My Best Friend's Dad

Sandy and I became friends freshman year in high school. It was a little improbable, because she is so attractive, but she was the new girl in the neighborhood, and I was a bit of an outcast myself, so we became friends, and even when she became one of the popular girls, our friendship even deepened. I came out to her our sophomore year, which wasn't really a surprise to her. I had been called a fag, a queer, and worse for years, though I didn't actually admit that I was gay to anyone other than her, and that was long after the slurs began.

Sandy had lost her mom a few years prior, and her dad was devoted to her. He was a little reluctant to let me spend as much time with her as I did, especially when he wasn't around. We were not anyone's idea of a couple, we were close in size after all, but he was still concerned about what teenage hormones would do. When she told him I was gay, and I confirmed it, he relaxed a bit about it, and the more I was around them, the more he stopped worrying. He didn't care that I was gay, but my folks would have, so they were actually over the moon that I was spending so much time with Sandy. I would always say we were just friends, but they were hoping it was more than that, and anything that let them ignore the obviousness of my true nature was fine with them.

My junior year is when I admitted that I liked to dress up in a few of my stolen sister's clothing. I was more nervous about that confession than when I came out to her, but she loved the idea, and from that moment on, whenever I was over at her house she had me wearing her clothes, or some of her mom's old things, and even a few things that we bought just for me. I am not sure what her dad thought of it, but Mike seemed to take it in stride, and eventually just treated me as a teenage girlfriend of Sandy. He even would refer to us as "girls," and used the feminized version of my name, Danielle, that Sandy and I had been using.

Mike spoiled Sandy, and since her mom wasn't around to teach her, he actually paid for her to take make-up lessons, so she had quite a collection of cosmetics and knew how to apply them, and she loved practicing on me, and teaching me. Since my folks were so happy about me having a "girlfriend," and Mike was totally fine with having his daughter's teenage girly gay friend hanging out, staying over on the weekend became a pretty regular thing. Mike promised my folks that he wasn't allowing anything to happen between the two of us, which was totally true and took zero effort on his part.

By the later part of our senior year we had both already turned 18 and the occasional weekend sleepover morphed into me spending about half the nights there, with me dressing like a girl, fully made up, with breast forms and a wig we bought on-line. We would go out for dinner or to see a movie, sometimes just Sandy and I, sometimes with Mike taking us out. Sandy would occasionally date, but she never had any serious boyfriends, and we would like to look at guys when we went out, talking about them like any other pair of high school girls. The guys liked to look back too, and we would get approached quite a bit.

We made sure not to hang out where the kids from our high school hung out. It was one of these nights where we met Randy and Tom. They were really cute, and pretty insistent, and to be honest, we really liked the attention and flirted back, a lot. We ended up chatting with them for about 2 hours, and by the end of the night Tom had Sandy's number and a promise for a date. I was playing hard to get, well, because I didn't want to get found out, but at the end of the night, Randy moved in for a kiss, and I didn't back away. I let him kiss me, and it just felt so good. He was taller and stronger than I, and this was the first time I was in a man's arms. I loved it. Not him, he was just OK, but the feeling of being kissed and held was so nice. I just went with it, and definitely lost track of time. Not that Sandy and Tom cared, they were making out hot and heavy as well. I have no idea how long we were at it, but we did manage to pry ourselves apart. My head was spinning from the first time I had been kissed, and Sandy and I spent the rest of the night talking about it.

She had promised a date with Tom, and she tried to talk me into going out with Randy, but we both knew that it would be a bad idea in the end. I also wasn't really that into him. I wanted someone older, stronger, and someone who knew my little secret. I wanted Mike, though I didn't tell any of that to Sandy. So while Sandy went out with Tom, I stayed over at her place, partly so I could hear all the details after, but also so I could be alone with her dad. We did the usual dressing up and getting ready, both doing our makeup and me putting on my breasts and wig, but she went the full 9 yards and put on a sexy little dress and strappy sandals, while I was in a casual outfit. Of course, I didn't have to stay that way, and after she left, I changed into a sexy little dress myself, with stockings and high heels and just enough of a thong to keep my little 'clit' contained and went to put my own plan into action. I knew he looked at me, I knew I looked like a hot teenage girl, what single dad wouldn't look at his daughter's hot teenage female friends. Heck what married dad doesn't sneak glances?

Mike was watching a game on TV so I just wandered in and stood behind him for a moment. I draped my arms over his shoulders from behind and put my head next to his, not saying anything, hoping that the aroma of my perfume would soften him up just a bit. My arms innocently moved down his torso, just sliding down his body absentmindedly. I placed my cheek next to his, feeling both the warmth of his skin and his slight stubble against my smooth skin. After a few moments, I whispered in his ear that I really appreciated everything that he did for me, planting a soft kiss on his cheek as I did. I let my hands start to wander on his chest and rub him through his shirt, as I began to nuzzle his neck. Mike moved his hands to cover mine and keep me from rubbing his chest, so I just moved to phase 2 and climbed over the back of the couch and onto his lap, straddling him. I made sure to wiggle my ass a bit on his lap, and was rewarded with the feel of his hardening cock. He started to protest, but I just moved in and kissed him on the lips, wrapping my arms around his neck. I moved my hips, grinding myself against his cock, feeling it against me, feeling it get bigger and fuller as I dry humped him. He continued to protest, but he never pushed me away, and the rapidly swelling cock I was sitting on told me he wouldn't.

Slowly, his mild resistance faded and he started kissing me back, then I started to feel his hands tentatively caress my back, then both got bolder, and soon we were hot and heavy, with his tongue invading my mouth and his hands cupping my ass. It was his turn to start kissing my neck, which got me to start moaning. I could feel his cock really stretching his pants, and I loved the feeling of it growing beneath me. I could feel my own little soldier rising to the occasion too, and me moving around on his lap was creating some nice friction for both of us. Feeling the effect I was having on him, I slowly disengaged from our make-out session and slid down his lap until I was kneeling between his legs. My hands reached to his belt and pants, opening it for access. He helped me out by lifting himself off the couch a hair, letting me slide his pants and underwear off, freeing his cock. It was so much bigger than mine, well, I don't have much of one to begin with, but his was definitely manly and beefy. I wanted to savor the feel of it, but I also wanted to make sure that he didn't have a sudden change of heart and back out. And, to be honest, I really wanted to suck that cock, which is what I started to do.

It was my first cock, but I fell in love with it instantly. I loved the feel of it in my hands, the heat of it as I rubbed it against my face, and how girly it made me feel as I opened my lips and took the head in my mouth. I also loved the look of lust and satisfaction on Mike's face as I began to suck it. I'd watched enough videos, mainly by myself but also occasionally with Sandy, so I kept in my mind that I should keep trying to make eye contact, lick him, kiss the head, lick and suck the balls... I guess I was doing it right, because he was definitely loving the attention. I also got my first taste of cum, well, other than my own, that began to leak out of the tip as I worked his cock. I felt more like a woman than I had ever felt before, sucking on a cock, looking up and seeing the lust and desire in his eyes. He gave me small words of encouragement, as well as moans, letting me know I was doing it right. I couldn't take much of him, so that just meant the tip of his cock got all the action. I slipped it in and out of my mouth, rolling my tongue around it, all while my hands stroked the shaft. I think he knew that I was inexperienced, because he mixed in the encouragement with some instruction, telling me how to suck his cock, not to take it too deep...

After a good five minutes or so he took me by the hand and pulled my face to his, initiating a deep and passionate kiss. It was so hot, feeling his hands pull me close. I wrapped my arms around his neck, then I felt him lift me slightly and I wrapped my legs around his hips as he stood up, letting him hold me off the ground while we kissed. He slowly started walking, carrying me toward his bedroom. Once there, he laid me down on the bed, quickly stripped naked, and moved over me, our lips still working over each other. Lying there beneath him, I parted my legs submissively, which made the short dress I was wearing ride up, exposing the tiny thong which was no longer able to keep my small but very hard cock from jutting out. I had no idea what Mike would do, but I was not expecting him to drop his head to my crotch and take my fully engorged little cockette in his mouth. Oh my god, I almost lost it right there and exploded in his mouth. He licked the length of it with long strokes of his tongue, telling me what a sexy clit I had. I was moaning from the intense pleasure, and my hands just instinctively moved to his head, caressing it as he bobbed his head up and down. It didn't take long, a minute, maybe two, and I was cumming, letting loose stream after stream into his mouth..

"Oh my god, I am so sorry," I began to apologize, but he just moved over me and went to kiss me. I expected to taste myself then, but all I got was a hint as he had swallowed my entire load. I would learn later that this was the first time he had ever done anything like that, but for now, all he did was kiss me and move his body into position with his cockhead teasing my virgin hole.

He would rub against me, pushing ever so slightly with the spongy head, lighting up the nerves that had never been stimulated like that. I could feel a little wetness, I had lubed him up a bit with my blowjob, and the precum was still coming out, adding a little slickness. It was just enough for the head of his cock to start to part my rosebud, eliciting a moan from me. He kept teasing my entrance, pushing just hard enough to get the ring to part, but not hard enough to truly enter me. I was lost in my own sensations and didn't see when he had grabbed some lube, but I did feel it drop on me, on us really, making his hard cock much slicker and giving me the lubrication needed to finally let him inside.

The teasing had done its job, because I was able to relax as he pushed against me, getting the head of his cock in past the ring. He paused there for a moment, telling me how tight I was, how it had been so long since he had sex with a beautiful teenage girl. Little by little he began to push deeper into me, thrusting a bit, pulling back, then thrusting deeper. He was so patient and tender, letting me get used to his length and girth before going deeper. I was begging him to fuck me, telling him how good his cock felt inside me. He kept pushing, deeper and deeper, until I could feel his body against mine, signaling that he was fully inside me. Then he began small thrusts, pulling himself out before burying himself again deep inside me. I had my legs wrapped around his waist, my thighs wide open and wanting his cock deep inside me. I would occasionally reach up to try and pull his head down for a kiss, which he always accommodated, exploring my mouth with his tongue just as his cock was filling my ass.

Even though I looked like a girl and felt like a girl, I had the raging hormones of a teenage boy and my little cock was hard again. I began to play with myself as he fucked me, but I could barely focus enough to do so. Every time I would stroke myself and he would drive deep inside me, My eyes would roll and I would almost black out. Little by little I was able to get into a rhythm, loosely jacking myself in time with Mike's deep strokes, my nails occasionally teasing the tip of my cockette. I felt myself building up and I exploded, cum spurting out of me as my entire body orgasmed. I could barely process what was happening, but my convulsions clamped down on Mike's cock deep inside me and he came too, filling me with his hot seed.

He continued to pump, his own juices adding to the lube, but alas, he began to soften and slipped out, leaving me missing his cock deep inside me. We cuddled for a few minutes until I realized that other need, and excused myself to the bathroom. After a few minutes I emerged to Mike running a shower, and he beckoned me to join him. I was a little apprehensive, because this meant getting fully naked, and that while I had the body of a slim teenager, it was still the body of a teenage boy. He put me at ease, telling me how beautiful I was, never once seemed at all put off by my extra appendage, even without the fake breasts and wig. I guess the year of me being Danielle really did condition him to think of me as a girl. We took a nice and relaxing shower, playing around with each other and doing a lot of kissing. Finally, we got out of the water and dried off.

Mike started to have 'that talk' about how we can't do anything around Sandy and she can't know what is going on when we were interrupted by Sandy calling out from down the hall, "too late for that you two. Besides, from the way you two have eyed each other for months, this was inevitable." She gave us a few minutes to put on robes before she knocked on the door. She gave me a big hug and gave her dad a kiss on the cheek before taking me by the hand toward her room. "I'm just borrowing her for some girl talk, dad, I'll send her back to her new bedroom in a bit."

I moved in immediately after graduation, taking all the boy clothes that I needed to keep my folks from getting suspicious but leaving them boxed in the attic. Sandy and I became even more like sisters, except for the fact I was sleeping with her dad on a nightly basis. She did tell me that she was not going to call me mom, which was perfectly fine with me.