Rick’s Story; Beginnings

Monday morning Rick was nervous. He could not decide what kind of underwear to put on, which seemed a ridiculous thing to worry about. He stood there wondering what to do; what would Deb expect him to be wearing? Rick had the usual "tighty-whitey's" but he also had a few pairs in colors that were shorter than the usual briefs. He finally decided to wear the light blue pair; "not too racy and not too nerdy" he thought. He felt weird; he had expected to be turned on at the prospect of being naked before Deb all day. As Rick drove to her house, he became more and more nervous about actually doing it. By the time he got to her house, Rick was half fantasizing that Deb had changed her mind, wouldn't have the money and that he wouldn't have to go through with it.

For her part Deb was also getting nervous. Mostly she was worried that Rick would not go through with it, or wouldn't even show up for work at all. They had a good relationship going, and this was certainly going to change it, and she wasn't sure how. The "good girl" part of her mind was also getting more and more active. Deb couldn't deny that she was, on some level, cheating on Dave. True, it wasn't exactly having an affair, but she was going to be getting some kind of jollies from another man. A naked man. For the first time since having made the decision to see if Rick would do it, Deb was having some second thoughts.

When Rick got out of the car, he was full of butterflies. He grabbed the stuff from the hardware store, took a deep breath, walked up to the side door, and knocked. Deb started in her chair. "Well, he showed up!" she thought a little uncertain of how she felt about it right at that moment. She yelled to him "come on in, I'm in the office!" Rick opened the door and went into the house. The office was on the first floor; its decor was classic executive den, dark paneled walls with built-in floor to ceiling bookshelves, thickly carpeted, a window that looked out towards the barn, a large wooden desk with a red leather chair and two leather chairs in front. As Rick came into the office Deb was standing behind the large desk. She was wearing tight denim cutoffs with a tight light blue tee-shirt that showed off her nice tits. "Good morning!" she greeted him, smiling broadly.

Immediately she noticed that Rick seemed very nervous, and she got a little worried. Rick walked to her desk and handed her the receipt. She said "oh, right... I'll add it to your regular paycheck on Friday. Are you okay Rick? You ready to work naked all day?"

Rick thought "So much for her not going through with this!" He said "um... Yeah, I guess. You have the money?"

Deb looked straight at him and said "Rick if you're uncertain about it we don't have to do this."

"No, I'm fine; just a bit nervous as I've never done anything like this. But I do what I say I'm going to do, like I said -- you can trust me." Said Rick.

"Okay!" Said Deb "And like I said you can trust me too. There's just one thing: once you start there's no turning back. Agreed?"

"Agreed." Said Rick.

"Then here you go; the half upfront." said Deb as she handed him the envelope full of cash.

Rick quickly looked into the envelope and counted the cash. Rick thought to himself "well there's definitely no turning back now!" Deb relaxed as he counted; he clearly knew what he was going to have to do. When Rick finished counting the money, he looked at Deb and said "It seems we're good to go!"

There was a long pause between them, that Deb finally broke when she said "Okay! Then it's time for you to get started! You can leave your clothes right there on the chair and get them back five!" She was looking straight at him. Rick looked back at her. This was it, and he was very nervous. Rick first took off his shoes and socks. He then slowly pulled his polo shirt off over his head. Looking at her the whole time, Rick folded it neatly and then turned and placed it on the chair behind him. Turning back to face her, Rick unbuckled his belt, undid the waist button, unzipped his blue jeans and then slowly slid them off. Rick carefully folded them and put them on the chair. Rick was now standing before her wearing only his blue briefs. "Nice!" Thought Deb to herself; "no tighty whitey's! He's not as innocent as I thought!" Rick looked back at her, and she was staring straight at him grinning. "Next!" She said. At that Rick turned around towards the chair, closed his eyes and gave a little sigh which Deb didn't notice. Rick then tucked his thumbs into the waistband and slowly slid his underwear down his legs and stepped out of them. Still facing away from her Rick folded them neatly and placed them on the chair on top of his other clothes. Rick was now completely naked in her office. Deb stared at his ass and licked her lips.

The moment Rick was naked, he started to feel he definitely shouldn't be naked here and the electric buzz of arousal began to run through his body. "Nice ass!" Said Deb.

Rick looked at her over his shoulder and said "I'm glad it meets with your approval boss!" She laughed and Rick laughed too. With that Rick slowly turned and faced her. Rick could barely contain his arousal and his cock started to grow. He managed to keep it from getting hard, even though Deb's eyes locked on his member immediately.

Deb thought that Rick's cock was as pretty as his ass. "mmmmm! Perfect!" She said, staring at his semi soft dick. After what seemed an eternity to Rick, she raised her gaze to his eyes and said "well I guess you'd better get to work; same room upstairs. I'll be in to check on you in a bit!"

"Yes ma'am!" Rick replied as he grabbed his shoes, the apron, the gloves, and the steamer plate and turned to go up the stairs.

Deb sat down and stared intently at Rick's ass as he left the office and went up the stairs. "Jesus boy! That thing's more delicious in the flesh than I had imagined!" Rick's ass was nice and compact, with evenly round, deeply scalloped, muscular cheeks. Deb felt elated. She had done it! She wanted to see Rick walking around her property naked and here he was really doing it! She felt completely satisfied. "Man am I going to enjoy the next two weeks!" She thought to herself.

As Rick headed up the stairs, he became more and more aroused. By the time he got to the top of the stairs he was fully erect. Entering the room the feeling of being high with arousal really began to hit Rick. Trying to get a grip on himself, he began to reassemble the steamer. Rick couldn't believe this was actually happening! He was now standing in Deb's house completely naked and rock hard!

Almost in a stupor, Rick put on the apron, tying it behind him. While it covered his front it indeed left his ass completely exposed. This too was a turn on. Rick set about steaming the wallpaper, getting it ready for stripping. Rick couldn't fail to notice the irony that he was now "stripping" more than just wallpaper! Fortunately performing a routine task settled Rick down. Eventually his erection subsided and his cock settled into a mild state of semi-engorged arousal.

Soon Rick had removed enough wallpaper that he needed to take it up to the barn. The barn! Rick had forgotten all about it! This would mean leaving the house completely naked and going up to the barn with it! Rick could be seen from the road almost the entire time! While the barn was a long way away from the road, the house was much closer to it! That thought made Rick nervous all over again, and his cock became completely flaccid. Rick started down the stairs carrying the wallpaper towards the side door. The portion of the route from the side door to just past the corner of the house was very visible from the road.

Rick opened the side door and carried the wallpaper between his naked body and the road, stepping out onto the side steps. Rick looked towards the road nervously; and then stepped down off the steps and onto the gravel driveway attempting to rush up to the corner of the house where he would be less likely to be seen. However, Rick wasn't wearing shoes and the gravel was sharp. He had to walk slowly up the driveway. There wasn't anything Rick could do to hide his nudity; he couldn't really carry the wallpaper between himself and the road anymore, so his bare-naked ass was visible to anyone driving by! Rick's pulse was racing, and at first, he was freaking out. Fortunately, no one drove by, and as Rick went past the pond and got closer to the barn the inevitable thrill of being exposed with no means of escape began to take over his mind and body. That electric buzz returned, and his cock again began to swell. By the time Rick got to the barn it was already semi erect. Rick placed the wallpaper in the waste bin and turned to go back to the house, now hard again.

Deb had heard Rick coming down the stairs with the bundle of wallpaper and pretended to be doing some paperwork as he passed within view of the office. She quickly glanced at him as he went by again seeing his pretty cock. She waited until she heard the crunch of gravel as Rick walked up to the barn, then shifted to one of the side chairs and watched him as he walked up the drive. Deb thrilled watching his cute ass as he casually strolled along. His ass cheeks wiggled back and forth and bobbed up and down just perfectly, with a splendid steady rhythm. It was just what she had imagined!

She watched him as he went into the barn. She was looking forward to watching him walk back to the house completely naked. Suddenly the phone rang, jolting her out of her reverie. Deb picked up the receiver. "Hello?"

"Hi babe! How are you doing?"

"Dave!" Said Deb. "I'm fine. How are you? I assume you got there okay?"

"Yeah" said Dave "but it's been a really long day and a lot of travel. I just wanted to let you know that I got here safe and that I love you! But listen, I forgot to bring a few numbers with me; they're in my files in the office. Can you look for them for me?" Holding the phone receiver between her shoulder and chin, Deb turned to open the file cabinet and began searching for what Dave needed. Because the file cabinet was behind the desk opposite the window Deb missed the sight of Rick coming back down the drive.

As Rick stepped out of the barn door and headed back down towards the house he could see the pond, the house and the road just beyond it. Rick was acutely aware that he could be seen by anyone driving by. That drunk feeling returned, and Rick started walking slowly down the driveway, his now throbbing cock swaying back and forth in front of him. God he was so turned on! At one point a car did go by on the road, but it went by at such speed that Rick was certain no one saw him (although they might have!). His cock swelled even larger and throbbed at the very idea. Rick quickly entered the house through the back door this time and went back up the stairs into the room. Rick had to sit down and relax for a few moments. Eventually he calmed down and began working, his cock again softening.

Rick had been working for about 45 minutes when he heard Deb's footsteps coming up the stairs. Even though she had already seen him naked in her office, somehow the fear and thrill of her seeing him work naked electrified his arousal, and his cock instantly shot to attention. When Deb entered the room, Rick was steaming a particularly difficult piece of wallpaper. He was facing the wall holding the steamer up slightly above his shoulders, with his exposed back and ass pointing straight towards the door as she walked in. "Mmmmm! That apron frames your ass just perfectly!" Said Deb.

Rick's cock pulsed upon hearing her words. He glanced back smiling and said "I knew you would like it!"

Deb stared straight at Rick's ass as she asked "it seems like that piece of wallpaper is pretty stubborn?"

"Yeah, I've been working on it for a while. I think I've got it pretty soaked right now so it should be ready." Without thinking, Rick set the steamer down, picked up a scraper and began to strip the wallpaper off the wall.

"Hey wait a minute!" Said Deb. "You're only allowed to wear the apron while you're using the steamer! You've got to get naked again before you start scraping the wallpaper mister!"

"Whoops! I forgot! Sorry!" Rick put the scraper down, took off his gloves, and his shoes. Still facing the wall, Rick started to untie the apron. Just as he did so, Rick suddenly became acutely aware of his rock hard cock; while Deb had seen him completely naked earlier, Rick hadn't been erect in front of her and in just a few seconds that was going to happen. Rick could feel his heart thumping in his chest, and he started to blush. Rick was both scared of her possible reaction and incredibly turned on. Rick was still turned slightly towards the wall as he removed the apron, but he was pretty sure she caught a glimpse of his erection from the side as he tossed the apron on a small table. Rick picked up the scraper and turned back to the wall.

"Holy shit!" Deb thought "is he...?" Deb came up beside Rick and looked down and saw Rick's hard cock. Deb's eyes opened wide as she just stared at Rick's erection. She thought two things: "his cock is beautiful" and "Jesus is he hard!" Rick glanced at her; she looked him in the eyes for a moment, but her wide eyes went right back to his erection. This made it even harder, and Rick was sure it was going to explode. He had never felt so hard in his life.

Still staring at Rick's cock, Deb said: "So... Um... Wow!... UHH... Nice! It's a... good to see that you're so happy in your work!" She smiled as she said it, but it felt like a nervous grin.

Rick still felt awkward and nervous but turned on as all hell too. "Uh .... Well... yeah I have to admit I am enjoying it ... at least a little bit!" and smiled at her.

She looked at Rick briefly but then her eyes went right back again to his hard on. "More than a little bit I'd say from the looks of that thing!" There was a long pause between them: Rick trying to focus on stripping the wallpaper, while Deb just looked and looked at his stiff cock. "Well... good work! Keep it up!" She said with a giggle, "I suppose I should leave you to it for a bit!" She then walked backwards out of the room, her eyes never leaving Rick's rigid member.

As Deb walked back down the stairs she felt stunned. She entered the office and slumped down into her office chair. The image of Rick's beautiful cock dominated her mind. In all the time she had fantasized about Rick working naked, it had never occurred to her that he might have an erection too! She felt silly; how could she have never thought of that? Anyway, the amazing reality of it was now here. She ran through the image of Rick's cock in her mind. The helmet was beautifully big, red, and shiny like Dave's, but unlike Dave's, Rick's cock was so straight and so hard! Her mind roamed over the shaft, remembering the beautiful articulated veins that were thick but not too thick. His balls surprised her; "wow! he shaves them!" she thought. They were nice and even pulled tightly upwards against the base. As the images flew through her mind, Deb became dimly aware that her pussy had started throbbing. She was losing control, and that disturbed her as she was a woman who always liked to keep control of herself and the situation. But now that situation was Rick, whom she was paying to be naked for her, and now he was hard, hard, hard. Deb was unsure what his erection meant exactly. Obviously, he was aroused, but was he turned on by her? She suddenly felt like she no longer knew where things with him were heading.

As soon as Deb had left the room Rick felt dizzy with arousal. "What was that??" he thought. Rick looked down at his cock; it was pointing almost straight up, the helmet was huge and his urethra was pulled wide open. His cock started to involuntary spasm and pulse rhythmically. Precum appeared on the tip and Rick felt like he was going to ejaculate right there even though he wasn't even touching it. Rick slumped against the wall. "Maybe I should just jack off right now" he thought to himself; but he wasn't sure it was allowed, and he strangely felt he could not cum without his employer's permission. Through sheer force of will Rick held off his orgasm. A lot of pre-cum flowed from the tip of his cock and onto belly and his thighs. Rick managed to rub it in before any of it hit the floor, but it was close! Rick slid to the floor, naked and panting for a few minutes.

Rick managed to regain some composure and even though he was still in a daze he started to again use the steamer and the scraper to strip the wallpaper. The familiar routine once again had the effect of calming Rick down, and his erection again subsided. Even though Rick was still aroused, he started to feel weirdly normal working in someone else's house completely nude.

Deb decided that she needed to calm down and if Rick was hard at lunch that wouldn't do it. She decided to go into town over his lunch break, even though the devilish part of her wanted to see that hard cock again. A short while later Deb called out "Rick! Time for lunch! I'm going into town, so you'll be by yourself; but remember you must stay naked!"

"Yes Boss!" Said Rick out loud and silently to himself "As if I need to be told that!" Rick heard the door close as Deb went out of the house. Rick turned off the steamer and took off his apron, gloves and shoes and started down the stairs. Quickly glancing towards the road, Rick dashed over to his car parked just off the driveway, grabbed his lunch and froze. Where should he eat? Standing not far from the road, Rick quickly looked around and decided that sitting on the back deck would be the best place to eat lunch. "I don't want to sit my bare ass down on the furniture!" He thought. It was a nice warm day, and the deck was partially in the sun, and partially shaded by a large oak tree.

Rick sat on the part of the deck that was in the sun and began to eat his lunch. The sun felt good, as even though it was a warm day, the room he had been working in faced west, and therefore was a little cool, at least if you were stark naked. He was out of easy sight from the road, although he could hear the occasional car or truck going by. As he basked in the sun, his arousal returned, and he thought about Deb's eyes riveted on his naked cock. Rick started getting hard again. He felt great. He was outside completely naked, and it was perfectly okay with his employer! When he finished eating, Rick laid in the sun with his eyes closed fantasizing that Deb was fondling his erect cock. Rick started to play with himself. It felt so good to be laying here in the sun stroking himself as if it were completely normal. Several times he almost came but he managed to let go of his cock in time and so managed to hold off the orgasm. There was a lot of pre--cum that Rick let spill onto the ground beside the deck. Rick lost track of time and was playing with himself when suddenly he heard a car turning into the gravel driveway from the road. Quickly glancing around the corner of the house he realized that it was Deb. His status as her employee suddenly cut through his reverie. Jumping up he said to himself "I'm late!" Without thinking he dashed into the kitchen side door and ran up the stairs, his cock bobbing up and down and slapping his belly. When he got into the room he was out of breath, and suddenly realized how silly his reaction had been. Rick chuckled to himself "Wrong move buddy! I think Deb probably would've wanted to see you on the deck!" It was just so hard to quit the habit of getting paranoid about being seen. Shaking his head, he turned on the steamer and got ready to return to stripping the wallpaper.

He heard Deb enter the house "Rick I'm back! Everything okay?"

"Yeah! Just fine!" He answered, thinking "if you ignore the fact that I'm stark naked, rock-hard and throbbing!" Once again, the routine of working on the wallpaper had its calming effect and his cock relaxed. While he was still turned on, for the first time it wasn't so much that he felt normal working naked, it was more that he could relax with his arousal. In a way it was just like when he was laying outside on the deck feeling finally free to be naked somewhere "public." He was starting to enjoy working naked for Deb.