Ann: A Love Story Ch. 88

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As I drove south down the winding road away from the Turnpike with the light on inside the car, I looked at the map, confirming that I was going the right way. Looking back at the road ahead, I turned off the light. But not before I had to adjust my position in the seat, finding it difficult to get comfortable; my cock feeling the constraints once again.

I couldn't get the image of that amazing woman out of my head. She was so beautiful, so playful...so hot. I'd wished I had more time. But that didn't stop my cock from growing. I wasn't thinking about Marcy, the hot little tollbooth attendant that had flirted with me...and flashed me to boot. She was all those things; beautiful, playful and hot. But who she wasn't, was Ann, my dream woman...and that's who I was on my mind.

"I can't believe she made me wear this," I said of her and her choice of wardrobe for me. She and Tina had a bet, the stakes of which I wouldn't know until I talked to her later that night. Part of the bet was that she would somehow get me to walk into Tina's shop naked. The other part was that I'd wear a special outfit on the way to West Virginia.

Sure, they'd have no proof other than my word. But just that I put it on and got in the car to drive off was enough for Tina to concede defeat. She knew if I said I would wear it then I actually would the entire way. It truth, it really wasn't that bad. It wasn't like I was wearing a dress. I was wearing a pair of Tina's shorts though. White spandex gym shorts, to be precise. To say they were short and tight on me was an understatement. I was surprised they stretched enough to fit over my hips and accommodate my thighs, but they did. They also did what Ann hoped they would, showing off my legs and my crotch in an almost obscene way.

She also had me wearing a baby blue T-Shirt that was about two sizes too small. She wanted to show off my body, just like I'd asked her to do many times before. Frankly, I didn't care. Nobody would really be able see me and even if they did, who cared. I liked the idea of pleasing her. And I loved the idea that it kept us connected as I drove.

It was hard not to think of her, considering how she'd left me...which was hard. She'd seen to that by strapping my cock and balls, telling me I couldn't take the restraints off until I talked to her. I'd given her my word that I would do what she asked and for the most part, it wasn't a problem. But a couple of times an hour, I'd think of her and the last thing she'd said to me before I left, the very thought making the veins in my thick cock throb to the point it hurt.

She had leaned into the open window of the car to kiss me goodbye. Putting her arms around my neck to hug me, she whispered, "Remember baby, the next time you fuck me, I'm going be your wife, and you're going to be in charge!"