It was strange for Brad to not email me or connect online for more than a few days. It had now been a week since our last meeting, and I still hadn't heard from him. A week became two and two became a month. Five emails I wrote to him had gone unanswered. I was alone at home. I stood naked in front of a mirror. I rubbed my belly which had become very well pronounced to the point where I just looked fat. My breasts had become far more subtle and fatty than ever before. My other hand cupped my right breast as I started to feel myself up. I imagined what they would feel like with an implant. It didn't take long for my cock to get hard.

I allowed my hand to slide slowly down my belly to my cock. I gently started to stroke it, allowing myself to take greater pleasure in feeling it get harder. It didn't take long for me to have a raging hard-on. I watched myself stroking my cock in the mirror for a few moments before making my way back to my room. I dug out a seven-inch dildo from one of my drawers and fell onto my bed. While continuing to pleasure myself, I slowly inserted the flesh-colored dick into my ass, very slowly and deliberately filling my hole. Once it was in, I started sliding it in and out, slowly, so I could enjoy it. I loved the feeling of having a cock inside me. Slow and deliberate became more aggressive. I was stroking myself at a more rapid pace and knew I would cum soon.

With all seven inches of my dildo filling me up, streams of cum shot out onto my belly. I started wiping up the cum, licking it off my fingers, and swallowing as much as I could. The taste of my own cum in my mouth gave me great delight. Swallowing it all made it that much better. I masturbated again for the only purpose to be able to taste myself again. While it wasn't as much cum as the first time, the taste on my tongue was just as enjoyable.

It took a few more months but I finally gave up on Brad and I dealt with my heartbreak by giving up on Jenni as well. I filled two large garbage bags with clothes and with little remorse, dropped them all into a clothing donation box. It took about six months to get back into shape. I found a new job with absolutely insane hours and used this opportunity to completely cleanse myself of the past. Eventually, my broken heart healed, and life moved on.

*******

It was fourteen years later that I checked into a hotel room on a business trip. In one suitcase, my work attire, and in a second bag, I had a separate set of clothing and accessories. After a complete post-Brad purge and years of self-imposed exile from sexual exploration, I couldn't resist the urge any longer. While the America Online chat rooms were no longer populated like they once were, I found new websites to play around in, when I had time. I was perfectly content with living my alternate lifestyle as a fantasy until I met "Trucker_Greg" in a random, yet appropriately named, chat room called "Truckers4Sissies".

Greg and I had a series of incredible online chat sessions spanning over two years before graduating to a phone call and a chance to talk to each other in person. Both of us seemed cautious and unsure of how to proceed and the first phone call ended awkwardly before either of us really said anything of substance. Confident Jenni, who turned tricks on street corners in college for fun, had been replaced by conservatively awkward Jenni, who wasn't anywhere as free-spirited as her former self. I wondered if I could ever recapture her original spirit.

An hour after our phone call had ended, Greg sent me an email. He apologized for the abrupt end to our call and said he would very much like to try again. The second phone call went much better. He and I spoke for over thirty minutes, sharing our backgrounds, experiences, fantasies, and desires. Greg did in fact drive a truck for a living and as I learned, he was not lying about where he lived and where he was typically on the road. Work frequently took me around the Midwest so I suggested the possibility of meeting either at my hotel or a place that we could both be comfortable. On this call, I described to him in detail about how I would suck his cock in his truck and swallow all his cum. I could hear him moaning on the other end of the phone as he brought himself to climax. It was on our next call we decided to meet.

It was a task to go back and purchase what I would need to bring Jenni back into my life but as I looked over everything I had spread out over the bed in my hotel, I was confident I had done a respectable job. The extensive makeup kit was gone but I had enough of the basics to get the results I wanted. I visited a local adult store and bought a sandy brown, shoulder-length wig.

For my outfit, I went with something cute but not too outlandish. I was pushing forty years old and no longer the youthful gal I used to be. While my body had recovered, it never really regained its slender form. Finding the right look was challenging. I walked around a mall window shopping for hours. It wasn't until I wandered into JC Penny of all places that I found what I was looking for.

One of the mannequins was dressed in a blue dress with a horizontal black leather sash than ran from the shoulder to the hem. The outfit was accented by a black, waist-length leather jacket and an unbelievably cute pair of ankle-high black booties. A woman about my age was looking it over so I figured I had found the winner. The rush of adrenaline hit as I wandered through the women’s department looking for the outfit I had seen on display. An older woman, wearing a store name tag approached. Her name was Gale.

"Sir, you look confused, maybe lost. Can I help you find something?"

"Well Gale, as a matter of fact, you can. I was looking for that outfit," I said pointing at the display. "Can you help a poor guy out?"

"Of course, sir, it's right this way. Who's the special lady?"

"I'm sorry, what?" I asked.

"I figured you weren't buying the outfit for yourself," she said with a wink.

I explained to her that it was for a special lady in my life and her name was Jenni. She had been through a lot, and this was a special gift for her to help get her back on her way. We took a short walk to a rack with the black leather jackets first and another short walk to the blue dress. Gale was a godsend. For some reason, I was so nervous, but Gale was great. She even suggested a discount shoe store in the mall to get the same shoes on display for half the price. While not the best salesperson for JC Penny, Gale was awesome.

"I'm sure Jenni will love everything. You can check out right around the corner," Gale said pointing to her right. "If you think Jenni would like to try that outfit on, the dressing rooms are located just past the register on your left," she said with another quick little wink.

"Thank you, Gale. I think we're all good," I said with a little smile back.

I looked over everything I had on my bed and was confident I could pull this off. Applying my makeup and getting reading was like riding a bike. Once I got started, it felt like I had never stopped. I watched as Jenni started to appear in the mirror in front of me. In a matter of ninety minutes, I was sliding into a pair of black suede booties and pulling up the short zipper on the side of each. I was a little wobbly on the three-inch heels but after a few trips around the hotel room, I was as confident as ever.

Walking through the hotel and the parking lot to get to my car was both nerve-racking and exciting at the same time. It had been so long since I heard the heels of shoes clicking on the pavement. I had forgotten how such a simple sound was so incredibly intoxicating. I could feel myself moving my hips and walking in a much more feminine fashion than normal. Everything about my short walk to the car felt incredible and it didn't take long before I was on the road. I could feel my heart pounding under my outfit. I was nervous but at the same time, I had a growing desire to have a hard cock in my mouth.

Greg and I had agreed upon a rest stop that was about thirty minutes from where I was staying. I pulled off the expressway and into the front parking lot. There was a small unassuming building that was in the center of two parking lots, one for cars in the front and the back lot for trucks. Greg had given me a detailed description of his truck and it was hard to miss it parked second from the far left in a row of about fifteen trucks. I took a deep breath as eyed his truck.

It was about a hundred-yard walk past the building, into the truck parking lot, and to his truck. It seemed more like a mile. As I sat in my car for a moment, checking my makeup and reassuring myself that this was going to be incredible, four cars pulled into the lot next to me. I looked across the clearing to see a few trucks pulling in. Paranoia set in. The longer I sat in my car, surely the more suspicious I would look. Maybe this wasn't the right time or place. I contemplated leaving. A minute later I was opening my car door to start the walk to Greg's truck.

I'm not sure what overcame me, but a little voice inside my head told me “Fuck it!" and off I went. A husband and wife walked out of the rest stop building and looked my way and smiled. I became so focused on Greg's truck that as I passed the building, I had not realized I was walking on the sidewalk right toward two other truckers who were going to use the restroom. I couldn't walk into the grass wearing my booties, so I just kept my pace. The first didn't even look up. The second stared me down and smiled as I walked by. I glanced back as we passed each other to see he had done the same. I shot him a quick smile and put a little more emphasis on moving my hips and ass to give him a more enjoyable look.

About forty feet from Greg's truck, he looked up and we made eye contact. His eyes and face told me he was as excited to meet as I was. He was exactly as he looked in the pictures that he had sent. Greg was in his mid-fifties, a short salt and pepper haircut with, as he described it, a typical fifty-year-old body. He opened his cab door and climbed down to greet me.

"Holy shit, you're beautiful!"

"Well, that makes a girl's night for sure. Thank you, sweetie!"

He gave me a very polite hug with a slightly less than romantic feel to it.

"Let's go around to the other side and I'll help you up there. I must admit, you are way hotter than I imagined. And did you say this is the first time you've dressed in like, fourteen years? Amazing!"

Greg opened the passenger side door and helped me up as I tried to navigate climbing up into his cab in a dress and heels. I surveyed his cab as he made his way back around to the driver’s side of the truck. He was perfectly accurate describing his cab. It had a small couch which pulled out as a small sleeper and a table that folded down from the back wall. It wasn't very spacious, but I knew it would suit the two of us just fine.

"So, this is all the magic is going to happen?" I asked while pointing back behind us.

"I know it’s not much room, but I use it sparingly enough that it's all I really need."

"It'll be perfect. Want to?" I asked, motioning with my head to go back. Greg obliged.

There was not a lot of room for both of us to sit so as I sat next to Greg, he put his right arm around me. As our heads both turned toward each other, Greg slid his hand to my neck and pulled my face toward his. Our lips touched first, his facial hair tickling me as our mouths connected. I felt his tongue slide over my lips, and I quickly allowed my tongue to find his. Greg was an outstanding kisser. As his hand rubbed the back of my neck, I started rubbing his thigh. With each stroke, I moved up his leg and closer to his cock. Even though I hadn't made contact yet, the movement I could feel was a great indication that he was getting hard. After a few minutes of kissing and rubbing, my hand found the bulge in his pants. I felt the outline of his cock and realized it was bigger than what Greg described.

"From what I'm feeling, not exactly average size. Can I see?" I said like a cock hungry slut.

"Absolutely! I wasn't sure how fast you wanted to take this, but hell yes you can."

I helped Greg get his jeans and briefs off leaving his big dick sticking out for me to see. His cock was long, eight inches, and had a slight upward curve to it. The head was enormous. I slid down and maneuvered myself on the floor in front of Greg. I took his cock in my hands and stroked it while smiling up at him. I remembered how much I loved sucking cock, especially big cocks like this. After admiring his rock-hard dick and feeling its soft skin sliding in my hand, I had to have it in my mouth. My lips attached to his head, and I slowly took as much of him in as I could. My lips sucked tightly on his shaft while my tongue licked around it. My hand found Greg's giant balls and I started massaging them as my mouth went to work.

I could have sucked Greg's cock all night. My tongue licking across the soft skin on his shaft. My lips sucking the head of his erect penis. The taste of precum forming around the tip of his cock. I licked down to the base of his cock and took one of his balls in my mouth. I continued stroking his cock while I worshiped his balls with my tongue, first the left and then the right. I felt Greg's hand on the top of my head and looked up at him. He was smiling down at me, obviously very satisfied.

"Take them both at once. I want both of my balls in your mouth."

I opened my mouth as wide as I could and took his right ball in my mouth and then tried to stuff his left one in as well. They were so large!

"Come on baby girl! You can do it. Stretch that mouth. I want you to gag on my balls. Take them!"

After a moment, my mouth was filled with two huge, cum filled nuts. As much as my mouth was filled, my tongue still managed to lick Greg's balls. I could feel them pulsating in my mouth and knew he was awfully close to cumming. As much as it hurt, I loved having two giant balls filling my mouth. I let them both slide out of my mouth and my lips and tongue made their way to the tip of his cock. The taste of his pre-cum was incredible and I relished that I could still make a man cum after so many years. Greg sat up and moved to the edge of the cushion. His hand moved to the back of my head.

"Let me fuck your pretty little slut mouth! Oh fuck, you're such a little whore. Fuck!! I love your lips on my dick."

I felt Greg start thrusting his cock into my mouth and his hips against my face. His hands forcefully pushed my head onto his cock, holding it until I gagged at times. I looked up at him as I came up, gasping for air, my heart racing.

"Suck my cock, you whore! Don't take your mouth off my cock! Suck it! Swallow all my cum! Oh god, yes, baby!"

His pace quickened as I let him ravage my mouth with his cock, his hands forcefully guiding my head on and off as he wanted. I tasted his first shot of cum, a small amount on the back of my tongue, as his hands released my head and he reclined back against the seat. What followed was an initial load of his sweet jizz that quickly filled my mouth. Without a second thought, I swallowed his first three or four shots of cum and quickly realized my mouth was filling up again as cum continued to shoot out his cock. I swallowed again just a few seconds later. I kept stroking his cock, slowing the pace as I did. My lips kissed the tip and my tongue licked up the final remnants of his explosion. My hands slowly stroked his cock, squeezing out every drop of his cum into my mouth. I licked my lips clean and showed him my empty mouth.

"Fuck! Good girl. God damn you are a good little cock sucker. I wish I had more time with you today."

"You tasted so fucking amazing. I am so glad I found my way to you tonight. I absolutely LOVED this."

"Baby girl, would you be up for meeting again? Maybe next time we could get a little more time? I'd love to be inside you. I bet your pussy is so tight."

My head was resting against his leg and while Greg gently stroked my hair, I softly kissed his cock and balls.

"We definitely need to meet again. This was so hot, I loved it."

"Not that I want to share you with anyone, but I have a friend who would absolutely adore you. His name is Tim. He drives and he's on the road a lot more than I am. How long are you in town?"

"I'm here for two more days before I head back. But then I'll be back in about a month or so."

"Let me see if I can contact him. He'd be calling from a Pennsylvania number so keep an eye out."

I sat up next to Greg and kissed him once more on his lips.

"Thank you for this. I really needed this night."

As I was sitting there, I realized I had not shed a single piece of clothing. I was so hungry for cock I went right to work. I reached into my purse and pulled out my lipstick and a small mirror. After fixing my lips and hair, I realized it was time to go. Greg helped me out of the cab, and I made the walk back to my car. I looked like a slut. I felt like a slut. I loved being a slut. I saw Greg pulling out of the parking lot at the same time I had reached my car. I made sure my phone was on when I got in the car just hoping that Tim would call. I wanted more cock as soon as I could get it.