Single in the City Ch. 04

*****

Part 4 of the Single in the City series.

A new girl joins the fun, and some instigation leads to a wild group night.

Hope you enjoy the read!

*****

"Ready to get sweaty?"

Tiffany's ever-teasing tone and flashing blue eyes began to lift the morning fog in my brain as she stood in the doorway to my apartment. Form-fitting athletic gear hugged her curves, which she used to every advantage, posing against the door jamb.

"Hey sexy lady! I do remember our morning run plan, but... I am not ready yet". I mumbled, still surfacing into consciousness.

"Big night last night?" she asked, squeezing past me in the door, rubbing her tight body across mine as she came into my apartment. Tiffany lived to tease; a trained actress and flirt, she lived on attention almost as much as oxygen, food and water. I was still adjusting to being single after recently ending a long term engagement, which made me no match for Tiffany's master-level flirtation...my obvious reaction to her sexy body against mine made her giggle.

"Easy big guy, we need to go for a run so I can get ALL of the details from your big night with Shelly!"

"OK, OK," I laughed, "let me throw on some running clothes and I'll rally."

Once I finally got myself ready (Tiffany's watchful eye proved a distracting challenge to keeping my mind on the task), we left my apartment and began a brisk jog into the park nearby. I answered Tiffany's many questions about my night with Shelly, one of my younger sister's friends from back home who I had recently reconnected and enjoyed a wild night with.

"So since you've know her for so long, do you think she wants a relationship?" Tiffany asked, in a brief gap between questions about the dirty details, which were drawing some surprised stares and stumbles from other runners in the park.

"I was a little nervous about that, since I am in no way ready for that yet, but she actually brought it up first...she told me I should be seeing lots of girls right now, and focusing on enjoying myself, so I think we're on the same page."

"I like this one!" Tiffany laughed. "Maybe you can introduce us some time...?"

"One step at a time; she IS still good friends with my sister, not sure I want to mix those worlds quite yet. As interesting as getting you two together sounds, I think we'll wait on that."

Tiffany shot a quick pout in my direction, then changed the subject.

"Speaking of waiting... you better NOT wait to make a move on Krista, she's leaving for the summer next week."

Krista was one of Tiffany's two roommates, along with Elsa who I had hooked up with for the first time recently. They were all good friends who I had known for years and each definitely had their own individual vibe going. Tiffany was the blond, blue-eyed flirt whose never-ending innuendos added spice and potential to any situation. Elsa was strawberry blond, was the quiet and steady one of the bunch who shyly dressed conservatively to hide her amazing chest. Krista was the flower-child of the group, long curly brown hair over a dazzling smile. She gave long, tight hugs and bounced through life with joy and enthusiasm. She also had the best ass I had ever seen, and according to Tiffany had a crush on me from the very first time we met. At that point, I was in a relationship so nothing came of it, but now that I was single the possibility of exploring that attraction was exciting.

"Hello, still with me?" Tiffany's voice brought me back from a line of thought that was starting to get distracting.

"Ha, sorry. What do you mean?"

"Krista is headed up to the mountains to be with her family for the summer. She's bummed because she thinks she may miss her chance with you."

I gave a quick glance, and Tiffany read my mind.

"No, she doesn't know you and I hooked up, but Elsa did tell her about you two. In fact, she told her ALL about it! She also encouraged Krista to go after you before she left town... being single is bringing out a whole new side to shy little Elsa I've never seen before!"

"I'm pretty sure I know who is responsible for that!" I laughed, giving a quick pat to Tiffany's ass as she ran.

"Careful, you know I like that!" she responded. "Any more of that and I'll drag you into some of these bushes and make you fuck my brains out."

A couple running past us turned their heads sharply after hearing Tiffany's comment, the guy drawing a quick punch to the shoulder from his girl as his gaze lingered a little too long. Tiffany glowed, the center of attention as ever.

"Anyway, I told her she should ask you to grab a drink before she heads out of town, and maybe she'll get lucky. She's going to call you today."

I shook my head, amazed at this sexy wing-woman who was dragging me through my early single days with such abandon.

"What about you and Elsa?" I asked. "Don't you two want to say goodbye to her too?".

"Oh don't worry about that, we'll get our goodbyes!" As always, anything Tiffany said sounded vaguely sexual, and I allowed myself to briefly imagine what it would be like to be with all three of them. Tiffany was definitely bisexual and had told many stories of being with other girls, but I wasn't sure about the other two. I know they hadn't ever done anything with each other though, because Tiffany would have told me. Imagining the possibilities with these three sexy girls who I'd been friends with for so long filled my brain and I ran in silence for a while. This line of thought soon started to have its physical effect and I realized I was about to have an issue with my excitement showing through my running shorts.

"What do you say we cut this run off and head back to my place?" I asked.

"You read my mind" Tiffany responded with a twinkle in her eye.

*****

We were barely inside my door before we attacked each other, sweaty running clothes hitting the ground as we stripped down and headed for the shower. We kissed passionately, the endorphins of the run and sexy conversation combining to stoke the fires. My hands ran down Tiffany's tight body, drawing an appreciative shudder in response. I felt her cool hands circle my hard cock and I moaned into her mouth as we continued to kiss deeply. A quick nibble of her neck as she began to slowly stroke me drew a gasp from her, which proved to be the final straw as she pulled away and led me into the bathroom, pulling me behind her.

Once under the hot water of the shower we began to soap each other up, hands running over each other's bodies with slippery joy. I moved behind her and ran my hands up and down the front of her body, while sliding my soap-slick chest against her back. She moaned and leaned back against me, turning her head to steal a kiss.

I slid down enough to allow my hard cock to slide between Tiffany's legs from behind, and rest against the outside of her pussy. I slid one hand down to press my cockhead against her as I thrust back and forth, while sliding my other hand up to cup one of her soapy tits. She moaned and covered my hand with her own, grinding back against me. The feeling of her entire tight body sliding against mine, slick and soapy, was driving me crazy.

"Oh fuck Keith, you are going to make me cum like that, I can't believe...!" Tiffany was cut short as a powerful orgasm caused her to shudder and fall back against me as I kept up the pressure and rhythm of my hard cock against her clit. She came in waves, grinding against me and reaching around to pull my ass towards her. I lightly bit her neck from behind and pinched her nipple as she gradually slowed her movements, then moved away with a sigh.

"I can't believe I came that fast! You must have had me all worked up with those dirty stories. But now you're in trouble" Tiffany purred, pushing me away, then bent over, leaning her hands against the cool tile and presenting her soapy and toned ass to me.

"Now fuck me like you mean it" she said.

I didn't need to be asked twice and moved up to her, grabbing her slippery hips with my hands and guided my throbbing cock to her inviting pussy. I held back for just a moment, allowing the head to lightly part her lips, then she growled "Don't tease me Keith, just fuck me!"

I slid my length inside her and marveled at how hot and tight she felt around me. I began driving inside her with long, slow strokes, gradually began picking up speed as my self-control dissolved. Tiffany was moaning and pushing back against me, encouraging me to fuck her harder.

"Let me know when you're close, I want you to cum all over me," Tiffany said between moans. I felt her hand slide over my balls as I pounded her from behind which began a fire inside me.

"Careful, that will drive me over the edge," I warned, struggling to keep control as I fucked her from behind, the view of her soapy and slick body overwhelming my senses.

"That's what I want, baby!" Tiffany responded, but withdrew her hand as another orgasm began to take hold. "Oh fuck, I'm going to cum again, don't stop!" she commanded, then became silent and tense as a deep orgasm crested and broke while I fucked her hard and fast.

Once we had gradually slowed, she pulled off then turned around and went down to her knees. "Your turn, big guy, I want you to cum all over my tits" she purred, face flushed from two quick orgasms. She grabbed my dick and slid her lips over it, taking most of my length down her throat. She began a quick and aggressive blowjob, her hands and mouth moving together to create amazing sensations that were making control impossible. She looked up at me with her amazing blue eyes, and the sight of my cock disappearing into her mouth drove me further to the edge. I felt her other soapy hand slide across my balls and I could sense the dam about to burst.

"Oh shit Tiffany, you are going to make me cum so hard!"

She grinned mischievously, slid her off-hand further back and I was stunned by the feeling of one soapy finger squirming into my ass while her palm continued to massage my balls. I let out a yell as I began to cum from the surprising sensation, and Tiffany quickly pulled her mouth away and began furiously stroking my cock.

"Yes, do it, cum all over me!" she yelled while both her hands continued their assault on my body.

I grabbed the shower bar and my body convulsed with an orgasm as powerful as I'd ever had. I began shooting all over Tiffany's soapy tits, as she guided and aimed my cock to cover her chest. The sight was amazingly hot, and I came for what seemed like minutes. When I finally couldn't take it anymore, I pulled away from her, light-headed. She pulled her finger out of me, and washed off under the shower, turning back around to wink at me.

"Well, THAT was fun!" she said, glowing with pride at how she had absolutely wrecked me.

"That was intense!" I stammered, gradually recovering. "That's also a first! Never had anyone's finger go exploring before."

"Really?" Tiffany replied. "Oh, you have been so sheltered...time to bring you up to speed!"

*****

After Tiffany left I slipped into a deep, well-earned sleep, so when my phone rang it took me a while to register. I groggily picked it up before seeing who it was and heard a perky voice on the other end.

"Hey Keith! Did...I wake you up?" Krista's voice was as sparkly and recognizable as ever, and it quickly cleared the rest of the fog away.

"Uh... maybe" I replied, sheepishly glancing at the clock and seeing it was mid-afternoon. "What's up?"

"Well, I'm not sure if you know, but I'm going to be going away for the summer. I know we haven't had a chance to hang out since you and Emily broke up, so I wanted to see if you wanted to grab a quick drink before I go away?"

I smiled, knowing from Tiffany that much more than a "quick drink" was at least a possibility.

"Of course! My schedule is wide open all of a sudden, so let me know when and where and I'll be there," I replied.

"How about tomorrow night? Tiffany told me about a cool bar in your neighborhood, we could meet there?"

I smiled quietly again, hearing Tiffany's mischief behind Krista's plan. The bar in my neighborhood was where Tiffany and I had met up before hooking up for the first time, when I was newly single and thought I was just meeting a friend for a sympathetic talk.

"Sure, that sounds great! Sorry to hear you're going away, but it'll be great to see you before you go," I responded.

We finalized our plans and I slipped back to sleep, excited as the prospect of seeing Krista. I wasn't sure if anything would actually happen with her, but allowed myself to imagine several enticing scenarios as I drifted off to continue my well-earned nap.

*****

The next day I was walking home from the gym when my phone buzzed with a text from Tiffany.

< heard u and Krista have a date tonite! >

I laughed and typed back:

< not sure it's a "date", and I KNOW u didn't just "hear" about it, mastermind! >

< LOL, whatever do u mean?? > she responded, with a devil head emoji.

< K had an interesting bar suggestion > I teased.

< It's your lucky charm!! > she texted back, followed quickly by:

< Elsa and I are going to dinner, so you have her all to yourself! >

< U are Hall of Fame wing-woman > I responded, with a trophy emoji.

I truly could never have hoped for the craziness that had happened since my ex and I had broken up, and Tiffany had been at the center of most of it. I had previously been mired for months staring at a half-empty apartment feeling sorry for myself. Since then and thanks to her efforts, I had now been swept up in a tornado of sexy single life that I never could have imagined possible before.

< make me proud! > Tiffany responded.

*****

As it got close to the time Krista and I had agreed to meet, I could feel excitement starting to grow. I tried to temper it by reminding myself there was no guarantee of anything but a friendly drink with a friend, but my gut wouldn't listen and I found my mind wandering. I had never realized Krista had a crush on me when we met on our coed softball team, but I sure had noticed how amazing her ass looked in the athletic yoga pants she wore during games. She was one of the friendliest people I'd ever met, but it had always had an innocence to it; she did not have the suggestive and flirty nature of her roommate Tiffany. She had even briefly dated another guy on the team, but that only lasted a few weeks. They had been so discreet about it I only found out afterward when someone warned me not to put them next to each other in the field, since they had just broken up.

That innocence and discretion made me think it was most likely to truly be just a goodbye drink, with maybe some light flirting, but likely nothing else. Of course, I had thought the same thing about the third roommate, Elsa, who was shy and responsible, and had completely surprised me by taking the initiative and making a move on me, which had turned into a wild and hot night with Tiffany listening in the room immediately next door.

Could this night work out that way too?

*****

With excitement and anticipation, I ended up heading down to the bar a bit early to grab a drink and wait for Krista. I grabbed a private table near the back and sipped a whiskey to calm my nerves and pass the time till she arrived. Before long she texted that she was on her way and I ordered her favorite drink, a Jameson and ginger ale, to be ready for her when she arrived.

When she came through the door, she lit up the entire bar with her trademark smile, and bounded across to the table before crushing me in one of her amazing hugs. I thought I felt a little extra squeeze, but with Krista it was hard to tell... she hugged each time like she hadn't seen you in years.

We broke the hug and settled down to our drinks. She told me about her trip and how excited she was, and also about how much she'd miss Tiffany and Elsa while she was gone. She asked a few tentative questions about my breakup and reached across to touch my arm while I talked about it. Our first drinks went down quickly as we caught up and we ordered a second round.

"So how is single life, after all that time?" Krista asked shyly.

"Honestly a little crazy," I responded. "It's been so long since I was single, I don't really know how to get back into it."

"I've heard you haven't had TOO much trouble" she teased, blushing a bit and looking me in the eye.

"Well... yeah, it's starting to come back to me a bit," I laughed, blushing a bit myself and trying to hold her gaze.

This seemed to be as close as Krista was comfortable getting, so the conversation drifted back to her summer plans. She told me she had been seeing someone, but it hadn't really worked out, so she was looking forward to a fresh start and spending some time with her family. My hometown was in the mountains nearby where she'd be going so we talked about the area for a while, and I started to get the sense that my initial impression was true; that this would be a mildly flirty conversation and drink with a friend but nothing more.

We had each finished our second drink and I decided to test the issue by suggesting a third drink at my apartment.

"Sure!" Krista responded brightly and jumped up from her chair. Maybe I still had a chance?

******

We walked up the hill to my apartment and a new energy seemed to be building between us. Once at my apartment I followed her up the stairs and got a close reminder of what an amazing ass she had. In the glow of two drinks, it was all I could do to remind myself that this still was just an innocent drink with a friend, and not to do anything to jeopardize that.

I poured us drinks and we took them into my backyard, the trees blocking the streetlights and allowing a view of the stars. We stood close together and sipped our drinks while chatting. With a twinkle in my eye, I teased her a bit about how Tiffany had told me she had a crush on me when we first met. She laughed and lowered her gaze, but didn't deny it.

"Yeah, Tiffany has a big mouth sometimes" she said, looking back up at me. "Actually all three of us had a crush on you, but Elsa and Tiffany both had boyfriends, and then we found out you were engaged, so I was out of luck too!"

It was my turn to blush a bit, but luckily the dark starlit backyard hid my reaction.

With a little whiskey aiding my courage I decided to take a chance.

"Well... I'm not anymore" I said softly, and moved closer. She lifted her head to me, and that was the response I needed to take the plunge and kiss her. I heard her take a sharp breath through her nose and moan while pressing her whole body into me. I broke away long enough to set both our drinks down, then slid my hands onto her hips and pulled her back to me. We kissed deeply and passionately, years of attraction coming to a point.

She reached around to squeeze my ass which caused my cock to begin stiffening. I reached around myself and grabbed the ass that I had sneaked so many glances at over the years. It was just as firm and round as I had imagined, and I actually opened my eyes briefly in amazement before her soft moan brought me back and I nuzzled her neck.

It was then that her phone buzzed. We both ignored it at first; then it buzzed again.

"Ugh, one second!" she said and checked who was sending her messages. "Oh, it's Tiffany...she and Elsa are at dinner and they're wondering when I'm joining them."

"What?" I tried to hide my frustration, and pulled her into me again. "Are you going to dinner with them?"

"Well, I kinda said I might, since it's my last night in town" Krista responded, while snuggling up to me. "I never thought anything like this would happen, so I told them to let me know when they went out."

"Can you meet them later?" I asked, running my hands along her sides. "Or much later...?"

Krista put her phone down and pulled my head down to hers, kissing me with the same energy she used in her hugs. She slid her hand the front of my jeans, feeling the hardness below and gave a soft sigh. I grabbed her ass again and pulled her tight to me, just in time for her phone to buzz again.