Where it happened: Grandmother's house
Langauge: English
Sex: Female
Rating: 9
Category: Straight
My first time, believe it or not, was with my grandmother. She was my step-fathersÆs mom. My parents divorced when I was 5, and my mom remarried when I was about 8 years old. My (step) grandmother was a classy woman and very beautiful. She had been a lawyerÆs wife until her husband died 10-years prior to my momÆs second marriage to her son. She was always well-dressed and mannered but all the while enjoyed the company of her grandchildren. For some reason, her and I clicked from the very beginning. I spent a lot of time at her house across town, sometimes with my siblings or cousins, sometimes by myself.
When I was only 8, 9, 10, maybe even 11, my grandmother would invite me to sleep in her bed, especially when there was storm or we just watched a scary movie. She would hold me close to her, stroking my hair, whisper nonsense stuff in my ear. Ofcourse, as time went on and I got older, I would remain in my own bed for obvious reasons and my overnight stays became less frequent.
I had just turned 15 when my grandmother asked me to stay at her place for the weekend. She told me there was a birthday present at her house waiting to be opened. That Friday evening, on the way to her mansion of a house, we stopped at a nice restaurant. While I was sitting across the table from my grandmother, I noticed for the first time how not only beautiful she was (which I always had known), but also how attractive. Ofcourse, I was at that age when I was already noticing the curvature forms of my teachers, friendsÆolder sisters or moms, other various matriarcal figures in my world. So, I guess it was only natural to notice my grandmotherÆs form. She always had her hair and face beautifully madeup, but today I was noticing her very attractive body. At age 64, she still had maintained a youthful figure. She was wearing a business type of black skirt and jacket that enhanced her endowed form and lovely silver hair. She wasnÆt wearing a blouse or camisole underneath her jacket, so her cleavage was exposed with her every movement. The jewel that hung from
Her necklace rested between her breasts. My god, this was my 64 year old grandmother, but that night, she was so attractive to this fragile and impressionable 15 year old boy. All through the meal and our conversation, I kept taking peeks at her jewel that was snuggled in her breasts. This was causing me to reach a uncomfortable and embarrasing point of feelings and sensation that I hadnÆt learned how to deal with or handle.
At some point, my grandmother interrupted her thought she was conveying to me and asked if I was alright. She looked down at her breast-embraced jewel and then at me, and I think at that moment, she realized what was monopolizing my mind. She kind of smiled and continued with what she was saying. As we were walking to the car in the parking lot, my grandmother took me by my arm and held me close to her side and told how proud she was of me and how handsome IÆve become. She asked me if I had any girlfriends, I told her I didnÆt. She couldnÆt believe I didnÆt have at least one girl. She told me the girls were foolish for not snatching me up, because she certainly would. She then matronly kissed me on the cheek. We continued to chitchat on the way to her house about all kinds of subjects, all the while I kept noticing her beautiful breasts.
I went directly to the den where I flipped on the TV while my grandmother went to change into something casual. We usually watch a suspenseful or horror video, this time was no different. She had already been to the video store. So as I was waiting for grandmother, I went ahead and popped in the first video and was fast forwarding past the previews and credits. My grandmother came in the den and I almost choked at the sight of her. She was wearing form fitting jeans with an equally tight white tank top, still wearing the same necklace with the jewel nestled between her breasts. Her breasts looked very full and large in her tank top. I had a hard time keeping my eyes of her tank top. She sat close to me which also made my heart leap into my throat. She broke the silence by saying she couldnÆt help but noticed the focus of my attention at the restaurant. I felt embarrassed and remain frozen in my sitting position. She said it was alright and she understood the changes young boys go through and the feelings they experienced having raised two sons herself. I turned and gave her a slight sheepish smile, still feeling embarrassed. She then scooted closer to me allowing her breasts to be next to my arm. She asked me if I liked how she looked. I slowly nodded my head. She said she didnÆt care if I looked at her. She said it was easier if I start by looking at her eyes à.., so I did. She placed her hands on either side of my face and slowly guiding my eyes to her nose, then to her lips, to her neck, then finally and slowly, she guided my line of sight to her breasts. She held my face the whole time as I stared at her breasts as a way to let me know itÆs okay to look at her.
She asked me if I wanted to look alittle closer. I nodded my head. She slid her hands to the backside of my head, stroking my hair, and slowly guiding my face closer and closer to her full ample breasts. My nose was now rubbing against her stretched tank top. She quietly and softly asked I would like to look alittle closer à.., I nervously nodded my head. She slowly lifted her tank top over her head revealing the beautiful sight IÆve ever seen. She was wearing a gorgeous lacy DD bra which was making this 15 year old very uncomfortable. She then guided my face into cleavage as she stroked my hair. It seemed like an eternity while I rested my head on her breasts. I hadnÆt noticed, but my grandmother had unsnapped her bra allowing it to fall to the floor. I now was resting my head on her fully exposed breasts. She then offered one of her breasts to me, rubbing her nipples against my lips, like a mother trying to get her baby to suckle. I slowly sucked her breast as she stroked my face and hair.
While I was sucking her enlarged nipple and breast, I felt a hand between my thighs moving towards my crotch. As her hand softly cupped testicles and penis, I thought I was going to pass out. She sensed that I was about to lose and she held me tight against her breast as she continued to massage me. She then began to unbuckle my belt, unbutton my jeans, unzipp my fly, then I felt her warm soft hand slip into my underwear wrapping her fingers around my very hard penis. She told me that everything was alright and this is what grandmothers are for, to help their grandsons realize their potential. She then suggested that we should move to her bedroom. She said it would be like when I was younger, she will hold me close in her bed.
I followed her half naked form to her bedroom. This time, unlike when I was young, my grandmother completely undressed herself before slipping into bed. She asked me to do the same. As I slipped into my grandmotherÆs bed, I felt her warm hands and arms around my waist pulling me close next to her body. She pulled my face into her breasts offering once again one of her large nipples. My swollen penis rest against her thighs, as she manuevered herself so my young dick was eventually between her legs. She then slowly rolled onto her back taking me with her so I ended up on top of my grandmother. She reached down between my legs and guided my throbbing penis into her wet warm pussy. She placed her hands on my butt pulling me already inside her as she wrapped her legs around me. She held me tight so I couldnÆt move telling me to be still and just enjoy the moment. It felt so good to be on top of my grandmother with my hard penis deep inside her and her holding me tight. I could feel her pussy tighten and contract, tighten and contract, over and over again. All of sudden, I felt a sensation I have never felt before. I was embarrassed, I apologize to my grandmother for peeing in her pussy. She started to softly laugh and explained that I was not peeing in her pussy, I was releasing semen or ejaculating for the first time, and she said that it felt wonderful.
I was still very hard. My grandmother asked me to pull my penis out and before it leaves her pussy, push it back in, and repeat that motion over and over. So I obeyed my grandmother. It didnÆt take very long for me to ejaculate for the second time, all the while, my grandmother expressing her pleasure with intense moaning and goans. She then held me tight as she rolled us both over putting me on my back and my grandmother on top. She lifted herself off my dick, which was still very hard, allowed the cum to drip out of her pussy onto my stomach. She explained to me that was semen or cum, not pee. Without hesitation, she lowered herself back on my dick and began to pump up and down on me. Her breasts were swaying to the rythmn over my face with her nipples swollen as large as manÆs thumb. Once again, it didnÆt take very long to cum again inside my grandmotherÆs pussy. This time, my balls ache alittle from cumming 3-times in 30-minutes. She kept pumping me, riding me like a horse. She said she wanted me to cum one more time. This time, as her breasts swayed back and forth, she allowed her breasts to hit my face, and let suck them every now and then as she continued to pump my dick with her pussy. It took alittle longer, but I finally cummed for the 4th time. She slid off my dick, and slid up to my face placing her pussy on my mouth. She asked if I would mind putting my tongue inside her. How could I say no, though I never done this before àà, so I did, anything for my beautiful grandmother. She also asked me to keep my tongue inside as I suck on her pussy lips. At that moment, I felt her body shutter and quiver as my mouth was filled by juices mixed with my cum. She asked me not to let any of it drip out à., I nodded my head. She shuttered and quivered again, filling my mouth with her juices à, again. My grandmother asked me if I could and if I wouldnÆt mind, to try to swallow as much of her juices as possible. As I was slurping and drinking her juices, she cum for the 3rd time. I could barely keep up, trying to swallow of it. My face and hair was completely wet, as she lifted herself off my face allowing her remaining juices to drip all over my face and hair.
After laying there for awhile, we both cleaned up ourselves and returned to bed for a long deserved sleep. Grandmother held me close to her breasts all night. And probably 6 or 7 times during the night, she would wake up and stroke me with her hand until I cum. Each time, she would rub the cum all over my dick and balls like lotion.
In the morning, during breakfast, I asked about my birthday present ààà, she said I got it last night. Upon that, my grandmother led me to the bedroom for another 2 or 3 hour repeat of the night before. By the time I went home that afternoon, I was very very sore and exhausted. But my grandmother had introduced me to the most wonderful experience. Once a month, I would spend the night at grandmotherÆs house learning more and more about that wonderful woman until I left for college.
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