The Trailhead: Discovery

"Listen I didn't tell you earlier because I didn't want to ruin things but there's a meeting at work I've got to be at tomorrow so I'll be gone for a good part of the day. I really should go to bed now."

And that's just what he did.

I eventually cried myself to sleep on the couch.

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I woke up with a hangover, a text message from Dee, and a dawning realization of how badly I had fucked up last night.

-Hey grl! How was last nite? Yr hunk have any hot kinks? ;) -

Ugh. I dropped my phone back on the coffee table and got up to use the bathroom and look for Russ. I never found him but there was a note on our fridge-mounted whiteboard that said "Home by five -R" I went back and collected my phone before heading to the toilet. It was 10:50 in the morning, I had slept for more than eight hours but I still felt like shit and it wasn't the wine's fault... mostly.

While peeing I debated what to text Dee, finally just opting for simple and direct since my head was still spinning and anything more was too much work.

-Pegging- I Sent. A few moments later a reply:

-OMG!!!-

My heart dropped again. Oh. My. God. If even Dee was shocked by this it couldn't be good. An irrational fear that maybe it was worse than I thought, that maybe Russ was gay or something popped into my head unbidden. A minute passed while a rush of horrible thoughts filled my head one after the other too fast to count.

-That's so awesome!!! :D - Then:

-We've got so much to talk about!!!-

I was slammed sideways by an entirely new wave of horrible emotions. Russ wasn't a freak, I was just a stuck-up judgemental bitch who humiliated him after he opened up to me at my prompting. I broke out sobbing uncontrollably.

After a few minutes my hands stopped shaking enough for me to text her back -Don't get yr hopes up. I fcked up bad-

A few minutes later: -J wants to know if u can meet us at the cafe 4 lunch?-

Then: -Our treat-

I broke out in fresh tears but told her I'd see them in an hour.

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When I got to the Cafe, Dee and Jay were already there, seated at an outdoor table under the awning and well away from everyone else. Three steaming cups of coffee sat on the table in front of them. Jay noticed me first and bumped Dee's shoulder, she looked up and waved enthusiastically at me. "Got you a coffee," she yelled when I got close enough, "Don't know how you take it though" She said with a smirk on her cute face.

"Black, like my mood," I said as I dropped into the chair opposite them.

"Oh babe, I told you it might be a bit rough, but what happened?"

I proceeded to tell them about the conversation last night, how well it had gone at first, and how my reaction at Russ's confession had totally ruined things. They listened to me with compassionate attention, looking concerned but not surprised at what I had to say. This was the first time I'd seen Jay without sunglasses and was surprised to see his eyes were green-grey and totally mesmerizing.

"Mmmhmm, tried to warn you. I made the exact same mistake and tried to save you the trouble but I guess everybody's got to learn the stove's hot in their own time" Dee said, shaking her head slowly for dramatic effect.

"Boy did you ever," Jay chimed in.

"Wha... What happened to you guys?" I asked.

"When Jay finally decided to open up to me about wanting to cum on me, cum, in my mouth, all that stuff, it really shocked me. He made a joke about making me a cocktail, emphasis on the cock, and I... I blurted out that I'd rather die than drink a glass of his cum."

"What! No!" I exclaimed, horrified.

"Oh yeah she did," Jay said. "Totally floored me. I was so embarrassed."

"I knew I screwed up the moment the words came out of my mouth," Dee said in a low voice, her eyes downcast. It was the first time I had seen her less than cheerful. "And what's worse is that it wasn't even true! I had already given him a million blowjobs by that point, I always swallowed, I was a good girl!"

Upon hearing the phrase "good girl" I was again rocked with a wave of unidentified emotions. Russ had said last night he thought that I was a "good girl", but now maybe wasn't sure. I wanted to be good for him. I wanted to please him, I just wanted to please myself too. Did that make me a bad girl?

Dee continued, "I must have already swallowed gallons of his cum, another glass wouldn't have killed me, but for some stupid reason those words came out of my mouth." She sighed heavily. "Damn I still hate myself for that." Jay reached over and rubbed Dee's shoulders and neck with one hand while the other clasped her hand on the table.

"So how'd you recover?" I asked.

Dee laughed, "an immediate, sincere, and heartfelt apology. Continued conversation, and other things," Dee mimed jacking a cock off in front of her face while she said the last bit with a smile and a wink.

"We talked honestly about both my desires and her reactions to them, about how we could come together." Jay added.

"Literally!" Dee shouted with a laugh. We all broke down laughing after a moment.

"OK, how am I going to recover?" I asked, my voice quavering.

"Well," Jay said, "First off you've got to accept that there's nothing at all wrong with Russ or his fantasies."

"I Do!" I practically yelled, "I just had no idea he was into anything painful or humiliating like that." Jay and Dee turned to each other quickly and then shared a questioning look at me. I briefly described the porn videos I had seen.

"Hon, those were FemDom pegging videos, Female Domination. And not that there's anything wrong with it as long as it's between consenting adults with a safe word, but you should know it's not necessarily what Russ had in mind." Dee said gently.

"I love getting pegged, but I'm not remotely into that, either in porn or real life," Jay said, totally carefree. "But then again we're not really into Domination and Submission stuff at all really. We've got a blindfold and some wrist restraints, but we really never use them. Russ might be the same way."

I was shocked that Jay just told me he loved getting pegged. On the hike last week he had seemed so... so masculine, so in control even when he was orally pleasuring Dee that it seemed like she was his sex-puppet. I couldn't imagine the same person would submit, would be the passive, receiving partner in any way.

My look must have shown because they both broke out laughing. "Oh girl," Dee said between laughs, "You really are wound a little tight about this!"

Jay said, "When she pegs me, it's with the same kind of love and passion as when I fuck her," he smiled at Dee as he talked. "Normally I take the lead in the bedroom, but it's nice to take a break and see things more from your partner's perspective, and it honestly makes you a better lover."

"And it's hot as fuck." Dee said deadpan.

"That too," Jay responded. "Some of the most intense orgasms I've ever had were when she was pegging me."

"No no babe, it's hot as fuck for me," Dee said earnestly. "I don't care about your orgasms, I just want to get off fucking your hot, tight ass." She reached down and must have pinched his ass because he jumped in his seat as she broke out laughing. "Of course I care about your orgasms. I care about his orgasms." directing the last to me.

Jay glanced at his watch. "Listen, I've got to run, but you've got this right?" He asked Dee, she nodded back. "All under control Babe."

"Good luck! Have fun you two!" Jay said with a smile as he walked away from the table with the bill for the coffees in his hand.

"He's helping a friend move a couch, good news for us cause now we can be totally uninhibited!" Dee said with a wicked smile as she got up from her chair and grabbed my hand, "Come on, we're going shopping!"

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Intellectually, I knew stores like this existed, but I had no idea there was one so close by. Or that it would be as nice as it was.

"You've got the afternoon off right?" Dee asked me. "I can spend all day in here." She said as she waved to the cashier, a cute black girl around our age.

I nodded as I looked around in wonder. There were aisles and aisles of toys, books, clothing and DVD's, not that I had a DVD player mind you. "Yup, we're going to have fun here." Dee said as she saw me gawking. "Let's grab a cart, shall we?"

As we toured the store we talked more about pegging and what it meant to Dee and Jay. "It doesn't mean he's gay, not one bit." Dee said authoritatively. "The prostate is like a guys' version of a g-spot, so having it fucked hard with a big toy attached to a hot woman can be a turn-on to the straightest of straight guys. However," Dee looked over at me seriously, "It might mean he's into more than having a piece of silicone pushed up his butt."

"So... what, like Bi or something?" I asked, feeling so out of my depth.

"Sure, maybe." Dee said, looking over a rack of lingerie. "It's not some sort of binary or trinary thing. Gay, Straight, Bi, they're all just points on a compass with a million tiny degrees between them. For instance, I know Jay isn't gay," She gave me a knowing glance. "And I'm pretty sure he's not Bi..."

"Wait! You're not sure?" I asked incredulously. "I thought you two talked about everything!"

She chuckled. "Safer to say I don't think Jay thinks he's Bi, but he's never tried it so who knows? What I do know, and what he'll freely admit to you is that he's really turned on by dicks, and cum." Dee steered us down an aisle full of dildos as if for visual effect. "Does that make him Bi? I don't know. The way he explains it is that he's not attracted to traditionally masculine features, hard bodies, body hair and the like. But he has had a lot of fun playing with the only dick he's ever touched -his own- and that he might like playing with someone else's given the opportunity." She shrugged, "Honestly I think he'd rather suck a guy's dick than kiss him on the mouth."

I was left speechless by all this. Dee continued, "So just be aware that Russ could be anywhere on a spectrum of a lot of different possible kinks, you know one tiny piece of information, so don't be surprised is all."

"What else might he be into?"

Dee laughed, "No way for me to know, like those videos you saw he might be into humiliation or degradation, if he grew up in a conservative household it wouldn't be unheard of." She probably saw the look on my face because she hurried to add "But probably not. Like Jay he could just have a thing for role-swapping, ass-play, and phalluses." She laughed. "Given how quick Russ came on your face he might have a thing for that too, or like Jay, a general thing for cum."

"What's that about?" I asked, trying to keep my voice level so Dee wouldn't see that I was practically boiling with excitement at this point. I was under total overload of the senses, the racks and racks of sex toys around me, Dee's open sexual commentary, my own pent-up needs combined to a heady mix that threatened to overwhelm me.

Dee shrugged, "Stuff of life and all that, symbol of their masculine vitality, maybe they just like squirting their fluids over everything. All I know is that Jay's got a thing for cum. Cumming on me, cumming in me, having me play with his cum or lick it up after the fact, feeding him his cum..."

"What!" I interrupted.

"Sure. Not that weird at all, look it up on Pornhub."

"How?" I asked stupidly.

"Oh lots of ways, I can have him cum in my hand or mouth then I spit it into his mouth," she said with a wicked grin, "that's called Snowballing. But my favorite way is to have him cum in me when I'm riding him then as soon as he's shot his load deep in me I clench tight and swing around into a 69 or just slide up and sit on his face while he eats his cum out of my sloppy pussy."

I tripped. Full on, fell-on-my-face-tripped in the dildo aisle of the adult-toy store. Dee was bent double laughing at me and the clerk ran over to see if I was all right. I waved her off as Dee struggled to help me to my feet while also not falling over laughing. I was redder in the face than I've ever been but otherwise unharmed.

"My god girl, you're like looking at me through a time machine from three years ago! Wound up tight as can be!" Dee laughed and finished pulling me to my feet. Let's get you kitted out so you can work out your kinks and blow your boyfriend's mind."

Dee got me two bottles of lube, a three pack of curiously shaped buttplugs of ascending size "These ones are angled to hit his prostate, and have a T-handle that sits between the butcheeks and is comfy all day, trust me these are the ones you want." She said confidently. And last but not least she brought us over to the aisle that had the strap-ons. "You can get one of the basic ones that sits on your pubes and just holds a dildo," she said pointing to some harnesses. "But if you really want to enjoy it then this is the style to get." She pointed to several dildos that were vaguely L-shaped, 3-5 inches long on their short sides and 7-10 inches on their long sides. Their girth, color, and texture varied but the general idea was clear, the shorter end was meant for my pussy while the longer end would jut out like it was my cock.

"They're called strapless, but truth be told, unless you've got pussy muscles of steel, you're going to need a special type of harness to help you keep it in." She added one of these in my size to the cart and told me to pick the cock that appealed to me. I settled on a blue and purple swirled one that was about the same size as Russ, with a defined head but no attempt to make it look realistic at all. "Good choice, he's gonna love it!"

We finished our tour through the store while Dee gave me advice on how to use the new toys. "Start with a well-lubed finger, no such thing as 'too much lube' then put in the small plug. After a few minutes or a few hours go up to the next size and so on. If it hurts, go slower and use more lube or just stop for the day and pick it up later. You can use the strap on as a role-play item if he seems interested, you can have him suck on it like he's giving you a blowjob for instance." We got up to the cashier and Dee told her to put it on her account before exclaiming that she forgot one thing and running off into the store. A few moments later she returned with another pack of buttplugs, these ones also had a T-handle but were cone shaped, not angled like the other set.

"Almost forgot. These are for your ass!"

-----------

When Russ got home from work I was ready and waiting for him. I met him by the front door and fell into a quiet embrace with him without ever saying a word. I rested my head on his chest and whispered "I'm sorry."

"It's OK."

"No, it really isn't, but I'm going to make it up to you."

"You don't have to."

"But I'm going anyway." I held a finger up to his lips to silence any further protests and pulled him by the hand towards the bathroom. I let the bathrobe fall from my shoulders as we went, revealing nothing underneath. Russ kicked off his shoes and loosened his tie as we walked.

I love the shower in our apartment, more than big enough to fit the both of us, with a flexible showerhead and decent water pressure, it's one of my happy places. I finish stripping Russ once I've got the hot water running and pull him inside with me. This is all totally normal, we take showers together all the time. I go through the ritual of soaping up his lean body, and if I spend a moment longer on his anus than I normally would, it's not enough to call me on. He rinses and then performs the ritual on me and he certainly takes an extra moment to wash my holes. I suppress a shudder of pleasure and push him away with a playful grin on my face so that I can rinse off. I quickly turn off the water and pull him, still trying to towel off, into the bedroom. All this is normal, next he goes down on me.

Only this time I change the script and I push him forward ahead of me and guide him so that he's on the bed on his hands and knees facing away from me, but because there's a well positioned full length mirror in front of him I can see his face perfectly, and he can look back and see me perfectly too.

So he gets a good look as I gently rub his wet ass cheeks with my hands, pulling them apart slightly so I can get a look at him, all of him.

God how have I been with this man for three years and never seen his asshole? I take all of my boyfriend in. His tight, muscular legs leading into powerful, compact buttocks. His slim crack with a tiny dusting of his pale and fine body hair. His perfect, pink little star of an asshole, looking just as delicate as any porn star's. His heavy balls hanging just below, full and swollen looking. His long cock was mostly hidden from my view because it was so erect that it was almost pressed flat into Russ's belly, but I could see the long drip of precum hanging down and pooling on the bed sheets. I looked up over his muscular back and sandy hair to meet his eyes in the mirror.

Once I had his gaze locked in mine I slowly bent down and put my face between his cheeks. Still looking straight into his blue eyes I reached out with my tongue to gently probe his puckered butthole. It tasted clean, like our brand of soap, with a slight metallic tinge underneath, but not unpleasant. What was totally pleasant was watching Russ's eyes practically roll back in his head with pleasure. It was the exact same look of sheer abandon that I had seen on Dee's face as Jay did this to her. I continued to lick in small, gentile circles around his ass.

With my hands I gently pried his buttcheeks apart as far as I could and buried my face in his ass and licked with wild abandon. I felt Russ shake and quiver under my touch. When I reached under with one hand to smear his precum around the head of his cock he practically collapsed forward onto the bed. I had to grab him around the thigh with my other arm and keep him up and pressed against my mouth.

When I pulled back for a moment to catch my breath I noticed how his ballsack had contracted, now pulling his balls tight up the base of his cock, looking impossibly swollen and full, no way he could take much more than this. And just like that a new idea popped into my head. It was risky, pushing things further than I had planned to tonight. I was tempted to take it slow, go easy, and be careful. But I had done that for years and it had left me crushed. Everything good that had happened in the last few days had been because I had taken risks.

I turned Russ over and pushed him back onto the bed. "I need you in me now Baby!"

"Ungh, I'm really close Babe, I'm not going to last long." He said as I straddled him.

"Don't care. Need your cum in me." I breathed into his ear as I sank my sopping wet but incredibly tight pussy down onto his twitching cock. The moment my lips pressed into the base of his long shaft he grunted and pulled me down onto him even harder as his cock convulsed and sent jet after jet of hot cum into me.

After a moment he relaxed slightly and looked at me sheepishly and said "Sorry Babe, I guess you didn't have time to cum?"

"Mmm, I think you can still take care of me." I said as I pulled myself up and off Russ's cock, it slapped down heavily on his belly, covered in our collective juices. Moving swiftly I turned and placed my knees on either side of Russ's face, lowering my pussy lips to his lips while looking back into the floor mirror to see my cute ass perched above his face. As I watched, a tiny trickle of white cum started to leak from my slick pussy lips. After only a moment's hesitation Russ licked from my clit almost to my asshole, the resulting wave of pleasure caused my excited pussy to clench and a huge glob of pearly cum to smear all over Russ's lips and nose. The sight alone was enough to tip me into orgasm. I rode his face for what felt like hours, reveling in the slick, sloppy feeling of his cum, saliva, and my juices mixing together as his tongue flickered over my clit and his mouth slurped the cum out of my pussy.