Jan and John s Sexual Exploration
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An Evening Of Exploration 4 free porn video
I pulled up to a spot just down the street from the hotel, and stopped to
catch my breath. Things seemed to be happening in such a whirlwind! I had
half my feminine wardrobe in my car and I was completely dressed, about to
meet up with my friend Karen, with whom I had experienced one of the most
amazing and sexually charged evenings of my life.
We had explored each other's bodies and mutually expanded our sexual
boundaries. And now tonight we were also going to be dressing with another
pair of crossdressers who had hit on us the previous night when they had
been in drab.
One of them, Joseph, had been my first male kiss that night, and I had
even given him my first ever blow job. I was so excited to see what these
sexy and handsome boys would look like once we got them into some panties
and dresses! I looked in my rearview mirror to check my makeup and then
looked over the simple outfit I was wearing, my light blue wool coat
matched well with the sky blue sleeveless turtleneck I was wearing. A slim
black pencil skirt, black heels, and relatively simple light blue lingerie
underneath completed my feminine ensemble. I had also left my two inch
butt plug in me to keep me loose in anticipation of the good times ahead.
I opened my door and stepped out of the car, dressed and out in the open
for the first time ever in daylight! I was so nervous all of a sudden. I
pulled on a pair of sunglasses, hoping that it would help me avoid eye
contact with anybody on the street, and then pulled my overnight bag and
purse onto my shoulders. Normally, these bags wouldn't have presented a
problem, but with the way that I was dressed, I realized that I couldn't
bend, shift, or lug around as much as I could in boy clothes.
I struggled with the suit bag, containing my three dresses, when I
suddenly felt a hand on my shoulder, and a husky voice asked, "Can I help
you with that, Miss?"
I turned around and looked into Joseph's eyes. He was wearing a tee shirt
and jeans, and his smile seemed to make me melt right on the spot. What
was I thinking? Here I am, a man, and I was totally attracted to another
man and acting like a smitten schoolgirl. I pulled myself together and
mumbled a shy thank you as I looked away. Joseph tilted my head towards
him, and lifted up my sunglasses. We were about the same height and build,
but I was slightly taller than him in my heels, and was looking down on
him slightly. He looked into my eyes, whispered that he'd missed me, and
then leaned forward and pressed his lips into mine. I felt his firm lips
lock onto mine, and responded by thrusting my tongue into his mouth. It
was a passionate kiss filled with excitement and expectation. I dropped my
bag on the ground, and my arms wrapped around Joseph's body, as his did to
mine. He reached down to my ass and gave me a playful squeeze, and I
countered by brushing my hand against his erection, feeling a large lump
in his jeans.
"Excited to see me pretty boy?" I asked.
"My panties can barely contain me," he replied, and then moving his hand
across the lump that had formed in my skirt, he said, "and it looks like
neither can yours."
We both laughed and then I asked him what he was doing here. He told me
that he lived in the neighborhood and was actually on his way home to
gather together his girl clothes before meeting us at the hotel. I asked
if he was excited for our girl's night out, and he responded in the
affirmative. He then offered to help me carry my bags up to the hotel, and
I happily acquiesced. I held my purse in front of my lap to hide my
unladylike bulge, and we walked over to the hotel, with him carrying my
bags.
We chatted as we walked, and I learned that he was a struggling artist who
spent his daytime hours as a consultant. It paid the bills and allowed him
to maintain the two wardrobes of his chosen lifestyle. He was a
fascinating person, and I realized that I wanted to talk and talk with him
to find out more, but too quickly we walked into the lobby and a bellboy
took the bags from Joseph. Joseph pulled me close and whispered into my
ear that the next time I saw him, he'd be ready to return the fantastic
blowjob I'd given him the night before.
I kissed him and told him I was looking forward to a taste of his cock as
well and maybe a little more, but that I wouldn't be kissing anything of
his until he was wearing nothing but silk and lace, and giving his cock a
squeeze, I turned to get on the elevator with the bellboy. Joseph gave me
a wave as I watched him walk away while the elevator doors closed. I
sighed and smiled, thinking about the night that awaited me. As the
elevator rose, I noticed that the bellboy seemed uncomfortable. He
fidgeted and avoided my glance, and I realized that he had most likely
read me as a man. I looked over and said to him, "Is there anything you'd
like to ask me, sweetie?"
He cleared his throat and looked me up and down. He was a skinny kid, not
very tall, and probably only about 18 or 19 years old. He opened his
mouth, but nothing came out. Then, after clearing his throat again, he
asked if I was a crossdresser. I laughed and replied, "What do you think?"
He shifted and cleared his throat again and for some reason, I leaned over
closer to him and placed my finger under his chin, lifting his face
towards mine. "Do you like wearing panties too, honey?" I asked.
The question seemed to startle him and he managed to stammer out that he
didn't. I leaned even closer and told him that it was okay if he did, and
asked if he was wearing them right now. Another no squeaked out of him,
but unconvinced I reached over and slid my hand down the front of his
pants. He almost jumped right out of them, and tried to pull away, but I
had learned what I wanted to already as I withdrew my hand. I'd felt the
silky smoothness of panties and pantyhose. It seemed ridiculous. How many
crossdressers could I come across this weekend?
The elevator rang and arrived at our floor, and he quickly walked out into
the hallway. By the time I exited, he was already waiting at the room to
our door. I knocked and Karen opened it. She was wearing a simple red wrap
dress, black hose, and three inch pumps. Her mane of red hair was once
again piled in a bun on top of her head, and she looked absolutely
ravishing.
The bellboy scuttled into the room to deposit the bags, and then I took a
step in, and pulled Karen into a deep embrace. Our lipsticked lips played
back and forth with each other and our tongues melded together. I felt her
hands travel down to my ass, and then across to the front of my body and
onto my newly erect cock. She gave it a squeeze and whispered that we'd
get to play together soon enough. The bellboy, bright red from my earlier
teasings, beat a quick retreat out the door. I smiled and made a mental
note to revisit him at a later date. We took each others hand and walked
over to my bags so that I could show Karen the wonderful outfits I had
chosen.
We walked into the entry room of the hotel, and I pulled the three dresses
I had chosen out of my suit bag, and hung them in the closet. They
included my pink wool shift and matching jacket, which were one of my
favorite and girliest outfits, an emerald green strapless gown of smooth
satin, and a light blue split sleeve ruffled dress. Karen gushed over my
choices, and told me how she would love to see me in all of them,
especially the green ball gown, but that she didn't feel right starting
the dress-up portion of the evening just yet. I smiled at her and reached
over to feel her body through the silk wrap dress she was wearing.
My hand slid down her chest, to the bow holding her dress together, and
slowly untied it so that her dress fell open at the front. Underneath she
was wearing a black bustier with red lace trim, attached garters, black
stockings, and a matching black and red lace thong. Her cock bulged
prominently underneath the thong, and my hand ran over it now, massaging
it, and then freeing it from its lacy prison.
I smiled at Karen, and told her that I had missed her little secret, and I
as I dropped to my knees, she answered that she felt the same way. I
lightly touched the tip of her cock with my tongue, swirling the small
dollop of pre cum that had formed at its tip. She gave a little gasp as I
moved back and forth over her penis, licking, kissing, and blowing on it,
but never taking it into my mouth. She started to moan louder and louder,
and I began to play with her testicles with one hand, while the other
moved to her ass, and slowly massaged her butt cheeks. She reached down
with her hands and grasping my head, pulled my mouth onto her cock,
calling me a cock tease. I wrapped my lips around her penis and began to
suck away with abandon.
Feeling a real cock in my mouth again caused my own erection to stiffen,
and I felt my penis straining against my hose and panties. I pumped her
cock in rhythm to my sucking, and started to slide my fingers to her ass,
where I was pleasantly surprised to discover that she had already lubed up
her opening. My finger easily slid into her, and began to move as I
envisioned my cock would later tonight. Karen began to gasp my name, and
warned me she was about to cum. I redoubled my efforts, and soon I felt
her stiffen, she let out a loud scream, and her cock pumped several large
loads in my mouth, which I greedily swallowed. I continued sucking on her
penis even though she had softened, and Karen emitted soft gasps as her
sensitive cock head was stimulated by lips.
Eventually, she pushed me off of her penis and kneeled down next to me.
Taking my head in her hands again, she brought my lips to her and we
shared a slow, smoldering kiss. Her hands roamed my body and began to rub
the feminine garments that I wore. She ran one hand underneath my sweater,
while her other hand unzipped my skirt. As it fell to the floor, she
massaged my ass, rubbing slowly over my hose, and giving me a little
squeeze. Her other hand continued to grope my breast, and then slowly
started to slide my turtleneck up my body. She then used both hands to
work the collar around my head, taking care to keep my wig on my head. I
now stood, just in my bra, panties, hose, and heels, and Karen in the
same, although in garter and stockings, as opposed to pantyhose, and we
continued our intensive kissing and groping.
She started to slide down my body with her lips, and was soon at my
crotch, and started to kiss me through my panties and hose. I let out a
small moan as she worked my crotch, and smiled as I felt her start to pull
my pantyhose and panties down over my penis. My very aroused cock popped
out, and she left my hose and panties on, holding my balls in. She wasted
no time teasing as I had done though, and immediately took my full length
into her mouth. Her lips massaged my cock, and I felt her rubbing her
hands up and down my nylon covered legs, sending a little tingle through
my body. Her hands at my ass again found the butt plug I had held in my
ass all day, and she began to slide it in and out of my ass, stimulating
me further.
Then just as suddenly as she had begun, she pulled off of me and I felt
abandoned. I opened my eyes and saw her leaning over and reaching into her
purse and when she came back up, she was holding a condom and a bottle of
lube in her hand. She poured the lubricant onto my stiff erection and then
opened the condom. Slowly she slid it down my penis and then poured
another generous amount of lube onto my now rubber clad cock. Leaning over
she whispered into my ears that she wanted to feel my cock in her ass, and
being the gentleman, or lady, that I am, I felt it was the polite thing to
do, so I pushed her onto her back, spread her legs apart, lifting them up
to my shoulders, and then lined my cock up right at the opening of her
ass. I thrust my cock into Karen's ass, and began to pump in and out of
her, and
she matched my motion by pushing towards me. She started to shout out my
name, begging me to fuck her harder and telling me how much she had missed
being filled up by me. I ran my hands over her legs, and up her body,
dropping towards hers face so that I could kiss her luscious red lips. Her
wig had come undone, and the red locks flowed out, making her appear
disheveled and sexy at the same time. As we kissed and I pumped into her,
my hands continued to roam her body, and came back to her cock, which had
now become erect again.
We were so lost in the moment that we never heard the knock at the door or
it opening to admit our remaining guests, and in fact, we didn't look up
until we heard a quiet cough. We both stopped and looked up to see
standing before us Joseph and Damon, both wearing long coats, amused
smirks, and looking as handsome as they had when we left them the previous
night. They had dropped their bags at their feet and were watching us as
we froze, mid-thrust, before we all burst out laughing.
"Sorry, we didn't really want to interrupt, because this is one of the
sexiest things I've ever seen," said Joseph with a smile, "But we also
didn't know how we could get involved without breaking the flow up
somehow."
And with that, they both opened and dropped their coats to reveal that
though they were wearing pants, they also had on silky slips underneath
their coats, Joseph's in a dark blue, and Damon's in ivory. They then both
dropped their pants to unveil stockings and garters on their legs. Damon
reached into his bag and pulled out two pairs of black pumps, and they
each slipped them onto their feet. Joseph meanwhile pulled two wigs out of
another bag, a brunette one for Damon, and a blonde one for himself. He
also pulled out a tube of lipstick and after applying it to his lips,
leaned over and did the same to Damon, giving him a kiss once he was done.
The two pretty new girls who had now emerged introduced themselves as
Josephine and Diamond, before coming over to join Karen and I in our
crossdressing fun. During this entire time, my cock was still in Karen's
ass, and we basically hadn't moved since our handsome suitors' entrance.
Diamond came over and lifting up her slip, revealed that she wasn't
wearing panties and was sporting an 8 inch erection. She lowered her
crotch over Karen's head, and without a word, Karen slid her lips onto
Diamond's cock and began sucking away. Diamond looked up at me and told me
that Karen had promised to give her a blowjob the next time she saw her,
and that she was just fulfilling her promise. She then leaned in towards
me, and with our faces just inches apart, told me how she had wondered
last night how my lips might taste, and how jealous she'd been that
Josephine was the only one who'd gotten a taste.
Smiling I told her that it was never too late to sample my kisses, and I
pressed my lips against hers, hard. I tasted strong powerful lips, which
gently parted my own, and I felt her tongue snake into my mouth, wrestling
back and forth with my own tongue. I still had one hand on Karen's cock,
which I began pumping again, but my other hand now reached over to
Diamond, and massaged her sexy body which was wrapped up in a beautiful
lacy slip. Our kisses became more passionate, and my state of arousal was
heightened by the sounds of Karen's slurping and sucking on Diamond's
cock, when I felt my panties and hose being lowered over my ass, and my
butt plug slowly being pulled out.
I felt Josephine's other hand reach around to my breasts and begin
massaging them, and then her breath on the back of my neck. She leaned in
close and then whispered into my ear, "Finally I get to fuck your sexy
ass."
I felt a condom-covered and lubed cock come to rest at the entrance to my
ass pussy. Slowly, she began to push forward, and I felt her cock head
stretch my opening. I gasped as her cock entered me, and then finally let
out a moan as it slid all the way into me. As she started to pull back,
her hands at my hips now and her lips dropping kisses onto my back and
shoulders, I did the same with my cock in Karen's ass.
We began to fuck in rhythm, Josephine moving into me at the same time as I
was plowing into Karen, with her legs still up on my shoulders. During
this time, I had continued kissing Diamond, I was still jacking Karen off,
and she was still sucking on Diamond's cock. We were a tangle of bodies,
lingerie, and sex, and it was one of the most amazing sexual experiences
of my life. Four individuals completely wrapped up in pleasure. All of our
senses were heightened, and the only sounds you could hear in the room,
were grunts, slurps, and bodies grinding against each other. Each of our
girly cocks were being stimulated, and it was only a matter of time before
someone came and set off a chain reaction of orgasms in the group.
Diamond was the first of us to give in to their release, and as we kissed
I felt her start to let out a scream, and then pull off of my lips and
begin shouting Karen's name. Looking down, I noticed the cum leaking out
the side of Karen's mouth as Diamond's hips thrust forward into her, and
Diamond fell forward onto my body, relishing her post-orgasmic state.
At the same time, as I continued to pump Karen's cock, I felt her begin to
stiffen and then twitch in my hand, before shooting her load up and onto
both Diamond and myself. She also let out a muffled scream as Diamond had
not removed her cock from Karen's mouth and there was still cum dripping
out the side of her lips.
My orgasm had been building this entire time, and the pressure was almost
unbearable as I tried to last just a little longer and savor the feeling,
but when Josephine leaned forward to my ear and whispered that she was
ready to fill me with her cum, it was too much for me and I went over the
edge. With a final forceful shove into Karen's ass, I began to cum in
spurts, enjoying my most powerful orgasm of the weekend.
My head was dizzy, and I experienced an explosion of pleasure in all my
senses. Sweaty bodies, orgasms, cum, lingerie and lace, it was a fantastic
flood of femininity and sex and I loved it. I felt Josephine's cock get
rock hard, and she let out a low guttural moan before her final thrust as
well. I could almost feel the spasms in her cock as she came and pumped
her semen into the condom. I fell forward onto my hands, and felt
Josephine lean up against me as well as she came down from her orgasm.
All three of us, Diamond, Josephine, and myself fell to our sides, and as
I pulled out of Karen, and Josephine out of me, we rolled over and spooned
each other, Diamond behind Karen, and me sandwiched in between her and
Josephine. Our night was just starting though. As soon as we recovered we
still had hours of dressing up fun to come and multiple orgasms to achieve
with each other in a variety of combinations. It was going to be a
wonderful evening.
Grace
- 25.07.2022
- 15
- 0
