One Special Friday Night

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Guy meets woman he met on the internet & gets a surprise.
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As you prepare for your "date" you are nervous. Yes, of course you have been chatting with Sonya for several months now and you know that you two share a common bond, dressing in sexy women's lingerie, even though you are biologically a male. Maybe it's the anticipation of what might or might not happen.

I mean, your conversations with Sonya, or Red, as she likes to be called have gotten you so hot. You hope that you are not building this up too much and are going to be disappointed, but you quickly dismiss that thought as you recall Red's last email, "make sure you dress extra sexy when we meet as I am working on a surprise for you." That thought alone has fueled your libido and is probably the reason why you spent so much money at the lingerie shop this past week.

Not to mention spending quite a bit of money on a new pair of 5" high black open toed high heels, commonly referred to as Come Fuck Me Pumps. So, as you step out of the shower, after completely shaving off all of your hair from the neck down, you towel off and notice a tingling feeling. You powder yourself and then head into your bedroom to begin the transformation.

Red didn't exactly tell you what to wear, but she certainly made some very good suggestions. So, you start by gluing on some false tits that she told you about and notice that as you wait for the glue to dry that the breast forms seem to heat up and conform to your body. In fact as you get up, you brush against one of the nipples and swear that you can feel it.

This sensation is confirmed as you put on the black lacy bra and notice that as the nipples poke through the slits in the cups. You gently reach up and begin to lightly rub your protruding nipples, which causes a wave of ecstasy to ripple through your body and your knees to become weak. You can't believe what you are feeling and now know that no matter what Red has in store this alone will add to the excitement.

You then don a matching garter belt along with black sheer nylons. You debate about putting on the matching black lacy thong, and decide to do so just so you can complete the sexy image. Once you have the thong in place you find it extremely difficult to not have a hard on, but remember that Red explicitly requested that you hold off from relieving yourself for this week prior to your meeting so as to add to the enjoyment.

So, you refrain from taking care of your not so lady like problem and continue with putting on your new pair of heels. Thankfully, you bought them early in the week and have had some time to practice walking around in them. As you stand from buckling them you walk over to your vanity and begin to apply your makeup.

You start with a nice foundation, add rouge and eye liner. You add eye shadow in such a way that it makes your eyes look smoky and mysterious. You apply a bright red lipstick, as it matches your painted toe nails and will match your fingernails once you paint them too.

Once your fingers are dry you apply some perfume in all the right spots, comb out your hair, which you have been growing out and then head to your closet to don your dress.

As you settle it over your now very curvy body you look at your self in the mirror and realize that you are one very hot looking woman. You can't believe the image that is staring back at you and it isn't until you reach up to shift a lock of hair that you convince yourself it is you.

You look at the clock and realize that you are right on time and that you had better get moving if you are going to meet Red at the restaurant on time. You grab your purse, making sure you have your lipstick, some tissues, a tampon and a condom. You aren't really sure why you have to carry the last two, but Red suggested that a woman always needs to be prepared for anything.

You walk out to your car in the garage and quickly head out to La Petite Folie. As you arrive you notice the valet begins to tent his pants as he watches your luscious legs swing out of your car. You smile to yourself as you walk into the restaurant.

As the maitre d' leads you back to a rather secluded table you notice that several men in the restaurant have perked up and taken notice of you. As you reach the table you see that Red is already there and is enjoying a glass of wine.

As you sit down she slides over and greets you with a peck on the cheek. You smile at each other and make small talk until the waiter appears and takes your orders. During your salads you can't seem to take your eyes off of her, as you have never seen her before except in one picture, and that one didn't come close to doing her justice. She has auburn hair, with deep blue eyes that just seem to drink you in and ravish you. You notice that her make up is very similar to yours but quickly dismiss it as coincidence.

Suddenly while you are taking a bit of salad you feel her foot begin to slide up your leg and it causes you to jump. She doesn't stop until she is stroking your groin with her nylon covered toes. You stare at her with a wild expression; she just smiles back at you and continues with what she was talking about.

As the waiter delivers the main course she removes her foot and gives you a rather impish smile. The rest of the meal is uneventful unless you count the fact that between the two of you, you have polished off two bottles of really good wine. As Red asks you if you are ready to head to her place you feel the wine begin to take its affects on you and excuse yourself to the bathroom and tell her that you will meet her outside.

As you exit the restaurant, you see her standing next to a cab and she informs you that since you both enjoyed the wine so much she thought it better if you just caught a cab. As you pile in the back you notice her very short red dress ride up and reveal that she too is wearing nylons and a garter belt.

As you slide in next to her in the back seat you notice the cab driver give you both a very appreciative look, especially when Red begins to rub her hand up and down your nylon covered leg. You try to reciprocate, but she merely places your hands back in your lap. At first you feel hurt, but then realize it is to cover your "rising problem".

As the cab pulls up to Red's apartment you both get out and she unlocks the door and lets you in. You then follow her through the hallway into the living room where she tells you to relax on the couch while she makes up a couple of drinks. As she returns, you can't keep your eyes off of her and she notices you staring and asks if you like what you see.

You are so mesmerized by her beauty that all you can do is nod your head. As she places the drinks down on the coffee table she sits right next to you and leans in and gives you a very long, very passionate kiss, which you return in kind. As you part you realize that your lipstick is smeared but aren't too worried as she leans in again to kiss you some more.

While she is kissing you, her hands begin to roam all over your body, sending little shock waves flooding your system and all you can do is moan and melt into her embrace. After 15 minutes of kissing, she stands up and pulls you up with her and takes you by the hand and leads you into her bedroom.

Once there, she begins to pull up her dress revealing a matching set of lingerie as you are wearing only it is in red and looks simply awesome on her gorgeous body. She then begins to lift your dress and once you raise your arms for her to remove it she leans in and kisses you.

However, she quickly takes your hands behind your back and before you know what is happening she has put a pair of handcuffs on you. Your initial reaction is one of shock, but she merely continues to thrust her tongue inside your mouth and run her hands all over your sexy hairless body.

You decide to let go of your inhibitions and allow her to lead you over to the recliner that is in the corner. Once there, she sits down in it and pushes you down to your knees so that you are now looking at her neatly trimmed pussy peaking through the lacy material of her thong.

As you kneel there staring at her beautiful mound, she gently takes the toe of her foot and begins to stroke your groin area. You try to lean in so you can rub up against her nylon covered leg, but she stops you and spreads her legs, placing them on the arms of the chair, further exposing her pussy to you and signals you to come closer with her finger.

You eagerly mover closer and lean in to begin servicing her. You realize that with your hands secure behind your back, you can't really control how far you lean in and so you quickly find yourself bury deep within her folds. The scent of her moist pussy is intoxicating and just as you begin to try to lick her folds she reaches down and pulls her thong to the side.

You waste no time and dive in and begin to lick and suck on her. You realize she must be as horny as you because it isn't very long before she is bucking in the seat and grabbing your head and holding it against her while she writhes and moans in pure sexual release.

As she pulls your cum smeared face from her crotch she looks down at you and whispers that it is now time for your surprise. You can't imagine what it could be, when suddenly you feel another set of hands rubbing your shoulders and stroking your hair. You turn to see who it could be and come face to face with a rather large, rather hard cock. You start to look up, but Red quickly covers your eyes with a blindfold.

She then helps your turn around and whispers in your ear that since you like to dress like a girl she thought you would also like to do other things as a girl. As you open your mouth to respond she pushes your face forward until the tip of the cock is touching your lips. You tentatively flick your tongue out and touch it and as you draw it back realize you tasted something salty.

Red continues to whisper in your ear that it is your sexiness that has caused this cock to become so hard and that it is only fair that you get to enjoy it. You agree with her and open your mouth and lick the entire head. You then begin to lick and nibble your way down his shaft until you reach his balls.

As you are trying to figure out what to do so you don't fall on your face you feel Red undoing the cuffs and you quickly place your hands on this man's thighs and begin to suck and lick his balls one at a time. He continues to hold your head with his hands and moans as you bath his nuts with your saliva.

You then work your way back up to the tip and once there open your mouth and begin to take him a little at a time. Since he knows that this is your first time in swallowing such a monster he allows you to go at your pace and little by little you are able to take more and more of him in until you can feel your nose hit his stomach.

He then holds your head there and allows you to get used to having such girth not only in your mouth but also pushed down your throat. Instinctively you begin to breathe through your nose and he begins to pull your head back until just the tip is inside your mouth.

Well, something inside of you snaps and you attack his cock with gusto and begin to bob back and forth on it. In fact at one point you reach up and begin to cup and fondle his balls. After 10 minutes you feel him start to swell and instead of pulling off you bury his cock all the way down your throat as the first streams of cum erupt out of it.

You do your best to swallow it all, but being a novice some of it trickles out of the corner of your mouth. As he holds you there with his semi hard cock still in your mouth, you hear Red let out an orgasmic scream and then tell you how hot that was to watch. She then tells you to get up, take the blindfold off and lay down on the bed. You quickly comply and are once again greeted by her warm, moist pussy as it descends towards your eager mouth.

As she straddles your head and feeds her pussy lips and nectar to you she reaches down and begins to play with your nipples that are sticking out of the lingerie. This causes your own cock to stir at which point you feel some hands reach up around your waist and pull your panties down and off your legs.

You then feel Red lean forward as she takes your cock into her mouth. As she works you in and out of her mouth, not only does she push her own pussy lips down onto your face but she reaches under you and begins to play with your rosebud.

At first you are a bit taken aback, but she merely tells you to relax and just enjoy tonight. You do as she says and before you know it she has first one and then two fingers pushed up inside of you and you are moaning and thrusting your cock into her mouth. However, every time you get close to cumming she stops sucking and gives your cock a little breather to reel you back in. She keeps this up until you think that you will lose your mind in sexual frustration.

Just as you are getting close, you feel her remove her fingers, however, this time they are quickly replaced with what you can only guess is that wonderful cock you just sucked off. Sure, enough you feel his bulbous head pushing at your entrance and Red lifts her head and tells you to relax. You focus on relaxing your sphincter muscles and before you know it his head slips in.

As he holds it there to allow you to get used to it, you feel Red begin to shake and cry out as yet another orgasm racks her body. As you lap up her juices as they pour out of her sopping wet pussy you fell his thighs push against your own and realize that he is all the way in.

As you take in this new feeling and experience you start to get a warm feeling deep down inside. He then begins to slowly slide in and out of you and eventually builds up speed until he is thrusting inside of you and you are bucking your hips trying to get all of him inside of you.

He continues to slam his meat into you for what seems like forever and just as you feel him swell, he thrusts all the way in and holds it. As he pumps load after load of hot cum inside your bowels, you finally let loose with your own orgasm that seems to start in your toes and work its way through your entire body. You cry out and shutter and shake so violently that you can't believe the feeling of sexual release you are having.

Red, being the consummate cock sucker, swallows every last drop of your load and continues to pump your cock with her mouth and lips. As he deflates and slides out of you, Red turns around and impales herself on your still rigid cock.

As you feel her warmth and wetness envelope your member she starts sliding your head closer to the edge of the bed until it is hanging off of it. As she begins to ride your cock with wild abandon you suddenly are presented with the mystery cock and so without any hesitation you quickly take it into your mouth and begin to clean it off.

Since you just came not more than minutes ago, Red is able to ride you for quite some time and experience several more orgasms. You also succeed in getting him hard again and are rewarded with yet another load of his cum.

Finally, you explode inside Red and as she feels you empty your nut sack inside her she collapses on top of you, the cock disappears and before you know it you both fall asleep entwined as you are.

The next morning you awake, feeling a bit sore, but definitely feeling very excited about finally getting to meet Red in person. As you look around the bedroom you realize that she is must be in the kitchen as you smell coffee wafting in through the open door and wonder what today will bring.

THE END

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AnonymousAnonymousalmost 5 years ago
Geez

Post this in the appropriate category...Trans and Crossdressers...

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