Your Favorite Shemale fantasy

[a9127]

Note: To anyone who reads and enjoys these things. Thanks. If you want to skip the story and get to the sex stuff just go to "Part 2"

A few days later, I get a text “hey whats up its cindy wondering if u still wanted to go 4 a long walk”

“yeah sure know where I live?”

“stonegate of course c u soon!”

I am not yet dressed so I run around the house getting ready. Just in time too. There’s a loud engine noise from my driveway—she can’t possibly have another Hellcat like mine? No, it sounds totally different.

Going to the front door I open it and am amazed to find a brand new blaze metallic orange Nissan GT-R sitting in my driveway with Cindy behind the wheel.

Getting in I say “This is awesome! Where’d you get this?”

“From my parents for my birthday.”

“Oh. Yeah. Nice to see you again Cindy” I say as we kiss. “Sorry, I just got carried away when I saw that car in my driveway.”

“I thought you’d like it Andy. You know I’ve gotta take some stuff to my apartment down at IU. I was just thinking about you and thought you might like to spend an afternoon together. Oh and this is a real date baby. We’re totally off the clock” you say giggling.

Carefully you back out of my driveway and then pull onto Oak street. Turning onto I-65 you blow by all the other cars and skillfully merge onto the Interstate. We’re doing almost 100 and soon are safely out of traffic. You slow down to about 75 and we just cruise along.

Watching you shift, I ask “Where did you learn to drive like that?”

“Oh when I was a kid I wanted to be the first transgender driver in NASCAR. Really! My parents paid for a lot of driving ‘schools.’ I’ve driven everything from go-karts to real race cars. Maybe you and I can take that Harley sitting in your garage out sometime.”

Continuing, you add “You know I had a really nice time the other night Andy. I’ve been thinking very hard about a lot of stuff… That was really sweet you left that tip for me. You know you didn’t have to. I thought you might like to know I donated it to charity. They are an organization that helps transgender victims of violence and hate crimes.”

“I had a great time too Cindy. You do know I’m involved with a lot of that.”

“Yeah I know you are. I know a lot about you. Please don’t be upset with me. I have to know everything about my ‘clients.’ A girl can’t be too careful. I had a girlfriend who was murdered by someone she took home.”

“I’m sorry to hear that. But I hope everything you learned about me is good. So there wasn’t anything about the meth lab I ran in high-school?”

“You’re so silly. But yeah. It is all good…” you say smiling at me. “Besides you hated Chemistry. You were always good with computers and you got straight A’s in Math and Physics. You also were a 1st team all-state linebacker, had a full-ride football scholarship to Michigan State and your first girlfriend was transgender. You got thrown out of a game because you beat up an opposing player for making a derogatory remark about her.”

“You know all that?”

“Um hmm… anything else you wanna know?” you say laughing. “You know Andy, I’ve always had it pretty good. I feel very fortunate. I knew I was a girl almost as early as I can remember. I told my Mom and Dad and they were totally supportive. My Dad owns several companies and they both made sure nothing happened to me in school. They went to the superintendent and told him there would be hell to pay if I was bullied or beat up. It’s not like I haven’t encountered hate or discrimination, especially now that I’m older, but I pretty much grew up free of what a lot of my friends have had to go through.”

“You are amazing Cindy.”

“Thank you. I think you are too. Anyway, I thought after we drop off my stuff we can take a walk around campus. I know you got your Doctorate there so you must know all the woods and pathways. Then we can stop at Nicks. When you were a student you liked to go there a lot. I know the owner and can get us a private booth in back. It’ll be a great way to get to know each other better Andy.”

“But you aren’t 21 yet.”

“OK then. I’ll just say you’re my Dad…” you look at me and smile.

Soon we arrive at your apartment. I help you carry your stuff in and you show me around. “That’s my bedroom…” you say suggestively. I can’t help but notice the large bed and also how nicely everything is decorated.

Driving onto campus you park the GT-R and we get out. “I’m sure you remember quite a bit but there’s a lot that’s new since 2005.”

You show me some of the new buildings on campus and along the way we just talk. About lots of stuff. It’s nice just being together. Soon we are laughing and joking around and you take my hand as we head into the woods.

“I’ll bet you remember this place…” you giggle. Of course I do, it’s the gazebo. Legend has it that if you kiss your lover at midnight you will be married. “You probably kissed a lot of girls here, Andy.” We step inside and you move closer so we are facing each other. We look into each other’s eyes. I can feel your hard cock pressed up against mine. Classes haven’t started yet so no one’s around. Then you say “But it’s not midnight yet Andy…” as you put your arms around my neck and we kiss. I reach down and feel your ass and pull you tight against me. We continue kissing for a very long time. When we separate, you look up at me and say “I realize how we first met, but I hope you know by now the way I really feel about you Andy. Why don’t we go to Nicks?”

We walk back to your car. You hold onto my arm the entire way. I can tell there is something “different” between us now. Could we be falling in love? I’ve been “in love” so many times I’m not even sure anymore. And you are so young.

Copyright © 2017 AMS

[a9127]

Continued from Part 1 above...

It’s crowded at Nicks but for you that’s no problem. You call the owner on your cell and then drive around back parking in a reserved spot. When we go in there is a cozy booth in back just like you promised.

We order dinner and I notice you don’t order any alcohol. I assumed you could get away with anything and it would have been OK if you had but you just say “If you want a drink it’s OK Andy. You can get wasted if you want. I’m driving. It’ll just make it easier to take advantage of you later anyway” you say laughing.

During dinner we sit on opposite sides. We talk some more and I have the feeling I might be right about earlier. You can’t possibly be faking this Cindy. You have no reason to. Then you order dessert saying “I thought we could share this Andy” then you move over to my side. You kiss me then gently put my hand on your thigh. “You know this day may have been the nicest I’ve ever spent with anyone.” This time when you kiss me your tongue is all over the inside of my mouth. I run my hand up your leg and stroke your cock through your shorts. You feel my chest and shoulders gradually moving down to my cock. It’s a good thing we are in a private booth. As we make out I whisper “I want you Cindy.”

Placing your hand on my cock you say “Want me to climb under the table and give you a blow job? I bet your girlfriends never did that here. Or we could just go back to my apartment.” Seeing me get out my debit card you say “Don’t worry about it. It’s on me baby.”

We get up and head out back to your car. You look over at me and not saying anything take my hand and kiss me.

It’s starting to get dark now and as soon as we get to your apartment we are all over each other. There is a trail of clothes on the floor leading into the bedroom. You look so beautiful in the setting sunlight coming in from the window. Of course we are both rock hard and without saying anything, you get down on your knees and proceed to suck me off. Jesus! I’ve never felt anything like that before. The way you use your tongue. The way you slide your mouth up and down my cock. Pausing, with my cock in your mouth, you look up and giggle softly. I can tell you are thinking “What the fuck do you take me for, Andy, an amateur?” and “You ain’t seen nothing yet baby.” I desperately want to cum but you know exactly how to control the pressure and speed to keep me on edge. Just when I think it can’t get any better you put your fingers inside my ass and massage my prostate. My precum is flowing and you use this to your advantage as you continue to suck and massage. This goes on for like ten minutes or more. I’m not sure I can stand it any longer but you seem to know exactly when the right moment is and then drive me over the edge. My legs almost give out and I have to hold onto you as I shoot my cum into your mouth. You don’t gag like I did the other day at your place. The feeling is indescribable. I have to sit down on the bed and then you jump onto my lap facing me.

“Fucking Christ, Cindy. I’m not even sure what to say. That was like an out of body experience. It’s gonna take a while to recover baby.”

“That’s OK Andy. I’m glad you liked it” you say giggling. “Take your time sweetie we’ve got all night.” Then you kiss me on the forehead and hold me tight against you.

Lying down we talk some more about what a great time we had today. You tell me a little about your classes and ask me a little more about what I teach. “Just relax baby. Whenever you’re ready we can go again.”

“I think I would be a dead man if you did that again, Cindy. I’ve never felt anything like that.”

“That’s so sweet Andy. I’ve got an idea, hope you like it…” I know you have something awesome in mind. My cock is already beginning to get hard again in anticipation. Noticing this you say “I’d better get ready then… if you want to wash up there’s a bathroom in there, Andy.”

When you come out you are totally naked except for a leather collar. You are carrying a bunch of scarves. Seeing this makes me fully hard again and ready to go. “Andy, I’d love to be tied over the bed and spanked. I just can’t trust too many people. But you can do anything you want to me.”

You lie face down over the edge of the bed and I tie your wrists to the bedposts with two of the scarves then, spreading your legs far apart, tie your ankles to the other bedposts. I tie them loosely so you could get out if you wanted. Noticing this you say “I see what you are doing baby. That’s sweet Andy but you can really tie me up if you want, I trust you.” So I tie you very tightly stretching you out so you can hardly move. “That’s much better” you say. “Fuck that feels good.”

I have tied you in such a way that your cock is pointed down tightly against the side of the mattress. In this position I can do anything to it. Also your ass is totally exposed. It’s not like we’ve never been together before but I’ve never seen your ass quite like that. Fuck, Cindy, you are so sexy. I am hard now and feel like I badly need to cum again. Moving to the other side you look up at me and smile. “My nose itches” you say. I brush your long blonde hair out of your face and rub your nose. “Ooooo… that feels so much better, thanks baby.”

I gently massage your gorgeous body with oil and run my hands up and down your long legs. Your arms, back, and shoulders look so muscular yet slender. I pause to kiss you then move to the other side of the bed. Your cock is very long and super hard. Ever so slowly I stroke and tease it. Kneeling, I lick the tip. Especially around and behind the head. You pull against your bonds and moan and say “Fuck Andy. That’s torture! God it feels so awesome…”

Kissing your ass I insert my fingers inside and gently massage your prostate. Then I give you a smack on your butt. “Geeze Andy what the fuck was that big guy? I thought you were gonna spank me?” you say giggling. So next time I do it a little harder. “Um… I know you can do better than that sweetie.” This time you gasp and say “Owww… that was much better. I like that…” I spank you until your ass is red then I carefully insert my finger in you and fuck you that way for a while. You are moaning and straining against your bonds. Then I enter you from behind, very gently at first, then gradually fucking you harder and harder. As your orgasm builds, your body tenses. You are very strong. It’s a good thing I tied the scarves tightly.

I hold off as long as I can and we both come at the same time. This time I’m not wearing a condom and I ejaculate inside you. I am sure you will pull out all the scarves. You cum all over the floor as you let out the loudest scream I’ve ever heard. Then “Oh God. Shit. Motherfucker. Fuck. Jesus. Damn. That feels so fucking good to have you cum inside me Andy.” Then you go totally limp on the bed. I can hear you let out a sigh. I return to the other side and you look up at me. Your hair is matted to your face. I kneel down and we kiss. I touch your face. You look up at me and say “Andy, if we can’t find anything else to build our relationship on, sex will be just fine.” Then at almost the exact same time we both say “I love you.” Laughing at our “timing” we kiss again, then I untie you.

Lying together in bed after, you say “I’ve had the greatest time of my life Andy. I don’t want this day to ever end.”

Copyright © 2017 AMS

[a9127]

“I’ve never felt like this about anyone before, Andy” you say across the dining room table “you are so fucking good to me baby.” The room is dark except for candlelight. It’s the end of your mid-term break, a cold October night, and, to celebrate your 21st birthday I made you dinner. There is a roaring fire in the fireplace. When we first met I had absolutely no idea where this relationship was going. I mean especially considering how we met (Pretty Woman 2017).

“I love you Cindy” I say as you smile at me. “I love you too Andy.” We have been through several bottles of wine already and I can tell you are a little drunk. “Andy, I have never been in love with anyone before. I have everything anyone could ever want. My parents are rich, I always got good grades in school, I was the most beautiful girl in my class. But I always thought most guys were jerks. I started my own call girl business because I love sex and didn’t want the commitment. You pause, then add “But there was something special that first time we were together. I know you felt it too. Didn’t you?”

“Cindy I’ve been with many women. You know I’ve been married twice. This divorce has been very hard on me. I saw your ad and I thought ‘what the hell’ I figured we’d have a good time and never see each other again. What I didn’t count on was falling in love.”

“Yeah. Well I realize what’s been missing from my life. I had no idea. That trip we made in August to take my stuff down to school. I’ve never spent a day just being with someone—even just talking—it was so different. You know I liked when we just held hands and walked around campus. And of course when we made love later that evening then snuggling up with you after… I’ve never woken up with someone that I really cared about Andy.”

You get up and walk over to where I’m sitting. You fill both our glasses and say “Why don’t we go sit in front of the fire?”

We lie there together and talk some more. You tell me how your classes are going. You say “I told my girlfriends that have had you in class not to say anything or give you a hard time. I know a few of them that would love to fuck their prof. I told them if they ever come onto you I’d kick their ass.”

“How do you feel about being in a relationship with someone in his 30’s, Cindy?”

“Christ, you’re in better shape than any guy I know, Andy. Plus you’re smart and successful. I’m not interested in ‘boys’” you say laughing. “I feel like I’m 21 going on 30 anyway. You and I have a lot in common. So I think it’s OK. You teach at a different university—it’s not like I’m your student. My parents really like you. My dad thinks it’s cool that you teach and also have your own company.” Giggling you add “What? Would you rather see me dating a 23 year old unemployed douchebag who lives in his parents basement?”

Without saying anything more we kiss. It is long and passionate. I was hard hours ago. Now I’m even harder. Laughing we both quickly down the rest of the wine then you lay back on the rug in front of the fire. Your slit skirt shows off your long legs which are slightly parted and very inviting. Running my hand up your thigh I feel your hard cock and slowly stroke you as we kiss some more. You moan as I gently take you into my mouth. I work your shaft and head over with my tongue until you can’t stand it anymore.

“God. Fuck me baby.” Continuing to work on your cock I insert my fingers into you and gently massage your prostate. I can tell you SO want to cum. But not yet baby. Not yet. You are squirming on the floor moaning and pleading, gripping the rug. When I can tell you are ready, I enter you. I hold your wrists down as I fuck you slowly at first. I can feel our orgasms building. Your cock is dripping precum and I begin to jack you off as I continue fucking you. You are fucking me back just as hard. Your eyes are closed and I can tell you are about to cum. We explode together. I shoot my load deep inside you and you shoot yours all over your tummy, me, the rug, everything.

We both collapse and just lie there for a few minutes. Looking me in the eyes you say “Christ Andy that was awesome.”

We grab a couple of pillows off the couch and snuggle up under a blanket. Outside the night has gotten very cold and there are snow flurries but lying there with you in front of the fire it feels so good. Holding each other we gradually drift off to sleep.

Copyright © 2017 AMS

[a9127]

Halloween 2017 was the coldest I can remember and there wasn’t much activity. Unlike other places I’ve lived, trick or treating here mostly occurs in the daylight and is essentially over by 7:00. Some costumes were very creative. My favorite was a giant toilet bowl and of course after 40 years “Star Wars” remains popular.

After the last group of kids, I go into my den and work on the computer for a while. This has been a lonely Halloween. I’m still getting over a breakup with my longtime girlfriend and my current lover is spending tonight with her parents. Around 9:00 I sit down in front of the fireplace. The warm fire feels good on a night like this.

Suddenly the doorbell rings. Nobody’s been by for over two hours. And I wasn’t expecting anyone. Standing at my door is one of the most beautiful women I’ve ever seen. Her face is gorgeous. She has long black hair, green eyes, and bright red lips. Topless except for pasties, she is wearing a blood red cape and thigh boots. On her head is a very realistic pair of horns. I also can’t help but notice the sexy bulge under her bright red panties. “Trick or Treat!” she says.

Normally I’d do her on the spot, but tonight I’m just not in the mood. “Did Sam and Grant send you?” I ask.

“Who?” she says.

“You seem really sweet and that’s a great costume, but…”

“You were thinking about me, Andy.”

“How did you know my name?”

“I’ve known you for a very long time. I just thought you might like a friend tonight.”

Thinking to myself, she IS very beautiful and seems nice enough. So I say “Why don’t you come in? You’re probably freezing your ass off.”

“Well I usually like it much hotter than this” she says, smiling.

“Can I get you something to drink?”

“Sure, got any Bacardi 151? No ice.”

Coming back with her drink, I can see she’s made herself at home on the couch in front of the fire. Sitting with her long legs crossed I get a good look at her fantastic body. Maybe this won’t be such a bad Halloween after all.

“Here you go…”

“Thanks. By the way, all my friends call me Luci.”

“Nice to meet you Luci. What were you doing out on a night like this anyway?”

“Well as I told you I knew you were thinking about me. You have been very depressed about breaking up with your old girlfriend and you have been really angry. I’m kind of worried about you.”

“Hardly anyone knows about any of that stuff. Did my friends put you up to this?”

“No. Why don’t you join me Andy. I hate to drink alone.”

Sitting down next to her we share a toast to “evil thoughts about people who have fucked us over” then we both laugh. She downs her Bacardi in one gulp. “Would you like another one?” “Sure” she says “Thanks…”

I get her another drink and when I return she is leaning back against the couch. Through her panties I can see the outline of her cock—it looks huge. I can’t even imagine how big it is hard. She notices this and smiles as I sit down next to her. Her eyes begin to glow red. All I can think about now is sucking her cock and fucking her. Her body glistens in the light from the fire. “It feels so good in here, Andy. I love the warmth.”

Then she puts her glass down, leans over, and kisses me. Instinctively I place my hand on her thigh. Her skin is so silky smooth. She giggles slightly as I run my hand up towards her cock. She lays back on the couch. I slide her panties off. I’ve never seen a cock that size before. It must be 15” at least!

We position ourselves in a “69.” At first I think I’m imagining it but my cock continues to get bigger and bigger—until it’s almost as big as hers. She looks at me and I can see her eyes are glowing red again. I can also feel what she feels. It’s quite a turn on. When we cum it’s like nothing I’ve ever experienced. It’s like my body is on fire. Then everything goes black. Recovering I say “Fucking Hell, Luci.” She laughs and says “You’re right about that baby.”

Lying there we pull a comforter over us and she asks me “So, are you still mad at everything?”

“No. That was amazing Luci. You can take those horns off if you want…”

“They don’t come off Andy. Go ahead, feel them if you want.”

“Well I’ll be damned...”

“Not yet Andy. You are a good guy. I also happen to know that your young friend Cindy (“Pretty Woman 2017,” “A Long Walk,” and "It's Been Awhile") really loves you. You turned her life around. Just be careful with her, she thinks she’s the world’s greatest driver. That GT-R she has is a very fast car.”

Luci continues “You don’t realize it but we almost met when you were 19 and totaled your Corvette. You were so upset over Stephanie moving to New York. You weren’t paying attention like you normally do. You were very lucky. Oh, and I think it’s cool that you drive a Hellcat. What a great name for a car! Wish I could stay and go for a ride with you.”

“But we were having such a great time. And you seem to know so much about me. Who are you anyway? I wish you could stay with me tonight and tell me more about yourself.”

“Sorry Andy. Before the clock strikes midnight, I have to leave. But we still have an hour together. You wanna go again?” you say, your eyes glowing red.

“Sure” I say. Suddenly my cock gets as big as before and I feel like I have to cum. Luci just laughs and lies back saying “Fuck me like you’ve never fucked anyone before. I love it rough. Do anything you want to me baby. You’d be surprised what I can take.”

It’s almost midnight. We fuck each other so hard we destroy half the furniture in the living room. Part of me wishes I could spend an eternity with her. Already I’ve lost track of time. Luci notices the time and says “You ready baby?” “Yeah.” Just like that we both come. Again, my orgasm is more intense than anything I’ve ever felt with anybody else. And it feels like it won’t stop. I don’t know if I’ve ever felt so relaxed. Afterward, Luci holds me gently.

“Do you really have to go?” I ask.

“Yes Andy. You know who I am. I’ll be there whenever you think of me but be careful what you wish for. And take good care of Cindy.”

You put your cape on and I walk you to the door. It’s about five minutes before midnight. You just look at me and smile. Turning around you head out into the cold. I watch you walk down the driveway towards the street then disappear into the night.

Copyright © 2017 AMS

[Boner]

Great story Andy!

[Alis]

my fantasy is to let it happen)
but it would be just great if my bf would present me a night with a shemale staying to watch... or participate)