Sandy's Journey

AUTHOR'S NOTE: This story is completely fictional. All characters are 18 or older.

Sandy's Journey

CHAPTER 1: Oops

The whole thing started from an accident. Well, kind of, anyway.

My name's Sandy James. For some reason known only to potheads, my parents named me Xander. When I was two, I couldn't pronounce it, and told everyone my name was Sandy. My parents either decided to let me choose or forgot what my birth certificate said, and I've been Sandy ever since.

Anyway, here's what happened. I was getting ready for work one day and realized I didn't have any clean underwear. I had a big meeting with the brass scheduled, and going commando in my tailored suit didn't seem to be a great idea. The boys needed to be corraled. What to do?

Then I remembered there was a clean pair of woman's panties in my sock drawer. A cute little thing named Tanya had forgotten to put them on after a late night of drunken sex. She'd called an Uber to get home, and I'd found them in the sheets the next morning. I'd washed them and put them away in case I ever got another shot at her tight little hole.

They were red lace thongs, but I figured they had enough fabric to keep my junk confined. I quickly pulled them out of the drawer and skinnied them up my legs. My balls just barely fit into the gusset, my soft cock stayed put. They weren't the most comfortable thing I'd ever worn, but they would do.

I finished getting dressed and wolfed down a bagel and a cup of coffee for breakfast, then headed out for the walk to the metro. It was only a block, and the weather was nice, so I swung along easily. Underneath my clothes, things were happening. I'd never felt a satiny fabric like this thong against my balls, and I found it much nicer than the cotton I was used to.

Then there was the other feeling. The thong strap began working its way up between my cheeks. I couldn't very well adjust anything out there in the street, so I went with the feeling. Soon it was rubbing against my asshole with every stride I took. I'd never worn anything like this, and never felt anything like that -- well, except for that crazy chick in Sheboygan with the long fingers, but that was different. This was soft, barely touching, and it felt good. It felt like a silken fingertip just rubbing softly rubbing against that sensitive opening. It felt naughty, like the first time you rub your cock and feel it start to tingle.

I made the train station in no time, ran my pass through the machine and headed for the platform. I had a few minutes before the next train, and I found myself thinking about asses and panties. I glanced around at the other men on the platform, wondering if any of them were dressed like me underneath. I wondered what they would think if they could see my lacy red thong. I checked out women's asses as well, with their much more visible lines. I could see some that appeared to be wearing thongs, and wondered if they liked the feel of the string rubbing their assholes as much as I did.

The morning commute was crowded, and I stood for most of the ride. For the first two stops, one of the women I'd judged as wearing a thong stood in front of me, her ass close enough to my cock for me to feel its heat. What would she think of my thong, I wondered, and the cock inside? I was getting hard and had to hold myself away from her so as not to poke her with it. Then she got off, and I was pushed forward by people entering the car behind me. I wound up with a chubby little woman in front of me, but a tall, slender gentleman standing very close behind. This time I could feel the heat from his groin. All sorts of kinky thoughts rolled through my head. My ass felt exposed, covered only by the cloth of my suit pants, and part of me wanted to rub my cheeks back against him.

My fantasy partner got off the train one stop before I did, so I had a few minutes to get my thoughts under control. Where did all that come from, I thought? Other than the usual fumbling childhood exploration, I'd never been interested in men. Maybe these were magic panties, I thought, bringing a smile to my face.

It was only two blocks from the station to my office building, and I started getting my game face on. I had to be sharp today. I had to brief and be ready to answer a whole lot of questions. No more thinking about sex and panties, boy. We're in the big leagues now.

My boss Tom Whitman was in the elevator when I got in, and we exchanged nods. Nobody talks in elevators, just nods. When we got to our floor he came up alongside me, grabbed my elbow and said, "You ready, Sandy?"

"Yowzah, bossman," I replied, and we exchanged a smile. The meeting started at 9, so I had enough time for another coffee, and to check that the AV guys had my presentation charts ready. At 8:30 I went to drain the lizard. The stalls were all full, so I took the last urinal in line and turned myself slightly to hide my red panties as I worked my cock out, peed, and put it away. Then I went to the big conference room and found myself a seat along the wall, back away from the major players, but close enough to the front so I could visually communicate with the other members of my team, and be heard if I was asked a question during someone else's presentation.

I won't bore you with all of the details. My presentation sailed through perfectly, I had all the answers, and I came across like I actually knew what the fuck I was doing.

We broke for lunch. My team had lunch arranged in a smaller conference room, where we strategized for the afternoon session. A couple people came up to compliment me on my performance. Then it was time to get set up again. I went to the men's room again to drain the main vein. I wasn't thinking about what I was wearing, concentrating instead on the work to come. I stepped up to a middle urinal. As I unzipped and reached in, my boss' boss, Dave Candell, stood up to the one next to me. As he stepped in he clapped me on the shoulder. "Great job, Sandy!" he exclaimed. Taken by surprise, I turned towards him slightly. His eyes went down to be sure I wasn't going to piss on his leg, and they caught me with a handfull of red lace as I worked my cock around it.

He couldn't have missed it, I knew, and his reaction showed he hadn't. His eyes got really big for a second, then he gave a tiny smile and continued to do his business.

He covered quickly, asking me a question that might come up in the afternoon session. Then we went our separate ways back to the big room.

Damn, I thought. It's bad enough anyone saw them, but my boss' boss? Shit, shit shit!

I was a little distracted as we started back up, but pulled myself together and concentrated on what we were doing. Somehow I got through the day, and everything turned out well. I didn't see either boss afterwards. I got home and you can be certain I did laundry that night. The red thong got washed and put back in the sock drawer. As embarassed as I was, I couldn't bring myself to toss them.

CHAPTER 2: An Education

The internet is a wonderful thing and a horrible thing all in one. You can find anything out there, more than you wanted or should see.

A couple days after the incident of Chapter 1, I got to thinking how nice that red thong felt, and I got to looking. It didn't take long to come up with the search string Men's Thong Underwear, and from there a whole new world opened to me. Men's thongs were a thing, and I was immediately directed to sites specializing in "exotic" men's underwear.

Thongs of all colors and shapes, fabrics from cotton to silk to satin to lace. Wow. I even found bra and panty sets designed specifically for men, with tiny or no breast cups.

Part of me knew I was on dangerous ground here -- the land of transgenders, gay crossdressers, cock suckers and ass fuckers. But the larger part of me remembered how the red thong had felt on my nether parts. Why should women have all the fun, I thought? Why can't I have underwear that rubs all my sensitive places? I decided to buy myself a few presents.

Shopping was its own experience. A lot of the cheap pieces looked exactly that -- cheap and poorly made. Ebay had a lot of junk from China. There were Amazon stores that looked like they carried the same stuff, but offering delivery from US sources. Just crap.

I thought of looking at panties for women, but that didn't work out -- just looking at them, I could see they didn't have enough fabric down low to hold my junk. I kept looking, and finally found a couple of sites that sold well-made men's thong underwear, with a pouch big enough to hold me, and the soft fabrics I wanted to try. I bought four panties -- one in black cotton, one in red cotton, kind of as a baseline. I went further with the other two -- one was a black full panty, low-cut in kind of a ruffled black satin. The last one was a male version of Tanya's panties -- low-cut, red thongs in see-through lace.

My cock had gotten hard while looking at all of these sexy things. Many of the pictures showed young men modeling them, with some impressive bulges. I told myself it wasn't the young men, but remembering how sexy a thong felt. I switched over to porn sites on the computer. I was curious about how the panties would fit, and I knew there'd be an answer in pornland. Another quick search for men in panties, and I found myself right on the beach of transgender island.

There was almost zero heterosexual porn featuring men in panties, but endless pages of gay porn. I found myself drawn to the crossdressers. It looked like they had the same problem with women's panties that I did -- inadequate support and coverage. Then again, I realized that wasn't the point, especially when they got hard and their cocks poked inches out above those tiny fabric patches. Still, the forbidden nature of this other world excited me, and in no time at all I was coming hard to video of a man in bra and panties sucking cock. I didn't stop to question what that said about me, just went with the moment.

My new panties came in the mail a few days later (gotta love Amazon Prime.) They were in my mailbox when I got home from work, and I wasted no time at all trying them on. Trotting to my bedroom, I stripped completely and pulled out the first pairs, the cotton thongs. Stepping into them, I quickly pulled them up into place. They had just the right amount of room to support my package. The waistband sat low on my hips, and oh, that string up the back nestled nicely into the crack of my ass. I walked around a little, and they felt perfect. I stepped over to my full length mirror and adjusted the front, then turned and looked over my shoulder to check out my ass. Damn, that was sexy. I'm not in perfect shape, but those twin globes divided by that black strip just looked amazing.

Next I tried on the black ruffled full panties. They were advertised as sissy panties, and they weren't kidding. Looking at them in the mirror, sissy would be the absolute first word to describe a man wearing them. I could see the attraction, though. (as an aside, these became one of my favorites over time, and I'm wearing them as I type this.) They were low-cut too, and the top of my ass crack was quite visible from behind.

Finally, the red lace thong, and I loved it. It fit me perfectly. I rubbed my hand across the bulging pouch in front, feeling the lace against my skin. I turned and admired my ass in the mirror, then ran my hands across my back cheeks. I'd never done that before, and it felt sexy. I pulled my cheeks apart, and the string slipped into the crack until it rested against my asshole. I walked around my apartment that way, feeling the friction on that sensitive hole. I resisted the impulse to stand in front of the window and show the world how sexy I felt, but my cock started growing.

Soon, like the guys in those videos, the tip squeezed its way out the top. I started rubbing my balls, and my cock rose to its full seven inches. Damn, it made me horny. I sat down on the couch and leaned back then pulled the pouch down under my balls, the lace rubbing my perineum, and started to jerk my cock. Within a few minutes I came, splashing my load up on my chest and belly.

I cleaned myself up, then ran a load of laundry with my new panties in them. I wondered what one of those bras would feel like. Maybe some stockings.....?

CHAPTER 3: Just a Dream?

That night I had a dream, the first really sexual one I'd had in years. I was with Tanya again, rolling around in my bed, alternating heavy make-out with playtime, tickling and laughing, then kissing as our hands roved over each other's soft spots, caressing and exciting each other. She rolled me onto my back and was sitting astride my groin, rubbing her sweet spots against my hard cock. I was naked, she was wearing the red thong panties that had started all of this.

I tickled her flanks, then reached for her wonderfully perky c-cup breasts, squeezing them gently as I pressed her nipples between my fingers. She moaned and placed her hands over mine. She leaned forward, kissing me hard as I supported her with my arms. She sat up again, putting her hands on my chest and grinding hard against my hardness. I started to reach down between us, wanting to feel her wet pussy directly against me, but she grabbed my hands and put them on her hips, kissing me again.

"Now I'm ready for you," she said. Rising up on her knees, she pinched her nipples with one hand while the other rubbed the crotch of the red thong. Then she pulled her hand away. There, creeping out the top of the red lace triangle, was the helmet shape of a hardening circumsized cock.

In my dream I was stunned, but curious. Reaching down I rubbed a fingertip over the tip of her cock, feeling the wetness of precum. I felt it hardening further, growing longer. I grabbed the side strings and pulled them down, and Tanya raised her knees one at a time to allow me to strip the panties off.

There was her cock and her balls, shaved as I remembered her pussy had been in reality. Reaching down, she grabbed both of our rods and began masturbating them together. Then she lay forward onto me, our cocks pressed between our bellies, and ground the two organs together.

We kissed like that for a while, her breasts and cock writhing across my chest and belly. She rolled over, and moved her body 180 degrees, then grabbed my hips, pulling me into a 69 on top of her. Tanya had a deep throat, and in no time my cock had pushed past her mouth and into her throat. She was fucking my cock with it. My cock felt great, my head less so.

I was up on my arms, looking down at her hard cock below me. It was so nice, so smooth, with a wonderful purple helmet. I was seriously conflicted, even in dreamland. What would it mean if I touched a trans cock? I wanted to, but what would that make me? Tanya decided to help me decide. Reaching down with one hand, she held her cock erect, pointed at my mouth. Her other hand ruffled my hair and gently pushed my head forward. More o please my own curiosity than her desire, I lowered my head. I kissed the head of her prick, tasting the precum there. Closing my eyes, I opened my mouth wide......

and that's when I woke up.

I was sweating, my breath rasping as I gasped. I'd never felt a dream so real. I could remember every tiny detail -- the way her mouth tasted, the feel of her nipples between my fingers, the smell of her perfume and her natural musk. My cock was hard as stone. Most of all I remembered the feel of her cock as it began to pass between my lips.

I had wanted cock in my mouth. I lay there on my back, feeling like a line had been crossed. I wanted to wear panties, and I wanted to please a cock. Content that my internal conflict was resolved, I grabbed the shaft of my cock. Holding it as it slowly went down, I drifted off to sleep.

CHAPTER 4: Toys

My interest in panties continued to grow. I even bought bra/panty sets in two different colors -- pink and black. The panties are kind of granny style, being full coverage, with open lace at the sides. I've found the satin of the bra feels as good on my nipples as the panties do on my balls.

This was still a private hobby -- all of my girly things were kept in a locked box in the back of my closet, and I usually only wore them when I was at home. Now and then I'd put on one of the thongs when I was running out to the store for something. Sometimes I'd have a playtime evening at home. Wearing nothing but panties, I'd set up crossdresser porn on the computer. I'd rub my cock through the panties until it outgrew them, then pull them to one side and jerk off to the sights and sounds of a CD sucking cock or getting fucked.

Cocks became objects of sexual desire to me for the first time in my life. It seemed the biggest ones were in gay porn. I'd watch men fucking just to see how big their cocks were, but I saved my orgasms for CD porn.

I'd never touched any cock other than my own, and mine was just too far away to get it into my mouth. I didn't know any gay men, and didn't know how to meet any without risking exposure. So, what to do?

Toys.

Once I'd started looking for panties online, ads had begun to pop up for sex toys. Back to online shopping again. Amazon does have sex toys, but I found other sites with much better prices. I looked, and looked, and thought about what I wanted. Finally I made a few purchases. The first was a dildo, only about 1" in diameter, but 8" long. The second was a vibrating dildo, about 6" long. I needed one more purchase to qualify for free shipping, so on a really naughty whim I added a small butt plug. I knew the taste of the dildos wouldn't be the real thing, but I wanted to see what it felt like.

It took a few days for my purchases to arrive. I went to work every day in full male regalia. No one had mentioned my little wardrobe malfunction, so apparently Dave could be discreet. I spoke to him at the office a few times, and he didn't even wink. Business was business, outside was outside, and they were happy enough with my work not to bother with any little kinks.

My new toys arrived quickly, a UPS box sitting at the door when I came home a few days later. I couldn't wait to check them out. First I unwrapped everything and gave each piece a good cleaning with plenty of hot water and antibacterial soap. I laid them out on a towel on my bed to dry and changed into my bra and panty set. I felt incredibly sexy, and my cock quickly rose to celebrate the occasion.

I absolutely had to play with the slim dildo first. It was soft and clear. I lay back on my bed, enjoying the feel of my satiny lingerie. I closed my eyes and held it against my chest. The hot water wash had warmed it up nicely. It was 8" long with a pronounced head, just like a circumsized cock (I think those are prettier.) I slowly brought it up across my chest to under my chin, then rubbed it across my lips. I stuck my tongue out for a taste of the plastic.

I knew it was all fake, but my heart was pounding, my cock was straining, and I just needed to put the dildo in my mouth. I brought it up so it was vertical, the head pressed against my lips. Very slowly I loosened my lips. I reached out with my tongue to meet the invader, and slowly lowered it into my mouth. God, that felt wonderful. If cocks felt this good, I'd never stop. I can't explain it, only say it was what I never knew I needed.

I kept pressing it deeper, until the bulbed head was pressed up against the opening to my throat. I sucked on it hard, then moved my tongue all around it. I imagined it was the real thing. My right hand was drawn to my cock, tenting out my pink panties. Reaching inside them I rubbed my hand all over my cock and nut sack. I began moving the dildo in and out, fucking my mouth with it. I practiced keeping my teeth covered with my lips. I practiced sucking hard. I withdrew the tool and laved it with my tongue. It had been awfully dry at first, but saliva quickly collected in my mouth, lubricating the dildo and allowing it to slide in and out quite easily. I varied the speed, taking long soft strokes and short hard ones. I loved it all.