Jug Loving Jerry
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First Time With Jerry free porn video
First Time With Jerry
Penned by: Miss Deborah Leigh Johnson
It was a rainy afternoon, a hot summer afternoon. I was with my friend
Jerry. Jerry and I were both sixteen. But that was the extent of our
similarities.
Jerry was tall, about 5' 8", while I was almost 5' 4". Jerry was stocky. I was
lithe, in fact, I was often teased for looking more like a girl than a boy.
Jerry was a jock, no surprise there. I was not. I compensated for my lack of
physical prowess with an alert bright mind that I used to learn everything that
I could about anything.
Jerry had really dark brown hair, and it was short, like a crew cut style. Mine
was light blond and I wore it to my shoulders. It was thick and naturally
wavy too. In fact, if I wore short, it would all kink up in tiny little curls that I
hated. That was why I wore it long. The weight of it long kept it from
kinking up on me all the time.
Jerry and I were friends out of necessity rather than any other reason. No one
knows why, but our parents had chosen to buy a remote chunk of land on the
side of a mountain. We were nearly three miles from the nearest town, and
there was only us to grow up and be friends with. If we were not friends,
we'd be two very lonely young people.
This particular afternoon, we were together. Our parents had decided to leave
for an over the week end fishing trip, and they left the two of us to keep each
other company. That was okay. We had grown to like each other, even
though we were so different from each other.
As per usual, I was making our lunches. We had learned by trial and error
that between the two of us, only one of us had any kind of culinary leanings,
and so it always fell to me to take care of the domestic needs as they arose
between us.
Jerry was in his room playing with the new computer that his parents had just
bought him, in some kind of hope of sparking any kind of a more intellectual
spark in their son.
I took the hamburgers and the salad up to his room. He already had a bar
refrigerator up there that he kept stalked with sodas. I made my way into the
room.
He looked up at me with glee when he saw that I was bringing food.
Naturally, his plate had nearly twice what mine did.
"Ahhh The fair young maiden arrives with tributes of repast for her master."
I blushed. I was almost getting used to these kind of comments from him. It
had seemed to start a few weeks before, come to think of it, it had started just
shortly after he had gotten his new computer. He had started to make little
comments about my effeminate nature. He'd tell me that I was pretty
sometimes. Sometimes, he'd just comment on how girlish I seemed to be on
some particular day. His comments were never rude or demeaning, just point
blank observations from him about me.
I had started to get used to it. I knew there was no point in trying to let him
know that his comments made my uncomfortable, as I was sure that if he
knew that, for sure he would intensify the activity. So I just grinned good
naturedly and pretended like nothing at all had happened out of the ordinary.
We had our lunch. Then he really floored me. We talked about sex with each
other of course, as most teen guys do, but this time, it took a very different
turn.
"Dougie?"
"Ummm?"
"You know what a transvestite is?"
"No. What is it? I don't think I have ever heard that word before. What is it?"
"A transvestite is a guy who feels better when he wears girl's clothes."
"What? I never heard of such a thing."
"Yeah, and from what I have been seeing on the net, some of them are better
looking than real girls."
"Wow Hey, isn't that what they call a fairy?"
"Yeah? I guess. I never thought of that. Yeah, I guess that you are right. Any
who, I have found some web sties that are all about TVs."
"TVs?"
"Yeah, short for transvestites. CDs means cross dressers. TGs means
transgendered people."
"Transgendered?"
"Yeah. That is a guy or a girl who feels like they should have been born of
the other sex, so they live like a person of the opposite sex."
"You have got to be kidding."
But, for some unknown reason, I was feeling a strange stirring in my jeans. I
did not know why, but the idea of a guy wearing girl's clothes and living like
he was really a girl was exciting to me. It made me blush, and it made me
really nervous. I wished that he would talk about something else.
'So? Why tell me this stuff?"
"I thought that you might like to see some of the pictures that I have
downloaded from the net."
"Pictures? Pictures of what?"
"Of some TGs and some TVs."
"Why would I want to see some of those kinds of pictures Jerry."
He looked at me for a very long time He seemed to make some kind of
decision, sighed and started to tell me why he thought that I would like to see
those pictures. "Well, because I think that you would make a very pretty girl,
and I think that you should see some of those pictures to see that there seems
to be lots of guys who would rather wear girl's clothes."
"You You think that I would be a pretty girl?" I was stunned.
"Let me put it this way Dougie. If you were wearing a mini skirt right now,
you'd be a knockout."
"Get real, Jerry? Me In a mini skirt? I'd look like a clown."
"No, you wouldn't. You want to see some of them? There is one in particular
that I think is what you would look like if you was a girl."
"If I say yes, you will drop this whole stupid thing?"
"Yeah."
"Okay then, let's look at some."
I spent the next ten minutes or so looking at some beautiful women, and all of
them had cocks. I was astounded. Then he used his viewer to open up
another directory. In this directory, all of the beautiful women were with
men, as though on dates. Some of the men were even kissing them, or
holding their hands. Those ones took about three minutes to go through.
Then he opened another directory. In this directory, he had a large collection
of pictures of pretty TG's all dressed in sexy lingerie, and all of them were
sucking cocks.
I was floored. I had never even dreamed that pictures like that would ever be
made available to the public. I knew that the internet was purported to be full
of smut and porn, but I had never dreamed of it. The pictures were bright
coloured, looking like the TG girls had posed for them in front of a
professional photographer.
I was shaking, I was so nervous. I did not know what was going on, but all
of this exposure to this kind of perversion was really having a deep effect on
me. I hated to admit it, but the idea of being one of those girls was really
turning me on.
"So, you like those pictures, sweet heart?" he intoned in a soft voice in my
ear.
I tried to cover up what was going on inside of me. "Well, they certainly are
different."
"Yeah. I bet you liked them, eh? I bet they made you really hot, eh?"
Then, without warning, he reached over and cupped the crotch of my jeans in
his hand. I had no time to hide the erection that I had. I nearly feinted from
the burning redness that flashed across my cheeks. No one had ever touched
me like that, certainly never another guy.
"Hey, looks like I found out what really turns you on eh, honey? I bet that
you would just love to dress up really pretty, and let a guy take you out on a
hot date eh?"
"Jer Jerry. I ain't no fairy?"
I was ashamed of the almost pleading tone that was in my voice. I sounded
like a whiny little girl.
"No? Then what is this?" His hand was still on my crotch, and I did not have
the will to move it away. He made me feel like I was under his control in
some way, and in some way, I kind of liked the feeling. It made me feel
weak and vulnerable, and girlish.
"Please Jerry, don't touch me like that?"
"Hey girl, I do not see you pushing my hand away " He grinned lasciviously
at me. He knew the power that he was having over me, and I knew that he
knew it. I did not want to feel like this, but I did feel this way.
"I got some special stuff for you, and I want you to put it on now. Take off
your clothes honey."
I just sat there, stunned as I watched him get up from the desk and go to his
closet. He pulled out a large shopping bag. He took it over to his bed and sat
it there as he turned around to look at me, and he once again told me to take
my clothes off.
It was like he had some how taken control of me. I did not want to do it, but
he seemed so masterful in some new strange way, and I could not resist him.
I kicked my shoes off, and I stood up and pushed my jeans down my legs. I
pushed the underwear down too.
"Jerry, please don't make me do this?"
He just grinned. I slowly unbuttoned my shirt, and let if fall on top of the rest
of my clothes. I felt so weak and so exposed and so very vulnerable.
"Now girl, come over here and see what pretties that I have for you."
I took the few steps to the bed, wishing that a crack in the floor would open
up and swallow me. He seemed to be so much bigger and stronger than me
now. I trembled. But, strangely, even though he kept calling me girl and stuff
like that, I was not afraid of him. I knew that he would not really hurt me,
though he could if he chose to for certain.
He dumped the bag on the bed and rooted through the stuff in it. He held up a
light pink satin bra and panties. He handed them to me, and like a dummy, I
reached out my hand for them.
"Put them on honey. Let me see you pretty you can really be."
I felt like I was in a trance. Before I realized what I had done, I had put on the
bra, and I was stepping into the panties. Oh, how they felt so cool, so dainty
and ever so feminine. I had never worn anything so light and delicate before.
And I nearly swooned when I felt them on my erection.
"Ahhh I can see that you love wearing your new lingerie. And you look so
pretty in it too."
He handed me a pair of rubbery breasts that I inserted into the cups. I could
not believe how delightful the weight on the bra straps felt to me. He handed
me a pair of delicate nylons with a lacy elasticized top on them. I sat on the
bed, very aware of how the soft satin panties felt on my bum cheeks, and I
slowly worked the hose on, making sure not to ruin them.
He knelt down in front of me, and he put a pair of high heeled sandals on my
feet. They had straps that went up and buckled around my ankles. They made
my feet arch in a decidedly feminine fashion, and I loved how the high arched
instep felt on the soles of my feet. He helped me to stand up and it took a few
minutes of helplessly leaning on his strong shoulder before I was able to start
walking without the fear of breaking my neck.
When he felt that I had mastered the art of wearing the high heels, he reached
into the pile of clothes again, and extracted a pink satin slip that matched the
other lingerie that I was wearing. It was beautiful, and had a full six inches of
delicate white lace at the hem of my slip. When I raised my arms, and he
lowered it down over my shoulders, as the soft satin caressed my skin as it
slipped down over me, I felt as though I were being enveloped in a new
sense of girl hood. I trembled too. I knew now that I would never ever be
happy wearing boy clothes again.
He stepped behind me and put a soft silky white blouse on me, reaching
around me to button it up. I felt so under his control as he pressed his body
against my back. I felt helpless to resist him. I no longer wanted to resist
him. I wanted to become his girl for him. I could also feel his erection as he
pressed it against me as he did up my buttons. I was surprised that it did not
offend me. In fact, it was kind of flattering to know that I could make my
best friend react to me like this.
I could not help it. I moaned, and I felt myself leaning into him. I heard him
chuckle as he lightly kissed my right ear lobe. "I just knew that you would
love being my girlfriend. I just knew it. You are so sweet as a girl. I think I
am falling in love with you sweet heart."
His words were strangely intoxicating to me. I had a near painful erection in
my panties. I had never been so turned on in my life. I could feel every
feminine stitch that I was wearing, and it made me feel natural, like I should
have been born as a girl. It was highly erotic.
He came around in front of me, and reached for my wrists. He did up the
French cuffs. The blouse was a soft satin material. It had black box type of a
design around the cuffs, the large collar, and it had delicate and pretty little
six inch high silhouettes of dancing girls, two in black and two in red over
each breast. I could also see the pink of my slip through the material.
I stood still, and had to lean over with a hand on his strong shoulders, as he
bent down and helped me step into the skirt he wanted me to wear. When he
raised it up my legs, tucking my slip and blouse down into it, He stood very
close to me as he reached around me, and did up the zipper. It was a dark
blue pleated mini skirt. I knew, though I had not even seen myself in a
mirror, that I was hot.
When the zipper was done up, he stayed where he was. I was blushing. I
finally raised my eyes to look into his eyes. With my eyes, I pleaded with
him to explain why he had done this to me.
His eyes were smiling with a mischievous mirth. I felt his hands alight on my
hips and he pulled me gently till my tummy was pressing against his erection.
Then, I saw him lower his head, and I knew that the boy was going to kiss
the effeminated me. I trembled more so. I wanted to be a girl, and receive the
kiss of an amorous boy. I do not know where the desire came from, but I
closed my eyes and waited for his kiss with anticipation.
His lips were hard and thin, which made my own feel full and soft. I smelled
his cologne. I felt his beard stubble on my cheeks. He was so manly, and I
was not. I could not stop the whimper of delight that escaped my lips as he
pressed his lips against mine.
I nearly feinted with the intensity of the emotion that was raging through my
psyche. I was torn between my desire to be his attractive girl, and my guilt
for having let this boy effeminate me, turning me into his personal fairy. My
worst dread though was the realisation that I loved what was happening to
me. It was like some one had just turned on a light switch deep inside of me,
and suddenly I was alive for the first time in my life.
I could not stop my hands from pressing on his big hard flat chest, and I
marveled that they knew what to do, as they pressed their way up ward, over
his shoulders, and caressing the back of his neck. I loved how the short
prickly hairs felt on my finger tips. I also loved knowing that this was what
girls feel too.
He pulled me tighter, wrapping his strong arms around me, and I yielded like
an obedient young lady. He had a huge erection that he was pressing into me,
and I pressed back. I could not believe that I was acting so much like a real
girl. I did not know where I had learned to do these things. I heard him
chuckle as he whispered in my ear that he loved how I was doing that to tease
him like that.
It had not occurred to me that he might think that I was trying to tease him, to
seduce him to become my man lover, a man lover of me as his girlfriend.
But, when he said it, I knew that it was true. It seemed to me as though I had
awakened a girl personality that had buried deep in my psyche. She wanted to
be free.
I sensed her coming awareness even as his tongue began to part my lips, and
I received him into my body. Yes, she wanted out, and she wanted to live. I
loved how she felt to me. I loved her. I wanted to become all of her, and I
ceded my will up to her to take over my life. She felt so much nicer than I
ever had, and I loved the novelty of how she felt. She was very feminine.
I sucked on Jerry's tongue, because I wanted him to know that I was
receptive to being his girl.
Jerry held me like that for a long time. Then suddenly, he scooped me up and
lay me on his bed. I watched him as he undressed himself. His erection was
massive, or so it seemed to me. He stood over me, and watched the girl me
as I lay there on his bed, looking up at him, lovingly, waiting to see what he
was going to do to me.
He told me once again that I was very pretty, and that I was very sexy. Then
he lay down on top of me with his full weight crushing me into the mattress.
I wrapped my arms around his neck, and I welcomed him. Somehow, having
the weight of a man on top of me seemed right and normal to me, now that it
was happening. I sucked his tongue back into my mouth, and he knew that I
was hungry for him to treat me like a girl.
I felt his cock pushing up at the crotch of my panties, and it felt so right, so
erotic to me.
We lay there like that, locked in the embrace for what seemed like hours.
Then he told me that he wanted to feel my mouth on him.
The words shocked me, shocked me into realising that I wanted to love him
the way that his girlfriends loved him. He would always let them suck him
off because he did not want to get them pregnant. Now, he wanted me to be
one more girl conquest of his.
He looked at me, perched up on one of his elbows, and asked me if I wanted
to suck his cock for him.
He smiled down as he saw what was going through my mind. He was son
confident that I was going to do it, that my struggle seemed to please him.
I finally nodded that I would.
He put my hand on his cock and told me that he wanted me to suck it right
away, as I was driving him crazy, because I was so fuckin' sexy.
It suddenly dawned on me that for a girl to submit herself to a man like this
must feel really special to her. I wanted to feel all that a girl gets to feel.
"Jerry, if I am going to do that, I want you to stand up."
"Why Babe?"
"Just stand up Jerry."
He crawled off of me and stood up. I stood up too, and went over to wrap
my arms about his neck once more. I kissed him, and I enjoyed the feel of his
strong fingers as they explored my pantied bum cheeks through my skirt.
"Why did you want me to stand up sweet heart?"
"It is hard to explain Jerry."
"Try. I want to know."
"Well, it seems to me that if a girl kneels down in front of a man, that she is
in effect surrendering herself to his superior strength. She must enjoy that
sense of surrender, because girls seem to like doing it so much. I figured that
since you have turned me into your girlfriend, and since you want me to do
what all your other girlfriends do to you, that I would like to know
everything that they get to feel about."
"Well Babe, get to your experience. You are driving me nuts, you are so
fuckin' hot. Man, I am just about to tear those pretty little panties off of you,
and fuck you till you can't walk straight for two weeks."
"Ummm, maybe another time?" I teased back. The idea of having him ram
that big thing into me sent shivers of fear through me. He'd rip me apart.
I kissed his chest, spending a lot of time sucking his hard little nipples. Then
I slowly kissed my way down till I was kneeling on the floor in front of him.
I had never seen a cock this close before. I gently felt it all over as I examined
it. I liked his cock, and I felt a genuine desire to please him.
I looked up at him. He was smiling down at me, and the look of masculine
superiority in his eyes made me feel so very girlish. I loved that feeling too, I
was now able to admit to myself. I loved feeling like a submissive sweet little
girl sexy thing for Jerry. He was so manly, so completely unlike his sweet
effeminated friend. I liked being his girl.
I rubbed his cock along my cheeks, marveling at how hard it was under the
sheath of satin smooth skin. It felt like piece of iron pipe. I admired him for
having so much manliness in him. Then I kissed it. I could hardly believe the
sense of relief that I felt. I had been so scared that I would not have the
courage to actually put my lips on it, and here I was, dressed pretty, and
planting adoring little kisses of honour all over his cock head.
"Suck my cock honey, that is why you are here."
I looked up at him again, and I hope that in his eyes, that I was sweet and
pretty. "Yes sir."
I felt such a sudden emotion of giddy freedom as I heard my own words
freely admit to a desire to suck his cock.
I put my lips on it, and began to relax them, as I pushed my head forward.
It felt so wonderful to have that dry hardness ever so slowly moving across
my ultra sensitive lips. I felt his cock as it entered me far enough to touch my
tongue. I began to lick it, feeling terribly free to be a real girl. I took a bit
more of it into my.
I could hardly believe it. I wished that I had a camera. I wondered what I
looked like to him, kneeling there with his cock buried inside of my mouth.
I drew back, licking him as I did so, and I took him into me again. Over and
over again, I moved my head as I sucked him. He put his hands on the sides
of my head and began to pump himself into me. I was getting fucked.
When he was ready, he almost screamed out as he erupted into my eager
mouth. I locked my lips as I did not want any of it to spill out and ruin my
pretty blouse. He filled my mouth. I did not know what to do, as he seemed
to have more to give me.
I swallowed his cum, knowing that I was receiving inside of my body what
women have taken from their men ever since the dawn of time. I had just
joined the ranks of woman hood, and I almost felt his spermatozoa in my
stomach.
When he stopped jerking, he let go of my head and nearly dropped to the
bed. He sat there, looking spent, his hands draping between his legs.
"Man, you are the best cock sucker I have ever had, and you know that I've
been blown a lot of times. You are fantastic."
"Thank you?" I was not sure if it was a compliment, but to the girl me, it was
a definite compliment. She'd done what women do. She'd made a man give
his baby juice to her, and she had it deep inside of her body.
I smiled at him as I watched him regain his stamina.
"Man, you are not only a gorgeous chick, but no one can suck a cock like
you can. I am certain now. I do not care what you got in your panties, you
are not a guy. You are too much of a girl to ever be a guy."
"I I kind of feel like a girl too Jerry."
"And I bet that you love the feeling, eh?"
"Yes. I do."
"Well, as far as I am concerned, you can wear your pretty clothes and make
love to me anytime that you want to. Man, you are too sweet for words. I
love you Miss Debi."
"Debi?"
"Yeah. You look almost exactly like one of the TG chicks, and I have some
pics of her sucking off her husband if you want to see what you looked like.
Anyway, you look like her, so I am going to call you Debi from now on."
"Jerry?"
"Yeah honey?"
"You will never ever again look at me and see your life long friend will you?"
"No I can't. What I will always see, no matter what you are wearing, is a
sweet chick, giving me the best blow job of my life."
"So, you will see me as a faggot cock sucker every time you look at me, is
that what you are saying Jerry?"
"No, that is not what I said. Society might classify you that way, but sweet
heart, to me you are a girl that I love who seems to really know how to take
care of me the way a loving girl should take care of her boyfriend. I want to
you dress up as Debi every time that we are going to be alone for a few
hours. Would you like that Miss Debi?"
"Yes Jerry, I believe that I would."
Virginia
- 13.02.2022
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