Caring
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Careful
My story begins almost one year ago. I remember because it was just a
few weeks before my birthday. The last few years my wife has given me
one night where she does what I want for my birthday. Recently, it had
been her wearing a special sexy outfit and one night when she tied me
up and had her way with me. It was all very tame. This year however, I
had been working up my nerve to ask for something I had always
fantasized about, but never had the guts to admit.
I have been married for six years and have known my wife for almost
fifteen. We met in college and even though we were always dating and
romantically involved we developed a strong friendship. We always refer
to each other as best friends and we can always seem to talk out our
problems. Over the years we help each other deal with various problems
but we were always there for each other in the end. The sex had always
been only fair, but for whatever reason it had started to improve as we
reached our middle thirties.
I always felt comfortable talking to Jennifer about any subject. Any
subject except one. Ever since I can remember I have been fascinated by
attractive women and notably what they wear. When I see a beautiful
woman I normally will only remember her clothes later on. I am
fascinated by watching women in high heels and skirts walking. I have
always wondered what it would feel like to be the one in the skirt and
heels. What would it feel like having your skirt swish when you walk?
Is it drafty under there? I had fantasized about women's clothing for
years but I had never acted on it. Now I had finally decided to ask
Jennifer to help me live out my fantasy.
One night just before my birthday Jennifer and I were in bed together
when I brought up the subject of my birthday. "May I make my usual
birthday request?" I know my voice sounded shaky and she must have
noticed.
"What kind of request?" she answered coyly.
"Well you know, kinda of my sexy present from you," I asked. I noticed
my hands were as cold as ice.
"OK, what do you want this year, sexy?" she snuggled up to me and
caressed my chest.
I immediately thought of just asking for something else. I had no idea
how she would react. Maybe I should just forget it. No I had to find
out. I had thought about it for too long. I summoned up my courage and
spoke, although my voice barely made it over a whisper. "I would like
some lingerie, a shirt, blouse, and a pair of black pumps," I said.
There was silence for a few moments. Jennifer seemed a little confused
but she replied. "Yes and is there anything else you would like me to
wear or do?" she asked.
Oh no she had misunderstood. "Well not exactly," I paused trying to
gather my courage. "I was hoping you would buy them for me."
"What?" she asked with and edge to her voice. She took her hand off my
chest.
"Oh no," was all I could say.
"You must be kidding?" she softened a bit. My mind told me that she
might come around after the initial shock.
"No, it something I have wondered about for a long time. I have always
wondered what it would feel like," I replied, trying to sound
convincing.
"Wondered what what would feel like?" the edge was back. "Say it!"
"I have always wondered what it would feel like to dress in women's
clothes, I'm sorry sweetheart," I pleaded.
"You are disgusting, do you think I would allow that?" she was really
pissed. "You must be crazy? Are you gay?"
"No, God no honey, I'm not gay," I said.
"Well I can't believe you asked me that," she said starting to settle
down. "No way, that is sick and I will not be a part of it."
With that she turned over and gave me the silent treatment for the rest
of the night. Over the years there had not been too many nights that we
went to bed angry but this was one of them. I hardly slept.
Nothing more was said about the subject. My birthday came and went.
There was no sexy surprise and really not much sex at all until a few
weeks had passed and we both pretended like I had never asked.
Finally one night after we had put the kids to bed, and my wife had had
a few drinks she sat down on the couch with me. She had a somewhat
nervous demeanor.
"We need to have a talk about your birthday request," she said opening
up the conversation. "I have been thinking and I realize this is
important to you. Why I have no idea, but I at least wanted you to
understand me and why I cannot share this with you."
"Ok, go ahead," I replied, surprised she had brought up the subject.
"Well I feel like you are asking me to participate in something that
changes our relationship. You dressing up would be almost like cheating
on me."
"I don't see the connection."
"You are asking me to allow you to do something that would change the
way I think about you, maybe it already has. I don't want to see my
husband, my lover, parading around like a gay man."
"I told you I'm not gay," I said defensively. "I have always just
wondered what it would be like, or feel like. I'm sorry it is my
fantasy."
"I wonder about things too you know. I wonder what another man might
feel like. But I don't act on it, because I know it would betray your
trust and change the way we think about one another. How would you feel
about me sleeping with another man?"
"This is different." I said, but in my mind I knew what she meant. "You
think about other men?"
"Well sometimes, no one in particular, but I wonder," she said.
"I guess I understand, but I still wish we could find a way to try it
out." I replied relenting. I knew she would not change her mind once it
was made up.
"Try what?" she said, she wanted me to say it.
"My dressing up." I said. I still blushed every time I said it.
"Well, ask yourself this question, are you willing to let me sleep with
another man?" she paused to let the statement sink in. "If not, then I
am not willing to participate in your fantasy." She replied raising her
eyebrows just slightly.
"No, I'm not." I said. I was not sure if she had made me an offer or if
she was asking a rhetorical question.
"Well, think about me with another man the next time you have your
little fantasy. That should help calm you down." She said with a
giggle. "I'm sorry, I do love you."
"I love you too." I said. "I am glad we can at least talk and
understand each other."
I had a hard time sleeping that night. I kept running her words through
my mind. Did she really want to sleep with another man? My wife? My
best friend? Or was she simply trying to prove a point. That must be
it. She was simply trying to show me how much she was against the idea
of me dressed up.
Nothing was said about it again for a while, but unfortunately, if she
was trying to suppress my fantasy, her strategy had the opposite
effect. My mind kept telling me that if I really wanted it, all I had
to do was say so. I didn't really think she would go through with
sleeping with another man. Not Jennifer, no way.
To make matters worse, Jennifer continued to enjoy sex more and more.
She had even begun to initiate sex. This was something she had never
done during all of our years together. She even began to wear more sexy
lingerie. I told myself she was doing it to keep my desires at bay. If
she wore more of it, I could get my fix that way.
Another change was a more lighthearted approach to the subject of my
birthday wish. She began playfully teasing me about it. One night we
attended a social function where she looked fantastic. She wore a black
dress, heels, and black stockings. On the way home she slipped off her
heels in the car.
"I can't believe you want to dress like this, my feet are killing me,"
she laughed and placed her shoe in my hand.
I was at a loss for words and only smiled and handed the shoe back to
her.
She giggled again at me. "What's wrong? Cat got your tongue? My girly
man," she said as she slowly slid her hands over her stocking covered
legs. "Or maybe this is not your style," she said as she reached down
and caressed my quickly hardening crotch.
"You can be cruel," was all I could think to say.
Weeks went by with out much more than an occasional joke from Jennifer
about if I liked an outfit she saw in a catalog or again if something a
woman was wearing was my style. As for me, my fantasies were running
rampant. I continually turned the scenario over in my mind. What would
she say if I accepted her offer? Was it really an offer? Would she be
even more upset that I was willing to let her sleep with someone else?
Deep down though I still thought she was bluffing.
As I said earlier she had started to wear more lingerie, particularly
on Saturday nights, which was our usual night to be intimate. One
Saturday about two months after our talk I noticed that she locked the
door to our bedroom while she was getting ready. She took quite a while
getting ready, but the results were fantastic. She finally came out
wearing a black above the knee shirt, a very flimsy blouse, stockings,
and a pair of red heels that she had not worn in years. The heels were
from a wedding she was in years ago when she was the maid of honor. The
best man that day was almost six five so she had to wear four inch
heels so that he did not tower over her in the pictures. She looked
incredible. She came into our living room and sat across from me.
"You like?" she asked.
"Yes, you look great but why all the trouble?" I said.
"No reason, sometimes I just like to dress up," she said with a
mischievous smile. She slowly crossed her legs. I could hear the
wonderful sound of the stockings on her legs rubbing together.
We sat back and watched TV for a while. I made her some margaritas and
she had a couple in the next two hours. The whole time I could barely
take my eyes off her. Her legs looked incredible and to add to my
frustration she would cross and uncross them and run her hands over
them every once in a while. Finally around midnight she came over to my
couch and sat next to me. She laid her legs across my lap and I ran my
hand over them gently. I was so turned on I had lost my ability for
thinking clearly.
"Ok, I accept your offer," I said, my voice cracked in the middle of
the words.
"What offer?" she asked with an innocent look on her face. I knew by
looking at her she knew what I meant, but she wanted me to say it.
"You know, about my birthday request," I said my voice shaking.
"Oh," she said feigning recollection. "Remind me."
"You're bad," I replied. "You know, about what I would have to agree
to... to get my fantasy."
She smiled at me, a knowing smile. "You need to say it, sweetheart."
"Ok, ok, I agree to let you experiment," I said, I had a hard time
saying the words.
"Experiment?" she would not let me off the hook. She slowly moved her
stocking cover legs. One foot rubbed the other leg slowly.
"Fine, I will allow you to sleep with another man, if I can dress up,"
there I said it; I hoped she would be satisfied.
"Really, you're sure?" she had a wicked grin on her face.
"Yes," I was taken aback, I expected her to be mad, but her reaction
was more of curiosity.
"You are prepared for this, you can handle it?" she said with a more
relaxed smirk.
"I think so, you're teasing me has made me willing to do anything to
try it," I said. I used the "it" word again.
"Ok, this might be fun," her smiling face looked rather wistful. I was
suddenly backpedaling. I thought I was calling her bluff but it felt
like I was playing into her hand.
"Why, do you have someone picked out?" my question was defensive.
"No, not at all," she looked surprised at the suggestion. "But it will
be fun looking."
"Just one though," I tried to throw in a condition after the fact.
"We'll see." she said.
"What do you mean we'll see?" I asked.
"Well, we will have to see if I like it," she answered raising her
eyebrows again. "What if you like dressing up, will you stop at just
one time?" she laughed at me.
"Ok we'll see," I said, I was again at a loss for words.
"Good, and by the way, I go first," she said.
We dropped the subject. That night we had great sex. She was very
aggressive.
The conversation was not mentioned again. I was too scared to bring it
up. But as time passed, a part of me hoped that we would just forget
about it, but another part was eager to feel all the feminine things
that women enjoy, the feel of pantyhose rubbing together when they
walk, panties hugging their buttocks, and their feet in a pair of tight
high heels.
A few months later, a friend of mine called. We had been friends for
years. When we got out of college he and I hard worked together. We had
always got along very well. In fact there was even a Thanksgiving that
he, I, and Jennifer had spent together when none of us could get home
for the holiday. Jennifer had known him as long as I had but they had
never really seemed to hit it off. Rob was single, he had several
relationships but for reason unbeknownst to me they always seemed to
end badly. A few years ago Rob had moved away form our area. We still
kept in touch and he and I talked on the phone every once in a while,
mostly about sports.
He had called to ask me if it was ok if he came for a visit. He was
traveling through our area and thought it would be nice to catch up. I
agreed, I thought it would be good to play some golf with him and watch
some basketball. Jennifer said it was fine with her and we made plans
for him to arrive the next Friday.
Rob arrived late Friday night. I had arranged some tee time for us the
next day so we caught up for a little while and went to bed. The next
morning Rob and our family had breakfast before we headed to the golf
course. He really seemed to enjoy spending time with the kids and
Jennifer.
We had a great time playing golf, it was just like old times. It was
nice catching up with Rob,
After our golf we head back to the house. I was planning to have some
dinner and watch some of the games that were on that night. When we
arrived at home I was surprised to find that Jennifer had taken the
kids to my mothers for the night. "She wanted to watch a movie with
them and spoil them a little," my wife explained. We decide to grill
some steaks and then watch a few games. While I helped prepare dinner
my wife mixed up some margaritas. Since I do not drink, she made enough
for her and Rob. She made more than enough.
After dinner Rob and I sat down and turned on ESPN, we were looking
forward to a long night of hoops. Jennifer continued to pour the drinks
for her and Rob. After awhile, Jennifer came up with a suggestion.
"Why don't we go out?" she asked. "We never seem to go out anymore, the
kids always keep us home, it will be just like old times,"
I was not too excited about the idea, but Rob chimed in, "sounds like a
plan."
"Ok, give me a few minutes to get ready," Jennifer said, she seemed
excited to be getting out.
After about a half an hour Jennifer came back into the living room. She
was dressed in some nice black slacks and a red silk top. Not too sexy,
but she was wearing a pair of open toed black pumps that gave the
outfit a sexy flair.
"Ok I'm ready," she said.
We all headed for my car.
"Steve can be our designated driver, or chauffeur tonight," Jennifer
giggled. She got in the front seat and we headed off.
We headed to a sports bar that was not to far from our home. Rob and I
had gone there many times to see games when he still lived near us. We
figured Jennifer could enjoy being out of the house and we could still
catch some games. When we arrived we decide to sit in a booth near some
of the big screen TV's. The first sign I got that something was up, was
when Jennifer slid into the seat next to Rob across from me. Rob gave
me a puzzled look and I looked at Jennifer. She just smiled at me and
raised her eyebrows. My stomach immediately went in knots.
They ordered a few drinks and we all sat and chatted about how much
things had changed since Rob moved away. I noticed Jennifer leaning in
close on Rob and touching him whenever he said anything remotely funny.
I got up to head to the bathroom and Jennifer told me to grab them each
a drink from the bar. As a walked away I knew.
When I walked out of the bathroom I looked over at our booth, Jennifer
and Rob were talking very close to one another. I immediately
remembered the times in college when I saw a friend of mine "hooking
up." All the signals were there, innocent touching, laughing at every
joke. Jennifer was definitely sending out signals. I realized that to
an unknowing observer, Jennifer and Rob appeared to be the couple and I
was the third wheel. My head was spinning. Could she really be going
through with this? I took my time at the bar and watched them for a
while. They did look good together.
When I arrived back at the table with the drinks, I seemed to be
interrupting their conversation. Rob had a strange look on his face and
Jennifer was all smiles. They finished their drinks and Jennifer said
it was time to head home. We paid the bill and headed to the car.
When we arrived at the car, my suspicions were confirmed when Jennifer
got in the backseat with Rob. I asked her what she was doing and she
replied that I was the chauffeur so she should sit in the back.
The ride home was torture for me. I knew what was going on, but yet I
was powerless to stop it, I had already agreed to it. I kept my eye one
the rearview mirror but there was really nothing to see for the first
part of the ride. Finally, Jennifer made her move. We were about five
minutes from home when I noticed the car suddenly was very quiet. I
looked in the mirror but could not see anything. After a few
adjustments I saw what I hoped I would never see, Jennifer kissing
another man. The silence for the rest of the drive was deafening to me.
We got to our home and headed inside. I had no idea what I was supposed
to do. We all sat down in the living room. Jennifer sat next to Rob on
one couch and I on another. Instinctively I turned on the TV. As I
watched, I noticed the incredible silence again. I turned around to see
the two of them making out. I got up and went into the kitchen to get a
drink. Jennifer joined me a few minutes later.
"Hey sweetie, I love you," she said as she came up behind me. I turned
to face her, but I had no idea what to say.
"Listen, it is getting a little weird, would you mind leaving Rob and
me alone?" she asked. I couldn't believe what I was hearing. Did I
really agree to this?
"Ok," was all I could manage.
"Sleep in the guest room tonight, I will see you in the morning," She
said and she kissed me on the cheek and was gone.
I basically stumbled down our hall on my way to our guest room. I had
no idea what to do. I had a million thoughts running through my mind. I
knew I could not stop what was already in motion. A part of me wanted
to, but I knew it was too late. Another part of me was happy for
Jennifer, she was about to experience something new, something
exciting. After I short while I crept back toward our living room and
peeked through to doorway. It was eerily silent again. The television
provided the only light in the room. The site I saw made me feel
strangely aroused. Jennifer and Rob were locked in a passionate
embrace. Jennifer's blouse was gone but she still had her bra on. They
were kissing. I watched for a few minutes when their kiss broke. I
heard Jennifer say, "Come with me."
I immediately retreated to our guest room, which was half way between
our living room and our bedroom. As they went by the guest room I heard
them giggling to each other. When they went into our bedroom, my
bedroom, I listened to the door close and as it closed I heard the
extra click of the lock being fastened from the inside. My heart sank.
I knew it was already done but the click of the lock made it feel so
permanent. I moved down the hall and sat outside the door to our
bedroom. I am not sure why, but I did.
I listened outside the door for a while, not sure what else to do. I
really could not hear much for the first 10 minutes. I could hear some
sounds like movement on the bed but I couldn't be sure. Then Jennifer
broke the silence. I heard her moan then say, "wow" in a breathless
voice. I heard some more movement and then a radio turned on. The music
was not loud but it drowned out everything else. I continue to sit
there for the next hour and a half. All I could hear was the radio, but
at least I would know how long they were at it.
At last the radio stopped. Now at least I could hear voices. They were
talking to one another in whispers. I could not decipher anything that
was said, but by the tone it was two lovers in the afterglow of great
sex. They laughed a few times but mostly they just talked. I was
starting to get tired, but I wanted to wait until I thought they had
gone to sleep. I checked my watch, they had now talked for almost an
hour and finally it grew quiet again. The same silence I had heard
before. Then suddenly the radio started again. "Oh no." I thought. This
time it only played for about twenty minutes, but when it stopped they
were silent. I had been sitting outside that door for over three hours
and I finally dragged my self back to the guestroom and lay down.
I awoke from a fitful sleep the next day very early. I still had no
idea what to do so I headed for the kitchen and made some coffee. I had
two cups and watched some TV before moving back down the hall toward
the master bedroom. It was still very quiet. I sat down and waited to
hear any sounds. Finally around 10:30 I heard the shower start. For
whatever reason, this made me feel like I should do something. So I
went in the kitchen and started making breakfast. After a while
Jennifer walked into the kitchen.
"Good morning," she said. I turned to her, she was glowing.
"Good morning," I relied half-heartedly.
"I love you," she said and she gave me a big hug. I was surprised.
"It's going to be ok, sweetie," she reassured me. I immediately felt
better.
"I love you too, I missed you last night," I said.
"I bet you did," she giggled.
The rest of the morning went ok. Breakfast was strange but I muddled
through it. After we ate Jennifer left Rob and I alone for a few
minutes.
Rob broke the ice first. "Are we Ok?" he asked.
"I guess so." I said. I had no idea what to say to a man who had just
spent the night with my wife. I did not blame him, I blamed myself.
"Good." he said, he seemed to be relieved.
I was really worried about what he thought about me. "Are you ok?" I
asked timidly.
"Oh yeah, I'm really ok," he laughed. I laughed along with him but his
laughter made me feel ridiculous.
After breakfast Rob left. We said our goodbyes and it appeared on the
outside as if it was just another visit from a friend. After Rob and I
shook hands, Jennifer moved forward to give him a hug. I turned away as
the hug turned into a passionate kiss and a few giggles.
The rest of the day was very hectic as we picked up the kids and tried
to finish up the chores of the weekend. I was still at a loss as to
what happened and had no idea what to do next. That night though, I
could not help myself and I tried to initiate sex. Jennifer declined
and told me we would have a talk soon. What she meant I had no idea.
The next few days I tried to get myself back into a normal routine and
pretend that nothing had happened. However, I could not get the picture
of Jennifer and Rob out of my mind.
Finally, two nights later Jennifer approached me. "We need to talk
about this weekend," she said.
"I know, is everything ok?" I said. I was still not sure what to say.
"I'm ok, are you alright?" she asked.
"I think so," I replied. "Will you tell me about it?" I was not sure if
I wanted to hear her answer.
"No, I don't think we should get into details," she said.
"Were you safe at least?" I asked. I had to know.
"Kind of," she answered sheepishly.
"What do you mean kind of?" I asked
"Well, I won't get pregnant I can promise you," she said somewhat on
the defensive.
"What's the 'kind of" then?" I couldn't understand why she was so vague
"Well I did swallow, but that all I'm going to tell you, that's your
only detail, I promised Rob," she blurted.
It felt like a punch in the gut.
"Promised Rob? What are you talking about?"
"You need to understand, I think I found out why Rob has had such bad
luck with relationships. He is a very jealous guy," she said. "We spent
a lot of time talking last night, among other things, and I really got
to know him."
"Go on," I said.
"Rob thought you were crazy to let me sleep with him, he told me he
would never have done that," she said. "He made me promise that what we
did would always be between just him and I."
"Ok, does that mean that this will be a one time thing?" I asked.
"Well Rob understood that I had your permission to sleep with other
men, but he told me he was not ok with that," she told me.
"What does that mean," I asked.
"It means I won't sleep with anyone else but Rob," she paused for
effect. "Not because I am being faithful to you, but because I am being
faithful to Rob."
"I hope that does not include me," I said stunned.
"No it does not, but he did ask me to make you wait a month," she
smiled, "as a punishment."
"Why does he get to dictate anything in our sex life?" I could not
believe what she was saying.
"Well he is part of our sex life now, I told you things would change,
but you wanted to push your little fantasy on me," she had taken a very
firm tone. "Plus we need to take a break from sex anyway."
"Why?" I asked.
"Right now, when I think of sex, I think of Rob. If you and I had sex
now I would only compare you to him," she said. "And believe me, you
don't want that."
Her last comment stung. I was totally on the defensive but still I had
to ask. "Was he that good? Was he bigger?" my second question came
straight from my insecure machismo.
"Yes and yes, but sorry no details," her tone was now lighthearted. She
was defiantly enjoying watching my manhood crumble.
About two weeks after our talk things were starting to get back to
normal. I had somewhat accepted my new position in Jennifer's life. In
fact I was staring to get antsy about when I would get my half of our
deal.
It was a Wednesday night and I was watching TV when Jennifer came into
the living room carrying a box.
"This came today," she said. "It's from Rob"
"Really?" I asked as she laid the box down on our coffee table.
"This was in the box," and she handed me a letter.
I took a few minutes to read it rather apprehensively,
Dear Steve and Jennifer,
I want to say thank you for the great visit I had with you. I
appreciate how you welcomed me into your lives. I would also like
to thank Jennifer for choosing me.
Sincerely,
Rob
I was a little surprised, but I realized he probably would have sent
something any way even if nothing out of the ordinary had happened.
There were two gifts inside, a small one for Jennifer and a bigger box
for me.
"You first," I said and I handed her the small box with her name on it.
She opened it and took out a note. She read it, smiled, and handed it
to me.
Jennifer,
I will never forget our time together. When you wear this I hope
you, and Steve, will think of me.
Rob
I realized that his comment "and Steve" was a shot at me, but figured I
deserved it. I tried to take it in good humor.
Inside the box was a gold bracelet. Jennifer really seemed to like it.
She immediately put it on.
"Ok, your turn," Jennifer handed me the bigger box.
"What did he send me? A golf shirt?" I joked as I opened the paper.
As I opened the box my heart stopped. There was a note to me as well.
Steve,
Enjoy your big night. Think of me when you wear these.
Rob
PS Send me a picture!
Under the note were a black garter belt and two packages of black
stockings from Victoria's Secret.
Nadene
- 19.10.2020
- 18
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