"Jack, I think it's so sweet you are taking the girls out."
My pretty neighbor Amy was at my place, complimenting me for my plans to take her gorgeous daughter Tina and Tina's hot friend Sophia out for dinner. I felt guilty and anxious, but my cock twitched thinking about it.
"It will be good to get you out of the house and they will love that Italian spot you chose. I'd join you if I didn't have go see my mom in Austin."
Amy's face became mischievous and she reached over to stroke my leg. Her hand moved softly up along my skin towards the top of my shorts. My cock twitched again and I suspected she noticed.
"You do need to start going on real dates though Jack. In the meantime, I am just next door if you need some...inspiration."
Amy had 'inspired' me previously by encouraging me to jack off while looking at her bare tits. I hadn't taken her up on her rather open invitation to repeat in part because I was getting so much inspiration from her daughter and Sophia. I stammered and Amy finally left me alone to think about the evening ahead.
I spent almost an hour deciding what to wear. This was completely out of the ordinary for me, but I vacillated from trying to look 'cool' and young with not wanting to look like I was trying to hard with being disgusted with myself for lusting after these two girls less than half my age. I ended up wearing an all black outfit, black pants and shirt and a black jacket. I looked sharp and felt like I would be in control wearing this.
I sat in the outfit alone for about an hour before the girls were supposed to come over so I could drive them to the restaurant. I felt like a boy waiting anxiously for his prom date. I shuddered when I realized that my prom was over 20 years ago, but the two girls had theirs just a couple of months ago.
I finally heard the girls giggling as they walked up to he door. I waited a few seconds before answering their knock, not wanting to seem too anxious.
Tina looked stunning in a white sundress with a flower pattern. She looked like an H&M model with her long legs were displayed proudly. Tina kissed me on the cheek, "Hi Uncle Jack. Don't you look sharp!"
I found myself tongue tied before I said anything at all and suddenly saw Sophia in front of me. I looked down quickly and saw she was much less dressed up, wearing no make-up, a tight t-shirt and jeans. She looked so sexy with no effort at all, I thought as she leaned against me and kissed my cheek. I could feel she was not wearing a bra and my cock started to swell.
"Hi Jack" she cooed with a smirk. The last time I had seen Sofia she had me on my knees, jacking off as I kissed her ass. We had agreed she should call me 'Mr. Brown' and I suddenly became nervous she may have told Tina about her visit.
"Errr,,,well...ummm...let's go?" I suggested.
The two girls giggled and I wondered if it was obvious to both of them how nervous I was. Certainly Sophia knew she could wrap me around her finger, but I hoped to keep my dignity with Tina. Tina sat in front with me on the way there and I got hard just looking at her bare long legs. It looked like she had oiled them they were so smooth.
When we arrived it seemed that everyone in the restaurant turned to see me and these two beautiful young girls. I felt embarrassed...but also.proud. Tina seemed very comfortable in the nice setting but Sophia seemed impressed.
I ordered a nice bottle of wine at Tina's suggestion. I knew the girls were too young, but I needed a drink and certainly didn't want it to be awkward. We were already on or second bottle before the food came. Tina was doing much of the talking, seeming even more vivacious with some alcohol in her. She told us several stories about her swim team. The stories culminated in one where she and a female friend on the team sabotaged the other team while at a swim meet in another town. The two of them targeted the other team's star, flirted aggressively with him, and ended up giving him a two girl hand job just hours before the competition. He didn't come close to his normal times and Tina's school won easily.
I choked a little when she got to the dirtiest parts but Tina just giggled and continued. I wasn't sure what was appropriate, after all we were all adults. Sophia was much quieter, but any time I looked at her she had a subtle smirk and looked right into me with her big brown eyes. I was looking at her full lips and flushed cheeks when Tina blurted out,
"So what do you do for sex now that you're back Uncle Jack?"
I coughed, genuinely taken aback and started to try to answer,
"Well, I'm not...I mean..."
Tina laughed and Sophia giggled. Sophia, who had not been joining in Tina's risque talk, suggested,
"I guess you have to jack off a lot now?"
