• Home
  • /
  • Stories Hub
  • /
  • Transgender & Crossdressers
  • /
  • Jill's Date with Deshawn

Jill's Date with Deshawn

12

My name is Jill. At least when I slip into nylons, heels, dresses, and long blonde wig. The moment I do so, I am transformed into a submissive lady whose reason for existence is to give the most intense pleasure possible to men. Especially men of color. I have had many real life experiences with men - some more satisfying than others. Lately, I have been meeting some very horny, very sexy, very demanding Black men.

Most are married to Black women who take them for granted. I, however, do not. What you will read next is my most recent hookup.

Goodbye AOL chat rooms. Hello Craigslist.

I posted my first ad. It made me nervous at first. It stated that I was a submissive white CD with long sexy legs. I enjoy wearing nylons and heels. Then, I wrote that all races were encouraged to apply.

Within 15 minutes, my inbox had 20 or more emails from men of all races responding! I had to delete the ad. After all, I wanted to give each man the courtesy of a reply.

There were Mexicans, Asians, whites, and, of course, Black men asking for my favors. I went Black.

The man I was to meet was 20 years younger than me. He was in his early 20s, very dark, very muscular, married to a Black woman, and anxious to have me take care of his every sexual need.

Our entire correspondence was via e-mails. No phone calls. We trusted each other that we were both for real.

He wrote, "Will ya wear nylons and a short dress when we meet?"

I wrote back, "Of course. Do you prefer that I wear sheer black thigh highs or pantyhose?"

"Do ya have any fishnet stockings?"

"No, I've never worn them. And we're going to meet at the hotel soon."

He wrote the sweetest thing, "I'll buy ya some before I get our room. What size ya wear?"

I was stunned. This was the first time any man offered, before the first date, to buy me anything!

I told him my size,

He told me when to arrive at the hotel. He said I would not have to show ID or a room key to enter the hotel tower. I breathed a sigh of relief. He knew I would arrive in my men's clothing and change in the room.

As I drove to the hotel, I went over in my mind what I would be wearing. Black dress (short, of course - I'm 5'10" and love showing off my legs!); deep purple panties; black 3" heels; and an intoxicating perfume. I brought along several pairs of nylons. It was a Saturday night at 8 PM, and I didn't expect my Black lover to be able to find fishnet thigh highs at that hour. You see, a gurl like me is always prepared.

I parked, and got on the elevator, carrying my bags. I got off on the 15th floor, and found the room. It was slightly propped open! What was this all about?

I listened at the door. A radio played softly.

I called out quietly, "Oh Deshawn..." No response.

I called out more loudly, "Darling,,, it's Jill. Are you there? Can I come in?" Still no response. The soul music got me even more excited, and I boldly pushed on the door, expecting a security lock to engage. It didn't.

The room was dark, but my eyes soon adjusted. No one was there. But the light in the bathroom was on. I figured he had stepped out for a moment. I had to change for him, so I entered the bathroom and locked it.

I took off my awful, rough, male clothes, and took a moment admiring my smooth pale body. My legs and feet are incredibly sexy. My nipples, always sensitive, were erect. I walked to the sink, and what did I find?

A brand new package of black fishnet thigh high hose!!! I swear, I almost swooned with joy. This young Black man had done it. Little did he know that he had thrilled me to my core. I carefully opened his present to me.

These were, quite simply, the sexiest pair of stockings I ever had. More so because they were a gift from a young Black man than for any other reason. I was so glad I had shaved my legs the night before.

I pulled up the first stocking. My 'clit' got hard as a rock. It was so hard that I had trouble putting on the second one. But I did. I quickly put on my panties and dress. Then I looked in the mirror. Even without my makeup, perfume and wig on yet, I looked fabulous! I was already showing a lot of white thigh, and the contrast with the black fishnets would drive Deshawn wild!

After applying a lot of makeup, I put on my long blonde wig. Then I heard the door open!

"Yo, Jill...I see ya found em"

"Yes deshawn, I did. And thank you, darling. They are beautiful."

"Yeah, I like white gurls in fishnets."

I heard him lock the door. Then I heard the bed creak. Was he sitting, or laying down? I wasn't going to hurry. I brushed my wig so it looked very natural. I pulled up the stockings, stepped into my heels, and opened the bathroom door.

"Oh Deshawn, can I join you?"

"Yeah. Hurry. I had to go out and make a call. Had to give my wife a fake reason for not coming home from work."

I walked demurely to his bed. He had a ball cap on backwards, light colored boxer-briefs, and t-shirt. No shoes. And god, he was handsome. He looked at me and his smile made all my preparations seem worthwhile.

"Ya got great legs, gurl."

I did a slow spin move for him so he could admire both sides of my legs. I faced him as I stopped, and flung my blonde hair backwards. I licked my lips. Was there any doubt that I was a bitch in heat? That me, a slender submissive white gurl wanted nothing more that to be touched, kissed, fucked, possessed by this young stud at his sexual peak?

He patted the bed. Of course I obeyed and sat down next to him. But I didn't move. He sat up and moved next to me. His dark brown thigh touched my pale white one. A jolt of sexual energy surged thru me. I crossed my legs to hide my hard clit. But he knew.

He reached out and stroked my hair. "Ya like the fishnets?"

"Yes, Deshawn. Nobody ever did something like that for me before." I felt waves of heat flowing from his body. I touched his muscular dark brown thigh with my cool, pale hand. He felt hot. I turned my face towards him. I gazed into his brown eyes. He looked into my blue ones.

He moved his hand to encircle my waist and pulled me into his arms. His lips found mine and I knew that I would be happy this night. My thin lips were no match for his broad, soft ones. He held me tight and slid his tongue against my lips, tasting my red lipstick.

"Hmmmmm" was all he said. I relaxed against him, letting him explore my legs with his hands. His gently stroked my legs. They parted for him automatically. I knew that a white gurl should submit to Black men's desires. Both would find the ultimate joy in each other's embrace. I didn't want to break the kiss, and neither did he. His tongue thrust into my mouth suddenly.

"Ahhhhh" I groaned into his mouth as he completed the invasion. His tongue owned my mouth, and it just felt so right. My dress was up to my waist. I saw his eyes feasting on my legs. His dark hand traced small circles against the white skin above the stockings, and I knew I wanted him more than I had dared admit to myself.

Finally, he broke our soulful kiss.

"Ya mine, now."

And I was. So when he, without warning, let me go and sprawled on his back and put one foot on my lap, I knew what he wanted.

I repositioned myself on the bed, and my heels slipped off.

"Put em back on. Now! Ya sexy in em. Makes ya legs even sexier."

How can a gurl resist a command like that."

"Yes Mister Deshawn" was all I could think to say as I put them back on. Now for what he wanted.

He was wriggling his toes, as I gently took his right foot into my hands, and raised it to my lips. We made eye contact. He grinned in a very nasty way. I kissed his foot. It was a bit pungent, but only in a sexy, male sort of way. I began slowly licking each toe. I felt a bit degraded, but I liked it. I realized that it made him feel good, and that is what I wanted for him.

"Suck on em. My bitch wife don't dress sexy, got fat, and won't do no freaky shit like this."

I took his big toe between my lips first. Then each toe in turn. My tongue licked them each like they were lollipops. He groaned his approval and began rubbing his cock as I licked and cleaned his feet with my mouth. I could tell that he enjoyed watching a sexy white gurl service him this way. When I finished with his first foot, I did the other. I saw his black cock making a tent in his shorts. I thought how lucky I was to have him here. With me.

Did he wait for me to finish his second foot. Hell no.

"Git up here, Jill." He motioned to his waist.

I crawled into his arms first. He hugged me close. I heard him sniffing.

"Shit ya smell good."

"Thank you, darling. For you. Only for you"

His cock was pressing against me as I slid down to his nipples and began licking the thin sheen of sweat from his chest. Salty. His nipples got erect between my lips. I was in heaven. And he was my god.

""Fuck gurl, keep goin' down. Gimme head. Now!"

These words I so love to hear. Unlike genetic girls, we special gurls enjoy being women for our men. Giving our men what they really want.

I looked into his eyes and saw the burning lust that gurls like me crave. It means we were doing things right for our man. He reached down and pulled his cock out. Kicked off his shorts. I touched it. It was purplish black and hard as steel. I won't exaggerate, like so many stories do. It was probably 8 inches and rather thin. At first. I didn't mind. I knew I could deep throat this Black man and show him that I was a worthy gurlfriend.

My lips lowered to the head. I tasted him and licked away the precum. The head was velvety and textured. He was circumcised, so I made sure to pay close attention to the flap of skin that is so sensitive. One of my hands was gently stroking his shaft as I sucked the head. The other hand had cupped his very large balls. My nails gently raked his sacks - just to make him tingle with added pleasure.

"Jill, I luv it when ya cup em like that. My wife never ... oh fuck her..."

I took my mouth off his cock just long enough to say, "Deshawn darling, I love tasting you, licking you, sucking you. I'll wear whatever you want me to wear and do anything for you. I keep my stockings on all night, so you'll feel them whenever you want."

Now I felt in control. I resumed sucking the head. I swear he had gotten even longer and thicker. I took two inches into my mouth. Then two more.

"Yeah, feels goooood..."

Then I gave him the gift that he needed. I angled my throat just so, and dropped down, taking all of his cock into my throat. His pubes tickled me. His scent drove me wild. Black musk - what every white gurl craves. Inhaling deeply, my clit hardened even more. His dark thighs were so close, and smelled so good, that I wanted his pleasure to overwhelm him.

"Ahhhhhh sheeeit. Ya suck so good."

I slowly raised my head. He would have none of that. His strong hands grabbed my blonde hair and pushed me back down onto his superior African cock. Now he was back in control, and I loved it. There is no feeling so sublime as being a white gurl under the control of a Black man. Try it gurls...you'll see. You'll have the most intense orgasms of your life. Trust me.

But I still had a surprise for him. My tongue swirl. My tongue began licking his shaft slowly up and down. He moaned, but still kept my head impaled by his cock. It was a battle of lust now. Could he keep from cumming, or would I prevail, make him cum, and release that torrent of salty protein pleasure?

Now the swirl began. My tongue stopped licking just up and down. Now it touched the tip of his cock and swirled around it until it reached the base. Then I started back up. It was a move I knew would please him. I would learn what turned him on the most. Maybe giving him a blow job in his car. In public. At a stoplight, maybe. Hmmmmm.

"No...not gonna cum yet...nooooo..."

But I knew better. He was out of control. His cockhead swelled. His cock hardened even more.

"Jillllllll...I'm cummin'....."

God I love those words.

I felt the cum rocket up his shaft. The first blast was a long stream of creamy white that went right down my throat. Hardly tasted it. And I wanted to. I pulled back, keeping just the head in my mouth. The second blast filled half my mouth as my tongue swept across his cockhead, intermittently interrupting the stream, but allowing my tongue to be bathed by this Black man's essence. His flavor was strong. I could tell that he had many more sperm than usual. Black men will impregnate the world! I swallowed just before the third and fourth streams erupted, filling my mouth. I savored every drop. Sitting up, I opened my mouth so he could see how he had filled me up. Then I swallowed for him. A queen swallowing her king.

I saw his eyes. His face grimaced as I stroked his balls, urging every drop to come forth. Wait, he was not done cumming! I took him again between my thin lips.

"Uhhhh...Uhhhh....Uhhhhh..." He came until he could not cum any more.

After I swallowed the very last surge, not spilling a drop, I saw his eyes open again. His lust was momentarily sated. I think I had pleased him. I certainly hoped so.

"That was da best, Jill baby."

His legs wrapped around me and one dark brown leg wedged against my hard clit, rubbing up and down.

"Deshawn, stop, or I'll cum."

He grinned and locked me in his leg embrace. His leg rubbed against my clit and would not stop. He laughed at me. He knew he was controlling me... in all ways.

"Oh god, Deshawn...oh no...I can't stop it...I cannnnn't stooooop."

Cum shot into my panties as this Black man's leg delightfully tortured my white thighs and crotch. I came deeply, feeling both love and lust. Finally, I couldn't cum anymore.

"Darling, I need to clean up. I don't want to displease you."

He pulled me on top of him. My wet crotch against his.

"Ya ain't gettin away from me, gurl. Roll on your stomach and keep that dress hiked up."

I did as I was told. I straightened my stockings so my legs looked good to him. Raising my dress and moving my hips upward did not go unnoticed by Deshawn.

"Ya got a damn tight body, gurl."

I wiggled for him. "Why, do you like me?"

He didn't say anything, but suddenly I felt his body press against me and felt his hot breath against my ear. He blew into it and I got shivers. He stroked my nipples until they felt so hard they would burst. Then he squeezed them. I dreamed for a moment that I was feeling a Black baby nursing at them. His Black baby. But then, I'm only a gurl.

God - he was hard again! His cock pressed against my panties. He was mounting me from behind!

"Gonna breed ya now, white gurl. You liked swallowin' my seed. You gonna take it the way a real woman should, and you gonna like it even more."

He was going to treat me like a real white girl. One who wants to have a Black baby to please both herself and her Black man.

He suddenly yanked my wet panties off me. Not down over my legs. He just ripped them off. Then he sat back.

"Damn fine ass for a white gurl. Uh huhhh." He slapped my bottom so hard I cried out. He laughed, then rubbed the sore spot. Then he slapped it more gently, before leaning on me again. Only this time I felt his cock slide between my ass cheeks, just bumping into my ass-pussy. I took an involuntary deep breath.

"Deshawn, I didn't bring anything for back there..."

"We cool. I got stuff for ya. Some nice KY. Warm ya up."

His fingers began running up and down my ass-slit. It felt so good. Then I felt the warmth. My ass-slit felt the heat spread, and it made me relax my sphincter. I couldn't help it. His cock touched me there again. The heat of this engorged Black cock sliding up and down my white ass-crack was making me feel more submissive to him. I could deny him nothing.

"Feel good? Ya like this Black cock?"

"Yeeeessss. But it feels so big..."

"Maybe I stop now, huh?"

"No!"

I reached backwards and tried to pull him into me. He hadn't pushed himself into me yet. I was so eager for his BBC that I didn't even care that we didn't have a condom. I knew that was wrong, but when a passionate white gurl meets a passionate Black man, all hell breaks loose.

"I see what ya want, Jill. Let me put some KY on my cock first. This might hurt ya at first..."

"I don't care. I don't care! I want you in me. Please, darling."

Then I felt it. His cockhead, covered in the warm KY, pushed into me. Just an inch. For all his tough bravado, I knew that he didn't want to hurt me. Too much, that is. I opened for this hard Black man like I had been born just to please him. Maybe I was. He gently pushed another inch inside me, and I gasped.

"Ya OK?"

"Yes...yes...you're just so big..."

"Bigger than your white boyfriends?"

"Oh...yes. You taste better too."

"Gonna ever go back to em?"

"Oh god - no. Fuck me, Deshawn...make me your woman in all the ways you can. I am sooooo lucky to have you."

"Damn straight. Try some more."

He laid completely on my back now, as I felt him push more deeply into me than any man, Black or white, had ever done. His heavy Black ball sacks rested on soft, white ass cheeks. I knew now that I was born for this.

"My goddddd. Ohhhhhhh. Yes, darling, yes... Don't ever stop fucking me."

He began pulling back and plunging in. His hardness was driving me onward and upward. I heard the slurping sounds of the KY mixing with his precum as he coated my insides. Once, he stopped and turned my head for a deep soul kiss. It was a kiss that told me that I was his, and nobody elses. I sucked at his tongue and he obliged by sending a stream of saliva into my waiting mouth. He tasted good - all over.

Then it was back to him possessing me in the ancient ways that men have possessed their women since the caveman's days. He was pistoning in and out. Furiously. I felt and loved every stroke. My clit was getting harder and harder again, and the knowledge that he was inside my body, about to cum, and cum inside me made me clamp down on his cock.

"Shit gurl, ya so tight! Ya da best I had."

"I want you, baby. I want you to cum so deep in me that I can't walk. Your cum I need. You I need."

"You dress like this, and suck and fuck like this, I be back."

Then he slowed down his fucking. Slow strokes now.

"I wanna remember how my Black cock looks splittin' ya in two. Wanna see if ya spill any cum."

"Oh Deshawn. Fuckkkkk me. Don't stop!"

With those words, I came again. The sheets got soaked. As I came, I clamped down harder on his beautiful cock. The added friction pushed him over the edge.

"I breedin' ya now. Feel it. Feel it. Uhhhhhhh..."

And came he did. He timed it so every down stroke into my ass contained another stream of his cum. How many? I lost count. All I can say is that I felt his sperm enter me, run inside me, and make me his woman. I only wished I could get pregnant and carry his Black baby.

He collapsed on top of me, and we both enjoyed the feeling of each other's bodies, so different in color, but so alike in passion. His cock was getting limp, but he kept it in me as long as he could.

A tear came to my eyes as his cock popped out. I could tell he was looking at my fine white ass as my muscles constricted and i did not spill a drop of his seed. That seed that was so very precious to me.

We crawled to the top of the bed and he wrapped his arms around me and brought our lips together. As we soul kissed, I realized there was a chance I could fall seriously for this man. I didn't care what the world thought. I needed his strength. His kiss. His lust. His cum.

I felt him pull the sheet and blanket over our wet bodies. He was protecting his gurl from the cold cruel world. And I would protect him.

"I gotta call my wife, let her know I'll be even later..."

"Don't leave me, Deshawn. Please, darling."

I held him close. We slept. I dreamt.

12
  • Index
  • /
  • Home
  • /
  • Stories Hub
  • /
  • Transgender & Crossdressers
  • /
  • Jill's Date with Deshawn

All contents © Copyright 1996-2023. Literotica is a registered trademark.

Desktop versionT.O.S.PrivacyReport a ProblemSupport

Version ⁨1.0.2+795cd7d.adb84bd⁩

We are testing a new version of this page. It was made in 19 milliseconds