The Trailhead: Ascent

Author's Note:

This is Part Two of an ongoing series, please start by reading The Trailhead: Discovery, to meet the characters.

Like in Part One, while this story involves some specific fetishes like cum-play and pegging, it's more about kink and sexuality in general and how they fit in a loving and honest relationship.

Lastly, to everyone who read my first story when it first came out and gave it such kind reviews: Thank you for your kindness, your comments and your patience, I am so sorry it has taken more than a year for me to finish part two. I could say something cliché like "life got in the way" but to be honest, I'm simply a procrastinator. I might also say that I'll try to get the next chapter out sooner... and I just might.

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I fell upwards through hazy layers of comfort and consciousness, waking from pleasant dreams to even more pleasant realities. It must have been early, the light sneaking past our curtains was rich and warm with the tones of sunrise. I could feel Russ's body through every part of my body as he spooned me from behind, snoring so softly you wouldn't hear it unless your ear was right by his mouth like mine was.

I felt him stiffen -in more ways than one- as he stopped snoring and, like me, groggily moved from sleeping to waking. I smiled privately and stretched out under Russ's embrace in a way that caused my ass to gently stroke his length. "Mmm, morning babe." he said, his voice gravelly with sleep. "Need to pee."

He got up, causing us both to grumble a little bit. I turned over to watch as Russ walked to the bathroom and pulled his half-engorged cock free of his boxers, unleashing a powerful and noisy stream of pee. After cleaning up he came back to the bed and sat next to me, he leaned over to kiss my head while his hand stroked the small of my back in the way he knows I like in the morning. "Sleep well last night babe?" He asked softly.

"Mmmhmm." I purred as he massaged my stiff back.

"Have fun last night?"

I woke up fully in an instant. Last Night. The best sex of my life. By far.

Did I have fun last night? Ha! I thought back to last night, we had started strong with me giving Russ his first ever Rimjob, then I upped the ante by having him eat out my soaking pussy that he had just cum in. Later in the night we made love in the more traditional manner, but it was still heightened somehow and I had had several orgasms as Russ gently fucked me while staring into my eyes or nibbling on my earlobes or my pert nipples.

I sat up and grabbed Russ's head with both my hands and pulled him into a powerful kiss. After a minute I pulled back and, looking him in the eyes, said "I loved you before. But last night you gave me more physical pleasure than I thought possible. I'm serious. If you keep doing that I will do anything, any-thing that you want."

"How about coffee?" Russ said with a smile. I kissed him again and then hopped up to obey, a goofy smile plastered on my face.

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As we sat around the kitchen table, drinking our second cups of coffee, I showed Russ the sex toys that Dee had bought for us. We had never gotten around to opening them up last night, but I had given Russ an idea about what was in the bag.

"Wow!" Russ said as he pulled out the strap-on dildo that I had picked for him, a colorful, softly curved phallus roughly the same length and girth as Russ himself. It had a shorter angled end that would sit in my vagina and -if Dee was to be believed- transmit the feelings of penetration back into me. "I can't believe you got this for me, for us!" Russ exclaimed.

"Well, Dee pointed me to the section, I just picked the size." I smiled and blushed. "Keep going." Russ pulled out the two sets of buttplug multi-packs and bottles of lube. "Those are for you," I said, pointing at the curved set of plugs. "Apparently they press on your prostate gland. While these," I said holding up the more traditional cone shaped plugs "are to stretch out my butt for you."

Russ almost dropped the bottle of lube he had been inspecting and I had to stifle a laugh. "You... you'd be willing to do that with me?"

I nodded. "I've never really thought about it much or done it with any of my other boyfriends, but... I don't know. I think I want to do everything with you, know what I mean?" Russ nodded so I continued, "I want you to have all of me. I want you to be the first to touch me there. And..." I hefted the strap-on "if I'm going to do you in the butt, I want you to do me in the butt too."

"Uhh wow, I never imagined in a million years that you'd be willing to try any of that." Russ said, visibly surprised. "I guess I never really imagined any of this," he said gesturing to the table "could actually happen. This is like something out of a porno."

"That's what I thought. The first time I mean, watching Jay and Dee on the trail. I thought, how can this be real?" I said as I put slices of bread in the toaster. "And then I talked to her and realized she just lives like that, all the time. But it's not dirty or wrong, and they love each other so much." I was almost shaking with excitement as I said this. "And I want that too, I want it with you." I got down on my knees in front of Russ's chair and looked up at him. "I want everything with you."

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We reaffirmed to each other that we both wanted to go to dinner at Dee and Jay's place this evening, and having done so, split up to take care of chores and random tasks that had been forgotten about during our chaotic weekend. It was around five when Russ came into the bedroom where I was folding laundry and surprised me with a question.

"Hey babe, uhh... since we're being all bold and naughty, uh what do you think about us wearing buttplugs to dinner?" He asked, barely meeting my eyes that were certainly wide with shock. Who was this new person in my boyfriend's body? What had happened to the conservative gentleman? I nodded dumbly. "Do you want to put yours in yourself or... or would you like help?" Russ asked. There was the gentleman at least.

"Uhh..." I thought back to my conversation with Dee in the Adult-Toy store, she had talked at length (snort) about anal sex and how to prepare for it, so I had a pretty good idea how we should prepare. "Why don't we do the first parts ourselves, in private, then we can help each other put the toys in." I said, smiling.

Russ looked confused. "First parts?"

I briefly went over what Dee had told me, and grabbed a shopping bag I had tucked away with a couple of enema kits from the drugstore that I had bought on Dee's recommendation while coming home from the Toy store. "Use this, then use the bathroom and clean yourself up. Afterwards you can use some lube on one of your fingers to make sure you're clean and prepare things a little bit. Dee says we'll both have more fun if we get ourselves warmed up first, I guess it's too easy to get tensed up and hurt before you get used to it."

I gave Russ some privacy and waited outside until he called me back in the bedroom a few minutes later. "All clean," he said, then handed me the bottle of lube and the smallest of the curved plugs and, with a deep breath, turned and got down on all fours facing away from me on the bed, his cute asshole showed a slight glisten of lube.

Carefully, I knelt down behind Russ on the bed and applied a dollop of lube to my finger. Then, after taking a moment to prepare myself, ran the finger around my boyfriend's tight, puckered hole. He flinched away at the first touch of the cool lube to his sensitive orifice but quickly shifted back, letting me continue to gently stroke his anus and surrounding areas with my slick fingers. After a few moments I started to tentatively dip the tip of my middle finger into his tight hole. I relished the feeling of the muscle tense and relax as my finger probed ever deeper. I applied more lube and then in one slow movement inserted my finger all the way into Russ's asshole. I could feel his body heat, his pulse. Holy fuck. Is this what guys get to feel with their cocks?

"Ungh, oh my God Babe," Russ moaned out while putting his head down on the mattress. I removed my finger and applied a coating of lube to the buttplug, then putting it up to his puckered hole, watched with fascination as the head slipped past his sphincter and practically sucked the small plug in all the way to the base, eliciting another, louder moan from Russ.

I worked the plug in and out for a few moments, letting more lube dribble down his asscrack from above and slick the length of the plug. "How's that feel Baby?" I asked gently, feeling strangely powerful with my tiny form in such a commanding position over my boyfriend in such a vulnerable one.

"It actually feels really good. I... I think you could move up to the next size." He stammered, looking back into my eyes, looking for acceptance.

I was not going to commit the same mistakes I had the first time Russ and I had talked about our fantasies, I had botched that badly and almost doomed our whole relationship. Never again. I smiled and said "Of course Baby, let me get it." I grabbed the middle sized plug, this one a bit thicker than one of Russ's thumbs, and headed back to the bedroom. I went through the same motions of slowly working the plug in and out, making sure it was more than well-lubed. Russ moaned and grunted, keeping his head low, his cock was only half-hard, but leaked a constant stream of precum that got all over our sheets. After I was done with the second plug I leaned under Russ and sucked the sweet liquid from the head of his member, making him shudder and groan.

"Next size up?" I asked, but Russ declined saying this was his limit for right now. "OK then, see you in a bit!" I said as I gave his ass a playful slap and skipped to the bathroom.

I used the enema, a slightly undignified, if not totally unpleasant experience. Then, after applying some lube, began to gently touch my own anus like I had Russ's a few minutes earlier. This was a new experience for me and I was slightly shocked by how sensitive my little ring felt. As I dipped my finger in for the first time a little gasp escaped my mouth. So hot! So tight! I couldn't believe I could be that tight, even my skinny finger seemed like it was stretching me to the max, I couldn't comprehend how I'd ever fit anything the size of Russ's considerable cock in there. But one step at a time I told myself, and spent a minute dipping my lubed finger in and out while I looked at myself in the vanity mirror over the sink I was leaning on.

As I looked in the mirror I liked what I saw, my naturally curly brown hair framed my heart-shaped face, freckles dusted my pale skin. With no makeup on I looked cute. Wholesome. I wondered what I'd look like with Russ's cum dripping off my face? I hadn't had a chance to see myself after the incident on the trail, I was the only one out of the four of us that hadn't I realized with a shock. I wanted to see myself coated with Russ's cum, absolutely coated so there was no sign of the wholesome girl, only the sex-goddess, maybe more than just Russ's cum... I broke that line of thought off with a start as I slipped my finger all the way into my tight butthole with a bright, intense flash of pain and pleasure.

A minute later I was laying on my back on the bed. I held my legs up to my chest and let Russ get a good look at my ass. His tongue practically lolled out of his mouth like a cartoon character as he stared at my little puckered anus with unfettered glee. I wondered how long he'd secretly harbored these desires without telling me, I wondered how long we'd wasted, not talking to each other about what we wanted.

He knelt and began to lick up and down the length of my lips, occasionally flicking my hypersensitive nub with the tip of his tongue. At the same time I could feel his larger fingertip gently running around my soaked asshole. I grunted as his girthy digit probed into me for the first time, the pain overwhelmed by the feeling of fullness that somehow radiated up to my pussy and combined with the waves of pleasure his mouth was rocking me with. The tip retreated and I felt cool lube squirt on my ass. I knew what was about to happen and looked down and met Russ's eyes and nodded 'yes' to the man I loved. I was still shocked as his slick finger entered me and continued on deeper than I thought possible. My mouth dropped open in an O of shock as Russ gave an upwards lick on my lips and then must have slipped a finger, no... two fingers, into my drenched pussy. Oh god! I could feel the finger in my ass and the two in my pussy slide past each other with only a thin, hypersensitive membrane of flesh between them. When Russ sucked on my clit and flicked his tongue over it I came. Hard. While I was still mid-orgasm Russ removed his finger from my asshole and replaced it with the smallest of my buttplugs, it stretched me ever so slightly more than his finger, but was smoother and tapered so it fit comfortably.

Much later, after I had regained some semblance of control over my body, Russ asked me if I wanted to go bigger. "Ha!" I replied, I could barely deal with the intense feelings radiating from my opened butthole as it was, and this was the smallest plug! I let Russ know I was at my limit and we got in the shower together to get cleaned up for dinner.

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I frowned as we pulled onto the street that Dee and Jay lived on. It wasn't that it was a bad neighborhood per say, more just run down and ramshackle. Several of the yards of the well-separated plots were completely overgrown with weeds and the road was a minefield of potholes and cracks. We pulled up in front of their address and I was similarly unimpressed as we walked towards the door of what looked like a rather small and old-fashioned cottage, the yard was also a mess of weeds. I was actually almost having second thoughts, wondering what we were walking into when through an open window a spill of light, music, and the smell of something incredible cooking washed over me. I knocked on the door maybe a bit too enthusiastically.

"Holy crap girl!" Dee exclaimed as she opened the door. "I thought you were the police or something! That's some knock you've got," she said as she lifted my arm. "Bet ya keep him in line no problem." She laughed as she hugged Russ while pulling us inside.

The inside of the house was a hundred and eighty degree flip from the impression the outside had left me with. It was warm and bright and full of funky furniture and funky music and some amazing smells that were both familiar and exotic. The longest wall of the main living room that we entered was almost completely taken up by two elegant and rakish sea-kayaks hung from hooks on the wall. The other side was filled with bookshelves that were overflowing with books and random curiosities where there weren't windows. A small TV sat in a corner looking rather forlorn. Jay waved at us from the kitchen and beckoned us in. As I took it all in I looked for any conspicuously erotic art or books, but aside from a rather adorable sculpture of two balloon-animal doggies going at it in the titular style, I didn't see anything. Maybe they kept it in the bedroom.

Dee gave us a quick tour while Jay made us drinks. There wasn't much, the house was small -it had been Jay's grandmother's they were told- but cozy. The main floor held the living room, kitchen and small dining area, bathroom, and a stairway leading up that Dee said led to a small bedroom that took up the entirety of the upper floor. But the best part was out back. The rear of the house had a screened-in porch filled with comfortable furniture and beyond that a deck with a charcoal grill on one side and a covered Jacuzzi or hot tub on the other side. A well kept lawn stretched away into the deepening twilight but I could make out at least two fire pits with chairs and benches ringing them, tall trees blocking out the sky, black on near-black, and around it all a very tall wooden fence.

"Wow." I said, standing on the deck looking out. "I can see why you guys don't have any tan lines!"

"Yup, we spend a lot of time out here in the nude, it's one of the reasons we love this place, no nosy neighbors!" Dee replied.

"Jealous." I said honestly.

"Oh come over anytime!" Dee said enthusiastically. "I'd love to have company while working on my tan, both of you, really feel free to come over whenever you want. You can use the gate on the left side of the house so you can even come over even when we're not here."

"Um, wow... thanks." I replied lamely, imagining myself tanning alongside this beauty. Then a shiver ran up my spine as I imagined Russ tanning nude alongside Dee!

Thankfully I was saved by Jay arriving with a tray of cocktails for all of us.

The next two hours were spent -first preparing and then enjoying- what has to have been the best dinner I've ever had. I got put to work slicing bread still warm from the oven while Russ was tasked with setting the table out on the screened porch. Jay was a buzz of constant activity; making drinks, packing pipes, telling jokes, and generally getting in Dee's way as she put the finishing touches on dinner, sneaking the occasional kiss from her as he passed.

The food was amazing, the drinks plentiful and refreshing, even if (I suspected) not terribly alcoholic. At first, while we were all stuffing our faces, Jay and Dee took turns keeping us entertained with stories from the bars they had worked at, but afterwards our conversations wandered in odd tangents and roamed freely. I'm not sure why, but the talk never turned to anything sexual or erotic, and that coupled with the buttplug that was constantly drawing my attention to that area of my body and trying to make me think of nothing but sex... was terribly distracting and rather excilerating.

It wasn't until after the dishes had been done, and we were all sitting outside around a small campfire that Jay had kindled in the smaller of the two firepits in the backyard -the "chill pit" as he called it- that the topic of sex finally came up.

"So can we talk about sex?" I blurted out.

Dee, bless her, broke out in loving laughter and got up and sat next to me on the rough-hewn log bench me and Russ had been sharing.

"I'm guessing things went better last night?" Jay asked with a smile as he used a stick to adjust a log in the growing fire.

"Uh, yeah, you could say that." Russ said while shaking his head and staring wide-eyed at the flames. "I... I don't really know how to thank you guys for what you told Nicole. And uh, umm... bought us." Maybe it was the firelight, but I'm pretty sure he turned a shade redder as he said this.

"OK good, I wasn't sure if she had told you about that, didn't want to start asking about things at dinner and ruin the surprise." Jay said.

"No, it's OK, I told him everything last night, even about the drop of cum, and," I said with a grin "showed him the toys this morning."

"What drop of cum?" Jay asked, eyebrows narrowed slightly.

"On the trail, after you came on me, we had a little kiss with a drop of your cum." Dee broke in, looking right at Jay.

"You never told me that." Jay responded, a little hurt, a little sharp.

"Wasn't my secret to tell Babe." Dee responded cooly.

"I'm sorry," I broke in. "It was all me, I just did it, it wasn't her fault."

Both Jay and Dee turned to me, Dee putting her arm around my shoulders. "It's not a problem, and if it is it's not your problem," Jay said "I don't blame you or anything, but I think you," he said looking at Dee, "should have told me. I don't have a problem with it, but I might have, and I shouldn't find out well after the fact."