Jenna

By Jenna Shannon

Published on Nov 2, 2001

Transgender

Sometimes a "girl" like me just needs a man to scratch her itches. Sex with another transvestite is so wonderful. T-girls are always smooth, perfumed and gentle with each other. Guys on the other hand are harry, rough and totally self-centered, which is just the perfect combination of traits for the sort of cravings I occasionally get.

I don't go out of my way to dress especially nice when I need a man. The kind of guy who is going to have me doesn't give a whit whether my panties are $30.00 dollar silk, Victoria's Secret bought especially to match a $70.00 dollar chemise. All he cares about is putting that long, hard, delicious fuckstick in something warm and soft. For that matter I don't care either. It's a match made in heaven.

It's easy to dress for this kind of sex. My rule is if you want it rough and wet, dress that way. Of course I shave, a girl does have to be smooth, but I don't make that extra effort to cover up my beard shadow. Clothes are even easier, dress like a chick with a dick. Tonight was no different. With an eye towards my own pleasure I had dressed in a black leather mini, white satin button up blouse and a black leather jacket. Under my ensemble I wore my favorite cream satin bra and panty set with lace top, off black thigh highs. I know I'll be on my knees at some point so there is no reason to shred up my good pantyhose. Of course I had over done my make-up. Way to much eyeliner and mascara mixed with a heavy smoke gray shadow, brought out all the slut in this girls bright blue eyes. I had painted a deep red lipstick over my pucker and slathered it with gloss to give a pouty look to my lips. I had my long brown hair pulled back with a headband to create a fuller effect around my face and to keep it out of my mouth in case I found a hard cock that needed satisfaction. When I'm finished dressing this way there is no doubt as to my intentions or my gender. Why confuse the poor dumb sods; let them know what you want and they will deliver. I blew one last kiss into my make-up mirror, grabbed some condoms and headed for the local gay watering hole.

I love the way the chill October wind runs across my nylon clad legs as I walk across the parking lot to the bar. I always park as far from the entrance as possible just to enjoy the clickety clack of my heels. Just the act of entering a place dressed as women arouses me. I can feel my boy clit straining against the fabric of my panties. I just know tonight will be wonderful.

Gay bars are always smoke filled dens full of loud music and deep shadows. The door opens and I am inside. The press of other bodies is warm and familiar. I recognize other T-girls around me as well as some past dates. It 's nice to be in a place that I know and it knows about me. I make my way to the bar and order a large creamsickle, (that's a Zima with a popsickle in it). I use a straw, that way I won't muss my lipstick. I put my coat over the barstool beneath me and hop up on the stool. I'm careful to show a discreet amount of leg and just a peek of my thigh highs. The sign is now out on the road; it's time to bring them in.

I talk with my usual crowd of gal pals comparing notes about guys and clothes, while each of us enviously eyes the others attempts at slutdom. I had just gotten a new pair of earrings from Walmart. Long, golden, dangley, autumn leaves that flashed from the strobes on the dance floor. Whenever I shook my head I could hear their gentle chiming. They were driving my friend Amber crazy. She claimed she just had to have them and promised me as many blowjobs as I wanted to have (or take from her) to get them. With a light kiss on her cheek I whispered that if I didn't find someone soon she'd find them on the pillow next to her in the morning. We both giggled at that. We'd been standby lovers for a long time and she'd cum in my well-lubed asspussy many times.

The man I'm looking for is forty something, "straight" (whatever that means) with a hag of a wife. She's fat and gross and away to visit a sick relative or whatever, so he's out tonight to live his "SECRET" fantasy. That's me, the girl with "something extra" in her panties. (I've often thought of getting a necklace with just the word fantasy written across the front of it.) As though being in a known trannie bar hides either of our secrets. That's OK the little wifey at home will never know about this side of her strong man. She'll never know how he aches to be filled up by another guy's cock, or how he would love to suck and swallow another mans salty seed.

La dee da, people come and people go. It's about eleven thirty when I spy my quarry for the evening. There he is, in conservative khaki pants and a dark jacket. I just know he won't be to large and he'll be polite as hell, just a little embarrassed to be around me at first, but his embarrassment will pass quickly. I can tell he's eyeing the T girls and not the other guys. Perfect! I make sure my drink is low because he'll want to buy me one. That way he can establish his territory over me. As I walk by his table I flick my left earring and cause it to fall in his lap. His first reaction is to look down at what's there to see my hand following the earring. Of course while picking it up I accidentally brush my hand against his crotch. I apologize furiously and the only way to make for my faux pau up is to sit down and enjoy a drink with him.

Chat, chat, chat, they always want to chat. He could just put his lips next to my ear and whispered "Can I suck your cock?" He'd rather ramble on about how all this is new to him and how he's never done anything like this before and all the other inane things that he needs to get over, before he gets down into my panties. At least he doesn't bring up sports! Finally he's done and ready to party with me. He's bought me two drinks so his dinner ticket is paid for. Everything that I suspected about him is either true or suspected. I can tell he wants to play, but is having a hard time asking for what he desires. Finally I can't stand it anymore.

"Could you walk me to my car?" I ask with a smile. "This isn't the nicest of neighborhoods and its nice to be with someone"

"Sure" he replies. Here is something he can handle, protecting the little lady.

We walk out together and he helps me into my coat in the foyer. I shiver from the cold and ask him to put his arm around me. Another good reason I park away from the entrance is because it's much more private. We reach my car and I dig my keys out of my purse. I pretend I can't see the door lock very well so I bend over to slide the key in. He's lined up perfectly behind me and I push my ass against the front of his pants. A little grind and I can tell he's hard. With the door open I turn back around towards him and give him a hug. Which of course turns into a kiss. His lips are wet and warm, as I slide my tongue into his mouth. Our tongues dance as we stand together. I'm not a shy girl at all. I quickly slide my hand down to his crotch and grope his cock. He's standing tall.

"Just so we know all about each other maybe you'd better have a feel too." I purr at him. His hand slides down my leather skirt, which I hike up a little, to rub the hard, satin covered, cock he finds there.

"Is this what your looking for Hon?" I ask with a leer.

"Yes it is." Comes his trembling reply

Taking his hand I open the back door of the car and ask if he wants to make me feel good. We get into the back seat and start kissing again. My hard shecock is pulsing in my panties as he slides his hand up my skirt to explore the lacy tops of my thigh highs. It doesn't take him long to move up further and begin to stroke my hot hard cock. He strokes my hardness in his hand as his thumb smears precum all over the purple head. Here is the moment of truth. Will this good little suburban cowboy swallow my dick or will I be shredding the knees of my nylons begging for his cum. Ten years of the missionary position make up his mind.

With a gentle push on my chest he crowds me back against the opposite door, hikes up my skirt, and slides my panties down to my ankles. I quickly spread my legs for him as he grabs onto my hard rod. Slowly he lowers his head and slurps my shecock up. He is a gentle careful lover and since he knows what he likes he naturally understands what I want. His smooth soft lips and gentle sucking motion soon make me gush into his mouth. He gags a little as the first rush of cum hits him but he manages to swallow the entire load. When he's finished sucking me dry he gently kisses my deflated cock and brings up his head to look at me.

Turnabout is such fair play. Now it's my turn to perform for him. If half of what he told me is true this is the first blowjob he's ever given. Poor guy, it seems that it is also to be the first one he's gotten in a long time too. The little women at home refuses to satisfy him this way. Her loss, my gain! He leans back against the opposite door raises his butt up and slides his pants down. The gleam of his tighty whiteys glows in the dim street light. I could be a true cunt like the chubby crotch at home and leave him hi n' dry, but it is not in my nature to be such a bitch.

I am this good little straight boys fantasy and I want him to remember this for a long time. I start by coming to his lips first. I can taste the salty flavor of my cum as I kiss him. As we kiss I work his cock out of his undies and begin to jack it. He's uncut which is a plus for me. I'm sort of leaning in between his legs and I arch my self backwards so that our two cocks are close to each other. I take both of us in hand and begin to rub my flaccid clitty cock against his. There is enough light in the car that he can watch my hand as I pleasure us. It doesn't take me long to get hard again and I want to make sure he can see what a nice cockfight looks like.

"You were such a good cocksucker." I whisper to him. "Now it's my turn." With that I release the both of us and slide down towards my favorite toy. We've been playing long enough that any of the finer tricks I've learned would be meaningless, so I just quickly engulf him with my wet warm mouth. "Gentle with the teeth girl." I remind myself as my head begins bobbing up and down his love stick. I stay up by the head and use my tongue to rub his special place. I feel his hands come down on my head in the most natural way and I am in heaven. Within moments I begin to feel him straining and stretching his dick into my mouth. I'd love for this to last longer but he really needs to cum now. With a gasp he tumbles over the edge and his cum streams into my throat. Three full spasms later and it begins to trail off. I know he will be really sensitive so I'm careful to match my pace with him. With a pop he falls out of my mouth and I just nuzzle the head with my lips.

Cuddling is for girls. I don't want to be held or told how great I was, so when his breathing is back to normal, I slip him back into his undies and sit back. I know I look a mess but what's a girl to do? My hair is all over the place and who knows where my panties have ended up. I sit back next to him on the seat and try to fix myself up. It's odd how awkward it feels for two people after the heat of passion abates. Just moments ago I was slurping his most private member and now he won't even meet my eye. Poor thing, wait till the next time his fat, suburban, cotton pantied wife wants some and all he can think of is rubbing cocks with a slutty trannie girl.

If you've enjoyed this story please let me know! From mild to wild there's lots more.

Hugs

Jenna Dera029@aol.com

Next: Chapter 4: Jennas First Time 1


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