The Adventures of Ann This Adventure is Titled Boats and Snakes
- 2 years ago
- 33
- 0
Erika's Adventure Part Three free porn video
All of my stories are complete fiction, all the characters and situations
are also fiction. You should be at least 18 yrs of age to be reading
this. This is the adventure of a young twenty something tgirl, who is on
a journey of self discovery, and her adventures and mishaps along the
way. Some stories involve sexual content and the main story is about
sex, while other stories involve Erika's day to day routines. I hope you
enjoy it.
Erika's Adventure Part Three
I was still dressing up once a week, and I was building quite a wardrobe.
I did a little shopping in person, always in guy mode, but most of my
shopping was done online, it's so easy. I did enjoy shopping in person
but even though I dealt with the idea of a guy buying women's clothing a
bit better, I was still a bit shy about it. As far as dating goes, I
haven't had a date in a while, neither men or women. I wasn't really
interested in meeting a woman right now as I wanted to explore these
feminine feelings I was having, but so far I had no luck meeting men.
There are a lot of men out there that are interested in tgirls, but most
of these "admirers" are either former or current crossdressers, or they a
bit too kinky for me, or the biggest one, they are just online fulfilling
a fantasy and have no real intention on dating a tgirl. I had to admit
it was beginning to be quite frustrating. I would get hit on all the
time when I was online but it never went anywhere. I told myself that I
would continue to be very picky because I know what I was looking for and
if Mr. Right didn't come along then I would just wait, after all I was
still having fun dressing up, and I made a bunch of tgirl friends online.
My life was going pretty well for the most part, my work was going well
and in fact I was looking at buying a condo for myself, and getting out
of my apartment. I was able to keep my boy life separate from my girl
life for the most part, and I liked it that way. I had to admit that I
hardly ever thought about women the way I used to. Now when I see a hot
girl when I am out, I am checking out her clothes and her makeup, when I
see a hot girl on TV, watching "Friends" now instead of wishing I could
date Monica and Rachel, I wish I could be Monica and Rachel (I like
Phoebe, but not that way :) When I am at home and I am really horny,
I'll look at transsexual porn and of course I wish I was the tgirl
getting fucked. I can't remember the last time I masturbated to a woman.
In fact the other night I had the biggest wet dream of my life, and from
what I could remember, I was dressed up as Erika and I was getting fucked
by a well build black guy, and he was fucking me good. Anyways I
remember waking up with a big mess in my pants and a big smile on my
face.
When I went to work I now noticed the men in my office a lot more. I
found that I was attracted to the older guys in my office, I really liked
guys over 40, in fact two of head bosses in my firm were very attractive,
both were in their late 40s, one had graying hair and I thought that
looked cool. Also at the gym I found that I was attracted to bigger
guys, well build guys, I mean most women like a man with some muscle, but
I like the idea of how small I would be in their arms. I would always
sneak a peek when I was in the showers and some of the men had monster
cocks, their cocks made mine look like pathetic. I was always very
careful not to get caught sneaking peaks, and that may cause a lot of
problems. The only guy that really caught me looking was JR, who I met
with Jessica who turns out to be part owner in the gym. I am pretty sure
he caught me looking once or twice, but he never mentioned a thing.
One Saturday night I decided to get all dolled up and to take a walk
outside at night, and maybe go to the mailbox down the street as I did
need to mail something, and this would give me a chance to get out of the
house as Erika. I went a bit casual, I was wearing a tight pair of
skinny jeans, they made my ass look amazing. I waited until it was dark
around 9pm, then I put some things in my purse, I put on my new jacket
and took a deep breath and opened my door and I peeked out to make sure
no one was around. I locked my apartment door and I double, triple
checked that I put my keys in my purse, the last thing I wanted to do was
to get locked out of the house dressed as Erika. I started walking down
the hall towards the elevator, I am much more confident with my girlie
walk, I have been practicing quite a bit, and you'd be surprised on how
many good tutorials are online nowadays. I pressed the elevator button
hoping that it didn't take long to arrive. While I waited I checked
myself out in the mirror, I was pretty happy with my makeup, I was going
for the girl next door look. The elevator arrived and I got in and no
one was inside. I live on the 11th floor so the trip down felt like an
eternity, I was almost on the ground when it stopped at the second floor.
Two women who I have not seen before got on, I didn't make much eye
contact with them. The elevator made it to the ground floor and I let
the other women off then I got off. As I headed to the door I was
shocked to see Jessica outside the main door, she was ringing my buzzer,
but the time I noticed I had already opened the door and she grabbed it
and thanked me and enter the building. We didn't make eye contact at all
and I quickly left the building. I was in a complete shock, I mean,
Jessica has come over before but never unannounced. What are the chances
that she comes by just as I am leaving the building dressed as Erika.
Anyways I wasn't sure what to do, I kept walking and decided to head to
the mailbox to drop off my letter. I calmed down a bit, in fact I think
the clicking of my high heeled boots had a calming effect on me. There
were a few people out on the street but I passed by them without
incident. Once I arrived at the mailbox, a man arrived at the same time
as I did, and he told me to go ahead, I remember he said, "ladies first."
I gave him a smile and dropped my letter in the mail slot. I headed home
when I got a text from Jessica, it said. "HEY U, I STOPPED BY YOUR PLACE,
I KNOW GUYS LOVE THE POP IN, ANYWAYS I WAS JUST IN THE HOOD, I THOUGHT I
WOULD DROP OFF YOUR DRILL, C U TOMORROW." I felt better now, but I
wanted to make sure she wasn't still at my apartment, I started to text
her back when to my surprise her car drove right past me. I decided to
head back now before she turned around. I made it into my apartment
without any incidents, I took a deep breath once I got inside and looked
the door. I decided to get some wine and sit down at the computer. I
was chatting online with a few tgirl friends, and of course I had one or
two admirers trying to chat me up, but their chats were going nowhere.
It was getting late and I was just about to log off when I received an IM
from "greatone69." Now I haven't chatted with him before but he did send
me a message a few weeks ago, I checked out his profile and he seemed
okay. I wasn't going to chat, as I was tired but I decided to have
another glass of wine and I returned his message.
GREATONE69: Hello Erika, how are you this evening?
ME: Hi there, I'm doing okay, thanks. ( now I should tell you that I
generally only chat with people online if they have a photo in their
profile. His profile did have a pic, it was kind of hard to see, as
these photos are a bit small, anyways he had a beard.)
GREATONE69: well that's good, my name is Wayne by the way. I really like
your profile pic btw.
ME: Thanks, nice to meet you Wayne. I like your pic as well.
GREATONE69: So what are you up to tonight?
ME: (here we go, most guys start with that line when they want to hookup)
Not much, I was just about to head off to bed, I had a good night, I got
to dress and I went for a walk as Erika tonight.
GREATONE69: That sounds like fun do you go out often dressed, by the look
of your pics it looks like you are pretty passable. Are you a full time
girl?
ME: Thanks, I am somewhat passable, I am only a part time girl, in fact
this was only the second time I have been out in public dressed as a
girl.
GREATONE69: Wow, good for you, well you look amazing, you should go out
more often. Maybe I should tell you a bit more about myself, I'm Wayne,
I am 43 years old, I see that we are from the same city, I am 6'3 about
225 lbs and I'm single.
ME: Thanks Wayne, well I'm 23 years old, I'm 5'7 and I women don't like
to talk about their weight :) but I am less than 160lbs, and I too am
single.
GREATONE69: Wow your description sounds great, especially the single part
:) two bad I am so much older than you :)
ME: age is just a number to me.
GREATONE69: I don't want to get too personal, but do you date men?
ME: no worries, I do date some men, but I am very picky.
GREATONE69: being picky is a good thing, glad to hear that you date me, I
have dated a couple of tgirls before, do you date older men?
ME: To be honest I have not dated many men, the whole idea is still a bit
new to me, but I would have no problem dating older men, in fact I think
I prefer older men.
GREATONE69: Good for you, older guys are great :) What are you looking
for in a man?
ME: Good questions...Well like I said I like older guys, not too old of
course :) I like a masculine man, preferable taller than me. I like a
guy who knows how to treat me like a woman, and guy who is genuinely
nice, with a good sense of humour...and being well endowed helps as well
( just kidding)
GREATONE69: I like your sense of humour, and you kinda described me with
your descriptions, even down to the well endowed part :)
I was actually enjoying our chat, so I grabbed another glass of wine. We
chatted for another 30 minutes or so, the chat never got too sexual as
most admirer/tgirl chats do get. He seemed like a pretty nice guy and
even after I told him that before I would ever meet anyone I chatted with
online, that I would have to get to know first, and we would have to chat
for sometime before hand. he seemed okay with this, some guys who are
just looking for sex cut off the chat right away, but he kept chatting.
It was getting late, so we stopped out chat and he said he would like to
chat again, and I told him if he saw me online to feel free to say hi.
Then I was off to get undressed and talk off all my makeup, I had a long
day, especially with my first girlie outing in a long time.
Over the next two weeks Wayne and I chatted from time to time, he seemed
like a nice guy and our chats were always fun. To tell you the truth he
has yet to pressure me to meet him, most guys want to hook up right away,
since I tell guys I want to get to know each other before we meet, most
guys say they are cool with that but drop off the face of the earth once
their hardons go away. Wayne seems genuinely interested. Most time we
would talk about everyday things, but we would talk about sex from time
to time, but each time he never took it too far, and he was always the
first to bring it up.
GREATONE69: you've told me what you look for in a man, but what do you
like to do when you are on a date with a man?
ME: Well most of the time I would get dressed at his house, this takes me
a while btw :) then I'd like to sit and chat a bit, maybe with some wine.
I love to take photos when I'm dressed so taking pics would be fun.
GREATONE69: That sounds good, I actually just got a new camera :) and no
worries about taking you a while to get dressed, I am sure the end
results are definitely worth it. I don't want to get to personal, but
when it comes to being intimate, what do you like.
ME: (I paused for a bit, because this was the first time we were actually
talking about sex, and what we were looking for when it comes to sex, I
always find this a bit uncomfortable, but I know it is important so that
we can decide if we may be a good match.) So here comes the sex question
hey?
GREATONE69: Sorry if that was too personal.
ME: No problem, not too personal, but maybe you can tell me what you are
looking for? (I hate to through the question back to him, but I find that
if I tell a guy what I am looking for, then the guy just agrees with me
and tells me he is looking for the exact same thing, when they actually
are pretty kinky, which I am not into.)
GREATONE69: Okay can do. When it comes to sex I am a top and I am
looking for a bottom. I am not into anything weird, I like to have a
tgirl to give me a blowjob, and I like to give her anal sex. I am a bit
dominate, in that I like to take control when we are having sex, nothing
over the top, but I'm a man and I know what I like, and I do like sex,
especially with a hot tgirl :) I hope I am not scaring you off.
ME: no worries, when it comes to sex I like to take my time, I am not all
that experienced with men, or women for that matter :) I guess you could
say that I am the bottom and I like to play the role of a woman. I
really enjoy sucking cock with the right guy and I like getting fucked as
well. I also like a lot of kissing ( not sure about kissing a guy with a
beard :) and cuddling. I enjoy sex very much as well, especially with
the right guy.
GREATONE69: wow sounds great, you are turning me on right now :) how long
will it take to get your hot ass over here :) kidding. Oh and by the way,
I know my profile pic, I have a beard, but that's an old photo.
ME: Ha Ha, that's not going to happen, at least not right away :) but I
have to admit I am a bit turned on as well. So no beard he, well then
you need a new pic :)
GREATONE69: oh well, I had to ask, actually I am not even in town this
weekend, I am at the cottage. I can send you a new pic if you like?
ME: sure
GREATONE69: okay here comes two pics :)
ME: (I started to download the photos, the first one took a while to
download, but the second one he sent just opened, and it was a picture of
his erect cock) Oh wow your cock doesn't have a beard anymore, congrats
:)
GREATONE69: Sorry about that, I am not sure how that happened :) Did the
other pic work?
ME: no not yet.
GREATONE69: okay, well in the meantime, what do you think of the other
pic?
ME: Well you have a very nice cock there, good for you...it does look
pretty big :)
GREATONE69: well thank you very much, I take good care of it. It's pretty
big about eight inches...I've been told it's a mouthful :)
ME: Well very nice, eight inches is pretty big, and since we are talking
about size, I hate to disappoint you but I am only about 4.5 inches, and
no I am not sending a pic :) You other pic doesn't seem to work?
GREATONE69: okay, that's weird I'll send another pic. No worries on your
size, I like my tgirls small down there :)
ME: ( the new photo opened up, I was just about to type him back, when I
was shocked to see the photo was actually a photo of JR from the gym. I
was totally shocked, could this be real. I tried looking back at his
photo with a beard and the photos were the same even though it was hard
to tell, but one thing's for sure, this new photo was indeed JR) Sorry
BRB
I was blown away, I wasn't sure what to do next, I mean I was talking
about some very personal things with him, and now it turns out that we
know each other, I mean we've only chatted a few times and of course I
checked out his package a bunch of time but now what do I do. I stepped
back from the computer. I grabbed another glass of wine. Do I tell him
who I really am, do I tell him I recognize him? What do I do? About five
minutes had past.
GREATONE69: still there beautiful?
Okay I had to say something to him. I was going to tell him that we
actually knew each other, so I sat back down at the computer.
ME: Sorry about that, your photo opened, you look very good without the
beard. (I now chickened out and I was just going to tell him that I was
heading to bed.)
GREATONE69: Thanks, I actually have a goatee right now. Glad you like
it.
ME: well I like a bit of facial hair, listen I have to get going, I've
had long day.
GREATONE69: okay, well I enjoyed our chat once again, and let's talk
soon, have a goodnight sleep Erika.
ME: Goodnight
I logged off the computer and I actually started to laugh a bit, I mean
what are the chances that I first of all I start chatting with a guy
online, and I hit it off enough to keep chatting with him and it turns
out to be someone I know. This is really too bad, I was actually getting
pretty comfortable talking with him, but I can't take the chance now, we
know each other. I headed off to bed, and in fact I masturbated once I
got into bed, and yes I was thinking of JR's cock when I jerked off.
Lizbeth
- 27.03.2021
- 34
- 0
The Adventures of Ann This Adventure is Titled Boats and Snakes
- 3 years ago
- 31
- 0
Evelynn s strange adventure Part 4
- 4 years ago
- 45
- 0
