This is a work of fiction. The characters, incidents, and dialogues in this story are of the author's imagination and are not to be construed as real. Any resemblance to actual events or persons, living or dead, is completely coincidental. All characters are of age, 18+, even when not specifically stated.
I (20/m) moved back in with my parents this summer after completing my two-year degree to study for some exams. We have been living in this apartment since my birth.
Our neighbor (I usually call her Aunt Jen or generally Aunty) is a working mom of two who just got divorced this past year. As far as I know, it was due to her not being able to tolerate her junkie partner. She is financially independent, so it was not an issue for her to conclude that chapter of her life. She has two sons (10 and 13) who treat me as an older brother; I let them play games on my PS, thus the frequent interaction and friendship. I also help Jen whenever she needs help with stuff, for basically two reasons: one being she is incredibly hot and I pounce on every opportunity I get to go near her, two being my mom who is really good friends with her, just forces me to go anyway and help.
Aunt Jen is a very fair and beautiful woman. Despite being a mother of two, she has big juicy tits and a heavenly ass that I can look at without blinking. She is around 5'11" or 6'. On the other hand, I would say I am average looking but athletic and tall.
So, beginning with the story, it was a Saturday morning, my parents had just left to attend a wedding out of station and were to return early Monday morning. Everything was going normally; I had the house to myself. It was around noon, and I hadn't jacked off in 3-4 days, so I was feeling horny. I placed an order and went to my room to jerk off.
Just then, Aunt Jen called me to fix her son's bicycle. The chain had come off. I went to their garage and quickly settled the chain. Just as I was about to leave, she came and offered me some water, which I drank. She was wearing a nightgown that was clearly showing her cleavage, and it got me super turned on.
I went back home and jacked off super quick while thinking about her. It was pretty normal for me. If there was one woman in the world I would have liked to sleep with, it was her, so this was not new. My lunch arrived, and I ate up and dozed off.
Hours later, I woke up with a very bad stomachache. I took some meds, but it just wouldn't go away. So, I called my mom and asked her about it. She told me to try another medicine, which I took, but it was of no use. I was in immense pain for the next 3-4 hours. My mom called again around 9 PM; I replied that it was still hurting, so she asked Aunt Jen to check up on me.
Aunt Jen rang our bell, and I went and opened the door. She was probably ready to go to sleep, but since my mom called her, she came to check up on me.
"What's happening?" she asked.
I described everything, and she said, "Just drink a full bottle of water and use the washroom."
I did as asked and came out about 30 minutes later and informed her that the pain was a bit lesser, but my head was hurting now. Mom called her to thank her, but she said it was okay and that she was going to spend the night alongside me in case I felt pain again. Mom thanked her once again for taking care of me in her absence.
Now, as I started to feel better, my cock was slowly turning hard at the thought that Jen would be alongside me. We went to my room, and she asked me to lay down on my side and try to sleep.
"Can I do something to help you sleep faster?" she asked.
"If you are fine with pressing my head," I replied.
"Yeah, why not?" was her answer.
I asked her if her kids were alone, and she said, "They are asleep."
She pressed my head slowly, but after some time, she slid her hand behind my shirt and started rubbing my back. I tried my best to sleep, but it was very awkward for me, and I was incredibly horny with a full boner. I couldn't move; if I did, she might spot my boner, but I couldn't make it go away just lying there.
Minutes later, she moved her hand towards my stomach to feel if there was any cramping or warmth. She must have thought I was asleep. When her hand touched my stomach, she rubbed it a bit. Just as she moved her hand a bit down, my boner touched against her hand. She was startled; so was I.
"Are you okay?" she asked slowly.
"I don't know, aunty. I didn't mean to... I just can't sleep... I'm sorry."
"It's completely normal for boys to react like that to other women's touch, so don't worry."
I slowly muttered, "Okay, Aunty," and closed my eyes.
Something must have gotten into her; she grabbed my boner. I gasped loudly, but she shushed me and said, "Try to sleep, and I will try to make it go away."
She gestured for me to turn face up, and I did. She slid her hand into my boxers and started jerking me off. All the while, my eyes were closed; I could feel her hips touching my side and her hand going up and down on my cock. I would be lying if I said I lasted a minute; it was the most erotic moment for a virgin to get a hand job from an incredibly hot and experienced woman. I moaned with every movement, and after like 5-10 jerks, I exploded inside my boxers and shifted in my bed quite a bit from the orgasm, which was by far the best of my life!
"Try to sleep now before it happens again," Aunt Jen said, laughing.
I laughed as well but dozed off immediately from the fatigue of the entire day, not even changing my boxers.
I woke up in the middle of the night to find dried cum stains on my boxers. Jen was also asleep a hand's distance from me. I got up to change my boxers and came back to find her hands inside the side of her robe, definitely on top of her mound. She must have been pleasuring herself and then slept off.
I decided that this was the time to maybe progress things a bit. I went back to where I was sleeping and acted as if I was asleep, putting an arm on her tits. She must have been awake, as I heard her arm shift, but she didn't take my arm off; instead, she came closer to me, and we cuddled. I was totally thrown off by this. Did she want me as much as I did, or was she just asleep?
My boner was poking her in the thighs. She caught hold of it and started jerking me off again. I tried my best not to cum, but I couldn't last any longer than a minute and orgasmed again as I thrust myself in her direction; such was the magnitude. My boxers were wet, but I couldn't care less and dozed off facing her tits.
The next morning, I remember waking up late, around noon. I felt fine; the headache was gone, and I was totally hungry. I woke up to find myself in my cum-dried boxers with morning wood. I felt nasty, so I went and brushed together while taking a bath. I came out to find a message on my phone from Jen.
She asked me to call her once I was fresh awake. I felt a bit shy at first; now that last night's events were gone, it was a whole new scenario. I did as asked, and rung her up, but there was no answer. I assumed she would have been busy, so I decided to eat some fruits that were there since I was hungry.
Just then, I heard our bell ring, and in came Jen.
She was looking very sexy in that vibrant yellow gown she had on. My naughty eyes could clearly outline her black underwear too. My god, I just wanted to squeeze her tits and ass so bad, but I was brought back to my senses when she wished me good morning and said, "Your mum will be back by dawn; she asked me to prepare some simple food for you since your stomach's upset..."
I cut her off mid-sentence and said, "No, aunty, it's fine. I will make do with the fruits."
She replied, "Just go and have a seat." She went to the kitchen and started preparing.