The Biking Buddies

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.

Bill smiled as he looked Dan over.

"Oh yea, that's exactly how I wanted to see you. Now lift your dress and give me a little peek at what else you're wearing."

Dan pulled the hem of the dress up far enough for his friend to see the large white nylon granny panties he was wearing. His face was as red as a tomato as Bill gazed at him.

"Oh god, those are perfect. You look very enticing in those panties. Shall we get started."

Dan shook his head back and forth. As he lowered the dress he could see a bulge in Bill's pants.

"Yea, I'm not sure if I can do this?"

"Well I don't want to have you do something you don't want to do but from what you posted online it seemed to be something you were interested in trying. As a friend I was going to help you out."

"I know and I appreciate that but you being a friend is what makes it feel weird. I guess I need something less friendly."

"You mean someone more dominating who just makes you do the things you really want."

"Yea, I guess something like that."

"Well, let's try another approach and see how it goes."

"Okay but I'm still not sure."

Bill had Dan move directly in front of where he was sitting and turn around. When Dan was in position, Bill reached into the bag he had gotten from his car and pulled out some leather wrist cuffs.

"Put your hands behind your back for a second."

Dan chuckled nervously as he placed his hands behind him.

"Okay. But what are you going to do?"

Almost immediately Dan felt his wrists being bound together.

"There. Now stay facing away from me and get on your knees."

Dan was getting more nervous and no longer chuckling as he followed Bill's instructions.

"Oh fuck. I really don't know about this."

With Dan on his knees, he felt Bill putting something over his head. Before he realized what it was, a ring gag was pulled into his mouth and tightened.

Dan was virtually helpless and could no longer speak. Bill gave out a sinister little laugh then grabbed Dan's hair and spoke in his ear.

"Well friend, it's time that I make you get friendlier."

Bill helped Dan get back on his feet. After having his friend turn back to face him, Bill unbuttoned and opened the dress Dan was wearing.

Dan's face turned red again at having both the bra and panties he was wearing now fully exposed. Bill got a smirk on his face and grinned.

"It may be a little strange but I find it enticing to see a hairy old guy with a beer belly wearing a bra and panties and wanting to get friendly. Now let's see what's inside your pretty panty."

Dan's face got redder as Bill pulled the front of the white nylon panty down. When not aroused, Dan's little penis pokes out no more than two inches.

Bill chuckled as he looked at his friend's little nub.

"My god, that's not much bigger than a woman's clit. And it's shaved too. Very sexy! Is that all part of your desire to feel womanly?"

After he pulled Dan's panty back up Bill said the two needed to switch positions. Dan took a seat in the chair and Bill stood in front of him.

Bill removed his shirt. His big hairy belly hung over the top of his pants. He then unbuckled his jeans, slid them down his legs and stepped out of them.

As Bill stood in front of Dan wearing only white boxers he had a smirk on his face. He reached out and slid the dress off Dan's shoulders.

"Oh yea, that's much sexier. I want to have a full view of your bra and panties while you're doing the things a woman would do."

Bill chuckled, thinking of the fun he was about to have and knowing Dan no longer had a choice in what would happen. He placed his thumbs inside the waistband of his boxers and pulled them down.

As Bill straightened up he became fully exposed to his friend. After Dan glanced at the hairy overweight old man body and very big belly, his focus turned to the thick uncircumcised cock and large scrotum hanging below it.

Bill's half erect penis was sticking straight out about six inches. The flesh was pink and smooth like a sausage casing. It came to a tip at the end and looked similar to the unopened petals of a flower. Two large balls hung about three inches underneath in his big sack.

Dan felt nervous as he looked at Bill's manhood. Although he had fantasies about being in this position with a man he never thought it would happen. Now he had no doubts about what was going to happen.

As Bill moved closer to Dan he put a hand on his head. He then gripped his penis with the other and pushed it into Dan's open mouth.

"Oh god yes Dan, you have a cock in your mouth and it wants to be your new friend. Stick your tongue on the tip and lick it."

When Dan put his tongue on the tip of Bill's penis he could feel the opening in the foreskin. As he pushed his tongue inside against the cock head he felt the slit.

"Oh yea, lick the slit. Mmmm, yea that feels good. I've never had a man do this to me but I can tell you already that I like it."

Dan could feel Bill's cock getting bigger and harder inside his mouth. The reality of what he was doing was setting in and it became more real as Bill began to slide his cock in and out.

"Oh god yes Dan, you've just officially become a cocksucker. Now suck my cock."

After only a brief moment of enjoying the pleasure, Bill removed his cock from Dan's mouth, It was standing three quarters erect, had grown to seven thick inches and the tip of the head was peeking out of the foreskin.

As Bill stood in front of Dan he began to stroke himself. With each stroke he pulled the foreskin back fully exposing the big pink head of his penis.

"My wife always told me this thing was a mouthful for her. Did you think the same thing? Or maybe you need to sample it a bit longer to decide?"

Bill again put his hands on Dan's head and pushed his cock back into his friend's mouth. As he began to slowly move it in and out he moaned with pleasure.

"Oh god, this is great. It's nice having a friend who wears women's underwear and sucks my cock. I could really get used to this."

Bill was doing his best to take his time for enjoying himself but the entire scenario was quickly getting him more aroused. After only a few minutes he began to increase the pace of his thrusts into Dan's mouth.

Dan could feel Bill's grip getting tighter on his head and his cock pushing deeper into his mouth. His moans were becoming groans as he rocked his hips and fucked his friend's mouth.

"Oh yea Dan, I'm feeling really friendly now. Maybe even friendly enough to let you eat a load of my semen."

Bill chuckled as he put his hands behind his friend's head and pulled him closer. He was pushing his thick cock deep into Dan's mouth.

Dan gagged a number of times as Bill's seven inch cock hit the back of his mouth and pushed into his throat. Drool had started running down his chin as the thick penis rapidly moved in and out.

For some time Dan had wondered what it would be like to have a man ejaculate in his mouth. When he felt Bill's cock start twitching and throbbing, he knew he was about to find out. There was no way to stop what was now inevitable.

"Oh yea, oh yea, oh god yes Dan, I'm ready to give you a big load of friendliness!"

Dan simultaneously felt a large amount of warm fluid flow into his mouth followed by several strong spurts squirting into his throat. It was more than he imagined it would be and after the squirting stopped, a large amount of bitter salty semen continued to drain from Bill's cock.

Bill had been groaning loudly for the entire time he was shooting his load. After several seconds he slowed his pace and stopped moving his hips. As he stood quiet with his cock still in Dan's mouth he sighed with satisfied pleasure.

"Oh god, I can't remember the last time I cum that hard. You really got a mouth full of friendliness to swallow."

Bill continued to hold Dan's head and kept his cock in his mouth to make certain no cum could escape. He smiled as he watched Dan's neck muscles working.

"Oh yea, that's it. Swallow it all."

As Dan finished swallowing Bill's load and his first cock sucking experience came to an end, he realized that his panties were wet. He had been so engrossed in what he was doing that he never realized he had cum as Bill was ejaculating in his mouth.

Bill removed his cock from Dan's mouth. It was still hard and about half erect. He smiled as he began to slowly stroke himself again.

"God, I love Viagra. It takes me no time at all before I'm ready to go at it again. I hope you enjoyed that as much as I did."

As soon as the words had left his mouth, Bill noticed the large wet spot in the front of Dan's panties. He rubbed his fingers against the wetness and grinned as he felt the stickiness.

"I guess I didn't need to ask if you enjoyed it. That creamy load you shot in your panty makes it pretty obvious. I'm guessing you will enjoy what we do next too."

Bill helped Dan to stand up then pulled his panties down and had him step out of them. As he turned them inside out, the large amount of thick sticky semen Dan had deposited in them was visible.

"Oh my Dan, you sure made a mess in your panties. You creamed them just like an excited woman would. And they sure look delicious don't they? You've probably eaten your cum many times so I'm sure you won't mind letting me watch you eat it now."

Bill put the front of the panties over his finger and pushed them into Dan's mouth.

"Now suck them. Suck your own cum out of those panties and swallow it."

As he held his finger inside the panty in Dan's mouth, Bill could feel his friend sucking the cream from the silky material.

"Mmmm, that tastes so good doesn't it. Since you're enjoying them so much I'm going to let you keep them in your mouth a while longer."

Bill removed his finger but left the panties hanging in Dan's mouth. He instructed his friend to turn around then helped to get him in a kneeling position on the chair.

"You know I never paid attention to that girly butt you have Dan. It's plump and round, it looks like you shave it too. So nice and smooth. I like it and it's looking very friendly."

Bill chuckled and patted Dan on his butt. He pressed his cock between his friend's butt cheeks then began to slid it up and down.

"Oh yea that's feeling good Dan. You're giving me a nice big boner again."

After a brief moment of rubbing his cock in Dan's butt crack, Bill got a tube of KY Jelly from his bag. He nonchalantly whistled as he rubbed the slippery lubricant on Dan's anus then slid a finger into his rectum.

Dan moaned as Bill worked his finger in and out. After a short amount of time Dan felt a second finger being inserted.

Over the next minute or so Bill continued working his fingers in and out of Dan's tight butt. He removed them completely twice and added more lubricant each time he put them back in.

When Bill removed his fingers for a third time, he again patted Dan on his butt cheek.

"That ought to be enough to get friendly. Now lay your head on the back of the chair."

While Dan put his head down. Bill grabbed him by the thighs. He re-positioned his legs and spread them wider.

"Oh yea, that's better."

Bill pulled apart Dan's butt cheeks. He put the head of his penis against his friend's puckered hole and began pushing it in.

Dan whimpered as he felt the thick cock head slowly pushing past his sphincter. He moaned louder and tried to relax when he felt the full head inside his rectum.

Bill slapped Dan on the side of his butt cheek.

"Oh god yes, I do like your big girly butt. It looks so sexy and it's so tight. Now let's get friendly."

At the moment those words left his mouth, Bill shoved the full length of his cock into Dan's tight virgin hole.

As Dan groaned Bill grabbed his butt cheeks and began to fuck him. He grabbed the strap of the wrist cuffs holding Dan's hands together as he thrust his cock in and out.

"Oh yea Dan, are you ready to know how a woman feels when she's getting fucked by a man? My wife liked getting it deep and hard. I'll give it to you the same way."

Dan had fucked his own butt with a dildo but it was much smaller than the thick cock that was now inside him. Having Bill's big cock thrusting deep inside him was painful at first but as he got relaxed it became more pleasurable.

Bill noticed Dan had started moving his hips in sync with the thrusts of his cock.

"Oh yea that's it, ride my cock Dan. Ride it like a woman."

Bill reached around his friend. When he found that Dan's small cock was erect he began to rub it.

"It's good to know that you are enjoying this as much as I am."

Over the next few minutes Bill enjoyed himself as he thrust his thick cock in and out of his friend's tight butt hole. Dan was enjoying it as well. He was disappointed when Bill removed his cock.

"I know you were enjoying that but I have another idea that I think you will enjoy too."

Bill helped Dan off the chair then led him into a bedroom. After having him sit on the edge of the bed, Bill removed the panties from his friend's mouth.

"Now that your mouth is empty again you can have a little more of this."

Bill put his hand on the back of his friend's head and slid his cock into Dan's open mouth.