Weekend in Chicago Pt. 02

"I'm sorry, but you keep flaunting that tight little ass in front of me and I just can't take it anymore," I whispered in her ear. "Not to mention I have been wanting to finger, taste, and fuck this pussy ever since you texted me last night." Reaching down her shorts I couldn't help but notice that she wasn't wearing any underwear, that her pussy was very wet, and the little bit of hair that I had seen on my phone the night before was no longer there.

The elevator started to ascend and Cheryl responded, "Oh fuck, you better do all of those things," as I finger fucked her. "This pussy hasn't had cock for nearly 4 months and it is ready for you."

Sliding my finger up and down her pussy lips and all over her clit, the elevator came to an early stop. I had just barely withdrawn my fingers before the door opened. Another young couple came on the elevator and I'm pretty sure they knew something was up because I was still very close to Cheryl. Cheryl stepped back into me so that they could hit the elevator button for their floor. The young woman pushed a floor about 10 floors up and then moved back towards her man. With Cheryl's ass pressed into my groin I slowly raised my fingers up to my mouth and licked the pussy juice from them. I then turned my thoughts to my dick, which Cheryl had reached behind her to grab and rub. As the elevator door opened 10 floors later, the couple walked out and the man wished us a nice evening and then gave me a nod, knowing what was about to happen.

As the elevator closed, Cheryl began to laugh, while she kept rubbing my dick through my jeans.

"Do you think they knew something was up?" I asked.

"Well if the giant bulge in your pants didn't give it away, I think the smell of sex in the elevator did," Cheryl said.

The elevator eventually reached the roof and as the doors opened Cheryl bent over and grabbed the bottle of champagne. As she did I slapped her on the ass and watched as her little butt cheeks jiggled. Stepping out of the elevator we began walking down a short hallway to a door that accessed the roof. Nearing the door we passed the emergency stairwell and that's when I took control again. I grabbed Cheryl by the arm, opened the door, and pushed her into the stairwell. Grabbing the bottle from her hand, I tried my best to put everything down carefully without losing the immediate need to be all over Cheryl. The bottle of champagne made it safely to the floor, but the two glasses shattered as I pressed up against Cheryl and began to passionately kiss her. Her hands grabbed my face and our tongues began to wrestle while I returned my fingers to her shorts and finger fucked her. With nobody there to interrupt us, I continued my assault on her pussy as Cheryl moaned into my mouth while kissing me. Fingering was fun, but what I really wanted was to taste that pussy. I turned Cheryl towards the stairs and led her down a few steps before turning her back around and pushing her down so that she was bent over on the stairs. I then peeled her shorts down and spread her ass cheeks as I proceeded to lick her pussy from behind. With my nose buried in her ass, my tongue went up and down her pussy, bathing my lips in her wetness. As I love to do, I would also occasionally tongue around her asshole which elicited additional moans from Cheryl.

"Oh fuck, I'm gonna cum," Cheryl said.

Hearing this I focused my efforts on her clit. I found that she had begun to rub herself too so my tongue battled her fingers for the attention of her clit. Cheryl's body began to shake and a few seconds later she began to come all over her fingers and my face. It wasn't a lot, but Cheryl began to squirt a little too. This really turned me on so I lifted her up from underneath her legs, causing Cheryl to have to take her hand from her pussy and put both hands on the stairs to support herself. With her legs up in the air I ate that pussy through her orgasm until Cheryl literally had to kick me to get me off of her sensitive clit. I slowly lowered her back down to the stairs and then gently rubbed her pussy, causing her to jump again.

"Fuck, stop, my clit is so sensitive right now. Oh my gosh, that was fucking incredible. Carly said you were good at licking pussy, but that was way better than I could have possibly imagined," Cheryl said sounding exhausted.

"Well the appetizer in the elevator tasted so good, I just had to have some more," I replied.

I then put out my hand to help Cheryl stand up, and as she did I helped her pull up her shorts. "Last night that pussy had a little hair on it, didn't it?" I asked.

"Yes, but Carly told me you liked a shaved pussy so I shaved it for you earlier today."

"Oh really? How did you know I wanted to see it?" I inquired.

"Let's just call it a horny girl's intuition," she replied.

I carefully picked up the bottle of champagne, being careful not to cut myself on the broken pieces of glass. "Sorry about the glasses," I said.

"No worries, the orgasm was totally worth it," Cheryl said smiling.

We finally made it to the roof and it was a beautiful night. There wasn't a cloud in the sky, the hum of the traffic from 58 stories below was barely audible, and even the stars could be seen despite the bright lights of the city below. The rooftop was also nicely decorated with couches, tables, and 2 grills which I'm sure made for great BBQs in the summer. Having lived in the city for years, Cheryl showed me a few of her favorite sites from the rooftop. Then Cheryl walked me over to the east side of the building to show me the view of Lake Michigan. The east side of the building was somewhat secluded from the main part of the rooftop, hidden behind some electrical boxes and huge HVAC system. As we stood there looking at the lake in the distance, I excused myself and came back carrying (ok, really dragging) a small patio furniture couch for us to sit on. Giving me another smile, Cheryl grabbed the champagne and said, "let's do this." Like a woman who has enjoyed many bottles of champagne, Cheryl had no trouble opening the bottle and shot the cork about 20 yards behind us on the roof. A little bit of champagne also sprayed out, probably from when I threw it down in the emergency stairwell.

"Well, since we don't have any glasses, cheers to you and your new place," I said.

"Cheers! And thanks for helping me move and a wonderful evening," Cheryl replied lifting the bottle to the air. Cheryl then took a big swig from the bottle and handed it to me so I could have a sip.

"I don't know, I don't want your germs," I joked.

"Oh, I understand, let me just wipe my pussy juice from your face," she said laughing.

I took a big drink and then the two of us sat down on the couch and passed the bottle back and forth as we spoke. The couch was not very big but at one point I lifted Cheryl's legs up onto my lap so I could give her feet a massage. Feeling relaxed, Cheryl leaned back onto the arm of the couch and closed her eyes. Her feet were well maintained and had a nice shade of pink on the nails. I rubbed her feet for a few minutes and then began to slowly slide my hands up her legs. Her skin was silky smooth and with each rub I went further and further up her leg. Her little short-shorts got closer and closer until at last my hand reached up her shorts and squeezed the inside of her thighs. Cheryl didn't move or make any objections so I allowed my thumbs to very gently come together and stroke her pussy lips. The wetness coming from her pussy was almost immediate and I knew I just had to taste that again. I slowly removed my hands from the bottom of the shorts and grabbed the waistband. With her eyes still closed, Cheryl lifted her butt off the couch just enough so that I could pull her shorts off of her tight ass. As I slowly pulled them off, Cheryl lifted her legs straight in the air, causing me to have to stand in order to get the shorts off. Smashed between those perfectly tanned thighs, was the prettiest, pink, shaved pussy I had ever seen, and it was glistening in the nighttime air. As I maneuvered the shorts over her feet, Cheryl opened her eyes and locked onto mine. Then she slowly spread her legs, giving me an unimpeded view of her delicious honey pot, as she slid a finger between her moist lips and around her clit. I gave Cheryl a small grin before I lowered myself onto my knees and fell face first in between her legs.

I loved every minute of being face deep in Cheryl's pussy and it wasn't lost on me that we were out in public, where someone might see us. As my tongue did its laps around her pussy, I began to play the whole evening's events in my head and needless to say I found myself getting hard. At this point my licks and kisses to Cheryl's pussy had been sensual and erotic. But when Cheryl grabbed me by the back of the head and pushed me deeper into her love canal I found myself starting to get more aggressive. From between her legs I reached up under her shirt, across her stomach, to her breasts and for the first time I found myself holding her perky, 32-B cup titties. Quickly her nipples began to harden between my fingers as she grinded her pussy harder and harder on my tongue. Almost unable to breath, I ripped my head from Cheryl's grasp and pussy and stood straight up. She gave me a somewhat confused look as I bent over and grabbed her shirt at the neckline. I then ripped her shirt open across the chest, exposing her breasts to the nighttime air. For a second I thought about kissing and licking those hard nipples, but instead I flipped her over and put her on all fours, so that I could bury my face back into her ass and pussy. Reaching underneath between her legs, I stroked her clit with my right hand as I licked her pussy and asshole, occasionally dipping my tongue into each hole. With her tits free but her arms still in her shirt, Cheryl's breasts swayed back and forth as she rode my tongue.

"Damn, I've never had my asshole eaten out before," Cheryl moaned as I gave her ass a tease.

Removing my right hand from her clit, I then spread her ass cheeks and proceeded to give her ass a tonguing it would not soon forget. Squirming in my hands and moaning deeply, I had no doubt that Cheryl was loving the attention. But what I didn't know was that she was also reaching for the bottle of champagne. Without warning she turned around and poured a bit down the small of her back, which leaked right into the crack of her ass and into my mouth. I don't think I missed a drop as she did this 2-3 more times. Eventually Cheryl returned the bottle back to the ground and pulled off the ripped shirt from her body. Now completely naked, Cheryl stood up and had me sit on the couch.

"I love your tongue, but the next time I cum, it better be on your dick," Cheryl said. Then reaching down she began to unbuckle my pants and frantically work them down my legs so that she could get to my dick. With my pants at my ankles, Cheryl ripped my shoes off and finished removing my pants. Then she grabbed the waistband of my underwear and pulled them off of me rather aggressively, causing my hard-dick to catapult up and hit me on my stomach. Within seconds my entire shaft was down Cheryl's throat and the Gluck-Gluck sounds of a women deep throating a man were ringing in my ear.

I'm not going to pretend that Cheryl's blow job was the best I ever had. One or two times she clipped my shaft with her teeth, probably because of how aggressive she was being and the fact she was probably a little intoxicated. But I will say she did a great job keeping my dick lubed up with her spit and an even better job working her hands up and down my dick. At one point she had her index finger and thumb, on both hands, wrapped around my dick, going up and down, and twisting in opposite directions as she sucked my dick. This movement, combined with her tongue focusing on the underside of my penis' head, had me seeing stars. She even gave a good amount of attention to my sac, taking each one of my balls into her mouth while she stroked my cock. If I just focused on the wonderful feeling that she was providing me I'm sure I could have come in less than 5 minutes. But I knew I also wanted to fuck this girl so a couple of times I found myself thinking about things like work, sports, etc., just so I didn't end the night early.

Eventually Cheryl took my cock out of her mouth and stood up, making me think it was time to bury my cock in that pussy. But instead Cheryl stood up on the couch, with a leg on each side of my thighs, turned around so her ass was in my face, and then bent over to suck my dick some more. With her pussy just mere inches away from my face I grabbed around Cheryl's waist and pulled her wet slit to my tongue. That's when Cheryl lifted her left leg off the ground, put it on my shoulder, and then did the same thing with her right leg. I was now sitting down, fully supporting her weight, as we 69'd each other. Being in a somewhat upside-down position, Cheryl had to pull her mouth off my dick a few times in order to catch her breath. But she never complained and worked her mouth up and down my dick like a professional.

After a few minutes my arms started to get a little tired and Cheryl could sense I was losing my strength. She slowly took her legs off my shoulders and again worked herself up to a standing position on the couch, with her tight ass facing me. She then bent over, burying my face in her ass, and then proceeded to slid her wet pussy down my chin, chest and stomach until it came upon my saliva soaked cock. Leaning back now against my chest, Cheryl took my dick in her hands and worked it up and down the lips of her pussy, and then whispered in my ear, "Are you ready to fuck this pussy?" With the head of my dick right at the entrance to her pussy I did not answer her questions with words. Instead, I thrust my pelvis forward and rammed my cock between her waiting lips and deep into the depths of her pussy. Cheryl arched her back and moaned in ecstasy as I held my dick up in her pussy. Then ever so slowly she lifted herself up so that the head of my dick was back at the entrance to her pussy, and then she slid back down feeling every inch of my hard dick. For the next two minutes Cheryl gave me what I considered a slow, sensual lap dance, except my dick was working in and out of her pussy at the same time. I also had my hands wrapped around her chest, playing with her breasts and tweaking her nipples.

Eventually Cheryl began to pick up the pace, and when she did she put her feet on the floor and bent over to touch her toes so that we were in a seated reverse-cowgirl position. We got into a good rhythm of fucking where I had my hands on her hips and pulled her onto my cock, while she bounced off my dick waiting for me to pull her back. From behind the site I was seeing was incredible. The outer lips of Cheryl's pussy were stretched around my dick and her juices coated my shaft as she went back and forth. A gave her ass a few spanks and every time I did Cheryl responded by picking up the pace. Because of the position and the movement I was not able to reach around and rub Cheryl's clit. However, with Cheryl bent over it exposed her ass, and not one to miss an opportunity for ass play, I licked the thumb on my right hand and slowly began to insert it into her ass.

Faster and faster Cheryl bounced on my dick. Deeper and deeper my thumb began to sink into her ass, harder and harder Cheryl rubbed her clit. The whole scene was just to much and no matter what I tried to think about to keep myself from cumming, it's like my dick had a mind of it's own and wasn't going to be denied. I started to feel the build up of an orgasm.

"Fuck Cheryl, I can feel it starting to build," I said as I continued to work her pussy with my dick and her ass with my thumb.

"Your cock feels so hard in me," Cheryl replied while still rubbing her clit. "I am so close to cumming, please don't stop...please don't stop." We continued our fucking, each one of us knowing we were close to an end. "Oh, fuck my ass with that finger," Cheryl moaned. In and out my thumb went, Cheryl's asshole squeezed tightly around it. "Fuck, fuck, fuck, I'm going to cum, oh shit, please shoot your load in my pussy, fill me with your ccccuuuuummmm!!"

And with that Cheryl came all over my dick and 5 pumps later I exploded into her pussy with my own orgasm. My thumb slipped out of her pussy and for me the orgasm was so intense I lost my vision for a few seconds as I felt shot after shot of cum coat the inside of her vaginal walls. Cheryl's orgasm lasted a good 15-20 seconds and she kept slamming back onto my dick until her orgasm subsided. Then she slowly leaned back on my chest, gave me a kiss on my cheek, and thanked me for a wonderful fuck, all while my dick was still buried inside of her. We laid there for a few moments and eventually my dick slipped out of her pussy. Cheryl then stood up, turned around to face me, and pressed the lips of her pussy up against my shaft. Sliding her pussy lips back and forth along the shaft of my dick, Cheryl then squeezed the cum from her pussy onto my dick and stomach. I can't imagine Cheryl got all my cum out, but the size of my load that now covered my dick was very impressive. Once she was done, Cheryl bent down and proceeded to lick the cum from my body and swallow it all. Licking her lips and showing me that there was nothing left, she then reached her arms around my neck, straddled me and gave me a long, thank-you, French kiss.

"Thank you so much, that was WAY better than I imagined," Cheryl said, followed up by three quick kisses to my lip. Then reaching behind her, she grabbed my now softening penis and said, "And this guy, what a great performance."

As Cheryl stood up I noticed she had the champagne bottle in her hand and I gave her a look like where did that come from? She asked me if I wanted a drink and I was still somewhat perplexed how she got the bottle. That's when I turned around and standing right behind me was Carly. Fear immediately set in and my heart dropped into my stomach, knowing I was caught.

"Didn't I tell you he was great," Carly said to Cheryl. "I mean thank goodness nobody else was up here because you two are loud mother fuckers when you fuck. But I must say you do put on one hell of a performance."

"I know, right?" Cheryl replied. "And why didn't you tell me he enjoys ass play so much? I mean if I had known that I would have used my butt plug this week to get ready."

"My bad, I mean it was a couple of weeks before he started doing stuff to my ass. I didn't think he would try it with you so fast," Carly said.

I still had no idea what was going on. Was I caught and in trouble? It sure didn't seem that way. These two friends were talking like me fucking Cheryl behind Carly's back was no big deal. The girls must have sensed my confusion by the dumbfounded look on my face.

"Have you figured it out yet?" Cheryl asked?

"No, what's going on," I responded.

Carly then came around to the front of the couch and said to me, "Happy early birthday! You are going to get a threesome for your birthday. The thing is, before Cheryl agreed to it she wanted to fuck you to see if she felt comfortable with you. We have one more night here in Chicago, and my hope is that you remember this trip for the rest of your life."

"I'm sorry, what?" I asked. "You mean this was all part of a plan? You mean you weren't passed out drunk?"

"No, half those drinks and shots tonight I poured out onto the floor to make you think I was drunk. When we were at the bar and Cheryl and I went to the bathroom, we talked about how great our plan was working. In fact, she let me lick some of your cum off of her fingers. I told her to take her panties off and give them to you at the bar. I told her to go into the bathroom while you were showering to get a good look at your dick. I even texted her before we fucked on the balcony last night to give her a head's up so she could watch. I mean Cheryl is super hot, you are a man, and I knew if she pressed you hard enough you would have no choice but to cave and fuck her."