Weekend in Chicago Pt. 01

This is a two-part story about an old girlfriend that led to a sexual encounter with her best friend.

***

It all started when I began dating this girl named Carly. It was a Thursday night and Carly was having a girls night out with two of her friends. The girls were sitting at a table by the bar when my buddy Drew and I struck up a conversation with the three lovely ladies. I was drawn to Carly immediately because she had this cute, wholesome, Midwest look about her. She was about 5' 6" tall and I guessed she weighed about 115 lbs. It also didn't hurt that she had long blonde hair, beautiful blue eyes, milky white skin, and a pair of black pants that looked like they were painted on. For much of the night Carly did not say much as her two friends dominated the conversation. Still I was drawn to Carly as every time I looked at her I caught her staring at me. She would then smile and look away all shy-like. At around 11pm Carly excused herself and said she had to go home because she had work early in the morning. Being a gentleman, I offered to walk Carly to her car and I was happy when she accepted. We ended up chatting outside her car for about 10 minutes when I noticed Carly shivering a little. It was early spring so there was a little bit of a chill in the air. I offered to let her go, so that she could get in her car and warm up, but instead Carly invited me into the car so that we could continue talking.

We shared a little more small talk and eventually I asked Carly if she would want to go out to dinner tomorrow night. She agreed and I pulled out my phone to get her phone number. I then leaned over to give Carly a quick kiss on the cheek goodbye but was met with a full on kiss. Carly's lips were soft and sweet. They were also very moist and when she flicked out her tongue to meet mine it ever so lightly rubbed across my lips before circling my tongue. Fearing that the kiss might end, I reached my right hand up to her face and gently stroked her cheek. Carly responded aggressively by reaching her left hand across my lap and began stroking my dick through my pants. To say I was shocked would be an understatement, as my cock had not even begun to stir. But with her strokes over my pants that changed and quickly an 8 inch tent appeared in the front of my pants.

Breaking the kiss Carly said, "I'll go out to dinner with you tomorrow if you give me some dessert tonight."

Carly then reached into my pants, pulled out my dick, leaned over, and began to give me a blowjob right in the parking lot outside the bar. Here I was thinking this girl was a cute, shy girl. But as she went up and down on my dick, it quickly became clear I was wrong. Carly's blowjob was a very wet, sloppy blowjob, which I like. The added saliva from her mouth allowed her to go up and down my pole much quicker and smoother. I also liked the slurping sounds as my cock hit her in the back of the throat. Nearing my orgasm I began to grab the back of her head and slightly pull on her hair. The head of my cock began to grow and grow as Carly took me deep down her throat. I then exploded into her mouth as Carly squeezed the shaft of my cock and jacked it for all it was worth, trying to get every last drop out of it she could. As my body recovered from the orgasm, Carly sat up, licked her lips and thanked me for the dessert. Having swallowed my load, she then helped me stuff my dick back into my pants and gave it one last squeeze, causing a small amount of jizz to leak onto her finger. Not letting anything go to waste Carly cleaned the cum from her finger with a long, seductive lick from her tongue. Carly and I exchanged a little bit more small talk and set up plans to meet the next night for dinner. I even promised to return the favor after dinner, but that is a story for a different time. Playing back the earlier events from the bar in my head it hit me that I never saw Carly have one alcoholic drink. She was just a sober girl who wanted some dick.

Fast forward to about 3 months later, and Carly and I were still dating, mostly because the sex was spectacular. On this particular weekend Carly and I went to Chicago to see Carly's best friend Cheryl. Cheryl was moving apartments and Carly agreed to help her move. Being the boyfriend, that meant I was going to be helping Cheryl move too. I had seen pictures of Cheryl but that weekend was the first time I met her. Cheryl was an investment banker and lived in a 1 bedroom apartment in downtown Chicago. I guess work was going well because Cheryl was moving into a 2-bedroom apartment on the 44th floor of an upscale, luxury building about 3 blocks from her current place.

When we got to Cheryl's place on Friday afternoon Cheryl was already busy boxing up her family room. Cheryl was about 5' 5" tall, with shoulder length blonde hair, and she had a beautiful smile. I guessed her to have B-cup tits but I knew almost immediately her greatest asset was her little, tight butt. Wearing a pair of short athletic shorts, I could see the bottom of her butt cheeks when she walked into the family room after letting us in. After introductions and a little bit of small talk, Cheryl served us some wine and a few appetizers while we started packing. The girls worked on the kitchen and I got assigned Cheryl's closet to pack up her clothes.

With the girls in the other room I had no one to talk to so I made quick work of the closet. Afterwards I took it upon myself to start on her dresser and this is where things got a little interesting. The first drawer I came across was her sock drawer. I emptied most of her socks into a plastic bin and then came across a small, purple, felt bag. My hope was that this was some sort of sex bag so I was excited to see what was inside. Not wanting to get caught I casually walked over to the bedroom door just to verify the girls were still in the kitchen working. Then I walked back to the dresser and opened up the bag. The first thing to fall out into my hands was a pair of nipple clamps. Connected by a long silver chain, the end of the clamps were pink and had a long silver screw to adjust the tension on them. The next thing to fall out of the bag were four condoms. There was still some weight to the bag so I tipped it over to empty it out and out fell a string of anal beads. Growing in size from the bottom to the top, the ten pink beads rolled around in my hand as I began to imagine Cheryl using them. I quickly brought them up to my face and I breathed in what I imagined was a mixture of Cheryl's pussy and ass...and I must say it smelled good. I quickly returned the items into the bag and threw it into the bin with the socks.

Now being slightly aroused, I opened the next drawer and was happy to discover Cheryl's underwear drawer. I'm sure there were some old, nasty pairs of underwear in the drawer, but my eyes were only drawn to the sexy pairs. My first handful of underwear included a pair of red, white, black, and leopard print thongs, which I held in my hands for a few seconds before putting them in the bin. Returning my attention back to the drawer of underwear I picked up a few more pairs of panties and in doing so I uncovered a small cigar box located at the back of the drawer. Looking at the box I had a strong feeling I wasn't going to find cigars in this box. Again checking to make sure I wasn't going to get caught, I could hear the girls still laughing in the kitchen. Lifting the lid to the box I knew immediately this was Cheryl's main sex box. My fingers first ran across a smooth, solid gold vibrator.

Next was a battery powered purple and pink rabbit vibrator, with ass stimulator. Rounding out the contents of the box were a small pocket rocket vibrator, approximately 12 more condoms, and 2 flesh colored dildos of different sizes. I quickly put the box and it contents into the bin with the rest of the clothes and continued emptying the dresser. Eventually I came across Cheryl's bras as well. Like with her panties I was drawn to the sexy lace bras. I noticed most of them were size 32B but there were a few 32C as well, making me think she was on the larger size of the B-cup. As I was emptying the last drawer of t-shirts and tank tops both girls walked into the room to see how I was doing. I told the girls I had emptied out the closet and dresser and made sure to look at Cheryl to see her reaction.

"Did you get everything out of the dresser and into the bin?" she asked.

"I sure did, everything," I replied.

Cheryl gave me a small, sexy grin and said, "Well thank you VERY much."

"No worries, it was my pleasure," I said with a wink.

The whole exchange seemed normal to Carly, but I could tell Cheryl knew what I had seen. Afterwards the girls and I changed and got ready for dinner. As a thank you, Cheryl took Carly and I out to dinner to a great Mediterranean restaurant and we spent the evening eating, drinking, and laughing. Even in very casual outfits both girls looked great and I felt like a million dollars being out with these two smoking hot girls. By the end of the meal we were all a little tipsy and decided to head back to Cheryl's place since the next day we had to finish packing and move to the new place.

It was only 11pm when we got back to the apartment. Cheryl quickly went to the bathroom and then said good night and retreated to her room. Carly excused herself to the bathroom to get ready for bed and I pulled out the sofa-bed. I then stripped off my clothes, leaving just my boxer briefs on, and brushed my teeth in the kitchen before getting into bed. As I laid down Carly walked out of the bathroom wearing just a pair of purple panties and a white tank-top that barely even covered her belly button. Carrying the rest of her clothes in her hand, Carly dumped them on the floor before she jumped into bed and began getting all touchy-feely with me. If there was one thing I loved about Carly it was her sex drive and willingness to have sex in wild and random places.

Reaching for my briefs Carly found my flaccid cock and whispered in my ear, "I'm going to need you to get that dick hard and slip it in my tight, little pussy." Giving her panty covered pussy a little rub, she then reached into my underwear and began to roll the head of my penis between her fingers.

"Are you sure you want to do this with Cheryl in the other room," I asked.

"Absolutely," she responded. "My pussy is on fire right now, and I need your dick to put it out."

With my cock at about half of its erect size, Carly placed it into her mouth and began sucking my dick to help it along. After a few laps up and down the shaft, Carly began to tickle my ball sac with her tongue and even sampled the area between my scrotum and anus, all while pumping her hand up and down my saliva drenched shaft.

Now at my full 8 inches, Carly stood up and removed her panties and tank top. Carly's natural C-cup tits jiggled slightly as she slid her fingers down to her pussy for another little rub. Then she turned around and shook her ass as she walked over to the sliding glass door that went out to the balcony of Cheryl's apartment. Being only six floors up, the view from the balcony was not spectacular. But the swaying of Carly's dimple covered ass was nothing short of spectacular. Oh how many times I had cum on those dimples, and I had a feeling tonight might be more of the same.

Opening the sliding glass door, Carly stepped out onto the balcony completely naked, exposing herself to the buildings that surrounded us. She then grabbed the railing with her left hand, bent over, and with her right hand reached back and spread her ass cheeks.

"Are you coming or what?" she said.

Rolling off the bed, with my rock hard dick sticking straight up, I kicked my underwear off my feet and walked towards Carly. Once outside on the balcony I could see numerous buildings overlooking our scene, with many windows still lit up as it was not that late. Standing behind Carly, I positioned my cock at the entrance of her pussy and gently slid the head of my cock up and down the outside lips of her pussy. Reaching down between her legs with her right hand, Carly grabbed the shaft of my cock and guided it deep inside her. Carly was right, her pussy was on fire and dripping wet. Despite her being relatively tight, I was able to slide into her with ease. With the moon shining down on us and being exposed to anyone who was looking outside their windows, the whole scene was exciting me and making me rock hard. I think the same was true for Carly as well, as after only a few strokes I could see Carly's wetness coating my cock with it's milky-white color. In and out I continued to slowly guide my dick into Carly. In turn, she worked her clit with her right hand while holding onto the railing with her left. Every so often she would take her right hand and massage my balls as they slapped into her ass cheeks from behind. Our rhythm continued for a few minutes until Carly began to feel her pussy loosen up. Once she felt comfortable with my 8 inches splitting her from behind she decided it was time to pick up the pace.

"I'm going to need you to fuck this pussy harder," Carly said.

I responded by grabbing her by the hips and driving my dick deep into her love canal. Flexing the muscles in my cock, the head of my penis ballooned slightly and Carly let out a little moan as I had pushed myself deeper than she could handle. I then picked up the pace and began thrusting into her with more aggression. Still bent over, holding the railing, Carly's tits swung like pendulums with our movements. My abs and midsection smacked into her ass cheeks, causing a clapping sound every time they touched. Reaching around, I tried to rub Carly's clit or grab her titties while I fucked her, but our movements were too much and I had to hold onto her hips with both hands. With her moans coming more frequent, Carly pushed back on my dick faster and faster.

"Oh fuck! Just like that, I love it! Keep fucking me so I can cum all over your big dick! Carly began to moan. "Oh shit, those people over there are going to see me cum all over your dick."

Looking up to my right I could see a window with at least 4 figures looking down on us having sex. Knowing that there were people watching gave me a sudden burst of energy and for about 30 seconds I began to ram my cock even faster in and out of Carly's pussy. Even with as wet as Carly was though, I could feel the strokes begin to get a little rough on my penis. Grabbing my shaft, I quickly pulled my dick out of Carly, swung her around, and pushed her down to suck on my cock. She anticipated the movement very well and was quickly taking my dick in and out of her mouth, presumably also enjoying the taste of her pussy that still coated it. Once I felt she had thoroughly lubricated my cock with her sloppy, saliva filled blow job, I pulled her back up by the back of her hair, spun her around, and bent her over the railing again. Only this time I also lifted up her right leg and placed it on the railing as I plunged my dick back in her pussy.

It was a good think that the railing on the balcony was sturdy, as I continued to fuck Carly from behind with reckless abandon. My left hand was holding her hip while my right hand was pulling on her hair. With each pelvic thrust forward into her ass, I would send Carly bouncing forward towards the railing. But with a strong fistful of hair in my right hand I was able to pull her back onto my dick and start the movement all over again. As Carly's orgasm neared she again began to vocalize her pleasure.

"I can feel my orgasm building, please keep fucking me," Carly groaned. "Oh, I'm going to cum all over your dick...fuck, fuck, FFFFUUUUCCCCCKKKKK."

As Carly came on my dick I did my best to keep fucking her and not cum myself. For about 10 seconds I continued the pace as I felt Carly's body being taken over by her orgasm. Finally I could not hold out any more and after one last thrust that I held deep inside her, I pulled my cock from her cum soaked pussy lips and shot load after load onto her back and those beautiful butt dimples.

Returning her right foot to the floor, Carly began to stand up and my cum dripped down her back and into the crack of her ass. Reaching behind her she scooped a little bit of cum from her ass and jokingly offered me a lick. I have never tasted my own cum, nor have I ever wanted to, so I only had to laugh at Carly and she knew to lick it off her own fingers. Exhausted, Carly leaned back over the railing with her tits sitting on the railing itself. I then cuddled up to her from behind, with my dick in the crack of her ass still dripping cum. Reaching around I gave her boobs a nice squeeze and gently kissed her on the cheek. Reminding her about the people watching us, we both looked up to our audience and gave them a quick wave. Two of the figures quickly ran away from the window, as if they were caught doing something wrong. The other two figures remained at the window and returned our wave.

"Thank you," I said to Carly. "And here I thought I was just here to pack boxes."

"Oh, you sure packed my box tight this evening," Carly said laughing. "Besides, I had to reward you with something since Cheryl's not paying you."

"Well my dear, I think you covered my work for today. But I think I'm going to need a little more tomorrow after we move Cheryl into her new place," I replied.

"I'm sure we can work something out," Carly said.

And with that we both walked back into the apartment and into the bathroom to clean up. I had grabbed my phone on the way into the bathroom and sat down on the toilet to take a piss and look at ESPN to catch up on the day's scores. Carly grabbed some toilet paper and had me help her wipe the cum from her back while she wiped the cum from her ass and pussy. She then cleaned her pussy with a little water and used Cheryl's shower towel to pat herself dry. Carly then left me on the toilet to look at my phone, while she went to bed. Unlocking my phone I noticed two text messages from a number that I did not have assigned to a contact in my phone. The first was a 40 second video of me fucking Carly on the balcony, taken from inside the apartment. The second text was a picture of a royal blue vibrator, piercing a set of pussy lips with a small patch of blonde hair in the shape of a landing strip. And underneath the photo was the comment, "looks like you didn't pack all my toys."

To be continued...