'JENNY' & 'MIKE': DATE NIGHT

Hi guys, I hope that you enjoy this story that deals with Pegging and
Gender Role Reversal. The idea of pegging has always been a hot topic
for me. I have tried it in my personal life, though not in the same way
as the characters in this story, and have found it to be a highly erotic experience. I have wanted to write this story for a while but have been
putting it off. But after I read silkstockingslover's Kinky Tales: I
pegged my Husband, I knew I had to start writing this story.

This time my story does not take place in the city of Dubai. I'd rather
leave the location of where the events take place up to the reader's imagination. I'm sure that a lot of couples around the world have done something similar to what's happening in this story, and I hope that
some of those couples read this story.

Note: Thanks to shyone245, trigodreamer, ckquail, vertexwild for editing
my story.

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CHARACTERS:

James Winchester / Jenny

Michelle Winchester / Mike

NOTE: This story is told from James' POV.

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It's Friday night, but for me and my wife it's Date Night. Most couples
have date nights on Saturday, but we have it on Friday nights to get an
early start on the weekends.

Michelle and I have been married for a little over two years now and we
live a very happy life. I was not always so happy because I am a
crossdresser and have been dressing up ever since I was 15. I met
Michelle when we were in college in 2005. She was studying law, while I
was in the IT field. We met at a college party and there was an instant attraction between us. I would say that it was love at first sight and
we've been together ever since that night.

We've always had great sex and I had found Michelle's preference to take control in bed really hot. In our second year of college, I finally
found the guts to reveal my secret to her. Most girls that I had dated
had found that to be utterly disgusting and had broken up with me over
it, but after many heart breaks I had finally met my true love.

Michelle was not like most girls. I was amazed at how understanding she
was of my fetish, even supportive of it. I had never expected someone to understand it as well as she did, she even started to help me. We
experimented quite a bit after I opened up to her about it.

She helped me choose the right outfits to wear, that would suit my body
and put emphasis on the right places, and had helped me become quite
adept at make-up techniques. She even called me by my CD name, Jennifer,
or Jenny for short. Our sex life improved quite a bit after that. She
often preferred me being dressed while we had sex, and eventually she introduced anal play in the bedroom. We started with her finger fucking
me and we gradually moved on to using small dildos and butt plugs.
Although she took charge in our relationship, it wasn't until our first
year of marriage that we tried pegging.

She loved the power of the role reversal between us and I enjoyed her
control over me while she wielded her strap-on. Eventually Michelle
started embracing a more masculine role whenever I took her cock up my
ass. She would dress up more like a guy while I dressed up all sexy for
her and we would usually end up fucking like rabbits.

She suggested once that we reenact our wedding night as part of a
fantasy role play where I dressed up in her wedding dress and she
dressed up in a dapper tuxedo.

She asked me to call her 'Mike' that night and the sex was amazing! That
is where she got her manly name from. Calling her 'Mike' in the throes
of passion only made her pound me harder, and it was definitely the best fucking I had received. Of course we did have vanilla sex every now and
then, but we had both discovered that the sex was always hotter when we switched roles.

This week had been a pretty busy one for Michelle. She'd been coming
home late because of a new client that her firm had taken on and was
stressing about her workload. So this morning, I had suggested that she
try to get home early and maybe 'Mike' and 'Jenny' could have a date
night. She seemed pretty enthusiastic about it, and we agreed that
tonight we'd spend the night at home with some take-out and a movie,
with a good sex session for dessert.

I mainly work from home as a Technical Consultant for a Finnish company
and mostly only leave home when I have meetings or when a client faces
some major issues. So it was easy for me to get everything ready for our evening in. I was getting really excited and my mind began to wander
with possibilities about tonight. Around 5pm I called up Michelle at
work just to see if we were still on for tonight. The phone rang and she
picked up on the second ring. "Hey babe," she said, sounding and stressed.

"Hey honey, what you up to?" I asked.

"Just busy with this ton of paperwork lying on my desk, it's beginning
to look like a pig sty in here," she said. I chuckled upon hearing that,
mostly because I know Michelle to be an organized person. She doesn't
like anything at home or at work to be messy at all.

"You find that funny?" she asked playfully, irritated with my laughing
at her.

"Yeah, kind of. Especially since I know how much of a neat freak you
are," I said, this time trying to control my laughter.

"I just hate it. Just when I think that everything is going to get
better, more paper work gets shoved on my desk!" She sounded really
stressed and I wondered if she would end up working late again,
cancelling our date tonight.

"Well, are we still on for tonight?" I asked her, hoping that she could
still make it.

"Yeah, yeah. I've already told the boss that I'm leaving on time today
and that I really need to de-stress and relax," she replied, her words comforting me a bit.

"Ok. That's good to know! Can you pick up some take-out on your way back
home?"

"Yes, I can definitely do that. What are you in the mood for?" she asked.

"I don't know. Just get whatever you want." I replied.

"How about I get us something from the Golden Dragon?"

The Golden Dragon was one of our favorite Chinese restaurants in the city.

"That sounds fine babe," I replied.

"Ok then. Have you decided on a movie for tonight?" she asked.

"Yea, Basic Instinct," I said with a Cheshire cat grin.

"You know if you turn on something like that, I basically won't be able
to keep my hands off you," she chuckled into the phone.

"That's the idea!" I said in a sexy feminine voice.

"You're getting me really horny now and the sexy voice isn't helping at
all!"

"What can I say? I love getting you worked up," I snickered.

"You know you're going to pay for that later tonight!"

"Promises, promises!" I sighed.

"You're such a tease!" she retorted.

"Well, you better get back to work if you want to get home early," I said.

"Ok, bye. I love you." she said and I heard the receiver click on the
other end.

"I love you too babe," I replied, beaming.

Now, I was even more excited. Mostly because we would get to have some
intimate time today, so I spent the rest of the evening getting ready.
First, I took a nice long shower and made sure that I was completely
shaved and hair free around my legs, arms and chest. I spent the next 30 minutes just deciding what I was going to wear. I wanted to be ready by
the time Michelle got home and I really wanted to wow her.

I decided on a blue colored sundress and beige colored 4 inch strappy
heels. But first, I took care of my make-up. I made sure that I kept it
minimal and classy rather than going for the slutty look. I mean we were
just going to be home and having a relaxing night, which would possibly
turn into some hot loving. Although, when I did slut it up, Michelle
seemed to be even more turned on and would pound me like I was a whore.

After I was done applying foundation, mascara and a light touch of lip
gloss, I put on my blonde wig that went well with my blue eyes. I
slipped into a strapless black bra and stuffed the cups with silicone
breast forms. They were not too large, just about a C cup size. I put on
a lacy thong to match the bra and then quickly got dressed.

I was ready by 6:30pm and headed downstairs to make myself a vodka and
orange. Once my drink was ready and as I was about to sit down to have a
sip, I heard the front door open.

"Hey babe," I greeted.

"Hey honey," she replied with her back to me while she locked the door.
She turned around looking surprised. "Wow, you're already dressed," she
said, smiling and looking me up and down.

"Yeah, I wanted to get a head start and be ready by the time you got
home," I said, moving closer to her and giving her a kiss.

"Well, you look really good," she complimented.

"Thanks! I aim to please." I said.

"You sure do!" she said and kissed me again.

"Is that dinner?" I asked, pointing to the unmarked plastic bag in her hand.

"Yeah, I got us egg rolls, rice and your favorite Szechuan chicken."

"That sounds wonderful," I said.

She leaned in for another kiss and our tongues battled with each other
as it became passionate. I pulled away, not wanting both of us to get
all hot and bothered right away, and heard Michelle sigh as I pulled back.

"Why don't you go upstairs, take a nice hot shower and get dressed and
I'll just make sure the table is set for dinner."

She smiled and replied, "Ok."

I grabbed the bag of food from Michelle's hand, and as I moved towards
the kitchen, she gave me a playful smack on my behind. She gave me a mischievous smile and wink as she headed upstairs to the bedroom. I
spent the next couple of minutes setting the table while sipping on my
drink.

It wasn't long before I heard Michelle coming downstairs and smiled
brightly as I saw her. She had her shoulder length hair in a ponytail
and wore a pair black denim pants and a black cotton jersey t-shirt. I
noticed that her chest area was flat instead and her tits were hardly noticeable. God she looked so sexy when she was binding. She didn't
bother with any makeup either, and although she didn't really look like
a guy, her feminine features were hardly noticeable. I always noticed
that whenever she dressed up as a guy, there was this masculine aura of confidence that carried her. As she moved closer to me, I noticed a
bulge in her crotch area and knew that she was packing our little big
friend.

She flashed me that mischievous ear to ear grin which told me everything
I needed to know about how the night was going to end.

Dinner was a casual affair, and like every other day, we spoke about how
things at work were going. "It was good of Henry to let you come home so
early. I thought you would be late again and we wouldn't be eating
dinner together," I said.

"He knew I'd been working really hard with this new client and told me
that it was ok to leave early. In fact, he told me that I could take a
long weekend and have tomorrow and Monday off," she said with a smile.

"Really?"

"Yeah. He told me that he knew how stressful it can get and that I
should take the time off for all the hard work I'd put in the last
couple of weeks," she replied.

"Why didn't you tell me this before?" I asked.

"I bumped into him when I was leaving and we discussed how difficult the
new client was to work with and he just told me."

"Wow, that's great," I said with a smile. She nodded and smiled back at
me, that gorgeous smile of her capturing my full attention.

"I was actually thinking that maybe, we could you know, have some fun
and make it a long weekend," she suggested very sexily.

"Oh really?" I answered playfully.

"I mean we haven't switched roles like this in a while and I thought
that maybe we could stretch the weekend before I go back to work on
Tuesday," she said.

"You mean..." I trailed off, realizing what she was saying.

"Yes," she said, smiling very widely now. I can just sense what is in
store this weekend.

"Sounds like a plan," I said, smiling as I looked back at her.

"Yeah?" she said, her eyes dazzling with delight and I felt my heart
flutter from her feeling very excited. I noded my head responding to her question. "But, I have one condition," she continued.

"And what is that?" I asked, intrigued with what she had in mind.

"Let's not break character the entire weekend. I'll be the husband and
you can be the wife. I'll call you Jenny and you can call me ... Mike."

"Kinky..." I said with a giggle.

"So, do you accept the challenge?" she asked me with a hint of
competitiveness.

"Yes, I accept" I said, beaming with excitement She just smiled as we
continued to eat dinner. I wanted to immediately jump Michelle...I mean
'Mike'. But I decided to wait. I had deliberately chosen a hot movie,
Basic Instinct. Watching sexy movies usually gets her hot and bothered,
which since our roles were reversed, I would get fucked nice and hard.

I started the movie and made myself another drink, while I got Mike a
beer. It was fun and kind of sexy spending an evening like this. As the
movie went on, Mike began to put her best guy-moves on me. She faked a
yawn and then put her hand around my shoulder and every now and then
pulled me a little closer to her. She even went to second base with me
while we watched the movie. I felt like we were in high school, only I
was the girl now!

As the sex scenes in the movie came up, Mike began to twitch and move
her body around a bit. I could sense that the action on the screen was beginning to get to her. She turned to face me and I stared right back
into her eyes. We began making out on the couch as her hands roamed from
my leg all the way up to my tits. Even though they were fake, she still squeezed them as though they were real.

She slowly took my hand and moved it over to her crotch rubbing it all
over her bulge. She broke the kiss as I continued to rub her hard-on, my
own cock straining against my panties. "Why don't you get on your knees
and give me a blowjob sweetie..." she said.

I slithered down and kneeled right in front of her and began to unbuckle
her pants. She raised her hips a little and I pulled her pants down to
her ankles and her fake cock sprang up. I saw that she had put on her
harness that looked like a man's brief's called the Tomboi and a 7 inch
dildo attached to it.

I began to jerk her phallus and licked the base of the shaft all the way
to the tip. I repeated the action a few more times while she watched,
making her moan.

"God, you look so fucking hot!"

I smiled at the proclamation and took her cock into my mouth. I began to
suck it slowly while stroking it with my hand. Mike began to moan as the
base of the cock rubbed against her clit.

Mike put both her hands behind my ears, grabbing me and began to force
me down on her big cock, pushing deeper into my mouth. "Oh yeah baby,
that's it. Take it all inside your pretty little mouth."

As the cock went inside my mouth and hit the back of my throat, she held
me in place for a couple of seconds. Luckily we had been using this
dildo for a while and I had had enough practice taking the entire
length. She then let go of my head I released the cock from my mouth
gasping for air and leaving a trail of drool all over her dick and my lips.

"Stick your tongue out," she said, placing her hand on my chin. I did as
she ordered and she grabbed her cock and began smacking it on my tongue.
She groaned as she slapped her dick all over my tongue and my mouth. I
grabbed her shaft and began to suck on it again. I kept working on her
for a few more minutes and then I heard a flash go off! I looked up to
see that she had taken a picture of me!

"God, you're such a slut!" she said, continuing to take more pictures.

"Only for you baby," I replied innocently, loving that she was taking
these sexy pictures of me. She flashed me a wicked grin as I continued
to suck on her. I maintained eye contact with her as I continued blowing beautiful Mikey.

"Get up here!" she commanded. I gave the dildo once last lick and got on
top of her. She pulled my dress up and began to grope my ass. I felt the
cock against my butt cheeks and I began to gyrate my hips in a teasing
motion. She pulled me in for a deep and passionate kiss as she continued
to knead my ass cheeks in her strong hands. "Now, get on all fours!" she demanded.

I got off her lap and placed myself on my hands and knees next to her,
facing the back of the couch. She removed her pants from around her
ankles and got right behind me. She hiked up my dress a little further
up my back and pulled my thong to the side. "Ooooh, look at that pretty
little hole, begging to get fucked," she teased, rubbing her index
finger on my rosebud.

She licked her finger and slowly stuck it inside my ass. I moaned in
delight as she began to slowly finger fuck my ass hole. "Are you ready
to get fucked, my little slut?" she asked me, as if it was even a question.

"Ohh yes," I replied with a breathy desperation, dying to be penetrated
by her cock.

"Yes what?" she teased me.

"Yes, I want to get fucked," I replied. She rubbed her cock against my
anus and began to tease me further. It was pure, wonderful torture and I
wanted it to end.

"Please just put it inside me," I moaned. She snickered as I begged for
her cock. She went to the entertainment unit and opened a drawer and
removed a bottle of lube. She then put some on her finger and rubbed it
on my rosebud and then a generous amount of the lube on her dildo.

She teased my hole a little more and then pushed on it firmly. Since I
was already used to her fucking me, my ass instantly gave way to her
cock as she slowly pushed the entire length inside me. I gasped aloud as
my ass was filled by her cock. She leaned forward, putting both arms
around me and hugging me tight.

"All the way in," she whispered into my ear. "Only whore's and sluts
take such big dicks in one fucking go!"

I moaned as she began to slowly grind into me repeatedly.

"Are you a slut, Jenny?" shed breathed into my ear, sending chills down
my spine. "Are you my slut?"

"Yes," I said in a breathy reply.

"Yes what?" She stopped grinding into me but still held me tight.

"Yes, I'm a slut!"

"Whose slut are you?" she asked.

"I'm your slut, Mike!" I replied, staying in character as best I could.
She grabbed my hips and slowly began to fuck me, giving me every inch of
her hard cock.

"Push back on my cock!" she ordered. I immediately complied and began to
push back on the dildo, lowering myself on the beast. She bent a little
lower and grabbed her phone. I heard a familiar sound and saw the flash
pop, lighting up the room for an instant. She was taking more pictures
of me as I continued to push my ass onto her cock. She leaned down once
again and pointed the front camera towards us and took a picture. She
showed me the picture of my ass stretched and filled and giggled.

She threw her phone back on the couch and grabbed my hips again. This
time she thrust into me mercilessly. She slowed but drove her cock hard
inside me harder with each thrust. She would pull her cock out almost
all the way out and then pump it right back in. My ass was on fire but I
was in complete heaven. I began to moan louder and whimper as she
started to fuck me faster. She leaned forward and pulled my cock out of
my panties and began to jerk me off.

"Annnnhhh...Annnnhhh...annnh.." I moaned.

"Yeah, take it like a fucking whore!"

Each stroke of my cock was in sync with her thrusts and I was beginning
to go over the edge. I heard her whimper as the base of the dildo was undoubtedly rubbing against her clit. She began to pound me harder and
faster. "Are you ready to cum?" she asked me.

--------- page 2

"God, yes," I replied, helplessly on the verge of coming.

"Good, I'm about to cum too," she replied. "Jerk yourself off baby."

She released my cock and I began to jerk myself. She moaned and grunted
as she drove her cock deeper and deeper into the depths of my anus. And
then I felt my balls stir. "I'm almost there," I said.

"Hold on baby, just a little bit more," she said. I tried my best but I couldn't. Jets of cum began to fly out of my cock.

"I'm cumming!" I moaned. This must have driven her wild; she screamed
out like a banshee. Her own orgasm had hit her, but she continued to
fuck me, grinding her pelvis into me and working her clit harder and
harder. Once she was done, she leaned on top of me again, hugging me
tight once more. I stayed as I was and let her catch her breath. Once
she was ok, she let go of me and slowly removed her cock from my ass. My
ass felt empty, once the shaft and head popped out of me.

I fell back on the couch and she got on top of me. We shared a kiss as
my flaccid cock rubbed against her erect phallus. "This is going be such
a fun weekend!" she said, looking into my eyes and smiling. I smiled at
her and pulled her in for another kiss.

TO BE CONTINUED...

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I hope that you enjoyed the story. I welcome positive feedback and
criticism. Part 2 is now in the works and shouldn't take me long to
write. If there is anything in particular you would like to see 'Jenny'
& 'Mike' do in the next couple of planned installments, please do feel
free to mention them in the comments or write to me through the contact
on my profile.

*-*-*

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COMMENTS (17)
COMMENTS

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17 COMMENTS
Anonymousalmost 2 years ago
MMMMMMMMMMM Delicious xxx
This has been such a delightful erotic experience to read as you weave
us through your story ... Cant wait t get to the next chapter to see
where you take us as we follow Mike & Jenny . Thanx for sharing xxx

Anonymousalmost 3 years ago
Laughably bad
Even for fiction this was just horrible. Too funny for words.

1 star

tonitemptstonitemptsalmost 3 years ago
Thanks
I love this. Its going to be a long night.

MonicaCDMonicaCDabout 3 years ago
Wonderful
A truly great story about a loving couple. I love these type of stories
more than any other. No humiliation nonsense, just pure love and lust.

Tootight1Tootight1over 4 years ago
good, very good
For a couple to be able to explore each others fantasies, there has to
be a lot of trust, but most people know that. This is a good story and
I'm enjoying it.

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