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The business man
Being a T girl has been exciting for me over the years and
I have always enjoyed meeting a variety of men for fun times.
I love being treated as a woman, being kissed and caressed
and more. I prefer to entertain men at my home, but since
my son has moved in with me it has become much more difficult
to have a private life at home.
Tom had emailed me from an old ad that was still up on craigs
list and complimented me on my appearance and said he would
be in my area the following week. He asked if I would like
to get together after we exchanged a few emails. I explained
my living situation and he suggested I come to his hotel
room. Now, I like to be already dressed and made up when I
meet someone so I declined. I got to thinking about it and
his interests and wrote back that if he still wanted to meet,
I would get a room locally and he could come to see me.
I checked in in the afternoon and after shaving very smoothly
and taking a relaxing bubble bath (which softens my skin)
I decided to wear my red lacey thong and matching bra, followed
by black thigh high stay up stockings, my new red, tight
mini skirt and a new black tank top with lace at the breast
line. I applied my make up, always with bright red lipstick,
or cocksucking red as I like to call it. lol. Brushed my long auburn
wig and placed it on, followed by my breast forms and jewelry.
It was only 6 pm and Tom wasn’t expected til 7, so I poured
some wine into the little plastic cup and sat down to check
my email on my laptop. My friend Bob from another site had emailed
me again, still wanting to meet up with me as soon as we can
both schedule it. I replied back that I was actually in his
area, but already had plans to meet someone, and that I was
still interested in him, but another time.
Tom arrived as scheduled and we sat together on the bed making
small talk, then he ran his hand along my leg and kissed me
deeply. we lay back on the bed kissing and groping and I could
feel him getting harder as I caressed him thru his pants.
I undid his belt and unbuttoned his pants and he helped me
lower them and take them off. I caressed his hairy balls
and wrapped my soft hand around his average sized shaft
that was now leaking precum. I love precum almost better than regular cum as its so sweet. I leaned over and licked it
from the tip of his hard cock as he moaned. (I love making
men moan). I took his cock deep into my mouth, pressed my tongue
against the shaft as he was buried deep in my wet mouth.
I began stroking him with my lips as I caressed his balls.
I stopped so that we could kiss and make out some more, and
played with his cock as we did. He stood up and then pulled
me to the edge of the bed, my skirt rising to my waist as I slid
on the bed. He lifted my legs and quickly placed a condom
on his cock, I pulled my thong to the side and he slid his cock
into my tight ass. As he wasnt really very big he kept slipping
out and I turned over and suggested he do me from behind.
He struggled to find my hole this way, but eventually did,
altho he had gone soft by this time. Then he asked if I had
any toys and I got up, went to my bag and returned with my 8″
dildo. He fucked me with it and played with my little clitty
as I sucked his cock up and down. When he started thrusting
up into my mouth I knew he was close and I just kept on sucking.
I felt the dildo being thrust deep in my ass and he moaned
and grunted and said “take it bitch”. I went
down to his balls with my mouth and he let loose with a warm
stream of hot cum. I kept it in my mouth for a minute to savor
the taste and then swallowed. He pulled the toy from my ass
slowly and I licked his softening cock and balls to be sure
he was clean of any cum that may have dripped from my mouth.
Then he got up, got dressed, thanked me and left. WTF, I thought,
I was expecting a long night of lovemaking and hot sex, and
it was over within a half hour.
I went back to my laptop with another cup of wine and noticed
Bob had replied to my email. He said that he wished he had
known sooner I was in the area. I apologized and told him
about my brief less than memorable encounter, without
all the details and hit send. Then I switched on IM chat
and in less than a minute Bob was IM’ing me. He told me
how horny he was for me and how he wanted one of those blow
jobs he had seen in my videos. I said I was still at the motel
and if he wanted he could experience it tonight. He went
on to say he had never done anything like this before with
either a girl like me or another man and was nervous, but
very excited to try it. Said he was afraid he wouldnt last
very long as he was so horny and excited and didnt know if
he would chicken out or go thru with it. I said I would give
him an out. Said if he wanted to come over to see me, I would
excuse myself to “powder my nose”, and if he
didnt like my appearance he was free to leave while I was
in the bathroom with no hard feelings. Ive used this technique
with other newbies and first timers before and no one has
ever left. I gave him my cell number and he texted me that
he was on the way. I fixed my makeup and hair, straightened
out my skirt, and a few minutes later another text saying
he was there. I gave him the room number and then a knock at
the door. He was taller and thinner than I had expected.
I had only seen his cock pic on his profile. He also looked
younger than his 37 yrs, but I wasnt complaining, I like
being a cougar. I offered him some wine, but he had a beer
in his hand and he drank that. He just stood there staring
at me and looking at the porn video I had pulled up on the laptop.
I excused myself to freshen up, told him to make himself
comfortable and went into the bathroom, hoping he would
still be there when I returned.
to be continued