You Pass This Way But Once

By: B W
(© 2013 by the author)

The author retains all rights. No reproductions are allowed without the author's consent. Comments are appreciated at...

Chapter 8
The Next Level. 

Before we knew it, we were entrenched in our school routine again and back to football practices.  Football had gotten off to a great start, because not only did we have a strong team, but Seth and I had also made some good friends at the same time.  We were now hanging out with Jeff, the starting quarterback who had caught us with erections in the shower the previous year, as well as Keith, our third linebacker, and two seventh graders, Tom and Robbie, who had just joined the squad.  The six of us were becoming very close and started spending most of our time together.

The football season was going great and the team was already 4-0.  Jeff, Seth and I were really clicking together on offense and the coach had even set up some pass plays for us to run.  We were just coming into the fifth game of the season and were really psyched, because this was the game against the team we were playing when I broke my leg last year.  They hadn’t really done anything wrong or illegal, but we really wanted to beat them anyway. 

We started out with a straight tailback dive, with Seth following me through the hole, and the next play was a cross buck, where Seth followed me into the hole, but Robbie got the handoff going the other way.  Most of the defense followed us, since we were usually the ones carrying the football, so Robbie was able to rip off a sizeable gain.  On the next play, Jeff faked the handoff to Robbie, who was following me, before he threw the ball back to Seth on a delayed screen pass to the weak side.  Seth went into the end zone, untouched, for the score.

We held them on defense after they got the ball, although they did rack up a couple of first downs, but they ended up punting to us.  When they did, Seth had a big return and I got to level the first guy who came downfield trying to tackle Seth.  Now that we had the ball, the coach called the next play and I got the handoff on a straight dive right, while Jeff and Seth carried out a fake option left.  We followed that up with the same play, except this time Jeff faked the handoff to me and then he and Seth carried out the option. 

Since we just had made back-to-back first downs, we now had the defense looking for the run.  Therefore, on next play, Seth followed me on a fake slant off left tackle, while Jeff made a pass downfield to Robbie, who had slipped past his defender.  He scored and it was all down hill from there.  Having only won by a touchdown the previous year, this time we slaughtered them.

The six of us went out to celebrate after the game, since our parents agreed to take us to the local burger joint to eat and then out for ice cream afterward.  From there, they took us over to the arcade for a while, before we finally split up and went home.  It was a great deal of fun, especially since we were with our friends and able to celebrate the big win our own way.

That weekend, we all stayed over at Tom’s house on Friday night and Saturday.  This meant that Seth and I had to not only forego our special time together, but we’d also have to watch that we didn’t make any slip ups in front of the other boys.  Even though this was a considerable sacrifice on our part, we looked forward to spending time with our other friends.  On Friday night, Tom’s parents ordered pizza for us when we got there and then they took us to watch the high school team play.  When we got back afterward, we played some video games before we turned in.  We all slept on the floor in their living room, but Seth and I slept apart from each other, so we didn’t accidentally try to cuddle during the evening.

Saturday morning, we had a rough football practice, so after that we decided to go over to swim at the local YMCA pool.  To our dismay, the lifeguards on duty lacked a sense of humor and yelled at us several times for horsing around.  Eventually, they kicked us out for the rest of the afternoon, because we wouldn’t stop having a good time.  We were all disappointed by our early exit, but decided to go over to the arcade next and kill some more of the afternoon there, before we headed back to Tom’s house.  We played some more video games once we returned to Tom’s house and then we collected our things and got ready to go home.  Seth stayed at my house Saturday night, which gave us a chance to enjoy each other for a little while longer.

That evening, we had dinner with my parents, and of course they pumped us for details about the big sleepover the night before.  After we told them all about it, except we omitted the fact that we’d been kicked out of the pool, they offered to let all of the boys stay at our house any weekend we chose.  Seth said he was going to see if his parents would do the same thing, so it looked as if we were going to be doing this all over again.  After dinner, we sat down with my parents and played Yahtzee, Rack-O and Phase 10, before Seth and I turned in for the evening.  We had a few other games planned for just the two of us.

While Seth went to my room, I made a trip to the toilet, brushed my teeth and retrieved an item we were going to need later.  As soon as I finished, I went back to my room and Seth hurried over to the bathroom to do his thing next.  When he returned a couple minutes later, I had everything ready.  I had a bunch of tunes keyed up on my iTunes, which I thought would help drown out any of the other noises we might make while we were doing this.  Then, we both undressed and moved toward the bed, because we had already decided that we were going to give anal sex a try.  We had spent quite a bit of time reading up on it and thought we were ready to see what it was like.

I grabbed Seth and pulled him to me, so our mouths could come together and our tongues unite.  We remained in this embrace for many minutes, while we enjoyed the love that freely flowed between us and savored the taste of each other once again.  When we had satisfied or oral desires, I grabbed the bottle of baby oil I’d brought in with me from the bathroom and squirted some of it into my hand before I reached the bottle out to Seth.  I rubbed the oil around in my hands and then rubbed my hands over Seth’s penis to prepare it for its next endeavor.  Once he was ready, I hopped onto the bed, lying on my stomach, and spread my legs wide.  This was so Seth could prepare me for what was to come.

Seth took the baby oil and poured some of it over my hole, and then he started to spread the oil around the outside first, before he let his first finger press against my rosy pucker and force its way inside.  I tried to relax as his finger entered my passage and then he began to twist it around and manipulated it in and out.  After doing this for a short time, he added more oil to his hand and then inserted two fingers. 

I gasped as they entered me, because a slight twinge of pain shot through my rectum, but it lasted only momentarily before it subsided.  Seth had stopped when he noticed me react, but now I urged him to continue his actions.  When he did, he started twisting his fingers around, in order to widen my hole for his penetration.  He also slid his fingers in and out of my tunnel of love repeatedly, as he lubricated the entire area.  At last, I was ready.

Eagerly I raised my butt up, so it was slightly off the bed, as Seth slid between my legs.  He moved forward, aimed his erect penis at my willing rosebud and placed the tip firmly against its target.  I forced myself to relax and push down slightly, as he began to apply enough pressure to slip inside.  The head of his cock eventually slid past the muscular ring that guarded my secret place and then the rest of his dick soon followed.  Except for that one small instance of pain, I felt nothing but fullness when Seth entered my passageway. 

Once he had given me time to adjust to his penis being in me, Seth began a slow, steady rhythm, as he plowed his boyhood in and out of my chute.  I was feeling nothing but pleasure now, as Seth’s dick kept brushing against something deep within my interior and sent bolts of electricity shooting throughout my entire being.  My mind was suddenly flooded by these awesome sensations and caused me to see colors and lights in my mind.

Seth was receiving his own enjoyment from doing this, while I was continually reveling in the pleasure I was receiving.  He was so engrossed in the feeling of his cock being enveloped by my warm, satiny lining that at first he didn’t notice I was also using my anal muscles to clamp down on his stiff meat.  The friction was incredible, as he repeatedly rocked back and forth in my intestinal tract, and this activity provided him with a new high, as his juices began to boil in his loins and then bubbled over in overwhelming pleasure.  At this point, the churning in his lower abdomen signaled his release and his cum exploded up the slender tubes inside his penis and washed deeply within the lining of my bowels. 

Shot after shot of his boy cream flooded into my hole and allowed me to feel the warmth of the love that he was depositing there.  When his ejaculation finally subsided, he collapsed on top of me, totally spent.  A couple of minutes later, he rolled off of my back and let gravity pull his deflating sausage from my well-used hole.  Then, he lay beside me recounting every second of that wonderful ride, while my hole was still tingling from what we’d just done.  I threw my arm across his chest, kissed him on the cheek and then remained motionless beside him.

“That was freaking incredible,” Seth croaked out, once he’d recovered.  “I never believed it would be that good.”

“Yeah, it was pretty awesome,” I agreed.  “You were wonderful, so are you sure you haven’t been practicing with someone else?”

“There IS no one else,” he shot back.  “There’s only you and me, now and forever.”

“And what about Timmy?” I asked.

“Oh, we can help him out too, but it’s still really only you and me as partners,” he insisted. 

I merely nodded in agreement, because I’d known this all along.  I just wanted to hear him say it.

Once he was ready, we traded places and it was my turn to get Seth ready.  He quickly lubed up my stiff pole and then I spread the oil on my hands to grease up his hole, inside and out.  I worked him with one finger first, then two and finally three.  I knew I would have to spread him a little wider than he had done to me, because my penis was slightly thicker than his, since I’d grown more than he had over the past few months. 

Seth took the digital preparation like a pro and never complained about any discomfort or pain, not even a little.  Now that I had him loosened up, I moved into position behind his firm bubble butt and prepared to mount him.  I pressed my stiff piece of meat against the exterior of his tunnel of love and the muscle soon gave way, which allowed me to enter the land of enchantment.  It was a wonderful feeling, as his warm, moist intestines caressed my intruder and sent me into the ‘Promised Land.’

I began to pump in and out of his sweet boy ass and reveled in its tightness, as well as the pleasure it was giving to my probing tool.  The pressure of his lining against my raging hard-on was causing all sorts of wonderful feelings, which were beginning to radiate outward from my groin.  These intense sensations began to overload my senses with pure pleasure, because it was like slipping your hand in and out of a very warm, tight glove on a cold winter day. 

He must have learned from what I did to him, because he was using his anal muscles to squeeze the lining of my woody too.  As this feeling grew, I began to pump into him faster and faster and could feel my release growing ever closer, until my boy juices could not be contained any longer.  Those precious fluids shot from my dickhead and flooded his intestines with a super-sized load of spunk, which totally drained me.  As the last of my load oozed out of my wand and drained into his chute, my body quivered one final time from the ultimate pleasure and I rolled off of Seth’s back.  My cock ‘plopped’ from his hole and I lie beside him on the bed.

“Fucking A!” was all I could think of, as my mind began to clear and my voice returned.

“Yeah, I think that’s what you did,” Seth responded.  “You fucked my a alright.” 

It took a second for his comment to register in my foggy brain and then I joined him in a little chuckle.

“You were right, Seth, and that was absolutely fantastic,” I told him.  “I knew it would be good, but that was totally incredible.”

Seth agreed and we continue to lie there a while longer before we cleaned up, put our briefs back on and then cuddled up with each other.  We spent quite a few minutes just enjoying the closeness and reliving what we’d just done, before we went to sleep.  It was even more wonderful tonight, because Seth spooned back into me and his cloth-covered butt cheeks surrounded my dick again, but this time my penis knew how great it was to be nestled there. 

The next morning it was kind of hard for us to hide how truly wonderful we both felt, so I think my parents began to suspect what we might have done the previous evening.  They didn’t get mad or say anything, but I had a feeling my father might want to have one of his private chats with me again, sometime in the very near future. 

The football season came to an end just before Halloween and we finished the season 7-1.  We lost our next to last game when we failed to convert a point after touchdown, but although this left us disappointed, we were not totally disheartened.  We’d had a great season and were pleased with our accomplishments, so we held our heads high and looked forward to the next year.  This meant that Jeff, Seth and I would be moving up to the junior varsity team, while Tom and Robbie still had another year playing modified. 

Soon after the football season ended, Seth, Keith, Tom and I were all going to start wrestling, while Jeff and Robbie tried out for their respective basketball teams.  We all made our various squads, but we still planned on hanging out together too.  Even though our practices, matches and games would now be at different times, we hoped to continue spending one to three weekends together each month, as we had done ever since school started. 

We were now heading into the Thanksgiving holiday, so Seth and I got in touch with Timmy again.  We had spoken to him by phone, texted each other and exchanged emails several times by this point, so we were all pretty familiar with what was going on.  His parents had even agreed to let him spend a few days with us between Christmas and New Year’s, but they had also invited Seth and I to stay at their house during spring break, which was in April.  Fortunately, it worked out that both of our school districts had scheduled spring vacation for the same week, so we were looking forward to being together then too.

On the Friday night and Saturday after Thanksgiving, the six of us spent time at my house.  We watched some DVDs, played video games and enjoyed some football games on TV.  We also played a three-on-three touch football game of our own and then we all slept together down in our family room, after devouring all of the snacks my mom had bought for us.

The period after Thanksgiving went by in a blur, so it seemed like no time at all before Christmas vacation was upon us.  We told our friends about Timmy’s upcoming visit, including the fact that Timmy was about the same age as Tom and Robbie.  We also told them that it might be possible for us to still hang out together during part of the time Timmy was here, except on the weekend.  We thought we should use that opportunity to entertain Timmy privately, while also spending time with our families.  Our friends said they understood and everything was cool, so after celebrating Christmas day with our families, Timmy caught the bus and came to visit.  He left his home the day after Christmas and we picked him up that same evening at the bus station. 

The three of us were going to spend the first night together at my house, the second night at Seth’s place and the following night we were staying with all of the other guys at Robbie’s house.  Timmy approved of our plans, as long as we agreed that we’d be able to spend some private time together too.  We were pretty sure we knew what he had in mind, because we were looking forward to the same things, and we got to enjoy our first time alone that evening at my house.

We had a big family dinner with my mom and dad, two brothers and little sister first, but the three of us were more than cool with doing this.  My mom and dad immediately fell in love with Timmy, seeing he was on his best behavior.  He was extremely polite and totally charming the entire evening and my two little brothers thought Timmy was great.  They wanted him to spend the night in their room, but Timmy thanked them and explained that the three of us had a lot of talking and catching up to do, because he wanted to know what we’d been doing since we saw each other last summer.  My parents intervened and nicely herded my brothers away from us, and even though we had some catching up to do, I didn’t think there would be much talking involved.  We did watch a couple of sitcoms with my family first, before we excused ourselves and went up to my room for the rest of the night.

Timmy was eager to tell us about Ray, even though he had filled us in on some of this during our previous conversations and emails.  He said Ray hadn’t bothered him at all, and in fact Ray had stepped in to protect him when another boy had started to give him crap.  That boy then complained to Ray that he was just doing what Ray had taught him, but Ray countered that he had been wrong about Timmy and he wasn’t a bad guy after all.  Ray told the other boy he’d found this out when they were together at summer camp, but we all knew that wasn’t exactly what Ray had learned at camp.  As long as it helped Timmy though, we weren’t going to contradict him. 

After talking about this some more, we concluded he was most likely scared that we’d come and tell his friends about the locker incident, if he didn’t protect Timmy himself.  Timmy said after that had happened, some of his old friends told him they wanted to make up and start over, but he wasn’t sure if he was ready to forgive them.  He admitted to us that he hadn’t yet made up his mind if he still wanted any of those fair-weather friends back, because he was afraid they’d do the same thing again later. 

After hearing what he had to say, we told him he’d probably be better off without them, as long as he still had other friends to hang out with.  That’s when he informed us that he didn’t really have any other friends, so we suggested he might want to take them up on their offer and use them while he could, similar to how they had used him, as long as he made sure to take the proper precautions.  That’s because we all agreed with Timmy that they’d most likely all desert him again, if they discovered he was really gay, so we just wanted him to be careful. 

After that discussion ended, Timmy wanted to know if Seth and I had tried anything new since we were last together and this caused Seth and I to quickly glance at each other before we answered him.  It wasn’t that we didn’t want to admit what we’d done, but we were unsure if we wanted to let Timmy know about it, because we figured he’d want to try it too.  The problem was we weren’t sure if he was physically ready for that yet.  Just seeing how we were reacting, he could tell we weren’t being totally open with him and said so.

“What are you guys hiding from me?” he pressed.  “I thought we were friends and were honest with each other.”

“We are friends, Timmy, but we just aren’t sure that you’re ready to take the next step,” I told him honestly.

“Why?  You guys think I’m just some little kid, don’t you?” he countered, angrily. 

“No Timmy, that’s not that,” I explained.  “It just that Seth’s body and mine have gotten bigger and this was hard enough for us to do, because we had to accommodate each other.  We just didn’t want to end up hurting you.”

“Don’t you think I can make my own decision about that?” he asked, very bluntly.  “I don’t need you guys to protect me any longer, although I do appreciate everything that you’ve both done for me in the past.  Please just tell me what it is that you’ve been doing and then let me decide whether or not I want to try it.”

“Ok.  You’re right and we should let you decide for yourself,” I relented.  “We were just thinking of you, but we know you’re capable of making your own decisions.  Like I said before, we just didn’t want to hurt you, so we’re sorry we didn’t let you make the choice.  We’ll tell you what we’ve been up to, but we’ll even show you if you want, and then you can tell us what you want to do.”

Seth then proceeded to tell Timmy about our experience with anal intercourse and Timmy immediately announced that he wanted to try it.  We both knew he would, because that was why we had been reluctant to tell him, so this didn’t come as much of a surprise.  We knew we would probably have to spend a lot of time preparing him first though, before we could allow him to do it.  I also suggested that we should let Seth do him first, since his weapon wasn’t quite as large or thick as mine, so Timmy should be able to handle it easier.  He could then take his turn doing me afterward, if he wanted to try that as well. 

Once these issues had been settled, Timmy gave both of us huge, sloppy, open-mouth kisses to thank us for agreeing to this, before we had him lie on the bed for Seth to prepare him for entry.  Timmy got on his stomach and pushed his cute little butt into the air and I spread his ass cheeks, so Seth could lube up his opening.  Tenderly, Seth plied the baby oil to the exterior surface first, before he placed his index finger against Timmy’s pink, little pucker.  Seth then applied more and more pressure, until his finger slipped past the sphincter and this caused Timmy to gasp.  When we asked if he was all right, he told us he was, but he was just surprised when it happened.  He then urged us to keep going. 

“Breathe deeply and push down with your butt muscles, like you’re trying to push out a stubborn turd,” I told him, just to make this easier for him.  “That will open your butthole more, so you can accommodate what Seth is doing.”

Timmy did as I told him and Seth’s finger slipped entirely into his channel.  Seth started to wiggle it around and Timmy began to squirm in pleasure, as Seth’s digit brushed his boy prostate.  Seth then finger fucked him for a brief time, before he removed his finger and then coated two of them with more oil.  This time, he inserted both digits into the opening, and felt Timmy’s butt tighten around them.  When Seth asked if he was ok, Timmy admitted that he had experienced a small bolt of pain shooting from his tight hole, but urged Seth to keep going. 

After seeing Timmy’s reaction, Seth waited for a few seconds, before he started to apply his two-finger massage to open Timmy’s rectum further.  Just to be safe, Seth pulled his fingers out and oiled them again, before he reinserted them.  After slipping the twin digits in and out for a while, he pulled them out one more time, squirted some more oil on three of them, and then he used those fingers to open Timmy’s butt up even more.  It was immediately clear that this was just about more than Timmy could handle, but Seth and I both knew we had to do this, especially if Timmy still wanted Seth to fuck him.  Timmy was brave though and handled the discomfort very well, so now we felt he was ready to accept Seth’s intruder.

Seth crawled up behind Timmy and asked if he was sure he still wanted to do this, and after receiving Timmy’s positive reply, he placed his hard dong against Timmy’s pucker.  Slowly, he began to apply enough pressure so that the head of his dick was able to pass through the guardian of the sacred tunnel.  Timmy let out a little yelp as Seth entered him, but then quickly indicated he was fine and Seth could continue. 

Steadily, Seth pushed forward and moved, delicately, into the tight, virgin chute until his pubes were tickling Timmy’s ass cheeks.  At this point, he gave Timmy a few moments to adjust to the invader, before he began pumping in and out of Timmy’s hole.  This immediately sent waves of ecstasy radiating thru them both, because Timmy was so tight that his channel gripped Seth’s cock like a fist, but it also cause Seth’s penis to brush against Timmy’s prostate.  Since Timmy was so tight, it also brought Seth to an early climax and Seth was drowning Timmy’s cavity with his love juices long before he wanted to.  Once the last of his seed had flowed into Timmy’s rectum, they both crumpled on the bed, while relishing the rapture they had just endured.

I waited for the two of them to recover from their lovemaking, before I asked Timmy if he wanted to keep going.  As I expected from our sex-starved pre-teen, Timmy wanted to do that and more.  Since he was eager, I grabbed Timmy and pulled him on top of me, so our bare chests were rubbing against one another, while I kissed his mouth deeply and covered the remainder of his face with butterfly kisses. 

While we were doing that, Seth was busy preparing me for Timmy’s love making, although we knew it wouldn’t take much prep for Timmy’s smaller penis to enter me.  Even though he had grown quite a bit since we’d last seen him and even added a few scattered hairs to the base of his cock, he was still smaller than Seth, whom I could handle easily.  As soon as I was ready, I quickly oiled up Timmy’s pole, as Seth instructed him about what he was going to do next. 

Timmy knelt behind me, as I lay chest-down on the bed, and lined his joystick up with my boy-hole.  He entered me completely, with just one good push, and once he was inside, I tightened my ass muscles as much as I could, to give him as much pleasure as possible.  Timmy was so excited that he began humping me machine-gun style and banged my rump faster than any rabbit.  We thought he might hyperventilate before he completed the task, but he continued long enough to get his reward. 

After just a couple of minutes, Timmy drove into me as far as he could go and stayed there momentarily, as his body shuddered with his release.  I couldn’t tell if there were any secretions from his lovemaking, although I was positive he’d enjoyed an orgasm.  While Timmy was savoring the results of his labors, Seth gave me a blowjob to relieve my unmet needs.  After that, Timmy slept and cuddled between us, as he took turns squeezing and caressing us both.

To be continued...

Posted: 06/07/13