My First Time

“Sure Thing” Network: Part 1

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“Sure Thing” Network: Part 1
The girls network, and Fifty shades of virginity.

Based on a post by reader4175.

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First Time.



Kaitlin.

Being nearly a year older, I developed physically and

mentally at a pace the other guys couldn’t keep. It helped me get the girls’
attention and interest.

Sadly, my academic development was nothing to boast about.

Kaitlin was a sporty little blonde, with tiny tits, a tight

ass, brown eyes, a great smile and perfect teeth. I'm not sure what really even
made me interested in her, other than her smile. It was always there and kind
of infectious. She was different from most of the girls, because she would take
time to talk to anyone. It didn't matter who you were, what you did or what you
looked like, she would still talk to you.

I did not think that I had a chance in hell with her, but I

didn't think that I had a chance in hell with any girl right about then. She
was right in front of me one day leaving class and I had a question about an
assignment, but the teacher was busy, so I asked Kaitlin.

She turned, looked up at me and said "Come over to my

house after school and I will help you with it."

Thàt was not the answer that I was expecting, but I was not

going to turn down her invitation.

We both had our own cars, so I met her in the parking lot

after school. I followed her home and she invited me into her empty house. We
sat down at her kitchen table and she wanted to get right to work. I was having
a hard time doing anything. I was really just staring at her and wondering
where this might go. She noticed that I was not paying attention, looked up and
asked me what was going on. All I could say was that I usually took a bit of a
break when I got home from school before I started my homework.

She asked me if I wanted something to drink,

 I said “yes”, and then watched her walk away.

She told me; “come to the fridge and pick what you want.”

 I was looking over her shoulder and all I really wanted was

her. I said that I would like a Mountain Dew so she handed one to me. I started
back towards the table, and she said “why don't we go into the living room.”

I sat down on the couch and she sat down right next to me. I

really was not expecting that, so I turned to look at her and she just smiled.
I took that as a good sign and put my arm around her. She just snuggled in and
put her head in my chest.

I really didn't know what I was doing, but I lifted her chin

with my hand and leaned down to kiss her. She didn't say a word and kissed me
back. I scooped her up into my lap and slid my hand up her shirt as I continued
to kiss her. Again she didn't try to stop me. I squeezed her tits and tweaked
her nipples for a few minutes while I kept kissing her. When I tried to move my
hand from under her shirt to the waistband of her pants, she pulled away and
said “that's enough, we are done.”

I must have looked disappointed, because she said “it's not

your fault, this is only as far as I am willing to go.”

 I ask “so what now?”

 She said; “we could go back to our homework or you

could take matters into your own hands.”

 I asked what that was supposed to mean and she said that

she wouldn't help me, but if I wanted to finish myself, she would take off her
shirt, sit in the chair across from me and watch.

I was hard as a rock and she could tell. I asked her to get

me a towel. She came back with the towel in one hand and her shirt and bra in
the other. I stood up, peeled off my shirt and dropped my pants.

Her eyes lit up, so I dropped my boxers and sat back down.

She took her seat and started to play with her own nipples. When I started in
on myself, she licked her lips and slid one hand down her pants. I really got
going watching her do her own thing. When I was getting close, I spread the
towel over my stomach and chest. She gave me a funny look and I just said
“wait.”

When I finally came, I shot three big ropes up onto my

chest, almost to my face. She must have really enjoyed watching me, because
just as I finished, she shuddered and came. I folded up the towel, but then
asked her if she wanted a taste. She nodded her head and said “yes.”

 I stood up, walked over to her and jerked the last few

drops into her mouth. She played with it for a few seconds and then swallowed
it.

We both got dressed and she asked me if I still wanted to do

that homework. I told her that I thought I would be able to concentrate now.

 She laughed and said “let's go do it.”

I had not performed for a girl before, but she must have

been impressed and told her friends about it, because the next day in class she
told me; “Meredith would be interested in helping you you’re your homework
tomorrow night.”

Kaitlin and I never got together again, but she would always

give me the sweetest smile and occasionally direct me to another girl that she
thought would like me.

Meredith.

Meredith had a different look than most of the girls at my

school. She was a dark haired beauty, with dark eyes, pale white skin and a
toned dancer's body. She could have easily played Wednesday Adams.

It was not the next day as Kaitlin had implied, but one day

at lunch, Meredith sat down across from me and said, “I heard that you could
use some help with your homework.”

 I asked her what Kaitlin had said. Her reply was; “You

are a sure thing.”

I asked her what she had in mind. She said that her parents

would be out Friday night and that she would like me to join her in the hot tub
for an adventure. I had not been in a hot tub before, let alone in a hot tub with
a girl, so I showed up to her house Friday night in jeans and a T-shirt with my
swimming trunks in my hand. She said “you really don't need those, but if you
would be more comfortable, we can start with swimsuits on.”

 I said that I thought that was best.

She pouted a little and I said “don't worry, we will get to

where you want to go.”

She just said “Goody,” and showed me the bathroom. When I

came out, she was waiting in a tiny black bikini.

She led me outside to the hot tub and we climbed in. I sat

down and as soon as I was settled she sat down on my lap facing me. She then
said “we can do this the fast way or the slow way, but either way we are both
going to cum.”

 I told her; “ I’m not in a hurry, so we can take it

slow.”

 She said; “that would work for me.” and then leaned in to

kiss me.

My hands had been resting on her hips since she sat down,

but they crept up to her ribs, and then her perky little tits, as we continued
to kiss.

She broke our kiss and told me; “take my bikini top off,”

which I happily did.

 As soon as it was off, she held up one of her own tits and

said “suck it.”

 I didn't hesitate and latched right on. She started

grinding on my lap and then whispered in my ear "I'm not going to fuck
you, but you're going to cum really hard."

I didn't know what she had in mind but I liked the sound of

it.

Meredith stood up, stripped her bikini bottom off and sat

back down in my lap facing away from me. She guided my left hand to her tits
and my right hand down to her pussy. I didn't really know what I was doing, but
she put her hand on top of mine and guided my fingers to where she wanted them.
Once I got going, she tipped her head back onto my shoulder and started moaning
in my ear. I must have been doing it right because she shuttered and stiffened
in my lap. When she finally relaxed from her orgasm, she turned and kissed me
and then told me; “ it’s your turn.”

She told me; “stand up and take off your trunks.”

 I did and then she had me sit down in front of her. She

pulled me into her with her left arm and reached down to stroke my cock with
her right hand. I hadn't gotten a hand job from a girl yet, let alone a reach
around under water. I leaned back into her and just let her do her thing. When
she started talking dirty into my ear I knew I wasn't going to last very much
longer.

I told her that I was going to cum and she told me; ”stand

up and shoot it into my mouth.”

 I just wanted her to finish me, but I wasn't going to pass

up this chance, so I stood up in front of her and started jerking myself off.
She sat up and opened her mouth. I leaned in and put my hand on the edge of the
tub next to her. I got as close to her mouth as I could and fired shot after
shot onto her waiting tongue. She took it all and swallowed it down. Just as I
started to back away, she leaned forward and sucked the last drops off the head
of my cock. It wasn't a blowjob, but I now knew I wanted one in the worst way.
I sat down next to her and pulled her in tight.

She told me not to get attached, because this wasn't likely

to happen again anytime soon, but she would direct me to a few friends who
would be interested in helping me with my homework.

 I leaned in to kiss her again and she gave me a sideways

look. I said that I didn't care and pulled her up onto my lap facing me. When I
started to get hard again underneath her, she hopped off and said “that's not
going to happen, but the other girls will love you.”

Sara.

Meredith must have spread the word, because I started to get

smiles from a lot of girls that didn't usually even look my way. I was starting
to wonder if there was something wrong until Sara sat down next to me in class
and asked me if I needed help with my homework.

I said; “I wouldn't mind studying with her.” In truth, I had

had my eye on her for years.

Sara was my type, just over five foot tall, a big smile,

nice teeth, brown eyes, dirty blonde hair, glasses and some of the biggest tits
in our class. Those boobs had drawn me to her since they first popped out.

I asked her what day she had in mind and she said “Friday

would really be the best, because my mom has an evening shift.”

Friday rolled around and Sara was waiting at the door for

me. We headed out to my car and waited for the parking lot to clear out. We
headed for her house down by the lake. It wasn't very big and there wasn't much
in the refrigerator. I suggested that we go back out to the corner store for
some refreshments. She gave me a sideways look and I said that I needed some
fuel, before we would be doing any homework. She turned around and we headed
back out the door.

I don't really remember what we picked up for food, but I

know that I got a bottle of Mountain Dew. We got back to her house and sat down
for a few minutes. Apparently Meredith had talked up the fingering skills that
I didn't know I had. Sara said that she wanted me to do for her what I had done
for Meredith in the hot tub except that she did not have a hot tub.

I really didn't know what the hell I was doing, so I

suggested that were go to her room and I started by giving her a massage. She
was a little shy and turned her back to me when she started to get undressed. I
peeled my shirt off and waited for her. She turned to face me with her hands
covering her tits and just a small patch of hair between her legs. I asked her
if she had any oil or lotion and she reached for a bottle, showing me one pointy
nipple. I told her; “lay down on your belly and I will start on your back.”

 I started at her neck and worked my way down to her calves

spending a little extra time on her ass. I really wasn't interested in feet, so
I stopped there.

She rolled over with half lidded eyes and asked me to do the

front. I started at her shoulders working on her arms and spending a lot of
time on her tits before work my way down to her legs and skipping over her
pussy. I moved back up and just kneaded her mound with the palm of my hand.
When she started to squirm, I knew it was time to go a little farther. She had
a chair near by so I sat down and told her; “come sit in my lap.”

 She sat up slowly and took some unsteady steps over to me.

I cradled her back with my left arm and started to work my fingers into her
with my right hand. I could only get my middle finger inside of her, so I
started working it in and out. I slipped my finger out and split her lips so I
could find her clit. I put my thumb on it and then slid my finger back inside
her. Then I started working both my thumb and my finger at the same time. I
turned my head towards her and could not resist sucking on her nipples. I got a
good rhythm going and locked onto one of her nipples. It didn't take long and
she shuttered and came.

I carried her over and laid her in her bed. I started to get

undressed and she asked me what I was doing. I said “it's my turn now.”

 She said; “I’m not very good at hand jobs.”

 I said “that’s okay; I had something else in mind.”

 She got a concerned look on her face and I said “don't

worry, I am going to use your tits.”

 She looked relieved and confused all at the same time. I

picked up the bottle of oil and straddled her chest. I oiled up her tits and
laid my cock between them. I held her tits together while thumbing her nipples
and started to fuck them.

When I really got going, my head started to pop out the top.

She looked down and stuck out her tongue. I wasn't going to make it inside her
mouth, but if she kept it open, she was going to get part of my load. I sped up
and started to bump the head of my cock on the tip of her tongue. That was just
the added stimulation that I needed to finish and I shot three good ropes at
her face. The first one went in her mouth and the other two hit her chin and
pooled on her neck.

She must have swallowed the first shot because she licked

her lips and said “thank you.”

 I asked her what she wanted to clean up with and she said “don't

worry about it,” as she smeared my cum all over her chest.

I was done, although I probably could have gone another

round. I asked her if she wanted anything else and she said “no, but you could
join me in the shower if you want to.”

 Why not, I would love to wash those tits. I spent a lot

more time washing her than she did me, but she gave my balls a nice fondle and
stroked my cock a little. We dried off and got dressed. She gave me a nice kiss
and said “see you in class on Monday.”

Carolyn.

Sarah must have talked to Carolyn because she sat down next

to me at lunch one day and said if you give me a ride home today, I will help
you with your homework. I didn't know what she had in mind, but I was game for
just about anything.

Carolyn was the smartest girl I knew and I think I was

always drawn to her because of that, but she did have a tight little body with
an amazing ass. She has blue eyes and auburn hair that she kept just below her
ears. She didn't exactly graduate a year early, but she finished her senior
year at the local community college.

Carolyn was waiting for me near the main entrance after the

bell rang. I was never in a big rush to leave the parking lot, because it was
always a madhouse and I had almost been rear-ended a few times in the bumper to
bumper line on the driveway. My stereo was shit, but we sat there listening to
some music in my car until the parking lot cleared out. She lived really close
to school, so a few minutes meant nothing.

We got to her house and she said today is the best day

because everyone else is out. Word must have gotten around because she led me
to the kitchen and handed me a Mountain Dew and then offered me a sandwich. I
accepted and she got right to work making it. She didn't make anything for
herself, but just sat there and watched me eat. When I was done, I looked up
and asked her what she had in mind. She said that it was time for her afternoon
snack and that we should move to the living room.

She told me; “get undressed and sit down,” as she removed

her shirt and bra.

She knelt in front of me and started rubbing my legs before

playing with my balls and starting to stroke my cock. It didn't take long and I
was rock hard. She leaned in and started licking up and down my shaft. Then she
sucked the head of my cock into her mouth and swirled her tongue around the top
of it. I knew she got a little bit of precum, but she didn't care. When she
started bobbing up and down I reached out to put my hand on her head.

She pulled off and told me to put my hands down. I would get

a chance to use them later. She started bobbing again and before too long, she
was taking everything that I had. She grabbed my balls and started fucking her
face with my cock. I couldn't hold back and shot my load into her mouth. She
gulped it down and kept on sucking until I went soft. She looked up, licked her
lips and said I want a massage. I said you're going to have to give me a few
minutes to recover. She scampered off to the kitchen and brought me another
Mountain Dew.

When I finished that, I said let's go. She gathered up our

clothes and led me to her room. She stripped off her jeans and panties and
showed me a bald little pussy. She handed me a bottle of oil and I proceeded to
give her the same treatment that I gave Sara. When I got to her pussy she told
me that she wanted me to finish her while she was laying down. I decided to lay
down next to her for a better angle and more access. I started rubbing my
finger up and down her slit until her lips parted and I could work my way in to
find her clit.

When I started rubbing circles around it, she started to

squirm, so I replaced my finger with my thumb and started working my finger
into her. I got one in and it felt like there was room for a second. When I got
that one in, she just shivered. I started working both my finger and my thumb,
then I leaned in to suck on a nipple. Her tits were nowhere as big as Sara's,
but they were perky. I kept up the same rhythm until she shuttered and came
with a little squirt.

I was hard again and she reached down to grab my cock. She

got her bottle of oil and lubed me up. She used both hands on my cock and balls
and just kept working up and down, corkscrewing and swirling on the head of my
cock. When I came, it wasn't as much as the first time, but she bent down and
slurped it all up. I must have passed out because she was sitting up next to me
smacking my cheek and telling me that it was time for me to leave. I got up and
got dressed and she took me to the door where she kissed my cheek and told me
to expect to hear from her again.

Carrie-Ann.

When wrestling season rolled around, we got a surprise. My

buddy's older sister Carrie-Ann decided that she was going to wrestle. I didn't
think much of it because I was a heavy weight and she was around 160, but I was
wrong. All of the guys in her weight class refused to wrestle with her. She
wasn't the prettiest girl, but what the hell, if she could wrestle with us, she
would do better at her own weight.

Well, she didn't do all that well with us, because I was

usually riding her ass and when we were standing up, I had her by her wrists so
she couldn't move. We knocked 20 pounds off of her and she wore my fingerprints
as bruises around her wrists for a month after the season ended. I didn't mind
wrestling with her on the mat, but I wanted to take it to my bed.

We had a match the next night and everyone was happy to have

an afternoon off. Because I had been spending so much time with Carrie-Ann, I
thought nothing of asking her what she was going to be doing. She said; “I have
some homework to do.”

 Without really thinking about it I asked; “Could you come

over to my house and help me with an English assignment.”

 She said; “I had heard about helping you with homework,”

and told me that I had better be ready for everything.

The next day after school we headed for my house. She had

driven herself to school so she followed me home. We headed inside, I dropped
my bag and headed for the kitchen. I rummaged around for a snack and drinks.
She was just as hungry as I was.

Carrie-Ann wasn't the perfect girl, but I liked her

attitude. She had worked some weight off, but she was still thick. She had long
brown hair, but she had dreadlocked it for the season. She had bright brown
eyes and a constant smile.

We finished up in the kitchen and headed for my bedroom. We

had not seen each other naked, but our hands had been everywhere, so without
even thinking about it, we both just started getting undressed. We eye each
other up and she said "You're going to let me be on top today."

I grabbed her wrists and asked her if she was ready to

wrestle for it.

 She said "No, you're just going to lay down and take

it."

I was game for whatever she wanted, and I lay down on my

bed. She stood up over me on the bed and just said eat it as she dropped her
pussy onto my face. I didn't know what I was doing, but I just started licking
everything until I got my tongue inside and then she told me; “suck my clit.”

 I was already rock hard and sucked on her until she yelped

and told me; “go easy.”

I pushed her back and told her that this wasn't fair. She

told me that I was never fair at practice. I said “how about you turn around
and work on me while I work on you.”

She put her hands on my chest, spun herself around and

backed her pussy up to my face. She didn't dive right in to blow me, but she
started playing with my balls and gently stroking my cock. I got back to her
pussy and from this angle, I was able to spread her open with my hands and used
my tongue on her clit. When she started to buck her hips, I drove one finger
from each hand into her and latched down hard on her clit. She screamed and
locked up pinning my hands between her legs. When she loosened up, she rolled
off of me and told me that she had won that round.

I said that she could look at it that way if she wanted to,

but I was the one that made her cum. She said “well then, it is my turn to make
you cum.”

 I told her to give it her best shot. What I didn't

tell her was that I had taken care of myself that morning so that I would last
longer with her. She started blowing me, but it was nothing like Carolyn had
done, so I was a little disappointed. She had been down there for a while when
she looked up at me and asked me what was taking so long. I said “if you want
to make me cum, you're going to have to go for a ride.”

Her eyes got wide and I reached over to grab a condom that I

had stashed next to my bed the day before.

 I tossed it to her and told her; “climb on if you want to

beat me.”

 She didn't hesitate, rolled it on and straddled me. I never

expected that it would go this far, but why the hell not. She lined me up and
lowered herself down. When she was fully seated, my jaw dropped open and she
gave me a strange look and then said “is this your first time?”

 I nodded my head and she said; “you asshole, if I had known

that, I would have made it better.”

To be continued in part 2. Based on a post by reader4175,

for Literotica.

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