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A mostly true story of when I was 15 and hooked up with my 55 year old neighbor.
This is a mostly true story of my first experience with my older neighbor. Sorry for any grammar and structure issues. Definitely not a writer. Just wanted to share my experience.
The house I lived in shared a long driveway with our widowed neighbor Mrs.Gloria. She was a 55 y/o white widow, very petite, very sweet/caring, silver hair, flat ass and some amazing saggy breasts. She wasnt the prettiest woman but definitely not the ugliest. With that being said, before this experience I never really looked at her sexually.
My mom and stepfather would often go out of town for business. I guess they trusted me not to throw parties or get into trouble while they were away. They had good reasons to trust me. I was a bit of a nerd so I never had the guts to throw parties or trash the house. They stocked the fridge and my sisters didnt live too far away if I ever needed anything. So they never worried about me.
We had a basketball goal that was positioned in the middle of our driveway that I would often use. Well while my parents were away on one of those business trips I decided to go shoot some hoops. While playing around Gloria came over to conversate. She was wearing a summer dress that went down to the top of hwr knees. Dont exactly remember how the conversation went, but I told her my parents were out of town and they would be back in a couple of days. She showed sympathy that I was alone then told me she was going to blockbuster (back when that was a thing) to rent a movie and asked if I cared to join. I had nothing better going on so I agreed. She returned about 30 minutes later and invited me over.
She rented “Basic Instinct” of all movies. At the time I didnt know about the “scene” or the other “scenes”, honestly I was a little disappointed that she rented that movie. Seemed like it was going to be boring (boy was I wrong). But being the polite kid that I was, I just decided not to say anything and watch it with her. Well she loaded up the movie and brought out the popcorn. She sat right next to me with the popcorn sitting on both our laps.
Well anyone who has watched the movie knows about the nudity. Not sure if she fully knew or not. But when the nude scenes came up, I definitely became interested. Gloria never stopped the movie or asked me if it was alright. That interest boiled down in my pants. I hid it best I could, but the warmth of Gloria’s leg and the image of Sharon Stone just kept me hard. I eventually excused myself to go to the bathroom. I tried to cover myself as I got up, but I know she saw. I was a little over 5″ at the time (or maybe less, teenagers always add a little extra to the ruler), but the tent was visible. I heard her giggle as I walked to the bathroom.
At that point in my life I had become an experienced masturbator, but I was to timid to just masturbate in Gloria’s house. So I spent what seemed like eternity in the bathroom till I was finally soft and ready to come out. I sat back down and she asked if everything was alright. Of course I said I was fine and continued to watch the movie. Well it took no time at all before Sharon Stone and Mrs.Gloria’s warmth got me hard again. I started shifting around, probably being obvious with what was happening to me. At that age I couldnt control it.
Eventually Mrs.Gloria asked if everything was alright. I tried to play it cool by acting like nothing was wrong. She giggled a little then went quiet for a bit. She asked again if I was ok. I just nodded. “You know that girl is very pretty and im sure seeing her girly parts makes young men very uncomfortable down there”, she said. Im sure my whole face turned red at that point. I was too embarrassed to even reply. “It’s ok. All young people go through that stage. I understand”. I felt like suffocating myself at that moment. Being a stupid teenager I thought that my life was over. I thought that now I will be seen as a perv, Mrs.Gloria would tell everyone what a perv I was, and I would always be classified as a perv. Then she said, “Its ok if you want to take care of that little problem you have down there. I dont mind. In fact I encourage you to do it”. I looked at her dumbfounded. Then I started to get up to leave. “Where you going?”, she asked. “Ummm….I’m going home to take care of it”, I replied timidly. She chuckled and said, “No silly. Take care of it here. Right now. Im a grown woman. I know what boys and men do. Ive seen it all before. I dont mind. Really”.
I didnt know what to say. My mouth dropped. I just sat back down next to her and contemplated what to do. I wasnt sure if she was serious. Or if i was hallucinating. Or if I feel asleep during the movie and was dreaming all of this. She chuckled again, “Go on. I really dont mind.” So I did just that. I unzipped, pulled out, and started stroking. I was a little shy and nervous at first, but the pleasure I had and approval from Mrs.Gloria quickly changed my mood. I gotta say, jerking off never felt so good. I started using my spit as lube. Mrs.Gloria kept glancing over at the movie, then back at me. Every now and then she would let out a soft moan, telling me how nice I looked stroking myself.
After a few minutes I watched her move her hand up her dress and her moans start to become louder. I couldnt see much since her dress and hand were in the way, but I definitely knew what she was doing. “You dont mind if this old lady does the same. Do you?”, she asked. I just nodded. Her body was slowly moving to the rhythm of her hand. She was becoming more and more vocal with her moans. Then I eventually started to smell her. The first time I ever smelt a womanly scent. I instantly became hooked to the smell. The smell caused me to stroke harder and faster.
After a while the movie was nothing more then a background noise. Mrs.Gloria was watching me and I was watching her. She lifted herself up slightly and pulled her dress up, revealing a pair of very wet white granny panties. She lifted her legs and pulled off her panties, revealing a slightly hairy graying bush on top of a very wet pussy. She smiled as she handed me the panties , “Try rubbing these on you. Im sure the silk will feel just as amazing on you as it did on me”. I did as she said and rubbed it on my throbbing member. She was right, it felt amazing.
I could feel myself getting closer and closer to climax. I was sort of edging myself, going slower to try and last longer. She must have known I was getting closer. “Would you like to experience something different?”, she asked. I was only able to mutter out a weak “Yes”. She slowly sat up on the couch and pushed my hand away from my cock before gripping it and slowly stroking it. Her hand was so warm. I almost came once again. I definitely wasnt expecting her to lean down and kiss the head before taking me in her mouth.
To this day I have never experienced such an amazing blowjob. She knew how to swirl her tongue around my shaft. Making slurping noises as her saliva dripped down to my balls. She was taking it deeper and deeper into her mouth until she had every inch in it. I couldnt hold it any longer. I didnt last long before cumming in her mouth. She accepted every drop. Sucking me till I tried to pull back from the sensitivity. She finally pulled it out of her mouth, licked down the shaft, and pleasured my balls with her tongue till she licked every drop of the saliva she left on them.
She sat up, trying to catch her breathe, giggling as she sucked in air. “Thats a good boy. Now can you do something for me?”. At that point I was willing to do whatever she wanted. I nodded, “Anything”. She lifted up her dress and unclamped her bra, revealing her sagging breasts. She climbed on top of me and pushed her nipples into my mouth. I started to suck them hard, flicking my tongue on her nipples. “Oh my god thats so good. Nibble on it hunny”. I started to use my teeth gently. Trying not to hurt her. “Bite a little harder”, she demanded. I did. I felt her fingers combing through my hair and holding my head close. My cock was throbbing once more (i dont even think it went soft), and pressing against her wet warm pussy.
“Time you became a man”, she said as she reached behind and positioned my cock as she lowered herself onto me. She was very tight. It almost hurt at first with how tight she was. It didnt take long for her pussy to accept me. The feeling was so amazing. So tight and warm and inviting. I moaned with her nipple in my mouth. She slowly rode it. Her head tilting back as she enjoyed the pleasure I was giving her. She kept saying, “oh my…oh my….oh my”. I didnt think I could last long, but I did. Much longer. Long enough for her to orgasm again and again. Finally she stopped with my full length inside her. Grasping me as she panted.
She pulled herself off and sat back on the couch. She was covered in sweat. My cock was still throbbing and aching for more….she knew. She got up and grabbed me by the cock. “This way big boy”, she said as she pulled me to her room. She climbed up on her bed on all fours and motioned me over. I positioned myself and rubbed my cock against her trying to find the hole. I even slide across her ass, she reacted by telling me “Not there hunny. Not yet at least”.
I pushed myself inside her and started thrusting hard. “Slow down baby. Im not young anymore”, she said trying to calm me down. I did slow the pace somewhat. Slowly I learned how to keep a rhythm. But as I started to near climax my pace got faster and harder. At that point I didnt care if she told me to slow down again, I wasnt. I needed to cum. To my surprise she didnt tell me to stop. She just kept on saying, “oh my god yes!!!”. With one final thrust I unloaded everything I had inside her. “Yes baby!!! Fill me up!!! Give me your seed!!!”, she said while she gripped the sheets. We stayed in that positioned for a couple of minutes before I pulled out and fell into her bed. She was breathing loud and chanting to herself, “That was so amazing! Oh my god that was so wonderful!”.
When she got her breathing under control she laid her arm across me and pulled me in close. She looked me into the eyes and lowered her lips to mine. We kissed for a few minutes then I felt her tongue brush against my lips. My mouth opened slightly and my tongue found hers. Seemed like eternity that we were making out, but eventually sleep took over and I was out.
Sometime during the night I started to feel something warm and wet brushing against my balls. When my eyes finally adjusted I saw Mrs.Gloria pleasuring them. She was gently squeezing them as she licked and sucked each one. Then licking between my balls and thighs. My cock didnt take long to get hard, but she never touched it. She was teasing by not giving it pleasure. When I reached down to grab it, she brushed my hand away. “Let me show you other pleasures hunny”, she said before going back to work on them. I didnt argue. She was sucking and licking them for a very long time. My cock was aching. But then she started to do something different. Her tongue was wandering lower down. First to my taint. Back up to my balls. Lower down close to my ass. Licked back up my taint. Then she pushed my legs up, exposing my asshole to her.
I honestly didnt know what to think or how to react. This was completely new to me. Her tongue flicked across my ass. My mind was wandering. Ive never seen this in porno. Never talked to friends about it. Never even fantasized about experiencing it. But I was curious because everytime she licked my asshole, I found it pleasurable. Even moaned. She licked all around the rim, explored the inside with her tongue. She knew I liked it. I was finding this very exciting. But then she started to rub it with a finger and tried to stick it in. That I did not enjoy. I pulled back and made a low painful grunt. She pulled back and asked, “Do you not enjoy my finger?”. I whimpered a “no”. “Thats fine hun. But I know you enjoy this”, she started to lick it some more. Im not going to lie, her tongue sent me to heaven. A type of pleasure I never thought possible. I felt her hand grip my cock and she started to stroke as she licked me. Her tongue finally made its way back up to my balls, then my cock, and she started giving me another amazing blowjob.
This time I didnt cum quickly. I enjoyed every second of her mouth. I was on the verge of cumming when she stopped and rolled over to her nightstand. She pulled out a bottle of lube and handed it to me. Then she instructed me to rub it over and inside her ass. I lubed it up nicely, sticking a finger deep inside her tight ass. She told me to add another finger, then another. Her ass was getting nice and loose before she told me to pull my fingers out and give her my throbbing manhood.
Even after getting it loose with my fingers, I still had a hard time getting it in. She told me to be gentle. Not to use her ass like I used her pussy. So I did….to an extent. But I couldnt help myself. I started thrusting harder. Then slowing my pace when she started to complain. So it was a constant battle between fucking her gentle and hard. But eventually my adrenaline kicked in and I started going at my own pace. She was screaming, “oh my god, slow down!!!! Slow down baby!!! Oh my!!! Oh my!!! Slow…..oh my!!!! Just cum in me baby!!! Cum in my ass!!! Give it to me!! Oh god yes!!!! Use my ass baby!!! Fill it!!!”. So I did. I came deep in her ass. I grunted loud as I did. She collapsed on her bed and I followed behind, never pulling out. When I finally did pull out I feel fast asleep.
This continued for the next couple of days until my parents came back. After that I would visit her every couple of days. When my mom finally asked why im going to her house I lied and said I was helping her clean her garage or move things around. You know, doing the neighborly thing. After that I tried to be more discreet. Sneaking over at night or right after school when my parents were still at work.
We had fun for a few months. Then she either had her fill of me or the fact she was fucking an underage kid finally caught up with her. She told me there would be no more fucking. I was pretty upset about, even tried to force myself on her. But she would just push me off and tell me to go home. Things got awkward after that. She quit saying “hi” or even acknowledging me when I was near. I actually started hating her for brushing me off. When I was 19 she became terminally ill. I went to go visit her in the hospital, first time we spoke in years. She apologized to me for “taking advantage of me”. I told her the times we spent together was the best times of my life. She didnt take advantage. She just made a young man very happy in his young life. She smiled when I told her that and I kissed her for the last time. To this day it’s still true. She was one of the best, if not the best, sexual partner i’ve ever had. Mrs.Gloria, you were amazing.
So again, this is a true story. Now our first time wasnt as eventful. There was some sexual acts (rimming and anal) we didnt do the first time. But eventually they did happen. Hope you all enjoyed and could read it all the way through. Keep on groving my sexual friends.
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