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confessions of a crossdressing cocksucker

More Bigby stories at; http://www.asstr.org/~Bigby/

and; ftp://ftp.asstr.org/pub/Authors/Bigby/ in plain text

I sure do appreciate getting some mail back; bigbystories@hotmail.com



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!"

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? 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,

anyway.

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

choice.

"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

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.

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 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,

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 and hot saltiness fill 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.

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

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.

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

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 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; http://www.asstr.org/~Bigby/

I sure do appreciate getting some mail back; bigbystories@hotmail.com