Go Back   Literotica Discussion Board > Main Literotica Forums > Sexual Role Playing

Reply
 
Thread Tools

Old 03-08-2012, 10:32 PM   #1
Orgasmicallyfun
Literotica Guru
 
Orgasmicallyfun's Avatar
 
Orgasmicallyfun is online now
Join Date: Feb 2011
Location: New Jersey
Posts: 10,513
Hooking up with a MILF(CLOSED)

Matt Williams: Age 19 Height 6'2 Black Hair Brown Eyes Tan muscular body

All throughout high school girls were all over Matt always trying to get him to go out with them, but he had eyes on one girl only, Pamela. Their relationship started their junior year and last all the way to graduation. They had a textbook high school romance. He had been with a couple girls before her and they all had sex with him, Pamela was a different story but he was patient with her because he truly had feelings for her.

Matt was always over at her house and got to know her mother pretty well and they ended up being good friends. About a month and a half after graduation during the summer their relationship came to an abrupt end. He never really told anyone why when they asked why they broke up. He no longer saw her mother either which was a shame because he really enjoyed talking and hanging out with her.

After almost two months of a depression like phase Matt decided it was time to move on. He got an idea to go to a beach resort in the Cayman Islands to have some fun and enjoy his life. After all it had been a long time since he had sex so he hoped this would change things. He packed his bags and headed for the resort. It was an amazing place, beautiful building white sand beaches nearby, pools, this place had everything and he knew he made the right choice coming here.
  Reply With Quote

Old 03-08-2012, 11:01 PM   #2
teazme
Literotica Guru
 
teazme is offline
Join Date: Dec 2008
Location: Midwest
Posts: 4,490
Tanya Jones, aged 37 with a fantastic body. Wherever she goes she turns heads. She is 5'4, 120lbs, her boobs are a fantastic 34D. She runs and does yoga everyday so she has a very toned body, especially her ass. It is a daily occurance that a man grabs her ass. She has long blonde hair and big blue eyes to complete her apperance. No one would ever guess she is a mother of an 18 year old, along with two other children.

Tanya noticed her daughter Pamela's boyfriend and was quite impressed, he was a good looking guy. Tanya was always nice to him and was attracted to him, but he was dating her daughter, it would be wrong of her to go after him. So Tanya decided to admire from afar. Suddenly in the summer the two broke up.

Tanya and her husband of 17 years had just spilt up, they had married because of the unplanned baby and stayed together just for the children. They decided they couldn't deal with it any longer so they spilt amicably. The children however, did not take it well. Pamela, Tanya's daughter took it especially hard and no longer talks to Tanya. Tanya decides to go do to the Cayman Islands for a few days to relax, unwind, and get some ass.
  Reply With Quote

Old 03-08-2012, 11:10 PM   #3
Orgasmicallyfun
Literotica Guru
 
Orgasmicallyfun's Avatar
 
Orgasmicallyfun is online now
Join Date: Feb 2011
Location: New Jersey
Posts: 10,513
It was around noon when Matt finally checked in and was showed his room on the first floor. It was a great room it had a big living room with nice sectional couch and a recliner and just about everything else you would come to expect from a five star resort. The bedroom had a king sized bed with satin sheets and two nightstands on each side of the bed with a long dresser stretching across one of the walls with a mirror in the center over looking the bed. When he opened the patio door in the bedroom he was amazing at the sight. His patio had a couple chairs and once you stepped off the patio your feet were in the sand of the beach.

The bathroom had a stand up shower with a glass door and a jacuzzi tub in the corner. 'Damn I gotta find a girl to share this amazing room with.' He thought to himself as he stripped down and pulled on a pair of board shorts and tight tank top to show off his muscles and six pack. Putting his sunglasses on he headed over to the pool area to see what kind of girls were hanging around.
  Reply With Quote

Old 03-09-2012, 10:19 AM   #4
teazme
Literotica Guru
 
teazme is offline
Join Date: Dec 2008
Location: Midwest
Posts: 4,490
Tanya arrived at the resort and was given a smaller room because the resort had lost her reservation. Tanya decided not to be bummed out, she was on vacation, besides she can always go to the guys room. Tanya walks into her room and is still impressed with the large bed and furnishings, not as nice as a suite, but it will do.

Tanya quickly puts on her little black bikini, heels, sarong, and sunglasses and heads for the pool. The pool area was absolutely amazing, it had a swim up bar and an infinity look to it. Tanya was quite impressed. She walked down and found a recliner and set up her spot. She laid down the towel and untied her sarong. She sees a good looking guy and decides to go over and have him buy her a drink.
  Reply With Quote

Old 03-09-2012, 10:26 AM   #5
Orgasmicallyfun
Literotica Guru
 
Orgasmicallyfun's Avatar
 
Orgasmicallyfun is online now
Join Date: Feb 2011
Location: New Jersey
Posts: 10,513
After scouting out the girls he wasn't sure where to start there were so many good looking girls. He pulled his tank top off and laid it on one of the chairs along with his sunglasses and dove into the pool swimming around for a little he ended up over by the bar. This was when he spotted someone who looked very familiar. It was Tanya, Pamela's mother and she was looking as good as always. She wasn't with her husband though and seemed to be talking to another guy. After thinking about it for a little he approached her from the side. "Tanya?" He asked
  Reply With Quote

Old 03-09-2012, 10:39 AM   #6
teazme
Literotica Guru
 
teazme is offline
Join Date: Dec 2008
Location: Midwest
Posts: 4,490
Tanya heard her named and jumped, no one was supposed to know her here. She turns around and smiles widely, "Matty." The guy Tanya was talking to walked away, knowing he could never compete with Matt. Tanya gives Matt a hug, pressing her firm breasts into his muscular chest. Tanya leads Matt back over to her lounge chair and settles him in next to her, "help me put lotion on my back while you tell me what you are doing here." Tanya just knows his big strong hands are going to feel amazing on her back.
  Reply With Quote

Old 03-09-2012, 10:46 AM   #7
Orgasmicallyfun
Literotica Guru
 
Orgasmicallyfun's Avatar
 
Orgasmicallyfun is online now
Join Date: Feb 2011
Location: New Jersey
Posts: 10,513
Matt hugged Tanya back with a grin on his face. No one else ever called him Matty and he liked when she did. She lead him right back her chair and right away asked him to put sun tan lotion on her back. He couldn't say no so he grabbed the bottle and squirted some onto his hands and started rubbing up by her shoulders working his way to her lower back slowly while he talked. "Well the break up with Pam messed me up pretty bad so after sitting around doing nothing I decided I needed to get back in the game so that's why I'm here. I actually just got here about two hours ago. How about you? What brings you here Tanya?" Matt was now rubbing her arms and sides before he was done spreading lotion over her body.
  Reply With Quote

Old 03-09-2012, 10:52 AM   #8
teazme
Literotica Guru
 
teazme is offline
Join Date: Dec 2008
Location: Midwest
Posts: 4,490
Tanya smiles as she listens to Matt tell her the break up with Pam hurt him pretty bad. Tanya turns her head, "why did the two of you break up? Pam never did tell me." Tanya moans a little as Matt rubs lotion into her back. She takes the lotion from him and proceeds to put some on her legs and moves to coat her torso. Most of her boobs are hanging out of the bikini, only a tiny little bit is covered. Tanya decides to be honest with Matt, "well Matty Mr. jones and i decided to get a divorce. I am here to kind of get my groove back a little bit. Mr. Jones didnt appreciate me any more."
  Reply With Quote

Old 03-09-2012, 11:08 AM   #9
Orgasmicallyfun
Literotica Guru
 
Orgasmicallyfun's Avatar
 
Orgasmicallyfun is online now
Join Date: Feb 2011
Location: New Jersey
Posts: 10,513
So it seemed they were both here for the same thing, it was definitely a small world. "I'm so sorry to hear that. He had to have been a fool to let you go" He leaned back onto his chair letting the sun hit his muscular body trying hard not to watch Tanya rub the lotion over the front of her body. It wasn't until then he realized how tiny her bikini really was if it was an smaller her breasts probably would have broken free.
  Reply With Quote

Old 03-09-2012, 11:11 AM   #10
teazme
Literotica Guru
 
teazme is offline
Join Date: Dec 2008
Location: Midwest
Posts: 4,490
Tanya notices Matt looking at her breasts, "you didnt answer my question Matty, why did you and Pam break up?" Tanya really wants to know why her daughter was stupid enough to let this good looking man go. Tanya lays on her back and puts her sunglasses on, "tell me Matty, I dont talk to Pam any more so it is ok."
  Reply With Quote

Old 03-09-2012, 11:16 AM   #11
Orgasmicallyfun
Literotica Guru
 
Orgasmicallyfun's Avatar
 
Orgasmicallyfun is online now
Join Date: Feb 2011
Location: New Jersey
Posts: 10,513
"I really don't like talking about it but lets just say she didn't like one part of me" That was the most he ever told anyone about the break up and he felt himself wanting to tell her more for some reason but he waited to see if she asked more about it first. He folded his arms behind his back and let his eyes scan over the pool while he sat there with Tanya.
  Reply With Quote

Old 03-09-2012, 11:20 AM   #12
teazme
Literotica Guru
 
teazme is offline
Join Date: Dec 2008
Location: Midwest
Posts: 4,490
Tanya smiles, "what part of you didnt she like? Because everything i see is wonderful to like. My daughter is an idiot for leaving you." Tanya seems him looking over the pool, "so you looking for a pussy to help you get over my daughter?" Tanya rolls over onto her back and unties the top of her bikini, she hates tan lines. She smiles as she sees a few other women without a top and decides to take her top off.
  Reply With Quote

Old 03-09-2012, 11:25 AM   #13
Orgasmicallyfun
Literotica Guru
 
Orgasmicallyfun's Avatar
 
Orgasmicallyfun is online now
Join Date: Feb 2011
Location: New Jersey
Posts: 10,513
Matt leaned up in his chair and turned to lean down close to Tanya trying hard not to start at the sides of her breasts visible now. "Well.." He paused for a second wondering if he should actually tell her. "She was a virgin and once she found out how big I was she was too scared it would hurt her more than make her feel better."
  Reply With Quote

Old 03-09-2012, 11:28 AM   #14
teazme
Literotica Guru
 
teazme is offline
Join Date: Dec 2008
Location: Midwest
Posts: 4,490
Tanya smiles at Matt, "ok Matty, tell me how big you are. Mr. Jones was average, only about 6 inches. I have always wanted to experience a larger cock." Tanya looks down at Matt's board shorts, "im guessing about 8 inches or larger." Tanya has no worries about hitting on him since she knows she looks good for her age.
  Reply With Quote

Old 03-09-2012, 11:33 AM   #15
Orgasmicallyfun
Literotica Guru
 
Orgasmicallyfun's Avatar
 
Orgasmicallyfun is online now
Join Date: Feb 2011
Location: New Jersey
Posts: 10,513
He couldn't believe that Tanya started asking him how big he was. Matt wasn't sure he never really measured his cock before so he just estimated. "I'd say about ten and a half inches when hard but probably a little bigger since I'm not good at measuring length."
  Reply With Quote

Old 03-09-2012, 11:36 AM   #16
teazme
Literotica Guru
 
teazme is offline
Join Date: Dec 2008
Location: Midwest
Posts: 4,490
Tanya looks over at Matt, "wow, that sounds like a good piece of cock." Tanya smiles at Matt, "so have you found a girl you might want to fuck with that rod. Or do you think you should stick to a mature woman, one who knows how to handle a cock." Tanya lets the suggestion sit, she would love to go back to Matt's room and fuck him silly all week, she only hopes he finds her attractive.
  Reply With Quote

Old 03-09-2012, 11:42 AM   #17
Orgasmicallyfun
Literotica Guru
 
Orgasmicallyfun's Avatar
 
Orgasmicallyfun is online now
Join Date: Feb 2011
Location: New Jersey
Posts: 10,513
'Is this really happening?' Matt thought to himself as he was caught off guard by all the questions Tanya was asking him. "Well I haven't had much time to look around considering I just got here, but it sounds like you want me to go with the second option." He said with a grin as he leaned back into his chair again.
  Reply With Quote

Old 03-09-2012, 11:46 AM   #18
teazme
Literotica Guru
 
teazme is offline
Join Date: Dec 2008
Location: Midwest
Posts: 4,490
Tanya smiles at Matt, "well if you were to ask me to go to your room, I would follow quite willingly." Tanya winks at Matt, letting him know she is serious. Before Matt can answer a girl about his age with blonde hair, blue eyes, big tits, toned tummy and legs walks over, "hi there, I noticed you and your mother over here and thought I would rescue you. Me and my friends, are going to a bar and thought you would want to join us." She spins and shows him her ass with the thong she is wearing.
  Reply With Quote

Old 03-09-2012, 12:06 PM   #19
Orgasmicallyfun
Literotica Guru
 
Orgasmicallyfun's Avatar
 
Orgasmicallyfun is online now
Join Date: Feb 2011
Location: New Jersey
Posts: 10,513
Matt eyes the teen girl up and would have loved to go with her and end up fucking her into oblivion but he didn't want to be rude to Tanya. "Well this isn't my mother and we were in the middle of a conversation here so I'll pass" Even if he didn't end up hooking up with Tanya if she was just teasing him he could get any girl he wanted here so he had plenty of back up plans.
  Reply With Quote

Old 03-09-2012, 12:09 PM   #20
teazme
Literotica Guru
 
teazme is offline
Join Date: Dec 2008
Location: Midwest
Posts: 4,490
Tanya smiles at him, "its ok Matty, go with her." Tanya smiles, this little girl is no challenge to her, she knows how to tempt someone like Matt. The girl smiles, "listen to her come with us." The girl pulls him out of his chair, "you won't regret it." Tanya nods her head in encouragement, once he gets fucked by a young girl who will run at his size, he will come running back to her.
  Reply With Quote

Old 03-09-2012, 12:14 PM   #21
Orgasmicallyfun
Literotica Guru
 
Orgasmicallyfun's Avatar
 
Orgasmicallyfun is online now
Join Date: Feb 2011
Location: New Jersey
Posts: 10,513
"No I couldn't do that to you Tanya we have a lot of catching up to do it has been a couple months since we saw each other." He sat back down on his chair knowing the girl would be disappointed but he didn't mind. It was nice to talk to Tanya after not seeing her in so long.
  Reply With Quote

Old 03-09-2012, 12:22 PM   #22
teazme
Literotica Guru
 
teazme is offline
Join Date: Dec 2008
Location: Midwest
Posts: 4,490
Tanya smiles at Matt, "i will be here all week, go with this girl and we will catch up tomorrow." Looking over the pool Tanya sees a good looking guy about her age and she goes to talk him up. She wants Matt to go with the girl, so he learn that he needs an older woman to give him the pleasure he deserves.
  Reply With Quote

Old 03-09-2012, 12:30 PM   #23
Orgasmicallyfun
Literotica Guru
 
Orgasmicallyfun's Avatar
 
Orgasmicallyfun is online now
Join Date: Feb 2011
Location: New Jersey
Posts: 10,513
"Alright" He got up and went right up to the girl placing his arm around her shoulder. "Sorry about that I didn't really feel like leaving her but I realized a girl like you could use a guy like me by her side" He said with a smile as he leaned back and looked down at her ass that bouncing with each step she took.
  Reply With Quote

Old 03-09-2012, 12:34 PM   #24
teazme
Literotica Guru
 
teazme is offline
Join Date: Dec 2008
Location: Midwest
Posts: 4,490
The girls and Matt head out to a bar in town and the girl who picked up out at the pool, Kate, danced with him. But it wasn't just dancing she was grinding and thrusting her hips to him in a preliminary fuck. She looks at him, "want to go back to the hotel baby? Im sure you could use a good fuck right now." Kate was a college girl who was having the time of her life, she just wanted to get laid hard and often. She spotted Matt and his muscles and immediatly moved in.
  Reply With Quote

Old 03-09-2012, 12:49 PM   #25
Orgasmicallyfun
Literotica Guru
 
Orgasmicallyfun's Avatar
 
Orgasmicallyfun is online now
Join Date: Feb 2011
Location: New Jersey
Posts: 10,513
Matt held onto Kate's hips and sway his hips to the beat of the music as she grind into him. "Yeah let's go your room or mine?" He asked over the loud music his face near her ear and they were both very close to each other their bodies basically glued to one another.
  Reply With Quote
Reply


Thread Tools

Posting Rules
You may not post new threads
You may not post replies
You may not post attachments
You may not edit your posts

vB code is On
Smilies are On
[IMG] code is On
HTML code is Off
Forum Jump



All times are GMT -4. The time now is 06:37 PM.

Copyright 1998-2013 Literotica Online. Literotica is a registered trademark.