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.
We knew it was time to take a shower and get dressed. Of course we both took a shower and I sucked him off in the shower and swallowed. After that, we packed up our things and was about to leave. Before he opened the door, I caught a glimpse of his polka dot panties and grabbed him from behind. He was confused and said we should really get down stairs, but that didn't stop me from moving my hand down to his cock. I slid my hand in his pants and rubbed his cock. Then I unbuckled and unzipped them to reveal his panties. He wasn't hard yet, so i turned him around, kissed him then undid my pants and lowered them. I left my underwear on and rubbed him that way. He and I were both starting to get hard, when I lifted him up onto where the tv was resting. After making out with him for a bit, I lowered myself to his cock and said "I know you hold in your voice when we fuck. But this time, I want to hear you fucking moan." I then put his legs on my shoulders and swallowed his cock and started fast movements and then I slowed down for a while. I then brought my lips to his tip and stirred it around a little. He started getting louder and his breathes were getting faster. I could feel his feet on my back going wild. he kept moving his hips to receive more pleasure. He twisted and turned as if he wanted me to let go but i didn't, until he finally came. He would thrust and twitch a little until he was empty. I gathered all his cum on my tongue and opened up to show him. I brought my face to his and he stuck his tongue out and gave mine a little lick and then stuck his tongue deep in my mouth. The best part? I could feel some of his cum oozing out of the side of my mouth and running down to my chin. I don't know what it was, but the thought of drinking his cum didn't bother me anymore, it only drove me wilder. After i gathered his cum and stuck it in my mouth, I told him I was harder than I've ever been in my entire life and asked for him to relief me. He did and swallowed it all. I didn't mind. I tasted a little of myself before but not a lot of it. I just wanted to have his in my mouth.
We then went down stairs with five minutes to spare. When the five minutes were up the teacher did a head count. While he was doing it, I noticed to guys were looking at me weirdly. They were pointing and whispering to each other. I looked behind me to see if there was anyone there but there wasn't. This continued until roll call was over and we got on the bus. I, Freddie, Jessica, and the other two girls sat as far back as we possibly could. The two guys that were laughing and looking at me, sat in front of us. After the bus was a few miles on the road, the guys turned around and one of them asked how we all liked Seattle. We all answered that it was fun, or great, and then the guys asked me specifically what i enjoyed the most. I answered that I liked the look of the city. I didn't really have a great time outside of my hotel room so that was the best answer I could come with. They inquired if there was anything else I liked about it and I just said thats it. After the pair chuckled a little, one guy asked if I had some fun at night. I looked confused and said that we weren't allowed to go out at night so, not really. They chuckled some more and one of them said "Yeah, that's true. Maybe you had some fun inside your room?" Thats when it hit me that these two guys shared one of the bedrooms on either side of us. I'm guessing the right since the bed was against the right wall. I just shook my head and said no. They then asked Freddie and he said the same. Then, my world shook. "Really? Cause, that's not what we heard." There was no doubt in my mind that these two knew what we did. It was no secret that Freddie was gay, so when you hear stuff like that coming from the same room as Freddie's that hes sharing with his best friend? Its no wonder these two came to that conclusion. Freddie then asked what they heard. They said that the two of us must had too much fun last night. Freddie just said he didn't know what they were talking about, while i was trying to come up with the best lie i could. They continued on like this, until one of them said "We know you two were fucking last night." Freddie and I froze while the other girls listened. They were obviously uncomfortable with the situation. Other students were listening in on the conversation. Freddie then said "What if we were? I don't see it would be any of your business." They ignored the last part of that sentence and asked if we were and I said no we weren't. they asked if I was sure, I responded with that Freddie was the one that was gay, not me. That I didn't look at any man like that. They just said sarcastically "Suuuure you wouldn't" One of the girls got fed up and said if they don't stop then shes gonna call the teacher over. They then reluctantly turned around. For the whole trip, the five of us didn't say a word.
Once we got back, we had to still go to class. We gathered our things and went to class. I couldn't look anyone in the eye as I left. After school i met up with Freddie. He was waiting for his family and told me we should talk on Friday. I just said ok and left.
When Friday came I went over to his place with some stuff. I followed him to his room. "Close the door" he said. I did. "What do you see me as?" he asked, as I looked on confused.
"What do you mean?"
"Back on the bus, you said we never had sex and you never would."
"You said the same thing."
"No. I said that it was none of their business if we did or not. I never outright denied it ever happening."
"Well… like you said, it was none of their business if we did so it just came to mind."
"……Do you love me?"
"What?"
"Do you love me?"
"Wha… I thought we were talking about about what happened on the bus."
"This is about what we are to one another."
It was starting to get harder for him to not cry. Because he started to.
"'What we are to each other?' Why do you need to know? It should be obvious what we are."
"Well it's not to me. Even after we got back together, you still ask me to not tell anyone. I should've realized that it's because you only wanna fuck me."
"That isn't true! You're my friend, Freddie. Its not just about the sex!"
"Is that it? I'm just your best friend who you fuck?"
"No! Thats not it. We do other things. We hang out, we talk."
"That's something friends do withe each other. I'm talking about more than that, like holding hands or going on a date. Can you say that I'm your boyfriend? Can you at least say that?"
"……All this is just coming out of nowhere and its a lot to take in."
"Please just tell me what you think of me."
"I… I think you're pretty and You have a great personality. I like doing those things with you but I like hanging out with you too."
"I don't want to just hang out. I want to do things as a couple……….. You called me pretty?"
He smiles and looks down. i walk over to him and grab his shoulders and tell him I do think hes very pretty. he then looks up at me.
"That's something you say to a girl. I'm not a girl. I like to dress up in womens clothing but that does not make me a girl. You haven't changed since we split. You only find me attractive because of that. Before we got together, you were always asking me about cross dressing. You were the first guy friend I made in years and I didn't want to push you away, so I cross dressed for you. I thought I found someone who accepted all of me. Not some; all."
I was speechless. i couldn't say anything to ease his fears, cause it was either a lie, or I was just afraid to admit to myself that I wanted to be with him, not her. He told me to leave, and I did. I closed his door behind me, then heard him fall to the floor and cry. I left his house and went home. The next few days Freddie skipped school. He came back eventually but we didn't speak. We even stayed away from each others friends. Then a month later Freddie started going to a different school. I never saw him again.
I thought about seeing him, but still couldn't admit that I liked him as a man. I couldn't openly start dating him or hugging him, kissing him, none of that. i'm different now. I would take him out to places now, and openly kiss him. Not like that kind of mentality can help me now.
Well, thats it. that was my experience. well, from what i remember anyways. I dont' regret most of it and regret some the most. i just wanted to get that off my chest and take a walk down memory lane even if it was painful.
Source: reddit.com/r/gonewildstories/comments/3goaxc/my_first_sex_with_a_cross_dresser_bur_not_my_last
Thank you for sharing it.