Bikini Bottomed

Since I can remember I loved wearing panties but my ex hated the thought of it. It almost ended our relationship early on. I decided that I loved her more than wearing panties so I quit for the first few years of our relationship.

The urge to wear panties came and went often but I was able to avoid them. That all changed one day I was home alone and horny. I went to our bedroom to masturbate. Her panty draw was open and this time I couldn't resist the urge.

I went over to her panties and grabbed a pair. I started rubbing them on my dick. At first I was only going to masturbate with them but the urge was too much and I had to put them on.

I loved the silkiness on my balls. How girly they made my perfect ass look. They felt incredible. I didn't last long. I exploded all over myself.

After laying there for a few minutes I took them off carefully making sure I didn't get any cum on them. I put them back in their exact spot and she never noticed.

From that day was hooked and I would secretly wear panties any time I knew I wouldn't be with her. I loved the thrill of possibly being caught.

She almost caught me a few times but never did. The risk of getting caught was even more of a turn on and I started wearing panties more and more. I had been wearing them for about a year when she finally caught me.

One day she surprised me at work to go out to lunch. I was wearing panties that day. I was going to taking my panties off but I figured nothing would happen at lunch because we haven't been to sexual lately I decided to keep them on.

I was wrong. While eating she leaned over and whispered to me "I know we haven't been sexual lately but I miss him." As she said that she reached under the table and started rubbing my dick outside my pants.

I should have stopped her but I never had my dick touched while wearing panties and it felt amazing. I knew I was about to be caught but I kept letting her rub me hoping when she saw them she would be turned on.

When she undid my pants she felt my silk panties, which were actually hers. At first she didn't notice I was wearing panties because I normally wear briefs and she kept rubbing.

My breath was getting heavy and faster and I was about to cum when she looked down and saw her purple and white striped panties. She instantly stopped rubbing my dick. She looked at me with disgust, got up and walked out of the restaurant.

I buckled my pants to run after her but she was already gone. I tried calling her but she wouldn't answer. I didn't hear from her the rest of the day.

I was afraid to go home. I was expecting her to break up with me. To my surprise she did not. She told me she wanted to try and work through this but she was a different person from that day.

She stopped having sex with me. We didn't have sex for months. I would try but she had no interest. I would masturbate to girl on girl porn but that became boring. I didn't want to cheat but needed some thrill in my life. I started looking up different kinds of porn.

I found all kinds of kink and fetish porn but I often found myself watching porn that involved men wearing panties. I started with men wearing panties while having sex with women but I found myself really turned on watching two guys wearing panties have sex.

Even though I have never had a sexual encounter with a man the thought started to turn me on. I mentioned a 3 way with another guy to her. I could experience another man and spice things up with her, but again she wanted nothing to do with me.

After trying everything to stay with her I decided that a non-sexual relationship didn't work for me. She told me she couldn't get over the fact that I liked to wear panties so we went our separate ways.

The worse part of the breakup was I had bought an all inclusive vacation for us to try and fix things. They were non refundable so I thought about giving the tickets away or asking a friend to go. Ultimately I decided to go by myself. A solo get away would be good for me.

The trip was a couple days and I wanted new vacation clothes. I went to the store and bought all new shirts, shorts, swim trunks. I also decided since I was now single I would wear nothing but panties on this trip.

I walked over to the panty section, took a deep breath and walked in. My heart was beating a mile a minute. I had never bought my own panties. There were a few women also shopping. I thought they were going to judge me but they just smiled and went back to shopping.

This eased my nervous and I started shopping. There were so many different styles I didn't know what to buy. I finally found some cute pairs in my size. I also found a bra that was cute and bought it was well.

I was ready to go pay when I looked over and saw the women's swimsuit section. I never have wore one. They always looked super sexy on my ex. I figured since I was here why not go look at them.

I picked a few out and instead of taking them home to try them on I decided to do it at the store. I walk over to the dressing room. The lady smiled and me and showed me to a room. I tried a few on that did not look good on me.

I was starting to get disappointed. Maybe it wasn't meant to be but I had one left. It was a bright pink one. I put it on and it fit me perfect. The bottom grasped my apple bottom ass and the top was just the right size. I knew I had to buy it.

I walk out and hand the ones that didn't fit to the worker. With a smile on her face she asked if I found anything I liked. I told her yes and smiled back. We got to small talking and I told her all about my trip.

After talking for awhile I told her a had to go pack. I went to check-out but as I walked through the swimsuits one more caught my eye. It was an all black one piece. I had to try it on. I walked back to the dressing room.

The worker asked if I found more I'd like to try on. I told her one more and showed her. She walked me back again and told me if I needed any assistant let her know. I tried it on but it was to big.

I called for the girl working and asked if she could get me another size. As she brought it over she asked me if I'd like her opinion and I told her yes. (that's a story for another day.)

The new size fit perfect just like the pink one and I had to buy it also. As I leave the worker hands me her number and tell me she wants to know all about my trip when I get back.

As I packed all I could think about were my bikinis. I double and triple checked that I packed them.

The day finally came. I got up super early and got ready. I slipped on a pair of my new panties and some comfy clothes. While waiting for the plane. I thought about texting that girl from the store but decided I'd wait till I got back.

There was no one cute was sitting next to me on the plane so I just kept to myself and thought about the next week. Was there going to be any cute single girls? When would I wear my new bikini? Will anyone say anything to me about it? What stories will I have to tell? I was excited.

I land and head to my hotel. I want to head straight to the pool. I couldn't wait to show off my new bikini.

I put my pink bikini under some white shorts and a shirt. You could see the pink through my shorts which is exactly what I wanted.

I get to the pool and it is busy. There are people from all over the world wearing all kinds of different swimsuits. Women in bikinis, one piece swimsuits. Men in trucks and speedos.

I grab a chair and slip off my shorts. I keep my shirt on for now letting people think it's just a pink speedo. I walk over to the pool and get a few looks but no one says anything to me.

I hangout in the pool for awhile and have a few drinks. I was hoping someone would come over and talk to me about my bikini bottom but no one did.

After being there for about an hour I decided I was ready to take my shirt off and reveal my top. I head back to my chair and take my shirt off. Some people looked at me then went right back to their conversations.

I did get a few looks of disgust but there was one person who wouldn't take their eyes off of me.

He was around 30 years old, about 6'3" tall, tan, tone wearing a bright orange speedo. I smiled at him and laid down to dry off and tan

While tanning I started thinking, was I going to have my first gay experience today? Was I ready for it? These thoughts excited me and I knew I was ready.

When I opened my eyes I looked over at him and he was starring at me. I stood up and walked over his side of the pool to give him a better look. I slowly walked by to make sure he got a good look my ass. I bent over right in front of him as I jumped in.

I swam to the other side of the pool to make it look like was not desperate. I would look over at him and he would be staring. I would turn away and continue drinking my drink.

I go to order another drink but the waiter already had a drink for me. He told me it was from the gentleman right over there. I look over at him, smiled, put the straw in my mouth sexually and gave him the come over here nod.

He quickly got up from his seat and walked over to the pool and got in next to me. He introduced himself as Sam. He was 33 years old and from England. He owned his own business and was here on a vacation.

We talked, laughed, drank and flirted for hours. He kept playing with my bikini top and my squeezing my ass. I welcomed it. I would brush my hand over his cock slightly touching it.

We were starting to get a little drunk and I tell him "I've never been with a man." He grabs my ass and tells me "I'll change that tonight."

We continue to tell sex stories. He came out 6 years ago but has known he was gay since he was a freshman in high school. He dated girls throughout high school but he knew. He had his first gay sexual encounter when he was 19 away at college.

He had quite a few stories but told me he had never been with a cross dresser and had always wanted to. I told him about my most recent relationship and the months after.

He smiled and ask me if I wanted to go up to his room. I smile back and nod yes. We get out of the pool and dry off. As I was about to put my clothes on he grabbed them and told me to walk to his room in only my bikini.

At first I thought he was joking but I saw a dominant look in his eye and he was serious. This turned me on even more.

We walked through the hotel and I felt everyone's eyes on me. I was embarrassed and excited at the same time. I could not wait to get to his room.

His room was huge and had a perfect view of the ocean and pool. I walk over and look out of it. As I was looking at the view I felt him walk up behind me.

He started rubbing his cock on my ass. I reached back and started rubbing his cock outside his speedo. He moaned and whispered in my ear. "You're so sexy in your bikini. I can't wait to fuck you while you're wearing it."

With those words I turn around and drop to my knees right in front of the window for everyone to see. I pull his cock out of his speedo and put it in my mouth.

I let out a moan. It was as good as I hoped it would be. The taste, the feel, it was everything and more. I was in heaven, I was in a hot pink bikini sucking my first dick.

Even though I had never sucked a dick before it felt natural. I thought about what I liked and did it on him.

I grabbed his shaft with one hand and played with his balls with my other. I got it as deep as I could in my mouth.

I had been sucking him for about 10 minutes and I heard his breathing get heavy and I knew he was about to cum.

I wanted to taste him. I sucked harder and faster. I crept a finger toward his asshole and when I started to finger his ass he let out a loud moan and exploded in my mouth.

It tasted so good. I tried to not let any spill out but it kept coming and coming. It dripped down my chest and onto my bikini top. I felt like such a slut.

After swallowing what I could I took his penis out of my mouth and I looked up at him. His eyes were rolled in the back of his head.

I stayed on my knees in front of him wondering what was next. He didn't move. He just stood there trying to catch his breath. His cock was still hard and I wanted more so I started sucking it again.

When I put his dick back in my mouth I felt his body shake. He grabbed my head and started face fucking me. His cock was hitting the back off my throat. I chocked a little but I wanted all of it.

When he decided he was done face fucking me he grabbed my shoulders, stood me up, and turned me around.

He started rubbing his penis on my bikini covered ass. I put my hands on the window and push back a little. I wanted him in me. I wanted to feel all of him. I begged for it.

He pulls my bikini down just below my ass but still covering my dick. He teases the outside of my asshole with the tip of his dick. I push back more trying to get him to enter me. He pulls away and tells me to keep my head forward and not to turn around as he walks away.

I didn't know where he went but I listened to him. He comes back and I feel a cold gel on my ass. He uses his fingers to rub the lube in, slipping one in every now and then. I shiver with anticipation knowing what's coming.

His fingers felt great but I wanted his cock. I reach back, grab it, and put it on my asshole. His hands grab my hips and I feel him enter me.

I push my ass back until the whole thing was in. Before he starts fucking me I stop him. I want to take in the moment and feel my asshole filled for the first time.

We started slow with just him fucking me and it felt amazing but I wanted my ass to be pounded not just filled so I start pushing back. His balls were slapping my ass as I screamed for more.

"Fuck me. Harder. Harder. Right there. Fuck me. Oh fuck my ass. Finish in me. I want to feel you inside me."

As I say that he grabs my bikini top and starts fucking me harder and faster. He explodes. I feel him cum in me. I scream out a moan and beg him to keep going.

After a few more minutes he starts slowing down. He collapses on my back still inside me.

We stand there trying to catch our breath. He slowly pulls out of me leaving me leaning against the glass. He walks away for a minute.

When he comes back over he pulls my bikini back up over my ass. He slaps it and tells me to go shower and clean up for dinner but not to touch myself.

I walk to the shower with his cum still inside me. As I'm showering I can't help but smile the whole time thinking about my first gay encounter. The whole time I want to masturbate but know I can't.

When I get out of the shower I dry off and see a note on the counter.

It tells me to go look on the bed for a surprise and to meet him at the restaurant. I set the note down and walk over to the bed to see an outfit laid out for me with another note.

"I know you want to cum so badly. If you wear this outfit to dinner you will have an even more imaginable evening. Now get dressed and come to dinner."

On the bed there was matching black and pink bra and panties, thigh highs, a garter belt and a yellow dress.

I had so many thoughts run through my head. How did he find these clothes? Is he a cross dresser? Am I going to be wearing women's clothes this whole week? What's going to happen tonight?

As I'm thinking all these things I start to get dressed. I slid the panties up my legs, they fit perfect. Next I wrap the garter belt around my waist. Then I grab the bra and clasp it around my chest. I look at myself in the mirror and grin. Next I grab the thigh highs and roll them up and connect them to the garter belt.

Lastly I grab the dress let it drop over my head. I looked stunning in it. it hugged my hips just right. I look at my self in the mirror one more time and went to dinner.