Your Favorite Shemale fantasy

[a9127]

I noticed you the moment you walked into the bar. All during the evening I had been checking you out. And I could tell you were checking me out as well. Eventually we made eye contact. I went over and offered to buy you a drink. At just a little over 6'4", mid 30's, with a football player's build and (so I've been told... LOL) a nice ass, I'm used to getting hit on frequently. In fact I was an All-American linebacker at Michigan State and played two years in the NFL before tearing my ACL. Fortunately I finished my degree, saved my money, and started my own company. Now it’s one of the largest Business Analytics solution providers in the world. I’ve had so many beautiful women in my lifetime that picking up somebody in a bar is no big deal. But there is something very special about you. You seem different somehow from all the others. Maybe it’s your smile. Your self-confidence. The way you laugh. Or the way you looked at me when our eyes first met. I don’t know how else to explain it—but I felt like you knew me. There’s no question that you are absolutely drop-dead gorgeous. But something else makes me want you more than any woman I’ve ever had. What’s funny is that I’m actually a little nervous approaching you because I don’t want to mess this up. Close up you are even more beautiful and I notice how blue your eyes are. You are a little taller than I first thought, maybe 5'9". And I would guess you are about 24 or 25. Through your cropped t-shirt I can see the outline of your natural breasts and can't help but notice your toned abs. Your tight jeans nicely show off your long shapely legs, perfect ass, and a very sexy bulge. The attraction clearly is mutual. We talked for a while and it wasn't long before you climbed into my black Lamborghini Aventador and came back with me to my place. The warm summer night is magnificent and there’s a full moon. We chat a little on the way and it’s obvious there is definite “chemistry.” The gate opens automatically and we pull around the circular driveway. I leave the car sitting there not even bothering to park. Just inside the front door alone in the dark entry way, with moonlight streaming in through the windows, we kiss for the first time. Things progress rapidly and as I grab your ass and pull you close to me I feel your hardening cock against mine begging for attention.

Getting down on my knees I unzip your jeans to reveal a perfect 7" cut cock. I take you into my mouth and slowly bring you ever so close to the edge. Then suddenly I stop. You ask why. "I have something very special planned. Tonight will be a night you will never forget. Like another drink?" You say “sure.” I go to the bar and make us both a Bacardi 151 and Coke. We sit down on the couch and quickly finish our drinks. You giggle as I down mine in one gulp. “Not in a hurry are you?” We kiss again and soon we are all over each other, feeling each other up, tearing at each other’s clothes, knocking over furniture, and generally trashing my living room. This “wrestling match” ends with you on top sucking my raging hard on. God, I want you so bad. It takes all of my self-control to keep from fucking you right there on the living room floor. It’s only because of what I have in mind for you later that I don’t. With your long strawberry-blonde hair, beautiful face, freckled nose, pretty blue eyes, amazingly fit body, and muscular legs that are to die for you look like a dream. A dream who at the moment is pinning me to the ground with her thighs, giving me a blow job. Could this night get any better?

When you pause for a moment I ask if I could show you something. Sitting up, you give me that “look” and say "OK…" then follow me downstairs through a heavy steel door. I tell most people who visit that it’s a “tornado shelter.” Very few guests have ever been down there. Dimly lit, it’s difficult to see much at first. For a minute I'm not sure if you are going to say "get me the hell out of here," scream for help, or maybe dial 911. While you are checking out the “furnishings,” you reveal that you have often fantasized about being tied up and had even experimented with bondage in a previous relationship but never anything like this. You explain to me that it’s hard to trust someone that much. I can tell that you were about to say something else but then you look up at me, adding that while you don’t like pain, you are really turned on by the idea of being at the mercy of a powerful lover and have often wondered what it would be like with the right person. You describe some of the more extreme things you have seen on the Internet and how you have often wished you could be one of the models in those videos. From the way you talk I can tell that this really excites you. Looking straight into your eyes I ask if you trust me. You say "yes" and then kiss me. Without saying anything further, I blindfold you, take you gently by the hand and lead you to a specially designed chair in the center of the room. You seem to know exactly what I want you to do.

Continued below...

[a9127]

Continued from Part 1 above...

After everything is ready, I remove the blindfold. With the torches on the walls now lit, the room looks like a dungeon with a large mirror on the wall facing you. You are tightly bound to the chair with leather straps. Your legs are spread very far apart leaving your cock, balls, and ass completely vulnerable. Without air conditioning, the temperature down here during the summer often reaches over 90 degrees Fahrenheit. Your exquisite body glistens with sweat. Saying “I promised you this would be a night you wouldn't forget…" I lean over and we share a very long, passionate, open-mouthed kiss. I ask if it’s OK to gag you. You nod “yes” and open wide as I insert a rubber penis gag and buckle it in place. I know you’re not going anywhere so I take my time exploring every part of your incredible body—your breasts, your thighs, your ass. But I pay special attention to your nipples and cock. You moan softly through your gag and look at me with those beautiful blue eyes. I smile as I look back at you. I sense a little anxiety but mostly excitement and anticipation. I would never hurt you. But right now I can tell you aren't 100% sure of that. We had agreed beforehand on a safe “signal” to use if anything wasn’t right and you wanted me to stop and release you. And I would. But you don’t use it. I can tell that you are very turned on as your cock is hard and there is already precum flowing from it. I reach down and ever so lightly run my fingers along the shaft and around the head and as I do you strain against the straps and let out an "mmmph!" I start to jack you off but before you can cum I stop and concentrate on tormenting the head of your cock with my mouth and tongue. It is amazing how sensitive the area around the glans is. When I begin to slowly stroke your cock, you scream through the gag and buck wildly against your bonds. I can tell from your eyes you desperately want to cum. "Maybe after a few more hours…" I say playfully. The look in your eyes this time says “Fuck you, you bastard!” But I also take note of the fact that you don’t indicate that you want me to stop.

Searching through my collection I find something called a "gates of hell." "This will be fun" I say and kneeling between your legs I fit the rubber rings over your cock and balls making sure everything is tight. I kiss your thighs and holding your cock gently in my hand, I take a surgical steel “sound” and carefully guide it ever so slowly, deep inside you. Although I use lubricant, there is so much precum that it slides in easily. I can tell you’ve never had this done to you before. At first I don’t know if you like it or not. Very slowly, I pull the sound back out and slide it back in, fucking your cock. You close your eyes as you lean your head back and sigh. After a few minutes your cock is throbbing, desperately trying to escape its restraints. As you grip the arms of the chair, the noises you are making through your gag tell me that you are thoroughly enjoying this “torture.” I look into your eyes again. They are soft and beautiful as you look back at me and I wonder what you’re thinking. I know what I’m thinking. I think you are the most beautiful and amazing girl I’ve ever met and I’m hoping that tonight is just the start of something wonderful. Before this night is over I want to give you the most mind-blowing orgasm you have ever had in your life.

During our fun and games my own cock has become incredibly hard and I also need to cum very badly. At this point I’m sure neither one of us can stand it much longer. I remove the “gates of hell” and rubber gag. We kiss for a long time and you tell me that you are ready. The chair you to which you are bound was designed to hold someone in such a way as to allow anal penetration from the front. I should know, I built it. I have always preferred this position to going in from behind. It’s just so much more intimate to me. Your ass is very tight and I proceed slowly and gently using plenty of lubricant. The feeling of being inside of you is indescribable and I try to relax so I don’t cum too soon. As we fuck, my 9” cock massages your prostate with each stroke. The pace speeds up and soon we pass the point of no return. Looking into each other’s eyes we cum at the same time. The feeling as I explode inside of you is beyond intense, a release of all the sexual tension that has been building up since we met. It’s like I can’t stop cumming. The wave after wave of pleasure that accompanies this causes me to blackout for a second. You arch your back and let out the loudest scream I’ve ever heard. Every muscle in your body stands out. Your own orgasm is so powerful that you break a couple of the straps holding you to the chair. You shoot a huge load and your semen is thick and creamy. Some of it gets on my face and I lick it off. It tastes great. Afterwards, you lie back motionless with your eyes closed. Your body appears totally relaxed. It almost looks like you have passed out. For a brief moment I think I see a smile on your face. Still inside of you, I hold you gently and rest my head between your breasts just listening to you breathe and the sound of your heart beating. Totally exhausted and completely covered in sweat, we lie there together for a while. I feel closer to you than I have to anyone. Ever. Once I have regained enough strength, I help you undo the remaining straps, then both of us head upstairs and take a shower together. We don't say anything to each other. We don't need to. I have an extra bath robe that you put on, and after you have finished drying your hair, you climb into bed. The sun is just beginning to come up. Somehow you look even more amazing. As you snuggle up to me I tell you “I love you.” You pull closer and say "I love you too."

Copyright © 2016 AMS

[a9127]

After I get off my shift at Pizza Hut, I drive across Detroit to the worst part of town and pick you up in my rusted out Ford Pinto. You are only 29 but all the drugs you have done make you look 60. You say “What’s up asshole?" I say “Not much.” You climb in and we go back to your crummy 1 bedroom apartment. The elevator is out of order so we have to climb 7 flights of stairs. I’m so out of shape that you have to drag me across the doorway. Before you transitioned, you were a bodybuilder so you are still very strong. We open a bottle of Jack and smoke a joint. You say “Christ, you are a pathetic little motherfucker…” and throw me on the bed. First you make me suck your dick till you come all over my face then you chain me to the bed and proceed to whip me with your belt then fuck me in the ass, hard. Blindfolding me you say “I have a surprise for you dickhead…” I can tell there are other people in the room. You say “Show us your tiny cock, dumbass.” I pull my little stub out of my pants. All your friends start laughing. “It looks like a fucking clit” someone says. “OK. Show us what you can do…” you tell me. Kneeling in the middle of all your friends I begin to jack off. Fully erect, my cock only measures about 2”. When I do finally cum it’s just a dribble. Laughing, your friends all shoot their loads onto my face and a couple piss on me.

When it’s over you say “See you next time, loser!” and kick me down the first flight of stairs. “Fuck you” I say. Very drunk, I stagger down the remaining flights, manage to find my Pinto and drive back across town to my filthy trailer where I climb into bed, smoke another joint, and go to sleep alone.

[lordscott]

My dream wedding is that i found myself a virgin shemale and that she waits till marriage like me since I'm a virgin,I'm saving my virginity til marriage & i expect her to do the same and on our wedding night well you'll get what i mean so i don't need to feel in the blanks do i i properly will not/never find a virgin shemale anyway more likely she'll be a none-virgin & i doubt she'll like a guy with a small penis like me anyway.

Since I'm cursed that i have a small penis sorry for that repeat and those of you who have the same curse as me then you'll understand what i mean and understand my concerns like i said this is not really my shemale fantasy it's more of my dream wedding with a shemale if i did end up finding a a virgin shemale that she waist till marriage like me .

[a9127]

The following is based on events in The Open Cybersex Roleplay Thread as well as my earlier Kirsten stories:

As soon as Kirsten and I got home we started talking about Shawn’s party.

“That was really like totally rude for us to leave like that. Let’s go back!” she says.

“I agree. But you will have to drive baby, I still have too much of a buzz.”

“OK. I’m going to change into something more comfortable. We’ll take my bike and you can sit behind me. Yeah, and there’s something else I want to do…”

When you come downstairs, you are wearing your motorcycle boots, short leather jacket and the sexiest black panties that do little to hide anything. You smile at me and head out to the garage. I think I know what you have in mind…

Hearing your Harley firing up, I go to check on you and you say “Omigod! You wouldn’t believe the texts I’ve been getting about Shawn, ila, and Red! It sounds so sexy!” Climbing on I say “don’t forget your helmet.”

“Fuck my helmet! Just once Andy, I want to do it with you on the bike. You know I’m a careful rider. You taught me everything. Don’t worry, I’m not gonna have an accident.” My better judgment says we shouldn’t be doing this but you look SO fucking hot and the idea of sex with you while we’re riding is just too much to resist. Plus I haven’t come since two nights ago…

“Where are we going?” I ask.

“Back to Shawn’s but I thought we’d take the long way.”

Skillfully you merge onto the Interstate and head North. It’s the middle of the night so there is little traffic. It has been unseasonably warm here lately with temperatures in the 80’s (F). At 3 am it’s still in the mid 70’s and there’s a half-moon. You look back at me and we kiss then you turn your attention back to the road.

Carefully I reach inside your jacket and feel your breasts. Your nipples are hard and you moan and lean back slightly and rub your ass against my now rock hard cock. I’m so turned on but at the same time amazed that you can maintain expert control of the motorcycle under the circumstances. Gradually I run my hands all the way down your body to your thighs.

Lightly I start to stroke your cock through your panties. You look back at me and smile but shake your head “no.” The look in your eyes is saying “I’d love that Andy, but you’ve got to be fucking kidding. You want me to lose control of this thing and hit a tree?” so I stop.

You slow down, stand up slightly, and scoot back a little. I move forward so that I’m under you. Pulling your panties to one side with your left hand, you gradually work your ass down onto my cock. Unlike the time we made out on my motorcycle in the garage ("A Ride on my Harley") this is potentially dangerous and it’s important that you control all the action.

As you pay attention to the highway, I hold onto you and we fuck each other, very slowly at first and totally “in synch” and it isn’t long before we cum. God it feels so good! Having gone that long without an orgasm, I ejaculate deep inside you and it feels like it won’t stop. My cum runs down the back of your thighs and also the seat and I almost lose my grip. Fortunately, you grab my arm and keep me from falling off.

How we did all that without getting killed I’ll never know. You are thinking the same thing. We both start laughing. You turn around and kiss me. I hold you tightly around the waist and lay my head on your shoulder. The wind blows your beautiful long blonde hair in my face. Over the loudness of the Harley I can hear you yelling “That was awesome baby! I love you!” Pulling over at a rest stop, we get cleaned up and change clothes. Then we head back to Shawn’s party.

Copyright © 2016 AMS

[a9127]

I have never travelled much and after my retirement decided to visit Thailand because I’ve heard so much about it. I was excited during the long plane trip and my anticipation grew with each passing hour. I knew that I would meet the ladyboy of my dreams and maybe even take her back to the US where she could live with me.

It was nighttime when I arrived and the first thing I did was head to the nearest bar. The most beautiful woman I had ever seen approached me and offered to buy me a drink. As I downed it I began to feel dizzy. Then everything went dark.

When I woke up I couldn’t move. Nor could I see. I soon realized that I was encased in a tight rubber bag and bound with leather straps. They had placed a rubber hood over my head and my mouth had something very large in it. It felt like a rubber cock! And my ass had an even larger one inserted deeply. I could only breathe through tubes placed up my nose. The rubber was very hot and I was very uncomfortable. Strangely it seemed that my cock was the only part of me that was exposed as it was rock hard and I could feel air circulating around it. Soon I could hear someone talking—it sounded like the girl from the bar. She laughed and said “Silly tourist you came here looking for fun now I’m going to make sure you have fun.” She removed the rubber cock and replaced it with her own. Then she made me suck her huge cock which must have been at least 9 or 10 inches long. It was so big I almost choked. Then she came, shooting her load down my throat. I coughed and gagged as she made me swallow every bit of it. Locking the rubber gag back in place she began to go to work on my own cock. Giggling at how "small" it was, her expert fingers teased me for what seemed like an eternity. Then she slowly milked me—not allowing me to come. Afterward she locked me in a tight chastity device and said “If you are good, maybe in a month I’ll let you cum.” “Now you are my sex slave for life!” she said as I heard her walk away. Left in total darkness desperately needing to cum, I lay there wondering what was next…

[a9127]

In my lifetime I have met many celebrities. Mostly in sports and auto racing. My career is teaching and it just so happens that our university is located not far from the Indy 500 track. I am “chair” of the “Motorsports Management” program and also have a consulting practice. Many local celebrities are clients. Almost daily I run into players from the Colts, Pacers, Indiana Fever and of course auto racing. I am no stranger to athletics as I was once a starting linebacker for a “Big 10” university. I have also raced cars as an amateur. I have many friends that have played in the NFL. When I was very young my dad was transferred to New York City and we used to see famous people regularly. My favorite was probably Liza Minnelli who smiled at me while we were riding the subway. My dad's career was in advertising and sales so he came into contact with people from movies and TV as part of his job. Very similar to my own situation.

As a boy, like many my age, Michael Jordan was my biggest sports idol. When I was very young I discovered exercise as a way to increase strength and gain self esteem as well as excel at sports. I also happened to become friends at around age 12 with a very feminine boy that identified as a girl who lived down the street from us. I have told her story elsewhere on TLB. Her name was Stephanie. We were much more than friends, we became lovers and dated throughout high-school. She was in fact my first girlfriend.

I had many posters in my room as a teenager. Most were car, sports, or music related, many were popular actresses from TV. One was a former Olympic Decathlon champion. I believe from the 1976 games which happened a few years before I was born. His accomplishments made him very famous and he was married to a gorgeous model in real life.

Interestingly enough although clearly “male” I found his appearance, with his long hair, short shorts, and tight tank top to be somewhat “feminine.” He was well muscled but not in the way of say “Arnold” or even myself. One time alone in my room I started jacking off to his poster. I guess I just found him “hot” at the time. LOL I remember having a very powerful orgasm and mostly just glad that my mom didn’t walk in on me. It never bothered me however. One, I didn’t think it was “wrong” or “gay” or whatever even back then. Two, you will remember I was dating someone who was transgender at the time. It never occurred again. But many years later he resurfaced as the star of a reality show and then one day announced he was transitioning. As a woman she ended up on the cover of a popular magazine and while she is more than 30 years older than me I find her even more attractive today.

[a9127]

A picture is worth a thousand words...

[a9127]

Ever since I was in 6th grade and played sports I’ve always been into working out. Except for a couple times when I was sick or had surgery I’ve never missed a workout. Even earlier this year, I had surgery for a “sports hernia” and was back in the gym less than 24 hours after being on the operating table. My doctor had told me not to lift “over 10 pounds.” Yeah, right… LOL Well, I did back off. A little. As I get on into my 30’s it is really starting to pay off. Usually I like to go late at night. There is a gym that is open 24 hours just down the street from me and typically I workout around 1 or 2 AM. Usually there is no one else there. Maybe some “older guy” who just wants to use the treadmill but that’s it. I don’t go to “socialize” either. I have lots of opportunities to meet people and I’m not lacking for any kind of “social life.” Recently here in Indiana, it’s been very hot and humid with severe storms and temperatures well into the 80’s (F) even at that time of night. The air conditioner is usually turned “down” at night. Members can’t access the thermostat so it’s usually warm. I like that.

Around 1:30 I hear the door and see you walk in. I’ve never seen you here before. You are definitely not an “old man with insomnia.” At 6’ tall with long bleached blond hair you are absolutely stunning. Even with your clothes on it’s obvious you have the body of an athlete. You are too far away for me to say hello and besides I’m sure you didn’t come here to get hit on. I go about my business and you go into one of the dressing rooms to change. When you come out, it’s kind of hard not to notice how amazing looking you are. You are wearing maybe the shortest black shorts I’ve ever seen and a grey tank top. You have the sexiest ass I’ve ever seen and legs that are totally to die for. Your arms are muscular and you clearly have a well defined upper body. I’ve seen professional athletes that aren’t in as great shape as you are. As much as I’d love to approach you, I don’t, so I continue with my workout pretending that I didn’t notice you. All I’m thinking is “if there really IS a God…”

For such a large place, there is only one drinking fountain. And of course purely by chance we both end up there. We make eye contact and you smile at me. I say “Hi” and we both resume our workouts. About half an hour later, our “circuits” have brought us to the same area and you ask me if I “still need the lat machine?” I say “no.” And then add “I’m glad I’m not the only one who’s up this late…” dumb, but that’s all I could think of. LOL Looking over at the bench press you say “wow that’s a lot of weight!” As I’m usually by myself I didn’t bother to unload it. There are five 45 pound plates on each side. Then, noticing my t-shirt you ask me “if I played football there.” You also ask me if I ever played for the Colts. I say “Yes, a long time ago. But no, I never made it to the NFL. My senior year I really fucked up my knees and that was that.” You reply, “I’m sorry you got hurt. I used to play too. I was a Wide Receiver. What position did you play?” “Middle Linebacker and occasionally Defensive End.” Laughing you say “Oh. So you were one of those ‘bad boys’?” Continuing, you add “You know, I love sports but I never thought I was big enough for football. And as I got older I realized that I was doing it mostly for my family. By the way, my name’s Kirsten.” “I’m Andy, nice to meet you.” We talk for a while about the university we both attended, and it turns out we actually lived in the same dorm! Only you are seven years younger than me. Your major was Chemistry and you work at Eli Lilly. You ask me what I do and I tell you that I went back to school got my Doctorate, teach at a university in downtown Indianapolis and have a consulting practice. It turns out we have a lot in common and I ask you if you would like to go out somewhere after we finish working out. You say “In Indianapolis? At this time of night? Why don’t you just come back to my place?”

Zionsville is not very large and it turns out you live in one of the apartment complexes near me. You ask where I live. I say “Stonegate, we’re practically neighbors.” After we go back to your apartment, you ask what I would like, I say “anything’s OK.” “Anything?” you say giving me a sly look. Making us both a Jack and Coke you join me on the couch and we talk for a while. After a couple of drinks you say “It’s really hard to meet a nice guy. I’d like to get to know you better, Andy.” Normally I’m the one that makes the “first move” but before I get a chance you are on top of me. We kiss and our hands are all over each other. We are still wearing our “workout” clothes. I run my hands up your thighs and feel your firm ass through your tight shorts. As we make out I can feel your cock getting hard. You pull your tank top off and practically rip my shirt off. Sitting on the couch you lean back with your arms stretched out and spread your legs far apart. Kneeling between your legs, I pull the waistband of your shorts down revealing your beautiful cock. It is one of the biggest I have ever seen. And you are already dripping pre cum. I say “God, Kirsten, you are so gorgeous” and proceed to suck you ever so slowly. I can tell exactly when you are about to cum and back off slightly keeping you on edge. You moan, and say “Oh God Andy, that’s like torture, I love it! Fuck that feels good.” Eventually I “let” you cum and you literally explode in my mouth. Your cum tastes great and I swallow all of it. You arch your back and wrap your legs around me. Then you collapse onto the sofa. You say, “That was awesome Andy, now it’s my turn…” Trading places you pull my shorts off and go to work on me. You start by playfully biting my nipples and slowly working your way down. You lick my cockhead and shaft and then begin to slowly suck me off. Just like I did to you. You tease me ever so slowly that when I finally do cum it feels like it won’t stop. Afterward we lie close together and you say “I think that you are the best workout partner I’ve ever had, Andy.” “You too Kirsten” I say. We have another drink and sitting up, you look at me and say “I’d like to show you my bedroom. I know you live close by but you are welcome to spend the night. I’ve really enjoyed tonight. I’m glad we met.” “I wasn’t planning on going anywhere, Kirsten. I’ve had a great time too.”

We are both a little drunk and giggling we lean on each other as we manage to make it to your bedroom. Your bed is huge and on each corner it looks like there is some kind of “attachment” and on the headboard there are metal rings. I can feel myself getting hard again. You notice this and smiling at me you say “so you like this kind of thing?” We stand there naked and start kissing and feeling each other up all over again. Barefoot we aren’t really that far apart in height. You are only four inches shorter than me and I work my way down, kissing your neck, your breasts, your incredible abs, and your thighs. When I start to suck your cock, you stop me and say “Andy, this time I want you to fuck me. I love to be tied up and I can tell you are someone I can trust. Do whatever you want sweetie.” As you lay back on the bed I tie your wrists and ankles to the bedposts. You say “Andy, this bed can do much more than that… look underneath.” Looking under the bed I discover a “ratchet like” mechanism. I ask you “are you sure about this Kirsten?” “Yes I’m sure. I’ll tell you if it’s too much.” Slowly I turn the ratchet and soon you are tightly stretched spread eagle on the bed. I am very careful not to hurt you. Every muscle in your body stands out. God you look so fucking hot. I feel like I could cum without even touching myself. I can tell you are so turned on that your cock seems even bigger than before and the precum is flowing. I find some oil and gently massage your amazing body occasionally stopping to stroke your cock. You just moan and say “that feels so incredible, I can’t wait to have you inside me.” When the time is right I undo your legs and tie them to the headboard. Your legs are spread so far apart and your ass is in the perfect position. Climbing onto the bed I enter you very carefully using lots of lubricant and begin to fuck you. Slowly at first. As we both cum the feeling is even more intense than the first time. Your cum shoots up onto your stomach and breasts. We both lie there for a while. Then I untie you. I stroke your hair and look down at you. You touch my face and smile at me. “That was the most incredible first date I’ve ever had, Kirsten. What would you like to do next time?” “How about a movie?” you say.

Copyright © 2016 AMS

[franalexes]

My fantasy:
A9127 falls in love with me.
The rest is just personal details.

[a9127]

Originally Posted by franalexes

The rest is just personal details.

Like you tie me to the bed?