I once had sex with a guy

We were in high school. He was my best friend. We had giving each other countless hand jobs and blow jobs. He wanted to know what it was like. It did not last long... not more than one stroke in fact. I entered him and it was too much for him. I pulled out. He was nearly in tears.

Strangely, I've wanted it to feel him inside me even more... but I left it alone. I held him while he adjusted his composure. He was embarrassed that he could not take me. I was embarrassed that I did not have the experience to give him what he wanted in a pleasurable way.

I want to know what it feels like to give that pleasure to a man. I want to know what it feels like to feel the pleasure he gives.

Break up sex... to say goodbye

Some 13 years ago, I packed her things and told her it was time to move on. I knew she was cheating on me and I had been cheating on her... with my ex. We talked it out. We cried. We decided we wanted one more time together as our way of making a clean break. We took off each others clothes, kissing as passionately as the first time we kissed. We rolled around in bed... touching and kissing. She climbed on top of me and slid my cock inside of her. We didn't use a condom this time. We wanted to feel each other. Yes, that was a risk, but it was one we left to fate. I slipped my finger deep into her ass... something I had never done before. She didn't take her lips from mine, or her hands from my cheeks, the entire time we made love. It was amazing. Parts of us questioned if we should part... we were so good together in bed. But we both knew it was time. The emotional after-shocks were tough for some time, for both of us. I still love her. We're both married now, me to the ex I was cheating on her with. Her... I am not sure. We didn't keep touch.

I took it all the way!

I've played briefly with toys in my ass before... a small butt plug... a thin flexible vibe... once I tried my wife's full size dildo... about the same size as my own cock. I admit it hurt like a bitch and I stopped after just a couple of seconds I decided I wanted to know how it felt. If my wife can take my cock in her ass, why can't I handle it? So last night in my hotel room, I'm looking at porn and I happened to bring along a couple of my wife's dildos and my pussy flesh light.

I got out the smaller of the two dildos. A very thin, vibrating, blue waterproof toy shaped like a penis ribbed with some pretty harsh ridges. I managed to get it inside me a good few inches. I turned on my camera and the vibe and fucked myself with the fleshlight. It felt pretty good.

Tonight though... I took her big one. It's by far larger than me... both in length and girth. A vibrating, cyberskin realistic cock. It took me a while but I got it inside me a few inches. I had some trouble getting it in very far. I turned on the vibe and tried to relax and watch some porn. A good 45 minutes later, with is still in my ass, I pulled it out and relubed. I slid it back inside me and sat on it. Wow!! All the way in. It didn't hurt like I thought it would. I toyed with sliding it in and out and had on some good female on male strap-on porn. I came pretty hard but I have to say that the best part is how I felt afterward. I felt more satisfied than I can ever remember after jacking off. I really wonder how the real thing feels. Even now, over an hour later, I feel fulfilled. I'm so proud of myself for taking it. I can't wait to do it again.

Cumming on Cam

I brought my webcam with me on the trip this time along with an anal vibe. The vibrator is "jointed" and the ability to bend it allows the angle to be just right for hitting the prostate right where I need to.
I got on yahoo messenger with a guy from Newbie Nudes and we jacked off together. He did a really good job of chatting me up and helping me to get off. Between the vibrations in my ass... which were at full speed by the time I came... and the hot chatting about group sex involving our wives, it was a really good time.

I came pretty hard and watching him jack off while he watched me doing it was really hot! I have to admit that it was also hot.... and a little humiliating... when he asked me to turn around and show him the purple vibrator I had stuck up my ass. He told me to pretend it was his cock... well, I was already doing that!

I can't wait to cam again!