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THE MAKING OF MONICA CH. 08
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Becoming a crossdresser.
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SamanthaMeyers
SamanthaMeyers
86 Stories326 Followers
Losing my anal virginity!

About a week and a half after Jessica and I had our first sexual
experience. I wanted to spend the night with her. Even though we had
just had an oral experience, I knew in my heart that I wanted more. I
wanted more of her. I wanted more dick and I wanted her to be part of my
life. I texted Jessica and asked her if she would like to spend the
night. I told her maybe we could go out for dinner, then a movie
perhaps, then home for desert and to spend all night together.

She seemed pretty excited about it, but she just wanted to be sure that
I was comfortable (at this point of our dating) for an overnight guest.
I told her I was and she agreed.

Late Saturday afternoon Jessica arrived at my place. She had a small
overnight bag, which contained some clothes, toiletries and other
personal items she needed. We hung around my place for a bit until we
got hungry.

Jessica was wearing a tight pair of blue jeans, a lose fitting white
shirt and brown ankle boots. I wanted to match her outfit, so I put on a
nice pair of jeans, a lose fitting pull over shirt and my cowgirl boots.
We headed down to a Chinese restaurant, in the same area we had our
first real date some weeks ago. As we sat and dined the waitress kept
calling me Ma'am. I think she knew I was a boy dressed in women's
clothing. But I didn't care. As I said before Jessica is completely
passable, with her sweat high tone voice, her sexy skinny body, her
developing breast, while me -- on the other hand - still needed some
work. Either way, I was out being all the woman I could be, with a trans
woman and someone I cared a lot for.

After dinner we went to a sappy romantic comedy and sat in the theater
arm in arm. We held close leaning into each other throughout the whole
move. I was absolutely smitten with her. I wanted every bit of her. I
could smell her hair shampoo; I could almost taste her light perfume. I
wanted to kiss her in the darkness of this place. I wanted to undress
her. I wanted her dick out. I wanted to suck it. I wanted her to suck
mine and most importantly and without reservation I wanted her to fuck
me in the ass.

After the movie we went back to my place. We sat around on the couch,
not drinking but the mood and atmosphere was intoxicating. I wanted us
to move forward. I wanted us to be wrapped in each other's arms, naked,
sexual, erotic. And even though I was nervous she was gong to be there overnight, I was just as excited. I think sometimes -- at least at first
-- its hard to "plan" that first overnight. Sometimes I just has to
happen during the natural course of dating, and I knew what she meant
when she questioned me about being comfortable. But I was happy she was
there and I was hoping my nervousness would ease.

Jessica and I cuddled on the couch watching TV. Neither of us making any
real sudden or fast moves to get the other into the bedroom. Believe me
I wanted to; but I didn't want to put any undue stress or anxiety onto
the situation. But in my mind, I wanted to walk her to my bedroom. I
wanted to seduce her; or better yet wanted her to seduce me. As we
cuddled, we softly kissed and petted, but nothing that was leading to a
full make out session. But you can bet your ass, the butterflies in my
stomach were going 240 miles an hour and I was on the edge of being
ready to be played with.

When the moment did arise that Jessica and I engaged in a heated kiss, I
felt passion inside of me that I hadn't had since out last time
together. I wanted her. I needed her and tonight she was going to be all
mine. Jessica pulled from our kiss, looked me in the eye and said, "Why
don't we take this to your bedroom. I have something special for you."

"Okay." Was my response, as she helped me up and off of the couch.

Jessica walked me down the hallway to my bedroom, guiding me by my hand.
As we got there she softly spoke, hinting for me to wait on my bed, as
she grabbed her overnight bag and ducked into the bathroom.

I took her hint and wandered over to my bed. But that's when the
nervousness really set in. Do I get undressed and wait for her naked? Do
I put on more erotic clothing? Do I put on some music? Do I dim the
lights? Have no lights on at all? Do I just stayed dressed and let her
undress me?

I always envisioned my first time of full-on sex, that I would be
dressed to the 9's. I would have my matching panties and bra on, my high
heels, my thigh high hose, a long flowing wig. Make-up done perfectly,
my nails long and painted. My perfume light and bountiful. And it would
be me, walking out of the bathroom in an outfit that would make my man
hard. But here I was in my room, in jeans and average looking woman's
shirt trying to not panic and set the mood. I laid on my bed, and pulled
my hair back up into a ponytail. By this point my hair was getting long
enough that I could pull it back in a pony tail, so I usually wore my
wigs, only if I wanted that long flowing hair look. But tonight, I
wanted to be as natural and as free as I could be. So, I just laid there
nerve racked, until I heard the bathroom door open.

Jessica walked out of my bathroom wearing a pair of see-through black
panties and matching bra. She had on thigh high pantyhose and a pair of three-inch black heels. Her hair was back in a ponytail and she looked absolutely amazing. Her dick was held tight and deep in the panties and
I could see it through the material. I watched her walk, slowly and
sexually over to my bed.

"Do you like?" She asked.

"Oh, yes. Yes, I do." I replied.

Jessica knelt onto the bed, edging down and coming to rest next to me.
We starred deeply into each other's eyes before having that first deep
kiss. Her lips gloss, came into contact with mine as we made out deeply, sexually and erotically and before I could even worry about being
nervous, I was hard as a rock. Her warm body pressed up against mine.
Her legs intertwined with mine and we became one. We both rubbed and
touched each other while I slowly rolled my hands over her sexy outfit.
We dove deeper into our lust. I wanted her so bad. My cock was hard, my
body tingled and my ass was begging to be fucked.

I unhooked Jessica's bra letting her little natural tits out. I softly
kissed around her neck, her shoulders, along her collar bone, until I
made my way down her chest to her soft smooth tits. I kissed and licked
and sucked both nipples as I heard her moan out in pleasure. My hands
were cupping her ass cheeks, as my face was buried deep in her breasts.
Jessica lightly guided my body upwards pulling off my shirt. I had my
breast forms in my bra, which she promptly removed as she pulled my bra
cups down. Her mouth engaged in licking, sucking and nibbling on my
nipples sending sensations through me that I couldn't even fathom.

I reached behind me and hooked my bra, pulling it off, while pushing it,
along with my breast forms onto the floor. As we laid back down onto the mattress, with her body partially on top of mine, she had no idea how
hot and erotic this was for me. I knew where I wanted this to go, and I
hoped she would indulge in every pleasure and fantasy I was concocting
in my head.

Jessica kissed deeply, softly and lovingly for a while until I felt her
hand running up and down my outer thigh. Her soft touch was highlighted
by her deep kiss and the fact that I wanted my dick out. More
importantly I wanted her dick in my hand, in my mouth and up my ass.
Jessica fumbled with my jeans button for a second until I felt it pop
open. Her fingers gently slid down my zipper and her hand started to rub
up and down my crotch. I was rock hard and I knew she could feel my cock bulging inside my panties.

Jessica lifted herself off of me and edged downwards, pulling off my
jeans, revealing my pretty blue panties which were covering my hard
cock; which, by that time was poking out of the top of them. I could see Jessica's hard dick through her see-through panties, sticking straight
up, pressed against her skin and I was more than enthralled about being
with her, than I was before.

Jessica came to rest on top of me, right in between my legs. Her warm
body pressed up against mine, as I felt my hard dick being pressed
between us. I could feel her hard cock on top of mine as she began to
slowly pump back and forth, as if she was dry humping me. I raised my
legs up a bit further resting them at her sides. I wanted her to be in
me. I wanted our panties off. I wanted her to be fucking me like this. I
wanted to feel her thrusting back and forth deep inside of me. I wanted
her to be my first anal experience. And I wanted her to cum in me.

The passion of the moment overcame me and I rolled Jessica off of me and
onto her back. I laid on top of her for just a few seconds, until I
started kissing my way down her body. I stopped to caress her tits a
bit, but my goal, my want and my desire, was that dick. When I got to
her panty line, I grabbed both sides of her hot see-through black
panties and slid the down. Jessica opened her legs up, as I was looking
up and down her body, with her hot, sexy, hard cock sticking up in the air.

I gently and slowly kissed my way up her legs, making sure I got the
overly sensitive areas inside of her thighs. I put Jessica's hard cock
in my mouth and slowly slid it all the way in. All the way down my
throat as far as I could go. I wanted to suck it into me. I wanted to be everything she has ever wanted and I wanted this to be the best blow job
and fuck she has ever had.

I slowly bobbed up and down on her shaft, getting her cock soaking wet
with my saliva. I had long come to terms with the fact that I liked
sucking dick, but with hers it was a whole new dimension of desire. I
wanted to suck it all night long. All day long. Anytime she wanted it
sucked, I would suck it. I wanted her to be pleasured beyond belief. I
slurped up and down on her, making deep eye contact as I kept ramming it
in and out of her mouth. Her beautiful light-colored skin, her little
tits, with perfect nipples, her pretty face and beautiful ginger hair
made this one of the most erotic nights of my life.

I felt my cock pulsing. I felt feelings inside of me, I had never had
before and I wanted her in me. I needed to be fucked and I needed her to fulfill that desire.

I pulled Jessica's cock from my mouth and edged off of the bed. I walked
over to my dresser where I kept my toys and my lube, grabbing the bottle
from the drawer. I shook the bottle in my hand as I walked back to the
bed. I saw Jessica lying there naked, hard, awaiting my return with a
big ole smile on her face.

I stopped as I reached the edge of my bed and slid my panties down and
off. My cock popped out like a spring, hard, full, plump and raring to
go. I edged back down onto the bed, where I had been and got right back
down, face to face, with her hard dick. I softly kissed the tip, licked
up and down the shaft and just pleasured her for a while, making sure
she stayed hard and ready. I popped the lube top open and poured a good
amount onto my left palm. I used it to slowly stroke Jessica's hard
cock, up and down, slowly making it overly slippery and wet. I watched
myself giving her a long-wet hand job, just seeing the pleasure on her
face and in her eyes as we started at each other.

But I couldn't take it anymore I needed her in me. I put Jessica's cock
back into my mouth and felt the cool smooth lube along her shaft as I
started sucking her cock again. I reached behind me and was rubbing my
asshole with my lubed fingers, preparing myself for penetration. I slid
a finger in and moved it in and out a few times, just making sure I was
ready. The nerves hit hard and the stomach was turning, but I wanted her.

I raised my body up, pulling her cock from my mouth as I edged on top of
her. I climbed over her cock and was just in the position of lining up,
as I squirted a bit more lube on my hand. I reached behind me and soaked
my asshole with it and then grabbed her cock stroking her harder and
longer getting her slippery wet. Jessica and I both knew neither of us
were unsafe; since I had never been penetrated by anyone before and her
only in long-term safe situations, we weren't overly concerned about protection.

I grabbed a hold of her cock and started to sit down on it, lining it
up. I felt the tip at my asshole and I started to push down. I missed
the correct angle the first time; but on the second try I felt Jessica's
cock slide right into me. I gasped for air, as her long sexy cock
started to slide deep inside of me. I got so hard, and my skin stretched
so tightly on my cock, I thought I had grown an inch longer. I took
Jessica's cock all the way in, just as I was starting to turn and make
my upwards momentum. Her hands resting on top of my thighs as I started
riding her slowly and deeply as I raised up, then down, feeling her hard
cock sliding in and out of me.

My mouth wide open, breathing very shallow, as I was sliding up and down
on her hard cock. Nothing I had ever experimented with; the toys, the
dildo's, the butt plugs, Strap-on's and all the videos, were nothing
even close, or ever as stimulating as it was being here riding Jessica's
cock. I was beyond aroused. Beyond fascinated and beyond pleasured. I
was riding up and down on her dick feeling it sliding in and out of me,
as I looked down on her. Her hips shook, swayed and thrusted upwards at
times ramming her cock deep inside of me. I was hoping I was doing this
right since all my experience had been with inanimate objects. But
apparently, I was doing okay, because she was still hard, still
thrusting into me and had that look of absolutely pleasure in her eyes
as I continued bouncing up and down on her hard cock.

My cock started flapping up and down as I started to get a faster
momentum and rhythm. Jessica, would occasionally, reach out and cup my
balls or stroke my cock as I continued bounding up and down on her. It
was INCREIBLE!!! I had a dick in me! I was fucking loving it! My first
real dick, buried deep inside of me, pleasuring me. And I wanted to feel
it more and more.

I wanted her to roll me over and put me on my back and ram that cock
deep into my ass. I wanted her to nail me from behind, pumping and
thrusting into me like never before. I wanted her to shoot her load all
over my balls. On my chest, on my back, but most importantly up my ass.

"OH, Fuck Jessica. Your cock is amazing". I groaned out as I continued
to ride her.

"You like that dick in your ass?" She asked.

"Yes. Yes, I do." I replied.

And I did. It felt amazing. It felt exciting, it felt erotic. It felt
taboo and I was in love with it!! Period.

I knew who I was and where I wanted to be. I was all woman, and I wanted
cock! Forever! Period. Dick. Dick. Dick!!! Period.

I continued riding up and down on Jessica's throbbing cock. Felling it
sliding in and out of my ass, while my cock stayed rock hard and ready
to explode.

I must have ridden her for the better part of ten minutes. Time to time,
I would lean down and we would kiss deeply as she would be the one
thrusting it in and out of my ass, only for me to return upwards and
take it as deep as I could by my momentum. As fast as I could and as
hard as I could, as I stayed erect and overly excited to be getting
fucked. Jessica's beautiful face and gorgeous eyes starred deeply into
mine as we continued making love.

"Baby you're going to make me cum." She blurted out as I was riding her
hard cock

"Fucking cum in me baby." Was my reply.

I was overly excited and arouse to hear that and it made me want this
even more. I wanted her to cum. I wanted to know I was the one that made
her get off. I wanted to feel her blasting her load in my ass, while I
came from it.

I started riding her harder and deeper. Jessica's hips started thrusting upwards, as her head leaned backwards rocking from side to side. Her
hands rubbing every bit of me, but also rubbing every bit of her.

"Fucking cum baby! Fucking cum!" Kept flying from my lips as I bounced
up and down on her hard cock.

"I'm gonna cum," she squealed out. "I'm gonna cum."

Jessica started raising her hips so high off the mattress ramming her
cock even deeper into my ass, as I was moving up and down, that I felt
like there was a street light post sliding in and out of me. I was so overwhelmed and feeling pleasures in places I had never felt before. I
was so hard, stroking myself as she was thrusting that cock deep inside
of me, bringing herself to orgasm.

"I'm gonna cum!" I cried out as my hand stroked my dick hard and as fast
as she was pumping me from below.

"I'm cumming!" She cried out, as I felt her cock starting to thrust and
pulse deep inside of me.

"Holy fuck, You're cumming in me." I cried out, as I felt her cock
shooting her cum deep inside of my me.

The absolute pleasure and passion of her cumming in my ass sent me into overload; and before I could even stroke myself further, I started
shooting my cum all over her stomach and chest. It was flying
everywhere. With every thrust up and down, I was shooting cum in all directions.

"Holy fuck!" I cried out, as I was blasting my load into the air, as she
was blasting her load deep into my ass.

Jessica pulled my body down on top or her, our faces met and we entered
into a deep passionate kiss. Her hips still lightly thrusting up and
down as she was expelling the last bit of her cum deep in my ass. My
cock still lightly pulsing and oozing the last bit out of the tip.

I want more. I want to fuck her more, I thought to myself. I want to
suck her cock. I want a line of cocks here now, waiting to fuck my tight
as. Holy FUCK! This was amazing.

Jessica pulled from our kiss, looking me deeply in the eye and
whispered, "That was amazing!"

And it was. But she had no idea how amazing it was for me.

I stayed on top of her for a long time, just feeling her cock inside of
me, feeling the wetness of the lube and her cum slowly seeping out of
me. Feeling what it was like to be coming down after orgasm, with a cock
deep inside of you after being fucked, while the cock slowly recedes.
Feeling the sweat of your bodies as you rest chest to chest. Knowing you
want more. You want this forever and you want more!

Before the night was over, Jessica and I had sex again. This time, we
just sucked each other off in a long side by side 69, until she came
deep down my throat, and I into hers.

That night changed me. I knew from that moment on, it was always going
to be wanting dick. Hopefully hers!

I knew I wanted to be all the woman I could be. I wanted to get tits. I
wanted to have my dick cut off an get a pussy. But in all reality, I
liked my dick and still wanted it! I knew I was going to suck dick and
be fucked for the rest of my life. I knew it! I accepted it! And I
wanted it! I was never turning back.

Over the next few months Jessica and I became a deep loving couple,
developing our relationship even more. I started HRT and was becoming
Monica even more. I came out to some people. To some friends and even to
some co-workers. I had Jessica at my side. I had her faith, her love and
her support.

But I had to come out completely. I couldn't be Matthew anymore. It was
time to take the biggest step I had to take. Coming out to my parents
and after a bit of time, asking Jessica to marry me.

I'll tell you all about it in the next chapter.

To be Continued...

This author has many others https://www.literotica.com/stories/memberpage.php?uid=5622989&page=submissions

The first Monica one starts --- https://www.literotica.com/s/the-making-of-monica

first of another series
https://www.literotica.com/s/mikes-first-transgendered
the first penetration is in the below https://www.literotica.com/s/mikes-first-transgendered-pt-04

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