Weekend at Alice's Cottage

We'd had our high school graduation ceremony on Wednesday and now the holiday weekend was here and summer could begin.

Alice had been accepted to a college in Southern Ohio whereas I would be going away to a college near the Pennsylvania border. I wanted to be closer to her, but our relationship was so open it was okay. However, the upcoming weekend was going to be a great start for our summer.

Alice's mom, Kathleen, picked me up at my house at about 2 in the afternoon. My parents bade me a good-bye and told me to be a gentleman and be helping in putting the dock in and assisting in opening up the cottage.

It wasn't far to the cottage, about an hour and a half, and unbeknownst to my parents Kathleen had been out there the week before during the day. She'd hired local workers to put the dock back in the lake and get the cottage ready for summer.

As the big Cadillac sedan pulled away, Kathleen said to me, over her shoulder while driving, "You know this is your great chance to find out what it is like to be a girl. We agreed, when we talked about this, that you wouldn't wear any male clothing all weekend. Since this is a holiday weekend it means we've today, Saturday, Sunday, and until we get back on Monday for you to be as girlish as you want."

Alice sat up front with her mom, and turned to me, smiling, saying, "We've some wonderful plans for you as a girl. I trust you are wearing lingerie under those yukky boy jeans and that shirt."

"Yes, I am," I grinned, not knowing the full extent of their plans for me.

"Good," Kathleen enjoined, "As soon as we get there you can help us unload the car and then we'll get you all fixed up as a girl to start things off." That made me eager.

Little else was said about the weekend and we passed the trip talking about the scenery we were passing and various summer plans and, of course, our college plans.

The cottage, I found, was at the far end of the 2 mile long lake and up on a long hill which placed it about 100 feet above the lake and nestled back under a dense stand of tall oak and fir trees. Making it quite secluded, just as they'd told me earlier.

Between the cottage and the road they had a gravel parking area sufficient for about 4 cars parked side by side perpendicular to the pavement. From the parking area to the back door of the cottage was only about 15 feet. A small porch, at the rear door, was at the end of the building and afforded a nice view down through the property to the lake shore well below. To the left of the porch was a meandering set of flat stone steps that worked their way down to a large flagstone patio in front of the cottage with a picnic table and some chairs overlooking the lake.

Inside I found 2 bedrooms were on the upper level. The master bedroom had a smaller bedroom adjacent to it. Between the two bedrooms was a bathroom with full shower.

The stairs, just inside the door and at the end of the upstairs hallway, led down the a large living room, when one turned left, with a full wall of windows facing the lake below. The flagstone patio outside the living room had more steps that wandered down to the water. Near the bottom, and hardly visible from above, was a smaller patio area holding a large swing for relaxing and looking out at the lake.

The living room had two large sofas and fire place centered on them with a couple of overstuffed chairs added along the far wall facing the fireplace and sofas. Farther on, in the living room, was a dining area with a round table and 6 chairs and a small kitchen to the left backed up against the wall dug into the hillside. Tucked under the staircase, behind the paneled wall, was a second bathroom with a small shower under the steps.

The two of them had me take the outside steps, through the ivy ground cover, to the kitchen area as we unloaded the car. Soon, the groceries were put away and luggage was tucked away in the bedrooms with my things placed in the living room.

"You'll be sleeping on the pullout bed," Kathleen advised me. "We need to look proper to any neighbors that might come by. However, you can feel comfortable since we're so remote few people wander up this way.

"Now, it's time to transform you into the girl Alice has told me you want to be for the weekend. You will learn to behave like one of us in all ways. First, though," she went on, "You need to strip and we'll begin teaching you how to walk properly like a girl in high heels. You hunch your shoulders and walk like a sailor," she told me.

Alice got a laugh out of that, and Kathleen told her it was true. Alice confessed her mother was right and I needed to walk like a young lady when I had high heels on and not like a boy dressed as a girl.

Kathleen said she'd be busy getting unpacked, etc., but Alice could take care of me.

I was a bit taken aback when ushered into the upstairs bathroom and Alice began preparing an enema bag.

"What's this?!" I wanted to know.

"Dear," she answered, "If you want to walk like a girl you there's a device that will help you hold your posture and take steps in heels like we do. Just trust me."

So saying, she had me get on all fours on the large beach towel on the bathroom floor and inserted the enema nozzle and released the warm water into my anal canal. It felt different and a bit strange, then I began to feel full and my tummy looked a bit distended. Just as I began to feel uncomfortable, Alice had me get up and sit on the stool and void the contents from my anus.

I thought that was it, but they repeated the enema. This time, though, they'd changed the nozzle when I wasn't looking. Alice had replaced the tip with a dildo that was of medium/small size. As she began inserting it I noticed it felt larger and commented that somehow this was more difficult.

"Just preparing you for the plug you will need to wear for awhile, Dear," she said. "It is what you will need to help you to walk like a girl, stand and move about like one."

After I had once again emptied the enema contents, I took a quick shower and was toweled dry and dusted me with a nicely scented powder. My "peepee" as already at attention and she laughed, reminding me we needed to hide that for now.

Then it was time for painting my toenails and applying false finger nails of a bright red color to match them. After that Alice started in on my make-up. Kathleen stopped in to help with applying false eyelashes and critically survey the results.

Alice marched me into her bedroom, and had me lay over the side of the bed with my knees on the floor. She put on some rubber gloves and then began slathering a lubricant around my anal opening and then working some inside. Getting more goop, she made sure there was plenty there to accept the butt plug. I felt silly and helpless.

Showing me the device I was a bit stunned and I could feel my "peepee" and balls begin to shrink as my concerns grew with the size of this thing I knew they were going to shove in me.

Just as I tried to peek at myself Alice began to nudge the end of the medium sized butt plug against my anal opening and managed to work it into me. It was a bit of a struggle, with her telling me to relax and let it happen. "Once it is in you will love the feeling."

I wasn't so sure about that, but finally she had it all the way in me and the flared base could be felt touching my bottom cheeks. It was then I realized it felt rather nice, filling, and very sensual. Suddenly I realized my hard-on had returned!

She had me stand and put on a pair of silky sheer pink brief style panties. These were followed by a Jantzen "Postage Stamp" panty girdle just like I saw a classmate buy at the store a few months earlier.

"Okay, Darling," Alice directed, "Walk a few steps for us and see how it feels for you."

I was stunned by the immediate sensations in my bottom. It felt like I was being gently fucked with each step I took and the look on my face gave it all away to them.

"I think he likes it, Mom," called out to Kathleen who was now downstairs which brought back laughter from her.

Telling me to carefully sit on the side of the bed she pulled out a pair of nylons I'd brought and had me attach them to the panty girdle. My cockette was starting to stir with all these sensations and the obvious delicate scent of the body powder on me.

I stood and marveled at how pretty my toes looked through the nylon stockings. "Girls are so lucky in what they can wear and do," I thought once again.

Next came a pink satin bullet bra which Alice helped me don and then Kathleen returned with the promised silicone breast forms with the stiffened nipples that stood out just right. Suddenly I realized I'd felt feminine before but not as much as this. With the bra on I felt so proud of how I looked and loved the change of appearance.

Kathleen opened pockets on the panty girdle and inserted foam pads in them. In the mirror at the end of the room I could see I now really had a lovely girlish figure.

"Okay," Alice told me, "Step into these slacks and zip them up." The slacks were quite tight and emphasized my figure nicely. They were rather stretchy with a floral pattern and white background. My undies were easily outlined in them. I had a little trouble zipping them up as the zipper was now in the back instead of in front. Definitely they were girl's slacks but I loved the look, the exposure of my undies, and the tight hug.

Quickly Alice handed me a lightweight pink satin boat neck pullover top with an elastic waistband that wasn't very tight. It felt lovely against my skin and she ruched the sleeves up to below my elbows and then put a dangly bracelet on my right wrist. She then clipped a pair of earrings on, in gold to match the shiny bracelet, and started in on my hair. My hair had just enough length to allow her to style it into a feminine style.

Moments later I was walking down the stairs to the living room where Kathleen awaited my entrance as a girl.

It was wonderful wearing what I had on. The false breasts seemed so real and moved about just like a girl's would. The girdle was quite comfortable but I found myself still unprepared for all the sensations of the butt plug in what I was to learn is my "boi pussy." My nylons still allow the tight fitting slacks to slide over my legs and tease me with the wonderful rubbing against my stockings.

They had given me a pair of black patent leather "flats" to wear until I got used to the outfit and the butt plug. The also didn't want me navigating the outside steps, in high heels, just yet.

"I think you look terrific," Kathleen exclaimed, "Well done Alice!"

"Mom," she said, "This panty girdle was a great idea you had. It not only holds "Erica's" butt plug in place but keeps his cock from giving away his true sex."

Kathleen reached up and rubbed over where my cockette was tucked back between my legs and agreed. It was tucked up in so well it almost gave me a "camel toe" look to my crotch and I loved that look!

"It isn't uncomfortable, is it, dear?"

"N-no, i-it isn't but this plug thingy is making it hard to keep hidden."

"Aha, I knew it would turn you on. Well, let it and that we'll take care of later. In the meantime enjoy what it does to you and begin trying to walk in a more girlish manner. As you do the butt plug will let you know if you are doing well as it will begin to feel even more sensual to you," Kathleen finished.

We had some lemonade on the patio and discussed dinner plans. Alice wanted a pizza and Kathleen made a call from the kitchen to order one. "It's Friday and they're busy," she sighed upon returning, "So I'll take the car and run down there in a few minutes

and be on hand with it comes out of the oven. Why don't both of you take your lemonades and go down to look at the lake while I'm getting the pizza?"

It sounded like a great idea and would give me a chance to further explore the new surroundings. Walking down the flagstone steps was a bit arduous as the butt plug seemed to take on a new life. It seemed to be bobbling up and down inside me and felt larger than before.

The tight slacks, that came to the middle of my calves, felt so sexy and tight and it seemed to make my girdle and panties rub together in a most delightful way. Walking down the flagstone steps took concentration and the clothing I had on made that difficult.

Once at the shoreline we strolled out onto the dock and looked at the lake. We were really quite remote from the other cottages, the nearest being about 500 feet away and through a fairly thick growth of trees. Boats were being put in down the way and we could hear their engines being fired up, but none were in our vicinity except for a small Sunfish which was Alice's little sailboat.

A neighbor did spot us from down the shoreline and gave a wave of greeting.

Alice suggested we move back up to where the large swing was and we could sit there and enjoy the view as we finished our lemonades.

As we started to walk up the butt plug really began to feel like it was thrusting up and down inside me and felt even larger. I almost buckled from the sensations only to make Alice giggle.

"Feels pretty nice, doesn't it, Dear?" she inquired. At my nodded agreement and struggle to not only walk like a girl but not make it noticeable what was happening to me the butt plug began to buzz and make noise!

"Wha?!" I cried out and Alice burst out laughing.

"It's a remote controlled butt plug, Honey," she said. "With this little device," she went on, holding up a small square pad in her hand, "I can make it do all sorts of things to turn you on and maybe even cum in your panties."

"I-if y-you d-don't s-slow i-it d-d-down I'll c-cum r-right now!" I muttered as I struggled up the last of the steps to the small hidden patio with the large swing. It was all I could do to not start thrusting my hips to work in rhythm with the toy in me.

Easing myself down onto the swing, carefully, Alice turned the squirming butt plug down and the noise quieted with it. Finally, she just turned it off but the sensations seemed to continue.

"Turned on, Darling?" she asked as she sat next to me.

"Very," was my quick reply, "And loving being here with you and your mom and living like a girl to see what it is like," I added. "I can hardly wait to see what all we'll do."

We sat there enjoying our cooling drinks and chatted about what I had on and how I did love wearing make-up, having my toenails painted, being dressed this way, and even admiring how much nicer and more feminine my hands looked with the false nails.

Kathleen looked at her watch and admitted her mom would not be back for at least a half hour so we had time to relax and discuss what all I'd get to do over the weekend.

I learned that tomorrow I'd spend the first part of the day wearing the "flats" and the afternoon would find me undergoing lessons in walking "like a lady" in high heels. "You'll spend a bit of time practicing in heels tonight," she added.

Slacks and top in the morning and then a sort of summer dressy dress the rest of the day. At night I'd sleep in a nightgown just like them, but maybe a different style.

Sunday was somewhat unplanned but certainly more of the same.

It sounded wonderful and Alice kissed me deeply as she finished telling me of the agenda.

We'd just pulled back from our embrace when the young man who waved at us from afar walked up from the shoreline holding a drink in his hand.

"Hi Alice," he called out as he made his way up the steps. "I see you've brought a friend."

He was dark haired and looked to be about our age. He had large blue eyes that fascinated me and a handsome face. Otherwise he seemed of medium build but a bit more athletic than me.

"Oh, hi Clyde," Alice replied. "This is an unexpected surprise. How have you been."

"Lonesome for you all winter," he replied as he eased himself onto the swing between us. "My name is Clyde and my family has a cottage just down the lake," he said turning to me. "Alice and I dated last summer. Who are you?"

"This is my friend 'Erica'," Alice broke in. "She's staying with us for the holiday weekend. What are you doing with a cocktail in your hand? You're 18 like us, not 21."

"It's ice tea, Alice," he replied slightly put off by her rebuke. "I've missed you and expected a nicer greeting than that," he concluded.

"I'm sorry," she replied and leaned over and kissed him on the lips. I was a bit taken aback but knew she was also doing it for me. Then she leaned toward him again and kissed him again for a much longer time, this time I could see her tongue enter his mouth.

Finally coming up for air, she asked him, "Wearing your panties for me?"

Clyde immediately began to blush, but Alice calmed him down by giving him a quick peck and said, "Don't worry about Erica, she understand and likes guys in panties. We both find guys wearing panties a turn on."

Clyde turned and looked at me sitting next to him and I just smiled sweetly and nodded a 'yes' as there was little else I could do. Maybe I could figure a way out of her and leave them alone - if she wanted to pet with him it was okay with me as I was having a ball being a girl. However, escape was not allowed.

"Maybe you can show us your panties," Alice said kissing deeply again and running a hand under his shirt to play with his nipples as she did so.

It was clear he was responding to her treatment and moaned when she rubbed his chest and kissed him yet again.

"Feel him," Alice muttered to me, "And see if you can tell is he has panties on under his slacks." The look of surprise and embarrassment on Clyde's face was obvious.

While it was stimulating for me to watch them I had no thought to feel to see what he had on under his slacks. It was apparent Clyde didn't want me checking, either.

Yet, the question seemed just normal without giving it another thought I reached down to his crotch to see if I could tell.

No, I couldn't tell but I was amazed that I could feel a nice sized hard-on growing in his pants. At the same time, Alice turned the butt plug on to a low buzz only I could hear but certainly react to!

"Is he?" she insisted.

Now it was all beginning to get to me and I knew I couldn't, wouldn't, and somehow didn't want to resist her command.

"I, I can't really tell," I managed to whisper in as feminine voice I could muster - these being my first spoken words in Clyde's presence.

"Unzip his slacks and see," Alice went on as she continued working him up to a fever pitch with her French kissing him and feeling his nipples.

Still not thinking clearly, I did as told. I managed to unzip his slacks and he eased his hips up off the swing enough to let me slide his trousers down over his sheer white panties that displayed a growing hard-on inside them.

"Ye-yes, he is," I managed to muster and couldn't resist stroking him through his panties.

By now Clyde was going nuts due to the ministrations of "two girls" and surrendering to the work we were doing to him.

"Alice just loves jacking guys off," Alice muttered when she next came up for air. She said this to me with an arched eyebrow indicating I had better do as she said or I'd be exposed as not being a girl.

"You don't mind if she slips it out of your pretty panties, do you Clyde?"

All he could do was shake his head and allow me to slip his panties down a little more and ease him out of them. I wasn't even thinking about anything other than complying with Alice's directive to me.

"Jack him, Erica," Alice intoned as she began suckling on Clyde's now amazingly stiff nipples. "Get him nice and hard for us."

Soon I was finding myself really turned on to jacking of a guy for the first time in my life. It was as if I needed no direction from Alice but wanted to do it all by myself. Feeling another guy's cock in my hands was a new experience and an unexpected thrill.