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Authors name: LaffWithMe
Story totle : Bob Dresses for Halloween
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Bob Dresses for Halloween
By LaffWithMe
(c) 1995, 1999 LaffWithMe Press
Internet laffwithme99@yahoo.com
Synopsis: With his wife's blessing and encouragement
Bob ventures out on his first cross-dressing foray.
Let us say he is deeply impacted by the experience.
(MM, First time, Dress)
Bob was trembling as he walked through the women's
section of the large department store. There were very
few people in the store this morning, yet he was
certain that each of them was watching him. Seeing his
wife should have calmed him but it didn't.
"See, Bob, I told you the floor would be empty this
morning. Come back to the fitting rooms, I think I've
got some great outfits for you to look at."
"Jesus Casey, I don't know if this is really going to
work. Maybe we should forget it." Bob replied.
"Oh no, you're not going to chicken out on me now."
Casey grabbed his arm and pulled him through the
curtain, then into a small cubicle. "You said you
wanted to do it and I think it's a turn-on. Anyway,
you'll never know if you like it until you actually
try it. And what better time than Halloween?"
The 'it' in question was something that had haunted
Bob since he was a teenager, maybe even before that.
The 'it' was his fascination with women's clothing -
no, not a fascination, a desire to dress in women's
clothing. It was more than just dressing the part,
he knew down deep, that he wanted to experience being
a woman.
"Now strip while I go get your new wardrobe". At this
point it seemed that Casey was more excited about this
adventure than Bob. As the cubicle door swung closed,
Bob stripped to his nylon bikini shorts. He watched
himself in the mirror as each piece of clothing was
removed. Then, almost naked, he examined himself more
closely, trying to imagine how he would look in...
Shit, he had a hard time even thinking of the word...
'drag'.
Still, he did think he had a nice body, for a man or
a woman. His five foot eight inch frame was lean and
firm. He had continued to swim and run marathons, the
sports that had gotten him small scholarships in
college. His rich brown eyes made a nice contrast to
his fair Nordic skin and collar length blond hair.
His nose was very straight; it almost seemed to be a
pointer to his lips that were slightly large and full
in appearance. He shrugged his shoulders, flexed his
muscles slightly, noticed his nipples move as he did
so. He absent-mindedly pinched one and brought it to
erection. His nipples were almost as large as Casey's
were and very sensitive. His bikini shorts were snug
and he could clearly see the outline of his cock and
balls. Turning to view his profile, he decided that
he had a nice ass atop his well-shaped legs.
Casey was suddenly back with an armload of clothing.
"Preening?" she said. "Here, start with these panty
hose, but don't get attached to them. I think some
nice patterned nylons will look better.
Bob opened the package and removed the pantyhose,
pausing to feel the texture. Casey watched and smiled.
As Bob slipped on the stockings he saw the look in
Casey's eye. That same look when she had caught him
trying on her pantyhose a few weeks before. He had
been embarrassed and ashamed when she walked in, fully
expecting her to be furious. Instead she had a devilish
look in her eye and a clearly mischievous grin on her
face. Bob had known early in their relationship that
Casey enjoyed some unusual sexual activities. In fact,
when he met her, he thought she was gay. Thus it was
no real surprise when she was the one to suggest that
he dress for Halloween.
Casey knelt in front of Bob and smoothed the stockings
from ankle to thigh. The feel of her hands sliding over
the nylon on his legs, the press of the panty top
against his cock caused his cock to swell. Casey looked
at the sharp outline of the hard cock bulging against
the thin shorts and sheer pantyhose. She could clearly
see the balls separated by the seam of the stockings,
the shaft pressed to the side, the flair of the cock
head.
She pressed her face to the knob and kissed it lightly.
"Well sweetheart, I see we're going to have a problem
hiding this little monster" she laughed. Not that Bob
had a monster. On the contrary it was probably slightly
small, but in Casey's view was perfectly shaped. The
shaft was very straight with a prominent blue vein down
the side. Casey loved feeling this vein bulge and pulse
as her tongue caressed it. The shaft was crowned with
a large head that looked like some kind of helmet. What
Casey enjoyed most was the fact that this cock would
get extremely hard. When Bob got aroused his cock truly
felt like a bone wrapped in warm skin.
"Casey, I don't think we should do anything here. Let
me just try on the clothes before anyone comes in." Bob
knew that his wife loved sex just about every way
except in the bedroom with the lights off. Despite his
hard cock he didn't want to be fucking in the women's
fitting room of the biggest store in town.
Casey rubbed her cheek against the solid bulge. "But
sweetheart, you can't try on clothes with this big cock
sticking out. It'll ruin the line." She was hooking her
fingers into his briefs, pulling down the panty hose
and briefs together. In a second his cock sprung free
of the confinement.
Casey talked to the cock swaying in front of her nose.
"Oh poor baby, you're so pale and white. Hasn't daddy
let you play out in the sun? Let mommy kiss that pretty
pink head of yours."
She grabbed the shaft, brought it to her lips and began
kissing the end. She held the tip to her lips and
french kissed it several time, licking the point of her
tongue into the hole. She soon was rewarded with drops
of precum oozing out to meet her tongue. She tightened
her grip on the bone; watched the head turn a darker
shade as she squeezed the blood engorged shaft. The
blue vein swelled and she licked it then sucked the
cock into her mouth.
Bob groaned and gave up to the pleasure. He held her
head and began pumping his cock into her mouth as she
expertly sucked and tongued the shaft. Her hand worked
the shaft back and forth, jacking him off into her
mouth. She reached down, pushed her hand beneath her
waistband and began finger fucking herself in time to
the cock fucking her mouth. Bob could hear voices in
the distance but it was too late to stop. He felt his
juices begin to boil. He moaned and fucked her face
harder. Casey let her tongue work it's magic and
quickly brought Bob to a climax. She felt his cock
pulse in her hand; she sucked and drank as the cum
spurt into her mouth. She rubbed her own clit rapidly,
achieving a small orgasm for herself.
"Now, don't you feel better?" she said as she stuffed
his now limp cock back into his briefs, then pulled
them up along with the pantyhose.
Casey stood, retrieved a lacy black bra which she
slipped onto him. Bob shivered with excitement as she
snapped the bra in place. The bra had padding in the
cups and he could feel the structure of the bra pushing
against his pectorals. "I was thinking of going for
bigger boobs," he said, as he looked down at the small
cups.
"Oh shit, you guys and your tit mania! Look, big tits
will look really fake on you. Look in the mirror, this
thing actually gives you a little bit of cleavage."
Bob turned to the mirror and leaned forward slightly,
amazed at how sexy he felt in bra and panty hose.
Marveling that indeed this bra managed to push his
chest enough to give a hint of rounded flesh.
"Here you go, baby, you're going to like this." Casey
pulled a black sheath from behind some other dresses.
"Slip this on."
Bob wiggled into the dress, feeling it cling to his
body. He felt as if he was wrapped in black SaranWrap.
The dress fit perfectly. It had a long slit up one
side; no sleeves, a high neck and a heart shaped
opening in the bodice. The point of the heart accen-
tuated the newly formed little tits that the bra
forced up.
"Here. Step into these shoes." Casey slid a pair of
low heeled, black, open shoes onto his feet. "Move
around a little bit now. Let's see how this is going
to work."
Bob stepped haltingly back and forth in front of the
mirror. Wobbling on the low heels, he looked rather
ungainly yet he was clearly going to be striking in
this outfit. He moved his leg and watched as the slit
on the dress opened to reveal skin almost to his ass.
"Goddam baby. You do have a pair of legs! Let's see
how that ass looks." Casey turned him to view a
profile. His ass bulged out seductively; his chest had
a nice curve as if he really had firm small breasts.
His cock was again throbbing and pushed out at the
material! "Oh shit, sweetheart. We just have to do
something about that cock of yours. We'll have to try
some tummy tuck panties, maybe the elastic will be
enough to contain you."
All in all, even without makeup, Bob had become a very
sexy looking girl. He could hardly contain his excite-
ment.
"Let's try on a couple of these other dresses, but I
think that one is going to be the best", Casey said.
Reluctantly, he removed the dress and tried on the
others that she had brought him. However, nothing
could top the sheath with the slit up the side.
In the days that followed, Bob practiced walking in
his new heels. He insisted on wearing his new outfit
every night, to the point that Casey had to stop him
lest he wear it out before the big night.
She taught him how to sit, how to walk. She tried to
teach him how to dance. This turned out to be the
second most difficult part of the transition. They
made some progress but decided not to worry about it.
They would be together and would only be dancing with
each other so they figured no one would notice who
was leading whom.
Even more difficult was Bob's voice. Unfortunately,
although his body was not large, his voice was very
deep. They decided that Casey would do all the talking
whenever possible. Bob would limit himself to one word
answers or better, just utter 'uh huh', 'ummm', etc.
Finally, Saturday arrived. Bob was so nervous he
couldn't shave himself. Casey, carefully shaved his
face, then his legs and arms and underarms. She helped
him dress, then draped a towel around him as she
applied the final touches of makeup. When she was
finished, they both agreed that he was now a very
attractive she.
Casey, would be the husband tonight. She dressed
quickly and didn't worry too much about it. Although
she had been to a few lesbian affairs where she
dressed as the man, she didn't get excited about it.
Even so, her athletic body allowed her to be a very
passable male. As they were about to leave, they
paused for one final look in the mirror. They looked
like any couple dressed to go to dinner or dancing
except that Casey wore a black eyemask and Bob wore
a rhinestone crown on his head. Beyond that, the
only thing that looked unusual about them was the
fact that 'Bobbie' was a few inches taller than
Casey.
When they pulled up to the valet parking at the hotel,
Bob started to open the door. Casey caught his arm.
"Wait, honey, let the boy open it."
Just then a grinning teenage boy opened the car door.
As Bob swung his legs around to get out, the slit in
the dress opened to reveal his complete leg. He heard
the sudden gasp of the boy as the teenager helped him
exit the car. Bob's heart jumped. He looked at the
boy's face and saw the horny young eyes staring at
the body in the black dress.
Casey came around. "C'mon sweetheart. Let's not get
the boy's hopes up", she laughed. Bob was thrilled,
that kid was actually looking at him and seeing a
woman.
They made their way into the ballroom, which was
nearly filled. The range of costumes was phenomenal,
some obviously rented for the occasion; others looked
as if the wearer had prepared for months for this
evening. All of the tables anywhere near the dance
floor were occupied. Casey spotted some empty tables
in a distant corner and directed Bob to one of them.
They were both getting into the role reversals and
Bob allowed Casey to pull a chair out for him.
As they walked across the floor, Bob pulled his
shoulders back and pushed his small boobs forward.
He was rewarded with a few glances from men in the
area.
Casey ordered whiskey sours for both of them. She
flirted with the waitress who didn't seem very
interested, or maybe realized Casey was female in
drag. Bob drank his drink rather quickly and Casey
ordered another. "Slow down sweetheart. We're going
to be here for a few hours. I don't want you to get
sloppy drunk and run off with some guy" she laughed.
They chatted and watched the crowd, finished the
second drink.
"Ok, before you start your third drink, I think we
should dance", she said.
"Not yet. I don't think I can do it here in public."
"C'mon. I'll lead, you just follow. Nobody's going to
see you if you just sit here in the corner" she
coaxed.
That was the magic word. Yes he wanted to be seen. He
wanted to flaunt his new persona, see heads turn to
look at him. The music was loud and fast. Bob started
cautiously but was soon dancing as seductively as he
knew how. The dance floor was crowded and perhaps not
as many men were looking at him as he imagined. Still
he was certain that many of the errant bumps against
his ass were not errant at all. He felt an occasional
hand grab his well-shaped ass.
The band worked its way through several fast tunes
with an occasional slow piece inserted to give them
a rest. The band took a break; Bob looked at his
watch. "Geez, almost 11. This is hot, I know some guy
grabbed my ass", he said as they dropped into their
chairs. Casey ordered another round of drinks.
The band returned, the music started. Just as Casey
was about to take Bob out on the floor again, a man
approached the table. "Excuse me, would you mind if I
danced with your wife?"
"No, go right..." Bob began, only to be quickly
silenced by Casey as she said, "I think she'd love
another partner."
Bob froze. The man extended a hand, "Thank you, you
do look fabulous tonight."
Bob hesitated. "Go ahead Bobbie, I'll just sit and
watch," Casey said as she nudged Bob under the table.
"She's a little shy, self conscious about dancing with
strangers," laughed Casey.
Bob looked at the man dressed in a Spiderman costume.
He appeared to be about 40 or 50, maybe six feet tall
and slightly heavy. Probably once was athletic but
obviously did not exercise. Bob allowed his hand to
be grasped by the stranger. Casey and Bob both noticed
the man looking at Bob's leg exposed by the slit in
the dress.
"My names Ted. And you're Bobbie?"
"Uh huh."
"Is that short for Barbara?"
"Uh huh."
At last they were on the dance floor. At least it was
a fast dance so Bob didn't have to worry about follow-
ing. Also, the loud music and distance between them
negated Ted's attempts at conversation. As the song
progressed, Bob again began enjoying shaking his body.
He found it very arousing knowing this man was watching
every move he made. He felt the man's hand glide across
his body whenever they were close.
The music stopped, Bob turned towards Casey at the
table.
"How about one more? My wife's gone off with a friend
and I really feel like dancing", Ted said as he grabbed
Bob's hand. Bob saw Casey staring across the floor at
him; she was grinning wildly.
"Well, Bobbie? Just one more? It doesn't look like
your husband will care."
The music started. Bob turned and smiled at Ted, "OK".
Another fast dance and Bob was now at his sexiest to
date. He saw Ted's eyes savor the views of his leg as
he thrust it out through the slit in the dress. He
noticed that Ted frequently looked at the heart shaped
opening, trying to see past the material to what Bob
wished were real tits.
The music ended, Ted grabbed Bob in a final spin,
holding him close for a few seconds. Then Ted took
Bob's hand and walked him back to Casey. "That's one
hot number. I want to thank you for making my evening.
In fact, would you let me buy you two a drink?"
"Sounds like a good idea" Casey replied as she pulled
a chair around for Ted. She placed the chair so that
Bob was between them.
"You folks staying at the hotel?" asked Ted.
"No, we live here in town." replied Casey.
"Oh, we do to. This is our third year coming to this
and we decided that it would be fun to get a room.
That way we don't face driving home plastered." Ted
laughed. "My wife met a friend and deserted me just
when I was getting warmed up for some dancing. That's
why I asked you," he said looking at Bob, "that and
the fact that I saw you on the floor."
"Oh," Bob smiled.
As the music played, Ted bought a couple of rounds of
drinks. He carried most of the conversation. Bob
managed a few "uh huh's". Finally Ted asked Bob to
dance, again a nice fast dance. Bob, feeling the glow
of his whiskey sours, didn't hesitate this time. Casey
didn't have to coax him; he was up quickly holding
Ted's hand. When the dance ended, Ted held Bob's hand.
"Another?"
"OK," Bob whispered.
The music started. It was a slow dance. Bob felt Ted
wrap his arm around him, without thinking about it,
Bob was dancing. As the dance progressed, Ted pulled
Bob against him. Bob became aware that Ted had a rather
substantial hard on. He could feel Ted pressing his
cock into him. He felt Ted's hand begin to rub his ass,
soft firm squeezes, pulling Bob into the hard meat.
Bob's cock responded, it grew stiff and hard, pressing
against the tummy tuck panties, pushing out against
the panty hose, making a bulge in the black sheath
dress. He was sure that Ted could feel his hard cock
just as he felt Ted's.
"Umm, Bobbie. That feels real good. You are very good.
How long have you been doing this?"
"Huh?" Bob worried.
"Dressing. How long have you been dressing?"
"Uh uh, uhno," Bob mumbled. His cock melted as he
realized that this man knew.
Ted placed both hands on Bob's ass, pulled firmly and
ground his cock into Bob. "You're the hottest I've
seen. You can talk to me. Tell me, how long?"
"First time?" Bob mumbled, unsure what to do.
"Un-fucking believable. This really is just your
Halloween costume? I don't believe it, you're too good
and too into it for this to be just for Halloween."
"Really, this is the first time. I, uh..uh.." Bob was
nervous. He still felt Ted's hard cock pressing into
him, still swayed to the music allowing Ted to grind
the hard meat against him, was still enjoying the
firm hands on his ass.
"Maybe, but you like it. I can feel it. You like
showing off your legs, fantastic legs! You like
having me look down your dress, checking out your
tits. You feel my cock don't you? Feel it hard. I
could feel you get hard to. I feel it getting hard
again, right now," and Ted pressed his cock into Bob.
"Yeah, I do, I like it," Bob said, realizing that he
was doing something he had always wanted to do.
The music stopped. The two returned to the table.
Casey had been watching. She could tell that Ted had
figured out Bobbie was Bob. What she wondered was how
Bob was going to react.
"This thing's almost over. Would you two like to come
up to my room for a nightcap? My wife won't be back
for hours."
"What do you think Bobbie? Sounds like a good idea to
me," Casey said.
"Ahh, I don't think so. If your wife comes back she
might be upset." Bob fidgeted.
"Look, don't be shocked. She's gone off with a man we
met here tonight. We have sort of an open relationship.
She doesn't get turned on by some of my interests so
we each have our own fun occasionally."
"What kind of interests? Casey laughed. "Not a serial
killer I hope."
"No, no, no. Can I be honest? I'm bi. I get really
turned on by TV's and TS's. I just thought it would
be nice to talk for a while. I just can't believe this
is Bobbie's first time out."
Bob flinched at this reference. He had never thought
of himself as a transvestite or transsexual or even
bisexual. This was going further and faster than Bob
had anticipated. On the one hand he was reveling in
Ted's attention and compliments, had gotten more
excited than he ever imagined when he felt the man's
hard cock pressing into him on the dance floor. On
the other hand he was frightened at the prospect that
this was probably leading to his first sexual contact
with a man.
Once again it was Casey who pressed the situation.
"OK Ted, lead the way."
Casey and Ted did all the talking on the way to the
room. Once there, Ted mixed them all a drink. The
room was large with a small couch and chair forming
a sitting area at the foot of the king-size bed.
Casey was quick to settle into the chair leaving Bob
to share the couch with Ted. It was clear that Casey
was signaling to Bob that she wanted him to go for it.
Ted handed them the drinks, "Hope these aren't too
strong. Do you mind if I change out of this silly
costume?"
"Go ahead."
Ted stepped into the walk-in closet and in a minute
reappeared in sweatshirt and loose cotton shorts.
He settled in next to Bob. The slit on Bob's dress
exposed most of his leg; he shivered as he felt Ted's
bare leg now pressing against it.
Ted dropped his hand onto Bob's thigh, "You know I
heard a couple of women on the dance floor envying you
these legs. I can't say that I blame them. This feels
exceptional." Ted slowly rubbed the warm thigh.
Bob's cock started to get hard. "Thanks. I run a lot."
He didn't know what to say or what to do. He looked
down at Ted's lap and saw the cock outlined in the
short pant leg. The outline reached almost to the cuff.
Ted's hand worked slowly up the inside of Bob's thigh
and was now rubbing next to his balls. Ted seemed to
be avoiding actually touching Bob's balls or cock,
both of which were throbbing inside the panty hose.
Then Ted withdrew his hand, moved it to Bob's hair. As
he stroked the shoulder length blond tresses, he
included caresses of the neck. "You have beautiful
hair. You are very lucky. It is so sexy to find someone
with real hair rather than a wig. Do you like this?
You feel tense. Just relax."
"Yeah, that feels good. Especially on the neck. I like
that."
With that encouragement, Ted began an affectionate
massage of Bob's neck. Then with his other hand he
took Bob's hand. Ted softly but firmly pulled Bob's
hand onto the bulge in the cotton shorts, then pressed.
Another shiver of excitement. Bob squeezed the cock.
It was hard and very warm.
Bob grabbed the cock through the material and gently
stroked it. He looked down and watched his hand rubbing
the lump in the shorts. He watched as he pulled back
and the pant leg drew back. He saw the tip of Ted's
cock peek out from beneath the material. He did this a
few times, each time exposing more of the dull red cock
head. Then when the head was in full view, he moved his
fingers over to touch the naked skin. He rubbed the
flared head along the ridge then down to the piss hole,
felt the slick precum, rubbed the precum around the end
of the shaft.
He moved his fingers down the length of the shaft,
drawing it out from beneath the cotton shorts. It
looked larger than his own cock. Both longer and
thicker. It was hard but didn't have the same feel
that his own cock had. This cock felt softer, more
like a sausage or hot dog. Ted reached down and drew
aside the leg of his shorts, completely freeing the
warm shaft and the balls beneath.
Then as Bob lifted the thick meat to better view the
balls, he felt Ted's hand return to the inside of his
thigh. This time the hand worked its way under the
dress then proceeded to the hard cock. Bob spread his
legs and enjoyed the feel of the panties being rubbed
against his cock, the feel of the hand pressing against
his shaft.
He looked at Ted's balls. A huge wrinkled sack that
moved up and down as Bob stroked the cock up and down.
He slid his hand down to feel the balls, he cupped
them in his hand, lifting them slightly, feeling their
weight. His hand returned to stroking the shaft.
Bob glanced up at Casey. She sat quietly, clearly
enjoying the show. She had a hand inside her shirt.
Bob knew she was pinching her nipples. The fact that
she was there added to his excitement removed his
apprehension and fear.
As Bob bent forward to enjoy the sight of this cock in
his hand, he felt Ted's hand still caressing his neck,
fondling the blond locks, but now also gently pressing
Bob closer to the cock. "Go ahead Bobbie, get next to
it. Touch it. Touch it with your tongue."
Bob didn't resist, he knew that he wanted to feel the
cock on his face, in his mouth. He allowed his head
to be pushed next to the cock. Bob moved his hand back
to the balls, he saw Ted's hand wrap around the thick
cock then rub the warm shaft against Bob's cheek. Ted
rubbed the firm meat all around Bob's face, then rubbed
the head against his closed lips. Bob could feel the
slippery precum as the tip slid across his lips. "Lick
it, Bobbie. Give it a nice kiss."
Bob stuck his tongue out, licked gingerly on the very
end, felt the piss hole with his tongue. He licked
around the head, gaining confidence and enthusiasm.
Ted's hand dropped away from the shaft, Bob opened his
mouth and swallowed the head. He licked around the
head while holding his mouth still, his lips locked
just over the high crown of Ted's cock head. He felt
Ted move up and down very slightly, ever so slightly
fucking Bob's mouth. Bob went down further on the
shaft but gagged when he had only half of it in.
"That's ok Bobbie. Just suck the end. Just lick and
suck, you're doing great. Squeeze my cock while you
suck it, ok Bobbie. Hmmmmm."
Bob felt both of Ted's hands on his head now, running
his fingers through Bob's hair. Bob worked the thick
shaft in and out of his mouth, swirled his tongue
around feeling the flared head, probing the small pee
hole. His jaws were getting tired. He pulled his face
off the cock, rubbed the wet shaft around his face
again. Ted's hands still on Bob's head now pulled him
up. Suddenly Ted was kissing him. Without a thought,
Bob returned the kiss, sucked the tongue that Ted sent
into his mouth. Returned the tongue favor to Ted.
"I wanna fuck you. I wanna fuck that beautiful ass of
yours. I wanna feel those fabulous legs over my
shoulders", Ted breathed into Bob's ear.
Bob realized that he had known all along it would come
to this. He was so excited and so scared that he
couldn't speak. He wasn't really afraid of being fucked
in the ass. Casey had fucked him a few times with a
dildo. He liked it. He was really afraid of finding out
that he liked having a man fuck him in the ass.
Ted didn't wait for an answer. He lifted Bob to his
feet and began undressing him. Bob didn't resist; he
just sort of allowed Ted to control and direct him now.
With an alacrity that bespoke much experience at this,
Ted soon had Bob naked and on the bed. Ted shed his
shorts and sweatshirt, retrieved some lubricant from
a shaving kit, and lay down next to Bob.
Ted pulled the trim young body close, stroking his back
and ass. Bob felt the warmth of Ted's body against his
own. He felt his own hard cock pressing into Ted. He
felt Ted's thicker hard cock pressing back. He reached
between them, found the hard shaft and began stroking
it, rubbing it against his belly. Ted resumed kissing
Bob. Almost immediately the two were feverishly
tonguing each other's mouth. Ted took Bob's cock,
pulled it to his own, then held both cocks in his hand
and squeezed them together. Bob's cock felt the warm,
hard cock. Ted continued this double jack off for
awhile as they kissed.
Ted rolled over on top of Bob. Bob looked down his
belly and saw the two cocks; Ted's on top of his. Ted
rocked back and forth, rubbing his cock on top of Bob's
as Bob watched in excitement. He watched as Ted applied
lubricant to the thick cock, liberally greasing the
dark red head.
He tensed with anticipation and anxiety as Ted lifted
Bob's legs to gain access to the virgin ass hole. Bob
felt Ted's finger rubbing lube around the ass hole
then slide in. Ted slid his finger in and out a few
times, as he did this he stroked Bob's hard cock. Then
Ted brought his own large cock to replace the finger.
With gentle firm prods, Ted pressed against the
puckered hole. The head of Ted's cock slowly spread
the opening a little more with each slight push. Bob
tried to push his ass into the cock, anxious to feel
it inside of him.
Bob winced as the head finally gained entry. Ted
paused to let the ass hole adjust then pressed in a
little more of his cock. The cock now moved more
easily. Ted began slowly fucking Bob's ass and at the
same time stroking Bob's cock.
"You like it Bobbie? You like my big cock in your
sweet ass?"
"Oh god yes. Oh shit it feels so big in my ass."
"That's because you've got the tightest ass I've ever
fucked. And the hardest cock. Shit your cock is like
a rock."
"Fuck me. I want to be fucked!"
Ted could feel Bob's ass hole tighten around his cock.
He pressed deeper on each stroke so that he was soon
burying the full length of his cock in Bob's ass. He
rubbed some more lube on the shaft of his cock, then
began fucking faster. He looked down at Bob beneath
him. Even without his dress, he still looked gorgeous.
His makeup was still quite good, his shoulder length
blond hair, his delicate features. And the kid was a
virgin! Ted was in heaven.
Once Ted added the additional lube and had buried all
of his cock in Bob's ass, Bob started to feel really
good. He could feel the thick shaft as it moved in and
out of his ass, he could feel the huge balls slap
against his ass. He liked it! He loved it!
Ted could feel himself getting close to cumming. He
stroked Bob's cock expertly, trying to get the young
man to cum close to the same time as himself. He knew
that was the best. To be shooting his hot load into a
guy's ass and jerking the guys cock to shoot cum all
over at the same time.
"Are you close Bobbie? Do you feel it? Feel my cock
ramming you. Are you ready to cum baby?"
"Do it. Do it harder. Yes I'm close, jack me off, fuck
me, fuck me, fuck my ass!"
Ted couldn't wait any longer. His balls ached and his
cock throbbed as he rammed into Bob's ass. He groaned
and buried his cock deep into the ass as he felt the
cum bursting forth. It was now down to a few great cum
strokes, feeling the cum fill the ass, feeling the cum
squeeze around the hard cock and dribble out down his
balls.
Ted stroked Bob's cock hoping for a mutual climax from
his partner. When Bob felt the sudden warmth in his
ass, felt the juices filling him, heard the groans of
pleasure from Ted, Bob's body responded. As soon as
Ted was finished cumming, Bob's cock spewed forth a
jet of cum that shot several feet in the air.
"Yes! Yes! Ohh yes! Shit yes!" Bob yelled as he
continued to spurt cum from the sinewy bone. Ted
marveled as burst after burst issued from the cock in
his hand. With each burst, Bob rammed his ass back
forcing Ted's cock deeper into his ass.
Ted started to pull out.
"No, wait. Leave your cock in. I want to feel it in my
ass a little longer."
Ted tried to hold his cock in, tried to keep it hard
but it was soon soft and slid out of the slippery hole
that was now stretched wide by the furious fucking,
was now slick with lube and cum juice.
"That calls for another drink!" Ted moved to the liquor
bottle.
Casey came to the bed. "That was hot sweetheart. I
think you waited to long for that."
"Geez Casey. I had no idea. I mean..."
"Shh. I understand," she pressed a finger to Bob's
lips.
Ted returned with fresh drinks, "You two want to stay
the night, or I guess I should say morning," he
chuckled.
"No, I think we'll go."
"Well, give me your number. I'd like to get together
again. I meant it when I said you are fabulous."
"Why don't we take your number? This is a new area for
us. Maybe you'll just have to wait until next
Halloween," Bob laughed.
They finished their drinks and said goodnight.
The End
The author welcomes your comments, ideas and discus-
sion. Half the fun is writing a story, the other half
is knowing that someone actually enjoyed it.
Please write to laffwithme99@yahoo.com
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It's okay to *READ* stories about unprotected sex with
others outside a monogamous relationship. But it isn't
okay to *HAVE* unprotected sex with people other than
a trusted partner. You only have one body per lifetime,
so take good care of it!
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Kristen's collection - Directory 10