Rileys first DP experience
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Riley's Summer free porn video
Chapter 1
I was at my auntie's cottage by the sea this summer vacation, as I always
do. She has a cottage just outside a pleasant little fishing village, and
I've been there each summer since I was twelve. My parents work so much,
so they don't really have time to look after me, or have a vacation at
all. I really like my aunt Ann, she has always been there for me, and she
is also very generous. Her husband left her quite a lot of money, so she
spends her days travelling, but each summer she stays at her cottage.
After a couple of days I noticed that there were some lights in cottage
next to ours. That cottage had been vacant for many years. I asked my
aunt about this during breakfast the next day. Apparently some people
from Durham had rented it this summer, but my auntie hadn't met them yet.
Intrigued I looked closely at it when I passed it on my way to the beach.
It was renovated, and looked much nicer than last year. Other than a BMW
in the driveway, the cottage looked as empty as it always had been.
I laid the towel on the warm sand, and opened my book. Although there
weren't any people in my age in the village, I spent the summers in
blissful solitude. The books were my escape and companion. As I applied
sun screen to my slim and not very manly body, I gazed around the empty
beach. No one. I removed my trunks, and revealing my black Speedo briefs.
I got them for swimming lessons once, but I really enjoyed how they
fitted me. I only wore them openly when I was alone, or with my aunt. I
guessed she didn't know that it was a little strange to wear them to the
beach. I had viewed myself in the mirror, and from the behind I looked
like a girl. I guess that was a result of all the cycling I had done in
the past years. As no sport fitted me, as I was too scrawny to play
football and rugby, I found road cycling very appealing. I was doing
quite well, but the result was that I had grown larger thighs, but still
had a slim upper body. This added to keeping my fascination of wearing
speedos a secret.
After dinner I sat in my room looking at the mysterious cottage. It was
lights on now. Thinking of myself as a stealthy assassin, I decided to
check it out. I slipped out and crossed the driveway as quietly as I
could. I waited along the wall of the cottage and listened after noises.
Nothing. It was very dark, and I peeked into a window. A man was reading
a book next to the fireplace. He looked normal. A woman came into the
room with a tray. She also looked normal. I was a little disappointed. It
had to be something suspicious about them. I rounded a corner, and went
over to the next window with lights in them. I remember vividly what I
saw. It was a girl facing the window. She was only wearing a bra, but I
couldn't see more of her, as she was sitting at a desk. She was applying
make-up. She was very pretty, and she looked to be about the same age as
me. Finally some action, I thought. I was getting a hard on. She didn't
have large breasts, but just seeing a girl in her underwear was well
exciting.
The lights in her room made it difficult to see me. My patience seemed
almost endless, and I must have watched her a long time. God, how much
time do girls spend doing their make-up! I hoped she would get up, so
that I could see more of her. After a while she did. She wore matching
pink panties. Something wasn't quite right, though. She had a bulge in
front of her panties. I didn't quite get it, not until she moved her
hands inside her panties and reposition her "junk" between her thighs.
Shocked I moved backwards, and fell into some gardening tools. The noise
startled the girl/boy as well, as she went to open the window. I got up
and ran back to the cottage.
I kept thinking of this all night, and I didn't tell anything to auntie
the next day. Not to arouse any suspicion I went to the beach as I always
did. The beach was as empty as it always was, so I dressed down to the
speedos. As I didn't sleep much that night, I fell to sleep. I woke when
I heard something rattle. It was a boy on a bicycle. Embarrassed at
wearing speedos I flushed, but tried to act natural.
"Hi," I said sheepishly. The boy was about my age, and I didn't realize
the connection yet.
"Hi, I'm Jamie. Are you Riley?" he asked.
"Yes, I am. How do you know?" I was surprised by his directness.
He fixed his gaze and said, "I spoke to your aunt. Apparently you are
about the only boy in the area, and when I see you now, you look like the
guy I'm looking for." I got up, and not feeling very confident in my
speedos.
"You're looking for me, are you?" I asked.
"Yes, you spied on me last night." This boy wasn't very shy, was he. How
could he be so confrontational when he's the one who has been dressing up
like a girl? I hated being caught doing something wrong, and my instinct
told me to lie.
"I don't know what you're talking about. I don't have a habit of spying
on people. You know, you shouldn't go around accusing people." I was
taken by surprise as he jumped me. I fell backwards on the sand, and he
straddled me keeping my arms pinned.
"Don't lie to me, Riley!" I tried to fight free, but he was stronger than
he looked.
"Let me go! Sorry, yes, I did spy on you," I shouted while trying to
squirm myself out of his grip. He let go, and sat down next to me.
Embarrassed I sat up facing him.
"I'm sorry. I just wanted to know who the neighbors were, and I didn't
except to see..." I trailed off, but Jamie finished my sentence.
"To see me in drag?"
"Exactly," I said and blushed. We sat silent a little while. Jamie picked
up a handful of sand, and said
"I have known for quite a while that I enjoy wearing feminine clothing,
and even my parents thinks that it's ok. I'll be here all summer, and I
gather so are you?"
I nodded.
"I say that we should try to have a good time, and forget about you
lurking around in bushes," Jamie suggested.
I nodded in approval,
"Yes, I'd like that." After a while the conversation went more smoothly,
and it appeared that we had pretty much in common, like films, music and
books.
"Do you want to go for a swim?" I suggested, as it was becoming very warm
and I had a lot of sand sticking to my sun screened skin.
"Sure," said Jamie, and got up. He pulled off his tee and shorts, and
even though I shouldn't be, I was surprised when he stood there in a
bikini bottom.
"Sorry," I said. "I didn't mean to stare, but how do you hide your,
your..." I asked and pointed to his flat front.
"I use a gaff," he said and walked towards the water. I shrugged, and
went after him. I couldn't help looking at him. His ass was very sexy and
he looked very feminine in his bikini.
The rest of the day went by really quickly, and we came got along really
well. Jamie invited me to come over after dinner. His parents were very
nice, and showed me to Jamie's room. We kept talking like we had been
friends for ages.
Jamie suddenly looked serious and asked, "Now you know my secret, what is
yours?"
"I don't have any," I replied.
"Come on, Riley, everyone has something they keep away. What are your
secrets, Riley?"
I felt pressured, and racked my brain for something to say. I looked down
on the floor and said, "Actually, well, I haven't told this to anyone." I
looked up and Jamie lifted up one eyebrow.
"You won't tell, will you?" I asked.
Jamie promised.
"Well, I enjoy wearing the speedos very much. The one you saw me
wearing." I blushed.
"That's it?" Jamie laughed. I nodded.
"That gives me an idea. Will you allow me to feminize you?" Jamie said
eagerly. I guess he noticed my apprehension, and he said, "It won't hurt
you, in fact, it will be fun!" Why not, I thought, I guess it's just
harmless fun."
"Okay, Jamie, but it will be our little secret." Jamie smiled. We agreed
that I should spend the night, and while Jamie asked his parents I rang
auntie. Jamie asked me how I would like to look, and as I didn't have a
clue I said:
"Perhaps like you? Well, like you did yesterday?" Jamie smiled. He had a
very pretty smile.
"Okay, then, take you clothes off," Jamie said. I did, and Jamie looked
at my body and told me to turn around. It felt all right to be naked in
front of him. He was a boy after all.
"We need to shave off a little hair on your chest. It's not much, but it
has to go. Secondly, we need to remove the hairs on your legs. That'll
hurt a little, but not too much." I thought that this was going to be
fun. I went over to the mirror, and started shaving. Jamie found wax
stripes, and applied them to my thighs. It hurt like hell when he tore
them off, but soon after my legs were completely hair free.
"This is a gaff," he said, and told me to step into them.
"This might be a little strange, but you need to push your testicle up,
like, into you," he said and smiled. He laughed when he saw the
skepticism written in my face.
"I'll show you," he said, and before I could object he had his hands on
my testicles. He told me to hold them in place, while pulled the gaff
into place. He tugged gently at my penis, and pulled it between my legs.
I've never worn a thong, so the feeling of the skin colored gaff was very
strange. I looked down, and the front was completely flat. It wasn't
particularly uncomfortable, just strange. Although no one had touched my
penis before, I found it actually to be not very unnatural. Jamie was
very confident about this, and I guess his know how affected me. It was
in fact happy about not feeling any inhibitions about the human body.
Jamie gave me a short pink fleece robe to wear. I walked around his room,
while he prepared the make-up. The thong actually felt good, and my junk
was firmly tucked away.
"This will take some time," Jamie said, and pointed to the chair in front
of him. Jamie sat down on the bed, and started laying foundation on my
face. It was actually quite interesting, as he told me about all the
different kinds of make-up he used on me.
"So what kind of lingerie do you like?" Jamie asked. I was dumbfounded
and said I really didn't know.
"Do you like the slutty ones? Classy ones? Or just plain cotton?" I had
looked into lingerie catalogues, as any boy, and the ones I found sexiest
was the ones which was the shiny black with lace trimmings, so I told him
that.
"Well, and I do think thongs are most sexy. What do you like?" I asked.
Jamie smiled and said he was pretty much agreeing with me, and that he
also liked to wear garter belts. He put on a blonde wig. At this point
Jamie sat up straight, and said:
"I'm finished with your face. Take a look in the mirror. You are so
beautiful, Riley. I am very pleased with the result. I'm sure you won't
recognize yourself."
He was right.
The girl in the mirror was really beautiful. I couldn't believe my eyes.
I didn't look like a drag queen; I looked like a girl on her way to a
party. I felt like a doll when Jamie removed my robe and put on a shiny
black bra with lace trimmings. It was so bizarre, yet cool. Jamie applied
some make up to my chest so that it looked like I had cleavage. The
padding in the bra added to the effect. I now looked like I had small
perky breasts. I couldn't help smiling. Jamie was really good at this.
"These are my favorite," he said and handed me a matching thong. I
stepped into them and pulled them up.
"Wow, Jamie, this is incredible!" I exclaimed. I wasn't finished and
Jamie helped me put on a black garter belt and fastened the stockings.
The stockings felt very sensual as he gently pulled them up my legs. He
fastened them to the garter belt.
"You look even hotter than me," he said almost jealous. I laughed and
told him to dress up as well. I turned around, so that I could see my bum
in the mirror. It looked so hot. The thong cut between the cheeks, and
you couldn't see the gaff underneath. The suspenders framed my tushy and
created a very sexy look. I was surprised as I felt turned on by this,
and slightly worried if I would have an erection.
"I will, but first we will have to find you something to wear. I tried on
numerous dresses, and settled on a black cocktail dress. It was a little
short, but not too short. Finally some pumps to finish the
transformation.
"Ah, perfect! Mum must see this," Jamie said, and opened the door and
yelled for his mother, before I could object.
"No, no! This was our secret, Jamie!," I said desperately, feeling my
knees weaken.
"Come on, Riley. My mother is the sweetest. She was so helpful when I
told her about me cross-dressing. Don't worry," he said, and took my
hand.
"Yes?" Jamie's mother Deb said as she came in. I was transfixed, and
couldn't move.
"Oh, look at you, dear. You look so beautiful! Is this your first time?"
she asked. I nodded.
"Well, isn't this nice? Jamie had some problems in Bishop Auckland, so
I'm glad he found a friend here. I'm very thankful for being so
understanding."
I tried to smile, but it wasn't my best effort. Deb talked some more
about Jamie and Bishop Auckland, but left to leave us alone.
"Now I'll do my make-up," Jamie said. I couldn't believe Deb was so
understanding. She was really nice, but this was a little much for me. My
unease faded after a while, and I looked at Jamie doing his make-up. I
was fascinated by his skill. Soon after he was finished, and I recognized
the gorgeous girl I saw the day before. Jamie stripped, and I noticed his
cock to be a little swollen. It hung, but definitely not completely
flaccid. I expertly tucked away his boy-parts, put on a gaff and a pink
satin bra. He had the same figure as I did. He pulled a matching satin
thong up his hairless legs, and fastened his stockings on a garter belt.
He put on a sexy blue tube dress. Jamie taught me how to walk as a girl,
and how to sit. We had a really good time. We tried on many outfits, the
most revealing was a sexy nurse costume. I began to think of Jamie as a
girl, and become very aroused by the sight of him changing in and out of
different outfits.
The time was now about 2 am, and we were both exhausted.
"Where am I sleeping?" I asked.
"In the double bed with me, silly." The thought of sleeping in the same
bed was strangely exiting.
"You can sleep in this," he suggested, and handed me a light blue satin
nightie. I held it up. It had thin straps. I took off my dress, and Jamie
told me to put on a pair of white lace briefs. Jamie found a black lace-
trimmed baby doll, and black panties. We tiptoed out to the bathroom, as
Jamie's parents had gone to bed hours ago. We giggled as we did our night
care. I almost ran, and jumped into bed, revealing my lace clad butt.
"You should be proud to have such a nice ass, Riley. It's really sexy,
and I'm sure a lot of men are going to want to fuck it," Jamie said as he
got into bed.
"Well, that's not going to happen. I'm not a faggot," I said. Jamie
looked offended.
"Oh, sorry, I didn't mean it like that. I have nothing against gay
people," I said trying to deflate the tension. Suddenly, Jamie burst out
laughing.
"Relax, Riley, I'm not easily offended. Yes, I'm as gay as Christmas, but
you should not dismiss the idea being fucked in the ass. It's really
fucking great." I looked at him, and after a pause I asked:
"Have you had sex with other guys?" Jamie nodded,
"Yes, a few times." I was intrigued.
"In the ass?" Jamie nodded again.
"How is it like?" I'm not sure why I wanted to know. Jamie lay back on
the mattress and said,
"The first time it hurt quite a lot, but after that it was just heaven. I
mean, the feeling of a rock hard cock sliding in and out of you while
wearing lingerie is intense, and I am actually getting a hard on just
talking about it." We got in under the sheet, and Jamie turned off the
lights. Jamie leaned over me, and kissed me on the lips, and whispered
"Good night, girlfriend". I was lying there, listening to Jamie's breath.
What was that? Is he into me, or does he view me as a girlfriend? I was
thinking about this, and the fact that I was wearing a nightie. It's just
fooling about, isn't it? Or is it something else? I didn't sleep much
that night either.
Myra
- 02.12.2020
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