Smut book

Part 1 GXB

A Shy Teens Very First Time

The following is a true story with just the names changed. This takes place in a little town in Western Massachusetts where I lived at the time. I was in high school and just turned 19 in my senior year.

I was very, very shy while growing up. I didn't really expand my friends much in high school. I was super quiet and extremely shy. I barely spoke to any girls, except for one. She was in my Temple USY (Jewish religious youth group) and a little younger than me at 18.

Somehow we became close friends and spoke almost daily on the phone. We would talk after school most days. She was also dating my best friend. So I'd see her over his house and at USY activities. Somehow, squishing next to her in car pools. She'd whisper something in my ear on those and get me smiling and I'd shush her so her boy friend Howie didn't catch on. Her name was Cary and she was a 5 foot cute girl with dark shoulder length hair, big eyes, really cute face and body and huge boobs. I was more interested in her older sister who was a year older than me and was more petite as big boobs were not my thing. But Howie was entranced by them. He spoke about those huge boobs all the time, more than the person inside. And Cary knew that, but still stayed with him.

And so it went with Howie telling me he was dieing to get in her shirt and pants and she was going to be his first. Then with Cary talking to me at other times telling me what Howie wanted to do to her and how she wasn't ready and he was pushing her. Then she told me she went on the pill with her mothers permission to be extra safe even though a condom was going to be used.

Nothing happened between them yet. Howie had been pushing for about 2 months and was getting aggravated in his wait. Time was passing. Soon enough I told Cary.

I was going to have the house to myself from Friday afternoon through Sunday late afternoon on a September weekend. My parents were taking my sister to a friends in Salem for the weekend and they were spending the weekend in Rockport. The house was mine to relax in. I only told Cary. I wasn't a partier, which my parents knew, so they weren't worried about that and they left me the other car as I had earned my drivers license a few months prior.

Cary suddenly loved the idea I was going to be alone and wanted to join me for the weekend. I said no as Howie would kill me. But she concocted a plan with a girlfriend of hers a few streets away. Before I knew what was going on, she was ringing the doorbell with a duffle bag of clothes in her hand. I let her in and she grabbed me in a big hug. OK, this was getting interesting. I was kind of shocked by the hug, but gently hugged her back. Having her so close to me gave me an instant erection that I hoped she did not detect. Her first words to me were "I'm starving, what's for dinner?"

I ordered a pizza and it was delivered and I paid the driver and gave a tip. I had been cutting lawns and doing odd jobs and had money and always paid my own way. Cary's family was wealthy (by my standards) and she didn't work other than the odd baby sitting job, and had a nice allowance each week. While waiting for the pizza, I showed her my sisters room and put her bag in it. She went up and changed into pj's and came back down. I had to admit, she looked good and snugly. She told me to go up and change into my pj's which I did. We made sure she was not visible when the pizza came as I knew the delivery person.

The pizza was consumed and we went and watched TV. This was before cable and only had over the air TV or VHS movies. We watched whatever was on. I sat in my usual spot on the couch and much to my extreme surprise, Cary set right next to me. And we started chatting, just like we always did on the phone, but in person. Talking about everything we always did. Only this time she told me how she took Howie's "thing" in her mouth and it exploded. She gave me much more detail than I ever would have wanted and was very thankful it was dark in the room so she could not see the tent in my pj's. Or so I hoped at least.