When Finally We Meet

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Older man has an evening of surprises with a crossdresser.
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oberon_52
oberon_52
160 Followers

Dear John:

This is the last e-mail you will receive from me before we meet. You had read my previous story, "Visit to an adult store," in which I had my first gay experience with a much older and stronger man and was forced to wear a sexy, off-the-shoulder, bare-midriff harem outfit while he ravished me.

Over the last several months, you and I have gotten so close through all our e-mailing back and forth. I love the fact that you are considerably older than my 22 years and bigger than my 5-7, 147-pound frame. You describe yourself as masculine and aggressive. That turns me on, as does you writing that you have a beard and moustache.

I've confided in you that with my tiny waist, curvy torso, feminine facial features and long, straight blond hair that I have been crossdressing almost exclusively for the last five months.

I have been taking female hormones, and have begun to develop soft, small breasts.

But your most-recent e-mail has led me to believe that I may have unintentionally given you the wrong impression about myself. You described what you wanted to do to me, and you seemed almost arrogant.

I'm not a notch on anyone's belt. I'm not an easy conquest. (I just stopped typing this, stood up and looked at myself in my off-the-shoulder nightgown in my full-length mirror. With my hair hanging straight down over one eye like Veronica Lake and my slim figure, I don't think any man could resist me right now. I am soft, yet firm and curvy. I am a knockout.)

I am also a lady.

If you want me, you're going to have to earn me, darling.

First, we would arrange for you to meet me one late afternoon at my apartment. You've never told me your real name, preferring to call yourself John Smith. That's fine with me. The mystery is intriguing. You would, of course, be very excited at the prospect of making love to me. Knowing how thoughtful you are, I am not surprised when I see that you have brought me flowers. But when you knock and I open the door, you are surprised to see that I am not wearing a sexy dress or penoir.

I am wearing a high school cheerleader's outfit. My blond hair is in pigtails. The only bare things are my arms, a little bit of my tiny waist and my trim, shapely legs, as my plaid skirt only comes down to mid-thigh.

"Robin?" you ask.

"No, silly." "I answer. "I'm Robbi, Robin's younger brother. Are you Mr. Smith? Robin told me you'd be coming. She asked me to keep you company until she got home. Are those flowers for Robin? She's going to love them. Please, Mr. Smith, come in and sit down while I put these in water."

You look puzzled as you come into my neat, one-bedroom apartment. I ask if I can get you anything, but you say no and sit down on the living room couch. The TV is showing VH1. Out of the corner of my eye, I see you studying me while I put the flowers into a vase. My movements are so youthfully feminine that if I hadn't told you I was Robin's brother, you would definitely think I was a young girl.

I sit down next to you on the couch with my knees underneath me. I smell and look fresh and look you right in your eyes as we chat about this and that. Your trip to see Robin. The weather. My high school. How sometimes -- like today -- I stop by my brother's apartment on my way home from school. I'm sitting a good foot away from you. You notice my blue eyes and how my trim upper body almost imperceptively shimmies while I talk and how the edges of my pig tails rest on my bare, young shoulders.

I ask you if you work out, and you ask me why I asked. I say that you seem to be in very good shape for your age. Then, realizing I had said something that could hurt your feelings, I bring both of my hands to my mouth and my eyes get very wide. I say I'm very sorry. I didn't mean it that way.

I reach out and touch your bicep, and you smile and make a muscle for me.

"My," I say. "You are awfully strong. I'm sure you must be stronger than the boys at my school."

I adjust my body so my legs are no longer under me. I'm not certain, but I think I spot you sneaking a glance at my thighs as I just happen to sit a bit closer to you. When I lean back on the couch, your left arm is behind me. You're very nonchalant as your fingertips begin to play with my bare shoulder.

My voice gets a bit nervous as I ask whether you like VH1. You say it's all right, but not your favorite.

"You know," I say shyly, "Robin has some tapes she won't let me see because she says I'm too young. But I guess that since I'm here with an adult, we could probably watch one."

You nod your approval, and I get up to fetch a tape and put it into the VCR. I come back to the couch and kind of snuggle up against you as the tape begins to show an older man and a young man making love.

"Do you like that?" you whisper in my ear as your arm again goes around my shoulders.

My blue eyes are wide and innocent as I stare, mesmerized, at the TV screen. The older man is sucking the youngster's dick while ramming two fingers up his rectum. The boy is in ecstasy, moaning and grabbing the man's gray, balding hair with both hands.

"Do people really do that?" I ask with a hoarse whisper.

Your hand applies more pressure to my shoulder, drawing me toward you. Then, you take my face in both your hands, tilt your head and place your lips on mine. I move slightly to withdraw, but you hold me fast. For a moment, my lithe body moves into yours and you can almost feel my lips start to open.

Then, suddenly I tear my mouth from yours and my trim body from your grasp. I quickly rise, gasping.

"Mr. Smith, no!" I say, my little chest heaving. "I'm only in high school. Why ... you're old enough to be my father."

You stand and put one arm around my tiny waist and the other around my back. As you crush me to you, my arms are helplessly on either side of my head.

"Mr. Smith, please ... "

I struggle, leaning away from you, but your strong arms hold me fast. You kiss me and I begin to melt. My arms slowly go around your neck. Our mouths open, my upper lip feels your moustache, and you suck my tongue into your mouth. Your tongue then invades my sweet mouth, and I moan as your hands begin to explore my tight, undulating body.

Then, you strongly grab my ass.

"NO!" I shout. Once again I tear myself away from you. I turn my back and I begin to cry. "Mr. Smith," I sob, my slender body trembling in the cheerleader outfit. "I'm just in high school, and you're a grown man."

"But you're so beautiful," you say as your right hand goes around my body. I can feel your erection on my back. Your left hand grabs one of my pigtails and tilts my head to the side. Your mouth goes to the opposite side to my bare neck and nuzzles it. I can feel your moustache and beard on my delicate skin.

"You know you want it," you say confidently.

I struggle, but I begin to weaken. Your mouth at the base of my neck is making me swoon. You turn me around. Your face is arrogant, overpowering. My will to resist is buckling, but then you take my dainty right hand and place it on your crotch.

"NO!" I shout, and this time you can tell I mean it. I break away from you, run to the door and open it.

"Get out!" My voice is low as I try to compose myself, my chest heaving, tears streaming down my face. "Come back in an hour. Robin will be home by then."

You look puzzled, but you walk toward the door.

"Don't tell Robin I let you kiss me," I say as I slowly regain my composure. "She likes you, and I don't want her feelings hurt."

You nod, look at me, a bit disheveled, yet so beautiful in my cheerleader outfit, and leave the apartment, wondering what to do for the next hour.

The next 60 minutes seem to crawl by for you. You drive off and find a McDonald's. You sit with a cup of coffee and stare into space, trying to figure out what had just occurred. It's almost dinnertime, so the McDonald's is fairly crowded. Lots of kids, moms and dads and a few businessman types who are probably padding their expense accounts with big meal charges while actually eating a Big Mac.

Your eyes wander aimlessly until someone catches your attention ordering at the counter. She's wearing a bathing suit top with the straps around her neck. Her little white shorts begin low on her trim hips. Her very-thin, curvacious torso seems to go on forever. Her straight, thick blond hair hangs halfway down her bare back. Her perfect posture with her shoulders back complements her toned, yet soft arms. Her legs go all ... the way ... to the floor with her feet in a sexy high-heeled clog. You aren't the only one to notice her. Every man in the place -- including the dads -- has his eyes on her. You wonder if her face is as beautiful as her body, but you can't see it. She orders only a milk shake, and as she turns to leave the restaurant, you catch a glimpse of her face.

Her features are soft, almost delicate, very lovely ... and somewhat familiar. If you didn't know better, you would think it was Robbi. Yet, this person was older, certainly by at least a few years. Robbi was a girl. This was a woman.

Suddenly, she was gone, out the door. A couple of businessmen at another table smile and raise their eyebrows at each other as if to say, "Wow! Wasn't she something."

You look at your watch. You still have 25 minutes to wait.

The minutes creak by until it is finally time for you to return to my apartment.

You knock on my door, it opens, and before you stands the "woman" from McDonald's. I'm still wearing the shorts but have changed out of the bathing suit top and into a cut-off T-shirt. It's cut almost halter close to my neck. My arms are bare except for my long hair cascading over them and reaching down over much of my long, bare torso.

"Robin?" you say tentatively.

I smile, take both your hands in mine and bring you into the apartment. "Of course," I say, "and you just have to be John."

I reach up and kiss your bearded cheek, then take one hand and lead you over to the living room. You notice how small my hand is in yours and how good my subtle perfume smells.

"I'm sorry I wasn't here when you arrived," I say. "I hope Robbi kept you entertained?"

You mutter something about him being very entertaining. You don't know what's going on. Is this the same person? Can it be?

"I only missed you by about 10 minutes," I say. "Robbi said you had an errand to run and would be back. He seemed kind of upset about something, so I went out and bought him a milk shake before he went home to our parents' house. It's hard to figure him out sometimes. Oh, by the way, thank you for the lovely flowers. That was very sweet of you."

I reach up and put my perfect arms around your neck and kiss you. Your hands go to either side of my tiny waist. I break the kiss momentarily.

"I've been wanting to do that, darling, ever since your first e-mail," I say. My arms are still around your neck, my T-shirt riding up my curvy torso. "I wanted to be all dressed up for you when you came here. I hope you're not too disappointed."

"Disappointed?" you say incredulously. "You're the most beautiful creature I've ever seen!"

I sigh and reward you with the most tender kiss of your life. You've never felt lips so soft, yet so passionate. This is not a normal kiss. This is a meeting of two souls -- one needing to dominate and the other needing to be dominated.

Up on my toes with my arms around your neck I surrender my flesh for you to despoil. When your hands grasp my bare sides and caress me, my body reacts almost involuntarily. It's the same everywhere you touch me, little jolts that send my lips harder into you as my moans are muffled by your passion. Your mouth and fingers can't get enough of me. As for me, I'm thinking that my body has been created just to give you pleasure. My soft, little breasts can feel how hard your chest is through our clothes. I'm so glad I'm pretty and you find me attractive.

You hesitate a moment, remembering what happened with "Robbi," then you grab my ass cheeks. To your delight, I moan and open my mouth to kiss you in abject surrender to your strength and overpowering will.

Our minds are both swimming. I can feel the hardness of your trapped penis as your right hand on my butt grinds me into you. As I lean back, your left hand plays with my hair. Finally, you break our kiss and move to lift my shirt and nibble on my nipples.

"Wait," I say, moving away from you. My little chest is heaving and my arms are palms-out with my elbows at my sides. You've never seen anyone you've wanted more.

"We're going out," I say with an impish grin. "You're going to take me out to dinner and dancing."

You stutter some words of protest, but it's too late. I duck into the bedroom and you hear the door lock from the inside.

You are very frustrated, and don't I know it. I'm terribly turned on, too, but I don't want to surrender to you too soon. You are too special to me. I lean my back against my side of the door.

"John, darling?"

"Yes," you reply.

"Do you want me?"

You reply that you do.

"Well ... you can't have me, at least not yet. You're very overpowering and I love how you kiss me, but I think we should get to know each other. Let's go out to dinner so we can talk, OK, darling?"

You say, all right.

"John, I'll just be a few minutes," I say. "I want to make myself beautiful for you. Why don't you watch some TV, and I'll be right out."

You hear the shower spraying and reluctantly walk over to the couch, sit down and turn on the TV. The tape you were watching with Robbi is still in the VCR, but when you turn it on you notice it has been rewound. The young man is a student and the older man his professor who tells him there is only one way he's going to pass the course. The boy has short, dark hair and is very thin, while the professor in a three-piece suit is sturdy-looking with a ruddy complexion. The boy stands, mortified, with his hands clenched at his sides while the professor unbuttons the boy's shirt and removes it ... ever so slowly ... over his thin shoulders. The older man hynotizingly looks the boy in the eyes and rubs his fingertips over the boy's sensitive nipples. Then, he orders the boy to remove his pants and underwear.

With the boy naked and ashamed in front of his fully clothed professor, the older man slowly approaches and rubs his hands lightly over the boy's chest and arms. He finally puts his arms around the boy and kisses him while the clearly miserable boy's arms hang limply down his sides. Stepping back, the professor takes one of the boy's hands and places it on the boy's penis. They exchange a glance. The boy is almost surprised to notice that his penis is hard and pointing almost straight up. Smiling, the professor forces the youngster's head down.

Your mind begins to wander as the boy opens the man's fly and takes out his fat penis. Soon, haltingly at first, he's sucking on the old man's cock. The boy is very attractive, but there is no escaping the fact that he is, indeed, a boy. You begin to wonder about me. Beneath my clothing, could I possibly be a girl?

Not that it matters that much to you. If I'm a girl, then you'll try to fuck me, anyhow, but you were all psyched up to make love to a boy.

You hear my shower stop.

"Robin!" you call out after a few moments.

"Yes, John," I reply in a soft, feminine voice.

"Robin, I don't know how to ask you this ..."

I peek my head out the door.

"Stay right on that couch and don't move," I say.

Then I open the door slowly and stand in the doorway. I am wearing only a white, mid-thigh-length terry cloth robe. It is open off my thin shoulders, revealing almost all of my softly taut chest. You can see the beginnings of my modest cleavage. The robe's terry cloth belt is tied twice around my impossibly thin waist. I pose with one foot ahead of the other, revealing a good deal of thigh, and place my hands on my very trim hips. From the couch, you can see droplets of water on my beautiful, soft shoulders and pretty chest.

I seductively shimmy my shoulders. You have never seen anything nearly half as lovely as the blond beauty scant feet away from you.

Slowly, ever so slowly, my left hand leaves my hip and grasps my robe at thigh-level. I smile shyly as I open the robe a bit, and out pops about 5 and a half inches of erect penis. After a few seconds, I cover it again.

"There, darling," I say, teasingly shimmying my bare shoulders even more prominently, "does that answer your question?"

Your eyes are filled with lust. I retreat back into the bedroom, and you hear the lock click again.

You can't help but have an erection, and you are getting very tired of being kept from what you want ... what you need.

You look at the television, and the naked boy is sitting, facing the professor on his lap. The professor is still fully clothed, but it's obvious his cock is out and buried deep into what had been a virgin ass. The professor's hands run all over the youngster's back while the boy -- eyes closed -- bobs up and down. This goes on for a very long time, and when the professor forces an open-mouthed kiss on the boy, he eagerly responds and begs for more.

You open your own fly and take out your huge, pulsating cock. You know you need relief, and you need it very soon. You hear me rustling near the door and you quickly put your hard-on back into your pants.

When the door opens, your breath is taken away by the sight of the classiest, sexiest person you've ever seen.

I am wearing the staple of every woman's wardrobe: The Little Black Dress. It has short sleeves, a moderately low-cut neckline and ends very high on my shapely thighs. It is so tiny that you don't see how anyone could get into it, but you can tell every time I move that my curves fit beautifully and comfortably. I am wearing tasteful silver earrings and part of my hair hangs straight down over my left eye like Veronica Lake and the rest flows down my perfectly postured back.

You are mesmerized as I slowly walk toward you, undulating under that little dress with each little step. As I come close to you, I turn my back. There are a few inches left unzipped near my regal neck.

"Be a darling and zip me up, will you?" I say as I lift my hair so it won't be stuck in the zipper.

You take hold of my arms and bring your lips to the back of my neck. I instinctively back up and I can feel your hard cock on my back through your pants. As your wet mouth continues to nuzzle my neck, I shudder and involuntarily let out a little groan. My eyes are closed.

"Come on, John, darling," I say plaintively. "We're going out."

Your voice is commanding as your hands run up and down over my curvy torso.

"No," you say, sternly. "We're not going out."

Your left arm pulls me tightly into you and your right hand runs slowly up and down the inside of my right thigh. Your mouth is doing wondrous things to my neck.

"We're ... we're not?" I whisper.

You turn me around, grab me around the waist, your hands going almost completely around it, and look intently into my blue eyes. My hands are lightly up against your hard chest.

"You've been teasing me ever since I got here," you say. "I'm through being played with. I don't care how beautiful you are. You are still my boy and you're going to do what I tell you to."

You kiss me -- hard. I struggle, but you're far too strong. Your tongue invades my mouth and soon you can tell my resistance is melting. My body slowly begins to undulate into yours. Finally, I am able to free my lips from yours.

"Let me go," I say.

"You don't mean that," you say confidently. You love being in control of such a beautiful, classy person. You lick my left earring and then run your tongue into my ear. Your hands are all over my body, finally settling on my ass, which you grasp repeatedly.

oberon_52
oberon_52
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