From a Husband to a Dutiful Sissy Ch. 04

I keep walking and I look at the guy in the other car, he does make eye contact with me and he smiles. I smile back and keep walking as sexy as I can. As I begin to walk across the front of his car I take my right index finger with it long ruby red polished nail, lick it and gently glide it over the front of his car. I saunter past my high heels clicking away with each sexy step. I feel so turned on but am still very scared as I am alone and who knows what this guy may want, but I keep sexy and confident looking.

I get back to my car, turn around and smile as I start to walk back again. I soon get past the car with the driver and I figure about 10 ft. past his left side I will stop, gently bend over, take my hands and run them up each black stocking clad leg, smoothing the stockings out and making sure the lace tops show as such. I see he is now transfixed on me and my pretty hot looking body. As I stand back up and adjust my skirt, I hear his driver's side window go down. I toss back my hair and turn to look at him.

His window now open he coughs and says, "Um.. ahhh... HI!.. if I can... I'd like to tell you that you look very sexy, very hot."

I smile and reply, "Thank you, I do try. I like to feel and look sexy and hot."

He replies, "Um... ahh... are you Chantel?"

I smile again and reply, "Yes, my name is Chantel, do you like what you see?"

He pauses and then says, "Um, fuck yeah, you have sexy legs, I love those heels and your ass. Mmm nice."

I am very excited as I say, "What is your name?"

He replies, "Um my name is Brad." Brad is a white male about 30-35 years old, brown hair and a beard, his car is a nice lightly aged Infinti G20.

I walk up to his driver's window, bend over in my heels, pushing out my nice little mini-skirt covered ass and look at Brad, "Are you looking at having a bit of fun Brad?"

Brad says, "Yes, it would be great. I saw the ad you placed in Craigslist saying you are a sexy vixen of a crossdresser who is eager to be a tarty, lil slut, but is new to being a slut."

I bite my ruby red lipstick coloured lips and say, "Well Brad, I have decided to with my Mistress wife to become the cding woman that I want to be and I want to be taken like a slut by hot and horny men. So yeah I'm new to cock sucking and to being taken by my sissy ass pussy." I sigh and add, "I'm quite hot and horny to begin to please men who may like me."

Brad smiles and says, "Um, you smell nice Chantel and yeah I'm pretty hot for you now."

I say, "Mmm sounds fun, what are you into Brad?"

Brad says after rubbing his chin, scanning me from head to toe, "Um how about a blowjob?"

I toss my hair back and smile, "Ok, a blowjob could be fun as long as you are ok with me being newbie at it. Also my Mistress wife wants some video made of my slutty acts tonight, will you be ok if we get a cell phone video of it?"

Brad smiles and says, "Sugar, you are so sexy hot looking I'm pretty sure your pretty mouth will give me a Hell of a blowjob. As to the video, why not?"

I ask, "Where do you want to do this Brad?"

He takes his right hand and taps his passenger side seat and says, "How about right here inside my car?"

I say, "Ok darlin." with a smile as I stand back up and begin to walk around to the passenger side of his car. I open the door and gracefully step inside. I am very nervous but now I am on a mission, to suck my first man off and me as a real tranny slut.

Once inside I grab my cell phone and see Brad has his seat fully back and already has his pants and briefs pulled down enough for his ever hardening oh maybe 6 inch, nicely thick cut white cock to hang out, his right hand gently pulling it. I think, 'Well Chan, this is it you are finally going to suck a man off, years of fantasy, many times you had your cock sucked as you lived a man's life and now you are a slut about to suck a man to his pleasure.'

I turn on my video camera and hand him the phone asking him to hold it and keep a video going. I now take my left hand and carefully take over from him using his right hand on his cock. He watches as my lovely ruby red finger nailed fingers gracefully tug on his now hard cock. My right hand then cups his balls and my nails tickle the base of his ball sack. This causes him to pulse his cock in my hands as I compliment him on his nice looking cock. Brad is very horny now and begins to tell me to please take his cock into my sexy mouth, past my ruby red coloured lips. I look up at him as I begin to lean into his lap, I take my right hand and pull my hair back, then re cup his balls with it as I lean to his cock. The bulbous head touches my ruby red lips, Brad sighs in lust. I now gracefully let his cock part my lips as it the slides into my mouth and my tongue begins to feel it. I quickly try to work saliva up as I begin to do a mouth lock and tongue dance on his cock. I feel it lustfully play inside my sexy and slutty mouth.

Brad moans and says, "God Chantel, it feels fucking good... keep working at it you sexy bitch."

I am now rock hard in my panty, I'm loving being a sexy tranny slut. I can't believe how much sucking man's cock is turning me on. I begin to moan and suck, my tongue works all over his stiff shaft, saliva is all over his cock as he moans and I bob on his hard cock. Brad takes his right hand and gently places it on my head, running his fingers softly through my hair, it feels so good to me.

I keep on sucking on his cock, working my tongue all around his cock. My right hand keeps cupping his balls, my fingers with their long red nails tickling the base of his ball sack. I can tell Brad loves it. His panting, sighing and moaning are growing wild. He can't help but call me a little slut, tells me to keep going. I am hot and horny too, my sissy dick is so hard, but I keep focused on head bobbing on his cock.

Brad is moving closer to his eventual desire to fucking cum and to fill my mouth with his cum. He tries to hold my cell phone camera steady but he is so fucking horny and gets closer to cumming. I now want him to cum, I suck and bob more and more intensely on his stiff cock, my fingers work his balls. Brad's groans are near constant, his fingers pet my hair with more intensity as he gets closer and closer. I can sense as I work my mouth over his cock he is about to let go.

As he grabs my hair and begins to hold my head more firmly on his cock, he grunts and groans as he shoots out a thick blast of his hot, so fucking hot cum as he, "Ahhh..ohhh... damn, fine... fuck... fu...cking great Chantel... swallow it, swallow it all." as his cock spurts out more hot jizz.

My mouth is warm with a slick, hot goo. I begin to taste his cum as I then swallow it. I am fucking hot with sexy desire, I want to cum but I focus on pleasing Brad. He sighs and begins to pull his cock out from my mouth, his right hand lifts off my head as I carefully keep a tight lip lock so every drop of his cum is cleaned from his cock. As his cock flops from my mouth it is red with lipstick. I look up at Brad, he looks down at me, we both smile. I tell him his cum was delicious. He thanks me for a great blow job and he tucks his cock back into his briefs and does up his pants. I sit back up, he hands me my phone. We will have some video of it all, of the first time I sucked a man off.

Brad tells me he hopes to see me again, I tell him I will probably be back here again. I step out from his car, bend over smile looking into his passenger side window he smiles, starts his car up. I walk up to in front of his car and begin to walk back on the sidewalk. He tells me from his window I was great and a sexy bitch as he then says, "Cya sometime. and I smile as I say "Bye".

I'm back to walking the sidewalk of this rest area, I can still taste Brad's cum and its quite exciting. The evening is still pleasant, not too warm, not too cool, fresh from the early evening rain, wind breezes up my legs and skirt, it feels good.

About 10 minutes pass, it's about 10:30pm and as I walk towards the picnic table and I casually turn I see another car pull into the rest area, it parks in front of the walk way to the rest room. I stand about 30 feet away, but I begin walking slowly down the sidewalk. A guy gets out of the car, average height with male also maybe 30-35, reddish brown hair, clean shaven. He stops to see me but decides to walk to the men's bathroom. I get to the walk way to the bathroom and slowly walk up it and stand by the doors between the mens and ladies bathrooms, I stare at the bulletin board. About a minute later the mens bathroom door opens and the man steps out and sees me under the light. He is bewildered.

He says, "Um wow, you are quite the looker, nice fucking legs. What are you doing here?"

I smile and reply, "Hi, sir, um thank you I love my sexy legs, my name is Chantel and I am here for one reason, to give men who like me, pleasure?"

He replies, "My name is Ben and what kind of pleasure you into Chantel?"

I smile and say, "I love to suck and I am looking forward to a good fuck."

Ben says, "Um how about you give me a blow job?"

I reply, "Ok darlin, where would you like it?"

Ben coughs and says, "Come on inside and we can use a toilet stall."

I walk in there mens bathroom and my heels click loudly on its concrete floor. I smile and turn to face Ben and ask, "Well Ben do you like what you see?"

Ben very excitedly says, "Fuck yeah, you are pretty fuckin hot. How about you get into a stall, sit on a toilet and get ready to suck my cock."

I reply, " No problem sugar." as I enter a toilet and take from my purse a go pro on a suction cup base and say, "You wont mind if we get a bit of video? My Mistress wife and her boyfriend want me to get some video of this stuff."

Ben says, "No problem, you make a little video of me feeding you my cock and then treating you with my hot cum."

As I sit on the toilet seat, Ben enters, closes the stall door and has me undo his pants for his and then pull his briefs down. My nervous excitement is heightened from the front his briefs flips out his nice 7 inch and quite girth cut white cock, with those sexy balls hanging too. I take my right hand and my fingers with my ruby red finger nail coloured nails cup his balls, my nails dancing on the base of his ball sack. My left hand wraps its ruby red nail coloured fingers grasp his nice and stiff cock. I begin to tug on it and I see Ben enjoys this. From my position on the toilet seat I look up all doey eyed at Ben sanding over 6 feet tall and looking down at me, a big smile on his face as he says for me to take his cock into my mouth. I proceed to lean forward and I feel Ben's cock head touch my ruby red lips. I then slowly part my lips as his cock enters my mouth. I feel it slip over my wanting tongue. I sense Ben very horny for this blow job.

I begin to get my mouth worked up with my saliva and I feel the stiffness off his shaft on my tongue. I begin to bob my head and suck on it as Ben begins to moan telling me how good it feels. This makes me very turned on, my sissy dick is all stiff too, but I keep focused on sucking Ben's hot cock.

We work on this cock in mouth dance, Ben takes his hands and run them over the back of my head, running his fingers through my hair. His moans and sighs turn to calling me a good slut, a hot bitch, "Suck it Chantel, suck me off." Each phrase makes me want to bring Ben to his ultimate pleasure. I can sense my work is going to get him there as he moans and groans in lust I keep on sucking and bobbing on his rock hard cock. He feels close to cumming and tells me it will soon happen. As he gets closer and closer, his hands more firmly hold my head on his cock. As now I feel the warmth of hot manly jizz fill my mouth and Ben grunts then sighs as he pulsates his cock delivering me every last bit off his manly ejaculate into my so wanting mouth.

I swallow this hot cum with pride, pride of a new slut as he pulls his cock out from my mouth and his cock is smeared with my red lipstick. I then look up at him, smile and tell him his cum was delicious. Ben smiles, his right hand grasps my chin and he says that was a great blow job. I help him with cock, putting it back in his briefs and do up his pants. Ben steps out froth stall and says, he'd like to hook up again with me one day. I smile and agree as he then walks out and I grab the go pro and myself freshen up my lipstick looking at the mirror. I then walk out from the mens bathroom and begin my nighttime strut. I still need to hook up with a guy too take my virgin anal cherry. Some guy into it as such will be happy doing so. A part of me wants this to get on so I can head back home. I look at my cell phone an see it's 11:04pm. I keep on strutting in my tall red suede heels.

About 15 minutes pass as I see a car finally pull into the parking lot. I am sitting on the picnic bench and watch. The driver parks closest to the walk way to the bathrooms and sits. He begins to scan outside his windows and he sees me dimly lit about 30 ft. away. I decide to hop off the bench and walk towards the car, gracefully as each heel clicks with each step.

He is gawking at me and I smile at him as I come close and walk by the front of his car. I keep walking until I reach my parked car and then turn around to walk back. We keep eye contact as he nods and I smile. I saunter by him and walk up the walkway to the bathrooms, under the brighter doorways lights I stop, turn and lean back against the wall, looking towards this guy in his car. I pull out my makeup compact and fix/play with my hair as I cop a look at his car.

Another minute passes as I wonder if the guy is going to get out of his car or is he just going to get off looking at me. Finally he opens his driver's door and steps out. He's no stud as I see a guy who is likely near 40 and standing about 5'10' and a bit pudgy easily 240+ lbs. He is in a black t-shirt and black jeans. He walks towards me shoulders a bit slumped and his hands inside his front pockets. I watch him step closer and soon he stands before me about 5 ft. away.

He says, "Um... ahh.. I'm a bit nervous. I have only do...done this sort of stuff twice with a girl like you."

I say, "It's ok darlin, my name is Chantel, what's yours?"

He coughs and replies, "Um it...it's Rick, I knew you must be Chantel as I read your ad in Craigslist. Are you really into putting out?

I answer, "Ok Rick, yes I will put out, what do ya want?"

Rick says, "Um I'd love to first do this." as he walks close to me and takes his hands and places them on my thighs, feeling my stockings and lace tops. "I love your stockings, your legs look killer in those heels and that short skirt is wow."

I say, "I'm glad you enjoy it, so what do you want sugar?"

Rick leans close and says, "I really want to fuck you. Fuck you in the mens room, fuck your ass until I fuckin cum deep inside you."

I'm hot, excited and nervous as I say, "Darlin you know from my ad that this will be my first time, you will get the opportunity to take my anal cherry."

Rick says, "Lets go inside, lets have fun." as he takes my hand and we step inside.

Walking inside I go to a stall, pull out my go pro and stick it on the wall so I can get video of my devirgnizing of my sissy ass. I then take my tube of Astra glide from my purse, bend over the toilet, pull up my mini-skirt, pull my panty down and take dollop of lube on my fingers and carefully lube my butt hole, getting it ready for Rick to fuck me. As I am doing so Rick stands and watches, but soon moves in, asks for the tube and then he takes a dollop of lube on his fingers, leans forward and says he will finger lube me as my long nails makes it harder for me to do myself. I toss my hair back, look over my shoulder and smile as I accept him doing this.

To next feel a man take his hands and his fingers and run them in and around my butt hole is a very exciting feeling. But soon I am saying, "Ohh Rick, god please do me, please take my cherry, it's yours."

Rick steps back and drops his pants and his briefs, he is only modestly sized maybe pushing 6 inches, but is of nice girth, he is uncut and his cock is ready to find my hole. I look back at him and observe him move back in, his hands grasp my butt cheeks and begin to massage them.

As he next pulls them open to show him my wanting sissy pussy, he says, "God Chantel, this looks tempting, I am really hot at being the man who will fuck your sissy pussy for you first time."

I reply, "Ahh...mmm... please Rick... do it, do me now I want this bad."

Rick next begins to insert his modest cock inside me, he goes gentle and he makes sure I can happily accept his tool. He tells me to just relax and enjoy it, he is certain I will.

I reply to his insertion with an, "Ahhh...ohhhhh...mmmmm...yes...it...it feels.. so good."

Rick works into a good fucking rhythm and he is really enjoying this action as he moans and sighs with a more rhythmic fucking and as we get more and more in tune he works up to a harder fucking action. I can't help but begin to more and more groan and moan as I ask for more and more from him. This is for the anal virgin me a most incredible feeling. His hands firmly hold my hips and he pushes his cock back and forth, his sighs, and deep breathes turn me on more as my sissy dick is again rock hard.

As he fucks me harder I almost feel as if I will fall of my sky high heels as I keep my sissy back side up and ready. As we continue our fuck, with his moans and my groans the door to the mens room opens, another guy walks in, he does not at first realize what is going on in one of the stalls, but our fucking noises soon has him become aware. We kinda slow for a moment, but Rick leans over and quietly says, "Fuck it I could not care." and begins to pick his fucking pace and I am more and more sexually delirious by his fucking.

The guy standing at a urinal can't help but speak up. "Hey! I know it's late on a Friday night and you two sound as if you are really getting it on, but how about keeping it down in there?"

We do not reply, but do slow back down a bit. The other guy finishes and washes his hands to then leave. We then giggle as Rick picks his pace back up.

He takes his right hand and feels that I am rock hard and asks, "You want to jack off to this fuck girl?"

I excitedly reply, "Ahh...yeah..it would ahhh, feel good."

Rick keeps playing with my sissy dick as he keeps fucking. He is working up a sweat and soon drops from his nose fall to my backside as he bangs me harder and harder. He asks if I'm getting hot to cum myself and I am quickly getting there, it's not my place to cum but to make man happy but if he wants me to have such joy that it's a bonus. Rick hopes to bring me to coming about the time he lets go. He works his fucking constant and hard as he pulls my sissy dick with his right hand.

He asks, "Chantel are you getting there? Because I am going to let go soon?"

I reply with a sigh, "Ohh.. God, yes.. soon." and I moan more and more. Moments later I can't stop myself as my sissy dick shoots out a load of sissy cum to fall to the floor. My groans and sighs brings Rick to orgasm and he lets go inside me, I get the best prize a butt full of his hot, manly cum. Rick pounds and shoots until he has no more cum to give me, fill me with. My sissy dick is now dry as he pulls out and I turn and fall to a haunch before him. I take my hands and hold his softening cock to lick it clean, tuck it back into his briefs and pull up his pants.

We look teach other, me submissively up and him strongly down as he thanks me an I thank him. He hopes my first butt fuck will be long remembered. I tell him I will never forget it. Having him jerk my sissy dick off at the same time only makes it better. Rick says he hopes we can hook up again one day and I agree. As he steps out from the stall and then out from the men's room I take tissues and wipe my backside, fix my panty and skirt and I too walk out leaving small pool of sissy cum to dry on the floor.