tagTranssexuals & CrossdressersTonisshy gets Southern Hospitality

Tonisshy gets Southern Hospitality


***Writers Note***

This is purely fiction. I am in no way a writer I just enjoy these fantasies as I don't have any other outlet to actually dress and be the gurl within me.

Thank you and I hope you enjoy.


A little about me first. My name is Toni and I'm a crossdresser. I'm 24. I stand 5' 5" tall. I'm thin with long legs and a nice girlish figure. I've been described as a really cute tomboy even when I'm not made up. When I am all dolled up I've been told I am passable as a girl.

My friend Matt is a young stud. Tall dark and handsome. He is bisexual but says it's just beauty that's he's into. Not the gender. We've been friends forever. Sometimes lovers but mostly friends.

I live off a meager trust fund until I turn 29 or until I get married. It's only gonna be 5 more years!!

Matt plays cards for a living. Together we do okay but not great. I am at the beginning of a payment and have 3 more months to wait for a nice end of the year check. We just bought this car, a Dodge Ram. Second owner.

This is what happened when we went to one of Matts tournaments.

Matt and I were heading back to Philadelphia from Memphis, Tennessee when our truck broke down in a little town in North Carolina. We had enough money from his winnings playing Texas Hold Em at a tournament in Memphis, to get a room for a week while our truck was being fixed.

This little town, which I'll leave unnamed, is cute. Old southern hospitality, great southern people too. Matt found out online about a gay club which we went to. Nice, with a cabaret show and lots of gurls like me.

And the men, they loved us gurls. The night we went I didn't dress up. I went as my tomboy self.

Matt wandered off, probably to smoke a joint and left me alone at a side bar.

I never expected what was about to happen next. An older gentleman came over and sat down next to me. Good looking, grey hair matching goatee. He had blue eyes, an easy smile and he was built stocky.

"Now I'll stake everything I own," he started with a deep southern drawl, "that you would make every man in here go crazy all dolled up. Am I right?"

"What makes you say that?" I asked with a smile.

"Darlin, I know beauty when I see it. And you my dear are a beauty." He raised his beer to me and I toasted him.

"Why thank you, sir." I said politely.

"My name is Owen Turner and you are?" He extended a beefy hand to me.

"Toni Marten. Nice to meet you Owen."

"The young man you're with, boyfriend?" Owen asked.

I shook my head.


"No sir."

"Then he's plain old stupid?" He asked with a grin.

"No sir. Matt and I go way back. We've been friends forever." I explained.

"Well how bout you and your uh, friend join me for a barbecue tonight?"

I looked at my cell phone "its 10:30 at night!" I laughed.

"By the time I get home I'll be craving a steak, grilled potato and corn on the cob. How about it, Toni?"

"I'll ask Matt."

"And if Matt isn't game, will you at least join a lonely old man?"

"I hardly believe you're lonely."

He chuckled, "well I am tonight."

When Matt finally returned I introduced him to my new friend and extended the offer to him. The three of us talked awhile getting to know Owen.

Owen as it turns out was recently retired after selling his company. A furniture company. He's also divorced of 10 years. No kids so apparently no hassle either. The ex wife took a young lover and somehow Owen got out of a paying a huge alimony.

He loved the outdoors, car racing of course and baseball. He was also an avid fan of barbecuing.

Matt, despite himself liked Owen as much as I did. But he declined the barbecue. He said if I wanted to go I should. But he urged me to keep in constant contact.

So I told Owen I was going back to our hotel room to get a few things then I'd call a cab. So he gave me his address and said he'd get the grill going.

I told him I may be a little while. With a knowing grin he said, "I hope so Toni!"

There are so many joys I get from crossdressing, getting dressed up is one of them. Getting dressed up with the notion I may get lucky, is the best though.

I showered with a vanilla scented body wash and shaved what little hair I have. I left a nice landing strip down by my little boy clitty. After my shower I cleansed my boypussy. One can never be too ready and clean.

I put lotion on my legs to make them smooth and soft. I did my makeup, my hair and then had to choose an outfit. Maybe two.

I pulled on white lace panties and padded c cup bra. Then chose a light blue shirt dress that was clingy to my shape. The heels were 4" blue suede with tassels. Very sexy.

I threw in my backpack a few surprises and a couple extra outfits.

I was nervous, excited and ready. I called a cab, said goodnight to Matt and headed off for a new adventure.

I arrived at Owens house and was amazed. A brown rancher on the lake that was huge. Three car garage, beautifully landscaped from what I could see. Huge red double doors for the front entrance.

The door opened before I even got to it. Owen stood there smiling in his jeans, t shirt and bare feet. He is a bear of a man and so good looking.

"I knew it, darlin!! C'mon in. I just got everything ready to throw on the grill." He said as he led me in.

Through the long hall past a spacious living room, a nice office on the other side and into a wide open kitchen and dining room. To my left the whole wall was a window with a sliding glass door. A pool outside and hot tub. And before me through the cozy family room was the lake. What a sight even at this hour.

He made us each a mixed drink then we went outside by the grill. For the next half hour or so as he cooked and talked. A lot.

He was very interested in me too. Made it a point to ask the right questions and really listen to me. He also told me how he came to find a fondness for gurls like me. It was before his divorce in Miami at a club. At the time he really thought she was a female but she set him straight telling him all about her. He liked her as a person and after several visits down to Miami on business and not, they became very close before intimacy. When they took that step he never looked back. He knew this was the type of bisexual man he was. He just knew.

He hadn't considered it cheating because he had known for some time that his ex wife had had a lover. Actually, at that point she had two. So he didn't consider his affair infidelity.

We had a nice midnight meal of steak, potatoes and corn on the cob. Afterward he made us another drink and I helped him clean up. From there we went into the family room. There was a three stool bar where we ended up.

I was nervous but I was also eager to get past that moment, the sexual tension before one makes that first move.

Does that make sense?

He sat close, our elbows touching.

"Toni, I am nervous. It's been over a year."

I got off the stool and turned his toward me. As he sat looking into my eyes I opened his legs and stepped in. I put my arms up on his broad shoulders and leaned for a gentle kiss on his lips.

His hands went to my hips, moving to my ass. The kiss grew as I forced my tongue into his mouth. He groaned a little as we made out. My arms now wrapped around him. His hands pulling me in tight. I could feel his package growing against me. I wanted him.

"Can we go to your room?" I asked breaking the kiss.

He took me by hand and led me back through the house, me picking up my backpack along the way.

Once in his bedroom I saw the king size bed sitting up high and felt myself getting butterflies.

"Give me a sec," I said before disappearing into his bathroom. I slipped out of my heels, dropping my dress to the floor and reaching in the backpack for a pink barely there chemise. I took off my bra then slipped the sexy garment over my head and shoulders. Then I pulled out pink open toe 4" heels. I slipped those on then re entered the bedroom.

This time Owen took me into his arms and kissed me passionately, our tongues intertwining our hands exploring each other.

Owen takes me to the bed and laid me on my back, my heels don't even reach the floor. He kisses me gently on the mouth, my face, my neck. His kisses trace over my chest then to each erect nipple where he gently bites. His hands are on my thighs.

I'm dizzy with lust.

He lifts my chemise and kisses my belly. My knees bend as my back arches.

I'm reaching for his cock but he's just out of reach. Owen continues kissing me until he reaches my clitty. I'm tucked back in my panties as I always do. I grow nervous because I've always had a complex about the small size. But Owen buries his face in my crotch. I feel his nose, his breathing. His goatee gently tickles me.

Then he does something to me that has never happened before. He began licking me through my panties, licking me like I was a woman. My eyes rolled back as I bit my lip. Owen continued to work my clit as I shook uncontrollably. It felt like my body was vibrating, emanating from where he was working his mouth. My thighs locked around his head, I pushed down on the back of his head not wanting him to stop.

"Ohhhhhhhhhhh!!" I moaned!!

In one quick movement my panties went to the side and he took my little clitty in his mouth and I exploded like I can't detail in words. I seemed to keep cumming...my body tenses up as I'm nearly spent. I couldn't imagine anything like this before.

Slowly I relax my hold on Owen as he finishes me off and begins to stand. I lay there looking at this man as he slowly walks around the bed, his cock straining against his jeans. He was on the other side of the bed now taking off his jeans, no underwear. I couldn't believe my eyes when I saw the size of his cock. It was at least 8" long, cut and pulsing as he waited for me. The head was already dripping with precum.

I rolled over and seductively crawled to him. I opened my mouth and licked the precum away, kissing his head sensually. I made love to the head of his cock with my lips and tongue.

I never had a massive piece of meat like this before but I was determined to take him all in my mouth. Inch by inch I worked my way down coming back up then going further down. It took several attempts, a little bit of gagging before my nose touched his shaved crotch.

Owen moaned, his hand going to the back of my head gently. I cooed as licked his balls with his cock still down my throat.

"Roll over Baby..."

I did as he asked and on my back Owen slid all 8" plus inches back into my mouth and down my throat. He began to slowly fuck my mouth. His hands all over my legs, his musky scent filling my nostrils.

"Toni, ohhhhh sweeeetieee..." he moaned. "I want to be inside you."

I moaned in delight. Excited, scared and eager to take this man in my boypussy.

He pulled out of my mouth and I changed my position so my ass was to him.

"Face down Baby, ass up." I did as he commanded. "Ah what a perfect ass" he said. He opened a drawer in the nightstand next to the bed and took out lube.

In my position I waited for the cool gel to hit my hole but instead I was pleasantly surprised to get a warm tongue licking all around. He kissed both ass cheeks the licked my crack from bottom to top then returning to my hole. His tongue just on the rim.

"Oh my God!!" I cried.

His tongue protruded the hole and I gasped in ecstasy!!

He worked my sphincter until I was screaming for him to fuck me!!

He lubed my entrance and his cock. I felt the head on my hole, he rubbed it up and down my crack and back to my hole before slowly, gently he pushed in.

My back arched, my knees bent and I pushed back to take him inside me. I felt a slightly painful pop and he was in me.

"Ohhhhhhh!!" I moaned. A little more pain as he pushed through slowly but that pain quickly changed to sweet pleasure.

He held himself in place for a moment and asked, "are you okay, Toni?"

"Oh yes baby, please more. Please!"

And Owen continued in slowly until he was as far as he could go. I felt every inch of him my body having an all over tingling sensation.

The he pulled back only stopping when his cockhead reached my hole. My fists clenched the comforter as I pushed my ass back onto his cock taking him all the way back in.

"Mmmmmm," I moaned as I slid down his cock.

"Oh yeah baby, work that ass!"

I began moving my hips up and down on his massive cock. Taking him all the way inside me and holding him the before releasing and letting him glide almost out of my tight ass. I didn't want this to end!!

With his big hands holding my hips, I pumped his cock slow and steady.

"Move up on the bed, sweetie."

I did as Owen asked and now he pushed me on my stomach. Only my ass was up with him still inside me.

He started to ride me now. He has taken charge and was beginning to pick up the pace!

"Ohhhhhhh!" I groaned. Owen was laying on top of me. When he pushed in and out he barely came out of me at all. I had every inch of him inside me and I was floating on a cloud.

"You have the sweetest pussy, baby!" He grunted.

He was really pounding me now.

"Ahhhhhhhhhhh!!" I screamed "fuck me Owwwweeeennnn!!"

In a quick movement Owen lifted himself to position where he is pounding me hard. I felt him go all the way inside me where I'd lose my breath then come nearly all the way out. My legs was shaking uncontrollably as I came all over myself.

He was really going at my ass hard now, I was moaning loud. "Pleeeeaaaasssseeee cuuuuummm in meeeeeee!!"

Owen gave a grunt, tensed his body and then I felt him shoot his hot load deep in my boypussy. He seemed to never stop as he would push and shoot push and shoot.

At last he lay on top of me, completely spent. He kissed my neck, nibbled my ear. I turned to meet him and we kissed passionately.

He was still inside me and I never wanted him to back out.

"You are so sexy." He whispered.

"Mmmmm, thank you." I cooed.

"I'll get us a towel," and then, slowly he pulled out of me and I felt so empty. I watched him walk away and go into the bathroom. His large member still hard leading the way.

A moment later he returned with a warm towel. I could feel his juices flowing out of me then the warm towel wiping me clean.

Afterward we lay together with me cuddled up in his big powerful arms.

"That was amazing, Owen." I said kissing his chest.

He kissed the top of my head and gave me a gentle squeeze, "I'd like you to stay with me while y'all wait for your truck to get fixed."

I looked up at him and smiled. "Okay."

"Maybe you'd like to invite Matt too?There's plenty of room."

Matt, I forgot to text him.

"Toni, I'd like you to be my girlfriend while you're here." Owen said.

"Oh, that's so sweet."

I honestly have never had a boyfriend. A lover or two but never had I been anyone's girlfriend.

"We can have so much fun, I promise."

"Okay Owen." We kissed again before I fell asleep completely exhausted.

More later..!! XOXOXO

Report Story

byTonisshy© 2 comments/ 8327 views/ 14 favorites

Share the love

Similar stories

Tags For This Story

Report a Bug

1 Pages:1

Please Rate This Submission:

Please Rate This Submission:

  • 1
  • 2
  • 3
  • 4
  • 5
Please wait
Favorite Author Favorite Story

heartLucy2999, Dro1 and 12 other people favorited this story! 

by Anonymous

If the above comment contains any ads, links, or breaks Literotica rules, please report it.
by Anonymous12/03/17

no need to be mean anon

Tonisshy you keep being who you are and write how you want. We get better by doing it more and receiving helpful criticism. keep going gurl

If the above comment contains any ads, links, or breaks Literotica rules, please report it.

Show more comments or
Read All 2 User Comments  or
Click here to leave your own comment on this submission!

Add a

Post a public comment on this submission (click here to send private anonymous feedback to the author instead).

Post comment as (click to select):

Refresh ImageYou may also listen to a recording of the characters.

Preview comment

Forgot your password?

Please wait

Change picture

Your current user avatar, all sizes:

Default size User Picture  Medium size User Picture  Small size User Picture  Tiny size User Picture

You have a new user avatar waiting for moderation.

Select new user avatar: