Single in the City

*****

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.