Written by Big_thk_Bull
Mar 13, 2013
First experience with an older woman
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11 minute read
I was 18 it was my last year in high school and we had a smoking hot teacher for English class. She was younger than all the other teachers and her body was a knockout. Most guys in the class hit on her on a daily basis but ofcourse she always turned them down. She knew she was hot too because she would wear clothes that weren’t too revealing but still showed off her nice long legs, tight butt and well there was no way for her to hide her big tits. A group of us planned everyday things we could do like asking her to get the book on the bottom shelf or accidentally dropping the chalk duster when we were up at the board. Anything we could do to get her to either bend over so we could watch her ass or bend over in front of us so we could hopefully catch a glimpse down her blouse. She caught on to the tricks pretty quick and being a younger teacher she was really careful about what she said, wore or did.
I was a teacher’s pet and I loved it although I was a bit jealous because it also meant I didn’t get as much attention. One day near the end of the year Miss Tilcott asked me to stay back after class. I was kind of mystified because my mark was in the 80s and the final exams were probably going to be a breeze. My friends kept winking at me when they walked out of the class and then Miss Tilcott started talking to me. I was standing at her desk and it was a lucky thing because with no one in the classroom I was free to look at her huge, heaving breasts. I started day dreaming of what kind of bra she was wearing and how big her tits actually were. I was picturing unbuttoning her blouse, unhooking her bra and then I noticed she wasn’t talking anymore. She was waiting for me to answer and it was a lucky thing I was standing behind the desk because I had a raging hard on. I smiled and asked her to repeat the question she laughed and said I had great marks and she was wondering if I needed any help with the final independent assignment? I was one of her top students and she really wanted me to do well in the class. I really didn’t need help with the assignment but if it meant spending more time with her I was all in so I told her yes. She smiled and we went over to the door to turn the lights off and leave. I was hiding my hard on with my math text book but once she got to the door I figured with the lights off she wouldn’t be able to see it anyway.
Just as I moved the text book she bent over to pick up a piece of chalk on the floor and since I was standing behind her my hard bulge pressed up against her perky ass. It felt so good that for a minute I wished I could record it and play it over and over in my mind. Then I realized she could feel my hard on when she yelped out. She stood up and she looked embarrassed which made me embarrassed and I started apologizing over and over. Then I thought I was in some fantasy land because even though she was still blushing her gaze was on the bulge in my jeans. She gave me this curious look like she was trying to size me up and then she asked me if I wanted to work on the IA tonight? I wasn’t sure if I was ready for more embarrassment but I thought if there was another chance something like what just happened might happen again how could I say no. I followed her out to her car and she asked me if I preferred going to a coffee shop or, she kinda paused, we could go to her place if I was OK with it and she would give me dinner before taking me home. it was a little weird at first while we drove to her place the whole time I was staring at her legs and watching her skirt ride up further. I was quick to avert my eyes whenever she started talking to me but I think she knew I was staring because she never tried to pull her skirt down the whole way there. At one time I could see most of her thighs and I had my knapsack on my lap because my cock was soon going to pop through my jeans.
Just as I was waiting watching the skirt inch up higher dying to see a little piece of whatever panties she was wearing the car stopped and she looked over and smiled “We are here”. I quickly realized and smiled back looking out the window. I knew this neighborhood it wasn’t far from where I lived and I had passed by many times before. I started thinking about all sorts of things trying to get my hard on to go away. We walk up the steps to her house and when I get inside she closes the door and I notice that she had undone a couple of the buttons on her blouse and I could see her cleavage and her purple lace bra underneath. There was absolutely no way my hard on was going away now so I started trying to hide it the best I could. She showed me around the living room and told me to just grab a seat she was going to change and then she’d come and help me out. So I’m sitting there watching her walk up the steps and my teenage mind starts to think I should take a chance. My hands are sweaty and my heart is racing but I walk slowly and softly over to the stairs and look to see if she was already in her room or wherever she was going. I slowly start climbing the stairs almost wanting to turn back half way but I keep going my heart pounding so loud I could hear it in my ears. I get to the top of the stairs and spot a room with the door half closed so I quietly make my way over to it and peek in.
There she was at a dresser in only a pair of lace panties. My cock was rock hard by then I could see her big tits and nice dark nipples through her reflection in the mirror. She bent over to take something out of a drawer and I saw her ass spread. When she stood back up she had another lace bra in her hands that matched the baby blue panties she had on. Then I realized as she looked into the mirror that just as I saw her reflection she could see mine in the doorway as our eyes caught each other’s gaze and I froze. I didn’t know what to do or how she was going to react I was standing at her door peeping in on her standing naked in her bedroom. I couldn’t move and before the fright wore off and I headed back downstairs she turned away and ignored my figure in her doorway but her little smirk told me that she did know I was there. Then she said “I wonder which outfit he will find sexy?” putting two outfits on the bed. She turned facing me but never looked at me and put her bra on as I stared at her tits and my cock throbbed in my jeans. Then she picked up a pair of tight spandex shorts and wiggled into them her ass perfectly framed and her pussy perfectly visible. I could feel the precum in my boxers when she picked up the almost see through mesh top that was sleeveless and started putting it on which was my signal to high tail it back to the living room.
I sat in the same spot but I wasn’t hiding the huge bulge in my jeans because I knew she saw me at the doorway and it seemed like she was interested in more than just helping me with the IA. She came walking down the stairs and I stared at her legs my cock pulsing while I replayed the image of her naked in front of the mirror in my mind. She walked over to me smiling and sat on the couch beside me and said “Shall we get started?” I felt like a fool because there I was with a raging hard on almost tearing through my jeans because I thought she was interested in more than just helping with my IA and she was ready to get to work on the assignment. Then she turned to me smiled and jumped me it took me a minute to even realize what was going on before my hands were on her ass. She kissed me sliding her tongue into my mouth her lips were sweet. I grabbed her ass and squeezed not even believing this was actually happening. I could feel her nipples pressed up against my chest and I really wanted to peel the shots off her and feel how wet her pussy was I was just unsure how far to go.
She was moaning in my ears as I felt her hands move to my jeans and she squeezed the bulge and then started to undo my belt. I didn’t need any other hints after that I immediately started pulling down her shorts while she undid my jeans both of us panting and kissing each other. She pulled my jeans off and just stood looking at the bulge in my boxers like she couldn’t believe. I hoped she wasn’t suddenly realizing what was happening and was going to reconsider but then she finished sliding off the shorts that were halfway down her thighs. She got on top of me again and I slid my hand between her legs and felt the soaking wet crotch of her panties. She was kissing my neck and her hands were already inside my boxers stroking my cock while she moaned. I pulled the crotch of her panties to the side and slid a finger inside her soaking wet pussy feeling her pussy juices cover my finger while she moaned even louder in my ear. She started to stroke my cock harder and faster I guess turned on by what I was doing so I started to work her pussy. I slipped another finger inside her while I kissed down her neck eager to get to her massive tits. I wanted to get her nice and horny before I flipped her over and fucked her on the couch but she had a different idea. Before I knew it she pulled her hands out of my boxers and got up took her shirt and bra off tossed it on the floor. Wiggled out of her panties and then got on her knees infront of me while I sat up on the couch and watched.
She pulled my boxers down grabbed my cock and started to lick the pulsing head of my cock. I sat back watching her and couldn’t believe that it was even happening. Then she plunged my cock into her mouth and I watched her head while my cock slid in and out of her mouth. I moaned feeling her lips wrapped around my cock it was unreal and her mouth was so warm. It was making me more and more ready to fuck so I put my hand on top of her head and every time she slid my cock into her mouth I thrust to slide it deeper down her throat. She choked a little the first couple of times but she loved it and once she got used to it she started to slide it in and out of her mouth faster and faster. I was at the brink about to unload in her mouth when I heard keys at her front door. She didn’t even seem to care and just kept sucking my cock sliding her hand up and down the shaft. I was getting a little concerned though and when the door opened and this guy walked in I just assumed he must have been her husband. I never even stopped to consider if she had a husband and now there I was his wife naked and at my feet with my cock deep down her throat.