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How My Boyfriend Got Me Into Wearing Girl's Undies

by I_am_cute


I met Chad at a hangout. Just a casual encounter at a local gay hangout. Cute beyond means; mid-twenties,.very fit, short hair, jeans that showed a nice butt (I am a butt guy). Me, in my late 20s, tall, swimmer’s build. Both of us are very all American looking guys. We could pass for straight any day.

So, we started chatting and decided to ditch the bar and get some coffee at a nearby coffeehouse. It was nice to sit across a table from him, looking into his beautiful blue eyes. As he talked about himself, I could hardly even concentrate on what he was saying. I was slowly undressing him in my mind, just thinking about getting him out of his jeans and undies. I think he gathered that I was day dreaming, or maybe I should say night dreaming about him, because he got this grin on his face and asked me a question about what he just told me. Very shyly, I told him I was a bit distracted and couldn’t remember. He asked me what I was distracted about. I told him I was distracted by Chad!

He lived nearby in a new condo that I had seen built and always wanted to see. He asked if I wanted to come up for more coffee. I was a little hesitant, because I don’t normally sleep with a guy on the first date – and this really wasn’t even a date per se. I mean, we had met at a dance club, gotten coffee, and now I am going home with him. But, I told him, “Yeah, I would love to see your place,” before I could even think about not wanting to sleep with him on the first date.

So we walk back to his condo, lightly touching each other, very flirtatiously! When we got in the elevator to go to his 19th floor condo, he leaned into kiss me. Wow! I was really on fire by that point. I wanted to strip his clothes off and have him do me right there in the elevator. But I just savored his lips and tongue. He was a great kisser.

We arrived at his condo unit and went inside. He said to make myself comfortable. He put on a pot of water and asked I wanted tea or coffee. I chose coffee. He chose tea. I marveled at the view of the city. “What a view you have,” I said.

He was still in the kitchen and agreed, “Yeah, it is really something. I love just standing by the window watching the mountains. It’s so relaxing.”

I continued to look out the window and he came into the den area and walked behind me and put his arms around my ways. I could his budged pressed right against my butt. He was just a bit shorter than I am, so it was perfect. “That feels good Chad, really good,” I said, as I wiggled my butt to position him tighter.

Just the thought of his package against my butt separated only by two pairs of blue jeans and undies was enough to make me want to explode. He started kissing my neck and nibbling at my ear lobe. He said he really didn’t want any tea and wondered if I really wanted coffee.

“No” I said, “I want you!” With that I turned around and started kissing him and unbuttoning his shirt. What pecs this guy had. He said he worked out most days for 45 minutes – at least. He pulled off my polo shirt. I got on my knees and slowly unbuckled his belt and began to unbutton his jeans, rubbing my face against his huge bulge.

As I started to remove his jeans, I saw his undies. He was standing there in the cutest pair of pink bikini briefs. I lightly touched my mouth around the tip of his penis. My saliva wetting his pink bikini so I could begin to see his cock head. I put my hands on his butt, slowly putting them under the bikini line. He moaned in pleasure. Then he said, I hope you don’t mind me wearing pink panties. He said that he had been wearing girls panties for years. I smiled and said, “I don’t mind, anyway, you aren’t going to be wearing them long” and then slowly took them off and wrapped my mouth around his warm 8 inch cock. He tasted so gooooooooooooooooood!!!

He asked if I wanted to move to the bedroom! I immediately shook my head up and down, while not removing my mouth from his cock.

In his bedroom, he pushed me on his bed. He got on top of me and started to kiss me. I wrapped my hands around his body, making my way to his cute ass and inserted two fingers into his hole. When I did that the passion in him increased ten fold. He started to move from my lips down my neck past my nipples to my belly button. He unbuttoned my jeans and slowly unzipped them, with me lifting my waist so he could pull my jeans off. I was there in my black bikini. He slowly removed my bikini and gave it a toss to the other side of the room. He asked, “can I fuck you?”

“Yes, please, yes.” I said.

He slowly slid up to my hole, with me on my back. He positioned my legs on his shoulders and put his cock head at my hole. “Fuck me” I said. He put slowly pushed his cock into my hole. (I am rather tight, even though I am a total bottom). He could tell that I was a bit uncomfortable and asked if I wanted him to stop. I told him to get some lube and to try again.

He reached into his night stand drawer and lubed himself and my ass up. He then tried again and slid in without a problem. Man, did he feel good. “Chad, you feel so good in me. So warm. Please, don’t stop.”

He continued back and forth, my legs over his shoulders, with him leaning down to kiss me from time to time. I started jerking off to match his rhythm. I was I getting close to cumming, he said, “Dude, I am going to cum. Do you want me to pull out.”

“No” I said, “don’t you dare. Just keep fucking me and don’t stop. I want to feel your cum in me.”

He kept pumping away. As I began to climax, so did he. The pressure of his cock in my ass made me squirt the biggest loads of cum I have ever had in my life. And I could feel the rhythm of him cumming. His breath picked up and he said “I’m cumming, I’m cumming in your hot little ass ...” Afterwards, we just lay in each other’s arms; him on top of me and his cock still inside me. It was heaven.--I mean, really heaven! He pulled out and just got under the sheets. We didn’t even bother to clean up. We slept all night, twisted like pretzels, my cum covered chest and shoulders with his cum covered cock. It was great.

The next morning, I got up to get dressed. He looked really tired, but I had an appointment to go to. I found my black bikini and put it on. I was standing by his head rubbing his hair when Chad woke up, facing directly at my cock. He said, “Nice view.” Then he told me to take off my bikini, which I did. I started getting a massive hard on. He put his mouth on my cock and started teasing me, sucking me, and going completely down on me, which is pretty amazing since I am about 8 inches hard. He was a great cocksucker.

As I got to the point of climax, he took his mouth off my cock and asked if I wanted to fuck him. I told him that I was a total bottom, and that any fucking in this relationship would be him on me. I was going to be the girl and that he would be the man, and that he would be the one fucking me – end of story. He grinned. I then said I would like a nice blow job though every day and that I expected him to swallow.

“No problem,” he said. He then started to blow me again and as I was getting ready to climax, he took his mouth off my cock and said, “So, if you are going to be the girl and I am going to fuck you, then there is something I want you to do

“Anything,” I said being completely vulnerable, “just quick talking and finish this blow job and swallow my cum.”

He said that he could promise me better blowjobs then this if I let him pick out my undies to wear.

“Fine,” I said hurridly, “pick out whatever you want me to wear, just stop talking and blow me.”

So he put his mouth back on my cock. I was still standing by the bed, face-fucking him. Finally I blew. I mean, I reallyblew. I have never cum so much at one time. He seemed to be having trouble swallowing it, but he didn’t lose a drop. All of it went down his throat! Man, what a cock sucker!

So, I started to put on my black bikini (you know the jockey cute bikinis that are called elance). He said to hold on and that he would get my undies for me. I was like, okay if you suck cock like that, then I will wear whatever you want.

He went to his dresser, completely naked, and pulled out a really cute pair of girl’s panties. A side tie bikini. He said, “Wear this, you will look super cute, or I have a light pink thong – your choice.”

I am like, “Dude, what’s with this?”

He came over to me, sat on the bed, facing my cock, and coyly touching it with his lips. With one hand on my hip, he said, “You told me that you were going to be the girl in this relationship and that I was the man. As the girl, I am going to fuck you – every day. And, if you are going to be the girl, you are going to wear girl’s undies and look like a girl – at least when are at home together. So, put on either the side tie bikini or thong. When we get together tonight, I want to undress you to find you wearing girl’s undies. Then I am going to fuck you like you have never been fucked before!”

I said, “Okay,” and picked the side-tie undies. I got dressed and left wearing my regular guys clothes, but underneath girl’s undies. It felt really erotic. That night, after a movie, we went back to his place and we fucked all night long. He told me that he was more bisexual than gay and that seeing a hot guy in girl’s undies was even better than seeing a girl in girl’s undies. Plus, he liked the fact that I was a total bottom.

For the three years we were together, he always called me his girlfriend and fucked me just like I was a girl. He also bought me the cutest pairs of bikinis and thongs. I even started wearing girl’s jeans, which totally turned him on. He really liked to fuck too! Which was perfectly okay with me, because I loved him fucking me!

Anyway, that is how I started wearing panties.

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1 Gay Erotic Stories from I_am_cute

How My Boyfriend Got Me Into Wearing Girl's Undies

I met Chad at a hangout. Just a casual encounter at a local gay hangout. Cute beyond means; mid-twenties,.very fit, short hair, jeans that showed a nice butt (I am a butt guy). Me, in my late 20s, tall, swimmer’s build. Both of us are very all American looking guys. We could pass for straight any day. So, we started chatting and decided to ditch the bar and get some coffee at a nearby

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