Chapter 1: Mom Helps Me Get Ready

At sixteen Randy was a year younger than me, a junior at my high school. Randy and I each had some firsts with each other. To start, he was the first by I dated that was younger than me. There was the first time we dated when I gave him his first blowjob and got to be the first girl he’d had sex with. Interestingly it was also a first for me as he was my first and only virgin, at least so far.

Randy also had an older sister who went to a local college and lived at home. I’d never seen her as it seemed she was always out somewhere whenever I was at his house but Randy told me that she was twenty and pretty much ignored him most of the time. Sounded like a typical brother-sister relationship. As a general rule he seemed to dislike even talking about her. Not that they didn’t get along, he just didn’t seem to enjoy discussing his sister with his girlfriend.

As for Randy’s parents, they were pretty conservative and I was never quite sure if his mom approved of me or not. What I DID know was before I started dating her son that she had always given me “the look” when I would wear one of my skimpier outfits to a church event - typically the only time we crossed paths. Now that her son was dating me on a regular basis no doubt she wouldn’t have been happy unless I wore nothing but long dresses up to my neck with a chastity belt underneath!

After our first date Randy took me out a couple more times. It was difficult with school nights and such. It seemed unbelievable in this day and age but Randy’s parents imposed a 9:00 curfew on him if he had school the next day! thankfully Despite these obstacles he still found ways to fuck me a number of times. Really, what’s the point in dating a guy if I wasn’t going to get enough sex? We even did it one night on his porch while his parents were in the next room watching TV. He may have been scared the entire time but it just proved yet again a teenage boy’s dick operates totally independent of his brain!

It was a Saturday morning and Randy called me to tell me his parents were away for the day and his sister would be out for classes in the afternoon. He was excited since it was rare he ever had the house to himself and while my parents had no problem with him coming over, he was still shy about fucking me when they were home. So when he asked me if I’d be interested in coming over to his house to take advantage of the situation, it sounded like a golden opportunity so I quickly agreed. Although it wouldn’t be as exciting as it would have been if his parents were home, at least it was a step in the right direction.

This morning I was being lazy and hadn’t gotten dressed yet so after I hung up the phone I went to my dresser and picked out a tight pair of jeans and a thin cotton blouse. I was about to put them on when I thought about Randy and an idea came to mind. Rummaging through my drawer I found a new pair of white cotton panties and a plain white bra that clasped in front. It was rare for me to wear underwear to start with but the way Randy’s mom was I found myself wearing more underwear while dating him than I think I had all my previous dates combined! Just as I was about to put my pants on my mom walked by and saw me.

“What’s the occasion girl? Judging from the laundry, you’ve been wearing underwear lately. Anything you need to tell me?” she asked.

Seeing the genuine look of corn on her face I almost laughed. Did she think I might be pregnant or something like that? Then I then explained about how Randy’s parents were such stick-in-the-muds which was why I’d been dressing so conservatively lately. Then I mentioned Randy was going to be picking me up soon and that his parents weren’t home. Confiding such information with her wasn’t unusual for me as I tell my mom everything and she’s always interested in what I do with my boyfriends. In fact, I think it turned her on to hear about how my boyfriends fucked me and I knew she often masturbated after some of our mother-daughter “talks”. Therefore my mom already knew I’d been fucking Randy recently so it didn’t take much for her to figure out what my plans were for the afternoon. She stepped in my room and took a good look at me standing there in just my bra and panties.

“So ... what’s up with the innocent schoolgirl underwear today then?” she asked. “I know that Randy’s mother is a bit of a nutcase but if she’s not going to be there then why bother?”