My only male to gurl relationship - Sex Stories

My only male to gurl relationship

This story describes my only ever male to gurl relationship; of course I was the "gurl." I was living in Wisconsin about 30 years old and I'd just broke up with my wife of 6 years. While I was married I would regularly dress up in some of her little dress up outfits; mainly schoolgirl! I also experimented with dildos and plugs, but I considered myself straight and didn't indulge too much. Once we broke up I moved to a hotel (Extended Stay) for about 2 months while I got my life together. I kept my job and lived a normal life, except for what I'm about to write about. It was my second night alone and I was trolling Craigslist and curiously looking for older gentlemen, getting turned on by their cock pics and statements of desire. I had picked up a schoolgirl outfit and pigtails wig a day earlier and I decided to dress up for my own amusement. I am 5 9, 180 lbs and pretty athletic, so I fit my little outfit quite well. I had on a pair of white stockings (my favorite item), a plaid skirt, a white thong, a white button-down shirt and my long pigtails brunette wig. I applied lipstick but I was insecure about it, I felt like it didn't quite work; but what's a gurl to do? I was laying on my bed with my laptop stroking myself to the men on CL, looking for the perfect one, I wasn't sure if I was going to reply at that time. The night went on like that and I woke up the next morning dressed like a slut, but feeling very horny. I decided I just had to taste cum, so I did it the only ...

... way I knew how, and leaned off my bed on my back with my shoulders square on the floor and put my stocking-clad legs in my face and brought my cock as close to my face as I could. I am quite flexible and can almost touch my cock with my tounge; I furiously jacked myself and opened my mouth wide and put out my tounge. I came so quick and took every drop in my mouth; I quickly got on my knees and then to my feet, I walked to the bathroom feeling a little ashamed and spat my thick salty cum into the sink, I was too ashamed to swallow. I had a really crappy day at work, on my lunch I was on my phone looking for "my guy," suddenly I caught this one who lived very close, I remember he was 50, 200 lbs, 6 foot and and a great looking cock; he was specifically looking for a gurl he could play Daddy to. I replied to his posting and sent him one of the pics I had taken of myself in the schoolgirl outfit. I remember buzzing with excitement and getting a massive hard on as I responded. While at work I was constantly distracted checking my phone; and after 2 hours I got the reply that changed my life: He sent me another pic of his body and cock and asked where I was staying and if I was free after 7pm? He even signed it, "Daddy!" My heart started pounding and I made an excuse to leave work early. Once I got in my car I gave him my hotel and room number and called myself, "Mandy," I got a little scared, was this guy a pyscho, had I gone too far? By the time I got home I had 3 emails from him, ...