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.

The play had done its final showing and a months later I talked with Freddie. I apologized for making him feel that way and that I still cared about him. He told me he was sorry to and that it was a stupid fight. We made up. A few weeks later we were told our play was nominated for an award and the entire cast would be heading to Seattle to receive it. The good news? We would be staying overnight. The best news? We could chose who to share a room with, so long as it's someone of the same sex. I knew who I was gonna be staying with. After Freddie and I made up, we haven't had sex, and obviously we didn't have sex when we were apart. Yeah, you could say I was excited. When I asked Freddie if he wanted to share a room with me, he knew what I was really getting at because he was thinking the same thing. So, he agreed.

The day we were leaving for the trip, most people brought a few bags with them. Freddie was bringing four. I questioned him on this before we got on the bus and he told me he was taking care of his best friends stuff since she didn't have enough bags. I thought nothing more of it and we got on the bus. After a very long road trip, we reached Seattle and took a small detour at a gas station to grab some food and water. After that, we were on the road again. Next stop, the hotel. We finally reached the hotel and dropped off our stuff. In the lobby Freddie was about to grab all his bags when I came over to help him. I asked which bag was his friends bag so she could pick them up. He said that she would grab the bags later and that we should just put them in our room. My curiosity was rising but I just let it go.

When we were all done checking in, we all had a few hours to do whatever we wanted, since the award show was gonna be in the evening. There was a few nice stores around and a mall. I was in Freddies group. There was him and I and three other girls. After a few hours, Freddies best friend Jessica told the other girls that they should all split up. She suggested I went go with the other girls while her ad Freddie go somewhere together. I didn't really want to since I didn't know the other girls that well. But it would have been rude to just say "I don't want to hang out with them" so i just went with it. An hour later? It was so awkward. I eventually sent Freddie a text saying I was going back to the room. In the room I watched some tv and took a shower. Freddie came back and was hiding a bag behind him. I couldn't see what was in the bag or what store it came from. He just quickly put it in his other belongings and sat next to me. He held my hand and rested his head on my shoulder. I kissed the top of his head, then he looksed up at me and kissed me. I wanted to go further but the awards show was gonna start soon. So he took a shower and put on his suit and came out and saw that I was wearing mine. He told me I looked very handsome. I thanked him and went to the door.

The award ceremony was disappointing. We only won one award and the director won it so the cast just got dragged along. I had sit next to two people I hardly ever talked to during production. So that was a bore but my night was just beginning. Unbeknownst to me, there was an angel planning to make this night, a night to really remember.

After the awards we all went back to the hotel since it was 9'o clock. I couldn't find Freddie after the show and so I just went to the hotel and back to our room. When I went in I heard the shower just start. I assumed it was Freddie and just changed my clothes. I noticed that two of Freddie's bags were missing. I just thought Jessica came by and picked them up. After 30 minutes, the shower stopped. I thought I heard a zipper in there, but just went back to watching tv. 20 minutes later the bathroom door opened and what I saw shocked me. Freddie came out wearing some feet baring high heels, a striped mini, mini, mini skirt, a buttoned up pink shirt that had a knot in the middle and he was some light lipstick and blue eyeshadow. He had his wig on and it was curled. I've never seen him have it like this, but it was so good looking on him. In his wig he had a red headband on with a some flowers on the side. I asked what was going on. He said "Some people might call this 'makeup sex.'" I stood up and he walked over to me and untied his knot. I didn't notice it before but he was wearing a red laced bra that didn't cover his nipples. He asked if I liked what he bought today. I immediately lifted him up and stuck my tongue in his mouth and he did the same while he wrapped his legs around me and I thrusted him while he was pressed against the wall. He took off my shirt and let go of me so he could get me out of my pants. He sucked on my cock for a little bit and I told him i wanted to fuck him in the ass while holding him like i just did. He agreed and gave my cock one last kiss. I lifted him up and put his butt where the tv was sitting. He lifted his ass up while his arms supported him from the back and i stuck it inside of his ass. I had a tough time finding it first since we've never done it while facing each other. After it was in, I was to eager and started pounding him hard, but it either kept popping out or the angle was just weird. He suggested I sit down. I did and he sat on me and slowly inserted my cock in his white. After he was in he started riding me slowly and sped up bit, by bit. he would change his movements every now and again from going up and down to thrusting his hips. Till finally I was close to cumming. He came a little before me, and I was so turned on by the fact that he came, despite the fact that neither he or I touched his cock. The thought of him cumming because he had my dick in his ass was so hot that I came shortly after him. When we were done, he brought his face to mine and we made out, while he lightly move his hips with my cock still in him.

After about 10 minutes we were ready to go again. He grabbed a hand towel and wiped my cock and lifted his skirt to reveal his new underwear. A matching pair of red panties with his hard cock peaking out of it. I stood up and made out with him, then we fell on the bed. After making out for a while, I took off his shirt and bra completely and licked him a little before moving lower. It might have been our surroundings or the fact that we hadn't had sex for a while, I was feeling adventurous. I went lower down his abdomen, until I was between his legs. There I saw the tip of his cock again, peeking out his panties. He told me if I wasn't comfortable withe it, I didn't have to do it. I ignored him and pulled his panties just enough to expose his cock and make it point to the ceiling. I jacked him off a little bit and saw the tip of his penis was getting wetter. While grabbing his cock and starting at the base of the cock, I slowly brought my hand up and when I reached the tip, I took my index and middle finger and circled it on the head a few times, all while he was gasping, gripping the blankets and squirming his hairless, thin, white legs. I looked at my fingers and saw a bit of his white stuff on them. While panting hard he pleaded "Please stick my cock in your moth or jerk me off I don't care. Just make me cum soon." I was really turned on by this and brought my fingers to my tongue. After concluding that it wasn't bad I did this a few more times, until I brought my tongue to his tip and circled it a few times. When I brought my tongue in, I could feel some of his cum was on the edge of my mouth. I was really starting to leak some cum. I wanted to jerk off but first I brought my two fingers to the head of his penis and rubbed a bit of his cum on my dick. I did this a few more times until my cock was wet from his, and my cum. I then slowly licked his cock a bit before sticking it inside my mouth. He involuntarily thrusted his hips in pleasure and I nearly pulled out, but kept him in. He then started thrusting his hips up and down. I stroked my cock to the same timing as his thrusts. Shortly after, he came inside my mouth. I moved away quickly but not before some of it got in my mouth. On reflex, I spit some of it out and left my mouth open. I then closed it and moved the cum around a little before swallowing it. "How did I taste?" He asked. "Pretty good." I responded. I had yet to cum but was really close. I asked him if I could cum on his face and he said yes. I stood up and jerked off right in front of his face until I shot my load all over his face. He took some of it and brought it to his mouth and said "Oh my god, you taste so good." and brought more to his mouth. I didnt get a hard on but i still jacked off, since i thought him saying that was so hot.

After an hour of resting and making out, we were ready again. I could feel his dick against my stomach getting hard and twitching. I then started to make my way down his cock and started sucking it again. He then told me to bring my dick to him and I did. We started to 69 each other. I was thrusting downward while his was thrusting up. We were moaning so much as our dicks were in each others mouths. It was such a turn on. He came first and this time I didn't let go. After a few head movements I released his cock and took my finger around my lips and gathered his cum and put it in my mouth. He then motioned me to lie on my back with my cock still in his mouth. I did, and he took me as deep as possible while going as fast as possible. I came, he swallowed.

It was getting late but I really didn't want to go to sleep. I was having too much fun. He then slid his body down to my cock and started rubbing his chest on my cock while looking up at me and talking dirty. He did this until I came all over my stomach. He then licked it all up. He then swiped up the last bit with his finger and put it on his lips and told me to kiss him. I hadn't tasted my own cum in a while so I didn't mind doing it this way. I flipped him over on his back, got off the bed, grabbed his legs, and pulled him to the edge of the bed. Without saying anything I take his cock as deep as I possibly can in my mouth and started sucking. I try different techniques with my head, such as twisting as i go up, massaging it with just my tongue while its in my mouth. Then he finally cums. Again I hold onto his dick until he is finished and bring my mouth to his and we make out while his cum is still in my mouth. We use our tongues in and out of our mouths and after a while we back a way. I notice he still has some on the outside of his mouth and go in to lick it while he does the same for me. After this is done, I stroke his cock a little more and lick up what I can. We then go to bed, naked, while our cocks are touching, cuddling all night for the first, and last time.

Source: reddit.com/r/gonewildstories/comments/3gk4gb/my_first_sex_with_a_cross_dresser_but_not_my_last