Losing my anal virginity

I have been a closet crossdresser since I was a teenager and I have always wanted to have sex with a real guy, but It was really just a fantasy. At one point I got confident enough to go on web cam and let guys pleasure themselves while watching me play with my dildos. After some time I met a guy in a chat room who lived close by and wanted to have fun with a local crossdresser. We were around the same age and I figured since I just turned 30 it was now or never to live out my fantasy. At this point I had never showed my face to anyone, So I was a bit nervous to meet this guy in person but I couldnt stop thinking about it. I finally got up the nerve to meet this guy in person. We decided to meet the following day at a motel near our area. I got the room and started to get ready. I showered and shaved my entire body, put on my makeup and wig, Slipped on my little "fuck me" panties and bra. I then put on my tiny miniskirt, and paited my nails.I am very thin, 5"10" with my pleaser heels on, as I looked in the mirror I was impressed with the way I looked. I poured a glass of wine and now was the wait for him to arrrive. I had to wait for him to get out of work so I had another glass of wine, The wave of nervousness and excitement hit me. Here I was, one hour away from pleasing a man like I always dreamed.....for a moment I was afraid.....and I was going to cancel..... but my phone went off and it was him....he was on his way to to meet me. I couldn't turn back now, without realizing I gave him my room number....a few minutes later there it was, the knock at the door. My heart was pounding in my chest.....thinking.....you always wanted too be a slut, don't back out now! I answered the door and there stood this guy who had to be 6'5". He towered over me even with my 5" please heels on. He came in looked up and down and said "Nice outfit" ass I grinned, not knowing what to say. Before I knew it he was standing there with just his sexy underwear on. He called me over to him and I started rubbing his MONSTER cock through his underwear. Immediately I felt a tingling in my panties. as I felt my own bulge starting to throb in my little black panties. Wait....Im actually rubbing another guys cock...what am i doing? Next he laid on the bed and I took off my dress. I was standing there in just my panites,bra,and heels while this guy was stroking his cock. He then asked me to turn around for him, exposing my panties that said "FUCK ME" on my ass cheeks. Oh boy ithought here we go!! the moment I was wainting for!! He took his huge cock out of his underwear and leaned over to try to put it all in my mouth. It was huge....much bigger than any of the dildos I ever practiced sucking. He was moaning as I struggled to fit it all in my mouth. Then without notice, I felt a hand rubbing my ass through my panties, then a finger slid them to the side and then he stuck his finger in my ass!! Wow what a feeling sucking this huge cock while getting fingered like a true slut. I was in extacy, I though I was going Cum right there in my panties......before long I was so turned on the I bent over to take off my panties and great big hands picked me up and threw me on the bed doggy style. I remember saying outloud in my girly voice "Please go easy on me, this is my first time." Before I could say anything else, there it was! the hugh cock pressing against my ass....no turning back now.......he rammed me from behind and began thrusting....All I could think was....oh no what am I doing???.... but yet it felt so good. After a couple minutes he pulled out and laid down on the bed and said" get on top" I didnt hesitate and hopped on facing him and guided his huge cock into my virgin ass. It felt so amazing. I was boucing up and down on his cock and I felt like a real girl. My own little cock was bouncing up and down on his stomach and after a few minutes my little cock came all over his stomach and I felt a wave like I never felt before and I realised I just came without anyone even touching my cock!!!!He said "I'm gonna cum now since I made you cum already" he stood up and jerked off while I rubbed his balls and he shot a large load of cum into the back of my thoat. as I realized I was cumming again on the floor. This is a true story, and we have met over the years on a regular basis......more stories to cum.

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