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GETTING PAID FOR TAKING IN THE MAIL
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Crossdresser virgin fucks his first girl.
3.4k words
4.5712.6k182
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TammyPanty
TammyPanty
70 Stories795 Followers

Living in a suburban subdivision in the late 1960's we had good family
friends that lived in the house that backed up to ours. A wooden set of
stairs was installed over the block wall fence so we could easily go
between the two back yards.

Our backyard neighbors, Shirley and Don, had no children. Shirley was
about 15 years younger than her husband Don. She was very cute and very
outgoing. When they would go on vacation in the summer they would always
pay me to take in their mail and feed their dog and water their lawn. I
was just about to turn 19 years old the last time I was hired to do this
chore, and I received the most memorable payment I ever had.

Both Shirley and Don had returned from their vacation. It was the Monday
after they returned and both of my parents were at work and Shirley's
husband, Don had gone to work too. It was summer time so I had all day
off. I climbed over the wooden stairs and went to the backdoor to return
the house key and get paid for my job.

Shirley came to the door wearing a cotton blouse and a coulotte skirt.
She had on summer sandals.

"Hi Tom. Did everything go okay while we were gone?" Said Shirley.

"Everything was fine. You got all your mail, right?" I replied.

"I did. Thanks for sorting it out."

"Well, here's your key and we agreed on ten dollars for the week." I said.

"We did. Follow me while I get my purse. I hope you don't mind a check.
We spent all our cash on vacation." She said.

"Not a problem at all."

I followed Shirley down the hall and into the master bedroom. Her purse
was sitting on her dresser. She got out her checkbook and wrote me a
check. I stood quietly as she did this.

"Here's your check. Did you find anything you liked in my dresser
drawers?" Said Shirley very casually.

"Pardon me?" I replied.

"Did you find anything you liked in my dresser drawers?" She said again.

"I'm not sure what you mean." I replied.

"Tom.....It's okay. I can tell you have been going through my dresser
drawers. I am very particular on folding my lingerie and it is obvious
to me it has been disturbed."

Shirley was right and I knew it. When I would take care of their house I
would feed the dog in the morning wearing only my pajamas and a robe and
then make a beeline for the master bedroom. The first time I did this I
could not believe my luck when I opened the drawers and found the
beautiful lingerie I found. Two of the three dresser drawers were filled
with it. My favorites were her breath taking nylon and lace white bikini
panties. They were so sexy and feminine. She also had a half dozen nylon
and lace petti pants in all different colors. The second drawer was
filled with folded nylon and lace full slips and half-slips, again, in
all kinds of colors.

Even though I was a week away from my 19th birthday, I weighed only 110
pounds and had a very slight build. Shirley's panties and slips fit me
perfectly. I was very naïve sexually. I had never had a girlfriend and
to the best of my knowledge I had never ejaculated. My long thin penis
would get hard the moment I saw the lingerie, but I did not know what to
do after that as I pulled on her panties and topped it off with a full
slip. Some days I wore the petti pants and liked the way the nylon and
lace hugged my legs.

"I only looked at it." I stammered as I answered.

"I think you did more than look at it. It has definitely been removed
and put back. You didn't by any chance try some of it on did you?" She
asked slyly.

I swallowed a little bit hard and did not make a sound.

"I can tell by what you're not saying the answer is 'yes." She said.

I stood quietly stunned not knowing what to do or say next. Wearing her
panties and slips was just the start as I also found under the lingerie
her vibrator and her diaphragm as it was obvious having sex was
something she did on a regular basis.

"You want me to tell your parents what I know?" She asked.

"I sure don't. Can't you please keep this to yourself?" I pleaded.

"I think we can find a way for me and you to keep this between us." She
said with a smile.

"Oh thank you..........Thank you." I said quickly.

"How about you take off all your clothes right here and I'll show you
what you were missing in my dresser." She said in a matter of fact way.

"Take off my clothes? Now? Right here?"

"You heard me. Unless you want me telling your parents, not to mention
what will happen when I tell my husband Don." She replied.

"Okay......Okay.....no. I don't want you telling anyone." I said a
little panicked.

"Now you've got it. Put you clothes in a pile on the floor."

I did as she told me to. I was only wearing shorts and a t-shirt over my
jockey underwear. I stripped completely nude in front of her.

"Oh wow....for almost being 19 you have hardly any pubic hair between
your legs. Have you gone through puberty yet?" Asked Shirley.

"Yes I have gone through it. I'm just really slow to mature." I said meekly.

"You really don't have much of any hair on your entire body. Do you
shave it off?" She asked.

She had caught me again.

"I do shave my chest and my legs. It has not grown back in since I
shaved it the first couple of times." I said.

"I like the look! You're almost 19 and I'm almost 39. I've always wanted
to show a young boy what sex with a mature woman feels like." Said Shirley.

"Is that what we're going to do?" I asked. "Because just so you know I'm
a virgin and not really sure I can ejaculate."

"Don't worry about it, everything is going to be fine." She said.

"But what about Don, your husband? Won't he find out?" I asked.

"He won't because you won't say anything or I'll tell him and your folks
you forced me to have sex. Besides.......if it makes you feel any
better, I'm a virgin at this too. I've never fucked someone as young as
you. We'll learn this together." Said Shirley.

I was standing next to the foot of her bed totally naked and Shirley had
all of her clothes on. She was looking me up and down and my long, thin
penis was starting to grow.

"Turn around........lets me see your naked ass."

I did as she asked.

"Oh my..........young, 19 year old ass. You're getting me hot little
boy. Unless you'd rather play in my panties and slips as you did when we
were away."

"Not unless you want me to." I said as I turned back around exposing my
ever growing cock. "Since we're getting so intimate, I did want you to
know you have beautiful, sexy panties and slips in your dresser. You are
ultra-feminine and it turns me on." I continued.

"I'm glad to hear you say that. I love wearing sexy lingerie under my
everyday clothes. My husband Don knows I do it and he calls it
'playtime' when we're undressing for bed." She said with a sigh.

"Well, it really turns me on. And as long as we're sharing, I wear my
mother's panties and bras and slips with a nightgown on over it when
she's not at home. I love the feminine feeling it gives me." I confessed.

"Then why don't you come over to me and unbutton my blouse?" Said
Shirley. "I'll talk you through what to do."

I approached her as my erection kept growing between my legs. I reached
for her top button and slowly unbuttoned her blouse all the way down to
her waist.

"That's a good boy. Now open the blouse and slide it down my arms." She
said.

I did as she asked which exposed her white satin and lace bra. Shirley
did not have overly large breasts, but when she gave me my next
direction I saw what she did have.

"Now reach around my back and unhook my bra and slide it down my arms.
I'm sure you know how to do this if you wear them as much as you say you
do."

I followed her directions and slowly pulled her bra down her arms. She
had flatter than normal breasts but she had bigger than normal areolas
and nipples, and her nipples were sticking straight out and a little bit up.

"Other than my mother, these are the only mature woman's naked breasts I
have ever seen." I said.

"Do you like what you see?" She asked.