A Highland Holiday Pt. 01

Mike invited me to spend a couple of months at his parents place over the Summer Break, far up north in the remote Scottish highlands; I had nowhere to go, and nothing else to do, and I'd never been to Scotland, so I gratefully accepted.

We were class mates at Imperial College London, both third year students majoring in mechanical Engineering. Our studies were difficult, the pace was frighteningly harsh and people dropped out in to easier courses all the time. Mike was my only close friend, we didn't have much time to socialize as there was always another exam coming up, and each year by the end of the summer term, we were both physically and mentally exhausted.

Rumor control said final year was even more brutal than the other three combined, and we had a 3 months break before we dove back into the madness, a few weeks, or months, relaxing in the quite of the highlands was just what I needed to refresh my batteries.

My dorm was closer to the tube station and I was watching the BBC comedy "Monarch of the Glen" when Mike turned up on the night of our departure.

"It's not really like that Joe" he told me "well, not entirely anyway."

"I'll find out" I replied "but after last year, I could use some laughs."

We caught the overnight sleeper from London to Glasgow, then a regional train to Inverness, and finally a local train over towards the Kyle of Lochalsh. As our journey progressed the trains got smaller and slower, and the scenery become wilder, and remote.

Our connections had been on time, something of a miracle Mike told me, and we pulled into the Station just before two in the afternoon. His mum was waiting for us in the car park, sitting behind the wheel of a Gold Toyota SUV. Mike waved to her, and we rushed over, dumping our bags in the boot before jumping into the back seat.

"Have you had anything to eat?" she asked.

"Just some British Rail sandwiches, Mrs. Cameron" I answered for both of us.

She laughed "Call me Michelle, I think a late lunch is in order" she looked at me, "I can use the time to explain some things to you."

We shared a bottle of wine over a pleasant lunch. Cullen Skink sounds awful, but tastes wonderful, a gamey pheasant in raspberry sauce was followed by and apple and orange marmalade pie, Scottish cuisine wasn't nearly as bad as TV made out.

As the waiter cleared the last of our dishes, Michelle asked Mike and me to come with her. We went up a narrow staircase carpeted in some unrecognizable tartan faded from years of wear, to a bedroom at the back of the hotel. Two small suitcases were laid on the bed. Michelle's I assumed.

I'd never asked Mike just how remote his house was, but after 18 hours of riding the train, I was ready to stand still for a few hours. If we still had a long drive in front of us, I'd prefer to get another room and rest here for the evening.

At a nod from Michelle, Mike lifted one suitcase, smiled at me, and disappeared into the bathroom.

"I'm sure you're wondering what it is that I need to explain?" I never replied just stood looking out the window, waiting "Mikes sister died when she was 18" Michelle was sitting on the bed, a lit cigarette in hand, "it was a tragic accident, but it drove his father crazy, she was the center of his life, and afterwards he was severely depressed."

"He went to several psychiatrists, none helped, as time passed I grew more and more worried. I expected to find him slumped over his desk one night, discharged shotgun in hand" she took a deep draw on the cigarette, reliving that time was obviously painful "Colin's world was shattered, he was stuck in that moment and he always would be, unless we could find a way to snap him out of it."

"OK" I couldn't think of anything else to say.

Mike knocked on the door "Not yet Mike" she said "I'm telling you this, so that in a few minutes, you will understand what you're seeing."

She continued "I had to come up with a creative solution that would allow my husband some semblance of living. Mike loves his father very much, and he agreed to be part of my plan, although it causes him a great deal of pain."

"Now darling" she called to Mike.

The bathroom door opened and Mike came out, my eyes were immediately drawn to the long blonde wig he was wearing which reached down to his waist "Meet Fiona" his mother said.

"What the Fuck!"

"It's the uniform of St George's school for Girls" Mike told me "it's in Edinburgh, Fiona studied there."

I was stunned, my best friend, the man who helped me master math when I struggling during 2nd year, was dressed as a Scottish Public Schoolgirl, and carrying it off. He stood wearing sensible shoes, a just above knee length red and blue tartan skirt, a red jacket with blue lining and white blouse.

He was made up, pretty well done actually, he'd obviously had some practice, and he looked very feminine and at least 5 year younger.

I was staring at Mike, Michelle was sitting on the bed, she'd lit another cigarette and the acrid blue smoke was quickly filling the room, Mike was looking at me, nervous and worried.

"My dad thinks I'm Fiona, coming back for a quick break before heading off for my gap year" he told me "We've done this every year since she passed away." He came and sat beside Michelle on the bed, and her arm reached around and pulled him in close. "He's never even noticed I've not started first year yet."

"This is where it gets difficult" he said.

"Mike, you're standing their pretending to be your 18 year old sister; difficult doesn't begin to cover it."

"No Joe, I am my 18 years old sister, we all have to believe that, or maybe Dad won't." he paused for a few moments, "can you handle it?"

I smiled "It will take a little while to adjust, I wish you told me beforehand Mike."

"I couldn't explain this to you sober, mum thought it was better that we just rip the Elastoplast off so to speak."

"I could use a drink right now."

Michelle spoke up "We're not finished Joe, if we bring you back as Fiona's boyfriend, you won't have a moment's peace, he'll be watching you like a hawk making sure you're not getting into her knickers."

"Uh hu"

"If we bring you back as her girlfriend, he'll leave you alone, he just needs to see Fi for a few days over the holiday, and he'll be good for months."

"Mike!" I was looking at the second suitcase on the bed, I had a pretty good idea were this was going.

"I know it's a lot to ask Joe, and if you can't handle it, of course you'll be my boyfriend, or you can head back to London, I'll understand" his eyes were pleading "Please stay, you really will enjoy the highlands, and I'm not sure I can't do this alone for much longer."

He looked like he was going to cry, fuck, poor guy, as if the pressure of Uni wasn't enough, he had this to deal with.

If it wasn't for him I'd have dropped out of Uni last year. I'd probably be flipping burgers or something right now, he might not know it, or mention it, but I owed him. I was here for peace and quiet, not being harassed every second by a crazy father, so the question was, could I handle a little dress up?

I took a deep breathe "Well, if we're going to do it, we'd better get started."

Michelle came over to hug me, as did Mike, "Thanks Joe" he said "thanks ever so much."

His mother gave him the cars keys, then shooed Mike out of the room with instructions to wait on us, then she told me to strip and hand over my clothes.

"Michelle, I, I" I had never been naked in front of a woman before, well maybe my mum, but not since I'd first started playing with myself.

"Just think of me like your Doctor Joe, you can undress in the bath room if you want, but I'll need to help you get dressed, so."

There was no real choice, and soon I stood in front of her stark naked "I'll keep these" she told me taking my clothes and putting them in a bag "I'll give them back to you when you leave, I just can't afford any slip ups. "

She looked me over "You're a very attractive young man Joe, I like what I see" she grinned at me "but from now on, your name is Josie."

I blushed, and concentrated on keeping my cock from hardening in front of her. She sorted that issue by helping me tuck it between my legs, and then using some theatrical tape she secured it in place.

She opened the suitcase and helped me get dressed, white hold up stockings, white cotton panty and bra set, and the same uniform as Mike "You're both in your senior year, prefects, and captain and vice-captain of the hockey team."

"I know nothing about hockey."

"Neither does Colin "she laughed "girls' sports bore him, he won't ask you a thing about it, but you need details to hang a story on."

She took me into the bathroom and applied my makeup. The wig she had selected for me was a shoulder length bob cut, "Strawberry blonde" she said, "Scottish boys have a thing for Red Heads", I blushed, I hadn't considered we might meet other boys or men when I agreed to this, but it was too late to back out now.

I was given quick instruction on how to walk, talk, sit, stand, how to get in and out of the car, information was coming at me very fast "Don't worry, we've been through this before" Michelle said "Mike and I will be there to help you every step of the way."

We came out the back door of the Hotel, Mike had moved the car into the rear car park and with my hand in her arm, Michelle helped with my first unstable steps as a girl. My senses were overloaded, the shape and feel of the panties was very sexy, then the breeze touched me under my skirt, I was suddenly feeling very feminine, and I liked it.

I got into the back of the Toyota with Mike "Mike" I said quietly, my voice full of embarrassment, "I'm getting a hard on, will this tuck hold."

"Call me Fiona" he looked at me and I saw something I'd never seen in his eyes before, I blushed a little "we've got half an hour Josie, if you can't get it under control; we'll need to stop and let you handle it."

The idea of masturbating at the side of the road while Mike and his mother sat in the car was exciting, I could feel my cock get a little stiffer, damn what was happening to me.

I started to concentrate on my breathing, inhale, exhale, inhale, exhale; thankfully I felt my cock gradually soften under my skirt.

We arrived at Cameron House on time, it was a fucking castle, standing below a rugged Scottish Mountain, Grey Granite, Crow Step Gables, Turrets, Arrow slits, I goggled at Fiona, she live in a Movie set.

"My dad's the laird, 18th in line, going back to the 14th century. We're not rich, it takes a lot of money to keep an old heap like this up and running, but we manage, we get a bit of income from tenant farmers, and the rest from the hunting and fishing set."

"It's beautiful "I said.

Fiona laughed "wait until we get up there" she pointed towards the mountain "the light, the smells, it's a different world, if you're up for it, we can take a walk after dinner."

"Won't it be dark" I asked.

"We're really far north Josie, we won't lose the light until midnight. After that long train ride, I want to get up into the hills, get some blood back in my bum."

The only staff his parents had living in house was the cook, so we took our own bags inside and dropped them inside the front door; I heard another door open at the end of the hallway, to the right hand side of the mahogany staircase which rose majestically from the center of the marble hall.

Colin Cameron came rushing along, grabbing Fiona in a bear hug; he spun her around, her legs flying out a little as they spun "Oh my Fiona, welcome home."

She hugged him back, both laughing "Dad, this is Josie; she's my best friend from school."

"Welcome to Cameron House" he said, I too received a bear hug, but I was willing to bet he hadn't casually groped Fiona's bum during hers. I thought about that for a moment, this man had just felt my bum, and I wasn't worried about it, I actually felt quite good about the whole thing.

"Thank you for having me Mr. Cameron."

"Nonsense" he said" any friend of Fiona's is always welcome here. Dinners ready."

Dinner was all produce from the estates farms; potatoes, something called neeps, a type of turnip apparently, and Haggis. Fiona had a great deal of fun at my expense explaining exactly what a Haggis was, how rapidly they bred, how much time her father had to spend hunting to keep the population under control, I grew skeptical when she started on them having short legs and long legs and running around the hillside clockwise only.

"That's nonsense Fiona" her Mother disapproved "is that any way to treat a guest. Haggis, Josie, is the lining of a sheep's stomach with a sheep's heart, liver and lungs; minced with onion and oatmeal"

I think I preferred Fiona's explanation, but it actually tasted really good.

After Dinner Fiona took me to my room, it was next to hers. In the closet I found more women's clothes, the chest of drawer under the window had all sorts of interesting things in silk and satin. Fiona popped her head though my door "hiking boots, tweed skirt, Army Jersey and the Yellow Northface Jacket, 10 minutes down stairs" she breathlessly gave me my instructions, then rushed to her own room to change.

We walked slowly up hill, Fiona had suggested I go ahead; she wanted to be behind me in case I ran into trouble. She told me to keep to the path, the heather to either side could be treacherous to the ankles, and we start to gain height.

We had been walking for about an hour, we could see Cameron House far below us now "Are you peeking at my bum Fiona" I asked. During our ascent I'm sure I had seen her surreptitiously ogling me a few times.

"Eh, well the thing, is, hmm, it looks really nice in that skirt Josie" she stumbled through an explanation.

As before when her father had groped me, I realized I honestly didn't mind. "Fiona, we've been climbing for quite a while, what about a rest?"

I pointed to a large round rock just off to the side the path, we sat down with our back to it, and drank from our water bottles, looking out across the most splendid view I had ever seen. The mountains were greens and browns and purples, rugged, occasional obscured by a light mist, and in places outcrops of bare grey granite pushed up out of the colour. The light was made by god for an artist's pallet, if you could bottle the smell you would be richer than Channel, I had never really been an outdoors type of person, but I was very happy here.

"Joe" Fiona started.

"Josie" I replied "I'll find this easier if we keep thinking of ourselves as girls all the time Fiona."

She looked at me "I don't know why you agreed to do this, but it really helps, and I really don't know how to thank you."

I don't know why I said it, maybe it was the cool breeze playing under my skirt, maybe it was the clothes, maybe it was the roll playing, or maybe it was just everything "You could try kissing me."

She looked at me slightly startled, nodded, and leaned over to kiss me lightly on the lips, I was smiling at her with my eyes, I let my teeth gently bite her lower lip, her tongue entered my mouth, and my tongue rose to meet it, we rolled away from the rock to land in the heather, I ended below her, and we got down to some serious making out.

After about 10 minutes Fiona came up for air, "God Josie, what are we doing?"

My hand reached for her neck "Making out" I said pulling her back down. My cock was struggling against its hold between my legs, I was pretty sure Fiona was having the same dilemma, but my situation resolved itself as I shuddered and felt myself wet the back of my panties.

Fiona stared at me, "Did you just come?"

I nodded.

"Lucky bitch" she laughed "oh shit, we're losing the light; we better get our pretty arses back down the hill."

Michelle was waiting for us at the front door, a knowing smile on her face, "did you enjoy yourself girls?"

I blushed, "Yes Ma'am" and hurried up the stairs to my room.

I had a quick shower, put my wet socks and soiled panties into the hamper at the foot of the bed, and quickly slipped into a white satin nightdress which stopped just above my knees. The memory of Fiona lying on top of me, her hands feeling my bum, her tongue exploring my mouth, was still powerful and my cock got hard again.

At least now it was free, a tent pole for my nighty true, but free. I struggled against the feel of the smooth Satin against my cock; I desperately submerged into my Ipad, trying to distract myself from the hardness. After half an hour I had got the situation under control without resorting to self-abuse, when there was a light knock at my door, "it's not locked" I answered.

Fiona came in wearing a remarkable similar night dress, perhaps a bit lacier than mine, I lowered my eyes and smiled, her cock was obviously free too.

She lifted the light quilt "Scouch over Josie."

She took the lead again, and I lay back as she kissed me, first slowly, then with building fervor. I wanted to touch her cock; I wanted her to touch mine, I stopped her and sat up "I've never touched another one, have you?"

She shook her head turning towards me "why don't we see what it feels like together."

She took the nightdress off over her shoulders, completely exposed she lay down beside me, her hands dropped to her own cock and started to stroke it. I followed her lead dropping my nightdress to the floor, and letting my hands grip my cock.

After a few minutes her hand hovered over my cock, understanding I moved mine over hers, and with a smile and a nod, our hands reached out to take another cock in them for the first time.

I was something of a serial masturbator, so I was used to the feel of my own cock, but as my hand wrapped around Fiona's I wondered why I never felt the softness of the skin before, the ridges of the veins underneath, the contrast in colour between the glans and the shaft, the hardness was all I had ever been bothered about.

We got a rhythm going as our hands moved on our cocks, our breathing became heavy, and the bedroom window steamed over. We tried kissing, but we were too inexperienced to do that and keep the rhythm going.

I was looking into her eyes grinning as I received my first wank from another human being, I was lost in the sensations, her touch on me, her smell, her hardness. I felt a load stir in my balls, experience told it would only take five or six strokes before I came "I'm coming Fi, I'm coming."

Fiona continued to run her hand energetically up and down my cock, she pointed it at her belly, and as I exploded, the hot sticky white mess covered her belly.

She hadn't come, I thought we would come together but her cock was still rigid in my hand. I returned to the rhythm, working her cock hard, she let he hands move to her belly, her fingers rolled my spunk into her palm, then she raised it to her mouth and lapped it up. I felt my cock stiffen again.

Her hand grabbed painfully on to my shoulder, "now love" she moaned and shuddered through her orgasm. I wasn't quite as good an aim as her, and most of her spunk landed on my bed sheet. I bent my head and started to lick it off.

She giggled in my ear "you're hard again" I smiled invitingly at her "I can't get caught in here, you'll need to take care of that yourself" she got up, fixed her nightdress, poked her arse at me flirtatiously, and went back to her own room.

I waited a few minutes and put my ear to the wall "Fuck me Josie, oh fuck me" it seemed I was not the only one who had to take care of themselves.

Fiona needed some dad time, so I spent the next day with Michelle as she drove around the estate. I was in tweeds again, looking like a proper Scottish lady. I was introduced to famers and game keepers and their families, I was beginning to enjoy being a girl, I noticed the eyes leering at my bum as we walked around, and especially as I climbed into the car.