Username: freefall
Password: *******
As always, I checked out the chat rooms after I logged on. I searched
the list: sissy cross-dresser; cross-dresser for m; cross-dresser for
f; but all my favorites were full. I even tried them, just to be sure.
Access denied. Room is full. I hated when they were full. Also, none of
my buddies were online yet. So, I scrolled down the list of rooms,
trying to find one to enter. I never really chatted in them anyway. I
liked to enter, check out people's profiles, halfway follow the
dialogues, and hope someone would IM me. Or if someone looked
interesting, or local, I'd IM them. Usually just to found out a little
about them. If they were another cross-dresser, I'd find out what they
liked, if they had advice, or just have some interesting conversation.
A few months ago, before I decided it was better to be honest online, I
might mess with them. One night I'd be a horny female, the next a pre-
op TS or maybe just a young, hung stud looking for action. Now, I
actually had a real profile and told the truth, except for exact name
or location details. Tonight I was ready to go look elsewhere, when I
saw the cuckold husband room. I used to go here, before I decided to
concentrate on my sissy side and be honest in my conversations.
Cuckolds were men whose wife would have sex with other guys. The other
guys were known as bulls and often they liked to dominate the cuckold
as well as have sex with the wife. I'd play the role of pussy-whipped
husband, sent to find studs for his cheating wife. The horny bulls
loved it. Of course it was all fantasy. Most knew it, I think, but it
was still fun cyber. But once I decided to come clean with my real
interests, I stopped visiting the room. I had nothing really to tell
them.
The room was only half full. It didn't take long to see who was there.
There was just the usual mix of cucks and bulls. Little real room
action, most talking took place by individual IM. I was getting ready
to leave, when the IM window popped up.
"Cuck or bull?"
That was the standard entry from one male to another, especially when
the profile wasn't clear as to your preference. Mine wasn't. I talked
about my wife, state, and hobbies. Honest, but not specific enough to
single me out. I could tell from the name, MTNBULL, what he was. I
answered honestly.
"Neither, I'm a married cross-dresser."
"Does your wife know? Does she dress you?"
"No, I've fantasized about it, but nothing more."
"Too bad, I like fem husbands. I could get her to dress you, if you're
interested."
"I don't think so; she's pretty old fashioned."
"I know, but I have my ways. I've helped many sissy husbands find their
true place in their marriage."
From then on, we chatted. I admit he had a way to him. He was very
personable and friendly. Most of our chat was about my wife or me. He
was a good chat listener. I told him I loved to cross-dress, was prone
to be submissive, and my fem name was Missy. He gave me just enough
background to find out he had been a bull for some time. He said his
name was Clint and he lived in the mountains close by. Once we
established how close we lived to each other, he began to ask how he
might meet my wife. Did she chat online? Could we meet him at a bar or
a restaurant? His interest and charisma made this much more exciting
than other bulls I had talked with. Before I knew it we had talked for
nearly two hours. Finally, I had to sign off. As a parting message he
said to think about how we might get my wife involved. He said if I
could get her to talk with him, he'd guarantee that she'd be more than
willing to make me a fem husband. After I signed off, I chuckled.
Knowing my wife Jennifer, she would not be easily talked into anything
or most likely not even be interested in meeting or talking with him.
During the next few days, this conversation kept coming back to me. I
couldn't forget how assured he was. He knew he could convince my wife
to participate in my cross-dressing. This had long been a prime fantasy
of mine, and even though it seems remote, I couldn't forget it. As I
thought of that chat, it always progressed to how I could introduce
Jennifer and Clint. She rarely went online and never went to chat
rooms. So giving him her online name wouldn't really work. She always
deleted email from names she didn't recognize, so that wouldn't work.
If we went to a bar or restaurant, she was not the type to start
forming a friendship with someone we just met. We had only a few
friends we socialized with, and we had known them for a long time. We
occasionally did neighborhood activities, but again it only reached a
certain level of friendship. None of these encounters ever reached a
level of intimacy that would lead to sex or a cross-dressing episode.
When I would logon, Clint would IM me to see what was happening. He
always made a point of asking me about my cross-dressing. Real detailed
questions about what I liked to wear, my sizes, whether I wore makeup,
and if my hair was long or short. He seemed to enjoy my detailed
descriptions and encouraged me to be more feminine. And I began to do
that. For example, instead of getting my usual short haircut, I had the
stylist not trim much, but shape it. I told her I was looking for a
longer style for a change.
Clint never pressed me, but was clear that if I wanted her to put me in
skirts, he could deliver. Even then, he was casual about it. As if he
was just doing a service for me.
The one thing I knew that Jennifer was most passionate about was her
love of the Old West. Stories of gunfighters, gold rush towns, and
particularly the history of Tombstone, the OK corral, and the
principals involved were her greatest hobby. She knew everything about
them. Had researched, read, and bought all the books written on them.
Then it came to me. She had once had a long-range exchange with an
older, English professor who was studying the gunfight at the OK
corral. She had answered a question he had posted on a message board
about Tombstone. She had really enjoyed this and had often sent him
books or clippings for his work. We even exchanged Christmas cards with
him and his wife. This might be an avenue for Clint to make contact.
The thing was he had to let her make the contact and promote it.
Otherwise, she would likely stay remote. I thought about it for a
couple more days.
To make that route of contact work, I needed to know where the board
was. Then I could give Clint the information and he could post a
question. That would be the bait for Jennifer. It would then be fate if
she answered and was drawn into more exchanges with him. I waited until
I was sure she had gone to the board, and then checked the history
summary. It gave me all the recent places she had visited when online.
She had a Facebook page, a few favorite e-stores, auction sites, and
yes, a couple of Old West message boards. I found the one that she
looked at most often.
Now I had the information, but what to do? Did I really want to play my
wife that way? Did I really think Clint could deliver? Or was it just a
fantasy? The latter seemed most likely. In fact, I used the scenario to
my satisfaction to masturbate quite a few nights. But then, like all
fantasies it began to get old. It wasn't enough just to imagine it.
What I needed was that next step. If I gave Clint the board name, it
would juice everything back up. I could go for weeks expanding my
fantasy. And odds are, Jennifer wouldn't even see Clint's message or
respond if she did. Finally, I decided to go for it. Good fantasies are
hard to create and I wasn't ready to see this one die so soon.
I logged on and went about my usual online business. Soon the IM window
popped up - MTNBULL.
"Hi Missy, you got any ideas for me tonight?"
"Hi Clint, maybe so, I think I have a way that might work."
"Go on, what do we have to do? I'm dying to see you in some panties."
"She likes Western history. You know Wild West type stuff. Maybe if you
posted a question about history on a western board, she might contact
you. That way, it would look natural and she wouldn't be on guard. But
it would be up to you to make more contact, if she responded to your
post."
"Missy, I think you've got it. That is a subtle but workable approach.
And don't worry, once I get her to chat with me, you'll be wearing
skirts in no time."
"Well, we'll see. The board name is Tombstone_chat.org. You'll need to
ask a question about some aspect of the town's history. Maybe ask a
question about the famous gunfight or the main fighters. She knows it
all, so you must make it realistic. Do you think you can find
something?"
"No problem little Missy, I'm a fan of the Wild West myself. Actually
grew up on a horse farm. I'll check out a few sites, and see what kind
of angle to take. What's her e-name?"
"Not yet Clint, just let me know who responded to your post and then
I'll let you know if she is one of them."
"Great little Missy, I'll catch you later."
Now that he was gone, I had the first regret. You know it was like
lighting a fuse. Nothing had happened yet, but it was smoldering right
in front of you. You knew you were safe now, but in a while a real
explosion could take place. But it did give my fantasy the juice I
needed. It was great imagining how it might go. But even in my
imagination, it felt like a fantasy. Jennifer would never participate.
The next few weeks slid by. I was busy at work and when I logged on at
home, I never received an email or IM from MTNBULL. My fantasy
gradually became routine and I had just about forgot about the
incident. I thought of it as one of my riskier failures. Then at dinner
one night, while we were exchanging chitchat about our day's
activities, Jennifer gave me a jolt and re-awakened the idea. Casually,
she mentioned that she had seen a question about Tombstone on one of
her favorite chat boards. Turns out, it was a local guy who was real
interested in what happened to the Earp's after their history making
shoot-out. She had emailed him several times and he seemed real nice.
She remarked that it was refreshing to have someone local to chat with
about it. She often felt she was the only one in this area that liked
the Wild West. Plus he was also so polite and friendly, almost like she
had known him for years. Her tone gave me the chills, because I had
gotten the same feeling when I chatted with Clint. He honestly had a
way of making you feel both special and comfortable. I was real anxious
about this and had a knot in my stomach. I had assumed that even if
Jennifer and Clint interacted on the chat board, that she wouldn't be
more than mildly interested. I could tell from her recollection of the
interactions that she was more than mildly intrigued. Now, I wasn't
sure what might happen next. Plus, it was out of my control. Jennifer
and Clint were developing their own dialog and I was on the outside
looking in. Of course it fueled my fantasy, but now these masturbatory
events had a dark edge to them. Lurking in the background was the
possibility that this might happen. Even more sinister was the idea
that Clint was a sexual predator and he was longing to have sex with my
wife. Not only that, but he wanted to make me seem like less than a man
while he did it. Although this was great fantasy, I wasn't ready to
take that radical a step in real life. I spent the next few days in
both a sexual heat about the fantasy and a dreadful apprehension of
where they might be going. I kept checking online, but I had not seen
MTNBULL for some time, and I was afraid to email him. My one hope was
that perhaps he didn't know that the person responding to his questions
was my wife.
My fears about Clint were well founded. When he had posted the notice
on the Tombstone board, he had used another online name. He had a
couple of people respond, but with a little checking he found only one
was local. He figured this had to be her. Once he focused on her, he
had emailed almost daily. First with questions about Tombstone, the
Earp's, and the Wild West, then he gradually began to interject
personal conversations. He mentioned fairly early in their exchanges
that he had a steady girlfriend and talked about her often. This helped
establish him as a regular person with Jennifer, and not some online
stalker. Clint talked about how they did so many things together, but
that his girlfriend wasn't as interested in the Wild West as he was.
This was a further link with Jennifer. She had often complained to me
that I showed little acceptance of her hobby. As they became regular
email partners, Clint ratcheted up the action the next step. He noticed
when she logged on, and observed that it was almost exclusively during
the day, when I was at work. Finally he sent her an IM and began to
chat real time with her. This allowed him to work Jennifer with more of
his charisma and charm. Soon she began to IM him back and they often
would spend an hour or so chatting during the day. Although some of the
time was spent talking about their hobby, often the conversation would
drift to their partners, work, and everyday life. Clint was good about
extracting information, and always inquired about our home life or me.
This made him seem more like a close friend, almost like a girlfriend
Jennifer could confide in than a male. As he promised, Clint was good
at making himself liked. But he always maintained enough distance, that
Jennifer wasn't threatened. He was obvious master at the art of
conversation and relationships.
The newly developed friendship prompted Jennifer to go the next step.
She loved to shop and if given an opportunity loved to buy presents for
friends and family. Because Clint had demonstrated such an interest in
the Earp's, but seemed to be fairly uninformed about them, she decided
that one of her favorite books, "Wyatt Earp, the Life behind the
Legend", would be perfect for him. She spent several weeks shopping
online, until she found the book at just the right price. Jennifer was
feeling pretty good. She had found a great book, at a great price, and
now would be helping a fellow 'cow poke' to learn more about their
interests. This in turn, would spark more conversation and speculation
about the various uncertainties associated with the legends. All she
needed was his address, and when she logged on early that morning she
immediately began typing an email to him requesting a shipping address.
However, before she could complete the message an IM popped up from
Clint - EASTCOWBOY.
"Hi DESERT FLOWER (his nickname for her), how is everything going
today? Anything special going on with you?"
"Hi COWBOY, nothing special today, I just have a few errands to run
later. But I was just getting ready to email you. I need to have an
address for you that I can send something to. Would you let me know
that?"
"Sure I would, but I've got a better idea. I was just going to check
with you to see what your plans were for today. I've got some meetings
on the west side of Charlotte and thought maybe we could get together
for lunch? You pick the restaurant, somewhere you like and I'll meet
you there. How about it?"
Jennifer was surprised. Even though they lived but 130 miles apart, she
hadn't really expected to meet him in person. Not that she was worried;
he had made her very comfortable with their friendship. So, it didn't
take her a moment to respond. She could meet him at 12:30, if that was
ok, at the local Chili's. As they worked out the details, she smiled.
Clint had never asked for a picture and she was dying to see if he
looked how she had imagined him to be, sort of a watered down version
of Kirk Russell. Also, the chance to see his face as he saw the book
would be real rewarding. So the date was set.
Now she had to hurry. She had just planned on going to the grocery and
pick up some dry cleaning, and was dressed fairly casually. But with a
more interesting day planned, she began to choose her outfit. Nothing
too fancy, but she wanted to make a good impression on her new friend
and she figured he would be in a suit for business meetings. She
finally picked her new pink and black tweed pantsuit and black
turtleneck. She knew the outfit highlighted her bust and small waist
while hiding her larger bottom. The right amount of makeup, featuring
her lovely large brown eyes, and styling her hair efficiently with her
curling iron and she was ready with time to spare. Although she
wouldn't admit it, this was as close to a date as she had had in a long
time.
Walking into the restaurant, she scanned the bar looking for suitable
candidates. Clint surprised her as he stepped out from a side area, and
politely asked if she was expecting to meet a cowboy. Jennifer felt at
ease right away, but what really took her back was how he looked. She
had imagined an ordinary guy; about 5'10", appropriate in weight, and
hoped he would be decent looking. When she saw him at first she was
stunned. Clint was tall, probably 6'3"or more. He was thick across the
chest, but not heavy. He wore tight blue jeans, a leather sport coat,
cowboy boots of course and a white shirt. But what really caught her
eye was his mustache and thick dark hair; he looked like a younger
version of Sam Elliot. She was expecting to find a nice guy, but Clint
was much more attractive. The lunch went really well. They had a great
time. He loved the book and they spent a lot of time talking about
their partners. He even showed Jennifer a picture of Vicky, his
girlfriend. It was obvious that Jennifer and Clint enjoyed being
together. Jennifer promised that they would do it again and Clint
kissed her hand as they parted. All she could think was that he was a
real gentleman.
I nearly choked when she told me at dinner. Jennifer gave me the whole
story, although she didn't provide many details on Clint's appearance.
To her it was just an innocent lunch and a chance to firm up a new
friendship. She beamed when she described how he had reacted to the
book. All I could do was nod quietly. Was she telling me everything?
Had Clint told her we had chatted? Did he broach the subject of my
dressing? Had he tried to make sexual advances on her? A million
questions ricocheted in my head, but I just sat meekly and let her
finish her story. Finally, I softly replied that it sounded like you
had a good time and he seemed nice. I didn't know what else to say, or
do. I kept replaying the incident over and over in my head, each time
reflecting back on my fateful IM that gave Clint the key to contact
with Jennifer. Why? Why? It was just supposed to be a fantasy. Now I
had made it far too real. I knew Clint would pursue this even more.
Maybe if I could talk to him tonight, I could persuade him I no longer
wanted to involve Jennifer in my cross-dressing. It was a long shot but
all that I had.
I logged on apprehensively that evening. I had tried to come up with
the right approach to convince Clint to end this, but wasn't sure of
it. Before I could search or bring up a chat room, an IM flashed on the
screen.
"Hi Missy. Thank you, thank you, and thank you. You sissy cucks never
realize how grateful a bull is when you set us up with your lovely
wives. All you're thinking of is your needs, but a bull appreciates
what treasure you have."
I couldn't help but blush when I read this. I knew he would not back
off and his assessment of my motive was dead on. I tried to think of a
reply, but nothing left my fingertips.
"Your wife is stunningly attractive. She is going to be so much fun to
fuck. I could tell right away that she will be hot in bed and she is so
ready for it. You must have really been letting your husbandly duties
slide. It's rare that a woman that beautiful is so in need of a good
fuck. Thank you again."
Again I sat there, doing nothing. I wanted to tell him to stop. Don't
talk about my wife that way, but I knew he had seen that desire,
because it was true. Jennifer and I hadn't made love in months.
"Oh and don't think you can stop it now. I could've got her to a hotel
this afternoon and you would be none the wiser. I may not be perfect,
but I do know people and I can judge right away whether I can make the
sale. She is as good as mine. But don't worry that I'll back out of our
deal. After talking with her today, I can deliver my promise to you as
well. I will have no problems getting her to help make you a full blown
feminized husband. But it will be a cuckold sissy husband. That's the
price of the deal. So you can plan on it."
At this point, I finally replied. It was a meek response, with as much
of a challenge as I could muster: "Don't be too sure this will happen.
My wife is faithful, loves me, and wouldn't do anything to harm our
marriage."
"LOL. Who said anything about harming your marriage? She will be more
committed to it than ever. She'll still have you to provide for her,
and she'll probably start making you do the housework too. I will point
that advantage of a sissy out to her, once I get you in panties for
her. Plus she will finally get some real man sex. You never mentioned
it, but I could tell that you are less than endowed if you know what I
mean. The average male is about 6-7 inches erect, but I would bet that
you are much smaller than that, probably less than 5 inches when hard.
I don't normally brag, but I can give her much more than that. And I
really know how to use it. I know you've heard guys boast online about
size before or even show you one of those porn site cock pictures, but
I'm for real. Check your email and see for yourself."
I was shocked. He was so confident about her and being able to sissify
me. It was totally scary. Plus, I had to admit he was right about my
small size. When I was younger, I convinced myself that it was average
in length. But a few years ago, in one of my real submissive moments, I
had measured it. It was just over 4 ? inches hard and when soft it sat
there barely visible. I knew from locker room situations, that it was
much thinner and smaller than other guys. I had just put it out of my
mind.
"Missy, I've got to go. Be sure and check your email. Don't worry; I'll
let you know when I decide to close the deal with my new fuck toy. You
just be prepared to do as I say."
With that he was gone. I sat there, staring at the screen, until my
Mail icon popped up. Apprehensively, I opened Clint's email. My only
hope was that it was just another copy of the large guys featured on
porn sites. As the picture scrolled down my screen, all my hopes were
dashed. The picture showed the cover of the Earp book Jennifer had
eagerly bought for him. His cock lay across the cover with its head
right at the upper edge of the book. The way it laid there, it looked
huge. Not only long, but also thick as well, and a large bulging sack
at the lower edge of the book, indicated his balls were proportionally
matched in size to his penis. I quickly closed the email, and anxiously
reached for the book that was on a shelf next to the computer. I
fumbled through the desk drawers till I found a ruler. Hesitantly, I
put the ruler next to the book, just where his cock had been. My heart
sank as low as I could remember it. He was not lying; his cock was
easily over 9 inches and it hadn't even looked completely hard. I knew
Jennifer had never experienced anything like that with me. If Clint did
fuck her, as he said, she would likely be really disappointed when I
tried to follow that experience. I logged off and could do nothing but
fret the rest of the evening, Clint's boastful words flashing through
my mind.
Clint knew the next few weeks were critical. He never contacted Missy
and made a point to IM or email Jennifer every day. He was always
getting to know her better, to have her see him as one of her close
friends. Not that he didn't subtly begin to interject sex into some
conversation; it was just that he did it smoothly. Electronic flirting.
He was very good at it too. While Clint ingrained himself with
Jennifer, Missy worried more each day. The lack of interaction with
Clint was making him both nervous and a little more hopeful. Maybe
Jennifer had said no to him. Maybe Jennifer had gotten bored with him.
Maybe Clint had moved on to someone else. Clint was counting on this.
He needed Missy to be totally vulnerable, and to follow every
suggestion his new bull made. Not that Clint doubted that he could have
sex with Jennifer. He knew he could score. But what he loved was how
the husband looked when he took their wife. Especially, if Clint could
fem them - that was the total power trip. The rush from watching the
wife see her husband as a sissy and her realizing that she could still
have explosive animal sex, with him, and have a sweet little plaything
was something Clint never could get enough of. To be honest, Clint had
never found the right couple to take it as far as he wanted. He thought
with the right couple, he would aggressively feminize the man, while
enjoying the woman. Eventually he might move on from the couple, but
only after he had trained the husband and given control to the wife.
But the first step, where the husband willingly followed his directions
was critical. Missy had to take the initial steps himself; otherwise
Jennifer wouldn't be open to all that would follow. Most women would
not have sex with another man, in front of their husband, or watch him
prance around in lingerie, or be comfortable with their husband blowing
a man; Clint knew he had to make this transition just right or it would
fail. However, Clint didn't need to worry, luck was on his side.
I was busy at work, when the phone rang. It was Jennifer and she was so
excited she was almost breathless.
"Honey, do we have any plans for the first weekend next month?"
"Nothing really, what's got you so excited?"
"You won't believe it. There is a western convention coming to
Asheville, that weekend. They will have all kinds of memorabilia,
displays, and some lectures about the Wild West, including a special
session about the shootout at the OK Corral. I couldn't believe it. We
have to go. Can you make it a long weekend? We would go up on
Thursday."
"I guess so; I have plenty of vacation left."
"Great and now for the special surprise, we can stay at the Sheraton on
the River for free! You remember my friend that I chat with about the
west, Clint? He says his friend owns the hotel and he can get us a
room. He wants to meet us there. He seemed as excited about it as I
was. Can you believe it?"
I don't remember what I said, all I could think about was he had done
it. We were going to meet him. And we were going to his turf. There was
no way he wasn't going to try to close the deal. I was confident of
that. I was trying to think of way out, but knew it was hopeless. I
hadn't heard Jennifer this excited in years. So now I would reap what I
had sewn.
Clint couldn't wait for Missy to log on that night. He knew it was time
to seal the deal. Once he heard at the Clifton chamber meeting about
the convention for western memorabilia, he knew the game was on. A
quick call to Randal to line up the room and then he went for the kill.
Jennifer was so excited he got a hard on just talking to her. He could
see her already, naked, her breasts flushed and nipples hard, her cunt
lips glistening and swollen, begging to be taken, begging to feel his
hard cock, to feel the kind of fullness she had never had. And above
all he would be sure to have Missy know about it, to have him in
panties and submissive. That was the kind of image that made Clint
hard.
He wasn't sure why, but he knew he should log on that night. After
talking to Jennifer, he had stumbled through the rest of the day, the
events all a blur. After dinner, he sat down at the computer, and went
online. He didn't have to wait long.
"Hi Missy, you excited about the great news? The time for you to become
a sissy cuck is here."
"Hi Clint, yes I guess the time is here. I'm just not sure I still want
to do this. I mean, do you need to do it this way?"
"LOL. It's too late now little girl. I am going to fuck your pretty
wife. Give her the big meat she's never had from you. If you don't want
to play so be it. I'll just make her mine. But, understand, having her
sneak off to meet me to fuck will be worse than if you just follow our
plan. Not knowing when or how often she is meeting me will consume your
waking hours. But, I'll give you the option. You wanted me to get
Jennifer to dress you, put you into pretty things. I can do that but
you must follow these instructions."
"First, I want you smooth. You must shave everywhere. You can leave a
little patch over your tiny dick, but I want you smooth everywhere else
and I mean everywhere. Second, when we meet, I want you to follow my
lead. If I ask you to do something, I want you to do it. And do it with
enthusiasm. Finally, when I call you by your sissy name Missy, I want
you to call me sir. To show me the respect I deserve. You do these
three simple things and you'll get your dream. You've made the payment.
I'm going to make your wife my little fuck toy. If you don't want to be
the sissy you dreamed of then that is your choice, but I'm collecting
my fee."
With that, Clint signed off. I just sat and stared at the screen.
Like most things you dread, at first they seem a long way off. But
before you know it, the time is at hand. It was that way for me. I had
scheduled my vacation and we had packed everything for our long
weekend. The weeks of anticipation were over. Jennifer could hardly
wait to go tomorrow. I felt trapped. Standing in the shower, I began to
shave. Although I was not extremely hairy, it took longer than I had
expected. I half expected Jennifer to ask what I was doing. When I
stepped out to dry off, I could see how more feminine I looked without
hair, Clint was right, it was an important step. I quickly slipped into
my pajamas and got into bed. Luckily, Jennifer was already asleep.
The drive to the mountains was uneventful. Jennifer was planning out
her trip, talking about all the activities at the convention. All I
could think of was her fucking that huge cock. How our life would never
be the same again. Soon we were there. We checked into the hotel and it
was very nice. More than just a room, Clint had arranged for a nice
suite with a balcony and view of the mountains over the river. The
bedroom was dominated by a very large bed, with silk sheets and there
was a fireplace and Jacuzzi. It was wonderful, a perfect place for a
wild weekend of sex. I was sure more than ever that Clint was a master
at this.
Jennifer took a lot of time getting dressed. She wore a nice sleeveless
black shift, short and form fitting, with black lace underwear and
black ankle strap heels. It was a bit dressier than what she would
normally wear, but you could tell she wanted to look good. Finally we
left for the restaurant. We were to meet Clint and his girlfriend there
for drinks and dinner.
As we walked into the restaurant, Jennifer saw Clint at the bar and
smiling widely, waved at him. At the table, she introduced him to me
and vice versa. He explained apologetically, that Vicky couldn't join
us tonight. At the last moment she had to cover for another pharmacist.
He was at a small cocktail table sitting on a wide leather booth. There
was only one other chair, a small, high stool. So Jennifer slid in next
to him, leaving the stool for me. Before I could sit down, Clint chimed
up.
"Mitch, how about you getting us some drinks? I'm buying. Get me a
double Jack on the rocks, and you two can have glasses of white
Zinfandel."
"Sure Clint, I'd be glad to."
It wasn't lost on me that white zin was Jennifer's favorite drink or
that he had me drinking it as well. It was like I was too much of a
light weight to drink real liquor. I quickly got the drinks and brought
them back to the table. As I tried to give Clint back his change, he
shook his head no.
"Good job. You keep the change as a tip. You make a nice waitress. Have
you done this before?"
His laughter seemed genuine and Jennifer giggled along with him.
Sitting on the little stool, I felt like I was perched there. We
engaged in rapid small talk, mostly about the convention and Jennifer
laid out her plans. I sat there almost like a spectator. Before long we
had finished our drinks. Clint looked at me and peeled another twenty
from his wallet and gave it to me.
"How about another round of drinks for the table, waitress? You don't
mind getting them for us, do you little Missy?"
The name burned my ears, but I knew what he expected as a response.
"I'd love to sir. I'll be right back."
I said it in as playful a manner as I could. Like I was going along
with his joke about me being a waitress, but it caught Jennifer's
attention. I turned and left for the bar, before she could see my face
flush.
"You know Jennifer, I don't mean to be rude, but your husband is not
what I expected at all. I thought you'd have a real masculine guy for a
spouse. You know, a man's man. Given how attractive you are he really
surprises me."
"He's more of a man than you think. He's just being friendly is all."
"Oh he's friendly enough, but it is more than that. I can't think of an
easy way to say it. Jennifer, he is just a pantywaist. I know lots of
guys like him. They are not comfortable being a real man. You know,
taking charge, making decisions, being the boss. Not that there is
anything wrong with pantywaists. They can be real helpful, like getting
drinks."
"Well I think you're wrong about him Clint. He is pretty strong at
times. I would never call him a pantywaist. He just likes to go along
and help out."
Jennifer said this with as much conviction as possible, but she did
wonder about Mitch some times. In the past, she had often wished he was
more assertive, and not just when they had business dealings, but in
the bedroom as well. Tonight, he had just met Clint, but called him sir
and practically ran to get our drinks. Given how nice Clint had been,
she was a bit surprised by his comments, which made her value his
assessment of Mitch. Clint had been a straight shooter with her so far,
why would he say something if he really didn't believe it? Maybe she
just hadn't noticed Mitch's true nature.
"Well I can prove it to you if you want. I bet I can get him in a pair
of panties before we leave the restaurant. Earlier today I bought some
lingerie for Vicky. It's in my truck. I'm sure I can get Mitch to put
them on. If I win, we go out after dinner to a fun little cowboy bar I
know about. If I lose, then dinner's on me. Do we have a bet?"
Jennifer didn't know what to do. She really doubted Clint's claim, but
Mitch was acting so submissive. Finally she agreed to the bet, just as
Mitch returned to the table, partially because she felt sure Mitch
wouldn't agree. But if he did, then well, she wanted to see where it
went.
I still felt like I was blushing when I got back with the drinks. I
knew better than even to offer the change to Clint. I tried to sit
down, but he quickly spoke up.
"Good job, Missy. Just keep the change, because I have another favor to
ask. I need you to go out to my truck and get a couple of things for
me. On the front seat, there is a wrapped package and a small gift bag.
Take these keys, it's the black club cab Ford parked by the entrance
sign."
I took the keys, and then knowing he expected it said, "Yes sir I'll be
right back".
Jennifer couldn't believe her ears. She looked at Clint and then back
at Mitch. He certainly was acting like a, well at least not like a
tough guy. Clint resumed his conversation with Jennifer and soon she
was immersed in talk about their plans for the weekend. It almost
caught her off guard when Mitch returned with two packages.
"Thanks little Missy, you have any problems finding them?"
I blushed deeply even before I answered, "no sir, no problems at all".
I even gave up the pretense of trying to act like I was joking around.
I sat down, and couldn't look Jennifer in the eyes. Clint took the
packages and handed the larger one to Jennifer. She smiled and acted
very excited as she opened the gift. It was a book about western
gunfighters - she loved it and leaned over and gave him a quick peck on
the check. It was just a gesture a friend would make, but the look
Clint gave me, made me feel tight inside.
"Glad you like it Jennifer. When I saw it I knew it was just what you
needed."
Although she had just reacted with the kiss, Jennifer was surprised
after she did it. I mean it was just a friendly peck, but in front of
her husband. But Mitch didn't seem to notice, or more accurately didn't
seem to object. He just looked down at the table after a quick glance
at Clint. Maybe Clint was right, and she thought it, maybe Mitch was a
pantywaist. One thing she did know was that Clint was not. He was
making her hot and so she decided to see what might happen and not
worry about it. She looked at Clint and took his hand, as she answered
him.
"Oh yes, I've seen it in book listings, but since it was out of print I
could never get a copy. How did you get it?"
"Just perseverance, once I made up my mind I knew what you needed and I
just worked to make it happen. That's how I am in everything."
Clint grinned slyly at me, although it wasn't needed. I understood his
message and knew now there would be no changes in plans. Just how it
might happen would be the only surprise.
"Ok Missy, now you open the gift bag."
I didn't expect that. So I opened the bag and reached in with some
trepidation. I felt the silky material before I even took out the item.
I didn't know what to say or do when I pulled out the panties. They
were a lacy v-string style in a light blue color. I just held them
there, on the tips of my fingers, as we all looked at them.
"Well what do you think Missy? Are they pretty?"
"Yes sir, they are very pretty. But why give them to me? These are for
women."
"That's right those are women's panties, but I thought you might enjoy
them. Sometimes pretty lingerie is enjoyed more by the man than the
woman. Do you think they will fit?"
"I guess they might, but I wouldn't know for sure unless I tried them
on."
"Oh you want to try them on for us? I was thinking they would be a nice
gift for Jennifer, but thought it was too forward for me to give them
to her directly. I love to see Vicky in sexy lingerie and thought you
might feel the same way about Jennifer. But if you want to wear them, I
guess I understand. Lots of waitresses wear sexy stuff under their
uniforms."
"No, no, if they were meant for Jennifer then that is fine. She can try
them later. I was just confused by your question."
"Come on Missy, it is obvious you want them. Some guys like wearing
panties. It fits their nature to be in women's lingerie. I get the
impression you're one of those guys. It will be okay if you go to the
restroom and put them on. Isn't that what you really want to do Missy?"
I felt trapped. Like the night Jennifer told me about chatting with
Clint. I knew he expected an answer and wouldn't take no. So I agreed.
"I guess I can try them on sir."
"Good girl, and while you're at it try the matching bra in the bag as
well. It's got a bit of padding and shaped cups that I think will fit
your body type. They should enhance your look quite well. But don't be
shy, I expect you to wear them if they fit."
As Mitch left, I couldn't believe it. Clint had been dead on right
about him. I mean he was going to put on panties and a bra in a
restaurant. I had to smile though. It was hot to see Clint manipulate
him like that. I always wanted Mitch to be more forceful, as that is so
sexy. So, if he wouldn't do it maybe Clint could.
"What I tell you Desert Flower? He is a natural panty boy, so it looks
like we go out for a drink and a little dancing after dinner?"
"You were right Cowboy. I would have gone anyway, it sounds like fun.
Mitch would never want to do that." She gave him a big smile and
squeezed his hand. Maybe this weekend would be better than even she had
hoped.
"Well I'm glad to hear that, but I want you to do me a favor. I think
you need to find out more about Mitch and his sissy side. So if I
suggest something for him, will you back me up?"
Jennifer was intrigued by his request, so she smiled and nodded her
head yes. His forceful squeeze of her hand sealed the deal.
I knew I was blushing when I got to the table. I was carrying the bag
with my underwear, and could feel the straps and tight band of the bra.
I didn't even want to look up, but did so as I sat down.
"How did they fit Missy? I guess ok, because I can see your bra. It's
very pretty. You can show us the panties later."
With that he laughed loudly and Jennifer joined in. This was worse than
I even imagined. We then ordered dinner and I got through it somehow.
Every time I looked at Jennifer, she just smiled and continued to chat
with Clint. I sat there silently the whole time. Finally, after Clint
paid the bill, naturally, we got up to go. They had told me about the
cowboy bar and I just nodded my head. By this time, I had no resistance
to anything Clint suggested.
Clint offered to drive and indicated that I should crawl in the back
seat. Once we were in the cab of his truck, Clint turned to me.
"It's time to show us how your panties fit, little Missy. Why don't you
slip off your pants and let Jennifer see if you look sexy?"
"Yeah honey, I want to see if they looked as pretty on your little butt
as they did in your hands."
Jennifer giggled as she spoke, and Clint looked at her. He knew this
was a very good sign that his plan was working. I took off my shoes and
slid my jeans down to my knees. I wanted to only pull them far enough
down my legs so they could see the panty. Clint would have none of that
and grabbed the bottom of one leg and pulled. I slid off the bench
seat, with my legs in the air, and he grabbed the other pant leg as
well. With a strong pull, he finished removing the jeans. As he held my
pants, I got off the floor of the truck and sat back down on the bench
seat. My face was starting to burn with embarrassment as I realized my
bare legs were on display. In the humiliation at the restaurant I had
forgotten about my smooth hairless skin, but he pointed it out right
away.
"Do you keep your legs shaved Missy? That's a nice touch. I like the
way your panties look against your bare skin. You must be a natural for
them. I guess not being very big down there is a big plus for you. But
with your legs being so smooth, you should wear skirts and not hide
them under those rough jeans. I think I have just the thing."
Reaching under the front seat, he pulled out a small carry-on bag and
showed it to Jennifer. He opened it, reached in, and took out a pair of
lace-top stay-up stockings in a dark brown color.
"Vicky keeps this bag in my truck in case we get caught out in the rain
or she needs a change of clothes. Given how well those panties fit,
these clothes should do just as well. Here put these stockings on those
pretty legs, they will look better on your bare legs than the jeans. I
think she keeps a skirt, top, and some shoes in here too."
Jennifer looked at my shaved legs, glanced over at Clint and back to
me. I could see a puzzled expression on her face. She reached out to
feel how smooth my leg was as if to convince herself she was seeing
correctly. Then, with a smirk she took one of the stockings and rolled
it up. Looking me in the eye, she grabbed my foot. Putting the hose
over my toes, she worked it up my leg. "That is how you put on a
stocking. Clint seems to be right about you again, hose always make
shaved legs look sexier. Go ahead and try the other one, Missy."
"That's the spirit Jennifer. I couldn't have said it better." I could
hear the gloating in his voice as we both realized his plan was
succeeding. I reluctantly took the other stocking from Clint and put it
on the same way Jennifer had. I glanced quickly at her face and could
see the mix of confusion, anger, and pleasure in her eyes. I could tell
she didn't understand why my legs were shaved or I was acting this way,
but had decided to follow Clint's lead to see where it went. He
continued to direct the action.
"Take off your shirt and let's see if your new bra looks as pretty your
panties."
I unbuttoned my shirt and slid it off my arms. As I did so, I knew
Jennifer would notice my bare chest under the blue bra as well as the
lack of hair elsewhere. With my shirt off, I felt vulnerable and
somewhat instinctively crossed my arms as if to hide my breasts. "It's
okay Missy you can show it to us." I reluctantly moved my arms to my
side. Clint laughed and Jennifer joined in as I followed his order. I
sat there feeling as embarrassed as I ever had in front of my wife. She
was obviously enjoying the show. He continued and told me he wanted to
see me in the whole outfit. As he spoke, Jennifer reached in the bag
and handed me the skirt, a short mini in light blue with dark blue
flowers and white lace trim around the hem. After I took the skirt from
her, I slipped my legs in it, pulled it up to my waist, and zipped it
closed. She next pulled out the matching blouse, a sleeveless V-neck
with lace around the neck. Although embarrassed, I dutifully put it on
too. I was sure that she noticed my smooth underarms as I slid the top
over my head and down my body. With the clothes on, Jennifer handed me
the shoes. The 3-inch heels were navy slides with a double band and
they fit easily over my stocking feet. Jennifer looked me over and
decided I needed to be bigger on top, so she took some tissues from a
box on the seat and stuffed my bra. The whole time they were smiling
and laughing as if they were watching a comedy. Finally I finished
dressing. Jennifer looked at me intently, and took her hand to play
with my hair.
"All we need now is a little makeup and something for you hair and
you'll look real cute. There's a scarf attached to a hair band in
Vicky's bag and I have lipstick and eye makeup in my purse."
At this point, Jennifer was obviously enjoying this. I thought I would
too when I had imagined her dressing me. But now that it was real, it
was a much scarier and embarrassing situation. Using her hair brush,
she combed my hair backwards, and worked the hair band in to keep it in
place. The scarf covered most of it, giving the impression that my hair
was longer. Jennifer teased out some bangs so that it looked more
feminine and applied her makeup. She was grinning widely the whole
time, making little comments about how the mascara really opened up my
eyes, the shadow was perfect for my eye color, and the lipstick made me
look kissable. I couldn't believe how easily Clint had convinced her to
help feminize me. When she had finished my makeup, Clint started
driving while she fiddled a little more with my hair making me more fem
looking. I didn't even know where we were or how far we had gone, when
Clint pulled into a parking lot.
"Well little Missy, let's go, step out and we'll see how you look."
They both slid out of the front seat and he opened the rear door for
me. Not knowing what else to do, or what to expect, I got out.
Straightening my skirt and adjusting the blouse, I finally looked up to
see them standing there holding hands. We were just outside a log cabin
structure and I heard some upbeat music playing inside. I had never
felt as vulnerable as I did standing there and certainly wanted to
leave, so I spoke up.
"Can we leave now? I want to go to the hotel and get out of these
clothes."
"Come on Missy, let's go have some fun. You look very cute and after
all the trouble we did to get you dressed, you ought to at least show
some appreciation to your wife and let her check out this fun place."
"Of course, he will go. I mean you don't want to just stay out here in
the parking lot do you Missy?"
Not knowing, what else to do, I nodded my head and followed their lead
into the bar. I was petrified. I mean, I had never been cross-dressed
in front of anyone before, and now I was going into a dance place. It
was a typical layout, with a big bar in the middle, a lot of tables and
chairs next to a dance floor, and some secluded booths at the back.
There wasn't much of a crowd with lots of open tables. Clint headed for
a booth and pulled Jennifer in next to him. Peeling off another twenty,
he told me to get another round for them. I noticed he hadn't included
me in this drink order. Not knowing what else to do, I shyly approached
the bartender and spoke in a soft, hopefully feminine voice.
"Can I order a couple of drinks?"
"Sorry miss, but we don't take orders at the bar. Go back to your table
and I'll have a waitress come over."
Relieved that I passed this first test as female, I turned and headed
back to Clint and Jennifer.
"Where are our drinks, little Missy? Did you forget what you were
supposed to do?"
"Sorry Sir. The bartender wouldn't let me get them and said he would
send someone over to take our order."
"Well that's not going to cut it. Go back and get the drinks."
Not knowing, what else to do I went back to the bartender.
"Can't you let me order something to drink? My friends don't want to
wait and I really want to keep them happy."
"Like I said, only waitresses can serve drinks here, so unless you're
willing to volunteer to be one, I can't help you."
"Ok I'll do it, if I can take them a drink."
Smiling and shaking his head as if he had seen everything now, he
reached under the bar, feeling around to find what he needed. He
finally put a tray, a small metal cash cup, and a white eyelet apron on
the bar top.
"If you really want to do this, just put the apron on, and I'll mix
your drinks. What do they want?"
I told him the order as I tied the apron around my waist. It was a half
apron, with a scalloped lace edge. I noticed it didn't look too bad
against the lace trim on my skirt and blouse. After he poured the
drinks, I paid him, put the change in the cash cup, drinks on the tray,
and headed back to Clint and my wife. As I approached them Clint had a
big grin and Jennifer was openly giggling.
"Well, well, well. Looks like you have a real liking to be a waitress.
I must say that little apron looks good on you and pretty natural too."
Jennifer continued to giggle, but I spoke up, trying to explain
everything. I already knew the situation was out of control, but I
wanted to try to defend myself.
"I had to do this. The only way he'd let me bring you a drink, was if I
agreed to dress like a waitress."
I put the drinks down on the table, but didn't know what to do next.
Neither Jennifer nor Clint made a move to let me in the booth. As I
stood there, Clint reached in his pocket and brought out another
twenty.
"Since you seem to like your new role, why don't you go over and buy a
drink for those two cowboys sitting at the back table. That way you can
continue to be a pretty little waitress. Jennifer and I would like a
little time to ourselves."
I stood there a second and looked at Jennifer. She just smiled and
glanced over at Clint. Again, not knowing what else to do, I took his
money and went to the table. I told the men they had a couple of free
beers coming. They look real suspicious, but eventually smiled. They
told me what they wanted and I took their empties. At the bar, the
bartender seemed a little surprised, but he gave me the beers and
change. I took the drinks to the guys and was embarrassed when they
gave me a small tip. I tried to turn it down, but they just grinned and
told me to keep it cutie. Blushing I headed back to the bar. Not
knowing where else to go, I sat on a stool near the bartender. There
weren't any other customers near Clint and Jennifer or the cowboys, so
I just looked around. There was just one waitress, some people were
dancing, and a few couples sat at tables near the action. Clint and
Jennifer got up once and did a slow dance, holding each other closely.
I could see he was leaning in close, whispering in her ear. After the
dance they went back to the booth where they continued to sit close and
Clint talked to Jennifer. He had his left hand on her thigh and she was
holding his right one. She had a half smile on her face and whispered
back occasionally as they spoke. Getting closer to each other as they
talked, he leaned in and gave her a small kiss. I saw her eyes close
and she kissed him back, opening her mouth. It was just a brief kiss,
but it seemed like forever. I felt my insides twirling around. Not
knowing what they were saying or thinking was killing me. The only
thing worse was when they finally glanced my way. Then her smile
broadened and I could see his hand sliding further up her thigh. It was
excruciatingly painful. Clint looked toward me and motioned me over. I
nearly ran to the table, going as fast as I could in the heels.
"Talk about great service, Missy you busted your cute little buns to
get here. Are you having fun being a sexy little waitress?"
"It's ok."
"Well, that's what I wanted to talk with you about. Jennifer and I can
see you like swishing around, serving drinks, and being all cute in
your little skirt and heels. So we really don't want to take you away
before closing. But Jennifer is ready for me to take her back to the
hotel. She wants to be sure that would be ok with you. I told her you
would be fine with it. You don't mind if I take her back to the room,
let you stay here to be Missy the waitress, and then I'll come back to
get you when the bar is closing? You are okay with that plan, aren't
you?"
They both looked at me as he said this. I could see Jennifer's eyes
gazing at me; I had seen that look before. It was mix of anticipation
and desire. There was also a little bit of concern that she might be
doing the wrong thing. She was looking at me for approval. I noticed as
they looked up at me, that Clint's hand had gone further up her thigh
and now was totally up her skirt. He had also placed her hand on his
crotch, where her fingers were tracing over the outline of his cock.
The look in her eyes took on more lust, as her touch revealed what she
had imagined before. His size was becoming apparent to her, and she had
even more willingness to go with him. I knew before I answered that she
wanted to fuck him. I also knew that seeing me in panties, bra, heels
and stockings, trying to be as fem as possible, made her see me as less
of a man too. That perhaps she really could go have sex with a
masculine guy like Clint, because she knew I certainly couldn't supply
the kind of sex he would give her. That maybe I didn't even want to be
a man any more. Her reservations were gone. Clint had worked his magic
like he said he would. So I knew there was really no options now, it
was time to pay the piper for making my fantasy come true.
"I guess it would be ok for you to take her back."
I wanted to say no, that I didn't want you to take my wife. That I
wanted my life back like it was before, but I knew it was too late.
Clint didn't wait for me to change my answer or put conditions on it.
He knew time was critical now. Jennifer was hot. She had enough liquor
to lower her inhibitions, and seeing her husband as a pantywaist
compared to him had pushed her to ignore any reservations she might
have about having sex with another man as a married woman. Missy's
permission was the icing on the cake.
"Well since you approve of me taking care of her, then let's check with
the bartender to be sure you can work here till I can get back. Ask him
to come to the table and talk with me."
I went back to the bar and spoke with the bartender. He just looked at
Clint and Jennifer a little questioningly, but since he wasn't busy, he
stepped out from behind the bar and followed me back to their table. As
we approached, Clint stood up and shook his hand.
"Hi, nice place, I've always liked it here and you make a good drink. I
have a favor to ask. My friend Missy is having fun being a waitress and
isn't ready to leave. But he wants me to take his wife back to her
hotel. So I was wondering if you would mind if Missy stayed here. She'd
be willing to work, and do what you want. I'll be at the hotel for a
while, but will back to get her at closing."
The bartender got a sheepish look on his face, and looked back and
forth between me and Clint. He looked me up and down several times, and
it appeared that he was trying to figure this all out. He obviously
realized now I was a male, but I must have been convincing enough as a
female to pass earlier. He also concluded that Clint here was going to
have sex with my wife. Finally, he just shrugged his shoulders and
said, "Guess it's fine with me, I could use some help, as long as she
doesn't want any more than tips. We close at 2 AM, so be here by then."
It was not even midnight yet, so the fact that Clint and Jennifer would
be gone that long, pretty much indicated what they would be doing.
"Oh that will be fine. Just be sure to do as the man says Missy, you
understand? Stay here and I'll be back by closing."
Without waiting for an answer, he turned to Jennifer, helped her up and
started to the door. She glanced over her shoulder briefly, looking at
me with a small smile, and she mouthed have fun.
Then they were gone. I followed the bartender back to the bar and he
told me to start clearing bottles and glasses from the empty tables.
Clint and Jennifer walked quickly to his truck, he holding her hand
tightly. Inside she was full of butterflies, not knowing if this was
the right thing to do or not. She definitely wanted to have sex with
Clint, she had been thinking about it the last hour. But she also
didn't want to hurt her husband. She just reassured herself, that he
had agreed to this, and had to know what they were going to do. She
kept going back to the image of him, walking around the bar in the
heels and skirt outfit, and how he seemed to be natural at it. She had
noticed right away that he didn't stumble in his heels, and that he
actually smoothed his skirt as he sat down. It must be something he
really enjoyed. Now it was time for her to do something she really
enjoyed.
The trip to the hotel went quickly, surprisingly so, because Jennifer
had felt that they had gone a long way to get to the bar. She was
starting to have some second thoughts, but when Clint came around to
open the door, he swept her up in his arms. Carrying her to the room,
her reservations disappeared. He was obviously much more masculine than
anyone she had been with before. She opened the door and they entered
the room. As he closed the door, they embraced with a deep kiss. Their
tongues probing each other, as were their hands, gliding over each
other's body. She had never felt so eager for sex. Stepping back and
breaking the embrace, she reached and undid the zip to her dress. It
fell softly to the floor and she stepped out of it and her shoes and
went to the bed. This was what she wanted, but even so, her own
insecurities came out. She wanted to get under the sheets so in case
she wasn't as attractive as Clint had expected, that he wouldn't deny
her the sex she so desperately wanted. She slipped off her panties and
bra and pulled back the cover. Her breasts bobbed softly as she got in
bed, their nipples jutting out. As she lay down, she could feel her
pussy was wet and ready for sex.
From Clint's view she looked very sexy. Her body was attractive, well-
shaped, but what made her look so hot to him, was the knowledge that
she was a married woman. Not only married, but her husband knew of this
and had willingly submitted to his orders. He peeled off his jacket and
shirt, and reached down to pull off his cowboy boots. Straightening up,
he began to unbuckle his pants. From past experiences he knew this was
another important milestone. As others had before, Jennifer lay on the
bed and eagerly eyed him as he unzipped and stepped out of his jeans.
The bulge in his underwear was obvious; he had hardened significantly
since the bar, and now was close to his erect size. As he pulled off
his briefs, Jennifer looked at him, almost in wonder. He was definitely
the biggest man she had ever seen. Although a few woman balked once
they say how really big he was, she was even more eager. His long,
thick cock pointed straight at her and she reached out to grab it and
pulled him close to her.
Pushing her back, Clint spread her legs with his and lay down on top of
her. He reached to caress her left breast and leaned in to kiss her
again. She could feel the large cock nestled just outside of her pussy,
the heat from its touch radiating through her skin. She lost herself in
his kiss, and fell back opening her legs wider. She shyly reached down
and grabbed the large cock again, and positioned it at the opening of
her slit. Clint took the sign and slowly began to enter her. She was
very wet, but even so he pressed in slowly, giving her vagina time to
expand to his girth. He was amazingly thick as well as long, and he
knew that if he jammed in too fast it would be painful, but this was
going in perfectly. Jennifer couldn't believe the feeling of him
entering her. Before when other men had penetrated her, she could feel
the contact, but this was so different. Not only could she feel his
cock sliding against her, but it was actively stretching her,
multiplying the erotic stimulus she got. The emotions and sensations
were coming so fast and so strongly, like nothing she had ever
experienced. And it seemed like it wasn't ever going to end, he kept
sliding deeper and deeper into her, opening her up to new feelings. She
almost felt like he was touching parts of her sex that had been dormant
and unused before. All the while, they kissed and felt each other. Her
hands grasped his muscles along his shoulders and back, as he caressed
her breasts and face. The sensual feelings were building for both of
them. Finally he was fully into her and began to slowly, rhythmically
fuck her. He pulled back about half of his length, and then plunged in
till his balls gently slapped against her ass. All this was so new to
Jennifer, feeling so stretched and full, being totally aware of his
penis and balls. It was as if they were separated from him. It only
took a few strokes before she was overwhelmed by her first orgasm. It
happened so quickly, building rapidly to her climax, unlike any she had
ever had before. She shuddered, griped him tightly, and let out a moan,
soft at first but building in volume as she came.
This was what Clint lived for. The first climax he gave a new woman was
always special to him, but he had much more to do. He knew it was
important that she cum multiple times her first time with him. She must
see sex with him as so special that she will continue to want, even
need it. Generally, that was not a problem for him and he could tell
tonight would not be any different.
As her first climax ran its course, he slowed briefly, and then began
once again to piston his penis in and out of her. As he fucked her, he
slowly reached down and repositioned her legs, pulling them up and back
against her stomach, fully exposing her pussy to him. This position
allowed him the deepest penetration and he wanted her to feel totally
overwhelmed by his cock. He established a steady rhythm and reached up
and caressed her breasts with his hands and leaned forward to kiss her
hungrily.
Jennifer could not believe what she was feeling. He was now even deeper
in her and she felt tiny orgasms electrify her body every time he
plunged into her. The feelings continued to build and once again she
succumbed to another paralyzing orgasm. Only this time, she felt it
cycle through her again and again. She had never cum more than once
with Mitch, but this was so much more. It seemed like she would climax
forever. She could also tell that Clint was building to a climax, as he
increased his rhythm and force as they coupled together. Finally, she
felt him tense up and it triggered the most explosive climax for her
that night. They shuddered, groaned and clasped each other until the
emotions had been drained from them. As they lay still next to each
other, Clint gradually and gently repositioned her again, so that she
was spooned into him. His cock was still buried in her, and it
gradually softened but even so still filled her up. His strong arms
wrapped arou