Crossing the Rubicon

Whilst this works as a stand alone story, reading the earlier chapters will give you better context. In case you can't be bothered with all the previous 48k words, here is a synopsis for you:

Rune, the runt of the family, and only son, grew up with four over achieving sisters and, shunned by his parents and siblings, lived the life of a loner, dressed in his sister's feminine 'hand me downs'. He was befriended by Becca, a hot soccer player, at College. She discovered he had a pair of his sister's underwear and encouraged him to live the life he wants to live, dressed as a woman, something Becca, and 'her' landlords, finds a huge turn on. Along the way Rune's had an interludes with Becca, nights out with her team and a dirty weekend away with her landlords and lost her anal cherry to one of Becca's team mates. Add to that she's helped pick out outfits for Becca to go on dates and Becca has returned to her apartment after each event, having 'her' clean her up.

And remember, this is not real life. It is just a story folks. Any resemblance to anyone, anything and anyplace is purely coincidental.

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Summer had tried its best to hang on, but the warm days and nights had slowly been turned cool by inevitable change of season. Whilst there had been a lot of leaf fall for some time, the weather had remained unseasonably warm. Suddenly the real fall had arrived and things were starting to feel very different as the second half of November hit. The mornings were invigoratingly brisk and the evenings chilly, and laced with the scent of wood smoke, and the fashions around campus had moved to suit the times.

Hoodies and baggy sweatpants, blazers over oversized sweaters and baggy jeans, leather jackets and miniskirts over tights and tees, puffer vests matched with almost anything, one could see it all, and in all manner or colors and textures, in the space of a lecture or two.

And I had just finished my second for the day when a voice called me from behind.

"Hey Rune. How goes it stranger?"

It was Killian, all dimples and smiles, her brown eyes wide and clear. She was dressed in a vintage oversized grey Old Navy sweater, faded jeans and black boots with a heel. She closed the gap between us and moved in for a hug. I initially hesitated and she picked up on my vibe, but then I moved somewhat awkwardly into her embrace. The pleasant smell of lemongrass enveloped me as we hugged closely followed by the much recalled image of her ass cheeks from earlier in the semester.

"You heading for snacks?" she asked, as she the hold she had on me and pulled back slightly.

"Absolutely, Killian. You hungry too?" I asked as we started off towards the food hall.

She nodded.

"No Becca today?" She inquired. "You guys have seemed inseparable the last few weeks."

"Nah, she had some soccer meeting. You've seen us?"

"I haven't changed my schedule Rune. I've seen you pretty regularly, like always, but you've been so focused on her that you haven't seen me." At that Killian punched me on the arm. "Anyhow, what's up with the collar?"

"I'll tell you over some nachos, or wings. Your call." I said.

"You had me at nachos," she said, with a wide smile and fluttering eyelids.

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"Holy shit that's crazy," she said as she used her last corn chip to scratch away at some dried melted cheese on her plate.

I had just filled her in on the events since we had last talked. I was going to censor a few things, but Killian had joined a few dots and pressed for details, so I ended up spilling it all. It had been quite a list: the threesome with Becca and Simone, the weird interlude with Stella, Becca accusing me of being untruthful / unfaithful, the 'collaring', Halloween and the drugging, and then the constant time spent with Becca and her invite to Thanksgiving with her family.

"So you are okay walking around with that collar on?"

I reflectively touched the ring that dropped down from the center of the pink collar.

"I've grown used to it. She felt like she needed to assert more control over me, and she did. So far I haven't really had any issues with it. Look, I know on one level it is weird, but it has brought us closer together."

"So Halloween? Did anyone else discover your secret?"

I shook my head. "I don't think so. Most of the girls still treat me with a bit of contempt, but no one has said or done anything to suggest that my appendage is common knowledge."

I couldn't bring myself to tell her about my failure to ask about my sore ass in the days afterwards.

It was then my turn to ask questions.

I asked about her recovery and her family and why she wasn't at the soccer meeting with Becca.

"That meeting was about next year's program. My soccer days are over Rune. I seniored out remember."

"I like the vintage sweater Killian. I didn't pick you as the Old Navy type."

"It was my dad's originally. Mom claimed it as hers pretty early on when they started dating. I stole it from her and claimed it as mine years ago. She gets all nostalgic when she sees me in it, but also reminds me she had latched onto my dad by the time she was a freshman and I haven't done the same." She pulled at the hem. "I'm not sure they make them like this anymore."

I smiled and said, "That's a sweet story," and then went in for one of my last corn chips.

She used her napkin to wipe at the corner of her mouth and then looked at me, her smile dimming for a fraction of a second.

"Killian? What?" I asked.

She looked down for a second and then looked at me straight in the eyes.

"You hurt me with that last text exchange Rune. I know it sounds silly, as we only just struck up a...friendship...and I get it, Becca is possessive and you two are inseparable of late, but I thought you'd at least drop by, or catch up in passing, or something. I have just felt a little ghosted."

I didn't know what to say. I just sat there, processing. Eventually I just said "Sorry."

We sat there in continued silence, looking at each other. I didn't know what else to do or say. So I said nothing.

After what seemed like an eternity, Killian's eyes darted to my left and her hand rose and pointed. "Becca."

I turned and looked.

Nothing.

Puzzled, I turned back to face Killian. She was smiling like the cat that caught the canary and held a loaded corn chip in her hand. I looked down and my plate was bare. I looked up in time to see the chip and jalapeno pass between those beautiful lips. That was my last chip. I had saved it to be my final tasty morsel. Now it was naught but a smile on the girl across the table.

"You'll pay for that!" I cursed.

She used the napkin on her mouth corner again, stood and picked up her bag.

"I mean it though. Don't be no ghost Rune. Come and hang out and play Skyrim," she said and then turned and headed for the door.

"That jalapeno was reserved you know." I said.

All I got in response was her left hand showing me the bird.

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I studied in the library a while after my last class and then walked home. The late afternoon was a tapestry of long shadows and golden hues and the air was hinting at the chilly night to come.

By the time I rounded the corner of the last block I was famished and looking forward to just chilling for the evening. I made it to the door to my cellar apartment just as Becca pulled up with Simone riding shotgun.

They got out and made a show of the pizza, beers and small backpack they had with them. "There goes the quiet night' I thought to myself.

"So why beer?" I asked as we destroyed the pepperoni pie that had been in the top box, leaving the dessert calzone in the bottom box alone for the moment.

Simone answered. "That was my call. I'm just sick of bubbles and cocktails of late."

I moved to the heating controller, turned it up a touch and took a swig, and smiled. I somehow thought that we might be naked soon. There was no point in being cold as we did whatever else was about to be done.

She took a long pull from her bottle and then, setting the bottle down on the table, looked at Becca and then at me.

"You know Rune, I think I said that after the soccer season finished, I was going to destroy your ass." She said. "So here's what is going to happen. Becca and I are going to drink some more and have a little dessert. You are going to go clean yourself out and up for me. I want to see you looking real pretty."

She reached for her backpack and came out with a package and a shoebox.

"Here," she said. "I thought I'd help out by providing what I thought you'd look pretty in. Now go and prep. I want to really go to town on you fresh, clean and pretty little ass."

I looked at Becca and she tilted her head towards my bathroom. "You heard Simone, go!"

I turned and headed for the room, a little nervous but tingling at the thought of what was to come. By the time I made it past the bathroom door my cock was straining in its tucked position.

After dealing with the clean out, and applying an initial shot of anal lube, I dried myself and started with the clean up. Hair done, with a light makeup application, I fumbled with the package and eventually got it open. I slid a hand and retrieved a scalloped shelf bra in the same hot pink color as my collar. This was followed by a matching high waisted boy leg panties with an open back. I went into again and came out with a clear plastic sleeve which contained thigh high stockings, again in matching pink.

My erection was rock hard as I pulled the panties up. It took me a second to realized that the high waist cut had been chosen to contain my erection in front of me rather than in my usual tucked position. I adjusted the bra in position and tweaked at my artificial nipples. It didn't matter that the sensation was less than would have been the case if they had been real breasts, as the sight of me in the mirror doing so caused me to moan.

I slowly and carefully pulled on the stockings, taking extra care not to tear or run the delicate fabric. Simone hadn't gone cheap with these. They were not some cheap temu item.

I took another look in the mirror. I was a vision in hot pink. I turned left and right, admiring the scene from all angles, and making a few minor adjustments in the process.

I searched my bathroom drawer for a lipstick that would do justice to the outfit. I didn't quite have a hot pink but knew there was a pink pastel in there somewhere that would have to do. Once that was applied I spritzed myself with some perfume, including a light hint around my ankles.

Opening the shoe box, I found a pair of transparent high heels on a three inch platform and long straps.

I fastened these around my ankles and took another long look in the mirror and drank in the sight. The shoes had me pitching forward, putting my breasts on even greater display and pushing my ass out on a cute angle. I moaned at the sight and allowed myself a moment to revel in the feel of my hands on my breasts and body. My cock twitching under the fabric of my panties as I did so.

I opened the door with enough force to ensure that Becca and Simone would hear it but did not go out to them. I let them wait for a 10 count and then sauntered out into my bedroom and looked out into the kitchen.

Simone was standing by the table wearing nothing but a flesh colored 8 inch strap on and a smile. Becca sat in her chair, wearing a sports bra and cotton thong.

Simone gave me a twirl around signal and I complied. "Now that's what I've been picturing," she said. "But you look even more fucking delicious in real life." She pointed to her plastic cock and demanded I pay it the attention that it warranted.

I slowly strode the eight or so steps to her and knelt at her feet and looked up at her.

Without breaking eye contact, I crept my hand up the inside of her thigh. She took a sharp breath and trembled slightly at my touch. I reached out and wrapped my fingers around her member. It had a certain give to it. It felt good in my hand.

I rose up so I could spit down on its head and then stroked it gently whilst lowering my mouth to its bulbous head. Both Simone and Becca groaned, almost in unison.

Their sounds heightened my arousal. I had power in that moment, and that thought excited me. I felt my hardened member pulse.

I licked my lips. Simone gasped as my other hand climbed up her thigh and brushed at the point where her flesh met harness met the harness. I leaned forward, extended my tongue, and licked the underside of her cock from near where my hand was to the tip.

"Fuck that looks hot," rasped Becca.

I went back to the start and repeated the move but this time stopped at the apogee of my actions, with just the tip of my tongue on the slit of her cock and stared into Simone's eyes without saying a word. She gulped.

I then leaned forward again and, keeping my eyes locked on hers, wrapped my mouth around her hardness and moaned slightly. Simone sighed in pleasure.

I moved my hands around to her ass cheeks and pulled her into me and lowered my eyes and went to work. I started bobbing my head, slowly at first, then faster. I moved a hand back to grasp the base of the cock and jerking at it whilst swirling my tongue around the top half. My other hand started busily fondling her ass.

Becca moaned again. I shot a look in her direction and she had one hand inside her bra and the other down the front of her thong, her legs spread wide.

Simone gently put her hands on my head, not pushing or grabbing at me, just holding me and moving with my motions. I licked around her tip and down her shaft, making sure to trace every lump, curve and vein.

Every move we made heightened my own pleasure levels and caused me to work harder. I was thriving on the thought of the pleasure I was giving both of them and the feelings that were rising within me.

I was so fucking hot that I was turning these two fuckable fit babes on. That thought turned me on and continued the feeling loop that had me running on natural endorphins. I heard myself moaning more and more.

Eventually Simone's hands became assertive and guided me off her cock and onto my feet. I kissed at her flat belly and amazing tits as I rose, earning more than one moan from her.

She then spun me round and pushed me to the end of the bed and had me bend at the waist, legs spread, with my head and shoulders down on the sheets.

I thought of Stella and wondered if she might be on the other side of the wall.

"So are you going to fuck me now or what?" I asked, a little loudly.

Simone replied non verbally by spitting on the head of her cock and then grabbing my hips and spitting down into my ass crack. She then adjusted her angles and placed the head of her member against my asshole.

"This answer your question?" she said as she rammed into me.

I moaned loudly and let out an "Ohhhh fuck," my hands grasping at the sheets as she began ploughing into me.

Becca let out a "Jesus Simone," as I was hammered into.

Simone kept going, and going. I had to adjust my legs now and then to reposition my ass due to the force of her assault. At the end of each stroke I was feeling my insides move and at the height of her pull back I could feel her bulbous head testing the strength of my anal lips.

I was moaning, with deep guttural moans that reflected the pleasure and pain she was bringing me. Simone was dirty talking and breathing heavily as she did so. Becca just kept swearing at us. I couldn't see her but I could hear here fingers hammering into her sopping wet folds as she watched us.

Just as I thought I would take that last step from intense pleasure to orgasm, Simone pushed herself off and out of me and I immediately felt totally empty.

"Get on you back, bitch," Simone commanded.

I immediately felt relief in my hands as I let go of the sheets and my legs appreciated the change in position as I shifted. I hadn't realized the strain they had been put under by the heels and the force being applied to them.

Simone was covered in a film of sweat and had a look of lust in her eyes. She moved to my bedside table and located some lube in the top drawer and added some to her cock. She then moved to between my legs and pulled my knees up for me to grab. I pulled back on them, lifting my ass up.

The front of my panties sported a large wet spot and my hardness was clearly visible through the vibrant pink material. Simone squirted some lube on my rosebud and ran a finger through the liquid and into me, the intrusion a pleasurable feeling after the emptiness of the last minute or so. I thought she would ram back into me but she stepped back and drank me in.

"Holy shit you look fucking hot Rune. That slutty pink and the pale skin, the look on your face. You should do porn."

I shook my head. Becca chuckled weirdly.

"I'm serious Rune," she continued,"Guys would love your stunning female looks. Girls would also love your female looks. Everyone would lose it over your fucking amazing ass. You couldn't lose."

Becca shifted off her chair, shed her remaining garments, and stood beside Simone, a hand going around her waist. They both looked at me.

"Runeporn," Simone whispered.

Becca smiled and repeated "Runeporn..." And dropped her hand to Simone's ass. "Speaking of amazing ass," she added.

They kissed heatedly as Simone's hands went for Becca's breasts. Becca pulled at Simone and I watched on in awe as these two fit, sexy and turned on young women got caught up in each other.

Simone ended up pushing Becca back against the wall and maneuvered the head of her hardness into Becca's swollen pussy lips. Taking hold of her thighs, Simone lifted Becca, who assisted in the maneuver by jumping up into her lover's grasp. Becca's arms went around Simone's shoulders. Looking at how they moved so fluidly, I guessed that this was not the first time they had fucked this way. Becca, supported by Simone, sank slowly onto her lover's cock, moaning as she did so, until she taken it entirely inside of her.

Becca tossed her hair to one side with a flick of her neck and looked into Simone's eyes. She then bent in for a hard kiss, finally breaking it to give the all clear. "Fuck me..." she panted,

Simone bucked her hips and slammed Becca back into the wall, causing Becca to cry out in ecstasy. Ramming her hardness into Becca, Simone was soon swearing and moaning as she lost herself in the heady pleasure of fucking her friend and team mate. They went at it like two animals in heat, with Becca's body thudding against the wall, the noise and tempo sounding like an excited Japanese taiko drummer if not for the moans and curses the two were making.

I ended up pulling the boy leg panties down and stroking my erection as I watched them revel in their individual and combined pleasure. At times they increased the tempo and at other times they slowed things down but dialed up the eye contact and verbal lovemaking. It was an unfucking believable display of lust, pleasure, friendship and love.

Becca announced her incoming climax first, with Simone confirming she was not to far behind a moment later. The two swore dirtily as they peaked, with Becca's shuddering body being slammed heavily into the wall by Simone's final thrust that the wall shook. That sent Simone over the edge and she too began to quiver and shake with her own massive orgasm.

As they came down and un-entangled from each other, they tuned and looked at me.

"Sorry, I got a little distracted," Simone panted. "Give me a minute and I'll be right with you."

Becca made a time out sign and gasped for air. "Water...need water..."

The two helped themselves to glasses from a jug in the fridge and then Simone came alongside the bed and had me clean her cock. I licked and cleaned it, enjoying the taste and feel of Becca's fluids on the fleshy and still warm member. Simone then resumed her place between my legs whilst Becca came and sat behind me, holding my legs up for me and re-raising my ass for Simone.