Brandon and Danielle
- 1 year ago
- 27
- 0
Brandon, The Delivery Boy free porn video
I was 52, retired, and living in a small town in Montana. My wife passed
away last year and I was falling into a depression. I didn't really have
a lot of friends in the area. Social events were more my wife's thing.
I'd tag along on occasion, but mostly she bore the brunt of talking to
people. After she passed, the friends slowly stopped coming around to
check on me. That was fine, since I enjoyed my solitude. Heck, I bought
this house in the countryside just so I wouldn't have pesky neighbors
dropping by all the time! But it did often mean going days without human
company and I was becoming lonely.
When my wife was still with us, she hated my old bachelor porno
collection and made me get rid of all my videos, DVDs, and magazines
when we got married. Confession time...now with her gone, I found myself
drawn to online porn more and more. My frequent alone time translated to
naked time. I was masturbating at least 3 times a day, if not more. It
wasn't long before I started getting into chat rooms, even the video
chat rooms. It was nice to be able to "talk" to people again, especially
about my favorite subject - sex.
I started out looking strictly for women online, but I soon discovered
that there weren't nearly as many women on those sites as men. The ratio
really sucked. But at least I made a few guy friends in the group chat
rooms. It was a little strange at first, chatting with other guys, but I
figured we were all there to get our rocks off and were all in a similar
frame of mind. I found an odd camaraderie among the other guys. We could
talk about our cocks and jizz and what gets us off without any of that
puritan shame that goes on in the real world. Here was our own world of
sexual feelings and thought.
Another confession I have to make. I've always been a closet
crossdresser. Now with my wife gone, as well as access to all her
clothes and makeup, I was indulging in my hobby more and more often.
Thankfully we were mostly the same size. There were a few things (shoes,
pantyhose, a few skirts) that didn't fit me, but I had enough retirement
funds to splurge and buy myself a new feminine wardrobe. I had always
been into women, sexually, but with my new guy friends in my sexual
online world I've found myself actually getting turned on by wearing my
girl clothes and sex chatting with them. I still never wanted to be with
a man in real life, but I was sure having fun watching other men get off
while watching me. I would put on a pair of her panties, her bra, and
some makeup and whack my "clittie" until I came with three or four (or
sometimes more) male viewers all getting off watching me. I was loving
it!
It wasn't long before I was wearing feminine clothes full time. It
became just a normal routine to shave my body smooth, put on some
scented lotions, slip on a bra, panties, and a fun little sun dress in
the morning and put on my face before making myself a light breakfast
and settling down to my computer and my first chat of the day. Then at
night it was just as routine to wash off my face, apply more lotions,
put on a night gown and settle down into girly dreams. I still put on my
male clothes on the few occasions when I had to go out for groceries or
whatever, but otherwise I was dressed up feminine. Well, I did still
wear my panties and camisoles and bras under my boy clothes. In fact, it
all became so routine that I made my big mistake one evening without
thinking. I ordered a pizza.
I suppose in retrospect that I had wanted this to happen subconsciously.
I wasn't even thinking about any possible ramifications of my online
pizza order. I was hungry and didn't feel like making dinner, so I
ordered out. But when the doorbell rang, my blood suddenly ran cold as I
remembered what I was wearing. A black mini skirt, white blouse, and
black lace bra, somewhat visible beneath the blouse. Even though I was
getting pretty good at my makeup, I was still pretty obviously a man
under these clothes. Particularly with the bulge in my skirt. I had no
choice at this point but to accept whatever reaction I was about to get.
I walked to the door and opened it.
Standing there was a young adonis. Curly blond hair, buff looking body
with a tight polo shirt encircling his biceps. He was a couple inches
taller than me, making me feel small and vulnerable. He had deep blue,
piercing eyes. I judged him to be about 19 or 20 years old. His name tag
read "Brandon". He seemed slightly taken aback when I opened the door,
but he soon gave me a cock-eyed grin and said "I got your all-meat pizza
here. That'll be 17.59, uh...ma'am."
Now like I said, I'm not into men sexually. But the last few months
dressing nearly full time as a woman and engaging in sexual play with my
online "boyfriends" (as I'd started to think of them) and the stream of
anonymous viewers of my webcam had had an effect on my mind. I suddenly
felt flush with desire for this gorgeous young man. I patted my hips
where, if I were wearing pants, would've been where my wallet was. "I,
uh, have to go get my wallet. Please come in while I look," I said.
Brandon smiled and entered my hallway and closed the door behind him. He
followed me into the kitchen. I motioned for him to put the pie on the
counter while I went to find my wallet. I took out my credit card and
handed it to him. "Steven, huh?" He smirked as I gave him the card. "You
strike me more as a Chrissy, wouldn't you say?"
I was momentarily stunned. Chrissy was the name I used for myself and in
my online world. How could he have known?! My cheeks burned red with
embarrassment. Brandon laughed at me. "I'm right, huh? You're Chrissy,
aren't you?" I nodded shyly. "I knew it! I recognized you the moment you
opened your door. So this is where the magic happens, huh?" It dawned on
me that Brandon must be one of my admirers from online. I wasn't
expecting *that* at all! I wondered for a moment why I didn't recognize
him, but there had been so many men viewing my webcam that I just
couldn't process them all. I knew at least that he wasn't one of my
"regulars" who I carried on conversations with. That put a whole new
dimension to our meeting.
Brandon slid his finger across my hand as he handed me back my card. I
felt an electric tingle rush through me at the touch. I blushed even
harder. He smiled at me and confidently said, "You know, it's customary
to give your delivery boy a tip..." I didn't think it was possible, but
I blushed even harder when he said that. I could see the crotch of his
pants beginning to stretch out.
"You, uhhh...if you have seen me online, you know I'm straight. I've
never done anything with a man before in real life," I stammered out.
"Shhhh..." he replied, "I'm straight too. What I love about you is your
utter and complete femininity. I love that you're willing to give up
being a man because it's obvious you were never meant to be a real man
like me. You were meant to be a woman. A beautiful, statuesque woman."
He was hitting all the right buttons with me. My clittie dick was making
an obscene tent in my skirt. But despite that pesky reminder of my sex,
I never felt more feminine and submissive as I did right then. Brandon
took the opportunity to bend down slightly. I closed my eyes and pursed
my lips. Before I knew it, I was kissing a man. I was actually kissing a
man, as a woman, and loving it! His slight beard stubble felt so
wonderful against my cheeks. I felt his tongue exploring my mouth, his
rough hands holding my sides, pressing against my blouse. He pulled
back, smiled again, and said "I can't do anything right now, but can I
come back when my shift is ended?" I didn't hesitate for a second before
saying "Yes! Please come back!"
He turned to leave, but just at the door he turned back and gave me
another big hug and kiss on my forehead. "I can't wait to see you
again!" he said, breathlessly. I flushed again and watched him walk back
to his car thinking what a perfect looking ass he had in his jeans. I
quickly shut the door and ran to my bathroom, disrobing as I went. I was
meticulous about keeping my body smooth, but I still wanted to touch up
a bit. I also wanted to re-do my nails and makeup. I drew up a nice hot
bath and dropped in a floral scented bath bomb. I stepped into the warm
water and lathered myself with soap, then shaving cream. I ran my razor
all over my body and my face and ensured I was as smooth as a baby's
bottom. I patted myself dry when I got out and put on some lotion. I
pushed my nuts into my body and tucked my tiny clit between my legs then
put on a gaff to hold it all in place. I sat down at my mirror and
started painting my fingernails and toenails a bright cherry red. I sat
watching some porn while I waited for them to dry. When they were, I put
on some fresh foundation, eye liner, shadow, blush, mascara, and finally
lipstick. I slipped on a matching red lacy bra and panties set, a garter
belt and black stockings. Instead of a skirt and blouse combo, I opted
for a sleek black dress. With the gaff on, my crotch was as smooth as
any woman's. I put on a necklace that emphasized what little actual
cleavage I had and fixed my hair up. I was finally ready and with only a
half an hour before he was due to return.
He was due to get off work at 11:00 pm and at 11:15, my doorbell rang. I
suddenly had butterflies in my stomach and my palms started sweating. I
walked nervously to the door and opened it. Sure enough, there was my
blond adonis. He had clearly run a comb through his hair and bathed
himself in axe body spray. "Welcome back, Brandon!" I said in a sultry
voice. He beamed at me and swept me into his arms, kissing me deeply. I
just let him as my body went limp in his arms. "You look absolutely
gorgeous, Chrissy! I've had a boner all evening thinking about you." I
had my arms around his strong back while he was kissing me, but now I
moved them down to his ass and around to his front. For the first time
in my life, I felt another man's bulge under my fingers. He felt so hard
and big! And the heat radiating from his jeans was phenomenal. He moaned
as I rubbed my palm across his bulge.
I took his rough hand and led him into my bedroom. He saw my webcam
setup and seemed to get excited by it. "Can you film us, Chrissy? It
would be so hot to show the world how I took your virginity!" I smiled
at him and opened my favorite chatting site and set up my broadcast. I
was getting excited thinking about having the world watch my personal
humiliation of submitting to a man in real life.
While I was setting up the webcam, Brandon had taken off his shirt and
pants and was lying on my bed in his boxer briefs. I almost swooned when
I turned and saw him. His chest was hairy and he had a defined hairy
treasure trail from his navel going down into his briefs. His arms were
well muscled and looked like he could crush my head without a thought.
And his hard cock was clearly outlined in his briefs. I stepped out of
my dress and sank down on the bed between his legs and started rubbing
his cock through the thin fabric covering it. I was so thankful for the
gaff I had put on which kept my little dick contained and my panties
dry!
He started moaning and running his hands through my hair. I leaned down
and licked his bulge. The first time my mouth had ever gotten so close
to a real cock. The smell from his sweat was intoxicating. "Why don't
you take it out, Chrissy?" he asked. I trembled as I reached up to his
waistband and slowly started pulling his briefs down. More heavy fur
appeared before the head of his cock came into view. He was circumcised
and had a pink helmet on a thick stalk. I pulled down farther until his
entire cock sprang into view. It was easily 8" long, if not longer. I
had never seen a hard on like that so up close and personal. I slowly
wrapped my fingers around it and began steadily stroking him. It felt so
amazing and powerful within my hand.
I was keenly aware that behind me my webcam was recording all of this to
the presumed delight of my usual audience. It was embarrassing to be in
this position after such a long time insisting that I was straight and
would never do anything like this with a man. I knew what I was about to
do next would really flip their lids! I leaned down and took his cock
into my mouth. The taste wasn't anything to write home about, but the
idea of submitting to this man and pleasing him as a woman would sent an
electric thrill through me. I rested his cockhead inside my mouth and
swirled around the pee slit with my tongue, tickling the sensitive skin
under the head. I had had enough blow jobs from real women in my past
that I knew what would drive him through the roof. I began tickling his
balls with my fingernails, one finger trailing down to his taint,
lightly stroking it. My mouth began bobbing up and down on his cock,
taking a little more of the shaft down my throat each time until I was
kissing his pubes and leaving little lipstick prints around the base of
his pole.
He had his hands on either side of my head, guiding me up and down on
his pole as he writhed in pleasure beneath me. Eventually he let up a
little and allowed me to come off his dick. I kissed up and down his
shaft then up his taught belly to his magnificent chest. I buried my
nose in his chest hairs and smelled his youthful sweat. Then I kissed up
to his neck then his mouth. Our tongues battling it out together. "Oh
god, Chrissy, you are amazing!" he moaned when he finally broke free. My
fingers were running all over his body exploring him, feeling the solid
muscles beneath the skin and fur. "I need to get into that ass of yours
NOW!" he suddenly demanded. He flipped me over onto my back and got on
his knees behind me. He stripped off my panties, then my gaff. My little
clit sprang into sight. He chuckled a little. "That's even smaller in
person than on the webcam! It's so cute!"
I heard him spit and felt wetness at my hole. The feeling of his fingers
caressing the outside of my hole was indescribable! Then, without
warning, his cockhead was there, asking to be let in. He spread my
cheeks wide and slowly eased his rod into me. It was so painful! I
begged him to go slow, and he did. Never pulling back out, just slowly
easing his way in until finally he was past my sphincter ring and he
slid the rest of the way in. He was pinning me down with my face in the
pillow as he allowed my ass to get used to the size of his intruder.
Slowly he began to withdraw, almost to the tip before thrusting back in.
I yelped with surprise. He repeated the motion. Again. And again. He
began to settle into a rhythm and the invasion into my virgin ass turned
from pain into pure, unadulterated pleasure. I had never, in my life,
felt as feminine as I did just then. My tiny clit was throbbing and
dribbling precum on my tummy.
Before too long, he was panting and his breathing got more and more
ragged and I suddenly felt him burst inside me. I could literally feel
each spurt hit the insides of my intestines. The pleasure sent me over
the edge and my clit began spurting rope after rope of cum on my belly.
I hadn't even touched myself! It just came on its own. It was the most
mind blowing orgasm of my life! He collapsed on top of me. His sweaty
chest against mine. Our lips met and we kissed passionately. "I had no
idea sex could be like this!" I panted. "Get used to it, babe. I'm going
to be seeing a lot more of you from now on," he said. I smiled
contentedly.
Elle
- 30.10.2022
- 32
- 0
