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, and he asked more about what I was into; he told me he wanted to kiss me, hold me and own me, he asked if I liked anal. I was honest with him and he told me that I’m really going to enjoy myself tonight; he said he would bring condoms and lube and suddenly it started to feel very real. Around 6pm I started getting ready and my slutty little heart was pounding, could I call this off now, what if he still turns up, am I gay? We exchanged numbers and he texted my around 6:15 that he was on his way….oh my god!!! It was too late now! I sprayed my ex-wife’s Victoria Secret perfume and did a final mirror check, I was barely passible but I didn’t think my new Daddy was going to mind.

6:40pm I get that text, “On my way up babe, be ready!” I stood in front of the door feeling very ashamed, what a whore! I saw him there and I opened the door quickly so no-one would see my sin, he was much taller than I thought and he immediately kissed my square on my lips, he then looked me up and down and said, “mmm very nice.” I had never done this before so I only had porn to go on, so I turned around and grinded my ass on his cock. He lifted my skirt and held it and stared at my ass, I smiled and said in my girliest voice, “Do you like Daddy?” He then pressed me against the wall and ground his cock into my butt, I could feel his cock beneath his jeans. I turned around and started to undress my Daddy, he helped and just like that he was naked in front of me with about a 7 inch thick hard cock. I smiled and got on my knees and did the previously unthinkable, I kissed his cock, licked it, and opened my mouth to take it. I started to suck and go back and forth, my mouth was filled with saliva and pre-cum, that sweet salty taste, surprisingly a lot like my own. “Ooooh yes Mandy, what a good little slut you are,” Daddy put his hand on the back of my head and helped me find his rythm, I wanted to be good and I couldn’t tell if I was, but I could tell he was enjoying it. I wondered if he would cum and this would be our entire evening, me being his little cock-sucking schoolgirl? Daddy suddenly interrupted my thoughts with, “Bend over the bed you little bitch, I need that ass!” This startled me and was a little more aggressive than I wanted, but I obliged and said submissively, “Yes Daddy!” He slapped my ass hard and again, the slap sounds were super-loud and I suddenly became self-conscious, my neighbors must have heard, oh my god, what will they think, are they now pressing their ears to the walls? Suddenly my Daddy leaned over and kissed me, “Oh you’re such a good little whore, you ready to be owned?” “Yes Daddy!” He started to kiss my ass with his tounge, licking as deep as he could, I could see in the reflection of the TV that my skirt was on top of his head, I used to be married…what the hell was I doing? My Daddy walked to his jacket and pulled out a tube of lube and his condoms, I stayed bent over, my heart thumping, my face on fire. I heard the tube squirt and felt a slick finger rubbing my hole, he slowly entered and I moaned, “Oh yeah!” I felt two fingers and he started fingering me very slowly, I was mildly embarassed that it felt so easy, I thought I was going to be super tight and nervous. “Get up on the bed with your ass in the air,” my Daddy said, I quickly crawled and obliged him; I got a little scared, was he just going to pound my ass? I suddenly heard a click and turned around, he was taking phone pics of me, what the hell? “Daddy, that’s very naughty!” He quickly got up on top of me and pressed me down, “I own you remember? Daddy gets what he wants.” I loved that and felt very turned on, I then saw Daddy put a condom on his thick hard cock and he gave my little ass 2 last deep fingers. Oh my god, its too late for me now, well here I go! I felt his cock at my entrance and relaxed my ass as much as I could, “Fuck me Daddy!” His cock was way thicker than I thought, he slowly entered, moaning as he did, no thrusting, just slow pressure as he got deeper. “Oh my god baby, what a good girl you are,” he said. “Oh fuck me Daddy,” was all I could say, and that he did! He pressed me down and put his arms around my shoulders as I felt him thrust deep into my ass. I was expecting pain, but it honestly just felt really good with a very hot feeling in my ass. “Fuck yeah,” my Daddy was saying as he pounded me, I then saw his phone come over in front of my face, he has gotta be kidding I thought! “Smile baby,” he said in a very sleazy voice, “I smiled and didn’t protest realizing it was the video camera function, I played up to it like a good slut, “Oh yeah Daddy you fucking own me!” At that I heard him grunt and he dropped his phone and pulled out, “You nasty little whore, ride Daddy’s cock, look away so I can watch your ass.” Daddy rolled onto his back and I didn’t hesitate, I squatted down reverse cowgirl style and felt his cock stretch me a little, then I rode while he grabbed my ass to thrust me harder. My plaid skirt was hiding my cock and the large dick in my ass, “Oh this feels so good,” came out of my mouth, what the hell was I doing? He started slapping my ass and making a lot of groans, the neighbors had to hear, I didn’t care at that time, they can have me too. Daddy was pacing himself, so he pushed me off and grabbed my head and pushed it to his condom wearing cock. I cleaned it off and tried to get as much in my mouth as possible, Daddy grabbed my face and pulled it to his and surprised me with a deep kiss. I sat in his lap kissing him, he slid his dick into my ass while I faced him and kissed him; I slowly grinded and we kissed passionately; “I LOVE YOU DADDY!” What the hell did I just say? “You’re my secret fucktoy now, I fucking own you,” was my Daddy’s nasty reply, no love! “Alright bitch, now you’re gonna eat cum.” My Daddy rolled me over the side of the bed and got me in the pile-drive position, I had told him in my emails about how I started my day, oh fuck, he’s going to make me swallow his cum! I was losing all control and I yelled, “Fuck my ass Daddy!” He quickly grabbed his cock and forced it into my ass and fucked me deep. I looked up at him and realized that I actually really enjoyed this feeling, my cock was close to exploding, “Daddy I’m gonna cum!” He quickly grabbed my cock and forced it towards my mouth, which I opened wide and put out my tounge, feeling the tightness in my ass drove me over the edge and I came in floods into my waiting mouth, “Oh yeah you little whore, hold it in your mouth, I’m gonna cum all over your face!” After cumming I felt the usual remorse and saw the dick in my ass and thought how pathetic I was. At that moment he pulled his cock out and moaned loudly and shot thick streams of cum across my face, I am so pathetic. “Oh what a good girl, now come up on the bed and get under the covers with Daddy.” I wasn’t sure if I should swallow, but he turned my face next to his and said, “Okay now swallow like a good girl, then lie there with Daddy’s cum on you.” I instantly swallowed and found myself very turned on (no remorse). I looked at him again, “I love you Daddy!”

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