New sex story: Hindsight

Chapter 1
Mary Ellen Jakowski sat in her kitchen with her good friend Dana Carter having their usual morning coffee. The two women had been friends since the Carters moved into the neighborhood five years ago. Their husbands, Richard and Drew, had become buddies as well. They were "backyard" friends, as their privacy fences were connected. In fact, they rarely went to one another's house through the front door. It was a one-block walk around the neighborhood to get to the front door.
The two women normally shared a lively morning conversation but today for some reason, Mary Ellen seemed quiet. She had just had her 35th birthday and was feeling a little down. However, it wasn't only the age thing that was bothering her. It seemed that her relationship with Richard was losing its spark. She knew that that wasn't unusual for a twelve-year marriage and after two kids, but it was difficult to accept nonetheless.
Suddenly, as the women sat at the kitchen table, the door from the dining room flew open and the two Jakowski children came running through. "Leslie and Brett, slow down," Mary Ellen yelled as they chased each other out the back door. "Summer vacation is getting near and they will be home all day soon," Mary Ellen lamented, adding, "There goes my peace and quiet."
"Why aren't they in school today?"
"Some teachers conference or something like that."
They're getting big," Dana said with a smile, remembering how fast her daughter had grown.
"Brett had his tenth birthday two days ago and suddenly he thinks he is grown up," Mary Ellen laughed.
"Leslie is eight now?" Dana asked.
"Yes, going on fifteen. She is quite a handful already so I don't know what I'm going to do when she becomes a teenager."
"I know all about it. We had a tough time with Jill at that age," Dana said, speaking of her 19-year-old daughter who was now away at college. Dana had gotten pregnant with Jill when she was eighteen and just barely out of high school. Sometimes she regretted having a child that early. However, the advantage was that now Jill was out of the house and she and Drew were still young.
Drew was in his twenties when they met and married and he had wanted children right away. Dana had refused at first but she was young and eventually gave in to his pressure. It had all worked out for them anyway. They were financially well off now and life was good.
Mary Ellen sighed and gazed out the window at the children playing in the back yard. At least the kids were happy and well adjusted, she thought.
Rockmont was a great upper-middle class community with good public schools and plenty of public parks for kids to play. It had been a strain when they had bought the house eight years ago but it had been worth the struggle. Richard was making great money now with his PC support business and they had even joined the local country club. She knew that she should have been very happy but, unfortunately, there was a price to pay at home for Richard's success. He was rarely home since he started the business. He had promised in the beginning that the long hours and hard work was only temporary, until he got the business going. However, that was five years ago and he still worked eighty hours a week.
While Richard's work was a big part of Mary Ellen's problem it was not the entire issue. Sometimes she thought he worked just so he didn't have to be around her. It seemed they rarely even touched anymore. Then there were the issues in the bedroom. It had been a long time since they had been intimate. For a while she thought that maybe Richard was having an affair and even considered hiring a private detective. However, deep down she knew that there was a major gap between their desires for sex. Unfortunately, the gap was about as wide as it could get now. Besides that, Richard had always been hung up about sex and refused anything but the basic missionary position. She had tried to talk to him about it but he refused to even discuss the subject.
On the other hand, it appeared to Mary Ellen that Dana had the perfect life. Drew seemed to be around her all the time. The fact that he worked out of the house had something to do with it, however it was more than that. She could see how loving the two of them acted around each other. They were like newlyweds, always touching and whispering little secrets to one another. They just seemed compatible. Besides that, Drew was incredibly handsome and sexy. He was in his forties but looked younger, even with his slightly graying hair around the temples. He was tall and well built as well-the rugged outdoors type. He owned some kind of marketing company and appeared to make it work by the sheer power of his personality. Mary Ellen was envious. Not because he was so handsome, but because he was so attentive to Dana.
Dana knew that something was bothering Mary Ellen. They had been friends too long. She knew it had something to do with Mary Ellen and Richard's relationship because there had been several strong hints. While she didn't want to pry, she was her best friend. "What's the matter?" Dana finally asked.
"Oh nothing." Mary Ellen sighed and looked into her coffee cup.
"Sure something's the matter," Dana responded. "I've known you too long not to see it. We have always been able to share our problems. Come on."
Mary Ellen took a deep breath. She was dying to tell Dana but didn't want to burden her with personal problems. It was now or never she thought. "It's... it's just that... oh I don't know, something's missing in our... in Richard and my relationship lately. He doesn't seem to pay any attention to me anymore." She knew that she was dramatically understating the issue.
"Have you tried sexy underwear?" Dana laughed.
"I'm serious," Mary Ellen said and a little tear came to her eye.
Dana saw her eyes start to tear up and realized that she was indeed serious. "I'm sorry Mary Ellen. However, I wasn't entirely joking when I said to try new underwear."
"It's more than that," Mary Ellen said and paused.
"What then? Don't tell me you're old. I'm older than you are. Besides, you have the body of a teenager." The older woman looked at Mary Ellen's slim form and sighed. "I would love to have your shape. Nice sized boobs and a dynamite ass," she said with a wide grin.
"Nice sized boobs? They're too small, especially compared to your 36C's. And, my ass is much too big."
"Well, 36C aren't all they are made out to be. Gravity has a way of taking care of that. You will never have that problem. As for your ass, Drew drools over it. And, when you wear those little pink short shorts in the yard... well, I practically get raped." The older woman laughed loudly. "I should buy all your clothes for you," she added with a coy smile.
"He does? Drew drools over my ass?" Mary Ellen asked and then realized that she was acting a little too interested in what her friend's husband thought of her. Her face turned red with embarrassment.
"Yeah. Last week you were out back planting flowers and he saw you from his office window. I don't know how long he was watching you but when I came in to ask him if he wanted lunch... well, I thought you would have heard me scream. Boom, right over the desk." Now Dana's face flushed as she remembered what had happened that day. She knew that Drew was an "ass" man from the time that they met. In fact, they had started to have anal sex the first year they were married. Sometimes she thought that that was all they did. Not that anal sex was bad... no she loved it... sometimes it just seemed that she couldn't satisfy his lust. She worried about that.
"I never knew," Mary Ellen said thoughtfully. "Sure, I see his eyes on me but every guy does that." Again, Mary Ellen realized what she was saying about noticing her friend's husband's admiring glances and added, "I'm sorry."
"I'm sure every very guy 'does' look at that ass of yours," Dana laughed. "Even I'm amazed by how trim and shapely your hips are after two kids. If I was a man..." Dana paused and then said, "Now I'm embarrassing myself," and she suddenly looked away from the younger woman and blushed. If she told her the truth, sometimes she had a difficult time keeping her eyes off of the younger woman. Dana had never had a thing for women but if she did, Mary Ellen would be on the list.
Mary Ellen blushed again as well. "Well, thanks for making me feel better."
After a long and somewhat uncomfortable pause, Dana took a deep breath and said, "I still think you should consider the underwear angle. I hate to tell you this lady, but you need to spice up your wardrobe."
"What's wrong with my wardrobe?" Mary Ellen said defensively.
Dana looked at Mary Ellen and bit her lip, trying to decide if she should go any further. This was a touchy subject, especially because she was already obviously feeling depressed. Dana didn't want to make the problem worse but she thought that if your own friends won't tell you the truth then who will. Finally she sighed and said, "It has been getting a little shabby lately. I think some new things would do wonders for your sex life."
At first Mary Ellen looked shocked and hurt, but then her face showed resignation. "I guess you're right. I have been neglecting myself lately and I'm probably in just as much of a rut as Richard. The truth is that I'm willing to try anything." She fell silent for a minute and then said, "Maybe you could go shopping with me sometime and help me pick out some sexy clothes?"
"I'd love to."
The back door suddenly opened and Drew came in. "Hi sweetie," he said as he walked over to his wife and kissed her on the lips. Then he leaned over and kissed Mary Ellen on the cheek. "How's my second favorite lady?" he said and wrapped his arm around her shoulder.
Mary Ellen got a pretty pout on her lips and said, "Second favorite?"
"Well, only when my wife is in hearing distance," he whispered and then winked at her as he stood by her side and pulled her warmly to his hip.
Mary Ellen felt a little chill run through her when her shoulder touched Drew's hip. He was wearing a pair of shorts with sandals and a muscle shirt on top. His body showed the hours he spent at the gym and his bicycle riding. He was everything that Richard wasn't she thought. Mary Ellen sighed quietly. She knew that Richard wasn't a bad guy. He had provided them with a pretty good life and was never abusive to her or the children. Then, a little flash of guilt went through her. She loved Richard very much, but he was stuck in his ways. He came from a traditional Polish family and still held onto many of the old ways. Plus, he had begun to let himself go physically. Unfortunately, with his work, he didn't have time to work out and had let himself gain a good bit of weight. However, she tried not to nag him about it but she worried about his health.
"Hey, earth to Mary," Drew said with a laugh.
Mary Ellen shook her head and smiled up at Drew, admiring his handsome face and shining smile. Mary Ellen liked Drew. He was personable and funny. They had always shared good-natured kidding, often involving sexual innuendoes. Suddenly, after what Dana had said, the innuendoes took on a new dimension. That thing about him being an "ass" man struck a chord deep inside her. She felt a sudden pulsing in that secret place. That "place" that she could never mention to anyone.
Drew looked at Dana and asked, "I'm going up to Home Depot to get some things. Do you want to come along?"
"Yes, I need a couple of things at the linen store next door," Dana answered and got up.
"I'll see you at the car," Drew said to Dana and then kissed Mary Ellen on the cheek again.
When he pulled away, she felt his lips still on her cheek. Stop it! she scolded herself.
Both women watched the sexy older man walk out of the kitchen door. When Mary Ellen looked up, she saw Dana looking at her in a funny manner. Her face turned red again.
"Nice butt there huh?" Dana laughed.
Mary Ellen didn't answer. She couldn't without embarrassing herself even more.
"Tomorrow okay to go shopping?" Dana asked.
"That works as long as we do it before the kids softball practice at three."
"Let's do it at ten. I'll arrange everything and drive. See you tomorrow sweetie," Dana said and bent over and kissed the same spot that Drew had.
Mary Ellen thought she was losing her mind as her face burned with the touch of her girlfriend's lips. "Uh... yes... yes fine," she stuttered and then watched the older woman leave.
Chapter 2
Mary Ellen cleaned up the dishes and looked out in the back yard to see where the kids were. They were playing with a wiffle ball and bat. Do I have time? she thought as the pulsing down below continued. Making her decision, she hurried up to her bedroom, quickly closing the door and turning the lock. Suddenly, she felt so naughty. It was the middle of the morning.
As she passed the mirror on the back of the closet door she stopped. She was wearing a pair of baggy shorts and old shirt. A frown crossed her pretty face as she saw herself in a different light. She reached down and pulled her baggy shorts tight and turned so that her buttocks were facing the mirror. The shorts outlined her shapely rear, her panty line showing through. Maybe some new clothes would help! she thought as stared at the contours of her backside. Then she turned this way and that, bending slightly forward. She could feel her vagina continue to pulse with excitement. So Drew drools at this? she thought and a chill ran down her spine. On impulse, she pulled the seat of her shorts upward until the seam buried between her cheeks. "Ohhh!" she moaned when she felt the material touch her "there".
She bit her lip and she felt embarrassed as she looked at the drawer where she hid her pleasure devices. Making her decision, she rushed over and searched in the back, behind her underwear and various other "toys," to find the vibrator she had bought from a mail order catalog. It was long and tapered toward the end with a battery control device. There were rounded ridges up and down the shaft. The commercial said it was ideal for anal pleasure. It was!
Mary Ellen found some lubricant and rushed over to the bed. Her hands were trembling as she stripped off her clothes. She climbed onto the bed and got onto her hands and knees. When she looked back at the closet mirror she gasped. Her buttocks were pointed straight at the mirror and her tiny anal hole was almost pulsing between her cheeks. It was so obscene... but so exciting. Quickly she lubed up the shaft of the clear blue vibrator. Without touching her vagina, she placed the tip on her anus. A moan escaped her lips as she began to press the shaft into her tight hole. She pushed her hips backward and the long shaft began to slip into her.
"Oh Jesus," she moaned as the ridges bumped past her tight sphincter. Suddenly, she began to tremble all over and a vision of her handsome neighbor came into her mind. He was kneeling on the bed behind her and he had his long penis in his hand. It was huge with a large red head that was shining with his sex juice. "Do you want me to lube it?" he asked breathlessly in her fantasy.
"No, just fuck my ass! Please!"
Another groan escaped her lips as she pressed the vibrator deep into her anal canal. She pressed the button that made it squirm. Suddenly, she could feel it vibrating and twisting deep inside her. Her eyes closed tightly as she imagined Drew sliding his large penis into her virgin ass. "Ohhhhh God," she moaned as chills ran up and down her spine. She began to pump the long vibrator in and out between her spread ass cheeks as she spread her legs even wider. The tips of her naked breasts rubbed on the cover making her nipples swell with pleasure and sent ripples though her body. Suddenly every muscle in her body went stiff as waves of pleasure began to consume her. It felt like she might pass out as the long tip of the vibrator brought on spasms deep inside her bowels. It started with little shock waves in her stomach like it always did. Then they began to grow in strength until her entire groin was electrified and her anus pulsed, squeezing the invading tool. Her vagina pulsed as well and juice dripped to the bed. She squeezed her anal muscles on the squirming vibrator and her mouth opened as if to scream. Instead of screaming though, she bit her lip hard-the kids could be in the house now. She gasped and shook as a strong climax consumed her.
Finally, the satisfied woman fell exhaustedly to the bed. The long vibrator was still humming deep inside of her. As she lay gasping for breath, the twisting device began to slip out of her rear hole. Then, she heard the kids playing in the back yard and sighed contentedly. It was always the same when she had something up her rear. The climaxes were strong, almost earth shattering. However, in the after glow, like now, she always began to feel embarrassed and guilty. It was so against everything she had been taught. After all, she was a grown woman and for her to sneak into her room and do something like this... well, mothers didn't do that. Yet, she knew that she would do it again.
Mary Ellen had been very young when she first realized that she got a special thrill from her anus. It had happened almost by accident. She was masturbating with her fingers one time when she touched the tiny rear hole. It brought such a shock that she had to do it again. She felt nasty but still she pushed a finger inside. The feeling was so intense that she pulled it back out right away. She did it again, leaving it inside longer. Deep inside her, the muscles of her canal reacted, squeezing down onto the invading finger. At the same time, chills of pleasure like she had never known began to ripple through her. She began to move her finger in and out slowly, building speed until her hand was a blur. Within minutes her body began to tremble with an incredible climax. It went on for a long, long time until she collapsed onto the bed.
Over time Mary Ellen experimented with various means of pleasuring herself vaginally, but none equaled the times when she used her finger... or something else on her anus. She often thought that she was sick and that maybe she should see someone. However, she knew that she would be far too embarrassed to ever admit to a stranger that she loved paying with her anus. She would have to admit all of her little secrets. Like the times that she would go to the mall with Dana and walk around with those little vibrating balls up her butt. (Dana would certainly be shocked if she knew.) Or, how she fantasized about her ass being violated by a room full of men in a wild bacchanalia of anal pleasure.
The guilt that started long ago was still with her today as she lay on her bed in the afterglow of a very satisfying orgasm.
Chapter 3
"I told Mary Ellen how you drool over her ass," Dana said out of the blue as the two of them drove to the store.
"You told her what?" Drew asked incredulously.
Dana laughed. "We were talking about how depressed she was and I was trying to cheer her up. Besides, it's the truth."
"Yeah, but you don't have to tell my best friend's wife that I ogle her ass," Drew said. However, there wasn't any anger in his voice and he had a smile on his face.
"She needed some cheering up. It seems that Richard isn't taking care of her."
"The man must be crazy," Drew said as the smile grew on his handsome face.
"I guess it's not unusual for sex to get stale." She reached over and took Drew's hand. "I'm glad we're not like that anymore."
"Me too sweetie. I love you."
She squeezed his hand and said, "I love you too."
"So what else did you tell her... maybe that I like anal sex?"
"No, but she did seem to get pretty excited when I told her about you looking."