This is a continuation of "Life's Lottery". Steve is delving deeper into his Sarah persona.
This story contains sexual scenes.

I bit the bullet and took some pictures of myself as Sarah. Nothing
outrageous, mainly just myself in various wigs and underwear. Then I
posted them on a few contact sites. I really did not know what to expect,
and to be honest I really don't know why I did it. I think I was seeking
affirmation that I was acceptable as a woman by men.

I did note in my profile I was a crossdresser. It seemed wrong to say I
was trans. I really don't know what I am. I wasn't expecting any
responses, but when I checked the next day I had an overflowing mailbox.

Many were men just wanting quick sex. A large number of these were very
crude. I noticed that the more thoughtful messages came from the older
men. The majority of the messages made me feel sorry for women. If they
had to put up with men asking for the sort of things they had asked, then
god help them. I did realise that most men seem to think crossdressers,
dress just for sex. That may be true for some, but not for me.

I think I saw it as being one step closer to being a woman. Women have
sex with men. If I had sex with a man it would make me more womanly. That
was my thought process anyway. I got some "toys" from eBay and had been
practicing. It was uncomfortable at first, but after several attempts, I
found it quite pleasurable. I grew excited at the idea of perhaps having a real-
life warm man inside me.

I found one profile intriguing. It read.

Phil. A mature guy wants to meet trans/cd gurls to have fun with at my
house. Single, so I can accommodate for overnight stays, and even short
breaks. I do not want this to be just about sex. I do want a sub girl who
dresses 24/7. A "Stepford wife" would be nice, and welcome to live full-
time as my wife.

Could this be true? Would someone want a man posing as a woman to live as
his wife? My heart pounded in my chest. This was something I had never
expected. The idea was giving me a huge thrill. It would be like being
trapped. Forced to maintain a facade as a female full-time. If I
committed to something like this, it would be a full-on experience. I had
spent a few days as a woman and loved it, but I knew that I would change
back after a few days.

I could not get the idea out of my head. I wrestled with my feelings for
a week, then I messaged Phil. He was a perfect gentleman. I asked if he
was gay but would not admit it. Was that why he was seeking a
crossdressing partner?

He explained that he wasn't gay but bisexual. He had slept with women and
a few men. He adored femininity and women but enjoyed men. He had found
that with crossdressers, he could get the best of both. That sort of made
sense.

He arranged to pick me up from my flat and take me to dinner in a quiet
Italian restaurant. This would be one of many firsts for me. He assured
me that I would pass easily for a woman when I told him how nervous I
was. I knew I could not waste a chance like this.

I took an age to bathe and shave. I selected pretty, but down-to-earth
clothes. Super high heels and a mini skirt are fine if you want to be
read, I just wanted to pass. Nothing to see here. Just a woman having a
meal.

I wore a black corselette over my black lace knickers. Black stockings, a
full-length slip, a dark blue silky blouse, and a calf-length black
pleated skirt. I wore my two-inches heeled, black boots with this. I just
loved women's boots. They were ruched leather, with gold buckles.

When I had done my makeup for the third time I was ready. I sprayed an
extra dose of perfume on my neck and waited at the front door. My stomach
was doing cartwheels. The anticipation and my nerves fighting to see who
would win. Part of me was hoping he would not show, and part wished he
would.

Then there was a knock at the door. I held my breath and opened it. There
stood Phil. A handsome man with a head of grey hair. Just like his
profile picture. He looked taller than his picture. He was a good 6
inches taller than me at 6ft 2.
He had a broad chest that made me look slight in comparison.

"Sarah. My, my. You are more beautiful in person."

He held out his hand and I saw the rose he offered. I took a deep breath.
What a wonderful gesture. My eyes teared up. This was a unique gesture
that only women are offered by men. It meant so much to me at that
moment. I melted. He could have asked me to do anything and I would have.
He saw my reaction and understood.

"Oh, Sarah. It's alright. A beautiful woman like you should get used to
getting flowers from admirers."

"Thank you, Phil. It's just that......"

He kissed me on the cheek and led me to his car.

On the way to the restaurant, we talked about our lives. He asked me why
I did not live as a woman all the time. I told him that I needed to work
to support myself. I was sure I would get fired if I came out. He looked
thoughtful.

When we arrived he opened the car door for me. Another first. We had
parked a few hundred yards from the restaurant. He made sure he stood on
my right side as we walked. I remember I had read that in the Middle
Ages, knights wore their swords on the left side of their bodies which
allowed their right arm available for a quick response to protect their
lady.

This gave me a thrill. He had an old-fashioned sense of chivalry. I knew
I was in for a full experience of what it was like to be a woman in
perhaps the 1950s. I caught a glance of our reflection in a shop window.
We made a handsome couple. As I walked, I felt my suspenders tugging on
my stockings, the swish of my skirt about my knees. I even felt my lace
knickers slowly moving into the crease of my buttocks. It felt so
sensual. With the sound of my heels clicking as a background, I went into
mental overload. I wished this would never end. If this is what women
felt like all the time, I never wanted to be a man again.

He opened the door and we were shown to our table. The waiter pulled out
the seat for me and we sat down.

"Shall I order for you Sarah? Would that be alright with you? I don't
mean to offend."

I smiled. He really was an old-fashioned guy. I loved it.

"Please do. I'm sure you know best Phil."

I couldn't believe I just said that, but this whole thing of acting as a
submissive woman was a new and wonderful experience.

Between courses, as we chatted he gently touched my hand. I didn't draw
away. By the time we had coffee, he leaned across and kissed me on the
mouth. Another first. My loins tingled when he kissed me. I knew then
that I wanted him.

"I know this is forward of me on our first date, but would you like to
come back for a nightcap?"

I looked into his eyes and saw a need. A fierce hunger for me. This
lovely man wanted me. Well Sarah, not Steve. Sarah was a desirable woman.
Steve had never really been desired by anyone. Even his ex-wife never
really desired him. Steve slipped away a little more and Sarah dominated.

"Yes. I think I rather would."

I winked at him. We both knew what was going to happen. Nightcap, coffee,
etchings. It was all the same. It meant sex.

When we got to his house, no sooner were we through the door than we
lunged at each other. The sexual tension in the car on the way was
tangible. His musky masculine smell, contrasted to my sweet feminine
scent. I felt more feminine than I had in my entire life.

Our tongues explored each other's mouths as our hands explored each
other's bodies. I felt his hands grip and squeeze my buttocks as my hands
went for his belt. His trousers dropped to the floor and I followed them.
I paused as I saw his growing erection. This would be another first.
Steve said no. After this, you'll be a cocksucker. Sarah said good, lots
of women are.

Steve watched in horror as Sarah's hand with its pretty pink nails pulled
down Phil's boxers and his hard member sprang out. Steve's voice was
silent now. Waiting for a line to be crossed. A line that you can't come
back from and still call yourself a man. A least that's how Steve saw it.

I licked the tip and heard Phil groan in pleasure. I used my hands to
pull his boxers completely off as I slowly engulfed his cock. My right
hand stroked the shaft, while I tickled his balls with the nails of my
left.

Phil moaned. "Oh, god yes, yes"

I was pleasing a man, I was pleasing a man as a woman.

I bobbed my head up and down and swirled my tongue under the shaft as I
sucked. I felt him stiffen then to my surprise he pulled away.

I looked up, my disappointment must be obvious.

"You almost drove me over the edge, Sarah. That was incredible. I just
want to have more fun and let you enjoy the pleasures of being a woman."

He helped me to stand and started to unbutton my blouse. I unbuttoned his
shirt and ran my fingers through his hairy chest. Steve never had any
hair on his chest, Sarah was glad about that.

Phil took in my underwear.

"What wonderful old fashion lingerie you are wearing. You must be a mind
reader. I love the 50's look. Is that a corselette?"

"Yes, look"

I lifted the hem of my skirt and petticoat, showing my stockings held
tight with the straps from the corselette. A look of sheer lust came
across his face. He grabbed my hips and pushed me into the kitchen
counter. I felt the back of my skirt lifted and his hand caressing my
backside through the nylon lace of my knickers.

"Oh god, that feels so good," I whispered.

"Where have you been all my life, you sexy bitch."

Bitch? Oh yes. I did feel like a bitch on heat. I felt my feet being
gently forced apart. My boot heels skidded slightly as my legs spread.
His fingers probed my hole. I shivered. I had played with myself plenty
of times, but this was someone else doing it. It felt so good.

"You're lubricated? You naughty girl. Expecting me to fuck you were you."

"I had hopes Phil. It always pays to be prepared. I have more lube in my
handbag."

He reached in and found the lube. I could hear him lubing himself up.
This is really going to happen I thought. I was going to have sex as a
woman. My breathing quickened in anticipation. He pressed himself against
me. I could feel his cock pressing between my buttocks. His hands reached
around my bra cups and found my nipples.

"Oh Phil, yes, yes!"

I had read online that some men have almost no feelings in their nipples.
My nipples are so sensitive that I once came by just playing with them. I
thrust my behind towards his cock. One hand left my right breast and I
felt the head of his cock push into my hole. I groaned out loud as he
slowly slid into me.

This felt so much better than my toys. It was warm, and hard, but most of
all I wasn't in control. I was being, fucked, used, and perhaps even made
love to. I felt my knees begin to buckle. The sensations were
overwhelming. The feeling of him sliding smoothly in and out. The
slapping sound as his balls met my buttocks. His hands returned to
tugging and squeezing my nipples. I could feel something building in me.
I was going to come without touching myself.

I looked around the kitchen and imagined myself as a suburban housewife.
I would live this life every day. Wear this sensual underwear, and feel
sexy walking in heels. Men might look at me with lustful thoughts. My
life would be filled with cooking and cleaning, makeup, dresses, and
trying different looks to make myself more attractive. I would wear sexy
undies in the bedroom to turn on my husband.

At that moment, with his cock inside me, his hand squeezing my nipple,
and his hot breath in my ear. I wanted nothing more. I wanted this
feeling to never go away. Steve's voice in my head was silent. He was
getting fucked out of Sarah until only Sarah remained.

I felt his right hand reach into my straining lace knickers and grip my
hard little "clittty".

"Cum for me. Cum for your husband like a good little housewife," he said
almost directly into my ear.

I shuddered and had the most powerful climax of my life. My knees
buckled, if he had not been holding me I would have fallen to the floor.
He continued to pump into me for a few more moments, then grunted as he
shed his pent-up load deep inside me.

I felt so satisfied. Sex had never been like this before. I enjoyed my
climax but was so happy I had satisfied him. He kissed the back of my
neck as I tried to compose myself.

"That was amazing Sarah. You are just too perfect. Will you stay the
night?"