FionaFortune
10-01-2023, 11:38 PM
Part One
by Fiona Fortune
I want to hear from you about this story whether you like it or want to try it again with me.
Now on to the story. Let me set the scene.
My name is Mike, as a "Gurl" I go by Fiona. I am a gay man, late thirties,
white, 5' 9' 165, reasonably handsome, both in and out of women's clothes.
One of the ways I express my sexuality is to dress as a woman and get fucked by
other men. Preferably in a humiliating situation, with several guys fucking me.
Just one of my kinks.
~
This night was the second time I had gone with Anthony. The first time was
the Friday Night before.
I dressed in 3 inch heels, fishnets, black garter with thong panties over
them, a black latex mini, a black leather corset which reduced my waist 5 inches
to 27" and gave me a very sexy hourglass shape.
On top a Black Sports Bra 40C with falsies and over that a sheer black
see-through blouse. Curly Auburn Wig.
That night I was cruising the downtown Portland's Fantasy Adult Book Store
Video Booths, looking for cock.
He came up behind me as I sashayed down the corridor of the booths licking
my lips, he slapped my
ass and said in my ear "Bitch, the only way that mouth could look hotter is
if my cock was in it".
I turned, smiled and said "No, it would be hotter if your cum was on these
lips too", as I groped his crotch.
Nice package, heavy balls, flaccid, his cock was about the width of a Red
Bull can, I judged it to be eight or nine inches long.
Jackpot !, Good enough for me by half. When I hit the ABS, I just go to get
whatever cock comes my way,
not a size queen at all, just love to be dressed and on my knees or bent
over for any man.
He then steered me into a booth, I put a five in and picked out a tranny
vid, I dropped to a squat in front of him
and started tearing at his belt and zipper. "Whoa bitch, Take your time" He
said. I looked up into his brown eyes,
Licked my lips and just smiled. He the undid them and pulled his boxers
down. Nice! It flopped out out onto my face.
Darkest Ebony, with a foreskin, half erect, but at least eight inches long,
leaking a big drop of pre-cum.
I Opened wide and quickly deep throated all I could, 6 or so inches, in one go. As I did
that I just heard him take a very deep breath and let out a deep "Ahh, damn bitch".
I then went work, both hands twisting on it for a bit while I suctioned the head.
Then I moved the hands to scratch/flick the skin of his balls as I took it all the way
down. I heard another deep "Ahhh Damn" as I sunk my nose into his curly black
pubic hair, while tonguing the base of his balls, the full way in, deep throating the whole thing.
Not to brag, but after much practice, I have learned to suppress my gag
reflex and use my deep throat muscles to milk even the biggest cocks. I pulled
him all the way out, then slowly took the fully engorged prick into my mouth and
once again suctioned the underside while flicking my tongue over the
sensitive underside and slowly swallowed the whole thing again and again.
Fully erect now, it had to be 10 inches long and It curved downwards near
the head. A big damn cock !
I pulled off it and stared at the thing it all it's erect glory, Wow,
jackpot indeed. This time I just relaxed and went for it, deep
throating the whole thing in one go. He was in heaven as my skilled throat
milked his manhood. I heard a steady stream of
"Ahhs and Damn Bitches" I felt his approaching climax as he started to
tense. I had to act fast as I wanted him to cum in my ass
not mouth. I pulled off quickly and tightly pulled down on his balls. That
did it, it derailed his orgasm for the moment. He looked
down and "Hey bitch, thanks, I was on the edge there". I said " no worries,
I want to savor this too".
I reached into my purse and took out a packet of lube and a maxxum (I keep
for special ones), I lovingly rolled the condom down
and turned, lubed up and bent over in anticipation. I was hoping the size
of his cock and the downward curve would massage my prostate
wonderfully. He lifted my latex mini, pulled the thong to one side and
presented his gorgeous man meat to my whore hole. Unnghh!
I felt the huge black cock push it's way in, pain, I tried to relax and
push out but he was either new at fucking ass or didn't care about my
pleasure.
He pushed about 3/4 of the way in, stopped, grabbed my waist, then forced
it the rest of the way in. He said "Balls Deep, Bitch, you like that?"
"Unngh!" was all I could mutter as I concentrated on relaxing my whore
hole. He just laughed and began to long dick me. after a minute or two the
pain washed away and was replaced by sheer electricity as my pussy crackled
in ecstasy at the huge intruder's thrusts. Boy was I right, the downward
curve on his massive member hit my prostate just right.
It was Bitch Butt Bliss as his dick dominated my asspussy. I reached down,
pulled my cock out of the thong panties and began stoking like mad. Fuck yes !!,
this is what I live for, being ass reamed by a black beast in a bookstore booth.
He kept up the long strokes, eventually pulling all way out and watching my hole
gape for a moment and then snap back a bit. He would then ram it all way
in, balls deep.
Fuck, all of it in one go, my hole was reamed and wrecked. He then started
to pick up the pace again, "Thap, Thap Thap" his balls banged against mine
as he
butt banged me. I was really feeling it too, and from somewhere down deep,
my orgasm started to build. The spasms started small, a quiver in my queef,
but they
built on themselves and soon I was uncontrollably jerking around like a
pinball, stroking my rod for dear life all at the same time. The spasms
contracted my
reamed rosy ringlet very hard as well, literally squeezing the massive cock
thrusting inside me like a juice orange in the hands of a giant. "Damn
bitch, you
gonna make me nut" was all I heard as my orgasm flowed over me and I
squirted blast after blast of hot jizz on the booth floor. I then felt an
iron grip on my
waist and he went all in, nuts to nuts and held it there as he unleashed
his orgasm too. I felt white hot spurt after spurt, shoot inside me as he,
the macho man,
let out a funny 'ahh ooh' kind of squeek as his climax subsided. Whoa, I
steadied myself against the wall as the last of his man cream emptied into
my pussy.
He pulled it out, ripped off the condom and looked kind of sheepish, shy
even. I said "man that was nice, we should do that again. Can you get it
up ?"
He didn't say anything back, just looked kind of blissed out. Oh Well, I
thought to myself.
I began to rearrange and clean myself, after a bit, I was ready to get out
of the booth.
I wrote down his info and then handed him my card (phone and email). I
only give it to guys I would mind seeing again. I send out emails notifying
"my list", when and where I play. This has made for many memorable almost
"Gangbang" nights (well at least 10 partners, if not all at once). He was
still a bit
stunned at that point and I left. I blew a couple more guys at Fantasy
booths and then things died down. From there, I caught the drag show at
Embers.
Sucked off a tranny chaser in his car in the parking lot across from
Embers. After Embers closed, I hit the Paris theater. That was kind of dead
too. Although I did
give 2 more blowjobs before I called it a night.
Fast forward to the next Friday night. I got home from work around 6pm,
showered, shaved, enema-d and got dressed. 3 Inch Heels, black nylons,
garter belt,
pink thong worn over the garter, Black leather mini, Black leather corset,
Black sports Bra with Falsies 40C and over that a sheer black see-through
blouse plus on top, a curly long Blonde Bimbo wig. I checked my "FionaFucked"
email before heading out and, lo and behold, an email from Anthony.
The email said he wanted to see me tonight with a group of his friends,
err, gang.
I found this quite odd because he seemed a straight acting, macho dude who
would rather be caught dead, than be seen with a gay man or transvestite.
So I called him up, he explained that he was in a group, as one part of the
initiation rites each of them had to fuck a tranny in front of the others
to mentally prepare for them for
the possibility of prison. Since tranny sex would be the only sex they
would get in there if they were caught. That sounded reasonable, but still,
those type of guys seem hyper-macho and anti-gay.
He said in their world, the shame was on the person being penetrated. Okay,
but I asked, why me ? Didn't they have a regular "gurl" for these things ?
He said "She" was
currently doing a 90 day stretch at Inverness Jail. I was still very unsure
about it though, we went round and round about it for a while, and finally
I got an assurance of complete
security, a hard rule of condoms required for all anal and a $500
payment. Still, I was a bit worried, but also rock hard excited. I really
get off on gangbang scenes, being
used by a group of guys, being banged at both ends gets me off so well. I
have had more than my share of gangbang scenes over the years and I always
fucking love it.
Anyway, he gave me the address and said be there in 2 hours.
Good, That gave me some time to work on opening my pussy and throat, I
worked from medium to my biggest dildos being careful not to cum yet. The
anticipation was very titillating
and I felt my pussy tingling, ready for almost anything. The time came and
I cabbed it, first stopping for a few boxes of condoms, normal to Maxxum,
then over to the address on
NE Ainsworth near MLK. The cab driver laughed derisively as we pulled into
the home's driveway and Anthony came out to meet me. I brazenly said back
to him "I know what you
are thinking, It's true and I am going fucking love every minute of it,
bitch". He kind of looked shocked after I said that. I paid him with a
smile and a lick of my lips. Anthony then paid me,
and we reiterated the rules - condoms for all anal, then he walked me to
the backyard where about 7 guys were milling around listening to beats and
chilling.
All eyes were on me as I entered the backyard. With my 3 inch "Fuck Me"
heels, leather mini, corset, and Blonde Bimbo wig, I looked ready to ride
and then some. I felt quite scared walking into this lion's den, but my
excitement at the possibilities drove me to slut it up, I suggestively licked
my lips and swayed my ass, as Anthony led me
through the yard to a wooden chaise lounge chair. I sat on edge of it and
was immediately at crotch level. Anthony then said "Get to work Bitch" as
he undid his pants and pulled
down his shorts, freeing his mammoth meat. I then just did what came
naturally to me. I relaxed my throat and took 3/4 of it down in one
go. "Bitch got Skillz" was what heard next
as I worked on that huge cock. All eyes glued to me now, I love an
audience. I concentrated relaxing my throat even more, then looking into
his eyes, I took him all way down, nose
buried in his pubes while working the balls with both hands. My technique
was to begin with taking a breath - suction on the head, then swallowing it
whole while milking it with my
throat muscles, after 3 minutes of this I could feel the cock grow to it's
maximum 10 inches while becoming cement hard. Then unexpectedly, while my
nose was buried Anthony
grabbed my head with both hands and held it while he blasted off streams of
hot white man juice down my throat. He held me there Impaled, for about 45
seconds and I was beginning
to really struggle for breath when at last he finally let up. I pushed off
just as the last spurt landed on my lips. "Ahh, Fuck Yeah Bitch" he said as
I licked my lips of the cum for all to see,
damn that tasted sweet. After that, all 7 of the remaining guys pushed
forward cocks in hand. "Jackpot Bitch!" I thought to myself, Black Cock
Heaven for me!
by Fiona Fortune
I want to hear from you about this story whether you like it or want to try it again with me.
Now on to the story. Let me set the scene.
My name is Mike, as a "Gurl" I go by Fiona. I am a gay man, late thirties,
white, 5' 9' 165, reasonably handsome, both in and out of women's clothes.
One of the ways I express my sexuality is to dress as a woman and get fucked by
other men. Preferably in a humiliating situation, with several guys fucking me.
Just one of my kinks.
~
This night was the second time I had gone with Anthony. The first time was
the Friday Night before.
I dressed in 3 inch heels, fishnets, black garter with thong panties over
them, a black latex mini, a black leather corset which reduced my waist 5 inches
to 27" and gave me a very sexy hourglass shape.
On top a Black Sports Bra 40C with falsies and over that a sheer black
see-through blouse. Curly Auburn Wig.
That night I was cruising the downtown Portland's Fantasy Adult Book Store
Video Booths, looking for cock.
He came up behind me as I sashayed down the corridor of the booths licking
my lips, he slapped my
ass and said in my ear "Bitch, the only way that mouth could look hotter is
if my cock was in it".
I turned, smiled and said "No, it would be hotter if your cum was on these
lips too", as I groped his crotch.
Nice package, heavy balls, flaccid, his cock was about the width of a Red
Bull can, I judged it to be eight or nine inches long.
Jackpot !, Good enough for me by half. When I hit the ABS, I just go to get
whatever cock comes my way,
not a size queen at all, just love to be dressed and on my knees or bent
over for any man.
He then steered me into a booth, I put a five in and picked out a tranny
vid, I dropped to a squat in front of him
and started tearing at his belt and zipper. "Whoa bitch, Take your time" He
said. I looked up into his brown eyes,
Licked my lips and just smiled. He the undid them and pulled his boxers
down. Nice! It flopped out out onto my face.
Darkest Ebony, with a foreskin, half erect, but at least eight inches long,
leaking a big drop of pre-cum.
I Opened wide and quickly deep throated all I could, 6 or so inches, in one go. As I did
that I just heard him take a very deep breath and let out a deep "Ahh, damn bitch".
I then went work, both hands twisting on it for a bit while I suctioned the head.
Then I moved the hands to scratch/flick the skin of his balls as I took it all the way
down. I heard another deep "Ahhh Damn" as I sunk my nose into his curly black
pubic hair, while tonguing the base of his balls, the full way in, deep throating the whole thing.
Not to brag, but after much practice, I have learned to suppress my gag
reflex and use my deep throat muscles to milk even the biggest cocks. I pulled
him all the way out, then slowly took the fully engorged prick into my mouth and
once again suctioned the underside while flicking my tongue over the
sensitive underside and slowly swallowed the whole thing again and again.
Fully erect now, it had to be 10 inches long and It curved downwards near
the head. A big damn cock !
I pulled off it and stared at the thing it all it's erect glory, Wow,
jackpot indeed. This time I just relaxed and went for it, deep
throating the whole thing in one go. He was in heaven as my skilled throat
milked his manhood. I heard a steady stream of
"Ahhs and Damn Bitches" I felt his approaching climax as he started to
tense. I had to act fast as I wanted him to cum in my ass
not mouth. I pulled off quickly and tightly pulled down on his balls. That
did it, it derailed his orgasm for the moment. He looked
down and "Hey bitch, thanks, I was on the edge there". I said " no worries,
I want to savor this too".
I reached into my purse and took out a packet of lube and a maxxum (I keep
for special ones), I lovingly rolled the condom down
and turned, lubed up and bent over in anticipation. I was hoping the size
of his cock and the downward curve would massage my prostate
wonderfully. He lifted my latex mini, pulled the thong to one side and
presented his gorgeous man meat to my whore hole. Unnghh!
I felt the huge black cock push it's way in, pain, I tried to relax and
push out but he was either new at fucking ass or didn't care about my
pleasure.
He pushed about 3/4 of the way in, stopped, grabbed my waist, then forced
it the rest of the way in. He said "Balls Deep, Bitch, you like that?"
"Unngh!" was all I could mutter as I concentrated on relaxing my whore
hole. He just laughed and began to long dick me. after a minute or two the
pain washed away and was replaced by sheer electricity as my pussy crackled
in ecstasy at the huge intruder's thrusts. Boy was I right, the downward
curve on his massive member hit my prostate just right.
It was Bitch Butt Bliss as his dick dominated my asspussy. I reached down,
pulled my cock out of the thong panties and began stoking like mad. Fuck yes !!,
this is what I live for, being ass reamed by a black beast in a bookstore booth.
He kept up the long strokes, eventually pulling all way out and watching my hole
gape for a moment and then snap back a bit. He would then ram it all way
in, balls deep.
Fuck, all of it in one go, my hole was reamed and wrecked. He then started
to pick up the pace again, "Thap, Thap Thap" his balls banged against mine
as he
butt banged me. I was really feeling it too, and from somewhere down deep,
my orgasm started to build. The spasms started small, a quiver in my queef,
but they
built on themselves and soon I was uncontrollably jerking around like a
pinball, stroking my rod for dear life all at the same time. The spasms
contracted my
reamed rosy ringlet very hard as well, literally squeezing the massive cock
thrusting inside me like a juice orange in the hands of a giant. "Damn
bitch, you
gonna make me nut" was all I heard as my orgasm flowed over me and I
squirted blast after blast of hot jizz on the booth floor. I then felt an
iron grip on my
waist and he went all in, nuts to nuts and held it there as he unleashed
his orgasm too. I felt white hot spurt after spurt, shoot inside me as he,
the macho man,
let out a funny 'ahh ooh' kind of squeek as his climax subsided. Whoa, I
steadied myself against the wall as the last of his man cream emptied into
my pussy.
He pulled it out, ripped off the condom and looked kind of sheepish, shy
even. I said "man that was nice, we should do that again. Can you get it
up ?"
He didn't say anything back, just looked kind of blissed out. Oh Well, I
thought to myself.
I began to rearrange and clean myself, after a bit, I was ready to get out
of the booth.
I wrote down his info and then handed him my card (phone and email). I
only give it to guys I would mind seeing again. I send out emails notifying
"my list", when and where I play. This has made for many memorable almost
"Gangbang" nights (well at least 10 partners, if not all at once). He was
still a bit
stunned at that point and I left. I blew a couple more guys at Fantasy
booths and then things died down. From there, I caught the drag show at
Embers.
Sucked off a tranny chaser in his car in the parking lot across from
Embers. After Embers closed, I hit the Paris theater. That was kind of dead
too. Although I did
give 2 more blowjobs before I called it a night.
Fast forward to the next Friday night. I got home from work around 6pm,
showered, shaved, enema-d and got dressed. 3 Inch Heels, black nylons,
garter belt,
pink thong worn over the garter, Black leather mini, Black leather corset,
Black sports Bra with Falsies 40C and over that a sheer black see-through
blouse plus on top, a curly long Blonde Bimbo wig. I checked my "FionaFucked"
email before heading out and, lo and behold, an email from Anthony.
The email said he wanted to see me tonight with a group of his friends,
err, gang.
I found this quite odd because he seemed a straight acting, macho dude who
would rather be caught dead, than be seen with a gay man or transvestite.
So I called him up, he explained that he was in a group, as one part of the
initiation rites each of them had to fuck a tranny in front of the others
to mentally prepare for them for
the possibility of prison. Since tranny sex would be the only sex they
would get in there if they were caught. That sounded reasonable, but still,
those type of guys seem hyper-macho and anti-gay.
He said in their world, the shame was on the person being penetrated. Okay,
but I asked, why me ? Didn't they have a regular "gurl" for these things ?
He said "She" was
currently doing a 90 day stretch at Inverness Jail. I was still very unsure
about it though, we went round and round about it for a while, and finally
I got an assurance of complete
security, a hard rule of condoms required for all anal and a $500
payment. Still, I was a bit worried, but also rock hard excited. I really
get off on gangbang scenes, being
used by a group of guys, being banged at both ends gets me off so well. I
have had more than my share of gangbang scenes over the years and I always
fucking love it.
Anyway, he gave me the address and said be there in 2 hours.
Good, That gave me some time to work on opening my pussy and throat, I
worked from medium to my biggest dildos being careful not to cum yet. The
anticipation was very titillating
and I felt my pussy tingling, ready for almost anything. The time came and
I cabbed it, first stopping for a few boxes of condoms, normal to Maxxum,
then over to the address on
NE Ainsworth near MLK. The cab driver laughed derisively as we pulled into
the home's driveway and Anthony came out to meet me. I brazenly said back
to him "I know what you
are thinking, It's true and I am going fucking love every minute of it,
bitch". He kind of looked shocked after I said that. I paid him with a
smile and a lick of my lips. Anthony then paid me,
and we reiterated the rules - condoms for all anal, then he walked me to
the backyard where about 7 guys were milling around listening to beats and
chilling.
All eyes were on me as I entered the backyard. With my 3 inch "Fuck Me"
heels, leather mini, corset, and Blonde Bimbo wig, I looked ready to ride
and then some. I felt quite scared walking into this lion's den, but my
excitement at the possibilities drove me to slut it up, I suggestively licked
my lips and swayed my ass, as Anthony led me
through the yard to a wooden chaise lounge chair. I sat on edge of it and
was immediately at crotch level. Anthony then said "Get to work Bitch" as
he undid his pants and pulled
down his shorts, freeing his mammoth meat. I then just did what came
naturally to me. I relaxed my throat and took 3/4 of it down in one
go. "Bitch got Skillz" was what heard next
as I worked on that huge cock. All eyes glued to me now, I love an
audience. I concentrated relaxing my throat even more, then looking into
his eyes, I took him all way down, nose
buried in his pubes while working the balls with both hands. My technique
was to begin with taking a breath - suction on the head, then swallowing it
whole while milking it with my
throat muscles, after 3 minutes of this I could feel the cock grow to it's
maximum 10 inches while becoming cement hard. Then unexpectedly, while my
nose was buried Anthony
grabbed my head with both hands and held it while he blasted off streams of
hot white man juice down my throat. He held me there Impaled, for about 45
seconds and I was beginning
to really struggle for breath when at last he finally let up. I pushed off
just as the last spurt landed on my lips. "Ahh, Fuck Yeah Bitch" he said as
I licked my lips of the cum for all to see,
damn that tasted sweet. After that, all 7 of the remaining guys pushed
forward cocks in hand. "Jackpot Bitch!" I thought to myself, Black Cock
Heaven for me!