Close to the Edge

Story Info
A married crossdresser meets a boy, accidentally.
15.5k words
4.49
9.4k
10
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

Close to the Edge

(or The Accidental Boyfriend)

Sabrina G. Langton

***

Author's Note: Something fun and bubbly to get us through the winter, over that crazy terrain, and even closer to the edge, ha... hold on. Hope YOU like it.

***

I had to admit, I wasn't really ready for it.

"Hey everyone, This is Sabrina."

"Finally, we knew it would happen sooner or later."

"He has been tellin' us about you, I'm tellin' ya nonstop."

"If you are as incredible as he says, I am taking you home for myself."

"Oh my god, I love your nails."

I had to admit, I wasn't ready at all.

***

So surprisingly, I had a new boyfriend. Well, 'A' boyfriend. He treated me wonderfully, I couldn't believe how lucky I was. Three weeks ago, I was just working as a retail buyer, just minding my own business, I worked for a large department store, right here in Pasadena, California. It was beautiful. We had the Rose Bowl, we had the mountains, we had a huge highway running right through us, and we had a million malls. I met him at one of them.

"Hi, is anyone sitting here?" I was in Starbucks and a man about my age, quite good-looking, big smile on his face, wanted to sit across from me, right in front of my coffee of the day, right next to my Victoria's Secret bag.

"Um, no."

"Thanks, it's quite crowded, you know for a Tuesday." He smiled, I smiled back.

I wasn't used to talking to men. I really wasn't used to talking to anyone, especially the way I was dressed.

"Work at the mall?" He looked up pretty optimistically, but I was hoping he was going to be on his phone, or listening to music, and ignoring the 'woman' at his table.

"I do, but not today."

"Busman's holiday?"

"I guess." I smiled, I was quite nervous, he seemed too nice, too interested. No one ever talked to me in Starbucks, or Wendy's, or Victoria's Secret, or any other place I happened to go on Tuesdays.

We ended up talking for ninety minutes, we had four coffees each so they wouldn't chase us out. I was having a surprisingly wonderful time, I went to the restroom a lot. He invited me to dinner, I said yes. I didn't know what I was thinking, There was no easy way I could have dinner with him, with a man. I can't stress enough that I definitely wasn't looking for one. You know, a man.

The wife would be so mad at me if she found out.

***

I hate even telling you this, but, I was a crossdresser. I was, back then. It's not that I didn't love it or was ashamed of it, quite the contrary, I loved it probably a little too much. It was my favorite activity, my favorite hobby, my absolute favorite thing to do in the world.

I was married for almost two years, I was twenty-seven, 5'8", pretty average, and definitely not on the skinny side. My wife Marie was two years older than me, worked nights, well most nights, she was in real estate. She was quite busy and she loved her job, her office, the people she worked with. We had complicated schedules, we saw little of each other during the week, sometimes we were together on the weekend. But, lucky me I had off on Tuesdays.

Tuesday's, for a crossdresser, was fantastic. Life was less busy, less crowded, less everything. That was the day I got to dress up at home, and sneak out, go shopping, go crazy. Well, not really crazy. I had been dressing since I was about nine. I had access to my sister's clothes, she was two years older, she had so many, she never missed them. I had access to a bathroom in the basement, the toilet didn't work, the sink was always black and the vent made lots of noise. Noise to cover me getting dressed, playing with myself, practicing my voice, and clicking with my sister's heels on the cracked tiles.

I can't believe I am telling you this, but I even remember the first time I had an orgasm, I must have been, mmm I don't know, young. I was looking in the mirror, I had a little bit of makeup on, the little bit I was able to borrow from my mom. I was wearing my sister's pale yellow dress, it was short, it was tight, it made the washcloths that I used inside the bra for breasts look fantastic. I was brushing my hair trying to get a somewhat feminine hairstyle, I was acting so girlie, I was giggling, and I was leaning into the sink. I started pushing into it, my crotch leaning against it, it started to feel pretty good. As I played with my hair, adjusted my boobs, and fixed my lipstick I kept on leaning and putting pressure on the sink, my crotch at a perfect height. It didn't take long before something started happening, something I didn't understand, the girl in the mirror was surprised, she was going to have to do this again.

And again.

***

Where was I? Oh yeah, I was going to have dinner with Farrell on Friday night. Farrell, that was his name, he was Irish, he didn't have an accent or anything, and the more I looked at him, I realized he was probably a couple of years older than me. I'll say thirty-one, thirty-three. He had nice eyes, wide shoulders, big hands, and a bigger Jeep, he worked for the City and he loved my name, he told me it was Irish like his. I don't know what I was thinking, I was married, I was nervous, I was male. I also didn't think I passed all the time. But on Friday night I wasn't any of those things. I was busy, I was confident and I was getting ready for a date. My first date as Sabrina.

I was home alone, Maria was still showing houses, she would be out for most of the night. Once she was done her team went out for drinks, it was okay, I got to dress up some more. She wanted me to work regular hours to have time to clean and cook, while she got to shmooze and mingle with others in her field. We had a little apartment and I played in the little bathroom, I was used to it, it reminded me of when I was young and hid in my parent's basement.

I was in the shower, I was shaving my legs. The entire leg, not just the part from the upper knees down that could be seen, the whole leg. I figured it was March, it was cooler, I probably wouldn't have to show Maria my legs until at least June, that was the plan. I then decided to shave my arms, then my underarms, that wasn't a great idea, but when I was done it looked fantastic, it was one less thing to worry about and suddenly I wanted more. My body didn't have much hair, to begin with, plus I was light blonde, I was half Irish and half Swede, I had nothing but blondes in my heritage anyway. I took the razor to my chest, stomach, neck, every place I could reach. I then soaked in some of Marie's best bath balms, they were pink and put me in the right mood. I figured I had to do everything, a chance to date a man doesn't come up too often.

I was going to meet Farrell at the mall, right where we first met, right in front of Starbucks. Our Starbucks. It was going to be romantic, we were going to tell our grandchildren. I lied to him and said I was working. Well that wasn't the only lie, but what was I going to do, I wanted to go out with a man at least once in my life. At least before I turned thirty.

I was getting dressed, I looked up online to find out what to wear on a first date. I even made a friend, Jeffrey, on social media, she told me not to worry and just be myself. Also not to wear too much makeup. So I looked up some makeup tutorials and then at the few femme things that I had. I found the most perfect dress at the bottom of the box. I had everything in one box, all my female clothes, shoes, bags, baggies of makeup, and plastic nails. I was like a woman on the run, on the lam, in a box.

Of course, the greenish-blue dress was a mess, completely wrinkled. I wrestled with the idea of wearing something of Marie's. Before we were married she found some of my stash of clothes, she was mad, she was a little disappointed. She held up every item one at a time and glared at me. I lied and said I didn't dress up too often, every once in a while, once a year... maybe. I had to promise never to wear her clothes, never even to open her closet unless I was cleaning or organizing. Never to say anything to anybody.

So, I ironed.

I ironed some of Marie's clothes too, for the heck of it.

I put on my makeup, I was quite confident, I was usually quite pretty. I watched YouTube videos, I was quite an okay makeup artist, I had been practicing for years. I put on my false lashes, a little mascara, and some eyeliner. My skin tone matched my foundation perfectly, took me so long to find and use the right colors but it was worth it. It was worth all the money and experimentation. I put on a light pink on my lips and cheeks, I put on my long fashion-length nails and painted them the same color as my lips. Soon I was in front of the mirror in a beige waist cincher, a beige bra holding my C-cup silicone forms and I had on beige padded panties and pantyhose. I slipped on the cyan dress, three-quarter sleeves, and short hem, just reaching the middle of my thighs. I slipped on my four-inch light pink pumps, bows right on the toes, a necklace full of pastel-colored stones, and some 'Bombshell Nights Eau de Parfum.'

"Look at you, ready for a first date," I told the blonde in blue in my mirror. "You are so cute."

I then realized I looked more ready for Easter, which just passed, even my pink bag, maybe I should take some eggs just in case. I filled my little pink pocketbook with licorice and jelly beans instead. I rattled a little bit when I walked.

*

Walking through the Mall on a Friday night was a whole different experience than a Tuesday afternoon. That day I always made sure I left the mall before the kids got out of school, I didn't need the scrutiny of a sixteen-year-old beauty queen. Now I was maneuvering through the crowds, who were shopping, eating, standing around pointing out crossdressers with pink heels. I suddenly felt so obvious. I was in a short dress, high heels, long nails, of course I was a CD. I stopped. I looked in a long mirror next to a gadget store, I avoided the gaze of people angry that I stopped in front of them, banging their shopping bags into me. The woman in the mirror looked quite nice in blue, she had great hair, long and blonde, full and well passed her shoulders. It was slightly hiding her eyes. I lifted a little with my long fingers, I wanted to check my earrings, make sure they didn't come loose and fall. They were big, they were gold clip-on hoops. I made a little satisfied face, I looked pretty good, maybe I was just another beauty queen looking for a new tiara, new king. Maybe I just wanted to point out some crossdressers, you know, just for cover. I kept on looking, I played with my hair, it was real, it was all me, it was the main thing that made me passable. I always had girl hair.

I started to move, then started to get nervous again as I got closer to our rendezvous point, I was focusing on the sound of my heels, I was looking down, I was thinking how was I going to get into the house tonight. Leaving as a woman was easy, but getting back in heels with Marie in the apartment might be tough. She would be in bed, she might be making a quick trip to the bathroom. I was distracted, I looked up, I was in front of Starbucks, Farrell was here, he walked over to me. I would have other things to worry about now.

*

"Now that is a great dress."

I smiled I wasn't used to compliments if that even was one. "Thank you, it's cyan."

"Is it? Do you give all of your dresses names?"

I could tell he was nervous, almost as much as me. It was the first date for both of us. We left the crowded mall, the nosy crowds, he took me to his favorite Japanese restaurant nearby. It was on a nice beautiful block, trees, lights, children in carriages. It was much quieter here. I was kind of wishing we had the loudness of the mall as a backdrop, disguise my voice a little, disguise the sound of my heart beating a little too loudly.

In the restaurant, the little booth, we had sushi, we had saki, I couldn't stop looking at him. It just didn't feel real, it was a fantasy of mine come to life. He kept glancing down at my breasts, at my hands, he was making me smile. I taught him how to use chopsticks. For dessert we had oranges and he smiled as I ripped one open with my long nails. He couldn't stop watching me, I felt pretty good, I felt more femme than usual. He fed me an orange, I fed him some jelly beans.

"That day we met at the mall I was checking my texts and I saw you in Starbucks, I wanted to meet you. You looked like you needed company."

I smiled, I did need company. I always wished I had a friend to share my crossdressing adventures with, the few that I have had. I never guessed I would have a date before a friend.

"I'm glad you sat with me, I love a bit of company. It was fun."

We talked, it was wonderful, I was having a great time, he seemed to like me right away. I felt I always made a good first impression, but after that, it had to be all downhill, those were the odds. My wife would tell you the same exact thing, but don't ask her.

He was now glancing at my breasts again, the large protrusions on my chest, my lips, my hair. Pink and blonde, my two favorite colors, oh and cyan. I was thinking I liked this so much better than being with Marie, she would say we were spending too much money, leaving too big of a tip, couldn't wait to go home and watch TV. But I realized it was mainly because I was in a dress and heels, I smelled like oranges and perfume. Maybe I could bring it up to Marie again, maybe we could start going out as women. Well, it could happen, we just couldn't spend any money. I'm sure she would make me sit at a table in a corner by myself, she would be pointing me out to other crossdressers and beauty queens.

After the restaurant, we went for a walk around town. Pasadena had so many things to see, especially at night, everything was always lit up. The weather was quite nice, he pointed out places he knew with two hands, my voice got softer more feminine as I talked and walked. After sixteen minutes, he held my hand, he pointed things out with just one.

I felt like he was showing me off, he said hello to everyone we passed, he took me window shopping, and watched me in the reflective glass. I had quite a nice figure with the waist cincher, I actually had hips. I was five foot eight and probably a hundred and fifty pounds, my legs were slightly thick, but my body was quite tight, I exercised like crazy, I did weights and squats, they gave me a great ass.

After an hour of wandering around, we suddenly stopped, we were in front of a huge mansion, the steps led right down to the sidewalk, right down to us, to me, looking up. We were surrounded by brightly lit trees.

"I'm home." He smiled. I looked up again, we shifted, we moved for a man and his dogs. "Well not really, but I do know someone who has a house just like this. I want to take you there one day."

"Okay." I smiled, I was enjoying holding hands. I was enjoying the idea that he wanted to be with me again, one day.

Farrell faced me, I was looking up at him. Cars passed us, I was glad people were seeing me with a man, a handsome masculine man, one that was smiling down at me.

"When would be a good time to see you again?"

It was a question I didn't think about before, I figured he would say he would call and then he wouldn't. I would be totally fine with it. I would go back to Starbucks alone in a different wrinkled dress and heels. But deep down I was loving this, I was having the best time of my life. I was actually doing something I had only dreamt about. So I grinned big, I showed my white teeth. "Anytime. Whenever you want, it was such a great night."

Yes, I told him anytime. You heard that correctly.

I was standing in the middle of the sidewalk. I started acting like a woman with time on her hands, just waiting around for men to call and take her out. Just lying around, washing my hair, doing my nails, you know the drill. He wanted to pick me up at four the next day, Saturday. I wouldn't tell my wife I had a second date. I wouldn't tell her he kissed me goodnight.

I definitely wouldn't tell her he made me cum in my panties.

We were standing next to my car, my little red Toyota, red was for girls, I was a girl holding hands with a man. Marie hated my car. Real men don't drive little red cars, she would tell me, real men would have bigger cars than their wives. But, I loved it. It was perfect, I loved driving in heels, hanging in parking lots brushing my hair. Plus it almost matched one of my favorite skirts. It was also less expensive than my other car, the one I had before we were married. Marie wanted a nice car, something her clients would respect, with room for extra passengers. One of us had to downgrade, I didn't mind if it was me, I didn't even tell her. I traded in my big four-door Chevy and got something cheaper. I now loved my two-door, it was now perfect for me.

"Here we are. Here's my baby." I said patting the hood, being cute.

He smiled, "It's nice, a great color. Can you text me your address later?"

"Okay," Yeah, like that was going to happen.

And then he kissed me, I was surprised, just to the right of my lips. I fell slightly back against my car, my clean red car, my car with my boy clothes in the backseat. I could see the paper bag in my peripheral vision.

"You are so pretty, thank you for having dinner with me." He smiled, he looked at my plump lips, I wanted him to kiss me again. I put one hand on his chest, watched my fingers on his shirt, my long pink nails wandering around his hard chest. I looked up, I smiled. He kissed me, again.

I put my arms around his neck as his tongue went into my mouth, I felt my head move sideways, we were making out, in a parking lot at the mall. He wouldn't forget our first goodbye kiss to end our first date. His body was right against me, one hand on my waist the other on my perfect red car. My hands started roaming through his hair. I felt myself pushing into him, he felt nothing like a sink, he was a man, a big sturdy man, and I suddenly started to feel something, my body started to vibrate, I suddenly started to cum, I was completely surprised. I was tucked tight and I was cumming. I just had slight friction between my silky legs.

What the heck!

"Ahh," I said into his lips. My first kiss from a man and I had an orgasm, I couldn't let him know, I couldn't even let him realize. I pulled away slowly, I was a little embarrassed. "I better go. I can't wait 'til tomorrow."

"Me too. What's the name of the dress I will be seeing you in?"

"Um, Morgan?"

"Ha, okay." He helped me enter the car, I gave him the rest of the jelly beans from my bag.

He watched me start her up, put on my music. He bent down and kissed me again through the window. It was nice, it was cute, I gave him my tongue, I let him suck it, I ran my long nails on his cheeks.

"Bye, thank you for being so nice." I had to go, I smiled, I waved out the window. I watched him in the rearview, he was getting smaller. I had to push on my crotch, I was getting bigger, I pushed, I came again. Twice in ten minutes. I was cruising at ten miles an hour, who'd a thought?

I had to go on more dates with men.

*

"What do you mean your busy today, we are going to my parents for dinner." Marie was a little pissed at me. You remember Marie, my wife, the realtor, she was angry. "You came home so late last night and now you are going out again. What the hell?"

"Something came up, I didn't plan it."

I didn't really know why she was so agitated, sometimes she didn't even take me with her. She glared at me, but I was prepared, I bought vodka for her father, Lemoncello for her brother and she grabbed the couple of shopping bags I had filled with the dessert I made two days before so she could take it to their house. I was busy but I still got her everything she needed for the day. She wouldn't miss me anyway, she just wanted me to feel a little guilty. It always worked.