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GETTING PAID FOR TAKING IN THE MAIL
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Crossdresser virgin fucks his first girl.
3.4k words
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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.

"Very much.........Your bra and your breasts are very sexy. And your
nipples seem to be getting bigger." I replied.

"Well so is your penis! If you haven't bothered to notice." She shot back.

"I'm feeling it, and I've never felt this way before."

"I'm sure you haven't. Now unbutton and unzip my culottes. The button
and zipper are on the side. Let them slide down to the floor." Said Shirley.

I followed her instructions and underneath she was wearing a pair of
beautifully sexy petti pants. Light yellow nylon with white lace around
the legs and up and down the slit between her legs.

"You are gorgeous!" I blurted out.

"Well you're not so bad yourself." She replied.

As she stepped out of her culottes she sat back onto the bed and pulled
herself off the floor. She laid down propping herself up with one of her
elbows. She was still in her petti pants and I was still naked growing
my erection.

"Come lay next to me on the bed Tom. Let's pretend it's feeding time for
you and I'm the one feeding you your milk." Said Shirley as she went
down on her back.

I climbed on the bed and got up close to her.

"That's good. Now gently bring you mouth down to one of my nipples and
use your tongue to lick me and get me wet, then take my nipple between
your lips and start to suck on it. Do the same to my other nipple and
keep doing this back and forth until I tell you what to do next."

As I did what she asked I could tell she was slightly spreading her legs
apart and she put her hand between her legs over her petti pants. She
began to breathe deep breaths as I continued to gently, but firmly suck
on each of her nipples. I could feel them getting bigger, and rounder,
and harder every time I sucked them between my lips. Shirley's breathing
got deeper and I could hear a wet sound coming from between her legs
inside her petti pants.

"Oh my God..........For a young beginner you are wonderful! So soft and
gentle." She gasped.

"I hope I'm doing this right." I said meekly.

"You're doing it perfectly! Keep doing what you are doing."

It was just a few seconds later that Shirley's legs began to twitch as
she pushed harder between her legs and she really gasped for air.

"Oh that's it!.........That's it!.............I'm cumming!" She said in
a gasp.

With that her whole body seemed to tense up and then relax and then
tense up again and then relax. Her nipples quivered in my mouth as she came.

"Whew Tom...........You really have me hot! Are you sure you've never
done this before?" She asked.

"I'm sure.........You are my first." I replied.

"How about you sliding down my petti pants and getting them off my
legs?" Asked Shirley.

"I'd love to!" I said quickly.

"Do it slowly..............pull from the bottom of the panties and let
the waistband slowly reveal my pussy to you."

I did exactly what she asked. Her petti pants were soaking wet between
her legs and she slightly lifted her butt so I could easily slide them
down her legs. When I had them off of her I saw her very wet pussy which
had pubic hair, but closely trimmed pubic hair that did not hide her now
bulging vaginal lips.

"You're really wet!" I said.

"It's because I'm really turned on!" She said quickly. "Go into the
closet and get the baby doll nighty top and put it on." Said Shirley.

"What?!" I replied.

"Don't 'what' me. Just do it. I know you know what it is. You've
probably worn it before. And get back on the bed quickly. I want your
long, hard, young, cock inside me right now!" Said Shirley in an urgent
tone.

I quickly got the light yellow baby doll top and put it on over my head
and got back on the bed. Shirley had spread her legs wide open and was
fingering her pussy in an up and down motion.

"Oh yes. That's what I want to see. I want your cock inside my pussy and
I want it now. You're such a sweet little boy in my baby doll."

As Shirley was saying this she was reaching for my erect cock. As she
felt it, she pulled it toward her now soaked vaginal lips. She was
pushing the head of my cock against her body in several places as if to
feel for her opening. On the third or fourth try I felt her lips engulf
my penis as I slid inside of her with ease.

"Is this it? Are we fucking?" I asked breathlessly.

"Oh honey we are doing more than fucking, you are filling me with young
boy cock and I love it!" Said Shirley as she smiled in delight.

"Shouldn't you have your diaphragm inserted?" I managed to grunt out.

"I don't want to wait for that. I want your cock to fill me full. Now
lean down and suck on my nipples again like you did before." Directed
Shirley.

"What if I get you pregnant?" I asked quickly.

"Don't even think about it. All I want is for you to cum inside me. Fuck
me Tom and don't worry about what happens. Now slide you cock back
without letting it come out of me and push it in again. Keep doing this
over and over." Said Shirley.

I followed her instructions while I sucked on her nipples. Her eyes were
rolling back in her head and I felt her pussy lips squeezing my erection
and letting it go and then squeezing it again. Shirley was gasping each
time I felt her squeeze me and all I could do was keep sliding in and
out of her and sucking on her nipples. She began a full body muscle
spasm as she gasped loudly and said;

"Oh dear God, oh dear God..............I've never cum this hard in my
life! I'm really cumming like never before!"

Her body was rising up off the bed from the waist up and she hugged me
tight to her with her arms.

"Come on pretty boy! Cum for Shirley! Ejaculate inside me and fill me
with your semen! You can do it! Keep pushing! You can cum! I want you to
cum!"

She was right. I felt something I had never felt before. I felt as if I
had to pee, but I could not stop it. In fact what was happening is I was
ejaculating for the first time in my life. And I was ejaculating inside
a woman who was 20 years older than me and married to another man.
Everything about this seemed wrong but that did not stop me from
twitching and shooting stream after stream of fluid out of my rock hard
cock. I felt five different shots come out of me and with each one
Shirley moaned in delight.

"Oh my God that felt good!........ That felt
wonderful!.................I asked you to fuck me and you did it! You
did it with a pretty nighty top on and you filled my pussy with your
semen and sperm. That's so naughty.......but I loved it...............I
really loved it!" Said Shirley as she was catching her breath.

We were still joined at the genitals as it took some extra time for me
to begin to get soft. We did not kiss, but Shirley directed my mouth
back down to her nipples which I kissed and licked.

"Do you still want to play in my panties and slips?" She asked.

"I'd much rather play in your pussy." I responded.

"I'd like that too. But next time I'll have to plan for it and put in my
diaphragm in before we fuck. I want you cumming inside me, but I don't
want you getting me pregnant. Before you go I would like to show you how
to suck on my clit."

"You mean you want my face down between your legs?" I asked.

"Yes honey. It's the ultimate way a boy makes love to a girl. You'll
like it. I'll spread my legs and you slide down between them."

I did as she asked and saw her soaking wet pussy in front of me. The
white cream of my ejaculate was dripping out of her vaginal lips.

"Okay Tom, use your tongue and lick at the top of my pussy lips until
you feel a little bump."

I did this and immediately felt the bump and when I flicked at it, it
immediately began to get bigger.

"That's it! That's my clit! You've found it. Keep licking it and when it
gets big put it between your lips and suck on it!" Said Shirley as she
breathed deeper.

I was gently sucking on her enlarged clit as she began to twist her
pelvis and then she gasped out loud and her body convulsed as she was
having another orgasm. As her vaginal lips twitched in and out I felt my
semen come splashing out onto my chin.

"That's it.................That's it.....................You're doing it
to me again! I'm cumming so hard!" Said Shirley.

I just kept sucking and licking her clit and she came a little less
violently a second time. She was totally out of breath and my young cock
was starting to get hard again. Shirley used her hands to pull my head
off her pussy and bring it up to her face. We were both fully nude next
to one another on the bed.

"I know you like playing in my panties so I'm going to give you a pair
to keep. Don't let your parents know and keep them hidden. I wear the
most sexy, feminine panties I can every day to remind me what a pretty
girl I am and to have them on if a man gets me into a compromising
position." Said Shirley.

"What other man would that be?" I asked.

"I have a couple of 'fuck buddies' that call me infrequently to get
together with me just to fuck." She said.

"Does your husband Don know about them?" I asked.

"No..........Not at all. But he and I have a very active sex life so I'm
sure he doesn't care if I get a little more on my own time." She said
confidently.

"Wow, I had no idea." I replied.

"Well now you know, and now you are going to be one of my 'fuck
buddies.' When I call you I'll expect you to be ready to service me in a
way I tell you to."

"I would love that." I said.

"Good. You're the first 19 year old I've ever fucked. I was a virgin
until I got married at 25. I never fooled around with boys when I was
young. Your sexual stamina is wonderful! I can't wait until we find more
time to fuck again." She said with a smile.

"I'm happy to know I can ejaculate." I smiled.

"Oh you can ejaculate alright. In fact you filled me more than I have
ever been filled. Let's hope I don't get pregnant. I think we'll just
miss my period so we should be okay." She reassured me.

"Well.........I really loved the experience. You are a very beautiful
and sexually aggressive lady. I'm so happy you let me lose my virginity
to you."

"Believe me, the pleasure was all mine. Now take off my nighty top and
get yourself a pair of panties and remember to keep this as only a
memory between the two of us." Said Shirley.

"I always will." I replied.

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TammyPanty
TammyPanty
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2 COMMENTS
sissyboi69Aricsissyboi69Aric6 months ago
I love this story; I too lost my virginity to a much older woman. Please
continue with this story.

fran969fran9696 months ago
Fantastic Every young mans dream...~~