Author: OwlPlenty4828

My first time having a strapon used on me [MF]

I have been fortunate enough to have a variety of sexual partners. Younger than me, older than me, short, tall, black, white, skinny, thick and every type in between.

I am straight. But love my ass being played with. Cupping the cheeks, a finger a tongue I’ll take what I can get.

I’ll build up to the strap on play.

I had sweet girl named Becky, she was a virgin the first time we met. Not for long. She asked “ What’s your fantasy”. I told her I wanted to try a finger up the ass blow job. From there I was hooked on ass play.

Heidi was an absolute freak nothing was off limits. 8 years older than me always horny always drunk. She would lick my ass when ever I asked and she was the first one who used a toy on me. Little mini egg vibrator. Yum!

After that I was in a long term relationship with Cyndi she loved her ass licked. And would occasionally lick mine and finger every once in awhile.

Fast forward a few years I am with women that just weren’t into it. Next!!! Read more »

Yup I did a thing. We didn’t plan on having sex [MF]

We didn’t plan on having sex but.

That’s how this story ends and starts. I had just moved to Fort Myers Beach from New England. I had set up a new business down here and had spent the week settling in. Getting to know the area and doing a little marketing and introducing myself to some pertinent business in the area. I had known some people down here so Steve was taking me around town showing me the nooks and crannies of the area and where the locals go. So I am thankful to this guy. Buy him dinner we are having drinks and then he calls his sister Jen. She joins us. I’ve met Jen a few times she’s a couple years older than me she’s cute but I don’t think anything of it. She’s married and I am in a committed relationship. We are just 3 people having fun.

Then someone says the line we’ve all heard a thousand times. “I know a dry cleaner that’s actually a place to get Coke”. Brilliant idea when you think about cars coming and going all day. Shit I had done that stuff in a long time so I figure what the heck we are having a good time. It’s a beautiful afternoon. Why not. Run to the cleaners do a bump or two in the car, swing by the grocery store get some food and liquor. Read more »

My first time [MT]

I’ve received a quite a few requests so here it goes. My first time with a Trans woman. She was a man transitioning to a woman, well into hormone therapy and a few surgeries, but she still had her penis. My fascination, like many I am sure, started with the first time I stumbled across a trans porn video The star was Camilla DeCastro she was Brazilian, tan slender, feminine but with a big cock. I was hooked. I wanted to see what it was like. So after some online research I found Craigslist and then the ever famous Casual Encounters T4M section. I had just moved to St Petersburg, Fl I was single so I figured “What the Hell?” I knew I wasn’t into men per se but these feminine creatures with their cocks were intriguing for sure. Read more »

I am straight but…. [MT]

I am happily married masculine guy that is in good shape. But when no one is home I will but on some lingerie and use some sex toys to pleasure myself. I love the feeling of the soft stockings on my body. Occasionally my wife will use a strap on me but it’s rarely. Once year maybe and while it excites her because we are “pushing limits” she will also complain “That things a pain in the ass to put on etc” (kind of the point 😁) Our sex life lately is I do the foreplay massages etc and when she cums a few times and am told to hurry up. Now she is a stay at home parent and when I am not on the road I am home with no work obligations… we have time. But all this is within the realms of normal. Read more »