Sex Stories by Letter ] [ Sex Story of the Week ] [ Story Forums ] [ Adult Personals ]
Sex Toys & Videos ] [ More Sex Stories ] [ Submit Stories ] [ Links ] [ Webmasters ]
Archived Sex Stories

confessions of a crossdressing cocksucker


More Bigby stories at;
and; in plain text
I sure do appreciate getting some mail back;

Confessions of a cross-dressing cocksucker; by Bigby, 2001

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.

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 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

"I don't know," I whined, "I'll do whatever you want, anything."

"Anything? 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 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; 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 that it's a black cock? Are you afraid you
hate it too much, or are you afraid you might like it?"

Sean's cock was now hard. It was in my mouth, and I was sucking it like he
said. 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,

It was the only way out, I was telling myself. I'm not queer, I have no

"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? I'm coming now,
Blondie. You better be ready, 'cause here it comes."

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 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?

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.

"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 awhile, 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.

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.

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 two 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

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.

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

"I don't want to wear makeup like a girl, Delilah."

"But honey, you've been sucking dick and swallowing come. 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,

"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,

"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 and hot saltiness fill my mouth. But this time, I wanted

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.

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.

I strapped my cock backwards against my ass, which wasn't as uncomfortable
as I had expected 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.

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

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.

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 my
Delilah's thighs. Sweet and sour, pain and pleasure, jealousy and joy. So
wonderfully perverse.

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, 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.

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

"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 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

More Bigby stories at;
I sure do appreciate getting some mail back;


Sex stories by alphabet: a b c d e f g h i j k l m n o p q r s t u v w x y z


© 2003 Sex Stories Archive. All rights reserved.