My Not-So-Hot Valentine Virginity Story

It's Valentine's Day, and tomorrow is the anniversary of the day I lost my virginity at age 20.  I got to reminiscing, and although the lucky fellow was only in my life for a few brief months, I can't forget him, even if I wanted to. A girl never forgets the day she loses her virginity, whether it was a pleasant experience or not. The day after V-Day I always think about that day, many many years and men ago. I feel both giddy and wistful.

I was a late bloomer---I really didn't become very attractive really until I hit my 40's. All during my childhood years I had unruly hair and glasses. By 6th grade, I did have a knockout body.  By high school, although flat irons hadn't yet been invented, I did learn how to properly blow-dry my unruly curls out straight. I had my first serious boyfriend, although we never got past 2nd base. It just didn't occur to us I guess. We graduated and went our separate ways, and by my second year in college, I had contacts but no social life. I was a serious student till I met Jesse.

I was working at a fast-food restaurant, and one of my co-workers, Glenda, was a blonde bombshell with an equally cute boyfriend named Frank. Frank came into the restaurant late at night often to hang out and wait for Glenda and the restaurant to close and drive her home.  Frank would often wink at me when Glenda wasn't looking, and it made me titillated and uncomfortable at the same time. Jesse was Frank's best buddy.

This was during the time period when "Rocky Horror Picture Show" was playing at midnight in all the theaters. Frank worked in one of the local theaters, and one night, after work, he drove me and Glenda to the theater to see the midnight showing. Waiting for us there was his friend Jesse. We hit it off immediately, and I guess we became boyfriend and girlfriend.

After a few weeks of dating, which included heavy petting at drive-in movies (we ditched the theaters), it was Valentine's Day. I don't remember why he couldn't see me ON Valentine's Day, but we got together the day after. I went to his house; I think he lived with his dad, I don't remember, but we were alone. He took out a joint, and although I was quite a prude at the time, I didn't want him to know it, so when he passed it to me, I took a hit off it. It didn't take much to make me high. One thing led to another, and all our clothes were off. He was so good-looking---think Erik Estrada in his hey-day (which was during this time period!)

All I remember is, it went in. Yep, slid right in. It hurt, I bled a little, but it went in. We did it exactly once, and he broke my heart and broke up with me the following week. I sobbed for days, then realized at least he'd given me the gift of breaking my hymen so I was able to FINALLY, at age 20, wear tampons!!

I think back to that moment, so long ago, and how it affected my future sexual relationships. I don't think it has a thing to do with how I've ended up a swinger/polyamorist, although I do remember something very hot that happened with Frank and Glenda one night. Glenda had taken me along on a family camping trip one hot summer weekend, and we shared a tent, just the two of us girls. Unbeknownst to her parents, Frank snuck in and visited us one night. It was a beautiful summer night, the dark sky filled with stars, and everyone was quiet in their tents. We sat by our small campfire talking for awhile, then went into our tent. It was a very small tent. I crawled into my sleeping bag, and Glenda and Frank were in her sleeping bag. As I tried to fall asleep, I heard them whispering, but left them alone. Like I said, it was a very small tent. They were within touching distance, had it occurred to me. It wasn't long till I heard very heavy breathing, and soft moans. I was shocked and aroused, laying there in the dark, facing away from them. Wide-eyed and horny, I heard my friends fucking and wanted desperately to watch. Although it was dark, I'm sure I could've seen quite a bit given that the campground had some dim lighting. I laid there as still as a statue, and afterward, as soon as I was certain they'd fallen asleep, I masturbated, laying right next to them. It was by far the naughtiest thing I'd ever done.

Sure pales in comparison to the naughty things I've been up to ever since.

Do you have a loss of virginity story you want to share with me? You can write me at naughtyannahotwife@gmail.com. I'll keep it to myself; I'd just love to hear it.