Sasha's First Time

"Alright Jack I think that's it for this year, have a good Christmas," the broker yapped into my ear as I sat back in my ergonomic office chair and watched orders blipping off the electronic market, one by one.

"Thanks for your help Jonty, talk to you in January. Best to your wife and kids," I replied mechanically through my headset, before pulling it off my head and laying it down on the desk. Relieved of duties, I leant back in the chair and stretched. I'd been a decent rugby player back in my youth and even now I turned out for a local club, but the muscles you needed to push a scrum were not the muscles you needed to sit at a desk all day. Pushing my chair back, I stood up and ran through a series of full-body stretches I'd once been given by a physiotherapist.

"Starting the warm up already?" The smartarse was my colleague, Callum McCarthy, the only other bloke single enough to be in the office late on the last working day before Christmas. He was holding an open bottle of Galapagos beer in one hand and had a closed one in the other, jiggling it in my direction.

"I was thinking about hitting the gym, actually," I told Callum, eyeing the beer cautiously. "In any case, I'm sure I read something in the employee code of conduct about no alcohol consumption on-site."

Callum grinned. He was a Scot through and through and instinctively felt that any rule made in England was a rule made to be broken.

"Well, I looked around and there's nobody else here, except for Elsie on the front desk and I'm not going to tell her." Callum jiggled the bottle more vigorously.

I reached over and took it, then had to pick through the keys on my keyring to find a bottle opener before realising it was a twist-off cap.

"You just watched me looking for an opener when you knew full well I didn't need it," I said, indignantly, and Callum burst out laughing.

"Come on, Jack, we'll have this one and then a bachelor's bar crawl. Screw the gym, it'll be there tomorrow to help you work off your hangover."

I looked out of the office window into the darkness. The offices of Westley & Charles Natural Energy Products (WCNEP) were perched at the top of an office block in the newly-improved riverfront area of Liverpool, and I could see the streets down below teeming with people. There were quite a few posh restaurants and swanky bars around here and I had to admit, a solo trip to the dingy gym near my flat didn't appeal nearly as much as some bar-hopping in the pre-Christmas atmosphere.

"Go on then, you twisted my arm," I told Callum, taking the beer as he cracked a smile. WCNEP paid its crude oil department pretty well, especially by Liverpool standards, and for a single guy with no responsibilities that meant cash to burn. There was no better time than Christmas.

Callum settled himself into a spare chair as I downed the first half of the beer in one go to quench my thirst, then started shutting my computer down.

"What do you reckon to dinner at that Thai place near the conference centre?" Callum asked, rocking on the chair, tapping his fingers on his bottle.

"Went there last week," I told him, dismissively. "Wasn't worth it."

"Fair enough," Callum said. "I'm in the mood for something spicy, though."

"I could go spicy," I agreed. "What about Chennai Palace? They're usually not too busy and they do some fiery options."

"Bit of a walk," Callum mused.

"What else are you doing tonight?" I pointed out, the computer's fans whirring to a halt. "And anyway, there's a ton of decent bars around there."

"Alright smarty pants, Chennai Palace," Callum announced, and we clinked the necks of our bottles together to seal the deal before necking everything that was left.

"That Galapagos beer is shite," I told Callum as we went to the lift, empty bottles stashed in his briefcase to hide the evidence. I'd left my case behind, since I wouldn't need it over the festive break.

"Ah, it's not too bad," Callum replied, pressing the button for the ground floor.

"No, dickhead, it's shite. You bought it because the advert has that blonde lass in the outrageous bikini in it," I pointed out.

"So what if I did? That's the point of adverts, after all," Callum said, defensively. "A single bloke can admire a lady's backside in a bikini without it being a big deal."

I chuckled. "Yeah, but you don't usually have to buy a crate of piss-tasting beer after."

"Women are usually much more expensive than a crate of beer," Callum pointed out and I had to agree with him as we spilled out of the lift into the foyer.

"Merry Christmas, Elsie," Callum said cheerfully to the permanently-miserable receptionist.

"Merry Christmas," Elsie grumbled from behind her hand as she studied a wordsearch puzzle.

"Fun sponge," Callum said, the second we were out of her hearing.

"She really is a miserable old bat," I said, shaking my head. "Not a single bit of tatty Christmas decoration anywhere on her desk."

Chennai Palace was very busy when we got there, but they'd opened an extra section of seating at the back so we were ushered in no problem. We shared the fiercest curries we could find and doused them with three rounds of lagers, before stumbling out ninety minutes later feeling a lot more content.

"Right, Jacky," Callum said, taking a deep lungful of cold winter air. "Let's start drinking."

Chennai Palace was right next to the old Crown and Anchor, which had been taken under new management and completely overhauled to try and keep the old clientele away and attract a new, trendier crowd. This had failed, of course, and I followed Callum across the threshold to be met by a sea of lager-drinking old boys glued to their Daily Mails or loudly discussing the need for Liverpool FC to purchase a new midfielder.

"Two pints?" Callum asked, pulling out his wallet.

"Go on, then. We'll get onto the spirits later," I grinned.

After the Crown and Anchor, we breezed through a couple of more upmarket bars, paying twice as much for drinks but at least not having to dodge around beer guts to get to the bar. By the time we arrived at Fernando's, a Spanish bar which I would normally never go into (I was more of a beer-and-sport-on-TV person), which specialised in Spanish and Portuguese wines but also had a decent selection of spirits, I was feeling well lubricated and definitely in the festive spirit.

"What are you in the mood for?" Callum asked as we stood at the bar, eyeing the array of coloured spirit bottles. I also eyed a slim brunette in a low-cut white cocktail dress as she walked past.

"Rum and soda," I said, pulling out my card. "I'll get this round."

"In which case, I'll have a double JD and coke," Callum laughed, patting my shoulder.

There was a good atmosphere in Fernando's, just enough people for it to feel lively but not so many that it was crowded. Instead of moving on, we stayed for one more, which turned into two more. I caught the eye of the brunette a couple of other times when she came to the bar to order glasses of wine, but I was having a good time with Callum and, to be honest, trying to hit on women in bars wasn't really for me.

Callum sank his last inch of whisky and coke and looked over at me, then at his watch.

"Alright, I think that's me, old chum," he announced, but my attention was momentarily distracted by a dark-haired girl in a gold dress with a fantastic bum who walked past and made eye contact, giving me a momentary smile. Without being too obvious, I looked over my shoulder to see where she was going, and watched her slide into a booth with the pretty brunette, who looked at me too. It felt like this was more than coincidence and I looked back at Callum.

"I'm going to stick it out for one last drink," I told him, and we shook hands. "Good to see you, have a safe trip home and a great Christmas."

"You too, mate, you too," Callum said, zipping up his coat, grabbing his briefcase and giving me a quick wave as he stepped back out into the cold.

On my own now, I signalled the guy behind the bar and ordered another rum & soda as well as two glasses of white wine. Well, I was fairly drunk and those two girls really were gorgeous. I knew I'd regret it if I didn't at least try.

Trying to look casual, I strolled over to the booth with the dark-haired girl and the brunette. They looked up at me as I approached and I was taken with how good-looking the brunette was - dark brown eyes, a narrow face with high cheekbones, the kind of face they looked for in models. The dark-haired girl was Asian with a rounder face, but she had a button nose, small mouth and also looked hot. She was wearing a lot of makeup and looked more nervous than the brunette.

"Hi ladies, mind if I join you for a drink?" I asked, putting the wine down on the table.

"Of course," the brunette said, swapping sides of the booth to give me somewhere to sit. I did so, taking a sip of my rum and trying to gauge just how drunk I actually was before I said or did something stupid.

"I'm Jack," I said, as an introduction. "Are you two having a good time tonight or just a couple of quiet ones?"

The brunette laughed. "We'll see how the night goes, I think. I'm Charlotte, and this is my friend Sasha."

Sasha smiled at me but didn't say anything, just picking up the wine I had brought her and sipping it. Her dress was a shiny gold with ruches, high-necked so her small boobs were completely covered, but clingy around her waist and hips. Her fingernails were gold, too, and she had dangly gold earrings, and I had to admit that up close, she was having a big impression on me.

Charlotte, on the other hand, was more of a conventionally sexy woman. The low-cut dress she was wearing made it obvious she wasn't wearing a bra, although it was looser around the hips than Sasha's. She exuded confidence and, ordinarily, I probably would have felt a little intimidated. But, I was here for a good time, not a long time.

"Nice to meet you Charlotte, and you Sasha," I replied, giving both of them a smile.

"What about you? Who was your friend?" Charlotte asked, looking in the direction of the bar.

"A work colleague. We were both working late today and were the only ones in the office, so we thought we'd grab a few drinks to relax," I explained.

"Interesting," Charlotte said, tilting her head slightly. "Let me guess... you're a finance guy. Finance director."

I grinned. "No, sorry." I looked at Sasha. "What do you reckon?"

Sasha seemed shy, and as I took another mouthful of rum I noticed over the table that Charlotte had reached over to her and they were holding hands.

"Stockbroker," Sasha said, quietly. She had a beautiful voice, a low register which was so much nicer than the shrill scouse ladies I usually had to contend with.

"Close. I'm a crude oil dealer," I said, sitting back a little. "Exactly as boring as it sounds."

Charlotte let out another little laugh. "Well I'm a solicitor so I know all about a boring job. There's very little excitement in contract law."

"What about you, Sasha?" I asked, keen to get her talking.

Sasha glanced at Charlotte who gave her an encouraging nod. There was something off about their relationship, but between the several drinks I'd had and my general lack of understanding about women, I couldn't put my finger on what it was.

"I'm a nurse," Sasha said.

"Oh, that's great," I said. "At least one of us is doing something worthwhile."

Sasha smiled at me shyly and took another sip of her drink.

I got talking with Charlotte about some of the other bars in the city, asking which she'd been to and comparing notes on which ones we liked. Charlotte was much more talkative and definitely seemed interested in me, keeping eye contact and laughing at my most feeble jokes, but as much as I felt flattered I couldn't shake how alluring Sasha was. She didn't speak much, just occasionally saying something to agree with Charlotte or shaking her head, but in some ways that was even more attractive. Her wavy hair was brushed to one side of her head so her cheek and jawline were exposed on the other, and the more I looked at her the more sexy she looked.

"Okay, I think I've had enough," I said when I reached the bottom of my drink. I was having a good time chatting to the two girls but it was getting late and the bar was beginning to empty, and I didn't want to overstay my welcome. "So nice to meet you both."

"Aw, no, don't go," Charlotte said, pouting. "Or, at least, let us leave with you."

"Sure, okay," I said. I'd decided I'd at least ask for Charlotte's number when we left, if not both of them.

"Just need to freshen up, first," Charlotte said, and she and Sasha shuffled back out of the booth and headed for the ladies'. Sasha really did have an incredible arse and she walked slowly in her heels, her arm linked with Charlotte's. I sat back and loosened my collar slightly. What a weird situation I'd got myself into. But in any case, even if Sasha was too shy, I wouldn't mind getting a date with Charlotte.

A few minutes later, Charlotte came back on her own, walking briskly, and sat down smartly opposite me.

"What do you think of Sasha?" she asked, leaning forward and keeping her voice down.

I was a bit taken aback. "Um, yeah, she's great, really like her," I said. "Why?"

Charlotte smiled. "Would you be interested in... getting to know her better?"

I narrowed my eyes. I could see through the innuendo but the whole thing between Charlotte and Sasha was still off. "For sure, but why can't she talk to me herself?" I pushed.

For the first time that evening, Charlotte looked unsure. She fidgeted with the sleeve of her dress for a moment.

"Okay, let me fill you in, but please listen with an open mind," she said, looking right at me.

"What's going on?" I asked, suspicious now. I wondered whether this was one of those tricks where a girl pretends to be interested in you only for you to find out she's a hooker later.

"Sasha's my... partner. In a way," Charlotte said.

I stared at her. "Eh?"

"Sasha and I are married, is what I mean," Charlotte continued, slightly flustered. "We came here looking for the right... man, to possibly join us tonight."

"Like a threesome?" I asked, my voice low, still confused. "But aren't the two of you lesbians if you're married?"

Charlotte fidgeted more with her sleeve. "Look, I'll just put all my cards on the table," she finally said. "Sasha... Sasha is actually my husband. She's a he, underneath." She pointed down between her thighs to drive the point home.

The world was spinning. It felt like I was being set up in some way. "So Sasha's trans?" I asked, mystified.

"Not exactly," Charlotte said, looking despairingly at me. "My husband, Sam, has always been interested in... being feminine. Tonight is the first time he, or she, has ever had the confidence to go out in public like this."

I rubbed my eyes. "So Sasha is a guy, dressed up as a girl?"

"That's a blunt way of putting it, but, yes," Charlotte conceded.

I puffed out my cheeks. "Well, fuck me," I said. "I never would have guessed. She's absolutely gorgeous."

Charlotte giggled. "Thank you. I helped her with her makeup and hair and everything."

"So how do I come into this?" I asked.

"We were planning to just have a few drinks and a nice time but Sasha saw you come in and we both... thought you looked nice," she admitted. "We've spoken about possibly bringing a guy home before, but, you know, things can get difficult. If you're interested, we'd like you to come back to our hotel room."

I looked at her for a few seconds.

"If you're not interested, that's okay, no hard feelings," Charlotte added.

Going back to their hotel room meant sex. It meant Charlotte taking off that dress. It meant Sasha taking off her dress. But Sasha wasn't female. But Charlotte was. I knew I wasn't gay, but Sasha was completely feminine. And very attractive.

"Listen, this is so, out of nowhere," I told Charlotte. "I'm... interested. But I'm not into men."

Charlotte's eyes narrowed. "To be clear, this isn't just a chance for you to fuck me while Sasha watches," she said, sharply. "If you're interested, you're interested in both of us."

"No, no, that's not what I meant," I said, quickly. "I-"

Glancing in the direction of the bathrooms, Charlotte interrupted me. "We've talked long enough, I can't leave Sasha waiting. In short, if you're okay with Sasha sucking you off and possibly putting your dick up her arse, we'd love to have you. If not, thanks for your time."

She stood up and went back to the bathroom, leaving me dazed. I told myself I needed to make a decision, but there was no decision to make: choose between sex with two incredibly hot women, or at least, two incredibly hot people, and going home with nothing? That was no choice at all.

"Which way's the hotel?" I asked Charlotte when she and Sasha reached the door of Fernando's, holding their coats. Charlotte smiled and Sasha blushed delicately.

They had a room at the Penny Lane Suites, a modern hotel a few minutes' walk away. It mostly catered to overseas tourists and I've never been there before. There was a bar next to the foyer which had a handful of business travellers sitting in it, but we walked straight past to the lifts. Charlotte had the room key in her hand and as we waited for the lift to reach the fourth floor, I noticed Sasha looking at me. She looked away quickly, but I still couldn't get over just how attractive she looked.

Room 412 didn't have much of a view to speak of, but I wasn't especially interested in that. The walk had made my mouth dry, so I ducked into the en suite to fill up a glass of water and then pushed the room's armchair into place facing the bed and sat down in it, legs apart, water in hand. Both Charlotte and Sasha looked nervously at me, and something about their expressions lit a fire in me. I think I was thinking: well, I'm here now, might as well make it as good as it can be.

"Come on, it wouldn't be a threesome without some girl-girl," I said, a little more forcefully than I had wanted, but it worked. Charlotte's mouth dropped open, but she looked sexy and ready, and Sasha's eyes flashed in Charlotte's direction. I watched as the two girls came together, Charlotte's hands on Sasha's narrow waist, Sasha's hands on Charlotte's shoulders. They looked at each other for a moment before kissing, and even I could recognise a look of love when I saw one. If I hadn't believed they were truly a couple before this, I definitely did now.

Every inch of the two girls in front of me was feminine, even knowing what I did about Sasha. Their kiss deepened, becoming more passionate, Sasha's hands in Charlotte's hair now. Their bodies were pressed together, tits touching, Charlotte's skirt riding up a couple of inches as Sasha's thigh pressed between her legs. I heard a soft, feminine moan from Sasha and I could feel myself getting turned on, so I sipped the water and tried to pace myself.

Charlotte broke the kiss for a moment and kissed Sasha's jaw and neck where her hairstyle exposed it, Sasha's eyes closed, lips parted, panting softly. With careful hands, Charlotte reached up Sasha's back, taking hold of the zip at the back of her dress and slowly, silently, unzipping it. I watched the tension in the dress dissolve, Sasha's skin pale even in the low lighting of the hotel room. Charlotte helped it down and revealed Sasha's thin black bra strap, then it fell to her hips, staying up only because of her curves. My cock throbbed as I watched Charlotte's slender fingers slip inside the dress and ease it over Sasha's hips, inching it down painfully slowly, uncovering sheer, seamless black knickers stretched across one of the most gorgeous bums I'd ever had the pleasure of seeing.

Sasha stepped out of the dress, still in her heels, and as she did she turned and I got a better view of her bra. It was sheer, lacy and matched her knickers, and I could see puffy brown nipples through the material. She'd clearly had some kind of padding inside the dress to give her more of a bust because I could see she didn't have proper boobs, but she still looked sexy as hell with her nipples peeking out. As I watched, Charlotte traced her thumb over one of Sasha's nipples, over the fabric, and I heard Sasha's breath catch. Charlotte giggled and kissed her again, putting her hands on Sasha's cheeks, and I happily watched the two of them kissing for a minute or so.