Naked by the Ocean

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An older married Crossdresser has a life changing affair.
12.4k words
4.75
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***

Authors Note: Something quick to get us through the cold, just a warm cliched story, an older, disappointed crossdresser goes away, meets a man, yadda, yadda, yadda, well you know, we heard it all before, ha. I hope YOU like it.

***

Naked?

I just turned fifty. I just had a fiftieth birthday party. I was having a mid-life crisis.

"Mmm, I think I could do naked." I was looking in this weird wavy mirror, I turned from side to side, I turned around, and showed the mirror my back. "Well, what da ya think?" I turned my head, tried to look over my shoulder, tried to see my ass. I saw enough. "Forget it, no naked." I sulked, I took a shower, I was tempted to put on swimming trunks.

I was in someone else's house, in someone else's town. I was three blocks from the ocean. It was January. My work rented a house here in Ocean Grove, New Jersey, in the off-season. This was the way off-season, there was so much parking, there was nothing but empty tables at the few open restaurants, there was so much bread and milk at the market. I only had yogurt, fruit, and almond milk in my fridge, I was now taking so many vitamins, I was doing too many squats, I needed to lose a few pounds. I wanted to look good naked.

I was leaving this beautiful town again, but I would be back, I would be thinner. I had my backpack full of clothes, I had a suitcase full of dresses, nylons, high heels even a maid uniform. I wore it when I cleaned the quiet house, I wore it when I took out the vacuum, made some lo-cal vegetable casserole, I wore it when I was alone in someone else's house.

This was where I did all of my crossdressing now. Never at my house anymore. Ooh, didn't I tell you? I was a horny fifty-year-old crossdresser, is that a thing? Is it cliche? Maybe I was transgender, I didn't know, who cares I was in crisis mode.

Because I didn't dress up at home I lost all motivation. Having a wife, having three kids and a dog made it quite difficult to become Giselle, to become a woman, even for a couple of minutes.

*

Forty days ago my supervisor called me into his office.

"Hey, we have a transmission server in the middle of New Jersey."

"Oh yeah?"

"Two AM, Monday through Friday, we are gonna do some tests, just need someone to make sure it happens, semi-supervise. Once it's working we can let it go off on its own, heh. Feel like visiting New Jersey?"

"For how long?"

"First week of every month, until the other systems are set up. Next month is the first test. We already rented a house."

Mmm, I was thinking, by myself in a house for an entire week? "Okay, sure." I got the keys that day, I checked out the pictures online. I bought a suitcase from Goodwill, and I loaded it up.

*

"I hate this mirror." I turned, I posed, the waviness was driving me crazy I would have to get a new one. This was the second month, the second time I have been in this house, I don't know how many times I have worn this maid uniform. I bet this house was never this clean. I was loving coming here, it was doing something to my body, it was doing something to my feminine mind, it was doing something crazy to my libido.

I would get here Monday night, I left after dinner, kissed everyone goodbye. I pulled into the driveway, I headed into the house. I took all my outfits, lingerie, and heels out of my suitcase and set up the closet. I took all my makeup, cleansers, applicators, and various other sundries to keep me beautiful and put them on the little vanity, with the big lighted mirror. I took the few male clothes I had, stuffed them in my backpack, and hid them in the coat closet right near the front door. I would be a 'woman' for the next four and a half days. The company let me work from home anyway, and this was my new home for the week, Giselle's new home. I even went to the transmission building completely femme now, it was late and no one was there. The building was eight by eight and hidden at the end of a parking lot. We didn't even have cameras set up inside it. It was perfect.

Once I was dressed up, I stood by the front door, gazing at the lonely neighborhood, this summer neighborhood in the heart of winter. I shrugged, I made a rash decision. I started walking around the block, in my new dress and heels. I even bought a coat, black which dipped right below most of my hems. I started walking further, I was getting closer to the ocean. I started shopping in the quiet little town, I figured no one would care if a transwoman was shopping, showing off her shaved legs or especially, her new boobs.

Well, MY new boobs. I went crazier I bought a Roanyer Silicone Breastplate. It was a perfect fit, it was D-cup and it matched my body coloring perfectly. I went to a shop in Manhattan and had them color-match me, it cost an extra two hundred dollars, but it was so, SO worth it. I didn't have to go crazy with foundation or worry about the difference between my arm coloring and my breasts. It was a perfect pale color and it gave me so much confidence.

Well, maybe too much confidence.

*

During my third month in Ocean Grove, I decided to visit a little restaurant, it was set up like a pharmacy, it's very quaint and cute. I loved it, so I went back, then I went back again. It was always quiet, the waitress and the cook were happy to have the company. Usually, it was me and maybe two to six other people. I sat at a table near the window by myself, looking beautiful, wishing I was waiting for a date, or having lunch with a late colleague. I wasn't good at doing anything alone. I wore my sunglasses, made believe I was reading a book, and I figured I was passing quite well, no one gave me any strange double takes. Most of the looks I received were from the men looking at my legs, in my shorter skirts. It was now March and it was still quite cold out. Quite windy in this town by the ocean.

I was very proud of myself for going out and mingling, it had been a long time since I had done this.

"Hi,"

I looked up, there was a man in a uniform, smiling at me. He looked a little older, salt and pepper hair, tall, stocky. He could be my type if I had one.

"Oh, hi."

"The streets are so quiet today." He smiled at me again, and I just smiled back. It was nice talking to someone, it was nice that he was focusing on my long pink nails stuffed into my book and not my new double Ds. We talked, well he talked for a couple of minutes, then he got his food to go and he left.

"Bye."

I went back to my soup, I was bouncing my leg, shaking my heel wishing more people would say hello to me. I was way too shy to say anything. I was way too shy to keep up a conversation while wearing a dress.

The door opened. "Hey, I'm sorry, I was thinking can I sit and eat lunch with you?" He was back, I shook my head. This was a very interesting development.

*

I was back in front of my annoying wavy mirror, I just had lunch with a man. I decided to put on something a little slutty. I went a little over the top with my makeup. I had long eyelashes and lots of mascara. My lips were lined, filled, and glossed a dark plum, matching my twenty fingers and toes. I had a brush running over my cheeks and forehead, I wanted to look like the women selling real estate in town. There were three of them on Main Street in Ocean Grove, and all the women working there were older and quite attractive. I wanted to fit in, I couldn't help it if I was just a little bit sexier.

I wanted to practice my banter. "Hi, Ethan, how do you like my skirt." Oh, by the way, that was his name. I smiled, I posed, I even spun. I was a little too excited about having lunch with a man, an officer, a guy in such a masculine uniform. "Please don't arrest me, Officer Ethan, I won't wear a skirt this short in front of the tourists, ha, I didn't know it would turn them on." I laughed, I was getting silly, I was becoming my genuine self. I was becoming that twenty-seven-year-old girl that lived somewhere in the back of my mind. I wish she could stop flipping her hair.

Every November I shaved. That was the month I went crazy again, I soaked in the tub and shaved. I put cream on my arms and the hair fell off. I even made a nice little triangle of reddish blonde in my panties, it was so sexy hiding in the silkiness, I felt it was something I had to do to stay sane.

Now I was showing off my smooth bare arms. I had on a tight black sleeveless top. I was thinking, I was doing the math, mmm, maybe two months until I had to wear shorts again, even short shirts. I was always cold anyway. The top was all lace and showed my wonderful silicone breasts underneath. I had on a short leather mini-skirt. It had a zipper right above my thigh and I had it opened a little too far up. I was wearing nude pantyhose and black six-inch platform heels. I was even holding a black leather clutch with a gold chain. I was taking so many pictures.

Underneath this sexiness, I had on a waist cincher and that was kinda it. No bra, no panties, nothing just me. I wanted to show off my fifty-year-old hairless body. I had lost eleven pounds, I felt fantastic, my midsection was rotating I think it wanted to grind against someone.

My wig was new too, it was long and streaked blonde. It came down to my elbows and was a style way too young for me, but I didn't care I would never show anyone, I would never show Officer Ethan. Today he met me in my shorter light blonde one, it dipped just below my shoulders. It showed my own hairline, that wig was another perfect match. Strawberry blonde, I was born with a feminine hair color.

We met for the rest of the week for lunch. We sat at the same table, we talked. It was a perfect setup. Conversations about the wind, the weather, the ocean. It was nice, I was enjoying myself. He kept touching my hand with my long dark nails, he kept looking at my overlined lips and I kept smiling, showing off my white teeth.

"So I'm guessing you live here in Ocean Grove." He smiled, he was playing with the spoon in his coffee.

"No, unfortunately. I live far away in Brooklyn." I smiled.

"Oh, visiting?"

"Mmm, kind of." And I told him what I was working on, told him I was here a week a month, told him about the little building in the big parking lot.

"Oh, that's what that's for, I was wondering."

I told him I worked from the house, told him I only went to visit that building in the middle of the night, under the cover of darkness, and he laughed as he touched my hands again.

"You have a crazy job." He smiled.

"I do." I squished my face, I was trying to be cute. We talked a little more, it was the longest lunch we ever shared. It was the longest I had talked to a man while presenting feminine in so long. I was enjoying myself but I was slightly shaking, my mouth was constantly dry, then I was speechless.

"Do you think we can go out for dinner tonight?"

"Um, go out, um."

"Are you busy, I don't want to bother you."

"No, no it's fine." And I gave him the address of the house that was less than two blocks away. I even gave him my phone number. I gave a police officer my phone number. After I collected my bearings, realized the new situation, we took a picture together, I wanted something for my contacts. I wanted to see a man's face when he called, I wanted to imagine, I wanted to see his wide grin.

We walked outside, I walked him to his police car. I was keeping him safe.

"Okay see you at seven, I promise to get you home before you have to go to work in that lone parking lot." And then he kissed my hand. It was so unexpected, it was so nice. All I could think about was, when am I going to tell him about myself, then all I could think about is what he looked like naked, maybe with just his police hat and badge.

Ow.

*

I was going through the things in my closet. I had half of them on the bed. I couldn't decide what to wear on a first date. "Oh my god, I am going on a date," I told the wavy mirror, I had to sit down. My phone rang, I got nervous he was going to cancel, he did a background check and he found out that I buttoned on the same side as him.

I closed my eyes, I picked up on the fourth ring, "Hello."

"Hey what's goin' on." It was the wife. I used my female voice, she didn't even notice, I had to stop. Maybe I was merging both sides of myself into one and even I didn't notice anymore. We talked for a little while, I told her I was going out to eat, then work, then probably leave in the morning. I didn't tell her I wanted to sleep in my new seethrough black nightgown, my new almost black thigh highs, I might even wear my new five-inch sandals to bed. I had done that before. Oh, and I had a date with a man, a policeman.

I told her to have a goodnight instead.

"You too."

The talk with the SO, freaked me out a little, I felt whatever was in my panties was now tiny and trying to hide. I was nervous I was thinking it was a sign. I called Ethan, I was too tense, I would cancel. This was such a horrendous idea.

"Hello."

"Hi, Ethan, it's Giselle."

"Oh please don't tell me you are backing out on me, heh. I got us great reservations at someplace you are going to love."

He seemed so happy, exuberant, I couldn't let him down, I took a deep breath and I lied. "No, no, don't be silly. I just have to do a little work before we go, can you come to get me at seven fifteen?"

He laughed, even more, he seemed relieved. I hoped he wasn't going to be disappointed.

*

"How's this?" I asked the wavy mirror, I think it looked okay, I couldn't get my whole body in the mirror no matter how much I bent or moved. I decided to wear black. A little black dress, perfectly modest for a fifty-something divorcée, returning from the mall, roaming the neighborhood, looking for handsome men to misuse. I paired it with gold pumps, three-inch, quite under the radar. Underneath was a different story, I had on my black waist cincher, hip pads, and expensive Wolford pantyhose, beige. They had a nice shine and hid every blemish, not that I had any. With the nylons I had incredible legs, hopefully, Ethan will get a chance to feel them.

The dress was quite low showing a little more cleavage than I was used to. I looked in the mirror, I checked every side, I even bent forward to see how they looked, how they swung, they were very sexy I was loving them and they felt nice and snug in my Maidenform bra. I put a gold collar around my neck to cover the seam. I had on the shorter blonde wig again and big golden hoops that appeared through my hair whenever I turned quickly enough.

My makeup was perfect and subtle, no overlining, no big false eyelashes, just little ones like the ladies in the real estate office, I could assimilate when I had to. My lips were mauve matching my press-on nails, matching my toes hidden in my pumps.

I put on my Chanel and I filled my little red purse. Extra pantyhose, lip liner, lipstick, mascara, compact, a credit card, and a key. "I'm ready." I told the mirror, "I am so ready" I told it again. There was a slight tremble in my voice. Then there was a bell, I walked to the door. I took a deep breath, I was so nervous, I was hoping my antiperspirant was going to be working. I practiced my smile and then opened the door.

"Hi." Officer Ethan handed me flowers. "Here, these are for you." He smiled as I took the bouquet. It was quite big, it was full of hyacinths, sweet pea, lily of the valley, and freesia. It smelled incredible. I loved flowers, they did something to my feminine essence and senses.

"Thank you they're beautiful." I sniffed again and then brought him a glass of wine as I put the flowers in a vase. He watched me, it was nice. I showed him my house for the week, well the rest of the day. I asked him to sit, I had something important to tell him.

He seemed quite concerned, he sat close. "Ethan, I'm, I'm so sorry, but I'm married."

He tilted his head. "Yeah, that's okay, so am I."

And I giggled, I don't know why, it seemed the only legitimate response. We talked about our significant others for a little while, we sipped our wine. I let him look at my legs, it made me not worry about the wives.

"Ethan one more thing." I swallowed, this I hated telling people. Throughout the years I had to have this conversation, I didn't understand why. Why did anyone need to know, what was the big deal, what were the implications? But I told him anyway, "Ethan, I'm transgendered." That's what I have been saying for the last couple of decades and everyone knew what it meant, it wasn't like when I was young and people wanted more information, wanted to know weird details, now everyone just looked on Google afterward if there was something they didn't understand.

He studied my eyes like that was what you did. "Really, okay. I'm Italian." He laughed, he then grabbed my hand, he stood up. I stood up with him. "The restaurant is really fancy is that okay?"

I just looked at him, he was fine, he wasn't asking stupid questions, he wasn't asking to see anything or feel something. It was going to be fine.

"SO, okay. I love fancy, it's my favorite flavor." He smiled, he helped me on with my coat, we headed to Asbury Park, the next town over.

*

The ride was nice, the restaurant was even better. We met the chef, we met the owner, and he was happy we were local. Ethan from Holmdel and Giselle from Ocean Grove. He asked me so many things I couldn't answer, so I just shook my head, he invited us for brunch on Sunday, and unfortunately, I had to decline. I was a little sad. I would be living a different life. When we left we also said goodnight to the waitress, and the chef, it was quite nice. So many more people knew my name.

We went for a brisk walk on the main Avenue, it was quiet, it was windy, I held tightly onto Ethan's arm. We walked over to the little canal, we sat on a bench, I was freezing but I was enjoying myself. He had his arm around me.

"When do you come back to Ocean Grove?"

"Next month. The first week of April."

"Can we do this again?" And then he kissed me. I wasn't expecting it, but I slowly opened my mouth, I let him put his tongue inside of me. I moved closer to him, I had my leg over his and he started to rub me. His big hands were exploring my pantyhose, my thigh. "I'm trying to keep you warm." He smiled.

I squinted "Are you?"

"I am, it's not that I have been dying to touch your legs all night or anything."

I gave him another suspicious look and I kissed him, I initiated it, I wanted him. I had my cold hands around his neck and I held him close, I wished someone was watching.

We stayed on the bench until the wind blew us away.

*

It was after midnight, I would have to be at the transmission server in less than two hours. We were standing by the door, I wanted him to come in, but I felt funny asking.

"Would you like me to keep you company until you have to go to work?"

"Really? I would love that." And he sat on the couch as I got cleaned up. As I brushed my windswept hair and fixed my messy makeup. We talked for less than two hours. We talked about the wives, our life, our work, I even talked about being bi-gender, but we mostly talked about things we wanted to do, things we wanted to see. I still had my leg over his, he still caressed my thighs. Right before I had to go he kissed me again.

"Mmm, I love kissing a woman wearing lipstick."

"Really, is that one of your fantasies?" I was teasing, I kissed him again but he pulled back.

He was thinking. He was looking at my lips, then my eyes, my long lashes. "You know, I think so. I have lots of fantasies."

I smiled, and we kissed again. His hands went to my breasts, I felt him rub, I felt him fondle. He started breathing a little irregularly so I searched blindly for his manhood. I tickled him with my long nails, I slightly squeezed. I released his tongue from my mouth, my mauve lips. "When I come back, can you fill me in on some of your fantasies?"