I have always been interested in shemales. I played with a few and even explore my bi side with men but I soon got married. My wife and I did a little swinging with bi men but she wasnt attracted to shemale.
After several years, we stop swinging and our sex life slowed down to maybe a couple times a month. Like every male I started watching tons of on-line porn and jerking off. I even started cruising a few "straight" dating sites. But I started to noticed a few women look to possibly be trans women(?) I message one that caught my eye. She was in her late 30's, Latina, long black hair, 5'7" average build and nice ample breast. I was excited when she replied a few days later but she quickly tells me she is a transgender woman and if that was OK. I replied I was hoping she was.
We chatted for a month or so but she was a little leery about meeting a married man. Tell me that wasn't her thing. I don't know if I wore her down or she was enjoying our picture exchange. But one day she texted me asking if I had time to swing by her work for a quick meet and greet. I jumped at the opportunity. As soon as I was off work I texted her and she replied with her address.
When I arrived it was an office building and I texted her I was outside. A few minutes later I see her walking out. She looked sexy, long black flowing hair, wearing a sexy silky top, a short skirt and heels. I'm still sitting in my vehicle and she walked up to my window and we chat for a bit when she says; aren't you gonna invite me into your truck.
I do and she hops in and suggest moving under some shade. As I'm parking, she placed her hand on my leg and we chat. I lean in and we start making out.
OMG she was a damn good kisser. She must of thought the same because her hand was sliding up and down my inner thigh. Nervously I cupped one of her breast and she moans softly in my mouth. I tease her nipple but suddenly she pull back we need to stop, you're making me hard and I can't go back to work like that.