tagFirst TimePleasing Mrs. Jones

Pleasing Mrs. Jones


This story was inspired by the book "THE CLUB: How I met the love of my life in a sex club."

It includes bisexual male-male, male-female, and female-female activities. It also includes light pain, bondage, and mild force. All the activities are completely consensual, but consensual non-consent is discussed.

Edited by the 'Erotic Confectioners.' Many thanks to yourMasterBaiter, Jasmine27, fewella, and Luxx.

yourMasterBaiter put many hours in helping me with this.. just want to thank him for his time and effort.



It was your average Saturday. I was playing some b-ball at the park with the guys. Being a senior and having turned 18 a month ago, it seemed like all the punks I'd dunked on before where trying to get their shots in before the end of school and my leaving for college. Let's just say it didn't end very well. One black eye and several bruises later I headed home sporting a somewhat swollen, sweaty, and dirt smudged face.

I was still panting heavily as I crossed the main foyer in my building when I saw Mrs. Jones getting in the elevator. I normally take the stairs, but today was definitely not a stairs day.

"Hold the door, please!" I said as I rushed in.

The smell of her perfume awoke that lower part of my brain that turns on when I'm around any women. In my current state, it was more animal than usual. My arm brushed against hers as I leaned in to push the button for my floor. Her skin was so amazingly soft. So tender and yielding against my muscle. The sudden thought of fucking her in the confined elevator combined with the lighting made me slightly dizzy.

"How are you Mrs. Jones," I said as I glanced at her perky breasts. She noticed me looking and pulled her sweater tighter together. She wore black dress pants and turquoise top that hugged her tits nicely.

"Did you get in a fight or something?" she asked.

"Actually, it was a foul...You should see the other guy." I said, half-jokingly. Mrs. Jones is my school principal, so I was not sure I should have been admitting I was fighting to her. It wasn't like I was fighting at school.

As the elevator stopped Mrs. Jones stopped me from exiting.

"Brent, I have a few things that I need moved around. Would you mind stopping by later this evening?"

"Sure! How about six?" I asked

"Sounds good. 32C" she said.

"Excuse me?" Shit, did she just tell me her bra size?

"My apartment is 32C.," she said, with a crooked smile.

"Oh, right. Well, I'll see you at sex... I mean six!" I said quickly while the door was shutting. I could hear her laugh as the door closed.

I showered and decided to chill out and play the Xbox to pass some time. I grabbed a bag of peas from the freezer and placed it on the nice shiner I was now sporting. Before I knew it, six o'clock was here. I really wasn't looking forward to this. I just wanted to chill, not hang out with anyone from school, let alone the fucking principal. Being the nice guy that I am, I had a hard time saying no, especially to a lady.

I took the stairs this time, only heading down one flight. I made my way to 32C, thinking Mrs. Jones had to be a D cup at least.

She opened the door on my 3rd knock, and holy shit, Mrs. Jones looked a hell of a lot different outside of her business like school-clothes! She sure had one hell of a figure, for an older woman. She wore a tight green sweater that showed off her cleavage and jeans that hugged her hips.

Her red hair was pulled up into a messy bun, her eyes a beautiful shade of green, which seemed to be looking right through me.

'Damn, she is sexy.' I thought.

"The dresser is right in here," she gestured with her hand as she spoke. Her apartment was immaculate. Not one single thing was out of place. I guess you could expect that from a principal.

I followed behind her, unable to take my eyes off those swaying hips and perfect round ass.

She led me right through into her bedroom where she had a few things packed in boxes, neatly lined up on the wall. It smelled like heaven in there, soft and sweet, like a girls perfume and hair on a summer day. Her bed was a big wooden four poster. The wood was dark, and had a soft white comforter on top. I was so distracted by the smell and thinking about her bed that I barely noticed when she spoke.

"These boxes are going to the school for the annual yard sale. And I would like this dresser moved over to that wall." She turned and looked at the opposite wall.

The dresser was solid oak, which matched the king sized bed. Then it hit me; I was in a woman's bedroom and she slept in that bed. Images flashed through my mind of her in a nighty, quickly followed by me bending her over the bed. 'Damn, guy get it together. This is your principal, not some random hoe.'

I quickly moved around to the other side of the dresser, hoping it would hide my growing boner. A few deep breaths and some math tables in my head and I hoped it would go away.

"You grab that side and I'll grab this side and we will move it together." She said as she took hold of the end. On three, we both picked it up and moved it; surprisingly, with ease. She was a hell of a lot stronger than she looked. She was petite, and thin, but her arm muscles flexed as she picked up the dresser, seemingly without much effort.

"Do you need help with those boxes?" I asked, trying to find a reason to be around her longer.

"No, I will get those later." She said. "How old are you Brent?" Her voice was different.

"Eighteen as of last month Ma'am."

Then she did the most shocking thing ever. She looked me in the eye and smiled before walking over and placing her hand on my crotch. This caught me off guard, and I jumped back in shock.

"Stop flinching. I know you want this." She said with a smile. And then she took a step back and said, "I saw you looking at my tits earlier." Suddenly she pulled her top over her head letting her breasts spring free. They were perfect; large and bouncy with big nipples. She grinned at the look on my face and pushed her breasts together.

With one hand on her breast, she leaned closer and started rubbing my cock through my jeans. It was growing hard again. So much that my jeans were now tight and uncomfortable. I was not sure what was going on or what to say or do. I stood there in shock and just enjoyed her hand stroking me.

I wasn't completely clueless about sex. I'd spent plenty of hours jacking off to porn. However, at that point, I was still a virgin. Not that I didn't have opportunities to have sex. I just wasn't into all the high school drama with girls my age. One kiss and they were planning marriage. Plus my main focus was on my photography.

Mrs. Jones lead me to a chair that was set in the corner of the room. My brain was still trying to catch up to my aching cock. Before I sat she unzipped my pants. In one swift move, she had my pants and briefs down to my knees, freeing my throbbing cock from its restraints.

"Look at that massive cock," she said with wide eyes, right before she took me in her mouth. She licked my shaft down to the bottom and back, then circled her tongue around my tip. She brought her mouth over and took off sucking at a good speed. As she massaged her tongue against my shaft, her hand reached down, and she began fondling my tight balls. She was in complete charge of my body as this was all so foreign to me.

It took everything in me not to thrust my hips and blow my load in her mouth. She began sucking harder, and faster and I couldn't take it. Should I come? Girls don't like it when you come in their mouths right?

"Stop!" I yelled.

"Why did you stop me?" She asked with concern on her face.

"I didn't want to come in your mouth," I said feeling really nervous now. The look on her face changed, and I could see the question forming before she even asked it.

"Brent, how many girls have you been with?" I thought about lying. I was certain she would stop what she was doing if I told her the truth.

"None" I spat the words out before I could change my mind. It was more like I moaned the words out. She just smiled and continued sucking my dick. I was still trying not to blow my load.

"Damn, that feels so fucking good." I desperately didn't want her to stop; I threw my head back and moaned loudly as she pumped my cock in her hand.

"Relax and come for me." She said as she put her mouth back on my cock. It took only a few more seconds before I shot my load down the back of her throat. As she started to get up, she saw a string of cum on my dick. She bent back down and licked it off.

"I think I have a lot of teaching to do here. The first lesson will be oral. You will learn how to properly eat pussy." Her naughty words were making me excited, but she stopped me by saying, "You've been here long enough to raise concern with your parents. Go home and come over again when you are ready for that lesson."

Later that night I laid in my bed with thoughts of my first blowjob. Who would have thought it would be with Mrs. Jones? I couldn't stop the memories flooding my mind. Her thick full lips around my hard dick. Her head bobbing up and down, and those wide green eyes looking up at me.

I couldn't take it. I had to get off again. I took a hold of my cock and began stroking. It didn't take long before I was coming hard and fast.

I was satisfied for a little while, but I was still restless and images of Mrs. Jones just kept coming up in my mind.

It was almost midnight when I decided to make my way back to her apartment. I figured it was late, and no one would be in the halls to see me. I threw on sweats and t-shirts. I closed the door as quietly as possible not wanting to wake my parents. I darted to the stairs just in case someone was up in the middle of the night. Luckily, no one saw me as I knocked on the door.

She opened the door on the third knock. Before I could lose my courage I walked in, shut the door and pushed her against the wall. I began kissing her with everything I had. I wanted her to know how bad I wanted her.

I was ready for lesson two.

"Fuck, I'm glad you are here." She said. "I kept thinking about your cock and how bad I wanted your tongue licking my pussy."

My dick was fully hard again poking her in the stomach.

"Come over here," she said leading me to the couch. She pulled her silk nightgown over her head and tossed it to the floor. I was surprised to see her without panties and really blown away when I noticed her cunt was totally bald.

She sat on the couch and opened her legs. She was already soaking wet and glistening. I sat down in front of her. Holy shit! I was inches from a real pussy!

"Brent, I want you to start slow and watch my body for signals. When you get to my clit put pressure on it and don't just flick your tongue. Swirl your tongue over and back and forth. I'll show you what to do."

She slid one finger down her center, and down each fold. Her fingers circled her clit, up and back down. She moved back to the top and started rubbing her clit. Her fingers moved up barely an inch, and then she began moving her fingers faster.

"It's your turn," she said as she brought her wet fingers to her mouth and sucked her juices off her hand.

I was so nervous I couldn't keep my hands from shaking. What if I messed up, and she didn't like it? What if I didn't like the taste?

I got to my knees and brought my tongue to her slick, juicy pussy. One light stroke up her center, and back down each side of her lips. She let out a small whimper, and I began to lick and suck her clit. She tasted so weird! Not like anything I'd ever had in my mouth before. Sort of like sushi crossed with ham and a little ocean water. I can't describe it.

I flicked my tongue a couple of times over the sensitive nub. She backed away, but I put more pressure on her clit. She grew wetter and wetter as my tongue brought her pleasure. Taking a chance, I did what I'd seen guys do in porn and slipped one finger up inside her. She moaned, so I guess I did it right.

Her hands were on her breasts and I couldn't help but notice how she rubbed each one. Coming down from the top and then pinching the nipple. I continued licking and sucking as fast as I could. I now had two fingers in her, pumping in and out.

She put her hand in my hair and buried my face in her pussy. This made her wild, and she began bucking her hips.

"I'm going to" Her words were cut off as her orgasm ran through her. Her pussy tightened around my fingers, and it felt like she was convulsing.

I pulled my fingers out after the pulsating stopped. I mimicked her and sucked all of her juices off my hand. She tasted a lot sweeter than I thought she would.

"Brent you are a fucking natural at eating pussy." She said after she finally came back down.

"Now I'm going to bend over the back of the couch. I want you to get behind me and enter my pussy with your lovely cock. Ease it into me, don't just slam in. You are quite large, and you need to let me stretch around that massive dick of yours."

I did just as she said. I touched and rubbed her ass cheeks, spreading them, and glancing at her puckered asshole before I put my cock to the center of her cunt hole. I slowly guided my shaft, inching my way in, and inch by inch; the skin on my dick pulled back.

"Fuck, your pussy is tight," I said as I slid all the way in.

"Is it ok to move now?" Making sure I gave enough time for her to adjust.

"Slowly back out and come forward. Not too fast." She said in a low voice.

I wasn't sure how long I would last. She was so tight and I was afraid if I moved I would instantly come. I pulled out slowly, and pushed back in. I did this several times before she moaned.


I did just that. I grabbed her hips and began slamming into her. She brought her hand to her clit and started rubbing. She screamed out as her insides clamped down on my cock, milking me.

I stopped moving until she came back down and then I continued fucking her. I fucked her hard and fast, thrusting a few more times before exploding inside her.

Panting hard I pulled my withering cock out of her and sat on the couch next to her. She laid her head on my chest, and we sat like that for some time. Eventually, she got up, went to the bathroom and brought back a damp cloth. I washed up and got dressed. We walked to the door and she kissed me on the cheek.

"You are a natural at sex. I can't wait to give you your next lesson. But not during the week. You have to focus on your school work. We should wait for the weekend. I'll let you know when we can get together again."

When I got home I laid on my bed, exhausted, happy and my cock sated. I fell asleep that night with ease.


It had been several days since my first time and I was starting to worry if I would actually meet with Mrs. Jones again. No, that's not true. I was wondering if I would get to fuck her again. Everything in me wanted to run down to her, but I had a lot of editing that had to be done for the school paper.

Wednesday evening my parents were going out for their weekly shopping and errands. Right after they left, there was a knock at the door. I answered and it was her standing there in heels and a long jacket.

"I saw your family leave. Will they be gone long?' She asked as she took off the jacket. She wasn't wearing anything underneath. Mrs. Jones was here in my house wearing nothing but heels.

"About an hour or so," I said before she claimed my mouth with her lips.

She went to her knees and pulled out my now throbbing cock. She swallowed my cock with ease taking it all the way to the base without even gagging. She fondled my balls, and gave them a gentle tug. I almost lost it at that moment. She knew I was close because she stopped and stood up.

"Your next lesson. Always give as much as you take. You won't have a problem with this, but always make sure she gets off before you do." She smiled and led me down the hall, dragging her coat behind her.

"Where is your parent's room?" She asked, and I took the lead, guiding her through their door and over to my parent's bed. I was freaking out but she just walked up to the bed, spread her legs and bent over, resting her hands on the covers as she looked back at me expectantly.

Her ass was up in the air, and I was eating her pussy just like before. Licking and sucking. Two fingers stretching her hole, and the other fondling her breast like I had seen her do to herself. She came hard and fast in just a couple of minutes.

"Yes, yes. Right there. Fuucckk" She yelled out as her orgasm washed over her in waves. Her juices were now running down her legs. My face was covered in her juices. She rolled over onto the bed and spread her legs inviting me to fuck her.

I didn't waste any time. I had her legs spread out on my shoulders, and I slowly slid into her. I waited like she told me and let her adjust to my thickness. Then I started moving in and out. I found a steady rhythm. Not wanting to go too soon I took it slow. I rubbed her clit in a circle with the pressure I knew she liked.

She was soon convulsing around my cock again. I slowed down until I knew the waves were done. Then I started banging into her fast and hard. My cock exploded in her, and I yelled out as I emptied into her tight pussy.

Suddenly, I heard the door shut, and I knew they were home. "Fuck, that's my parents. I grabbed my shorts with lightning speed. And threw her jacket to her. We raced down the hall to my room. She said "You were showing me your yearbook work." so I pulled out my laptop and brought up the current photographs I had taken.

"Oh, there you are. I called for you" my mother said.

"Sorry I didn't hear you. Mrs. Jones wanted to see the pictures I had been working on for the yearbook." The lie slid out of my mouth with ease.

"That's nice of her to come by and work with you here." My mom said with a question in her voice.

"Mrs. Lockwood, you have a very talented son." Mrs. Jones said in a completely sincere voice. "You should be proud. With his hard work, and talent at photography, he should have a full scholarship to college." She winked at me as she said this.

"Brent, I will see you at school. We will go over the rest later. I'll probably need help with those boxes as well, but I will let you know when they are ready." She said before leaving.

"What was that about? She has never been here before."

"I saw her down in the lobby, and she asked about the yearbook pictures. It was just easier to show her than to describe them."

"Well, your dad and I dropped Stacy off at the library, and we realized we forgot the grocery list." Mom's always forgetting "The List." She grabbed it and headed back out.

'Shit, that was close.' I thought. 'Fuck, fuck, maybe I shouldn't be doing this. No, this is exactly what I need to be doing.' I laughed. I got into the shower and thought of the face Mrs. Jones made when she was getting off. I pleasured myself several times until the water got cold. I just let my come run down the drain. Then a thought hit me: I needed to ask Mrs. Jones if she is on the pill.


I wanted so much to go knock on her door, but I knew if I was pushy and didn't follow her instructions to wait until she asked, it might lead to me never fucking her again, so I managed to control my desires.

I spent the remainder of the week at the park, fooling around, and playing basketball after school and taking pictures. With everything I did, visions of Mrs. Jones came with me. I pictured her legs on my shoulder and her perfect snatch in view right before my cock slid in. I pictured her as she looked up at me with her lips around my dick. I jacked off a lot.

It was almost two weeks later when I was sitting in Algebra class. I got called to Mrs. Jones office. The other kids in the class all called out how I was "In for it now!" and asked me "What did you do, Brent?" Nevertheless, I was just excited to see her again.

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