My First Anal Treat

Story Info
White crossdresser dates her first Black man.
1.9k words
4.53
126.3k
32
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here
leggyjill
leggyjill
57 Followers

Hi everyone - my name is Jill - at least after I shed my drab old male clothing and slip into my real clothes. You see, I am genetically a male: caucasian, blond, blue eyes, tall, slender, and very submissive. I love wearing makeup, sheer black nylons and garter, long blond wig, short dresses, and heels. I won't bore you with how I started - but let me tell you, I love it! My encounters with men have been all through this most wonderful of inventions - the PC. Thank you, Bill Gates and Steve Jobs (not necessarily in that order). After hooking up online, I would meet them at local motels and do everything for them but anal. I guess I was afraid. Then, one day, things changed.

I hooked up with my first Black man. He was married to a Black woman who had let herself go, refused to give him any oral, did not dress sexy, and generally ignored his sexual needs. Altho he still loved her, he needed more. So he sought out white transvestites - maybe that made him feel less guilty. But I was so glad he preferred those like me!

We spoke once over the phone, and his deep baritone voice had me wanting him even more. We agreed to oral only on the first date, and decided to meet at a motel that was mutually convenient to us. I got the room, as I wanted to change for him and get pretty for him before he arrived. The night before, I took a long hot bath, shaved myself silky smooth, and went to bed. The next morning I awoke and shaved again, put my nylons, garter, heels, teddies, long blond wig, and short black dress in my luggage and drove nervously to the motel. I was so nervous. I mean, I had fantasized about Black men, and absolutely loved looking at sexy pics of white women with their Black lovers...but now I was going to experience my fantasy!

I got the room and prepared. I knew he liked black stockings, heels, and teddies, so that was how I dressed. I also applied extra makeup, as he said he wife never wore that anymore. I wanted to please him in every single way!

There was a knock at the door. I slowly walked to it and looked thru the peephole. It was Richard! We had exchanged pics, and I had been afraid he had sent me one of him as a younger man. But he hadn't. My heart pounded as I opened the door and smiled.

"Hi Richard! I'm so glad you could make it."

"Hello Jill. I got out of work an hour early. My God, you look fantastic!"

"Please come in and sit down. You look wonderful yourself." He was wearing jean shorts and a t-shirt, both of which showed off his dark skin and muscles. I went weak at the knees.

"I'm sorry. I'm still hot from work. I'm a foreman at a construction site, and didn't have time to shower or change. I was in such a hurry to get here."

His scent had already intoxicated me. His short curly hair had a few beads of sweat and I longed to hold him, sweat and all, close to me.

"Oh, sit over here." I pointed to the only chair in the room. I sat opposite him on the bed. We talked for a few minutes. He was such a gentleman! And so handsome and strong and, well, dark! I crossed my legs and my teddie rose up a bit higher, showing him the tops of my stockings and revealing the soft white skin of my thighs. I could wait no longer. I patted the bed and he sat next to me. I licked my lips and my eyes closed halfway. No he took charge.

His right arm encircled my shoulder and held me as he leaned in. He said, "I love your red lipstick." Just before I felt his lips on mine, I murmured, "I wore it for you." Our lips met - black on white. I had never been kissed by a Black man before. His lips were soft yet demanding. His tongue entered my mouth and our tongues began a long slow dance together. I moaned as I felt his hand touch my knee. It moved slowly up my thigh and my teddie was soon at my waist. I had tucked myself beforehand so I hoped he felt nothing but my womanly body and tasted my desire for him. Our kisses went on for many minutes and my heart was racing!

He lowered me onto my back on the bed and stood next to it. He began to lower his shorts. My God - he wasn't wearing underwear!

"I hope you don't mind. I took the liberty of taking them off in my car before I got here."

"Mind? I'm flattered." But my eyes were not on his as we spoke. I followed the progress of his shorts dropping to the floor. He kicked his shoes off and removed his socks. Before me stood my first Black man. Yes his cock was larger than any white man I had been with. It was longer and looked both menacing and delicious. But it was not so big that I feared it.

"Jill, I want you."

"Richard, please hold me." I couldn't think straight anymore.

He laid down next to me, and pulled my close, kissing me again. I held his head to mine. I wouldn't let this man go. He gently pushed my legs apart and rolled over on top of me. "I love your long legs and the feel of your stockings. It's been so long since I've had a woman dress like this for me."

"Oh darling, you make me feel like such a woman. I'll always dress like this for you. You are the sexiest man I've ever known." I felt his cock get harder as we kissed again.

"Richard...may I do something?"

"Anything Jill...anything..."

I rolled him onto his back and began trailing kisses down his chest, letting my tongue touch both of his nipples. He rewarded me with a groan. His strong dark hands stroked my long blond hair as I moved to the top of his pubic hair. It was short and tightly curled. His sweat added spice to this oral dessert. My hands then touched his manhood. My lips rained kisses on it. My tongue rode up and down his shaft as I looked lovingly up at him.

"Oh Jill...you love sucking Black cock, don't you?"

I could only mumble hmmm hmmmmm as by now my man's cock was in my mouth and I refused to let it out! I was in heaven and did not want an exit. He got harder as I began pumping his cock in and out of my desperate mouth. My hair was all over his hot Black skin and the contrast drove me to even greater heights of passion and love. My red nails lightly stroked his very large balls and reached gently to his ass. One tiny finger stroked his asshole and he almost came on the spot. I retreated. I wanted this to last a long time - for both him and I.

I wanted him to have the greatest pleasure he had ever had. He was a hardworking Black man and he wanted a tall, blond, submissive TV to satisfy him. I would not disappoint.

Suddenly I stopped and took his precum covered cock from my mouth.

"Jill - what's wrong? I was almost cumming..."

"Do you remember earlier that you said you wanted me?"

"Yeah, of course. I want you even more now."

"Well, I want you too. I want you inside me. I mean really inside me."

"But I thought we agreed not to...on the first date."

"I know. But a woman has a right to change her mind, doesn't she?"

Without a word he pulled me to him and kissed, more passionately than ever.

"Straighten your stockings. The seams aren't straight. Then roll over on your stomach. I'm going to make you mine."

I obeyed. He was my man. I was his woman.

He pulled my panties to the side, and I expected pain. But instead I felt his hot wet tongue running up and down my hole. I shivered and begged him to keep going.

"I figured you don't bring any KY on your first date, so I'm applying some of my own natural kind."

"God, Richard, I need that hard Black cock so bad, darling. Please..."

I felt his get into position to mount me. His strong thighs touched mine. I felt the tip of his manhood against my tight, virginal hole.

"Richard, I'm a...a virgin."

"I'll go slow." Did I feel his cock get even harder after I told him I was a virgin? Yes...it did.

The head opened me and I gasped. It hurt just a little, but my man was keeping his word. He went slow. I felt him lean forward and about two inches entered me. The pain was sharp, but I tried to relax. When I willed myself to relax my anal muscles, four more inches suddenly invaded me. Now the pain was gone, and a feeling of such fullness, lust, and desire filled me that I began to cry.

"Am I hurting you?"

I had to catch my breath. Richard was both horny and sweet. I wasn't about to let this man get away from me!

"No, darling...please...more..."

He pushed into me and I felt those delicious black balls slap against my soft white ass. He began to slowly pump in and out, in and out. Our breathing was ragged. His hands reached under me and rubbed my nipples. My nipples are always very sensitive and now they were at their peaks! My small clit was at full attention. He was still moving in and out when I turned my head to him. He kissed me again. What a loving man! Our tongues met and I sucked his saliva into my mouth. He seemed a bit surprised but then locked his open lips on mine and I drank of him like a thirsty whore in the desert.

I broke our kiss. "Sweetheart, I need something else..."

His total weight was on me and his cock was deep inside me. I felt fulfilled as a woman, but needed just one more thing...

"Anything, my Jill..."

"Please cum inside me."

"You know I'm not wearing a condom."

"Two things: I never want you to wear a condom, and remember you never have to masturbate as long as you have me."

He kissed me. Again. And again. And did not say a word.

His thrusts became harder, and deeper. He was a man possessed. I knew he wanted me as much as I wanted him. Black into white. It felt so right. He was breathing so fast I was concerned for him. He leaned back, gripped my hips and roared out the primal scream of pleasure as he drove to my depths and began spasaming his very essence into me. How many thrusts? How many spurts of black cum were deposited deep inside me, his white submissive girlfriend? I lost count. But when he was done, when I had fulfilled him as a woman should, I asked him not to pull out. He didn't. We slept. He was mine and I was his. The seams on my nylons were in delightful disarray.

leggyjill
leggyjill
57 Followers
Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
16 Comments
AnonymousAnonymousabout 1 year ago

nothing like the feeling, and knowing you pleased a man anally then keep his cum in you.

algolfcrazyalgolfcrazyover 1 year ago

I wish that was me.Loved the story

AnonymousAnonymousalmost 7 years ago
wow

my keyboard is sticky now! I wish i was Jill

AnonymousAnonymousabout 8 years ago

I didn't go out to pick up a black guy, just the way it happened. I thought I looked just passable late at night mid week. Dressed in a black dress, my best feature is my legs, I am tall, I like to wear pantyhose at home but here I was venturing out for the first time. Twice before I had dressed to go out but at the last moment didn't. What if, what if, that's all I could think. I sat at a table near the back of the bar, I need not have worried, no one seemed the slightest bit interested in me until the bar was about to close and a tall middle aged black guy walked over and handed me a bourbon and coke and said last drinks, so I bought you one, mind if I sit. No, o.k, I saw you walk back from the bar, you have great legs, oh, thanks, do you dress up often, I must have looked horrified, he smiled, took my hand, oh don't worry, you look fine,very classy, in fact I was wondering if you would like to come to my home for a late night drink. I looked at him, yes, I think I would like that. He stood, took my chair and then linked my arm, leading me to his car. This was nice, he drove, a very nice apartment, he got me a drink, he had a small balcony overlooking a small park, I stood there, he moved behind me, pressing against me, then one hand under my dress, feeling my hosed bottom, my cock grew hard. I turned, wow, he held my face, kissing me, his tongue finding mine, if ever there was to be a first this was it. I pulled back, he put his hand on my bottom, leading me forward, guiding me to his dimly lit bedroom. I sat on the bed, he took his clothes off, his trousers and underwear last, wow, what I could see certainly looked big, my hand seemed to automatically reach for his cock, I slowly stroked him, then his hand went to the back of my head, pulling me forward, my mouth circled his cock, I had sucked cocks before, he held my head, moving it back and forward, I tasted his pre cum, my hand went to his large balls, he moved faster and there it was, his cum filling my mouth, holding my head as he released into me. MMm, he pulled back, then pushed me back,lifting my legs, I pulled my hose down and up, almost to my knees. My cock was rock hard, I watched as he knelt down, I thought he was going to suck my cock but no, his tongue and mouth went to my anus, working around, I was in heaven as he expertly rimmed me, opening my hole with his tongue. He completely removed my hose, I saw him get a tube, squeeze some of it onto his cock, then lift my legs, a lubed finger just moving around my hole, I felt the head of his cock, I said please its my first time, he leaned forward, his tongue again finding mine, slowly rocking back and forward, I wanted him and then a sharp push, yeoow, and he was in me. I felt pain, I tried to push him out but as I did I felt him sliding into me, little by little, his tongue working mine as he pushed deep into me and then began fucking me. How did it feel, like I was being made love to, far better than I thought once my bottom adjusted around his cock, in fact it wasn't long before I pulled my mouth away and said im going to cum, he pushed up into me faster, cum for me baby, cum, oh yes as my cum blasted between us, intense, draining as he made love to me, my insides clenching his cock. I felt his cock grow, I held him pushing up as he coated my no longer virgin bottom inside with his warmth. We stayed like that for quite some time, until he moved back, leaving me feeling wet and empty. Better than I thought, especially after staying overnight, he woke me in the morning, his cock hard again and fucked me from behind stroking my cock as his cock moved in and out of me, causing me to cum which caused him to push in deep and again his warmth shooting into me. That was the start of a relationship with Stanley that lasted for quite some time.

AnonymousAnonymousabout 9 years ago
hot

Describes my first black cock perfectly.

Show More
Share this Story

Similar Stories

A Slut is Born Young man forced to be a womanin Transgender & Crossdressers
Party Slut Never fall asleep at parties!in Transgender & Crossdressers
Like Mother, Like Sissy A sissy learns he is a princess . . . and a sperm whore.in Transgender & Crossdressers
Jill's Date with Deshawn White CD's date with married Black man.in Transgender & Crossdressers
Black Man's White Sissy A white punk learns to be feminine to his black master.in Transgender & Crossdressers
More Stories