Single in the City

*****

Part 3 of the Single in the City series.

Adventures continue, with a sexy wing-woman at my side.

Hope you enjoy the read!

*****

"A little tired, big guy?"

Tiffany and I were sipping coffee and rehashing the night before, when I had hooked up with her roommate and my good friend Elsa, aided in no small part by Tiffany playing provocateur all night.

"I think I heard some noises coming from your room pretty late too... how are YOU feeling this morning?" I returned the tease, although I was also truly wondering what Tiffany thought about all this. She had clearly pushed Elsa and I together, but Tiffany and I had also recently acted on long-time attraction and had a wild night ourselves, despite her out-of-state boyfriend. She had since pledged to be "wing-woman" for my single life, but how would she react to the sounds of me fucking her roommate right in the next room?

"Not going to lie, I was feeling a little jealous listening to you two at first. But it also really turned me on, and 'Blue' had to make an appearance."

My questioning glance was quickly answered: "My vibrator, Blue!" Tiffany clarified loudly, turning some heads in the coffee shop. She giggled and continued, "If it wasn't for him, I would have felt pretty lonely. I don't think I kept up with you two, but it did the job!"

I laughed, noting the sudden hush and the still coffee cups around us. The hipsters making up most of the crowd were all pretending not to listen, but activity had virtually stopped, and Tiffany was eating up the attention.

"So we're cool?" I asked, wanting to clarify since this was very much uncharted territory for us.

"Oh yeah! As long as I get a turn now and then, I want you to get into as much trouble as possible," Tiffany responded, giving me a dazzling smile and a wink of one of her incredible sapphire-blue eyes.

"That is a deal I can get behind," I responded with a laugh. "Actually, I just got a message from Shelly, one of my sister's friends from back home. She's in town this weekend, and offered to meet up and talk about my breakup, if I wanted a female perspective."

"Yeah, that means she wants to fuck you," Tiffany responded with her trademark deadpan directness. "Remember, I offered to 'talk' too. Really, I just wanted to jump your bones."

"We'll see," I laughed. "I've known her since high-school and she's one of my little sister's best friends. There was always a little attraction, but nothing ever happened between us. She really may just be reaching out to talk."

"Bullshit. You just better tell me every detail after you two bang," Tiffany replied, again loud enough to carry around the café, several people blatantly turning to listen now. Tiffany always loved an audience, and had quickly captured the attention of the entire group of coffee-hounds.

We shared a tight goodbye hug and left the café, hearing some laughs and whispered conversations begin as we passed through the door, especially when Tiffany reached out and gave my ass a playful goodbye squeeze. So far this wing-woman was making my single life anything but boring!

*****

I texted Shelly to let her know I could meet her that weekend. She was planning to meet some mutual friends at a local bar that always had a familiar crowd, so I offered to join her there. I tried to get some clue as to her intentions, but Shelly had always been very composed and while her messages were very friendly, I didn't get any hint that she was after anything more.

I had always been attracted to Shelly, ever since she first came over to the house with my sister while we were still in high-school. She was petite but athletic, very much a runner's body even back then, and had amazing blue eyes that twinkled when she smiled. This paired with her shy but friendly demeanor had captured my attention right away.

My sister was only two years younger than me and it was a small town, so in high school our groups of friends mixed freely. Even though she was my sister's friend, Shelly had always seemed to spend a little extra time near me whenever she could. She had made me curious, but she was so reserved I couldn't tell if she was actually flirting or not. High school being high school, the timing never seemed to work out between us and I ended up dating one of her friends instead.

Since then, in groups she had always made a point to check in with me when she was around, and was always ready with a hug and bright smile for me. I had several friends who had tried to date her, but she never seemed interested, keeping a bit more in the background of the high-school drama and antics. She ended up going to the same college my sister did, so I would see her occasionally but by then she had begun dating someone seriously, and after college had gotten engaged to him. That all fell apart when he suddenly decided to join a fringe religious group and let her know (via email, showing he had no class OR brains!) he could no longer "live in sin" with her.

With that crazy experience behind her, we had traded some emails after I had broken off my own engagement. Learning her story had been a great way to keep my own breakup in perspective... and I think our talks helped her a little too. I even got her to laugh a bit about some of the more absurd turns in her story, and was looking forward to seeing her even if it really was just to talk. A part of me definitely was interested to see if the night held something a little more fun in store, but I was willing to roll with whatever happened.

*****

I caught a cab to the bar, and walked in with a flutter of excitement, ready to see where this next adventure might go. While I truly believed it was most likely innocent, Tiffany's words had me considering the night's potential. I saw Shelly across the bar talking to a group of mutual friends but before I could approach a buddy of mine hurried up to me with a concerned look on his face.

"Hey man, you should know Emily is here and is pretty drunk." The reference to my ex-fiancé put a quick damper on my excitement...what were the chances she was in the exact same bar I was meeting Shelly?

I struggled to maintain a flicker of optimism that this night could still end in excitement, but a slow dread invaded my stomach as I thought about how I would have to incorporate my drunk ex into the equation.

I caught eyes with Shelly; she nodded her head briefly towards my ex, and then shrugged with a sweet smile. She looked amazing, her trim body shown off well in tight jeans that accentuated her fantastic ass, earned from miles of running. Her dazzling blue eyes were set off by her long black hair, which she tucked nervously behind one ear as she walked over cautiously.

We hugged tightly but she pulled away quickly, casting a quick nervous glance in the direction of my ex. I got the sinking feeling that even if there HAD been some chance of us hooking up, my ex-fiancé making an appearance had snuffed that out pretty thoroughly.

"So... might not be the best place to talk about your breakup, huh?" Shelly had slid her hands into the back pockets of her jeans, and I was struggling to maintain eye contact as her chest arched slightly forward.

"Yeah, not ideal," I responded with a sardonic laugh, as I saw my ex turn toward me with eyes blurred from alcohol. We hadn't had an angry breakup, but she could get quite emotional when drunk, and wasn't opposed to making a scene when in that state.

"I'd suggest heading somewhere else but I'm crashing on Stephanie's couch tonight and need to get her key. I'm supposed to meet her here, but she's out on a date and I haven't heard from her" Shelly had to lean in to be heard in the noisy bar, and I felt a quick charge of excitement as one of her hands rested on my arm.

"Well you know, you're welcome to crash at my place, if you want to?"

Shelly looked up at me, cocking her eyebrow and smiling with a slight blush. "Um, I'm not sure that would be a good idea. Plus, I'm a little worried about Stephanie."

My ex had turned and looked back at us talking a couple times during this exchange, and I sensed a confrontation soon, especially if I kept talking to Shelly.

"OK, well I should probably go quickly check in with Emily anyway, before she makes a scene. Maybe by the time that's taken care of, Stephanie will be here and we can find a quieter place to talk?"

"OK! Good luck with that," Shelly said, with another arm squeeze and a sympathetic smile.

By now my ex was just staring directly at me with watery eyes and a red face, so I walked over to her to say hi and hopefully defuse the situation.

"So are you dating Shelly now?" was her first slurred greeting as I walked up.

"Hello Emily. And no, I'm not dating anyone. Shelly is in town visiting friends, and we were just talking."

"Well you could sure fool me," she said, swaying in her stool.

"OK, I can see you've gotten a head start on the beverages, so why don't we talk another time. It was great to see you."

I turned back to the bar, noticing many heads immediately swivel away; I clearly was not the only one expecting a scene. With a sigh, I tried to locate Shelly, but couldn't find her. What had initially been an exciting meeting with an intriguing chance for more had turned sour quickly, and I realized I needed to get out of the situation before it degenerated any further. After another unsuccessful scan of the room, I stepped outside to get some air and escape Emily's line of sight.

Shelly was outside, looking at her phone. I sidled up next to her and leaned back against the wall with a deep, frustrated sigh.

"Hey there! How'd it go?" she asked, leaning slightly over and bumping shoulders with me.

"Not amazing, but not full eruption. I think she's been drinking for quite a while, though, so it may only be a matter of time if I stick around. Any word from Stephanie?"

"No, she's totally AWOL," Shelly replied, looking back down at her phone in frustration and concern.

"Well, offer still stands," I replied. "My place is only a cab ride away, drinks are on the house, and guaranteed 100% free of drunk exes."

Her eyes flicked towards mine and a slow smile came over her face. I realized she was actually considering it, and a slight flickering of my previous optimism sparked in my brain.

"Well, let me text her one more time, and if she gets back to me so I know she's safe, we can go," she said. "I'm going to go back inside to say goodbye to some friends, and I'll be back out to meet you soon."

"Sounds like a plan!" I replied.

When "soon" had become 15 minutes, I chanced another peek into the bar. I didn't see Shelly anywhere, but noticed Emily was still rooted to her stool, although now was leaning heavily against the bar and seemed deep in conversation with a friend who was nervously looking around for a graceful exit. The friend saw me peaking in, and in what was a clear bid to extricate herself from a drunken monologue, whispered to Emily and pointed towards me.

I ducked back out of the doorway and considered my options: A) I could stay, risk near certain meltdown with my ex, all for the SLIGHT chance at hooking up with Shelly, or B) I could call it a night, avoid the scene, and possibly reconnect with Shelly another time. When another quick scan of the room still proved fruitless and "soon" had now become almost 30 minutes, I made the decision and went with option A; hailing a cab to head home.

I was relieved to be away from my volatile ex, but still slightly disappointed overall that I hadn't had the chance to talk to Shelly. She had looked really good, and had seemed more friendly than usual. Could that be flirting, or just sympathy for my situation?

My phone buzzed in my pocket, and I pulled it out to see a text from Shelly.

[SRY! Got caught in the bathroom with a crying friend. Where R U?]

[Hey! Thought U may have left, so now in a cab home] I responded, curious about how she would respond.

[Oh! Well Steph finally called and she's OK. Offer still stand?] I smiled in the dark backseat of the cab and typed my response.

[Yup! Stay there] I shot back, then told the cab driver to take me back to the bar, excitement in my voice.

*****

I saw Shelly standing outside the bar, and instructed the cab driver to pull up next to her.

"Hey pretty lady, need a ride?" I asked, hanging my head out the window. Shelly giggled and hopped inside.

"Should we try to find another spot, or just talk at my place?" I asked.

"I think I'm done with bars for the night," Shelly responded with a smile and a sigh.

"Let's call it a night and talk at your place."

"Sounds perfect," I replied. "Drinks are cheaper there anyway!"

For the rest of the ride Shelly caught me up on the drama that had gone on in the bar while I was outside, and I thought I detected a bit of nervous body language from her. Could she have had similar thoughts about our meeting up? Was there really a chance I could salvage something from what had seemed to become a complete disaster thanks to my ex?

*****

We got to my apartment and I walked in behind Shelly, taking the opportunity to admire her incredibly tight ass as she walked up the stairs in front of me. She had chosen jeans that were like a second skin, and despite her lean build, running had given her some nice athletic curves in her lower body. I had always been more focused on women's' chests, but Shelly's athletic ass was causing me some serious stirrings and I felt my cock begin to stiffen as I walked up the stairs behind her.

Once inside, we walked into my living room, Shelly dropping heavily onto the couch while I went over to my bar to make us some drinks.

"Nice place you have here," Shelly said from the couch, stretching out a bit.

"Thanks. Still getting used to living alone, though," I replied.

"Oh, I'm sure you're making good use of it," Shelly responded. "I know a bunch of girls have had crushes on you for a long time."

"Oh, really? Like who?" I already liked where this conversation was heading.

"Well, pretty much all your sister's friends had crushes on you at one point or another. We all joked and teased each other about it, in fact."

I handed Shelly her drink and sat down next to her on the couch.

"Man, too bad no one ever told ME about this!" I laughed. "That could have been useful information!"

"You've almost always been in a relationship, so no one had the chance," Shelly replied, fixing me with her bright blue eyes. Was she talking about the girls in general, or sending me a subtle message about herself? I decided to press the issue a bit to find out.

"What about you? Every have a crush on me?"

Without saying a word, Shelly answered me by setting her drink down, then suddenly leaning over and kissing me passionately. At first I was too stunned to react, but quickly returned the kiss with equal passion, my heart racing. My hands went to her sides, and I felt her shudder slightly against my touch. We finally broke our kiss and I pulled back a bit to look into her eyes.

"Does that answer your question?" Shelly asked quietly.

It was my turn to answer non-verbally, as I leaned back in and kissed her fiercely, years of pent-up attraction overwhelming my willpower. Shelly moaned and pressed her body into mine, one hand fumbling frantically at my belt and the other pulling up my shirt, without ever breaking our kiss. We finally came up for air, and I pulled back to allow her to take my shirt off. With that completed, I picked Shelly up in a tight embrace and carried her into my bedroom, her tight runner's body lightly resting in my arms.

Once in the bedroom we frantically undressed each other, clothes dropping to the floor while our hands explored newly exposed skin. Once we were both completely naked, I tossed her onto my bed and crawled after her, sliding my body up over hers. I started kissing and nibbling her neck, teasing both of us by gently bumping the head of my rock-hard cock against the outside of her pussy. I could feel her warm, wet heat, and my teasing caused Shelly to moan with every gentle contact.

Her hands were grabbing my ass, trying to pull me into her, but I had plans for her before the main event. I pulled away and began kissing down her body, first her neck, then spending time kissing and nibbling her perky tits, finally kissing down her body until my mouth was right above her pussy. I could smell the light, sweet muskiness of her excitement, and I stole a quick glace up at her before moving any further. Her eyes had an animal hunger as they met mine and she was almost completely still as she waited for what was coming next.

Without breaking eye contact, I gently extended my tongue and slowly licked the entire length of her pussy, starting at the bottom and ending with a light flick of her stiff clit. Shelly moaned loudly, arching her back and throwing her head back while grabbing at the sheets. After a few more agonizing slow licks I could tell she was already beyond foreplay and so began focusing more and more on swirling my tongue around her clit, while sliding two of my fingers inside her. Shelly began breathing heavily and moving her hips against me, one hand buried in my hair and pulling me into her.

She grew suddenly quiet and I realized she was already on the brink of orgasm. I applied slightly more pressure while keeping my rhythm and she came hard against my tongue, her lean strong thighs tightening against my head and a scream stifled into my pillow. I reached my free hand up to play with one of her nipples as I rode out her orgasm, keeping up stimulation with my mouth and fingers.

Once she had recovered, she tried to pull me up, but I had thought about this for too long, and wasn't going to let her off that easy. I maintained contact with my mouth, easing up on the pressure and rhythm to allow her a small break, but keeping up the sexual energy. Over the next 20 minutes I drew out two more strong orgasms with my mouth and fingers, before Shelly finally begged mercy and dragged me up for a sloppy kiss. Her juices were all over my face after three orgasms, but she didn't hesitate at all, hungrily kissing me deeply.

My cock was straining against her, and she was so wet that the head slipped in briefly as we kissed, drawing quick gasps from both of us. I would have happily pushed further, but she wiggled away from me with a wicked grin.

"Oh no, you're not getting off that easy," she said, flipping me over onto my back. "It's MY turn to torture you like you just did to me!"

She kissed down my body, sliding her tight, toned body along my stiff cock as she made her way down. I was as turned on as I could ever remember being, and just the feeling of her body against mine was driving me crazy. She finally made it down until her mouth was hovering just over my twitching cock. After a teasing lick, she took mercy on me and slid her warm mouth down, taking me inside her mouth. After so much build-up, just actually feeling her mouth on me felt incredible, but I gasped in surprise as she kept going down further and further, stopping only when she had completely taken me into her throat.

Shelly began an incredible blowjob, sliding her mouth from the base to the very tip of my cock and back, her hands gripping and stroking in rhythm. It was an incredible sensation, and I had to look down to see what her technique was that was causing such amazing results. The feeling paired with the sight of her lips wrapped around me cock almost sent me right over the edge. I took a deep breath and somehow regained my focus while her assault on my cock continued.

Finally I couldn't take one more second without coming and so pulled her away. I would have loved nothing more in that moment than to shoot my load into her mouth, but I was not going to miss the chance to fuck her first. I flipped her over onto her back, and slid on top of her, positioning myself between her legs. We kissed urgently as I slid my cock up and down the outside of her wet pussy, prolonging the moment until I would finally be inside her.