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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, Escort Çukurambar 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 demetevler escort 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. dikmen escort bayan 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.

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