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               K R I S T E N' S    C O L L E C T I O N
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Chelsea's First Time
by Cliff Dweller (blissful@comcast.net)

***

While visiting Gwen, my college lover, I was introduced 
to Chelsea, her fourteen year old sister. When Gwen was 
called away unexpectedly, Chelsea gave me a sloppy 
blowjob -- her first. That night, this girl snuck into 
my bedroom where I lapped at her young pussy with my 
tongue, followed by torrid unprotected sex. (M/f-teen, 
ped, 1st, rom)

***

Over the winter break of my sophomore year in college, 
Gwen invited me down from Connecticut to her parent’s 
house in one of the wealthy Main Line towns just west 
of Philadelphia. We attended the same university, and 
although not into the official boyfriend / girlfriend 
type of relationship, we did have one thing in common – 
roommates who always went home for the weekend. 

This left us with the privacy of two empty dorm rooms 
in which we experimented sexually with one another for 
hours without interruption. Although not centerfold 
material, Gwen did have a pair of large perfectly 
formed breasts appended to a short trim body and a 
vivid imagination on how to best use her assets. I 
looked forward to the visit since Philadelphia had more 
than its share of museums and great restaurants, as 
well as the prospect of fucking my friend from college.
 
Gwen’s parents, who were both college professors, owned 
a big rambling Queen Anne-style house dating to the 
late 19th Century. I was greeted at the door by Gwen’s 
fourteen year old sister Chelsea, a freshman in high 
school. I liked historic architecture and Chelsea gave 
me a royal tour of the place. While Gwen and her 
parents each slept in bedrooms on the second floor, 
Chelsea had taken over the largest of the third floor 
bedrooms, a spot originally built for servants. Other 
smaller third floor bedrooms were now vacant unless 
used by visiting house guests, and I was given one just 
down the hall from where Chelsea slept. 

The two sisters got along royally and indeed had 
similar bodies, although Chelsea, who was still going 
through puberty, had noticeably smaller breasts and a 
slighter swell to her hips. It was apparent that 
Chelsea tried to emulate everything her older sister 
did. So when we walked down tree-lined streets and Gwen 
snuggled her arm under mine and stuck her hand in my 
jacket pocket, Chelsea did the same thing on my 
opposite side. 

Returning from our walk, the three of us sat on lawn 
furniture in an unheated back porch. I had grabbed a 
box of Whippets before leaving Connecticut, and pulled 
them and an empty seltzer bottle from my daypack. Gwen 
was an old hand with this stuff and was delighted, 
while Chelsea, who had never seen a Whippet, was 
suspicious. 

I explained that Whippets were small metal cartridges 
of nitrous oxide intended for home use in whipped cream 
charging bottles. When making whipping cream, the 
seltzer bottle was first filled with heavy cream and 
then pressurized with the Whippet cartridge, which 
caused the frothing action. For our intended use, the 
nitrous oxide alone was released into the charging 
bottle. 

I warned Chelsea about the dangers inherent with the 
inhalation of any compressed gas (make sure you get 
enough fresh air, don't freeze your lips, and sit down 
before inhaling to ward off dizziness). The 
physiological effects of a lungful of nitrous would 
last approximately a minute and then dissipate, 
although the residual after-buzz could last for some 
time afterwards. Basically, nitrous oxide gas produced 
an anesthetic effect, used by dentists and popular at 
campus parties. 
 
To further reassure Chelsea, her sister and I took the 
first hits so she could see what was coming. Gwen and I 
inhaled lung-fulls of nitrous, pulled some fresh air 
down on top and then held our breath. Within seconds, a 
light tingling came over us, increasing in intensity 
and frequency. The sensation felt like erotic waves 
pulsating up and down our bodies from head to toe. 

There was disorientation as the pulsing sounds and 
feelings increased, wrapping over one another. As the 
pleasurable throbs subsided, we both lay there with 
eyes shut in a dreamlike state, in which the external 
world had essentially ceased to exist. After taking her 
first Whippet, Chelsea floated backward into a piece of 
porch furniture and lay there with one of the biggest 
shit-eating grins I had ever seen. 

We asked Chelsea what she had thought about her first 
Whippet. She hesitated, and then said it was like 
masturbating, only better. I had heard this from people 
at college, but never from a fourteen year old. This 
girl was precocious! In jest, I suggested that Chelsea 
come to by bedroom later for another Whippet. 

We each did another hit of nitrous before walking back 
into the house on wobbly legs, high as kites. The 
girls’ parents were running out the door on their way 
to teach evening university classes, and the three of 
us sprawled out on the living room couch to watch 
television. There was a phone call for Gwen – she had 
an oral history class and had been playing telephone 
tag with her interview subject, who was leaving for 
England the next day and was available only right then 
to do an interview. 

So Gwen dashed out the door saying she would return in 
a couple hours. When her car left the driveway, Chelsea 
slid from her side of the couch towards me. I playfully 
grabbed a barrette that held up her auburn hair, 
allowing it to fall to her shoulders. I told her she 
looked prettier with her hair down, and giggling, she 
snuggled close against me as if she was my kid 
sister... but Chelsea was not my sister. 

The television program we were watching was dull, so 
Chelsea and I discussed college life and middle school 
angst. We agreed that sex, social status and the dread 
of being dissed were central to the life of both 
worlds. We played footsie in our stocking feet. Out of 
the blue, Chelsea asked me if I had sex with Gwen, and 
if I loved her older sister. I was taken aback! As I 
attempted to explain the difference between being 
lovers, versus actually being in love, Chelsea kissed 
me on the lips. 

Soon, we were making out in the glow of the television 
and rubbing each other through clothing. Chelsea 
plucked at a couple of buttons on my shirt, and 
slipping her hand through the gap, began to rub my 
upper chest. She then said that Gwen had referred to me 
as her “Fuck Toy.” The little hussy! She had known all 
along that I was screwing her sister. 

I knew the two girls where close, but I didn’t think 
they were confidants. So I asked Chelsea to define this 
term. It turned out she didn’t like the analogy, 
equating it to the time she had attempted sex with a 
boy of her own age, whose actions consisted primarily 
of groping and quick ejaculation. His self-centered 
behavior had left her unsatisfied. 

I thought back to my own experiences just five or six 
years earlier, and told her I understood what she was 
going through. But I also warned her that once in 
college, she would still encounter guys who were 
drunken, exploitative jerks. 

Chelsea was being honest with me, so I described the 
relationship Gwen and I had at college, attempting to 
provide a more positive definition of “Fuck Toy.” Her 
sister Gwen and I greatly enjoyed sex and were 
imaginative in its application, but we were friends and 
not in love. We both dated other people and did not get 
jealous about it. I said that young women did enjoy sex 
as much as young men. 

At this point, Chelsea said she could love me, and 
began to kiss me far more fervently than she had a few 
minutes earlier. But being inexperienced, she was 
unaware that her actions were causing a tingling in my 
penis. With her lips pressed fully against mine, she 
undid the remaining buttons on the front of my shirt. 

I slipped my hands up under her loose sweater and 
cupped small bra-encased breasts before reaching behind 
her back to unhook bra claps with fumbling fingers. We 
continued to kiss as she slipped the strap of the bra 
first off one arm and then the other, and pulled it out 
of the sleeve of her sweater and tossed it across the 
room. 

Chelsea’s still budding breasts were now liberated from 
this undergarment and my hands roamed freely beneath 
her sweater, cupping and tweaking each small nipple. I 
then pulled the loose sweater over her head and threw 
it in the direction of her bra. Her upper torso was now 
naked and both our hearts were racing. My palms cupped 
her chest and my fingers flicked tiny nipples that 
turned hard in my touch. Chelsea whispered that until 
that moment, she didn’t know they were that sensitive. 

My dick became so hard that its tip began to peek out 
of the top of my jeans. Chelsea’s hand accidentally 
brushed against it, there was a pause, and then she 
rubbed it again not so accidentally. She shifted 
positions, and laying her head on my lap, and began to 
carefully examine the denim clad shaft of my penis and 
its shiny exposed head, which was now emitting a syrupy 
clear substance. Chelsea’s prior sexual experimentation 
had introduced her to sperm, and she said that this was 
something different. 

I gasped that it was pre-cum, sort of a lubricant. 
Taking this as a cue, she rubbed the stuff all over my 
glans, which she began to tease by lightly kissing and 
gently blowing on. I had been rubbing her naked back, 
and now pushed my hand down the back of her pants and 
beneath her panties, cupping her small soft buttocks. 
God, I thought I would die!

I wanted Chelsea to switch to sucking, and asked her to 
undo my belt and fly. My engorged penis and hard, tight 
balls jumped straight out at her. Wanting to get a 
closer look, she again laid her head across my lap only 
a few inches distant. I pumped my dick up and down with 
my free hand, saying this was how I jerked off. 

Chelsea said she had once seen a girlfriend give some 
guy a blowjob, but had never done it herself. She said 
she wanted to do it, so I told her to create a vacuum 
by pursing her lips, and then use them to surround my 
penis. I also told her that a wet cock looked sexier 
that a dry one, and to use her salvia to lubricate my 
penis. So Chelsea proceeded to lick my dick up and down 
its full length until it glistened. On one of her 
upward swings with her tongue, she lingered at its head 
and sucked it into her mouth, running her lips all 
around the rim of this knob. 

Chelsea engulfed my cock head fully in her mouth, and I 
guided her hand to my shaft and begged her to pump it 
as she had just seen me do. 

The sensation was intense, and I grabbed a handful of 
her hair with one hand, and twisted a small bare nipple 
with the other. We were both gasping. It would be over 
in seconds. A groan that I was cumming caught Chelsea 
by surprise and the first hard spurt jetted fully in 
her mouth. Chelsea jerked her head back in astonishment 
and watched wide eyed at the geyser she created. She 
tugged my dick again and a second shot of ejaculate 
formed an arc over her head and splattered against the 
arm of the couch, leaving a stick white contrail in its 
path across Chelsea’s cheek and forehead. The third and 
fourth blasts followed a similar trajectory and 
embedded in her hair. 

As I lay there breathlessly, Chelsea licked her lips 
which were covered with gobs of cum. She scooped some 
from her cheek and nose and put it into her mouth after 
she had thoroughly examined it, exclaiming she didn’t 
think there would be so much. She moved my cum around 
in her mouth with her tongue before swallowing saying 
it tasted kind of salty. Totally fascinated, Chelsea 
continued to fondle and play with my cock well after 
the spasms subsided, causing it to remain aroused. 

Suddenly, Gwen’s car flew back up the driveway and we 
both dived for discarded clothing. When Gwen entered 
the living room, Chelsea and I were models of chaste 
propriety, perched on opposite ends of the couch with a 
half eaten bowl of popcorn between us. In the glow of 
the television, our flushed faces at first looked 
normal. But as Gwen put her coat away, I gestured to 
Chelsea that she still had some smeared sperm on her 
face. 

She gasped and bounded up the stairs to the bathroom, 
grabbing her discarded bra along the way. In her 
absence, Gwen sat on the couch next to me and asked if 
I had been bored. I secretly was thinking that I had 
come to Philadelphia to screw the girl now sitting next 
to me, and instead had just received the first blowjob 
her fourteen year old sister had ever given. 
 
Their parents returned from the university shortly 
thereafter, and we all watched the tube while the two 
girls chattered away. Eventually they told Chelsea to 
go to bed because it was a school night. Shortly 
afterwards, I excused myself and climbed up the stairs 
to my bed in the third floor guest room. The heating 
system in the old house was inefficient, and despite 
cold temperatures outside, the upper floor was very 
warm. I ended up sleeping naked beneath a single 
blanket, completely forgetting that I had invited 
Chelsea to my room for a Whippet. 

About 3 AM, she tiptoed barefoot into the guest room, 
sat on the edge on my mattress and shook me awake, 
saying she wanted to again taste nitrous oxide. She was 
wearing a long sleeve cotton night shirt that buttoned 
down the front, stopping a couple of inches above the 
knee. I sleepily encouraged her to just go back to bed 
but she was adamant. 

What was I to do? I was naked, and retrieving the 
Whippets required me to crawl out of bed. Chelsea had 
not considered this, and let out an audible gasp as I 
pushed the covers aside and crouched down to paw 
through my belongings to find the things. This young 
teenager hadn’t seen too many guys naked before, and 
now there was one in her private third floor domain. I 
ended up sitting cross-legged on the floor, eye level 
with her knees as she sat in front of me still perched 
on the edge of the bed. I did the first Whippet, and my 
body was quickly flooded with pulsating erotic waves as 
the laughing gas took effect. When my mind again gained 
consciousness, I discovered that my hands were rubbing 
her calves and knees. I had also developed a raging 
hard-on that poked up at Chelsea while she stared back 
at it in open mouthed wonder. 

Chelsea started to play footsie with my penis, rubbing 
her bare feet up and down the sides of my engorged 
shaft. A warm sensation began to build in my balls, and 
I pushed my arms further up her inner thighs. Each soft 
stroke got tantalizingly closer and closer to her 
crotch until my thumbs made contact with one another at 
her crotch and pushed against her pelvic mound, which 
was encased behind bikini panties. This tickled, and 
Chelsea jumped and giggled, saying that she now wanted 
to do a Whippet. 

I had failed to mention that Whippets only give the 
illusion of an orgasm, and they can make people very 
horny. Whoosh went the nitrous oxide as it entered 
Chelsea’s lungs and she slowly and dreamily fell 
backward onto the bed, her legs still dangling over the 
side of the mattress. She had no awareness of me 
pulling off her panties and sliding her night shirt 
above her slim waist, exposing a pussy topped with a 
tiny thatch of amber pubic hair.

Still kneeling on the floor, I positioned myself so my 
mouth was at her clit level. I began to softly kiss the 
outer lips of Chelsea’s vagina, teasing its lips with 
my tongue and stimulating the area around her clitoris. 
Engaging her clitoris directly with my lips and sucking 
hard, I could actually feel it harden and swell with 
blood. I had found her pleasure button and didn’t take 
my lips, tongue or mouth away from it. 

As I wagged my tongue back and forth across Chelsea’s 
clit, I felt like a thirsty dog lapping at an ice cream 
cone. Chelsea, for her part, wrapped her legs around my 
back and began to push her pelvis into my mouth. My 
hands fumbled with the buttons of her nightshirt, and I 
loosened enough of them to expose her small breasts, 
which I cupped and fondled. Reaching further up, I 
traced her lips with one finger, which she then sucked 
into her mouth. I was on the home stretch! 

Chelsea began to buck and her legs started shaking as 
she thrust her vagina deeper into my mouth. She was in 
the throes of ecstasy and went over the edge in a mind 
blowing orgasm. I cupped the palm of my hand over her 
mouth to muffle the moans, and then kneeled there with 
my head using her pussy as a pillow while Chelsea spun 
down and returned to earth.

We crawled atop the mattress, making out and messing 
around with each other’s bodies. Eventually, I ended up 
lying on my back with Chelsea sitting astride my hips. 
Loosening the remaining buttons on her nightshirt, a 
pair of small perky tits poked out at me in near 
darkness. I asked Chelsea if I should cum inside her or 
upon her, implying that I didn’t want to make her 
pregnant by unprotected sex. She said she didn’t use 
any birth control and agreed we shouldn’t fuck. 

So I directed Chelsea’s hands to my hardened penis 
thinking she would begin to masturbate me. But she had 
other things in mind and began rubbing my cock-head 
against her still engorged clitoris as the nightshirt 
slipped off her shoulders, leaving her naked. Time for 
me to inhale another Whippet! And another rush with 
increasing intensity, the sensation causing erotic 
waves to pulsate up and down my penis.

When I opened my eyes, the fourteen year old was 
fucking me and I was shoving back! She had closed her 
eyes and focused all her attention on the feelings she 
was giving herself. Chelsea was incredibly tight, and 
only the first couple of inches of my shaft had 
disappeared into her cunt. But she was slick from 
cunnilingus, and eventually my entire dick was 
swallowed up, aided by my hands which were wrapped 
around her small buttocks. We had thrown caution to the 
wind. 

As our passion mounted, Chelsea fingers teased her clit 
and I pulled on her hard little nipples. She again 
began to cum just as I began to feel that tingle 
sensation in my balls that signaled my own orgasm was 
but a few seconds away. On one of Chelsea’s pelvic 
upstrokes, I jerked my engorged penis from her vagina 
and watched as it spewed gobs of cum all over her 
torso, splashing against the underside of a breast. 

In her fervor, Chelsea continued to dry hump me for 
another minute, during which my fingers circled a tiny 
nipple until it was slick with cum, eventually rubbing 
all of my seed into her chest and belly as it were hand 
lotion.

Afterwards, Chelsea snuggled close to me and said she 
had to go back to her bedroom. But soon we were fast 
asleep in each other’s arms. Gray light was streaming 
into the window when her mom, calling up the stairs 
from two floors below, told her she would be late for 
school. 

Chelsea jumped from my bed, ran naked to the top of the 
stairs and yelled that she would be right down. She 
then returned, grabbed her nightshirt and dashed off 
down the hall. A few minutes later, she came back into 
my room fully clothed, planted a big sloppy kiss on my 
lips, and skipped downstairs to breakfast and another 
day at middle school.

END

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The author does not condone child abuse, this story is
meant as an erotic fantasy not real life. Anyone acting
out such scenarios in "real life" can look forward to
many unproductive years getting it up the butt by a 
fellow convict in their local prison system.
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