3 comments/ 12581 views/ 14 favorites Single in the City Ch. 01 By: LumberSexual 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! Single in the City Ch. 02 ***** Part 2 of the Single in the City series. Part 1 described a first encounter with a sexy friend, and ended in bed after the first time together. This story picks up right where Part 1 left off. Hope you enjoy the read! ***** "Wow!" Tiffany and I were lying in bed next to each other, breathing heavily and recovering from what had been an intense fuck. She had been a friend for a long time, and after my recent breakup she had offered to give me a girl's perspective on things. One thing had led to another, and even though she had an out of state boyfriend, we soon ended up in bed fulfilling a long-standing sexual tension between us. She turned on her side toward me and pressed her toned body against mine. "Oh yeah, me and my roomies all had our eyes on you since that first softball game when we met you. Elsa had told us about this hot guy she started the team with, and when we showed up at the very first game Krista had targeted you. When she found out you were the engaged one, we were all pretty disappointed!" Tiffany's body wiggled against mine as I couldn't help but picture her and her two roommates. Elsa was Swedish, thin but not as athletically toned as Tiffany, very cute with huge tits and was always very sweet. Krista was the hippy child: long curly brown hair, one of the best asses I had ever seen and a smile that lit up the room. They each were very cute and sexy in their own way, and hearing that they had all been interested in me was just the boost my ego needed as I began single life. "You're thinking about them right now, aren't you dirty-boy" Tiffany teased, reaching down to squeeze my cock. It stirred in response, despite the vigorous sex we'd just had. "Maybe. Sure is a nice thought," I responded. Tiffany giggled and moved closer. "Oh you have no idea. We're constantly naked in the apartment. I get to see Krista's sexy ass and Elsa's amazing tits every day. Just imagine if you came over some time? Maybe we could all play." Even though I knew Tiffany was just teasing me, that thought combined with the feeling of Tiffany's sweat-slicked body rubbing against mine brought my cock back to life and it swelled in her hand. "Oh, is someone ready for round 2?" she said, gently stroking me. "Because I sure am!" I moaned my desire as her hand squeezed against my hardness, and we kissed passionately. "You are so sexy, Tiffany. You're driving me crazy." "Good," came the whispered response, as her dazzling blue eyes met mine. "It's been so long coming, we need to make up for lost time." I pulled her close and rolled onto my back, feeling her heat as she rubbed her pussy against my hardening cock. We kissed again, hands exploring each other's bodies and she began to move against me. When neither of us could stand it any longer, Tiffany rose up a bit and guided me into her waiting pussy. She began riding me slowly, rolling her hips and keeping me trapped deep inside her. After our wild first encounter, it was now time to enjoy each other and we took our time to savor the feeling. I reached up and grabbed her soft tits, nipples standing out proudly. She moaned and covered my hands with her own, guiding me to pinch her nipples. The sight of this hot blonde riding me was incredible, and I began to slowly pick up the pace, thrusting inside her with more urgency. "Oh fuck, Keith! Yes, right there!" Tiffany cried out, grinding against me as I thrust up deep into her. I moved my hands down to her ass to pull her towards me even tighter and began rocking her up and down on my cock. This must have hit the right spot, because her face flushed and her breathing got shallow as a quick orgasm approached. "Oh my god, I can't believe you're going to make me cum again so fast" Tiffany whimpered. "Yes, cum for me baby, I want to feel you cum on my hard cock" I responded, while squeezing her tight ass. That sent her over the edge and she groaned as her orgasm bloomed, one of her hands shooting down to her clit to help it along. If we hadn't already had sex once, that would have been more than I could handle and I would have cum myself from the sight, sound and feel of Tiffany climaxing on my hard dick. I was glad for the extra stamina, to see how long this could last. When Tiffany had ridden out her orgasm, she pulled off me and lay back on the bed, lighting rubbing herself with her hand. "Wow, that was incredible! I haven't had sex in months; you're going to leave me sore tomorrow!" "Well I am first and foremost a gentleman," I teased, "so let's see what else we can do that won't leave you sore." I straddled her torso and pushed her tits together, creating a slick passage between for my cock. "I like where your mind's at!" Tiffany replied with a smile, moving her hands up to squeeze her tits around my stiff cock. I began stroking back and forth, while she slipped a tongue out to lick my head whenever it appeared above her tits. It felt absolutely amazing, and the sight of her beautiful face licking my cock while it was surrounded by her incredible tits was taking me to the edge almost right away. "I want to see you finish yourself all over me this time" Tiffany demanded, taking a break from licking me. "I love to watch that, it is so fucking hot." "Like I said, always a gentleman," I replied. "Happy to oblige the lady's request." Tiffany went back to my cock, now sucking in the entire tip when it got close, and I couldn't hold back any longer. "Oh fuck, here it comes" I warned her. "Do it Keith, cum all over me" she encouraged in her sexy voice. I pulled away from her chest and began stroking over her. Her hand shot down to her clit and she rubbed in time with me, her eyes glued to my cock. She moaned and kept up her verbal encouragement, telling me over and over that she wanted to see me cum all over her body. It was finally more than I could take and I shot my second load of the night all over her jiggling tits as she brought herself to another orgasm with her fingers. A stray shot landed on her lower lip and her tongue snaked out to taste it as I pulled back and finished over her body, leaving her covered in my cum. "Oh. My. God. That was so fucking hot!" she purred, rubbing her hands over her tight body, slicking her body with a mixture of sweat and cum. I collapsed next to her, spent from my second round with this wild girl. "If Elsa and Krista only knew what they were missing!" As always, I couldn't tell if Tiffany was just teasing me or not, but again the thought of her two sexy roommates popped into my brain, and I couldn't help imagine what it would be like to fuck Elsa's huge tits like I had just done to Tiffany, or watch Krista's tight ass bob up and down on my cock. "You're killing me, T!" I laughed. "Have mercy on this poor guy, I still don't even know how being single works." "Oh, I think you're going to be JUST fine," she responded, giving me a mischievous look. We brought our bodies together and tumbled towards sleep, exhausted from the intense experience of finally acting on such long-standing attraction. I drowsily wondered where this left us. As far as I knew Tiffany still had an out of state boyfriend, and either way our friendship was definitely going to change. I hoped I could avoid the tornado of chaos that seemed to follow her at every turn, but those thoughts drifted away as sleep came like a hammer. ***** The next day we grabbed coffee after one more quick sexy session in the shower, and to my relief there was no sense of awkwardness at all. Tiffany declared that she had assumed the position of wingman for my single adventure. "I'll help you, but you have to tell me every detail. And make time for me every now and then too!" This started to answer my questions from the night before. Apparently Tiffany had no intentions of leaving her boyfriend and wasn't looking for me to replace him, but still wanted some occasional hookups with me while her boyfriend was so far away. I wasn't quite sure how I felt about that, but I wasn't sure what her arrangement might be with her man and fucking Tiffany had been so amazing I was content to let that situation stay ambiguous for the time being and let her manage her own relationship. If she wanted to use me now and then, it was fine with me! "So who do you have you eye on?" she asked, getting right to the task at hand. "I have no idea, my head is still swimming from that wild sex last night" I responded with a laugh. Her eyes sparkled as she returned my smile. "Oh, don't worry, that's happening again! But you need to get yourself out there and find some more hotties! I think you should start with Elsa, she just broke up with that jerk boyfriend of hers and needs some action." That was news to me. None of our group of friends had ever been a fan of Elsa's boyfriend, who was wildly over-protective and possessive, while maintaining a cool distance with everyone in the group. "I don't know T, Elsa is a really nice girl and I'm not looking to get right back into a relationship so soon after my breakup," I responded. "Who said anything about a relationship? She just needs to get fucked as well as I did last night!" Tiffany exclaimed loudly, drawing interested stares from around the coffee shop. I blushed and looked down at my coffee while Tiffany basked in the attention, ever the actress on stage. "I'm not sure she'd be down for that as much as you, Tiffany. She seems shy when it comes to that stuff, and I've known her for such a long time. Hell, I only met her because she was a friend of my ex-fiance!" "Oh, she'll surprise you; don't be fooled by the shy-girl cover." "Ok, ok, I surrender! But I still think you're wrong, I just can't see Elsa going for a casual hookup, especially with a close friend," I responded. "Now that you're on the market, you might be surprised who makes themselves available," Tiffany replied with a wink. "There's been a waiting list for you for a long time." "Ego officially restored!" I laughed. We hugged tightly and then parted ways, Tiffany saying goodbye with one last squeeze of my ass. I could hardly believe everything that had happened between us, and walking home I got another rush as I passed the bar where we had met up the night before. 24 hours earlier, I didn't even conceive of the chance we'd actually do anything together, and the reality of what had actually happened had been so far beyond anything I expected that my mind was reeling. Her words had started a fire though, and I went through my mind thinking which of my hot female friends might be available. Tiffany headed the list of course, and apparently her two roommates were there as well. There was another girl I had always flirted with a bit on the softball team, Kate-Marie; would she be a possibility? She was taller and leaner than any of the roommates, acting a bit more like a tomboy (and cursing with an eloquence any sailor would be jealous of) and blessed with an incredible pair of tits setting off her lean, athletic build. There also was a very sexy sales rep that always came into my office and had flirted with me in the past, Jessica. She always seemed to wear a low-cut top when she came into the office, and seemed to find an excuse to bend over whenever we were alone, showing off her enormous tits. I had never responded because I had always been in a relationship, but now that I was single maybe it was time to explore that possibility? I had also just heard from Shelly, an old high-school friend of my sister who lived nearby, and had offered to grab coffee sometime and "talk", since she'd been through a recent break-up as well. I smiled to myself as I realized this being-single thing may turn out just fine. ***** Tiffany and I had agreed to keep our dalliance a secret since she had a boyfriend. I still had no idea what was going to happen between us moving forward, but she showed right away that she was serious about playing wingman for me: a few days after our wild night I got a text from her inviting me out for drinks with her and her roommate Elsa. In any other context that would have seemed like an entirely harmless night out with friends. After all her teasing however, I knew she had a plan that went well beyond just that. Any question about her intentions went out the window when Tiffany texted me the day of our "date", letting me know that Elsa had told her she was looking forward to going out and seeing what happened while she and I were both finally single. Tiffany was stirring up the pot, like she always loved to do, but this time I was happy to let her go since I stood to be the main beneficiary of her plotting. As I was getting ready, my imagination began to roam. Elsa didn't seem nearly as wild as Tiffany, so I didn't think there was really much chance of anything actually happening, but that didn't stop images from flashing in my head about what she would look like naked, her huge tits freed from the conservative clothing she usually wore to avoid attention. She normally acted fairly calm and shy, but Tiffany had taken it upon herself to bring her out of her shell, especially after she had broken up with her jerk boyfriend. I had known her for so long though; I just couldn't imagine her changing so drastically. Making things even more complicated, she was friends with my ex who she'd known before she even met me and although now Elsa and I had become very good friends, she and my ex were still in contact and saw each other regularly. I finally decided to stop thinking about it and just let things develop however they may go. It had sure worked with Tiffany! We three all met at a bar near the girls' apartment. Right away Tiffany was the ringleader, keeping the conversation lively and teasing, telling us both over and over how jealous she was we were single and could "go crazy" in the city. "I'll have to live vicariously through you two, since I'm taken," she said, "even though I haven't actually been able to fuck my boyfriend for months. I've got blue balls!" I couldn't help but quickly catch her eye, but she turned it right back on me. "So Keith, how long has it been since YOU'VE gotten any?" Elsa blushed deeply and sipped her red wine, not able to meet my eyes. "Well, as you two know, Emily and I broke up two months ago, but we had stopped having sex about 3 months before that. I'll let you two do the math" I replied, enjoying the fact I hadn't actually answered Tiffany's pointed question, but hadn't lied either. Tiffany gave me a mischievous smile and decided to let that stand, since she only wanted to see me and Elsa squirm, not actually let the cat out of the bag. "Oh poor baby!" she pouted, "You must want to bang everyone you see now!" "Right?" I responded, "Especially hanging out with sexy girls like you two. I don't stand a chance!" My teasing comment had deepened Elsa's blush, and she glanced quickly up at me to acknowledge the compliment. I was enjoying this flirty banter, but still didn't think Elsa would be up for much more than that, single or no. After we finished our drinks, I offered to buy another round, but again Tiffany seized the controls. "That's silly; we should just go back to our apartment! It's close and the drinks are free there," she said, making eye contact with me as I realized it was the same line I'd used with her on the night we'd spent together. "I can't argue with that logic" I responded, and to my surprise Elsa nearly jumped out of her chair in her rush to get going. We walked back to their apartment along the busy sidewalk, my arms around their shoulders. I got some jealous stares from guys passing by, and ate up every minute as I squired these two sexy ladies back to their place. Tiffany the actress was playing her role to the hilt, leaning into me and stealthily grabbing my ass while eating up all the attention she was getting from passer-by. Elsa was much more sedate, but snuggled up under my arm and held my waist. I could feel the side of her amazing chest pushing into me and I began to feel blood flow to my groin. We made it to their building, a nice old Victorian and tromped up the stairs to their second floor apartment. Tiffany immediately broke out a bottle of wine and poured three generous glasses. We sat down in their living room, and Elsa began telling us about her break up. Either Tiffany had heard this story too many times, or wasn't going to let the party stop, because she quickly cut her roommate off. "Enough about that asshole, good riddance! It's time you get yourself out there and tear this city apart!" Elsa flashed another quick glance at me, and then responded "I'm not like you, Tiffany, I can't just go out to a bar and bring a guy home." "You just did!" gloated Tiffany, pointing to me. From there it was another round of drinks, more teasing and innuendo from Tiffany, and Elsa gradually loosening up to the point where she was keeping up with her lively roommate. I started to think there was a chance of something happening, and if only Tiffany didn't have a boyfriend there was a real threesome vibe starting to happen. Tiffany again took charge of the situation, dramatically yawning and claiming exhaustion. She downed her last drink and said goodnight, with one final teasing look while telling us not to be too loud and keep her up, since Elsa's room was right next to hers. Now that it was just Elsa and I it got quiet. "So, what do you want to do n-..." My sentence was cut short by Elsa's mouth pressing against mine passionately. I returned her kiss, and pulled her toward me. Any wondering whether or not she'd be interested in a fling went down the drain as she straddled my lap and ground against me urgently. My cock sprang to life, and I heard her whimper as she felt it harden against her. She pulled back and looked down on me. "This is just for tonight, OK? Just two single people enjoying each other. We're still friends." "Whatever you say," I responded, and pulled her face back down to mine. She kissed me frantically, the placid shyness a thing of the past. I slid my hands under her shirt and drew them up her sides, pulling her top off. Her tits were amazing, at least DD, and I was anxious to see what they looked like freed from confinement. Her top flung aside revealed a black lace bra struggling to contain the mass of her ample chest. The choice of such a sexy bra hinted that she may have had more wildness in her than I thought. She pulled my shirt over my head and I pulled her into my body, feeling the lacy material of her bra press into my chest. I kissed down her neck and gave her earlobe a quick nibble, earning a light moan in response. I moved my hands around to her back to her bra clasp, and she moved away. "Let's move this to my room," she whispered, pulling me up off the couch. I followed her down the hall, sneaking a peek at Tiffany's door and wondering if she was still awake and listening to us. I thought I saw a light under the door, but wasn't sure. Once inside Elsa's room, she carefully closed the door and then approached me, a bit of her earlier shyness coming to light again as one arm covered her chest. I stepped towards her and moved her arm away, pulling her body tight against mine and bending down to kiss her. I felt a tentative hand move down to my ass and squeeze as I moved my hands to unclasp her bra. The black lace fell to the floor and I stepped back to take a look at what I had only imagined so many times. Her tits were incredible, their soft mass falling slightly out to the sides while staying firm. Her pale nipples had hardened at being exposed, and cast small shadows in the soft light across her pale pink areolae. She looked at me with a nervous question in her eyes, then relief as I smiled and pulled her back into me for another deep kiss. Single in the City Ch. 02 I picked her up and laid her down on her bed, hands roaming across her body. She squirmed against my touch, very soft moans leaving her lips. I realized she was being quiet because of her roommate in the next room, and I was immediately turned on even more by the combined effect of having to be quiet, and imagining what Tiffany might be doing to herself as she listened for noises. With a gleam in my eye, I pulled back to slide Elsa's pants off. She was looking at me hungrily, and I slid back up her body, giving the insides of her calves and thighs little kisses and nibbles as I went. I could smell the light musk of her excitement as I got higher, and ended my attack with a light kiss right at the source, still covered with black lace. "Pretty nice underwear for a night out with friends," I teased her, looking up at her blushing face. "Well, I..." I quieted her fumbling response by hooking my fingers around the lace and pulling them down, exposing Elsa completely. She closed her legs at first, then hesitantly opened them again as I moved back up her body. This time I wasn't just teasing, and pulled her leg over my shoulder as I let my tongue slide across her pussy for the first time. Elsa let out a moan, cut off as she remembered her roommate again. I smiled, realizing Tiffany had almost certainly heard that, and began licking Elsa with purpose. She was incredibly wet and when I felt her hand move down to my head and pull me closer, I began swirling my tongue against her clit. She immediately arched her back and pushed against me, breathing heavily and stifling her moans with her free hand. "Oh my God, Keith, that feels SO good! Shawn would never do this for me..." Normally a girl bringing up an ex during sex would not be a great thing, but in this context it got me even hotter as I saw how appreciative Elsa was to feel my tongue. I saw her pinching one of her nipples and I reached up to do the same to the other, earning another stifled moan. The view was incredible, her heaving, pale tits lit softly by a candle on her nightstand, and her reddish-blond hair spilling across her pillow. Her eyes were closed and I felt a new urgency as she pushed against me. "Oh yes, just like that, I think... I think you're going to make me cum," she whispered. I slid a couple fingers inside her to massage her g-spot as my tongue held pace and heard her whispered moans gain power. "Oh, yes... oh... YES!" Elsa came hard against my mouth and I struggled to maintain contact as her hips bucked wildly. I managed to keep my tongue firmly on her clit, while my fingers pistoned in and out of her wet pussy, riding out her orgasm. Her self-control slipped as she came, and she moaned loudly until she could compose herself again. Seeing her flushed face over her jiggling tits had me hard as steel, and once her orgasm had subsided, I moved up her body, making sure to stop and kiss each proud nipple on my way up. I kissed her flushed chest, then neck, then finally her lips. She kissed me tentatively at first, her juices still all over my face, then reached a hand around my neck and pulled me closer for a more passionate kiss. "Keith, that was incredible! I haven't had that in SO long...Shawn thought it was gross." "Well, I love doing that, and watching you cum like that was insanely hot," I responded, getting an appreciative wiggle in response. "Your turn!" Elsa whispered, reaching a hand down and squeezing my hard cock. It was pressing against her wet pussy and I was dying to fuck her, but she flipped me over and slowly kissed down my chest, her nipples grazing heavily against my body as she moved down. Her mouth settled down over my cock slowly and her hand began rhythmically stroking me in time. It felt amazing, and the sight of her huge tits squeezing out on either side as she moved down my cock was driving me wild. I knew I wasn't going to last very long under this treatment, so when I couldn't stand it any longer I pulled her up towards me, sliding her body against mine until I could feel her wet heat against me. She pulled back a bit and stared me in the eye, seeming to drink in the sight of me. "I can't believe you're in my bed," Elsa whispered, a strand of her long strawberry-blond hair falling across her face. "Me either," I responded, "but I'm glad I am!" Elsa smiled and moved her hips against mine, rubbing her pussy up and down my length. Another brief thought of Tiffany came into my mind; she had definitely heard Elsa's moans as she came, and I hadn't been as quiet as I could have been either. The thought of Tiffany playing with herself while listening to us overwhelmed me, and I grabbed Elsa's hips to guide myself inside her. She gasped as I first entered her, then pushed against me as I slowly slid all the way inside her. We remained still for a moment, my cock filling her up, then she slowly began grinding against me. She sat up and I got the amazing view of her tits bouncing to the rhythm of her motion. I reached up and grabbed their firm softness with my hands, squeezing gently and pinching her nipples between two fingers. She threw her head back and picked up her pace in response, riding me with more energy. I moved my hands down to her hips and guided her motion, increasing the pressure and depth as her tits bounced free. She began to ride me harder in response, causing her bed to lightly knock against the wall, and the thought of Tiffany popped into my head again. I realized that I was so turned on I wouldn't be able to sustain this much longer, and pulled Elsa gently off my dick. "Will you fuck me doggy-style," she whispered, "that's the way I can cum the easiest." My smile was all the answer she needed, and she moved forward on the bed, grabbing the headboard and presenting her ass to me. I moved behind her, grabbed her hips and slowly slid inside her. The slight break in action had restored my control, and I began fucking her gently with long, slow strokes. She pushed back against me and I felt a quick flutter against my balls as I realized she was rubbing her clit. That was all the encouragement I needed, and I picked up my pace slowly but steadily. She whimpered into her pillow and I could feel her fingers fly underneath me. "Yes, just like that...just like that," she gasped as I continued to fuck her deeply, grabbing her hips and pulling her back into me. Then with a scream stifled into her pillow she began to cum, her body contracting as the waves hit her. I kept up my pace and fucked her steadily as she came, her fingers urgently rubbing her clit and bumping against my balls. That was almost more than I could bear, and I could feel my own orgasm building. But there was no way I was going to let the opportunity to fuck those incredible tits go by, so once Elsa had recovered, I flipped her over onto her back and straddled her torso. She saw my intention and squeezed her massive tits together, a hungry look in her eye. I slid my hard cock between her soft globes, the gentle but firm pressure feeling amazing. The sights of my cock disappearing between those pale masses, her stiff nipples, and her orgasm-flushed face were huge turn-ons, and I knew I wasn't going to be able to last much longer. "Oh Elsa, that is so fucking hot, you're going to make me cum like that," I whispered. "Do it," came her whispered response. "Cum for me." That was the last straw and my discipline dissolved. I felt myself go past the point of no return and I thrust quickly, erupting between her tits. The first shot hit Elsa's chin and I continued to spurt across her chest, riding out an intense climax as she squeezed her amazing tits around me. All semblance of quiet was gone, and my loud moans paired with the bed knocking against the wall removed all chance that Tiffany hadn't heard us. I collapsed next to Elsa, both of us flushed, smiling and breathing heavily. "I can't believe we just did that," she whispered. "I know," I responded. "We're still friends, right?" I could hear the genuine concern in her voice, and I turned to her with a reassuring smile. "Absolutely. Elsa, you and I will always be friends no matter what. This was a lot of fun, and you are incredibly sexy, but most of all I want to make sure we stay friends." "OK good," she whispered. "I really wanted to do this, but I just broke up with Shawn and I'm not sure what to think about anything right now." I laughed gently and moved my hand to the small of her back, rubbing lightly. "Elsa, don't worry about it. This can be whatever you want: one-night stand, casual fling, whatever. I'm still working out how the hell to deal with single life myself, so let's just not worry about it." She snuggled up to me and sighed in relief. "That sounds great. Now I need some sleep!" We began to doze off in each other's arms, before Elsa turned to me one last time. "I wonder if Tiffany heard us?" I smiled in the dark, imagining the same thing. "Oh... I'm sure she was asleep," I reassured her, knowing there was no way that was true. It seemed to be enough for her though, and she settled back down, falling into a deep sleep almost immediately. I closed my eyes and replayed the entire crazy night again. Just before I fell asleep myself, I thought I heard the sound of someone closing a nightstand drawer in Tiffany's room next door. I smiled to myself, and drifted into unconsciousness. ***** Hope you enjoyed chapter 2! Thanks for the feedback, there are definitely more stories to come and it encourages me to hear that some of you are enjoying reading them. Please give me any feedback, I'm happy to hear it!