Sexy Story: The First Time

Even as I sit here I can’t believe I’m putting these words to paper. I never thought I would be one of the women in the stories of sexual adventures, but life has a funny way of leading you in directions that you can’t always predict.

I had been married to my husband about 8 years when our entire relationship changed. He was my only sexual partner but for years Chuck shared with me his dreams to have a threesome. It was no shock to me; he is a man, afterall. However, what I was totally shocked to hear was that he wanted to see me in bed with another man. I always thought of Chuck as more courageous than I, and didn’t think I’d ever have the guts to go through with having sex with anyone else. We talked about it on and off each time I would get so turned on thinking about it that my g-string would be completely soaked. But I never really thought it would happen. Some fantasies are meant to stay fantasies, or so I thought.

One night we were out with some friends and drinking heavily. Pretty soon I was in full on flirting mode with one of our friends, Jake. Flirting with Jake was like breathing air; you don’t even realize you’re doing it because you get swept up in him. He is a ladies man to say the least; charming, handsome and a little bit dangerous and always flirting back.

Soon we were at the bar doing shots and I felt a hand on my leg. Thinking it was Chuck I didn’t say anything. Except I realized that Chuck was sitting at the table a few feet away, so it was not his hand reaching farther and farther up my thigh. When I looked down I realized it was Jake, who was wearing a devilish smile from ear to ear. My pussy began to tingle with excitement as he leaned in and said to me “I’ve always wanted to fuck you until you scream for me to stop”. By this time my g-string was dripping wet and at any second my hard nipples could come bursting out of my shirt. I looked over and Chuck raised his glass to me, he had seen the entire interaction and from the growing bulge in his pants he was enjoying the view.

When Chuck joined us Jake took his hand away and tried to act like we were just two friends at the bar. Chuck took Jake’s hand and put it back where it had been, high up on my thigh and pushed it closer to my wet pussy. Jake realized I was completely shaved, and he could feel how wet my pussy was. Without another word we settled our bill and headed for our house.

We made it home and picked back up where we left off. I had worn my sexy lingerie underneath my dress that night so I lay out on the bed in my black lace bustier and matching g string while both men revealed their excitement in the form of rock hard cocks. Jake started to kiss me while Chuck took his tongue to my bald pussy. Soon I began to moan into as Chuck made me want to scream. I was stroking Jake’s cock which was amazing to look at. It was long, thick and rock solid. I was begging to be fucked and Chuck said it was Jake’s go first.

I hesitated for all of 3 milliseconds when I realized we were actually going to do this. I looked to Chuck for confirmation that he was OK with it and was greeted by his cock being shoved down my waiting throat. I gagged a little at the shock of how deeply he thrust it into my mouth. Having known Chuck for a long time I could tell he was more than OK with the situation by the cock pulsating in my mouth. Jake was taking his time rubbing my clit with the head of his gorgeous penis. It felt like heaven and hell all in one, I was so ready to be fucked!

I was licking Chuck’s cock all around when I started to feel Jake push his warm, hard cock into my pulsating pussy. He was bigger than Chuck, but not so much that it hurt, it was sheer pleasure. I was instantly moaning and thrashing around while I had one cock in my mouth and one in my pussy.

Chuck was about to cum and he asked me where I wanted it. I pointed to my face just in time for him to shoot it all over my waiting cheeks, eyes and lips. He took his cock and rubbed his cum all around my face and then I licked his cock clean.

Jake was fucking me harder and harder now and I felt like I was about to explode. I stopped myself just in time and managed to get the words out that I wanted to be double penetrated. Chuck was quick to his feet at my request. And we positioned ourselves so that Jake was deep inside of my pussy while Chuck lubed up his cock for round two in my ass.

Jake got me going again and I was begging for more when Chuck slowly slid his cock into my waiting asshole. The fullness and pleasure of double penetration took me over the edge and I sprayed cum out all over both cocks in an explosion of sheer ecstasy. My pussy and asshole tightened around their cocks so hard that they both came with me. We rolled over into a heap of sweaty, naked bliss.


It was a night I could never have imagined until I tried it. And it was better than I ever could have dreamed. Chuck and I were closer than ever after that night. We agreed to keep our options open about having Jake over again. And the options were certainly open the next time we saw Jake in person… but that is another story for another time...