Building a Life in Chicago

"You did great," I answered as I watched Jessica turn back around to Danny and resume kissing him. Danny wrapped his arms around his girlfriend and pulled her on top of him. I could tell that Danny was hard by the way he started to grind his groin on her.

I adjusted in my seat so I could watch as Danny moved his hands to Jessica's sides and started to pull down her jeans shorts. Jessica lifted off him, and Danny slid her shorts and pink thong down to her ankles, where Jessica kicked them off. At the same time, Jessica pulled Danny's shorts and underwear down far enough for his hard, six-inch-long cock to pop out. Jessica held onto his cock as she inserted the tip into her vagina, let go of it, and slid down his shaft.

Danny moved his hands back to Jessica's ass, squeezing her cheeks as he helped her to move up and down his shaft. They kissed again as they worked up to a steady pace, with Jessica moving her body up and down and Danny pressing his hips up into her.

Danny moved his hands up her body, taking the bottom of her tank top in them and pulling it up. Jessica ended the kiss, unwrapped her arms from around his neck, and let Danny take the tank top off. She then reached behind her back, unhooked her white bra, and slid it off her arms as Danny whipped off his shirt. Jessica continued to bounce up and down his shaft as Danny reached forward and grabbed onto her breasts.

Watching them strip naked, I became aware that I still had my shirt on. Keeping my eyes on them, I pulled my shirt off, followed by my black sports bra. I instantly grabbed my B-cup-sized breasts in my hands and squeezed them, using my fingers to rub and pinch my nipples.

I thought about walking over and kissing both of them but didn't want to disturb them as their bodies moved together. I also thought about going to get my dildo but didn't want to miss anything.

Instead, I stayed on the couch, keeping one hand on my breast and moving my other hand down to my clean-shaven pussy. I was still extremely wet from Jessica eating me out and now watching them fuck, and I easily slipped a finger inside myself.

As I pulled my finger out and pushed it back in, I moaned, causing Danny and Jessica to look at me, Danny over Jessica's shoulder and Jessica turning around to do so. Danny smiled and said, "You can come over here; there's plenty of room."

"I know, but I like the view from back here," I responded, looking down as I watched Jessica's ass raise up off his cock before sliding back down it.

Jessica continued to ride Danny as I played with myself, one finger sliding in and out of my pussy while my other hand pinched and rubbed my nipples. I watched as Danny moved his hands all over Jessica's body, squeezing her ass, rubbing her breasts, and helping guide her hips up and down.

Feeling my orgasm coming, I moved my hand off my breast and down to my clit. I rubbed it with my two of my fingers, pressing down hard on it, until my orgasm washed over my body. I tried to keep my eyes open to watch Danny and Jessica fucking, but couldn't, as my eyes rolled into the back of my head, and I nearly fell off the couch.

Jessica was bouncing up and down on Danny as he held her hips and helped her, pressing his hips up into her as she came down. As I watched, Danny made eye contact with me, pushed hard into Jessica, and moaned as he came. "Oh yes," Jessica said. "Fill me with your cum." She slowed down her riding as Danny pumped in and out of her, and they leaned into each other to kiss.

I stood up from the couch and walked towards them as they ended the kiss. They rested their foreheads against each other and were both breathing deeply as they recovered from Danny's orgasm. Jessica looked over at me with a smile and said, "I've missed you watching us."

"Me too," I replied back. "But, I think me and you need to go into the bedroom while Danny recovers."

"I like that idea," Jessica said, giving Danny one more kiss before standing up off him. "Are you going to come watch, baby?"

"I'll give you guys a few minutes, then I'll be in," Danny said.

I grabbed Jessica's hand with mine and started to walk towards the bedroom. Following behind me, Jessica said, "Oh shit, I can feel Danny's cum going down my leg."

Hearing her say that made me even more excited, and I closed the door behind us, pulling Jessica towards the bed and pushing her down onto it. Jessica put her knees up and spread her legs as I climbed in between them. Smiling, I could see Danny's cum dripping out of Jessica's pussy as I leaned down and used my tongue to lick it up.

"Oh, my God!" Jessica moaned as my tongue touched her.

I swallowed Danny's cum off my tongue and licked off the few drops that had gotten on Jessica's leg before saying, "I've always wanted to do that."

"I thought I was going to cum when you touched me," Jessica said, breathing deep again as she looked down at me.

"I guess I'll just have to try again," I said as I moved back to Jessica's vagina. She had a slight hint of hair around it, and I used my tongue to lick up and down her slit, making Jessica moan every time I darted my tongue in and out of her as I moved it around.

I hummed as my lips kissed her pussy lips, sending vibrations into her. At the same time, I brought my arms up, resting one of my hands by my mouth while I continued to reach up with the other until I felt the soft flesh of her breast. I took one of her breasts in my hand and squeezed it, feeling her hard nipples in my palm.

With my hand by her groin, I slowly rubbed all around her, finding her clit, and brushing my fingers across it. "Oh yes," Jessica moaned as I touched her. I left my fingers on her clit, pressing down on it, as I licked the inside of her pussy and rubbed her nipple with my fingers. I switched from one breast to the other and back again.

"God, you're good at this," Jessica moaned.

"Believe it or not, it's my first time eating out another woman," I said after taking my tongue out of her.

"I'm so close," Jessica said.

I dove back in, rubbing her clit even harder with my thumb and index finger, making little circles around it. I darted my tongue in and out of her, licking her slit and sucking on her pussy lips. Jessica put her hand down on my head, pressing my face into her, and I soon felt her juices flowing out as she started to orgasm. As she pressed her hips up and howled with excitement, I eagerly lapped everything up, swallowing it as quickly as I could.

"Oh, my God!" Jessica said as she came down from her orgasm, and I continued to rub her clit and lick up the remains of it. "That was amazing."

I laughed and said, "Are you ready to go full lesbian now?"

I started to move up to lay down next to her, keeping my hand on her soaked vagina, as she replied back, "Nah. As good as that felt, it'll never replace Danny's cock."

"I agree. Do you think your moaning got him turned on again?" I asked her.

"If it did, he can come in. For now, I just want you to touch me and me to touch you," Jessica said, her hand coming up to bring my face to hers. Her lips pressed against mine, her tongue pushing to get into my mouth. I gladly opened my lips so our tongues could swirl together.

As we made out, we wrapped our arms around each other. I grabbed at her breasts and nipples, and she did the same to me. One of her arms went around to my backside, down to my butt, and she used her hand to squeeze my buttcheeks.

After a few minutes of kissing and touching, I pushed Jessica back onto her back. I ended the kiss on her lips and moved down to her neck, leaving kisses all over it, before moving down to her chest. I kissed all over her breasts, briefly brushing over her nipples. I lifted my head up and looked down at Jessica's breasts. She asked what I was looking at, and I said, "Just admiring your breasts."

I smiled and lowered my head down over her left breast, sticking out my tongue and flicking it against her nipple. As she moaned, I wrapped my lips around it and sucked it into my mouth, continuing to suck it into my mouth the entire time. I reached up with my hand and cupped her right breast in it, squeezing it, and rubbing her nipple with my fingers.

I released her nipple from my mouth and moved over to her right breast. I gave it the same treatment, flicking it with my tongue and sucking it into my mouth with my lips. As I played with her breasts, Jessica wrapped her legs around me, pulling our groins together, and started to rock my body up and down hers.

"Oh, God, Kourtney," Jessica moaned.

"Still pretty horny?" I said with a giggle as I switched between her nipples again.

"What's the girl equivalent of please just stick it in me?" She asked.

"I'm not sure. Maybe a dildo?" I responded.

"Or, we could just go get Danny so we can have the real thing," Jessica said, and I agreed.

I rolled off her, checking out her ass again as she got off the bed and walked out to the living room. She returned a few moments later, giggling and doing a cute little jog to rejoin me.

"What?" I asked her. "Did you scare him? Or was he playing with himself?"

Jessica scooted next to me and said, "Neither! He's asleep!"

"So, I guess it's just me and you?" I said, moving back next to her.

"Where's your toys at?" She asked, and I pointed her to the nightstand. I watched as Jessica opened up the drawer and pulled out my two dildos, setting the bigger one on the nightstand. She handed me the smaller of the two and said, "Maybe I'll take the big one later. Or just use it on you.

Jessica lay back down on the bed, spreading her legs open for me. I leaned over her to kiss her lips as I ran the dildo all over her breasts, stomach, and groin.

I brought it up to her mouth, ending the kiss as I pushed it against her lips. Jessica wrapped her lips around it, staring into my eyes as I pushed the dildo into her mouth. I only got a few inches in before hitting resistance, so I pulled it out and stared into her eyes as I wrapped my lips around the dildo and slid it into my mouth, holding onto the base as I swallowed the five-inch-long shaft and head.

I pulled it out of my mouth and brought it back down to Jessica's groin. I rubbed the tip against her vagina before pushing it past her pussy lips and sliding it inside her. I listened to Jessica moan as I pulled and pushed the dildo in and out of her. She closed her eyes, enjoying the feeling of me sliding the dildo in and out of her, going fast and hard, then slow and sensual.

As I watched her face, full of pleasure, I leaned down and started to kiss her neck. Softly sucking her skin into my mouth, letting go, moving to another part of her neck, and kissing there. Over and over, I kissed her neck as I fucked her with the dildo.

"Oh, Kourtney, that feels so good," Jessica moaned. I kissed down from her neck to her breasts, taking her nipples back into my mouth and sucking on them. I felt Jessica's arm sliding down between us until it reached my groin and started to rub my clean-shaven pussy. She slipped a finger inside me, slowly pulling it in and out.

I moved back up and passionately kissed her, our tongues swirling together as we pleasured our vaginas together. I ended the kiss and sat up, causing Jessica's finger to slip out of me. I looked down, watching the dildo sliding in and out of her. I moved my free hand over to her groin and started to rub her clit with my fingers.

"Oh yes. Yes. Yes. Oh, my God!" Jessica moaned, her hips lifted off the bed as she orgasmed again. Her hands went to mine, pushing the dildo deep into her, grabbing at my hand as I pushed my fingers against her clit. I leaned down, kissing her lips against as she rocked through her orgasm.

As Jessica came down from her orgasm, I pulled the dildo out of her, and she opened her eyes to see me sliding the dildo, covered in her cum, into my mouth, where I sucked and licked it all off. I put the dildo down as she said, "Your turn."

We switched positions, me lying down on the bed while Jessica lay on her side next to me. She reached over me to grab the bigger dildo on the nightstand next to the bed. She held it up in front of her. Seven inches long, black, veiny, and thick. I watched as she licked the tip and sucked on it for a second before moving it down to my groin.

I moaned loudly as Jessica inserted the dildo into my pussy, pushing the entire seven inches inside me before pulling it back out, pushing it back in, over and over. She started to do the same things I had done to her, kissing my neck and sucking on my nipples. I watched as she wrapped her lips around the nipple on my B-cup-sized breasts and put my hand on the back of her head, helping to guide her from one breast to the other and back again.

"I still can't believe you can take this whole thing inside you and not hurt afterwards," she said as she stopped sucking on my nipples and looked down at the thick dildo as she fucked me with it.

"I love it," I told her. "It's the closest I've found to just having a real cock. Oh, my God!"

As I finished talking, Jessica reached her hand down to my groin and started to put pressure on my clit. She rubbed it with her index finger, making little circular motions on it. I closed my eyes as I felt the pleasure from it washing over my body. "Jessica, holy fuck, keep going," I moaned out.

I could feel Jessica moving on the bed and let out another moan when I felt her warm breath on my groin. "I'm so close," I said as she slid the dildo in and out. "Yes. Yes. Yes. Oh my fucking God! Yes!" My back arched off the bed, my legs clamping shut around her hand and arm, and a massive orgasm hit me as Jessica put her lips on my sensitive clit and sucked it into her mouth.

She pushed the dildo in as deep as it could go, continuing to suck on my clit, as I bucked my hips up and down, grinding my groin on her face and the dildo. I reached down and grabbed a hold of her hair, pulling Jessica's head away from my pussy and up to my face. Once there, I pushed my lips onto hers and passionately kissed her. I could taste myself on her lips and wanted more, opening my mouth and letting her tongue into it.

We made out as my orgasm ended, and I lowered my hips and back down to the bed. Jessica started to slowly slide the dildo in and out again. We ended the kiss as Jessica pulled the dildo out of me. I watched as she brought it up to her mouth and, again doing the same thing I did, wrapped her lips around it and sucked off my juices from it.

"Wow," I said.

"I know. It's too bad Danny missed out. He told me that watching us was a fantasy for him," Jessica said.

"There is always tomorrow," I said. "Plus, honestly, it was kind of us to have our first time not be watched by somebody."

"True," Jessica replied as she sat the dildo on the nightstand and laid down next to me.

"Has Danny told you his other fantasy for us?" I asked her. When Jessica said no, I explained it to her, and we spent the rest of the night working out the details until we fell asleep, still naked, cuddling with each other.

I woke up the next morning when I heard my bedroom door opening. I opened my eyes to see Danny poking his head in. When he saw I was awake, he came in, wearing only his boxers, and said, "I guess I missed the fun last night."

"How did you figure that?" I asked him, sitting up in the bed, letting the covers fall off me to reveal my naked body.

"Besides the dildos on the nightstand and you both being naked?" Danny said, laughing and shaking his head.

"Yeah, it was pretty fun," I said, looking over at Jessica, who was lying on her side next to me.

"What exactly did you do?" Danny asked.

"We fucked," I responded.

"It was wonderful," Jessica said, surprising us that she was awake as she sat up next to me, the blanket falling off her as well.

"So, are you ready to continue the fun?" Danny asked.

I said yes, but Jessica said, "I need food first." She then leaned over, kissed me on the cheek, got out of the bed, kissed Danny on the ass, and skipped out of the room.

"God, she has a nice ass," I said with a laugh, and Danny agreed.

We followed Jessica out into the kitchen, where we all grabbed some cereal and poured a bowl of it. We sat down at the table, me and Jessica still naked, Danny in only his boxers, and talked while we ate.

"So, really, what is the plan today?" Danny asked, making it obvious that he was staring at our breasts.

"Well, since you missed out last night," Jessica started. "We figured we could make one of your fantasies come true this morning before we head out to explore more of Chicago. Then, we'll come back tonight, and you better not fall asleep again."

"I promise, I won't! What fantasy are you going to make come true?" He asked.

"You'll just have to wait until breakfast is done," Jessica teased him.

"Damn. Are you sure we have to go explore more? I have plenty we can explore right here," Danny said.

"Yes, we do," I answered him. "That frozen pizza we got last night was not a good representation of the pizza you can get here in Chicago. I need to take you guys out for a good deep dish pizza."

"Pizza is the one thing that could get me out of this apartment," Danny said as he finished his cereal.

After me and Jessica finished eating, we left Danny to clean up while we got ready. We brushed our teeth and did our hair, before putting on the outfits we knew Danny would like.

We stood in front of the mirror, looking ourselves over. Jessica, standing five feet tall, had her brown hair in a braided pigtail going down her back. With bright red lipstick on, she was wearing a white tanktop that showed off her C-cup-sized breasts, especially with her not wearing a bra. She turned slightly so she could see the thin string of her pink thong going between her ass cheeks before turning back around to make sure her vagina was completely covered.

In contrast to Jessica's fair skin, my Native American ancestry gave me tan skin all year long. I was a foot taller than Jessica, but with shorter brown hair that I had done into two pigtails. I was also wearing a white tank top, with the hard nipples of my B-cup-sized clearly visible. I have also picked out a pink thong, happy that me and Jessica had matching colors to wear. Jessica passed me the lipstick she had just applied, and I puckered my lips as I used it.

Both of us had athletic-looking bodies. My legs, ass, and abs were more toned and shapely than Jessica's, and her hips were wider than mine, but she was in just as good of shape. After I finished the lipstick, we turned to each other, and she said, "Do you think we might give him a heart attack?"

"Let's go find out," I said, grabbing her hand with mine and walking out of the bathroom.

Danny was sitting in the living room when we walked out. He looked up, saw us, and dropped his phone that he had been holding. "Holy shit," he said.

We giggled as we walked up to him. I helped him to stand up, and he walked around us, looking up and down at our bodies. "I don't know what fantasy you're fulfilling, but my head just filled with a few more," he said.

Jessica let go of my hand and stepped closer to Danny, pressing her body on his. She got on her tippy toes to kiss Danny before saying, "You don't remember telling me that you hoped to get a blowjob from the both of us? And you've always told me how hot you find a woman that wears a white tank top. And we both know how much you love thongs. So, we just combined them."

Me and Jessica both squatted down in front of Danny. At the same time, we both reached out and grabbed at his cock through his boxers. As it grew hard at our touch, Jessica pulled Danny's boxers down his legs and off his feet, tossing them behind her.

I wrapped my hand around his thick, six-inch-long cock first, rubbing up and down his shaft. I pointed his cock at Jessica, who stuck out her tongue and licked his tip before wrapping her lips around it and sliding down the first few inches. She bobbed her head up and down a few times before releasing his cock.