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It has been quite some time since my last story and I've had many experiences in that time and especially from when my last story ended, enough that I can't really remember what happened after the last story so I will continue with random stories that are all 100% true.....so anyways here we go
Over the years I have evolved greatly in my sexual appetites, I started as a Vers bottom in my younger days and eventually I went through a top stage where I preferred the younger thinks, I even went through a cross dressing stage which I will explore in this next story.....
I was in school in Vancouver and was away from the wife and kids and was free to really explore, I had started fantasizing about dressing in women's clothes, I went to a store in the mall and even bought some, panties, a couple of dresses, a bra and some lingerie. I would dress up and prance around my dorm room with my hard cock bulging out of the panties, I felt very hot and pretty, I am very fit and I must say I did look very hot.
One day I posted an ad on Craigslist looking for someone I could dress up for, I had several replies but nothing really caught my eye until I saw one from a guy named Ron "hey there I saw your ad and I think this looks fun, I used to have a friend just like you who would dress up for me and I thought it was a hoot how he lost himself dressing up for me, I have lots of clothes and toys we can play with and I have my own place as well, I hope to hear from you" and along with that he sent pics of the toys and clothes he had and his dick of course, I was immediately intrigued and so I answered him back and we chatted a bit, he told me about his friend and how he used to pretend that he was a female relative of his, he was an older guy in his sixties and wasn't sure if he still had it in him to really fuck anymore but he had plenty of toys for me and I could suck him all I wanted, I told him I'd like to meet. I had kissed guys before but I told him it wasn't really my thing so that may not happen and he said that was disappointing but he understood, the truth is I do love to kiss but only with someone I am very attracted to, I'll suck anyone's dick but won't kiss just anyone lol. We continued to talk and I said it would be hot if I pretended I was his daughter and he loved it, we decided that I would be Donna, the name of his real life daughter I might add and from then on he was simply known as Daddy. Anytime we talked after that I went into my persona of Donna and he was My Daddy.
We Finally came up with a time to meet after school one afternoon, I was at trade school at the time. I packed up my clothes and caught the sky train to his place, I was incredibly nervous, despite having talked quite often we had only exchanged body pics at that point and I really didn't know what my Daddy looked like. I arrived outside of his building and texted him, I was shaking and very nervous but he came down and I was pleasantly surprised, he wasn't a large guy, about my height, slim and I was very happy that he was actually quite handsome with a white goatee and the white hair to match. We had our introductions and I could see he was also nervous, after a silent elevator ride we arrived at his apartment, once we got inside I immediately turned into Donna, I spoke in a girly a voice as I could do lol, he mixed me a very strong drink which I slammed down and he showed me his clothes and toys that he had on his bed.
I told home to sit down and I would start to get dressed up, I was feeling that drink already, I took off my clothes and put on some panties, stockings and a very tight dress to start, I came out of the room and he had mixed me another drink, I stood in front of him and showed myself off, I acted as feminine as I could and he explored my body with his hands, we sat on the couch beside each other and started talking while having our drinks, we were bit very much in Character, I WAS Donna his teenage daughter who was curious about boys and we played along with that, he was telling about what boys expect from girls and I just looked at him and kissed him fully in the mouth, our tongues explored each other's mouths and I sat in his lap and continued to make out, he was very happy because he was really into kissing, it was very nice. "Daddy?" I asked and he replied with a yes "Can you show me your penis? I've never seen one before" he stood up and removed his pants and underwear, he had very nice and thick 7" uncut cock already dripping with precum, I told him it was very nice and asked if I could touch it, he said of course Donna, so I grabbed it and started stroking him
"is this what the boys like Daddy?"
"Yes Donna but there is something else they will want"
"What is it Daddy?" "
"Do you know what a blowjob is Donna?"
"No Daddy what is that?"
"Put your mouth on my penis Donna and stroke it with your mouth"
So I did, I put his cock in my mouth (I had sucked many cocks before and my skills are pretty damn good) I worked his shaft and licked his balls, I deep throated him and took it all down, as his cock was buried in my throat I stuck my tongue out to lick his balls, clearly I was no amateur but we stayed in character of course, I changed clothes several more times and would come out an put in a show for him, dancing seductively, we would kiss and I would suck him some more, he had the most Precum that I have ever came across in all the dicks I have sucked and I loved it, I was pretty drunk at his point and all inhibitions were long gone, I was Donna and I was feeling very slutty. I had one last outfit, a nice black teddy, a g string and some black stockings, I was looking very hot and slutty, I came out again showed off for him, I Bent over and his hands explored my ass, he put his finger to my hole and said the I had A very nice pussy, I was loving this
"Daddy?"
"Yes Donna"
"Can you tell me what sex is? I hear the boys at school talk about it all the time"
"Yes Donna of course, Sex is when a boy puts his penis in your vagina"
"Really Daddy?"
"Yes Donna"
"Daddy?"
"Yes Donna?"
"Can you show me?"
"Yes I can Donna, let's go into the bedroom"
We went into the bedroom and he took out his toys, he had three and they varied in size, small, medium and large, he got me to bend over on the bed for him, he lubed up my hole and stuck a finger in
"Oh Donna, you are very tight, we will start with a smaller toy and go from there"
"OK Daddy, you know what is best for your little girl"
He took the smaller toy and slowly worked it into my pussy, I took it No problem, I was eying his cock the entire time, that was what I really wanted but he was reluctant, he felt at his age he couldn't fuck very good anymore, but his cock was hard as a rock so I thought I would just play along for now. He worked the toy in and out of my ass, slow and deep as it would go, he asked if I wanted the next size up, I eagerly said yes, so he grabbed that one and put it in, it slipped in as I was loosened up now and also pretty drunk, I was in full slut mode and I wanted that cock in my ass. He fucked me with the toy
"Oh Daddy I like that!"
"Good Girl Donna"
"Will the boys like me Daddy?"
"Oh yes they will my little girl"
"Daddy, I want your penis inside me"
"I don't know Donna"
"Please Daddy, I want it so bad, it is so hard Daddy"
"Alright Donna, since you have been such a good girl"
He then took the toy out and I went to the edge of the bed and presented myself for his clock, he put the tip to my hole and eased it in, it was wonderful, he pumped in and out very slowly, grabbing my shoulders and putting every inch in, he picked up the pace a bit and started fucking me good, he had definitely underestimated himself, after some time he pulled out and told me to suck his cock which I happily obliged, he lay on the bed and I put him in my mouth and cleaned my ass juices off of his cock, he told me he was getting close to cumming so I picked up my pace and went deep and hard on his cock
"Oh yes Donna, keep going my girl, yessssssss!!!"
His body spasmed and shook as he filled my mouth with his cum, I took the cook out of my mouth an let a little cum drip down my chin while I happily swallowed the rest, he wiped the drip from my chin with his finger and put it in my mouth
"Make sure you get it all Donna, that will make the boys happy"
"Yes Daddy"
"Donna, I want you to cum now, play with your clit for Daddy, put a toy in first Donna like a good girl"
I grabbed the largest toy and he said
"Donna I don't know if you are ready for such a big toy"
"I want to try Daddy"
I put the toy on the bed and slowly sat down on it, it kind of hurt even my worked in ass, it was a pretty big toy, but I got it in and I started grinding on it while stroking my clit, I looked so sexy and slutty in my women's clothes, Daddy was enjoying the show I was putting on for him, I stoked my hard clit faster and faster
"Daddy I'm going to cum!!!"
And I did, all over his chest, I was so turned on that I let out a very large load
"Donna you made a mess on Daddy, you are going to have to clean that up"
I started to lick my cum off his chest, the very large toy still inside me, after I finished, I snuggled up to Daddy
"Was I a good girl Daddy? Will the boys like me?"
"Oh Donna, the boys are going to love you, you are quite the little slut taking that toy in your pussy, take it out and clean it for Daddy"
I took it out and started to lick it clean, it was much too big to go in my mouth. Afterwards we snuggled and kissed, I then dressed in my normal clothes and with that I said my goodbyes, unfortunately I was unable to meet him again as our schedules just did not work but nonetheless it was a great experience
-- Jim Hamm