tempting. Just the thought of knowing that I could go to the store and buy anything was a thrill in itself.
The doorbell went again and I opened it to see Jason standing there. "Since when do you ring the bell?" I asked looking past him in case there was a reason.
"Just felt like it. I wanted to drop the Lamborghini off. The deal was we could keep it until prom, and since it's over I thought I better give it back before Alex took off with it, never to be seen again." He smiled. We went out to the driveway and the car was waiting. Such a beautiful machine. I opened the garage and Jason pulled it inside. He came in for a bit and we hung out like we haven't done in a while. We played a few games of pool, worked out in the gym and took a swim to get a few laps in, then sat and watched a movie.
Both our phones went off at the same time and we were receiving a text from the `Q'.
Incoming Email' is all it said. I opened the laptop to check the email Reminder of the upcoming Art Gala. Members are expected to be at the Main Art Gallery at 8am Saturday to be prepared for the show which runs from 5 to 11pm. Get lots of sleep and make sure you are shaved smooth. Also do not forget it is pledge time. Submit your suggestions for this year's pledges by Saturday. Decisions will be made in three weeks, and nominators will be notified.'
"Wow, I can't believe it's been almost a year since I went through that." I said.
"Wonder who we should choose." Said Jason.
"Well, the first two that come to mind are Kyle and Aaron, although I'm not sure that Aaron is ready yet." I suggested.
"Kyle for sure" agreed Jason. "What about Gavin? Didn't you tell me he was wearing a bisexual bracelet at the party?"
"True. Maybe." I said as we continued to brainstorm for others.
"Wait a second. Don't the rules say that if you fail the pledging process that neither you nor any member of your family may ever be made a member?" I said as I thought about Aaron. Brandon was his brother and had come so close last year, but dropped out only a partial task from finishing.
"Yeah, I think so, but it seems unfair that he couldn't be included. Maybe we could ask for special consideration."
"Maybe. I'll check with Jake." Or Colin, I thought to myself.
"We threw out TJ's name, Brent from the bowling alley that was supposed to be Jason's friend (as far as Brent knew). I suggested Brody just for fun, but that would have been wishful thinking. Nathan was also a possibility. Jason said Josh might be a good candidate too. Looks like we weren't going to have trouble coming up with names, we just had to make sure we picked guys, that if selected could complete the tasks. I was definitely submitting Kyle as no one deserved it more, in my opinion. Then we talked about the Art Gala thing.
"Any idea what that is about?" I asked.
"Nope, but it sounds like a long day. I guess we'll be setting it up though as it doesn't start for 9 hours after we get there."
Jason quickly checked his email to make sure his wasn't something different, as we learned not to assume things with the `Q'. His was the same.
"Can you give me a ride home?" He asked after saying he should get going. I got the Lamborghini out and drove Jason to his house. I had the car to myself again and drove around a bit enjoying it and the looks it got. Finally I headed home for a late dinner as I'd told Kyle I'd cook since he'd done so much at the party.
I pulled into the garage and went into the house where Kyle was dancing to a video game. Gotta love the type where you don't need the controller. He saw me and stopped.
"What do you want for dinner?" I asked him.
"Pizza" he said grinning.
"Not much work for me in that." I laughed but agreed that I could go for that too. We ordered it and I joined him in the dancing. We enjoyed the pizza and took the plates and glasses back to the kitchen.
"Justin, I wonder if you can help me" said Kyle as he flopped onto the couch sounding frustrated.
"Sure buddy, what do you need?" I asked sitting beside him.
"Well, a couple of nights ago Aaron and I tried to fuck, but neither of us could handle it. I think we're just too big for each other. His dick felt like he was trying to put his whole arm up my ass."
"Oooo, fisting. Kinky bitches." I laughed.
"Haha" he said without much humor. "What if we can't fuck at all? Does that mean we're stuck with just blowjobs? Or will we have to break up?" He asked quickly.
"No need to rush anything, Kyle. Just take things slow. All you need is to open your ass up by getting used to putting bigger and bigger things in there, until you can handle it. There are some easy things that you can do that will help. Without sounding gross, if your ass is empty, it will feel more comfortable as there's less resistance. Then use lots of lube, breathe and relax." I said giving him the best advice I could.
"We did all of that. We even fingered each other for a while, but when it came to putting our dicks in, neither of us could handle it." He said sounding dejected.
"The next thing is maybe try dildos, start small and get used to it, then get bigger and bigger until you can accept one the size of your boyfriend. Work on each other together."
"Can I ask a big favor" he said looking at me sheepishly.
"Ok" I said hesitantly.
"Would you teach me? Fuck me so I can learn how to do it?"
"I think that is something you should share with your boyfriend." I said, but in actual fact I loved the idea of fucking him. "Remember what I told you, that you should do everything with him first, before involving others."
"I remember and technically we did try" he said with a weak smile "If it makes any difference, Aaron and I talked about it, and he agreed that I could ask for your help to teach us how to fuck."
I grinned. "Did he agree that you could get advice help and maybe show you a few things, or did he agree that I could fuck you?"
"Ummm, we didn't discuss it specifically, but help is help, right?" he said as he leaned against my shoulder. "Please" he begged, wrapping his arm around me. I guess he knew my weak spot. "I also have another reason for asking. Aaron turns 16 next week and I want to surprise him by having him fuck me. He surprised me on my birthday, so I wanted to do this for him on his."
"All right, I'll show you a few things to help." I agreed. He beamed and sat up.
"Should we go to your bedroom, or what?" he asked like a typical horny teenager.
"So, I'm guessing you want it now?" I laughed as I stood up. "Why don't we start in the bathroom and I'll show you stuff there first." He followed me upstairs.
"I'm just going to tell you like it is okay. Nothing sexual in it, just the basics okay?" He nodded. "The first part of anal play is to make sure you are clean inside. Nothing grosses someone out more than rimming and fucking when you're full of shit." I laughed.
"Fortunately we have two bidets on the house, which you can use anytime to make sure you're clean; but for the first time we'll use the portable one that hangs on the shower head as it has a smaller nozzle. The bag on it holds about a litre of water which is enough for now. Use water that is warm to the touch, but not hot." I instructed him as I got the shower enema kit out for him. I hung it on the shower head and filled the bag with warm water and primed the hose so that there were no air bubbles in it or he'd be farting air for hours. He was watching each move closely and I loved being his teacher.
"All right buddy. Time to get naked." I told him. He didn't hesitate and was quickly standing naked in front of me with his dick already semi hard. I wanted to give him a blow job, but we were on a training mission. "Put some lube on your finger and push it into your hole. It'll make the nozzle go in easier." He did it. "Now lube up the nozzle."
He was ready. "I prefer to do it close to the toilet so you can empty yourself into there. The best way to start in on your knees so the water can flow into you easier." He got onto all fours and waited for me to push the hose into him, but I wasn't always going to be around to do this, so he had to do it on his own. I handed him the nozzle and showed him the clip to release the water when he had inserted it all the way in. I used the slimmest nozzle so it would go in very easily. The bidet was much thicker and would take him a couple of times to get used to it. He pushed the nozzle into his ass and took it pretty well.
"Okay, flip the clip and once all the water is in you, clamp your ass tight and pull the nozzle out. I find it best to sit on the toilet and hold the water as long as you can. Then just relax your ass completely and let everything flow out of you. It'll feel weird at first. Once you're done, flush and we'll go again. I'm going to give you privacy to do it as I'd hate it if someone saw stuff coming out of me. I watched the water flow into him and he did as he was told, pulling the nozzle out and sitting on the toilet.
"Fuck this is really uncomfortable. It's giving me a stomach ache." He complained.
"You get used to it, but just hold it for as long as you can. It loosens things up inside you. Call me when your empty and have flushed." I went into the bedroom and closed the door as I exited. I turned on the TV so I couldn't really hear the noises that go with an enema. It was only a couple of minutes before I heard him call me. He was standing waiting as I went in.
"You're right that really was gross." He admitted looking embarrassed.
"Okay, time to do it again. This time you do it all." Kyle filled the bag and followed each step I had shown him. He's a fast learner and was soon back on the toilet with another litre of water in him. I returned to the bedroom and waited. This time he lasted a couple of extra minutes before calling me back.
"Was the water cleaner this time?" I asked.
"Definitely." He admitted looking pretty pleased with himself.
"Okay, take the bag down and we'll clean it up later. Jump in the shower and use soap to thoroughly wash your ass. Make sure you pull the cheeks apart and get right against your hole." He quickly took a shower and dried off. I took him into the bedroom with some towels; grabbed some of the toys out of the night table and showed them to him. First we had the baby dildo and butt plugs, followed by about five sizes of dildo, some thick, some thin. I laid them out in order that I figured we would use them. He looked them all over with great curiosity. Once he got used to seeing those, I chuckled and brought out the big dildos. The first one was a thick as a beer can and about 8 inches long. The other was 11 inches long but a regular thickness. "If you can take this one, you can take your boyfriend." I grinned as I wiggled it at him. His eyes were like saucers as he stared at it. What he probably didn't realize was that I really wasn't kidding. It was only two inches shorter than his boyfriend.
"I always like to start with rimming because it's totally hot, but I've rimmed you a couple of times, so we'll skip that. Next is to use a finger or two depending on the guy. Always use lube as spit can dry up to fast. Once you know your partner, you'll know what he can handle, but to start, use lube. Water base is fine, but if you plan on going for a while, use silicone as it doesn't dry as quickly, although it's a bitch to wash off. I'm going to use silicone as it feels better, especially for your first time." They sure don't have sex education like THIS in school. It's more about Part A goes into slot B. They sure as hell don't talk about oral or anal. Is that Part C and Slot D?
"Hold out your finger and I'll give you some lube that you can out in your ass." He gave me the finger. Forefinger. I put some on it and he rubbed his finger and thumb together. "Wow, this really is slippery." He said admiring it before he fingered some into his hole.
"Get on your hands and knees and I'll add a bit more." Kyle quickly bounced into position and turned his head to watch. I poured more down his ass crack and told him to work it into himself. I almost shot a load when I watch his finger go into his hole. Thank god I was still wearing my shirt and shorts.
"First trick when someone touches your hole is just to relax. Instinct is to tighten up to prevent entry. Maybe it's your body's way of protecting itself, but eventually you'll rewire your brain and tell it to chill out and let things in." I put my finger at his hole and he quickly clamped it shut. "See that's what I'm talking about. You felt my finger and your ass pucker tightened. Now, take a deep breath and relax as if you were going to take a shit." So graphic, yet so necessary!
He took a breath and I felt his ass ease up a bit. I added more pressure and he tightened again. I laughed. "If you want my finger in there, you have to stop clamping shut, dude." He relaxed again. I put my other hand on his ass cheek and rubbed it to take a bit of his attention off my finger. I pushed in a little harder and when he began to tighten a third time, I slapped his ass. He jumped, but his ass loosened and my finger went inside. "Just remember when you're doing this to someone, trim your nails as the ass is sensitive and you don't want to rip it with long cat like nails.
"How's that feel?" I asked as I slowly moved my finger back and forth.
"It hurts a little, but it's more weird than anything. Feels like I have to go to the bathroom." He told me as he moved forward a bit as if to get my finger out. I probed his ass a little and moved around in it. I felt for his prostate and once I detected the walnut size bump, I rubbed my finger over it.
"Hoooo." He said as he turned his head to see what I was doing.
"Guess I found your prostate." I informed him. "That is the part of your ass that you want stimulating. As we get going I'll show you more about that." I pulled my finger out and lubed up the baby dildo, which was only slightly larger than my finger, but was a lot smoother and I always thought it felt much better than a finger. I pressed it against his ass and he went to tighten up again, but I ignored it and pushed the dildo into him fairly quickly. He gasped and put his head on the pillow.
"You ok?" I asked just to be sure.
"Yep. Just trying to get used to it."
"Keep remembering; breathe and relax." I told him as I fucked him slowly with the little rubber dildo. I felt under him and his cock was rock hard. Of course with Kyle, the thing barely went down anyway, so this was no real surprise. The surprise would be if he was soft, then I'd know he wasn't enjoying it and we'd stop for sure.
"Okay, time for us to get a bit bigger." I got the 6 inch slim dildo ready and put it against his ass. This was probably a bit smaller than the average guy and a bit thinner, but I liked it because it started to open you up a bit without being uncomfortable. Kyle relaxed and took a loud deep breath, almost as if he wanted me to hear him do it. I pushed in and he readily accepted the insertion. I went all the way in and he groaned.
"Still ok?" I asked. To me it was important to ask too many times than not enough. He nodded and moved back towards me to try and get the dildo in a bit more. A nice move, so I fucked his hole while I rubbed his back with my other hand. He slowly moved back and forth with me as I did it. Kyle was definitely enjoying himself, but so far, we were nowhere near the size of Aaron, or even me.
"Before I move to the next size, I'm going to do a couple other things." I explained as I pulled the 6inch rubber toy out of him. The first is a butt plug, which you can insert into your ass and leave there for a while as it stays firmly in place. I always found it good to use when I knew I was going to get fucked as it made it easier. Once it goes in, your ass clamps around the narrow part to hold it in. The weird feeling is when you pull it out." I lubed up the short stubby butt plug first and pushed it into him. As his ass stretched to accommodate it, he tried to move away a bit and was breathing rapidly.
"Just relax. The widest part is the worst, but your ass should clamp shut, about... now" I said as I pushed it the rest of the way in. He jumped and reached behind him. I held his hand and rubbed his ass cheek. "Take a deep breath. It's only a second or two to get used to it." He calmed down.
"Howz it feel?" I asked.
"It hurt a bit going in when my ass closed, but now it feels ok." He said breathing normally again.
"So try this. Sit up on the edge of the bed and wiggle around on it." He carefully moved and it was cute to watch as he was being so careful. It looked like he had a pole inserted in him, the way he was moving. It was only three inches long, but it was thicker than the dildo. He sat gingerly on the edge of the bed with the towel under him. He wiggled around on the butt plug and his face showed the mix of pleasure and discomfort. His cock seemed to be enjoying the pleasure part. I got on my knees between his legs and grabbed his cock to stroke it a little. Kyle wiggled his cute little ass on the bed even more.
I jerked his cock hard for a few strokes then instantly released it. He gasped and then moaned. "Asshole."
"I'm guessing you like that butt plug then?"
"Yeah, it actually feels ok." He admitted.
"Ok, turn around and kneel beside the bed. I'm going to pull it out and put the bigger one in. This is a lot longer and a bit thicker. It might hurt as it goes in, but once your ass clamps around it, things should be better. This plug was about 5 inches, but at its widest point was thicker than an average cock. It might give him the idea of what it was going to be like when he was entered by his boyfriend. I used lots of lube and even fingered a bit more into his hole. "Deep breath and relax. If you feel pain just stay relaxed as it gets better quickly." He nodded.
I pushed the butt plug into his ass and for the first half he was ok, then he started to try and move against the bed to stop the forward movement. I pushed harder and he reached his hand around to stop me. I waited until I felt the grip on my wrist ease up. I pushed a bit further in and he tightened his grip slightly. "Just another little bit and it's in buddy. You want me to continue?"
"Yeah. It hurts but I want to take it. Just go slow, ok!" He said as he acknowledged me. There wasn't much further and I knew from my own experience with this plug that it would sting a bit as his ass clamped shut. I added the required pressure, and pushed past his ring to allow the ass to suck it in the rest of the way. I let go and watched it settle into position. Kyle groaned again and I waited as I rubbed his back and ass cheek.
"It's in. Just let your ass get used to it. Then when you're ready, try sitting down again." I told him. He waited a good 30 seconds before moving. He kept his legs apart and ass pushed out, as he lifted himself up and turned to sit down. This one he would definitely feel as he applied his body weight to it. As he slowly lowered himself, I grabbed his cock again to take his mind of what he was feeling for the first time. He sat down and paused.
"God that feels tight in there." He said. "I feel like I have to take a giant dump."
"Just stay like that until you feel like moving." I told him as I sucked the head of his dick into my mouth. By doing that, I was also applying a bit of pressure to his thighs, which would in turn push the plug further into his hole. I sucked him as he sat there getting used to having the dual feelings throughout his body. I stopped and cupped his balls, pulling on them to watch his cock bounce up and down. Kyle looked down at me smiling and wiggled his ass on the bed. He also used his hands to lift himself up and down to feel the pressure of the plug in him.
"So far, so good?" I asked.
"Yeah, it's actually ok. I kinda like the feeling in there. Just wish it didn't hurt so much going in."
"Well, if it makes you feel any better, a real dick isn't tapered like that, so doesn't really hurt as much. These are designed to stretch your hole. That's probably why they hurt just before they go all the way in. Wait till you feel it coming out. Get back on the bed on your hands and knees and I'll remove it." I told him. He turned carefully and got on the bed in position. His ass was way up in the air and his head lying flat on the pillow. I grabbed the base of the butt plug and told him to take a deep breath. I learned that taking these out is like ripping off a Band-Aid. Don't' go slow, just pull. You get a bit of pain, and then it's over fast. "Here we go." I told him and pulled the plug until I felt the pressure of his ring trying to hold it in. I pulled hard and the butt plug popped out.
"Ho, fuck!" gasped Kyle as his ass relaxed. "That was amazing." I guess he like the out motion, more than the in. I grinned to myself.
"Okay, the next thing is a bit of fun, before I put a much bigger dildo into you. This one is about the same size as the 6 inch dildo, so relax as it goes in. After lubing it up and sliding it easily into his hole, I paused.
"How did that feel?" I asked.
"That was so much better than the others. I kinda liked it." He told me. I grinned as I was about to give him a very bizarre sensation. I grabbed the controller at the end of the wire, and after debating it in my head for a second as to whether to go slow or hit him with the full experience, I pushed the switch to full and the dildo began to vibrate. Kyle almost shot off the bed as he hit his head on the top of the headboard.
"Whoa! What the hell?" he gasped as I laughed at him. The dildo was still vibrating but slowly sliding out of his ass. I grabbed it and held it in place as I pulled Kyle back into position.
"This is a vibrating dildo. I love this thing. You can sit on it, turn it on and jerk off. I often use it when no one else is around, and frankly if everyone died tomorrow I'd still be happy with just this." I moved the vibrating toy in and out of his ass. Kyle was squirming all over the place and I was thinking he might actually cum. On any other guy, I would have got on my back, slid under him and sucked his cock while fucking him with it so I could get his load. Today, we were on another mission; to open Kyle up enough to accept his boyfriend. A very tall order. Before he shot his load, I turned off the vibration and fucked him a few times with the dildo before taking it out.
"Okay, lie down and relax for a bit. We'll give you a second to cool down, before we go to the next level. He flopped onto his back, making sure to keep his lubed up ass on the towel.
"This is so fucking hot!" he said as he leaned up to kiss me. "Can I see what I've taken so far?" I showed him the toys that had been inside him and I think he was a bit disappointed that they weren't bigger. "That's all I took, huh?"
"Don't worry about it. As your ass gets used to it, the bigger ones actually don't feel as bad. The hard part is getting you opened up at first. You can take these to your room later to practice with." He kept looking at them and then grabbed the 11inch one.
"Can you take this one?" he asked. Now it was my turn to blush.
"It took a while, but yes, I can take the whole thing as long as I prepare myself properly and my ass is totally empty."
"Cool. Will you show me sometime?" He asked.
"Maybe." I grinned. "One thing at a time." I measured off 9 inches and showed him how much he needed to take if he was going to let Aaron all the way into him. That shut him up as he contemplated what he might be getting himself into.
"Don't worry, even if you can't take all of him, at least you'll be able to take some of him, which would be more than he's expecting." I said as I saw him frown with worry.
"Okay, let's try more." He said as he flipped onto his hands and knees again. I'll give him this, he's no quitter.
I lubed up the 8 inch dildo which was about the same thickness as my own cock; added more lube to Kyle's ass and pushed it slowly into him. He breathed rapidly and relaxed; nodding when I asked him if he as ok. He stopped me a couple of times but to my surprise he took the entire dildo rather easily.
"Looks like you're getting used to it." I told him. "That's 8 inches all the way into you. Your boyfriend will be thrilled with that, I'm sure. I slowly fucked the dildo in and out of his hole, making sure to add lube so that it could coat the entire inside of his ass. "That's probably enough for today. I think you've done amazing."
Without saying anything, Kyle reached for the large 11inch dildo and handed it back to me as he stayed in position.
"I dunno buddy. It took me a while to do this one. Maybe we should let your ass rest and try it another time." He wiggled it at me.
"I want to try it. Please. Just go slow." He begged. I really wasn't sure, but he could always say stop if it began to hurt. I pulled out the dildo that was in his ass and put it aside. For a first timer that was actually an impressive accomplishment. I reluctantly lubed up the long dildo making sure it was well coated.
"Are you absolutely sure? I asked one last time. He reached behind and positioned the dildo at his ass and began to insert it into himself. Well, I guess I had my answer. I slowly pushed it in and it went easily in for the first 6 inches or so. Then we began to slow down. He was breathing heavier and stopping me a number of times.
"Are we there yet?" he mumbled from his pillow. It looked like he was trying to eat it.
"You probably have about 9 inches in, so that's far enough to take Aaron. You did it buddy, you're officially able to handle your big dick boyfriend."
"Yay." He mumbled again. Then he held my hand tight and backed hard against me slamming the cock the rest of the way into his ass. I heard him yell into his pillow. Fuck. I hope he wasn't doing this to impress me, I was already well beyond impressed. He felt the dildo to make sure it was all the way in.
"Take it out please." He said from the depths of his pillow. I slowly removed it and once it popped out he collapsed onto the bed face down. "I did it." He panted as he looked at me. "I really did it."
"Yep! I'm proud of you buddy. I didn't think we'd get anywhere near this far on your first time. You might actually be a natural at it." I rubbed his back as he lay there sweating.
"I think you're ready. All you have to do is keep practicing. Take the dildos to your room and keep riding them. Try different positions and speeds so you can see what you like the most. Use the bidet in your bathroom too. It's the same principle as the dildo; lube it up, slide it in and turn on the warm water until you feel full enough. Any questions?"
"Just one. Now that I'm ready, would you fuck me for real?" he asked as he sat up to face me.
"You should save that for your boyfriend." I said reluctantly.
"Please Justin. I really want you to take my virginity. It would mean a lot to me for it to be you." He leaned in and kissed me. I was torn. I will remember my first time with Alex for the rest of my life, so I had to believe that Alex would remember his first fuck as well and it should be special.
"Kyle, it really is a moment in your life that you never forget. It should be with someone you love." I said as I put my hand on his knee.
"I do love you, and more importantly, I trust you. I really want it to be you. Aaron will be fun, and I won't tell him that he's not my first; but I want you to be my first more than anything else. Please." He said with such passion that there truly was no way to refuse him.
I leaned in and kissed him hard pushing my tongue into his mouth. I continued to move forward forcing him onto his back. I lay on him as we hugged and kissed for a while. He held my ass and squeezed my cheeks through the shorts. My cock was rock hard and must have felt it against his body. He pushed his hands inside the back of my underwear and lowered them until they were being cupped by the bottom of my globes. He squeezed my bare flesh a bit before he reached under and freed my cock, then pushed my underwear down so that I was completely exposed to him. I kicked them the rest of the way off. He quickly pulled my shirt off over my head so that I was as naked as he was.
"Please fuck me Justin." He begged again and turned so that I fell off him. He lay on his stomach presenting his ass for me. I licked down the length of his back and as I got to the top of his ass, I grabbed a towel and wiped the extra lube off before I opened his hole to rim him. If we were going to do this, I wanted him to experience everything the way it should be.
He was such a sponge for knowledge that I had no doubt he would be memorizing everything to use on Aaron. I licked and tongued his hole for a while and ran my hand under him to grope and stroke his cock and balls. He was leaking like a faucet and was so ready to be taken. I licked back up his body and pressed my cock along the crack of his ass, moving it up and down as I leaned in to kiss his neck and nipple on his ear. "Are you sure?" I asked cautiously just in case he changed his mind at the last minute.
"Yeah. Definitely." He gasped as my cock continued to tease his crack.
"Okay, remember what I told you. Just relax and breathe." I felt his cheeks go softer and his breathing increased. I wondered if this was how I sounded and felt on my first time. Aiming my cock at his hole, I guided it with my finger to make sure it was at the entrance. I slowly applied pressure and my cock began to enter his virgin hole. Kyle was seconds away from the pop of his cherry; about to give up what he could only give away once; and he had chosen to give it to me. I felt overwhelming emotion as my cock pushed past his outer ring and his hole gripped around my mushroom head. I waited to let him get used to it.
"You ok?" I asked. He nodded and kept still. I moved a bit further and his breathing increased. I paused again to let him adjust. Slowly and carefully I entered, each inch waiting for him to tell me to stop, but he never did.
"That's it buddy, you've got the whole thing inside you. You're no longer a virgin sweetie." I leaned down and kissed the side of his cheek. He turned to make sure I kissed his lips too. I fucked him slowly but with deep strokes to give him the full effect. "You have no idea how hot your ass is baby. It is an incredible feeling. Are you ok?" I asked again.
"Uh huh! This is WAY better than the dildos. Fuck me!" He begged.
I fucked gently and slowly for a little longer before pulling him into a kneeling position. He was now doggy style as I grabbed his hips. "This is a good position, because you can jerk off while being fucked. You ready to take it a bit harder?"
He nodded and reached for his cock. "Don't jerk yourself off yet. You'll probably come too soon and I want you to enjoy this longer." I picked up speed and fucked him harder and harder; my balls slapping against his. I moved one hand to his shoulder and held on tight as I kept slamming in and out of my young friend. He was doing way better than I had done my first time, that's for sure. "Okay tighten your ass around my cock and see if you can notice the difference in how it feels."
I should have been specific as he clamped his ass so tight I thought he was going to crush my cock. Damn this boy had amazing ass muscles. He could crack walnuts in there, and I may just let him as a party trick next time. I slapped his ass and he jumped in surprise which eased his grip on my cock. I pulled out and he groaned in disappointment, but I wasn't done yet.
"Turn over" I told him. He flipped over and I pushed his legs back to his head, pressing his knees flat on the bed, and put my cock back into him. I held his legs down and fucked. "This position is the one that allows the deepest penetration as you can feel. Plus you can jerk off, kiss and watch your partner. I prefer this one." I told him. I pushed as deep as I could into his hot tight hole and he gasped. He looked at me as if I'd electrocuted him. I smiled. "Told you this was the best position." Leaning forward I kissed him as I continued to fuck his beautiful ass. Kyle was a hottie and Aaron was definitely going to enjoy his birthday present. I decided that he'd probably had enough for his first time, so I got into a more upright position, pushed on the back on his legs at his knees and began to bounce on his ass. He got a hand to his cock and began to jerk himself off.
"You ready for my cum, baby?" He nodded and I fucked him as fast and deep as I could. I groaned and let him feel the warm jizz enter his ass for the first time. He sighed and I think that's truly when he realized he was no longer a virgin. I pulled out and decided to give him one more lesson after I wiped my cock dry on a towel. I lowered his legs and straddled him. I poured lube onto his cock and sat on him taking him deep inside me. He would get a chance to do it better on another day, but I wanted him to release himself into my ass too. I bounced up and down; my hands on his chest tweaking his nipples. I leaned forward to kiss him and he took over doing the fucking as if by instinct.
"I'm gonna cum!" he announced loudly. I pressed my lips hard against his and rammed my tongue as far into him as I could. He grunted and thrust upward as I felt his load splash into my hole. He seemed to cum forever before he finally breathed again and I got off him. I wiped his dick and looked at him. He had a tear running down the side of his face.
"Are you okay?" I asked concerned that maybe we'd done too much too fast.
He nodded and looked at me. "Thank you!" he whispered. I lay beside him and he hugged me tight. I felt special and wondered if I'd lost some of that emotion by fucking so many guys instead of making love to just a few, or one. We fell asleep in each other's arms. In the morning, Kyle decided to continue his training initiative and woke me up by riding my cock. It looks like he was going to be a bottom, at the very least. Something told me I'd opened up another can of worms. Lookout world, here cums Kyle!
(Author's note. I don't normally stop in the middle of a story, but I feel it's prudent to comment here. This is a fictional story designed to be erotic and not to debate barebacking vs. safe sex. I chose to write it this way for fun, but I always recommend using a condom, especially in a situation such as this, with a young guy doing it for the first time. Bareback only when you know your partner is safe; usually in a monogamous relationship with you. I thought it was important to mention it as I know some younger people may be reading this story. The adventure will continue with barebacking, but please use condoms when having sex with strangers or multiple partners. Here endeth the public service announcement...now onto Art gala!)
Now where was I? Right...the next chapter is coming soon. I look forward to your comments and suggestions for the story. outinwest@gmail.com or see what else the guys get up to at www.pridecanadabc.com and click on the stories link. Enjoy!