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Subject: {ASSM} My Weekend With Erin 2/2 (M/F)
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Date: Sat, 13 Nov 1999 16:10:00 -0500
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My Strange Weekend with Erin
Section 2 of 2
I removed my underwear, my cock dangled between my legs as I moved to
pick
up the red outfit I had picked out. As I picked up the red thong, I
looked
at Erin, she nodded as if to continue. I put the thong on, adjusted my
cock so that it was secured behind the triangle shaped front. Erin
reached
out and rubbed my crotch through the thong. I couldn't believe how good
this felt. My cock jumped to full attention. She smiled and said, "You
like this don't you?" The verbal reply wasn't necessary, the answer was
obvious considering the bulge in my 'thong'. She removed her hand and
said,
"Go on." I picked up the garter belt, and wrapped it around my waist
and
hooked it. I grabbed the stockings from the bed, and tried to pull them
over my legs. I was having a hard time with them when Erin said, "Here,
let me show you how to do it." She grabbed the other stocking and put
her
arm through to the toe, slid the length of the stocking down her arm to
her
hand and held it out for me to take. I took the stocking, let a little
of
it out looking for the red stripe, wanted to make sure i had them on the
right way and slid it up over my legs. "Do it slowly she said, not so
fast." I slowed the pace, remembering seeing it done as she suggested
in
movies and how sexy the woman looked as she did it. I hooked the
stockings
to the garter. The sheer hose actually provided a rather satisfying
tingle
on my legs. Erin nodded her approval so I continued. I reached for the
bra, decided to go with the matching bra for the set and slipped it on.
I
fumbled with the hook on the back. I couldn't get it to catch. She
said,
"Turn around, I'll get that for you." I did as she asked. "There you
go."
I turned around to face her, kind of embarassed standing here wearing
womens
underwear right in front of her. She said, "I like that outfit on you,
you
are a sexy lady." She reached up and gently pinched my nipples
underneath
the smooth fabric of the bra. My nipples stiffened upon her touch.
This
feels soo good, i thought. She said, "turn around slowly, place your
hands
on your hips and model it for me." I did as she said. "I like what I
see,
go ahead and finsih." I reached for the dress and slipped it over my
head,
pulled it down until everything was in place The dress stopped about mid
thigh, just below the tops of the stockings. Without her saying
anything,
I turned around for her as she had requested before. She said, "There's
one thing missing." I gave her a puzzled look. She said, "Where are
your
shoes?" I nodded, picked up the red shoes I had picked out. The were
obviously too small for my feet. She said, "Look in the closet, there
is a
larger pair in there. I picked them up a while back hoping to someday
get
a chance to have someone wear them." So I am the first guy that she's
convinced to do this. Am I normal? I had alredy gone this far, so I
went
and grabbed the two pair of oversized heels. The heels were about 4
inches.
I slipped the red pair on, they fit fairly well, I adjusted the straps
and
attempted to stand. I lost my balance and almost fell. I regained my
balance and stood there for a minute adjusting to the feel of the heels.
The shoes were a bit uncomfortable, I couldn't see how a woman can walk
around in these things all day. I tip my hat to you ladies out there.
"Walk over towards the door and back for me, I want to see how it will
look in motion." I walked toward the door, there was a full lenght
mirror
on the wall. My head wasn't visible since the heels lifted me up. I
was
impressed with the reflection I saw in the mirror. My cock pulsed
harder.
Wow, this was a real turn on. I was thinking that I may just like this
little fetish. I returned to face her.. She said, "go sit in that
chair
over there and cross your legs" I did as she said, though I had a hard
time getting my legs to cross as she expected them too. She then leaned
down a bit and started staring up my skirt. I could see what the point
of
this was, now it's her turn to stare up a womans skirt. I liked it. I
decided to 'tease' her as she did to me at work. So I put my leg down
and
pressed my knees tightly together. I could tell by the expression on
her
face that she was bothered by that move. I was acutally enjoying the
attention I was getting from her, I imagined myself as anoter attractive
woman that is fighting off stares. Is this normal behavior? Is
something
wrong with me? She motioined for me to return to her side. I did as
she
asked. We repeated the same process with the black outfit.
By the time I finished modelling the outfits, it was pushing 10:00. My
the time has passed by so quickly. She said, "It's almost too late to
go out anywhere, by the time we get dressed and get there it will be
close
to midnight. Let's plan to stay here and have some fun. I want to take
advantage of my new female lover while I have the chance." She got up
and
went into the bathroom, returned with a make-up kit. She looked me in
the
eyes and said, "It's OK, don't worry, I will not do anything permanent."
I
nodded and she continued with the makeup. She gave me a complete
make-over.
When she held up a mirror, I couldn't believe that the face I saw was
mine.
I liked the bright red lipstick that she had put on me. She went into
the
closet and came out carrying a brunette wig. Placed it over my head and
said, "There, now that's about as close to a woman as I can make you
without
surgery. Now, go look at yourself in the mirror and tell me what you
think"
I went to the mirror and really liked what I saw. I was still wearing
the
black dress and heels. Going along with the fantasy she wanted to
fulfill,
I said, "Looks good, honey. Am I as pretty as you expected? Am I
pretty
enough to be with you?"
"Oh yes. You are a knockout sweetie. Though you could use some larger
tits. Now come over here and let me taste that cunt of yours."
I walked over to her, she lifted my skirt and pulled my panties to the
side.
My cock popped out and landed in her hand. She wrapped her lips around
my
shaft and worked it deep into her mouth. Her hand moved to cover my
balls,
she gently squeezed my balls, then worked her finger back towards my
asshole. Raking her finger across my ass, she poked at the hole a few
times. I knew what she wanted, and I've read about women doing this to
men so I said, "Oh yes, baby, stick that finger in my hot cunt. Lube
your finger up and shove it in my tight cunt." She guided me to where
I was on my back laying on the bed, she unhooked the garter from the
hose and slipped my panties off, then reconnected the garter straps.
My skirt had slid up around my hips, my rock hard cock and ass were
exposed uner my skirt. Erin went to the dresser and took a bottle
of lubrication from her 'toy' drawer. She squirted some on her hands
and began rubbing it around my tight asshole. She slowly worked a
finger into my asshole. At first it hurt a little, I flinched a little
and she stopped and held her position. I relaxed myself and the rest of
her finger slipped into my ass. I could feel her finger probing around
inside my ass. It felt kindof good. I said, "Cmon, baby, fingerfuck
my cunt while you suck on my big clit." She worked the finger in and
out while her mouth and tongue devoured my cock. I could feel another
finger probing at my asshole, it slipped in without much effort. "Oooh,
baby, I like that, I like the way you stretch my cunt out. Give me
more, please, I want more." She worked a 3rd finger inside my ass,
I was in disbelief at the wonderful feeling I received from the anal
penetration I was receiving by her fingers. She worked her fingers
feriously in and out of my asshole.
I was on the edge of exploding in her mouth when she pulled her head
away from my cock saying, "Not yet baby, You are going to have to wait
before you do that." She got up and went back to the dresser saying,
"Don't worry about anything. Whatever happens in this room between you
and me stays in this room. I will never tell a soul what he have done
or what we do in the future. It will be our secret."
I looked up to see what she was doing, was adjusting something around
her waist, her back was turned I couldn't make out what she was doing.
She turned around, and there was a 8" dildo strapped to her. I said,
"Whats that for? I'm not gay, I don't want to be fucked in the ass."
"Come on sweetie, your my little lesbian bitch, I want to fuck your
cunt. Please, this is one thing I've wanted to do. I want you to
experience the same pleasure I do when I get fucked in the ass. You
will like it, trust me. It might hurt at first, like the fingers, but
once it is in, you will beg me for more."
All kinds of thoughts were rushing through my mind. What if someone
found out I got buttfucked by a woman, would they say I was a queer?
What if I do like this? What will I be like afterwards? Does this
make me gay? Once again, I was confused.
Erin could see the confusion, she said, "Don't worry, trust me!"
I said, "Oh Erin, I'm such a little slut. I've been a naughty little
girl. I need you inside me so bad. Please be gentle though."
"On your knees!" Erin demanded. I did as she requested. She walked
towards me, the dildo was bouncing up and down. I watched it as if I
was a naughty girl anxiosly awaiting the chance to hold that hard
prick.
She stopped in front of me, held the dildo up to my face and said, "Open
up and say ahh you little whore." My mouth opened, I reached up and put
my hand on the shaft of the dildo. I worked the head of the dildo into
my mouth. She drove it to the back of my throat. I almost gagged. She
said, "I'm gonna have to teach you how to deep throat someday sweetie."
She withdrew the cock and I went to work on it as she had done for my
cock. I looked up at her and she was smiling, I could tell she was
enjoying it as much as I. "That's enough, now on assume the position,
I want to do you doggy-style."
I complied, I pushed my chest as close as I could get to the floor and
still have the strenght to support my weight. I raised my ass up as
high as I could. I said, "Fuck me like the little whore that I am, go
easy though, you have a really big cock, It might hurt". I could feel
the coolness of the lubricant as she spread more around my puckered ass.
I felt her fingers entering my ass again and felt her stretching my
asshole in opposite directions. "Oooh baby, that feels good, stretch
my ass, I mean my cunt". She removed her fingers, the next thing I felt
was the rubbery head of the dildo pressed against my tight asshole.
"Ok, you little slut, you're gonna get what you deserve now. I know
you want this hot prick shoved deep inside your hot cunt."
She pushed the head of the dildo through the outer ring. My asshole
clasped tightly shut around the head of the dildo. I whinced a little
then after the initial shock I was able to release the pressure. She
continued sliding the lenght of the shaft into my bowels until I was
completely full. I was shocked at how good it felt to have that dildo
shoved deep inside. It was exploring never before touched territory
and I liked it. She worked it in out slowly. Put some more lube on it
and gradually picked up the pace. "Oh baby, fuck me.. fuck me harder"
I moaned back to her. "Fuck this little slut good." She was working
the dildo in and out very rapidly. She was making nasty comments about
what she was doing. She reached around and begain stroking my cock
with one of her hands. I was on the virge of cuming by this point,
my cock had been rock hard just from the pounding my ass was taking.
The pleasure was that of something that is hard to explain. My cock
began to swell, I could feel the pressure in my balls then she removed
her hand.
"Not yet, you little slut, your gonna drink my cum and swallow it. Roll
over onto your back. Thats it, now use the bed to support yourself,
raise your ass high in the air and curl forward so that big clit of
yours is pointing to your face. That's right just like that." She
climbed onto the bed and reinserted the dildo into my ass, it went in
much easier this time, didn't take as long for her to regain the same
pace she was at earlier. "Now, rub your clit until your cum squirts
into your mouth, keep the mouth open, I want to see that cum go down
your throat." I followed her command, I started stroking my cock,
within a few minutes I shot my wad, the first blast went into my mouth,
the second hit me on the cheek, the rest oozed down my hand. "Look at
you, you little whore, got cum all over your face, but you liked that
you little tramp. Now, swallow that load in your mouth." I had tasted
my own cum earlier in the evening, so the taste wasn't that much of a
surprise, but having to swallow it was a little different. I figured
I'd come this far, may as well finish. I swallowed the cum, it felt
strange but erotic as it slivered down my throat. I then licked my
fingers clean of the cum that oozed onto them. "Thats a good little
bitch," Erin said, "Now, wipe that cum off your face." I did as she
said, and licked it from my fingers. By now I was used to the feeling
of it slipping down my throat and I didn't mind it as much. She
withdrew the dildo from my ass. I let myself fall to the floor. I was
exhausted. I got up looking at the clock, it was 12:30. This had gone
one for a while. I was growing tired, and I could see that Erin was
dragging a little bit. She said, "It's getting late, lets get ready
for bed."
Erin went to the closet and came out carrying two long silky
nightgowns. She said, "Here, this one is perfect for you." Handing
me a purple gown. I took the hint that she wanted to 'sleep' with a
woman too. I wasn't sure if I was supposed to wear panties underneath
my gown, so I removed my dress, stockings, and garter slow enough to
watch Erin put her gown on. She slipped a skimpy pair of panties on
underneath the gown, so I knew that the answer was yes. I found the
black panties I had on earlier, slipped them back on, adjusted my cock,
and put the gown on. I received the same sensation as I did earlier
when her robe was rubbing against me, but this time I was wearing her
panties and the feeling of the material rubbing against my cock was
better than before.
She pulled back the covers, we snuggled up with each other and Jeanna
said, "Thank you baby. You don't know how much this means to me. I've
been waiting for this a long time. I really enjoyed it as much as I
thought I would. I hope you liked it too."
"At first, I didn't know what to think, but I did actually like what
we just did. I hope that don't make me a fag or anyting. As I told
you earlier, I'll do anyting for you. Well, not anything, I won't
touch another man, nor allow another man to touch me, in case that
happens to be one of your fantasies. If it is one, I want you to be
forwarned now."
"Don't worry bout that baby, that's not in my plans. I don't like the
idea of two men anyway." She put her lips to mine, we kissed. "Now,
go to sleep, we have a long day ahead of us tomorrow. Goodnight my
new lesbian lover."
"Good night Erin".
END
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