In my last story about Anne losing her virginity to me, I mentioned how easy my cock went in and the lack of blood which seemed strange for a girl losing her virginity. Over time she explained it and told me about her sexual history before me.
In past stories I mentioned Anne had a sister, Katie, who was 3 years older. She also had a brother, John, who was 2 years younger. She remembered when she was about 10 there was a time her brother came running into the house crying and screaming about Katie. It turned out John had pulled down his pants and showed Katie his little penis, and her reaction had been to give it a hard pinch. Their parents were angry at Katie but didn’t care that their little prince had displayed his pecker to his big sister. Anne hadn’t seen it, but the event made her think about penises. She hadn’t seen one other than on an infant before but was curious.
Their house was small and their parents had an active sex life which they could hear through their bedroom door. Anne didn’t really know what they were doing, just that they were “doing it”. Then one day when their parents were out of the house, Katie took her into their parent’s bedroom and took a book out of their dad’s drawer. It was an old sex manual, very outdated featuring advice that pretty much everything but intercourse was perverted. The main thing that stuck in her mind were the illustrations which were surprisingly explicit. It was the first time Anne saw what a man’s penis looked like (if only a drawing) and learned what having sex really meant. It seemed gross at the time, but she continued to be curious about penises.
Katie surprised her again one day when Anne was 12. They shared a bedroom with twin beds, and one night they were laying in bed your Anne heard her sister squirming and making strange noises. Anne asked her what she was doing and Katie stopped. She proceeded to tell her what had happened at a sleepover the night before. Katie’s friend Sandy (see previous stories) had taught her how to masturbate. She said it felt really good. Anne didn’t know what it was and Katie said it was playing with your cunny. Anne asked what a cunny was and Katie said her “girl parts”. Anne asked her to tell her more but Katie said she was too young and to go to sleep. She did, but several times she heard Katie “playing with her cunny” in the next bed and finally convinced her to show her what she was doing. Katie pushed the covers down and swung her legs over the side of the bed. Her panties were already around her ankles and she lifted her nightie and spread her legs. The sisters had seen each other naked many times, but this was the first Anne had seen Katie’s, or anyone’s, spread open pussy. Then Katie showed Anne how she rubbed her finger up and down and mentioned how particularly good it felt rubbing her “button”. Anne wanted to try but Katie once again said she was too young and climbed back under the covers. Of course the first chance Anne got when she was alone she tried it but didn’t get much out of it.
Fast forward to Anne at 15. Katie and Sandy snuck Anne into a drive in theater to see a soft X movie. There wasn’t any graphic sex, but there were bare breasts, butts, beavers, and PENISES! They were all soft, but it was Anne’s first view of a grown man’s penis. The movie made her feel “funny” and when she got in bed that night (Katie had her own room at this point). She tried playing with her cunny again for the first time since Katie had showed her how it’s done. This time it felt much better. She did it until she felt like she needed to pee and got up to go to the bathroom. When she sat on the toilet she was surprised at how wet her vagina was. When she was done she went back to bed and went to sleep. She did it again regularly after that, stopping when she “had to pee”. One day she told her sister what she had been doing and Katie said, “Good for you.” She told Katie how she stopped when she needed to go and Katie laughed. She told her that feeling meant she was going to have an orgasm. From what Anne had read in her parents’ book, she thought only men did that. Katie said she would show her. That night Katie came to Anne’s bedroom. Katie’s bed had been removed from the room and replaced with a desk. Katie turned the desk chair to face Anne’s bed and sat down. She lifted her nightie to reveal she wasn’t wearing panties. She pointed at Anne and said “You too!”. Anne sat on the edge of her bed facing Katie and slid her panties off. They proceeded to start masturbating in front of each other. Soon Anne said she was getting that feeling and Katie told her not to stop. Suddenly Anne felt her first orgasm wash over her body. Within seconds Katie came also. They didn’t masturbate together again, but when Anne did it herself she didn’t stop to go to the bathroom from then on.
So when she first saw me standing up with her sister at Sandy and Garry’s wedding she had a couple years of solo orgasms behind her. She claimed that she thought of me when masturbating after that and had decided she wanted me to be the first guy she had sex with. A year later when we bonded at Garry and Sandy’s anniversary party and made a date, she fully intended on seeing my penis. The next day Katie asked Anne if she was planning on having sex with me on our date. She said she wasn’t planning on intercourse, but that she really wanted to see my penis. Katie told her it was probably a good idea but that I’d expect a handjob at least. Anne thought she could do that but asked what she should do when I orgasmed. Katie told her guys liked ejaculating on girl’s breasts, and if you read the earlier story about our first date you’ll see Anne took her sister’s advice. After our first couple sexual encounters, she started taking the pill and planned on losing her virginity to me.
She had learned much more since seeing her parents’ ancient sex manual and knew about the pain and bleeding that usually accompanied a girl’s first time and she didn’t want that happening. The next time she masturbated she eased a finger into her pussy for the first time. Before she had just rubbed on the outside when playing with her cunny. It happened that the next day Katie asked her if we were having intercourse yet. Anne told her that she had started on the pill and was planning on doing it soon, but expressed her concern about being deflowered. Katie told her to hold on and stepped out of the room. She returned to hand Anne a jewelry case and told her it had been a “gag gift” from Sandy for her birthday and that she could use it but that she’d want it back. Anne opened it to find a penis shaped dildo! Katie offered to help her with it but Anne said she’d rather do it alone. If you knew Katie, you would be shocked to know she gave her sister sex training, that she might have posed for the naked photos mentioned in an earlier story, and that she had a dildo!
That night, Anne got the dildo out, and after masturbating enough to get her pussy wet, she licked it to get it wet and pressed it against her vagina. Since it was bigger than her finger, there was some resistance so she pushed harder and it pushed through. It did hurt and there was a bit of blood but she continued to push it farther in. When it was all the way in she slowly slid it back out and then pushed it back in. She did it a couple times but it continued to feel uncomfortable so she stopped for the night. She tried it again the next night and it wasn’t as bad, but still uncomfortable. It felt much better the third night and she actually used it until she orgasmed. She used it one more time before returning it to Katie.
The next thing in her pussy was my cock, which she said she liked much better.
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