Sexy Hung Red Head

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Well hung shemale meets well hung stud.
2.3k words
4.33
74.6k
83

Part 1 of the 2 part series

Updated 06/07/2023
Created 10/27/2015
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mrstanley
mrstanley
305 Followers

This story is written from the Shemale's point of view. "Francine" is based on a real Transgender woman from California. She gave me the outline of a meeting she had with "Jonathan."

*****

My name is Francine and I am a natural red head blue eyed 34 year old Transsexual. My skin has a very light complexion with numerous freckles. I have been on hormones for ten years. I have been living as a full time woman for eight years. My height is almost six feet tall and I weigh 160 pounds. My measurements are 38-28-37 and my chest is a small C cup. Even though I am thin I appear to be a tall muscular woman. I lift weights for definition and my forearms, biceps and calves are heavily muscled. I can bench press 230 pounds and dead lift 400 pounds. When I work out in the gym all the women that I work out with are amazed at my strength.

I live in the Las Vegas area and work as a real estate agent. No one at my business knows I am a T girl. My male co-workers flirt with me all the time. I am very passable and receive frequent compliments on my appearance from both males and females. My face has undergone two plastic surgeries. My adam's apple has been shaved and I have implants in my cheeks. I look like a pretty cat with prominent cheeks that accent my eyes. My body is natural and the hormones have helped develop my feminine shape. I date only outside of Las Vegas due to my concern about privacy. I know in the world today people show more acceptance of Transsexual women like me. I still have a great fear of being discriminated against.

My appearance greatly resembles that of the T girl porn star Mia Isabella. I have been stopped several times and asked for my autograph by people thinking I was her. When Mia visited an adult club in Las Vegas recently we actually met. She thinks we look like sisters. The only major difference in our appearance was our size Mia is 5'5" and weighs 120 pounds. I have seen her videos and know we are about the same size where it counts. She has my number and we are going to meet the next time she comes to Vegas.

I have three days off this week and am going to Phoenix to play with a man. My red F type 2015 Jaguar could cover the 300 miles in less than two hours. I figure I better take it easy on the drive and give myself about five hours of traveling time. No need to run up too many speeding tickets. It is a warm day for May as I begin my drive. I am wearing a light weight low cut red dress and four inch high heel thong sandals. My nails on my hands and feet are a sculpted hot pink. My arms and legs are smooth with a light coat of body oil. My sizable bulge is held in place by a red pouched G-string.

As I think of my boy toy for this weekend I grow erect. It is just past 7 am as I leave Las Vegas on the road toward Phoenix. I am meeting a sexy 27 year old hunk named Jonathan. We met only three weeks ago on the internet in a chat room. He knows that I am a shemale. We already know a lot about each other. We have video chatted on numerous times this past week. I think of all the things he said to me. He detailed how he would suck my cock and swallow my length when I arrived. I challenged him to see if he could accomplish that. No one has ever been able to take me all the way orally. He is well hung as well and wants to top me. I plan on seducing him when I arrive. Thoughts of hot steamy sex run through my head as the miles of highway remain ahead of me.

My car arrives in Scottsdale at noon. It takes me a few minutes to find his place. His house is a massive structure in a old Spanish style. He opens the door and walks out to the driveway

.

"Hello Francine. I love your outfit. How was your drive?" He asks as we hug.

Jonathan is a little taller than I am. I estimate his weight at 190 pounds and he has the body of a Greek God. His hair is fairly long nearly shoulder length. He is dressed in a flowered shirt, khaki shorts and sexy Gladiator sandals. His legs and arms are smoothly shaven. My eyes travel to his crotch and I can see a sizable package that looks to be erect.

"Thank you. My drive was nice I thought of you as I drove." I respond.

"Come in to the house Francine."

He opens the door and I follow him in. He gives me a tour of the house. I can see he is nervous as we take a seat in his living room.

"Jonathan do you have any iced tea?"

"Yes that sounds good Francine." He says as I notice his eyes on my body. I watch his eyes as he gazes at my tits. His eyes move over the rest my body. He looks at my waist, my legs and my feet. He licks his lips as his eyes lock onto my thick bulge that has grown into a thick erection. After a few seconds of looking me over he leaves the room to get our tea.

I decide to surprise him and remove my dress. I have only a red thong G-string and my thong sandals on. My cock is now fully erect and pushes against the silk pouch in anticipation. I patiently wait for him with my legs crossed in my chair.

He walks back into the run and nearly drops the tray with our glasses of tea. Our eyes meet as he places the tea on the table.

"Cat got your tongue? I ask.

"I see you got more comfortable. You are so beautiful I can't wait much longer Francine. "

I move my sandaled foot to his crotch and move the points of my toes along his thick erection.

"Did I do that? Or were you already hard?"

He places the drinks down and we slide into the love seat next to each other. We kiss and melt into a lustful French kiss. His hands slide over my slick smooth body as he buries his tongue in my throat. I rub his calves, ankles, thighs, butt, chest and sides. I use the very tips of my fingernails on his sides. His hands caress my breasts and hips. He attempts to remove my thong and I stop him.

"I want to please you Jonathan. Let's get all your clothes off." I remove his shirt and squat on the balls of my feet before him. My face is level with his crotch as I unsnap his shorts and slide them down his ankles. His erection tip springs out and hits me across the nose. We laugh as he steps out of his shorts.

"Wow, I had no idea." I say.

"No idea about what?"

"You are so big. I love how thick and smooth you are. I love a shaved cock and balls. Is your asshole shaved as well?" I ask.

"Yes I am totally hairless. I wanted to surprise you Francine. Are you happy with me?"

"Jonathan this changes everything." I say as I grasp his cock with one hand and tickle his balls with the other.

"Is it too big for you Franny?''

"No, it is what I have been looking for. I have never found a man equal to me in that department."

My tongue snakes around his helmet before I engulf his thick long shaft with my soft ruby lips. I don't just suck his dick, I make love to it with my mouth. I start very slowly at first, and my lips wrap around his curved thick tip as my hand caresses his shaft. His hands run through my thick red hair as I fellate his organ. I never break eye contact, and the look of lust in our eyes is mutual. My lips circle along the sensitive undercarriage of his thick helmet before I swallow most of his length. I spit him out and run my tongue back to his tip. I tease him by lightly biting his cock head.

"Watch this Jonathan." I swallow his huge thick veined penis down about half way. My lips travel back up to the rim of his head and I swallow again until I have him down balls deep. I tickle his balls as his cock slides into the back of my throat. His grip on my head tightens and he meets my bobbing head with strong thrusts of his hips. I grip his calves as he fucks my throat. His cum filled testicles slap my chin on each down stroke. I gasp after deep throating him and a strand of thick semen drips from his cock. I swallow his pre cum and smile into his eyes. "I don't want you to cum too soon Jonathan." I say as I stand up and run my hands over his heavily muscled chest.

"What do you have in mind Franny?"

"I think it is your turn. Get on your knees you pretty boy and see if you can handle Franny."

I slip my thong down my legs and kick it across the room. I am naked now accept for my thong sandals.

"My god Francine you are bigger than me!" He says as he reaches out and grasps my thick cock.

"I am pretty big Jonathan. The hormones have not affected my size. I am a size queen. Big cocks are what I like. You told me you were big, so I thought I would see for myself. You have a huge cock Jonathan Your penis is about 8 inches right?"

"Yes 8 and ¼ inches and 7 inches around. You are at least a full inch bigger Francine."

"My last boyfriend had my cock bronzed. That was the first time anyone actually measured my penis. I am exactly 9 and ½ inches long and six inches in circumference. Your cock is very thick. I had a little trouble deep throating you."I rub his head with my hands as I move closer to his tongue that is pointed toward my cock.

"I hope the view is as good as the one I have Francine," He whispers before swallowing the head of my erection.

I think my view is amazing as my long thick slippery cock slid into Jonathan's sucking mouth. I gazed in wonderment as he takes me farther down on each swallow. His eyes bulge out as I grip his head and fuck his mouth.

Jonathan is gagging and comes up for air. "Fran your cock is too big for me to deep throat. How far did I go?"

"Baby you had me down almost 8 inches. I have never been deep throated. Most people can't take me half way down. I have an idea. Let's see if you can take all of me in the ass."

"Okay, but take it slow." Jonathan says.

"Roll over on your back John." I say as I untie his sandals and slide them off his feet. I grasp his ankles and move his legs high in the air and move my head toward his smooth shaven rosebud. My tongue rims his asshole and my tip penetrates him. He moans as my tip vibrates into his open anus. I spit in his ass and slip my index finger deep in his rectum and probe his prostate. His cock jerks and leaks drops of semen. I swallow the semen by engulfing his tip. I return to milking his prostate and add two more thick long fingers. After about five minutes his sphincter is loose and relaxed.

"Fuck my ass Franny. Go slow, don't hurt me with that big prick."

"I will go slowly at first. You will beg for me to bottom out before I am finished." I place the head of my veined erection at his anus and push about three inches deep. He groans and gasps as I slide out and push another inch deep. I repeat this until I have about six inches in his ass. He is relaxed and I fuck him at this depth for about ten minutes. His cock is hard and I jack him off as I piston my cock into his ass.

"Franny fuck me with all of your cock. I want all of you. You feel amazing."

I move off my knees and slid his torso so his ass hangs off the love seat. I stand and place my heels on the floor. My smile met his as I reenter his anus with my tip. I grip his ankles and drive my prick into his ass as deep as I was before. I now use the leverage of my high heel thongs to plow balls deep into his anus. My cock is hitting his prostate on each stroke. I watch his thick erection pulse and spasm in the air as I fuck him. I move his legs higher and wider as my ball sack slaps his cheeks on each down stroke.

"AAAArrrrrrrr! AAAArrrrrrrr!AAAArrrrrrrr! AAAArrrrrrrr! AAAArrrrrrrr! I am coming Franny fuck me hard." One huge bolt of thick semen shoots from his cock. I quickly slid out of his ass and dive toward his orgasm. I swallow his entire thick penis in one gulp and ingest about six or seven huge shots of thick cum.

I gulp his seed down my throat until he is finished cumming."Wow Jonathan you are amazing. You took all of me. Did I hurt you?"

"I am sore, but I will adjust to your size. I think it is your turn." Jonathan says.

"Let's get cleaned up first Jonathan. I think you need to rest a while since you just came."

The lovers enter the shower holding hands.

To be continued...

mrstanley
mrstanley
305 Followers
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AlessiaTravestitaAlessiaTravestitaover 2 years ago

Superb story, very erotic. Got me totally horny. Alessia. xxx

AnonymousAnonymousover 8 years ago
That is a scorcher

Hi sexy. Please post a photo?

AnonymousAnonymousover 8 years ago

I got broken in by a tranny. I was 48, I picked her up off the street, she was a bit older than the others. I had driven around about 8 times before I stopped. I also watched as she got in and out of 3 cars. Black, a bit plump, but looked like a woman. When I stopped she came over, a nervous hi, hello sweety, um, ah, first time eh, let me get in and we will talk. Her dress rode up, I got a glimpse of red panties, her hand on my leg. If you want my lips around your cock, that's a fifty, she leaned sideways displaying her pantied bottom, if you want to slide in there, that's a hundred, in the car, in a room another fifty. Silence, well big boy, um how much for both, she looked at me as if I was dumb, then said for you $100. O.k, I gave her the cash, lets drive, she directed me, all the time feeling my cock through my trousers, I was hard. Pull in there, park length wise across the marked spots, I did. Only other girls come here, its pretty good. Hop out, she did too, lifting her dress, what do you think, mm, nice, she certainly had a big round bottom. She sat on the passenger seat, door open, o.k, pull them down. I did. mm, nice cock, feeling it, nice and hard, as she moved forward, taking my cock in her mouth, mm, I think your ready, I was. She undid a condom, rolling it on my cock,, then she turned, kneeling on the seat, felt for my cock and holding it in place, pushed back, opening for me, my cock sliding into her, rather easily I thought, then said, o.k but go easy, I went slow at first, you o.k, yes, fuck me, so I went at her. now I am not that big, 6 inches I guess, but I am thick and her ass grabbed my cock beautifully, milking me, I felt my cock growing, and then my cum left me, ohh, I heard her say no, don't stop, I kept pumping until I was done. I stopped, no keep going, don't stop, I went for a short time, then she pulled away. She turned, with tissues, removing the condom, I looked down, her cock was sticking straight up. Wow, your thick, I could feel you moving in me, I nearly got off.I looked at her cock sticking out from under her dress, my hand moved to it, stroking, hard, bigger than mine, not as thick, can I suck it, she moved to me, it was not my first time, as she moved back and forward,but I just couldn't get her over the line. she pulled back, thanks, I was so horny now, a big woman, with a big cock, I said put a condom on, she looked at me, my first but I will give it a go. I watched as she did, on your knees, lower, that's it, I felt my hole exposed, then cold lube worked around and just inside. I was nervous but relaxed after coming, my cock was semi hard as I felt the head of her cock, a sharp push ,aaagghhhh,, she was in, small movements, then push, I felt my insides expand, there was pain but my cock was hard, then she started, that's it, take me, oh yes as she fucked me, long pushes, in and out, I felt I felt her cock grow bigger. I had to touch mine and I did and 2 strokes more cum left me,i heard her oh fuck and she felt much bigger in me then gradually slowed. She pulled out, ouch, cleaned me and then herself. We drove back, when I stopped she said anytime, you know where I am and got out.

AnonymousAnonymousover 8 years ago
I want her!

Best Tranny story ever. I jacked off and fingered my ass after reading this.

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