Unexpected pleasures 1
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Unexpected Pleasure Part 1 free porn video
Unexpected Pleasure Part 1
By Ms. Jenny Ann
I wrote the following story, it may be downloaded or shared at free site
only. It starts as a retelling of events, however, then it is more how I
wished it would have been. You may send comments to me
[email protected]
Chapter 1 Did not know
Jimmy should have known that his asshole could be a source of pleasure,
however, it was how he became aware of the delightful pleasure that gave
him quite a shock. It was Jane his girlfriend, that had opened him up to
the pleasure and it could not be denied it was by far the best sex they
had ever enjoyed. She fuck him with one then two fingers and his
pleasure was totally better than the climax he normally felt with his
cock and that was the problem.
Jane had found out that he was a crossdresser, and she did not like it,
however, she knew and said, "We are not going to get married, unless you
stop."
I told her, "I can't stop, I thought I could, and I really tried you mean
a lot to me, so I guess you don't want to be with me anymore." I had
tears freely flowing from my eyes.
Jane said, "We could still date and even have sex, we can try that."
I was trying to have the best of both worlds I could not be the man that
she wanted, but for now we could still be together. I knew that it would
not last and someday we would break-up. Now it seems that that day is
getting closer. Whenever I tried to stop dressing up in women's clothes,
I would fail, and I would make myself more feminine with my appearance, I
liked to not just wear women's clothes I wanted to look like a woman when
I was dressed.
I had lasted for over two months this time without dressing up as a
woman, the hair on my face was back and my body hair as well, however, I
knew that after I dropped Jane off, I would have a late night and before
I went to bed, I would be hairless again. It was not my fault if she had
not finger fucked me and made me get off like a woman from the pleasure,
I would not have the overriding need to feminize myself and I waxed my
hair off, the face, hands and arms, torso and feet and legs. I did look
more like a woman than a man, Jane was going to be pissed-off.
I really wanted to look they way I felt, however, I was tired, and I
could dress-up anytime I wanted over the next three weeks with my
hairless feminized body, and I knew I would. Just a quick look at myself
in the mirror, I pulled my waist length hair over my shoulders and
covered my lack off breasts tucked the cock and balls between my legs and
was amazed at how much I looked like a woman and I could feel my cock get
hard, I squeezed my thighs and did a little walk looking at my reflection
and I could feel the cum running down my legs and that was the only thing
that I like about being a guy, however, if I could get fucked in my ass,
I might not miss it, I would rather have many whole body orgasms then
just the one. I need to clean up Jane knows what dried cum looks like
and she can think all she wants, but without the evidence, what am I
thinking, one look at me and she will know. As I drifted off to sleep, I
was thinking if I could talk Jane into fucking me with a vibrator or a
life like dildo, I wondered at the types of dildos an adult bookstore
sold, I had never been in one, if she agreed then I would find out.
Morning came quickly as I went to bed at 4:30 am, so at 8 am I felt like
leftover crap, I really needed coffee. I made my way to the kitchen and
started the coffee maker and then a quick trip to the bathroom, no need
to shave and that is why I liked waxing, so I look more like a woman
without a trace of facial hair, if I were brave enough, I would do my
eyebrows into a nice feminine arch, however, that would make a statement
and I was not ready to make it. I put my coffee in a travel mug and went
to pick up Jane. I arrived at Jane's parents house and she got in the
car and spotted my hairless face and arms and said, "you just had to do
it."
I said, "Let's not get into it right now, I do not want to get upset
while I am driving, what would you like to do?"
She replied, "We need to talk, so we can do that better at your place."
If I told you could hear a pin drop, I would not be far from the truth.
We got back to my apartment and she started in with the, "Why do you keep
waxing your hair off, it makes you look more like a woman!"
I said, "Fine, I will tell you why I felt the need to wax my hair off,
you fuck me with your fingers in my ass and it felt good, so good in fact
that I had to make the outside match what I was feeling on the inside. I
came like a woman and needed to look more like a woman."
She said, "No way are you going to say it is my fault."
I said, "You may not have thought it through, but the end result is what
you see, I really wish you could understand how hard it is for me to try
to be a man, I know I am male, however, at times I really need to look
and dress like a woman and the way you made me cum like a woman, it
proved to much for me keep from doing what I had been trying not to do,
it is just the way I am."
She said, "You are right I did not put enough thought into what I did.
However, I do not want anyone to think that we are girlfriends, I told
you that I am not into girls, so maybe we need to take a break while your
hair grows back. Even dressed in blue-jeans and a tee-shirt you look
like a woman. It would be better if you just took me home."
I replied, "I think you are right we need a break."
Chapter 2 A New Reality
Dead quiet on the ride, however, my mind could not stop thinking about
how good it would feel if I could be fucked in the ass. I dropped Jane
off, I did not know if this would be the last time, I said, "I know it
will take at least 3 weeks to how my hair return, I will call and keep in
touch."
I did not bring up her fucking me in the ass it was a non-starter, so I
would have to get the pleasure by myself. I got home and put on a pair
of knee high hose and put on my 3 inch high heels put a pair of hoop
earrings in my pierced ears and went to find the adult bookstore.
I found the adult bookstore and went in and I was lost there was so much
stuff leather outfit, sexy lingerie, magazines, books, movies and the
dildos in all sizes and in two colors flesh tone which I took to be white
and no doubt the other was black. I knew nothing about what size to get,
so I decided that I would look at the choices of movies that they were
showing in the private rooms. As I was looking and trying to make a
choice, I heard him come up behind me, my heart was racing and he said,
"Miss, if you would like some company, we could watch one together."
Ok, I knew from the back I indeed looked like a woman I did have the
waist length hair and I was wearing three inch high heels, but I really
am male, and I needed to let him know that I was male, however, I like
being thought of as a woman. I turned to face him and said, "I get that
a lot, and I really do not mind as I am quite feminine, I would rather
people think I am a woman then cut my hair. Do you still want to watch a
movie with me?"
He said, "My name is Todd and I really would like to see a movie with
you. Which one would you like to see."
I knew when I saw it was made for me, the cover had a shemale giving
head. I said, "I really like this one." I pointed it out to him.
He said, "That is just the type of action that really gets me hot, are
you sure we have not met."
I could not believe I was doing this, I wanted him, I said, "only in my
dreams, however, I like this reality much better."
He took the choice to the clerk, and said, "This movie, please."
The clerk took the movie and said, "I will set it up for room #3, it will
be ready in just a few. Anything else?"
Todd said, "A bottle of Locker Room and a roll of quarters."
I did not know what that was, as I was new to this, however, I was sure
that Todd knew best. I said, "This is the first time I have been in an
adult bookstore and you could say I am a virgin." I looked at Todd and
he was smiling. I looked him over and knew he must be some sort of
professional type of man, his hair was cut short, and he wore a casual
suit and I wanted him. I thought of Jane and knew that I would not want
to be with her after today.
Todd and I made it to room #3 and he explained how it worked, I was to
put $5 in quarters into the slot and the movie would start and if it
stopped and we were still enjoying ourselves I was to feed it more until
we were done. Not much foreplay in the movie or story line, it was an
extremely hot and dirty movie and were both were enjoying the action and
I found myself on my knee facing Todd, he slid his slacks and boxers down
so I could get to his cock, I had never been looking at a man's cock this
closely and I knew what I wanted I licked the tip of his cock with my
tongue I ran my up from its base to the rim and traced around the head, I
held it to my lips and opened my mouth and took it in just past the head
then back to the tip then past the head each time going down more,
however, it was my first blow-job and I could not deep throat him, I must
have been doing all right for he was hard as a rock, then he pulled out
of my mouth and I felt the loss I was about to put in back in when he
said, "I want to fuck you, stand up and drop your jeans and let me have
that nice ass of yours bend over the bench and snort some of the Locker
Room." He showed me and while I was having a mind blowing high, he
entered my asshole the high was so intense I did not feel any pain;
however, I could feel a little as I was coming down, but it quickly
turned to extremely the best total body orgasm, it would build to high
peaks and then start all over, I felt it all over it was the best sex
ever and I knew that I would never have sex with Jane again. I reached
for my small cock and it was indeed hard I stroked it I could feel as it
soon would climax, it seamed that Todd knew and as he entered, I was
pushing back I wanted him in me all the way. I started to cum and when
my asshole started to clamp down on Todd's hard shut it sent him over the
edge, I could feel his hot load filling the deep recesses of my bowels.
We both were done; however, I still want to feel him in me and as he
started to pull out, I said, "Please leave in in for just a few more
minutes, it feels so good in me."
Todd said, "Ok, if that is what you want. So, did you like the movie?"
I said, "Yes, I could see myself as the shemale, however, my boobs are
way to small!"
Todd said, "That does it, I do not want to let you out of my life. I
would like to see you with breasts like hers and I can help you get
them."
I said, "Yeah, right I bet you say that to anyone like me."
Todd said, "NO, you are the only one I have said that to, and I can help,
my full name is Doctor Todd Lewis and I have wanted to have a shemale
lover and that would be the price for my help. Ask yourself, do I really
want to have breasts if so, then I am your man! What is your name."
I looked at the shemale on the screen and said, "YES! You can call me
Jenny Ann."
End of Part 1
Nadine
- 19.03.2021
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