Tom's Nipples

By Neo

Published on Apr 22, 2024

Gay

Author's note:

This series is based loosely on my time going through middle school, high school and up until now. Mostly true, but somewhat enhanced.

Remember to always practice safe sex and never do anything that both you and your partner don't agree to.

If you are underage, please try to understand this is not a place to get educated. This is a place for educated adults.

Help Nifty continue to exist by sending a donation using the Nifty donations page at http://donate.nifty.org/donate.html.

Please e-mail your comments and thoughts to: neobiguy at myyahoo dot com.

I appreciate hearing from all of you and the thoughts, comments, and feedback are VERY much appreciated.

Thank you to those of you who have taken the time out of your day to write me about my story. - NEO


Part 34

Feeling much better about the situation between myself and Tom, and also knowing that things were ok between him and Ricky I lay awake in bed this morning trying to come up with a way to get the three of us together for some fun. In particular break in Ricky's boy pussy! I wasn't coming up with any good ideas and the clock was ticking so I hit the shower to get ready for school.

With the thoughts of the other day at Tom's fresh in my mind I blew a huge load on the shower wall just to bring myself back down to earth! I had been soo high ever since that rendezvous with Tom. A quick breakfast as I hurried out the door running slightly late, and there I was sitting in my first period class plotting. Thinking. Scheming. Nothing to do with the class mind you!

Between classes I caught up with Tom, "Hey we need to come up with an idea of how to get together with Ricky for initiating his butt. Ya got any ideas?"

"Is his birthday coming up soon?" Tom asked.

"Nope. Not until next year."

"hmm, well I'm sure you will come up with something. I gotta get to class now." he said and was off. Then suddenly he stopped and spun around calling me back, "Hey I got a thought. You know spring break is coming up in a couple weeks, maybe we can plan something then?"

"Yeah" I said, "Not sure what but that gives us a whole week to work with. I'll see ya later."


A few days went by with no real brain stormin ideas. I mean, how do you plan for something like this.... especially when it involves 3 people. It'd be different if it was just me and Ricky hookin up, but with it being three of us AND especially considering WHO the three guys were.

After no real luck one day I just decided to go over to Ricky's and hang out and see if something might pop into my head. Sometimes things just seem to come to me out of nowhere like that. So after school one day before his mom got home from work I went over to his house, letting myself in without as much as a knock even.

"HEY don't you ever knock dickhead?" yelled Ricky.

"Nope, not when I'm hopin to catch you jerkin off! hahahaha"

"Well as you can see I'm working on a school report, sorry to say."

"In your underwear...sexy ones no less?"

"All underwear look sexy on this bod!" he smugly leered at me.

I couldn't resist his sexy body any longer. It had been too long since we fooled around. I tore off my shirt and crawled on his bed, tossed his notebook aside and laid down on top of him.... chest to chest, crotch to crotch. "You know it's been a long time since we have just done this?" I reminisced.

"Yeah I know", he said humping his pelvis up and wiggling it around a little bit, "but there's more fun things to do that feel more intense."

"For sure, like sucking and fucking" I groaned as I really started grinding myself against the growing bulge in his briefs. "But how about we do this just once for old times sake?"

"Someone must really be horny" he said as he started to match my grinding motions. "You might want to take those pants off because clearly you are the one who is going to cum first, and I don't want to see you going home with a huge wet spot showing what we were up to."

"Ok you might be right.... this time" and I was up in a flash stripping off my pants but leaving my briefs on. I jumped back on top of him and ground my now hardening cock against his encased equally hard cock. I raised my torso up and looked down at his sexy muscular body. Damn he had really grown and the time in the weight room was obviously paying off.

I let out a small whimper of a moan and said, "You know how good this feels?" as I gazed at his muscular shoulders and how they tapered right into his big guns.

"Yeah it feels pretty awesome actually" and knowing the effect he was having on me he flexed his pecs making them do a little dance. "Bet Tom can't do that" he grinned.

"You should know as well as I do" I quickly replied glad to get the conversation involving Tom. "You know something though" I said, "with all that the three of us have done with not only each other but others as well, this is one thing that only you and I used to do all the time. And it still feels good, even as simple an act that it actually is."

With that being way stronger than myself he just grabbed me in a bear hug and rolled us over, now putting him on top. Then raising himself up on his hands while pushing his hard bulge into mine he says, "But it's even better when we're completely naked."

And with that he grabbed my briefs and yanked them down my thighs, where he got no resistance from me as I kicked them off completely with my feet. Then returning the favor I pulled his briefs off and that left us completely naked with our cocks hard and dueling to make each other cum first.

Usually when we would do this our cocks would be side by side pointing up on our lower abs, rubbing together, grinding out an orgasm. But this particular day I maneuvered mine pointing down between his legs so it was resting between his ass cheeks.

Tom slightly surprised says, "That's only going to make you cum sooner."

"I know, but it will feel good!" I laughed to keep it a light mood.

"Maybe you should try that on Tom. I think he might like it." Ricky said with a changing tone to his voice.

"I know. I heard all about it. Not only from you but from him also."

Ricky realizing what he just brought up tried changing the subject, "Yeah I was going to ask if you knew how he was handling the breakup with Erica and the news about Cole?"

"Well that's what led to me going over to his house the other day. I went to check on how Tom was doing and we got talking, seems he is resigned to the fact that Erica is gone and he is feeling like she wasn't really the one for him, and that he was just hung up on her sexy body. And he also admitted that Brandi was never anything more than a sexual outlet for him. Then his mom left to go shopping for awhile and well one thing led to another and we ended up sucking each other off. All in all I'd say he's doing alright and it has been at bit of an eye opener for him."

Ricky started to say "Well that's good to hear that he isn't falling into a deep depression over........ WAIT. DID YOU SAY WHAT I THINK YOU SAID?"

I said, "'All in all it looks like he is doing ok, and it has been a bit of an eye opener for him." and smirked big time. "What part didn't you understand?"

"Yeah yeah yeah I got all that, but what was the part about who sucked who off??? I think I misheard part of that."

"NO. YOU HEARD CORRECTLY!" I said beaming from ear to ear, as I started sliding my now rock-hard dick up and down Ricky's sweet sweaty muscular ass valley.

Ricky looking confused told me, "Stop sliding that cock of yours up and down my ass crack it's confusing me on what you are saying. Did you just tell me that you BOTH sucked EACH OTHER off?"

Not listening to his request, I actually continued by increasing the pressure against his puckered hole and really started humping his muscular glutes.

Ricky was getting worked up now, "Are you going to answer me or not?"

The more I humped his ass valley, even though I was doing this with him lying on top of me, chest to chest and our faces where nose to nose, my motion was really increasing the stroking his cock was receiving from being sandwiched between our abs. And he was rock hard, leaking pre-cum like crazy and I could tell he was getting close. But he had lost concentration on our grinding jerk-off contest and was totally focused on what went on with Tom.

I had him right where I wanted him....again. Ricky is wicked strong and a crazy wild man especially when it comes to sexual adventures. But I have one advantage over everyone else that he encounters.... I know him too well. He was trying to carry on a conversation with me but all the grinding and humping along with the sexual talk about who did what to who had him completely out of control. I love it when this happens because he isn't stupid, and he knows me as well as I know him.... so he knows what is happening, but he can't stop it!!!

He asked again, "Are you going to answer me or not.... prickhead!"

I smirked back with our noses practically touching and politely smiled and said simply...... "Nope".

"You are such an ass sometimes!" Ricky half moaned and half yelled as I grabbed his ass cheeks with my hands increasing the friction his cock was feeling between our abs.

"You are such an ass all the time" I laughed back as I squeezed his bubble butt and started sliding his whole groin up and down all by my grip on his ass, causing his rock-hard cock to go into overload.

OHHH OHHH OHHH Ricky groaned NOOO YOU DON'T. NOOOOOOOOO I'M NOT GOING TO CUM. STOP IT RIGHT NOW.

I was relentless continuing to work on stroking his cock between us while massaging his ass crack tight against his hole with my cock.

OOOOO STOP. IT. PLEASE.

"You want me to stop? Why doesn't this feel good? I asked playing with his mind now.

NO. I MEAN YES..... IT FEELS GOOD. BUT NO DON'T STOP.

"Oh so you don't want me to stop?" I persisted.

YES. PLEEEEEEEZE DON'T STOP! I MEAN NO. STOP. DONT.... AAAAGGGHHHHH I HATE YOU!

I smiled at him and leaned my face toward his ear and whispered ever so sensually, "You are going to cum when I let you, and not a moment before."

"OH PLEEEEEEEEZE DON'T. STOP. NOW

Then I stuck my tongue deep into his ear and whispered as best I could with my tongue so far out of my mouth.... CUM RICKY CUM!!!!!

And then I slid my tongue out of his ear and bit down on it as I gave his cock an extra grind with my abs and hands on his ass.... it was all too much for him!

AAAAAAGGGGGGGGGGHHHHHHHHHHHHHHHHH DAMN YOU.

And his body went rigid and he let out his usual animalistic sound like a wild boar in the jungle grunting a wild deep groaning sound I suddenly felt his cock harden even more if that is possible and then it tried poking me in my stomach as it spasmed out the first of many shots of hot gooey teenage boy cum creating a slippery slime coating between our two hot teenage bodies.

With our abs pressed together so tightly it didn't have much room to go anywhere so the layer of white creamy jizz just got thicker and thicker with each blast that his cock shot out.

Seeing his facial expressions and feeling his breathing and his pulse and heart rate all going into overdrive and feeling his cock twitching and spasming against my lower abs just above my pelvic bone was all too much for me. Especially with my cock being encased by his tight ass valley which by now was very slick with warm sweat. My cum was just about to begin also.

I felt it starting deep in my balls, but I doubt that he felt that. But when the first blast was getting ready to fire and my cock lurched up tight against his ass I am SURE he felt that..... AND I'm sure he felt my hot volley of boybatter land on his back somewhere, I couldn't see where. It could have hit the hair on the back of his head for all I know. It felt like it had the force to hit his bedroom wall. That would be one of those errand blasts of white goo that never gets cleaned up because it's lost in the excitement!

Blast #2: Usually my heaviest shot, maybe not the farthest tho I raised my head to look for and eyed it landing in the middle of his back.

Blast #3: I lost sight of again but think it hit his tailbone and eventually as we finished slid down his ass crack because I felt it and the remaining shots slide down his crack and coat my cock along with his crack and hole.

The opportunity to work with that cum as lube and slide my still hard cock right up his ass was great!

MMMMMMMMMMM Boy would this be an ideal time to turn his ass hole into a boy pussy!!! BUT I promised Tom we were going to both be together when this happens. Plus Ricky still having a virgin butt needs to be stretched out and opened up properly. So as bad as I wanted to slid my cock right up in there this very moment..... I resisted.

And besides.... the cum I just had did feel pretty damn good! :)


We both lay there not saying anything as we caught our breath and calmed back down.

Ricky spoke first, "Damn I don't remember it ever feeling THAT good!" WHEW

"Yeah that was fairly hot I gotta say..... and by the way you lost! I outlasted you. Again. Hahhaahhaa"

Ricky rolled off top of me and we looked at our fronts both covered with his load smeared all over our torso from our pubes up to our chests. I licked some off of his rock-hard abs tracing each line with my tongue. He then realized my load that I shot all over his back just got soaked into his sheets when he rolled over.

"We got too much of a mess, this is going to require a rinse off in the shower and new sheets on my bed.... so we might as well lay here and enjoy it for a few minutes before getting up. Which is thee perfect time for you to tell me what you said about you and Tom sucking each other off."

I laughed, "Oh that. That is simple. I don't know why you were getting all worked up over that. Tom and I sucked each other's cocks. That's all."

Anything else? I was still messin' with him.

Ricky sat up, "Whoa whoa whoa..... not so fast mister. I want details. Don't lay there and act like it was a casual no big deal thing. I know you better. IF Tom sucked your dick.... or any dick for that matter it's big news! So spill your guts buddy."

I sighed, "Ok so here's the deal. I went over to see how he was holding up with the breakup with Erica. And once his mom left well one thing kind of led to another and I gave him a blowjob. And it was a killer blowjob if I do say so myself. I deepthroated him and then when he came I pulled back so I could taste it and let him shoot in my mouth. After licking up the little that got away from me, I said something to him about how good his cum tasted and he asked me if I was serious or was I just saying that to be nice.

I asked him if he had ever tasted his own cum and he seemed shocked at the idea, which I'm not sure I believe but anyway I shared some of his cum with him and he seemed to be alright with it.

Then he really shocked me. We were both standing there, naked in his room facing each other and I hadn't cum yet so he just out of nowhere reaches down and grabs ahold of my dick and starts strokin it. I was like WOW this is great... because up until that point he had never touch my dick before. I told him how great that felt and how I was surprised since he never did anything like this before. He just shrugged and said he felt that after all the times I did him without ever expecting anything in return it was the least he could do.

Then he says that we have a problem though because his mom was due home very soon. I freaked thinking my opportunity was going to escape me when he tells me "shhhh" and he drops to his knees and kisses the head of my cock!!! After he explained it was going to be his first time so don't expect too much as he started sucking on it. I was beside myself and assured him that being a guy he'd know what to do. That it would just come naturally too him. He did a pretty good job too for being the first time.

Ricky was amazed.... and speechless through out the entire story. "Did he let you cum in his mouth? Did he swallow? Tell me, I gotta know."

"Why is that soo important that you HAVE to know, I mean that is kind of personal information after all." I acted offended, still playing him.

"Ricky thought for a moment and said "I guess it's not that important and maybe none of my business, but.... we are all friends and friends share these kinds of details with one another. I mean look, both Tom and I told you about the fight and how that ended up."

I stared off in the distance, still playing him acting like he brought up a sore subject and didn't say anything.

Ricky sensing this says, "Look Neo I'm really sorry for taking Tom's cherry knowing how much of a crush you have on him. Like I said it just kind of happened. When I went over to confront Erica about Tom and Brandi I had no idea where it was going to go. It just happened and I am really sorry.

"Ricky, it's not a contest to see who does what to who first. It doesn't matter. What's important here is that the three of us are still friends despite all we've been through."

"Yes cool. I agree totally."

"And to answer your questions no I didn't cum in Tom's mouth because he was worried his mom was going to be home any moment and didn't want a messed up looking face. So I shot on his chest and licked it up, and this time I shared some of my cum with him to taste."

"Did he like it?"

"Of course! It was MY cum..... which happens to taste great! In fact he liked it soo much that he came a second time just after tasting it just from me rockin my ass against his still hard dick!"

Ricky lay there thinking about all that I had just said. I could see him staring out into space.... doing some deep soul searching.

Finally he spoke, "Ya know what I think... I think Tom is coming to the realization that he might be gay, or at the very least bi."

I looked at Ricky and nodded saying, "You know what I think, all three of us are coming to the same realization about ourselves."

< silence.... very tense silence >

As I said that to Ricky my eyes were glued to him for his reaction.

I needed to know if he was at the point that he was willing to admit that to me, his closest friend... or was he still keeping it inside his head. Would he be willing to share his feelings not only with me, but also Tom. I mean he had fucked Tom after all, but it was under the guise of being in a fight that got out of hand.

This was a BIG moment.

The air was very tense. (and it was also heavy with the smell of teen boy cum that we just shot all over each other.... no homo. Yeah right)

< still.... more tense silence >

FINALLY Ricky looked at me and said, "Yeah I think you're right."

YES! I screamed, but only inside my head, while using restraint I didn't realize I even had. This was a HUGE moment in our lives!

I reached down and scooped a little more of his cum off my stomach and told him to roll partially on his side.

"Why?" he wanted to know.

"Just do it" and quit always being so difficult.

He rolled his eyes and rolled part way on his side and I scooped up some of my cum off his back.

"Ok you can lay back down."

"What on earth are you doing now?" he asked perplexed.

"This is my cum that I shot on you showing him my one hand. And this hand has your cum that you shot on me." Then I took both globs and mixed them together and told him, "We are going to make a pact, sealed with a mix of both our cum." Give me one of your fingers. And as he did I put a dollop of our cum mixed together on his finger and kept the remaining dollop on my finger.

"Here's to our friendship, a special bond that will last as long as we both shall live. We can fight, argue, disagree, or call each other names. We can also be nice to each other every now and then if we feel like it. BUT NO MATTER WHAT, WE WILL ALWAYS.... ALWAYS, BE BEST BUDS! This pact is sealed with this special mixture of our cum. May it never be broken."

Now do as I do. I put my finger in his mouth. He followed my lead and put his finger in my mouth, and we sucked each other's cum covered finger clean. Then I leaned in and gave him a kiss. It was just a small delicate simple kiss on the lips, but it was intense as it sealed a life-long friendship.

We need a shower now! We both agreed and headed off to shower.... together. Of course ; )


After changing the sheets on his bed and feeling fresh out of the shower we sat down and I told him I had something to share with him.

"What's up now?" he asked.

"Well when I went to see Tom and check in on how he was with the breakup between him and Erica we got talking and realized something."

"What's that?"

"Here's what I realized. I have had a guy fuck my ass. Tom has had a guy fuck him in the ass. You have fucked a guy's ass, however......"

"So what are you saying?" a somewhat unsure Ricky asked.

"What I'm saying is you need to get your ass fucked!"

"Oh I'm not so sure about that!" Ricky exclaimed without hesitation.

"Now hold on and listen to me." sounding like the strict authoritarian. "Think about it. You've fucked a number of people in the ass including Tom, myself and Erica." Did any of us seem to be in real pain when you did that? Yes it hurts a little the first time, especially at the beginning but if you prepare for it by warming up with fingers or toys and lube, stretching the opening properly it isn't that bad. And after you get used to it things actually feel pretty good. I'm sure you remember the time I fingered your butt hole to make you cum. Remember how awesome that cum was? That's because my finger was massaging your prostate gland. Just imagine how much greater that feeling is with something larger like a cock. I'm telling you..... you're missing out! Seriously."

Ricky thought awhile before answering by saying, "I'll give it some thought."

"Well here's the deal. We've decided for you already."

"huh"???? a speechless Ricky was at a loss for words.

Tom and I talked about it and decided that you need to get fucked properly, and it should be with one of us since we are your best friends."

"Ohh, so just like that it's been decided?"

"Yep"

"Sometimes I can't believe you!" a surprised, but not angry Ricky said. The fact that he showed no anger told me we were ok. "And just exactly which one of you is going to do the deed..... that is 'IF' I agreed to this absurd idea of yours"?

"That's the cool part! We don't know!"

"You're not making any sense!"

"Oh yes I am. We don't know, and you won't know either." That's part of what makes this so special! Think about it. How often does someone get to have one of their first sexual experiences be so special?"

Ricky still seemed confused.... but interested, which was promising. "I don't get how this is going to work?"

"Like this..... Both Tom and myself will come over. We'll both be showered, clean and ready... but we won't know who is going to be the lucky one until we get here and draw straws. You meanwhile will be blindfolded so you won't know which one of us it is. Simple."

"How did you dream up this idea, because it has 'Neo' written all over it. Tom wouldn't dream up an idea like this."

"Doesn't matter, what's important is it's super exciting.... for all of us really!"

Rick finally showed signs of going along with the idea when he said, "I do have to agree it does sound kind of exciting. But there's a few issues that concern me."

"Like what"? I asked. "I'm sure minor details can be worked out."

"If I'm blindfolded how am I sure you aren't pulling a trick on me, like bringing over that little twerp friend of yours?"

"You mean Ollie?"

"Yeah him. Or Tom's young cousin Alex?"

"Ok so first of all Ollie is NOT a little twerp, and yes he is a friend so I'd appreciate if you would stop calling him that. He's just kind of a quiet different kind of person that's all. I actually like the guy. And secondly because he is sort of a guy who sticks to himself pretty much, I don't see him into this kind of thing even if we did ask him. But I haven't even seen or talked to him, or Alex for that matter in a long time. But to assure you we could do this at your house when your mom is gone, and you can lock your bedroom door with some type of noisy trap that you would hear if it opened."

"Ok I suppose I could always just pull the blindfold off and peak too." he smiled at his ingenuity.

"Nope! Not gonna happen. You're gonna have two choices. We either tie your hands to the bedposts which will not only prevent you from taking the blindfold off it also will keep you from touching the person with you because you could tell right away if it was Tom or me. The other option would be to tie your hands behind your back if you're worried we're going to run off and leave you tied to the bed. We might also get some heavy black cardboard and cover your one bedroom window and seal under the door so you room is pitch black."

"I don't know about this." Ricky was getting skeptical again.

"Look Ricky thing about it logically, Tom and I are in on this as much as you. None of the three of us have come out as gay. Do you think either of us would want ANYONE knowing about this? I mean really WE would get more razzing than you ever would.

"If I agree to this I want a safe word. If I say the safe word you have to stop AND remove the blindfold and untie me IMMEDIATELY.... otherwise, I'm reporting it.

"Absolutely. That's how they always say to do it in any of the websites I've read about this kind of stuff."

"And also we were thinking the other person would stay in the room to insure the 'lucky person' doesn't get too carried away." I added.

"I'm not crazy about an audience" mumbled Ricky, "but at the same time I might be willing to go along with that. I trust you, but Tom I haven't known as long or as well as you .... and he might be thinking payback for what happened after our fight."

"I get not wanting an audience, but it'd be your two best buds whom you've both had sex with already." I assured him it wouldn't be so much like an audience as just the three of us hangin' out having a good time.

"Alright I will think it over and let you know in a couple days. In the meantime NOBODY else ever gets word of this. If they do before it happens the whole thing is off."

"Ok deal."

End part 34

to be continued....

A few notes from the Author: No cliff hanger here! As I told Ricky it's already been decided because I know him and his taste for the exciting, erotic, and unusual sexual exploits. It's too tempting for him to pass up. Especially when it involves his lifelong best buddy who he trusts with his life. And while he doesn't know Tom as well, he knows him well enough to know he has probably the sexiest body in our school that a guy could possibly hope for to take his virgin ass and make it a proper boy pussy.

....but we'll give Ricky until the next chapter to decide so that he thinks he has some say in the matter. ;)

While I'm at it, a BIG thanks to all of the readers who take the time to email me a note of encouragement, appreciation or compliments/criticism letting me know how I'm doing. It's my first story and your responses are my only gauge to go by. I can not emphasize enough how meaningful and important this is to me.

Allow me to recommend you check out the new beta version (trial version) that Nifty is working on. http:// new.nifty [dot] org

Improving the site with some cool improvements.

You can click 'Favorite' at the top of any story page, which makes it easier for you to find the new chapters when they come out.

You can also 'Follow Author' on any story page by following the link with the authors name, located under the story title.

If you feel so inclined, please consider rating my story by clicking on the stars at the bottom of any chapter. 5 stars would be nice ;))

Until next chapter.... Happy reading! Neo

Next: Chapter 35


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