The Day I lost my virginity

Hi there, I am Matt, the one who actually set up this account. A very close friend of mine, Linda, kind of got me started by offering to write a story that I submitted under my pen name, iamscrwd. Thank you Linda…you are so hot!!!

A little about me, I am, now, a married nineteen year old male that did not even lose his virginity until I was sixteen years old. Heck, three and a half years ago, I thought my sex life was going revolve around Rosie Palmer and five sisters, but that all changed when my mother, Kathy, and step father divorced right after my sixteenth birthday, with my mother moving my younger step sister, Katie, and I to a town were her sister lived. It was a whirlwind change as my mother filed a restraining order, got a legal separation, filed for divorce, and negotiated a final settlement, then moved during the course of a couple of months.

Katie, my half-sister, is about a year and a half younger than I and even then at fourteen soon to be fifteen, she had a great looking body. She started blossoming during her twelfth year and over the last couple of years her confidence grew into her being a constant flirt and tease to almost every male from thirteen to forty. Because of her extroverted nature, I pretty much followed her lead as we went through indoctrination at the new High School we both would be attending. Almost immediately, Katie struck up a friendship with an absolutely knockout of a girl named Jen. Jen is a fairly tall girl with a figure that any twenty something would die for. She possessed a rack that was at least a 34 C coupled with a 21” waist on a 5’6” frame and she was only fifteen…holy molly, almost wore out Rosie Palmer and her five sisters dreaming about her. Of course, I had to stay attached to Katie’s hip so my proximity to Jen would be close.

The week before school was to start, Jen called and invited Katie over to her house to go swimming in their pool. Of course, I asked if I was invited too, and received the ok. Katie donned a skimpy bikini that my mom gave her (even though I knew it was wrong, I now had a different scenario for Rosie and her sisters) and just threw a t-shirt over it. Not having a swimsuit, I just wore a pair of cotton gym shorts.

Mom drove Katie and I over to Jen’s, who met us in the driveway and led us to the pool as our mom drove off. Approaching the swimming pool, I noticed a woman with short blonde hair laying face down on a towel and from my perspective did not a have any clothes on. Jen walked right up to her and announced “mom, I want to introduce you to my new friends”. Holy shit, the woman just turned over on her back, peeked under her sun glasses and made absolutely no attempt to hid even one inch of the most gorgeous body I had ever seen, not even in magazines. My eyes tried to take in as much as I could; you have to remember that the only real female parts that I have seen were flashes of sister’s (her teasing) and mother’s (me peeping) parts. Laying on her back, her tits pointed straight up defying gravity with quarter size rings going through her nipples and scanning downward she had a pierced navel, a small barbell that held her clit exposed, and two smaller rings on each side of her smooth as a babies butt pussy. She opened her legs slightly and exposed her slit. I must have been gawking, because she had to say excuse me a couple of times while offering her hand to me to help her up. She stood up, faced me (she was at least 5’8” tall) and introduced herself to me as Linda, Jen’s mom and from my expression, that I must be a virgin. With that, she told us she had errands to run and would be back later that evening. She reached down and grabbed my cock through my cotton gym pants, then leaned forward whispering in my ear that it makes her feel good that a young man can have that kind of reaction to an old woman. She stroked my cock through my shorts a couple of times and then her nipple rings made contact with my chest. My cock involuntarily spasmed, as I shot my wad into my shorts. Then she walked away.

Katie looked at me, the wet spot in my shorts, and Linda walking into the house and said “wow”. Then she looked at Jen and started laughing. Jen looked at me with a crooked smile and asked “so, you really are a virgin aren’t you?” They both had a good laugh as they discarded their overshirts and jumped into the pool. Deciding that the pool was the best solution to my embarrassing situation as my cum was now running down my legs, I too jumped in.

As I was swimming, one of the girls swam underneath me and yanked my shorts off.