Prior to this incident I’m about to tell you about, I hadn’t been with a man in 3 years, but the stories I’ve been writing, and the feedback I’ve received have inspired me to get back out and find some cock. There’s only so far you can go with vibrators, dildos, and memories, and at this point, I have definitely taken that road as far as it can go. I figured it was time to make some new memories, and so here we are.

Most stories I’ve written on here have been about my exploits when I was much younger, and figuring out that I was a sissy, or describing encounters that shaped me into the sissy I am today. This particular story is about something that happened just a few weeks ago. I’m in my mid 40’s now, which means a few things when it comes to sexual encounters.

For starters, I’m unable to spend a lot of time looking around for fun like I once could. My days are busy, and despite what you might think about the supposed “ease” of internet hookups, actually meeting someone who is real, sincere, and serious about hooking up is very hard to do. Following through seems to be the biggest online issue. Someone almost always flakes out, and I would be lying if I said that I had never done so myself. I absolutely have flaked out on guys who weren’t as advertised, or who said or did things that made me uneasy about a situation.

Another thing is my age. Let’s face it, hookups are more for younger people looking to explore their sexuality. Those people are almost always looking to and have fun with other younger people, so an amateur sissy in her mid 40’s isn’t going to be appealing to a guy in his 20’s.

Sissies that are in their 20’s have been working full time at being a thirst trap for men since they were teenagers, and they are usually almost always out of the closet, so their families and friends know about them, and they’ve been living their lives as girls full time for a while.

I’m none of that stuff. I still have a regular job, and still haven’t revealed myself to anyone outside of the men that I’ve been with. I’m only a lingerie obsessed cum guzzling whore behind closed doors, so I’m never going to win any sissy beauty pageant online. The other girls are far more beautiful, and will almost always outshine me in a lineup.

It takes a special daddy to see the potential in me, especially if the daddies online are all 20 and 30 something years old. I don’t get offended if they’re not into me. I’m an amateur, and for all intents and purposes, I’m a crossdresser, no matter how I feel on the inside about my sexuality.

I fully understand that these guys are looking for something far more advanced than me when it comes to stages of sissyhood. As I mentioned earlier, some of these younger sissies have had electrolysis, breast and/or butt enhancements, and are on hormones, etc. They’ve been wearing bras and panties and dresses since they were 13 and 14, all with the support of their families and friends. They are girls at this point. I’m happy for them, and totally jealous, but that’s not my reality.

Every so often, that special someone comes along, and those parameters all get thrown out of the window. Such was the case with Larry. I was looking around on a hookup site, when Larry popped into my DM’s. He wasn’t a wordsmith, and he had never been to charm school, but he was a 24 year old young black man who was at least willing to say hello to me, which immediately got my attention.

He had no picture in his profile, and I usually don’t reply to people who don’t show pictures. He also had little to no info in his profile, which is another red flag when searching for men to fuck me online. Out of about 20 profile questions, he had answered about 5. He was 24, 250 pounds, black, he was a top, he drank occasionally, and he couldn’t host. While looking around, I noticed that my DM box started blinking. The message was from “Larry24Top.”

“Sup” was all he typed into the message box. Again, that’s another red flag that I’m probably having a conversation with a bot. I’ll usually give them a one or two word reply then wait. A bot will usually immediately send you a picture of a drop dead gorgeous guy with a raging 9” cock and 8-pack abs. No supermodel man is looking to hook up with me.