Cunt! Ch. 08

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Big Dicks

Around six in the morning I awoke snuggled up against Mark, his arm draped over my body and my ass pressed against his crotch. I was wearing only my bikini top. Realizing how incredibly incriminating this might look if his parents happened to wander into our room, I scooted out from under his arm, got up, took off the bikini, and threw on some athletic shorts and a T-shirt. I stuffed the bikini and the cum-shirt into the front of my suit case and hopped back into bed, having to push Mark back over onto his side as I did. I was asleep again soon after and didn’t wake up until my alarm went off at 9:30 AM.

Mark was already out of bed and no longer in the bedroom. I got up and went looking for him, nervous that things might be awkward this morning given how intimate (and not drunk) we were the night before. But once again, to my surprise, Mark just said “Good morning!” and was acting as if nothing had happened. He was sitting in the kitchen, eating his morning of cereal. Was he drunker than I thought last night? I hadn’t see him drinking very much, we each had a few but there was still a ton left in the bottle, it didn’t make sense. He wasn’t acting drunk at all.

“My parents are spending the day golfing, so we have the whole day unsupervised, well at least until around five or so. What do you want to get into?” He asked.

“I don’t know,” I replied as I poured some cereal into a bowl, “Pool, Beach, Ocean.”

“I was hoping we could walk down to the pier today, there is a cool beach shop that sells some neat souvenirs.”

“Okay that sounds fun!”

“Oh, and this awesome burger shack, it’s seriously one of the best burgers I have ever had.”

“Well, do you want to eat and head down to the pool, and we can swim and chill until about eleven or so and then head to the pier.”

“Let’s do it!”

Mark and I finished breakfast and headed to our room to get changed. I still was confused by him not acknowledging anything that had happened last night, but whatever, maybe he really was that drunk and I just didn’t notice. Or maybe this was how he had chosen to deal with the situation: just act like it didn’t happen. Whatever his thinking (or not thinking) was, I guess I could be happy that he is acting normally.

The pool was pretty crowded, all kinds of ladies were lounging out in the sun working on their tans. There weren’t any lounge chairs left around the pool, so Mark and I set up at a picnic table. Mark threw his stuff down and immediately jumped in the water, I sat down at the table and took my time. I stared at all the different women, admiring their beauty and femininity. I was mentally awarding them with prizes: best bathing suit, best hair, cutest beach outfit, etc. But mainly I was wishing I could be any of them.

I wanted to be admired for how much effort I had put into looking nice. I wanted people to see me in a bathing suit and think “Wow! She is beautiful!” I wanted guys to be attracted to me and I wanted girls to appreciate me. I wanted to tan my legs in the sun and not think twice about it. I wanted to have boobs, fill out my bras, spice up my outfits, and tease boys with my cleavage. I wanted to feel pretty. I wanted to be a girl.

After about 15 minutes or so, Mark got out of the pool and came to sit with me. I guess I was being quiet because he asked, “You’re quiet! Is everything okay?”

“Yeah… I’m just feeling a little drowsy today. I need to wake up!”

“I feel great! You should get in the pool, it woke me right up.”

“Maybe, in a minute. I don’t feel like it at the moment.”

“Okay, well, hey, can you put some sun tan lotion on my back. I can’t reach everywhere and I’m afraid I’ll burn if I don’t put any on today.”

Mark handed me the bottle of sun screen and I squirted a blob of it onto his back, then began rubbing it in. He moaned as I massaged the lotion into his skin. “Mmm… That feels awesome!”

“You’re enjoying this too much. Don’t make it weird!”

“You’ll have to give me a massage later! Your hands are amazing!”

“You do me first and will talk!” I shot back as I finished rubbing the last of the lotion into his skin.

“Your turn!” Mark said excitedly.

I lifted my shirt off and turned my back to him. Mark squirted some of the lotion into his hands and rubbed it all over my back, with long, slow, sensual strokes. It felt really good! He had squeezed a bit more than necessary and began rubbing the access on my shoulder, neck, and down my arms. Then he returned my shoulders and gave me a firm shoulder massage. “Oh… that feels really good!”

“Now, you are the one making it weird!”

Mark went down my back one last time and actually went into my shorts a little as he did, lightly touching the top of my butt. I turned and looked at him over my shoulder. He was grinning at me widely. I turned back and blushed; maybe he did remember last night after all!

We finished applying the sun tan lotion and sat quietly waiting for it to set in. Two women got up from some of their lounge chairs, packed up, and headed to the beach. We quickly grabbed the seats they left and laid down to tan in the sun. sariyer escort After a couple of hours of alternating between the sunbathing and hopping in the pool, Mark asked if I was ready to head down to the pier.

The walk to the pier was hot! I had to put on my t-shirt because I could feel my shoulders starting to burn as the sun beat down on us. I people-watched the whole time, appreciating all the beautiful women I wished I could be like along the way. Mark was also checking out all the girls, but I guarantee, for much different reasons. “Ash, would you bang her?” he asked about a busty brunette, a little taller than me.

“Of course, who wouldn’t? She is gorgeous!”

In my head, I was wishing for her breasts. She was probably a bit too endowed for the top she was rocking. Her cleavage was popping out of the bikini. But then again, if I were her in would probably be doing the same thing. The male side of me was lusting after her hard and I noticed that I didn’t think like that much anymore. Every day I seemed further alienated from natural gender.

After a thirty minute walk, we had arrived at the pier. Mark was so excited to show me the beach shop. It was pretty cute! “Ash, I can’t tell you how many memories I have here, we come here every year!” Mark immediately left to explore all the trinkets, oddities, and weaponry you only see at the strange place that is, the tourist beach shop. But low and behold, I saw something that interested me so much more.

Along the wall, were bathing suits, so many cute bathing suits and bikinis, that I could hardly contain my excitement. While Mark was off exploring, oblivious to me, I started grabbing everything I wanted to try on. I grabbed probably six bikinis, three linen cover-ups, two cute women’s T-shirts, three beach dresses, and four pairs of flip flops. Then I made a beeline for the dressing room.

After a mini fashion show, I walked away with a bikini(green with white polkadots), a one-piece (black), a cover up (linen, white), a beach dress (floral), and a pair of tan, Rainbow flip-flops. I rushed to the counter, hoping Mark wouldn’t catch me. I don’t know why I presumed he wouldn’t ask me what I had purchased, but I wasn’t really thinking and was just hoping he wouldn’t ask what in had bought.

“$86.93, miss” the middle eastern man at the counter said once he had scanned everything. I blushed knowing he had mistaken me for a girl even the I probably looked like the biggest tomboy on the world right now. I handed him my debit card and he handed me my bag. I waited patiently until Mark was finished exploring the store and had purchased his souvenirs. Immediately, he asked what I bought.

“Just some gifts for family!” I replied.

“Cool! Let me see!” Before I could react, Mark playfully snatched the bag from me and started rummaging through it. “Ash, these are all girl’s clothes? You buying for them for Derek!”

“Haha! That would be hilarious! No, I bought them for my cousin, she ask me to grab her some cool beach clothes for her trip to Hawaii she is taking with my Aunt and Uncle this summer, after she graduates.”

“Hmm… You pick out bathing suits for your female cousin?”

“Yes… I don’t tell many people this but I love fashion and she trusts my judgement.”

“Really?… That still seems very strange!”

“Welp! I don’t know what to tell you.”

“I don’t believe you. I think these clothes are for you.”

I was silent for a few seconds while my brain worked on thinking up a good enough response to maybe convince him otherwise. “Haha… Well, be-“

“Ashley, it’s okay! You have put on a bikini two nights in a row now. For most guys, it would take a lot to get them to do such a thing and risk their masculinity, you did it pretty willingly.”

I said nothing and just looked at him. I could feel tears building in my eyes. It took everything in me to hold them back.

“You did a great job putting on make-up last night and you seemed so comfortable wearing the bathing suit, it makes me think that this isn’t your first time doing either… so what I’m getting at is… if you want me to believe the story about your cousin, I will, and we’ll never mention this again. But I want you to know, that it is okay if you like crossdressing, its okay if you like dressing up like a girl, I accept you, and I’ll keep your secret. You are one of my good friends, this doesn’t change anything.”

A tear escaped and rolled down my cheek, I looked at him watery-eyed and said, “You mean that? You’ll still like me even though I like dressing like a girl! You don’t think I’m a freak?”

“Yes, Ashley, I promise I still like you. You are not a freak! Lots of people do it! And for the record, you make a beautiful girl.”

I couldn’t contain myself anymore and I grabbed him, hugging him as hard as I could around his stomach with my face pressing against his chest. I began crying against him, doing my best not to sob, just letting out small whimpers. “You don’t how much this means to me… I have no one I can talk too… I have felt so confused and broken.”

Mark hugged me back and held on eskort until I calmed down a bit. After a few minutes I had regained my composure and Mark led me over to a bench by the store. We just sat quietly until I was ready to talk again. “So yes, I’m a crossdresser I guess. I really enjoy wearing women’s clothes. Honestly, if I could, I would do it all the time. I started doing it around Christmas and I really just love doing it. I have bought a small collection of things and try to wear them when I can, but it’s hard with the parents in the house.”

“So why do you like doing it?”

“I don’t know… I just feel comfortable and attractive. I like the way I look, I have a confidence I never knew I had. It feels good! It feels right!”

“So you have been dressed in public before?”

“Just some drives here and there, hanging out in the backyard, and I went to a restaurant and had dinner, once!”

“Really? Wow! How’d that go?”

“Amazingly! No one knew I wasn’t a girl! I fit right in!”

“That’s awesome! Oh, that reminds me, wait here!”

Mark left me with our stuff and ran into the beach shop, about five minutes later he emerged with a small plastic bag. “Here!”

“What’s this?”

“Open it!”

Inside were a pair of women’s sunglasses. They were turtle shell patterned with big, round lenses. They were very popular at the time and super cute. “What’s this for?” I asked.

“For you to wear back!”

“But I am guy me!”

“I thought you might want to wear one of your new bathing suits back!”

“What? No, I can’t! What if people notice?”

“So what? We don’t know these people! And I guarantee no one notices.”

” I can’t!”

“I dare you!”


“I dare you to wear your green bikini back to the condo.”


“I bet you fifty dollars you won’t wear that bikini back to the condo!”

I knew what he was doing, but I was looking for a reason to dress. Mark gave that to me and I really appreciated it. I noticed a restroom near the parking lot of the pier.

“Fine! I’ll do it! You better have the money waiting when we get back.”

I grabbed my bags and headed to the bathroom. It was just as gross as all public restrooms on the inside. Luckily, I was just changing! I sat my stuff down on a baby-changing table and fished out the green bikini, cover-up, and flip-flops. I took off my t-shirt and swim trunks, crumpled them up, and chucked them in the bag.

After removing the tags from everything, I pulled on the bikini bottoms, tucking my genitals the best I could, followed by the top and looked in the mirror. It was just as cute as when I had put it on in the store twenty minutes before. I didn’t have any beasts to fill out the top, but it didn’t look unnatural. And my tuck-job seemed to suffice as I had no noticeable bulge. I threw on the linen cover-up and put on my new flip-flops. Once I had gathered up all my bags, I opened the door and headed back to Mark.

I had butterflies in my stomach as I walking towards him. Mark was looking at things in the window display of the beach shop. I reached up and tapped on his shoulder. He turned around and it looked like it took him a few seconds to realize it was me. “Whoa! Ashley! You look very pretty!”

“Thank you!” I blushingly said in my girl voice.

“I like your outfit!”

I twirled around giving Mark a view of the back.” You don’t think anyone won’t notice I’m not a girl.”

“Not with that ass! How can a guy have a better butt than like 90% of women we saw on the beach today!”

“Just lucky I guess!”

He stared a little longer, smiling at me. Maybe he was taking it all in. “Well, let’s go grab that burger!”

We started toward the burger joint then Mark turned and said, “Oh, here!” and handed me the sunglasses he bought me. I put them on, he looked at me and smiled, “They look real good! I have excellent taste!” I replied, “I mean, when you’re right, you’re right!”

The restaurant, aptly named “Beach Burger”, was a tiki themed burger shack that seated a maximum of twenty people. We were still a little early for the lunch rush, so we grabbed a table right away and each looked over the menu. The waitress came over and asked us for our drinks orders. I always got nervous when I had to speak using my girl voice, I had practiced it for months but I still didn’t think that it was anywhere good enough. “I’ll have a coke!” Derek stated.

“I think I’ll have the same!” I followed.

The waitress said she’d be right back to take our food orders.

“I like your girl voice Ashley, it sounds very natural and pretty.”

“You think so, I have been practicing it for a while! I still don’t like it.”

“Well, I do! It suits you.”

The waitress returned with our drinks and we ordered our meals.

“So what do you want to get into after this”

“I don’t know, we can just head back to the room so I can change!”

“Why? You were just saying you never get to do this! Let’s keep you in that bikini as long as we can.”

“Haha! Okay. I’d like that. It won’t make you uncomfortable?”

“Uncomfortable? beyoglu escort Do I look uncomfortable now?”


“Okay, then it’s settled. We are just going to enjoy the day, doing whatever, and we can head home around dinner time.”

“Okay Okay!” I was blushing and smiling.

“So do I still call you “Ash?”

“Yeah, I think that’s fine or Ashley, it works both ways so I don’t mind.”

“Easy enough. So tell me what you like about being a girl.”

“Everything, I think! It started with the way the clothes felt; everything was so soft, comfortable, and fit so well, unlike any of my male clothes. Then, seeing myself dressed up and wearing make-up, I looked good. It looked natural and I felt pretty. I have never felt that way as a guy! I feel like I make a strange looking guy but I think I make a pretty, attractive girl.”

“I’d agree, you are very pretty like this!”

“Thank you! Then, I started shopping for clothes and I fell in love with doing that. There are so many colors and styles to choose from, everything is bright and pretty, many more exciting options than guys clothes. I bought a makeup kit and started learning how to do that. I would practice after everyone went to bed, reading beauty blog after beauty blog, trying to replicate the tutorials and pictures I found; and even that was fun. I really didn’t think I’d like doing my makeup.”

“This may a bit inappropriate to ask, but, do you wear women’s underwear?”

“Panties, every day, that are so comfy! I haven’t warn any boxers since I started dressing. Well, not until this trip! And bras, only when I can.”

“I wish I had known about you earlier, so I could have let you know that you could have warn panties down here and it would have been fine!”

“Thank you! Mark, it means so much that you accept me for who I am, don’t make fun of me, and that I can trust you to keep my secret.”

“No problem! And who knows, maybe I’ll try on some panties, the way you talk so highly about them!”

“Really? Are you interested?”

“Haha! No, not at all!”

“Haha! Never say never!”

” So do you think that you want to be a real girl?”

“… I don’t know! What exactly do you mean?”

“Like go to a doctor and get on hormones and stuff.”

“Yeah, I don’t know… I haven’t decided yet. I have looked into it, but I’m still not sure that I actually want try to be a woman.”

“I will say that this is the happiest I have ever seen you. You haven’t stopped smiling since I first saw you in the bikini.”

“It does make happy! I just need more time to decide! I’m worried what my family will think.”

“That’s understandable. So do you like guys? Do you still like girls?”

“That’s also confusing! I never thought I would say this. But the more I dress, the more I admire girls and feel attracted to guys. It’s strange! I’m definitely open to it, I’d say.”

“So… no more girls?”

“I didn’t say that, the were like thirty girls on the beach I’d fuck if they let me!”

“Awesome! I had to make sure I hadn’t lost my wingman.”

“Haha! Nope! I feel like a confused mess, but right now I am enjoying being able to be me and not having to hide.”

“Good! That’s what I wanted. Whatever you decide, whenever you decide, I just want you to be happy.”

At that exact moment the food arrived. Mark was right about the place, it was one of the best burgers I had ever had in my entire life and their fries are were superb as well. When the check came, Mark insisted he pay, citing the fact that I had probably just spent most of my vacation money on clothes. I still had more than enough left, but I wasn’t going to fight him on it. It made the whole meal feel like a date and I have to say I kind of liked that. “Where to next?” he asked.

We decided just to hang out on the beach, since we both felt like we hadn’t spent enough time there yet. One of the large resorts had open chairs and no one seemed to be watching, so we snagged two of them and laid down our towels. Then, we undressed to our bathing suits, hid our stuff under the chairs, and ran towards the ocean. This was my first time in the water in a bikini and I have to say it was nice, there wasn’t anything particularly different from all the other times I had done it as a guy, I just felt more free I guess.

I dove into the ocean to get my hair wet and when I came back up Mark was staring at me. “What?” I asked. Mark smiled and started rapidly splashing me in the face. I closed my eyes and dove under the water again to avoid the onslaught, then I swam around him, and jumped on his back. I went for the choke hold but he easily swung me over his shoulder and caught me in his arms. I was now in the classic bridal carry pose. I think that might have been Mark’s plan all along because he leaned down and kissed me passionately.

I hadn’t been expecting this, I never expected him to kiss me in public, but that didn’t deter me. Soon, we were exploring each other’s mouth furiously; it was sloppy and reckless but neither of us cared. This went on for a few minutes until Mark broke the kiss and laid me back in the ocean on my feet. I looked around an saw an older woman (early sixties?) shaking her head in judgement of us. “Let’s head back to the chairs!” Mark said. I looked at him with a look of panic on my face. “I can’t… I uh… I have a boner!”

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