Date: Sun, 4 Jan 2015 22:48:56 +0000 (UTC)
From: Beaumonte Bill <oral_guy_2000@yahoo.com>
Subject: Bill and Ann Part 9

I am an older married man who has dated many cross dressers and transgender
women over the years.  At first it was a kinky "walk and the wild side" but
over time I came to really have feelings for the person, and that became
more important than the intimacy we had.  The movie "Soldier's Girl" was
very moving and helped me realize that I really wanted to LOVE a
transgender woman.

I have had several truly wonderful loving relationships, and have come to
believe that if I knew what I know now when I was young, I would have
married a transgender woman.  This series is a fantasy in which I imagine
what that life might have been like.  It is set in the late 1960's, when I
was a teen.  –Bill (oral_guy_2000@yahoo.com)


Bill and Ann Part 9

I made my way to Ann's house.  Ann advised me that her Social Security card
had arrived and she was ecstatic!  We planned a date in town and would open
up a bank account for Ann.

I arrived and was greeted with Ann's customary kiss, which I always found
wonderfully welcomed.  Upon entering Ann proudly presented her new Social
Security card.

"This is wonderful, dear. It is much more than just a little card," I said,
"it is part of the official government record of Ann Marie Martin.  Next
year you can get your driver's license which will be further proof of who
you are."

Ann excused herself to finish getting ready for our date.

Helen sat down next to me and began, "You have been a great blessing to Ann
and myself."

"To you as well?" I asked.

"Yes, to me as well," she responded, "Raising Ann alone had been a
challenge, but since you have joined our family it has been easier – I
love the way you are tending to Ann's future."

"Well, in order to marry her properly, we have to have everything in
order," I said.

"That's one thing I wanted to discuss with you," Helen continued, "please
think about what sort of work you and Ann will do, and if one or both of
you will be going to college.  You need not be in a hurry to rush into
marriage.  In many ways it is like you are already married.  Any time you
want intimacy, you can go to Ann's room and I will never interfere."

"Thank you, Mom," I said, "there is indeed much to think about regarding
the future.  She and I are both very good in math and science, so I think
that college for both of us might be right.  Of course we will have to
figure out how to pay for it."

"You are indeed mature beyond your years, dear boy," she said, "but there
is one more thing I want you to think about."

"What is that, Mom?" I asked.

"Ann cannot get pregnant," she said, "which is certainly convenient for
now; you will never be able to father a child with her."

"I understand that quite well, Mom," I replied, "Raising children is quite
a big deal. Many people do it badly, and I'm not sure we will be up to the
task, but if we do want children, we can adopt."

"Well said, and apparently well thought out as well," Helen said, "I'm so
glad to have you in the family."

I arose and kissed her on the cheek, and hugged her.  "Thank you," I said,
"that means a lot to me."

Ann appeared, ready to depart, so we left for the bus stop.  When we
arrived in town, we went to the bank to open Ann's account.  Ann proposed
that we open the account jointly, but I refused, insisting that Helen be
the joint owner.  She agreed, though with some reluctance.  When the teller
asked about funding the account, Ann took fifty dollars from her purse.

"One more thing," I said, and placed $300 on the table.  Ann looked at me
with surprise, but I signaled her to just go with it.

As we left the bank with Ann's brand new bank book, she asked, "Why would
you not be the joint owner of my account, especially when you have put so
much money in it, and what is that $300 about, anyway?"

"The account is yours," I answered, "and while I feel I have a claim on
you, my lady, I have no claim on your money.  The $300 was what was left
after I bought you ring – you remember I saved $500 for your birth
certificate, which I did not need to spend, so I resolved that I would
spend it all on you."

"You are a very stubborn man, but I love you more than you can imagine,"
she said, "I shall be very proud to be your wife one day, but meanwhile
there is one remaining duty for you to attend to."

"Oh, what have I overlooked?" I asked.

"Your lady is still a virgin, and I am looking forward to your changing
that!" she said with a big smile.

"I shall lose no time in correcting that oversight," I said, holding her
closely and kissing her.

"We went to Brenda's Diner, which had become our usual place to dine in
town.  We enjoyed a nice lunch and I suggested that we see a movie, but Ann
reminded me of our "unfinished business", so we caught the bus home
instead.

When we arrived at Ann's house she left her bank book on the table and we
went upstairs to her room.

I prepared a warm wet wash cloth for cleanup and placed it on the
nightstand along with a jar of lube.  I was determined to make our first
time perfect – a memory she would cherish always.

We undressed each other, slowly and lovingly, and then embraced nude, our
skin warm against each other.  I guided her to bed.  I laid on my back,
with a couple of pillows supporting my head and shoulders.

"For this time," I said, "I want you to use a position called the 'cowgirl'
position.  It will give you complete control, so entry will be at your own
pace."

"Cowgirl?" she asked, "do I get to wear a hat and spurs?"

As we both laughed, I replied, "Maybe next time.  For right now get your
pretty buns up here and I will prep you while you suck me to erection."

Ann eagerly took her place as I described.  I kissed her wonderfully clean
rosebud as she sucked me.  It was truly heavenly to join with her in this
manner, but today I had a higher duty.  I pulled back and said, "Better
stop for now, or we will have a miss-fire."

She giggled and stopped as I lubed my fingers and inserted one, and then
another in her tender rosebud.  Ann moaned with delight.  I gently inserted
a third lubed finger and worked all fingers in and out, making sure there
was plenty of lube on and in her.

"Okay, time to get into position," I said, "kneel over my hips and slowly
lower yourself onto me.  When you touch, stop and then very gently press
down.  If it seems difficult, just stop for a bit, and continue when you
are ready.  There is no hurry, so please move at your own pace."

Ann did as I instructed as I put lube on my cock head.  I felt her pressing
against me, and then firmly down.  She opened rather easily and I slid
inside.  She paused for a bit and then continued to press down until I was
fully inside her.  Her eyes grew wide and she said, "This is fantastic –
we shall have to do more of this!"

"Now let's go for a little ride, cowgirl" I said, placing my hands on her
shapely hips and guiding her as she tentatively bounced up and down.  Soon
we settled into a rhythm and Ann was fully in control of the ride."

I fondled her breasts, now grown substantially, and gently squeezed her
nipples.  She gasped with delight as I did, and rode a bit faster.  I put
more lube on my hand and began fonding her clitty, which was bouncing up
and down as she rode.

After a few more minutes of fondling Ann's clitty she reached climax and
screamed a bit.

"Everything ok?" asked Helen at the door.

"Yes, it's wonderful," Ann blurted out, "Now do come in and see for
yourself!"

"Oh my!", said Helen, "I shouldn't be seeing this!"

While I was initially shocked, I regained my composure and said, "Perhaps
you should, Mom.  Please sit down and enjoy this wonderful event with us."

"My virginity is gone now," Ann said.

"And mine too," I added.

"I can see that you are coupled, though I would not have expected this
position," said Helen.

"You didn't cum, did you?" Ann asked me.

"No but you did!" I replied.

"Mom, thank you for being with us at this wonderful time," Ann said, "Would
you please excuse us while I finish with Bill?"

"Yes, of course," responded Helen, "Make sure you take good care of him –
he has obviously taken good care of you.

Helen left and Ann dismounted.  I wiped her clean and she wiped me clean
and then sucked me to climax.

Afterward Ann laid her head on my chest and we lay quietly together for a
time.

We got dressed.  I went downstairs and Ann went to freshen up.  I saw Helen
and said, "I hope that was not too vulgar, Mom.  I'm glad to share such a
special occasion, though I hope it didn't embarrass you."

"I'm not the least embarrassed, but certainly surprised, "just as I was
surprised to see your generous gift to Ann in her bank book."

"I just wanted her to get off to a good start," I responded.

"Starting with today, I will match any cash gift you make", Helen added,
"after all, her future is important to me as well."

"Thank you, Mom," I replied.

"I was surprised that you were a virgin," she said, "You seemed more of a
man of the world than a virgin.  So how was your first time?"

"Amazing!" I said, "Being joined to Ann like that was better than I could
have imagined!"

"Now that you have 'broken the ice', so to speak, I'm sure there will be
many more," Helen said with a smile.

I thanked her for being so wonderful to both of us, and departed for home.

To be continued . . .

Feel free to contact me with your comments or requests.  –Bill
(oral_guy_2000@yahoo.com)