I woke up with my arms wrapped around his soft, warm body. My cock was pressed against his butt. I started getting hard thinking about the things we did last night and the fact that I was holding him in my arms. I took my hand and started groping his chest and lightly moved my hips back and forth between his butt cheeks. "Well, I see you two are finally up." He said. He said he'd been up for a few minutes. I looked at the time and saw that we only had a few minutes before we would get our wake up call. I told him this and suggested a little morning fun. He then pressed his butt against my cock and started grinding it. I stuck my cock between his cheeks, without penetrating his ass, and humped him. He then said he wanted some morning milk and asked me to give it to him. He turned over and kissed me and then we both got up. While on our knees and on the bed, we touched tips again and again. Almost like our cocks were giving each other a light kiss. I said I'll give him his morning milk and laid him down on the bed. This is when we got our wake up call. Luckily we still had an hour before we had to be in the lobby. I then got on top off him and brought his legs around my waist and started humping him. After doing this for a while we both came at the same time. All our cum landed on his stomach. I told him to lay there and moved down to his stomach. I scooped up some of our cum and put it in his mouth and told him not yet. I then went back down, scooped up some more and brought it to my mouth. I then gave him some, and finally myself some, before sitting him up and frenching him. We exchanged out mixed cum for a while before swallowing and making out.
Author: honest_here
My First Sex with a Cross Dresser, But Not My Last (Part 3)
We tried to make our visits a bit more scarce so we didn't want to arouse suspicion. Sometimes it was hard, really hard. He'd tease me from time to time by showing me a glimpse of his panties, or lift up his shirt to show me his nipples. I tried to spend the night at his place as much as possible, not as often as we used to. But we still got a little further with our escapades. We were actually able to have anal sex with me not having to lube up either my dick or his ass. Then a few months in, we had a big fight. He said I was only using him for sex, because I hardly ever jack him off, and I never suck him off, or let him fuck my ass. I told him I just didn't feel 100% percent comfortable with it. The he brought up that he usually has to finish himself off with his hand. One thing lead to another and we stopped whatever kind of relationship we had. I was hurt of course. I did just use him. I only only saw him as attractive when I first saw his panties, and even more so when I knew he liked to cross dress. I rarely fucked him without some sort of woman's clothing or without the wig. I don't blame him for thinking that.
My First Sex With a Trap, But Not My Last (cont)
The next morning we woke up and went to school. We hardly said anything to each other. Not because either one of us was ashamed but because it was a whole new experience. We gave each other side glances and giggled at one another all the way to school. When we got out of the car I told him we should keep it between us for now. He agreed. When the bell rang for first period we then went our own ways.
I was looking forward to the following Friday so we could spend the night again, but before that, for almost the entire week I practiced sticking a finger in me to see how it felt. With some soap I was able to stick almost all of my middle finger in there. I first started jacking off with just the finger being idle. Then I tried thrusting it in and out, moving it around. It felt good. Got a little too eager and tried to stick two fingers in. Not so easy so I just stuck with the middle one for now. Finally Friday came.
My First Sex With a Trap, But Not My Last
For a long time I've had an attraction to men who dress up as girls, despite the fact that I don't consider myself gay. I don't know what it is or when it started but I just know I find a feminine guy in a skimpy outfit sexier than a girl with a skimpy outfit. I still might find the girl attractive but for some reason I'd rather have the outfit on the guy.
When I was in my freshman year in high school, I got along normally with my peers. I talked with girls, and made some guy friends. Well one day a schoolmate of mine caught my eye. Freddie Simmons. He was kind of smaller than me, slim, and was very feminine. he had brownish hair and the style where it covers a bit of his eyebrows I first saw him walking the courtyard while we were headed to our next period. He was tying his shoe on one of the benches. Originally I looked over his way because I thought I heard one of my friends. I know its not fair to judge someone on their looks but i guessed he was gay. Just the way he stood up from the bench was kind of feminine. And the way He ran was sort of girlie. Not that I hated him for it, I just thought "Huh. A gay guy."