This story is entirely fictional. The names of those present has been changed for protection.
Every year my aunty Delilah would take my brother, my sister and I to her place individually for our birthdays into the city. Every year it was something new, except for me. My brother always looked for the social scene: bars, clubs, malls etc. My sister always looked for scientific/educational things to do: the zoo, the science center, provincial museum etc. They also went to get their nails done and other girl things.
But for me, it was different. I was into flying so we would always go to the airport and I would get to fly a small airplane around the city with one of the school's teachers. Every year was the same thing. I enjoyed it, but what I really wanted I knew I couldn't have. I matured much faster than most of the other boys and found interest in girls sooner too. I found that older women were more attractive than my classmates through much of high school. I would always imagine going to aunties house and finally asking her if we could have sex. But this dream was far fetched because I was under age. It was always a really good fantasy of mine. But one year this would change.
It was a few weeks after my eighteenth birthday when I went to the city on the train to spend the weekend with my aunt. She couldn't afford the flying this year so she had other things planned.
Since I turned 18 I always had a condom in my wallet just in case. I made sure it was there as I was so confident it would happen this year that I even bought an extra in case I lost the first.
I boarded the train for the city and arrived about two hours later. There she was. She was beautiful this year. She died her hair brown to see what it looked like as it was usually blonde. She weighed about 165 lbs. maybe and had the perfect hourglass shape. Her breasts were smaller than usual but her ass was a little bit bigger than average. I didn't mind at all. She was wearing a tank top with a denim skirt that cut off just above her knees.
"Hey," she said when I got off of the escalator and hugged her.
"Hey aunty Delilah," I said back to her.
"How was the train?" She asked releasing me and leading me to the subway.
"It was good, took longer than I thought," I said letting her get in front of me so I could watch her ass sway back and forth. I also got a good look at her silky smooth legs.
"What do you want to do today?" She asked as we boarded the subway.
"Well I'm very hungry so we should take care of that first," I said then started to think, "Can we go to JR records? I have a feeling they have some new Aerosmith stuff there."
She nodded, "Sure. I heard of this great bar on the waterfront. Do you want to go there later tonight? Or do you just want to get a few movies and order pizza?"
"Aunty, you know me. I hate the social scene. Pizza and a movie sounds good," I replied. I was sitting but noticed there was nowhere else for her to sit. I stood up and said, "Aunty you can have my seat." After a bit of the back and forth of, "No," and ,"I insist," she eventually sat down.
She stood up when we arrived at our stop and we got off. We walked down the street to her apartment building and went inside. Once we reached her apartment we went in and I dropped my bag on a chair. I said, "hi," to the cats then we were on our way again.
The music store was on the same street so we walked a few blocks then I opened the door for her. She walked in and I followed immediately going to the Rock/Pop section of the store to check for some Aerosmith, Beatles, John Lennon and Grand Funk Railroad albums. Then I went to the basement to check for any Aerosmith LP's that the store might have so I could hang it on my wall back at home.
"You ready to go," she said looking bored.
"Yeah I got what I wanted," I said going to the front line
"What did you grab?" She asked as we got closer to the till
"Fly Away From Here the single by Aerosmith, Yellow Submarine by the Beatles and the single for We're An American Band by the Grand Funk Railroad," I said flipping through the cds showing my aunt.
"Cool, but don't you have all of Aerosmith's albums by now?" She asked not believing that I picked up the cd.
"Like I said, it's a single." I said mockingly. She gave me a friendly shove at the comment then we reached the counter.
After paying the clerk I held the door open for her then left. She then said, "You know you don't have to act like a gentleman on my account."
"You haven't had a boyfriend in so long even though you are so beautiful. It does matter," I said trying not to blush at the blunt comment.
She looked at me and smiled, "Thank you. You are so sweet you know that? I can't believe you haven't had girlfriend in so long either."
I smiled back at her, "I'm waiting for the right gal." I then winked at her. She smiled as if heeding my comment, "Don't worry. I'm sure she is closer than you think."
She gave me a hug from the side and kissed my cheek. I could feel my dick stirring in my pants at that. I tried to figure out if she was coming onto me or just being friendly.
We reached the subway to take it to the main mall which was several stories tall in the center of the city. We went in and she asked me, "Can I get your opinion on an outfit I want to buy?"
I couldn't resist, "Sure." She led me to the victories secret outlet in the store then picked out some black underwear and a bra. She put them on then told me to come in and tell me what I thought of them.
When I got in I got an almost instant erection. The bra fit perfectly and was very sex. The panties were sexy too, but not enough. "Maybe a different pair of panties. And for goodness sake, get a different colour than black. She frowned then sent me out.
She came out fully dressed and brought me around the store and asked, "What kind of panties should I get?"
I almost collapsed at the question. I walked around until I found the thongs. I picked up a white one that I though looked nice. I gave it to her saying, "You should... you know... show what you got."
She laughed at the awkward comment then grabbed a white bra and walked into the change room. Once again she called me in, "Jim, do you want to judge this one?"
Again I got an instant erection. The white made her features appear much bigger than they actually were. "Well what do you think," She turned around and showed me her ass. She then bent over to pick something up.
"That is so sexy," I managed to finally mumble out.
She giggled then told me to come close and take a better look. I knew she was teasing me now. I got close and she told me to check how the thong was fitting around her thighs and ass. I looked down and lost my mind. She was even more sexy in this practically naked state.
I put my hands on her thighs and moved them along her body along with the panties main elastic. I then followed the panties down her ass and under to her asshole and pussy. She moaned when I was over her pussy and coming up towards the front of the panties.
"Looks good to me aunty," I said in a soft voice.
"Just say Delilah. I don't want anyone to hear then get weirded out," She said adjusting the panties, "How does the bra look?"
"Damn sexy Delilah," I said mulling over her chest.
She giggled, "I like it when you talk like that," she said.
"Like what?" I asked confused.
"Like this," she said imitating my voice, "Now get out of here and I'll buy this underwear. Just for you Jim."
I bowed then left. I sat on the bench outside trying not to think about what I just saw and heard. I didn't want to get an erection in a mall. I'll whack-off in the bed that she makes me tonight I thought.
She came out and we continued walking. She leaned up and kissed me on the cheek, "Thank you for being honest. I'm not good at choosing good clothing."
"You've done fine up until now," I said to her.
She kissed me again, "You are so sweet." She took my hand and we walked to the video store to grab some movies to watch.
I picked an older movie, Canadian Bacon, which I was told was funny but never got to watch it. She picked out another movie then we continued walking.
We passed a sex store. She then stopped and we turned around. We went in, the first time I had gone inside on of these stores since turning 18. She went to check out dildohs which again gave me an erection. I checked out the magazines. She came over to me and asked me about a dildo.
"Jesus Delilah, I don't know anything about that shit. Buy what you want to," I yelled softly. It was awkward enough in there without her asking me if that was a good dildo.
She shrugged and walked away. I grabbed a magazine and walked up to the front of the store to buy it. Aunty came up behind me and looked at the magazine I selected. It was a magazine with mostly pictures of lesbians making out naked, "Mmm, I think it's so hot when two girls kiss". I blushed at that thinking of my aunt kissing another girl.
I bought the magazine when the clerk said, "You've got quite a catch there kid. Don't her get away." I smirked at him and waited for my aunt at the door.
She came over and again I held the door open letting her go out first, "Sorry about asking you about the dildo. I bought it, see?"
"I can see that aunty," I said not looking at her. We walked back to her place. It was already five pm so she ordered the pizza. For half an hour I played with the cats while she did work stuff.
The pizza finally came and we put Top Gun in and watched. We ate pizza until we were full. Throughout the movie we got closer and closer to each other until we were finally beside each other.
