Single in the City Ch. 01

Single life begins with a wild experience from an unexpected source.

Hope you all enjoy it! This story begins a little slowly, but builds to a hot finish. There are a lot more adventures in store, based on some of my real experiences. Please leave feedback, happy to hear what you all think.

*****

My recent engagement had just been broken off, and I was trying to figure out what came next. I hadn't been single in the last 10 years, so all my skills and instincts were rusty. I also hadn't had sex in over 3 months as my relationship crumbled, so everything in my body was screaming at me to get some attention, and quick.

As soon as people found out the breakup was final, I felt the love as my friends rallied to my cause; offering to hang out, grab a drink, or just listen to me try to figure out what single life in the big city would be like.

My friend Tiffany was one of the first. She was a short and athletic blond with stunning blue eyes, curly blond hair and a quick smile. She and I had met when her roommate Elsa brought her onto the coed softball team we had started together.

Right away Tiffany had made an impression on the team. She was extremely flirtatious and enjoyed pushing all the single guys as far as she could, savoring how she could make them squirm. She was an actress, and knew exactly how to tease and flirt to make even the smoothest guy stammer and blush.

As the one guy on the team with a long-term girlfriend, I was the only one who was spared the full "T" treatment, although I couldn't help but notice when she, Elsa and their third roommate Krista occasionally giggled and whispered while stealing glances in my direction.

Over time, we had all become good friends, and I had watched as all three of the roommates dated teammates and friends of mine, although each relationship seemed to end after a few wild months. Lately Tiffany had been dating a guy who lived 3 states away. She had brought him to one of our softball games once, but he hadn't made much of an impression, and definitely didn't match Tiffany's crazy energy. I didn't see what she saw in him but he seemed like a nice enough guy, if in a very average "khakis and collar" kind of way.

Over the course of our friendship Tiffany and I had shared some wild stories of our sexual past (usually after some adult beverages), and there had always seemed to be a strong attraction lying underneath. We never had been single at the same time however and so this had been shoved in the background, never acted upon. Now that I was single, I was happy to hear from Tiffany as I wallowed in my empty apartment, and allowed myself to wonder just for a moment if it might lead to something a little more fun.

"Hey sexy single man! What are you doing tonight?" Tiffany's voice was as bubbly as ever, and hearing her friendly words perked me up right away.

"Hey Tiffany. My plan was to keep staring at my half-empty apartment and figure out how to start looking for a new place. You?"

"Oh, that won't do at all! You need to get your cute butt back out there again! How about a drink and we can talk about it? It sounds like you need some help from a girl's perspective."

I couldn't think of any good reason to say no, and a drink with my sexy, flirty friend sounded like just what I needed to break out of my funk. Half a thought about what might happen after a few drinks fluttered in the back of my mind but I carefully shut it down, reminding myself about Tiffany's boyfriend.

"Sounds good! Why don't you come by? I just need to jump in the shower, and I'll be ready. Say 20 minutes?"

"Oooh, shower huh? Any hot girls keeping you company?" Tiffany's question caused a quick rush of blood throughout my body, and I felt myself stiffen up a little.

"Sorry to disappoint you, but there's been none of that since the breakup. Maybe if you introduced me to some of your hot single friends...?"

Tiffany laughed, "Oh, you have no idea what you're in for. More to talk about tonight... see you soon!"

Tiffany's call had entirely changed my mood. I now was looking forward to grabbing some drinks with my sexy friend and looked forward to getting her take on how I could rejoin single life.

As I jumped in the shower, I had to calm myself down. Tiffany had a boyfriend, and while I had only met him once and he lived out of state, she was definitely not available. She was just being her fun, flirty self and trying to cheer me up, I told myself. Right?

Despite that, it had been over two months since my breakup, and during that time my hand had been my only relief, leaving me anxious for some action. My mind began to wander a bit against my will, imagining what it would be like if Tiffany joined me in the shower, her tight body sliding against mine. I knew Tiffany was pretty wild and I began to recall all the stories she'd told me about some of her adventures...threesomes, public sex...could I be in store for some of that?

I cleared my mind of those dangerous thoughts, got out of the shower, threw some clothes on and walked down to meet Tiffany at a bar a few blocks from my apartment.

*****

I had beaten her to the bar, and sat sipping a Guinness while sitting alone at a small table. It was probably just my newly-single status, but it seemed like everyone else in the bar was paired up, and I felt exposed and out of place alone at my table. I started to have second thoughts about this night out and considered calling Tiffany to offer a rain check.

"Hey, sexy!" Tiffany popped me out of my daze, and I turned to see her walk up. I had been expecting a casual drink between friends, but Tiffany had dressed up as if for a date. Her long curly blond hair was pulled up, she had put on makeup that set off her dazzling blue eyes and was wearing tight jeans with a sleeveless top that gave a tantalizing glimpse of cleavage.

"Wow, T! You look amazing!"

"You don't look so bad yourself, big guy!" Tiffany returned smoothly, although I thought I detected a slight blush.

She gave me a tight hug, and feeling her tight body pressed against mine reignited some half-forgotten images from the shower. I felt my cock begin to stiffen, and quickly pulled back to sit down. She may be sexy and flirty, but I didn't want to ruin a good friendship by coming onto a taken woman.

We ordered a round of drinks, and Tiffany began asking me about the breakup. We all had been friends, and since my ex and I had broken up with mutual respect and very few bad feelings, Tiffany and the rest of my friends all had lots of questions. I tried to answer as best I could, and it felt good to get some things off my chest.

By the second round the topic had moved on to how I was going to approach single life.

"You know, there are quite a few girls who are going to want to 'talk' with you now that you're single" Tiffany teased. "You know what it means when a girl offers to talk, right? She's trying to get in your pants!"

I couldn't help raising my eyebrow at Tiffany when she said this, and another quick blush came over her face as she realized she had just inadvertently placed herself in that category.

"Oh, take it easy old man!" I was in my early 30's, and 27 year old Tiffany always enjoyed reminding me of the difference in age. We both laughed off the moment, but something lingered in the air between us. Two drinks had loosened me up, and I reminded myself again that she had a boyfriend and was just naturally flirty. I just hoped she realized my normal resolve was much weaker than usual due both to the recent dry spell for sex, and the beers I'd downed at the bar.

After looking at our empty glasses and seeing the long line at the bar, I proposed heading back to my place for another drink, since it was so close and the drinks there were free. I wasn't sure if T would take me up on the offer, but she surprised me by jumping to her feet with a smile.

"Let's do it!"

*****

Once inside my door, she took a look around and gave a low whistle. "Wow, your place looks so empty now!" My ex had moved out with her half of the stuff and since I was moving to my own place soon, I hadn't bothered to fill in the gaps.

I shrugged and grabbed us two cold beers from the fridge. The drinks at the bar had loosened me up, and now that Tiffany and I were alone in my apartment, the possibility that something might happen between us had me a little excited. I had to remind myself again not to do anything stupid, no matter how she flirted with me.

I handed her the beer and we clinked bottles, her dazzling blue eyes locked on mine. She stepped closer as we drank in silence.

"See? You'll be fine, you're already are bringing girls back to your place!"

I gave a nervous laugh. "It'd be nice if that girl were available," I joked. "That shows how bad I am at being single... I bring a girl home from the bar, and it's my good friend with a boyfriend who just wanted to talk."

Tiffany walked past me into the kitchen, slapping my ass on the way. "Oh, you never know when you might get lucky, big guy!"

I felt my cock stir again, and I had to calm myself down before following her into the kitchen. This was just Tiffany being her flirtatious self... or was it?

Tiffany was at the fridge, playing with some erotic poetry magnets and giggling at the sentences she was creating. From behind, her ass looked amazing in her tight jeans, and before I could think better of it I took a chance and walked up close behind her, leaning over her shoulder to see what she was assembling, while gently pressing my body against hers.

She leaned back into me slightly, and revealed her handiwork. The smell of her hair and the feel of her body against mine had me too distracted to read it verbatim, but I remember the words "frothy" and "shaft" were in there somewhere.

"Figure you to go straight for the dirty words!" I teased her, upping the ante slightly by dropping my hands to her hips.

"You know me so well!" she responded, with a slight wiggle of her hips against me.

Tiffany had not moved away, and was actually slightly leaning into me. The closeness of our bodies was beginning to charge the room with sexual tension, and staring at the explicit words on my fridge wasn't helping. She must have felt my cock hardening against her ass, but pretended to focus on the words while contemplating her next creation.

She reached out again and began forming a new sentence.

"Kiss Hot Slippery Tongue Hard." Not exactly Shakespeare, but in that moment it had way more of an effect on me than the Bard ever had, and I seized the moment.

I turned Tiffany around and took my chance.

"OK" I said quietly.

"OK what?" she teased, looking up at me with her lively blue eyes sparkling.

"OK, I will" I replied, pointing at her sentence.

She turned back to me and I leaned down, kissing her passionately. She moaned into my mouth and pulled me close, confirming that this had not just been a casual flirtation.

Our tongues flicked together and her hands moved down to my ass, pulling me into her. I was now rock-hard and she moaned again as she felt my stiffness against her. All caution left my body as the need for her took over.

We kissed urgently, running our hands over each other's bodies. I couldn't believe this was happening! Tiffany and I had always flirted, but I had never even considered that anything would come of it because we both had been in relationships. Now here she was, her petite athletic body pressed against mine, kissing me with a hunger that matched my own, and that feeling was all I could think about.

We pulled back, and I realized this was the last off-ramp. We could separate, call it a drunken kiss, and be friends again tomorrow.

Tiffany made the decision before my addled brain could, grabbing my shirt and pulling it over my head, then leading me to the bedroom.

Once in bed, we attacked each other, clothes flying off as years of pent-up desire erupted all at once. Her hand closed over my straining cock and I gave out a strained moan, the intensity of my desire washing over me.

I slipped my hand down the front of her jeans and felt just how turned on she was as well. Her pussy was dripping wet and she let out a light gasp as my fingers explored her hot folds.

She threw me back on the bed and ripped off my underwear, leaving me completely exposed. She crouched over me and I felt her hot mouth slide down my cock while her hand gently cupped my balls.

"Oh shit, Tiffany that feels amazing!" I sighed. This was too much; the sight of this sexy blonde's mouth sliding up and down on my hard cock was driving me crazy. It had been months since I'd had any contact, and the taboo of getting a blowjob from my taken friend was pushing my excitement to an even higher level.

I was dying to explode in her mouth, but wasn't going to let her off that easy especially since I knew this could be a one-time opportunity. I pulled her off my cock, and threw her back onto the bed, pulling off her panties.

I leaned over her, kissing and nibbling behind her ear then making my way down her neck while allowing the head of my cock to gently prod her slick pussy. She moaned and squirmed against me, our need for each other getting hotter and hotter.

I made my way down to her soft, full tits, licking her stiff nipples and giving each a little nibble while my hands massaged their ample mass. Years of softball and running together had given me a preview of her toned, athletic body in exercise clothes but seeing her exposed was better than I could have imagined.

She was trying to pull me back to her, but I pushed her arms back and trailed kisses down her body, ending with a light lick between her legs. Tiffany arched her back and moaned loudly.

I pushed one leg up and began exploring her pussy with my tongue, circling and testing to see what drove her wild. She was thrusting against my mouth and in only a few minutes breathlessly warned me "Oh my fucking God, Keith, you're going to make me come like that!"

I redoubled my efforts and slid two fingers inside her, pushing her over the edge to orgasm. She came hard and loud, squeezing my fingers inside her and thrashing around on my bed. I kept up my rhythm and pressure, carrying her through her climax with intensity.

Making Tiffany come with my tongue had me hard as steel, with pre-come pearled at the tip of my cock. Tiffany recovered quickly and pulled me to her, kissing me urgently and tasting herself on me.

I could feel her hot pussy sliding against my hardness and couldn't take it anymore. I pushed myself up over her, stared deep into her eyes, and pressed the head of my cock against her. She caught her breath and we stayed still for a moment, both drinking in the moment.

I started gently rocking, rubbing my tip across her, eliciting frustrated moans of pleasure. I reached the limit of my discipline and finally eased myself into her, feeling every inch as I slowly slid inside her.

This was the first girl I'd fucked since my ex, and the excitement of a new body was almost too much to bear. I was able to maintain my composure at first with long, slow strokes, taking the time to savor the intense feeling as we moved together.

Tiffany bucked against me, grabbing my ass and pulling me into her deeper and faster. The last of my composure dissolved and I began fucking her hard, driving into her with years of pent-up desire powering us both to a frenzy.

"Oh fuck, you feel so good Keith, I've wanted this for so long!" Tiffany whispered into my ear. "Fuck me hard, I want to come on your cock!"

That send me over the edge, and I began pounding Tiffany wildly until she came loudly for the second time, her fingernails leaving trails across my back and her tight pussy squeezing my cock as her orgasm ripped through her body.

Watching her come was so sexy it took me to the edge myself, and I could feel myself about to come as well. Tiffany felt me swell inside her and, recognizing what was impending, looked me straight in the eye and whispered "Keith, I want you to come in my mouth. Will you do that for me? I want to taste you."

Listening to that drove me past the point of no return, and an inadvertent moan escaped my lips as she flipped me over and replaced her pussy with her mouth. Her hands slid up and down on my shaft as her head bobbed on my cock, and the feeling was too much to resist.

I arched my back and warned her I was about to come. She broke off for a moment and encouraged me again "Yes, do it Keith, come in my mouth", then sucked me with renewed frenzy as I exploded into her waiting mouth. My body spasmed as I shot over and over deep into her throat. Tiffany moaned encouragement and milked every last drop out of me, torturing me by stroking and sucking well past when I had become so sensitive it almost hurt.

We collapsed next to each other, sweating and smiling, and totally overwhelmed by what had just happened. I couldn't believe I had just fucked sexy-flirty Tiffany, my long-time friend who had caused such turmoil in our group of friends as guys struggle to respond to her blatant sexuality and tight body.

Our eyes met and we both laughed, and then leaned in for a hot kiss.

"That was WAY overdue!" Tiffany scolded me. "I have wanted to fuck you ever since I laid eyes on you years ago. And by the way, so have Elsa and Krista!"

My eyes widened and she laughed at my reaction.

But that is a story for another time!

*****

I hope you enjoyed my tale! It was great reliving it while writing it down, and it only gets crazier from here! I will continue my story, and the cast definitely grows!

Please let me know what you think, this is my first submission and I'd like to hear any and all feedback.

Thanks for reading!