My personal first time

My name is Mei-lani (may lani), and this is the story of my first time,
all of it is true, nothing is made up. Just so you don’t get confused. Sometimes people call me Mei-Lani, or they like to shorten it by either calling me Mei or Lani. This is the first time I have ever written an erotic story, however I am a frequent writer... It is very long and there isnt much action until the end, but I really wanted to put you in my shoes... feed back is appreciated.

Stephen was 3 years older then me and my parents would often ask him to
watch after me if they needed a last minute babysitter sense he lived
right next door. He usually always agreed, he never asked for any money
but my dad would often slip him $40 every night.

I always had a slight crush on Stephen. He was about average height,
skinny, and he had curly hair that he grew out and it suited his
handsome face to have the large curls dance around and frame his face.
He had soft green eyes with long black eyelashes and luscious lips.

I was always embarrassed of my appearance around Stephen. I was by no
means ugly, I was tiny reaching only 4'8" and weighing barely 105, I had
a great body with a nice bubble but and a good sized pair of breast for
my size being in-between a B and a C bra size. As for my face it had not
changed sense I was 11 (in fact even now I look exactly the same as I
did that day) so I was embarrassed about looking so young.

My crush on Stephen had been growing significantly throughout the
summer, I would often go over to his house and he had introduced me to
marijuana a month earlier and we would spend all day walking around the
woods behind our neighborhood smoking and talking. Plus we were both
really into music (I play the piano, guitar, bass, and I sing, while
Stephen played the piano, saxophone, drums) and would often spend long
days making music together. Spending all this time with Stephen having
him treat me as an equal and not as a little kid really made me
appreciate his company, even to the point where when I would masturbate
I would often imagine it was him touching me, imagining he was rubbing
his finger along my sensitive button dipping his fingers into my virgin
opening dragging the moisture from my hole to my button.

My crush was getting so intense I craved for Stephen to have similar
feelings for me, I even went to the extreme of getting my haircut like
his favorite pin-up model or as he would say "one of the sexiest women
to have ever existed" Bettie Page, whom I also greatly admired. Once I
even sneaked a peak at his porn collection on his computer which he
"cleverly" named as "moms wedding photos" which I knew was bullshit sense
he had never even seen his mother. Most of his pictures were of girls
being fucked in schoolgirl uniforms. It made me wonder if he thought I
looked sexy when he would pick me up from school. (I went to an all
girls’ catholic school.)

I figured I would try and excite him that night by wearing my school
uniform, I decided to wear my skirt from two years ago that still fit
but was hemmed too short for school. I made my "innocent" schoolgirl
attire complete with white cotton panties, white over the knee socks,
black maryjanes, and I put my hair in pigtails. I looked just like the
girls on Stephens computer, or at least I hoped I did.

"Mei-lani! Were leaving! Come on down and say goodbye!" I heard my dad
yell up the stairs, I hurried down the stairs and planted a kiss on my
dad, my dad made a puzzled face as he took in my attire "it's the middle
of summer, why on earth are you dressed for school!" I shrugged at his
response "I need to do laundry." I was surprised at my quickness with an
excuse. "Ha! I told you, you should have done it yesterday instead of
running around with Stephen. Oh speaking of which he should be here
soon." I sighed, trying to act like I didn't want him over, I didn't
want my parents to get suspicious of me wanting to be alone with him (I
was after all dressed like a typical sex icon) "ugh I'm 14 when are you
guys going to trust me to be alone!" my dad mimicked my sigh "it's not
that we don't trust you lani, it's just that we don't trust other
people. All right We will be back late tonight" "okay bye! Love you"
just as my parents opened the door I saw Stephen walking up the drive
way, "hi Stephen! Bye Stephen!" my mom said jokingly as she ran passed
him "later!" Stephen said as he approached the door, he literally
stopped when he saw me.

He stood there staring at me with a bewildered look on his face, I
squinted my eyes and bit my lip trying to look seductive and confused at
his obvious state of awe, "what" I asked "your hair." I was devastated
it seemed as though my outfit had no effect, "I really like it, the
bangs look good on you and pigtails suit your face really well." He said
finally making his way inside. "Oh, thanks!" I said, although his
compliment made me happy I really wanted him to look at my outfit and
want me like the girls on his computer. He walked into the living room
and I followed he then quickly turned around and held a joint in front
of my face, "Care to blaze" I noticed his soft green eyes look at me
from bottom to top and it made me feel better, "why sir! I do declare!"
I said in my best southern bell accent.

We sat on my back porch smoking and talking, when I suddenly got a
naughty idea I thought might excite Stephen, "hey what is that" I said
squinting into the grass about ten feet in front of Stephen "what's
what" he asked trying to see what I was looking at "that!" I said as I
walked about five feet in front of him and bent over and looked into the
grass, could feel my skirt rise and I knew he could see my underwear, I
was getting wet just the idea of him seeing them, not trying to be to
obvious I squatted in the grass and started patting the grass as if
trying to find something then I got on all fours being sure to stick my
butt up in the air. "Nice panties!" Stephen said playfully, while
giving my bottom a light pat. "Yah I bet you enjoyed that! Haha" I said
standing up he laughed, "you have a cute butt! What can I say" his
comment made me ecstatic. I sat back down next to him, only this time I
sat close enough to him that our knees would touch "my mom lost an
earring out here, I thought I saw something reflect the light I thought
it might be it." "Oh." He said as he looked directly in my face, he
made a small smile, and then I knew, I could just tell by the way he
looked at me, with his soft green eyes that he felt the same way about
me as I did about him. I felt my face get hot and I wanted nothing
more then for him to kiss me.

I looked down at my shoes in a nervous gesture and he turned his gaze
and looked off at the sky. "Hey," he said "yah" I responded to see he
had returned his gaze to me. He gave me another smile as he placed his
finger on my chin and brought his lips to mine, our kiss was quick, just
a peck and very nervous, he quickly turned his gave to the horizon, and
we both sat there in silence. I was overwhelmed with excitement, Stephen
hadn't been my first kiss, but it was the first that meant anything.
"Your 14 why on earth do your parents still ask me to baby-sit you" he
said obviously trying to get rid of the tension in the air, "they don't
trust OTHER people." I said mocking my father. "Hahahaha if only they
knew what we do together." I laughed at his reply and he looked at me
"I think you’re really pretty." I felt my face get hot and Stephen leaned
in closer to me and gave me another kiss, only this time he held his
lips over mine. "Damn, haha" he said after breaking the kiss while
pushing dirt around with his shoes. "I've wanted to do that for some
time now. I was just afraid sense you were younger then me, you'd think
I was creep." I couldn't help but laugh "I could never look at you as a
creep." He looked back at me smiling.

He leaned into me again starting with a soft tender kiss, he slowly
opened his mouth, and I followed pursuit allowing his tongue to enter my
mouth, as our tongues dance he leaned in closer to me and I could feel
the heat radiating from his body, he let his hand find my knee and he
slowly started to massage his way up my thigh, I felt my body grow hot
and I wanted nothing more for him to continue his pursuit and find my
eager vagina, he moved his hand to my inner thigh and I moaned into his
mouth when he let his finger brush over my panties, he quickly pulled
his hand away and broke our kiss. "Fuck." He murmured, "what's wrong" I
asked scared he was somehow angry with me, "we can't do this." He said
looking at me with his beautiful eyes. "Why not" I asked eager for him
to touch my wet vagina again, only this time under the panties.
"Because Lani, what will happen afterwards We will fool around tonight
and then what Tomorrow we just go back to normal We can't date
each other, your father will chop off my nuts he's so protective of you,
and then we won't be able to hardly ever see each other, it will be
pointless. And I care way to much about you to just fool around with you
for a night and then just act like nothing happened." I gave him a
playful push "my parents don't have to know about anything, no one does,
we could act normal with everyone else, then be a couple when we are
alone." He gave me an ensuring smile, "it can't hurt to try. But lets
go inside, to your room.... I don't want to get bitten up."

He held out his hand and led me inside, he ushered me to the stairs "lead
the way" he said motioning up the stairs as I walked up the stairs I let
my ass sway seductively, Stephen reached out his hand and gave my ass a
tight squeeze "goddamn your ass is nice" he said as we neared my bedroom
door, as I reached for the handle he wrapped his arms around me and I
could feel his hard dick press up against my ass, which I thought was
strange sense he was so much taller then me but when I looked down I saw
he was bent slightly at the knees.

I opened my bedroom door and Stephen followed me in closing the door
behind him he put his arms around my waist and held be from behind and
slowly grinded his cock on my ass, he let out of a soft moan and nibbled
on my earlobe, I could feel my vagina boiling over and I was tempted to
bring a hand over and relieve myself but decided against it, I wanted to
save it for Stephen. He led me over to the bed and had me sit on the
edge.

He looked at me with hungry eyes as he stood towering over me, he bent
over and kissed me hard pushing his tongue in my mouth, to my delight
his hand found it's way to my vagina and he began massaging my slit
through my panties. I was dripping wet and my body felt like a
radiator, Stephen slipped his fingers inside my panties and I let out a
moan when he slid his finger across my slit letting out a gasp when he
touched my clit. He was the first person other then me to touch me that
way, he got on his knees and silently pulled off my panties, I was
embarrassed by my swollen lips and he looked up at me smiling "I see you
shave." I giggled at his remark then suddenly became nervous, I didn't
know what to expect and I was afraid he was going to stick his dick in
me, I wanted it but I was scared of the pain, then to my surprise he
looked up at me and said "Can I eat you out" I had no idea what he was
talking about.

He must have noticed my confusion because he continued with "I want lick
your pussy" I just stared down at him scared and excited, he smiled up
at me and spread my knees and he stuck his head between my thighs, my
entire body was shaking and I was about to tell him to stop, when
suddenly I felt his tongue slide from my hole to my clit, the feeling of
his velvety tongue rolling around my vagina and flicking over and over
my clit my entire body started to shake, he grabbed me by my hips and
pushed me further onto his face, he sucked my clitoris into his mouth
and began flicking it with his tongue, I began to moan and slowly grind
my pussy onto his face, my pussy was pulsating and I could feel the
tingling sensation in my body telling me an orgasm was near. The new
feelings Stephens' hot mouth was introducing to me felt so amazing I
couldn't imagine how I could have gone so long without it. He continued
to lick all over my dripping cunt paying special attention to my button,
suddenly he pushed his tongue into my virgin hole, the feeling was
electrifying and then he replaced his tongue with a finger and went back
to sucking on my clit. I couldn't take anymore and I grabbed the back
of his head as I humped his face as an overpowering took over my body.
I closed my eyes shut and absorb all that was going on as the orgasm
washed through my body, I thought about how the amazing feelings taking
over me were being enticed by the guy I've been dreaming would one day
make love to me. My entire body was on fire and I locked my legs
around his head and furiously humped his face, he continued to flick my
clit with his tongue, I started to moan and scream until finally I
couldn't take anymore and I pushed Stephens face away from my pulsing
vagina.

He laid down next to me on the bed and gave me a soft kiss on the lips,
I licked my own juices off my lips that Stephen left on me, "You have
the most perfect pussy" he said his eyes looking deep into me. I turned
to my side and placed my hand over the hard bulge in his khakis, I
started to gently massage him through his jeans. He let out some soft
moans and I decided to go further.

I fumbled with his button and pulled the zipper down, I could feel my
vagina growing hot again as I pulled his pants down, I could see the
outline of his hard cock through his boxers, as I tugged his pants down
further, I saw the tip of his penis hanging out. I looked up at his
face and he simply smiled at me as he pulled his pants all the way off
and lifted his ass up in the air to take off his boxers. I watched in
awe as he pulled his boxers down, revealing to me the first penis I ever
saw in person. His dick was hard but instead of sticking straight up in
the air as expected it lay on top of his balls sticking out in line with
his legs. (I later learned due to the large size of his cock gravity
held it down) I placed my hand on his hard dick and started to stroke it
slowly, his dick was just thick enough for my fingertips to barely touch
as I wrapped them around his cock. I looked up at him to see his
reaction when he winced in pain "it's too dry, that hurts" he said
looking down at me "what do I do to make it wet" he gave me a shy
smile, "you can use lotion." I was about to get up when he said "or you
could use salvia, I think that feels better, you could just spit in your
hand or if you wanted, but I understand if you don't, you could lick
it." He was watching my face intensely to gauge my reaction. "Like a
blow job" He stroked my breast through my shirt, "yah" his gaze was
held on my breast as he gently knead them, his warm hands massaging my
breast made me let out a small moan, he gently pinched my nipple through
my blouse, "but before you do anything, would you unbutton your shirt, I
want to see your breast” I did as he was asked letting my breast free
from the cotton shirt, "no bra" he commented almost joking "I figured
I'd probably just end up taking it off." He gave me a sly look "you've
planned this all out haven't you" I blushed and looked down at my bed
"that makes it even hotter" he said as he rolled my bare nipple, I let
out a small gasp and started to take off the shirt "no, don't I like it
like this."

I moved over so I was kneeling between his legs and I lowered my head
and picked up his cock aligning it with my mouth, I started gathering
saliva in my mouth and I wet my lips and I frenched kissed his entire
cock from bottom to top, distributing a healthy amount of salvia with
each inch, I wrapped my hand around his cock and stroked him slightly
squeezing my hand so it pulsed lightly as I stroked him (a tip I learned
from a porn magazine I found in my dads closet) I stuck out my tongue
(which is very long I might add) and licked all around the mushroom
shaped head, paying special attention to the underside, which Stephen
would groan every time my tongue flicked under the head. I looked up to
his face and his eyes met mine, while keeping our gaze I licked all
around his head then popped it into mouth sucking hard as my tongue
danced across the tip, and my hand pulsed up and down the shaft. As he
through his head back he groaned "uh holy fuck, Mei, oh fuck that feels
so good." I popped his cock out of my mouth and began to pop it in and
out of my mouth rolling my lips on the underside. "Oh, fuck! Oh fuck!
Ungh, you have to stop you have to." I popped his cock out of my mouth
and removed my hand afraid I hurt him; I worriedly watched his face as
he caught up on his breath. "Oh god I was about to cum" he said sitting
up to meet my gaze, confused I glared at him "isn't that good"

He grabbed my breast and started rolling my nipple between his fingers.
"I'm not done with you yet." My eyes grew big and I inched closer to
his body, "are we really going to do it" He looked into my eyes gently
and cupped my face with his hands, "if you’re not ready, we won't do it, I
just thought..." "No, please, I really want this." I cut him off, okay
let me get a condom," "no, we don't need one." he looked at me confused
"I know you've had your period I was with you when first got it 2 years
ago. I don't want to get you pregnant." I laughed at his response "my
mom put me on the pill when I started dating Axel, she didn't want me to
get pregnant like my sister did." He put his head between my breasts and
licked my nipple, sending electric shocks throughout my body "we should
probably use one anyway just to be extra safe." I looked down at him
with pleading eyes "I want to feel you” he groaned and looked up at me
"oh god this is going to be perfect."

I leaned up against my headboard and as he held my knees to my chest as
he positioned his cock at my pussy. "This is probably going to hurt..."
I looked up at him and let out a nervous smile "I know." He rubbed his
cock up and down my slit and I gasped with indescribable pleasure, who
knew just having a dick rub up and down my vagina could feel so good.
He moaned and then positioned his dick at my virgin opening. I gasped
as he pushed his dick into me, it was an amazing filling as he slowly
entered me, I was pained by just the stretching of my vagina around his
intruder, I was afraid of the feeling of him breaking through my hymen.
He got his head in and he moaned loudly as his head poked my hymen,
"fuck your so tight," he said through clenched teeth, "okay we can do
this two ways, ungh I can push through it slowly or I can force my self
in with a hard thrust." "Do it fast, get it over with."

He pulled back so only the tip was in and he pushed in, "ungh! Ow!" I
gasped, "shit, I didn't break it, okay... again” I braced my self by
grabbing my pillows, "okay I'm going to try again" he pulled out so only
the tip was in again, then he thrust all the way in breaking through my
hymen causing a searing pain rush through my body "agh!!!!!" I screamed
as I wrapped my arms tightly around him holding him in place as tears ran
down my cheek while my vagina contracted squeezing his cock buried deep
inside of me. "Oh fuck! Ungh... are you okay" he said gasping
between words. All I could do was nod, "is there anyway you could stop
squeezing my dick with you muscles... your so fucking tight, the
squeezing is going to make me cum, I can only hold it off for so long."
His comment made me laugh and I felt my body relax as I began to come to
terms with the new feeling rising in me. Stephen was inside of me, it
felt so good just knowing he was inside me, just then I felt him slide
his dick slowly back and the pain began bearable, he slowly pushed back
into me and I couldn't believe how beautiful it felt to be this close to
him, even though physically I was in pain emotionally I was in pure
bliss. Stephen continued his slow fuck and he finally released my legs
from my chest, I wrap my legs around him as he continued to push deeper
and deeper into my tight cunt, "ungh, oh fuck lani you feel so amazing,
ungh" with that Stephen increased his pace, and while I was beginning to
gain some physical pleasure the pain oversaw it, but I just enjoyed
giving Stephen such pleasure I dealt with the pain. Stephen pushed
harder and deeper into me and with each thrust a loud slap could be
heard as our bodies collided, he started massaging my breast with a
vigor and soon his tongue was in my mouth as he kissed me with such a
force I thought for sure my face would be numb. He kept pounding my
newly deflowered cunt when he released his kiss and took hold of my legs
again, "uh, oh fuck, uh fuck ungh!" with one last vigorous thrust I felt
Stephens cock pulse from deep inside of me as a wash of warmth leaked
into me, I knew it was his cum and I looked into his face which was
twisted into a pain like grimace. Then he fell on top of me his body
heaving, I ran my fingers through his curly hair soaking in what just
happened. I can't even put into words how wonderful I felt. "You
didn't cum..." Stephen said his words muffled by my chest, "it's okay,
it started to feel good, but it just hurt too much." He lifted his head
from my chest a look of sadness in his eyes, "I'm sorry, next time will
be better, I promise." My heart leapt at the time he said 'next time'
for the past year all I wanted was to loose my virginity to Stephen, I
never really thought past it, but now not only did I loose my virginity
to him, he was now my boyfriend.

---Summary
Stephen, didn't lie, the next time was better, we were a couple in
secret for one year, then my dad actually caught us in the act, so for
the next year we were openly together, however sense my father caught us
it was very difficult to get alone, we resulted to being intimate
together in the woods, except the few rare times we were able to be
alone in our own homes. But by the end of our second year together
Stephen moved to Tokyo for a year, we broke up not wanting to go long
distance, we both dated other people, and when he moved back we stayed
friends for a year until we moved in together. I have plenty of other
sexual adventures to write about, including those with Stephen my some
other guys I dated, and the few females I fell in love with. If this
story does well and you want to hear more from me I'd be happy to dig
through my journals and recap some events.