Becoming the Neighborhood Slut

Ch.1-Busted

My wife and I had moved to this neighborhood about 3 years ago. It was your standard, stereotypical area. Upper middle class families. Kids playing in the streets, pta parents, neighborhood cookouts, all that sort of stuff you see on TV. It wasn't really our cup of tea to be honest. We didn't have kids. We were more, I guess you could say liberal with our views. We were younger then most of the others, although only by a couple years. But we got a good deal on the house, so we took it. Although most around us tended to be conservative or traditional with their views and values, they didn't look at or treat us any different. We were kinda the "cool couple" on the block. We ended up becoming fairly close with our next door neighbors, Mark and Jen. They were both a few years older than us, had a couple kids, but were pretty relaxed and down to Earth. Everything about them seemed stereotypical, until one fateful night.

I had been crossdressing since I was a teenager. I started like most others and just progressed from there. I told my wife early in our relationship about it. Luckily, she was into it. She loved the idea of me being feminized during sex. However, around the house, I always was my regular male self. It's not that I thought she would have minded, I just always thought that if it wasn't in the bedroom, I should be "her husband" for lack of a better explanation. But when I had time to myself, I loved to get fully dolled up and transform into my female counterpart. My favorite was the one week a year that my wife went on a trip for work. It was a week long conference she attended. I spent all my free time dressed up. I was looking forward to this one in particular because it had been a little while since I had the chance.

Her flight left Sunday morning and the minute she was gone I raced up the stairs. I took a shower and shaved my entire body. I've never really had much body hair, but when I'm fully dressed up, I like to have my arms and legs, as well as everything else perfectly smooth. I then did my makeup. I wasn't perfect at it, but I'm sure better than most, as my wife had actually given me tips over the years. After that it was my wig. A nice curly brunette. That's always been a style of hair that turned me on, so I decided to go with it. I then threw on a black lace thong and matching bra. I obviously didn't need the bra, but I liked the feel of it. After that i slipped on a pair of black thigh highs. I decided that was it. I kept it basic. I wrapped myself in my wife's short silk black robe, and a cute pair of black fuzzy slippers. I was ready to spend the day as a woman!

I started out fairly normal I guess. I grabbed a drink and just relaxed on the couch watching TV. It felt good to be doing normal, everyday things dressed up. I definitely had a plan to get off, but I wanted to wait as long as I could. So I continued doing normal things. Ate lunch, did some chores, relaxed some more. I did occasionally touch and tease myself, but was able to hold off on full blown pleasure. It was early fall and the sun had started setting earlier. Once it hit dusk, I couldn't contain myself anymore. I was so horny! I wanted to have a little fun, so I cranked some music. I started dancing as seductively as I could. I removed my robe, pretending I was a stripper. I was on stage baring it all for all the men to see! I was thoroughly enjoying myself. So much so that I never heard the back door open. Nor did I hear the footsteps behind me. What stopped me dead in my tracks were the hands that abruptly landed on my small biceps. They were followed by a voice in my ear.

"You look so fucking hot" he whispered to me.

I knew this voice. I was frozen in fear. "MARK?!?!" i shouted.

I tried to turn around but he tightened his grip on me. He started to kiss my neck. It was such a messed up situation. I shouldn't have felt like I did, but once I felt his lips on my skin, I got weak.

"If your gonna do this, you should probably close all of your blinds. I've been watching you off and on all day from the backyard." He continued to kiss my neck. His hands started to rub my arms.

"Mark....I....I" I couldn't find the words. I was so humiliated, so scared, and so turned on. It was a wave of emotions crashing over me all at once.

His grip loosened as his hands started caressing my smooth arms. I could feel my body tingle as he nibbled on my ear. I had never been with a man before. Melissa(my wife) had fucked me with a strap on, and I had used a dildo on myself, but never the real thing. I was bi-curious for sure, but just never pulled the trigger. Now, it may actually happen. The invasion of privacy most likely would have turned most people off. They would have been scared, which I was to a degree, but the other feelings were starting to topple fear. I could feel myself slowly losing control as his tongue played games behind me. I heard the zipper to his pants release and my heart raced. He took my right arm and brought it around my back. The next thing I knew, my petite hand had a hold of his thick manhood. He wasn't overly long, but man, it had girth. So much so that I gasped a little when I gripped it. It was a little awkward due to my positioning, but I slowly started stroking him.

"Mmmm. That feels so good. Jen hasn't touched me in weeks." He moaned into my ear. I started to get more aroused at his approval.

Before I knew what was happening he spun me around. I was face to face with him now. A man I had come to know so well over the past few years, yet somehow I didn't know this. Then again, as far as I knew, he didn't know about me either. I couldn't help but glance down. His thick cock was rock hard poking out of his jeans. I looked back up at him grinning at me. Before I could say anything, he leaned in and kissed me. Right on the lips. Tongue in my mouth. The whole nine yards. It was an odd sensation kissing a man for the first time. His go-t was a bit scratchy, but I didn't mind. He embraced me like we were long lost lovers. I didn't hesitate to kiss him back. I wanted it at this point. His hands drifted down to his jeans as he slid them and his boxers down to his ankles. He kicked them and his shoes off. I took the hint and removed his t-shirt. He had a bit of a dad bod, his chest had the slightest hint of hair. I found him to be very attractive. He seemed very manly, very much the opposite of me, and I liked it.

We continued our kiss, but I knew what he wanted. I slowly started making my way down his body. I kissed his chest and used my tongue to play with his nipples. I continued down to his stomach. There was something about his little gut that drove me crazy. Eventually I ended up on my knees, right in front of it. I looked up at him and he was looking at me with a smile on his face. This was about to happen. My first real cock. I reached out and started playing with it a little. Stroking it, playing with his balls. I was honestly stalling. I was nervous. What if I wasn't good? What if he hated it? What if he freaked out half way through? I didn't have time to collect my thoughts though as his hand made its way to the back of my head. Before I knew it, his thick cock was firmly in my mouth. It didn't taste like I thought it would. Hell, I don't know what I even thought it would taste like. All I know is that at that moment, I was in heaven. I loved it. I loved the feeling, the sensation, all of it. I could feel my own little cock getting hard as he moaned with pleasure.

"Fuck.....your way better than Jen" he exclaimed.

I relaxed a bit as I ran my hands up and down his legs and love handles. I could feel my backside puckering. I wanted him inside me. I needed it. I was no stranger to anal, but he was just a little thicker than anything I had before. I continued to suck him for about 10 minutes or so. I backed away and kissed back up his body. I was surprised as he pulled me in and again kissed me on the lips. I just decided to lay it all out in that moment.

"You wanna fuck me?" I asked as seductively as I could.

He didn't even answer me. He spun me around and I was bent over the arm of our couch. I felt his hand move my thong aside and felt the tip of his cock playing around down there. He was teasing me with his swollen head. It was driving me crazy! "You want this?" He asked in his deep voice.

"Yes!" I whined impatiently.

"Beg for it." He commanded.

Beg? He wants me to beg? My first time with a guy and now he wants me to beg for it. He knew I wanted it, he just wanted to hear it. I truly didn't want to. Deep down, I was still utterly humiliated by the whole thing. But my body won out.

"Please....please Mark....I need your cock in me. Fuck me. Fuck me like a whore". I just blurted it out. I didn't mean to really, it just happened. I heard him chuckle and then felt his spit as it rolled down my crack. He did it a second time and started rubbing my hole with it. It was a bit embarrassing that it turned me on.

I felt his head enter me. I wasn't too tight, but definitely wasn't loose. He didn't have to work overly hard to get it in. Once it was, I let out a little squeal which was followed by his laughter. Inch by inch he crammed himself into me. He was only about 5 inches long(I say only, but rock hard, at max, I'm only 3), but again, he was very thick. I could definitely feel him stretching me. It was a tad uncomfortable, but I adjusted. Once he was all the way in, he paused. He leaned down and started kissing my back. I lost it. I started moaning like you wouldn't believe. I don't know why it felt so good, but it did. His hands were exploring but ended up on my hips and he started thrusting. He started off slow but picked up the pace. My moans matched his tempo. Pretty soon you could hear the slaps of our skin over the music. It was so hot to me to hear him slamming into me. Not only did I feel like a woman, but I felt like a whore. It turned me on so much. After a couple minutes he reached around with his right hand and started playing with my cock.

"Always thought you'd be bigger" he said as I stroked me with in between his thumb and fore finger. "Thought you'd be one of those tiny guys with a big dick."

I didn't know it then, but he was 100% asserting his dominance over me. He was belittling me, and I liked it. The humiliation turned me on. I was small. I knew it. My wife knew it. And now Mark knew it. He knew it, and he let me know he knew it. It only got me more excited though as he rubbed me through my panties. I started to moan louder as I could feel myself getting closer to climax.

"That's it baby. Come for me." It was more like a command coming out of his mouth at that point. It didn't take much more force to make a mess out of that black lace. I've always been a pretty heavy cummer. It's something my wife has always loved about sex with me. I could feel it oozing out of the front of my panties as his hand retracted back to my hip.

His thrusts became faster and harder. His moaning got louder. I knew he was about to cum. Then it hit me. I didn't know if I wanted him to cum in me or not! This whole thing wasn't planned, and I was too caught up in everything to think about how this may end.

"Fuck.....fuck.." he started to moan.

"Mark.....wait!" I yelled. But I was too late. He let out a huge moan as I could feel his load fill me up. The sensation of cum being released inside of you for the first time is something that is hard to explain, at least for me. But in that moment, I truly knew I was bi-sexual. Some say they feel guilt or shame after, I didn't. I felt like I wanted more. I also felt his cock getting soft and pulling out of me.

My body kind of went limp as I just laid there, still bent over the arm of the couch. I pushed myself up so I was back to him. I turned around and was ready to give him a big kiss, but he already had his pants back on. Did he not like it? Was he embarrassed about it?

"Mark, that was-"

"It was great. But I gotta get home before Jen comes looking for me. I'll see you around" he said cutting me off.

He pulled his shirt on and leaned in and gave me a kiss on the cheek. Before I knew it he was gone and I was alone, his cum now leaking out of my ass. I felt a little cheap and used, but I also felt amazing! Although not planned, I had my first time with a man, and I loved it. Melissa was gonna be calling me soon, and I decided I wasn't going to tell her. She was always encouraging me to explore this side of me, but I thought telling her in person would be more appropriate. I also didn't tell her that while we were chatting I was slowly fucking myself with a dildo, using his cum as lube. I went to bed that night dreaming of the next time I would get to feel Mark's thick cock fill me up.