Cupid's Oops

Carl watched Jackie shake izzy's hand the two of them chatted. He swore he saw Jackie batted her eyes at Izzy. He reached out and took hold of Izzy's other hand. Man her skin felt smooth and warm. But still, the handshake was firm. Wow, the thoughts racing through his mind were incredible. What would Jackie be thinking? This was out of his frame of reference. He never even thought of anything like this. He loved Jackie but this girl was amazing. What the fuck was going on? The three of them were just staring at each other. All of them felt the electricity of attraction. None of them understood it.

"So like I said, I'm Carl and this is Jackie." Izzy nodded and smiled at each of them.

"So hello Izzy. What are you doing in Emilio's Cafe?"

"Just having lunch on my break.. And you two?"

"Just meeting for a quick meal. Carl came by to meet me and get a bite together. Trying to spend as much of our Valentine's Day together. Do you have someone to share the day with?"

"No... I don't do much celebrating on this day. I'm not seeing anyone. Been single for a while now. Just planned on reading a book and taking a bath. " she kinda slouched down in the booth. Oh shit, she was doing that talking thing she did when she was nervous. Be confident Izzy don't scare them off. She sat back up. "By my choice though. I figure at 21, I can be single and get married later on when I'm older."

Jackie had both hands on Izzy's hand kinda rubbing her fingers. "Oh yes, 21 is young enough. Heck Carl and I are in our 40s and we met. There's time for relationships in the future. But it's too bad that you are all alone today. Nobody should be alone on this day right dear?" She turned to Carl.

His hand squeezed Izzy's hand in a strong confident grip to reassure her. "No this is a day for people to be together. We used to be just like you. A year ago we went to a singles Anti-valentine's party." Carl went on to tell the story of how he and Jackie met. Jackie interrupted and corrected parts occasionally. They were so cute together. Jackie mentioned something about Cupid shooting them with arrows. The homeless guy n the corner made a loud bellowing laugh and mumbled something. Izzy listened and absorbed the two. They were perfect together. She wanted to be like that with someone. She wanted to be like that with them. What was she thinking with them that was silly? "So that's how we ended up here together. Big holiday for us. The anniversary of our meeting" Carl finished.

Emilio brought over food and the three started eating and chatting like teenagers. The flirtation was heavy. The conversations bounced from topic to topic. Jackie kept rubbing her foot against Carls's leg. Occasionally she would rub her foot against Izzy's leg. Izzy started returning the contact.

The homeless god in the corner finished his coffee. Seemed like the three were hitting it off. He almost spits out his coffee when Jackie mentioned him. "If she only knew then," he mumbled, "and if she only knew now." They were certainly going to get along together for a while based on the "TL" he put on there. Carl and Izzy certainly got a strong dose of lust. Jackie is going to be taken care of. It will probably be a long week. Then the older couple will have a young girl that will love them both for a while. He would check on them regularly. See how things progressed. If he needed to intervene he would but things looked good. Carl had made plenty of money a fact neither woman knew and he would be able to take care of both of them financially. Izzy had been floundering from bad relationship to bad relationship. He could never find the right person for her. I guess this accident was a good fit for all. No more 'idiots and losers in her life'. The winged baby headed for the door. He stopped and dropped a couple of hundred dollars in the tip jar when no one was looking. It was just Emelio and his wife working. They could use the money. He thanked the cafe owner and strolled out after a refill on his coffee. He was going to swing by the hotel Carl was thinking of and get them a larger suite and extend the stay for a couple of days. In his mind, it would make up for the mistake. He heads out to do more matchmaking.

There was a lull in the conversation, and Jackie said she had to go to the bathroom. Izzy joined her. Carl stood as they stood up. Izzy thought that was very chivalrous. Carl watched the two beauties walk away. They were chatting like school girls. Wow, they were hot. What the heck was he going to do? Did he stil propose? How did this change his relationship with Jackie? His thoughts were interrupted by his phone ringing. "Hello?"

"Hi sir, this is the Ritz, just advising you your room is ready early you may check in whenever you would like. The flowers you ordered are already in your room along with the champagne."

"Thanks, I stop by shortly. Hey can you add an additional bottle of champaign and grab another dozen roses?"

"Absolutely sir. Oh and by the way just letting you know, there was an opening and we upgraded you to a suite for no extra charge. I understand this going to be a special night sir?"

"Thank you yes, yes it is." In more ways than one Carl thought. Carl hadn't mentioned the engagement to anyone. How did the clerk know any of that? Oh well, a plus. The suite would help with Izzy in the room. What the fuck? Where had that thought come from?

The girls were in the lady's room. Jackie was adjusting her makeup. They were talking back and forth. Jackie mentioned that Izzy had such a nice athletic figure. Izzy was looking at Jackie's body. She told Jackie she had nice breasts. Jackie told her look at this and pulled off her shirt. The red lace bustier held tight against her hips and pushed her big breasts up. The lace fabric revealed everything underneath and accented all of it. The red was sexy against her pale skin. The woman had a nice figure, she was slightly overweight but Izzy could tell she worked out. Izzy wanted to peel off of her and suck on those breasts. Wow, where did that come from? Izzy thought.

"Wow that looks amazing," Izzy said distracting away from her thoughts. "I like how its almost not here in the back." Izzy ran her hands along the minimal fabric on the back as she stared at Jackies breasts in the mirror "That is so hot, Carl is a lucky guy. Are you wearing anything special down below?"

"Certainly," Jackie started to unbutton but then stopped, "I think i'll let that be a surprise." She laughed. Izzy laughed. Why wouldn't I show her? Who am i going to surprise, Jackie thought, Izzy? Her mind raced with excitement.

"I wish I had bigger breasts that I could show off with something like that."

"Oh, you have a hot tight body that men adore. Unzip that hoodie and let me see what you are working with." Jackie couldn't believe she just said that. Oh shit. But Izzy took off her bag, her hoodie and her shirt. She exposed her B cup-sized breasts in a sports bra. Jackie reached out and grabbed a hold of Izzy's breast. "See that, a handful or more is all it takes." Jackie was excited to touch this young girl's breasts. She needed to slow down and think this out. She didn't want to scare the young girl off. She couldn't resist touching her. "Your breasts a perky and young. They don't need support like mine." Jackie reached up and slid the sports bra up letting Izzy's breasts free. They pointed up and were capped by sharp nipples surrounded by dark areolas. She was staring at the perky young breasts in front of her. Her panties were soaked. "Oh my, they are amazing." Something compelled her to go further. She squeezed and massaged them. She had no clue where this was coming from. But she went with the feeling.

Izzy was in heaven this beautiful lady was caressing her breasts and it felt great. It had been a long time since someone touched her and it had never felt this good. She couldn't believe this was happening. Her body was reacting to the touch. "Oh that feels so good. You have such soft hands." Jackie encouraged by the young girl leaned in and sucked on one of her nipples. Izzy leaned her head back, "Oh god yes." Jackie went on to move back and forth from nipple to nipple. She reached and grabbed Izzy's ass with both hands. Jackie's tongue and lips moved from breast to breast. It felt so wonderful. Izzy could feel the sensation building inside her. She had never experienced anything so awesome. Jackie was sucking away on her breasts when a phone vibrated and an alarm sounded.

"Oh shit, I have to get back to work," Jackie said suddenly stepping away. Then she hesitated. Stepped forward and turned kissing Izzy passionately on her lips. Izzy grabbed around her and pulled her in closer. Their tongues danced and they leaned into each other. Jackie pulled away. "I'm taking the rest of the day off," she announced, " I have more important things ... um.. I should say more important people to.... um... well I guess 'do' would be appropriate." She smiled at Izzy. Jackie picked her phone up and called her work. "Hey it's Jackie, I'm taking the rest of today and tomorrow off."

Izzy heard her talking and decided to text her boss. Bike trouble is done for the day. And like that she was off. A perk of the job. Course she wouldn't get paid but she'll figure that out later. Suddenly she wanted this woman. She had never felt like this for a woman, heck not even for a man. There was something beyond, she wanted to know all about this woman. She couldn't take her eyes off her bustier. She had never been with an older woman before. Then she thought of Carl in his suit. She imagines Jackie and her stripping the suit off of him. She had never been with a man and a woman before. What would it be like? Her thoughts were interrupted by Jackie.

"So what do you think? Can you take the day off so we can hang?"

"I just texted my boss. My schedule is clear. I'm open to do whatever... or whomever I guess." she smiled slyly.

"I have an idea." Jackie helped her remove the sports bra then Izzy put just the hoody on. "Now leave it unzipped to just about mid-belly.'' Jackie stood behind Izzy staring in the mirror. She reached around and adjusted the zippered hoody perfectly exposing Izzy's cleavage. "There we go. I'm sure once Carl sees your hot new look he won't hesitate to join us."

Izzy stared at herself in the mirror. Wow, she looked and felt hot, Jackie was standing directly behind her her hands on Izzy's waist. It felt good. The two just stared at each other in the mirror. Izzy turned her head back to kiss Jackie. The two french kissed like teenagers.

"Let's go show Carl this sexy look. He'll have a boner before we make it to the table." She grabbed Izzy's hand and led her out of the bathroom.

Carl watched the two beauties walk toward him. They were holding hands and strutting like they were on a catwalk. Izzy's hoody was unzipped and he had a clear view of the skin all the way down. The sides of her boobs were showing. He was rock hard before but now it was hurting as it pushed against his pants. He stood adjusting himself as the ladies approached. "Wow Izzy that looks hot. I thought you were as sexy as ever when you went to the bathroom. Now I have to watch, I don't drool looking at you."

Jackie reached over with Izzy's hand in hers. She grabbed his hard-on through his pants. "Told ya you would have this effect on him." The two held their hands for a moment smiling at each other then sat down. "So Izzy and I have taken the rest of the day off. Not sure what we are going to... well let me correct that. Not sure where," she emphasized the word, "we are going to go but we want to spend some time together. What are your plans?" Izzy and Jackie were sitting down Jackie's arm around Izzy.

Carl noticed Izzy had some red lipstick the same shade as Jackie on part of her lips. It certainly wasn't there before. Man, this was getting hot fast. Images danced in his head of the two of them kissing as he sputtered out the next sentence. "Funny you should ask. I had gotten us a room for the night at a hotel." He said to Jackie, "They just called to advise the room is ready." He turned and looked at Izzy, "Apparently they upgraded us so there is plenty of room if someone wants to join us. We can head that way and then go out somewhere from there. Since Izzy seems to have some fresh lipstick smeared on her lips, I'm guessing you two got to know each other well in the powder room." The girls looked at each other blushing and laughed.

"I'm game what hotel? I'll ride my bike to my apartment then meet you there." Izzy said.

"The Ritz, we can put your bike in the cab and stop by your place on the way," Carl suggested.

"Or we just take it with us. I think you are fine coming with us as you are. Anything we need we can order from the hotel. As far as going out from there, I think we will figure that out later but I plan on getting out of these clothes and hanging." With that Jackie leaned in and kissed Izzy while staring at Carl. She slid her hand inside Izzy's hoody and squeezed one of her breasts. Carl watched in delight. "Her lips are so tasty It's tough to stop kissing them. I'm sure the ride over will be fun. I'm sure you will like the taste of her lips too." Izzy smiled and blushed slightly. Jackie was still amazed she was doing this, but it was getting easier and she stopped resisting.

"Yeah, I'm thinking of just going to the hotel. I'm pretty sure I won't need anything else. I'm feeling like i'm overdressed right now for the night's festivities. Especially based on the outfit Jackie showed me. Pretty sure you won't want to leave once you see it. It is stunning." Izzy stated. "I'll take care of the ride to the hotel." She grabbed her phone and texted away. Jacke was still fondling her breast. Her jacket just covered the nipple, but the entire left side of her right breast was exposed.

Carl stared in disbelief. Jackie was all over Izzy. He was happy but jealous. He wanted to be all over Izzy and Jackie for that matter. "Ok, I had other errands to run but after that display. I'll make some calls and ditch them till tomorrow." He grabbed his phone and walk to the counter to pay the bill.

The three of them waited outside the cafe for a few moments for a town car that Izzy ordered. Another messenger that she knew. They piled in the car. The driver said he would come back for her bike later and drop it at the hotel for her. Once in the car, Jackie took off her coat to reveal she was only wearing the red bustier underneath. Izzy and Carl were impressed. Izzy unzipped her hoody baring her breasts. Carl sat in the middle his hands wandering across each of the set of breasts on either side of him. Izzy and Jackie unzipped his pants and took turns sucking on his hard cock.

They would each go down for a moment then kiss and swap. He would lick the breasts of the girl that wasn't sucking his cock. The girls were each sucking and swirling their tongues around the head of his cock. Then deep-throating him. It was electrifying. Then they both went down and kissed with his cock in the middle. He felt the pulse in his balls. "I going to explode," he said.

"Yum" Izzy said and took his cock in her mouth. She sucked and swirled her tongue around the head. Caressing his balls with her hand. In her mind, she could not believe she was doing this.

Jackie whispered in his ear, "that's so hot watching her suck on you. She is so lucky to taste your cum. I can't wait to lick it off her lips." That was all it took. Between Izzy's talent and Jackie's words, he was cumming hard. Spurts shot out. Izzy took all of it in her mouth. Carl's eyes rolled back in his head as the electrifying orgasm traveled through his body.

"Holy shit that was amazing," he said. Izzy finished cleaning off his cock. She sat up. Jackie immediately French kissed her in front of him. Her hands pulled Izzy's head so their lips were locked. When they broke their kiss he could see they had shared his cum between them.

"The night has just begun... Or should I say afternoon since it's only 130... wait till we get to the room," Izzy said smiling.

As if on cue, the car pulled up to the hotel. Carl got out and spoke to the driver.

"How much?"

"Nothing man, I know Izzy she's good people. Just take care of her. You better not hurt her."

"No worries there. She's in good hands." The two of them watched as Jackie and Izzy walked toward the hotel hand in hand. He handed the guy a fifty. "Thanks."

Jackie had put her coat on and Izzy had zipped her hoody. The place was unbelievable. Carl spoke to the doorman. He called over to the ladies. "A bellman will show you to the room, I just have to check in then I'll be up." Carl handed the bellman some money.

The girls rode the elevator up with the bellman. They were leaning against each other. Staring into each other's eyes. The bellman walked them to the door and opened the room. It was a beautiful room with a table a couch and a chair. To the left was the bedroom with a king bed. The bellman explained there was champagne on ice and that if they needed anything to push the button for their butler on the phone. The windows looked down on the city and across to the taller skyscrapers. The bellman nodded and excused himself closing the door. The girls looked around. Two bouquets of red roses sat on the table. Looking through the doorway to the bedroom the bed was covered in rose petals.

Jackie told Izzy to stand by the couch. Then she slid the chair so it was in the middle of the room facing the couch. Then Jackie stood in front of Izzy and stripped off her coat tossing it aside. Her hands moved to the pants and she slide them down revealing a red lacy g-string. She was also wearing red thigh-high stockings. "This is the surprise i was keeping from you earlier."She tossed her clothes in a pile near the door.

Izzy's eyes lit up seeing Jackie strip in front of her. My god, she was hot. Jackie was 5'9 with a curvy body. She had big d cup breasts and nice shapely hips. She was voluptuous. Izzy was so excited. Her hand inadvertently began to stroke between her legs. "That is one hell of a surprise. You look amazing. So hot. Carl will love it. I just wish I had something I looked so good in."

"I know just the right outfit for you." Jackie walked over to the bedroom closet and came back with hotel robes. "As I said early, you have a body that looks amazing whatever you wearing. Let me help you get dressed." Jackie stepped over in front of Izzy. Jackie put her hands on Izzy's hips hooked her thumbs into the waistband of Izzy's bike pants and pulled down kneeling at the same time. She pulled the pants and shorts straight down revealing Izzy's bare body. Jackie grabbed Izzy's ass and stared at the young beauty in front of her. Her pubic hair was shaven except for a small tuft on her mons. Jackie massaged her ass and breathed heavily blowing between Izzy's legs. Then she inhaled taking in the beautiful scent of the dark-haired pussy.

Izzy felt the breath shoot through her legs. Goosebumps ran across her body. The hands grabbing her ass felt amazing. She unzipped the hoodie and let it drop to the floor. She looked down at the blond woman kneeling before her. She spread her thighs slightly. The blond beauty needed no further encouragement as Izzy felt the tongue dance across her mons. Izzy put her fingers on the girls head and played with her hair. She lifted her leg and stepped on the couch. Jackie pushed further running her tongue along Izzy's lips. Jackie's hand slid and her fingers danced around Izzy's opening. The touch sent waves across Izzy and she shivered with powerful excitement.

Jackie's tongue lapped the pussy. It was so tasty. Izzy had obviously been as turned on as Jackie was. She kept licking and licking her fingers teasing the opening but not penetrating her. Not yet. She would tease her until Carl was watching then she would give Jackie a huge orgasm. She teased for a few moments and then felt the girl quiver. It had been so long since she had done this she was encouraged to get the response. Not yet thought Jackie. Not yet. Her own pussy was dripping with excitement. But she had to stop she wanted the three of them to be together. She slowed her licking and moved up Izzy's body. Licking at each nipple then moving up to stand face to face. She kissed her deeply. "Let's get the robes on and surprise Carl. He can sit in the chair and watch as I finish that later" Jackie smiled.