Blackmailed
- 2 years ago
- 40
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Blackmailed free porn video
I remember my hands trembling as I opened the package, I knew where it
was from and I knew that it wasn't going to be good.
It all started about a month ago when I was out of town for the week on
business. As usual, I snuck some of my "girly" clothes in with my
regular stuff thinking that they would provide me with a distraction
during the lonely nights away from home. I have been cross-dressing for
quite some time now and since my job requires that I be out of town
frequently I have ample opportunity to dress up. I must admit that with
my small frame, tight ass and slim legs (the product of daily running) I
look quite sexy in my lingerie. I also learned to apply makeup by
watching my wife and with practice I had gotten good at it. Top all of
this off by combing my long hair into a wild look and I made a very
convincing female. Mostly it was harmless fun with me staying in my room
and eventually masturbating. Until that week.
I came back from some meetings and noticed a note asking me to call an
extension in housekeeping. The woman who picked up asked me if I would
be in my room for a while and if it would be okay for her to come up. I
agreed and shortly answered the door to a fairly attractive woman who
was obviously used to being in charge. She introduced herself as Gloria
and said that one of her maids noticed my unusual taste in clothing and
unless I did a favor for her my wife would be getting a set of panties
in the mail with a note saying that they were left in my room. I
couldn't believe that I was being blackmailed! I told her that my wife
would never fall for that and demanded she leave. She said that with a
few follow up phone calls, she would have my wife convinced that I had
an out of town girlfriend. Stunned, I sheepishly asked what she wanted
from me. What she wanted was for me to get dressed up and go on a "date"
with another guest!
She left saying that I had an hour to make up my mind and that the time
would be put to good use by bathing and shaving. I was in shock and
couldn't see any way out so I reluctantly did as told. I was shaving my
legs when I heard Gloria let herself in. I came into the room in a
bathrobe and saw that she had laid out my outfit for the evening. "Good,
I see that you have made the right decision, now get dressed and I will
do your makeup as I explain what is in store for the evening" Gloria
ordered. I got out of the robe and put on the white lace garter belt,
silky lace top stockings, white satin panties that securely held my
"secret" in place and white lace bra with some breast forms in it. I
finished getting ready with a white blouse, tight black mini skirt and
some white "come fuck me pumps". I sat in front of the mirror as Gloria
teased my hair into shape and skillfully applied my makeup while
explaining my date for the evening would be a regular guest that had
asked if she could set him up with someone like me. A night out for
dinner, drinks and dancing would begin when Troy picked me up in a half
hour. Finished with my transformation, she stepped back and exclaimed
that if she were a man, she would definitely be looking forward to
fucking me. She was right! I have never done such a good job with
makeup. It was perfect from the eye shadow that highlighted my green
eyes to the bright red lipstick. I couldn't believe that it was me! I
was so involved that I didn't catch on right away, what did she mean
when she said fucking me? The answer came soon enough. As Gloria started
to leave she snapped a quick picture of me and said that if I didn't
want my secret exposed I would show Troy a "good" time and that there
might even be a tip in it for me! I sat on the bed confused about what
had happened to me. I have never been with another man, but I was a
little excited sexually when I saw how complete my transformation was. I
was still a little dazed when there was a knock on the door and I
answered it.
Troy was very handsome with an athletic build and a smile that helped
put me at ease. I told him my name was Kelli and we left for a night on
the town. All through dinner and drinks Troy was the perfect gentleman.
He calmed my nervous tension and I was actually having a good time when
he asked if I wanted to dance. I was starting to feel comfortable with
my situation and did not protest as he held me tight and kissed me. I
could tell that he was as excited as me when he firmly put his hands on
my ass and held me close as our bodies rubbed against each other. After
a few dances Troy mentioned what a great time he was having but it was
time to go, so we left. Back at the hotel he kissed me again and asked
if he could come in. I had sometimes fantasized about being with a man
and at that moment nothing seemed more natural. I was completely
immersed in being Erica.
At the door, Troy held me tight and gave me a passionate kiss. He was
bigger than me and I felt strangely comfortable in his arms. I walked a
few steps away from him and slowly wriggled the tight skirt down my hips
and pushed it down to my ankles. Bending slightly at the waist to pick
it up I knew that Troy had a perfect view of my satin clad ass. He
whistled approvingly as I turned around and unbuttoned my blouse showing
off the rest of my new lingerie. "You look fantastic!" he said as I
moved over to him and got on my knees. As he got out of his shirt, I
unzipped his trousers and let them fall to the floor. He stepped out of
his shoes and pants as I lightly kissed the insides of thighs while
moving my hands up the back of his legs to the waistband of his briefs.
I kissed and licked my way up his legs as I pushed his briefs down to
uncover the object of my attention. He had a beautiful 8-inch cock! I
have never been ashamed of my penis but this guy had a lot to be proud
of. Not overly thick but rock hard with a perfectly shaped head that I
couldn't wait to suck on. Teasingly, I licked at the head and made
circles around it with my tongue. I knew what I liked and I wanted so
much to please this guy. Troy moaned as I started to slowly push my
bright red lips down his throbbing rod. With my hands on his ass cheeks
I took as much of him into my mouth as I could and caressed his manhood
with my tongue. Starting slow but gradually increasing tempo I worked my
mouth up and down the length of his cock. Troy groaned and I could feel
his body stiffen as I prepared to swallow his load. Wave after wave of
tasty cum splashed down my throat until finally he started to soften and
I let his spent rod drop from my mouth.
"You can really suck a cock" he said, "how about we lay down for a bit
and relax, I'm a little weak in the knees". I never expected to actually
be proud of sucking my first cock but I smiled as I lay down on the bed
next to Troy. We chatted a little bit and Troy suggested he give me a
back rub as a reward for all my fine work. He straddled my legs as I
felt his strong hands work my shoulders and back. His massage was
getting us both very hot and Troy was paying more and more attention to
my ass and legs. "I have been looking at your ass all night and won't be
able to leave until I've given you a proper fucking" he announced as he
started to pull off my panties. He opened the nightstand drawer and got
out some lube and a condom (how did they get there? - Gloria!). I
squealed my consent as Troy gently worked first one, then two well-lubed
fingers in and out of my virgin ass-pussy. After putting on the condom,
Troy grabbed my hips and pulled me up on all fours. I sighed excitedly
as he parted my cheeks and put the head of his cock between them. Slowly
he pushed himself into my hot ass-pussy. At first there was some pain
but Troy was experienced and he waited for my muscles to relax before
continuing. What a tremendous feeling. I wriggled my hips backward into
him as he plunged his rod deep inside me. I had a raging hard on as Troy
started fucking me. Out of the corner of my eye, I could watch us in the
mirror. What an erotic sight to see a sexy girl being screwed by this
stud and knowing that you are that girl. I was begging Troy to keep
fucking me as his rhythmic strokes increased in speed and force. I
stroked myself to an incredible orgasm as I felt Troy cum deep inside of
me. I lay on the bed exhausted and satisfied as Troy pulled his now limp
cock from my ass and went into the bathroom to clean up. When he was
finished, Troy kissed me lightly on the back of the neck thanking me for
a great evening and then he left.
I woke the next morning surprisingly content and still in a little
disbelief about the events from the previous evening. When I went to
shower and get ready to leave I found a thank you note and a hundred
dollar bill from Troy. Oddly, I felt hurt by that but I put the bill in
with the rest of my stuff and checked out of the hotel.
After a few weeks the whole experience seemed like a dream until the
package came. It was from housekeeping at the hotel and when I opened it
there was a video of the night's events along with a note that my
reservations for the coming week were confirmed. No further explanation
was offered or needed and that is why I am on my way out of town again.
Lianne
- 09.06.2022
- 19
- 0
