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Not what I expected, but definitely what I wanted.
I guess it is something that goes through the mind of every new or closeted crossdresser. Shopping for new clothes as a guy is awkward because it is difficult to do without making it obvious it is for you. Yeah you can go online, but it’s tough if you’re not used to the sizing and the clothes never seem to look the same as the picture. Thus, when searching for playmates on Craigslist, if you find someone purging some clothes, you have to check it out. And that’s exactly what happened.

I was bored, AGAIN, and looking for a partner in crime. The wife was out of town on business and I had nothing to do. As I scrolled through the craigslist ads trying to weed out the fakes, weirdoes, and creeps, I would drop several messages that would go unanswered. Something I found to be a common occurrence on that site. Then I came across a rare opportunity. Every once in a while I can find another “girl” purging some of her clothes, or doing it for a friend. I of course responded and waited with great anticipation. Luckily within five minutes I heard back.

Now, like I said, I was bored. So besides confirming I was a real dresser and not just some dude looking for used panties, I tried chatting up my host. They were pretty brief in their responses, but I found that she wouldn’t be dressed and that she was stocky. It was a simple clothing pick up and that’s it. I was not satisfied and tried to see if my sharing would bring them around.

I decided to explain where the picture I sent came from. It was from the only time I revealed myself in public, which was to the take out delivery guy. I was dressed in a school girl outfit which, I explained, was very short and gave excellent views as I came down and went back up my apartment stairs. She suggested I come dressed. Showing up dressed was not something I was counting on, but I was desperate due to a lack of responses on other ads. I agreed.

The rest of the day at work, my commute home, and getting ready I was completely nerved up. The one time I went out in public was to my front step. Now I was going to have to drive to someone’s house and walk to the door. At the same time all those nerves were rushing though me, I also had an incredible wave of excitement. It was going to happen.

I got my little outfit out. Black lace thong, black fishnets, a black push-up bra, a VERY short black and pink plaid mini skirt, white tank top, and some six inch platform heels (thankfully, I had been practicing around the house with these). I looked absolutely slutty and I loved it. I love this outfit because I know that the slightest bend or sway in my walk allows for a tremendous view of the bottoms of my ass cheeks. It’s one of those views that I see on women, that pretty much leaves me paralyzed and drooling. However, I was not going to just walk out through my neighborhood to my car like that. So I put on some baggy sweatpants, a hooded sweatshirt, and some sneakers. I threw my wig and shoes in a bag and I was ready to go.

As I pulled into the long driveway, I was shaking with nervous excitement and anticipation. I dove into this having very little info and no idea what to expect. I stopped and turned the car off about fifty feet from the house, it was as close as I could get. I pushed back the driver seat, pulled off all my guy clothes, and put my wig and heels back on. I looked in my mirror and just told myself to relax and be Ashley.

Luckily it was night and the house was set back pretty far from the road, so I wouldn’t draw too much attention to myself as I approached. And just as that thought passed through my spinning mind, the motion sensor light came on as bright as anything I could compare. There I was in my slutty little outfit halfway between the car and house and I was COMPLETELY exposed to anyone looking in that direction. I decided to forge ahead. Gracefully keeping my balance on those heels, thank god for the practice, I made it to the door. Ding dong the bell went and I waited.

The door opened, and the man on the dimly lit porch apologized for the light being on and turned it off. He invited me in and said the clothes were in the spare bedroom. We came in from the porch to the kitchen which was well lit, so I could see my host. He was a large black man, I’d say about 5’11 and 240 pounds. Short black hair and light facial hair, probably just hadn’t shaved in a few days. He wore baggy jeans and a t shirt.

Honestly, I was a little disappointed. Even though he said he wouldn’t be dressed I kind of half hoped he would because I was going to and also, I’m not really into guys that are overweight. He made no advances other than to say I looked nice and he was amazed at how well I walked in my ridiculously high heels. He came across much more pleasant in person than over email. He showed me down a hallway to a spare bedroom. There were four large cardboard boxes, he told me to go through, take a look, try things on, and take whatever I wanted. He then left me alone.

I started going through the boxes. Unfortunately, I think his friend was closer to his size than mine. Everything was very big and very “Sunday best church ladyish”, which as you are probably aware by my outfit, is not my style. I had nothing else to do, so I figured I’d just keep sorting. I did find a black mesh tank top though. It was see though and only a little big. I took my tank top off, put it on and looked in the mirror. It was perfect for my outfit. The black bra showing through was especially hot. Then I heard a voice behind me, “You like it? It looks good on you.”

It was my host, standing there with another guy. He looked at the other guys and said help yourself. Almost immediately he was fishing through the boxes I finished with. He was another dresser in guy clothing. How much more boring can this night full of promise get? He was a skinny white guy, 5’10” and 180 pounds maybe. He had dirty blonde, medium length hair, clean shaven, wearing well-fitting jeans and a collared shirt. He struck me as a corporate type. We didn’t speak until our host came back to check on us. He was so friendly that we all had a nice conversation about who had come through already, the weirdoes he had encountered, past experiences, etc. Which was all very nice, but this is not the evening I had in mind. I eventually said I found all I wanted (just the tank top that I was still wearing) and that I was going to head out. Our host graciously offered to walk me out. I said bye to the other guy and headed down the hall.

I walked ahead listening to him talking, which I could tell he was distracted. I glanced back and caught him checking out my ass. I was immediately excited again. About halfway to the door, he broke of what he was saying and said, “Wow, you are a natural in those heels. I mean, I’m jealous… I could never wear anything like those.”

I simply replied smiling, “I’ve practiced a little at home.”

As we walked through the kitchen, he began telling me how great I looked in my outfit, especially for a novice, “A true natural,” he said.

Finally, we were back out on the dark porch where we had first met. His voice got lower as he looked back at the kitchen door. “You know… I’m sorry. I know you wanted some playtime, which I wasn’t really looking for originally. After seeing you in that outfit, I think we could have had fun. But then the other girl showed up. If she weren’t here, I’d love to have some fun.”

It was all I needed to hear to let the fun begin. Looking almost at the ground, with him behind me to the left as I was at the door, “Honestly, the way you were talking in the hallway, the way you watched me, I really thought you might at least like a feel…”

I could feel his debate about what was happening and what to do, “Um…”

“You did compliment the way these heels make my legs look, and how much you like my skirt. Don’t you want to feel my leg? Don’t you want to run your hand up it and feel my tight little ass?”

He reached down, mesmerized by my words, his gazed locked on my fishnet covered leg. I did nothing. I felt his warm hand on the outside of my thigh as he gently caressed it and slid up, until my skirt lifted giving his hand access to my tight little butt cheek and his eyes access to my cute panties.

Suddenly, he caught himself, “What about him?” he pointed back the other way.

Coyly I responded, “What does he have to do with anything? I mean, I don’t mind him here if you don’t…”

With that I backed up into him, allowing his large hand to really explore my ass as I gently slid a hand over the front of his pants. The growing bulge in his pants taunted me to go further. It didn’t matter that he wasn’t my type, he had a willing cock. I unzipped him, reached in, and started feeling around. I found his juicy cock, grabbed it, and backed him up to a couch on the porch. Keeping a firm grasp of his warm cock, I positioned myself on all fours on the couch. As I fumbled with is belt and pants, I could feel his hand reaching around behind me, grasping my ass, lightly fingering my tight virgin hole through my panties, and rubbing my rock hard tucked cock. He worked the whole area so well, I could feel my panties wet with precum.

Trying to ignore my own sensations, I finally had his pants open. Hastily, I peeled down the front of his briefs and out sprang a gorgeous black python. It sprang out only the way a semi erect cock does, just a quick spring out and hanging there, begging to be worshiped. I reached out, mesmerized. I’d never seen a black guy’s cock before and always thought it was just a stereotype. It had to be nine and a half inches and thick. Wrapping my little girlish hand around it, I began to massage it, feeling it grow. He let out a low soft moan of acceptance and continued to work my backside, now having his hand inside my panties and applying pressure to my tight hole. With the largest cock I’d ever seen only inches from my face, I decided I needed to taste it, and taste it I did.

Dipping my head to the plump set of balls now hanging over the waistband of his underwear, I extended my tongue as far as it would go, desperate to make as much contact as possible, I slowly licked him. Slowly and deliberately, my tongue explored the underside of his balls, right up the middle, seamlessly onto the base of his manhood, and traveling up the sensitive and sensual underside of that monster. Having my eyes closed the whole time while getting lost in my conquest, I received a glorious surprise.

As my warm outstretched tongue reached the beginning of his head, I got that intoxicating flavor of precum. It was sweet, and somewhat tangy. I loved it. With my hand massaging his cum filled balls, I reached the top and immediately impaled my face on his throbbing member. Being very novice, I had all I could handle, maybe I got five inches in me, it was suffocating. As my warm, wet, hungry, sissy mouth rode him slowly, his whispers of “yeah”, “just like that”, and “oh baby” had begun.

Just then, our wanton lust was interrupted, “Whoa… S-s-sorry… I… um…”

DAMMIT! We totally forgot about the other guy in the back. It didn’t matter, I was a crazed slut at this point, I was all in. Immediately I sprang up, my incredible hard cock pushing up the front of my skirt as my new lover had freed it from my panties, and I cut our friend off at the door.

“Why not stay?”

As he opened his mouth to respond I moved in and attached my mouth to his, immediately probing with my tongue. He dropped his bag of clothes and grabbed my ass with a nice firm squeeze. I reached down, hurriedly undid his pants, allowing them to drop freely. Dropping to my knees, in unison with his pants falling to the floor, I got a delightful view of the prettiest little pink lace panties covering a rock hard five inch cock…. It was beautiful. I gave our host a glance, he was now completely undressed staring at us stroking himself, I gave him a wink and a smile, and turned back to our friend. Those panties were just too sexy to remove, so I moved them to the side allowing his smaller, but still appetizing cock to spring free. I launched my mouth at it, being much smaller, my nose was buried in his neatly trimmed pubes as I took him to the hilt. His balls slapping my chin is a sensation I will never forget.

While working our panty wearing friend at a feverish pace, I noticed our host had repositioned himself right next to us, still stroking. For the next few minutes I alternated between them, mouth on one, hand on the other. The room was filled with their moans and taunts as well as my slurping and grunting as I worked them both like a feverish slut.

What came next was a dream come true. As I had my mouth around our host and stroking our friend, he tensed up, grabbed the back of my head, and drove his monster into my throat with force. It was far deeper than I had taken him or was ready for, he was about to turn me into his personal cum dumpster. With my air cut off by at least seven inches of black cock, he unleashed a giant load, it too much even as far into my throat as he was. It filled my mouth and dribbled out of the sides of my lips. The sight of this must have been too much as our other friend knocked my hand away, positioned himself closer and covered my cock filled face with his own seed.

The giant in my mouth popped back out of my throat and leaked just a little more onto my tongue while softening. My face felt numb, I could feel the cum running down my face, even off the tip of my nose onto the cock now withdrawing from my mouth. I eased myself back still kneeling and admired the two now limp cocks exposed before me. I was fulfilled, I felt used, whorish, and accomplished.

As my lovers got dressed, I wiped the cum from my face with my hand and delighted in its flavor. Once I got enough of it, I stood up, said thanks to the boys and walked out. I got to the car, kicked my heel into it, and drove away. Still dressed, cum stained top, and crusty remnants on my face and wig. Oh, the things us girls do or free clothes.

* Authors Notes * DISCLAIMER – This story is totally fiction and none of it is real. DO NOT MESSAGE ME ASKING ABOUT IT.

This story is protected by International Copyright Law, by the author, all rights reserved. If found posted anywhere other than with this note attached, it has been posted without my permission.

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