Josie Loves Todd

As I lie here writing this story I am first and foremost aware of my great fortune. I am secure financially and personally. I have the career I always wanted, I have wonderful friends and an ironclad support system. The joy that I feel on a daily basis is made manifest each day as I wake next to my husband, the man who helped me to become the person that I am today. We are not a traditional couple by any standard, he is almost thirty years my senior.

Other than that, we appear, on the surface to be the same as any other May/ September couple except to those who know us. Todd is a handsome 58-year-old contractor with cute silver hair and a still rocking bod. I am a 29-year-old college professor. I have long dirty blond hair with honey highlights and I am complimented incessantly on my looks, even by those who have no idea that under my no-nonsense teacher skirt is a pair of lace top thigh highs, a garter belt, and sheer sexy panties that shroud my petite, sensitive penis.

Todd was, and still is a friend of my father. They met and became pals not long before I went away to college at eighteen, although I did not meet him until the summer of my junior year. I have always been effeminate and slight of build and I was a loser in the love department. I was so enamored of girls but even when one was interested in me I spent most of our time just talking. One girl in high school told me that I must be gay, a thought that intrigued me. I hooked up with a couple of guys in college, an endeavor that seemed destined for failure as well.

So, I threw myself into my studies, taking the highest class load I could and going five semesters without a break, all the while maintaining a 4.0. It was in this period that I discovered cross-dressing and, I soon had a nice stash of panties, bras, and hose. My roommate Jack loved it. We spent many nights in our room fucking like hamsters. I knew I had finally found my calling and I was so sure that Jack was the one until I walked in on him and a well-known sorority slut going at it doggie style...on my bed. I stood there, unable to move, my hand covering my gaping mouth. They both looked at me and she, without blinking said.

"Look, Jack, your bitch is here."

After which they both collapsed laughing. I was devastated and ran from the room crying. Friends found me coiled up on a couch in a common area sobbing. One of my female friends retrieved the RA and I allowed to be her roommate for the remaining month of classes.

Mom and Dad, seeing that I was absolutely burned insisted that I take the summer off. I knew they were right; I needed a break badly and Dad said I could work for Todd over the summer.

Dad said, "He pays well and there is some traveling involved. The hotel he is working on is on the beach."

'That sounds great Dad but, you know I'm not the construction type"

Mom interjected, "He doesn't need a worker, he has those. He needs someone to run errands and keep up with paperwork...you know, payroll, invoices...I don't know what all, but he said if you were interested to let him know this week or he will have to hire someone else."

Interested? I was very interested. And not just in the job. I'd seen Todd a few times over the prior couple of years. He was 48 at the time with salt and pepper hair, devastatingly soulful blue-green eyes, and a short, well-groomed beard. Every time I saw him, he was wearing nice jeans and really nice tees. His clothes always seemed to fit perfectly, especially those tees. They were just tight enough to allow you to see the outline of his muscles and his abs. More than once at a gathering like one of Dad's barbeques, I would find myself mesmerized by his physique, the bulge in his jeans, even by his watch, his beautiful platinum Rolex.it looked so good on his wrist.

A couple of times I'd look up to find him giving me that that beautiful smile I'd loved so much since the first time I saw it. My heart would flutter, and my legs would go limber. I dismissed these thoughts as flights of fancy, Todd always had a beautiful girl on his arm, some of them nearly as young as I was. I thought there was no way he would ever want me. That did not stop me from masturbating to a mental image of him regularly.

I called him the next day, which was on a Friday, and told him that I did indeed wish to work for him that summer.

"Be ready to go Sunday morning, Josh," he said, "It's a three-hundred-mile drive so I like to get there and check into the motel so I can get some sleep."

"OK, Todd, thanks for the job."

"Oh listen, I know how smart you are so I should be thanking you. The paperwork on that job is absolutely screwed up...you'll have your work cut out for you."

We chatted for about ten minutes. He explained that he was the general contractor of choice for the company that built these hotels. In addition, his business did many local jobs which he left in the hands of his uncle. He oversaw the hotel jobs because they were so lucrative, He always drove home on the weekends to keep close tabs on the local projects.

I tried not to fawn and gush on the phone as we talked. His voice and mannerisms were so sexy to me. At the end of our conversation, he said,

"Pack enough for a week, Josh. Also, I try to leave the job little early on Friday and we usually get home by eight or ten pm."

My mind was racing as I thought about taking two long road trips every week and staying in the same room as him all summer. I quickly dismissed these as being silly, but I went to my room and put panties and hose into the inside pocket of my suitcase. I was going to continue my crossdressing under my men's clothing.

I was waiting on the porch for him at nine Sunday morning. I was wearing a collared shirt and khakis with sheer bikini cut panties and pink and black striped thigh high socks underneath. My long hair was pulled back into a ponytail and my face was as cleanly shaven as the rest of my body (Id spent an hour shaving in the shower that morning) Todd pulled up in his king cab truck and I climbed in and threw my bag in the back seat. Of course, he had on his jeans and one of those form-fitting tee shirts. I wanted to bite him.

He was so funny and confident in the way he spoke. This was really the first chance I'd ever had to chat with him face to face. I tried my best to seem aloof, but it was so hard. He affable nature was complemented by the way he seemed genuinely interested in me...in my academic career and in my opinion on everything from politics to pop culture. I was happier than id been in months, sitting there with my left leg crossed over my right, my back straight, my hands folded on my lap, attentive to every word, focused upon each word that fell from his lips.

We stopped for lunch at a popular chain coffee shop then we walked next door to a large convenience store. Todd grumbled about the gathering rain clouds, remarking that he hated driving in the rain.

"I need cigarettes," I said, "I will smoke before I get in your truck, I know you don't use tobacco."

"Oh, hell Josh, I don't mind. I have girls smoke in my truck all the time."

That statement brought the tinging urges back. Did he just call me a girl?

"Just crack your window, use an empty soda bottle for the ashes," he laid a hand on my shoulder as we entered the store, "And don't make a mess in my clean ride."

As he said that he squeezed my shoulder, massaging it. I turned to look at him and he was giving me his brilliant impish smile.

"Get anything you want; I always get a bottle here for later...What do you like to drink Josh?"

"Vodka," I squeaked, still quivering and trembling from my shoulder massage.

"Good choice, vodka it is."

I went to the candy aisle and selected some mint gum as I watched him out of the corner of my eye. He strode over to the liquor aisle and selected a big bottle of Grey Goose, lifting it for me to see and then he shouted.

"Is that OK?"

I felt the blood surge to my face and I just knew it was blood red. And the fact that everyone in the store turned to look at me made my face burn hot. I looked at Todd and nodded my head in agreement, as his smile returned. He retrieved sodas and candy for the road and as I was at the counter picking out cigarettes I watched as he stopped in front of the magazine rack and select the current Penthouse.

When we were back in the truck, I smoked with the window cracked when Todd's cellphone rang. He looked at the screen, told me he had to take it, put the truck in cruise control mode and started chatting with a concrete subcontractor. And as usual, I studied his form and his manner as he spoke, what seemed to me to be perfect Spanish to the man.

'God,' I thought, "Is there anything this man can't do"

Then as soon as I'd asked myself that question I answered,

'Yeah, I'll tell you what he can't do Josh, he can't fuck you because he is straight."

I considered the various young women I'd seen him with. They were all beautiful.

"There's no way he is going to go for me, he's just being friendly." I thought.

About the time I finished my cig, Todd wrapped up his phone call and we continued our conversation. I was a bit more reserved after chiding myself for lusting after this obviously straight man. After about 20 minutes the conversation lagged a bit and Todd pulled the Penthouse out of the bag and laid it out on the seat beside him. The traffic was light, and Todd thumbed through the slick pages, stopping at the pictorials he liked.

"Damn, Josh, look at these chicks. Do you like these?"

In fact, did. I'd been loving men's magazines for years, but I loved the women's forms, their beauty, their hair, their clothing, I was even a fan of the photography.

"Oh yes, "I replied matter-of-factly.

He pushed the magazine toward me,

"Which one of these is the best, Josh?" he asked grinning.

There were several pics of women in various states of undress. I studied it for a moment and put my finger on a picture of a beautiful brunette, wearing a sundress that was blown up by the breeze exposing her ass.

"What?" Todd laughed. "She's damn near respectable looking."

"I think she's pretty and I love her dress," I said.

Todd said 'Well, I see your point...I think." And with that, he snatched up the magazine to get a closer look. He grabbed it so fast it the slick paper slid out of his hand and It landed in the floorboard between his legs. He looked down and tried to scoot it with his foot to a place he could easily reach it and he only succeeded in pushing it under the seat.

"I'll get it," I said.

I slid down into the floorboard on my knees and crawled to Todd's side. He had managed to get it way under the seat and I had to push past his right leg. Since he had it on cruise, he scooted back a bit to allow me more room. I bent down and retrieved the errant magazine. When I looked up, I was staring right at his crotch. The outline of his cock was so evident, and I was mesmerized. I didn't move. I didn't look up; I didn't do anything for ten seconds or so but stare.

It was then he did something I will never forget. He shifted his right leg again...he spread it wider. I still had not looked at his face and to this day I do not remember making a conscious decision to do this but...I leaned in and took as much of his sizable bulge into my mouth as I could.

I took a big bite, clamping my teeth on it gently as I tongued it passionately. I opened my mouth wider and pushed onto the bulge further, clamping and tonguing. I made five or six such bites then I pulled my right hand off the floor and grasped it, squeezing, and continued to bite his wonderful cock. At this point, I still had not looked at him to gauge his reaction and he had not said a single word.

I became aware that we were on an exit and slowing down. In almost a minute of me gnawing on his cock, not a word was said. It then occurred to me that he could be pulling over to beat me up or kick me out. As soon as those thoughts entered my mind, I felt his big hand on my neck. He was massaging me! He squeezed my neck a few times then grasped my ponytail and pulled my face tighter into his crotch.

"Damn girl, let me get this truck stopped."

It was only then that I looked up. He was looking at me with a look I'd never seen before on his face. I know it well today. He was in the throes of lust.

"You will have to give me my leg back girl."

Girl...I loved being called that. I moved back and allowed him to move his foot to the gas pedal. As I continued to rub his cock through those jeans I looked straight up at his face. I could see we were in a tree lined area. I wanted so desperately for him to look at me again, but he was concentrating on his driving intently. Presently he said,

"I've pulled into a rest area here. I'm pulling down way past the other cars so we can have a little privacy."

As he said that he reached down and undid his belt buckle and the hook on his jeans. I needed no invitation at this point. Excitedly spread open his fly and with my slim trembling hands, I pulled the waistband of his boxers and pulled his magnificent cock out. I gasped with delight as I beheld it. His crotch was shaven clean except for a cute patch on top and his veiny uncut cock. It was the largest I'd ever seen, except in porn. When my slim hand grasped it and there was cock showing both above and below it. I knelt there, Todd's big cock in my hand, eyes trained upon him, awaiting instruction as he maneuvered the truck to a stop.

I felt the truck roll to a stop. Todd jammed the column gear shift upward into park, then ran his fingers into my hair and glanced about. He then lay down on the wide bench seat scooting toward the passenger side, pulling me with him until he was fully prone. I still had a firm grip on his cock (as I have had ever since). Todd still had a hand full of my hair, a fact that made me even hotter.

"Come here sweet girl," he beckoned.

Our lips met with a ferocity I have rarely experienced. God his saliva tasted so good as he thrust his tongue into my willing mouth...I was his...I was ready. As we kissed, he ran his hand down into the back of my khakis. When his fingers spread over my butt in those silky panties, he stopped kissing me. He pulled back and gave me that sweet smile again. The with a wink he said,

"Damn baby, I'm so horny. Suck your daddy's cock."

With that, he guided my mouth to his throbbing member using the hand full of my hair that he still had a tight grip on. This was my first go at an uncircumcised cock and I immediately fell in love with the silky foreskin, the way it felt in my wet little mouth. With Todd's strong hand guiding me, my dewy lips and curious tongue went down onto his luscious cock. After the sensation of the foreskin, I was immediately aware of his salty precum. My head bobbed back up and then I thrust down hard, taking more than half into my mouth.

As I slurped on his cock, I locked gaze with Todd. He lay there moaning and thrusting. The hand that had been pulling my hair was now cupping the back of my head and stroking my tresses. He spoke in a scatological manner, a trait that I've loved since that day,

"Damn girl...fuck, fuck me you are so...fuuuck."

The precum flowed freely as I tried my best to swallow his entire dick. After only twenty thrusts or so I grabbed the base of his cock and slapped his member against my extended tongue several times then impaled my face on his cock again. It was throbbing and spasming as I pushed my mouth down two, three times then he grabbed my head with both hands and pushed hard. The tip went down my throat, which set off my virgin gag reflex.

As I fought the urge to gag his cock erupted in explosive spasms of luscious creamy ropes of sperm. The first globules went down my throat, but I so wanted to see it as well as taste it. I pulled it from my mouth and pumped hard. The cum shot again hitting my cheek. I learned quickly, in the moment, when the next spurt would come. When I felt the spasm coming, I quickly put my mouth over the tip of his cock and nipped in rhythm with the spurting sperm.

When his cock finally stopped its volcanic spasming, I kissed the tip, looked in Todd's eyes and kissed it again. His cock was drained, and I was just so proud of myself,

"Did you like that Daddy?" I purred as that beautiful smile returned.

"Oh, baby girl," He said as he pulled me to him for a passionate kiss "That was the best blow job I've ever had."

We kissed passionately, my hand still grasping his pulsing member. As we kissed his hand continued to explore my backside and I noticed that his cock that had softened a bit after cumming was now, just moments later, rock hard once more.

"Damn, girl, pull those pants down." He whispered.

Oh my god, I would have done anything for the man at that moment. He looked so sexy, his cock was amazing, and he kept calling me girl. I had my shoes and khakis stripped off in a flash and I now knelt in my shirt, panties, and striped thigh socks. He grabbed me by my forearms and pulled me onto the seat beside him. I raised and glanced quickly about to see no one was near us. I felt so exposed and that only heightened my lust.

We kissed so deeply. My hand alternated between caressing his face and stroking his cock. He pulled my shirt up and sucked my little nips hard, making me squeal and whimper, as he rubbed my stiff she-cock through my silky sheer panties.

"I want to suck you, baby," he whispered. "flip around and lets 69."

"I love you," I blurted.

I could not believe these words came from my lips. I felt my face burning and I quickly covered my eyes with my hands to hide the tears of my embarrassment.

"Oh my god he is going to think I'm a freak," I thought.

"Baby," he said gently.

He pulled my hands away from my face and I looked down with my wet eyes, not daring to meet his gaze.

"Look at me, girl," he said pleadingly.

Slowly I looked at up and there was that smile. He reached over and cupped my chin as said.

"I love you too baby girl"

I was so overcome with joy I squealed. I put my arm over his shoulder, pulled close and kissed him again.

"I've had feelings for you since I first saw you, Josh,' he said, "I've never been with a..."

"Boy?" I said sweetly.

"Well yeah. But I don't see you as a boy, baby," he explained.

"Thank you, Todd," I said as I kissed him again, "Now, where were we?"

A soft steady rain had started falling as I raised up to take another quick look. We were at the far end of a long parking area and the closest car was at least a hundred feet away. Add to that the darkness of the tint on the windows and we were virtually secluded. I quickly spun about and after a bit of repositioning we were both cock to mouth.

His dick was stiff and twitching and I took it lovingly into my mouth again. I felt him pull down the sheer front of my panties and suck my hard four and a half inches in. This man who I always knew as a lady's man was sucking me better than anyone ever had. And, to my delight, he pushed my legs wide and massaged my tight boi pussie. He reached and spat on it and pushed his finger in.

I pulled my slutty mouth from his cock long enough to blurt,

'Oh God, Todd, use two fingers."

He did so gladly and his thick fingers stretching me was heavenly. I was no novice to ass play; I often used a dildo to masturbate and soon I was pushing my butt onto his fingers. I felt my orgasm rise from deep within my ass and prostate as I sucked passionately on Todd's sweet cock. When I knew for sure it was time I turned my head and moaned,

"Oh Todd, I'm cumming baby."

I was sure he would stop sucking and stroke me. I couldn't imagine that he would take my cum in his mouth but when he heard my words he shoved his fingers deep, forcefully into ass as he pushed his hot wet mouth tight onto my boi clit. The orgasm was epic. I came in spurts (which he greedily swallowed), pushing alternately into his mouth and then back onto his fingers. The spasms coursed through my entire body. I remember taking his dick out of my mouth at one point for fear that I might bite it the spasms were so intense.