Green Thong Leads To First Squirt

As the hotel door closed behind her, Chelsea finally felt like she was on vacation. She had spent most of her day traveling and dealing with packed planes, slow traffic, and checking in and out, but now she was ready to relax.

This was going to be Chelsea's first time out of state from her children, as well as her first real time to explore her new single life. Over a year ago, Chelsea and her husband got a divorce after 10 years of marriage. Between work, raising their children, and just life overall it broke the relationship they had; and the changes, therapy, and couple retreats didn't help fix it either.

While they both seemed to be happier now Chelsea did feel a sting of jealousy as she dropped her children off with their father this weekend. He started dating a new woman and she could tell he was much happier now.

Chelsea herself since the divorce had only been on one date. While it did end in an enjoyable evening of sex, Chelsea didn't meet the man again and rather focused on being a mother and her job more.

This bachelorette party for one of her college friends though, was just the opportunity she needed in order to let loose a little. She was already fourteen years removed from college as she was now 36, but her small group kept in touch well after school and were all still very much involved in each other's lives.

They all supported her through her divorce and all agreed this weekend she should enjoy it, and embrace the benefits of single life. While Chelsea agreed, she didn't want to just fly off the deep end and slut it up. She did end up buying some new dresses and skirts for the weekend, as well as some new lingerie.

While she wasn't the biggest fan of always wearing some, she wanted some new ones as everything else was a hold over and reminder of her failed marriage.

In the hotel room she unpacked her clothes from her bag and glanced over the options again. It was Thursday and she wasn't leaving till Monday mid day so she had quite a bit of outfits for different occasions.

Some for going to a club one night, which was a tight fitting red dress. A few summer dresses that went just past her ass for brunches and site seeing. A couple of nice dinner dresses for those occasions. And of course some bikinis for the pool, and lingerie just in case.

As she was putting it all away she saw one of the new dresses she bought. It was a tight green dress that tugged at her curves exceptionally well she thought.

Chelsea stood 5'6 without heels, 5'9 with her usual preferred heels. She has beautiful long brown hair and natural brown eyes. She gives off the cute librarian vibe at times due to her glasses.

Body wise she was very trim. She had a nice set of 34c breasts which she usually felt brought her more attention as she had a perky ass but it was rather on the smaller side.

She kept herself freshly shaven all over as it was an original request of her husband's, but one she had grown to enjoy more and meant less clean up at times.

Chelsea looked at the clock and it read 6:15pm. She figured she could go out grab some food and maybe hit the hotel bar for a drink since the rest of the ladies wouldn't be in till the next morning.

She looked again at the green dress and had a change of mind. Chelsea was going to get a drink at a bar first. The idea of letting loose finally, getting some drinks, and maybe even some male attention to feed her ego for the upcoming weekend.

Chelsea spent the next thirty minutes getting ready, with hair and makeup applied to her liking. Before she walked out of the hotel room she looked at herself in the mirror.

The dress looked amazing on her. Hugged her curves perfectly and made her nicely sized boobs, pop more and look juicy. She had on a green bra and green thong matching set, not really thinking anyone would see it that night but just to dress for the occasion.

As she walked to the elevator she pulled out her phone and found a few options for bars. After an elevator ride down from the forth floor to the lobby she found a good one and ordered an Uber.

As she waited outside she sat on a bench enjoying the breeze. She felt a quick breeze draft up her dress and it set a pleasant shiver across her body. Her thin lace thong allowing access for the breeze to hit her brought a calming smile to her.

Chelsea felt it was right. She deserved to let loose and enjoy life at times. She is usually so busy with work and kids she never enjoys time for herself, and she vowed to make the most of it this weekend.

The Uber came after a few minutes and drove her the 4 minutes to the bar she found online. She thanked the driver and got out, walking to the door and into the bar.

The reason she picked this bar was that there were a lot of positive reviews and more importantly for Chelsea it was a lot of reviews from women.

If it was a place with creepy men and bad vibes, you wouldn't have many women commenting positively about your bar she knew.

She walked up to the bar and ordered a drink. As she waited she scanned around the bar. There were about 20 people in the bar with some in groups sitting in booths and what seemed to be the individual section on the bar stools and sitting at the small tables.

Chelsea grabbed her drink and headed to a two seat table and sat alone. She pulled out her phone and checked up on the group chat for the bachelorette party and sent a picture of her drink to the group saying she was already enjoying the weekend.

She continued to text her group chat as she drank and mostly ignored the surroundings. She updated them on the fact that she was all unpacked and enjoying the freedom and they all encouraged her to do so.

Chelsea finished the first drink and went to the bar top to order another. While doing so she looked around again and noticed a few more people in the bar. She saw some cute boys, but that's what they were to her, just boys. They could have been no more than 22 and yes Chelsea was looking to have fun but not with someone that young.

She took her new drink, returned to her table and continued with her text conversation.

The next ten minutes Chelsea enjoyed her drink, which was now pretty much finished, and continued her text conversation with her friends.

"Would you like another drink?" She heard from her side and looked up. It was one of the young boy group she saw when she got her drink.

Chelsea was flattered but also felt like she was almost old enough to be his mom. She did have to admit she enjoy what she saw.

He was 5'11 with a great build. Strong arms but no vains popping or attention brought to them. He had a nice and warming smile to go with cute brown eyes and short hair.

"I appreciate that, but I don't want to intrude on your evening with the boys." Chelsea said as she turned around but noticed the group he was with no longer was there.

"They wanted to go to another bar with a different crowd." The young man said staring at Chelsea.

Chelsea was taken back by the young man and while impressed and definitely flattered she felt it was weird to get a drink with someone so much younger.

"Well now that I used a failed excuse I'll just be honest. I feel it's a bit weird to have a drink with someone so much younger than me. Don't get me wrong you are a handsome young boy, but as I said a boy." Chelsea said not wanting to come off as mean but just trying to get her point across.

"Well first thank you for the compliment. Second I don't think there is that much of an age difference and even if so we are both legal consenting adults. And finally you are looking far to beautiful tonight to sit here all alone." The young man boldly replied.

Chelsea was momentarily stunned and than smirked. She was intrigued by how confident the young man was and she figured she could give him the time of one more drink.

"You play a good game there young man. I'll have that drink with you." Chelsea said.

"Great." The young man said and reached into his pocket and pulled out some money. "Here is 30 bucks, get two of whatever you were having and we can enjoy them together."

"Oh sending me away already?" Chelsea said stunned by the request.

"Oh no, I don't want you worried about your drink, so if you buy it you can concentrate on our conversation and I can learn more about you." The young man said again very commanding.

Chelsea couldn't argue with the statement. She grabbed her bag and went and bought two drinks, leaving the young man at the booth and him slipping into the opposite side as she walked away.

While waiting for the drinks to be made, Chelsea took the opportunity to message the group chat about her handsome, but young suitor. She just finished her message as the bartender came back to her with the drinks and change.

She grabbed the drinks and turned back to head to the booth with the handsome young man she left waiting for her.

As she sat the drinks down she felt the vibration in her purse signaling a new message was received. Before checking she decide to thank the 'boy' for the drink.

"Well that was definitely a new experience. By the way I'm Chelsea." She said as she sat down and looked across the table.

"Thank you for grabbing the drinks and giving me an opportunity to talk to such an amazing woman. Also I'm Hunter." The young man said with a smile on his face and staring intently at Chelsea.

Chelsea wanted to check her phone but didn't want to be rude. She did agree to talk to Hunter and he did just buy her a drink, so she felt she should at least give him the shot to talk she promised.

Before she could figure out what to say, Hunter took the lead. "So what brings you out here, business or pleasure?"

Chelsea smiled at the pleasure statement as he had no idea how long it had been since she was able to feel that, but she couldn't lie to herself and say it wasn't an option she had thought of for this trip.

"Well one of my best friends is getting married next month and we are doing her bachelorette weekend here." Chelsea said as she took a sip of her drink and slowly slid her phone out of her purse.

"By we, do you mean the people you have been texting all night while sitting here all alone but totally eye catching?" Hunter asked her.

Chelsea smiled at the compliment and was intrigued as Hunter seemed to be eyeing her longer than she realized.

She was also happy her green dress was doing exactly what she wanted it to.

"Yes, I was the first one to arrive as the flight options in the morning would have gotten me here later than my friends." Chelsea admitted while looking at Hunter intrigued but also starting to admire his arms and face even more as she became more comfortable.

Hunter could tell Chelsea was starting to relax a little as they were both smiling and enjoying their drinks as they talked. Over the next fifteen minutes the two talked about Chelsea's work and Hunter's goals for after graduation.

"I need to use the restroom, but still want this conversation to continue, would you still be here when I return." Hunter asked her taking this as a chance to see how interested she was on this conversation.

Chelsea was definitely enjoying herself, now two drinks in, and feeling the excitement of the conversation she was having with Hunter. She decided to tease the young man a bit with her comment.

"Yeah I'll still be here, just don't take too long, some young handsome stud may try to come up and talk to me again." She told him with a wink and a smile.

Hunter smiled and got up and walked to the restroom. Chelsea took this time to check her phone and respond back to her friends.

Their chat now was just her friends encouraging her to enjoy herself and the free drinks from the young man, and since she didn't respond right away the jokes about her lack of sexual activity lately made her laugh but also think that maybe she should let loose and see where this goes.

Chelsea replied to the chat telling them how it was going, and as she finished that message she saw Hunter returning from the restroom. With the drinks flowing through her she decided she should also use the restroom.

"Glad you are still here." Hunter said as he returned to sitting on his side of the booth.

"Well I myself need to use the restroom and didn't want you thinking I ran off from our conversation." Chelsea said as she began to get up.

"When you get back should we continue the conversation with fresh drinks as it looks like we are both out." Hunter asked her.

Chelsea agreed and before she knew it Hunter slide cash out of his pocket and handed it to her again. "Well when you're done in the bathroom you can grab them and rejoin me back here."

Chelsea continued to appreciate the gesture and was impressed that the young man seemed so confident and assured in his actions and words. She grabbed the money from his hand, while letting their tough linger a bit as she felt a bit of excitement from it.

After using the restroom she stopped to check her messages and herself in the mirror. The encouragement and teasing from her friends in the chat continued, with a request to see a picture of the young stud. Chelsea figured when she got back to the booth she would sneak a photo of him.

She walked out of the restroom and ordered new drinks and a few minutes later she was back in the booth across from Hunter. When she returned she noticed an amazing smile on Hunter and returned it as she herself was feeling happy and excited herself.

"Is that smile for me, or is your chat with friends entertaining you more." Hunter said as he took his drink from her and took a sip.

"A little of both I would say." Chelsea replied as it was the truth and she could tell the drinks were starting to flow through her body.

Hunter smiled and replied. "Hopefully they are good comments you're laying out to them about me."

Chelsea giggled and said, "of course, they are just interested in how the evening is going and to be honest maybe what you look like."

"Well let's take a picture together and you can send them the results?" Hunter boldly asked her seeing if she would take the invitation, as he saw it as an opportunity to sit next to her than on the opposite side of the booth.

Chelsea quickly smiled and agreed. She got up from the booth and slide in right next to Hunter and as they both got close to each other she took a quick photo of them together. She showed Hunter and they both liked it so she sent it to the group chat and put her phone back down.

Hunter was happy when she did that she didn't attempt to go back to the other side of the booth. The two continued to talk and their conversation had no gone over the fact that they were both single, Chelsea even telling him that she has two kids back home and this was her first trip alone that she could remember since what seemed like college.

Hunter noticed that the drinks were now empty and asked, "should we get another round?" Hoping she would say yes as he was enjoying Chelsea and hoping to continue the evening.

Chelsea herself was also enjoying the conversation and the feeling of talking to Hunter. "Sure why don't you get them this time."

Hunter was shocked but happy with that answer as he felt that Chelsea was opening up and feeling comfortable now. "Will do, but you will have to tell me what your girlfriends said in the chat when I get back." He said and got up and went to go get the drinks.

Chelsea immediately grabbed her phone and checked the group chat. She smiled and blushed as she read her friends comments.

'Oh damn girl you locked in a young stud for the weekend.'

'Now we know why she went out a night early'

'Someone looks happy and giddy to have some fun attention.'

'Seems she is going to have a hot evening!'

Chelsea smiled at all the comments and even led to some thoughts of Hunter and replied back to the chat that she would let them know how the evening went but she was continuing to get drinks with him.

She put her phone back down as she saw Hunter coming back to the booth. She hoped that he would sit on the same side as her again which she was happy when he slid in.

"So what was the girl talk reaction?" Hunter asked with a smile on his face.

"A full approval of what they called a young hot stud." Chelsea smiled and giggled. Usually she wouldn't be so outgoing and honest about it but the combination of a night out, the fact that she for the first time in a while felt sexy and desired, and also the drinks helped.

Hunter smiled at that comment, "well would you agree with that comment?" He wanted to see just how interested Chelsea was in this potential situation.

Chelsea smiled and said, "ummm, well you sure do fit the description, but they also left out that you were sweet but smooth."

"Sweet and smooth is a nice description but figured that would be said by me at another time." Hunter confidently said with a grin on his face, seeing if Chelsea would pick up on the innuendo.

Chelsea did pick up on it and got a little wide eyed but also felt a rush come over her. She immediately thought how perfect timing that comment was, as the night before she did make sure she was fully clean and shaved everywhere for the just in case a situation arose moment.

She also realized that she couldn't remember the last time when someone ate her pussy, as her ex husband was more into a quick fingering and than fucking.

Chelsea decided to flirt back with the comment saying, "well we can both be sweet and smooth in our own ways."

Hunter became excited by the comment and happy with the fact that more and more Chelsea seemed to be enjoying herself and becoming more open. So he decided to pry more.

"Makes sense you would be, seems like you're the full package. Beauty, brains, and tasty." Hunter said with a smile and took a drink while still staring at Chelsea.

Chelsea could feel herself starting to very much enjoy the attention and flirting. She hadn't had much attention since her divorce with being so busy, but now she was feeling like she had been missing out.

"Oh such a smooth line." She replied as she laughed and she made a quick instinctive move and slide a light bit closer to Hunter.

Hunter laughed as well and said, "I have two out of three verified, but without first hand knowledge or references, I'll have to use my imagination."

Chelsea couldn't believe she was having this conversation, but she had to admit to herself that she sure did enjoy the flirting and teasing. She decided to she would play it out and see where it went. She wasn't to big on the one night stand idea. Though, if she was, Hunter seemed like a great option.

"To be honest, I don't know if I have references about my taste as you say, my ex wasn't too big into that type of foreplay." Chelsea admitted and took a quick long drink waiting to see where the comment led.

When Hunter replied she was pleasantly surprised by the remark.

"Such a shame, you put in such great work to look as amazing as you do. You deserve to lay back and enjoy a few orgasms from a very eager and willing partner." Hunter said that and stared at Chelsea to see her reaction.

Chelsea couldn't help but smile wide at that especially now with the thought that this young man was implying that he was more than a quick pump and dump type of man.

"Yep a very smooth man," she said with a giggle. She looked straight at him as he stared into her eyes and felt like her soul. She leaned in closer to Hunter hoping he would take the hint and kiss her.

He did just that. He got his opening and he wasn't going to miss it. He leaned all the way in and the two's lips met for the first time.

The kiss was something that Chelsea immediately knew was a great decision. It started out as soft and sensual and continued to a full on make out session she hadn't had since her pre kids days.

The two continued to make out until Chelsea paused for a moment as she felt Hunters hand slide onto her knee. The pause wasn't long as she got right back into the moment and felt another rush through her body. She wanted nothing more at the moment than for Hunter to touch her all over.