Erica and Jack
I guess like a lot of guys my college years were marked by chance
occasions with other men. Awkward glances in the lavatory turned
to smiles, which then turned to more than that. Often these trysts
were consummated in the bathroom stall, occasionally they would
drift back to a dorm room or apartment, but never did these entirely
sexual encounters lead to anything I considered a relationship.
So it is not surprising that I never considered myself to be gay.
Certainly, I had never had a
revelation, or any moment of seeing the light, where I knew I liked
men, as many of my gay friends have suggested should happen. My
attraction towards women never wavered. The sex I had with men was
entirely separate from the sex I had with women. It was almost as
though I were two separate people, a strong dominant top with my
girlfriends, and a submissive, girly, little thing with the men
I met in bars, restrooms and us station platforms. I thought I was
free to choose between men
and women as I saw fit. Seeing the difficulties my gay friends had
with their lives, I chose women. When I met a wonderful woman, I
decided to marry her, and live a life that the outside world would
see as normal.
Our married life was pleasant enough. I loved my wife, Erica, a
great deal. We communicated well, always doing our best to resolve
issues in the relationship before they grew out of hand. I trusted
my wife with some pretty intimate details about myself, but still,
I kept my biggest secrets from her. I never divulged the details
of my college trysts, and I certainly never explained to her what
turned me on about being with a man. I guess its nothing special
- a lot of men have sex with other men and
likewise have great and satisfying sex with women too. I admit it
though, I was embarrassed by my urges. I was embarrassed, because
when I was with another man, I wanted more than anything to act
like a girl.
Our first year of marriage was normal enough. As newlywed elation
drifted into the routine of daily life, I found myself thinking
about my old liaisons, and soon I realized I was craving sex with
men again. I repressed most of these thoughts, however. I didn't
want to jeopardize my marriage, and I certainly didn't want to do
anything that would put my wife's health at risk.
It was around this time that I started having fantastically vivid
dreams at night. In these dreams I was a wife or a stripper or especially
a young college co-ed. The girl I was in my sleep was like my alter
ego. She was strong and clever, with a quick wit and a wicked tongue.
I thought I could go on like this, if not forever, then at least
for the foreseeable future. Little did I know I had been talking
in my sleep.
Erica and I had a mutual friend, Jack. Jack worked as a fundraiser
for the large charities of our city. This was the perfect job for
him as his powerful charm, imposing presence, height and masculine
build lent him an air of total authority. It was easy to see how
Jack charmed old society women into writing large checks for whatever
cause or artistic endeavor he was pushing at the moment.
My wife and Jack had been spending an inordinate amount of time
with each other that season. Erica was putting together her notes
for a biography she was working on, and Jack was helping her target
those notes towards potential publishers and charitable foundations.
It was not unusual for me to come home from work to find them hunched
over the coffee table studying old manuscripts and sharing inside
jokes. Often, upon my arrival, they would put their work aside and
the three of us would spend long hours talking and laughing, drinking
coffee and flirting with each other in a ever increasingly ambiguous
way. I became a little uncomfortable with the number of late evenings
Jack was spending at our house, but managed to put these thoughts
aside. A relationship is nothing without trust after all. More than
that, I could not deny to myself the increasingly erotic feelings
I was experiencing as I observed my wife's closeness with this man.
I found myself dreaming of them together, of her kneeling in front
of him with his large cock in her mouth. In these dreams he was
laughing at me, telling me to get on my knees to watch my wife up
close. I often woke from these dreams with a start, the image of
Jack's hard penis burned in my memory.
One evening I returned home from work to find them already slightly
drunk. Erica's face was flushed, and one of the straps of her dress
had fallen off her shoulder. To my sober eyes, it seemed as though
the hem of her baby doll was worked too far up her smooth thigh
and it was unusually bunched around her crotch. I stood in the doorway
absorbing the moment. Jack, and my wife stared blankly at me, their
eyes a little glazed from the gin they had consumed, as the silence
"Darling, you're home! Well don't just stand there, come and
have a drink with us." Erica finally said, breaking the awful
silence and patting the couch between her and Jack. I didn't know
what to do. On the one hand, I knew I had just caught them in the
midst of an affair, on the other, my wife looked so beautiful, and
Jack so handsome, I admitted to myself that the thought of them
together was making me aroused. I figured there would be enough
time to untangle this mess in the morning. In the meantime I would
sit, let my wife pour me a drink and wait to see what would unfold.
The three of us all readily drank, and Erica ensured our glasses
were never empty. Her behavior grew more and more provocative, and
Jack seemed to revel in his manly control of the situation. He reclined
on the couch and draped his arm behind me and my wife. The ambiguous
flirting became intense and I felt myself grow more and more shameless.
I was acting coy, impetuous and cute. In a word, I found myself
acting more and more girly as the night wore on.
"All right" my wife said. "Enough joking around.
All this liquor has gone to my head. It's time for some fun. I want
to reveal my sexual fantasies."
I was too drunk to be shocked really, but I was surprised. My wife
was an extremely open and sensual, but she always maintained her
decorum among company. The way she had said 'sexual fantasies' with
her mouth open an her wet lips pouting left no doubt as to the fact
that she intended to live them out after she revealed them. Jack
and I waited in anticipation.
"I have always wanted to watch two guys get it on. You know
- Fucking. There I said it."
"Oh, come on!" I exclaimed. "Just what are you trying
to drum up here." I protested falsely.
"Don't play stupid with me." She said. "I hear you
talking in your sleep. Jack, would you like to know what my husband
really wants? Would you like to know what he really fantasizes about?"
Jack was grinning in a bemused sort of manner. It was clear that
he already knew what she was going to say. He shrugged, the humiliation
was for my benefit and my benefit alone.
"My husband wants to be a girl! What do you think of that,
Jack? But even better, my husband wants to be your girl. I heard
him just last night talking in his sleep. He was cooing like a little
bitch, asking you if he was pretty enough. You know what he actually
asked, Jack? He asked you if he could kiss the tip of your penis.
Can you believe it? Is my husband a little pussy cock-sucker, or
what?" With that she picked up my hand and to my amazement
placed it on Jack's lap.
I was surprised by the sudden change in the conversation. An hour
ago I had caught them on the verge of an affair, and now my wife
was calling me nasty names in front of this other man. My wife was
really drunk, and I could tell she was turned on to the point of
desperation. She whispered in my ear. She started cooing about how
much I wanted it, and how it was OK, how she was dying to see me
do it. She unzipped Jack's pants and pulled his thick, hardening
cock out from beneath his boxer shorts. She began to stroke him
right there in front of me, and I watched, my mouth agape as his
cock grew to a full nine inches.
"I know you want to suck it, you bitch. Go ahead and suck
it, you sissy, I dare you. It will be fun." Erica cooed.
Drunk as I was, it was hard to resist. I was in. I had gone since
college without a man, and I had been dreaming about sucking Jack's
cock. Even in my dreams though, I never imagined his cock would
be so big. Erica pushed at the back of my head, and in an instant
I had bent to my knees and had taken Jack's dick into my mouth.
Jack was really into it, his cock got fully hard almost immediately
and I bobbed my head up and down on it greedily. I was surprised
how quick the whole thing went. Jack grabbed my head, holding me
by the hair, arched his hips and came in my mouth. I looked up licking
"That was fun." I said a little drunkenly, figuring the
whole thing had been a drunken hoot, and now we could go back to
normal. But Erica protested.
"Oh no!" she yelled. "You think you're gonna get
away that easy. You think you can just tramp around like a little
cock-sucking whore, and get away with it? Jack read this."
She said handing him that week's copy of 'The New Yorker'.
"You, little girl . . . You are coming with me." she
said leading me into the bathroom, by the hand.
She told me she had figured out that I was a sissy by the way I
always read her fashion magazines. When she had discovered her panties
missing, it confirmed her suspicion. She had decided to give me
a treat, she was going to treat me like the bitch that I was. I
had to admit that she was right. Drunk as I was, I didn't have it
in me to protest. She was right, I did always wish I was a woman.
I desperately wanted to be, I mean it would be so much fun to flirt
and tease. I'm not very big, I'm only 5'7" 128 lbs., I'm very
thin and androgynous looking. I have almost no body hair, and I
enjoy wearing my strait black hair long, almost cut in a girlish
bob. I can pass for either a man or a woman depending on my dress,
but I've never really tried to look like a woman outside of the
house. It is obvious to almost everyone who meets me what a sissy
I am. Even my wife is stronger than me.
She started taking outfits from her Armoire, singing out to Jack
"Oh you're going to love her in this one." She asked me
which outfit I liked best, but it was clear my feeling didn't matter.
She had it thought out, she knew what she wanted me to wear.
She put me in a little, black, pleated mini-skirt. It certainly
wasn't skin tight, but it was definitely on the short side. It was
the type of skirt a woman would wear only if she didn't care if
her panties would show when she bent over. Erica had me put on white,
lacy, thong panties and garters and white ribbed cotton stockings
and Catholic girls school shoes she had bought at the thrift store.
On my top I wore a tight, youth-sized T-shirt, with a little pink
star between the tits so I could feel how
hot it felt to wear a tight shirt.
By this point, drunk and turned on, I did feel like the little
cock-sucking bitch my wife was telling me to be. Needless to say
we were drinking gin this whole time and laughing. Erica was cooing
about how pretty I looked and how she wished she were a guy so she
could fuck me herself. I was trashed and totally uninhibited and
to be truthful I really wanted to get fucked like I was a woman
by that big stud in the living room. I mean he was big, and I wanted
him, there was no way around the feelings. My wife must have seen
me looking at him, as his framed filled the bathroom doorway because
she slapped me.
"Not yet you little slut, I haven't done your makeup or your
hair yet." All I could do was smile like the little tramp I
was rapidly becoming.
My wife sat me on the toilet bowl and pushed back my head , she
pulled my hair into little pig tails, and started painting my face,
It felt so sexy, I can't describe it.
On my lips she put cheap, pink, lip balm, the kind a thirteen year
old girl would wear. On top of it, she rolled "Kissing Potion"
a glossy lip product marketed to junior high school girls. When
she was finished my lips looked shiny, full and wet. She painted
my eyes with a silvery eye-shadow, with some hints of dark, and
a drew a thick black liner at the edge of my lids. On my cheeks
she applied only blush. She didn't need any foundation as I am naturally
pretty fair skinned with out a lot of facial hair. As I had just
shaved that morning, I didn't have any hair to hide.
We were giggling and having a ball and my wife was helping me use
my voice to sound like a real girl instead of a cheap, male, imitation
of one. When I looked in the mirror, I saw a cute boy who looked
a great deal like a woman. I had to admit there was something sexy,
even hot about me, even though my chest was still flat. Jack stumbled
into the bathroom, staring as much at my wife, her tank top barely
concealing her large firm tits, as he was me.
I walked over to him and put my arms around his neck. Even in the
high heeled pumps, I needed to look up into his face, he was just
so much bigger than me. I lifted one leg, bending it at the knee
like a woman would. I felt sexy, like a women from the fashion magazines.
My wife was taking pictures of me with Jack, and she looked at me
as if to say 'There's no turning back now'. I didn't want to turn
back. I licked my lips and waited for him to kiss me. I felt vulnerable,
like a sixteen year old girl. I wanted to loose my girly virginity,
but I was still a little scared.
Jack held me with those huge strong arms, pulling me to him, his
desire rising in him. I felt his hard cock growing and pressing
into my stomach. He went to kiss me, but I said, "Stop."
My wife and he looked at me, puzzled. "I don't want you to
mess up the make up". I said giggly nervously.
Jack pushed me to the floor. I bent down on my knees feeling the
bathroom tile through my stockings. I looked up at the big stud
my eyes wide and submissive, my freshly painted lips pouting and
waiting. My wife was watching. I could tell she was feeling edgy,
and she started to touch herself through her jeans. I knew I was
about to get what I had wanted for a long time.
"Take my cock out, pussy boy." Jack said, and I obeyed.
I unzipped his pants, removing his thick, meaty penis. His dick
was half full with blood, heavy and hardening in my little girly
hand. I placed my little fist around his thick shaft easing the
flesh up and down over the bone. His pink mushroom head was right
in front of my lips, and I couldn't take my eyes off its beautiful
shape. I wanted it too badly. I needed to have it, to play with
it like a girl would, and to be played with as only a girl can,
by the man who owned it. I wrapped my pink painted lips around that
beautiful cock, loving the feeling of that piece of meat in my mouth,
the feeling of a man fucking my little faggot face. I blinked my
eyes as I looked obediently up at Jack, his cock filling my mouth,
stretching my lips. I was his girl to use.
I'm getting hard right now thinking about it, but at the time my
little girly dick was rigid against the sharp lace of my panties.
I felt joyful like a whore who needs cock and has just been allowed
to play with the boys for the first time. I wanted to get dirty,
and get used like the little pussy I was. Jack started to moan.
I was sucking him good, running my tongue over the sensitive underside
of his cock head, softly stroking his balls with my left hand and
working his shaft with my right.
"Don't let him cum, you sissy faggot. I want you to get fucked.
Don't you want to get fucked, you little panty bitch?" Erica
To be honest, I hadn't really considered letting a guy fuck me
until that moment. Sure I had fucked around with men before but
it had always been limited to a few hand-jobs and lots of fellatio.
As the fun had started that night, I thought I would dress up, suck
his cock, and that would be all. In my mind, I hadn't envisioned
my ass getting fucked. I found myself blushing because more than
anything I realized, I wanted to feel just that. I wanted Jack's
hard cock in my ass.
I knew I had been kidding myself when I got married. I thought
I was a man, but my wife had made me see just what a little, sissy,
cock sucking, bitch I really was.From now on I would be used by
men. I would exist to suck cock and get fucked, and that's how I
wanted it. I wanted to get fucked like a bitch, have my little pink
perfect asshole used like it was a pussy. Right then, I wanted Jack
to fuck me and call me the names I deserved to be called - names
like whore, tramp, slut, faggot, cock-sucker, sissy, pussy - Bitch.
I was all those things, and I liked the feeling. I couldn't wait
for him to slap my ass and use me for his pleasure.
My wife instructed my to get on the bed on all fours and stick
my ass in the air, she was really hot, stripped down to her panties
and tank-top. She had one hand jammed against her pussy, as she
massaged the cheeks of my ass with the other. I heard her voice
coo what a nice little girl I was, and what a pretty ass I had.
Almost brutally, she pulled my white, lacy panties to my knees.
I was constrained by them, my panties stretched against my knees,
but still my ass was bare and open. My wife scraped her finger nails
across my balls giving me a chill throughout my body.
"You're gonna get fucked now little girl, and your gonna love
it!" My wife whispered in my ear, still touching her clit with
her free hand.
She pulled the cheeks of my ass apart and put a drop of spit on
her finger ramming my little virgin ass-hole with it, getting me
ready for my man. Meanwhile Jack was getting impatient. He started
saying how bad he needed to fuck my tight little ass, how he wanted
to split my 'cunt' in two. This time I was shocked. I knew Jack
was going along with our fun, but I never expected him to speak
like that. I started to get a little scared. I thought I might be
in over my head, but I knew there was no backing out at this point.
My wife loved me, but she was so turned on, she would let Jack
rape me against my will before she would call her fun off. Even
though I was frightened I didn't want it to end. I felt so horny
on the bed, spread out on all fours with my sexy ass in the air,
waiting for that big man about to fuck me like a girl! I couldn't
help it I started wiggling my ass like a cunt, begging for Jack's
cock despite my wife being there.
"Please fuck me!" I begged, "Please give me that
big hard cock in my hole, I'm such a bad girl, I deserve it."
I said, giggling at how absurd I must sound. My wife was too turned
on to laugh. Her panties were off now, and she was touching her
little trimmed pussy. She started to yell.
"Yes you little bitch, you want get fucked like a girl, you
want that big cock in your ass. I thought I married a man, but what
I really married is a little fucking, faggot, pussy-slut of a girl.
God you bitch, take your hands and spread those ass cheeks of yours.
Beg that stud to fuck you like a woman."
And I did, my face pressed into the bed as I held my ass apart,
desperate, almost crying to be fucked.
Then I felt it. I felt the huge head of Jack's hard penis pressing
at the tight pink entrance of my asshole. He was pushing his cock
into me, almost splitting my hole as he worked it into me. It hurt,
but the hurt only made it better. I was getting fucked like a girl,
something I never allowed myself to imagine. His tremendous hard
cock filled me up as he started to fuck me good. I didn't really
scream as much as cry with exultation. It felt so good, and when
I thought it couldn't feel any better, my wife forced her head under
my waist and started sucking me, every so often licking my ass hole
where the big stud fucked me.
I felt the cock in my ass get harder and I knew he was getting
ready to cum. I yelled "Wait for me baby, wait" just like
I was a woman because I could feel myself getting near and I didn't
want him to cum first.
I fucked my wife's face furiously all inhibitions gone and I felt
my orgasm rising in me. Then I felt Jack yank his cock out of me,
hurting me in the most wonderful way. Jack slapped my ass just to
show me he was in charge. He grabbed my long hair and pulled my
face in front his cock, hot and fresh from my ass. I sat there for
a second, all thoughts gone. The room was silent until Jack began
"Yes, you hot, faggot bitch." He screamed as his hot
cum splashed against my face, coating me like a porn starlet. My
own cum came as Jack rubbed his softening cock over my sticky cum
coated lips. All my inhibitions were gone, I was now a panty bitch
I don't know what else to say. I touched my ass and rubbed some
of the cum from my face around my open hole. I felt dirty and sexy,
my fingers touching where my asshole gaped open like a pussy after
a good fuck. My wife kissed me her mouth full of my cum. She wanted
me to drink so I did. Jack held his cock, a little softer now, but
not flaccid by any means, in my face, and I cleaned it for him lovingly.
My wife and I gave him a knowing look. He took the hint and gathered
his things and left shortly after.
Since that night, the three of us have become sort of thing. If
Jack asks I will let him fuck me whenever wants, whether my wife
is there or not. Often, Jack makes me dress up and suck his dick
to get it hard for him, and then makes me guide it into my wife's
pussy for him. Often my job is to lick them where they join and
clean his cock and her pussy when they're done. I suppose there
are other nights too, when I'm not around that Jack fucks my wife
and the two of them laugh at what a
pathetic, little, cock-sucking, sissy I am.
Still, our best nights, are those when we pull out the gin, and
my wife starts rambling on again about her fantasies, and her dares.
And you know what? I can't wait to see what she comes up with next.