This is the second part of the Chicago trip in the Wanda series after Target.
Wanda woke to a steady knocking at the door. It took her a few moments to realized she was in a hotel room. Her roommate for the trip was her former rival from teachers school Ashley. Ashley was already getting ready for the college recruiting convention that had brought them to Chicago.
Ashley opened the door without thinking about Wanda's choice of sleepwear. Wanda's bag had gotten lost and her clothing choices were limited to what she had brought in her carry on bag. Wanda had slept in just a short cami top and her panties.
The two administrators from the college Dr. Hertzmoore and Professor Gropenhoffer were on the other side of the door. Dean Feely stayed home after he was filmed on the news groping a topless Wanda at a fundraiser. The rest of the school leadership decided the Dean needed to avoid Wanda for awhile.
The doctor and the professor made up for the dean's absence by ogling Wanda extra hard. Her bare legs looked amazing in her tight little panties. Wanda felt completely naked as the two older men looked her body up and down. Wanda hated it that the cold had made her nipples rock hard under her thin top. She could feel their eyes on her headlights under the material.
The cold was actually the reason the administrators had come to their hotel room. There had been heavy snow and not only was the conference canceled but they were actually snowed in at the hotel. The roads had been closed.
"That doesn't sound so bad." Ashley said looking forward to a day of doing nothing.
"It wouldn't be bad except very little of the hotel staff made it into work." Dr. Hertzmoore explained.
"Yeah, just the front desk guy and the bartender. It's cereal for breakfast and cold sandwiches for lunch and hopefully, they will fire up the fryer for chicken tenders and fries for dinner." Professor Gropenhoffer
"Pools open though?" Ashley asked referring to the indoor pool that was one of the big selling points when they chose this hotel.
"I guess so." Gropenhoffer responded.
"It's all good then. See you after breakfast." Ashley said and closed the door.
"A day at the pool sounds like fun." Ashley told Wanda.
"I can't go swimming, I don't have my swimsuit." Wanda replied.
"We'll work out something. A day at the pool is the reason we picked this hotel with the indoor pool." Ashley reminded her.
Before Wanda could respond Ashley was on the phone with Madison and Heather's room. Madison answered.
"Did you hear? We're snowed in. So it's a quick breakfast and hit the pool and flirt with cute baseball players." Ashley said referring to the young baseball players staying at the hotel for tryouts to get on with the Chicago baseball team's farm system.
"No, the ballplayers made it out before the roads got shut down. The hotel will be mostly empty. It's really just us and the little bit of staff that got trapped here." Madison informed her friend.
"Poo! In that case we're gonna get drunk as hell at the pool today. One thing though Wanda doesn't have much in the way of clothes since her bag got lost. Can you lend her something she can get wet?" Ashley asked.
"I doubt I have anything that will fit her." Madison said referring to Wanda's massive chest.
"I know but you are the closest to anywhere near her size. Just bring over what you got." Ashley told her friend.
Madison and her hotel mate Heather were over in five minutes with most of Madisons clothes for the trip. Despite the fact that Wanda was sure the creepy Doctor Hertzmoore and Professor Gropenhoffer would surely be hanging out at the pool to watch the girls from the college in swimsuits, Wanda agreed to go swimming in her black panties and Madison's bikini top. Wanda wasn't thrilled about how little of her breasts were covered by Madison's top but she didn't want to be a party pooper.
Wanda was right about the administrators. They were in the hot tub when the girls arrived at the pool. The joy they felt at seeing six college beauties in swimwear was obvious by their expression.
What was a surprise was that the Dominican baseball player from the night before was swimming around in the pool. Wanda and the rest of the girls couldn't help but notice how fit and firm his body was as he moved about in the water. He wasn't as heavily muscled as Wanda's husband Julie was but his muscles were rock hard. There was no other word to describe him other than toned. Wanda also noted how evenly tanned his dark skin was. Julie had a serious case of farmer's tan. His face and arms were a dark brown but he was very light-skinned where the shirt he always wore while out jogging shielded him from the sun.
"I thought all you baseball players left for the day?" Ashley asked the ballplayer.
"I overslept and missed my ride." He responded looking over the college girls
"You don't mind if we join you?" Heather asked as she entered the ramp through the shallow end of the pool. Water creeping up her orange one-piece swimsuit.
The ball player noted her silicon filled softball-sized breasts didn't bounce or jiggle at all as she moved down the ramp.
Lisa hopped in all at once and the ballplayer was quite taken with how much she looked like the Batgirl actress Alicia Silverstone in a blue string bikini.
Crystal was super pale and her skin was covered in freckles she wore a red and white gingham bikini that matched her red hair perfectly. The ballplayer was quite taken with her skin. Ginger girls were almost unheard of in the Dominican Republic.
Ashley dove in the deep end her tight athletic yellow suit looked painted on as she emerged from the water. Her perky breasts looked like little cones in her sports bra-like top. Her long black hair shone in the light as she pulled it back.
Madison really got the ballplayer's attention in her mismatched bikini. She was wearing a red bikini top and black bikini bottoms. The red bottoms were too revealing for public and she had lent Wanda her black top for the day. Madison had a killer body. While she wasn't as big-breasted as Wanda she had an amazing curvy ass that was flawless. Dominican culture was very big on the ass and Madison was blond too. To the Dominican ballplayer, she looked like a real movie star.
Wanda was very self-conscious in her black panties and way too tight black top. Her nips were covered just barely and the bottoms of her giant breasts were bare under the top. Wanda wasn't sure what made her the most anxious the administrators watching from the hot tub or the super sexy athlete she would soon be joining in the pool.
The girls splashed and frolicked for about an hour and enjoyed flirting with the baseball player they had learned was named Tony. The administrators were jealous of the attention the girls were lavishing on Tony the ballplayer. Then Ashley came up with a fun idea.
"Let's play truth or dare." she suggested.
"What is this?" Tony asked.
"It's a fun game. You can watch for a round to learn how to play." Heather answered.
The girls played a few rounds asking questions about underwear and position preferences and ages of first times. Ashley picked dare just so Tony could understand the game.
"Show us your ass." Heather told her.
Ashley complied and pulled her bikini bottoms down in the back to reveal her smooth pink ass. Tony was impressed. He had only seen white girls naked in the movies. This was the first time he had ever been so close to a bare white ass.
Tony jumped into the game the next round. Being the only guy in the game he quickly became the focus of the game. He picked truth in the first round.
"Do you have a girlfriend?" Ashley asked.
"Yes." He replied.
Tony picked Madison to no one's surprise. What was a surprise was Madison picking dare.
"I want to see your ass too." Tony said excited about the blond's curvy figure.
Madison swam up to the ballplayer and turned her back to him. She bent over and pulled her bottoms to her knees. Tony's eyes bulged from his head as he saw Madison's pussy from the back.
Madison chose Tony again and he chose truth again.
"Are you faithful to your girlfriend?" she asked.
Tony admitted he wasn't always faithful to the giggling group of girls.
Tony picked Lisa who also chose dare.
"Reach into my shorts." he ordered.
Lisa wadded over and shyly pulled the waistband of Tony's trunks out. Her hand disappeared into his swimsuit. The other girls laughed at Lisa's surprised reaction to the size of Tony's erection.
Lisa picked Tony who picked dare starting to get into the flow of the game. Lisa dared him to take his cock out of his shorts. He complied with no hesitation. None of the girls in the pool had ever seen an uncircumcised penis before. Crystal was so amazed by it that she cupped it with her right hand and fingered the foreskin.
"What's up with your dick?" she asked.
"He's not circumcised, dope. You better be prepared for that as nurses we're gonna be placing catheters." Lisa said laughing.
Crystal felt the uncut member pulse warmly in her hand. Tony growled with pleasure as she toyed with his sensitive foreskin. Tony grabbed the shoulders of her bikini and pulled the straps down until her pink breasts popped out.
It was Tony's turn to be enamored with something exotic. Crystal had the lightest pink nips Tony had ever seen. To Tony it looked like Crystal's nips were made of bubble gum. Tony had to find out what they tasted like. Crystal almost came right in the pool when Tony's warm tongue hit her areola.
The only thing stopping from going over in front of everyone was the creepy leering stares from the hot tub. Professor Gropenhoffer was practically drooling as he looked over Crystal's exposed breast and her struggle to maintain herself as the Latin ballplayer swirled his tongue around her sensitive breasts. Crystal finally managed to pry Tony reluctantly off her pink flesh.
Crystal picked Tony and he chose dare again.
