Paying For The Roadside Assistance

My wife Mandy and I were on our way back home after getting our son settled in at college. She was feeling a bit depressed over it, in fact she’d been feeling that way two weeks prior to Ricky’s move.
Empty nest syndrome is what her doctor calls it. I guess we guys handle things differently in fact I had plans to turn Ricky’s old room into my she cave. And I was actually looking forward to settling into the peace and quiet of a normal life with Mandy and Cindy as well. But now this shit was happening. Mandy would be on sleeping pills and anti-depressants until she gets past this ENS crap. And there’s no telling how long that’ll be.
Mandy had taken her anxiety medication before we left our son’s dorm and on top of that she took a Valium, so at the moment she was knocked out cold in the back seat of the Tahoe. Which meant that I was gonna have to make the twenty hour drive back home. Fuck my life!
I do alright driving by myself but when it’s night and I’m tired, I tend to nodded off. And the night we broke down was when I nodded off.
I clipped a guard rail but managed to get the vehicle under control but not before I hit something that flattened both the right side tires.
My poor wife was thrown into the floorboard and through all that she didn’t even wake up. Thankfully I managed to get her back in the seat. Heck I had to check her pulse to see if she was still alive. She was.
I tapped the side of her face until she stirred and she looks up at me,”What honey?”
“We had an accident baby, where is your cellphone?”
She mumbled something but she was unable to keep her eyes open or even pronounce a clear sentence.
I had left my cellphone with Ricky so he could use it and intended on buying me another one as soon as I got home.
I shook Mandy, “Baby wake the fuck up! Where is your damn phone?”
She wakes up and tries to nod off again but I sit her up. She was in such a zombie state.
I ask her again about the phone and she shakes her head,”Ricky has my phone,Jim.”
My heart sank,”Baby,I gave Ricky my phone before we left. Why did you give him yours too?”
She didn’t reply,because off to LA LA land she went again. I laid her back down on the seat and covered her up again. Then I got out of the Tahoe and walked around and inspected the damage feeling absolutely frustrated.
The passenger side finder was jammed against the tire and as I said,both the front and back tires were flat.
Well fuck! We were somewhere in Alabama and still eight hours from Asheville if not longer and we we’re broke down and with no way of calling for help. Talk about royally fucked!
Why the hell did Ricky take my cellphone when he already had his mom’s? Maybe he was gonna pawn one of them. I love my son but he can be a shifty little bugger.
The back passenger door opened and Mandy staggered out. She could barely walk.”Where are we and what time is it Jimmy?”
“Mandy you need to lay back down baby. I don’t need you out here falling on the ground and hurting yourself.” With that I helped her back in the vehicle and she instantly fell back to sleep, but before she did she said,”Cindy would know what to do.”
I climbed back in myself and realized I hadn’t turned the four ways on. So I turned them on. Maybe a cop would see them and pull over.
That was wishful fucking thinking.
It got to be three in the morning when my panic finally settled in because it started to snow and the needle on the gas meter was hovering in the middle of the empty quarter mark and that meant Mandy and I probably had just an hour or two of heat left before the gas would run out.
I needed to calm down. I thought about what Mandy said before she passed out again.”Cindy would know what to do.”
I needed to be Cindy. When I was dressed out in Cindy mode as I called it I felt a lot less stressed and I was more calm. Being Cindy did that for me and right now I fucking needed her!
I got out and walked to the back of the Tahoe where we had our luggage stored and opened it and climbed into the back.
I’ve been crossdressing as Cindy for almost ten years now and I love it. It started when I was laid off from the factory I was working. They decided to up and move to Mexico after I gave then 10 years of my life. Yeah you can say I fell in a depression, it got so bad I started to want to cut myself.I picked up a razor one day and was about to do just that when suddenly this overwhelming feeling to dress out over took me and I started thinking about when I was kid I would dress up in Mom’s clothing I was so petite as a little boy and I could easily wear her bras and panties and even her dresses. I had named that part of me Cindy.
And Im just as petite as a man today as I was back then. At a hundred and ten pounds I certainly have a feminine frame, my facial features, slender hips and my pooched out bottom.
It’s easy for me to wear my wife’s clothing because we’re the same height and weight. Well she claims she is a hundred and five pounds. NOT!๐Ÿ˜
When I started dressing as Cindy I started letting my hair grow out to the point I have a very nice mane of shoulder length blond hair. Mandy is quite jealous of it. She often tells me Cindy has better hair she does.
Yes my wife knows I dress out but she doesn’t make a big deal out of it anymore. She used to and when she caught me I thought that it would be the end of our marriage, but thankfully it wasn’t.
Heck she loves Cindy like the sister she’s never had. But anyways enough about that.
I rummaged through my wifes suitcase and found the clothing Cindy approved of. A pink long sleeve nit shirt and black yoga pants and a set of Hello kitty panties. I was ready to be Cindy. I put the clothes on and pulled my hair into a ponytail and tied it off with a cute yellow scrunchie. Then I went through my wife’s purse and with a bit of lipstick mascara and eyeliner my transformation was complete. I took my wife’s small white fuzzy shell jacket from her suitcase and slipped it on and stepped out of the back of the Tahoe.
Thankfully the snow had stopped falling but it was still deftly cold and I found that the yoga pants offer little protection at all from the wind. But thankfully I put on my wife’s white furry ugluggs at least my feet were warm. Thankfully Cindy talked her into buying these damn things.
I walked over next to the highway and just stood there. I knew someone would help a woman in distress before they would a man.
Four cars past by and so did a semi. But then maybe I was wrong too.
I was about to climb back into the Tahoe, when suddenly a big jacked up pick up truck put on breaks as he past and it quickly pulled into the emergency lane and came to a stop. Then it began slowly backing up. A spot light came on illuminating the entire front of the Tahoe.
I hurried over as the driver climbed out. He was a big man maybe sixfoot five and he wore
a pair of faded suspender cover all without a shirt. I could see a pair of massive arms sticking out. “Looks like you need a bit assistance, little lady.”
“Oh thank you for stopping,sir.” I said and I see the smile leave his lips and he gives me a hell of a confused look.
It was my voice that threw him off. Try as I may I couldn’t for the life of me conceal my masculine voice. And trust me I have tried every YouTube training video out there but nothing works.
The man just looks at me and chews on his toothpick. And he appeared to be pondering the idea of kicking my ass.
“Please sir, my wife and I need help.”
He suddenly laughs,”You got a wife?! Oh fuck ain’t that some shit.”
I wanted to punch his smart ass but then that would have been a stupid move on my part since he’d most likely pulverize me in a matter seconds.
“Let’s see what’s going on.” He turned and started walking over to the Tohoe and began inspecting the damage. He took the fender and pulled it out with his bare hands. Which impressed me.
“Wow!” I said.
He looked at me and winked,”Did you liked that sissy boy?”
Whatever I thought. Call me what you want just help us. “Yes, your very strong sir.”
He smiled,”They call me Big T.”
“I’m Cindy.” I said extending my hand. He took my hand.
“Please to meet you,Cindy.” He took a pen light from his pocket and shined it on the front tire.”Humm it’s looking like you have 275 slash 60R20’s.”
“What’s that?”I asked.
“That’s the size of your tire, sweetheart. I wouldn’t think it would be the size if your little boy clit.” He chortled.
“Oh?” I played dumb. Well I really didn’t have to play it to hard. Heck I knew nothing about a tire other than the fact that mine were fucking flat right now. The fucking idiot. And as for the size of my dick? Mandy sure don’t complain.
“Look sweetheart I run a salvage yard and we have several Tahoes on the lot. What do you say I just run back there and pick you up a set. I’ll bring them back and put them on and you and your…wife. that way you can be on your merry little way.”
“That sounds great. How much will you charge?”
Big T smiled,”Is your wife any good at blow jobs?”
My mouth dropped,”What?!”
He laughed and scratched his thick neck,”You heard me girl. Is she any good at giving head?”
“No way dude! My wife’s not blowing you!”
He smiled,”Well how about you. Are you any good at it? I mean you’re a little sissy. Aren’t you supposed to know how to blow?”
I just looked at him in shock.
“Ah come on,don’t tell me you haven’t done it,Cindy.”
I swallowed hard and looked away. I have given head to several guys before, but that was before I was married. And that’s been twenty years ago.
“Fuck this shit I got supper waiting on me back home.”, Big T stood up and began walking back to his truck.
“Wait,please.”, I said.
He turned around with a grin on his face.
“I’ll do it, but I get the tires first.”
He walked over and opened the rear passenger door and looked in at Mandy who was still knocked out. Then he laughed and shut the door. He walks over to me,”Hot Damn! Your way prettier than your old lady.
Gosh I was so glad my wife was asleep for that one, or she might have scratched his fucking eyes out for that stupid comment. And I didn’t know what else to say to his compliment other than,”Thank you.” And I gave him a little smile.
He takes me in his big arms and leans in to kiss me,but I push back,”Tires first and they better be good too.”
He smiles,”And you better be good at IT too. You little slut.”
Goodness I felt butterflies fluttering behind my navel now. The very same feeling I’d get before I… suddenly Big T slapped my ass and walked to his truck. I watched him drive away the sting of his hand still ripe on my ass.
I smiled and walked back and got back in the Tahoe.
I kinda felt excited over the thought of having a man’s cock in my mouth again. I had enjoyed it the last time I did it. Goodness I can’t even remember the guys name, but I could certainly remember the size of his cock. Am I getting hard? Maybe. No definitely there was a chubby coming on.
Mandy mumbled something from the back and I looked over the seat at her she was sleeping peacefully again.
It didn’t take Big T long to get back. His big red crew cab pick up pulled ahead and backed up until he was a foot off the front bumper of the Tahoe. He got out and walked to the driverside and tapped on the window.
I rolled my window down,”You stay in the truck sweetheart and keep warm while I change the tires. I brought some gas too.”
“That was sweet of you,thank you T” I said and patted his big hand. He smiled and got to work. I couldn’t help but wonder if his cock was as big like the rest of him. I smiled to myself and watched him work.
Hefted the two tires with rims mind you out of the back of the truck as effortlessly as that of someone on a pit crew team. Next he took out a large floor jack and picked the Tahoe and used an electric impact wrench to snatch the tire off and replace it with one of the used ones. He did the same to the back of the Tahoe. Afterwards he picked up my old tires and tossed them into the back of his truck. The he took out a red five gallon gas jug. He held it up for me to see it as he passed, I just smiled and gave him a cutey little wave.
I watched him in the side mirror as he emptied the gas into the tank. I saw my gas gage go up to just under the half mark. And I smiled in relief. He was doing this for Cindy and Cindy was going to gladly pay up.
I looked over my shoulder at my wife. Thankfully she still sleeping. I left the engine running and got out of the Tahoe.
T looks at me as he comes walking back around. Im so nervous I’m practically shaking. He takes my hand and gently leads me over to the back driver’s door. He opens it for me. “Ladies first.”
I smiled at him and climbed into the big back seat of the truck. T climbed in right behind me and slid close to me.
“T I haven’t done this in…”
He placed a finger to my lips,”Shhh it’s okay baby,girl. Just relax. He started uncliping the the brass buckles on his over alls and pushing his feet out of his work boots. “We can take our time and do this right. No pressure.” He leaned in kissed me softly on the lips.
I got a little dizzy because I haven’t kissed a guy in such a very long time.
T lowered his hand and pushed it between my legs and cupped me.
“I’ll tell you a little secret baby. I haven’t been with a sissy in quite some time myself.” He squeezed me gently and I could feel the blood coursing into my penis.
“Have you ever sucked a man off before?” I asked and T shook his head.
“No baby. I’ve never felt the need to.”
I smiled and pulled my yoga pants down to show him my Hello Kitty panties and he smiled.
“Oh yeah baby. I like those.” He rubbed my cock through the crotch of the panties. I was getting hard.
I pulled the bib of his over all down and he pushed himself up so I could get them down all the way.
My heart leaped at the sight of his cock. It was certainly bigger than mine. It was a girth seven inches something comfortable to suck. The sight of it made my mouth water.
I slid myself up on the seat and laid down on my belly and positioned myself so my head was just above his lap.
T ran his hand down my back and pushed under my panties and squeezed my ass. “You got a fine ass baby. He slipped a finger between my buttock and rubbed my puckered anus.”How’s that fell, huh.
I just smiled up at him and lowered my head into his lap. I took the head of his cock into my mouth and teased the edge of his cock head with the tip of my tongue.
“Mummm,fuck YESSSSSS! That a girl.”
I like how T referred to me as a girl. For at that moment I certainly was. I was Cindy and she loves cock.
I took him all the way into my mouth and chocked just a little on his size, even gagged a bit, but Cindy soon found her grove again and soon I was bobbing my head up and down on his shaft soo vigorously.
Oh it felt so good to have a cock in my mouth again and I became lost in the moment. It was so electrifying so surreal.
T groaned and pinched my little asshole in response. And without releasing his cock from my mouth,I reached back and took his fat digit in my small hand and pressed pressed it against the opening of my boy pussy.
T knew what I wanted and he unceremoniously stabbed his cock sized finger into my wanting hole.
I come up off his dick and gasped as he twisted and pushed and fucked my little asshole.
With his left hand he gripped my ponytail and pushed my mouth back over his cock.
I reached back to grab his wrist but he tightens his grip and I quickly pulled my hand away. He pushed down hard on the back of my head and thrusted his big hips until he was wedged deep inside my throat and with that he started bouncing his hims and fucking my throat.
I relaxed my throat and let him skull fuck me at hus pleasure all the while he fucked me with his fat index finger.
“Ohhh Cindy.Baby YESSSSSS.” He gasped.
He fucked my throat until he came,sending his hot load deep inside my throat. It felt wonderful to feel that gush again.
When he was done cumming there was still quite a bit of the tasty substance left over that I was able to suck it from his from his cock.
He pulled his finger from me and turned me over on my back. He leaned in and kissed me hard on the lips and pushed his tongue into my mouth tasting his own juices.
“Damn girl, you can take a skull fucking better than my fiance.”
Better than my own wife too. I added silently. I giggled and reached down and started stroking my hard cock.
“No let me baby. You deserve it.” He pushed my hand aside and began masterbating me. His hand felt so nice and he kissed me as he did it. I came so quick and so hard that I actually saw stars. He leaned over and did something totally out of I thought was his character…he licked me clean. Supping me up nicely and when he was done he smiled down at me.
I giggled and reached up and touched his face,”I didn’t think you sucked cock,T”
“I didn’t suck your dick,did I.”
We both started laughing.

I got out of the big pick up and T gave me a big hug and a kiss.
“Baby if your ever passing through Mobil again look me up.” He pressed a business card in my hand.”I’d love to do this again.”
I took a pen from his bib pocket and wrote my number on the back of his hand, “If your ever Asheville NC please do the same for me. I’ll make the time for you T.” I winked and turned and walked back to the Tahoe and climbed inside. I continued the rest of the trip home dressed as Cindy.
The End
By Taz Dragnor
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