Best.Girlfriend.Ever

Gina and I started dating my Sophomore year (her freshman year), and we were now a couple of years out of high school. Due to work and other responsibilities, I was attending JC part-time, but Gina was more serious about her studies. She had already completed her first year and was starting her second year. She was 19 and I was 20 when this incident occurred.

Gina is the oldest of four kids. Paul, George and Jackie were her younger siblings. The kids ranged from 19 thru 14. We had been dating for close to 5 years, so I was pretty close to all her siblings. I got along with all of them, playing video games with her brothers and allowed Jackie to tag along on several occasions. She was always a cool little kid and would always have a big smile for me when I came over to visit.

When we would go out for ice cream, my girlfriend would get upset that I would invite Jackie to come with us. However, we would always drop her off afterwards and go off on our own. My girlfriend would actually get jealous, accusing me of paying more attention to her little sister than her. I was only being nice to her since it would help me score some points with her parents.

Over the past four years, it was hard not to notice how well Jackie was developing. When she was younger, she would always come sit on my lap while I waited for Gina to finish getting ready. Her mom would always tell her to stop bothering me and get off my lap. As soon as her mom was gone, she would jump right back on.

This was cute at first, but as she grew older and her body started developing, it was hard not to notice her budding breasts and her cute little butt. She was growing into a sexy little girl with a very cute face with full lips. Over time, her pajamas evolved from a long sleeping shirts to a crop top with no bra and short cotton shorts that accentuated her cute little bubble butt. The crop top did a nice job of dropping a bit, giving me a peek down her shirt of her A cups with her stiff nipples. At 5’1”, she was light and felt really nice on my lap.

In November of that year, I came over for Thanksgiving dinner. Gina was helping with the Thanksgiving dinner so she asked that I go to the store for some last minute items. She asked Jackie to come with me since she knew exactly what was needed and knew where to find it at the store. Jackie was looking very sexy in a cute little girl way. She was wearing a button-down blouse and a short puffed up skirt that showed off her legs nicely. Without thinking, I paid her a compliment, telling her she looked cute in her outfit. She asked what I liked best about her outfit. I answered truthfully, telling her the skirt was nice and it showed off her legs really well.

“So, do you think I have nice legs?”

“Yeah” I answered nonchalantly. There was a bit of an age difference and I thought I was simply pumping up her ego.

She grabbed my hand and placed on her thigh as we were driving to the store. Fuck they felt nice! I knew that I was supposed to do, but it was simply not possible. Her thighs felt nice in my hand, making it impossible to pull my hand away. At first, she started moving my hand up and down as I caressed her thighs. By the time we got to the store, I was caressing her legs all on my own with no shame. She had long since removed her hands.

We got to the store, quickly grabbed our items and made our purchase before getting back in my car. After putting the car in gear, she gave me a pouty face and asked if I didn’t like her anymore. Asking why she would say that, she said because my hand was not on her thight, making her feel special. I gave her a look of concern, not sure if I should’ve even been doing that in the first place. Reading my face, she put out her pinkie and promised it would be our secret. I hooked my pinkie with hers and afterwards she grabbed my hand and put it back on her soft creamy thighs.

She kept her hands on mine, caressing herself with my hand. As we drove on, she got a bit braver and started pulling my hand up further and further until I felt my pinkie touch her panties. After a few times of bringing my hand up and down against her pantie-clad cunt, she actually started moving my hand up and down against her slit over her panties. She was masturbating herself with my hand. I was both totally aroused with an uncomfortable boner in my jeans and scared that someone would find out.

When we got back to her house, she looked at me with a big smile on her face telling me “Remember, pinkie swear.”

When I left after Thanksgiving dinner, Jackie gave me a hug and a goodbye kiss. Something we would normally do. However, this time half her mouth was on mine and she quickly licked my lips with her tongue. That night I drove home with a boner in my pants and went to bed thinking of Jackie, not Gina. I tossed and turned and jacked off twice to thoughts of making love to little Jackie, wondering how sexy would she look with her petite body and her little tits exposed.

The following weekend, it was more of the same. I was at their house waiting for Gina to finish getting ready while Jackie kept me company. Her brothers were in their room playing video games and their parents were out with friends. Jackie was sitting on my lap with her customary pajamas, a crop top and shorts, only the crop top was cut shorter than normal and it barely came under her tits, showing off her tight tummy. I couldn’t help myself and subconsciously started caressing her very smooth legs.

“Did you like my kiss from Thanksgiving?” she whispered. She was definitely getting bolder.

“Yeah, but you shouldn’t be doing that. I am your sister’s boyfriend and we’re gonna get caught.”

“Have you been thinking of me?” she asked as she brought my hand up to her crotch. She grabbed my my finger and slowly brought it to her pussy and once again she slowly started masturbating herself as she whispered to me “I’m not wearing any underwear and I’m getting really wet. Can you feel me?”

She had me in a trance. I was unable to think straight as she brought her lips to mine. She pressed her mouth against mine as I felt her tongue licking my lips, trying to entice me to open my mouth when we suddenly heard Gina open her bedroom door. Jackie quickly jumped off and I sat on the other couch unable to get up.

Jackie came around the corner and apologized for making me wait. I told her that she looked great and it was worth the wait. I had a raging hard on and in no hurry to stand up. Gina stood there staring at me, wondering why I wasn’t getting up. There was no way I could stand up and her not notice my dilemma. Thinking quickly, I asked her for a glass of water. This gave me the opportunity to stand up and rearrange my dick while giving Jacking a scolding look, which only resulted in her giggling.

The First Time I saw Gina, it was her hair that first caught my attention – her tits were a close second. At 5’4”, her C cups looked fucking awesome on her thin figure. She was on both the school track & field team and the cheerleading squad. All that activity helped her keep a thin waist and a firm ass. Her long auburn hair with curls gave her the sexy look that had all the guys in school checking her out, even some of the teachers.

That evening, after a get-together with some friends, we ended up at my place. I was still living at home with my parents and they were gone for the weekend. We had the house all to ourselves. Gina and I were in bed, talking after having made love.

“Your birthday’s coming up. Have you thought about what you want?” Gina asked me. We had been sexually active since her Junior year. She had made me wait for over a year before giving me her Virginity as my birthday present my senior year. The year after that, she gave me her anal virginity. She had certainly made up for making me wait since then. We had experimented a lot since then and she was usually up for any kinky thing I came up with.

“We’ve talked about it before, babe. Are you ready for a threesome?” She contemplated her answer before responding.

“Sure…..only if I also get one for my birthday.”

“Are you serious? Who would you want for your birthday?”

“I don’t know, I just don’t think it’s fair that only you get to fuck some skank and I don’t. Besides, who do you want fuck for our threesome?” I knew exactly who. The same little girl that had fingered herself earlier in the day. I decided to just go for it and not beat around the bush.

“Jackie.” I said, nonchalantly.

“Wait! What? What Jackie?!?” she asked with a puzzled look on her face, wondering if she had heard correctly.

“We only know one Jackie” I answered with a grin on my face.

“Holy shit! Are you serious? You want to fuck my little sister? But, she’s just a little girl.”

“A hot sexy little girl.”

She stayed silent for a long while. She wasn’t saying ‘no’ so I stayed quiet. She had a pensive look on her face and then turned to me and started slowly stroking my dick.

“You’re a fucking perv. Do you know how old she is?”

“Yeah.”

“And you want to fuck her? My innocent little sister?” After what had happened at Thanksgiving and earlier that evening when I picked up Gina, how could I not?

She pushed me on my back as she straddled me. She pushed my stiff pecker up again my stomach as she started gliding her pussy up and down my dick, telling me how hot it was going to be watching me fuck her little sister, asking me if I knew that Jackie had a crush on me. I told her I had known since we first started dating.

“Does she turn you on? Does her cute little ass look good to you? I’ve seen how she’s been dressing when you come over.” she commented as she continued rubbing her wet cunt hard against my prick.

“I love it when she wears her little crop tops.