Lessons For Jessica

Thanks so much to Angel Love for editing this for me.

(This story is a continuation of my previous two stories: 'Amber Conquers', and 'Sandi and Ashley are Great Teachers')

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Landscapers come across a lot of people in the course of their day. I had certain customers that I just loved to take care of. I would look forward to three of my weekly customers in particular. The hot months were the best because, obviously, girls dressed in a lot less. Oddly enough, my three favorite customers had pools. Ashley had a pool and we had a lot of fun in it, but Jessica was another. Regardless, during the hot days, I could count on Jessica lying out to get a tan. On the better days, she would have friends over and I could swear that she did it just to tease me.

Jessica was one of my friend's wives. I'd actually been doing their lawn as a favor to them. It normally would take me twenty minutes total to mow their front and back yard as they were both small. But usually I would set aside an hour to spend there if she was lying out. I would often talk to her while she was wearing one of her skimpy bikinis or lying on her stomach with her bikini top off.

I went to school with Jessica and Mike (her husband) and never thought of her sexually. I was two years older than both of them but saw them a lot at school and at parties. Like I said, we lived in a small town so you know just about everyone.

In high school, Jessica wasn't my type. She wasn't very tall, and was flat as a board. But shortly after her and Mike married, she went to the doctor and came back with C cups. Funny how that worked.

With her surgery, her tits were more proportional to her body. She looked great. She had sandy blonde hair that was cut at her shoulders. She had beautiful legs that as I could only imagine, led up to a wonderful treasure. Her ass was firm and fit well with the rest of her body.

I flirted with her as much as I could both in front of Mike and when he was not around. Mike knew what he had: A knockout trophy wife . . . who would never cheat on him because she wanted to continue to get the jewelry, cars, and other stuff that his stock broking money could buy.

Today I was going to their house and was hoping that she would be there . . . lying out once again. Fortunately, Mike was a hard worker and to my knowledge, never showed up at home before 7:00 pm.

I got there and decided to start on the front yard. I saw no signs of Jessica through the front living room window. The curtains were drawn so I could see right in. I made quick work of the front and started on the side. When I approached the side where their bedroom window was, I glanced inside and saw a figure facing opposite of me. There was a white lace curtain in the window but I could still make most things out in the bedroom. I kept the lawn mower running and grabbed my sheers to trim the bush by the window so I could see what was going on. It looked as though Jessica was changing but I couldn't see too well. She wasn't naked and not wanting to be a "peeping tom" I quickly put my sheers away and finished on the side yard. I was happy that she was home.

When I finished the side yard, I opened the gate to the backyard and pushed my mower through. I walked to the back and out of the corner of my eye noticed she was lying out already. I glanced over at her and saw her lying on her reclining lawn chair. She was completely topless! I was certain that she did this on purpose. She heard me mowing in the front yard and was still changing when I was working on the side yard. She knew that it would only take me another five minutes, if that, to get to the backyard.

Now let me tell you something. I've worked on her for more than four years now. I've mentioned to her that it would be nice for her to show me her tits. I tried to convince her that they really weren't hers and it didn't matter if I saw them. I also tried to convince her that she should show me as a "thank you" for me mowing her yard for free. All of these attempts were to no avail. In fact, sometimes she would flirt back and other times she would flat out shut me down making me feel stupid. I wasn't sure what had changed.

"Hey Jessica!" I yelled out.

She looked up and at once pretended to cover up. Even with her hands over her tits, I could still see her right nipple. "I didn't see you come in," she said.

I was still convinced that she had planned this. I went over to her leaving my mower by the gate.

"How are things going?" I asked.

She just sat there still trying to cover up. "I'm ok. How about you?" she asked biting her lower lip.

"Well I've never been better!" I said with an evil grin. "Today my dreams . . . heck my fantasies came true."

"Whatever," she paused. "I am so embarrassed. You better not tell anyone." She moved her head as if to point at her boobs.

I didn't respond. I continued to check her out. "You might as well take your bottom off too. You'd get a better tan, and now that I've seen your tits who cares if I see more. After all, you wouldn't want me to tell anyone would you?" She was wearing a nice bikini bottom that was primarily yellow with red, orange and green tropical flowers on it. It was a nice color to compliment her tan.

She glared at me. I could see in her eyes that she didn't know if she should be pissed off or turned on.

"Yeah right," she finally responded. "You already saw too much." She was still biting her lower lip.

I raised my voice a bit, "Jessica, don't try to act so friggin' innocent. You heard me mowing the front yard. What does that take me . . . eight minutes tops? You knew darn well that I hadn't done the backyard yet. Besides, you were just changing when I was mowing by your bedroom window."

She looked at me not knowing what to say. "Are you saying that I intentionally showed you my tits?" she finally asked. She began to smile as she lowered her hands.

I smiled back. I looked at her a moment longer hoping that she would do something to give me a hint. She didn't. For fake tits, they were magnificent. I love advancements in medicine.

We continued to talk a bit. In between conversations I mentioned that I better get back to mowing hoping that she would do something like pull my hands toward her breasts. She didn't. So finally I got up and moved toward my mower hoping the whole time she'd call me back. To my disappointment, she didn't.

So I decided that instead of mowing right now, I'd trim some low hanging trees hoping to give her some time to make a move.

A few minutes passed and with my back facing her, I could hear her moving. I glanced over my shoulder and noticed her with her body turned away, bending over taking the bottom of her bathing suit down. Holy shit! She lingered there pulling her suit from her ankles a little longer than most people would take and I got a perfect shot of her exclamation point. I couldn't believe what was happening. Here I'm staring at this hot chick that I've been flirting with for more than four years. Never once did I really think that she would break. What in the hell is going on?

I let out a whistle to her. She turned around looking a little embarrassed but she appeared quite confident about her body. Biting her lower lip again, she gestured me over. I quickly went over as most sane and straight men would.

"I know you flirt with me a lot. I would assume you find me attractive?" she asked.

I nodded my absolute yes to her.

"Well here's the thing. I know you and Mike are good friends. I know you and I are good friends for that matter. I have a little problem that I hope you can help me out with."

'Ok, what's going on here?' I wondered. I would be happy to help most any naked girl with or without a body like this.

"As you know Mike and I have been married for six years now. And even before that, we were high school sweethearts and I've never been with anyone else." I nodded again. "We are happy. I mean I'm happy and he acts like he is. I really believe he is." She almost sounded like she was trying to talk herself into this happiness. "I'm going to tell you something that only he and myself and now Ashley knows."

I waited for her to gather courage, not having a clue what could be the secret that people couldn't know . . . and somehow I could help out with.

"I can't have orgasms," she finally blurt out. "Well let me rephrase that. I've given myself one. But Mike has never been able to give me an orgasm. I was telling Ashley and she had mentioned to me that you might be able to help me. She told me a few things about you . . . and don't worry, I won't tell anyone. I could never tell anyone."

I smiled. "Why did Ashley think that I could help you?"

She looked nervous still. "I think her exact words were 'He knows his way around the female body'."

Laughing I said, "Well honestly I haven't failed yet. But it has a lot to do with you." I let that sink in. "What do you think about yourself?" I asked. "On a scale of one to ten, ten being the highest, what would you rate yourself?"

She thought for a moment. "I would say a six. Maybe a seven."

Amazed at her low opinion of herself I asked, "What do you think Mike would rate you?"

"I would say that he would rate me a seven as well." I think I knew what was going on here. I studied her beautiful curves a bit more.

"So what are the kinds of compliments that Mike gives you?" I asked.

"Well, sometimes he'll tell me that I'm hot. But usually it's when we are having sex," she answered.

"When I just saw you turn around at me fully nude and fully vulnerable, you looked as though you were very confident with yourself. I figured that you would think of yourself as a nine or a ten," I said. "I see a lot of women while I'm mowing lawns. I see a lot of them in their bikinis at their pools or lying out as you were. I can honestly say that you are at least a nine. You'd be a ten in my book if you laid out topless more often," I said with a huge smile on my face.

She smiled back. I could see some of her tension leaving and I could tell that she appreciated my complement.

"So why do you think that you can give yourself an orgasm but Mike can't?" I asked. "I'll tell you what. If you are asking me for help then let me do that . . . and do whatever I tell you," I demanded not waiting for her answer.

She looked at me as though I was going to do some funky crap to her. She reluctantly nodded.

"This will probably take more than one lesson," I said. I was confident that I would be able to make her cum today, but wanted this to last awhile. It probably didn't matter. I imagined that once she got some of this, she would be back for more anyway.

I told her, "I need you to lie back down and show me what you do to make yourself orgasm."

She raised her eyebrows. "That's very private. I'm not sure I'm comfortable with that."

"Do you want my help or not?" I was threatening to leave her be.

"You are getting a kick out of this aren't you? You just want to humiliate me," she responded.

Shaking my head, I reminded her that if she wanted my help, she would have to trust me.

Finally she laid back down on her chair. She started slowly touching herself. I could tell she was uncomfortable. Knowing that this was part of her problem, I told her to stop. "This isn't working. Let me think of something else."

I got behind her and started massaging her neck. "Lean forward a little so I can get you relaxed. I can tell that you are nervous and you shouldn't be." I said this as soothing to her as possible without sounding too gay. She finally started to relax after at least five minutes of rubbing her shoulders, neck and back.

Out of my own horniness, I reached over and felt her right tit. I cupped the lower part of her tit with my hand. I loved this spot. I moved my other hand from her shoulder to her left breast. Again I could tell her unease. I know she was not used to any hands other than her own and Mike's on those puppies. Her nipples started to harden up in the heat of the day.

"You have a beautiful body," I said.

She smiled as I continued to fondle her saline bags. Surprisingly, she started rubbing herself downstairs without me prompting her. "You are really turning me on," she said.

I bent over and gave her an upside down kiss. The kiss was fairly quick but she let her lips linger as I pulled away. I'm in charge here and it'll stay that way. I pushed her body forward so I could lower the backrest of the lawn chair to a flat position. I gently laid her back down on the chair.

I hopped on the chair next to her but laying my body opposite of hers. "I'm going to pleasure you with my tongue. You don't have to do anything with me if you want. I'm here to please you. I'm gonna lay on my back. Could you get up and then lay back down on top of me with your pussy by my mouth?" I asked.

She nodded knowing what position we were getting into. I started with one nice lick up and down her lower lips. Her hips shuddered when my tongue brushed over her clit. This was gonna be easier than I thought.

"Oh . . . oh. That's perfect . . . right there. Ooooohhh. Ooooohhh," she purred.

My dick hardened as she finally started to stroke me. I could tell that besides her years of being sexually active, the variety of her encounters didn't vary much.

I lifted my head long enough to breath. "So what position do you like the most?" I asked.

Breathing a little heavier now she asked jokingly, "Is there more than one? We usually do missionary."

I laughed and continued on giving her damp pussy a good licking. My tongue was getting a little tired by now. "You are so frickin hot," I said as she continued to moan softly. I reached my hand between her legs and rested it on her ass. I started rubbing her asshole with my thumb.

"That's off limits," she protested.

"Who's helping who here?" I asked. "Do I have to remind you again to trust me?" I needed to maintain control. I lowered my hand and fingered her pussy some more. I could tell I was making headway.

I pushed her up telling her that we were going to try something else. We both got off of the lawn chair and I gestured to the house. "Let's go in." We picked up our clothes and started toward the house.

She opened up the sliding glass door. I could feel the cold from the air conditioner try to escape. "Let's go take a shower," I suggested. I remembered how Mike always bragged about how he could fit a football team inside his shower.

She led me to the bathroom. I was watching her super fine ass shake just the tiniest bit as she walked. My dick stayed rock solid as we made our way through the hall. We made it into the bathroom and walked into the shower.

"Why didn't we finish outside? I'm not used to different positions in different places all at one time," she said as she turned on the faucets. "Besides you were getting me worked up."

I looked at the shower. Though I don't think an entire football team could fit, it was a mighty large walk-in shower with large tiles lining the sides and water coming out of the four silver showerheads, which were placed in various spots on the wall. I figured that I would look into getting one of these soon. After all, I needed something to spice up my sex life. I laughed at that thought.

We both got in and I grabbed a spongy thing from the shower shelf and started rubbing it over Jessica's tits and stomach. She was beautiful indeed. I started to kiss her like she was the only one I've ever kissed. She wasn't a bad kisser either. As we were making out, I felt her hand on my cock. She started stroking it back and forth. That was appreciated and I showed her that by working my fingers back into her pussy zeroing in on her swollen clit. Her body trembled as I found her sweet spot. This went on for a few minutes before I sat down on the built-in step, which came off of the side of the shower. I turned her body so her back was facing me. I had her sit down slowly and I gently guided my dick into her wanting pussy. She moaned loudly.

"I love your big cock . . . and I love how you keep it trimmed," she moaned.

I pushed her up until her lower lips were surrounding my mushroom tip before I pulled her back down. This went on for a little while and I was surprised that she didn't appear to be cumming in the foreseeable future. I loved reaching around and grabbing onto her saline sacks. For some reason I didn't care that they weren't real. They were tits and still enjoyable and almost lifelike. They made for good handles as we started increasing our speed.

"Mike would have cum already if this was him," she blurt out between moans. "He's given up on me. He would just cum and then get off me not even waiting for me to try." I could hear her breathing getting louder so I wished she would just shut up. But maybe she needed to focus on something other than her orgasm.

"Oh . . . oh. That's perfect . . . right there. Ooooohhh. Ooooohhh," she blurted.

After a few more minutes she was finally getting closer. It was now obvious that her orgasm was just around the corner. I continued to thrust my hips into her body until it was almost too late. I pushed her up. "What the hell are you doing?" she asked. "I could feel it. I was almost there."

Obviously I knew that but I wanted fireworks. I wanted to give her those fireworks and letting her cum now was only going to be a cheap bottle rocket.

I laid down on the bottom of the shower with my head opposite the four shower heads. "Hop on," I said as I motioned her.

She hovered over me grabbing my throbbing hard on. She knelt down with her knees facing upwards and laying back as her lips surrounding my cock. "Not like that. Move toward me so your tits are in my face. Rest your knees on the shower floor," I insisted.

The water was pounding her back as she bobbed up and down. This was great. This was going to be multiple years of pent up anxiety coming out all at once.

"This is a great position!" she exclaimed. "I can feel more this way . . . or maybe it's just your big cock," she laughed. "Aaaaahhhh . . .! That feels so good."

I reached both arms around her and grasped her ass. My hands went up and down with her body and she started moving faster and faster. I took my right hand, which was soaking wet from the shower and reached my middle finger to where I thought her asshole was. As she continued up and down I managed to slip a digit inside her ass. She groaned as it entered her but she didn't protest this time. This was getting her even hotter.

I continued to let her body come down hard on my cock and her ass on my middle finger. The position wasn't the best for getting more than the one digit in there but it was doing the job for her. She thrashed up and down. The shower echoed with her screams. I was close to cumming inside her but had the strength to hold off a little longer. I didn't want to do what her husband always did which was cum and be done. That wasn't my style. Besides, she trusted me to bring her to climax and that was happening right now.

"Oh, oh!" she yelled. "Harder, harder." I thrust up as hard as I could as she was coming down.

"Oh yeah. Oh Yeah." she kept yelling. "Fuck me, fuck me!" Her saline sacks were bouncing up and down in a circular motion.

I moved both hands back to her hips and helped her up and down. "Fuck me . . . fuck me . . . fuck me! Oh yeah oh yeah." This girl was a wild one.

I looked up and as she opened her eyes to look down, I could see a glimmer in her eyes that she probably isn't used to having. She was ready to cum and cum hard.

She closed her eyes again. Still moaning she started riding me harder. She could ride a wild bull for longer than eight seconds. I was sure of that. "Awwwww. Keep fucking me. Oh . . . oh . . . oh. Oh fuck; this is hot! I'm going to cum."

Just then her body started to spasm and she let out a loud scream. She continued to scream and moan as she thrashed back and forth on my cock. I pictured the Fourth of July fireworks in our city that happen every year. I thrust harder and shot my warm liquid as far up her cunt as I could. She kept going. I think she was climaxing again. She screamed and screamed until finally she let out a huge sigh and laid down on me pushing her big tits into my chest.