When i was in college, i had sex for the first time with a woman old enough to be my grandma.
I was 21 and in college at the time. I moved from my home town to study and rented a small apartment by myself. My landlady, Angela, was 60 years old and a typical granny, she was chubby, her hair was grey and she was very gentle. We got along very well, she was actually VERY kind to me, more so than to other tenants. She was essentially my only friend since i got there.
I was very shy, chubby… And a virgin. I had never had a girlfriend, partially due to my insecurity regarding my cock. It is only 8 cm long and i always felt insecure about it, plus my weight. As i moved i was hopeful that i’d find a gf in college, but that wasn’t the case. I hadn’t even made a single friend… Except for Angela.
I still remember our first interaction when i moved: she came up to me to give me the keys and welcome me, then she stared into my face, pinched my cheek and said i reminded her of her late husband (who i would MUCH later under non-related circunstances find out was my great-grandpa) and called me handsome.
Angela was also pretty lonely. She got married at 20 to a man double her age who passed away 20 years later. She never truly got over it and never dated again. Turns out he was her only ever partner.
She quickly took a liking to me and went to my place constantly to bring food, usually lasagna. She also invited me a lot to her apartment to have meals with her. We quickly grew closer and developed a bond, which i though was a grandma-grandson one but turned out to be something else.
When i started working out at home she noticed i was getting more muscular and i excitedly took off my shirt to show her my results and she got red. I started flexing and she told me i was very handsome and strong. I got embarassed but thanked the compliment.
One night she invited me to dine with her and we ended up chatting until late at night. I had class next morning so i said goodbye to her but she asked me to stay the night. I actually agreed but said i still had to get a pajama but she told me to just sleep with my briefs on. I tried to avoid the topic but ended up admitting that i was insecure about my cock, to which she promised not to look at my tool. So i showered, put my briefs back on and asked her where would i sleep, to which she replied that i should use her bed.
I was anxious about it all but laid on her bed while she showered. She then came to the room only in a towel and asked me to close my eyes while she changed. I did and when she told me i could open them she was only in undergarments, granny knickers and a large bra. My heart was rushing as she laid besides me and asked me to spoon her. I spooned her and felt calm as she started talking to me about how she missed spooning with a man. Her voice soothed me into sleeping.
Then i had a dream about fucking a classmate of mine. I was balls deep in her when she moaned my name loudly, leading me to cum inside her. As i woke up, i realized i had been humping Angela until i came all over my underwear. I sat up, rushing to explain myself but she caressed my face and told me to calm down. She brought her face close and we shared a kiss, which led me to fall asleep again.
When morning came around i woke up with the scent of dried semen and pancakes. She had made us breakfast. I tried to apologize for the smell but she said she had missed the scent of the male body. I ended up eating, going home, showering and leaving for class. As i came back, Angela came to my apartment to talk. I was very embarassed about the happenings but turns out she liked all of it. Then she made me an offer: living with her in her apartment. I wouldn’t pay rent and the only condition was for us to share a bed. At that moment i knew what would happen and honestly, i was horny for her but i was too insecure about my cock. Still, i accepted and moved my things to her place. She also gave me back the last month of rent money.
She asked me to sleep only in my briefs that night too and i somehow agreed. I showered first and waited for her to shower, she came to the room in only a towel, i closed my eyes and when i opened them she had a VERY old and VERY tight lingerie on, from when she was young. Her massive breasts were squashed by the bra and the panties barely covered anything. She asked what i thought about it and i could only stare silently. My cock went rock hard.
Suddenly, the bra couldn’t hold it, burst and her left boob was fully exposed. She was also suprised by it. I was taken by a primal lust and grabbed her, sucking her breast. I sucked it intensely and ripped the bra apart to expose her other breast. I pushed her onto the bed and sucked on her breasts like a maniac, as she moaned. I then ripped her already worn panties, exposing her hairy bush. I was about to take my dick out to fuck her but then my insecurity kicked in, freezing me. I apologized to her for losing control but she told me she wanted to be fucked like she was young again. I told her my dick probably wouldn’t satisfy her but she reassured me that she was craving dick and mine would be more than enough, but asked me to be careful, confessing that due to the time without sex her hymen had regenerated and she was almost a virgin again.
I took my briefs off, exposing my hard cock. I was embarassed but she said it was beautiful and well-shaped. That raises my confidence a bit and i put it in. I almost came just from putting it in her tight old pussy. I tried to get a grip and fucked her slowly, rupturing her reformed hymen, but was quickly taken by a primal lust and rammed my cock into her, she moaned as i fucked her pussy, dusting off the spider-webs. She moaned like crazy and i ended up emptying my ballsack inside her. We hugged after fucking and she told me it was amazing and asked for more. We fucked 2 more times that night.
Fucking her raised my confidence regarding my cock and i ended up becoming more social and pulling girls, but i kept fucking Angela.
