first threesome with my boyfriend
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My First Boyfriend free porn video
My First Boyfriend
My father died when I was too young to remember and I grew up quite
happily with my mother and sister; my sister Jenny being three years
older than me. I loved dressing up in my sister's cast-off clothes when I
was little and my mum thought it was a cute quirk. It was only after I
started school that she began to feel protective about my hobby and told
me never to let anyone know because they might not understand. When I got
to about nine she became even more uncomfortable with me dressing up and
from then on it was a secret, which I only shared with my sister. It was
never a sexual thing for me, just a feeling of relaxation when wearing a
dress and the much nicer materials of girl's underwear. I always loved
the way my legs moved against each other, a sensation that was totally
missing in a pair of boy's jeans.
I matured later than most of my contemporaries and, although I'd had
erections for a few years, I never really played with myself much. I got
as much pleasure from running my hands over my bottom, especially when in
silky panties, or feeling the softness of my tummy and sometimes pinching
my nipples quite firmly. I must have been almost fifteen when I had my
first orgasm and it was a bit of a surprise.
One Saturday evening I was alone and bored. During the afternoon I'd been
helping my mum clear up the loft and amongst lots of old clothes was her
wedding dress. Although I knew I shouldn't, it was impossible to resist
trying on that hugely romantic white dress. Apart from anything else it
was a symbol of my parents wedding and I missed having a father, somehow
wearing the dress brought me closer to him. I was slim and the fit was
perfect. Before slipping into the dress I had borrowed one of my sister's
bras, which I stuffed with a couple of silk scarves, then added a
suspender belt and a pair of white stockings. At that time I could still
fit into either my mum's shoes or my sister's, both were a size 5. I
chose a pair of cream coloured strappy sandals with 3" heels.
My sister had been teaching me how to apply makeup for several years and
that evening I went for the full moody look. My hair wasn't very long and
was difficult to style to look feminine, so I borrowed a white sunhat
from my mum's wardrobe; it finished the ensemble to my satisfaction.
When I eventually looked at myself in the full-length mirror in my
sister's room I was delighted. The dress was pure white, knee length and
had long lace sleeves. I spent ages admiring my reflection in the mirror,
turning this way and that and trying out different facial expressions and
poses.
For some random reason I decided to have a poke around in my sister's
chest of drawers and that was when I found her vibrator. I giggled when I
switched it on and it tickled when I closed my fingers around it. I sat
on her bed and suddenly knew what I was going to do. Propping myself
against her pillows, in such a position that I could see my reflection in
a mirror, I pulled the hem of the dress up to reveal my thighs and
panties.
From that point on I wasn't consciously thinking anything, just staring
at my reflection like it was someone else. The vibrator tingled against
my inner thigh and then crept between my legs until it was tickling that
place between my balls and my ass. The sensation was heaven and my little
cock, even now it's still less than five inches when erect, was so hard
it felt like it might break if I touched it. I think I must have blacked
out for a second or two because my panties were suddenly wet; my heart
was beating fast and my breath released in a moan. At first I didn't
realise what had happened, then my cock pulsed again as the vibrator
crept further back towards my ass and I moaned with pleasure at my first
orgasm.
Fear that I might have stained my mum's wedding dress was accompanied by
self-disgust, shame and embarrassment. I couldn't look at myself in the
mirror when I rushed to the bathroom and stripped off the dress and
underwear. I washed the makeup from my face so vigorously that my skin
felt sore.
Fortunately the dress was unmarked and, without thinking, I stuffed the
soiled panties into the wash basket, never suspecting that the evidence
would be noticed. The vibrator was returned to my sister's room. It was
the first time I'd felt any guilty about dressing and didn't understand
why it all ended so differently. A few days later there was a note from
my sister.
'You can borrow my vibrator again, but please use a condom over it.'
There were two packets in the envelope with the note and I blushed so
hard that I thought my face would catch fire.
From that day on I became fixated on masturbation. Three or four times a
day wasn't uncommon, but the best times were always when I was dressed.
My sister even told me to keep the vibrator in my room as I used it so
often. When I had the opportunity to dress completely, do my makeup and
adorn myself with jewellery and perfume, I sometimes achieved orgasm
simply by use of the vibrator. On those occasions it felt like I was a
real girl, as I didn't even have to touch my cock.
When my mum went on holiday with some friends I asked my sister if she
wouldn't mind me dressing when she was at home. She said it would be nice
to have a little sister around and encouraged me, even helping with
makeup again and giving me fashion tips.
"I can't call you Chris when you make such a pretty girl. You must have a
name you use in your head?"
"Kirsten," I replied. The name had been in my head for some years,
borrowed from someone I'd admired on television.
"Mmm, cute name Kirsten."
One Saturday afternoon Jenny was helping me to style my hair, which was
now almost shoulder length. It was straight and I'd dyed it with henna to
a red-black. She was stood behind me and we were both chatting to each
other in the mirror when she told me she had some friends coming round
that evening. It didn't seem to be any concern of mine until she said
that one was a really good friend who would like to meet me.
When she said this I went into a sort of panic, my mind couldn't process
what she was suggesting. Jenny just kept telling me about cute he was and
how she'd known him from when they were at school together. She was
saying that he had always been a bit confused about his sexuality had
confessed to her that he was addicted to videos of crossdressers on the
Internet. She had told him that she knew someone he might like to meet,
but had not said who it was. He'd asked if she could arrange a meeting
and she had said she would see what she could do.
"So little sister, Kirsten, do you think your ready?" she asked, as she
tied a second ribbon to finish putting my hair in bunches.
I couldn't trust my voice and just nodded.
That evening I was dressed in a short, flared, black skirt and a white
top with a wide scalloped neckline that Jenny had arranged so that it
dropped off one shoulder to leave it exposed. My bra strap showed, but
she said that was considered sexy. I had holdup stockings and some cute
black shoes with an ankle straps and four inch heels. I'd been practicing
all afternoon and, although my legs ached, I was quite stable.
It had all happened so fast that I hadn't had a chance to think about it
and run away from the idea. Then the doorbell rang. It sounded like a
huge crowd outside on the doorstep. Jenny held my hands and looked me in
the eyes.
"Just remember," she said firmly. "You're a very pretty girl and Jeremy
is going to be more nervous than you are."
She pushed me towards the door and I whispered, "You want me to open it?"
She nodded.
I opened the door and one of Jenny's regular boyfriends was there, she
had loads of them, along with a tall good-looking boy with dark hair.
Jenny was standing behind me; she grabbed her boyfriend by the hand and
dragged him into the lounge. Looking back over her shoulder she said.
"Jeremy, this is Kirsten. I told you about her."
I smiled and Jeremy smiled back. He was practically shaking with
nervousness, which made me feel somewhat more confident.
I took his hand and led him into the lounge. It was already dark outside
and Jenny had turned down the lights and put some music on. Her boyfriend
had bought a bottle of vodka and was filling four glasses with tonic, ice
and lemon. I wasn't used to drinking and sipped mine slowly.
Jenny and her boyfriend started dancing to a slow song. I looked at
Jeremy over my glass.
"So, are you going to ask me to dance?"
He hastily put his drink down but obviously didn't know how to hold me,
he start off by looking like he wanted to do a formal dance. I was
getting into this and draped both arms round his neck, leaning my body
close to his. He had no option but to hold me rather more intimately. His
hands rested on my hips.
I swayed my body against his as the music and the situation swept over
me. This was something I'd imagined so many times while staring into a
mirror so I knew exactly how to move. His hands felt so nice on my hips
and I could feel that he liked what he was holding by the reaction of
something quite hard against my lower tummy. I nuzzled my face against
him so that my lips were on his the junction of his neck and his chest.
He smelled gorgeous. I felt like a total tease as I pushed myself against
his growing erection.
His hands held me tighter and started to guide my body. I was shifting my
weight from foot to foot in time with the music and in a way that ground
me against him. Eventually one of his hands slid round to my lower back
and then down onto my ass. As it arrived there I tilted my head up a
little and kissed his neck. I felt his cock twitch at the same time.
I'd completely forgotten my sister and her boyfriend until she spoke.
"We're taking our drinks somewhere more private." And they left us alone
in the lounge.
Both Jeremy's hands were now moving across my ass, feeling my hips move
and creeping lower to cup ass and pull me against him. I felt him kiss my
forehead and again tilted my face up towards his. I was rewarded with my
first kiss, which was sensational. I'm sure I moaned as his tongue
entered between my lips, I certainly sucked it in. It felt huge and very,
very sexy.
We both wanted to get to the next stage but Jeremy was obviously unsure
how fast he could push me. I led the way by taking his hand and sitting
him on the sofa. I sat sideways on his lap and turned my face for another
deep kiss. His hand rested on the outside of my thigh and started
stroking it as our tongues intertwined.
When his hand drifted inside my leg, I signalled my approval by kissing
him even deeper. My ass was right over his hard cock and I knew that he
needed help.
"Can I make you more comfortable?" I whispered in his ear and then
followed it with my tongue.
"Please," was all he could manage to utter.
I slid off his lap and knelt in front of him. Slowly, I unbuckled his
belt and undid his zipper, never breaking eye contact. He looked as
though all his birthdays had come at once. As my hand freed his cock his
hips rose and it went completely rigid as it straightened out. I smiled
at him and wet my top lip with my tongue. I knew I was being a complete
tart and loving every moment.
I'd never seen another guys cock before and certainly never done what I
was about to do. But some things just come naturally to a girl. My lips
slipped over the head and I fed what I could manage into my waiting
mouth. He took a huge intake of breath and held it. Then he groaned and
his cock pulsed. A huge jet of cum shot into my mouth and I had no option
but to swallow. More came very quickly with each subsequent pulse. I lost
count and kept swallowing.
I was delighted with his reaction because I knew it meant that he found
me attractive. I realised that until that first jet of cum I was still
unsure of my appearance. I had hoped for a little action for me and maybe
for my ass, but I smiled like the cat that had got the cream.
"I'm sorry Kirsten, I didn't mean to..." Jeremy started.
I kept hold of his cock in my hand while I crept up his body to kiss him.
From the way that he accepted my wet mouth I knew that it wasn't his
first taste of cum.
We kissed for a few minutes like that and then Jeremy turned my slowly so
that I was sat on the sofa and he was half on top of me. It was his turn
to slide down my body and I spread my legs wide for him to kneel between
them. His hands were on my thighs, thumbs on the inside of my thighs.
They moved up until his fingers touched the bare flesh above my stocking
tops and he smiled at me.
"I'm not very big Jeremy," I said nervously, expecting him to hope for
something the size of his own cock.
"Girls aren't supposed to be that big Kirsten," he whispered.
He kissed the inside of my thigh and his fingers were in the waistband of
my panties. As he pulled them down his mouth engulfed my small hard cock.
I closed my eyes so as to concentrate on what he was doing.
My hands moved down to touch his head and my fingers ran through his hair
as he took the whole of me into his mouth, his tongue even stretching out
to tickle my balls, which were in the palm of one of his hands. His other
hand now reached up and his fingers found my lips. I sucked his fingers
into my mouth, making them wet with my spit, but not realising what
Jeremy was planning.
When he withdrew his fingers from my lips I missed them, but not for
long. His hand was under my ass and I felt a slick finger slide between
my ass cheeks and push gently against my little virgin hole. I half
moaned half grunted my assent and probably sounded like a dirty little
whore eager to be taken.
It was quite sudden when his finger popped into my ass and I pushed my
hips down to impale myself willingly on his finger. At that same moment
my cock exploded, I had no control. I whimpered with the exquisite
sensation of Jeremy's finger inside my ass and his mouth engulfing my
cock. Everything I shot, Jeremy swallowed. Even when I thought I'd
finished he kept working my ass and I lay back like the girl I knew I was
meant to be, savouring every thrust of his finger and my cock pulsed a
last few times.
When his finger slid out of me I sighed with contentment. He kissed me
and I could taste my own cum on his tongue, slightly different to his. We
stayed like that until I heard my sister's footsteps on the stairs. She
knocked on the door discretely, giving us a chance to tidy ourselves up
before she entered the lounge.
"I think you'd better join me Kirsten, we could both do with touching up
our makeup."
She took my hand and I left the room with her, both of us giggling as we
ran up the stairs and hid ourselves in the bathroom.
Grace
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