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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 - 2 
by Cliff Dweller (blissful@comcast.net)

***

The second story in a series about visiting Gwen, my 
college lover, at her parent's house over winter break. 
The day started fitfully when she discovered that I had 
fucked her fourteen year old sister the night before; 
however, a mutual lust won out -- Gwen and I first 
screwed in her parent's bedroom, followed by more sex 
in the kitchen, enhanced by marijuana and strategically 
placed gobs of jelly. (MF, rom, inc, mast)

***

I lay in bed pondering the course of events that had 
taken place over the preceding twenty-four hours. It 
was winter break of my sophomore year in college, and 
my friend Gwen had invited me down from Connecticut to 
her parent’s house just west of Philadelphia. Although 
not my girlfriend, Gwen and I did enjoy great sex with 
one another, and we looked forward to some time 
together over the school holiday. 

Gwen’s parents were both college professors who lived 
in a big rambling house well over a century old. She 
also had a fourteen year old sister Chelsea, a freshman 
in high school, who slept in one of the third floor 
bedrooms originally built for servants. 

I was now basking naked in an adjoining bedroom that 
was vacant unless used by visiting house guests. The 
previous evening, I had enticed Chelsea into giving me 
her first ever blowjob, while her parents were at the 
university teaching classes and Gwen had been 
unexpectedly called away from the house for a couple of 
hours. This initiated a passion that cumulated in the 
middle of the night, when Chelsea had snuck from her 
bedroom into mine – we had fucked while her parents and 
older sister had slept one floor below. 

Presently, I could hear Chelsea and her parents 
downstairs as they prepared for work and school. Once 
they left the house, Gwen and I would be alone for the 
day. Just after they departed, Gwen indeed appeared in 
the bedroom doorway clad only in a fluffy terrycloth 
robe, which she pulled opened to expose a well formed 
set of breasts topped by pert brown nipples, a firm 
smooth tummy, and farther down, a thatch of amber 
colored pubic hair. 

With her hands, she squeezed both breasts together to 
accentuate their rotund firmness. It was clear she 
wanted to fuck me, and I pulled aside the blanket 
exposing my naked frame and semi-hard penis that I had 
idly been stroking since first awakening. But when 
approaching my bed, Gwen’s bare foot stepped on her 
fourteen year old sister’s underwear, forgotten and 
discarded after Chelsea had snuck into my bedroom for 
several hours of illicit sex before she dressed for her 
day at middle school. 

It was clear to Gwen what Chelsea and I had done on the 
bed she was now approaching, and her sultry look 
changed to one of outrage. Wham! She slapped me across 
the face hard enough to rattle my teeth, and then 
stormed down the stairs to her second floor bedroom, 
slamming the door behind her. Holy shit! I had driven 
several hundred miles specifically to screw my friend 
from college, and had just been caught with undeniable 
evidence that I had instead fucked her kid sister. What 
to do?! Grab all my stuff and flee back up to 
Connecticut? Apologize to Gwen? Lie and deny 
everything?  

In a panic, I raced naked down the stairs to the second 
floor and found the door of Gwen’s bedroom slightly 
ajar. Apparently she had slammed it with such force 
that it had bounced back open. At least I was saved the 
drama of having to plead through a locked door. Gwen 
was curled up on her bed tightly swaddled in that 
terrycloth robe. But she didn’t resist when I lay down 
next to her, and hugged her tightly from behind in a 
spoon-like fashion. 

We said nothing for quite awhile, and I thought it a 
good sign that she didn’t shove me away or again hit 
me. I told Gwen that I deserved the blow. In an attempt 
to justify what had happened, I explained that Chelsea 
had referred to me as a "fuck toy," and that when I 
asked her younger sister where she had heard the term, 
she told me it was Gwen herself. This provoked a sigh, 
and Gwen admitted that she shouldn’t have been so 
forthcoming about me with Chelsea. As I suspected, they 
shared a lot of secrets despite a five year age 
difference between them. 

I told Gwen that her kid sister adored and emulated 
her. Gwen again sighed, and said I didn’t know the half 
of it. She then told me an amazing story, reminiscing 
about a Thanksgiving holiday that came a few weeks 
after her thirteenth birthday -- apparently Chelsea 
wasn’t the only sister to lose her virginity to an 
older guy in that spare third floor bedroom. While the 
adults slept off too much turkey and stuffing or 
watched television football in the living room two 
floors below, Gwen and her sixteen year old cousin 
Steve pawed at one another on the same bed where I had 
just spent the night. 

They had known one another all their lives and had hung 
out together when his family came to visit a few times 
each year from Virginia. But now her small breasts were 
just starting to bud and Gwen wanted Steve to take 
notice. At that time, her bedroom was on the third 
floor – the same one Chelsea had moved into when Gwen 
had gone off to college. She had "arranged" to be 
caught by Steve on her way to take a shower while 
wrapped in only a small towel. 

Apparently this took awhile – Gwen said she had paraded 
back and forth in this towel nearly a half hour before 
Steve noticed. Then the towel was discarded at the 
doorway to the guest bedroom. Steve’s clothes quickly 
followed, and they had together willingly lost their 
virginity. 

Steve was always assigned that guest bedroom while his 
family visited Philadelphia, and Gwen recounted a 
situation very similar to what had transpired between 
Chelsea and me the previous night – since it was 
isolated from other parts of the house where the adults 
slept, this room was where the two cousins made love 
whenever their families were together. 

This affair lasted for years, and I suspected that many 
of the more imaginative sexual techniques Gwen had used 
on me at college were learned here. She said that Steve 
now lived in California, but implied that the affair 
had never ended; rather, it had been put on hold due to 
the great distance between them.

I encouraged Gwen to keep talking, since this seemed to 
diminish her anger at me for fucking her kid sister. 
Also, I found myself becoming aroused as Gwen talked 
about herself when she was Chelsea’s age, and I slipped 
a hand beneath her robe to cup a breast and tweak an 
exposed nipple. Again, she didn’t push me away, so I 
asked what her most daring sexual escapade with Steve 
had been. 

Gwen recounted in detail a time about a year and a half 
later – she would have been fourteen – when in the 
middle of a hot, sticky and humid July night, she and 
Steve had dared one another to go skinny dip in a 
swimming pool located behind a house a half block away. 
They were already naked, and tiptoed downstairs past 
rooms of sleeping parents and out of the house still in 
the buff. They made it to the neighbor’s pool without 
incident, but Gwen told me their splashing awoke the 
owner, who turned on the floodlights just as she had 
wrapped her light frame around Steve’s torso as he 
stood in three feet of water. Rather than fuck, they 
had to dash from the pool and back into darkness. 

Gwen laughed as she described her seventeen year old 
cousin running in panic with a rock hard dick jutting 
out in front of him. This set dogs barking, and 
sneaking back to her parent’s house had proved 
challenging. Sweating, and sprawled in the cool grass 
between two houses with the empty street in sight, Gwen 
said she sucked Steve’s flagging penis back to life and 
had then straddled him for some fervent sex before a 
gray line of dawn appeared in the eastern sky, forcing 
them to sneak back into the house and tiptoe naked to 
their respective bedrooms. This story caused me to 
think about Chelsea giving me a blowjob the previous 
night. 

Gwen must have read my mind, because she said her kid 
sister apparently took after her. I thought that just 
maybe, I had been forgiven, and that Gwen would not 
pitch me out of her house with a boot in the backside. 
Still, I didn’t want to press Gwen for sex if she was 
not quite ready.

Gwen’s parents had turned the thermostat down before 
they left for work and the big house began to chill. I 
was naked and developed goose bumps, so Gwen led me 
down the hall to her parent’s bedroom, producing from 
the closet a large terrycloth robe similar to her own 
that was worn by her father. I perched on the edge of 
her parent’s bed, and Gwen for the first time noticed 
the red welt on my face where she had struck me. I said 
it still stung, and she began to gently kiss it. 

She found some lotion on a dresser, put some on her 
hands and rubbed it into my swollen cheek. I was about 
to say that an ice pack would have been better, but her 
salve covered hands then pulled my penis from beneath 
the robe and encircled its hardening shaft, which she 
stroked up and down. I hadn’t worn the robe for more 
than two minutes before I was again naked, this time 
laying flat on my back on Gwen’s parents’ bed. 

Gwen removed her own robe and climbed atop me. Again 
she grabbed my cock, whose slick head she now rubbed on 
the tips of each breast. With my free hand, I twisted 
and kneaded whichever nipple that Gwen was not rubbing 
my penis against. Slowly, Gwen slid forward and when 
she enveloped my hard-on between her large breasts, I 
squeezed them together with my hands. I was fucking her 
tits! As she slid back and forth on my torso, the tip 
of my dick, which was now tinged purple, would appear, 
then disappear, and then again reappear. 

If she kept this up, I would have exploded sperm all 
over her chest. But Gwen had something else in mind, 
and slowly slid further up my naked torso, until my 
lips and tongue could suckle her nipples, which had a 
faint aftertaste of hand lotion. 

I could now reach her vagina with my hands, but 
discovered that she had already beaten me to it, and 
was rubbing vigorously away on a hardened clit. So I 
probed further, sticking my middle finger into a 
slippery wet cunt, quickly developing a rhythm that 
matched Gwen’s hand as it masturbated her clitoris. 

Her breathing changed, and it now came in a series of 
ragged gasps, followed by a loud moan as the first 
orgasm hit. Gwen continued to frantically hump my 
finger and a minute or two later, she was again 
cumming. Pausing only long enough to catch her breath, 
she grabbed my rigid penis, rubbed its head a couple of 
times on her clit, and let her vagina swallow the 
entire thing. 

We fucked hard -- watching her breasts bounce up and 
down was as much a turn on as the tempo of my shaft 
inside her. From deep inside my balls, I felt the 
familiar tingling sensation that always preceded an 
orgasm, and shouted that I was about to cum. Gwen 
increased her pace, and we orgasmed together, my sperm 
deposited deep inside her vagina. Afterwards, as we lay 
side by side panting, it occurred to me that Gwen’s 
parents had probably conceived her in this very room, 
perhaps on this same bed! 

Hunger drove us from our reverie, and clad once again 
in bathrobes, we padded downstairs to the kitchen for a 
breakfast of coffee, toast and jam. By mutual 
agreement, we decided not to get dressed until just 
before Gwen’s parents and sister returned to the house 
later that afternoon. After we ate, Gwen produced a 
marijuana cigarette, and suggested we smoke it outside 
to mask any incriminating odors. 

So we put on boots, and trudged out into the backyard 
in our robes, crunching a thin skree of snow beneath 
our feet. It wasn’t bitterly cold, and the thick 
terrycloth held off the chill, at least for the time it 
took us to smoke the joint. Soon, we were stupid and 
silly, chasing one another around the yard. 

I pushed Gwen against a large tree and pulled open her 
robe – exposing flesh that quickly developed goose 
bumps in the chill air. Her nipples became rock hard 
knobs, both from the sexual energy between us and the 
cold. I then opened the front of my robe and pressed my 
torso against hers as we engaged in a passionate French 
kiss. 

My hard-on jutted upward pressed tight against her 
tummy, and she bent slightly to embrace it between her 
tits. We could have fucked right there, but a neighbor 
came out of the back door of his house and jumped into 
his car late for work. God, we were less than seventy-
five feet away and in plain sight of the guy! But he 
was fumbling with his car keys and never looked up. We 
ran back into the house, intent on having sex away from 
prying eyes. 

Gwen perched herself atop the kitchen counter in the 
midst of breakfast crumbs. I stood on the floor in 
front of her and we kissed some more. Spying a half 
empty jar of strawberry jelly, I pulled open her robe 
and placed big dollops of the stuff on each nipple, 
saying this would warm them from the outside chill. I 
then wrapped my lips around her right nipple, 
swallowing in the areola along with a portion of 
breast. When I stopped for a breath, the jelly had 
disappeared. This was fun, and I did the other tit the 
same way! 

Gwen’s cunt lips were not neglected, and again I 
swallowed all the jelly and applied another spoonful, 
concentrating my tongue on a very tasty clitoris. By 
now, Gwen’s robe had fallen from her shoulders onto the 
counter, leaving her virtually naked except for her 
arms which were still encased in terrycloth sleeves. 
Gwen wrapped both legs around my upper back and pulled 
my head hard into her crotch. Her orgasm was as intense 
as I had ever seen from a woman.

Gwen wanted me to switch places, and I found myself 
sitting atop the counter with my dick jutting straight 
out in expectant reciprocity at the nude figure 
standing in front of me. The girl’s blowjob technique 
was an expert combination of rhythm and moisture. She 
started by dumping gobs of jelly along the full length 
of my penis, and spread it around so it coated my 
balls. The majority of her blowjob involved licking the 
head of cock, and bobbing her mouth up and down on the 
upper couple of inches of its shaft. Gwen occasionally 
removed my penis from her mouth altogether and rubbed 
it over her lips, cheeks and neck as she lapped at the 
remaining jelly. In my mind, I pictured Gwen working 
out this technique with her cousin Steve when she was 
thirteen or fourteen. 

Gwen licked my dick up and down until every bit of the 
jelly was gone, and then sucked its tip through her 
lips and moved her head back and forth as though we 
were fucking. As the cum began to work its way up my 
shaft, I gasped that I wanted to shoot the splooge into 
her mouth. Gwen pulled a few inches away, and obliged 
me by opening her lips as wide as they would go. 

She grabbed my penis, stroked it once, stroked it a 
second time, and continued to do so as several streams 
of sperm jetted forth. Her aim was not good, and my 
first ejaculatory streak hit the bridge of her nose 
before lodging itself into her hair. The second shot 
followed a similar line of flight. But the third and 
fourth were right on target, and disappeared down her 
throat. Gwen then stepped back and gave me a self 
satisfied grin while a string of cum dripped from her 
face onto her breasts.

It was approaching Noon, and we assumed there would be 
at least three more hours of privacy before anyone else 
returned home. Gwen and I put back on our bathrobes and 
drifted to the living room couch, drowsy from the 
marijuana and a morning’s worth of sex play. She placed 
her head on my lap and soon was fast asleep... we 
didn’t hear the door open and were unaware that Gwen’s 
fourteen year old sister Chelsea had only a half day at 
school. I looked up and there she was, standing in 
front of the couch still wearing her winter coat! 

She caught me channel surfing the television remote 
control with one hand while idly playing with one of 
Gwen’s exposed breasts with the other. Neither Gwen nor 
I had cleaned up after having sex in the kitchen, and 
it was evident to Chelsea what we had just done. Gwen 
still did not stir, prompting her grinning younger 
sister to put a finger to her mouth and shush me quiet 
before I could say anything. She then scampered 
upstairs to her bedroom.

To be continued...

* * * * * * * * * * * * * * * * * * * * * * * * * * * *
It's okay to *READ* stories about unprotected sex with
others outside a monogamous relationship. But it isn't
okay to *HAVE* unprotected sex with people other than
a trusted partner. You only have one body per lifetime,
so take good care of it!
* * * * * * * * * * * * * * * * * * * * * * * * * * * *
Kristen's collection - Directory 32