What I Did On Summer Vacation

by Karen-In-My-Dreams

 

This account relates some of our activities the summer of the year we were 14. "We," being two sets of twins, our identical female cousins Kathy and Melody, my twin sister Samantha, and me, Darren. We started what we still think is some normal sexual experimentation two years earlier at our family's lake cottage. It began when our cousins taught us about tampons. I was the research subject of the girl's curiosity about erections.

We would alternate summers together so one set of parents was free to travel without kids. One summer the four of us would be at our cottage with our folks in charge, the next would be at Aunt Sue and Uncle Frank's house while our folks would have their summer alone. All four adults were teachers and liked to study and travel while school was out.

I like to wear girls clothes and do girlish / feminine things with my sister and cousins. They like it when I do, too. When we're alone and have a chance to act as a female foursome, I use the name "Karen," because it sounds so close to my real name. Over the years, all three girls have masturbated me to ejaculation, as I have them, too. Melody often asks to help me urinate by standing behind me and manipulating my penis. This year all three girls had "real" breasts, worthy of the name. Nothing monstrous, but more than mere buds or bumps.

We assume it is only natural that over time, our curiosity and experimentation intensified. The first summer was mostly talking and looking, with some touching. The second summer, we made a solemn pledge to investigate almost anything, but not have intercourse. The goal of our group has always been to satisfy any and all curiosity, bring as much pleasure to each of us, and do nothing dangerous or hurtful, either physically or emotionally. It has been more than 30 years now that we've been doing this. Our activities have become more complex and intense, but those stories are for another time – if you are interested!

The biggest change at the cottage that year was the garage. The previous fall, our parents had a two-story pole-barn / guest quarters / garage built. They felt we were getting old enough to need more space and privacy than we had in the main cottage. Upstairs was divided into two two-bedroom suites with a large connecting full bath. One suite was to be for me and Sam, the other was for Kathy and Melody. Each bedroom would have a second bed, so we could each invite a guest for a weekend or a even a week. There was also a large landing or commons area at the top of the stairs. Later, if we continued to use the cottage as adults, it was likely that there might be more people (spouses and kids) to accommodate than the cottage itself could hold.

Forgive what you may be thinking is unnecessary information; this building plays a significant role in many of our adventures from here on.

The thinking was that the first floor could be used to store cars, boats, and the small tractor out of the weather. If they wanted to have a party when it was raining, the smooth concrete floor would make a great picnic pavilion. They eventually built insect screen inserts for the garage door openings. That made being inside much more pleasant without biting and stinging creatures to contend with while allowing breezy ventilation.

There was a small kitchen counter area with a sink, microwave, propane four burner stove top (no oven) and refrigerator, plus a half bath on that floor. Insulation and heating ducts were put in by the builders, but no furnace yet. as there were no plans to winter there.

The propane appliances were Dad's hedge against a power failure. If a storm took down the lines, this kitchen would allow basic survival cooking during the outage. We had a large propane tank which would be plenty for up to a month. Some years later, he had a big propane emergency generator installed as well.

The job of finishing off the inside and some simple landscaping was to be our (the four of us teens) project that summer, and we were being paid for it! That included running the electrical wires according to the builder's plans to save having to pay electricians do it. They would return to actually install the switches and outlets and make connections at the panel. The builder's crew would then install the plasterboard upstairs and finish the joints, after which we were to paint the ceiling and walls and install the trim molding around windows and doors.

There were four big piles of topsoil to be spread around the outside of the building, grass seed to sow, some shrubs and flowers to plant, and we had to keep everything watered so it would grow. We thought it was a great adventure, and were really looking forward to doing it ourselves.

We decided to work every morning from 7:30 or 8 until about 11. We'd have the rest of the day to swim, sail, go biking and hiking, reading, or whatever (meaning particularly our special activities!). We had a radio and hi-fi for entertainment, but no TV or tape player. We would read and played a lot of card and board games. This was long before computers and CD players, too.

It took us about two weeks to get all the wires in place and get the dirt spread around. The builder had the ceilings and walls up in another week, and it took us almost two more weeks to paint everything. We got to live up there for the last three weeks that summer!

For the first two weeks, we were working hard and kind of tired in the afternoons, so most of our secret activity consisted of conversations in the sailboat. Tuesdays continued to be the day the adults drove back to our hometown to get mail, pay bills, shop for groceries, etc. That gave us at least four hours after lunch to engage in our erotic activities.

Among the things we talked about during our afternoons sailing was what we had done since the previous summer and what we had in mind for this one. I said I had brought along two packages of condoms, and had been thinking that I might like to have my bottom penetrated gently, perhaps by a finger or a tampon. Sam told the others that she'd had me remove her tampon several times and thought it might be neat to have me put in a fresh one. Kathy wanted to masturbate two people at once, first two girls and the "one of each," and finally asked to receive attention from the three of us at once! Melody told us about overhearing some girls at school discussing oral sex and said she'd like to try giving and receiving with both sexes if we were willing!

Melody and Kathy revealed that they had brought some special treats with them. The first was four pairs of identical panties. I had speculated last year at their house how nice it would be for all four of us to dress identically if we ever had the chance. The second was a seven page typewritten list of erotic passages from books they had read. (We thought we were pretty hot stuff to have IBM Correcting Selectric II typewriters, with the interchangeable elements, at home!) The third was a copy of the Joy of Sex!

That Tuesday morning, the six of us had a family breakfast, then Mom and Dad left in the car. We cleaned the cottage and put in three hours working on the garage projects. About 11:15, we came to a stopping point and decided a swim would be nice.

This was only the third summer I had been doing any cross dressing at all. At the cottage, opportunities were very limited, even with the assistance of my sister Sam and our cousins. We never gave serious thought to using cosmetics or fingernail polish because it would be very hard to apply, enjoy, and remove all traces without being discovered. The wardrobe available to me there was somewhat limited because it was a vacation place. Sam didn't keep very much in the way of frilly girlie dresses there, and the cousins mostly brought shorts, jeans, t-shirts and sweatshirts.

What we did have there and what we used in the past were panties, nighties, and bathing suits. Everyone had two or three bathing suits, so at least one would be dry. There were also some extra suits for guests: male and female, young and adult. My favorite was a medium blue nylon one-piece tank suit. The top had a built-in bra with formed cups. It gave me the appearance of having a modest bust without having to stuff it with anything which might fall out. Always before, I had just dressed upstairs in the bedrooms, but today we planned to be bold and actually go swimming! My hair was pretty short, but if I wore a rubber bathing cap, I looked like I had my hair tucked up to stay dry.

We all changed in the house. I admired the girl's breasts and they watched with great interest as I tucked my penis back under my scrotum into the crotch of the bathing suit, so there was no unfeminine bulge. The suit had a panel across the front which extended from the front of one leg opening to the other. I liked that because if one of the girls fondled me while I was wearing that suit, the panel created a little pressure to press their hand and fingers just a little more snugly against my penis.

Melody helped me get the straps fastened properly. My legs weren't shaved smooth, of course, but the hair was still on the fine and light colored side, so we thought we could get away with walking to the water from the house. I did take along one of my own suits folded in my towel, figuring that if anyone dropped in by boat, I could maybe quickly change suits in the water.

We all raced down the path and dived in off the end of the dock. After an energetic swim out to the sailboat mooring buoy and back, we stood in the water up to our necks, and traded some caresses. The excitement we felt was more from the daring, semi-public , sure hope we don't get caught sense of adventure than from true eroticism. Have you ever tried to fondle yourself or someone else in a late June fresh water lake?

After twenty minutes or so, we felt refreshed , hungry, and ready to have some special fun. We got out of our suits, with the girls hanging theirs on the outdoor clothesline, and mine went into the shower in the upstairs bath. We sat around the girl's bedroom as we dried out. I was curious at the way their nipples sort of puckered in the cold water, and they noted how small my penis and scrotum were as they reacted to the water in a similar way.

The girls brushed and combed their hair, and I admired their breasts and nipples. Fifteen minutes or so of that, and we were warm and dry again. Melody passed out the matching panties, white nylon, with dozens of embroidered butterflies. The crotch was two layers of a thicker satin-like material, but the rest of the fabric was much more sheer. I began to get an erection just holding mine, feeling the cool, slippery caress of the fabric as I drew the panties back and forth across my lap. I watched enchanted as first Sam, then Melody, and finally Kathy pulled theirs up and smoothed the fabric across their butts and tummies.

Next, it was my turn. I had quite an erection to begin with, but as I slid my panties up my legs, it became quite rigid! No chance of tucking my penis out of sight with these, like I did with the bathing suit. The girls each put on a pretty nightie, and offered me my choice of three other similar ones. I selected one of Sam's I'd had a chance to wear at home several times. It was a fairly plain, medium green, sleeveless, knee-length, two layer nylon (sheer, gauzy top layer over a heavier inner layer). It was fairly full at the hem, so if I twirled, the lower portion billowed out and caressed my legs. The effect of the two layers was intense pleasure when I ran my hands over my chest, my butt, my legs, or my crotch. Having the panties on made it even more pleasurable. What I really enjoyed was walking about with a gentle breeze blowing, feeling the nylon against my skin, as well as the small gusts of air. At home, I had worn the nightie with pantyhose a couple times, but we had no pantyhose here at the cottage.

We took turns lifting the hems of our nighties, teasing one another with glimpses of the matching panties. We also took turns hugging and tenderly kissing each other, and adding some caresses. I enjoyed having my chest stroked, and was quite satisfied with the tingle I felt. For some reason, I did not especially want to add a bra, even when Kathy offered me one.

We realized we had not yet had lunch, so we all went downstairs in our outfits and ate cold sandwiches, potato chips, carrot and celery sticks Mom had left for us. We sat around the kitchen table, just talking about how the garage project was coming, what subjects we would be taking in school in the fall, just good general conversation. After we finished, we cleaned up again. I washed, Melody and Kathy dried, while Sam put the dishes back in the cupboard.

Melody suggested we dance, so she and Kathy picked some tender, romantic slow dancing albums for the record player. I especially remember Wonderland by Night, Stranger On the Shore, Theme from Love Story, and Rose Garden. After each song, we would change partners. It was so special, holding someone closely and gently, swaying to the music, barefoot, in panties and nighties. By the second song, my erection had softened, and I found myself in a more romantic, sentimental rather than sexual mood. It was so nice.... It really was like we were four girls. Once, I tried following, but it was confusing to both of us, so I went back to leading all the time.

When the last album had finished playing, the girls said it was time for a demonstration of the condoms I had brought.

We went upstairs to the bedrooms. I retrieved the two boxes of condoms I'd bought at a drugstore near the college. Each package held twelve. One was sealed in square foil packets like ravioli, the other was packaged in overlapping thin metal disks, like mini-Frisbees. The looked a lot like the chocolate "coins" some folks put in Christmas stockings or give at Hanukkah.

The others were in the "dormitory," the biggest of the upstairs bedrooms. It had two sets of bunk beds, plus one single bed. Sam and Melody had claimed the two bottom bunks, Kathy had the one over Melody. The single bed was used more like a sofa., so that's where I sat.

I passed the packages across to the girls, who spilled the contents into their laps. Melody asked, "So what's the big deal with these things, anyhow?" Sam said, "Hey, there's only eleven in each box." I told them that I had opened one of each kind to examine it so we wouldn't all be beginners.

Melody asked if I had used them to have sex with someone. I sort of turned red, choked, and said, "No, but I did masturbate with them."

I said that they probably knew men wore them over an erect penis when having sex with a woman to keep from getting her pregnant. Kathy noticed that the boxes both had the legend "Sold for the prevention of disease only." Sam replied, "That's because in some places, selling them as contraceptives is illegal, but it is OK to say you are using them to prevent venereal disease."

The drugstore sold different brands and varieties of condoms, in packages of one, three, twelve and 36. The most expensive was made of sheep intestine, sold in individual packages which kept them wet and soft. They were said to allow the wearer to feel pretty much all the sensations that he would feel if not using one at all.

The rest were separated into lubricated or dry; plain end or with what looked like a miniature baby bottle nipple on the tip; and textured or smooth. The ones I purchased in the coin-like packages were smooth, non-lubricated, with the tip. The foil packaged ones were smooth, non-lubricated, plain end. I figured that since we were probably just practice putting them on and maybe masturbating, the lubricated ones would be unnecessarily messy. I was also practical, too. Lubricated and textured cost more than the plainer varieties.

I said that it was very, very important to make sure we didn't leave any of them around for the adults to find. We knew we had entered forbidden territory by investigating sex, even though we were not doing anything we thought was wrong or dangerous. I reminded them we absolutely had to be sure all the condoms and packaging was accounted for and disposed of. It positively would not do for Mom to find one in the bedding or on the floor, or in the trash.

I said that we could either let me keep them until we wanted to use them, or I was willing to give each of the girls three of each. We talked about if for a few minutes, deciding that it would be easier to keep track of them if I kept them together.

I asked the girls to open a condom by either tearing a corner of the foil wrapping or bending the coin one. Kathy claimed the right to go first, so she bent the coin-encased condom. The halves separated, and the rolled condom was released. All three eagerly but gingerly touched it. I'd brought a banana from the fruit bowl to practice with.

They soon discovered that one had to pay attention so the rolled condom went on in such a way that it would roll down smoothly. Upside down, and it just sat there. They took turns, each rolling it on, and then off the banana. Melody said it was time to try the real thing....

I lay flat on the bed, and lightly and slowly stroked myself through the nightie and panties. It did not take long before I had an erection. I asked if they wanted me to put the condom on, or if one of them would do it. Sam said, "You do it the first time." I pulled the hem of the nightie up, and then pulled the panties down, so my penis was free.

Here, I should tell you that one of the preferences I have developed about masturbating or engaging in other activities while wearing panties or other lingerie is that I absolutely do not like pulling the crotch of the garment aside. I like to feel the smooth fabric on my skin, so I can caress or be caressed through it. Pulling the crotch to one side puts side pressure on my penis and scrotum, lessening to a great extent the pleasure I seek.

If I am going to dress without planning to masturbate or have intercourse, I will wear panties or other garment. On other occasions, I will masturbate in what I think of as "girl style," which is rubbing my erect penis through the fabric. Generally that means my penis is tucked back between my legs, and I fondle myself by wiggling my right index and middle fingers, one on either side of the penis. For this, I am likely to wear a garterbelt over my panties.

If I will be masturbating "boy style," sliding a loose fist up and down the shaft of my erection, or if I will be having intercourse with a partner, I will snip a small opening in the panties for my penis to pass through. I may start with wearing two pairs of panties, the inner with the hole, the outer without. I may tuck my penis so that it nestles softly within the panties, so that until I have an erection or wish to use it, it is away from the hole. When the erection is firm, I can extend it through the opening and proceed.

Failing any of those techniques, I will lower the panties until my erection is free, or as an absolute last resort, will take the panties off completely. For these episodes, I wear my panties over the garterbelt.

Back to this episode: as a relatively inexperienced lad, I chose to pull the panties partially down. My penis stood quite firm and tall. Kathy passed me the condom. I placed it on the tip of my penis, and smoothly rolled it down. This was before that days of colored or tinted condoms, so it was just the standard, thin, milky-beige latex, like a surgical glove.

I rolled it up, lifted it off, then put it back on twice more. I asked if one of the girls wanted to do it, and Sam accepted first.

She did exactly as I had demonstrated, rolling it down slowly and smoothly, then just as smoothly, rolled it back up. Twice more, them Melody did three and finally Kathy did three. They had been nice enough to take turns fondling and stroking me through the nightie, which kept my erection firm.

It may be difficult to imagine, but I was getting tired or bored, even though the girls were enchanted. I told them that I would like to stop. Kathy said that we shouldn't waste the condom, that I should masturbate for them, so they could see the ejaculation.

We were all good about satisfying each others' curiosity, so I agreed. I said that I would lay on my back and masturbate for them until I ejaculated. Melody stroked my chest as she watched, Sam slowly rubbed my tummy with an open palm, so I could feel her warmth. Kathy stroked my thighs with her fingers. All leaned in to watch closely.

I started slowly, but any boredom fled as I treasured the almost-overload of stimulating touch. I found my eyes closing to help concentrate. I tightened my fist a little, then relaxed it, creating my own slow pulsation. I discovered I was making for a tighter fit as my fist descended, and loosened my grip just a bit as it rose again.

A dozen strokes and I found my hips gently thrusting to push more deeply as my hand slid down my penis, and withdrawing as I reversed direction. Maybe another dozen strokes and I warned the girls to watch closely, as it was about to happen...and then it was over. I felt a warm glow spread through my belly and chest. My hand and hips stopped moving, though I kept a snug grip on my penis.

I still had my eyes shut, but felt much pleasure as the girls described that they had seen. My penis appeared to become a little longer, and bigger around. The color deepened or darkened somewhat, then the milky ejaculate suddenly filled the top inch or so of the condom, obscuring the head of my penis.

Soon, the erection began to go away, so I sat up, then stood up, holding the open end of the condom so the liquid inside would not run out to make a mess of my panties or nightie. I asked Melody to help lift my nightie so I could take it off, while I held the condom in place. I got one shoulder out, then my head. I switched hands holding the condom. Sam slid my panties down and I stepped out of them.

I carefully removed the condom, holding it up for inspection. There was about an inch of liquid collected in the end. I stepped into the bathroom, and emptied the contents into the toilet. I explained to the girls I had a very strong urge to urinate. I did, then wiped my penis with some toilet tissue. I wrapped the used condom in the tissue and explained that we should not flush it because the cottage has a septic tank. We couldn't just drop it in the trash, and I didn't want to burn it. I suggested the best way to get rid of it was in the dumpster at the fire watch tower.

We changed into shorts and t-shirts, tidied up the girls' room, stashed the remaining condoms, and started a load of laundry including the nightie and panties I'd worn. We rode our bikes to the tower, ditched the wrapped condom in the dumpster there, and enjoyed a snack of cookies and pop sitting on the deck at the top.

By the time Mom and Dad returned, the laundry was dry and been put away and we had the table set for dinner.

We had other adventures that summer, and summers since, perhaps I shall share some of them with you in a future story.

Karen – Darren's alter ego.

  

  

  

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