The Winston Family Adventures Pt.01

Ben and Catherine Winston are blessed with three healthy children; a daughter and two ruggedly handsome sons. Their two oldest children are twins; a boy named Michael and a girl named Madison. The youngest son is Jerry. The twins celebrated their birthday just a week before school was scheduled to begin. They will be juniors at a private college preparatory school. From the neck up you can’t tell the twins apart. Michael and Madison are twins in every way except size and gender. Madison is 5’6”, small build, but large breast for her age, and weighs 110 pounds. Michael is big for his age. He is 5’ 11” slender build and weighs 165 pounds. Michael and Madison both have sandy blonde hair and piercing blue eyes. Michael was named after Ben’s grandfather and Madison was Catherine’s maiden name.

The Winston’s seem to be the archetypal American family. They live in a comfortable four bedroom, two-story home located in an exclusive gated community. Each child is fortunate enough to have their own private bedroom. Madison’s bedroom has its own private bath and the two boys share a ‘Jack and Jill’ bathroom that connects their two bedrooms. Ben Winston is a registered pharmacist and works for a national pharmacy chain. Catherine is a registered nurse and works part-time as a floor supervisor at a local hospital. Catherine’s paycheck is used exclusively to pay the tuition for their children at the college preparatory school and the rest goes toward building the children’s college fund.

Each child excels in school and is very well behaved thanks to their mother’s very active supervision. Catherine is a member of the PTA and serves on several committees at the school, but still finds time to devote full attention to her children. Ben also serves on school committees and helps some with coaching football. He tries to play golf most week-ends and he is also a Captain in the Army Reserve Medical Corp. He is required to spend one week-end a month at Army Drills and two weeks in the summer at some U. S. Army Base Hospital. He also devotes a lot of attention to the children, but not nearly as much as Catherine.

On the twin’s recent birthday they had a nice party around the family swimming pool. Madison was allowed to have a slumber party following the birthday party. Twenty of the twin’s class mates attended the birthday party, but only four of Madison’s closest friends were invited to stay over for her slumber party. Her best friends are Becky, Susanne, Rena and Sally. The slumber party went well until Becky heard a noise from Madison’s bedroom closet. Dad was summoned and found Michael, who is a horny sixteen years old, hiding among his sister’s clothes. When questioned by his Dad he freely admitted he was hoping to sneak a peek at some naked girls, or naked tits, or at least one of them wearing something revealing. He wholeheartedly expressed his fascination with the female breast. His Dad found it amusing; however his Mother found it troubling.

Michael had been secretly fantasizing about his sister’s tits since she first began to develop them. Madison often slept in a cotton t-shirt or cotton pajamas. He loved it when her nipples got hard and poked against her pajama top. From time to time he’s gotten a few glimpses of her bare nipples when she wasn’t aware of his presences. He once considered secretly setting up a camcorder in her room to film her private moments, but measured the consequences if he got caught and decided against it.

Michael and Madison are very close as brother and sister goes; even hanging out together on the week-ends. Michael is constantly hitting on Madison’s girlfriends. They pretend he is a nuisance, but each of them thrives on his attention. They love it when he checks out their breast and butts. He sincerely believes he was getting away with it without their knowledge, but he wasn’t.

When school let out for the summer break, Michael and Jerry spent two weeks cleaning the yard and getting the swimming pool ready for the summer fun. They got to enjoy the pool only a week before going off to camp for three weeks. Jerry went to the Cub Scout camp as a new Cub Scout; and Michael went along to the same camp as a camp counselor to assist a Den Mother. Michael’s mother had volunteered him for the counselor position saying it would be good experience for him. She also knew Jerry would be less likely to get homesick if his big brother was there with him. Jerry enjoyed the Cub Scout camp, but Michael insisted it was a waste of his summer vacation. He claimed he would have much rather stayed home and watch his sister and her girlfriends lounge around the pool in their skimpy swimwear.

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Cub Scout Camp Arrowhead was located in a 1000 acre forest reserve. There was a large lake in the center of the reserve with a very large lodge built solely from logs at the edge of the beautiful lake. That lodge served as the headquarters for Camp Arrowhead. It housed all the administrative offices and had a giant banquet room that served as a cafeteria and meeting hall. There are several other smaller log cabins scattered among the forest trees; all within one hundred yards of the main headquarter lodge. These smaller cabins served as lodging for every Den Mother and had all of the amenities of home. Each of the cabins had a mini-kitchen, a comfortable bedroom with a private bath for the Den Mother, and a large front room centered on a fieldstone fireplace. The front room was used as a meeting room for the Den. It was stocked with emergency first aid supplies and lots miscellaneous items to keep the young cub scouts entertained.

There were over 100 young Cub Scouts attending Camp. They were divided into Dens of ten cub scouts each. Each Den had a Den Mother assigned, along with a camp counselor. The Camp Counselor was usually a former Boy Scout or High School student. Jerry was assigned to Den #7 and Michael was the counselor for that Den.

The Den Mother was a 30 year old mother of twin boys. Her name was Cathy Glover and this was her first year serving as a Den Mother. Her sons, Dan and Don are Jerry’s age. She is 5’ 7” and weighs approximately 120 pounds. She has green eyes and shoulder length sandy blonde hair. She has a natural beauty and the only makeup she wears is a pink lip gloss. Michael fell in love with her straight away. She reminded him of his twin sister, Madison. He was habitually fighting an erection every time she came near him. The sweet aroma of her honeysuckle perfume alone caused him to have an erection.

Cathy was married to Tim Glover, an associate partner with a major law firm. He spent most of his waking hours trying to make full partner. He was content with making the living and left the task of raising the twin boys to Cathy. She loved the time spent with the twins, but missed the company of her husband. She realized Tim had to devote a lot of time to the law firm in order to insure their future, but that didn’t keep her from feeling lonely.

The cub scouts were housed in tents spread around the Den Mother’s cabin. The tents were on wooden platforms and each tent could accommodate two cub scouts. The Camp Counselor had his own private tent located fifty feet from the Den Mother’s cabin. There was a cabin between the Den Mother’s cabin and the Counselor’s tent that housed the latrine. The latrine had five shower stalls that were door less, five enclosed toilet stalls and five urinals with a divider between them for privacy. Michael showered and used the same bathroom and latrine facilities as the cub scouts. Cathy had her own private shower and bathroom facilities in the Den Mother’s Cabin.

The first morning the cub scouts of Den #7 met in Cathy’s cabin to learn the rules and regulations they would have to live by for the next three weeks. Cathy opened the meeting by introducing herself and Michael, the camp counselor for Cub Scout Den number seven.

“My name is Mrs. Glover and I will be your Den Mother for the next three weeks. This young man to my right is Michael Winston,” she said as she placed her hand on Michael’s left shoulder. He felt an erection budding as soon as she touched him. He tried to conceal it without drawing too much attention to himself, but was unsuccessful. His hormones ruled his teenage body.

“I expect you to rely mainly on Michael to answer any questions. If he is not available, then feel free to come to me. I want you to think of me as your Mother away from home.”

“Is Michael supposed to be our father away from home?” One of the boys asked.

“No…I want you to think of Michael as your big brother. In fact, he is the actual big brother of Jerry Winston who is a member of this Den. And while I am at it I want to point out my two real sons, Dan and Don Glover. I want all of you to consider our Den as one family with a Mother and Big Brother.”

Cathy saw Michael struggling with concealing his bulge. She felt sorry for his embarrassing condition, but also thought it was cute. She was somewhat flattered she had that affect on a young handsome man like Michael. She just wished her husband, Tim would respond that way when she touched him.

Week one passed without any major incidents. All of the young cub scouts seem to be having a wonderful time. So far none of them seem to be afflicted with home sickness. Michael had done a first-rate job of guiding the boys and has seen to it that they were kept occupied with lots of fun activities. Michael was beginning to feel more relaxed interacting with Cathy. However: he still got an occasional erection when near her, but had learned how to quietly slip away and relieve it manually.

The first week-end energized the Cub Scouts because parents were allowed to visit. Week two got off to a shaky start. During the nightly bed check, Michael found Jerry and the Glover twins naked in the same bed. They claim to be trying to keep each other warm. Michael decided to overlook the incident and not report it to the Den Mother. Later that week Michael encountered Cathy on the trail behind her cabin and realized she has been crying. Her eyes were red and blood shot. He was used to consoling his twin sister and offered to sit with her and listen to what was upsetting her. His offer was not taken well.

“I have NOT been crying,” She snapped at him. “You just tend to your cub scouts and not meddle into my personal business.

She stormed back to her cabin and Michael was left wondering what he did to upset her. Cathy slammed the door to her cabin and rushed into her bedroom and threw herself on the bed. She burst into tears and sobbed like a young teenage girl. She was ashamed of how she had treated Michael. She knew he was only trying to be helpful. She knew she needed to apologize to him, but didn’t know how to do it without discussing her very personal marital problems.

Cathy had invited Tim to come to the camp that first weekend, but he had chosen to spend that time on the golf course with his senior law partners. She wanted him to spend time with the twins, but she also needed some intimate time alone with her husband. It had been almost two months since they made love to each other.

The weekend came and went without Tim making his visit to the camp. Cathy fell deeper into depression and the loneliness was almost unbearable. She slipped into the habit of showering each night then masturbating until falling to sleep. The nightly masturbation sessions relieved some of her sexual stress, but she needed a real orgasm brought on by a real cock. She wanted to have an orgasm like Tim used give her when they first married. She badly needed a man’s hard cock and found herself wondering if Michael was mature enough to help her with some of those needs. Those thoughts filled her with guilt and made her avoid Michael on some occasions.

Tim failed to visit the following weekend and Cathy was becoming more emotional. The start of week three brought more agony and more sexual frustrations to her. Tim had missed his last opportunity to spend a weekend with his family. She was very angry at Tim for not coming to the camp for at least one of the two weekends. At the end of that week she would be returning home and she had mixed emotions. She had gone so far as to entertain the thought of seeking a divorce. She really didn’t want a divorce; what she really wanted was for Tim to spend a whole weekend fucking her brains out. An orgasm brought on by her fingers was just not the same as a really hard cock.

All the Cub Scouts were safely tucked away in their tents, so Cathy took a hot shower and masturbated, and then cried again. She got out of the shower; put on her PJ’s and poured herself a glass of ice tea then flopped on the sofa with a book. Ten minutes later there was an urgent knock on the door. She was lounging comfortably on the couch in her pajamas reading a book and didn’t want to be disturbed. She assumed that it was probably one of the young cub scouts. Being alone and relaxed in her cabin she decided to ignore it in hopes they would give up and go find Michael

“They’ll go away soon enough,” she said to herself. She wasn’t in the mood to deal with any juvenile problems at the moment. Right now her own problems were her priority. She sipped on her glass of ice tea and went back to her book.

They knocked again. This time it was louder and more urgent.

“Oh, what-EVER,” she said to herself aloud. Putting her book down with a sigh she went to the cabin door and looked out the window. It’s Michael; her young Counselor.

Hey Michael,” she cheerfully said opening the door. “What’s up?”

“I hate to disturb you this late, Cathy,” he said as he grimaced in pain, “but I tripped in the dark and skinned my elbow. I think I need a bit of first aid until I can go by infirmary in the morning”.

“Let me see your arm. Oh…you have a nasty scrap. I have a first kit in the kitchen,” she said. “Just follow me.”

She had tight cotton pajama pants on and a tank top with a sweatshirt over it. Her ass jiggled just a little bit with each step. Michael counted to himself backwards from one hundred to fight off the erection that was being to stir because of her ass. The years of motherhood and carrying babies hadn’t harmed her figure in the least. The curve of her ass blended into her shapely thighs and calves. Michael couldn’t help but get aroused as she walked hastily into the kitchen staring at her cell phone while waiting on Google to respond to her questions on first aid.

“I’ve Googled ‘scrapped elbows’ under first aid,” she said over her shoulder. The internet is running slow with the response, but it shouldn’t be much longer. Are you thirsty?”

She offered Michael a glass of ice tea and he accepted.

She turned around and reached up to get a glass from a kitchen cabinet. She was too short to reach the top shelf and rose up on her tiptoes, but it was still out of reach. She dropped back down on her feet and her breast jiggled. It was a clear indication she was not wearing a bra.

“I can get it,” said Michael, and quickly stepped up behind her, reaching over her to get the glass.

For the moment he had forgotten about the slight bulge in his pants, and in an awkward moment his bulge poked Cathy in her butt. She quickly turned around, not expecting him to have advanced so close so quickly. When she did, she found herself face to face with Michael; his arm over her shoulder, reaching. There was already some chemistry there. Now, face to face, even the normally socially oblivious Michael was feeling awkward. The feel of her breath on his neck only worsens his arousal and he was standing dangerously close.

Hurriedly, he grabbed the glass and set it on the counter. Cathy wordlessly began to pour ice tea in the glass. Her heart was beating wildly in her chest and she was sure Michael could hear it. She started to awkwardly mumble something about the internet’s slow response time, but before she could complete her sentence, she turned to replace the ice tea in the fridge, and her elbow accidentally hits the glass on the counter. The tea sailed against the backsplash and splattered all over her sweatshirt.

“Oh, crap,” she said, and grabbed a towel by the sink. “This sweatshirt was a present from my husband,” and she whipped it off and raced to the laundry room.

Michael was still reeling from their face to face moment. Awkwardly, he adjusted his erection and began to wipe up the mess and refill his glass. He took a shaky drink. He needed to go back to his tent and relieve his erection.

“I can go and come back later I guess,” he shouted to Cathy.

“No…no,” Cathy called back from the hallway, coming back from the laundry room. “We need to tend to your injured elbow. We don’t want to risk an infection.”

Michael looked at her as she came back in the kitchen. Now she was wearing only her tank top and pajama bottoms. Her hard nipples were plainly visible poking against her tank top. He could feel his cock growing harder in his pants and was relieved when she instructed him to sit at the kitchen table while she cleaned and bandaged his injured elbow. That gave him the opportunity to partially conceal his painfully hard cock.

Cathy placed the first aid kit on the table and sat in a chair next to him. He wanted to kiss her but was an inexperienced virgin and had never really kissed a girl. He had kissed girls, but not really kissed them like he wanted to kiss Mrs. Glover. His erection continued to grow, but he felt reasonably sure it was not as obvious since he was sitting down. He was wrong. Cathy does see the bulge in his pants and is tempted to touch it. She needed to feel a hard cock; any hard cock. She blushed red and her breathing was coming in short bursts. It was obvious an internal struggle was going on inside her.

Michael’s breathing became rapid and irregular also. He was on the verge of screaming. He didn’t have a clue how to proceed. He wanted her and he was almost certain she wanted him, but his inexperience prevented him from following his impulse. It took all of his effort to fight off the urge to pull her into his arms and do all the things he had seen on his favorite porn sites.

Cathy’s passion and frustration had built almost to a point of no return. She finally realized she couldn’t fight her urges any longer and on impulse she leaned forward and kissed him tenderly on the lips. Excitedly, he responded by pulling her closer, and ran his hand up her thighs to her crotch. It was like an electrical surge between them. All of the pent up emotions of the past two weeks came flowing out of them both all at once.

“Yes, yes, fuck yes,” she sighed faintly. She ran her hands up his shirt and lightly stroked one of his nipples and then lightly pinched it. His lips left hers and traveled down her neck. She emitted a low purring sound and wrapped her arms around his neck.

He picked her up and her legs wrap automatically around his waist. His natural instincts kicked in as their lips locked again. He hurriedly carried her to the bedroom. He laid her down on the bed and began working his lips down her neck and shoulders. All the internet porn sites he had watched were directing his actions. He lifted her tank top over her head. She helped him remove it then pulled his shirt off, eagerly kissing his chest and stomach as he sat straddling her on the bed. Cathy mewled again as he ran his tongue over her supple breasts, down to her navel. Slowly his hands moved up her body, over her breasts. She calmly pushed him over on his back and positioned herself on the edge of the bed.

She carefully unbuckled his belt and gently worked his pants and underwear down to his knees. While her hands worked the pants, she leaned forward and gently began kissing the head of his cock. Lovingly and tenderly, she started adding some licks and sucks to his rock-hard cock.

Michael whimpered as her lips finally wrap around his cock and her hands on his ass cheeks pulling him deep into her mouth. It was the first time anyone had ever put his cock in their mouth; it was exhilarating. Slowly she bobbed up and down on his cock while running her finger tip around his asshole. No one had ever touched his virgin asshole and he almost blew his load. He was actually entering a world he had only dreamed about while watching his porn sites.

She masterfully sucked his young cock until he couldn’t take any more. He was on the very threshold of cumming and tried to push her away from his impending explosion. She shoved her middle finger deep into his virgin ass. She sucked one more time and took him all the way down her throat until her nose was touching his belly. He was at the point of no stopping and uncontrollably unloaded his cum into her pretty mouth.

“Oh, shit,” Michael moaned. Cathy looked up and smiled as she pulled her mouth slowly off his quickly waning cock. His cum had disappeared down her throat, except for a slight dribble that Michael wiped off her lip.

Neither Michael nor Cathy spoke. He grabbed her waist and laid her back onto the bed, then peeled the rest her PJ’s off, kissing her legs as he removed the cotton bottoms. She started moaning and squealing as he began nibbling and licking her clit through a pair of pink satin panties before pulling them down. His hands found her nipples and he kept darting his tongue from her clit into her pussy, licking up and down the length of her cunt. His nose rubbing against her clit added to the overall sensation. Grasping his hair she held his mouth to her pussy and moaned in orgasm. After she recovered, she pulled him up to her lips and kissed him deeply as she wrapped her legs around his waist.

Her hands slid down his body as they kissed, and with one hand she grasped his cock, lightly stroking it. He was already getting hard again, but in a brief moment he was fully charged and throbbing as she guided him into her wet pussy.

“Slow, baby…,” she whispered as he entered her. “It’s been a while for me. I want to take it slow and make sure we both enjoy it,”

She wiggled and craned her head back; thrusting her chest in the air as he finally entered her fully. Slowly and rhythmically he pumped in and out of her, kissing her neck and stroking her thighs. She used her legs to pull him in deeper and deeper. With a final, deep kiss they both grasped each other tightly and began to rapidly pump in and out, in and out gaining speed as they neared a climax. Her body began to shake and convulse as her hands dug into his buttocks and pulled him down even deeper as he shot his cum into her belly. It took a good five minutes for them to recover. He kept his cock in her the whole time. Slowly, he pulled his deflating cock out and lay next to her. They were both totally exhausted.

“That was the most breathtaking experience I have ever had in my entire life,” he said as he gasped for breath. “Thank you so much.”

“That was your first time wasn’t it,” she said.

“How did you know?” he asked embarrassingly.

“I was a virgin once and I can tell you for a fact that you did really well for a first time; you have absolutely nothing to be embarrassed about.”

“Can we do it again before we go home?”

“I don’t know….maybe. I really want to,” she replied. “But I do know that we can never let anyone know about this. Not even your best friend.

Michael nodded his head yes.

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