Mr Richardson Ch. 01

The summer after I graduated from high school was a hot one. You would think that first summer after escaping from school would be carefree and fun for me. But it wasn't great because I was underemployed and worried about my future. I couldn't afford to go to university. My parents split up a few years ago and between them they couldn't afford to foot the bill and there was no way I could earn enough doing odd jobs. To make matters worse most of my friends were away at sports camps or family vacations and I had no one to hang out with. I guess I was feeling a bit sorry for myself too.  

I kept busy doing handyman work for people in my neighborhood. There were a lot of older people in the area who need help with gardening, lawncare, painting and small repairs. I guess I was doing a good job because I got a lot of calls and had all the work I wanted to take on.  

One of my clients was Mr Richardson who lived a block away from my house where I lived with my mom. Mr Richardson called me to see if I would mow his lawn. He was in his late fifties and very fit so he could easily do it himself but he was working full time and it was a big lawn so he figured he'd rather have someone else do it. We agreed on $60 which I though was on the generous side at the time.  

One hot Saturday afternoon I was mowing Mr Richardson's lawn. I quickly regretted not doing it in the morning. It must have been 100 degrees. Luckily the backyard was very shady. But it was still hot and I was really sweating. There was an in-ground swimming pool in the backyard that looked pretty inviting.  

I was nearly done when Mr Richardson came out to see me. I turned off the mower.  

"Dana you must be exhausted. When you're done why don't you come in the house to cool off. In the meantime there's a big glass of ice-cold lemonade on the deck for you."

"Thanks Mr Richardson, that would be great."

In ten minutes I was done and put the lawnmower away. I decided to come back in the morning to do the trimming. I downed the lemonade in one big gulp. It was a relief.

Mr Richardson's house was a big ranch style bungalow. It seemed even bigger from the back because the land sloped away from the house and most of the basement was above ground. There were big windows and large sliding glass doors in the lower level overlooking the backyard and pool. I kicked off my dirty shoes and knocked on the door.  

Mr Richardson was in the basement and waved me in. I slid the door open and was met by refreshing cool air.  

"Dana, you're soaked with sweat. Go upstairs and take a shower. We'll have a beer afterwards."

"Um, ok sure," I replied.  

"The bathroom is the second door on the left."

I went up the stairs and was struck by what a beautiful house it was. Mr Richardson was pretty well off. He started off as an engineer at a large manufacturing company but was now a senior manager. He split up with his wife years ago. He has two children, a son and a daughter. The son works in another state. His daughter Sally is in university. This summer Sally is travelling around Europe.  

The bathroom was luxurious with a standalone shower with glass enclosure and a Jacuzzi bathtub.  

I took off my filthy tee shirt, shorts and underwear and put them on the counter. Then I got in the shower and adjusted the water temperature. The stream of water was refreshing. I was just starting to lather up when I heard a faint knock on the door - then the door began to open.  

The door opened just enough for Mr Richardson's head to pop in. Instinctively I covered my privates with my hands. Mr Richardson took my dirty clothes and replaced them with a housecoat then apologized for the intrusion.  

After Mr Richardson closed the door I resumed washing myself. I was surprised to realized that I had an erection. I stroked my cock with my soapy hands. It sure felt good! I wondered what Mr Richardson would think if he barged in again and saw me jacking off. I felt strangely aroused and vulnerable standing naked in an older man's bathroom.  

After a good long shower I rinsed off and stepped into a big fluffy towel. I picked up the housecoat. It was more of a kimono made from a light silky fabric with a colorful tropical flower pattern. It would be cool to wear.  

I put on the kimono and looked at myself in the mirror. I'm a slim guy with fairly long curly blond hair. My lips are full and have been described as 'pouty'. I looked rather feminine in the colorful kimono. But the pointy bulge detracted from the look. My erection wouldn't go away and I didn't even have any underwear to help push it against my tummy.  

I couldn't let Mr Richardson see me with a boner so I started to focus on other thoughts in the hope that my cock would relax.  

I had been in the bathroom for ages and didn't want to delay any longer than necessary. Finally, after thinking about the chores I have to do over the next few days my little penis got soft again.  

"Feeling refreshed I hope," Mr Richardson said as I walked down the stairs in my kimono. "I hung your clothes on the railing to dry."

"Thanks Mr Richardson," I replied.  

"Oh just call me Stephen, Dana. Would you like a beer?"

"Sure, a beer would be great!"

This part of the basement was away from the windows and big glass doors, and was dimly lit. There was a well-appointed bar, a big leather couch and a giant flat-screen TV. It was refreshingly cool.  

Mr Richardson got two bottles of beer from the bar fridge and opened them.  

"Here you go Dana. Thanks for all your hard work today. I felt bad that you were out there in this heat."

"It's ok Mr Richardson, I mean Stephen, I should have come first thing this morning. I shouldn't have slept in."

In fact I didn't really sleep in, I went to bed last night wearing a pair of my mom's pretty panties and a bra. In the morning I jacked off twice watching sissy porn on my phone. Recently I'd been having uncontrollable fantasies about being a crossdressing sissy faggot whose sole purpose on this Earth is to please and pleasure older men. Men like Mr Richardson.  

Mr Richardson gestured to the couch, "have a seat Dana."

I took my beer and sat down on the cool leather. I discreetly tucked my dick between my legs because it was starting to stir again just from the thought of lying in bed this morning in my mom's panties and bra.  

Mr Richardson sat down beside me and we had a good chat while sipping our beers. Mr Richardson wanted to know all about me and my family. He knew my dad.  

I was tired from working in the hot sun and the beer was making me drowsy when Mr Richardson got up and fetched two more beers.

Mr Richardson passed me the second beer and sat down beside me again, only a bit closer this time.  

"Do you have a girlfriend, Dana?"

"No, I've dated lots of girls but never really had a girlfriend," I replied. "I haven't had a lot of luck with girls to be honest."

"You must be a frustrated young man, Dana. Do you get some relief from masturbating?"

I nearly choked on my beer!   couldn't believe Mr Richardson would bring up the topic of masturbation. He must be a real pervert, I thought. And here I was sitting beside him in a skimpy silk kimono and no underwear! The thought activated my weenie and before I knew it, a bulge appeared under my kimono. I held my beer in such a way as to hide my hard-on.

But Mr Richardson continued his naughty talk, "I must say I have to jack off a lot since my wife split. I usually do it right here watching porn on TV. Would you like to see some of my porn playlist?"

"Um I don't know Stephen. Would that be appropriate?"

"Why not? You're 18 aren't you? We're just two guys with nothing to do on a Saturday afternoon." He reached for the remote. "Let's see what's on."

Actually, I was happy to watch porn with Mr Richardson on his big TV in the privacy of his basement rec room. The setting was turning me on. I was glad when he dimmed the lights further so I wasn't as concerned about him seeing my hard-on.

The first video was a of a beautiful young woman wearing only panties and a bra on a bed with a big muscular black man who had an enormous cock. It was a thrill watching her work his cock. She licked his balls and then sucked the big head for a long time. With his cock in her mouth the man unclasped her bra and removed it. Her gorgeous tits hung down and swayed as she eagerly performed her duty.  

I imagined what it would be like to be in her place between the man's big muscular legs. My little cock was aching.  

After giving him some sexy boob action, the woman stood up and with her bottom facing the camera, slowly pulled down her panties. Then she turned around and revealed a small but hard cock between her legs! She was a tranny!  

Instinctively I touched my hard little cock.  

"Dana why don't you take your cock out and jerk off. You seem to be aroused by the video. I wouldn't want you go home frustrated." 

Mr Richardson got up and opened a drawer in a side table. He pulled out a small bottle and handed it to me.  

"Here's some lube."

I leaned over to put my beer on an end table and my erection peeped out from the kimono. I was embarrassed but I took the lube from Mr Richardson's hand.  

"Don't be shy Dana. We've both done it hundreds of times."

I was so nervous I fumbled with the lid on the bottle. I wasn't sure how to open it.  

"Let me help you Dana." Mr Richardson took the bottle and flipped the lid open. But instead of giving the bottle back to me he dribbled some lube in his hand.

"Would you mind if I jack you off Dana?"

"Gosh, I guess if you want to," I stammered. I was shocked by Mr Richardson's suggestion, but the idea turned me on. He was obviously trying to seduce me and I was happy to let him. I knew at that moment I would go along with whatever he wanted to do to me.  

With one hand Mr Richardson moved the fabric of the kimono out of the way allowing my perky little cock to stand straight up. With his lubed hand he wrapped his fingers around my cock. My small hard-on was completely held within his slippery hand.

I looked at Mr Richardson. He smiled and started to stroke my cock.

"How does it feel, Dana?"

"It feels wonderful Stephen. I can't believe you're doing this to me."

I closed my eyes and relaxed as his warm slippery hand firmly stroked my cock. It felt so good!

Then I felt Mr Richardson lean toward me and kiss me on the lips. With my eyes closed I returned the kiss and let him explore my tongue with his. It was the first time a man kissed me. I had been waiting for this moment for years. I just didn't expect it today.

Mr Richardson kissed my neck and ears.  "Your'e a very pretty boi Dana," he whispered. "I'm glad you're willing to play."

"It feels so good Stephen. I think I'm going to cum!"

Mr Richardson squeezed my boner harder and sped up his strokes. I squirmed and writhed on the couch as he kissed me and pleasured me.

Suddenly, I was overcome with that intense burst of pleasure as I came and spurted cum all over my tummy. I opened my eyes and I could see gobs of my cum spilling over Mr Richardson's hand which was still holding my cock.

Stephen smiled at me and held his cummy hand to my lips. He watched intently as I licked the cum off his hand. One by one I took each of his fingers into my mouth and sucked it clean. Quietly Stephen scooped up cum from my tummy and I licked that too. I had tasted my own cum many times and it was thrilling to taste cum next to this handsome older man.

I was still breathing heavily from my orgasm when Stephen said, "looks like you had a satisfying cum Dana."

"It was wonderful Stephen. I never expected you to make me cum today but I loved it!"

He turned toward me and kissed my cummy lips. I could feel his stubble against my cheeks. He whispered in my ear, "Dana have you ever sucked a man's cock?"

I immediately thought of the encounter I had recently with an older guy who convinced me to put on his sister's bra and panties and then suck his cock. I sucked him off twice that day.

"Gosh, no I've never sucked a cock," I lied.

Stephen kissed my ear and said quietly, "I'd love to be your first. I'd love it if you would suck my cock."

I took a deep breath. I could smell Stephen's aftershave. Looking down I could see a big bulge in his pants. I put my hand on the lump. His cock felt really big!

"Let me get your pants down," I said as I began to unbuckle Stephen's belt. He lifted his hips to assist.

Stephen's cock was so big and hard that I struggled to unzip him and push his pants down. Then I used both hands to pull his underwear down to his thighs. His big gorgeous cock stood at attention awaiting the pleasure only an eager sissy's mouth can provide.

I held Stephen's balls. His pubes were well trimmed and his ball sac was shaved bald. His balls felt big, warm and heavy in my hand.

Stephen picked up the lube and I held my hand out as he dribbled some onto my palm. I spread lube all over his cock and balls and continued to caress him. His cock was so big I could hardly get my hand around it as I moved it up and down his shaft.

Stephen whispered in my ear, "go ahead Dana. I know you want to."

He was right. I couldn't wait to take him in my mouth. I cupped his balls in one hand and braced myself with my other hand on his chest. I was surprised to feel how muscular Stephen's chest was.

I leaned forward and took the top of Stephen's cock into my mouth. It was soft and warm. My mouth filled with the delicious taste of precum. I started to move my tongue around his cockhead. Stephen moaned and ran his fingers through my hair.

Stephen pushed gently on my head - my cue to take him deeper and start sucking. I hit a satisfying tempo taking him quite deep and bobbing my head and shoulders up and down, and using my tongue as much as I could.

Stephen's cock was beautiful. A real 'wife pleaser' I thought. It was circumsized with a big purple knob that I had to open wide to take in my mouth. The shaft was long and firm with lots of big pulsing veins. I could feel Stephen's pulse with my hands and mouth. And Stephen's cock smelled and tasted wonderful - the clean taste of a well groomed man with hints of bodywash. I was in heaven making love to Stephen's cock with my mouth.

While I sucked his cock with abandon, Stephen pushed my head down with one hand and slid his other hand along the silky kimono to my bum where he hiked up the material and started exploring my bottom. It was a turn-on to be felt up by a man's big warm hand.

A finger slid along my crack and gently touched my love-hole. Stephen's hand still had some lube from jacking me off and he circled my hole with his finger, coaxing it open. My love-hole was quite accustomed to entry as I masturbated with a dildo nearly everyday. Stephen had no trouble slipping his finger inside me. I moaned with pleasure as he fingered me.

"You're doing a great job Dana! I'm not going to last long!"

"Enjoy yourself Stephen, cum whenever you like," I said between sucks.

I took his cock out of my mouth for a moment to rub my wet lips along his shaft while stimulating his slippery knob with my hand. Then I tried to get his balls into my mouth but I couldn't from my position kneeling on the couch. His finger in my bum felt so good I didn't want to move so I went back to taking his dick in my mouth as deep as I could and sucked hard and fast.

Then I felt Stephen's legs tremble as he pushed harder on my head. I would have gagged but his cock entirely filled my mouth as his first spurt of cum went down my throat. He started bucking hard - with each spurt the head of his cock was right at my throat. I was truly being used for pleasure and I loved it. As Stephen enjoyed his orgasm in my mouth I was in a dreamland imagining all the deserving cocks in the world that needed relief and how many I could possibly satisfy.

I snapped out of my dream as Stephen took his hand off my head. His finger was still teasing my love-hole.

"God that was the best cum I've had in years!" Stephen said, still panting. I let his softening cock slip out of my mouth.

"I'm so glad you enjoyed it Stephen. I enjoyed it too!"

I lifted myself onto my knees and turned toward Stephen. Our lips met in a loving kiss. He put his hands inside my kimono and held me. His big strong hands felt good on my body. Our tongues met and I knew he could taste his cum in my mouth.

After a few minutes of smooching Stephen looked at me, "I'm glad you're coming back tomorrow to do the trimming."

One of Stephen's hands slipped down to my cock. It was stiff again. He gave it a little tug.

"You really are a horny little slut, aren't you Dana."

"I can't help it Stephen. Everything about being here with you is so sexy!"

Stephen kissed me again. "I'm glad you think so Dana."

Then he broke off the kiss and reached for something in a drawer. Turning toward me he held up a pair of the prettiest pink panties I'd ever seen. They were very silky and rather transparent. The front had a bit of lace and the band and leg openings were trimmed with lace. They were full-back style and the behind was practically see-through with rows of ruffles. My cock ached to wear them.

"I want you to take these home with you. You can wear them to bed tonight and jack off thinking about sucking my cock if you like."

"Oh I can't wait to try them on Stephen," I replied taking the panties from Stephen's hands.

"Just make sure you wear them tomorrow when you come over. I will check to make sure you're wearing them."

"Don't worry Stephen, I'll be wearing them. But I don't mind if you check," I said with a wink.

"Oh, I'll check alright. You know I think we're going to have a lot of fun together this summer. I'm looking forward to seeing what other skills you have. And I'd like to give you some training and guidance, if you know what I mean."

"I think I know what you have in mind, Stephen, and I won't let you down. I'll be a very eager pupil, you'll see!"

"I like your attitude, Dana. Your training starts tomorrow."

... to be continued.