My obsession

This is my first story and let me set it up first of all. I am a gay male, and I live with my boyfriend who is 15 years older than me. He has three kids, two boys and a girl and all three of them are of age. This is also a true story. All names have been changed for obvious reasons.

At the time, the kids were living with us and Christine who was eighteen at the time was starting to develop rather well. She was also starting to wear revealing clothing to which I took notice. It was odd at first for me, being a gay male, to start noticing her in this type of way. Any chance I got to look down her top or just stare at her cleavage I took, obviously with precaution. Her breast weren’t the only part of her body that was developing her ass was also. Her ass was getting nice and round, not the fatty type, but just enough to fill her tight jeans. Like I said before any chance I got to look, I did.
One evening as Jeff (my boyfriend) and I were coming home from doing groceries, we parked the car in the driveway and before this incident, I didn’t realize that Christine’s bedroom window was right where we parked.
On this particular evening as I got out of our car, I realized that her window curtains were open and she had just gotten out of the shower and was wearing a towel around her hair was wet. Quickly thinking that Jeff might see me trying to peek, I quickly started gathering the groceries to get inside quicker.
As we were bringing the groceries in, I was thinking of ways to get back outside to see if she was dressed yet or if I was finally able to see her naked body. Just as we opened the door, I saw that the garbage needed to be taken out. I was in heaven. So I didn’t waste any time and starting getting most of the groceries away and then looked at the garbage and told Jeff I was going to take it outside.
So far nothing seemed out of the ordinary as usual. I quickly gathered up the garbage and headed for the door. I threw the garbage out and walking towards her window made sure no one was looking. (Our back door faced an alley and people could be around). From a distance I could see that she was still in her towel, score one for me. I got up to her window and realized that I wouldn’t be able to see anything unless I was further away. Quickly I looked around for something to stand on and just my luck I found an old propane tank someone had left in the alley. I brought it over and propped myself on the tank and took a peek inside. Just as I got my head over the bottom of the window, she had started taking the towel off to which I thought she wasn’t going to turn around. I almost fell off the propane tank, thinking I was the luckiest guy in the world right now when she did. As soon as she was facing the window and I knew she couldn’t see me my cock started getting the biggest hard on I’ve gotten in a long time. Her breasts looked so firm and they were nice and round as well a nice C cup at most. My first thought was to reach into my pants for my raging hard on, but I quickly realized that I was supposed to be only throwing out the garbage. I waited another second or so while also checking out her nicely trimmed clit, which looked like she was a virgin.
I slowly made my way inside happy as shit that I just saw what I’ve been waiting for, for a long time, but at the same time I was disappointed that I wasn’t able to please myself like I normally would have looking at what I was seeing.
When I got inside Jeff was already watching TV in the living room and had asked me what took me so long, to which I told him I saw a kitten and was trying to catch it down the alley. It was totally believable because I’m such a sucker for kittens, and our neighborhood is full of cats. He must have believed me because he went right back to watching his program.
That started my huge obsession with Christine which continued with casual strolls outside for several different reasons after she was done in the shower, and eventually one night I did get to bring my cock out and jerk off watching her getting changed out of the shower.

It’s been a weird couple of years obsessing about Christine and also my new found porn obsession shemales or tranny’s depending on what you call them.
The main reason why I wanted to write this story is because I had a dream the other night and can’t really tell anyone because of…well you’ll see why after.
I’ve had dreams of Christine before, and I’ve also had dreams of shemales before, but none of the dreams involved both, until the other night. I would also like to point out that none of the dreams that involved Christine were really that vivid after I woke up. I remembered she was in the dream but don’t remember anything after that.
This one dream the other night, had me thinking all day.
It started off like any other dream with her, she wanted to ask me something in her room, which she usually would. Then slowly start putting her hands on me and we started going at it. She started rubbing my thighs moving closer to my cock. My hands went to her sides moving up to her firm breasts. Then she would rub my cock and slowly start unzipping my pants and knelt before me and at first started stroking my cock before putting her warm mouth around it. Slowly sucking my rock hard cock then moving a little faster and faster, then slowing down again. The she stood up in front of me unbuttoned her top and took her shirt off. I reached up and decided to take the bra off myself and started fondling her tits. By this time I was already about to cum. Like every other dream I moved my hands down slowly and started unbuttoning her jeans and pulled them down to the floor. She was standing there in front of me with just her panties on and ready to fuck me like I’ve never been fucked before.
This is where the dream got weird/different.
I put my hands on her hips and slid them underneath the elastic for her panties and as I started pulling them down slowly looked up at her and she had this really big smile on her face, it wasn’t totally unusual but was different then usual. As her panties got further down her body and I was right in front of her crotch area I noticed she had a huge cock. Almost as if I already knew she had one (which I knew from experience) I grabbed it and started stroking it. As I was stroking it she took a step forward towards me as if telling me to start sucking, to which I obeyed. Her cock grew its full length inside my mouth and must’ve been at least nine and a half inches. I could barely fit the whole thing in my mouth. I was totally in heaven and was shocked at the same time. After sucking her for awhile I stood up and she turned me around and bent me over the chair I was sitting in.
She took a step towards me, reached in front of me and started stroking my cock with one hand, and with the other started sliding the other one in my ass. She let go of my cock for a second and grabbed my waist and started pumping her nice big cock into my ass. At first she started slowly, then started getting faster and faster. At the same time I was enjoying this I started stroking my own cock to double the pleasure. After what seemed like an eternity she told me she was ready to cum and wanted me to taste her. She pulled out of my ass and as soon as she did I sat back down and she started stroking her cock rapidly. She asked me if I was ready and I just nodded my head. She pointed her cock right at my mouth and unloaded her huge load right into it. It was probably the biggest load I’ve ever seen. As soon as she was done she sat me down in the chair and straddled me to let me fuck her. At this point I didn’t know how much longer I was going to last but right away she started sliding up and down my cock put her breasts in my face and was fucking me like I’ve never been fucked before. She let out a slight moan and that added to her tits bouncing up and down in my face just about sent me over the edge.
I grabbed her by the waist; she slid off my cock and knelt down in front of me. Not letting me stroke my cock and let my load in her mouth she quickly slid her mouth on my cock and started sucking me off. After a couple strokes of her mouth I was done for, I let go unloading it all into her warm mouth. She finished me off not letting a drop go by, and stood up in front of me, so I can look at her one last time nice C cup tits and a beautiful nine and a half inch cock.
Then I woke up. A second or so went by before realizing my dream, then looked down at my rock hard cock which had pretty much soiled my pajamas, looked over and Jeff said must’ve been quite the dream, do you remember what happened? To which I replied can’t remember a thing.

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