December 6, 2023
Crazy Lenny: Adventure with Best Lesson Teacher, Mrs. Chika (Part 1) [18+] (Legend Series)


Home » Crazy Lenny: Adventure with Best Lesson Teacher, Mrs. Chika (Part 1) [18+] (Legend Series)

Crazy Lenny: Adventure with Best Lesson Teacher, Mrs. Chika (Part 1) [18+] (Legend Series)

I smiled as the bell rang. The final bell on Friday always sounded so much better than any of the other bells during the week. I happily gathered up my stuff and arranged my school bag as I started looking forward to the upcoming weekend.

I was nearing the end of my senior year in secondary school and, having turned 18 a few months ago, I knew that I would have a weekend of freedom as my parents would be leaving town. Actually, they had been making it a near habit for nearly the past year to go to the family’s vacation whenever the weather was nice. 

They had stopped asking me if I wanted to go and I figured they enjoyed the time alone as much as I enjoyed having the house alone.

I organized my desk and grabbed the stuff that I would need to take home with me. As I did most days when I didn’t have lessons after school I headed toward Mrs. Chika’s room. Mrs. Chika had been my English teacher back when I was in junior class and had offered to tutor me after school when she noticed I was having a tough time in class. 

I went to her office nearly every day after school for almost a whole session and she would help me get through my work. Eventually, I straightened out my problems with English, but I still made it a habit to stop by Mrs. Chika’s room whenever I could through the rest of my years at the school.

I headed up the stairs to her office and started to plan out my weekend. A typical weekend would consist of going on a date or just going out flexing with some friends. I knew that having the house to me was a treat and I never abused that by having a big party. 

This weekend was a little different in that all my friends were otherwise occupied and I couldn’t get any dates lined up, so it looked like I would have a lot of time to myself. I thought that perhaps a porno or two would release some of the sexual energy that I seemed to constantly have bottled up inside me.

Sometimes I would wonder why I continued seeing Mrs. Chika regularly even through my senior year. We no longer even talked about my schoolwork and sometimes would just chat or she would have me help mark some papers. 

The truth was that I always felt grateful to her for helping me out back then and I wanted to somehow make it up to her. We had become pretty good friends through the years and she seemed to really enjoy my visits, so I didn’t feel weird about continuing to stop by. The fact that I had carried a crush on Mrs. Chika all these years didn’t hurt either.

I never asked but I guessed she was probably between 35 and 40 years old. She carried herself with an elegance that had always appealed to me. Her hair was short but always very elegant and always perfectly done. 

Mrs. Chika always dressed very properly which meant that she always wore skirts & high heels. I found that her style of dress was particularly appealing. Perhaps it was the fact that she never showed too much leg or too much of her boobs that made me desire what was underneath all the more. When I first starting seeing her for lessons I found it difficult to concentrate on the lessons instead of staring at her breasts. 

They were large but definitely not too large for her frame. “Just more than a handful” was the term that my friends and I had once jokingly used when we were discussing some of the more lustful things we wouldn’t have minded doing with their teacher. Through time I thought I had gotten pretty good at sneaking looks at her shapely ass or the perfect outline of her breasts encased in those teasing tops.

I entered Mrs. Chika’s room and found her busy at her desk arranging some new items for her class. I said hello and asked if I could help. Mrs. Chika replied that I could go get her a drink from the staff canteen and then if I had time, I could help her put up the new notice on the board. “Sure thing,” I replied since I knew I didn’t have any other plans for the afternoon.

When I returned with the drink, I found her standing on her tiptoes trying to figure out where she wanted to arrange the new items. Since I was a little taller than she was, she asked me if I wouldn’t mind doing that for her. She described how she wanted it to look and then left me to my work. Mrs. Chika returned to her desk to finish marking some papers.

After a short while, she looked up and saw that I had nearly finished. She picked up her drink and walked up behind me to compliment me on a job well done. She was standing right behind me when she said, “Looks good.”

For some reason, I had lost focus and was going about my work while daydreaming about what sort of porno I should watch later. Mrs. Chika’s words surprised me and caused me to jump and spin around suddenly. 

As I spun my elbow knocked into her drink and spilled the content all over the front of her top. I started apologizing profusely and grabbed a nearby roll of paper towels. I tore off several sheets and started to quickly try to clean up some of the stains from her top before any more of it soaked into the material.

I repeatedly apologized and although Mrs. Chika kept telling me it was fine and that she was just as much to blame for sneaking up on me it didn’t help me. I was very embarrassed at spilling the coffee and could only think about trying to clean off her shirt. 

Mrs. Chika kept telling me to stop and it wasn’t a big deal, but I wasn’t listening because I was too busy trying to apologize. She finally leaned over to set down her cup just as I was leaning over to grab more paper towels with one hand while still trying to wipe her off with the other hand.

I wasn’t sure exactly how it happened, but somehow through both of our movements, my hand was now rubbing Mrs. Chika directly on her right breast. I had been rubbing in small circles and had actually been rubbing her breast for a few seconds before I realized it. 

When I did notice I completely froze not knowing what to do. We both stood completely still for a couple of seconds with my hand still covering her breast. I finally came to my senses and quickly removed my hand with a hurried apology, but not before I felt the biggest charge of sexual energy I had ever felt. 

My dick shuddered in my trousers as I quickly realized I had really groped Mrs. Chika’s breast.

I looked up to see what Mrs. Chika was doing. As we made eye contact for the first time since the touch I noticed that she wasn’t angry at all. Instead, the look on her face was mostly blank but there was a slight twinkle in her eye that helped stiffen my growing erection. “I should probably be going,” I started to say. I was quickly cut off by Mrs. Chika saying, “I don’t think I can let you leave yet. You still have some cleaning up to do.”

That last sentence hung in the air as I tried to figure out exactly what she meant. Mrs. Chika finally broke our eye contact and made a quick glance down to the front of her shirt. 

Still not quite sure what she wanted, I grabbed some tissue paper and again started rubbing the front of her shirt. I started up by her shoulder and then moved down to her stomach skipping over her breasts. 

The sexual energy building in me was ready to boil over and I now had a full erection. I didn’t have much experience at reading these types of situations, but I was pretty sure Mrs. Chika was also enjoying the “cleaning”. I again started rubbing her shoulder but this time allowed my fingers to drop a little lower. 

“What the hell am I doing?” I thought to myself. As I tried to answer the question, I allowed my fingers to drop yet still lower. Mrs. Chika made no moves to stop me and I decided it was time to see how far she would let me go. I moved my hand down until I was now rubbing the top of her breast.

I held my breath and was already working on what I would say when she asked what the hell I was doing. She never asked. I rubbed the top side of her breast for a while and then allowed my hands to slide completely over her breast. 

I also brought my other hand up from my side and cupped her other breast with it. Mrs. Chika had closed her eyes and tipped her head back slightly, so I assumed that she had no intention of stopping me.

As I rubbed and caressed her breasts, I couldn’t believe how amazingly sexy they felt under her top. I could feel her nipples begin to stiffen and occasionally my fingers make small circles around them. 

Soon her nipples were standing very erect and were quite prominently sticking out from her breasts. 

Mrs. Chika’s breathing had become a little irregular and her lips were now slightly parted. Her breasts were very soft under my fingers and as I slid my fingers gently over her breasts I quickly wondered what they would feel like naked.

Before I could think about that any longer, Mrs. Chika opened her eyes and looked me directly in the face. She slowly moved toward me and pushed me back against the wall as her lips made their first contact with mine. 

The kiss started softly with our lips dancing lightly against each other, but soon she pressed into me harder and the embrace became less passionate and more lustful. She parted her lips slightly and started exploring my lips with her tongue. 

She then shoved her tongue into my mouth and started to roughly wrestle her tongue against mine. I was also aware of her hands slowly sliding up and down the sides of my hips and the charge I felt from her touch was almost enough to make me cum.

Mrs. Chika broke the kiss and sat down at the nearest desk facing me. She looped a finger under my belt and pulled me toward her until I was standing directly in front of her. 

Her hands returned to my hips and she again started rubbing my hips and then my thighs in slow up and down motions. Just as I thought I couldn’t take any more teasing, one of her hands slowly found its way to the throbbing bulge in my trouser. She slowly and softly explored my erection through my jeans before finally reaching up to undo my belt. She next unfastened the button on my trouser and very slowly unzipped the zipper. 

She pushed the trousers down around my ankles and I now stood in front of her with only my boxer shorts keeping my dick from pointing straight at her. She repeated her slow massage of my now exposed thighs and was allowing her fingers to slide higher and higher under my boxers until she was nearly making contact with my balls.

I couldn’t believe how hard I had become and didn’t know how long I could last. I noticed a wet spot on my boxers was I had already released some pre-cum in preparation for whatever was about to happen. Mrs. Chika also noticed the wet spot and began to rub her thumb over the wet spot until it grew much larger. Finally, I had to say, “I don’t think I can take much more.”

Mrs. Chika gave a devilish smile when I said that and replied, “I better put you out of your misery then.” With that, she grabbed the waistband of my boxers and pushed them to the floor with one smooth motion. 

My dick popped out of my boxers and stood straight out from my body pointing directly at Mrs. Chika. He could see it bent slightly. Mrs. Chika took a couple of seconds to simply stare at my dick as it danced in front of her. 

She finally reached up with her right hand and started to massage the area just at the base of my dick. She let my pubic hair run through her fingers as she rubbed the entire area around my shaft. Finally, she wrapped her fingers around the base of my cock. 

Her grip was very gentle at first as she just held my dick in her hand. She tightened her grip slightly and started stroking.

I was in heaven. I couldn’t believe how good this felt. Mrs. Chika started stroking faster with her right hand and reached up to cup my balls with her left hand. 

She finally whispered, 

“Cum for me Lenny. I want to watch you cum.” Hearing her say those words was more than I could take. Just at that moment, she started stroking me even harder and I moaned loudly as I started to cum. 

Mrs. Chika had shifted so my dick was pointed directly at her breasts but my first shot of cum was so forceful that it ended up landing near her shoulder. Stream after stream of cum erupted from my dick as she continued to stroke me. 

The entire front of Mrs. Chika’s top was now covered with my cum. Large drops of cum were sticking to her breasts and began to slowly drip down toward her stomach.

Mrs. Chika continued to rub and stroke my cock as it softened. She finally collected the cum that was still hanging from the tip of my dick with her fingers and quickly licked it from her fingers. She sat back slightly and looked at me as she spread her legs slightly and pulled her skirt up to her waist. 


She didn’t need to say anything as her body language clearly said it was her turn and I didn’t waste any time getting to work.

I quickly dropped to my knees between Mrs. Chika’s spread legs. I reached one hand out to each of Mrs. Chika’s knees and gently began to massage her thighs just above her knees. The feel of her firm but soft flesh really turned me on. 

I slowly allowed my massage to progress further up her thighs and began paying more attention to the insides of her legs.

As my massage continued I noticed how wet the crotch of Mrs. Chika’s panties had become. The smell also struck me. Mrs. Chika’s strong, musky scent had my head spinning and made my dick start to tingle again. 

My massage had now reached the very tops of Mrs. Chika’s thighs and I had started to allow my fingers to pass over her pussy. I couldn’t feel much through her panties, but I could feel her wetness. 

Without saying anything Mrs. Chika took my hands and guided them to the waistband of her panties and it slipped down to her ankles.

I looked again between Mrs. Chika’s legs and saw the pussy I so often fantasized about for the first time. Her pussy was very hairy and not like anything I had seen in magazines or on videos. Her pussy lips were swollen and covered in her own moisture. 

I could see the wetness glistening from her vagina and without thinking moved my hands up to feel the wetness. I slowly ran my fingers through the hairs on her pussy. I cupped her pussy with my right hand and felt her juices run over my palm and fingers. 

As I explored her pussy Mrs. Chika started to slowly rotate her hips. Occasionally I would look up at her face and found that Mrs. Chika was alternating between watching me and leaning her head back and enjoying the sensations.

Finally, I decided I needed to feel inside her pussy and placed a finger at the entrance to her vagina. I slowly started to insert my finger when Mrs. Chika rocked her hips forward and pushed herself completely on my finger. 

It was wonderfully wet and warm and I quickly inserted a second and then a third finger. I wasn’t sure exactly what to do so I slowly started to move my fingers in and out. 

With my other hand, I began exploring the area just above her vagina where I knew the clit was located. 

As I slowly finger fucked her I gently massaged her pussy with my other hand and paid particular attention to any areas that seemed to get a reaction from Mrs. Chika.

Mrs. Chika had begun rocking her hips more and more and was taking a more active role in the finger fucking. Suddenly she whispered, 

“Oh Lenny, that’s the spot. Keep your hand right there.” Hearing the lustiness of her voice at this moment completely turned me on. I had heard her voice many thousands of times over the past few years, but it had never sounded like that. I concentrated my massage on that small area and really began to watch Mrs. Chika’s reaction.

Very quickly Mrs. Chika again spoke, this time with more urgency in her voice, “Fuck me faster, Lenny.” I did as commanded and greatly increased the speed of my finger fucking. 

At this point, my whole hand was covered with her pussy juice. I felt Mrs. Chika’s pussy clench around her fingers and her body suddenly tightened. Through clenched teeth, she cried, 

“Ohhhh yes.” Her pussy spasmed around my fingers and I knew that she was cumming. I continued to finger fuck her as she came and then slowed the fucking as she regained her composure.

The room was silent for a few moments except for the sound of Mrs. Chika’s heavy breathing as she tried to regain her breath. She reached down and took hold of my hand around my wrist and removed it from her pussy. 

She slowly brought my hand up to my mouth and said softly, 

“Taste it. Taste me.” I did as instructed, slowly and anxiously at first, but then with more enthusiasm as I realized that I enjoyed the taste. Mrs. Chika moaned as she watched me clean off my hand. 

When I finished she released my hand and stood up. She stepped out of her panties and pulled her skirt down. She picked up her underwear and walked over to her desk. I was still kneeling on the floor with my own pants and boxers around his ankles. 

My dick was semi-rigid at this point as I watched Mrs. Chika. She stood at her desk with her back to me for a few seconds and then said, “I think you should go.”

I didn’t know what I expected her to say, but that wasn’t it. I mumbled a quick, “OK.” I stood and quickly got dressed. 

Mrs. Chika walked around behind her desk and sat in her chair. I thought I noticed her quickly glancing at me, but every time I looked at her she would look away. I gathered my school bag and book, with one last look back at Mrs. Chika, I left her office.

As I walked toward home, my head was spinning. I couldn’t believe the encounter I just had, but I was also confused at the way it had ended. I had expected a good-bye kiss or something but instead, I had been dismissed. 

Had Mrs. Chika played me and used me as a sexual ragdoll to get herself off, or had the whole thing been a wonderful spontaneous moment? I spent the whole rest of the weekend either trying to figure out what to do next with Mrs. Chika or masturbating to my memories of Friday. 

A couple of times I decided to call her, but I would be fearful. What if her husband answered the phone? What would I say? I ultimately decided that as much as I wanted to I would have to wait for Mrs. Chika to make the next move.

I walked to school on Monday scared of what might happen. How should I react if I passed Mrs. Chika in the corridor? Wouldn’t everyone see something was going on by my body’s reaction to her? I got to school and quietly went through the day. 

I was handed the note just before my last class. It read simply, “Mrs. Chika has requested you come to her office immediately after school today.” It was signed by the vice-principal. 

The last class of the day was a waste as I couldn’t stop thinking about what was going to happen after school that day. The last bell rang and I went directly to Mrs. Chika’s office.

I entered her office and shut the door behind me to try and give ourselves privacy. She immediately apologized to me for how she ended things on Friday and that helped put me at ease. She continued, “I did a lot of thinking over the weekend and had initially decided that we should end our lesson sessions. 

However, upon further thought, I realized that since you will be starting university soon perhaps it would be best to change the focus of our lesson sessions to best prepare you for the challenges that you will face there. 

Many freshers in the university are overwhelmed by university life and the lectures and cannot handle it. I know that you are very intelligent and will probably have no problems, but I would feel better if you allow me to try to get you as prepared as I can for university. What do you think?”

As I listened I tried to understand exactly what she was saying. Since I entered her office she hadn’t said anything about our encounter that would seem weird if overheard by someone else. 

Her question about lessons also would not sound odd to an outsider, however, I was particularly interested in the way she emphasized certain phrases and couldn’t help but think that the entire question was a coded way of asking me if I wanted to continue our newly established sexual relationship. 

I thought about my answer and said, 

“I think that sounds great. I appreciate the extra effort that you are offering to put into our lesson sessions.” As I said that Mrs. Chika smiled seductively at me and I was sure that I hadn’t misread the situation. I continued, “When do you think we should begin?”

She told me that we shouldn’t continue our sessions in a secondary school setting because she wanted to get me in a university frame of mind. I agreed and we decided to meet Friday evening after school and that she would take me on a quick tour of a nearby university campus. 

We parted with a simple handshake but we both were looking forward to the “lesson” arrangement held.


The week seemed to drag. Hours seemed like days. Finally, Friday arrived and when the bell rang, I almost ran up to Mrs. Chika’s office. She greeted me very professionally and asked if I was ready. I could barely contain my excitement as I said yes and we headed out to her car. 

As she drove me to the university she began to tell me about how most students fail at university not because of the lectures but because of the new lifestyle and freedom, both sexual and otherwise. 

She said her goal was to try and expose me to as many aspects of the campus lifestyle as possible so I wouldn’t be surprised or be tempted to skip my studies when I got to university. 

As she was saying this she pulled into one of the parking lots at the campus and got out of the car. For the next hour, she showed me around campus and gave me many important pieces of information about what to do when I arrived at university.

When we returned to her car, I thought I noticed her mood change slightly. She began talking again about campus life and how she felt it was particularly the sexual freedom of it that caused the most problems for freshers who were unprepared. 

I explained that teens that have lived under mom and dad’s roof are suddenly totally free and able to date and/or fuck as much as they want. I wasn’t sure where she was going with this, but I was very aroused to hear her talking so openly about sex. She asked if I understood and I said, “I think so.”

“Good,” she replied. “Now it was my understanding from last week that you haven’t had much experience sexually with women. Is that correct?”

I nodded.

“See, I think that could be a problem for you next year. There are going to be a lot of women out to get into as many guys’ trouser as possible and someone with no experience can get overwhelmed and lose their way.”

I asked, “So, what can we do about that?” I knew it sounded tacky, but I had to know where Mrs. Chika was heading with this.

She looked directly into my eyes and said, “I think that in the time we have left I want to give you as much experience as I can.” I nearly came in my trouser when she said that to me. 

The woman who had been the object of many of my fantasies had just said that she wanted to fuck me as many times as I could before I leave for university.

I weakly replied, “That sounds great.” she laughed at the complete lameness of my reply and pulled out of the parking lot. She headed the car to a deserted area. She parked the car inside the bush and told me to get in the backseat.

As she climbed in the backseat she leaned over and started to lick my ear. She gently flicked my lobe with her tongue and ran her tongue along all the folds of my ear. I moaned at this unexpected advance. 

She kept this up for a brief time and then moved her lips very close to my ear and whispered very softly, “It’s time for your first lesson.”

With that, she leaned over my lap and started to unbuckle my trouser. I helped and quickly we had removed my trouser and boxers so that I was naked from the waist down. 

She again bent over my lap and started kissing and licking my thighs. With a slight shift in her position, her head was positioned at the end of my hard dick. Just before she bent down to take me into her mouth she made eye contact with me and said, 

“Don’t worry about cumming. Just let yourself go and enjoy what I am doing to you.”

As soon as she finished speaking she parted her lips slowly and wrapped them around the very tip of my dick. She tickled the tip briefly with her tongue and could already taste my pre-cum. She removed her mouth and moved her head underneath my dick. 

She began to gently kiss and lick the underside of my dick from the tip to my balls. She tried to continue this treatment to my balls but couldn’t get to them properly from her position so she returned to the tip. 

Without wrapping her lips around me, she licked the tip of my dick with her tongue. She licked the tip for a while and paid particular attention to the tender spot directly under the tip. 

When she felt I had had enough of this treatment she again parted her lips and lowered her head onto my dick. 

This time she didn’t just stop at the tip, she took several inches of my dick into her mouth. 

She started to bob her head up and down; she gave me a proper blow job. As she started her lips would barely touch my shaft so all I felt was the lightest of touches and the warmth of her mouth. 

She gradually increased the tightness of her mouth and the pace with which she bobbed her head.

I couldn’t believe how amazing Mrs. Chika’s mouth felt. I had to work hard to not cum all over her tongue when she was licking the tip of my dick, but this was too much to stand. I desperately wanted to open my eyes and watch Mrs. Chika’s work, but I was so close to the edge that I knew the sight of her would be too much to take. 

I could feel her increasing the pressure on me with her lips and I could only throw back my head and moan. I wanted it to last forever but I felt my balls tighten and I knew I was about to cum. With a loud groan, I started cumming into Mrs. Chika’s mouth. 

I opened my eyes to see what she would do and I saw her quickly move her mouth so only the tip of my dick remained in her warm mouth. She was holding my dick very firmly now between her lips and quickly wrapped her hand around the base of my dick. 

Mrs. Chika began quickly pumping her hand up and down along my shaft. My dick was coated in her saliva so her hand glided smoothly as she pumped. I shot load after load into her mouth. After the first couple of jets, I noticed that Mrs. Chika opened her mouth slightly and was letting some of my cum dribbles from her mouth back down onto my dick. 

Her pumping hand quickly smeared the cum along the length of my dick until it was entirely coated with the sticky combination of my cum and her spit. I thought I was going to cum forever but eventually, my ripples subsided.

Mrs. Chika slowly removed her mouth from my dick and raised her head to look me in the eyes. We stared into each other’s eyes for a few moments and Mrs. Chika very slowly and deliberately swallowed the cum that remained in her mouth. She then very suggestively licked the cum off her lips and cheeks that had been smeared there. She then took the hand that had been wrapped around my dick and brought it up to my lips. 

Her hand was covered with my cum and at first, I pulled back. Mrs. Chika raised an eyebrow and said, “Now Lenny, for this to continue I need to have a willing student.”

I leaned forward and took the tip of one of her fingers into my mouth. I was hesitant at first but I quickly got into my work and soon had completely licked her hand clean. 

I wasn’t sure I enjoyed tasting my cum, but I was in no position to argue with Mrs. Chika.

Not long after I had cleaned her hand Mrs. Chika said, 

“OK, that is your lesson for today. Your next lesson will be in one week at my house. I have written the address and other details on this paper. Your homework for our next session is that you must not jerk off between now and then. Do you understand?”

I quickly agreed and started putting my trousers back on. Mrs. Chika drove me to my neighborhood but dropped me off several meters from my house so my neighbors wouldn’t see her. 

As she stopped the car I didn’t know what to say so I only said, “Thanks, Mrs. Chika.”

She laughed out loud at my formality and replied, “I think that, as long as we are away from school, you can call me Chika.” 

With that, she quickly grabbed my crotch and told me she had to go. I stepped out of the car and finished my walk home hoping nobody would notice the huge bulge in my trouser.

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