Weekend in Chicago Pt. 02

Rolling over on the pull out sofa the next morning, I could see Carly's soft, thin, left leg sticking out from underneath the blanket. Peaking under the covers I followed those legs, up to her thighs, right to the pair of purple panties that covered her pussy. Then pulling back the covers further I saw her hard nipples pressed against the white tank top she had worn for bed. I began to play the previous night's events in my head, recounting the fucking we did on the balcony for Cheryl's neighbors. Quickly my dick began to harden and I had to adjust it inside the boxer briefs that I was wearing. Quietly and slowly, I crawled off the bed so as not to wake Carly and I headed to the bathroom to relieve myself.

As I stood up I noticed the smell of turkey bacon and cinnamon rolls wafting through the apartment. The kitchen looked right into the family room where Carly and I had slept, so I was immediately alerted to the presence of Cheryl cooking as I turned around. Standing beside the sofa, shirtless and only in my briefs, I found myself speechless as I stood there looking at her, now remembering the text that I had received from her last night. Did she remember sending that to me? Or was she too drunk to remember?

Seeing my movement out of the corner of her eye, Cheryl looked up from the stove and our eyes met as she said good morning in a low whisper, so as not to wake up Carly. Cheryl had on the same short athletic shorts from yesterday that didn't even cover her ass checks. My sex crazed mind started racing and I thought there was no way she was wearing underwear beneath those shorts. And I'm pretty sure if she bent over that her pussy lips would see the light of day, maybe even some of that landing strip, which I had a picture of on my phone. My semi hard dick was now tented inside my underwear as I said good morning to her and started walking towards the bathroom.

Cheryl's gaze lowered to my crotch area and with a sly smile she said, "Looks like that guy is starting today where he left off last night."

As I walked by her I just chuckled and said, "Sorry, this thing has a mind of it's own."

Once inside the bathroom I closed the door and stood there for a second, with all kinds of thoughts going through my head. Yup, clearly Cheryl remembered last night. She remembered watching me fuck Carly on her balcony and I guarantee she remembered sending me that picture. But what did she expect me to say and do? I mean I was dating her best friend. The worst part was that I was in the bathroom feeling uncomfortable about everything when in fact I hadn't done anything wrong.

I lifted up the toilet seat and began to take my long, morning after drinking, piss. With my dick sticking straight out I had to lean forward and put my hand on the wall above the toilet in order to angle it downwards towards the water. I've always been super self conscious about having girls hear me pee, so I did my best to hit the inside of the bowl and not the actual water. When I was done I walked over to the sink to wash my hands. Looking at myself in the mirror, I did a quick check of myself before I went back out to the family room/kitchen area. I took note of my toned abs and the hip indents that Carly said she found super sexy on me. I also couldn't help but notice the huge tent still in my underwear, but I figured I would use that to turn the tables on Cheryl and make her uncomfortable.

Opening the bathroom door I walked back to the kitchen and saw Cheryl still standing over the stove, making scrambled eggs. I glanced over at the bed and saw Carly still sleeping, with her head facing away from the kitchen. I knew I probably didn't have much time, so I had to act fast. Standing right behind Cheryl, I reached around her, grabbed a piece of bacon off the stove, and whispered, "Wow, this looks delicious," all while gently pressing my bare chest and underwear covered cock up against her back and barely covered ass.

I know Cheryl felt my hard cock trying to penetrate her ass checks because I detected a slight twitch of her ass as she responded, "Well, I have to make sure you have enough energy for all the heavy lifting you have ahead of you today."

"No worries, I can go all night if we need to," I responded. I then turned to walk out of the kitchen and gave her a playful slap on her ass. Cheryl just laughed as I walked away and that is when I noticed Carly was beginning to wake up. I walked over to the bed and ripped the sheets off of her and playfully yelled, "Time to wake up sleeping beauty!" Carly continued to lay there half asleep so with my right hand I reached down to her purple covered, panty ass and gently slid a finger up her pussy lips and asshole.

Instinctively Carly jumped and yelled, "Hey watch it," as she rolled over onto her back. Then I leaned over and gave her a good morning kiss. The kiss lasted about 4-5 seconds and was interrupted when Cheryl yelled that breakfast was ready. Carly stood up from the bed and took a long, hard morning stretch. Then she strolled over to the table in her panties and sat down to eat. I played it a little more conservatively and put on a pair of shorts and a t-shirt before I sat down to eat.

Following breakfast I did the dishes while the girls finished up a few last things before the move. It turned out that Cheryl had hired a few guys, who had a truck, to move everything over to the new place. The move went surprisingly well considering the elevator in the building Cheryl was moving out of was kind of small. Luckily the new apartment had a huge freight elevator. The only bad thing was that the guys Cheryl hired only moved the boxes and furniture into the new place. That meant I had to disassemble and reassemble a number of pieces to include the kitchen table, Cheryl's bed, and a few other pieces of furniture.

What was interesting was how Cheryl's interacted with me throughout the day. I got a few "thank you" hugs from behind and each time she pressed her tits into my back. On one occasion she had walked in while I was bent over and she gave my ass a hard squeeze and yelled to Carly, "You're right he does have a nice ass!" Another time I moved a heavy piece of furniture into place at her new apartment and Cheryl began to massage my neck and shoulders. That alone wasn't weird, but when she then reached around for my chest to give me a hug, she let her hands slide down my stomach and over the front of my pants, lingering for 2-3 seconds. For much of the afternoon I remained frustrated by Cheryl's actions. Was I being crazy and overthinking things, or was she hitting on me behind her Carly's back?

By 6:00pm I would say that 75% of Cheryl's new apartment was unpacked and the girls appeared to be losing steam. We were all getting a little hungry and Carly suggested we just order pizzas so that we could keep working and get everything done for Cheryl. Cheryl was so happy with the progress we had made that day that she again insisted on taking us out for dinner. She said she could finish up the rest of the stuff later in the week and just kept thanking us for everything we had done.

Since the day was a lot of work for us I needed to take a shower before we went out. Carly jumped into the guest bathroom shower first and I tried to jump in with her, but she kicked me out because she knew I was going to try and get frisky with her and talk her into a blowjob. So I was sitting in the family room looking at my phone when Cheryl finished her shower and suggested I just use the shower by her bedroom. I asked if she was sure and she insisted, saying that then we could get going quicker. Cheryl gave me a towel and I went to the bathroom and turned on the shower. The finishes in her new apartment were very nice. Her bathroom had a gorgeous walk-in shower with a clear glass door, if you want to call it a door. It was similar to most of the showers I had seen in Europe where the glass is about half the length of the shower, near the end where the shower head is, and then open to the rest of the bathroom at the back of the shower. I never really understood the appeal of these showers since a bunch of water always got on the bathroom floor, but who am I to play interior designer. What I liked best about the shower was that it had two shower heads, your traditional shower head and then a waterfall one directly overhead as well.

I had both shower heads going when there was a knock on the door and then the door quickly opened. Before I could say anything Cheryl walked in and said, "Don't worry, I've got my eyes closed and I'm not looking. I just need my hair brush." I stood there frozen as she bent over to look in the cabinet under the sink. Dressed in just a pair of sky blue panties and matching bra, I was transfixed on her ass as she was bent over. Without even thinking about it my hand dropped to my dick. I don't know if it was in an attempt to cover it or stroke it, but it responded by stiffening up. With a little bit of fog on the shower glass in front of me, I leaned over to my left so that I could look out the end of the shower without the glass and get an even better look at Cheryl's ass.

The whole episode probably only lasted 10-15 seconds, but it felt like an eternity. Not wanting to get caught staring at her ass, I leaned back under the shower heads and pretended like I was washing soap out of my hair and that I wasn't uncomfortable with her presence in the bathroom. Eventually, Cheryl found her brush and when she turned to leave she turned towards the shower. Still somewhat bent over, Cheryl was at a height a little below that of my dick. Out of the corner of my eye I could see Cheryl take a peek at me and with my hands over my head trying to play it cool, I know Cheryl got a great look at my cock which was still hard and sticking straight out.

With Cheryl gone and my dick still hard as a rock, I had a decision to make. Either quickly rub one out or get out of the shower and get ready. I decided to turn the shower temperature down to super cold, lasted about 5 seconds under the water, and then turned it off and got out of the shower. After drying myself off, I wrapped my towel around my waist and went back to the family room to get dressed. I could hear Carly still in the shower so I figured she must be washing her hair. She took the longest showers and if she was washing her hair it meant we were going to be here for awhile until she was able to dry and style it too. I found a fresh pair of underwear and quickly dropped my towel to put them on. As if right on queue, Cheryl walked into the room just as I was pulling them up. I think she was a little disappointed that I was facing the other way and all she was able to do was get a glimpse of my white ass.

"Oh, sorry! I thought you were already dressed, Cheryl said.

"No problem," I said as I grabbed my jeans, pulled them on, and turned towards her.

I could tell Cheryl was looking right through my jeans and picturing the cock she had just seen in the bathroom. I saw her bite her lower lip as she slowly turned to walk back into her room.

"Carly is still in the shower, so we're probably going to be here another 30 minutes til she is done," I shouted to Cheryl who was back in the bedroom.

"She still takes forever in the shower? Well why don't you grab my phone on the counter and put something on the TV through the AppleTV," Cheryl responded.

I walked over to the kitchen counter and picked up Cheryl's phone. The phone was locked so I asked, "Do you want to come in here and unlock the phone?"

"The password is 6969," she replied.

Of course she would have a password sexual in nature. I unlocked the phone, opened her Netflix app, and put on an episode of "Walking Dead." After about 3 minutes I heard the water shut off which meant Carly was done with her shower. I then heard Cheryl walk into her bathroom and close the door. I probably should have just kept sitting there watching TV, but I decided to be a snoop and go through Cheryl's phone instead. The first thing I did was pull up her messages and found the message she had sent me the night before. I could see the clip of the movie she sent me and the picture of her pussy with the dildo. Then in the comment line I noticed something she had written to me but hadn't sent. It said, "Want to come in and play Just The Tip with me?" After reading this I quickly locked the phone and put it on the couch next to me. Within a few minutes Carly popped out the door ready to go.

"You're already ready?" I asked in a shocking tone.

"Yeah, I didn't wash my hair. I just couldn't get enough of the shower heads and the warm water. I think I almost fell asleep in there it was so good," Carly said.

"I'll be out and ready in about 3 minutes," Cheryl yelled from the bathroom.

Carly was wearing a cute, yellow skirt with a blue and white stripped shirt. Her legs looked great in the outfit and she had these little flat white shoes on to complete her look. When Cheryl walked out of the bathroom she was wearing a white romper with thin blue stripes. It had a little dip in the neckline, but nothing that allowed me to see the cleavage of her large B cup tits. But the romper was short, showing off her thin, tanned legs which I knew met at a beautiful pink pussy with a little bit of blonde hair thanks to last night's photo.

Dinner was great and even better was the fact that Cheryl picked up the tab to thank us for helping her move. After dinner we went to another bar for drinks. I forget the name of the bar, but it was a bar way to nice for me and the drink menu had a lot of over-priced, gimmick drinks. Cheryl ordered some drink that came sealed in a plastic bag and part of the drink was having the waiter open the bag so she could breath in the drink. Carly ordered some drink that came in a bottle with a ship. I just asked for a bottle of beer and both girls gave me a disappointing look. Later I ordered a drink that came on a covered tray and when they removed the lid a whole bunch of smoke came out. $5 for the drink $10 for the show. But again, miss money bags Cheryl paid so I couldn't complain too much.

During dinner and the early part of drinks I felt a little nervous around Cheryl, but of course things loosened up as the night went on and we kept drinking. The girls were reliving old stories and having a great time. I piped in when I could, but mostly I just sat there enjoying my drink and pretending like I was listening. What I did notice was as the girls kept drinking they kept getting louder and louder. At one point Carly excused herself to go to the bathroom, leaving Cheryl and I alone at the table.

"Hey, were you going to say anything about the picture I sent you last night?" Cheryl asked before Carly was even out of site.

"Well, honestly no. I mean your Carly's friend and I didn't know how to respond," I said.

Cheryl replied, "I figured that since you two gave me such a good show last night, and since I got to see you, that it was only fair that you should get to see me."

"Oh, I appreciate the picture very much and it will come in handy the next time I have to rub one out." I couldn't believe I had just said that, clearly I was having some liquid courage. But not nearly as much courage as Cheryl because after I finished this comment she slid real close to me and gently slid her hand over my dick, on the outside of my pants. Within seconds my dick became semi-hard. She then snaked her hand inside my pants and grabbed a handful of my dick. Then she began to slowly work my dick as she whispered in my ear, "I haven't had dick in nearly 4 months since my last boyfriend and I could really use a good workout." Faster and faster she began to work my dick, a little rough at times with friction, but I wasn't arguing. I probably should have been worried that Carly could come back at any moment, but I didn't care about that either.

Again whispering in my ear Cheryl said, "Ever since last night I have been so wet just thinking about you and your dick fucking me. Then when I saw your dick in the shower today I got even more wet and had to use my vibrator on myself in the bathroom while you and Carly were waiting for me to get ready."

The entire contact between Cheryl's hand and my dick could not have even been more than 1 minute, but her comments and stroking put me over the edge and I came from the handjob and all over her hand without warning. Like a boss Cheryl didn't miss a beat. Feeling my cum all over her fingers she released her grip on my cock, withdrew her hand, and licked a few fingers before excusing herself to go to the bathroom.

As she left the table she gave me a quick kiss on the cheek and said, "I hope there is more where that came from."

Sitting at the table alone I quickly downed the rest of my drink and ordered another one, along with three shots for everyone. Eventually both girls came back to the table together, Carly unaware of what had just happened, and Cheryl with a smile on her face knowing damn well what just happened. Eventually the shots came to the table and Cheryl proposed a toast. "To old friends who I love so dear, and new friends and whatever may come (cum) of them," she said lifting the shot. We each downed the shot and while we did I felt something pushing against the waist of my pants. Looking down below the table I could see Cheryl's hand stuffing something in my pants. It took me just a half a second to realize they were the sky blue panties she was wearing when she walked in on me showering. Turns out while she was in the bathroom with my girlfriend and her best friend she had removed them to give to me. At this point I came to understand that I was going to have another go with Cheryl before the night was through, I just didn't know how with Carly around.

The answer to this question came in the form of Cheryl. For the next hour Cheryl kept pumping Carly with drinks and Carly started to get sloppy drunk. At around 1am we decided to call an Uber and head back to Cheryl's place. The ride was about 15 minutes and when we arrived Carly was asleep/passed out on my shoulder. Cheryl and I barely got Carly upstairs into the pull-out bed. Cheryl helped me strip Carly down to her panties and then helped me put a t-shirt on her before tucking her into bed.

With Carly safely tucked into bed I looked over at Cheryl and we locked eyes knowing something was about to go down.

"This building has an awesome rooftop and I have a bottle of champagne in the refridge from my realtor as a house warming gift. Want to head up and have a drink?" Cheryl asked.

"Sounds great," I replied.

"Great, just let me go change into some bedtime comfy clothes," Cheryl said.

As she walked away I said, "Hold up, you might need these." Then reaching into my pants I pulled out her panties and tossed them over to her.

"Thanks," she said. "But hopefully I don't need them," as she winked and walked into her bedroom.

About five minutes later Cheryl came out in the super short shorts that showed her ass cheeks and a tight LSU Tigers shirt that was about 2 sizes to small for her. Since I usually slept in my underwear I didn't have any bedtime comfy clothes to put on, so I just wore my jeans. But I took off my dress shirt and threw on a gray, v-neck t-shirt. I also kicked off my dress shoes and socks and wore a pair of sliders. Cheryl grabbed the champagne from the fridge while I grabbed two glasses.

"Are you ready to go," she asked.

"Sure am. Do we need anything else?" I responded.

"I don't think so, let's go," Cheryl said.

We walked down the hall to the elevator and although we sat in silence waiting for the elevator, we both felt some serious sexual tension, or at least I did. When the elevator arrived I let Cheryl go in first. I could say it was to be a gentleman, but I really just wanted to look at her ass in those shorts. Once inside the elevator Cheryl bent over to put the champagne down before she pushed the button for the roof. To access the roof she had to enter a key before pushing the button. As she turned the key and pressed the roof button Cheryl found herself being pushed up against the wall. I had decided to try and take control of the situation and I pressed myself up behind her and aggressively shoved my right hand down the front of her pants, while still holding the champagne glasses in my left hand.