I have had the crossdressing bug for many years and have collected some items to fully dress with, such as a wig, makeup, fake boobs and all that makes me look as fem looking as possible. Being in my mid fifties however, there was really no way that I was going to be truly passable or that hot, so I thought  Over the years, I collected my lingerie, heels, wigs and experimented with makeup.  I mostly took it with me on travel to experiment with in the hotel rooms. I bought most of the stuff off of eBay, one piece at a time and hoping I got the sizing right.  In some cases, it was too big or too small and had to be sent back.  

I took pictures of myself and realized that when I went all out, I was a pretty fuckable looking little slut. I also found that when I was dressed fem, I got an incredibly horny feeling myself all over.  Feeling how nice the fake boobs felt through my favorite baby doll nighty got me very horny. I looked forward to traveling on business by car when I could take my whole wardrobe with me and spend the evening getting all dolled up, taking some pics and masturbating.  Of course eventually, my porn tastes moved to watching CDs getting their tight asses poked and I decided that if I wanted to be a total woman, I had to go all the way and let a real man take my ass the way it should be taken, instead of the toys that I had been using up till now.

So I starting cruising Craigslist and answering ads and eventually posted my own.  With the pics that I had, I seemed to be a good target for many other married guys here in the DFW area.  However, like most on Craigslist, many that responded were a total waste of time.  Eventually, I found one that seemed to be a good match. He was about ten years younger than me and wanted to meet at a Motel 6 nearby. That day, I gathered up all my stuff in a gym bag and headed up to meet him around lunchtime.  He went ahead and got the room in advance and said that he would meet me in the parking lot of a restaurant next door to give me the key for me to go get dressed while he waited. This worked out just fine. When I saw his car,  he tossed me the key through his window and said he would knock on the door in about twenty minutes.

I was so nervous with the keys in my hand. He looked like a nice clean guy, so I went ahead to the room, locked the door, got naked and started to get ready.  He did not want me in makeup, so this saved a little time.  First, I put on the fake DD boobs nice and snug, then the crotchless black pantyhose, the black heels, the black see-through nighty, and the short blond wig.  Looking in the mirror, I looked hot as hell I thought and ready for a good fucking.

Within a minute, there was a knock at the door, my heart pounded and I was ready as I ever would be to become a woman.  I stood behind the door, so no one from outside could see me and he came in as I closed the door.  "Oh my God, you are so fucking hot," he said as he literally pushed me against the door and forced his tongue down my throat as far as it would go. He then started to grind his hips into me.  At this point, I realized I liked this a lot and how submissive by nature I really was.  My heart was racing as he pushed me to my knees and dropped his pants revealing about a seven-inch cock that was getting harder and harder.  Without even hesitating, I opened my mouth willingly as he slid it in.  Within a minute, he was literally face fucking me, as I gagged and sucked.  Eventually, I was able to relax and take it down my throat without as much gagging.  Then I started to use my hand to add to his pleasure on his dick and balls.  I was now a cocksucker, liking it and apparently pretty good at it.

He proceeded to get totally naked and pulled me over to the bed where he laid down and told me to keep sucking. Like a good girl, I kept going, experimenting with angles and technique for about fifteen minutes.  I was liking this a lot! The control that I had of his cock and the control that he had over me, excited me to no end. "You suck cock better than my wife and any other woman that I have ever had you little slut," he said.   I was liking the dirty talk too! 

So by now, he was hard as steel and I felt his hand on the back of my head start pushing me down a little more and more.  I was now taking him naturally all the way in my mouth with his balls hitting my chin as he started thrusting more.  Without warning, he let loose and came straight down my throat, holding my head tight against his balls. "Good girl, you know how to take it all."   After a minute or two, he stroked my mouth a few times and then slowly withdrew. "My God, you are good."  I was totally thrilled and satisfied that a guy had used me to get off and liked it.

So the bad news is that he was one of those "one and done" types that had nothing left to give me the good fucking that I needed to get me off.  We laid in bed for about a half hour, with him slowly fingering my ass, but never actually getting into it.  At that point, he got up to get dressed.  Of course, his dick was squeaky clean from me draining him dry and taking every last drop.  He got dressed and left telling me that it was the best blowjob that he had ever had and he would fuck me next time.  Once he closed the door, I lay there very satisfied.  I had been a woman for an hour, satisfied my man and liked it.  I was now hard as nails too and proceeded to jack off to take care of myself before showering and leaving like the used whore that I now was and wanting more.