by: Lyssa
View Story Details
| Rating: R Add Review Read Reviews, Last Review 05/23/07 (1) Added: 05/23/2007 |
| Complete: yes |
| Synopsis: Discovered wearing non-male clothes, Tony is ask to change fully into |
| Jessica's clothes. |
| Categories: Caught with Consequences Crossdressing / TV |
Needs and Wants
by Lyssa
The waitress placed a glass of white wine on the table in front of me.
"I didn't order any wine," I said to her.
"It is compliments of the gentleman there," she replied in an accented
voice. I turned in my seat and looked the way she was facing. A man at a
table in the back corner of the dark Italian restaurant raised a glass
of wine towards me. "He also would like you to join him. You are both
eating alone so maybe you have some nice company. I bring your zuppa to
you there." She left without letting me answer.
**
Once in a while I just need to get out and do something different. This
time it was to see a play on Broadway. This is quite a normal activity
in New York, but I was spicing it up a bit. I wore a navy blue polo-type
top, jeans and sneakers. To the normal eye I'm just another guy out on
the street, but if you look real closely you'd notice that the neck
buttons on the top are reversed, the fabric is a little more drapey than
normal and the sleeves are slightly shorter, the jeans have a slightly
tapered leg to them, rather than straight cut. If you were to strip all
those away though, you'd fine a white floral satin camisole, panties and
a g-string style gaff, and pantyhose. From the time I stepped out of my
car two hours ago I was wearing completely women's clothing, including
my windbreaker jacket and white socks (to hide the pantyhose.) Outwardly
I believed I appeared as a normal guy with a hint of something
different, which really isn't anything uncommon in New York. The
important thing to me was that I knew what I was wearing, and it was
part of the thrill.
When I parked my car and changed I was in everything except the
camisole. With my body and shape it placed a quite obvious line across
my back so I didn't want to wear it should I sit somewhere that leaves
my back open. I have been to the restaurant before, and I knew there
were bench seats against the wall at some tables, so I'd add that item
once I got there. When I did walk down the steps and into the restaurant
I saw all the tables with benches were available. I asked for one of
those tables and ran to the bathroom before I sat down. After locking
the door I took off my jacket and shirt and pulled the camisole over me,
replacing the other two items before walking to my table.
I took a few minutes looking at the menu before selecting on the
price-fixe dinner (a three course meal at a set price, picking from a
select list.) When the waitress returned I placed my order of the daily
soup and veal parmesan, but she cut me off before I could order dessert,
saying she'd let me know after the meal what was available. A few
minutes later she returned with a glass of wine.
As I walked to the back of the narrow restaurant (there was one aisle
with tables on each side) I saw he was at a square 4-seat table. He was
sitting with his back to the back wall and as I approached he motioned
to his right, at the seat against the side wall.
"This would be a better seat for you here." I was going to sit across
>from him, but I accepted, curiously curious about why he wanted me to
sit there. "I hope you don't mind me being so bold, but why eat alone?
Italian food is festive and should be shared with others. My name is
Frank."
"Hello, I'm Tony."
"Is that with a Y or an I?" he asked.
"Why?" I replied, more of a question before realizing the pun. "Um, I
mean a Y." I answer in more of an annoyed tone.
"That is just an unusually masculine name for someone wearing something
so pretty." It was then that I felt a slight tug and turned to my left
when he was pulling on my camisole. I turned red in embarrassment as a
few inches of it was hanging out, not tucked into my jeans. "Do you have
a name that is more in line with how you are dressed?" I was still
frozen at being "read' and couldn't answer yet. "Why don't you have a
sip of wine first, and then you can tell me who I am dining with
tonight."
I picked up the glass and had more than one sip before putting it down.
"Jessica."
"Nice to meet you Jessica." Just then the waitress brought my soup and
placed it in front of me. I finished the soup before we talked again.
"So Jessica, what brought you into this restaurant?"
"I stopped here for dinner before I go and see a play." He asked me what
I was seeing.
"Oh, I heard good things about it. Are you seeing it alone?" I nodded.
"And do you have tickets yet?" I nodded again. "You know what, I've been
meaning to see that too. While coming here I noticed that half-price
tickets were available. How about I buy us a pair of tickets to see it,
and we can try and sell yours. Think about it for now and let me know
later." I'm sure he could see the hesitating look on my face.
The rest of the meal went well. We did talk during the meal, but he
never said anything more about my clothes or situation. After the entrée
dishes were removed the waitress told us the dessert selections. I chose
tiramisu and hot tea while he had crème brule and coffee. We talked for
a bit after we finished. The waitress took our plates and I asked for my
check.
"Oh, dinner is all paid for already." I looked at Frank.
"It is my treat for keeping me company during the meal, and hopefully
during the play as well." He looked at me in a happily questioning way.
I demurely nodded.
We walked together to the discount-ticket stand and he bought two seats
one row behind my original ticket, but on the other side of the house. I
was able to sell my ticket in front of the theater quickly, since it was
a nice front-row mezzanine seat.
**
After the play we walked down the street. I had mentioned that my car
was parked in a garage, so we were heading that way. It was about 6
blocks away and he walked with me the whole way.
"So Jessica, are these the only clothes you brought with you?"
Normally I would have been very tight-lipped about things, but he
already knew things and had put me at ease. "No, I like to dress up more
in the car on the way home."
"I would really like to see it on you. Would you mind if I came up with
you and let you change. I won't peek!" He smiled as he said the last and
it made me laugh.
"Ok," was all I could say.
When we got to the car he walked back to the staircase and gave me my
privacy. Over the years I had become and expert in dressing in the car.
I took off my top and camisole, and my socks and sneakers. Out of my bag
I unrolled a brown floral skirt and slip and slide them up my legs to my
waist. I put on a white bra followed by a white camisole and then a
white short sleeved blouse. I placed the wig on my head and then applied
some makeup base on my face and then red lipstick. I stepped into a pair
of low healed black sling-back pumps, checked myself in the mirror, and
then got out of the car.
He saw me get out and walked over to me. "Oh my, that is much better my
dear Jessica. Turn around for me." I twirled lightly around. In my heels
he was still about an inch taller than me. "On the way here I saw a
place we can get a nice pastry and coffee. How about we go there before
you drive home?"
"I can't go outside like this."
"Why not? You look fine. Anyway, you won't be alone, you will be with
me."
I didn't want to but he kept pestering me until I agreed. I picked up my
jacket and backpack and was about to close the door when he stopped me.
"That jacket doesn't go with the nice clothes you have, so leave it, and
the same for the backpack. Do you have a pocketbook?"
"Not with me, no."
"Do you have a small plastic bag?" I nodded. "Ok, take the bag and put
your lipstick and car keys in there." I grabbed the things and put the
car keys in the bag after locking the door. Then he took the bag from me
and we walked down the stairs.
I absolutely know that everyone in the city was looking at me, the freak
show reject, as I walked out of the garage. I was so…. SO nervous. He
sensed my hesitation and took my hand, leading me out onto the street.
"There, that wasn't so bad, was it Jessica?" I was still too stunned to
answer.
When we walked up to the Avenue we stopped at a souvenir store that
happened to also have things other than tee shirts and hats. I bought a
maroon pocketbook and placed the contents of the bag into it, then
handed it to me. I placed it on my right shoulder and thanked him. He
took my hand again and led me to the pastry shop. I pointed to what I
wanted, and he ordered for us, plus tea for me. He picked up the tray of
items and we walked to a seating area. The tables were all high, with
bar-stool high chairs to sit on.
We talked as I carefully ate my food. We were there for a good 45
minutes before I realized how late it was. "Before we walk back you
should touch up your lipstick. There's a bathroom back there, oh and
don't forget which one to use Jessica." I'm actually glad he said
something. Luckily it was a private bathroom, so I locked the door as I
reapplied the lipstick. He was waiting in the front of the shop for me.
As we walked out the door he put his arm inside mine and we walked back
to the car arm in arm.
"Thank you so much for the evening and everything. You really shouldn't
have paid for the meal and buying this for me. I don't know how to thank
you."
"Seeing Jessica like this, and seeing you happy makes it all worthwhile.
But if you really want to make an old man happy, give me one kiss before
you go."
I actually didn't mind the suggestion and I stepped closer to him. He
leaned forward and kissed me.
When he kissed me he didn't hold me or anything. There was nothing that
was keeping me close to him, but even so our lips didn't separate. I
think it was my hand that actually went around him first. The next thing
I knew he was leaning me back against the car while his body gently
pressed against me. It was minutes before we came up for air, but in the
meantime I could feel something pressing against me. If I was wearing my
jeans I probably wouldn't have noticed, but the thin layers of my skirt
and slip I could feel his hard arousal. I know I was too, but it was
trapped back between my legs.
Whether it was my arousal and knowing I caused his arousal, something
inside me made me want to do something else. With my back pressed
against the car I slid down, getting into a catcher's stance, with my
legs open around his. When my head was at his groin I unzipped his pants.
"Oh Jessica, you don't need to do this to pay me back. I was happy to do
everything."
I looked up at him, "I want to do this." I looked back ahead and slid
him into my mouth. He was moaning as I sucked on him. As I was doing
this I could feel myself leak into my panties. Normally I can control
myself by keeping my legs together but in this position I was
defenseless and just oozed out, not in an orgasm but still soaking my
panties. Just then he released into my mouth. I kept him in my mouth
until he started to go soft. He was leaning against the car with both
hands, but he stood up, reached down and took my hands, helping me stand.
He stood so close to me still that my legs were still spread and he
kissed me. Before I knew my skirt was pulled up and his hand went
between my legs. I jumped as he touched me there, and he rubbed for a
second before bringing his fingers up and feeling the wetness on them.
He took the sticky fingers and put them to my lips, and I gently sucked
on them, cleaning myself off him.
"I want to see you again Jessica," he said.
"I need to come back," I replied.