Chicago Hotwife

"Jessica, are you ready to go?"

"Yes. Coming now." She replied.

Jessica and I were heading out for a night in Chicago to let loose. Jessica is my girlfriend of 2 years. We had an on and off again relationship ever since high school but could never make it work until now. We are both in our early 30's at this point. Jessica is stunningly beautiful. She works very hard to stay fit and it shows. She has the most beautiful, matched with an amazing smile. She has blonde hair that goes just past her shoulders. She has a tiny little butt that is shaped perfectly! Needless to say, she turns heads when she walks into a room.

We were going to be staying at the London House just across the river from Trump Tower. We really enjoyed partying in the River North Area. The plan was to eat a nice dinner then bar hop around. However, I secretly had another plan in mind as well. Over the past year I developed a strange arousal to the thought of Jessica being with another man. It started one night when Jessica and I were exchanging sex stories from our past and I found myself incredibly turned on by her stories. Luckily for me, Jessica had a pretty naughty past and there was plenty to share. Ever since then I wanted her to so badly to be with another man. I either wanted to watch the entire sexual tryst with my very own eyes or have her give me every juicy detail while we fucked around.

About a month ago I finally told Jessica about my fantasy. We were starting to mess around in bed and we started talking about fantasies that we have never been able to live out yet. "To be honest, I have this weird fantasy of you being with other men."

Jessica looked a little shocked. "Are you serious? You wouldn't be totally pissed?"

"Not at all. I have thought about it for long time. I know I wouldn't be pissed. It would be so hot."

Jessica looked very intrigued by this conversation. "But what if I enjoyed it?"

"Even better. The more you enjoy the more I enjoy."

"Interesting..."she cooed as we continued messing around. "So like... you want to watch or... what?"

"I would either like to watch or hear every juicy detail about it when you got back." I was getting hotter and hotter as we continued our conversation.

"What if he was better in bed than you? Bigger cock? Wouldn't that make you feel uncomfortable?" I could tell she was excited but still genuinely concerned about how I would feel.

"Nope. Again, the more you enjoy, the more naughtier you are... the better for me."

Jessica was getting more and more into the idea. She began slowly sucking my rock hard cock. "So you'd like to see me sucking a big cock... just like this?"

"Oh my God yes I would."

Jessica pulled her head up but kept stroking. "Would you want to see him eat my wet pussy?"

"Yes!"

"Show me!" Jessica then laid back and spread her legs wide open. I could see her perfectly shaved smooth pussy was waiting to be licked.

I began fingering her warm wet hole as she started grinding on my fingers. I then went down and began sucking on her clit while continuing to finger her. Now she was grinding her mound on to my mouth. She always tastes so good.

"Right there... right there... don't stop... I'm going to come."

I kept sucking on her clit and plunging my tongue as far as I could into her sweet pussy until she erupted with a massive orgasm.

"Oh my God that was so good."

"Yeah... what were you thinking about?"

Jessica turned to me. "I was thinking about our conversation. Thinking about you watching me with some stranger eating me out. Thinking how fun it would to have you watch me, or to tell you about every little detail."

"God you are so hot!"

Jessica then got on top of me, grabbed my cock and slowly began sitting down until I was completely inside her. She immediately began grinding back and forth. She was so good at getting herself like this.

I leaned up to her. Kissed her mouth and moved down to pay attention to her hard nipples. As I continued to suck on her nipples she was grinding back and forth. She seemed to be extra into our sex tonight and I thought it must've been due to our conversation. "Baby, imagine me sitting down in the corner... watching you fuck a guy just like this. Playing with myself while you fuck his brains out."

After I said this she really picked up the pace. I give her a nice ass slap as she moved back and forth. "Fuck... I'm coming again....!"

"I'm close too... soo close." I could barely hold it but I wanted her to come.

And just like that we both came together. I shot a hot load of my cum deep into her pussy. My cum added lubrication as she continued to grind out her orgasm. I started to see my cum leaking out of her and down my shaft. Jessica then collapsed onto my chest as my softening cock was still inside her.

"Jessica... I think we need to make my fantasy a reality. We both seem to be really into it."

"I agree. I still have this inner slut that needs to get out." She replied out of breath.

Ever since that night we talked about it, fucked like rabbits while discussing it and thought of different scenarios. We were both from a small town so we didn't want people talking about Jessica fucking around so we decided to go to Chicago. Where no one would know us and there was bound to be a guy that Jessica was into. I wanted her to find the perfect guy because I wanted her to be so into that she would be extra slutty.

So we arrived at our hotel around 4:00PM. We checked in, went to our amazing room and began to get ready. We wanted to have a drink on the root top bar before heading out on our adventure. Jessica wore this tight, dark red dress that hugged her body to perfection. She looked truly breath taking.

"You're really going to get a lot of attention tonight."

"Thanks. I surely hope so. But we have to agree... we aren't going to force anything tonight. If it doesn't feel right we can just try another time."

"Totally agree."

We headed up to the rooftop bar around 6:00PM and it was pretty crowded. All the guys couldn't help but look at Jessica. Even the guys with their wives or dates couldn't help but steal a look. Much to the dismay of the ladies. Jessica and I started drinking just to loosen up. Our dinner reservations weren't until 7:30. Our heads constantly on a swivel to look for possible suitors. The excitement of the possibilities consumed us both.

"Hey what about that guy over there?" I asked. I know Jessica has a thing for guys with tattoos and this guy seemed to fit the bill.

"Hmm... nice body. Not really into the face though."

"No problem. We'll keep looking."

We didn't find anyone she was really into at our first bar but the night was young. We headed to our dinner reservation and kept looking for guys to fuck my girl. Jessica had her flirty eyes on and all the guys loved it. And I loved her getting all this attention.

Dinner finished up and we went to a wine bar just to continue loosening up for the night. Again... no such luck. I started to get a little frustrated because my hopes were so high.

We bounced around for a little bit and decided to go dancing. There was a club that we both like that always has great music. I had sort of given up on finding a guy so I thought we mind as well just have our own fun.

Jessica and I hit the crowded dance floor and she let loose. She danced on me so sexy. She would also let other guys dance and grind on her. They weren't her type but she enjoyed the attention... and so did I. We danced for what seemed like hours. Our bodies hot and sweaty from basically fucking on the dancefloor with our clothes on. We definitely needed a drink.

I head to the bathroom while Jessica heads to the bar to order us drinks. Unfortunately, there was a long line for the men's room which is rare. While waiting in line, I receive a text from Jessica. It read:

OMG... found the perfect guy. Take your time.



.

My cock sprang to attention. I was getting hot and bothered by her flirting with a guy she wants to fuck.

I finally return from the bathroom to find Jessica flirting with the bartender. This guy was about 6' tall, muscular, tattoo sleeve, chiseled chin and short hair. He looked like he was in his 20's. Jessica was sitting at the corner of the bar and no one was around so she could continue her flirtatious ways. I stayed just close enough to be within ear shot of their conversation.

"So Ryan, what time do you get off?

"Actually our Manager accidently over staffed us for tonight so I am going to be off shortly."

"Oh nice. What's a guy like you doing tonight after you get off?"

"That depends... there's this incredibly sexy woman I'd like to hang out with, but I saw her in here with a guy. So I'm not sure if she'll want to hang out." Ryan was clearly referring to Jessica.

"Oh him... don't worry about him. He actually gave me permission to have fun tonight. And this girl you're talking about would love to hang out" She replied with a sexy smile.

"Oh. Well looks like I'm one lucky guy tonight."

"You have no idea."

At this point it had seemed that Jessica had forgotten about me and was totally into this guy. Just then she turned around and shot me a wink, knowing that I heard their entire conversation. She pulled out her phone and began texting.

"This is definitely the guy."

"Think so? You really into him?

"Absolutely. I'm getting wet just thinking about it."

"And I'm getting hard thinking about it. What's your plan?"

"I think we are going to head to another bar. Quieter so we can all chat."

My fingers couldn't write fast enough I was so excited.

"Does he know about the situation? I want to watch?"

"Yes. He is fine with it. Just needs to be drunk."

I was so excited. I knew it wouldn't be a problem for a sexy girl like Jessica to find a guy to fuck, but the challenge would be to find a guy that would let me watch. This was our lucky night.

The bartender finally came out from the back and came over to Jessica. She then brought him over to me. "Ryan this is my boyfriend. This is Ryan." We shook hands.

"Nice to meet you."

Ryan ushered us out of the bar. "Ok I know a perfect spot to hang out for a bit. I ordered an Uber."

The Uber showed up a few minutes later. "I'll take the front seat. You 2 take the back." I said. I wanted to give them some time together. During the ride I could see his hand moving up and down her leg. Their eyes starting at each other like they wanted to fuck right then and there. Then we rolled up to our destination. It was a bar literally within our Hotel... it was fate.

We went to the bar and Ryan was right, it was much more quiet and we got to chat. Ryan was very polite and there was very little awkwardness between us. We finally got some alone time when Jessica went to the ladies room.

Ryan leaned in, "Hey man, you totally cool with this?"

"Absolutely" I reassured him.

"Awesome. She is fucking sexy."

I wanted to give him some encouragement to make the night worthwhile. "And listen man, the better you fuck her, the better it'll be for all of us. So don't hold back. She can take it... trust me."

Ryan just smiled and said "ok, you got it."

Jessica came back and we had a few more drinks. Ryan and Jessica's lust for each other couldn't be contained anymore. So I finally made the suggestion to go up to our room.

The elevator doors opened and we all got in. As the doors closed Jessica turned to Ryan and pulled him in for a kiss. They began making out right in front of me. "This is really happening I thought to myself." I was so turned on. They made out for the entire elevator ride.

Once the doors opened they held hands down the hallway while I opened the door. I sat down on the chair towards the corner of the room preparing myself for the show.

Ryan pulled Jessica towards the bed and they began another hot makeout session. His hands started to explore her perfect body and she started rubbing his cock from outside his pants. Ryan then lifted up her short dress to expose her black thong, showing off her amazing ass. His hands tightly grab her ass. I can already tell this guy likes it rough. They continue to makeout and I can see their tongues in each other's mouths and their lips smacking.

While still standing, Jessica undoes Ryan's belt and unzips his pants. She spits on her hand and puts her hand down his underwear to start stroking him. Jessica then pulls away from their kiss, drops down to her knees and pulls Ryan's pants and underwear to the floor. A massive 8" fat cock sprang out. This is something Jessica definitely would enjoy. She immediately began sucking this hard cock like a pro. You can see her spit building up on this shaft and she uses it to stroke him while sucking him.

"Fuck Jessica. That's so fucking good. Look at me like you suck my cock."

Jessica looked up with her eyes, locking them with Ryan's as she continues to suck this big cock. He then sits on the edge of the bed while she continues to show off her skills.

"Stand up." He commands. "Take off your dress."

Jessica did as she was told. Unzipped her dress and let it fall to the floor. She didn't wear a bra so she was just left standing there with her sexy black thong. Meanwhile, Ryan removed his clothes to show off a ripped body with amazing body art.

Ryan leaned forward and slowly pulled Jessica's thong to the floor. He then pulled her onto his lap while he sat on the edge of the bed. They began kissing until his mouth moved to her hard nipples. One hand tightly squeezing an ass cheek while the other reaches around and begins fingering her wet pussy.

"Fuck Ryan. That feels good." Jessica began slowly grinding onto his fingers. Ryan's fingers began working even faster. I could hear her wet pussy as he was bringing her to climax. "Fuck... I'm going to come. Keep going... fuck!" Jessica then exploded with a beautiful orgasm.

Just then, Ryan pulled himself and Jessica onto the bed. He spun her around into a 69 position. I had a perfect view of him licking her pussy while she bobbed up and down on his cock.

"My God, you're going to make me come again Ryan." Jessica was already close again. She couldn't even continue to suck his cock because she was moaning too much. "Fuck... don't stop don't stop..."

Ryan clamps down hard on Jessica's ass and buries his face into her hole.

"I'm coming!!!" Jessica let out another amazing orgasm.

Ryan pushes Jessica off of him, stands on the side of the bed. He forcefully pulls Jessica's legs towards him and spreads them. Exposing her wet pussy for me to see. He takes his hand on his cock and places his head right in the opening of Jessica's pussy... teasing her.

"Fuck me Ryan. Don't tease me... please, please fuck me."

"Beg me for it."

"Please please fuck me. I need it. I need it so bad."

Just then, Ryan pushes his massive fat cock into my girlfriend. I can't explain the feeling I had. It was a rush of arousal I've never felt before.

Ryan wasted no time. He was thrusting in and out of her tight hole. "Fuck... you feel so tight. You feel fucking amazing."

"My God, your cock is so big. Fuck me hard."

Ryan did just that. He began pounding her. In and out with massive thrusts. He then turned her around, bent her over, and he placed her hands on the headboard. Her amazing ass sticking straight out to him. He slowly guided his wet cock back into Jessica's eager pussy. Ryan continued where he left off and continued to pound away. Jessica's ass gave a slight jiggle every time Ryan slammed into her. You could also hear his balls slapping into her clit. Ryan was having his way with my girlfriend and I loved it.

Neither one could contain themselves. You could see the glistening of sweat off their bodies. Just the right amount of light showcased Ryan's ripped body has held on tight to Jessica's hips. Ryan grabs some of Jessica's hair and begins lightly pulling on it... bring Jessica to another orgasm.

"Fuck baby... I'm coming again. I fucking love your cock." She moans.

Both of these people are lost into this hard fucking. Ryan then smacks Jessica's ripe cheeks with the hand that isn't pulling her hair.

I start to see Ryan tensing up... moaning and groaning louder. I can tell he is close to coming. He starts thrusting faster and faster.

Jessica turns her head around. Ryan leans forward and they begin a sexy kissing session from behind.

They remove their mouths from each other, "are you ready to come baby?" Jessica asks.

"I'm so close."

"I want you to come. I want you to come deep inside me. Give me every drop."

Jessica begging for his cum was all he needed. Ryan let out a loud moan and pulled Jessica's hips tight and began unloading his hot cum into Jessica.

"Oh my God Ryan. That's so much. I can feel you filling me up. I fucking love it. Give me everything."

After squeezing every bit of his cum into my girlfriend, he leans forward, kisses her back. Then takes his softening cock out of Jessica's full pussy. I could see cum dripping from his head and starting to come out of Jessica. "Wow that is a lot of cum" thought to myself.

Ryan got out of the bed and began getting dressed. Jessica just rolled onto her back exhausted. Just letting the cum slowly come out of her fucked pussy.

"Guys... this has been amazing. I'm going to let you guys have the rest of your night to yourselves now that my job is done."

I just gave him a nod and said bye has he walked out of the room. Jessica still laying there catching her breath. I had been stroking my cock the entire time of their fucking and I wanted to come too. I ripped off all of my clothes and hopped onto the bed.

"That was fucking hot." I told Jessica as we began to makeout. "I want to fuck you so bad." I move in between Jessica's legs, getting a good look at her leaking pussy. Her hole still gaping from the massive cock as his cum still slowly leaks out.

I take my hard cock and slowly put it into her extra wet pussy. The mix of her excitement and his cum made her pussy feel so wet. I began thrusting in and out. I could feel his cum deep inside my girl. This added to my excitement and couldn't hold it.

Jessica began to talk dirty. "Can you tell my pussy was good and fucked? Can you feel his cum deep inside me?"

The talking was pushing me over the edge.

"Give me your cum baby. I want to guys' cum in me so bad. Give it to me."

Just then I unloaded another massive load of cum into Jessica. The mix of Ryan's cum and my cum completely filled her up. As I pull out, there a massive amount of cum at the base of my cock and leaking out of her pussy. It was an incredible sight.

"Wow Jessica. You are truly amazing."

"Let's keep this lifestyle going."

"Agreed." I couldn't have been happier. My fantasy finally played out in real life!