Trading Pics

Sitting at the traffic light, my left foot taps the car's floor anxiously while my other foot holds the brake, seemingly it's the only thing restraining my extreme sexual desires. All day I've been looking forward to getting home before my girlfriend. I generally finish work at least an hour before her. I need that hour to indulge in my hobby. Or fetish. Whatever you choose to call it. She would not be pleased with my fixation, especially my intentions. I had to get home and check my email.

Not just any email, it's my secret account. I've been using it to solicit nude pictures of men I've met on craigslist. Posting on the "casual encounters" section I put a few tantalizing pics of myself wearing women's panties. Just a few pics, to create interest and curiosity. Indicating my desire to trade pictures of me for pictures of men and their cocks and their wives, the amount of replies my slim, petite, frame adorned in sexy panties attracted was remarkable. All sorts of men wanted to fuck me. And they weren't shy about telling me so. It's just too bad for them I never intended to meet with any of them. To be fair, in my ad I never mentioned meeting, just trading pics.

Of course, these men wanted more. I can't blame them. My ass was very sexy. I had a skinny boyish figure at 5'7", 120 lbs on a good day. Hard to blame any of these men for wanting me, my tiny round feminine ass was mouthwatering in panties. I always felt so sexy and naughty wearing panties, taking pics of myself and sharing these pics with horny men. With an impressive collection of panties, my girlfriend had no idea I possessed so many or what I did with them or what went on in my mind while mincing around hard as stone in panties.

Though my ad did just fine supplying me with fresh nude pics of big hard cocks, I still liked to search craigslist for people with similar fetishes. That afternoon I came across this ad:

Seeking Hot Twink to Dress in my Wifes Panties - 45 - Chicago

I was intrigued. I wanted to know more. Opening the link, the ad stated:

"The title pretty much says it all. I can host. You dress in my wife's clothes and we'll see where things go."

There were a few pics attached. A pic of various styles and colors of panties strewn neatly across a well-made bed and a full body shot of the host. He had a thick build, appearing to be big and manly though not muscular. His cock was a thick piece of meat.

My imagination went wild. Picturing myself raiding his wife's panty drawer, prancing around in her clothes sparked something in me I had never felt. How sexy! Just the thought of it all and how naughty it would be made me shiver with anticipation. But there was this man who posted the ad to contend with as well. His ad was ambiguous, stating I could try on his wife's clothes, but I know when he sees me in his wife's panties and lingerie, he will want more than just to look. After looking at that cock of his I'm starting to think that it may be quite fun. A funny feeling came over me. Wouldn't it be hot to let a man see me in panties in the flesh? Wouldn't playing with a real cock be more exciting than jacking off to pics of one?

So, I replied with no intention other than wanting to tease him:

"Hi.

I'm very slim, usually wear a small to medium size panty. I'd love to dress up and dance for you. Put on your wife's dresses and skirts, sexy panties, give you a little show, sit on your lap and feel that hard on of yours. The thought of wearing your wife's clothes really turns me on!"

I attached a few of my sexiest pics to further entice this hunk. In minutes I received a reply.

"You have a nice body. I think you'll fit nicely in my wife's clothes. Actually, she'll be my ex-wife pretty soon now. What's your shoe size?"

And so our correspondence began. We emailed back and forth for an hour. Talked about our fetishes and fantasies. The whole time I was hard beyond belief. Told each other what turned us on the most. For me I told him I loved dressing up for men, making them hard and playing with their cocks (though I never actually had done this, only fantasized about it while masturbating in panties). He told me he liked skinny, feminine boys, that they really got him off. Unlike me, he had several experiences with that type of boy, which in reality was exactly what I was.

From what he told me his divorce wasn't final yet. It seemed that he was not pleased about the way things ended with his wife, and he saw this as an opportunity to get back at her. Having a guy come over and dress in her clothes while she was at work and seduce her husband was his way to get even and have a little fun too. Like many men, playing with a slim feminine guy in panties and lingerie is more exciting sexually than the mind games and drama of a real woman.

Seeing as how I live with my girlfriend, and she would be home soon, my window of sexual freedom for the night was rapidly dwindling. I sent one last message:

"Have to go, but I'll be dreaming of that fat cock of yours! Did your wife suck your cock? I'd love to see your member in action!"

Signing off, I then resumed my straight male life.

I spent the night in bed rolling around with an uncomfortable erection, dreaming of dressing up and going a step further, indulging in my fantasies of being in panties for a man and going down on that fat cock. My girlfriend was asleep but my hard dick would not let me sleep. Finally, I started jacking off slowly knowing a full-blown wank would wake her up. My hand felt so good on my cock, I knew that I wouldn't be able to sleep till I did something about it. She was on her side facing me, so I had to be stealth even with her asleep.

I guess I could've gone to the bathroom and jacked off but it was warm and comfortable in bed and kind of more exciting to try and jack off with her right there next to me. I pulled on my cock in light strokes touching the whole thing, not going fast at all. Then she moved and I froze. She kinda breathed real heavy and then went from her side to on her back. Slowly I started stroking again, zeroed in on her making sure she was asleep. Fuck, it felt so good, so naughty, I was so fucking hard and wanted to cum so bad. I increased the pressure and continued jacking slowly fantasizing about wearing that guy's wife's panties and teasing him, putting on a show for him and what it would be like to be all girly and actually suck his cock.

Just then she moved again and I froze again. She was not the type of girl it would be easy to explain why you are jacking off if she caught you. Luckily, she rolled on her side facing away and I went back to stroking. Not being able to fiercely pump my cock I grabbed it real firm and tight and jacked on it. I was so hard and aroused and had to watch my breathing but by holding my stroking back I couldn't cum! Was trying to figure out if I needed to move the wanking into the bathroom.

Finally, as I was pulling on it, I pressed my fingertips flat on the sensitive underside of my cock under the helmet. Fuck, that felt hot! Didn't need to do much, I was so horny and really close. Just pressing and moving the flesh of my three fingers on the tender underside of my cock head gave it all a new and effective sensation. Kept on thinking about wearing the guy's wife's panties and sucking his cock. At last, it happened. I started to cum, semen squirting out hard and fast almost like I was peeing cum there was so much and it came out for a long time. It felt so fucking good but the difficult part was stifling both my heavy breathing and an almost uncontrollable moan, which I did by holding my breath and then finally letting out a deep breath as my orgasm subsided.

She didn't move, good. I was covered in so much cum on my tummy. Reached for my tee shirt on the floor by the bed I sopped up the mess I had made all over myself. I needed that orgasm; I was so worked up about the possibility of getting to wear some guy's wife's panties. Rolled over and finally fell asleep.

All day at work I kept thinking of his dick. Just sitting around in torment, thinking of the possible emails waiting for me. When the clock struck 5, I was gone. In my car I was zipping home. I burst in the door, dropped my bag, threw down the keys and quickly sat down in front of the computer. Opening my secretive porn email, I saw six new messages. Some new ones and some from men wanting my ass who had emailed me before. Two were from my new friend. I decided to open his first in the order received.

"She didn't suck me too often. Thinks she's too good for it. She was never into it, not her style. I liked to fuck her with her clothes on. Skirts, tights, panties that kind of thing."

"Here's an old video of her sucking me. Hope you can do better!"

I clicked the link. It went to his personal site where the video was kept online.

The vid was shot with him, John, sitting on the couch nude. From the looks it he must have been holding his phone filming. His wife was on her knees between his legs. She was leaning forward with her hands wrapped around his cock, stroking. Up and down the thick length. She lowered her mouth down to his cock and began pumping it with her lips. It was a pretty crappy blow job. The kind you'd expect from a teen girl sucking her first cock. But she kept at it. Pumping his shaft, letting her lips lightly touch the head. You could see his breathing get shorter and more ragged. His hips bucking, trying to get deeper in her mouth, but she refused. John grunted and moaned indicating his imminent orgasm. His wife pulled her mouth off and pumped with only two fingers.

I got a good look at her face in that brief moment. She was above average, really not bad, with brown hair, a tiny nose and plain features. Still had her clothes on though you could see flashes of a bra with her blouse partially unbuttoned. John grunted and humped at her fingers as she stroked him. His hips drew back, his back arched, he shot a big thick spurt of cum into the air. Several more shots erupted and landed on all over her hand and his hairy naked body.

God, I was hard. Seeing her make him blow that big with a crummy bj/hj, I was hot thinking of how big I could make him cum with a real bj. Honestly though, I had never been with a man before. This was the closest I had come. Just talking to a man about sex and hearing about what he wanted to do to me made me as excited as I had ever been. I was possessed with a strange sort of sexual longing that made me feel in a way I never had before. It was like something had come over me and going through with meeting him was something I might actually do.

I opened his next message:

"Hope you liked my video! I'll be home alone all day tomorrow. Come visit me. We can have some fun!"

Included in the message were his address and phone number.

Overly excited, I impulsively replied:

"Oh wow! Thanks for the vid! Do you always cum that much!? I can't wait to see you shoot! When can I come over?"

The thought of actually meeting John and wearing his wife's panties was the most exciting and scariest thing I had ever felt. Kinda like the thrill I first got putting on panties and soliciting pics of guys cocks only many thousand times more exciting. Just the way John was casual, friendly, nonchalant and not creepy about it made me feel at ease. Inside me I could tell it was something I was really going to go through with, I could just tell. It was a mindset and feeling I had never felt. It was like being a secret agent going on a dangerous mission. Adrenaline was seeping out my pores.

During our short exchange I made my plan. I was going to leave for work tomorrow morning, then call in sick and go meet John instead. It was crazy for me to do this. But for some reason the thought of actually going through with this and doing it made me as excited and horny as I had ever been in my life. Get to wear panties and clothing of some guy's wife? Just the thought of it, the anticipation of it made my penis ache really funny. Then the possibility of playing with some guy's cock while wearing his wife's panties? Scary as hell but excited that this opportunity fell into my lap. My girlfriend shouldn't suspect a thing.

It was a long night. No jacking off, I wanted to save it for being with John. Tossed and turned all night. Was curious if I would chicken out in the morning. Slept, but it was the type of thin sleep you have when you have a big exam the next morning or are going on a long trip the upcoming day. In the morning I showered and shaved all the hair I could on my legs. Even shaved under my arms, have to say that made me feel feminine and sexy. Shaved my balls and though I knew I probably shouldn't have, shaved all my pubes except a "landing strip". Fuck, that felt sexy and naughty. Said goodbye to the girlfriend without things seeming weird.

I pulled into John's driveway. Sitting in my car I contemplated the weight of my actions. I was being unfaithful to my girlfriend, with a man, no less. If she knew, it would never be the same, she would probably break up with me for being gay. It was not the sort of thing that would be forgiven. But this was a part of me, something I needed to explore at least this once. I exited the car. His house was a nice two-story suburban home. Nicely manicured lawn, trees, flower beds, the works. I approached his unassuming front door and knocked, initiating the loss of my innocence. Immediately I had the instinct to bolt. Just turn and run to my car. But I had come too far and wanted this too badly. I could hear him approaching the door. My heart was pounding in my chest.

The door swung open to reveal a burly, mature man. He was tall, taller than me, 6 foot at least. Broad shoulders. Brown hair with bits of grey streaking the sides. Looking down on me he smiled broadly.

"Nice to finally meet you, Chris," as he extended his big manly hand.

I shook his hand weakly, and squeaked hello. His other hand clasped my shoulder and drew me inside. I could smell his aftershave, he smelled masculine. Just noticing his scent, his overt masculinity made things strange, it both scared and revolted me, yet it turned me on too with the excitement of what would surely be happening soon. His house was neat and clean inside. Releasing my hand, he moved his hand cupping my face in one big, rough palm. He turned my face toward his.

"You're cute. Not too masculine."

"Thanks," I replied sheepishly, dropping my eyes again.

"Relax, sweetheart. This will be fun. We don't have to go too fast." I nodded my head, feeling rather uncertain. "Let's go upstairs and you can see my wife's collection."

"Sorry, I'm just nervous. Never done this before," I tried to explain, I felt comfortable relating this to him. "Being dishonest with my girlfriend is wearing on me."

He extended his arm across my shoulders angling me toward the stairs as he told me:

"But it feels so good to indulge in your fantasy. I'm sure you've had these feelings for a long time, just like me. It's time we enjoyed them," John told me in what seemed to be a very comforting, matter of fact way in what I could only guess to be some sort of fairly thick Italian New York accent.

John walked me upstairs and guided me into his bedroom. The room opened to the left, with the head of the bed against the left wall. There was a door in the far-right corner of the room leading to a master bath. On the right wall close to the door was a long, low dresser. He left me and approached the dresser.

"Come, have a look," John said in a reassuring tone, after sliding the top drawer open.

I approached.

My eyes feasted on the treasure trove of panties before me. I started getting hard seeing all the lace, cotton, silk, variously colored and styled panties. It was fantastic and naughty to see all these wonderful items of John's wife. For me as a guy who was intoxicated by lingerie and feeling feminine it was a gold mine. My girlfriend had nothing even close, compared to what I gazed upon. It felt so naughty to be checking out a woman's lingerie without her knowledge.

"You can wear whatever you want," John told me. "This is all about you feeling sexy."

I let my hands dive into the drawer, sorting through this magnificent collection. "I can wear anything?"

"Absolutely. There are skirts, tops, and lingerie in the other drawers and dresses and shoes in the closet. I'll be downstairs when you feel comfortable." And with that he walked to the hallway. Pausing in the door he said, "Oh, and I left some things for you in the bathroom."

He gave me a wry smile, winked, and shut the door. Curious, I made my way to the bathroom, my interest piqued. Standing in the door to the bathroom I found his gifts. On the counter was a brunette wig and makeup. I walked in and approached the wig. Stroking the fine hair, I knew this would make my crossdressing fantasy complete. Well, almost.

I stripped off my clothes. Standing in front of the large bathroom mirror I admired my boyish figure. Narrow shoulders, slim arms, and as of this morning, hairless. I felt sexy. My shaved legs looked feminine. Always I had wanted to paint my toenails pink like my girlfriend's but could never get the nerve, even when she was away for a few days. I took the wig and positioned it upon my head. It took some adjusting, turning, moving back and forth, but eventually it fit. And it looked quite convincing. My new hair was very straight, the bangs were cut in a stylish arch over my eyes. I looked like a teen girl. I began looking through the make-up. Having never used make-up before I really didn't know where to start. Lipstick is always sexy, so I selected a nice red shade and began applying it to my upper lip. With both lips coated, it did look sexy. I decided to leave it at that for now.

Returning to the panty drawer, I came back to a silky lavender tanga I'd seen earlier. It felt smooth and sexy in my fingers, with a tiny bow and lace around the waist and leg openings. I set them out on the dresser, there were other things to put on first. Drawing a lacy little garter belt out of the drawer I slipped it around my waist. The white garter belt fit snugly. Its ribbons hung down my thighs, I began searching for a pair of thigh high stockings. Finding a pair, I sat down on the bed and slipped them on my legs. Standing, I attached the garters with quite a bit of difficulty to the buttons on the ornate, lacy dark tan cuff of the stockings. With the panties in hand I slipped them over everything. The panties fit so sensuously between my round little cheeks. On my hairless body the silkiness of the stockings and panties felt marvelous.

Rummaging through the closet I found a nice, simple dress. With so many lovely dresses it was tough to choose. This one was short and slim, with spaghetti straps. It was creamy beige color that complimented my fair skin well. I slipped it over my head, making a note to dress first before applying a wig and make-up, next time. I turned circles, admiring myself in the full body mirror. Damn, I looked hot. Like so many young sluts I'd seen flaunting their bodies in public. Then I remembered, I had a man waiting for me. I wonder what he'll think of me? A sly grin on my face, I needed one last touch; shoes.

In the closet I found many different shoes, I just wanted something simple. But sexy worked too. I selected a pair of gold rhinestone high heels with little straps that attach around the ankles and open toes, kinda like high heel sandals. I put them on and they actually fit OK. Awkwardly made my way to the door. Walking in high heels with the sensation of the stockings gave me a feeling of femininity I had never felt. The gold high heels and the beige dress paired well together, like they were meant for me, as if I knew what I was doing fashion wise. I felt and looked so sexy even though I was a little scared and very guilty about actually heading downstairs to have a gay encounter.