Shemale Stories

[a9127]

The following story was inspired by "Toni" the girl on the cover of "Small Town Transvestite" posted in the Drag Queens forum. Hope you enjoy it...

A few nights ago I was heading home from the gym. Located on Oak Street in Zionsville it’s only about three miles from where I live. Many years ago, this was mostly farmland and Oak Street was a dirt road. None of the Interstates existed back then and the “big city,” Indianapolis, seemed much farther away than it does now.

There is a severe thunderstorm that just sort of popped up. The forecast said nothing about storms. I chalk it up to living in Indiana. Suddenly there is a blinding flash of lightning. I pull over and then everything goes black.

When I wake up it’s a clear, beautiful warm summer night. Carefully, I pull back on to Oak Street. Something seems different. It’s really bumpy. I realize that the road is dirt! “Well that’s great… why didn’t they tell us they were going to be doing roadwork at night!” I’m kind of pissed because I could have easily driven my truck. The Hellcat sits so low I can hear it scrape. “Shit!” I check my cellphone and it’s not working. In fact none of the GPS stuff in my car or satellite radio is working! All I can get are “AM” radio stations and they are playing music that sounds like something my grandparents would’ve listened to.

Farther down, I see someone standing at the side of the road. It looks like a girl hitchhiking. As I pull up I can tell she’s wearing older style clothing. Maybe she went to a party? I have a thing about never picking up hitchhikers but I can’t just leave her there so I slow down and stop.

She comes over to the car and I roll down the window. I get a good look at how pretty she is. “Where you going?”

“Anywhere but here. How about a ride to Indianapolis?”

“OK. But I need to stop by my place first.”

“Where’s that?”

“Just down the road.”

Laughing she says “in the cornfield?”

Suddenly I realize my house is gone. In fact there’s nothing at all.

“Ummm… well it used to be here…”

“Are you drunk baby? I mean you are really cute but are you OK?”

“Yeah. I just think I lost my way up here.”

“You and me both...” she says smiling at me. I think I lost mine a long time ago sweetie. You have no idea."

Then you add “Why don’t you come to Indianapolis with me? Maybe we can have a good time.”

You climb in and I say “My name’s Andy. What’s yours?”

“Toni. Thanks for stopping by the way. I thought no one would ever come by.”

“What are you doing out so late?”

“I had a big argument with my family. They told me to get out. I was gonna go downtown and stay with friends. Wow Andy I’ve never seen a car like this. What is it?”

“It’s a Dodge.”

“Well it’s not at all like my dad’s” you giggle. “These seats feel wonderful. I feel like I could sleep in one.”

I head West to where I expect I-65 to be but there’s nothing.

“Andy, you really are lost! I know how to get to Indianapolis from here. Turn around.”

We head back East on Oak Street. In the moonlight, I can see there’s no houses. No gym. No Bentley dealership. Just farms. I recognize some of the buildings in downtown Zionsville but they look so much newer. At least now I sort of know where I am.

“Don’t worry sweetie, I’ll get us there. Jesus! Watch your speed. It’s only 25 out here!”

“25? What do they drive, horses and buggy’s?”

“Well sometimes…”

We drive very slowly but that’s OK, it’s a beautiful evening and we talk about many things. You tell me a lot about your family. “I was always considered the outcast” you say. “When I was younger I was picked on by the other kids in school. Noticing my size and build, you say “I wish I’d had a friend like you.”

“Well I’d never let anyone pick on you.”

“Awww… that’s so sweet Andy. You seem like a really nice guy. Are you married?”

“I was several years ago.”

“Have a girlfriend?”

“No. Not at the moment.”

“You know Andy. There’s a lot of things about me you still don’t know. I wish I could tell you.”

“Toni, you seem like a really nice girl. I’ve enjoyed just talking with you tonight. Can I ask you something?”

I can see you become a little apprehensive and you say tentatively “What?”

“Why are you dressed like that? Your clothes look like they’re from the 40’s or the 50’s. I mean you look great. I just wondered if you were at a party or something.”

“I like wearing dresses. Well at least most of the time. And it is 1949.”

OK. That explains a lot. Trying not to seem alarmed I realize that the storm earlier must have been a “time portal.”

“Well I hope you don’t mind me saying this but I think you’re beautiful.”

“Thank you. You know I hardly ever hear people say that to me.”

“I can’t imagine why not. If they don’t they’re fucking crazy.”

“Where DID you learn that word young man…” you say giggling. "My mom would wash out your mouth with soap!”

“Sorry. I just thought everyone used it.”

“Really? Where are you from anyway?”

“Actually I live right here in Zionsville. In Stonegate.”

“Stonegate? Well wherever you are from I think you are really sweet.” With that you lean over and kiss me.

Then you say “God I wish I could tell you more Andy.”

“It’s OK. It can’t be anything that bad can it? Even if it is I’d help you.”

“Yeah I know you would. I wish there were more guys like you. And yes many people would think it’s something bad.”

This time I lean over and kiss you. You open your mouth a little. Our tongues touch. You run your hands over my chest and arms. I place one hand on your thigh but you stop me before I can go “there.”

“Andy, I want you to tell me what exactly happened to you. Then I will tell you everything.”

“OK Toni.”

Copyright © 2017 AMS

[a9127]

Continued from Part 1 above...

“You know before I saw you driving down the road there was a very bad thunderstorm. I don’t remember anybody predicting one. There was a lightning strike. For a second I was dazed. Then there you were, driving a car that’s nothing like anything I’ve ever seen. And you say you are from around here but you don’t know where anything is. I want you to tell me the truth. Are you like some kind of spaceman or something? Do you work for the government? You know after the war they have had all kind of crazy things like atomic bombs, jet planes, TV, radar, computers…”

“Well I don’t really know what happened either but I was heading home from the gym and ran into a thunderstorm and suddenly there YOU were. Everything I know is gone. No, I’m not a ‘spaceman’ but I think the storm might have interfered with time.”

“Yeah. I’ve read stories about things like that. So what year is it Andy?”

“2017.”

“Oh my God. That would explain everything. I believe you baby. So what do we do about it?”

“I don’t know but we were making out and it was going great.”

“Yeah we were. I really liked it” you say smiling at me. “Now I’ve have to tell you something about myself. If you don’t want to be with me afterward, I’ll understand but please listen to me Andy.” Your face has turned very serious and you look me right in the eyes. They are watery. I think I know what you are about to tell me. You might be surprised at how I really feel about you Toni.

“Andy,” then a long pause “I’m really a boy. Like I have a… you know. Ever since I was very young I felt different. Like a girl. No one understood. They still don’t. The doctors were no help. They all said 'He'll grow out of it.' My mom and dad forced me to dress like a boy and play with toy guns and airplanes and play baseball and stuff like that. I kept asking Santa for a doll for Christmas. Everyone laughed at me. Whenever I got caught trying on any of my sister’s clothes I got a whipping. When I was in school I was always picked on by the other kids. I used to pretend that I was Snow White or Cinderella and invent imaginary friends. The only real friends I have are the ones in Indianapolis I was going to stay with. I’m not a bad person Andy. I’m just different. It’s who I am.”

You are crying now and through your tears say “If you don’t want to be seen with me I understand. But I just want you to know how much I liked being with you tonight. You can take me to Indianapolis now if you want.”

“Toni, I don’t know how else to say this but none of that matters to me. In my time things are different. Sure we still have a lot of the same problems, but you would be surprised at the number of people who are accepting of girls like you. Even fall in love with them or get married. Just like anyone else. My first girlfriend was transgender. Many of my friends are. There are celebrities who are. Unfortunately there are still people around who are just as bad as anyone you’ve encountered but they are in the minority and most people I know see those people as ignorant and bigoted. We even have laws against ‘hate crimes’ in some states. And you aren’t a ‘boy’ you are a woman. A very beautiful one.”

“Andy, nobody but my closest friends have ever referred to me as a woman. Not even my mom and dad. They all say I’m a sissy, a fag, or a queer. The only guys I’ve ever known are creeps who just want to have sex with me for a thrill. Any guy that I ever really liked already had a girlfriend or left me when he found out.” “Well I’m not like them Toni” I say as I hold you. You have stopped crying and smiling you say “Thanks Andy. So, do you wanna take up where we left off?”

You are a great kisser and this time when our hands start to explore you don’t stop me. We both gently stroke each other’s hard cocks through our clothes and breathlessly you say “Let’s wait ‘till we get downtown. I’ll get us a hotel room.” “Let me pay for it” I say getting out my debit card. Laughing, Toni says “What the fuck is that?” covering her mouth in mock shame for using a bad word. “A piece of plastic? Better let me pay for it.”

When we arrive downtown we check into the Grand Hotel of Indianapolis (now called the Omni Severin). Of course I can’t find a place to park. The garage I usually park in wouldn’t be built for almost another 50 years! Eventually I find a spot in back. We go up to our room and Toni orders champagne. There is thunder in the distance.

Toni asks “Do you hear that? Something tells me tonight will be our only time together. I wish I could go back to your world with you Andy. I don’t think you’d like living in 1949. I have no idea what the next 70 years will be like but I’m not going to give up. I really believe we’ll see each other again.”

As you lie back on the bed you take my hand and smile at me. You look so beautiful. We take our time enjoying each other as I slowly undress you. You are wearing thigh-high stockings and I kiss and caress each leg as I remove them. “God Toni, you are SO fucking hot.” You giggle as I use the “F-word” again. I kiss you all over then I go down on you and take your cock into my mouth. After a few minutes I can feel your body tense then relax. I swallow all of your cum. Sitting up, you say, “It’s my turn now baby. Just lay back…” Then you go down on me. “God, that feels awesome, Toni.” Laughing you say “I’ve never heard anyone use the word ‘awesome’ that way before. It must be great. Thanks.” I say “Well it kind of started in the 80’s.”

Afterward, we both lie there holding each other. The storm has gotten worse and we can see lightning outside our window. I don’t think we have much more time together. Looking over at me you get a tube of K-Y jelly out of your purse. You lie back on the bed and pull your legs up. Once I’m inside, you wrap your legs around me and say “Fuck me hard baby.” Our lovemaking is urgent, passionate. You look up at me and say “I love you Andy.”

“I love you too Toni.”

Our orgasms are powerful. Exhausted and still deep inside you, for the longest time I just lie there on top of you as you hold me tightly. You look so relaxed and content. I can feel your heart beating. The lightning is very intense now. If I’m right about what caused all of this, our time together is quickly running out. We don’t say anything. There’s no need to. We just smile and touch each other’s faces. We both know this night will have to last a lifetime. Then we kiss for what seems like forever…

When I wake up I’m back in Zionsville. It’s early morning. I must have pulled off to the side during the storm. Oak Street is like it always has been. My house is just up the road. I can see the signs for I-65. I head home and pull in the driveway. Very tired, I walk upstairs and fall into bed. I have a dream about meeting the most wonderful girl. But it seems so real. Did it actually happen?

Later this summer I attended an event downtown honoring one of the most important figures in Indianapolis LGBT history. Today is her 93rd birthday. After several speakers paid tribute to her accomplishments. I had a chance to finally meet her. She looked up at me and smiled. Instantly I recognized those beautiful eyes. I hugged her as she said “Nice to see you again, Andy. It’s been a long time, hasn’t it?”

Copyright © 2017 AMS

[Boner]

November is a depressing time of year and when you’re an 18 year old college freshman who’s stuck on campus for Thanksgiving break it’s even more so. Mom is off with her new boyfriend this year and I haven’t spoken to my father in years so I’m with nowhere to go over the long weekend. No girlfriend, no car, no job, and no money really limits my options. I’ll just hang in the dorm with some of the other losers I guess.

College hasn’t exactly been fun so far. I thought I’d get on campus and party and drink and hook up with girls. I didn’t exactly knock ‘em dead in high school and while I hoped I’d lose my virginity over the summer it didn’t turn out that way. Fact is even when I get to one of the parties, I’m too shy to hook up with anyone. All the girls seem to only like the upper classmen anyway and have no interest in dorky freshmen like me. Something look forward too I guess. So far my grades are good because my social life is shit.

I don’t mind the classes and the homework. It’s really what I’m here for anyway. Even though I’m just taking general education courses, I’m enjoying the subjects and getting good grades. By far my favorite course is Spanish 101 but it isn’t because I love the language, it’s because I can’t get enough of the teacher, Señora Ferraro.

I’ve never seen a teacher, let alone a woman, quite like her. She’s thin yet curvy with gorgeous golden bronze skin that sets off whatever she’s wearing. Her face is exquisite, large eyes and full lips with a perfectly formed nose under masses of lush blonde hair she either keeps pulled back with a colorful scarf or allows to spill across her slender shoulders. The way she moves, the way she speaks- everything about her is captivating. Needless to say I sit right up front and pay close attention while trying to conceal my excitement of being turned on by such an exotic creature. It’s hard not to stare let alone drool on my desk or squirm around in my seat because of a raging hard on.

Maybe I pay too much attention because other people have noticed. On the Wednesday before Thanksgiving , Miss Ferraro was going over some pronunciations, rolling her rs in that deliciously sexy voice of hers, I got so caught up in wanting to kiss those pretty lips I didn’t notice fratboy Fred Durant lean over and knock my books to my the floor. The class stopped short and Miss Ferraro spun around to see me sheepishly retrieving my books from the floor. To my surprise she gave me a soft smile before returning to the lesson. I felt like such an ass and wanted to kill Fred.

At last the bell rang and everyone hurriedly scooped up their belongings and headed for the door. It was later in the afternoon and in another hour the campus would be a ghost town. “Happy Thanksgiving Bob”, Fred said as he bumped my desk on the way out. Not having anywhere to go I wasn’t in as much of a rush.

“Adios Roberto”, Señora Ferraro called as I got close to the door. The last student slid by me as I turned to wish her a Happy Thanksgiving.

She gave me a smile. “How far is home for you?”, she asked.

“Actually I’m not going home this year, Señora. My mom is on vacation and I figured it’d be easier just to stay here on campus.”

“That’s no way to spend the holiday. Everyone should have a somewhere to go on Thanksgiving. Even if they don’t, they shouldn’t spend the day alone,” she said.

“Yeah well, I won’t be totally alone. I’m sure there’ll be other guys at the dorm. I’ll probably just watch football or something.”

“Do you like football, Roberto?”, she asked gathering up her coat and patent leather handbag. If there was one thing Miss Ferraro knew how to do it was dress. She pulled her white trench coat on and looked even sexier if that was possible. I felt the blood rush into my cheeks.

“Not really”, I said hoping my voice didn’t break. I felt an extreme need to get back to my room and get some relief.

“Well,” Miss Ferraro said and came a little closer. I’m doing a little entertaining tomorrow. My girlfriend is stopping by for a bit before we go out dancing tomorrow night. We’re not going out until later so if you’d like to stop by I’m sure I can fix you up with a home cooked meal. I can’t promise turkey but I wouldn’t want you to starve on Thanksgiving. My place is an easy walk from campus.”

Could this really be happening?

“I…uh….sure, I’d love to.” Smooth.

“Great”, she said and gave me a wide smile. “I don’t generally like for my students to know where I live but you’re very welcome, Roberto.”

She pulled a pen and a pad from her purse and scrawled out an address. Even her handwriting was sexy. She tore off the address and pressed it into my palm. I noticed how long and slender her fingers were, each tipped with an exquisitely manicure nail painted a hot shade of orange. The next thing I knew, one of those hands closed around my forearm and she leaned in to kiss my cheek.

“Until tomorrow,” she whispered and guided me to the door. My prick was a bar of steel and it was all I could do not to explode. I felt the dampness of pre-cum on my thigh. “Uh…yeah, thanks. See you tomorrow. Um…what time?”

“Not too early, Roberto. Why don’t you come around 7:00. Sofia should be there then. You’ll like her.”

As much as I wished it would only be the two of us, I wondered if Miss Ferraro’s friend would be as hot as her. Beautiful women always seemed to have beautiful friends. “Okay. See you then. Looking forward to it.”

“So am I, Roberto. So am I.”

Damn.

[Boner]

The next day I found the address Miss Ferraro gave me and knocked on her door. I wanted to bring a bottle of wine or something but being under 21 kept me from that and my funds were pretty low anyway. I did manage to scrounge up enough to get a meager flower boquet at the grocery store.

The door swung open and there she was, dressed to the nines in a shimmery purple dress and looking way hotter than any woman had a right to.

“Roberto!”, she squealed. “You brought flowers! How sweet of you. Come in and meet my friend.” She gave me a kiss on the cheek and tugged me through the doorway. I was afraid my cock was going to brush up against her as it was instantly rock hard.

“Robert…meet Sofia”, Miss Ferraro said and steered me towards the couch where a stunning red-head sat. I wasn’t wrong in my prediction that my Spanish professor had hot friends. This woman was off the charts gorgeous!

“You’re right Sierra,” she purred. “He is really cute. Come and sit by me big boy”, she said and patted the cushion next to her.

Miss Ferraro took the flowers from my hand and led me to the couch and her friend. Just looking at Sofia’s flawless white skin packed into a sleeveless leather dress was almost too much for me. Even though she was sitting down I could tell she was very tall and it was obvious that she spent a lot of time at the gym. I never thought anyone’s arms were sexy before but all I could think about was how much I wanted to feel her muscles.

I didn’t have to wait long because the grabbed my wrist in a strong grip and pulled me down to the couch. “Why don’t you two get better acquainted while I find some water for these,” Miss Ferraro giggled and sauntered off towards the kitchen. I was alone with this incredible woman.

“I bet you drive all the girls crazy, Roberto,” she said in a husky voice. “Got a girlfriend?”

“I….uh…no. No I don’t have one”, I managed to stammer.

“That’s too bad. Tell you what, kid. How about I be your girlfriend tonight? What do you say?”

Looking at this woman, masses of red hair piled up over a face that belonged in a magazine, what could I say? “Ummm….okay.”

She laughed. “All right then. Come here and give me a kiss, lover boy.”

I slid towards her and she pulled me closer, covering my face with kishes from those beautiful red lips. She then licked my cheek which sent a chill down my spine before driving her tongue into my mouth. My toes curled as she started yanking my shirt up over my head and raking my back with her long, red nails.

She ground against me and I started to grind back. She was as strong as I thought and our making out began to feel like top of me, grinding away. I was lost in feelings of lust I didn’t know I had in me and let out a little moan which on made Sofia more aggressive. My hands fumbled weakly around her back for the zipper to her leather dress. I had to see the giant tits that were pressing against my chest.

I was stopped when her hand shot up and clenched my chin in a vice like grip. “Not yet,” she hissed. Her mouth opened and closed over mine in another passionate kiss. Every part of me melted under her except for my cock which felt like a bar of steel. I could already feel a bit a pre-cum staining my jeans.

My hand explored her solid, strong body. I never knew a woman could feel like this! Every inch of her felt powerful. I pushed against her a little and she pushed back, letting me know she was firmly in control. “Your mine now, bitch” she whispered. “All mine. I’m going to do with you what I want. Do you like that?” All I could do was moan.

She laughed and forced me to turn over. Her fingers closed on my crotch and I knew I was going to blow my load soon.

“Hey, not so fast. We have to give him a little show first.” My head jerked around to see Miss Ferraro standing there in a skin tight pink cat suit. Her hair spilled over her slender shoulders as she raised her arms and put her hands behind her head. Her chest thrust forward and her huge tits were on the verge of popping free.

“You’re right,” Sofia giggled. “Why don’t you put on some music and dance for us?”

Sierra obliged and put on the stereo. A sexy slow bass line poured out of the speakers as she began to move. She spun and shimmied in time with the music. I was hypnotized as Sofia pulled me onto her lap, her hand softly massaging my cock as it strained inside my jeans.

Sierra spun and faced away from us and as I watched, she brought the straps of her slinky cat suit down from her shoulders and began to slowly peel it off. I so wanted to go to her and run my hands over the smooth skin of her back but Sofia’s arm had found its way around my neck and held me back. “Look but don’t touch, little boy”, she whispered in my ear. “You’ll get your chance.”

By now Sierra had shucked her outfit completely and I marveled at her round, tight ass. I licked my lips as she kicked the shiny pink fabric away. I could feel myself drooling as she turned around…..

And I saw her swollen cock pointing right at me.

“Surprised? Watch are you going to do now lover?” Sofia laughed and pushed me on the floor. I looked up and Miss Ferraro’s cock was inches from my face. She looked down and smiled.

Sofia rose from the couch and her own dress fell away exposing her massive tits and even more massive cock. Both of these ladies put me to shame. I was shocked, horrified, but for some reason my own erection still raged.

“If you want to get out of here you can, Roberto,” Sierra said. “But if you do, I hope you’ll keep our secret.”

“I….I don’t want to leave, Miss Ferraro.” The words were out before I could even think of taking them back. They hung there in the air as both ladies closed in.

Sofia placed her strong hands on my shoulders and pushed me towards Sierra. Instinctually, my mouth opened and was filled. Even though I never had done this before, I seemed to know what she wanted as I reached my hands around to cup her lovely buttocks. I heard Sierra sigh and was pleased that I could give her such pleasure.

I felt my pants being pulled off but I kept at what I was doing. I wanted nothing more than to satisfy the beautiful woman before me. Time had lost all meaning but soon I felt a gentle pressure in an area of myself I never explored before. There was a coolness as I felt something damp back there.

“Don’t worry,” I heard Sofia say from behind me. “It’ll hurt at first but I promise to go slow and, trust me, you’ll like it.”

She was right!

[a9127]

Wow! Very sexy and well written. If Señora Ferraro ends up getting fired over this I'm sure I can get her hired at my university. We always need someone to teach SPA 101.

I can understand why you would base a story on those two. Looking forward to more...

[Boner]

Originally Posted by a9127

Wow! Very sexy and well written. If Señora Ferraro ends up getting fired over this I'm sure I can get her hired at my university. We always need someone to teach SPA 101.

I can understand why you would base a story on those two. Looking forward to more...

Thanks Andy! I'm so glad you enjoyed my little tale of lust.

I wrote in 2013 for Bob's Tgirls. That was the first site I ever joined. I had just discovered Gia Darling a few days before and my mind was blown. I was looking for more Gia online and stumbled across Bob'site. This picture of Sirra was in the preview section and I joined immediately because I had to see more. She is and always will be special to me

As far as writing more, I started a story about Sexxy Jade but I scrapped it

[Smoothie]

I take showers every day.
True story.

It's like a VR headset trans shower vid, but less exciting because there's shampoo in my eyes.

[a9127]

Originally Posted by Boner

Thanks Andy! I'm so glad you enjoyed my little tale of lust.

As far as writing more, I started a story about Sexxy Jade but I scrapped it

Hope you saved a draft. Finish it and post it!