Date with Mom's Friend

During his senior year of high school Jeremy Richards decided he was going to work on changing his life, he had always gotten good grades in school and was always considered to be well behaved. He never tried playing sports and he was always thirty pounds overweight so this year he decided he was going to play sports along with his academics.

In the fall he played soccer and he did make the team but sat the bench most of the year getting to play in the last game for a few minutes. It had some of its desired effect as he lost a few pounds and made friends with kids that played sports. He got invited on a few outings and to a few parties so this encouraged him to play basketball.

He tried out for the team and surprisingly improved over the season where he got to play in a few games that were blowouts. Jeremy scored twelve points by the end of the season and was awarded the most improved player award. He also managed to lose ten pounds then he tried out for baseball season, he managed to lose ten more pounds and his coach and gym teacher helped lose the rest before school let out and he turned eighteen the day it happened.

For his birthday his father bought him a home gym and a treadmill and at his mother's insistence got him a car as well. Now he was eighteen in the best shape of his life, had a lot of new friends, ready to start college in the fall. He finally had courage to ask a girl out on a date, he had chances with a few girls that were in some of his academic clubs but he wanted to venture out with more popular girls.

So he decided to use the phone in the kitchen, he could of took the cordless for more privacy but his mother would just sit and bug him for what happened. She was sitting in the kitchen with her best friend Donna having coffee while started calling for dates. He had three girls in mind that he would try to ask out, so he opened up his address book and called the first one.

Jeremy dialed the number of Rebecca Culver a cheerleader he got to know during basketball season, he waited until her father answered.

"Hello sir, my name is Jeremy Richards, is Rebecca there?" He asked.

"No young man, she is at cheer camp for the next three weeks, did you know they actually give scholarships for that. How about you are you going off anywhere for the summer or going to college in the fall?" He asked after explaining where she was.

"Yes sir, I plan going to MIT and sorry to bother you and congratulate Rebecca on the cheerleader scholarship." Jeremy said.

"Your welcome, I will let her know you called." He said hanging up.

"Well strike one." He said looking up another number.

"Hello is Jennifer there." He asked a woman who was probably her mother.

"Hold on a minute." She said.

"Hello." Jennifer said picking up the phone.

"Hey Jen, it's me Jeremy." He said.

"Hi Jeremy, how are you doing?" She asked.

"Good I was wondering if you would like to catch a movie and get a bite to eat sometime." He asked.

"Oh Jeremy that is sweet of you to ask but I started seeing Ray Jones a couple weeks ago, I'm sorry if I was not I surely would have." She explained.

"Okay, that is cool Ray is a really good guy." He said saying his good byes and hanging up. "Strike two."

"Hello Janet, this Jeremy Richards, I was wondering if you would be interested in catching a movie and getting some dinner with me?" He asked.

"Oh I'm sorry Jeremy, I'm leaving tonight to go on a vacation with my mother and aunt, won't be back for a couple weeks." She said.

"Oh I guess I should of called sooner, well have a good time." He said.

"Thank you, I'm sure we will." She said hanging up.

"I'll call that one a foul tip; I'm going to try Karen from my math club." He said dialing a new number into the phone. "Hello Karen."

"Oh Hi Jeremy, what's up?" She asked.

"I was wondering if you would be interested in seeing a movie, maybe getting some dinner sometime." He asked.

"I don't think so, you know the whole time we were high school, I dropped you several hints that I liked you and you always ignored them." She said.

"Well you know me, I'm book smart, but I don't know women." He laughed.

"I think I will have to think about it and let you know later on, I just took a job interning at my dad's law office and I want concentrate on that, maybe I'll go into the family business." She said. "I'll talk to you later."

"Okay see yah." He replied. "Strike three."

He hung up the phone and looked really dejected, as he turned around to see his mother and her friend staring at him. He shrugged for a moment and then slumped his shoulders grabbing a diet coke out of the refrigerator and turning to leave.

"You okay honey." His mother asked.

"I guess, just kind of bummed out." He replied leaving the kitchen for his room.

"Poor kid, he worked so hard to get in shape and he has never had a date." His mother said. "He really hoped for one before college."

"He is such a handsome boy; you would think he would have an easy time getting a date." Donna said.

"I was hoping that with the losing weight and if he could get a date it would boost his confidence before he goes off to college." His mother replied.

"You know with Steve on the road for business all the time and I cooped up at home with three kids, I could use a break." Donna said.

"What are you getting at?" Jeremy's mother replied.

"Well Anne, I could go on a date with Jeremy, I went through the same thing after my third kid lost the baby weight and got my figure back, I don't look bad for a thirty six year old woman. Being home with the kids during the day and when they get out of school I could use a break and Steve is not home to give me one." Donna explained.

"You are saying you want to date my son." Anne said surprised.

"Well yes in a sense, to help he get his self confidence and to give me some time out away from the kids, it sounds like a win win if you ask me." Donna said.

"It does make sense, let's go up and talk to him." Anne said getting up.

Anne and Donna went up to Jeremy's room to find him lying on his bed watching television, he still looked pretty down. When they entered he sat up a bit and made room for his mother to sit down next to him and Donna sat at his computer desk.

"Jeremy we have an interesting offer for you if you want to listen, it may make you feel a bit better." His mother said.

"Okay mom." He replied.

"Well son I'll let Donna explain." His mother said passing it off to her friend.

"Jeremy I have been friends with you mother for a while and we have been neighbors for a while now too, I've watched you grow up into a handsome young man and I feel bad about you situation." She explained. "Any ways you know my kids are little yet and my husband is on the road a lot for work, so I get lonely and need some time away. So I was thinking maybe you and I could go out on a date as friends, it would make you feel better and I can get out of the house."

"Sounds like pity to me, besides your married and older; I don't mean it like that you're also beautiful." He said not trying to offend her.

"No it's not pity and yes I'm married, it's not like we are going to have an affair, we can go places no one will know us or see us and thank you for the compliment." She replied.

"Okay I guess over in Smithtown they got a theatre, we could catch a movie and get a bite to eat there." He said.

"Sounds like a date, pick me up at seven tomorrow night, we will catch the late movie." She said.

"Alright." He said as they got up to leave.

Jeremy had always liked Donna; she had a great personality, a nice body and tanned skin, blonde hair that went down to her shoulders and blue eyes. A few times he had seen her in a bikini and she has been in many of his masturbation fantasies over the years. He was now really looking forward to his pity date with her, it was better than nothing.

The next night came and Jeremy was ready early to go pick Donna up, he wore a nice blue button up shirt and a pair of khaki shorts. He drove his car over to her house and went up to the front door, his mother was there playing in the living room with her kids.

He was stunned when Donna entered the living room; she was wearing a black button up cardigan tee that was long sleeve and showed off her cleavage. Her makeup and hair was nicely done and she smelled very nice. Jeremy could not believe how hot she looked as she slipped on her heels, she was wearing a very tight pair of jeans that made her ass look fantastic, and he was surprised that his mother's friend would dress this sexy for a pity date.

"Look it Anne, my handsome date is here." Donna said as she went over to Jeremy hooking her arm around his.

"Now you two kids go off and have fun and have her or him home by midnight." Anne said with a laugh.

"Alright see you later, be good for aunt Anne kids." She said as she allowed Jeremy to escort her out.

The entire drive to Smithtown they talked about his college plans and what movie they were going to see. Jeremy found a nice little Italian restaurant nothing fancy a typical family owned place that had pizza or other items that was both eat in or take out. Everyone stared as he walked in with the hottest woman in the place.

They ordered dinner and Donna got a carafe of wine, they talked about the small restaurant and the smell of the food coming from the kitchen. In the light of the restaurant Jeremy noticed that Donna had the prettiest blue eyes he had ever looked into. He took a chance at flirting with her and decided that he needs to compliment her on them and how she looked.

"You look really nice tonight." He said.

"Thank you Jeremy, so do you." She replied.

"Has anyone ever told you that you have the prettiest blue eyes, I never noticed until tonight." He said.

"Not lately." She said smiling. "Very flattering."

During dinner they ate and had conversations about different things they had in common or that interest them both. Donna found she got a mild buzz from the carafe of wine, Jeremy paid and they went to the movie theatre catching the late show.

The got a couple sodas and a large popcorn to share between them, they settled in the middle to watch the movie. It was a romantic comedy with some raunchy humor from time to time and a couple love scenes, a couple times their hands touched when getting popcorn. Finally Donna decided that they had enough and put it on the floor, Jeremy had his hand on the armrest and she put hers right next to it, Then she took his hand into hers and they held hands the rest of the movie.

Jeremy felt all gushy inside as she did this and he felt his cock stir, the thought of this hot mom, his mother's friend sitting next to him in a movie theatre holding his hand. A hot married woman holding his hand while her husband was out of town. The movie was over and they rode home, Donna asked if it was alright if she could snooze. Jeremy gave her a blanket and a jacket from the back seat; she used the blanket over legs and the jacket for a pillow.

On the drive home Donna was reclined back and she was sleeping soundly, unaware that the position she was laying in left a lot of her chest on display. Jeremy could see right to her black lace cup that housed her left breast. His heart was beating rapidly in his chest, he could see some of the milky white of her breast where her bikini covered.

His poor cock felt as if it was going to burst, he kept taking mental pictures in his mind of the beautiful older woman next to him. He was sad when he finally pulled up in front of her house, he grunted and she woke up. She sat up in the car seat and smiled at him, rubbed her eyes and opened the door to get out; before she did she turned to say something to him.

"That was a nice first date; did you have a good time?" She asked him

"Yes I did, did you?" He asked.

"Yes, it was fun and nice to get out, maybe we will do it again next week if you're up to it or you can't find a date, let me know and I'll let you know when I'm free." She said.

"Okay thanks Donna." He said.

"Thank you Jeremy and good night." She finally said getting out of the car.

He watched the sway of her hips as they moved when she went in, he adjusted his cock so his mother would not notice his massive hard on which started to subside. When his mother finally came out he drove them home and his mother asked how he liked his date and he told her it was fun. He quickly went to his room and went to bed; only he had to masturbate thinking of Donna while he did so.

With his confidence up a bit he did try to ask out Karen again only this time she had other plans, so without his mother knowing he called Donna up at home. He knew she should have run it by his mother before talking to her best friend but he could not stop thinking about her and their date from last week.

"Hey Anne, how's it going?" She asked answering the phone.

"Um no, it's Jeremy, I got shot down again and was wondering if you were going to be free sometime this week?" He knew she had Tuesday through Thursday open, he knew with this being Tuesday night that gave him a shot at the other two.

"Sure how about tomorrow night, what did you have in mind?" She asked.

"I was thinking a picnic on Sutter's hill, I would bring my telescope and we could do some stargazing, I thought it would be something you never done and would be fun." He said.

"That does sound like a fun idea." She replied. "Let me pack the dinner, you bring your telescope and a blanket."

"Okay sees you tomorrow, I'll see if my mom will sit." He said.

"Oh alright, see you tomorrow." She said sounding surprised he did not run this by his mom.

His mother agreed to watch Donna's kids and he picked her up, she came out with a large basket and he got out helping her with it. Then he let her in the car and they drove up the hill, it was just turning dusk, when they found a nice secluded field he spread the blanket, she set out the food and he set up the telescope.

She wore a green strapless bra top dress that showed a lot of cleavage and leg, she looked really sexy. She had on a nice perfume and her hair was pulled back and up. When she had everything set up he was surprised when she pulled out a bottle of wine.

"Your mother said a little wine won't hurt you." She said pouring a glass.

"Oh thanks." He said taking a glass.

The two of them made small talk and Jeremy soaked up how sexy she looked tonight, he even mentioned that the green of the dress brought out the blue in her eyes. Before they knew it the food and the wine was gone, both of them had a little buzz feeling from it.

"Well you want to have a look at the stars?" He asked.

"Yes show me how this thing works." She replied.

He led her over to the telescope and found a cool constellation to look at and showed her, she wanted to see a planet and he found Jupiter for her. As she leaned over to look he stood behind her and showed her how to adjust the scope, she could feel his hard on brushing her leg. Donna thought to herself that this was kind of sexy being able to turn on a young man half her age.

After they looked at a few more stars and other celestial objects Donna suggested they sit on the blanket, she mentioned she was cold and he offered to go to the car to get a jacket. She suggested he sit closer to her to keep her warm instead.

"Jeremy has you ever kissed anyone?" She asked.

"You mean on the lips, like making out?" He asked.

"Yes." She said.

"No, never." He replied.

"Would you like to try it for a little bit before you take me home?" She asked.

"Okay." He said and they laughed.

Then without warning she leaned in and put her lips to his, he was stiff and nervous but she told him to relax and resumed kissing him. As their lips smacked together she pushed her tongue past his lips and let out a soft moan. The kid was a good kisser she thought and he was so tender, she wrapped her arms around his neck and pulled him down on top of her.

The two of them lay on the blanket kissing passionately under the stars; Donna could not help to think that she had never done anything this romantic with her husband. Then without warning she felt his hand run up her side and gently cup one of her breasts. Her nipple was hard and sensitive to the touch, mostly due to the cool night air and her growing horniness developing between her legs.

She decided a little boob fondling would not hurt and she enjoyed the gentle touch, her husband was usually rough when he got home and wanted sex. The other drawback to his aggressiveness was her husband usually finished sooner and rarely got her off. This was such a nice change of pace, but she had to be careful so this would not get out of hand.

Before she could react he had gently pulled the dress down enough to expose her bare breast, when he touched it he came in his pants. Donna could sense him stiffening up and knew what he did, she gently pulled the dress back up, they kissed a bit more and then suggested the go home.

When the got to her house his she gave him a peck on the cheek and said goodnight, then she went in and sent out his mother. They went home and he was ready to masturbate thinking about his first ever boob grabs. Like before he was done in no time, his cum shot all over his chest, he wiped himself off and fell asleep.

He did not even bother to try to ask anyone else out, he could only think about Donna and how far she let him get. As usual her husband was gone on Monday night for business trip and Tuesday night she called Jeremy's cell phone which surprised him.

"Hey Jeremy, your mom gave me your cell phone number a while back in case of emergency, I'm really bored tonight, would you like to come over and watch a movie on cable with me, I will pop some popcorn and we can have some cokes." She said.

"Wow that sounds really cool, what time do you want me to come over?" He asked.

"Come over around nine thirty, the kids will be in bed for an hour by then." She said.

He searched the internet, if there was going to be a repeat of last week, he did not want to go off early in case he could do more with her. It was recommended that he masturbate before going over and around nine o clocks he masturbated. At ten after he cleaned up and put on clean underwear, a pair of loose gym shorts and a tee shirt.

His mother did not seem to know he was going over to Donna's when she asked he just said he was going to hang out with friends. Donna did not inform his mother this time and he drove over to her house and parked in the driveway. The neighbors would think it was his mother just using his car and they were visiting, when he went to the door, he could smell the popcorn.

"Hey Jeremy come on in." She said ushering him into the kitchen.

"Thank you, you need some help?" He asked coming into the kitchen.

"Almost done, you can pour a couple glasses of coke." She said.

He noticed she was wearing a pair of satin pajamas; they were blue with white stars. He did not know at the time but she did not have anything on under them as they went into the living room. He sat down on the loveseat and she sat next to him, he was surprised that she had an erotic thriller loaded in the DVD player.

The movie had a good story to it, it had some nudity and some sex scenes that made Jeremy think of trying to see if Donna was interested. He glanced at her chest which was heaving in the pajamas; he could see her nipples sticking out. He decided that it was now or never to take a chance, so he turned his head towards her and leaned in, kissing her neck gently, then up to her ear.

"You look very beautiful tonight." He said in a low whisper.

She turned her head towards him, without saying anything she smiled at him and then kissed him. Again the two of them began to make out on the couch, no longer watching the movie. Jeremy did not go for her breasts, which surprised Donna; she was going to let him play with them again tonight. Without her realizing it, he undid the button from the bottom up, by the time she realized it he was on the last two and she figured she would let him undo them. Then gently he slid the top off of her shoulders, Donna could not believe it, she let him get her topless and she helped him by letting him slide it down off her arms.