An Evening Stroll

It was early evening and I was already feeling that special twinge down below. I decided to clean up my dishes from dinner and, being Friday, spend a nice evening looking at porn and jerking off. I settled down and began flipping through pages of various porn. Nothing seemed to be getting me going tonight. Maybe it was time I gave myself some special attention.

I thought to myself about possibilities; dress up in something special and take pics, or wear something over my sexy girl clothes and go out, and there's always the option of giving my ass some playful attention. I continued surfing different galleries as I thought about what I really wanted, or what I really needed.

That's when I came across a gallery that really stirred me up. A typical guy dressed in white stockings and a garter. I immediately began to stiffen. After a few pics he had inserted an anal plug and displayed his ass in various positions. I gently rubbed my crotch through the soft pajama pants I'd put on and feeling jealous, yearned to have my ass filled.

I didn't have a plug of my own. I was still too nervous to get one at the sex shop. But I did have an unused zuchini left over from dinner that might be just right. I went to the kitchen and brought it back to my bedroom.

First though, what to wear. I figured I would attempt to copy the gallery as close as I could, and although I didn't have white, I did have a pair of sheer, black stockings with lace tops and a matching black, lace garter. I slid the garter up over my hips. My cock starting to grow in anticipation. Then I sat down on the bed and slid the stockings up my legs, one by one, admiring how sexy my long legs looked in them. I clipped the garter to the stockings and admired the way my cock hung, semi-hard in contrast to the soft, feminine undergarments.

I looked over in anticipation of stuffing the fat zuchini up my ass, went to the dresser and opened a drawer containing condoms and lube. I fetched a tube of lube and a condom. I opened both and decided to lube my ass with a couple of fingers first. Slowly I worked the first finger in, getting lots of lube spread around the rim of my tight, little hole. I couldn't wait to feel something larger, but relished the moment and took my time working my ass and putting the second finger in.

After a few minutes, I felt ready. I lowered the condom over the zuchini and squirted lube down it's length, spreading it around the shaft. I squatted on the floor and began pushing, feeling it widen substantially. My cock twitched and jerked as my ass involuntarily squeezed. I was at that point where I wanted nothing more than that surrogate cock all the way in, but knew I would have to relax a little. I took a deep breath and relaxed every muscle in my body. I could feel my cock wanting to flex and my ass needing to constrict. I felt the widest part enter me and let my ass pull it the rest of the way in. My cock sprang to near fully hard.

Gently, I began easing it in and out. As much as this would have satisfied my cravings for the night, I had other ideas. I methodically worked it further into me. The pleasure I derived was driving me crazy. I wanted it all the way in so badly. I realized that it would be too much to get it all the way in so I pulled it out, cut off a few inches, and tapered the end so it wouldn't be too much struggle to pull it out.

I now felt confident that I could get that nice, stout, four inch plug up my ass and leave it there. Once I got it started it slid right in to my stretched ass. As the base neared my hole, I slowed. I felt it begin to disappear. Nervous, I tested to see how easily it would come back out. The condom was long enough to leave a tail hanging out of my ass and this reassured me that there would be no problem.

Finally I let it slide all the way into my ass. The physical feeling was good enough, but the thought of having this thing up inside me gave me butterflies. I took in the sensations and let out a sigh of pleasure. I slowly stood up and let my body adjust to our new friend. The feelings kept me semi-hard and I had urges to masturbate and enjoy this new sensation to its' fullest right away. But I was also in a patient mood, and wanted to see how far I could take this newfound pleasure. I grabbed a pair of sheer black panties with a little pink bow and stepped into them. I felt sexy. I felt like a slut that was ready for anything. If I was going to do this, I thought, I might as well go all the way. I got out the camisole that matched the panties and slipped it over my head. The movements of my body increased the sensation of the plug in my ass. The urge to grab my cock and start jerking it was intense. I was so aroused it took everything I had to relax and enjoy more.

That's when the idea hit me. It wasn't anything new really, but I decided to take one of the dogs out for a walk. The neighbourhood was pretty mellow so this would give me the opportunity to be out in public without the likelihood of much, if any, interaction.

It had cooled down with recent rains, so I'd be able to wear somewhat concealing clothing. I put on pair of gym pants and a light jacket. I decided not to wear a t-shirt thinking that it would be way more fun and not too risky. I threw on a pair of running shoes and checked myself out in the mirror. I looked like your average Joe, exactly what I wanted. I always loved knowing that no one would have ever guessed what was hidden underneath when I went out wearing ladies undergarments.

I called LuLu, the saner of the two dogs, put the leash on her, and took a deep breath. I made one last check to make sure I still had a good bit of condom exiting my ass. Everything seemed in order. I opened the door and stepped into the fresh, cool air. We took off down the street. It felt exhilarating to be out on the street like this. I was a little nervous but as we continued I felt more and more at ease. A couple cars went by, some people on bicycles. I grew confident and decided I would head down a slightly busier street. There were some shops and restaurants, a cafe, and a few galleries on Blossom Blvd. There would be people around but it was a very mellow scene. And doubtful I would run into anyone I knew.

I made my way down Blossom without anyone taking notice of me. A few people smiled at LuLu but that was about it until I neared the end of the strip. Three young women were coming towards me when one really took an interest in LuLu. As I stood there she knelt down to give LuLu attention. The other two just kind of stood there chatting to each other like their friend did this all the time. We made small talk, exchanging pleasantries, and I watched as her skirt crept up her bare thigh. The feeling of interacting with someone while hiding the things I was turned out to be quite exhilarating. I could feel my ass throbbing and cock twitching. We parted ways after another minute, my cock left semi-erect, pushing against my panties.

I turned the corner and made my way down the darker streets feeling a little safer with my stiffened dick. I thought about the woman and her legs, reaching down to rub my cock as I walked. The combination of gym pants and panties made for a nice feeling and my prick continued to stiffen. My awareness heightened and I glanced around quickly, realizing I was now rubbing my hard cock as I walked down the street. The plus was that my jacket hung down below my waist and I could at least somewhat conceal myself.

LuLu was content walking along minding her own business, needing little attention. I thought about what was under the woman's dress, what I might have seen if it had slid up enough to reveal her panties. Red maybe? Satin or lace? I pictured what her pussy might look like, trimmed pussy hair, or maybe a full, dark bush. I pictured her showing me right there on the street, hiking up her skirt, exposing her panties to me and asking me to rub my cock for her.

I slowed my pace and adjusted my panties. My hard cock easily popped out the side, now straining against my pants. I glanced around again, my stomach doing flip-flops. But I was so turned on and ready to cum. I reached into my pants. My hand brushed against the garter. I pushed down and felt the stockings on my leg, running my hand up the garter to find my prick. I was surprised by the amount of juice that had collected at the end of it. It was plenty to lube my engorged tip.

I watched the headlights of two bicycles come towards me. I waited until the last second and pulled my hand out of my pants. A young couple slowly strode by and even said "hello" as they passed. They probably couldn't even see my dick jutting out the front of my pants in the dark. I pushed my hand back inside and rubbed. The toy I had up my ass was causing all kinds of sensations and the constant reminder added much to the whole experience.

I was getting to that point, where I knew I would have to cum soon. Excited about my new adventure I decided to push it even further. I walked down the street and ducked into the first alleyway I came to. I was only a couple blocks from home now, feeling comfortable yet still a little nervous. My eyes darted back and forth until I slowed to a stop halfway down the alley. Now, I reached back into my pants and rubbed my cock again. With the cool air washing over me I pushed my pants down to my knees. As I stood there exposed the air on my skin felt exhilarating. I glanced around again, this time noticing some movement in the house through the fence behind me. I turned, my pants slipping to my ankles.

I peered through the fence to see a woman sitting on a couch, splayed in a sexy pose. She rubbed her tits through a turquoise teddy looking towards the other side of the room which was out of view. She reached one hand down to her pussy. I couldn't believe my luck! I settled in, leaned against the fence, slowly rubbing my cock now. I alternated between stroking my hard dick and playing with my ass. Beginning slowly, but working to a steady pace of sliding the home-made plug in and out of my hole as I watched this woman slip a hand under her teddy to rub and pinch her nipples. Her other hand still on her pussy.

She stood up, her thick legs supporting her slightly chubby body. She peeled the teddy off of her shoulders to reveal a pair of large, soft and round breasts. Her hard nipples topped large, pink areola that matched her fair skin. Her body looked soft and she slid her teddy the rest of the way down, revealing her trimmed pussy hair, her mound puffy and visible through the thin bush.

She brought one foot up onto the coffee table, still wearing a pair of shiny, black heels. One hand back on her pussy, she slipped a finger into her slit and rubbed. She was talking to someone out of view still and I was dying to know who. I scanned around again, standing there in the alley with my stockinged legs exposed, my panties now pulled down to my stocking tops, and my jacket open so I could rub my nipples through the silky camisole. LuLu had thankfully settled right down into a soft bed of overgrown grass and laid there.

I peered back through the fence. The woman now worked her spread pussy over. I imagined how wet it must be. And now I saw who the show was for. A man entered my view. He was fully nude, his cock sticking straight out in front of him. He was large, about 6 feet tall and 200lbs. His cock just as impressive, even from my vantage point it looked huge, maybe 8 inches or more. I had let go of my cock and focused on playing with my ass, not wanting to cum before things got good. I focused on my nipples and played with my ass, starting to slide my dildo in and out. My breath excited and becoming more audible, I tried to keep quiet but it became too much and small breaths and groans escaped into the night air.

I watched her wrap her hand around the meaty cock. God, it looked even bigger in comparison to her hand. She stroked it a couple times then appeared to order him down. He dropped to his knees and began licking her spread pussy. She held his head to her pussy, her own head thrown back. I maintained composure and kept my hands off my prick for now. And then something strange happened. It seemed as though he struggled to pull his head back from her pussy, and when he did I could see her yelling at him. He knelt there in front of her as she scolded him and released a smack right across his face.

"What the fuck?" I mumbled aloud.

And then I heard a voice from behind me, "She doms him all the time."

I spun around, my whole body instantly quivering. I was caught dead to rights, as they say. There in the shadows I could see the form of a man. I could see that he had a hand down his pants. "Don't worry, I sneak back here and watch them pretty regularly myself. Are they wearing the leather outfits tonight?"

I stood there staring at him, slowly putting myself together, half-stunned and ignoring his question.

"You're not going to stop now, are you? It's gonna get better." And he started walking towards me.

LuLu finally began to growl, and I forcefully told him to stay back. He stopped, put his hands up and said, "Chill man, I just came out here for some fun, not trouble. I jack off to these two all the time." I noticed his pants were open, and I could see his cock straining out the top but still contained in his underwear. "Let's just jack off together," he continued.

I turned back to the fence and could see the man back between her legs, his hands now cuffed behind his back. LuLu growled as the man took another step. I shushed her and told her to lay down. He came up next to me against the fence fumbling in his pants. My own cock began to grow again and the butterflies were subsiding.

I tried to keep covered up, hiding my preference for ladies clothing. I pulled my cock back out and began rubbing. After a couple minutes he looked over, "You know, we could...help each other out, if you want."

I was nervous again. "I don't know, uh, I, I'm not sure if..."

He reached out, "I could just help you a little." I felt his hand on the head of my prick. My whole body tingled. "You can just watch them."

I focused back through the fence and watched as the woman turned around, her ass in the man's face. He leaned forward, engulfed between her big ass cheeks. She watched him as he licked her ass and pussy. Pre-cum dripped out of me and my new friend rubbed it into the head of my prick. He moved behind me now. I could feel his body against my back. He reached around my right side, his hard prick brushing against my ass. With his left hand he slid my pants back down. His hand roaming over my ass cheeks, I was nervous.

"I like you're panties," he whispered in my ear. "Would you like to feel me against your ass again?"

I could only whisper a yes. He leaned into me again. As his cock nestled into the crack of my ass his right hand moved up my body over the camisole while his other hand found the garter straps and he traced them down to my stockings.

He whispered into my ear again, "I didn't realize you were such a hot, little slut." This sort of took me aback but I had become a lot more relaxed.

"You don't know the half of it," I responded. The woman was laying the man down on the couch. She teased his cock with her hand for a minute, then reached and grabbed what appeared to be a vibrator. He writhed in ecstasy as she brought it down the length of his cock.

"You shouldn't be hiding the slut that you are." He pulled my pants down to my ankles and I stepped out of them. My jacket came off next. I stood there in the alleyway wearing only stockings and garter, my panties and the camisole. I felt so exposed and free. "God, I'm so fucking horny now. I wanna fuck you so bad." He grabbed me tight from behind and thrust his cock hard against my panty covered ass.

I remained silent. He asked, "What's the matter, you're not sure about that?" His hand slid into the back of my panties where he found the end of the condom dangling out of my ass. "What's this?" He tugged at it as I wriggled a little. I relaxed my ass as he tugged gently. The zuchini began to slide out and I moaned as it did. He slid it in and out.

I was completely out of control. I was ready for anything now and wanted to feel any sexual delight possible. I felt myself loosening up. I felt as if I was dreaming as the words came out of my mouth, "Make me your little slut. I want it all." I could hardly believe it, to be honest. But it was true.

I hardly noticed what was happening in the house now. It seemed a waste but I was consumed with my new feelings. I wanted to be used. I wanted to be exposed. I wanted this stranger to have complete control.

He turned me around, telling me to keep my hands at my side. I did as I was told. He stepped close and our cocks came together. Both dripping, he rubbed them together. The feeling was incredible.

"Does that feel good?" he asked.

"Yes," was all I could say.

"You like my cock, don't you? You want it, don't you?"

He pushed me down by the shoulders and I dropped to my knees. "You're my little slut now. I'm gonna do what I want with you." The excitement welled up within me. "Suck my cock, slut," he demanded.

In the darkness, I looked at the glistening piece of meat. I had dreamed of moments exactly like this many times. Imagined so many cocks right in front of me, begging to be sucked. I took a breath, wrapped my hand around it and held it steady as I moved my mouth around it. I licked the tip first, swirling my tongue around it, then moving halfway down the length of it. Thankfully it wasn't too big around or too long. I guessed around 6 inches. I was able to slide it into my mouth without forcing my jaw open, a relief. I loved the sweet taste and the feeling of wrapping my lips around it as it slid along my tongue. I easily slid it in and out, comfortable with 3-4 inches in my mouth. I worked that cock over more and more, relishing the whole situation.

"I didn't think you'd be so good. Maybe you suck dick a lot?" he inquired.

I mumbled an "uh-uh" with his cock still in my mouth.

"Wow, so you just love it, huh? You're just a cock-loving little slut. My slut. Maybe I should share you? Let you suck some more cocks?"

I wasn't so sure about this but it did make me hot. I took a deep breath and pulled his hips into me as I forced his cock all the way into my mouth. The tip of his prick just filling my throat. I breathed through my nose but felt myself wretch a little. I was glad it wasn't any bigger! It didn't take long to get used to as I took that hard dick all the way into my mouth over and over.

I could taste the juice dripping out of him, sweet and sticky. He was moaning now, his head thrown back. He placed his hands on the back of my head and pulled me on and off of his prick. Then he stopped me. I craved his cock in my mouth as I stared at it a few inches away, he continued to hold me back as I tried to push forward and get it back in my mouth.

"Easy, baby. I want you to see what's happening in the house."

I stood and turned, peering through the fence. My eyes focused to see the man laying on the couch, on his back. The woman held him by his ankles, legs in the air and spread wide. She was wearing some type of harness and I realized she wore a strap-on and thrust into him with vigor. She appeared to taunt him verbally.

"Oh, shit," was all I said.

"Hot, isn't it? Watching him get fucked hard like that. He's a little cock slut like you are." He moved his hands over my ass cheeks as he shuffled behind me. He smacked my ass. "I asked you a question, slut. Answer me."

I barely uttered an, "uh-huh."

Another hard smack on my ass. "I said answer me. When I ask you a question I want you to speak clearly and you better give me more than a mumble!" He brought his hand down against my ass again. I was nervous about how loud it was. "Now tell me, it's hot isn't it?"