Annual August Holiday

I often have fantasies about being 18 again and enjoying sex for the first time. This story involves my Mother and Father, (I chose not to use their names and just call them mom and dad.), and their good friends Tom and Theresa. My sister, Shirley, and Tom and Theresa's daughter, Sarah, are introduced as they will undoubtedly have major roles in future stories. My name is Jim, though mom always calls me James.

Annual August Holiday

By peddler

Chapter 1 - Our Great Loss

It was late July in a year of many changes. I had just graduated high school and just turned 18. I would be voting for the first time in the November election so was beginning to take an interest in politics as well as becoming irritated with the multitude of ugly political commercials. I had been accepted into a local trade school this fall to become an electrician so was working this summer with a local electrical company as an intern. It involved running a lot or errands and doing a lot of the heavy lifting, but I was able to keep in shape and learn some of the trade along the way.

But the biggest change of year was the loss of my dad this past spring. Dad and I had always been quite close so when a sudden heart attack took his life my world was turned upside down. There would be no more days on the lake fishing with him, no more days together tinkering on the car or other garage projects, and especially no more times just talking with him about life and love. I really miss my dad.

As hard as it was on me it took a bigger toll on my mom and my older sister. My sister, Shirley, is twenty and just finished her second year at the university. Dad had always treated her special and would continually shower her with praise, hugs and presents. And he was quick to defend her against anyone or anything. It was not wise to ask her out on a date without the best of intentions.

Mother and dad were the picture of perfect love. I will never forget the pecks on her cheek, the love pats on her rear, and the way they would look into each other's eyes. There were times when they would have respectful disagreements but they seemed to always end by retiring to the bedroom and emerging the next morning with a special glows on their faces. It was obvious they had a wonderful love life and mom knew how to get her way. Dad's sudden death hit her pretty hard. She and my sister cried often for many days after.

I made a commitment to be strong, to be extremely sympathetic, and to try to fill dad's shoes as best as I could. Dad left a generous life insurance policy, so money was not a problem, but mom decided work would be good therapy, so found a job as a nurse. I took dad's lead and brought mom and sis flowers and little gifts often, gave those many hugs and spent as much time with them as I could. I considered it my place to make sure that the void, and do all I could to bring us closer together.

Mom and dad had several friends, but none as close as Tom and Theresa. They lived across town and yet would meet up often for a night out. Often they would come over for an evening of cards or a weekend Barbeque. Tom and dad loved to fish and often took me with them. It was an opportunity for me to learn the responsibilities of manhood from two of the finest. Theresa and mom went on shopping excursions, planned many parties together, and seemed to be in constant contact by phone or text. They had one daughter, Sarah, who was my age but attends a different school. She has become much more independent so I haven't seen her very often the last couple of years.

Tom and Theresa gave much comfort to our family at the loss of my dad. Tom continued to take me fishing, or maybe take me out for a burger from time to time. He wasn't dad, but he was a great help. Theresa spends a lot of time with mom and Shirley shopping, cooking and doing other girl things.

For as long as I can remember, every August our two families have taken a weekend vacation to the lake. We called it our 'August Holiday' and always followed the same routine. They would rent a three bedroom condo together, leave on Friday morning, stop halfway there for lunch at the same little café, arrive, unpack, go out for dinner somewhere, and settle in. Shirley and Sarah would occupy one bedroom, mom and dad one, and Tom and Theresa the third. I was left with the couch in the living room.

Saturday, we three guys would pack a lunch, and head out to rent a boat and spend the day puttering up and down the lake fishing. We practiced catch and release, so the ladies had to believe our fishing tales. When we returned we would share our days around the dinner table.

Now was the time for the ladies to model the things they had purchased. They would usually begin with a casual outfit such as dressed or jeans and shirts. Then mom, Theresa, and the girls emerged from the bedrooms wearing their swimwear. I squirmed in my seat trying to hid the effects this was having on my package.

Mom at 40 was a real looker. She was five foot ten with an hourglass figure. Her one piece suit was usually a very attractive print that covered all but just the right amount of cleavage while concealing her double D cups.

Theresa was a slimmer, very attractive five foot eight. She usually chose a modest bikini in a bright color. The view of her curves, midriff exposing her belly button, and legs made it difficult for me to breath. It was difficult trying not to stare at the material between her legs and the bra that covered her C cups.

It's been two years since Shirley, Sarah and I attended the August Holiday, but I still recall those skimpy bikinis. Shirley was 18, five foot nine with an hourglass shape much like our mom. Sarah was 16 like me, five foot four and her slender shape closely matched her mother, Theresa.

I began to look forward to spending some time in the swimming pool with the two of them tomorrow. We would play some of our silly games and I would surely get a chance to see more, and rub up against their bodies. Needless to say I would need some extra time in the shower to relieve myself and my dreams would be made up with wonderful story lines involving one, or the other, or both.

Sunday was football day. August was preseason time and there was much talk about how the teams would do this year. We usually slept in late, had a brunch around 11:00, and prepared for the afternoon. The girls usually spent the day at the pool, while the wives chatted in the kitchen sipping some wine, and brought us treats like popcorn or trays of finger foods as well as a few beers for the husbands and a soda for me as we sank ourselves into the game. When the game was over the guys would barbeque steaks on the grill and the wives prepared a fabulous supper for all. The evening was consisted of cards, conversation, maybe a dip in the hot tub or a walk to the lake. We were always saddened when Monday morning arrived as we packed and traveled back home, always stopping at the same café about half way.

The last two years these August trips had changed. Shirley had gone off to the university early for sorority rush and Sarah and I had each found summer jobs that were hard to leave, so mom, dad, Theresa and Tom had downsized to a two room condo and gone without us.

Though I missed the August holiday, I was beginning to spend more time with some of my high school friends as well as going on an occasional date. Though I thought about sex often, my dad made it clear that dating was not a time of conquest but a time of discovery. He would not take it kindly if I didn't treat my date with the upmost respect, care and consideration. I was to use a date to learn if the girl was a person I was willing to spend the rest of my life with, and that sex could ultimately lead to a lifetime shared with the wrong mate. Needless to say, I began looking for someone who was just like my mother and after only a few dates I'd usually find myself disappointed and break it off. My sexual experience consisted of an occasional kiss, a feel, and thoughts of what sex might be like someday. Oh how I miss my dad and his advice.

Chapter 2 - The Request

It was July and I was wondering if there would be an August holiday for mom this year. She had said nothing. Would she join Tom and Theresa, would they go without her, or would it even happen at all? Shirley as usual planned to go back to the University early, I had my job, and I hadn't heard anything about Sarah's plans, but assumed she was also preparing for her first year at the university.

One day when I arrived home after work, mom met me at the door. "James" she said. Though my friends call me Jim, she always calls me James. "I have a request."

"Of course mom, you know I'll do anything you want. Let me shower first though. It's been a grimy day." I quickly showered and returned finding mom waiting at the kitchen table.

"James", I could tell that she was a little hesitant. "Would you go with Tom, Theresa and I on our August holiday this year?" I began thinking about spending some time with mom walking to the lake, or playing some cards with my friends, and a day of fishing with Tom. I could sure use a few days to resting up before classes began.

"Mom, I think I can get a couple of days off. I'll check, but of course the answer is yes if I can. I'm so happy that you decided to go. I was concerned there might not be one this year. I will do all I can to make it happen."

She continued, "Before you give me a final answer there is something I need to tell you and I hope you'll understand. This is going to be a little difficult so please be patient with me."

"Of course mom. What is it?"

"It all happened two years ago when only the four of us went without all you kids. The trip began as usual but we made one change. Instead of going to a restaurant when we arrived on Friday evening, we went to a night club. The meal was great and after a few drinks we began dancing. Then Tom asked to dance with me and Dad asked Theresa. I enjoyed cuddling up with Tom and feeling his cheek against mine. I could feel his heart beat as I laid my hand on his chest. The sensation was invigorating and that night your dad and I experienced a wonderful night making love. Your dad was always good, but that night he was extra good. I'm sure he had enjoyed his dance with Theresa."

I resisted the impulse to ask mom for more details. If she would have wanted to tell me, she would have. Seeing her reluctance I urged her on by saying, "Go on mom."

"Well, the next day your dad and Tom headed for the lake as usual and Theresa and I began our usual routine. We enjoyed a morning coffee and began talking about the evening before. I learned that they had enjoyed the previous evening and night as much as we had. I also learned that she was not at all jealous as she trusted both Tom and I completely. I of course felt the same about Theresa and your dad. She is a wonderful friend. We spent the day shopping and eating downtown. On a whim we went to a shop and selected some very revealing lingerie. Theresa decided on a pink teddy that accented her slender features. I chose an almost see through blue baby doll set. We left the store and began to make plans to spring these purchases on our men. Needless to say we were getting quite excited with the anticipation of what the evening might bring. It was time to begin planning the reveal."

"Mom, is this something you really want to tell me? That sounds like some information that you might want to keep between the four of you."

"I know dear, and this is difficult, but I must tell my story before I make another request."

"Request?"

"Yes. I do want you to accompany us to the condo, but I have a second request, and I must first explain why."

"Ok mom, I'm listening."

"Well, the men returned with tall tales about their day of fishing. As you know they catch and release, so we had to take their word for it. And, we told about our day of lunch and shopping. Of course we didn't mention our little surprise.

After supper it was time for the reveal. We began by modeling a couple of casual outfits we had purchased and then we each opened a package with some flannel sleepware. We noticed their puzzled faces. We carried them into the bedroom but instead of the flannels we changed into our new lingerie, and covered ourselves with robes. We entered the living room, turned away slowly dropped the robes. When we turned back around their eyes were popped out of their heads and their mouths fell wide open. Their gaze traveled back and forth between us then they looked at each other. Tom studied me from top to bottom. My baby doll was almost see-through and I was beginning to turn red. I looked over to see the look on your dad's face. He couldn't take his eyes away from Theresa in her teddy. We posed and turned a few times then I went over and sat on your dad's lap. We began to kiss passionately as dad's hands explored my body. I looked over to see Tom and Theresa were doing the same. Then I noticed your dad was also checking out the action. I stood up and led him into the bedroom where another night of lovemaking took place. "

I again resisted the temptation to ask for more details as I kept wondering where this was going.

"Well, the next morning Theresa and I prepared brunch and set up the living room for the big Sunday football game. During the first half we enjoyed some wine and started putting together some naughty plans. At halftime we brought in beers and more snacks and joined them for the third quarter. When the fourth quarter began Theresa and I left long enough to slip into our swimwear. Theresa put on her bikini and me my one piece. I have never felt comfortable in a bikini. We announced that we were going to the hot tub after the game and they could choose to join us. I noticed you dad checking out Theresa's lime green bikini or should I say the parts it didn't cover. Her body is just made for a bikini. And, Tom did his share of checking me out. The men made it clear that we shouldn't go out there alone amongst the wolves. I moved several times rubbing up against your dad and showing off my legs at various angles. Theresa and I saw more of the end of the game than they did."

"The men changed quickly and we were off to the hot tub. Under the bubbly water your dad and I explored each other's bodies and though it was hard to tell, I'm sure Tom's hands were inside Theresa's bikini. We enjoyed watching each other make out with our spouses. We returned, showered, and dressed for our barbeque evening."

"Then Theresa and I announced that we wanted to get more comfortable, retired to our bedrooms and returned in our new lingerie. Tom put on some music and we began to dance. After a couple of dances we exchanged partners. It just seemed natural. I melted into Tom's arms and enjoyed the sensation of rubbing against his body. I looked up and my eyes and smile met Tom's. He looked over at his wife and she gave him a big smile and a wink. I saw Tom return the wink so I took her lead and gave your dad the same wink. Tom turned and led me into the bedroom where we spent the evening and the night giving each other much pleasure. Your dad and Theresa were doing the same in the other bedroom."

"The next morning we woke and fell into our own husband's arms to show our approval of the night before. Over breakfast we decided that this shouldn't be repeated then packed and traveled home."

"But mom, what do you want from me?"

"That was two years ago and before I explain, I must tell you about last year. The memory of our husband exchange lingered all year and we often commented about it. The decision was made last year to swap husbands for the entire weekend. The swap would be made at the café about half way to the condo, and we would swap back at the same café upon our return. If at any time one of us decided they were uncomfortable, the arrangement would end. Just as planed after we ate our lunch, I slid into the front seat beside Tom and Theresa slid into the back seat beside your dad. We spent the whole weekend as if we were married to each other's spouses. Everything else was the same. We went dancing, the men went fishing, we ladies went shopping, and the men enjoyed Sunday football. Our hot tub time, couch time and bed time were in our new husband's arms. After lunch at the café on the way home we took our rightful place with our rightful husbands."

"It was a wonderful weekend. It was made possible by the trust we have for one another. We love one another and would never do anything behind one another's backs.

We decided to make this an annual August holiday but with the death of your dad all has changed. Tom and Theresa don't want to go alone this year. Theresa even offered to send me in her place. She is a wonderful friend, but I couldn't leave her home alone. We decided that a threesome was out of the question. We were unsure just how our special weekend could possibly happen, when Tom came up with an idea. He said that he had seen how well you were taking dad's place in our home. He noticed how much you cared for me and your sister. So he suggested that you come along to entertain Theresa and that I be his wife for the weekend again. You would be welcome to be Theresa's sister, a date, or even her husband, whatever would make you feel comfortable. It would be your responsibility to make her feel needed and welcome. Tom trusts you completely."

Needless to say I was speechless. I really like Theresa. She has always been very nice to me and even though she is about twenty years older than I am, she is very attractive. I began to recall her face, her flowing shoulder length brown hair, her graceful trim figure, and her beautiful smile. "Mom, I don't know what to say. Of course I want to be of help. And, it sounds like I would have a wonderful weekend. But, I'm not sure how to treat a real lady. Dating a school friend is easy. We go to a fast food place, to a movie and home. Maybe a kiss on the doorstep, but I don't have to worry if she will like me tomorrow. We can always move on. But, Theresa is a lady. What if she doesn't like me? What do we talk about? How do I treat her? And, would my presence make you feel uncomfortable?"

"James, just treat her like you do me. You have been wonderful these last few months. You had a great teacher. I notice that you do many of the things for me that dad used to do. Just treat her -- like a lady. And, I'll do my best to consider you Theresa's date, not my son."

"And you'll be there as Tom's wife? ---- You know, I think that would be good for you. I've tried to fill dad's shoes, but there are some things I am not able to give you that dad could. I've decided I'd be thrilled to go with you on this year's August holiday."

Chapter 3 - The Holiday

The August Friday finally arrived. I had located dad's fishing gear and was packed for the weekend. Needless to say I was a bit nervous. Mom was smiling from ear to ear all morning and I was so happy for her. Tom and Theresa arrived, we loaded our things in their trunk and mom and I climbed into the back seat and I placed a package on the floor at my feet. As we traveled down the road Tom broke the ice with a challenge. "I bet I catch more fish than you do tomorrow."

I couldn't let that stand, so I responded, "You may catch more, but I bet I catch the biggest one."

A big grin filled Tom's face. "I tell you what - $10 on the most and another $10 on the biggest."

"You're on." Tom and I were going to get along just fine. Mom reached over and took my hand in hers. She looked great in her blue shorts and white nit pullover that accented her shape. The talk on the way to the café was very casual.

After lunch we returned to the car and I watched as Tom opened the door for mom to slip into the front seat. So I took his lead and opened the back door for Theresa. Tom and I took our places and I reached for the package at my feet, opened it and handed Theresa a single red rose. Her response was amazing. She took in a deep breath, looked me in the eyes with a wonderful smile and said, "It's beautiful. Thank you." Then she surprised me by unbuckling her seat belt and moving to the center of the seat, buckling the center belt and nested her head in the crook of my arm. I reached over and took her hand into mine. He slender figure looked amazing in white shorts and a button up blue blouse that was unbuttoned just enough to seem to ask you for more. Her breasts, though smaller than mom's, matched her figure perfectly.