Circumstances
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Circumstances by freethinker32@yahoo.com
This is a story of fantasy and fiction. Hope you enjoy.
When I was twenty, I moved out west when I switched colleges and began
classes soon after arriving. I shared off campus housing with three
other guys. One was a junior like me, and two sophomores. We each had
our own room and aside from casual conversation, we kept to ourselves
for the first couple months but within the second semester, I knew I
had to move out. The other junior was an ass and totally disrespectful
of everyone else and one of the sophomores had a drug problem and often
didn't have money for bills.
I had managed to get a good job as an entry level data entry clerk and
moved out into my own place at the end of the second semester. It was a
one bedroom apartment in a nice community and I was much better off. It
cost me more but I was making enough to take care of it since my loans
were handling my education expenses. And this all worked out until
summer break when they cut my hours at work. I was supposed to be
getting more but they hired some interns and paid them less and cut the
three most recently hired people's time. I guess they did that every
summer to help out other college students that wanted part time work in
the summer. Oh well, no biggie but that lowered my income a lot.
So I started looking for a new place to live but as luck would have it,
one of the interns, Jack, needed a new home so we agreed to share some
bills for the summer. He was only here for that long and that was all I
needed because in the fall I would be back to my normal schedule. So
all was good. And, as he had said, he wasn't there much anyways. He
usually stayed at his girlfriends place. They were moving in together
at the end of the summer and he just wanted somewhere to crash once in
a while. His old place he had to move out of because he couldn't afford
it anymore.
About my personal life, I didn't have much of one. I dated rarely
mainly because I just didn't have the time between school and work. I
was in decent shape although a bit on the shorter side and not ugly but
not handsome, kind of plain. The last date I had was with a man (yes I
am bi). He was much older than me (35) and a nice guy but he never
called me back. That was in April. Now that summer was here, my class
load was light and work was less so I went out more. I found a couple
good clubs and did some flirting. Had a date with a girl named Melinda
but it didn't go too well. She was nice looking and all but just
nothing in the brains department. Sure, I had sex with her but that was
it. I didn't call her back.
It was early July and I was out at a club having fun with a couple
friends when a guy subtly was flirting with me. This was a "straight"
club too so I was shocked. He was discrete though and made sure my
friends wouldn't catch on. The night went on, and he continued his
pursuit. He was nice and funny and kind of cute, maybe a few years
older than I. I gave him my number and said to call me sometime. And he
did two days later. We agreed to go to the same club that night, no
friends this time. We stayed there for a couple hours then went to
another club; this one was catered to anyone at all. Never been there
before but it was a cool place and the people were all laid back. By
midnight he was whispering in my ear that he wanted to fuck me. I was
tipsy, but that made no difference really, as I would have agreed if I
was sober.
We went to my place because it was closer and Jack was away for the
weekend camping. He had time to compliment me on a nice place before I
had his dick out and in my mouth. He liked that and he came in my mouth
in a matter of minutes. I fixed us a couple drinks and got changed into
just my boxer shorts and we sat and bullshitted for a little while
until I went down on him again. This time, after my shorts were ripped
off, we 69'd until we both came. Then we finally made it to my bed
where we had wild passionate sex until the early hours of the morning.
His cock was nice and I hadn't had one inside me in a couple years. And
he made it last too. He pounded me good though. Once then, and then
again in the morning.
He gave me his number then said his goodbyes. I was in a great mood. I
hadn't had sex of any kind in months and last night was wonderful. His
name was Larry and we stayed in touch and got together a couple more
times. He was a nice guy but forceful in bed and that was new to me but
a turn on. He liked to be a little rough and tell me what to do but it
was all in fun. Then we got caught by Jack. He was supposed to be in
Vegas. I didn't hear him come in right away. Not that we were far, I
was on all fours doggy style with Larry jamming into me. It wasn't
until I heard Jack's voice cry out that I knew he was there. Larry
stopped briefly, looked at him, and then went back to fucking me. I
tried to get him to stop but he wouldn't.
I begged for him to but he wouldn't let me go, instead he went faster.
Finally he shot his cum into me, smacked me on the ass gently and
gathered his clothes to get dressed. He introduced himself to a shocked
looking Jack with a smile. He asked me to call him again sometime and
left. Jack sat down on the couch and looked at me as I scrambled to
find some clothes. He looked angry but all he said was come here and
suck him. I didn't move right away, not sure what to do, then he asked
again and this time added please. What the hell, why not? I thought.
I pulled out his cock and went to town on my roommate. Holy crap was
his dick bigger than I ever seen. Not huge, but probably about 7" and
thick. No wonder he had good luck with the girls. I was drooling as I
sucked on him and he was loving it too. He held my head and leaned
back. I kept him going for at least 20 minutes before I finally got him
off. He shot a gallon of cum into my mouth and I couldn't handle it
all. He quietly got up and went to his room, closing the door behind
him. I didn't see him until two days later. He was gone when I got up
and in his room or out any other time. When I did see him again, it was
early evening. I was doing some reading in my room when he came home
and straight to my door.
I ok'd him to come in and he approached the bed. He asked me to just go
along with him here and as I was confused, he bookmarked my page and
set my book down. Rolled me onto my stomach and I said something to
which he just shushed me. I heard and glanced back to see his pants
coming down then he reached to me and pulled my shorts and underwear
off me. He kneeled next to me and said to me, "I am going to fuck you
now" and he placed a pillow under my stomach raising my ass up a bit. I
felt some warm lube on my ass then slowly he entered me. My god, it
felt so big! It hurt so damn much but there was no way he was stopping.
I even whined some and he kept pushing. Once all the way in and
adjusted, he began pumping me with that monster of his. It still hurt
but damn did it feel good too. He lasted about 10 minutes and after he
filled me up he said to wait here as he left. About a half hour later
he came back and did it again. This time faster and harder. For the
second time that hour, he filled my ass with his cum.
He thanked me and went to his room. I was still a little surprised but
all the same, it was fun! I never thought of him in any way like that
but now was glad he caught us. Not only was his cock nice sized, he was
a good lover too. I slept well that night and the next day was even
more of a shock. I came out of the bathroom and was putting some Pop-
Tarts in the toaster when he came in the front door. Was he was out
early. I said hi and he smiled and asked me to have a talk. I can only
imagine what this was about. I was close but not entirely what I
thought. This is what he said.
Jack: "George, I know we only barely know one another. Only a couple
months ago we met. You agreed to let me stay here when I needed a
place. Yes, you needed the help but you didn't have to let me. You
could've looked for someone else. I thank you for that. No, wait, let
me finish. I came home early the other night because I broke up with
Dani, the reasons don't matter why. I was pissed off as hell and was
only coming home to drop off some stuff, change, and go out and get
drunk. Maybe find a chick to bang."
He got up and grabbed some orange juice from the refrigerator before
continuing. He looked nervous but not scared.
Jack: "What I saw confused me a lot. I didn't know you were gay or bi
or whatever. Not that it matters to me; I don't care one way or the
other how someone lives to tell the truth. Just didn't expect to see
you getting plowed on our living room floor."
I blushed.
Jack: "I was angry, but not with you, and confused. When your friend
left I was still in shock. I still am not sure why I asked you to do
what you did, it just popped in my head. I have to say, that is the
first time a guy has blown me and you did fantastic. You're real good
at it."
I blushed more.
Jack: "I thought about it a couple days, playing that evening over and
over, and found I wanted to tag that ass of yours too. I don't know
where that came from but honestly, when I saw you that night from
behind, I would have sworn you were a girl. You have a fine butt and
yesterday I decided I wanted it. I thank you for going along with it
and letting me fuck you. Truthfully, you're a fine lay!"
Ok, I didn't think it was possible but I got even redder.
Jack: "But here is the thing. I would love to do that more but I don't
know if I can as it currently stands. I will admit, I must be a little
bi-sexual yet still it isn't all that comfortable. How would you feel
about being a girl?"
Me: "Uh, what?"
Jack: "Not totally, like in surgery. Just dress like one at home. Ever
thought about it?"
Me: "Not really, no."
Jack: "I tell you what, hear me out. I have thought about this a few
days and not sure how it will work but this is what I have come up
with. Now that Dani is gone, my parents will put me back on my
allowance. Yes, you had no idea my family is rich but they are but they
cut me off when I started dating her. Don't worry why, it isn't
important. But I have money again. I will support us. I will pay the
rent and the bills, even get a bigger place if you want, buy you
clothes, set you up nice. In return, you will be my girlfriend. I am
still not sure why this is so exciting to me but in only four days, my
life has radically changed and I want you."
Wow, this was too much. What was I going to do?
Jack: "It is a lot to absorb so take a couple days to think it over. I
will stay away at a hotel and come back after the weekend. Let me know
then. If you say no, all is cool. No harm no foul. Just wanted to offer
this. I can't promise anything long term at all. Hell, it may only last
a month. But it would at least be a new experience for us both and you
can start to save up some cash. Well, I will grab some things and head
out. See you Monday."
He did just that. Grabbed some stuff in a suitcase and smiled as he
left. I was still stunned by the proposal and sat there for some time
with many thoughts rummaging around through my mind. I never even
thought about doing anything like he said. Dress like a girl? Be his
girlfriend? It was all a bit surreal. I had to let it sink in. I spent
the next couple days trying to occupy my mind with things but all too
often, the conversation broke through to the forefront. I found myself
weighing the pros and cons and always the pros won. But it was such a
huge step. Would I do it? Could I do it?
Come Monday, I still was on the fence but leaning towards agreeing. It
was shocking but deep down, it was thrilling as well. I got home and
found a note on the table from Jack. It read:
George,
I was here earlier but only briefly and just long enough to leave this
note and pack a small bag. I have to make a short trip to visit my
parents for a few days but should be back by Saturday. Sorry. I know I
said I would return today but this has to be taken care of. I left you
a present on your bed. I will see you when I return.
Jack
The gift he mentioned was a wooden chest, like a foot locker, and
inside was a mixture of women's clothing. All manner of outfits from
slutty to seductive to prim and proper. All in my size. Also in there
was an envelope containing $1,000 cash with a short note saying:
I hope you enjoy the present. Use them or not, it is your choice. The
money is mostly for my share of the bills plus some for you to get your
car fixed. It is not intended as anything but one friend helping
another. No strings attached.
He was right; I did need to get my car worked on desperately. After
paying the bills and getting my car fixed, I had about $150 left over
which I put back in the envelope. Also, I could not help it but I spent
the next few days experimenting with the clothing. I found I liked it
which I am not sure if I was surprised by that or not. Each night I
dressed in something different and when I slept, I wore sexy nighties,
teddies, or just panties and a bra. I was quickly falling into a new
world.
I awoke Saturday morning with a light pink baby doll nightie on with
lace pink panties. I was smiling when I went to get some orange juice
from the kitchen. I showered and changed into jade green bra and
panties, a black knee length skirt, a grey short sleeved sweater with a
short zipper in the front, my favorite light auburn, long haired wig,
pantyhose, and 3" black heels. It all felt so good, especially since a
couple days ago I shaved my body for the first time ever. I was in my
room when I head the door open and close and came out to see Jack
there. His eyes went wide when he saw me and barely had a chance to say
hello before my lips pressed against his for a moment then I said
'Yes'.
I had played out this scenario since Thursday many times in my mind and
now onto the second part as I knelt in front of him, taking his cock
out of his pants, and gave him a blow job. He just leaned against the
door and moaned until I finished up. I rose, wiping my mouth, and said
'I am Holly, welcome home honey' with a big smile.
That ends part one. More on its way.