It was a sunny Wednesday morning. Dan had stopped to take a break on his daily bike ride. As he sipped water from a bottle another rider stopped at the same location.
As Bill dismounted from his bicycle the two men exchanged pleasantries. When he noticed the name of the football team on Dan's shirt, Bill commented about the upcoming season.
After introducing themselves and talking football for the next ten minutes they were ready to continue on their rides. Since both men were heading the same direction they kept up the conversation as they rode off together.
Over the next few miles of riding and talking, the two men found they had much in common. Both were retired, both liked the same pro football and college basketball teams, and both had lost their wives within the past few years.
The conversation never stopped. By the time Bill and Dan reached the spot on the trail where they would be going their separate ways, each felt like they had found a new friend.
"Enjoy the rest of your ride and have a great day."
"Yep, you too. I'm usually out here at about this time every day so I'm sure we'll be seeing each other again."
"Looking forward to it."
Afterwards both men realized they should have exchanged some contact information since they seemed to hit it off so well. It quickly became a mute point as they ended up seeing each other again the next day on their rides. This time they did exchange information.
Over the next few weeks Bill and Dan rode together nearly every day. They became good friends and started having drinks or meals together at a favorite Mexican restaurant.
Bill was sixty-eight with two adult children and five grandchildren. He was nearly six feet tall and weighed about two hundred fifty pounds, well tanned with gray hair and a bushy mustache. His wife had passed two years ago.
Dan was sixty-six with one child and two grandchildren. He weighed two hundred thirty pounds, was five foot eleven inches tall with salt and pepper hair. He had lost his wife three years prior.
Both men were overweight but neither was excessively fat. They each had that common older man beer belly. In clothes, they looked like any average man of their age.
When the pro football season started that fall, Bill invited Dan to his house to watch the games on Sunday. They drank beer as they cheered on their team and Bill grilled steaks for dinner.
The following Sunday Dan hosted Bill for the games. It became a weekly tradition and the two men rotated the hosting every other week.
What had started by a chance meeting on a bike trail that summer had quickly turned into a close friendship between the two widowed men. They had shared many talks and emotions.
Bill and Dan felt like they had known each other for their entire lives. In just over three short months they had become best friends. They could discuss anything.
The football season was a little more than half over and Dan was hosting. He grilled burgers that evening.
When they finished eating Bill mentioned there was something he wanted to talk about. Dan felt some concern by the odd expression his friend seemed to have.
"Sure what's up? Are you okay?"
"Yea, nothing wrong with me other than the game our team blew today. That fucking pisses me off."
"Yep, I feel the same. So what do you want to talk about?"
"Well before we talk, I want to show you something."
Bill had his phone in hand. He quickly flipped through a few things.
"You know, I haven't had sex since before my wife died. I don't know about you but I spend a lot of time online looking at porn and taking care of business."
"Yea, I admit I do the same. We gotta get relief somehow right?"
"Yep we do. It's normal. So anyway, I like to explore and check out a lot of sites. On one I visited recently I found something interesting that I know you'll be interested in too."
"Oh yea? And what is that?"
Bill handed Dan his phone. When he looked at the screen he felt his face turn red with embarrassment.
"I really like that picture of you Dan. I like some of the other ones even better."
Bill had discovered pictures Dan had posted on a website called "I'm a Sissy Wannabe." In the picture on the screen Dan was wearing bright red lip gloss and a dress. He was holding the dress up to reveal the big white nylon panties he was also wearing.
"Oh fuck. I never thought anyone that I knew would see these. God this is really embarrassing. I don't even know what to say? I really was just fucking around wearing some of my wife's old clothes. Not even sure why I wanted to post them?"
Bill had a smirk on his face.
"Oh yea right. Guys always post pictures online of themselves wearing women's clothes and playing with their cocks just for the fun of it."
"Well that is what I was doing whether you believe me or not."
"Hey, you don't need to get pissed off or be so defensive. I actually liked the pictures. They got me aroused and I'm just trying to help."
"I don't understand? How are you trying to help?"
"The description of yourself that you posted with the pictures says you're submissive and you want a dominant man to use you like a woman for his sexual pleasure. I was always dominant with my wife and would be happy to do the same with you."
Dan was quiet as he flipped through the pictures. His face was on fire and he had butterflies in his stomach. He couldn't believe he'd been caught by a friend and his secret desires were known.
"You know you want to do it Dan and so do I. I'm clean. We're friends and we can both fulfill a fantasy. I haven't had my cock sucked in a long time."
"I don't know. It seems really weird."
"Come on, why not? It's what you want and thinking about it is giving me a boner. Do you still have some of your wife's clothes?"
Dan nodded his head affirmatively.
"Great. Why don't you go get dressed, including the lip gloss. I've got some things in the car that I brought just in case we got to this."
"What kind of things."
"Just some of the stuff I used with my wife. She loved it. I'm sure you will too."
"Well I don't know? I guess maybe."
Dan had drank enough beer to lose some of his inhibitions. He sighed then went into a bedroom as Bill went out to his car. A few minutes later Bill was back and waiting in the front room for his friend.
When Dan returned, he was wearing a blue floral print button down the front knee length dress. His lips were coated with bright red lip gloss. The dress was pulled tight around the waistline by his big belly and his five o'clock shadow caused him to look even less feminine and more like just an old man wearing women's clothes.
