Kosher Virgins Share A Sabbath Tryst

A Shy Jewish Teen’s Very First Time By nutmegman - Listen to the ► Podcast at Steamy Stories.In 1981, I was a good Jewish lad, living in a little town in Western Massachusetts. I was still in high school and had 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 Carrie. She was in my Temple USY (Jewish religious youth group) and a little younger than me at 18. Carrie helped me overcome my shyness with her when we were very little, so that we remained close friends and spoke almost daily on the phone throughout our teen years.We would talk after school on most days. She was also dating my best friend. So I’d see her over at his house and at USY activities. Somehow, I was usually squished up next to her in car pools. She’d whisper something in my ear on those moments, and get me smiling, and I’d shush her so her boyfriend, Howie, didn’t catch on. She was just 5 foot & a cute girl with dark shoulder length hair, big eyes, really cute face and body; and huge boobs, really. I was actually more interested in her older sister who was a year older than me and was less curvy. Big boobs were okay, But I wasn’t obsessed with huge boobs, but Howie was. Howie was entranced by them. He spoke about those huge boobs all the time, more than the personality inside. And Carrie knew that, but she still stayed dating him. And so it went with Howie telling me he was dying to get to her tits & twat, and how she was going to be his first. Then, with Carrie talking to me at other times, she was telling me what Howie wanted to do to her, and how she wasn’t ready, and that he was pressuring her. Then she told me she went on the pill with her mother’s permission to be extra safe even though a condom was going to be used if & when Carrie did have sex. Nothing happened between them, yet. Howie had been pushing for about 2 months and was getting aggravated in his wait. Time was passing. A bit about Jewish views on fornication: Unlike Christian teaching that all sex outside a marriage is clearly a serious sin, Jews are taught to make a reasonable effort to follow the religious law. Once a Jew believes he’s tried to do his best, he doesn’t feel shame for ‘falling short’, spiritually. He met his obligation. A few weeks after the start of our senior year, I told Carrie that 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 friend’s home in Salem for the weekend and they were spending the weekend in Rockport. The house was mine to relax in. I only told Carrie. See, I wasn’t a partier, which my parents knew, so they weren’t worried about that. They also left me the other car as I had earned my driver’s license a few months prior. Carrie suddenly loved the idea that I was going to be alone and she wanted to join me for the weekend. I said; “No because Howie would kill me”. But she concocted a plan with a girlfriend of hers who lived just a few streets away. Howie evidently thought she was having an ‘all girl weekend’. He figured he wouldn’t see her at synagogue, either. Sabbath Night Late Friday afternoon, about 5 minutes after my folks were gone, & before I knew what was going on, Carrie was ringing the doorbell with a backpack of clothes in her hand. I let her in and she grabbed me in a big hug. Okay, this was getting interesting. I was kind of shocked by the hug, but I 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. I had been cutting lawns and doing odd jobs and had money and always paid my own way. Carrie’s family was wealthy (by my standards) and she didn’t work other than the odd babysitting job, and had a nice allowance each week. While we were waiting for the pizza, I showed her my sister’s room and put her bag in it. We made sure she was not visible when the pizza came, as I knew the delivery person. She went up and changed into some flannel 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. The pizza was consumed and we went and watched TV. 1981 was before cable TV (as we know it today) and we only had over-the-air TV. We watched whatever was on. I sat in my usual spot on the couch and much to my extreme surprise, Carrie came & sat right next to me. 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 that it was dark in the...