My Girlfriend Samantha
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A Boy Named Samantha free porn video
A Boy Named Samantha
by Deborah
I'm sure everyone who has attended a high school reunion has been
shocked for one reason or another. Some people change dramatically and
lives take directions no one ever would have predicted.
My five-year high reunion became quite the revelation. One of my best
buds in high school made a stunning entrance in a black strapless, side-
shirred and dramatically slit tulip-wrap dress. Sam looked gorgeous in
that dress and much better than I ever could have. But his name wasn't
Sam now; it was Samantha.
Where to start? Sam and I shared many interests back then, particularly
computer stuff. I knew he liked boys better than girls, sexually
speaking. Very pretty for a guy, he had a high pitched voice and the
jocks teased him incessantly. I figured Sam would end up a priest,
what with being Catholic and all. We lost touch in the years after we
graduated. He ended up on the left coast and me on the east coast.
Sam did visit me once in college and helped me reap revenge on those
who initiated my brief career in the world's oldest profession. But
that's a story for another day (Entitled "Revenge of the Coeds.")
I'm standing at the bar at the reunion chatting with a couple old
girlfriends when this what I thought to be a runway model approached me
and asked if we could speak privately. I saw the nametag "Samantha
Harrison." The only Harrison at our school was Sam the dude. My
initial reaction was that this was his wife, although I never figured
Sam for the marrying kind.
A Holiday Inn hosted the reunion. I let Samantha lead me out of the
banquet room and into the lobby. She dragged me onto the elevator and
pushed the button for the fourth floor.
"I simply must talk to you privately," Samantha insisted as we entered
her room.
A bottle of Glenmorangie sat in the ice bucket just waiting to be
opened. So I did. Glenmorangie, "Crafted by the 16 men of Tain," the
best selling Scotch Whiskey, at least in Scotland. I can't believe I
drank the whole thing. Well, most of it. Samantha had a couple shots.
I needed something to dull my senses. Our conversation turned out to
be more than I could handle sober.
"Deborah," Samantha began, "I don't know how to explain this to you.
Maybe we'll just play 'show and tell.' That way you will have no choice
but to believe me.
I just nodded, having no idea what in the hell she might be talking
about, but becoming incredibly curious.
"You know, Samantha," I observed, "You remind me so much of the
supermodel Frederique; about 5'11" and somewhat big-boned for a girl
with large hands and feet and a deep voice. Frederique is a native of
Holland but is now the quintessential New Yorker. She has done many
'Cosmo' covers, Victoria Secret catalogues, been on Letterman and Oprah,
and my fav, the Howard Stern show. I just love it when the ladies, and
it doesn't happen often, hold their own with Howard and don't just get
giddy and nekkid. Frederique more than held her own."
"You think I'm pretty then, Deborah?"
"Samantha, you are a total fox. Geez, I wish I looked like you."
"Oh yeah, well I always thought you to be the best looking girl in our
class and you still are, from what I saw of the other women at the
reunion."
"Say what, Samantha, you weren't in my class. How could I ever forget
you?"
"Yes, Deborah, I was."
"I don't understand, Samantha. Are you pulling my leg?"
"Nope, but if you pull my leg maybe you will understand."
Samantha unclipped her tulip-wrap dress and fully exposed the lace-top
thigh-highs. I noticed an unusual bulge in her stretch string thong.
No, it wasn't black; the color was "serpent purple." I knew because I
had the same thing in my lingerie drawer. At first I could only guess
the bulge might be a Kotex maxi pad or some such thing.
Soon I discovered the reason for the bulge. Samantha pulled down her
thong and revealed quite a nice looking large penis, about seven inches
soft. I felt faint for a moment and simply could not speak.
When I caught my breath I didn't know what to say so I began singing
lyrics from "A Boy Named Sue" by Johnny Cash ?
"Well, he must o' thought that it was quite a joke. And it got a laugh
from a lot of folk. It seems I had to fight my whole life through. Some
gal would giggle and I'd get red And some guy'd laugh and I'd bust his
head. I tell ya, life ain't easy for a boy named Sue."
"It's real, Deborah. You can touch it if you like."
I couldn't resist. I touched it. Then I began to stroke it as it
became erect and expanded to about ten inches. Obviously my
overwhelming curiosity now demanded that I see "her" breasts.
"Please let me see your breasts, Samantha."
Samantha pulled down the top of the strapless dress to reveal her
beautiful melons; very full and firm and her nipples were quite erect,
which I assumed my stroking her cock precipitated.
"I'm beginning to get the picture here, Samantha. You are Sam. And
just how in the hell did that all happen?"
"Do you really want to know?"
"You are fucking right I want to know. This is incredible. Now tell
me!"
"Would you suck my cock first? You are making me horny. Besides, I
probably won't have this cock much longer, if you get my drift."
"Well, I never sucked a girl's cock before. How come you never asked me
to suck your cock when you were a dude?"
"Deborah, you knew me way back when. Just too damn shy I guess.
Actually, a girl has never ever sucked my cock. Just guys."
"You know, Samantha, this is a really nice cock. One of the best I've
seen. Why would you want to part with it?" I began to nibble. "And
it tastes good!"
"I want to be totally a woman and experience everything that a woman
experiences. My doctor tells me that after the Sexual Reassignment
Surgery it is quite possible I may be able to orgasm just like you do.
I know that sounds incredible but that's what the experts say. My
doctor told me he will take sensitive tissue from my penis and use it
to create my vagina and clitoris, which will hopefully provide a degree
of erotic sensation. Exactly what degree of sensation, of course,
won't be known until some time after the operation. Some 'new' women
have no capacity for orgasm and others get off big time. Here's
hoping!" Samantha gleamed as she downed a shot of the Glenmorangie.
"Now, you promise, Samantha, if I suck your cock you will tell me
absolutely everything about this? I mean, you look so much like a
woman, who would ever know. Well, except for this!" I deepthroated
her cock. My pussy was becoming very moist because of this incredibly
strange and erotic experience.
"Samantha," I asked as I momentarily removed her cock from my mouth,
"have you ever had sex with a woman?"
"No, and I don't think I want to, at least not sexual intercourse."
"But you have had anal intercourse with guys?"
"Yes, I have, Deborah."
"OK, pretend I'm a guy and fuck me in the ass."
"Huh?"
"You heard what I said. If you want to get off, fuck me in the ass."
I laid face down on the bed and stuck my butt up in the air, and pulled
up the bottom of my blue velvet slipdress. Samantha had an open
invitation because there were no panties under the dress, just knee-
high fishnets. The Analeze had already been applied liberally. I had
to help Samantha find the right angle and eased her into me an inch at
a time with one hand, playing with my clit with the other hand. If you
can't figure that one out, just let me inform you I have very long arms
and I'm double-jointed. I can do some very weird things with my body.
Ten minutes later Samantha pulled out and shot hot cum all over my
behind while I moaned in post orgasmic ecstasy due to the butt fucking
and my own ministrations with my own fingers. Samantha had done it
just right. Girls are so much gentler when they stick it up your ass.
"OK, Samantha, I got you off. Now tell me all the juicy details. How
did you learn to act so much like a girl? Somebody taught you the
ropes."
"Hey, I read 'Creating a Feminine Carriage: Figure, Posture, Walk, &
Gesture' by Elaine Sagant. She is image and movement consultant to the
transgender community. Everything from bending and reaching to getting
in and out of cars in a ladylike manner. And I practiced with
girlfriends who are also suffering from Gender Dysphoria.
"Although as you know, I had a rather girlish face to begin with, I have
undergone considerable facial feminization surgery. A male and female
skull have basic differences, as any anthropologist will tell you. I
had orbital rim contouring to modify my forehead, cheek augmentation
utilizing implants, lower jaw chin surgery and thyroid cartilage
reduction for my Adam's Apple."
"What about your body?" I asked. "Your breasts are fantastic."
"You know, just the usual textured saline filled implants. Also a tummy
tuck, hip, thigh and leg suctioning, and of course electrolysis."
"Well, it's just extraordinary. I can't imagine anyone doubting you are
a woman, Samantha."
"Yes, Deborah, but for one important matter yet to be dispensed with."
She winked at me.
"Hey," I joked, "You could write a new tune for the Dixie Chicks, a
sequel to 'Goodbye Earl' entitled 'Goodbye Dick.' Are you going to
have a funeral or something for your dick? How do you say 'Goodbye
Dick' I wonder? Maybe you should see a taxidermist and get the sucker
stuffed."
"Great idea! Get it stuffed and stick it in my purse, and when someone
tells me to 'go fuck yourself' I pull it out of my skirt, lift my
skirt, and do it. That or get it pickled and exhibit it at the Tate
Modern for a million bucks."
"Geez, I wonder if Hallmark makes a card for this occasion, like 'Sorry
you lost your dick but glad you're now a chick' seems appropriate." We
both began giggling hysterically.
"They bury animals don't they?" Samantha questioned. "I think I should
bury my dick."
"No, no, let's slice it up for cocktail snacks! By the way, the proper
way to say farewell to your private anatomy is to make sure the doctors
keep you awake during the procedure and after they have snipped it and
are lifting it away with the crane start your most heartfelt rendition
of 'I'll be seeing you.' I don't even know what dysphoria means. Is
that the opposite of euphoria?
"And Samantha," I continued, "aren't you just a little concerned about
penis envy? And don't you watch Oprah? According to the he/shes on
Oprah recently, or trannys as the twit Brits call them, right before
the 'operation' they all went into a state of denial, which included
hallucinations. They all experienced nightmares and woke up screaming,
'Where's my dick?' Fortunately the drug Tehrahydrocannabinal
Flunitrazepam can be prescribed to mitigate this psychological trauma
known as MMM, Missing Member Mania."
Samantha wiped laughing tears from her eyes and got serious for a
moment. "There you go, pulling my leg again. I know what that TF drug
is; a combination of hashish and 'roofies,' you know the date rape
dope. What concerns me the most about all this is that I'll have to
pee sitting down."
"Yes indeed, the female anatomy is not conducive to standing. But at
least you won't have to stand in front of strangers peeing."
"Hey, I liked that part. Whenever a dude would look over at mine, I'd
say, 'Wanna shake my snake?' I got punched a couple times for that
one. Yeah, and I'll miss the graffiti over the urinals like, 'Don't
look up here, the joke's in your hand' and 'Don't throw toothpicks in ?
crabs can polevault.' Hey, I may have to pee sitting down, but no PMS,
unless it's psychosomatic."
"Let's go back down to the reunion," I suggested, my libido having been
somewhat diminished for the moment. My curiosity still overwhelmed me,
wondering if anyone else would suspect that this beautiful woman had a
big fat cock.
On the way down to the banquet room where the reunion was being held,
Samantha and I concocted a bullshit story. Sam had been killed six
months earlier, and Samantha, his wife, came to the reunion to meet all
his old friends.
We sat on bar stools sipping ice water because we passed off as straight
vodka. Like we weren't already trashed enough. Guy after guy hit on
us. Samantha gave them all the brush-off. She knew what she wanted;
Jimmy Joe Jefferson.
While we waited on Jimmy Joe's appearance, I continued to ask Samantha
questions about "her" past history.
"Samantha, obviously you didn't always look like a beautiful woman.
There must have been a transition period. Tell me about that."
"Well, if you insist. When I still looked more like a guy than a girl,
across the bridge from where I lived an old trailer had been converted
into an adult bookstore. It had everything there from magazines to
dildos to movies. Also it had my favorite; the booths.
"This place was run by some gay guys and they pretty much did not care
what went on as long as nothing happened that required the cops to be
called. I had been frequenting this place for a few months to buy
magazines and movies, and always wanted to go into the booths, but was a
little scared. Finally one night I made up my mind that I would do it.
"I got there about 1:00 AM and the place was packed. Guys stood along
the wall and I thought all the booths to be full so I stood next to one
door waiting. I reached to try the knob and the door opened. No one
inside. I went in and sat down and loaded up the machine with $5 worth
of quarters.
"On both walls in the booth were holes cut out just big enough for a
cock to slide through. Not being a virgin to sucking, I decided to
immediately show off what I was wearing. I stripped my clothes off and
stood there in a white bra and panties, feeling myself up when the
first cock came through the hole. Mind you I had imbibed in a
considerable quantity of alcoholic beverages before going that night,
so I felt pretty high.
"I sat back in the chair, crossed my legs and started playing with this
guy's cock; not all that big but pretty nice. After a few minutes, I
bent down and started sucking and it sure didn't take long for him to
cum, and then he just pulled up his pants quickly and left. I started
watching the movies again and soon someone entered the booth. The
first guy must have given this one the high sign because he wasted no
time in dropping his pants and sticking his cock through the hole. I
started sucking him when I heard someone knocking on the other wall. I
looked and had another cock on the other side sticking through. So
there's me in my bra and panties with two cocks to play with.
"I alternated sucking each one, but I needed some action too so I
slipped a condom to the one guy and he put it on. I bent to suck one,
dropped my panties to my knees and backed into the other guy. I took
it nice and slow into my butt, and he started pumping, as I continued
to suck the first guy. Let me tell you that was heaven! The guy I was
sucking shot his load in my mouth and when he left, I started playing
with myself while still taking it up the ass. Soon I came and I
quickly got dressed and left.
"Then this time I ?" Samantha paused. Jimmy Joe approached.
Jimmy Joe achieved considerable fame as the chief stud of our
graduating class. Quite the star athlete and really dumb shit. Rumor
has it he banged all twelve varsity cheerleaders and the forty year old
wife of the principal and cheerleader coach. Oh yeah, and Jimmy Joe
relentlessly harassed and humiliated the ultimate geek, my friend Sam.
Although Jimmy Joe's eight-month pregnant wife accompanied him to the
reunion, he still found it necessary to get him some strange stuff. He
had his eye on Darla, the homecoming queen who now stripped and did
porn, until he saw Samantha sitting on that barstool. Doing his
studmuffin routine, Jimmy Joe strolled on over and struck up a
conversation with Samantha.
"Hey, babe, you are hot! I already got the scoop on you. You are the
late Sam's wife. What did you do, fuck him to death? My condolences
but I can't believe a twerp like Sam got a foxy lady like you. What,
he had money?
Samantha played along. "Yes indeed he had money. But it's mine now."
They got real cozy. I moved over one barstool. Jimmy Joe put his hand
on Samantha's knee, and ran it right up her dress and struck pay dirt.
He put his hand on her cock and I thought the shit was going to hit the
fan.
"What's that?" he blurted, quite startled.
"A Kotex overnight maxi pad, silly boy. You know, the ones in the blue
package. Bad time of month. Very bad."
"Oh well, I guess I'm not getting any tonight."
"What, don't you like blowjobs?" Samantha whispered in Jimmy Joe's ear.
"Just because you can't do me doesn't mean I can't do you."
I stood up and said I had to go powder my nose and dragged Samantha
along with me. When we got there, I stammered excitedly, "Hey, I want
to watch this."
Samantha gave me the key to the room. "Hide in the closet. I have an
extra key."
Half an hour later Samantha and Jimmy Joe entered the room. Soon she
dropped to her knees and undid his pant. Oh my, he was wearing these
camouflage boxer shorts. Samantha lowered them. Jimmie Joe had a huge
boner before she even touched him. I felt like a peeping Tom but I
couldn't help getting excited. I slipped my hand down my panties and
began to tease my clit.
I thought I could really suck some cock but I had to give kudos to
Samantha. Such enthusiasm! She even taught me some new tricks.
Particularly impressive was the fact that she could get Jimmy Joe's
entire cock down her throat.
Five minutes later Jimmy Joe was screaming, "Suck me you fucking
whore!" as he pulled out of Samantha's mouth and shot cum all over her
face and hair. He grabbed his cock and rubbed the head around her lips
and she swallowed and licked up as much as she could.
Samantha stood up, and said, "OK baby, now it's your turn to suck mine."
She unclipped that tulip-wrap dress, the top had already been pulled
down to reveal her breasts while she sucked off Jimmy Joe.
Next Samantha took both hands and slowly and seductively pulled down her
'serpent purple' thong.
Jimmy Joe's eye's bulged out of the sockets, he grasped his chest and
collapsed to the floor. I immediately called hotel security and medical
personnel arrived quickly. But it was too late. Jimmy had passed away.
I stayed in town an extra couple days for Jimmy Joe's funeral.
Samantha didn't. Massive heart attack the coroner said, likely brought
about by some sudden traumatic event.
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