Crossing the Rubicon

Author's note: As always, reading the earlier chapters will give you better context.

In case you can't be bothered with all of that, here is a synopsis for you:

Rune, the runt of the family, and only son, grew up with four over achieving sisters. He lived in their hand me downs and was shunned by his parents and siblings, living the life of a loner. He was befriended by Becca, a hot soccer player, at College. She found him in a pair of his sister's underwear and has encouraged him to live the life he wants to live, dressed as a woman, something Becca finds a huge turn on. Along the way Rune's had an interlude, and an argument, with Stella, his female landlord and a night out with Becca and her team, after which Becca established that she can't be exclusive to Rune, but wants to keep things going with her.

And also, this is not real life. It is just a story folks!

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It was 4.15pm when I made it home. There was a small card stuck into the beading of the window on the door to my cellar studio apartment. Written in neat feminine script it offered "Come up for drinks around 5pm if you are free." It was from Stella and Steve. They were my landlords, and Steve had been home for several days from his job that kept him traveling around the country. I'd heard his voice as I'd come and gone from my cellar studio.

I'd had a crappy day with a double set of lectures plus a tutorial, and my laptop had been shutting down on me randomly every now and then. I just wanted to put on a tv show and eat something high in carbs and wallow in some self pity, not go socialize with the landlords. Especially since the last time I'd spoken to Stella was when she asked me to fuck Steve in the ass, and I'd got a little angry at her thereafter.

I gave myself 30 minutes of 'me' time on my bed, scrolling mindlessly through my socials. I couldn't be bothered changing out of my leggings, but I did change the tshirt I had on for a black polo and brushed my hair in a half hearted attempt to look a little better. I then checked myself in the mirror one last time, took a deep breath and headed up the stairs.

I was greeted with a 'come on in wave' as I passed by the window by their screen door and headed on in.

Stella rose from her seat at the breakfast bar and met me with a warm hug and a whispered "I hope I'm forgiven."

Steve stood near the sink and looked a little unsure of what to do. The last time he'd seen me I was the old me, the 'male' me. I looked at him, He looked at me. We both looked at Stella.

I decided to end the weirdness by closing the gap to him, extending my arms for a hug, which he reciprocated.

Stella smiled warmly at me as I broke away and claimed a seat next to her.

"Make the woman a drink please Steve," Stella asked.

I pointed to her Espresso Martini and nodded.

Small talk ensued for a while, more drinks were made and I was getting a bit tipsy by the time I agreed to their offer to stay for food. Steve fired up the BBQ and Stella made a salad whilst I talked about my classes, my dysfunctional upbringing and how my life had changed recently. Stella had known some of this from our previous chats, but this was all first hand information for Steve.

We were relaxing in their tv room, eating ice cream, with Stella and I on the sofa and Steve on an oversized chair on the other side of the coffee table, when I felt Stella touch me.

She had shifted so that she was facing me, had one leg under her and the other stretched out and making contact with my leg. She had long ago kicked off her shoes and was slowly rubbing the inside of her foot arch up the side of my lower leg whilst she was telling me about how she had met Steve in high school and they had fallen instantly in love.

I had not reacted to her contact at first, but eventually smiled at her as it continued, then looked at Steve.

"So...." He said. "Stella tells me she took you shopping and that things happened."

"Did she?" I answered.

He nodded.

"Stella showed me the picture she took of you, in the thong and boots. I can see why she decided to act in the moment. You looked pretty fantastic."

I looked over at Stella and she looked like the cat that got the cream. "I couldn't help myself." Stella said. "You saw those back dimples, Steve. Ain't she just a little hottie?"

He nodded emphatically.

I put the spoon into my empty bowl and placed that on the table.

I looked at Steve. "Did she tell you that she bit me on the neck? I had a bruise for days."

Steve laughed and shook his head.

"Stella tells me that you have an arrangement. So I'm not surprised she told you about what happened that day."

"Ohhh, she told me alright.' He said. "You really made her day, letting her take you shopping and then giving her some pleasure."

I looked at Stella. "Is that all she said?" I asked.

Stella's nostrils flared slightly. I took that to mean she had not told him that she asked me to fuck him in the ass.

"Yeah," he said. "Is there something else I should know?"

I looked at Stella, then at Steve.

"Look Steve, you need to know that I'm not interested in guys. I might dress as a woman, but I'm only interested in women. Please don't take that the wrong way. You seem great and all, but I just want to lay that ground rule down right now."

He studied me for a minute.

"That is a crying shame Rune. But I understand and I'm not offended. So now that we've cleared that up, how about you come away with us on Friday for a long weekend away?"

That offer caught me off guard. They were both watching me and waiting. Stella's foot stroked at my leg again. Steve smiled a knowing smile. He knew he'd caught me off guard.

"Maybe?" was the best I could answer with in the moment. I looked at them both and didn't really know what to think.

"You'd need to give me more information and I'd need to sort something out with Becca. I'm supposed to be going out with her and her team this weekend."

"Becca?" Steve inquired.

I told him that Becca was a girl I had a 'thing' going with. We were kind of an item but not exclusive.

Steve looked at Stella. "You knew this? And yet you still made a move on her?"

Stella nodded. "Yes, but I couldn't help myself. So shut up Steve!"

She then looked at me. "So anyway Rune, my cousin Valorie, the one who works in cosmetic surgery, says she would be happy to meet with you about breast enhancement options. She's in Chicago and she's happy for us to do a walk in. We could leave early and head up there for the day, see her, do some retail therapy and then head out to Steve's family's cabin out by Lake Holiday. We could spend the rest of the weekend just chilling or could go hiking, or swimming, not that it is really warm enough for that, or whatever."

"Or you two could just spend the weekend getting funky with each other whilst I watch." Steve added.

"Steve!" Stella exclaimed.

I could feel myself blush.

"Oh come on Stella," he added. "Its clear by the way you've been talking non stop about her that you've got an itch that needs scratching. Don't pretend to be of pure intention here."

Stella threw her hand in the air. "I just wanted to spend some time away with you two. That's all."

"Stella," Steve said, "are you telling me you could go the whole weekend away and just be platonic with Rune?"

"Maybe," She said, unconvincingly.

"Stand up Stella and stand near the fire place," he commanded.

She went to protest, but he asked again, nicely.

He then looked at me.

"Rune please stand over there, so you are about 10 feet away, facing her."

I did as he asked, looked at Stella and got a fit of the giggles. I don't know why I did, but it took me a good minute to settle down. Steve sat forward on the edge of his chair.

"Ladies, look at each other."

He paused.

We looked.

Stella was moving her feet slightly, and had her legs crossed and her hands hang by her sides, fidgeting at nothing.

I ran my hands through my hair, and didn't know what to do with them after that, so I crossed my arms in front of me.

"No ladies," he said, "Really look at each other."

I looked at Stella. There was a magical look in her eyes. She licked at her lips.

I could feel myself take a deep breath.

"You'd want to have things happen, with me, with Steve there?" I asked.

She nodded and bit her lip. The room suddenly felt a lot warmer.

Steve then issued the next direction. "Please take a small step closer to each other. Keep looking forward and maintain eye contact."

We moved forward. I dropped my hands and joined them in front of me. I felt flush with excitement.

"Stella, what was it like to kiss Rune?" he asked.

She took a moment and recalled the scene in her mind and smiled warmly. "Sweet, but complicated."

"Why complicated?" he asked.

"I knew I was crossing a line. Once that rubicon was crossed, things would not be the same."

"Yet you crossed it?"

"Yes." She replied.

"Rune, what about you? What was it like to kiss Stella?"

"It was nice. No...it was special."

Stella beamed a smile at me.

"Explain," he said.

"Look at her. She's beautiful. I never thought I'd kiss someone like her. Plus," I then hesitated, feeling a bit shameful of where I had started heading. "Plus she's only the second girl or woman I've ever kissed. Becca was the first just a few weeks earlier. And I'd wanted to, since I first came in that day as the 'new me'. Stella just looked so beautiful. That and, I felt something between us."

"Take another step closer to each other. Again, make it small."

"Stella, was there something there that first day?"

She tilted her head disparagingly, but kept here eyes on mine.

"I hate it when he gets like this," she said to me. "Yes. I had a little college nubile in front of me. We were getting on well and there was some sort of magic in the air, and then you called and broke the spell."

He laughed.

"I wanted to buy into some of that feeling again, when the opportunity arose, so I did. I took my shot."

"Yet you say you could go the weekend and remain chaste with Rune?"

She hunched her shoulders.

I refolded my hands in front of me several times. I could feel my mouth going dry. My heart rate was rising noticeably. I felt like I was panting and sweating. My dick strained against the bonds that held it tucked between my legs.

He left us there, looking at each other and into each other. After what seemed like an eternity he had us close the gap by another step.

Stella gulped. I think I did too.

"Did you enjoy sucking on Stella's tits?"

I nodded.

"What did you think of her cock, Stella?"

"It was nice. Hard. Wet. I wanted it. I wanted to suck it. I wanted to make her cum."

"Go closer. Another small step."

We were close. So close we could reach out and touch the other.

Stella looked like she was standing on a hot pavement on a mid summers day the way she was moving from foot to foot. He hands were visibly shaking. Her eyes lay bare the frustrated urges that were swirling inside her.

I felt jittery and so hot that I would spontaneously combust at any second. Or cum prematurely.

"Did you enjoying sucking her Stella? Did you enjoy it when she came into your mouth?"

"Yes." She hissed. "But I wanted more."

My head was spinning.

"Stella, I want you to take off your shirt and drop your jeans."

She did as she was told, not looking anywhere but into my eyes. I worried for a moment about what anyone out on the street might see, but lost that thought when Stella's great tits, encased in a light pink lace bra, were uncovered. I tried not to break eye contact with her but failed, her breasts were just too great not be looked at. She then unbuttoned her jeans and shimmied them to the floor before kicking them away. I dropped my gaze to her pelvis. She wore matching pink underwear. The lace panel on the front did little to hide her shaved mound and her dampness. She may have been on the other side of her mid 30s, but she had a great body.

Steve laughed. "I didn't think you'd be able to resist a look down there Rune. Stella, I think Rune wants to see you naked."

She cocked an eyebrow and I nodded. My heart felt like it would beat straight out of my chest and my legs felt like they might give way. My dick pulsed and I prayed that I would not blow my load standing here, like this.

She slowly removed her bra, revealing the nipple metalwork that I had sucked on at the thrift store during our interlude there. She then tugged down at the straps of her underwear, sending the diaphanous piece of material floating to the floor.

I shook my head in wonder. If you had said this was what Aphrodite looked like, I wouldn't have argued. Becca had a fucking fantastic fit and youthful body, but Stella had a woman's graceful curves and a hell of a lot of mature sexiness happening. She was like a treasured wine next to Becca's impressive tequila shot. Both are desirable in life, but only one is truly magnificent.

Stella took a finger to her mouth and bit into it.

"How did Stella's pussy feel as you slid your finger up inside of it Rune?"

She crossed her legs and let out an almost imperceptible moan.

"Hot, wet, smooth and inviting."

She whimpered. I bit the inside of my cheek. This was fucking torture.

"Is this getting to you my love?" He asked.

"You fucking know it is, you bastard," she replied.

"Yet you say you could go the weekend without your impulses getting the best of you? I know you better than that my love."

She cursed at him.

"Spread your legs, Stella."

She complied.

"Are you feeling wet down there?"

Her eyes were screaming at me.

"You know I am." She replied.

"I want you to both extend a hand out towards the other, but not to make contact."

We both put a hand out so that we were palm to palm with about an inch in between us.

You could almost feel the sexual electricity in the air.

"Rune, what do you see in Stella's eyes?" He asked. "Be honest. What do you see?"

I looked deep into her.

"Fire and frustration."

Stella blushed.

I felt myself fighting to keep my breathing going and my hand steady. I wanted so desperately to close the distance between our two hands and between us. I wanted to give in and have it now.

"And what might Stella be seeing in yours?"

I hesitated. This was not easy.

"Lust. Desperation..."

Stella looked like she might break the distance between us. She bit at her top lip and her brow creased, attesting to the battle being fought in her between her will and her urges.

"You would both go for it here and now if I let you, wouldn't you?"

We both responded with sounds that brought our mutual libidinousness to life.

"Okay you two, that's enough time standing at the brink of a hell of a sexual event. Step back two paces."

She shot a look of dismay at him. We all knew that the time would come when we could unleash our desires into action, but it would clearly not be in this moment. We backed off, and the room immediately felt cooler.

"Stella, I want you to slide a finger up into yourself, just to the second knuckle and hold it there."

"Steve, I'm likely to fucking cum the moment I do."

I really couldn't believe I was a party to this. My life had changed so much, so quickly. The me from a year ago would never have believed I'd be here.

She fought to steady her hand and then sent it across her hip and over her mound, before curling her middle finger, taking a deep breath, and slowly inserting it into her nether region.

"Oh fuck!" She cursed. Her left leg shook slightly.

He kept her there for about 15 agonizing seconds.

Beads of sweat formed on her brow. She began swearing at him. She was obviously fighting against her orgasm.

"Are you like Rune said? Are you hot, wet, smooth and inviting?"

She whimpered again and nodded her head.

"Slowly remove your finger Stella and hold it out to Rune."

She did as she was told. A line of her sticky fluids stretched out from her pussy lips to her finger, only breaking when her hand had traversed a good several inches from her wetness.

Her wet finger glistened before me. I could smell her fragrance.

She moaned and swayed slightly.

"Good girl. Would you like to spend some time with Rune getting funky like this, Stella?"

"Fuck yes."

"But I can watch and still get involved with you, can't I."

She nodded.

"But I'll leave Rune alone. He's all yours. Is that our deal?"

Both Stella and I nodded.

And like that, the deal was well and truly sealed.

He looked at Stella and nodded to the sofa, then at me and nodded to the door. "Stella, I want you on all fours up here. Rune, you should probably go. I need to fuck my wife."

I stood there spellbound as she positioned herself with her legs on the cushions and her arms resting on the back of the sofa. Her ass looked amazing and her arousal was now clearly obvious. He took his long erection in one hand and positioned it at her lips and thrust deep into Stella, making her groan in a primal fashion.

I backed away and headed out the door, casting one last glance through the window and seeing him buck into her forcefully and her body shudder as he did so.

I could hear them as I rounded the corner of the house and entered my doorway.

I hit the bottom of the stairs and fumbled my way out of my leggings, untucked myself and grasped my dick just as the tempo upstairs hits its crescendo. The insulation and sound proofing could only hide so much. They were still audible, although somewhat muffled. She started to swear and announce the arrival of her climax. It didn't take long after that for her to give a final yell and for me to fire off rope after rope of my semen onto the floor.