Bigby "Confessions of a cross-dressing cocksucker"
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All on Sun Jun 5 18:49:51 2022
Confessions of a cross-dressing cocksucker
My story starts when I was 15 years old.
I was a regular kid; that is to say, heterosexual and horny.
There was a woman who lived in our building, a black woman. I guess she
was about 30 years old at the time, and she was damn good looking. I
often used to meet her in the elevator when I was coming home from
school. She would be coming home from her job at about the same time.
She always used to flirt with me, at first just that little smile that
women use on men [and boys] with such wonderful effect. Then we started
having little snippets of conversation on the way up. Then one day, as
several other people crowded into the elevator, she stood behind me and
fondled my ass all the way up to the ninth floor.
�Why don't you just come on up to my place, baby.� She whispered in my
ear after the other passengers had got out.
I knew she was married, but this was a 15-year-old boys dream; a
beautiful experienced woman to take my cherry; no swell, no tell.
That's what everyone used to say. My dick used to get hard just from
Delilah's smile, and I was so nervous I couldn't even talk as the door
opened and closed again on my floor, and we rode on up to 12, and crept
down the hallway to her apartment.
I guess she was about my height, and probably she outweighed me
slightly. It wasn't that she was heavy, but rather that I was a skinny kid.
My first kiss; I can remember it clearly, the thrill, the excitement,
the anticipation of so much more to come.
Her body felt so wonderful against me, her black skin was so smooth and desirable under my white little hands.
Delilah undressed me, stripping off everything until I was completely
naked, white and vulnerable, a toy for her pleasure.
She kissed me and played with my white erection, and it was more
wonderful than anything I had ever imagined.
It was some time before her clothes were also away, and my hands were
filled with her breasts. Her hard nipples seemed to call my lips to
them, and she held my head in her hands as I suckled her.
She had high cheekbones and wonderful big clear eyes. Her complexion was wonderfully smooth, and I had no reluctance towards giving her my virginity.
Finally, she couldn't wait any longer; she pulled me gently into the
valley of her love, took my penis in her hand and guided it into her
inpatient wet vagina. Her hands on my ass set the rhythm, and soon
afterwards, with an orgasm so hard it hurt for hours later, I was no
longer a virgin.
Delilah and I made love nearly every day for the next month or so. She
taught me what she wanted from me, and I loved every minute of my time
with her. She loved to suck my cock, and the smile on her face and the
light in her eyes was simply beautiful to behold.
Then we got caught.
Sean, Delilah's husband, was a large man. I saw him first, staring down
at us with fire in his eyes and his fists clenched tightly at his sides.
I was lying on my back, and Delilah�s head was down in my lap happily sucking my young white cock.
A couple of awful seconds passed, and suddenly Delilah became somehow
aware that something was wrong. I suppose my body going tense and my
dick going slack might have had something to do it.
When she saw him, her body went limp, her mouth hung open and her eyes
bugged out in abject fear.
�Oh shit. Sean!�
My sentiments exactly.
Delilah stood up, as I scrambled for my clothes. �Oh God. I'm so sorry
Sean. I��
�Shut up, woman!� He growled, giving her a shove that propelled her to
the far wall. Then he turned to me, and I thought I was going to die.
�You little white piece of shit! I should break your bones, I should
ring your neck!�
�No, Sean! Please!� Delilah begged him, �He's only a boy! Don't hurt him, Sean!�
Sean really didn't seem to know exactly how he should react. I was no
match for him; beating me up could lead to a lot of trouble but little satisfaction. Not to mention that everyone would inevitably want to
know why he had done it; his friends and neighbors knowing about Delilah
being unfaithful to him with a little white kid like me would be worse
to him than the actual infidelity.
But I figured all of that out later, at the time I was just shit scared.
�You, Blondie.� He said to me, get down on your knees! Tell me why I shouldn't beat the crap out of you.�
�I'm sorry, I'm sorry!� I blubbered, naked on my knees, �It was wrong
of me, I shouldn't have done it, I'm only 15! Please sir, don't hurt me.�
Big Sean looked confused. He wanted to do something to me, but he
couldn't beat up a sniveling kid.
�You've been taking what was mine, boy.� He said, �How you going to pay for that?�
�I don't know,� I whined, �I'll do whatever you want, anything.�
�Anything? What could you do for me to cover this?�
He towered over me, scowling, as a100 possibilities rushed through my
terrified mind.
�All right, boy. Suck my dick.�
And he unzipped his trousers and pulled it out.
It was soft, black, and uncircumcised. A piece of slack hose about five
inches long. I stared at it in horror.
He seemed to be enjoying my reaction to his demand. �Go on, boy. You're gonna give me what you've been getting. If you don't want the beating
you deserve, you get your mouth around my dick.�
�No, Sean! Please, don't do this!� Delilah begged him, attempting to
save my honor.
�You keep quiet, woman! And you watch. You watch your little white
sissy boy suck my dick, because that's what he has to do now. He's got
to do it and you've got to watch. Open your mouth, boy. Go on, it
won't hurt. If you don't wanna fight me like a man, then you suck my
cock like a girl.�
It seemed like the only way. Nobody would ever know, so it wouldn't
really matter. I couldn't let myself get beat up by this monster of a
man; reluctantly, I opened my mouth.
�Wider, Blondie. That's a good girl, now take my black dick in your
hand. Now put it in your mouth. Suck girl, suck on it.
Now that's not so bad, is it? How long has Delilah been sucking your
little dick? Do you think you're better than my woman, white boy?
Delilah sucks cock, and you can suck cock too. What are you afraid of,
white boy? You afraid of sucking a cock, or you afraid because it's a
black cock? Are you afraid you hate it too much, or are you afraid you
might like it?�
I wrapped my white hand around the large dark organ. There; I'd taken
the first step. I could get through this, I told myself. He wouldn't
really make me do it, he was just testing me. He would let me go, I
told myself.
His strong hand on the back of my head pulled my face to his groin. His stiffening penis slid between my naive lips.
�That's the way, white boy.� Sean said.
Sean's cock was now hard. It was in my mouth, and I was sucking it like
he�d told me to. I was so humiliated and afraid I was ready to break
into tears; but as he said, having his cock in my mouth didn't hurt.
Not physically, anyway. But I was doing something I knew to be
completely unacceptable for a male to do, It was the lowest possible act.
It was the only way out, I was telling myself. I'm not queer, I have no choice. And anyway, I realized, it was ok; certainly better than getting
really injured by him. I had a man's penis in my mouth, it was sliding
in out, and I didn't feel any different.
�Lick it, Blondie. You show me a good time. That's what you owe me, Blondie, and you're going to pay. I'll teach you to fool around with
another man's wife.
�You look at me now, Blondie. I'm going to come in your mouth. Not
just yet, but when the time comes, I'm going to shoot in your mouth.
And you're going to swallow it, understand? Don't worry Blondie, it
won't make you queer, unless you�re queer anyway. All the girls swallow
come these days with no problem at all. Hold my balls. What's it like
to hold a real man's balls in your little white hand? Are you watching
this, Delilah? Do you like what I'm doing to your little white boyfriend?�
Somehow, what bothered the than most was that Delilah was there. I
could have done this easily, I found myself thinking, if only nobody
would ever see, and nobody would ever know.
I had more time to think about that later; I realized then that it
wasn't the physical act that was humiliating as much as having someone
know that I had broken this taboo; �cocksucker�, that's what I had
become. �Cocksucker�. The word meant scum, it meant I was worthless, I could never be a man.
But in reality, the cock was inert; it had no flavor of it�s own. The
balls were big and black; but they were dry, it wasn�t like they were
slimy or something. The cock didn't burn my mouth, it didn't do
anything. I realized I was getting off cheap.
�I'm coming now, Blondie. You better be ready, 'cause here it comes.�
Suddenly, I was terrified again. I was about to be polluted,
contaminated. I tried to pull away.
But Sean held me by the ears so I couldn't escape as his big pulsing
black cock began to eject a large quantity of salty hot semen into my
mouth. He clamped my head between his hands with the strength of vice,
and his powerful body shook as stream after stream of horrible slime
assaulted my innocent young mouth.
I was so disgusted, I almost puked. But then I thought about what he'd
just said; Delilah did it, most girls did it. If they survived it, so
could I.
�Swallow, white boy. Swallow it down.�
He needn't have even said it. With his dick still moving around and all
that slimy salty fluid in there, there was nothing else I could do, and
I was already swallowing involuntarily.
I was amazed at how easily it slid down.
�Get out of here now white boy. Get out and don't come back.� Said
Sean, breathing heavily with the aftermath of the orgasm, and looking
nearly as confused by it all as I was.
I was a very perplexed young man, and I kept to myself for a while,
wondering if there would be any repercussions from what had happened.
Would Sean come after me? Would I be forever damaged from sucking his
dick, swallowing his come? Was that slime even digestible, or would it
rot in my gut?
After about a week, I was just starting to feel as though perhaps I
would be able to put it all behind me, when I met Delilah in the elevator.
�Come upstairs with me.� She breathed in my ear, her breast against my shoulder blade, her perfume in my nose.
�No way, Delilah.� I told her. I might have been a horny little
bastard, but I didn't want to die, or suffer that horrible humiliation
again.
�But it's okay, honey. Sean said it would be all right.�
�Sean said that? Bullshit, I don't believe you. If he catches us, he's going to kill me.�
�No, no. Really, he said it was all right. Only��
�Yes, only what?�
�You have to, um, service him.�
The door opened at my floor. It closed again.
�I can't do that.�
�Why not? I do it all the time, it's nice.�
�But you're a woman, Delilah. It's different for you.�
�Why's that? It tastes just the same to me as to you. You start to
like it after a while, it's fun. Come on, honey! Don't you like me? I
sure like you. I miss you, I was really digging our little afternoons together. Come on inside with me honey, and I'm going to make you feel
so good. We can hang out together until 6:00, when Sean comes home, and
it will only take you five or 10 minutes to settle things up with him.
Three hours with me for five minutes with Sean; that's not a bad deal, honey.�
My dick was like a rock, her hands were on my shoulders, her handsome
black face close to mine. Her door opened and closed, our mouths opened
and met.
I thought I would slip out early, but Sean came home at 5.
He took in the situation coolly. �So. You two couldn't leave it out.
You know what you have to do, Blondie.�
My heart sank, but I wasn't afraid this time. I had to do it, I'd had
my fun with Delilah. Now I had to do it.
�Go on, sweetheart.� Delilah encouraged me quietly, �You go ahead, it will be all right. It's just something you have to get used to, I
remember I didn't like it at first either. But you'll see, it gets fun
after a while. And Sean had such a nice one! Go on honey, do it for me.�
I crawled up to him. His hands stayed slack at his sides as I unbuckled
his belt, opened his trousers and removed his nearly erect penis.
I hesitated, staring at the dark organ in my hands.
�Go on, honey.� Delilah said, �You can do it.�
When hard, Sean's cock was at least nine inches long, and so thick
around that my thumb and forefinger could barely meet.
It was a great, glorious cock, and I wondered why it was that Delilah
was so hot for me with my little white thing.
It was easier on me this time, and as I sucked the cock of my lover's
husband, I found myself thinking that it was all right; I'd had to hours
of ecstasy with Delilah, kissing and stroking, fucking and sucking,
sharing orgasms with each other. And all I had to do was this simple
little thing. It wasn't hard work, it didn't hurt [although it did take concentration]. It was Sean that wanted it, not me, so if anything it
was he who was the queer one.
Sean pushed me away. I felt something strange; disappointment? Impossible.
�I don't want it like this, standing in my living room. Come on in the bedroom, Blondie. I want to lay myself out and be comfortable. You
come too, Delilah. You better watch your boyfriend be a sissy.�
Delilah sat on the edge of the bed, staring down at me as I sucked her husband's dick. It didn't seem to bother her; in fact I think she liked
it. Well, she was clearly a kinky lady.
�Lick my balls, Blondie. That's it, you keep a hold of my cock at the
same time. You're not looking so worried this time, Blondie. You don't
mind much, do you? Do you like it, Blondie? I think you do. Sidle up
here, Delilah, give me a kiss while your boyfriend gives me head.�
He paid no more attention to me as he fondled and kissed his wife while
I did my best to pleasure his rod. Soon, his hand clamped my head and
his back arched; once more my mouth was filled with come. I swallowed
it without much conflict.
I didn't see Sean for about a week after that. But my adolescent libido
was kept satisfied by sweet Delilah. God, that woman sure loved to do
it. She was as hot as I was, and that's saying something.
�My sweet white baby� she used to call me. She loved my white skin, and she liked to cook for me too.
But the Piper had to be paid; I was told to report on Sunday afternoon.
Sean looked at me critically.
�I don't know, Delilah. I like making him suck my dick, but I feel
funny about it. Why don't you take him and dress him up in some of your clothes. And do something with his face, know what I mean?�
�All right, Sean. Whenever you say, honey.� Delilah said, seeming a little worried to me, and took me by the hand and led me into the bedroom.
�What does he mean, Delilah? What about my face?� I was more than a little bit afraid of the answer.
�Nothing honey, nothing.� Delilah reassured me, �We'll just put a
little makeup on you so you look better to him.�
�Makeup? No way, Delilah. I'm not doing that.�
�You don't have to do a thing, honey. I'll do it, you wouldn't know how anyway.�
�I don't want to wear makeup like a girl, Delilah.�
�But honey, you've been sucking dick like the sweetest little girl there
ever was. What difference does it make now?�
I sat numbly as Delilah carefully applied makeup to my face. Mascara, eyeshadow, blush, lipstick. She clamped earrings to my ears, and
brushed my hair so it fell around my face.
She found a pink dress, and insisted I try it on. It was a bit silly,
since Delilah has large breasts and I of course, had none.
Nonetheless, when I looked in the mirror I was amazed to see that I
looked like a young woman.
Delilah seemed awfully pleased with her handiwork. �Honey, you look
sweet! Let's go show you to Sean! I bet he'll be pleased.�
He was.
�Now that's more like it. A sweet little white girlie. What's your
name, girlie?�
�Peter.� I answered him. Almost the first time I had said anything to him.
�Petra. Your name's Petra, girlie. Do you want to suck my black dick, Petra?�
�Yes, Sean.� I answered him
�Talk softer, like a girl. Do you want to suck my black dick, Petra?�
�Yes Sean.� I said again, in a soft voice this time.
�That�s better. Go on, then.� He instructed me.
I was a girl. A pretty blond girl, and Sean's hard cock in my hand felt
right. I wanted to suck it, I wanted to pleasure him. I wanted to
bathe this wonderful object with my saliva, I wanted to feel its texture
with my tongue. I wasn't yet admitting these feelings completely to
myself, but they were already there. I had sucked cock, and I wanted to
do it again. I watched his handsome face while I sucked that wonderful
penis into my mouth. He watched me back, obviously enjoying the sight
of his black dick in my cute white face. Enjoying my strange
androgynous look, a boy who looked like a girl, a male who had made love
with his wife now sucking his cock like a female.
I tried take it deeper, with limited success. I felt the weight of his
big black balls in my palm, and found myself looking forward to feeling
them contract while my mouth filled with their fluid.
�Oh baby, you're one sweet thing Blondie.� Sean said after a time, a
time of pure delight. �I'm going to come now. Do you want it, Blondie?
Do you want to feel my stuff in your mouth?�
�Yes, Sean.� I paused to answer him, �I want it.�
�Well here it comes, sweetheart. Oh, yeah!� And once more, I felt the greasy sensation of hot saltiness filling my mouth. But this time, I
wanted it.
Sean never touched me or anything. He just liked me to dress up as a
girl, and then for me to beg him to let me suck his dick.
Delilah got me a pair of strap on silicone tits, and I got into wearing
high heels and stockings. I let my hair grow longer, so it was easy to
style in more a feminine manner for Sean.
And I liked it.
I liked being a woman, I liked giving head. I liked it when he came in
my mouth, and I was his girl.
I also very much liked being a man. I was all man with Delilah when we
were alone, fucking her like a champion stud horse.
But then she would dress me up for Sean, and it was like I could be
another whole person; another personality, a different sensuality,
subservient. Sean's white trash girl.
I know that what I was doing was completely homosexual; but I never
thought of myself as such. I was just a young man who had a secret
second personality. I had built a little wall in my mind, and separated
myself into Peter and Petra. Peter was mad for Delilah, her wonderful
feminine attentions. Petra loved Sean, she loved to feel his masculine
energy, wind him up and release him.
His big dick was wonderful, noble, a joy in my mouth and in my hands. I
wanted more from him, but I had all there was to get; my breasts were
false, without sensation, only for Sean's visual amusement. I wanted to
be held and kissed by him sometimes, but he would never kiss me, knowing
what I was. I wanted to get fucked by him, but I had no pussy. I knew
that it was theoretically possible to have his dick in my ass; but a big
dick like Sean had was not for an initiate. And I would never instigate something like that myself, anyway.
But when I was in my normal clothes, I had none of those feelings. I
was male. I had a kind of vague longing to become my female self, and
feel those odd urges, but I didn't feel the odd urges directly.
This went on for a couple of years. But then we all started to get
bored. We started to go out.
We went to clubs, and I danced and flirted with men while Sean and
Delilah kept an eye on me. I danced with Delilah, and kissed her openly
on the dance floor. Everyone thought we were lesbians, and the three of
us all loved the exhibitionist show.
I strapped my cock backwards against my ass, which wasn't as
uncomfortable as I had expected it to be when it became engorged. I
danced closely with a strange man, and felt his hard on with my thigh
between his legs. I let him kiss me, and the thrill was unlike anything
I had felt since my first experience with Delilah. I felt some conflict
about doing this; the poor fellow thought I was a woman, it seemed a
crime to deceive him that way. On the other hand, if he never found
out, what was the difference? He would be left with only pleasant memories.
Sean came and rescued me after a while, telling the man he was my
husband. We hurried back home, where Delilah gave me head while I did
the same with Sean.
It was dangerous experiment, but the three of us were so excited by the
nasty betrayal of the stranger, that we wanted to do it again.
Sean invited the next man to come back home with us.
�Sometimes, Delilah and Petra are more than I can handle by myself, know
what I mean?� He said to the poor fellow, an arm around each of our shoulders, �Why don't you come back to our place, we could have some fun.�
The man looked in my face, and the real excitement and anticipation he
saw there convinced him to take the chance.
Of course, I couldn't undress. My dick was pulsing painfully, and I
kissed the man, Fred, on Sean's sofa while Delilah removed her clothes.
I held him close so that he couldn't fondle my artificial breasts; he
opened the back of my dress, and stroked my back and arms, as I
shuddered in girlish delight.
I was afraid, he was getting close to discovering me; then Sean pulled
me away from him.
�Delilah, why don't you sit here with our guest. Petra honey, would you
like to show your friend how you suck my dick?�
�Oh yes, Sean. Yes.� I said with relief, and we sat opposite Fred and Delilah, me slowly sucking my masters great dick, while my new friend
Fred fondled Delilah's genuine black breasts, played with her twat and
kissed her while they watched us.
I didn't let my man come for a long time, and he enjoyed the ecstasy and
agony of it, while he let Fred go all the way with Delilah.
It was strange to watch his white ass moving up and down between our
Delilah's thighs. Sweet and sour, pain and pleasure, jealousy and joy.
So wonderfully perverse. I know for sure that Sean wasn't too happy
about it, but he wanted to make us girls happy. The only way he could
keep Fred from discovering the truth about me, was to let him have his
way with Delilah.
Delilah was clearly loving it, screwing this stranger in the safe
presence of her regular lovers.
Fred pulled out, and put his mouth to Delilah's clitoris; I didn't want
to leave Sean, but I had to try this new penis, white like mine but
masculine like Sean's.
Intellectually, it's impossible to say why one should feel different
from another. But I knew it to be a different penis that I was
servicing tonight, the penis of the stranger, the penis of a man who had
held me and kissed me, believing me to be a real woman. Pleasure and
betrayal, dark and sticky, sensuous and wonderful, smooth, hard and potent.
I looked up to see my sweet Delilah leaning over to suck her husband's wonderful cock.
�What about you, Fred?� Sean asked our new friend, �You want to have a go? Did you ever suck cock?�
�I, a, no thanks, Sean.� Fred answered him, to my happiness and disappointment. I would have liked to see my man's big black dick in
Fred's mouth, but by refusing, Fred had declared himself a real man.
And I had seduced him; his white dick was in my pink mouth, my blue eyes
were batting at him while my hand squeezed his dick, while my mouth
clamped and sucked him until he couldn't hold back, and I felt his hot strangers jism enter my eager sissy mouth.
I got up on the couch, and kissed sweet Delilah while Sean screwed her �normally�. I almost let Fred get my skirt up, but then I told him not
to and he respected that. Or perhaps he suspected, and didn't want to know.
We never saw him again, which was probably just as well.
I went away to school soon after that, and lived as a normal
heterosexual boy, dating girls and having normal sex with them. It was
good, it was fine. I had occasional pangs of longing for my makeup kit
and female clothes, but being straight was also all right.
I had cut my hair short, but when I came back home for the summer,
Delilah dressed me up for Shawn like she used to.
�Hey blue eyes, good to see you.� Sean said and gave me a hug; for a
brief ecstatic moment, I thought he might even kiss me.
I was amazed at how excited I was as I unpacked Sean's great cock an
hour or two later; I was trembling with anticipation, it had only been
so long since I'd had this privilege. I'd nearly forgotten the joy of
being a girl, of sucking cock and making a man come.
we all went out like before.
I looked wonderfully demur with my short hair, and it didn't seem to
have any detrimental effect on my attractiveness to men. I teased many
while under the protection of my man, but only once or twice did we dare
to take one home.
Once more, I enjoyed myself kissing and fondling, but it was Delilah who
had to finish the job. Not that she seemed to mind. It really
surprised me that Sean was willing to put up with it, but I guess
somewhere he also enjoyed the pain and pleasure of watching his wife
enjoy another man.
When I arrived home for the second summer, my darlings had a surprise
for me; a vibrating dildo, so small, something for the virgin ass.
Delilah sucked my cock and worked it inside, and the sensation was more
than I could have ever hoped for.
Slowly and lovingly, my darling stretched and prepared my ass, making me accustomed to penetration. And before I left to go back to school, Sean
did it to me.
We went out dancing first, and we made spectacle of ourselves; Delilah
and I did our girl/girl routine, and we both flirted with a table full
of college boys. Sean had been watching quietly, and came to collect us
when he'd had enough.
�Oh man, you're not going to take both of these ladies away, are you?�
One of the college boys asked.
�I'm afraid so, pal.� My main man answered him, pudding a strong arm around each of our slim waists. I was so into my role, I was so much a
woman, that I forgot myself. I took Sean's face between my hands, and I
kissed him.
And he kissed me back.
And it was wonderful.
We went home, and Delilah stripped me down for him. She reamed my ass
with a medium vibrator, she licked my ass hole, she greased our man's
love pole.
I was his woman, his sissy boy. His powerful hands on my ass pulled me
open, and my anticipation was finally relieved as I felt the tip of his familiar manhood in this unfamiliar place.
Sean pushed gently, and slowly he eased his large black dick into my
small white waiting body. He reached under my hip, and for the first
time ever, he took my penis in his hand. He squeezed me and fondled me
while he fucked me carefully, slowly, enjoying it as much as I was.
Delilah stroked my head and back, and soon I couldn't take any more; I
came, a wonderful powerful release of tension and passion.
Sean wasn't through, and he kept fucking me.
It's the wonderful thing about being a girl, or sissy boy. Even after
you come, you can still please your lover. Our man was good, and the
sensation of his hot hard member sliding in and out of my rectum was
painful but totally desirable. I felt myself getting hard again, and as
Sean exploded into my backside, I came again, although there was nothing
in my balls to actually ejaculate. I came like a woman, my muscles
contracting and spasms running through my frame, but with very little
fluid extrusion.
After my graduation, and then my marriage, I've only seen Sean and
Delilah once or twice a year. Only then do I relive these strange dark
desires of mine, and I've never done it without their protection.
I don't know how you found out about me, honey. But since you know, I
felt the compulsion to tell you everything.
I don't know if you can take me back now that you know about me. But
I'm glad I've told you anyway.
You know where I'm staying. I hope you'll call.
I love you with all my heart, Peter
Bigby, 2002
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