Date: Wed, 16 Sep 2015 16:20:28 -0500
From: Jack Parke <letsdothedeedagain@gmail.com>
Subject: Philip

Philip
(mm, CD, spanking, oral, anal)

This story involved men having unprotected sex with each other. If this
isn't what you like, go read something else. And if you have sex, use
protection. Also, if you like this story, I love comments and criticism but
I also erase scam! Hey guys, support Nifty, it's a great site and doesn't
run for free!


I had met Phil several years ago on a now defunct internet chat program
(mIrc). At that time, he and I met twice at his house and we enjoyed each
other's company... to a point. Phil was into cross dressing and this was
the first time I had seen that; it didn't freak me out but it was
different. He didn't go the full route; he wore women's panties and a short
nighty but nothing else feminine. He also spanked me a little but he didn't
really `get into it' very hard. One thing he did that was a bit brutal, he
tried to insert his finger in my anus but his finger was dry and it hurt so
I stopped him. He wanted to fuck me but at the time, I was still an anal
virgin and I didn't want to try it and that was the last time I saw him.

Move forward about 15 or so years and I happened to see him one day at a
sporting goods store at a mall. He didn't notice me, my guess was he had
forgotten what I even looked like but he had a distinguishing mark on his
face making it easy to recognize him. We didn't speak but it got the ol'
gears churning in my head! He was looking at a fishing reel and I walked up
next to him and picked up one also. I asked if he had ever used that type
of reel and he said yes but he wanted a new one. I mentioned that I hadn't
been fishing for a long time and was attempting to get back into the sport
but he didn't reply.

I decided `what the hell' and said "Phil, we met around 15 years ago at
your house and on mIrc." He spun around and took a long look at me and had
a puzzled look on his face; it was apparent he was trying to remember me. I
decided the `pregnant pause' had gone on long enough and I told him. "We
met twice but at that time, I didn't want to do what you wanted to do." It
was like the cartoon where the light bulb goes on in the head! He
immediately said "you're Jack?" I responded "yes, sure am. How have you
been?" "Good, hey, you want to get a cup of coffee?" I replied that I would
so we went to the food court, got a coffee and sat down across a small
table from each other.

We talked about a few things, mostly fishing, and then the conversation
turned to the fun stuff. I asked him if he was still doing the CD thing and
he replied that he had really gotten into it and had a full wardrobe. This
was a chance encounter, I wasn't about to pass it by without attempting to
rekindle the playmate from many years ago! I was lost in thought, trying to
decide on what to say to see if he was also interested in meeting again
when he said "do you want to head to my house?" I immediately replied that
I'd meet him there and we were off!

When we arrived and entered the house, he motioned for me to sit on the
couch and he sat in `his' chair. He asked if I was still into spanking play
and I replied that I was. Next he asked if I was still a virgin and I told
him that I wasn't so he asked about how I lost my virginity. I told him
that the guy I was with took his time and used lots of lube and didn't rush
things; he replied that he had learned the same thing and that he wanted to
fuck a guy in his ass but wasn't able to find anyone willing to let him so
he learned to slow down and allow the `fuckee' time to get stretched and
properly lubed up.

Next he told me that he enjoyed it when his partner would dress for him and
that he had quite a selection of women's wear; he said he liked to
role-play that both were women and then enjoy the fun of taking off `his
girl's' clothes and then ravaging her body! We actually had only talked for
not more than ten minutes and he really `broke the ice' and asked if I
wanted to play and I replied "damn right!"

He grinned from ear to ear and told me to go into the front bedroom and
pick out some clothes to wear and he was going to call me "Tammy" and asked
if I would call him "mommy" and I agreed. He said that he wanted to
role-play that I had been caught playing with Johnny down the street in his
basement and he was going to spank my bottom real good for being a naughty
little girl; that played right into what I loved doing. I went to his
`guest room' and he went into his master bedroom. I closed the door and
looked into the closet, I found all sorts of clothes to turn me into "his
little girl Tammy", including a blond, long hair wig that I decided to
wear.

First off, I'm an average guy, a little overweight but I had no knowledge
of what to pick out to wear! The first thing I did was to strip
naked. Next, I looked into a dresser next to the bed and found a pair of
women's panties so I put them on and then found a bra but the cup size was
way too big. I put it on anyway and got some tissue and stuffed it into the
cups. Then I found a blouse that fit well enough to wear and also found a
skirt and put it on also. I decided a little girl wouldn't be wearing any
hose so I skipped that and looked into the mirror and put on the wig. Next
I took some lipstick and put it on, I didn't use much because I knew I had
to get it off once we were done as I sure as hell wasn't going to be
wearing any of it when I left! As we had decided, I opened the door and
announced that "Tammy is ready, mommy!"

Not a minute went by when I heard `mommy' call my name, saying "Tammy, you
get in here this very minute!" I have to admit it put a bit of fear into
me, I remember my father yelling at me when I was growing up and I remember
the fear I had back then when he called for me and I knew I was in trouble
for doing something I shouldn't have done! As I walked towards the master
bedroom, I started to wonder if this was the right thing to do! Everything
was happening so fast and I was having trouble processing what I was
feeling. I opened the door and stepped in and there stood `mommy', wearing
a floor length quilted house coat and holding a leather paddle in her hand
and she didn't look happy at all.

"What was going on in your mind when you and your friend Johnny were in his
basement yesterday? Have you lost your mind? His mother just called me and
was very upset, she was watching the two of you through a basement window
and got an eyeful and neither of us are happy!"

"I'm sorry mommy; we were watching TV and Johnny started kissing me! He's
kissed me before but it was like you and daddy do but this time it was
different and it felt good! I didn't know what was going on and then he
forced my mouth open with his tongue and put it in my mouth!"

"That's no excuse at all, young lady; we had the talk about what boys want
to do and then you totally forget and go off and turn into a slut! What
else did you do? Did you do anything but kiss him?"

"Mommy, he touched me!"

"Where?"

"On my boobies. We were kissing and it felt good and then he had his hand
on my tummy and then slid it up to my boobies."

"And then what happened?"

"Mommy, it felt good. I've never felt anything like that and my cunny
started to sort of itch a little!"

"Oh my God, what happened then?"

"He was rubbing my boobies and then he slid his hand down and got under my
t shirt and then slid his hand up again and started to rub my boobies
again. It felt so good mommy, I'm so sorry!"

"Sorry isn't enough young lady! This is horrible... did anything else
happen?"

"He took my hand and put it on his pants and pressed it down kind of
hard. I could feel his wee wee get hard. Then he pulled his hand off my
boobies and slid it down over my cunny and started rubbing it through my
pants."

"I just don't believe this, how stupid could you actually be? You let him
touch your bare breasts and then rub your cunny? What do you think he
thinks of you now? Probably just easy" she snorted. I knew mom was really
mad at me but in for a dime, in for a dollar so I continued!

I decided to "expand" the story to add to the experience I was having so I
dreamed up what might be something two young adolescents might do when both
of them are experiencing raging hormones.

"Mommy, he slid his hand down inside my pants and put his finger on my
cunny and it felt so good. I felt better than I've ever felt before! And
then he unzipped his pants and pulled his wee wee out. It was hard and he
took my hand and had me rub it for him!"

"I just don't believe this; he had is finger in your cunny and you were
stroking his wee wee? Then what happened?"

"He sort of slid away from me a little and then he pulled my head over and
made me kiss the end of his thing. It had some kind of clear stuff on it
and it tasted good. He wanted me to put it in his mouth but I refused so he
took my hand and I rubbed it and then he must have peed some kind of while
stuff; I don't know what he did but he was groaning so it must have hurt
real bad!"

I don't know where the next remark came from but what the hell, I decided
to put it out there and see if Phil liked it or not! "Am I pregnant now
mommy?" I asked.

Phil almost broke out in laughter, he got a big grin on his face and I know
I was grinning when I asked if I was PG! I really do enjoy role playing, it
can help break the tension between two guys and allow them to `dip' into a
role that they dreamed of in their minds.

He immediately went back into his role and said "get yourself over here and
get ready for a good, sound spanking!" and sat on the end of the bed. I
walked over and he led me over his lap and pulled up my skirt, exposing my
panty clad bottom. I was unable to see what he was doing but then suddenly
felt a leather paddle land on my asscheek with a loud `pop' and I jerked
because it stung like crazy!

Mommy really got to work and landed swats to each cheek and it really
started to put some fire in my bottom! "Please mommy, no more, it
hurts!!!!" WHACK WHACK POP SMACK and on it went. The entire time "she"
spanked me, she was giving me "the lecture" that a parent gives a
recalcitrant child while they are giving them a spanking. And mommy was
really giving me a good spanking and it hurt!

I'm not a crier but I noticed my eyes were starting to water, much like
when a guy hits his fingernail with a hammer! Fortunately, mommy stopped my
spanking and told me to stand up, which I gladly did as I thought my
punishment was over. Much to my dismay, she stood and started unbuttoning
my blouse which she let fall to the floor and then she unfastened my skirt,
allowing it to join my blouse. Then she unfastened her robe which revealed
mommy was wearing a sexy "teddy" with lace panties! She removed her robe
and sat down, facing me and then she hooked her thumbs in my panties and
started tugging them down to the floor.

I tried to hold on to my panties and keep her from pulling them down, "Oh
please mommy, don't pull my panties down! It will hurt too much on my bare
bottom!"

"Shut up Tammy, you are going to get a spanking like you've never got
before. Down came my panties and mommy drug me back over her lap and
continued with her leather paddle again. I was amazed how much the thin
panties had protected my bottom from the earlier spanking but now the smack
when it fell was much louder. Mommy really was laying into the job now and
it really hurt!! SMACK SMACK SMACK Yeowwwww Mommy, PLEASE NO MORE!! Shut up
Tammy, this is just starting!!

Mommy continued the punishment and I knew she was really giving my ass a
red burner and it hurt like hell! I was pleading, begging, telling mommy
how sorry I was, all to no avail. Then just as fast as it started, it
ended.

I felt relief, knowing it was over! Goddamn, it sure did hurt and my ass
was hot and stung like a million bees had invaded me! Then I felt mommy
begin to rub my ass and felt a cool salve; mommy was spreading some aloe
lotion on my bottom to help stop the burn and prevent bruising. I have to
admit that it really felt good plus mommy was allowing her finger to rub
across my pussy too and THAT really felt good. I knew the spanking was over
and wondered what was going to happen next. Well to my surprise...

I could feel mommy reaching for something and then SSSPOP, SMACK SMACK
SMACK. Mommy had started again but this time, with her hairbrush and with
my bottom being "wet", it really hurt like crazy!! YEOOOOWWWW MOMMY,
PLLLEEASE NO MORE!!! MOMMMMMYYY, I CANN'TTTT TAKE ANYYYY MOOORE. OOOWWWEEEE
MOMMYYYY, PLLLEASE but on and on it went. She was spanking me with a short
break after each swat and she was timing them; "you think you are going to"
SMACK "play with Johnny in his basement" SMAAACCKKK "well young lady I have
news" SSSSMAAACKKK "for you" and that's when the damn broke and I started
bawling like the 8 year old little girl I was playing!

Mommy continued with the hairbrush and I was sobbing and yelling for her to
stop but she continued with the punishment. Then I just yielded to her and
went limp, sobbing my eyes out and slobbering how sorry I was for what I
had done and how I'd never do it again and on and on. I didn't realize it
but mommy had stopped spanking me yet I kept on sobbing and crying.

Mommy helped me up and I sat next to her on the bed, it hurt to sit but
mommy held me close and I nestled my head between her "breasts" and sobbed
and sobbed. Finally as I stopped crying, she pulled my face up and kissed
me tenderly on the lips. Then she broke that kiss and began to kiss my
face, kissing away the tears. Then she returned to my lips and kissed me
again, this time with more urging and I felt her tongue touch my closed
lips which I opened and allowed her tongue to invade my mouth.

While she was kissing me, I felt her hand work its way underneath me and
her finger start to rub my boi pussy, which was still well lubricated from
the aloe lotion mommy had spread over my bottom. I had to admit it did feel
good, what with the just completed punishment and my bottom being so hot
and now the invading finger, it was causing my `clit' to start to grow!

I took my hand and started rubbing her crotch and could feel her `clit'
growing, much like mine. Mommy and I slowly fell backwards on the bed and
laid side by side, facing each other and continued kissing each other. I
started kissing mommy on her neck and began working my way down towards her
titties. The teddy she was wearing was sheer and I took her nipple in my
mouth and began sucking it as though there was no fabric between my lips
and her nipple. She was moaning so I know she enjoyed what I was doing and
then I kissed my way down towards her belly button and once there, kissed
it and put my tongue inside it.

I tugged on mommy's bikini bottom and she raised her hips up which allowed
me to remove them. As I did, I could feel wetness on her `clit', it was
seeping a nice load of precum. I leaned over and took her in my mouth and
heard her moan. I worked up and down, licking her glans while stroking her
ball sac. She got harder and I could tell, close to cumming and suddenly,
she pulled me up and have me lie face down on the bed and pushed a couple
of pillows under my middle. I knew for sure what was going to happen and I
was ready!

Mommy mounted me and I felt her `clit' find my boi pussy and she pushed
gently, I was ready and relaxed and the head popped in. She stopped there
and allowed me to become accustomed to the feeling of her being inside
me. Then mommy slowly pushed her entire length into me and I could feel her
balls on my perenium.

She stared to fuck me in earnest and drove in, pulling almost all the way
out but stopping and then driving inside me. I could feel my cock being as
hard as I've ever know it to be, on each stoke, she was massaging my
prostate and I felt I was about ready to cum myself. I had been fucked
several times before but I had never cum while I had a cock in my pussy but
this was as close as I had ever felt.

Suddenly, mommy drove in and held her length, I could feel the crown begin
to grow and on her next out and in, she started to grunt and I was able to
feel her warm cum flowing inside of me and that's all it took, I had the
strongest orgasm I think I've ever had in my life!

She held her cock inside me and I felt it shrink and then plop out, and we
rolled face to face and began that tender `after orgasm' time and tenderly
kissed each other. But time dictated that I had to go, so I got up, wiped
off my lipstick, got dressed and left but not before making a date for a
couple of days later!

The End