Hi, I am Alex and this is a story I wrote a long time ago. It was
originally posted under a different title and pseudonym, but I have been
unable to find it (forgot title and name I used back then). I have made
some changes (mainly the ending due to some critiques (thank you)) and
did some other updates and additions to the story since originally
posting it. I have also changed my writing pseudonym and wanted to put
this story under my new name and email. The story is a complete work of
fiction and fantasy, I hope you enjoy it. Any feedback is truly
welcomed and invited, please send to
[email protected].
Chapter 1
As a kid growing up, I lived next door to a beautiful divorcee for about
15 years. Amy was smart, gorgeous and did very well for herself,
owning/managing a catering business. She had married young (18) and
when her husband made a lot of money, he left her 7 years later. Amy
got a good lawyer and got the house, half his business (which she sold
back to him), and a nice monthly alimony check. With the business and
the divorce settlement, she led a comfortable life. Over time, I got to
know Amy well because of her friendship with my parents and she paid me
to do odd jobs around the house for her, like yard work, clean out
garage, take her garbage out, get mail when she was gone, etc. I had a
key to her house and had access to anything or anywhere I needed. On
several occasions, I "surprised" Amy and caught her in various states of
undress. This led to many spectacular orgasms as I relived the moments
privately.
The other great thing about Amy was her nephew and niece, Ryan and
Becky. They were twins and about my age. They visited Amy a lot and we
became good friends over the years. For years, I lived next door
blissfully going about my life, catching the occasional glimpse of Amy's
beautiful body. Then one day things changed. It was a Saturday in
early June, Amy and my mom were lying out in the sun by our pool. Amy
was wearing a skimpy two-piece suit and I could not resist sneaking
peaks of her. Little did I know she caught me looking on more than one
occasion.
As I was relaxing in the pool, Amy turned to me and asked, "Could you do
me a favor?"
Startled and concerned that she had seen me watching her apply sun tan
lotion, I blurted, "What?"
"Can you do me a favor tomorrow??
Waking out of my daydream of massaging her body, I answered, ?Sure.?
?Great, come over tomorrow first thing, and we will get it done
quickly.?
?OK-? I got out of the pool and I ran to my bedroom. I needed to take
care of my boner.
The next morning, I headed over to her house and let myself in through
the garage. As I came into the kitchen, I found her standing there
wearing a short kimono. Her legs were bare and the top of the kimono
was open just so, allowing me a glimpse of her perfect breast. I
instantly became hard.
?Good morning,? Amy said.
As I stared, I mumbled ?Morning. So what do you need me to do today??
?Well, I need to ask a special favor, something a little different from
what you normally do.?
Amy has been very good to me, never doing me wrong, so I naturally
replied, ?Sure, anything.?
?Well before you commit, let me tell you what I need. I am making a
dress for Becky, for a dance she is going to. I need some one to stand
in as a model as I pinned it and so forth. Will you do that for me??
Shocked, I stood there just staring at her. Finally, I said, ?I don?t
know? seems kind of strange. I don?t think so. I can?t do that.?
She pushed a little and said, ?Please?!?! No one will know. Just you
and me.? At this point she turned back to the counter giving me another
glimpse of her breast. ?I tell you what. I saw you staring at me
yesterday? she turned quickly towards me ?and now!!?
?No, I..I..I w..w..wasn?t staring.?
?Yes you were and I don?t mind, it?s rather flattering. But if you do
this for me, you can feel them as well as stare at them.? Now at 16 I
had touched a few teenage breasts but only on the outside of a bra or
shirt and here was a real woman saying I could touch her breast.
?Only, if I get to go first!?
?OK? was all that she said before she dropped her robe on the ground and
stood there naked from the waist up. At 26 her breasts were perfect,
very perky and firm with little reddish brown nipples and areolas.
After taking in the magnificent view, I reached out to place my hand on
her left breast. Before I could touch it though, Amy took my hand in
hers and guided my hand to her chest. With my hand on her breast, I
lightly squeezed it, then moved to tweak her nipple. ?Would you like to
suck on it?? was all the prompting I needed to lower my lips to suckle.
As I softly nibbled her nipple, she began to moan and squirm slightly.
Amy step back to lean against the counter and pushed to keep my lips
locked on her nipple. As I did this I felt my cock growing in my
shorts. After about five minutes of playing in the kitchen, Amy
abruptly halted the action and pushed me back.
As she gathering up her robe, she said, ?OK, shall we do this?? and
headed for the stairs. ?Come on big boy, pay time for your fun.?
Being 16 and male, I though big boy was referring to my penis and was
embarrassed to find it pushing out my shorts. I hesitated before
running up the stairs behind her.
When we got up stairs, Amy led me into her spare bedroom/hobby-room.
Then, with a hint of command behind her words, she said, ?Take off your
clothes.? When I hesitated, she said, ?Come on now, you got to play
with my breasts, so it is time for you to hold up your side of the
bargain. Now strip.?
?But you?re here.?
?So!! You got to see me half naked. Besides, you will still have your
underwear on, what?s the big deal. Hell, I?ve been to your swim meets,
that little suit you wear for that leaves little for the imagination.
It probably covers less than your underwear.?
I thought about and she was right, my boxer briefs would cover more than
my swim team suit. I said, ?OK, you?re right.? and I began to remove my
clothes. Once down to my boxers, Amy lifted the dress and helped me
step into it. She then began doing her thing, pinning it off, measuring
and so forth.
?OK, we?re done,? she announced after 20 minutes.
?Good!?
?Awwww, it was not that bad.?
?I?m wearing a dress, it is bad.?
As she lowered the dress down for me to step out, my hard-on sprung free
of the dress. I quickly tried to hide it by turning, but I think she
still noticed my condition.
As I stepped off the little platform I had been standing on and before I
could even get to my clothes, Amy step toward me. She put her hand on
my shoulder and turned me around to give me a big hug, ?Thanks for doing
this for me, it was a great help.? My 16-year-old body pressed tightly
against her sumptuous 26 year old body. My raging hard-on was
compressed between us, yet she said nothing. As the embrace ended, Amy
seductively said, ?For being such a good sport about all this??she let
the words trail off as she let her kimono slide to the floor. I quickly
lowered my head to lick her breasts. With one hand on her right tit and
my mouth on her left, my hard-on pulsed with excitement. Again, Amy
began to moan. As she pulled my head tighter to her chest, she slowly
walked us into a position with her back against the wall. As she
approached orgasm, Amy pulled my lips up to hers and we began kissing.
My free hand found her available breast and began fondling it. Just
before her climax, Amy?s hand found my cock and gave it several rubs
through my underwear. When she came, it was with a squeal.
Amy stopped rubbing my cock, kissed me gently on the lips and said,
?That was wonderful.? I stood there a raging hard-on in my underwear
ready to explode. Amy picked up her kimono and began straightening up.
After a few seconds I realized I was not going to get to finish, so I
headed into the bathroom to finish what she had started. It took only a
couple of strokes I exploded with the biggest self induced orgasm in my
life. As I recovered, Amy came into the bathroom, I turned but I still
think she saw me with my cock in hand and cum all over it. Without a
word, I finished cleaning up, got dressed and headed home.
Chapter 2
Several days later, I was over Amy?s again cutting down some weeds and
moving a fallen tree limb to the back of her yard. It was a warm sunny
June day and I was getting hot, sweaty and dirty. When I was finished,
she asked, ?Would you like a Coke???
?Sure, thanks.?
She brought two Cokes out to the garage. As we stood in there drinking
the Coke, Amy asked, ?Could you serve as my dress model again? I need
to put the finishing touches on it?? (It did not occur to me that the
true finishing touches would need the actual wearer of the dress not a
stand in model)
?I don?t know. I felt kind of strange wearing a dress.? Playing the
embarrassment card, hoping beyond hope she would make an offer similar
to the last time and I would get to play again.
After giving it a seconds thought, she took a step toward me and
whispered in my ear, ?If you do this for me, I will let you see me
completely naked.?
Without a second?s hesitation, I smiled and said, ?OK! You have a deal.?
?Great!! Thank you so much, this should be that last time I MAKE you
wear a dress.? I did not catch the little emphasis on ?make? as we
headed into the house. When we got to the hobby room, she took one look
at me and said, ?You are too dirty to put on the dress. You need to
take a shower first and wash off all the filth, I can not have the dress
getting dirty.? As I turned to walk out the room, she asked, ?Where are
you going??
?Home to take a shower.?
?Don?t be silly, use my shower.?
?You sure??
?Yah! Why should you go home when there is a perfectly good shower
here??
?OK, I will take one here then.? I headed toward the bathroom attached
to the room. I closed the door and removed my clothes. I turned on the
water, let it warm up and stepped into the soothing stream of water. As
I stood there with my eyes closed, I let the hot water cascade down my
body and thought about getting to see Amy naked. These thoughts led to
an erection. Little did I know, Amy had walked into the bathroom and
was watching me stroke my 7? of hard manhood. As I got close, Amy
abruptly made a noise like she had just entered the room. I quickly
turned away from her and took my hands off my cock. ?What?s wrong?? was
all I could manage to say.
With a smile on her face, Amy replied, ?Nothing, I just brought you a
towel to use. The towels in here are decorative. When you are done
with that, just come out with a towel wrapped you. I?m going to wash
your clothes so you can put them back on later.?
Because I was trying to hide my boner, I was not paying a great deal of
attention to what she said and answered, ?Uh, uh, OK?Thank you.? With
my back turned to her, I did not see her pick up my dirty clothes. Once
I was done showering, I stepped out and was drying off when Amy came
into the bathroom again. Startled, I inadvertently dropped the towel,
exposing my soft cock.
As I tried to cover myself up, Amy apologetically said, ?Oh, I?m sorry,
I didn?t think you would be done so quickly and I needed to put these
things under the sink.?
Standing there, butt naked with my hands in front of my manhood, I said,
?It?s OK-? After giving me a quick glance, she smiled, turned her back,
and then held up a pair of boxer shorts.
?I figured you needed something to wear, so I brought these in. I
bought these for Ryan, but never gave them to him. You can wear them
while your clothes are in the wash.?
?In the wash?? At that point, I looked down and realized my clothes
were missing.
?I told you I was going to wash them when I came in last time and you
were trying to hide yourself. You know, I have seen a penis before, it
is no big deal.?
?Oh,? was my only response. I took the bright red silk boxers from her
and she exited bathroom. I dried off and pull the silk boxers up my
legs and over my ass and cock (this was the first time I ever had silk
against my cock and ass). The feeling was luxurious and once again gave
me a woody. I decided I should take care of this before I went out
there. So I proceeded to jack off in the boxers. With the silk rubbing
my cock, I quickly approached climax and pulled down boxers to shoot my
wad into some tissues. I did not realize the door was not completely
closed and Amy watched me stroke my rod to finale in the mirror. I
finished cleaning up and strutted into the bedroom wearing the bright
red boxers.
?Great, now you won?t get your dress dirty.? Completely missing her use
of ?your,? I stepped toward her and turned around. Amy then helped me
put on the dress. Once it was on, I stepped up onto the little platform
she had. Amy began doing her thing, but I could quickly tell from her
mumbling, something was not right.
?What?s wrong?? I asked.
?Well, the dress is not ?hanging? right.?
?Hanging right??
?Yah, it just does not seem to be ?laying down? they way it should.?
?Why??
?I don?t know, but hold on.? She looked me over, had me turn around,
and then ran her hand over the dress and my body (getting me very
excited). Then, all of a sudden, she says, ?I know what the problem
is.?
?What? Is it fixable??
?It?s fixable, but I not sure if I can ask you to do what it will take
to fix the problem.?
?Why? What more could you ask of me that you think I would say ?no? to.
You already have me in a dress.?
?Well, the dress is not hanging right because you are wearing boxers
under it.?
?So??
?Well, there is only one way we can get the dress to ?hang? correctly.?
?OK, how do we do it??
?We need to get rid of those boxers.?
?Get rid of them?? How???
?Take them off.?
?Take them off?? Are kidding me???
?No, it is no big deal, you are covered.? And with that, she reached up
under the dress and began pulling down my boxers. Once they were all
the way down, I stepped out of them. When I straightened back up, my
boner poked out the front of the dress.
?Oh.? Was her only response. Looking down, I became quite embarrassed.
Amy stifled a little laugh and said, ?Well that presents a whole new set
of problems.?
Still mortified that she knew I was hard, I meekly said, ?It was the
silk. What do we do now??
?Well ummmm. I know. I?ll just get your underwear out of the laundry
and those should,? Amy cleared her throat, ?contain you.? Again, she
stifled a laugh and left the room. Amy headed for the laundry room. I
stood there trying to think of baseball to get my erection to subside.
When she returned, she was empty handed and had a frown on her face.
?Your underwear is still in the washing machine, soaking wet.?
?No big deal, I will just run home and grab another pair.?
?What are you going to wear, all your clothes are in the wash??
?Shit, you?re right. And there is no way I can go outside wearing
this.? I pointed to the dress. Finally after thinking about it for a
moment, I said, ?Well, I don?t have an answer.?
?That?s OK, I will just have to do it another time.? She lamented.
As she sat on the bed thinking, I said, ?I promise to work as your model
one more time and you don?t have to hold up your end of the deal for
today. I won?t hold you too it.?
?Well thank you John, that saves me from having to ask again, but I
insist on finishing our deal. You held up your end. You put the dress
on. You deserve to be ?compensated? for that. Sit down on the bed.?
Amy then stood up, and began to get undressed. She took off her shirt
and lowered her shorts to the floor. She stood there like a goddess in
her pink lace and satin panties and bra. I was mesmerized. She slowly
undid the front latch to her bra to free her beautiful breasts. Then
she bent over to remove her panties. When she straighten back up, it
was more than I could handle. Here was a beautiful women, completely
naked standing within arms length of me. I just stared. Her size C
breasts poked proudly out with her nipples like little crowns on the
end. And then her pussy hair, neatly trimmed into a heart shape
glistened with vaginal juices. I was speechless. ?Let?s get you out of
that dress.? In my mesmerized state, I obediently stood up and let her
unzip and lower the dress to the floor. I just stood in all my glory,
all 7? of little John poking up to the sky. Amy looked down and saw my
boner, reached out and began stroking me. At that moment, I broke from
my dream state and become aware of my surroundings and what was going
on. The sensations of Amy?s hand on my cock though made me forget my
nervousness and I made no attempt to touch her as she expertly handled
my cock and balls. After about two minutes, my excitement had built to
the edge of climax and she stopped.
Amy let go of my cock and turned away from me. With her back to me and
a smile on her face she said, ?Well thank you John for all your help.
Hopefully we can work out all the details next time and get this
finished.? She headed toward the bedroom door.
Not knowing what to say, I just said, ?Yah that will be great.?
Walking down the hall she said, ?Put on the boxers and I will get you a
beach towel, you can go home like that and change clothes at home. When
your clothes are done, I will bring them over.?
I slipped the boxers back on just as she re-entered the bedroom, dressed
in shorts and a shirt. She handed me the towel, and led me toward the
front door. With a small kiss on the cheek, we said goodbye and I
headed home.
At home, I still had a raging hard on and the image of Amy in my mind.
I went straight to my room to take care of my hard-on. I slid my cock
out of the fly in the boxers and proceeded to jack off. After about
thirty seconds I exploded all over myself. After cleaning up, I headed
out to the pool.
Chapter 3
A couple of days later I was out swimming in the pool when Amy came up
to the gate.
?Hi John.?
?Hi!?
?What are you up to today??
?Just hanging out and swimming.?
?Could you help me with something over at my house??
?Sure, let me get a towel.? I climbed out of the pool and dried off,
threw on a t-shirt and followed her over to her house.
?This will be easy, I just need to get a couple of things out of the
attic. I will go up and hand them down to you.?
?OK, no problem.?
When we get into the house I followed Amy upstairs. Amy was wearing a
pair of tight, powder blue shorts and a white t-shirt. Neither of which
did anything to hide her sexuality. With my eyes glued to her ass, we
head into the hobby room. Laying on the bed is the dress with a couple
of boxes next to it. We headed over to the corner and she used a chair
and a boost from me, to get into the attic. She hands me down several
boxes of clothes; all of them are marked ?GIVE AWAY-?
?What?s all this stuff??
?Oh, just old clothes I am giving away to charity.?
?Damn, you have a lot of old clothes.?
?Oh, well, I am a woman with means. Can you help me down?? With her
legs dangling from the attic entrance, I place my hand on her calves to
guide her down. Amy lowers herself from the attic as my hands run up
her legs to her ass and then her back. We stood a moment pressed
tightly together. ?Thank you for your help.? She said as we split
apart. This little contact made my cock rise in my swimsuit.
?No problem, anytime.?
Amy just smiled. Then pretending to notice the dress for the first
time, she turned to me and asked, ?How about we finish that dress
fitting? I will honor our deal from last time.?
?Ok, why not.?
?Great I can get this done and move forward with my plans.?
?Where should we start??
?Well let?s get you in the dress. Take off your shirt and shorts for
me.?
I strip out of my shirt while Amy grabs the dress. She is standing
there waiting for me to remove my shorts, when I realize I have on a
swimsuit. I do not have any underwear on. ?Uh, problem.?
?What??
?No underwear again, these are a swimsuit.?
?Shit, I was really hoping to get this dress done.?
?Sorry, I wasn?t thinking.?
?Not your fault.? She stood there for a moment then said, ?I got an
idea. That is if you are willing.?
?What is your idea??
?Now hear me out before you say no. I really need to get this dress
done ASAP. In addition to the dress, I have bought, shoes, stockings
and other lingerie for Becky to wear. If you were to wear the underwear
I bought, it will solve the problem and I can finish the dress.?
I immediately said, ?No way! I don?t think so. I?m not going to wear
girl?s underwear.?
?Hold on. Before you say ?NO?, please listen to the rest of my deal. I
really need to finish this dress, therefore, if you wear the lingerie, I
will not only let you see me naked, I will let you touch me anywhere you
want.?
Wow, I sat there stunned and thought about what she was offering. I get
to see her totally nude and play with her tits and pussy (my first)!!
After several seconds of thought, I slowly said, ?OK, but it gets to be
longer than the last time.?
?Wonderful!!? She step toward me and gave me a kiss on the lips, ?It?s
a deal. Let me go get the lingerie.? As I sat there thinking how lucky
I was, she leaned over the bed, placing her ass right in my face, and
grabbed the first box next to the dress. She opened the box and began
removing items. First came a pair of silky pink panties with black lace
trim. Then she removed a matching bra and garter-belt. Next came a
pair of white stockings and she laid them all on the bed. .
What did I get myself into? I said, ?I thought you said it was just
underwear??
?Well, girls wear more that just panties for underclothes. I figure you
only want to do this once, so I got it all out. That way we can get it
all right without having to do it again.?
Quickly thinking her statement through and seeing the logic, I said,
?Ummm, ok, I guess it is worth it and a deal is a deal.?
?Well put these on while I go change clothes.?
?OK.? Amy left the room as I pulled my swimsuit down. Just as I step
out of them, she ducked her head back in the room.
?If you need help just holler.? I stood there in my birthday suit
trying to cover up my 7? of hard cock. Amy disappeared again and I
picked up the panties. What I did not know, Amy was actually watching
me from the hall using a mirror in the room. I quickly pulled the
panties up around my ass and they fit perfectly, except for my 7 inches
pushing on the front.
As Amy returned, having changed into yoga shorts and a looser top, she
took a quick glance up and down and said ?Good they fit. Now turn
around so I can help you with the brassiere.? Happy to be able to hide
my hard-on from her, I turned my back to her and she helped slide the
bra up my arms and attached it in the back.
As she reached for the garter belt, I asked, ?What is that for??
?It is a garter-belt, it will hold up the stockings. Now turn around so
I can put it on you.? She put the belt around me and attached it in the
back. ?Sit on the bed. It will be easier to put on the stockings with
you sitting down.? As I sat on the edge of the bed, Amy knelt down in
front of me. From this angle I got a great look down her shirt at her
tits (and she got a close up of my 7?s, but I did not think about
that.).
Amy rolled the stocking up and slid it over my toes. She then slowly
unrolled the stocking up my leg until she reached the middle of my
thigh. She then repeated the process with the other leg. Between the
view of her tits, her sliding the stockings up my legs and the feel of
the stockings, my hard-on began to ache and a little pre-cum dribbled
out into the panties. Once she had both stockings on, she said ?Stand
up so that I can attach them to the garter straps.? As I stood, my
panty covered cock was right in her face, I could hide neither my hard-
on nor the wet spot, but she said nothing. She attached the stockings,
stood up and stepped back. She stood there looking at me, ?Do a spin
for me.? I did a slow spin for her.
She smiled but said nothing (not even about my hard on). Then she said,
?Something is missing. Oh, I know what it is! Stay right there.?
?Where am I going to go dressed like this?? She ran out of the room and
returned with what looked like a pair of socks.
?What are the socks for??
She laughed and said, ?These are not socks; they are my little secret.
They are silicone breast enhancers. I use them when I wear certain
clothes, clothes that need me to be a little larger up top.? My mouth
just hung down, thinking no way she had to ever pad her bra. She fit
them into my bra and now I had tits. It was obvious how this was
effecting me, I still had a raging hard on. I kept putting my hands in
front to hide it, but Amy still made no mention of it.
?OK, now for the dress.? Amy held the dress open while I step into
it... She then carefully pulled it up over my shoulders while I slide
my arms under the straps. As she zipped me up with one hand, she hands
me a pair of heels with the other. I step into the 2? heels and
instantly I was almost 6?. ?Great, now let?s get to work.? As I stood
there on the little stage, Amy began to fuss over the dress. After
several minutes of pinning and primping the dress, she had me turn
toward the mirror. I got my first glimpse of John in a dress. At first
glance, it was a young lady, but as you came up to the face, it was a
young man dressed up like a girl. I was mesmerized by what I saw. As I
stared, Amy continued working on the dress.
When she had completed what she was doing she stood behind me and said,
?You know with a long hair and a little make up, you would make a very
cute girl.?
?Shut up, no I wouldn?t. I couldn?t fool anyone.?
?Oh, I don?t know about that.?
Amy finished with a couple of pins toward the top and asked me to do a
couple of turns to see how it flowed. Going into my own private world,
I began to wonder if I could fool people. I began to do some turns as
she requested and followed a few other directions she gave. I never
noticed her taking pictures as I stood there in a trance. Finally, a
flash from her camera broke my trance.
?Why did you do that???
?I want to take a couple of pictures to send to Becky, so she could see
it.?
?No way. You said no one would know, if there are pictures, people can
find out. No Pictures!?
?Please! It would really help me.?
?No way! No pictures.?
?I tell you what. I will cut your head out of the pictures; no one will
connect them to you. Let?s face it, you have tits in the picture, no
one would even suspect you.?
?What about developing? People there will see them and maybe make
copies.?
?It is a digital camera, I print them on my computer.?
Mulling it over and running out of excuses, I said ?OK, but make sure
you cut my head out-?
She proceeded to take pictures, having me turn this way and that, taking
close-ups and distant shots. After what seemed like 100 pictures, she
said, ?OK, that?s enough? and put the camera down. During this whole
time, I was hard as can be and almost creamed in the panties. I stepped
down from the platform and walked over to the mirror to look at myself.
It was amazing. Amy came up behind me and put her hand on my shoulder
and smiled. She said, ?You know what would be fun to do??
?What??
?Well, I have an old wig somewhere and if I put some make-up on you, I
bet you would make a very cute teenage girl. Let?s see how John the
teenage girl would have turned out.?
?I don?t know. It all seems so strange. Who cares what I look like as
a girl??
?Come on, no one will know and it will be fun, I promise to help you
clean it all off. Plus I still have to fulfill my part of our deal.?
Amy played with her top flashing a breast.
Without saying it too quickly or excitedly, ?OK, but nobody sees me and
you make sure we get all the make-up off.? Amy smiled, and reached into
the closet.
When her hand came out, it was holding a square black box. With a flick
of her wrist, the box was on the bed and the wig was in her hand. She
picked up a brush from the dressing table and began brushing out the
wig. She then step very close to me and place the wig on my head. I
failed to notice (being a guy) that the wig miraculously matched my
natural hair color. Once she had the wig in place, Amy turned me toward
the mirror. The reflection I saw was a teenage girl staring back at me.
It was utterly amazing, even without the make-up, I looked like a girl.
?You are beautiful. Even without make-up you make a pretty girl.?
?No, anyone can tell I am just a boy in a dress, no one would ever
mistake me for a girl. I have facial hair and I am way tall in these
heels.? But in my mind I was thinking ? damn, she is right, I am very
cute, I?d fuck me if given the chance (but then I was a 16 year old
boy).
Amy broke into my daydream and said, ?Let?s go to my room to put on the
make-up.? I followed her shapely ass into her room. As we walked down
the hall, Amy just smiled and cooed over how much fun this was going to
be.
As we enter the room, I was shocked with how austere the room was. I
expected Amy to have a very feminine room, but in reality it was very
architectural in design, crisp lines, hard corners, deep rich colors,
very sexual. The room first struck one as masculine, but after a
moment, one would definitely find it feminine, just not in a
pinkish/girlish way. It was very adult feminine.
Amy led me to her make-up table and began pulling out various types of
make-up. I was amazed at all the different types there were, ?How do
you know what to use, there is so much??
?It is something you learn over the years and you can go to people to
get your ?colors?-? She started with some foundation, then eye shadow
and mascara. Next came some blush and finally she opened a ruby red
lipstick and applied it to my lips. As she made me pat the excess off
my lips, she reached in a drawer and pulled out, a necklace, a bracelet
and a pair clip-on earrings. She stepped back and just stared, almost
speechless. ?You?re gorgeous!! It is amazing, I never would have
guessed you would make a very cute and sexy young lady.?
?No way, I am a guy, how can I be cute???
?Well you are, let?s go back to the mirrors and prove it.? We headed
back down the hallway to the hobby room. ?OK, close your eyes.? She
led me in front of the mirrors, ?Now open!? I just stood there
awestruck. It was amazing; a very attractive teenage girl was staring
back at me from the mirror. While I was engrossed with myself in the
mirror, Amy took up her camera and began taking pictures, from behind,
from the side and from the front.
After about five minutes, the spell broken, I said, ?Stop, No Pictures.
Don?t take any pictures!! You do not need anymore.?
?OK, gorgeous. You look beautiful in your dress though.? She put the
camera down (though setting it to continue taking pictures). I just
stood there staring at the mirror, turning side to side and to the back
to get a complete view. ?You are beautiful.? I blushed but said
nothing; I stood there just mesmerized and hard as a rock in the
panties.
After another 5 minutes of looking at myself, Amy broke the spell, ?Time
to take off your dress.? I sighed a little as she stepped over to me
and unzipped the dress. She then helped me step out of it and hung it
on the door. I again turned toward the mirror to look at myself. This
time I saw a young girl in lingerie, with a raging 7? hard on straining
to break free. A wide wet spot had formed on the front of my panties.
Amy stepped up behind me while pulling her t-shirt over her head. With
her breasts pressed firmly to my back, she began kissing my shoulder. I
stood there watching us, watching a beautiful woman kiss the body of a
teenage girl. I soon saw her shorts drop to the floor and felt her
hands slide around my stomach.
After several minutes of her attention and me watching in the mirror,
she stepped away from my back. ?Why don?t you turn around and check out
my end of the deal.? As I turned to face her, Amy stood there, a
goddess with a perfect body - 34C breasts, 25 waist and 34 hips, toned
and tanned almost completely over. She reached for my hand and placed
it on her right breast. As I gently squeezed, a moan escaped her lips.
I began playing with her nipple, teasing it, make the nipple surge out
for flesh. With one hand fondling her breasts, Amy guided the other to
the promise land. As my left hand found her pussy and she directed my
finger between her lips. A slight gasp gushed from lips as I slid my
finger forward into warm, moist love box. I lowered my tongue to her
breast and licked like a child to an ice cream cone. Amy?s sexual
mewing continued.
There we stood, a beautiful goddess, eyes closed whimpering in ecstasy
and me, barely a man of 16, wearing pink lingerie, my hand in her pussy.
As I lifted my head, our mouths found each other and entered in a deep
soulful kiss, tongues dancing in and out in a dual of lust. With the
intensity of her whimpering increasing, I introduced a second then third
finger. My free hand once again finds a luscious breast and begins to
tease and play with her nipple. As my hand did a walk through her
pussy, it seemed to generate deeper, lingering moans from her body. She
whimpered as I removed my hand from the joy it had found and gasped as I
pushed it hard back into heaven. Amy came with a loud squeal. As I
removed my hand from her love canal, Amy pulled our bodies together,
grinding her pubes into my groin. Just the slight added stimulation
caused me to cream in the panties. My body quivered with orgasm and I
was barely able to remain standing. Abruptly, Amy stepped away from me
and matter-of-factly stated, ?Ok, that completes our deal. Time for you
to be headed home.? I stood there dazed, dumbfounded and at a loss to
say anything.
Slipping on a robe, she said ?I?ll be right back, want a Coke? Sit down
on the bed and I will help you take off your stockings without getting s
run in them when I get back.? I sat down, and then laid back on the
edge of the bed. My hard-on gone but the panties obviously wet with
cum. After about 10 minutes, Amy came back into the room with the
Cokes. Without saying a word, she unhooked the first stocking and began
rolling it down my leg, following that with second leg. With her hands
on my legs and the several glimpses of her tits to bring it on, my
raging hard-on returned. Still horny and embarrassed, I tried to hide
it when she stood back up. As she looked down at me she said, ?Oh my,
what is this? Did I do that to you? Does little John like playing dress
up??
?NO, NO, I Don?t!? I said a little too emphatically, ?It?s just, you
are beautiful, practically naked and you just kept rubbing my legs?? As
I said this, she started to lower the front of my panties. I tried to
push her away, but she pushed my hands aside and proceeded to release my
cock from its lacy confines.
In a cutesy, playful voice, ?What is this all over the inside of Becky?s
panties? Did wittle John get all excited wearing panties and have a
wittle accident in his panties???
Mumbling, I shook my head and said, ?I?ve never done that before, all
you did was touch me once and I could not stop it; you were too much.?
Trying to hide my face.
With just my cock hanging over the waste band, Amy said, ?Well we will
just have to clean this up.? She then proceeded to lick the shaft of my
cock clean and then lowered her mouth to swallow me in. She sucked it
all the way in, licking the underside with her tongue. As I lay there,
she cleaned my cock of all the cum. As she lifted her mouth off my
cock, she grabbed my hand and said, ?Stand up.? Not wanting her to stop
the fun, I stood up as she asked. She then lowered the panties the rest
of the way. I stepped from them and she laid them on the bed. Amy then
kneeled down in front of me and took my cock in her mouth again.
I looked over in the mirror and saw an amazing site. Amy in a kimono,
on her knees, sucking my cock and me wearing a pink bra and garter-belt
(the straps hanging down on my ass and legs) with my 7 inches buried in
her mouth.
Amy licked and sucked my cock for about 5 minutes as she played with the
garter straps and my ass. I was all a shiver with the multiple
stimulations. It took only 2 more minutes before I blew my second wad
of the day. Amy caught every last drop. With rubber knees from the
orgasm, I fell back on to the bed in ecstasy, my very first blowjob.
Amy climbed up next to me on the bed and ran her fingernails up my body.
I turned to look at her and she leaned over to kiss me. As we kissed, I
felt her tongue on my lips. As my lips parted to receive her tongue, I
was given my third surprise of the day. Not only did her tongue pass my
lips, but so did the cum she had just sucked from my cock. Simultaneous
to our lip lock, Amy began stroking my cock as she rolled up over me.
Amy kept her lips forcible against mine, not allowing me to get rid of
the cum. Finally, after a few moments of tongue games, I swallowed my
cum.
After swallowing my cum, Amy directed my hand back to her pussy and I
started fingering her again. As we rolled around on the bed, we
continued kissing and playing tongue games with our mouths. I continued
to finger her very wet pussy. Amy reached above her head and grabbed
the panties I had spewed into earlier. After rubbing my cum all over
her breasts, she looked me in the eyes and said, ?Suck on my tits baby!!
Lick your cum off them,? With the invitation, I began to lick her tits
and I cleaned my cum off of them. While I licked and sucked her
beautiful 34Cs, I was adding fingers to her pussy. Amy then showed me
how to use my thumb to pleasure her more effectively. With my continued
attention to her breasts and my quick learning of the thumb technique,
Amy began whimpering. As her breathing got faster, she took my cock in
her hand and began stroking. As she blew in orgasm, she let go of my
cock and screamed in ecstasy,
After a couple of minutes of recuperation, Amy rolled over and said, ?It
was time for you to go. Just put your lingerie on the bed and I will
take care of it later,? and then she left the room.
As I stripped out of the rest of the lingerie it occurred to me that she
called it my lingerie, I figured it was a slip of the tongue and thought
nothing of it, I was still on my sexual high. I laid all the lingerie
on the bed and was standing there naked when she returned to the room
wearing her kimono. She came up to me and kissed me. ?You were
wonderful. I have not been that hot in a long time. I just love the
feel of silk and the way those straps dangled, ummmmm.? As she was
saying this, she fondled my cock again and gave me another big kiss.
?Now get dressed. I should not be seeing you naked.? I got dressed in
my street clothes. She then handed me some make=up removal towelettes
and helped me clean off the make-up... Once done, she grabbed me,
pulled me to the bed and gave me a big French kiss while she stroked me
through my jeans. The kiss broke and Amy said ?Thank you again for
being my model and for being such a good sport about everything I
needed. It was fun playing dress up like you were my daughter. I hope
you had fun too for a one-time deal. Bye, and tell your mom and dad, I
said ?HI??
I said, ?C?ya,? and walked out of the house.
Chapter 4
Other than normal work life, working around the yard, swimming at the
pool and a few glimpses of her body, nothing untoward happened for the
next week. Amy had gone away for a 10-day cruise. While she was gone,
I was going to stay at her house to make it look like some one was home.
As I stayed there, I took the opportunity to explore her house. I found
a few things and learned a little more about Amy. I was also able to
have a couple of small parties with some friends and we hit her liquor
cabinet kind of hard. The day she got back, I went over to make sure
everything was in order and OK.
As I came in through the garage, I caught her kissing this gorgeous
woman at the front door. Now the kiss was not of a sensual/sexual
nature, but it was more than just a Good Bye kiss. ?Oh, Hi Johnny!!?
(She is the only one who calls me that and it had only been during our
playtime that one day.) ?This is Tina, she was my cabin buddy on the
cruise.?
?Hi, Tina, nice to meet you.? And it was, Tina was about 29, blonde
hair, blue-green eyes, 36C, 26, 35.
?Nice to meet you too Johnny. I have heard a lot about you. I wish I
had some one to help me like you assist Amy.?
Concerned Amy told her what we had done, I blushed and asked ?What do
you mean??
?Well I live alone too and it would be nice to have some one to help
take out the trash, do the yard work, and take care of a few things
around the house as needed. Everyone in my neighborhood is older.?
?Oh, where do you live??
?I?m about 2 hours south of here. Well Amy, I had a lot of great time
and we need to get together more often, call me let?s get together real
soon.?
?OK, we will and I did too.? Amy replied with a smile on her face.
?Bye-bye Johnny. Keep up the good work.? With that, Tina, walked out
the door.
I said ?Bye.? As I watched her ass all the way down the walkway.
I turned to Amy and said, ?Welcome back. Just stopped by to make sure
everything was in order.?
?Yes, everything?s in order. Now, I have a special thank you. Follow
me...? I followed her upstairs staring at her luscious ass the whole
way. Without saying another word, she led me to her bedroom where she
proceeded to kiss me. As she unbuttoned her shirt, my hand found its
way to her breast and began massaging it. Amy slowly led us over to her
bed as we kissed. Then without warning she pushed me and I fell back
onto the bed. Amy then yanked my shorts down to my knees and took my
hardening cock into her mouth. As I lay there receiving another
blowjob, her hands explored my body taking extra time on my balls and
ass. As I approached climax, Amy took control of the situation and
slowed her motions, expertly backing me down from the point of
explosion. Amy slid her mouth off its ?lollipop? and climb up onto the
bed. She positioned herself where I would have access to her pussy and
said, ?Take my panties off, Johnny.? I reached under her skirt and
slowly pulled her panties down to her knees. I had them at her ankles;
she kicked them into the air and grabbed them with her hands. With
panties in hand, she grabbed my 7 inches and began stroking me with the
panties. The electricity raced through my body and I involuntarily
shivered. As she continued her ministrations, I slid my hand up her
skirt and slid two fingers into waiting pussy.
When she was wet, Amy looked me in the eye and said, ?I want you to lick
my pussy.? With that, she pulled up her skirt and straddled my head,
dropping the skirt over me. At 16 I had never done this and though it
smelled a little bad, I thought - hey I was getting some action from
this beautiful woman and I will do anything she asked to keep it going.
So I began licking her pussy. Amy coached me by giving some directions
and pointers to improve my technique. After a couple of minutes, I had
her moaning in delight. Amy then lifted herself up and reached into
the bedside table. She pulled out a vibrator I found during one of my
explorations while house sitting. As Amy lowered herself back toward my
waiting mouth, she put the vibrator into my hand. ?Slide this in me
while you lick.? I slid it into her pussy and proceeded to start
licking again. ?Turn it on you silly.? The instant I turned it on, she
went active. Amy began riding my face, I just held out my tongue as she
moved back and forth. After about 90 seconds of this, Amy was ready to
cum; she settled into my mouth and started screaming, ?Lick me! Lick
Me!? So that is what I did. Amy?s orgasm came in a rush. It was
amazing. Her body convulsed as I licked her pussy. I never knew women
could orgasm this big and long. After what turned out to be four
minutes of multiple orgasms, Amy collapsed on top of me. I turned off
the vibrator.
Once Amy recovered, she went to work again on my cock. With the panties
covering my cock, she engulfed it. She then worked my cock out a leg
hole and went to town giving me a blowjob. While she sucked, she used
the panties to tease my balls; she also began teasing my backside with
her free hand. As I approached climax for the second time, Amy did not
falter. But she did surprise my by forcing her finger into my ass. The
instant she pushed in, she pulled her mouth off my cock and I climaxed.
As the cum shot out of my cock, Amy caught it with her panties. I had
just experienced sheer ecstasy and I lay there completely fulfilled.
As I lay there recovering from the incredible sexual experience, Amy got
up to change her clothes. As I watched her remove her clothes, I
realized what how sensual an act it could be (not like a bachelor party
stripper). It was erotic to watch her; I was completely turned-on and
already getting hard again. When she was finished dressing she asked,
?Did you enjoy that? Watching me change my clothes??
?It was the most amazingly erotic event I have ever witnessed.?
Amy knelt next to the bed and began running her hands up my bare legs,
right toward my hard cock. Once there, she began playing with it again.
As she fondled my cock, I sat up and we began kissing, my hands quickly
found her breasts and began to fondle them gently. Abruptly, she
stopped my fondling and said, ?Lie still. Don?t use your hands?. Just
do what I tell you to do.? With that she pulled my shirt off leaving me
completely naked. ?How would you like a massage??
?Uh, sure, I would love one.?
?Ok, roll over on your belly, Johnny.? Once I rolled over, she began
giving me a massage. She started with my back, then my legs and
finished up on my ass. All this touching did nothing to relieve the
hardness of my cock. About 10 minutes into the massage, Amy began
adding little kisses and licks to her ministrations. After another 10
minutes of her caressing my 16-year-old body, she whispered into my ear,
?Roll over, baby.? I did as she directed. As I rolled onto my back, my
cock stood at full mast and she put it right in her mouth.
With my cock in her mouth, she explored my body with her hands. After
about 5 minutes of her continued licking and touching me all over, I
moaned in ecstasy and closed my eyes to enjoy the sensations. With my
eyes closed, I missed Amy grabbing the vibrator and was a little
startled when she applied it to my balls. The euphoria this caused,
sent me into a world of complete bliss. I even missed her lubricating
the vibrator with her tongue seconds before she lined it up for a push
into my ass. I jumped at the intrusion and pain. She giggled and said
?What????
?Well, you kind of surprised me with that. And to be honest, it hurts a
little.? She giggled again and went back to sucking my cock. After
about 30 seconds I settled back in to enjoy her skills. Then she turned
on the vibrator and my body just quivered. Amy?s mouth applied just the
right amount of suction to keep me from exploding to quickly. Finally,
after about 10 minutes of working me over with her mouth and the
vibrator, I shot my second load of spunk for the day. Once I calmed from
my orgasm, Amy deactivated the vibrator and crawled up next to me and
cuddled. Once we were face-to-face, Amy leaned in and French kissed me,
pushing my cum into my mouth again. She did not break the kiss till I
swallowed it. As she laid there looking at me, Amy licked some cum off
her lips and said, ?MMMMMMM-?
Satisfied and recovered, I went back to fondling her tits and fingering
her pussy. As I fondled, Amy shifted her way higher and once again sat
on my face so that I could eat her out. It took only a few minutes of
licking and sucking, for Amy to cum. Her love juices spilled out all
over my face. When her orgasm subsided, she lay next to me and
proceeded to kiss and lick her own love juices off my face, cooing the
whole time. We lay there cuddling and teasing for the better part of an
hour. I completely forgot all about the vibrator in my ass.
When we got up from bed, the vibrator slid out of my ass and onto the
floor. Without making a comment, Amy picked it up and put it in her
nightstand. ?Go wash up, we do not want anyone finding out what has
been going on here.?
I went into the bathroom and proceeded to wash my face and groin. As I
stood there with a huge smile I thought ? what incredible luck, I am 16
and getting laid by a beautiful woman. I finished up and strutted back
out into the bedroom, naked and with another hard-on (I had gotten over
my shyness). Seeing my hard-on, she commented, ?I just love young guys,
so much stamina!!? I just smiled and grab my shirt and put it on. She
held up my shorts and said, ?Here let me help you with these.? So she
got down on her knees and held them out for me to step into. I step
into them and she began to slowly pull them up my legs. As she got near
my cock, she stopped, kissed it, and then swallowed my cock again. She
rapped her arms around my ass and began to really pull me toward her,
moving my whole body to the rhythm of her licking. I started moving
back and forth. I began to fuck her face furiously. She again reached
down and picked up the vibrator, running it over my cock and balls and
ass as she sucked. At one point, she had both my cock and the vibrator
in her mouth, now that was an awesome sensation. After pulling it out
of her mouth, she slid the now lubricated vibrator into my ass. I did
not jump this time. After a few minutes of fucking her face, I blew my
third load of the day, which she promptly swallowed. She then stood up,
pulling my shorts the rest of the way up and kissed me, allowing just a
taste of cum on her lips. ?Sit down on the bed for me.? I sat.
At this point she proceeded to get dressed. She pulled on a pair of
navy blue silk panties with black lace trim, then a matching bra (I
finally learned how girls put bras on by themselves). She then put on a
t-shirt and a really short skirt. She walked back over to me and kissed
me. With the great view of her chest, I was once again getting a hard-
on. Upon noticing this, Amy said, ?You must like watching me get
dressed as much as you liked watching me get undress.? I shrugged, not
taking my eyes off her legs. We walked back down stairs and got a Coke.
While sitting there talking and drinking our Cokes, Amy got out her
digital camera to show me the pictures from the other day. She showed
me about 20 pictures, each where she removed my face from them (I
quietly said a thank you, forgetting that she took a hell of a lot more
pictures). I looked at the clock and said, ?Well time for me to go.?
?Let me get your money for your work this past week.?
?You don?t have to pay me.?
?Yes I do. Besides, I had fun today too.?
?OK, if you insist.?
Amy handed me $200 and leaned over and kissed me, ?Thank you for all the
work you did while I was gone. It is nice to have some one to count on
to take care of these things.?
Chapter 5
Over the next few days Amy had several projects she wanted to complete
and I helped her out with them, but we did not play anymore, only a
small kiss here and there and sometimes a quick shot of her breasts.
Then one Wednesday in late June, Amy asked, ?Would you like to see the
finished dress, I finally got it done??
?Sure, why not.? We went inside and back to the hobby room.
Amy pulled the dress out of the closet, ?Becky is going to love it.
Thank you again for your contribution.? She gave me a big kiss and hug.
I blushed, ?No problem.?
?OK, let?s get back to work.? I realized I felt a sense of
disappointment.
We were cleaning the garage out when Amy said, ?Becky and Ryan are
coming over this weekend for the 4th of July. We are going to have a
grill out and watch the fireworks over at the park. You should come
over, bring your parents too, it will be a great time.? Becky and Ryan
are a few months older than me and go to a different school, but we know
each other through Amy.
?OK, I will say something to them, I don?t think we have anything going
on.?
?Wonderful, Ryan and Becky have been dying to see you again.?
We finished up the garage, said our goodbyes and I walked home to my
house.
When Becky and Ryan got to Amy?s on Friday, they came right over. Then
we all headed straight for the pool. Now Becky is a gorgeous 16-year-
old girl. Tall just a bit shorter than me (5?9?), built (35B) and the
120lbs were proportion just right. She had strawberry blonde hair and
green eyes. Ryan is much the same in proportion, about 6?2,? 225lbs of
lean, toned body mass. We all messed around in the pool, dunking each
other, diving off the board, doing cannonballs to get Becky wet as she
sun bathed. But the whole time, I have trouble keeping my eyes off of
Becky in her little bikini. Around 4, Christy, a girl from the
neighborhood (and a friend of Becky?s from school) showed up at the
gate.
?Amy said you were all over here.?
?Christy!!!? Becky screamed. Becky jumped up and ran over to Christy.
What she forgot was that her top was not tied and it fell to the ground.
I got a great view of her tits. Becky let Christy in and gave her a big
hug, hiding her breasts. Becky then realized her top was on the ground.
Using Christy as a shield, she bent down and picked up her top.
?Amy said she has some errands to run but was going to order some pizza
and invited me to stay and told me to say something to John about coming
over.?
Ryan and I kept horsing around in the pool, but took minute to admire
Christy as she disrobed to her bikini. When we heard Amy?s car pull in
the driveway, Ryan and I got out and dried off. I hollered into the
house that I was going to eat at Amy?s. We all got dressed and headed
over to Amy?s.
Amy had all ready ordered the pizzas and was sipping on a bottle of
beer. She smiled as we all showed up. ?Wonderful, pizza should be here
in a few minutes, there is beer in the fridge. Just help yourself but
don?t over do it.?
?Great!? was the collective response.
?So what have you guys been doing all afternoon??
Ryan spoke first, ?We?ve been swimming and relaxing, what every kid
should do in the middle of summer.?
?And getting a tan too.? Becky chimed in.
The pizza showed up and we all sat down on the deck to eat. When dinner
was done Amy got a call from her catering crew. She came out on the deck
and said, ?I have go check in on my staff, we are short a person, help
yourself to beer in the fridge and I will be back later. Please don?t
drink yourself silly. If you need anything, John knows where everything
is.? As the sun went down, Ryan and I decided to light up the fire pit.
Once the fire was roaring, we all sat back, drank our beers and chatted
about our summer so far. After several beers each, our conversation
steered toward love interests and sex. After what seemed like a few
tall tails, Becky suggested we play a little ?Truth or Dare.? We laid
out the rules to be pretty simple; one person would ask a question, and
then the other three would answer. If you do not answer, or the others
deemed you lied, the questioner got to come up with a dare.
At first it was pretty innocent, then Becky asked, ?I am a virgin, are
you??
?Yes.?
?Yes?
?Yes?
Next came ?I have fingered myself to orgasm, Have you ever masturbated??
from Christy giggling.
?Yes?
?Yes?
?Yes?
?I have touched a girls naked breasts, what have you touched on the
opposite sex?? came from Ryan.
I said, ?I have sucked on a girls breasts and I have fingered and licked
a girls pussy.?
?John,? both the girls said, ?it?s called a vagina.?
?I have felt a guy?s penis and testicles a couple of times.? Becky
said.
?Well I have given a hand-job to a guy, plus while I did it, I lick his
cock a couple of times.? Christy chimed in all giggly.
?Oh, Christy, a blow job, way to go.? I said.
?No, no blow job, just a couple of licks, he came from my hand. What a
mess too.?
Ha-ha. I laughed, ?Ok, what has some one of the opposite sex done to
you? I have had a blowjob.?
?I have been felt up and have had my ?pussy? as you called it rubbed on
the outside of my panties.? Becky replied.
?I too have been felt up.? Was Christy?s reply.
?I?ve never had a girl touch me that way,? came from Ryan. We all were
a little suspicious but let it go.
After a couple of easy questions from the girls, Ryan queried, ?Have you
ever done anything sexual with some one of the same sex? I have not.?
?Never? came out of my mouth
The girls looked at each other, then Becky said, ?Well, one time at a
slumber party, all the girls practiced kissing. It wasn?t sexual or
anything, just showing each other how we do it.?
After a few seconds, Christy chimed in with, ?Yah, I was at that party
too.? But it seemed a little too easy and she seemed to be covering
something up.
At the same time, Ryan and I both said ?Bullshit!! We do not believe
you.?
?Since, 2 out of 3 believe you are lying, you must do a dare. I dare
you to show us your tits.?
?Ryan!? Becky cried, ?I think that is a little much.?
?No, that is ok, Becky, I will do it, those are the rules.? Christy
stood up, walked out in front of us and proceeded to take her shirt off.
She stood there wearing a matching bra to the one Amy had me wear. She
then unhooked her bra and exposed her tits. Ryan and I just blatantly
stared at them. When I looked back, I noticed Becky sneaking a peek
also, but trying to hide the fact. I said nothing to her.
My turn came next. ?Have you ever had sexual contact with some one a
lot older than you? I have ?played? with an older woman.?
Ryan ?No.?
Christy ?Yes?
Becky ?No and I don?t believe John.?
Christy ?Me neither.?
?Why would I lie about my own question??
?Prove it, who is she?? Becky asked.
?To look cool or to hide the lie to see about us. Since two of us think
you lied, I will set the dare. I dare you to show us your ass.?
?I can?t say, she would kill me if it ever got out.?
?Then you have to do the dare.?
?OK,? I got up and went out in front of everyone, turned around and
pulled down my swimsuit exposing my very white ass.
?Oh very cute, nice and tight." Came from the girls, but Ryan said
nothing.
As Becky went into house to use the bathroom and to get some beers,
Christy said, ?Let?s stop the truth or dare and just do the dares. Or
better yet, how about we each strip down naked for the others to see.?
Ryan and I agreed and we all waited for Becky.
When Becky came out, we told her of our new game. She thought about it
then said ?How about one additional wrinkle. While we are naked, the
others have to ?investigate? the naked person?s body. Say we each get
one minute to touch, feel, probe or inspect.?
?Each of us has to go up for one minute? I have to go up for one minute
when Ryan is up there?? I asked.
?Yes, you can do whatever you want for the one minute, but you must
touch them.?
We all agreed, though I was a little hesitant about Ryan.
Becky was first. She got up and began removing her clothes. First came
the shorts, then her top. Next she slowly removed her bikini top and
then bent over to remove her bikini bottoms. Ryan approached Becky
first. Since it was his sister, he was a little hesitant. He touched
her breasts and looked at them closely, then he had her spread her legs
and he looked at her pussy really close. When it was my turn, I went up
and put my hand right on her tit. I played with her nipple and she let
out a little whimper. I then felt her ass and found her pussy with my
other hand. I slid a finger between her lips and she gasped. About 10
seconds after putting my finger between her lips, my time was up.
Christy made her way to Becky. She put a finger on her nipple and blew
on the other. This made Becky shiver. Next she fondled her breasts and
slid her hand down to her crotch. To my surprise, Christy pushed a
finger into Becky. I think it surprised Becky too. Becky gasped and
began to whimper, and then Christy?s time was up. Becky put her bikini
back on and sat down, ?Who?s next??
?I?ll go? Ryan said.
Ryan got up and took off his shirt and removed his swimsuit. As I said
before Ryan is all lean and toned. His body was a great physical
specimen. His cock was currently thick and flaccid. Becky approached
him first. She felt his abs, then his pecs. Walk behind him and
started rubbing his ass. As she did this, Ryan started to get a little
aroused. Next I went up. Never having wanted to touch a guy, I
followed Becky?s path. I felt his muscles and then his ass. Ryan
continued to get aroused. His cock was now fully erect and around 7.5-?
For some unknown reason, I decided grab a hold of it. A gasp came from
the girls, but I continued to feel his manhood and balls. ?Well it?s
bigger than mine, but it feels the same.? I sat down. Now Christy went
up. She wasted no time on the muscles and went straight for the ass.
She rubbed it and you could tell Ryan enjoyed it. As she continued, she
took a hold of his cock with one hand and continued to feel his ass with
the other. She slowly began to stroke his cock. After about 10 seconds
of stroking, her time was up and she sat down. Ryan put his suit back
on and sat down.
?Nice? was all that she said.
Next Christy got up. She wasted no time getting naked; you could tell
she was very excited about this. She stood there for a second in the
matching bra and panties before removing them. Seeing her in same bra
and panties I had worn, got me really hard and very horny. Ryan went up
first and treated her the same as he treated his sister. He felt her
breasts, then her ass and finally her pussy. He did slide a finger
between her pussy lips but only for a second. Becky got up and went
right for her tits with both hands. She kneaded them and teased her
hard nipples. Then her hand found her pussy lips and slid a finger
between them. Becky then proceeded to finger Christy for about 30
seconds. When I got up next to Christy, her body was quivering.
?Beautiful? was all I could say. I bent down and took a nipple into my
mouth and began sucking. I followed this with a finger in her pussy.
Christy just stood there as I brought her right to the point of orgasm
when my minute was up.
I stopped what I was doing and removed my hand from her pussy. Christy
then said, ?Please don?t stop!! Just a few seconds more.? So I slid two
fingers in and used my thumb as Amy had taught me. Christy climaxed
right there on the deck, her knees going weak. As I held her in my
arms, Christy recovered from the orgasm and said, ?Your turn,? And
started helping me with my shirt.
As Christy pulled my suit to the floor, I stood there with my hard 7?
sticking out proudly. ?I?ll go first?, was all she said and Christy
went right to work. Her one hand found my 7? and my balls. She began
stroking my cock with one hand as her other hand found my ass. As with
Ryan, she stroked me slowly and rubbed my ass. When her time was up,
she grabbed her clothes and sat down. Becky came up next and picked up
where Christy left off. She started stroking my cock and playing with
my nipples. Then without notice, she dropped to her knees and put my
cock in her mouth. For about 30 seconds, she licked and sucked on my
cock. Her time was up and I was so near orgasm it hurt. Ryan then
approached me. He touched my shoulders and my ass. The surprisingly,
he grabbed my cock and started stroking it. After about 20 seconds, I
exploded in an orgasm. Shooting cum all over the deck and going weak in
the knees. Ryan, surprised himself, just said ?Sorry dude, I was just
curious what another guy felt like, did not mean to do that.?
?Uh, Uh? I stuttered, shocked, ?N