I woke the following day feeling sexy as ever, still in my thong and bra. I got up, made a coffee, and sat on the balcony in my underwear, enjoying the sun rising. I knew of a little beach cove not too far away and figured I would go for a walk there to start my weekend. I got changed into the dress, redid my makeup and lubed my plug, grabbed a bottle of water and made the few hundred-meter walk to the start of the little track.

I was confident nobody would be up and about by now, so I made my way through the bush walk to the beach, and it was a fantastic sight when I popped out through the trees on the other side. I sat there for a good half an hour just thinking about what I was doing and had done the previous night and knew I was hooked on this feeling.

A few older couples started to pop through now and then, so I decided to head back. To my utter shock, a young guy, id say his early twenties, was coming the other way in just shorts, carrying a surfboard. I kept my head down and let out a small Hello in the girliest voice I could when we passed each other. Looking back, I caught him doing the same thing, and he gave me a little smile.

I could feel my cheeks turn bright red, wow. I had just been checked out by my first guy. I couldn't wipe the smile off my face the whole way back, I kept thinking about what I would let him do to me and if he knew what he would say.

I decided to make a stop on the way back, if I had passed as a girl for him and everyone else, surely I could order at a coffee shop. When I got there, it was pretty empty with only one other girl. I made my way up and placed an order, and the woman serving didn't seem to realize I wasn't a girl.

"Sarah."

"Sarah."

It took me a few seconds to realize I had used my dressed name when ordering.

"Sorry," I said, slightly embarrassed and grabbed my coffee, and walked out.

Walking through the town, I passed a cute little beach store, I popped inside and noticed some swimwear off to the side. I realized I hadn't bought any bikinis with me, silly when you think about it coming to a beach town.

Quickly browsing through, I decided on a basic black set, it was a cute set that was a bit more than just a string bikini and had a clip on the back thinking it would make it a little easier for me. I also grabbed a lovely white spaghetti strap summer dress, something I figured I could wear to the beach to look a little more suited.

With the purchases I made, I headed back to the house and immediately tried all the new clothes on. Surprisingly, they worked well with each other, and I lounged around till lunch. Feeling horny again, I went back to play with my dildo, this time, I kept my bikini on and plugged in, and began to suck the cock.

I had it fastened to the wall in the bathroom and with each stroke, tried to see if I could deep-throat it. I managed to get it past the back of my throat a few times, which made me gag, but my little sissy clit was loving it.

I couldn't resist anymore and added lube, pulled out my plug, and drove the cock deep into my ass, it felt amazing as it slid deeper and deeper with each thrust until my ass slapped the wall.

Toying with my nipples as I did, I exploded onto the floor in a matter of minutes, as the cock fell from my ass, I got down on all fours and licked up all the cum I could. I cleaned up and put my plug back in before retreating to the pool for a swim, It was my first time swimming in a bikini, and it felt freeing.

Knowing it would be my last night tonight, I wanted to make the most of it and contemplated heading to one of the bars on the waterfront. The thought terrified me, but I knew it would be my only chance for a while to be able to go out and not worry about being recognized.

What the hell, I thought. I've come this way, I may as well. I practiced walking in heels and talking as much like I could for the afternoon before it was time to get ready.

I put on my black and green lingerie and stockings and decided to wear my black jeggings and shirt with my 4-inch boots. I sat in the little mirror and did my makeup while watching a tutorial, and it came out rather well. Looking in the mirror I took a minute to admire how good I looked, I finished my glass of wine before grabbing my phone and keys and heading off to the bar.

It was quiet when I arrived, with maybe only a handful of people scattered around. I went up to the bar and ordered a margarita, I had just thought about it at this point. The thought of getting asked for ID made me suddenly nervous, thankfully, I wasn't. I went up the stairs to their rooftop area and sat overlooking the street and water.

Looking down, I noticed the guy from earlier this morning walking in. I hoped to have the courage to talk to him, but I was nervous and afraid of what he would think of me.

A few minutes later, I heard footsteps coming up and turned around to see him holding a beer with a massive smile on his face.

"Hey, how are you?" he asked. "I'm Beau."

"Hi! Well, thank you, yourself? Im Sarah."

"Mind if I sit?" he asked, pointing to the chair beside me.

With no real turning back, I motioned for him to join me. He sat his beer down as he took a seat, I was nervous as id ever been, sitting just feet away from a gorgeous young man who had no idea who I was.

We sat and chatted for a while before our drinks had finished, and he asked if I would like another. I quickly obliged, and he took our glasses back down.

Watching him walk away, I couldn't believe a guy like that was interested in me, I sat there and knew at some point I would have to tell him that I was a crossdresser, and that thought terrified me.

He returned a few minutes later, and I decided to tell him now rather than later. He handed me my drink as I thanked him, and I said I had something I needed to tell him.

"What is it?" he asked

"Well, I'm not who you probably think I am, I'm a bit more complicated," I said

"How so?" he asked

Well, this was it, make or break time and I thought he would abuse me and leave.

"I'm not a girl, I'm a crossdresser," I said, slumping my head a little and blushing with embarrassment.

"I half thought you might've been something like that when I saw you this morning. Your voice is a lot better tonight," he said with a chuckle.

Surprised, I looked up at him and asked if he was okay with that.

"Well yeah, you're pretty, and you seem fun, I don't care. As long as you're genuine and nice, it doesn't bother me," Beau said

I could feel an overwhelming amount of relief hit me as we both took another drink, we continued to sit and chat till we finished our drinks when he asked if I wanted to head off for a walk along the beach path.

We grabbed our things, made our way across the road, and chatted while walking along.

It was nice, I hadn't felt this free and open in a long time, we talked about how I started this journey, to family, and all other things that would come up during the "First Date" conversation. We stopped at a little bench on a hill just as the sun was going down.

I felt his hand slowly reach my knee as we sat there looking. I looked down and back up to him as we made eye contact, and slowly both went in for a kiss.

I'd never kissed a guy before, but was it something else? His tongue, cologne, to hand on my cheek drove me crazy, it was a kiss of passion, soft and tender.

When it broke, I knew I felt for him somehow, we both giggled and held hands watching the sun disappear behind the hills.

We shared a few more intimate make-out sessions before I asked if he wanted to return to my place for another drink. He quickly agreed with a grin as we stood up and made our way back, stopping to get him some more beers and another bottle of wine for myself.

Walking in, I told him to take a seat outside and take a drink out for us while I changed into something more comfy.

I changed into my white summer dress, made sure my makeup was okay, and joined him on the outdoor sofa. Sitting down, I sipped my drink, relaxing back and letting my hand rest on his thigh, we looked deep into each other's eyes before he leaned down, driving his tongue deep into mine.

His hands began to wander, slowly working up my thigh around and caressing my ass, I could feel myself letting go and thinking I would let this man do anything he wanted to me.

I slowly through one leg over him and sat on his lap while never breaking our kiss, it was getting steamy very quickly, and I couldn't wait. I broke our kiss and lifted his shirt over his head, revealing his muscular arms and chest, my god, was he hot. He soon reciprocated the gesture and lifted my dress up and over my head before pulling me down to continue to kiss. His hand slowly caressed my ass.

I could feel him make contact with my plug, which made me jump.

"Well, well, looks like someone is prepared," he said with a grin.

"I always am," I replied as he toyed with it, pushing it deeper and letting it slowly retreat.

I let out a soft moan and slowly grind onto him, making the pressure of his fingers work the plug a little deeper and harder. After a minute, I got off of him and onto my knees, wrapped my fingers around the band of his pants, and pulled them off, letting his cock spring up. It looked so big and fat, a bit bigger than my dildo, but not much, I knew I should have no issue with it.

I leaned down and licked the tip of his cock as he let out a moan of pleasure, I worked my way down to his balls, licking back up before taking it in my mouth and giving my first blowjob. I was surprised I wasn't a little hesitant, but at that moment, I knew what I wanted, which was him.

Working his cock in and out of my mouth, I could pop his head past the back of my throat a few times, it felt so much better than a dildo, and I loved every minute of it. He pulled me up and took me by the hand as I led him to the bedroom, we didn't say a word, but both knew what was about to happen.

He spun me around and pushed me onto the bed so I was laying face down, his hands caressed my back and slowly started to pull my panties off, he slowly toyed with my plug a few times before pulling it from my sissy cunt. I let out a moan as it popped free, he quickly got down and started to lick my ass, and I fell in love as soon as he did, his tongue was darting in and out and all around.

"I want you to fuck me, but be gentle. I haven't done it before with anyone," I said

"Don't worry, baby, I'll take care of you," he said as he knelt behind me, lifting my hips to be on all fours.

I passed him some lube from the night table, and he lubed his cock and my awaiting ass. He didn't wait and slowly started to push his cock in, as I felt his head pop in, I moaned, somewhat from pleasure and a little from discomfort. He pulled out and went again, this time, he slid in, I could tell he was bigger than my toy, but the feeling was a million times better.

He worked his cock deeper and deeper with each stroke, and in no time, I could feel his hips hit against mine, feeling accustomed to his size and horny as ever, I told him to fuck me.

He grabbed my hips, and his pace began to pick up, with each thrust, I could feel myself losing control. I never thought the feel of a real cock in my ass would be this good, and I was moaning with pleasure with each thrust. He slowed his pace and pulled my shoulder up to him, turning around and kissing me while slowly fucking my ass.

He pulled out after and while and told me to roll over, I quickly did, and he lifted my legs to his shoulders and drove his cock back in. Holding on, he began to fuck me hard as our eyes were locked, my hands massaging my nipples. I told him I was going to cum, and he went even harder and faster, and before I knew it, I began to shoot strings of cum up my body. As I did, I heard him moan and push his cock as deep as he could and shoot his load into my now not-virgin ass, I could feel every spurt of his hot creamy load fill my ass.

Beau leaned down and kissed me as he slowly withdrew his cock from me. We lay there catching our breaths when he scooped some of my cum off me with his fingers and brought them to my lips. Our eyes locked, and with no words spoken, I sucked them clean. We lay there holding each other before we both fell asleep.