Jan and John s Sexual Exploration
- 3 years ago
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An Evening Of Exploration free porn video
As I stood at the door of the apartment, several thoughts crossed my
mind.
First was that I couldn't believe I was finally doing this. Second was
that I was scared out of my mind. And third was whether anything in my
life would ever be the same again. You see, I'm a crossdresser, and
this was going to be my first time out in the real world ever, fully
dressed. I was going to meet another CD who I had been corresponding
with online. Would I actually be able to go through with it? I took a
deep breath and then my first step out into the real world as a woman.
I had prepared and planned for a couple of weeks what I would wear. I
had showered and shaved my entire body, so that I was smooth all over.
I had moisturized and scented my body with some body splash, and then
put on a little perfume. I put on a silk robe and a pair of high-heeled
mules, and sashayed over to the vanity. First up was my makeup. I put
on a foundation and some powder, a bit of rouge on my cheeks, and then
set to work on my eyes. A light brown shadow to my lids, and then a
dark liner to give my eyes a slightly more dramatic look. Next I used
some mascara to lengthen my lashes and curled them. I had thinned my
eyebrows just a bit to give them a slightly feminine arch. I would save
lipstick for my very last touch, after the wig. I then filed and
smoothed the edges of my nails and painted each of them a dark purple
color.
I got up and strutted over to the dresser and looked over my lingerie,
which I had laid out earlier. I removed my robe and the heels and stood
naked. I wrapped the dark purple waist cincher/garter around my waist,
and sucked in while attaching the hooks. The straps dangled from my
waist and fell against my legs. I slid on the smoke gray stockings
slowly, rolling them up in a ball and then sensually sliding them up my
legs. I attached the garters and stood. I could feel the garters
tugging at my stockings as they held them up and the feel of nylon on
my bare legs immediately stirred my erection. I picked up the high
waist control panty, which was covered in lace, which had a satin panel
in the front to hold me in, and matched my garter and bra. I inserted a
maxi pad into the crotch area to absorb any leakage and to smooth out
my front. I pulled my penis back and settled the panty in to place. I
could feel my erection continue to build as I wiggled my butt a little
and smoothed my hand over my crotch and legs. I picked up the bra and
wrapped it around my chest, connecting it in front of me, then twisted
it around. I pulled what little of my chest I could into the cups, and
then inserted the silicone forms. They gave me a c cup once in, and I
ran my hands over my "breasts". The weight pulled the straps into my
shoulders a bit and I loved the shift in how my bodyweight was
distributed. I was feeling very feminine now. Next was the low cut
black control slip, which came to about mid-thigh.
I slipped it over my head and the cool silky material fell over my
body. I pulled the hem down and felt the slight compression of the
material, wrapping me in another layer of silk, satin, and lace. I
pulled my dress out of the closet. I had been torn between my pink
sleeveless shift dress with a scoop neck, which had a matching wool
jacket, a black and white diagonally striped silk wrap dress that
really hugged my body, and the dress I'd chosen to wear tonight. It was
a purple cowl neck sleeveless dress that cinched around the waist and
came down to just below my knee. It had a back slit, and was made of a
silky rayon material that clung to my curves. I put it over my head,
slid my arms through the armholes, and pulled the dress over my body,
feeling it rub against the silk slip and caress the entire length of my
body.
I padded over to my shoe collection and picked out my purple strappy
heels, which I slid onto my feet. They only had a 2 inch heel, but
added to my 6' plus height made me a very tall woman. I pulled out two
gold rings for my pinky and ring finger on my right hand, a purple
stone bracelet, and a pearl choker, and put on my jewelry. The pearl
choker in particular felt very sexy and girly as it wrapped around my
neck and covered my Adam's apple. I clipped on a pair of pearl
earrings.
I walked over to the vanity again and pulled the black shoulder length
layered wig off of the wig stand. I brushed it out and then pulled it
onto my head. I adjusted it and made sure the placement looked natural.
I pulled out the reddish purple lipstick and applied it to my lips. I
also applied a lip gloss to my lips to give them a sexy pouty shine. I
looked at myself in the mirror. I wouldn't win any beauty pageants, but
I appeared to be a young decently attractive and very tall Asian woman
with broad shoulders. More importantly than my look though, was that I
felt incredibly feminine. I felt like a woman, and that excited me to
no end. My erection strained against the panty and the pad, and I could
feel precum leaking out of my penis. I rubbed the front of my crotch
and felt an orgasm building. I stopped before things went too far and I
had to change my pad.
I pulled out my cute black clutch with the short strap and put my id,
credit cards, some cash, lip gloss, makeup, some tissues, an extra pad,
my cell phone, and a condom in it. After all, a girl can't be too
prepared.
Walking to the front closet, with my hips swaying as my heels clicked
on the floor, I pulled a long powder blue wool coat out of the closet.
I wrapped a scarf around my neck, and then pulled on the coat. I
checked my hair and makeup in the front hall mirror, opened the front
door, and took a deep breath. This was my first step into the real
world dressed as a woman. I walked out into the night towards my car
with the keys in hand. I felt the breeze swirl around my stockinged
legs and blow up my skirt. It was exhilarating. My heels clicked on the
sidewalk, and I felt the wig brushing against my cheeks and shoulders.
I unlocked my car, smoothed out my skirt before sitting down, swung my
legs in, and started the car. It was strange wearing heels to drive for
the first time, but I got used to it quickly. I was meeting Karen at a
bar in Boystown, which was friendly to crossdressers, and then we were
going to see where the night took us. I had never been with a man, but
thoughts about possibly meeting and making love to another crossdresser
excited me. As I drove, I got a couple of looks from other drivers, but
nothing out of the ordinary, and I told myself in my head that all they
saw was a young woman.
I parked the car and stepped out, opening myself up to complete view
and scrutiny. I walked with total confidence as a woman, and ignored
any stares, which were few and far between. It was a little chilly out,
so I pulled my coat a little tighter, but the cool air felt sensual and
erotic on my legs and face. I found the bar, showed the doorman my id,
which he barely gave a second glance to, and walked inside. The
lighting was low, which added to my self-confidence. I pulled off my
coat and walked with it over my arm, to the secluded back tables, which
were relatively empty. Karen was supposed to be waiting for me back
there. I saw her as soon as I rounded the corner. She sat at an
enclosed corner booth, sipping a mojito. She was tall, just like me,
with a wavy red wig that was piled up in a loose bun on top of her
head.
She had stunning green eyes and amazing bee stung lips. She was wearing
a white long sleeved satin blouse with a ruffled collar and a black
pinstripe pencil skirt. Her stockings were sheer black with a seam up
the back and she was wearing a simple pair of black pumps. She had on a
strand of pearls and a gold watch and her nails were impeccably done in
a light pink. Although she appeared perfectly feminine, one could tell
that her hands were just a little large, her shoulders a little broad,
and her frame a little too wide to truly be a woman. She was still one
of the sexiest things I had ever seen, and my heart beat quicker and my
erection grew harder again as I approached her.
"Karen?" I asked in my best sexy, yet female voice as I approached her
table.
"Rheanna?" she asked back just as questioningly with a bit of
hesitation.
I smiled and nodded and we both let out a laugh. She got up and gave me
a hug, and I felt her breasts press against mine as we embraced. She
smelled fresh and flowery. Lilac, I thought to myself. We reluctantly
pulled apart and sat down opposite each other. I ordered a whiskey
sour, and we began chatting like old friends, happy to finally meet in
person after talking online for so long.
We told each other all about our histories crossdressing, me getting
started with my mom's hanging lingerie in the bathroom, and her being
pushed into dressing as a girl while playing with her sisters. We both
experienced great shame through our teens, hiding our desires to wear
women's clothing, masturbating whenever the touch of silk and lace
reached our bodies, and we both had had our share of women to make up
for our insecurities. I had only recently begun dressing fully and
shopping, and this was my first trip out.
Karen had been doing it for the last few years, but also had waited
until her late twenties before taking her first step out of the house
in heels. We both had significant others who were accepting, but wanted
nothing to do with our crossdressing. My wife knew about my dressing
because I had told her early on, but did not feel comfortable with her
man wanting to dress like a girl, and after a couple awkward lovemaking
sessions with me wearing one of her dresses and panties, we'd decided
that dressing would be something that she didn't need to be involved
in, for both our sakes. She knew I still dressed, but not to what
extent. In fact she didn't know I was out tonight, as she was out of
town for business. Karen's wife was even less accepting and did not
know about the extent of her husband's dressing. In fact he kept all of
his fem stuff in a storage locker away from home so that his wife
wouldn't be exposed to it. We both loved our partners dearly, but
needed to express this side of our personalities, and also to explore
what this meant in terms of our sexuality. Neither one of us was
interested in leaving our families or beginning another relationship.
We just felt the need to satisfy our curiosities. This was our chance
to learn what we really wanted.
We continued to chat and drink for what seemed like hours and had
gotten a bit tipsy when a pair of handsome gentlemen came over and
asked to have a seat with us. They bought us a round of drinks and
chatted with us, introducing themselves as Joseph and Damon. We made
clear to them that they were unlikely to get very far with us, and that
we were in fact "special girls" and they surprised us by saying that
they'd already known this fact and just wanted to be friendly. After
they sat down, Joseph, the cute brown haired fellow whispered to me
that he and his friend were actually crossdressers too, but had decided
to stay drab tonight. When I told him that I didn't believe him, he
took my hand and slid it under his shirt, where I felt a silky camisole
top. As I rubbed the soft material against his chest, I felt myself
begin to get slowly turned on, and I heard a noticeable moan emerge
from his lips. I became bolder and slipped my hand down below his shirt
and into his pants, feeling the satin of his panties and a pair of
pantyhose. I rubbed the bulge in his panties, smiled and told him that
I'd love to see him completely dressed sometime, and he promised to
make a date where we could meet as girls. I nuzzled closer to him and
continued to fondle his cock. His hand was now on my stockinged leg,
and he was rubbing it slowly and sensuously. He slid the hem of my
dress up my leg and his hand moved to the tops of my stockings, where
he pulled on my garters. I looked across at Karen and was surprised to
see her kissing the other guy, her hands also in his pants, and him
rubbing her breasts. She caught my glance and gave me a smile and a
nod, and I nodded back. My hand was still on Joseph's penis, and I felt
a bit of wetness escaping and dampening his panties. His hand had now
pushed my dress all the way to my waist, and he was rubbing the front
of my panties. He pulled back at first when he felt the flatness of the
pad, but I whispered to him that I was just protecting my panties from
stains and that there was definitely a cock behind the pad that was
straining to get out. He rubbed harder and I moaned into his ear. I
looked into Joseph's eyes, and moved closer to his lips. I had never
kissed a man, but here I was inches from his face. He sensed my
hesitation and pushed his lips into mine. They felt incredible, firm
and strong. I surrendered to his kisses, and felt his tongue part my
lips and enter my mouth. I returned his enthusiastic kiss and we began
making out while rubbing each other's cocks through panties. I felt my
orgasm building, and my cock stiffening inside my panties. Joseph
seemed to know this as well, and he began stroking and rubbing harder
and faster. Before I knew it I felt the semen rushing out of my penis
and I came into the pad with unbelievable force, letting out a long
groan as he kissed my lips hard. I smiled and fell back, and saw Karen
glancing at me, and I could tell that she had come as well by the silly
grin on her face. Her foot touched my leg under the table and slowly
stroked it, and she mouthed to me that soon we'd be taking care of each
other. I smiled as well and then returned my attention to Joseph.
His hand was still on my panties, and mine on his, and I started
rubbing him again. I felt his hard-on begin to tense, and his groaning
returned. He whispered to me that he was going to come in his panties
and I simply smiled back and told him to wait. I wasn't sure what had
possessed me, but I slid down the seat, and positioned myself in front
of his crotch, kneeling underneath the table. He was wearing a cute
pair of royal blue panties, all satin and lace, and the considerable
bulge in them only excited me further.
I had never even been out of the house dressed before, but now here I
was totally dressed, with a new friend, and looking straight at another
pantied cock! I bent over, pulled his panties and hose down, and his
cock popped out. I had never seen another person's penis this close,
and I looked it over from all sides. Joseph smiled and told me that he
hoped I liked what I saw and that I might honor him with a kiss. I
laughed and told him a kiss was the least I could do after my orgasm. I
moved forward and licked off the pre-cum, which had leaked out of his
cock. I gave it a kiss on the tip, one on each side, and then slowly my
lips parted for the first time to allow a cock into my mouth. It tasted
slightly salty, and as the tip touched the back of my throat, I felt a
slight gagging, but I forced it down, and began to slide my lips up and
down his cock. Luckily the booth had a tablecloth, and from the outside
now it just looked like there were three people seated, two making out
(Karen hadn't been quite as adventurous as me...yet) and one sexy boy
with his eyes closed and an ear to ear grin on his face. I worked his
cock with my mouth and began to suck and lick the entire length,
holding it with one hand, and massaging his balls with my other hand.
His hands came down behind my head and he pushed me forward, sliding
his penis into my mouth faster and deeper, fucking my face. I felt him
begin to tense and knew what was coming. For the first time in my life
a man came in my mouth, shooting into the back of my throat and filling
it with his cum. I swallowed as quickly as I could, savoring the salty
semen and creamy texture. As I milked him dry, I pulled off his cock
and gave it one more kiss on the tip, then climbed back up onto the
booth seat. I had just given my first ever blowjob, and was incredibly
turned on, even though I had just come moments earlier. My cock was
hard again already, and I knew I needed more, whether I was going to be
sucking another cock, having mine sucked, or maybe even going further
and giving my virginity to one of these sexy individuals.
As I looked over, I saw that Karen's boy had apparently also come, but
she hadn't been quite so generous with her lips, and he had a larger
wet spot forming on the front of his panties. He had an embarrassed
smile on his face, and Karen was dabbing at the spot with a napkin to
dry it off a bit.
We stayed and chatted with the boys a bit longer and had one more
drink, but soon my horniness overtook polite conversation and this time
I wanted my new friend. We had been rubbing each other's legs with our
hands, enjoying the feel of nylon, and I leaned over and whispered to
her that I was ready to leave. She smiled at the gentlemen, and
explained to them that we unfortunately had to head home, but that
perhaps we might enjoy their company another time, and only if it was
an all-girl's night out. They readily agreed, we exchanged numbers, and
Karen and I got up from the booth.
I leaned over to Joseph and whispered to him that I had really enjoyed
my time with him, and that I couldn't wait to see him again. He told me
he'd be in touch and perhaps I could come over to his place and we
could have a slumber party and play dress-up. I smiled, gave him a kiss
on the lips, and told him I would be waiting for his call.
Karen and I walked out of the bar, hand in hand, with our heels
clicking in rhythm. As I asked her where she lived and what we might do
next, she surprised me by saying that she'd gotten a hotel room around
the corner. She explained that she hoped it hadn't been too forward of
her, but that she figured neither one of us could go back to our place,
and that this would be easiest. I gave her a hug and told her I was
happy she'd been so thoughtful, and gave her a quick peck on the cheek.
As we stood there on the sidewalk, arms around each other in a hug, and
both of us men dressed to the nines as sexy ladies, the excitement and
passion overtook us. We looked into each other's eyes, and our lips
came together in a passionate kiss. Our tongues caressed each other's
mouths, hands slid up and down silk and lace covered bodies, and we
both felt erections growing as our bodies pressed against each other.
We separated and smiled at each other, and then started walking over to
the hotel, excited by thoughts of what was about to happen.
Clover
- 27.03.2020
- 16
- 0
