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
Finally Ricky caught his breath from his most intense cum ever that didn't even involve me sucking his cock, or him fucking anything. No it came just from him jerking off his own dick, in his own bed..... but with some help from me fingering his asshole which was well on it's way to becoming a boy pussy whether he realized it or not.
It felt just way too good for him not to be back for round two. He shot cum 3 feet above his head splattering it on his bedroom wall with such force we could hear it hit with a loud "SPLAT". Twice too before the rest of his load landed in his hair, face, chest, abs, my face, hands, his cock and balls..... he was covered!
And he looked sexy as fuck too!!!
But now it was time to shower and clean up before his mom got home.
"Alright you made this mess happen, so now you're going to clean it up" Ricky said with a smile... "unless you don't want to?"
"Ok let's hit the shower" as I started to get up out of his bed.
"No no no, not so fast buddy!" Ricky grabbed my arm and said, "You were insistent that you liked the taste of my cum so before we hit the shower you're going to lick most of the big globs off with your tongue!"
So I took advantage of the opportunity to tongue bathe my hot wrestler buddy's body. I started with the cum in his sparce pubes and was thankful they were thin and few, not a thick bush, thus making the job easier and more enjoyable. Then I licked the little bit off his balls and cock before heading north to his abs. He laughed when I cleaned out his belly button. It wasn't long before I was up to his well-defined pectoral muscles which I traced the very defined edges all the way around, even if there was no cum there. I also licked and sucked his nubbins even though they didn't have any cum on them either. Most of it was on his face, hair.... well and the wall but I was going to just let the streaks on the wall dry as a reminder of what took place that day.
It was kind of erotic to lick his face. He was growing facial hair yet so his face was nice and smooth. When I got to the cum that shot across his lips I paused for a second and looked at him as if to say "Is this ok?". He didn't flinch. Didn't give me a glare, or a smirk, or a "Don't you dare look"....nothing. Just a blank stone cold look that knowing him as well as I do meant "Let's see what he does here?"
So I went for it. I licked the cum off his upper lip first, and then before swallowing that I came back for a second swipe of my tongue across his lower lip. And as I did that I sort of sucked his lower lip into my mouth, not far but just enough to know I did it... and he knew it also.
"Are you trying to kiss me?" a surprised Ricky asked.
"Who ME? Haa of course not!"
"Why do I have trouble believing you?" laughed a doubting Ricky.
I smacked him playfully and jumped up and said, "Come on let's hit the shower."
Naked the two of us headed into his shower, with me leading the way this time and it was Ricky who remarked "Nice ass buddy, I might like me a piece of that."
"You wish" I said kind of caught off guard by his remark. Things had become sort of one-sided with me doing everything to him, so a remark like that coming from him caught me by surprise. Was he serious or just being the typical smart-ass Ricky?
He turned the water on to get it nice and warm and we both got in what is a very small stand-up shower stall, square shaped and really intended for one person. Hence no matter how or where we stood we were up against each other.
Ricky stood under the spray of warm water first and as soon as his skin turned silky smooth and wet my dick started to chub up. He looks soo sexy with wet skin!
Grabbing the bottle of body wash I poured a generous amount over his shoulders and back and started massaging his skin with the lathered up water. It made him so smooth and slippery it was pure joy rubbing my hands over his skin. When I got down to his ass cheeks I gave them extra attention and eventually my soapy fingers found their way back to the puckered opening to his most private of places. I slid one finger in and wiggled it around before Ricky ask me what I thought I was doing. I noticed he waited awhile before asking me that though!
"Just making sure you're nice and clean back there. No extra charge!" I said laughing.
Still standing behind him I poured more bbody wash over his chest and began a most enjoyable washing, or massaging of his chest, arms and abs. All the while I was doing that I tightened up the space between his backside and the front of my body.
Basically I was hugging him. Naked body against naked body!
And, or course my dick that was 3/4 hard by now, had found it's way nestled in between his butt cheeks enjoying the slippery valley.
After washing his abs my hands slipped down to his dick, which was quite hard by now. I started stroking it with the soapy suds of the body wash and as I did that he started this little back and forth with his hips. This was causing my rapidly hardening dick to enjoy the back and forth, up and down motion similar to fucking.
I was getting turned on quickly. And it was easy for Ricky to tell because I was standing behind him holding him tightly, and the more excited I got the tighter I gripped his upper torso. Once I grabbed ahold of his pecs and squeezed them like you would a girls tits I wasn't about to let go. Plus if that wasn't clue enough, my mouth was right on the side of his neck by his ear where my heavy breathing couldn't be overlooked! And of course my hard dick sliding up against his asshole was a good clue too. LOL
Ohhhhhhhhhhhhh mmmmmmmmmmmm "This feels SOOOOOOOOOOOOO good I moaned! I don't know if I can stop!"
Ricky thinking that I was getting close to cumming said, "Go for it! Just let it happen!"
"You sure?" I asked thinking that he meant to go ahead and slide my dick inside him.
"Yeah" Ricky replied saying, "If it feels good just go with it and let it happen. I'm fine with it."
Well with all the fingering I did of his hole with the suds from the body wash, plus him being opened up (somewhat anyway) from our episode on the bed before getting in the shower, combined with how slippery my dick was from the body wash it didn't take much.....
I leaned back and aligned my now rock hard cock with his slippery grasping hole and pushed, gently, and slid into his ass!!!
WOW did that ever feel good!!!!!!!!!!!!!! "HOLY FUCK DOES THAT FEEL GREAT!!!!!!" MMMMMMMMMMMMMMMMMMM DAMN!!!!
however.....
Turns out that Ricky meant if it felt good rubbing my hard-on between his soapy butt cheeks, and that feeling was going to make me cum to just go ahead and let it happen. Meaning like cum between his legs and let it just wash down the shower drain..... NOT ENTER HIS ASSHOLE.
"WHAT THE FUCK DO YOU THINK YOU'RE DOING???" yelled Ricky, as he quickly moved forward pulling me out of him in a lightning quick move.
"You said if it felt good to go ahead and do it, so I thought you meant......"
"MEANT WHAT? ......THAT YOU COULD FUCK MY ASS???" NO I WAS SAYING YOU COULD CUM BETWEEN MY LEGS..... DUMB ASS!!!!"
silence
"Oh" was all I could think to say at that moment. "Sorry"
silence
"Did it hurt at all?" I finally asked.
"No not like I thought it would. I guess all the soap suds and warm water helped make it feel not so painful. More weird than anything, but you really caught me by surprise!"
"I'm really sorry, I just misunderstood what you were saying."
"Well numbnuts first thing you gotta do is wash your dick again. It's been in my asshole, even if you did clean it real good earlier."
I did and then he shut off the water and we got out of the shower and dried off. We both wrapped towels around ourselves and went back into his room and sat on the edge of his bed.
"You don't know much about butt sex do you?" Ricky asked me.
Embarrassed I meekly answered, "Well no I've never done it before."
"Well I've fucked ass before, but never been on the receiving end of it." Ricky replied, but you need to learn a few things before you go trying that again.
"What do you mean? What'd I do that was soo bad?"
"It's like this, body wash makes suds that make your outer skin nice and slippery, but it doesn't do such a great job inside the body."
"Oh..... opps."
"Yeah opps is right! For butt sex you want to use lube, or if you don't have any on hand some type of oil like coconut oil, or Vaseline, or even saliva."
With that Ricky got up and went over to his closet and dug down into a corner in his hiding spot and brought out a bottle of sexual lube. I'd heard of it before but never actually used it. The closest to that I ever used was saliva or lotion when I would jerk off.
Walking back over to his bed he said, "Stand up and lay your towel out on the bed and lay face down on it."
"What are you going to do?"
"Simple, show you how to properly use lube."
"Ok, but I want to know how did you learn about this?"
Ricky paused for a moment trying to decided if he wanted to answer my question. "Well ok, but you gotta keep this to yourself. Promise?"
"Ok I promise!"
"Well so Erica is not on birth control and doesn't like using condoms."
"WHAT??? With all the sleeping around that slut does she is asking to get pregnant!"
"Exactly!"
"I don't get it?" what's her deal I asked???
Simple, but you GOTTA keep this to yourself or she'll cut me off."
"What do you mean "She'll cut you off?"..... Cut you off from what???" I was so confused.
"Ok so Erica and me have been having sex for quite some time now, but NOBODY is supposed to know."
I interrupted saying that I've suspected that for a long time.
"Yeah, but what you SUSPECT and what everybody KNOWS are two very different things!"
"Ok so go on" I said.
"So if she doesn't want you as her baby's father she won't have intercourse, you know, real pussy sex. She will suck you off, or jerk you off, or grind you into cumming in your pants...... but no entering the pussy! So that's what we did for a long time. Finally after me reading up on ass fucking I convinced her to try it, and she was hesitant at first but after awhile got used to it and that's what we've been doing ever since."
"Ahhhh.....and so that's why she always is leaving Tom high and dry?" I asked.
"Sort of" Ricky went on to explain further. "Erica has the hots for Tom. She wants to have his baby. So she won't have ANY sex with him UNLESS it's condom free in her pussy. No blow jobs, no hand jobs, no nothing unless it involves his cum in her pussy."
"Wow" was all I could say. "Just Wow."
"And he hasn't figured this out yet. He thinks she's just a scared little virgin. HAA.... little does he know!"
Again.... "Wow was all I could think to say."
Ricky went on, "I know you and Tom have become close friends, and while it's none of my business I wouldn't be surprised if you told me that the both of you fool around like me and you do. And that's fine, I don't care. Tom actually seems like a cool dude, and has a nice bod... for a guy. I can see why she is after him, or why you like him for that matter also. BUT.... I don't care HOW close you are, dude you GOTTA keep quiet about this."
I said "OK" to Ricky, but right away I started thinking of how I can "clue Tom in" without actually telling him. I can't just sit back and let her trap him into her evil web, saddling him for 18 years by tricking him into getting her pregnant. I also told Ricky that Tom suspects that him and Erica have been fooling around, and that's why he doesn't care for him."
Anyway while I was digesting all that info, Ricky changed the subject back to butt sex.
"Spread your legs." came the command from Ricky.
To me it sounded like he was taking control again, so I said "Only if you say 'please' and ask nicely."
"BITCH.... SPREAD YOUR LEGS NICELY! PLEASE!" OK? geeesh
"Ok but don't be gettin all bossy like with me, you know I don't like it."
"Look, I'm doing you a favor by showing you stuff. Don't be getting all difficult with me. I'll ask you like you asked me before, 'Do you trust me?' or do you think I'm going to hurt you, my best friend forever?"
"Ok Ok..... I trust you." I said as I spread my legs open for Ricky.
"Good. Now remember when you fingered my butt with saliva and pre-cum? Well we're going to do the same thing now only using proper anal lube. And you're going to love the difference!"
And with that Ricky pour a bunch of cool lube down the crack of my ass cheeks and massaged it around with his fingers.
I wasn't sure how I felt about it at first. I mean on the one hand I was content to be the person doing things to other hot guys with nothing in return. I'd go home and re-live the experience and jerk off to it and have explosive orgasms. But on the other hand I had been complaining that things had become very one-sided, and so here was my best friend offering to do.... whatever he was going to do. So I figured what the hell...
Ricky had obviously been doing this with Erica because he was very smooth, and assured of what he was doing. He rubbed his finger up along my ass crack without actually entering it. Just massaging it, kind of teasing it. Back and forth he went. Then with each pass he put a little more pressure on the opening as he passed over it with his fingers.
It was clearly having the desired effect on me, as I was getting more and more worked up with each pass of his fingers. Finally one finger dug down and entered it's way into my opening. He wiggled it there a second before pulling it back out leaving me to whimper slightly. Then on the next pass he push it in further and left it there, wiggling it around a bit.
With that I was squirming on his bed, turning red in the face and my breathing was becoming ragged. I was getting so turned on I was out of control.
"You like how that feels?" Ricky asked?
Uh huh...............mmmmmmmmmmmmmmmmm
"Would you like me to put a second finger in?"
Delirious I could only mumble "Uh huh".
So Ricky added a second finger. "Your ass seems to be loosing up fairly well. Have you ever been fucked in the ass before?" he asked.
"NO! NEVER! Why would you think that?"
"Just because once you become accustomed to anal sex your anal muscles to stretch open easier as they become accustomed to it."
Embarrassed I said that I have had numerous toys back there in the past, and that was probably why.
"And when you fucked yourself with these fake dicks did you enjoy it?" he asked.
I was hesitant to admit to that so I mumbled something incoherent.
Ricky persisted, "Did you enjoy the feeling of having something penetrating your ass?
"Yeah it felt alright I guess."
"Would you like to know what it feels like to have a real live cock fuck you?
silence
Ricky persisted again, "I asked you a simple question, would you like to know what it feels like to have a real cock fuck you?"
"Will you promise me to be careful?
"Yes I will promise to be careful, but I gotta be honest and tell you it probably will hurt at first. But once you get used to it the pain subsides and it starts to feel good. But you're going to have to trust me on that."
"If I tell you to stop will you?" I asked.
Ricky paused and looked at me for a minute. "Honestly? ....... No. You gotta understand there is a point at which there is no turning back. You either want to do this, or you don't. Which is it going to be?"
I thought about it and was soo turned on by that point with all the fingering he had done on my hole I said "What the hell, go for it."
Ricky smiled and said, "This is going to be soo great! You're going to love it!"
He instructed me to turn over and lay on my back saying he wanted to see my expression when he took my virginity. I struggled with hearing it put in those terms. But he said that's exactly what's about to happen.
So I rolled over on my back, and then he raised my knees up and got between my legs and aligned his rockhard cock with my hole. It looked like it was already set to blast a load of cum and he hadn't even started yet. I'm not sure if I was more excited or nervous about what was just about to happen.
Sensing that he paused and looked down at me and said, "We don't have to do this..... if you don't want to you know."
"I know."
"Are you sure?"
"Yes I'm sure.... Fuck me please!"
He pushed his cock head up against the opening to my ass and paused there holding the pressure he was pushing with steady.
"You realize that once we do this you no longer will have an asshole, it will become a boy pussy by the time I am done with it."
"umm.... yeah I know."
"And you realize there is no going back. Once you lose your virginity, it's gone and never coming back. And once I transform your ass into a boy pussy you're going to have a boy pussy the rest of your life."
"Yes, I know."
He pushed a little harder, causing me to let out a moan.
"And you need to understand that once we do this you are going to cum like you've never cum before, and you will never want to go back to regular sex or jerking off. You will always be seeking me out to fuck your newfound pussy. You understand this?"
"YES YES YES..... GOD DAMN IT QUIT TALKING AND FUCK ME ALREADY!!!"
And with that he slowly but steadily pushed his plum shaped cock head into my opening, past the muscles keeping my ass closed, until the flared edge of the crown of his big cockhead popped into my ass....... now my boy pussy!
It was bigger than any toys I had previously tried and so the pain was more intense than I was expecting. But Ricky knew to stay still and let me adapt to the feeling before doing anything else.
I lay there and couldn't believe it. I was about to be fully impaled on my best friends big cock. AND I was agreeing to it!
After a few minutes he asked "Are you alright?"
"I think so yeah, it's just bigger than I thought it would be."
And then he pushed, or nudged it just a little bit not really going in any further but just applying more pressure.
Again he asked, "Are you still alright?"
"Yeah. Go ahead and slide it all the way in..... just please go slow."
"First let me put a pillow under your ass to align you better and here put your legs up over my shoulders." In this position I was quite vulnerable, but I could see where I was lined up perfectly for Ricky to sink his big cock deep down into my insides.
By this point I was soo ready..... there was no going back now.
And with one slow smooth long stroke he slid his entire cock all the way into my depths until I felt his sparce pubes rubbing up against me.
FUCK ME..... NOW!!!..... PLEASE!!!
End part 21
to be continued....