Exploring My Feminine Side Ch 02

About a year had gone by since my tryst with Robert. Since then I continued to fantasize and chat with men online. By now I had a collection of pictures of me dressed in various outfits and had created a profile on a popular gay hookup site.

I ended up meeting an older man named Paul. Paul and I talked for a couple weeks and exchanged pictures. Our thing was when I got home from work I would set up my phone towards the shower then give him a little strip show before getting in the shower naked for him to watch which he very much enjoyed. After seductively drying off for him I would have a couple cute outfits picked out to try on for him. He seemed to enjoy it and even sent me a picture of his cum all over one of my pics which really turned me on.

Before long Paul began to bore with our online relationship which brought an ultimatum, either we meet or we were over. Paul was a sweetheart that I had come to trust. He wasn't bad looking and had a private home to host. I didn't want to lose him so I agreed to stop by for a quick visit after work. At the time I was working construction and had to explain to him that I would not be very gurly. Paul understood and asked me to stop by anyway.

Paul greeted me at the door and closed it immediately behind me. He was dressed in a button up shirt and some tighty whiteys, I was filthy dressed in jeans and a t-shirt. Paul took my hand and walked me to his bedroom where he had placed a fancy red cocktail dress on his bed that he wanted me to wear for him. I took off my boots and slipped out of my clothes to put it on while he watched. The dress fit perfectly and I immediately felt much sexier. We approached each other and embraced for a kiss while exploring each others bodies with our hands. His hands felt amazing squeezing my cheeks and pulling them apart. I relished in the sensation of making out with a man while we groped each other. My hand had found it's way through the slot of his underwear and I was ever so gently tugging his dick while we kissed.

Paul broke from our passionate make out session and lustfully asked me to go down on him. I did as asked and made my way down to my knees teasing his body with my lips and tongue on the way. I began sucking on his dick for a moment before I began to notice a musky smell that I could not ignore. I tried my best to satisfy him with my mouth but had to stop as I did not like his manly smell.

I tried convincing Paul to fuck me and I would have certainly let him but we did not have a condom and he wasn't willing to take a chance. He settled on fucking me from behind but in between my thighs, not in my ass where I wanted him. Paul finished up between my legs. Before putting his dick away he squeezed the last drop of cum from his dick and fed it to me on his fingers. I got dressed and left. Paul never contacted me again and ignored my messages.

About another year went by and I was asked to go out of town for work. This was the first time I had ever been away from my wife since we met and I was eager to take advantage of a night away. Problem was I would be staying in a real small town with an even smaller population. I posted the ad on Craigslist to the closest major city as soon as I found out I was going but was yet to get a response.

I checked into my room that night feeling kind of desperate. I was starting to lose hope that I would find a man willing to help me explore my feminine side a little more. I removed my clothes and slipped on a bright blue thong I had brought with me to wear while I was away.

I lay in bed in my panties and found some sissy porn to watch while I hoped for a response to my ad. About an hour went by and I had been edging myself the whole time. My panties were a slimy mess! I briefly clicked back over to my email as I had what seemed like every couple minutes since I got to my room but this time there was a message from a man named Steve that however unlikely lived in the same small town I was visiting for work.

Steve was married and his wife was out of town a few days. He had a nice big house in the country in the middle of nowhere off a dirt road. We talked briefly before Steve sent me his address. I put on my jeans still wearing panties and started on my way to Steve's home. Steve greeted me outside. It was pitch dark when I arrived but when I pulled into his driveway he had one of those motion sensing lights that came on illuminating his property like it was high noon.

I got out of my truck practically already in Steve's arms. We hugged before he walked me into his home and straight to his bedroom. Steve had remembered to have a glass of ice water waiting for me as we had previously discussed. The room was lit by a few candles Steve had lit prior to my arrival and the scene was very romantic. Steve kicked off his jeans leaving his boxers on before climbing into bed. I kicked of my jeans exposing my lacy blue thong before following him.

We began making out and feeling each other. Eventually I started making my way down his body to his hardening dick. I began mouthing Steve through his boxers making sure he could feel the warmth and wetness of my very eager mouth before removing his boxers completely to take him in my mouth.

Steve's dick wasn't as long as it was thick. I had a hard time taking Steve very deep but I did my best and could tell he was enjoying it when

n I started to taste his precum. I was on all fours in my panties with my ass facing him while sucking his cock when I felt his fingers slide under my thong to finger my ass. It was new to me and I hoped it would feel better but it was hot and he was having fun so I went with it.

After a few minutes I heard Steve whisper that he wanted to fuck me. Without giving it a second thought I agreed. Steve moved to standing at the edge of the bed. He wanted to fuck me missionary so I maneuvered placing my ass on the edge of the bed for him with my legs up and open. Steve grabbed both my legs and put them over his shoulders before attempting to enter my tight virgin anus. Steve tried his best to penetrate me but he was very thick and wasn't going to fit so he lay down and I attempted to ride him. I tried and tried to work him in but my virgin ass was shut tight! We were starting to lose hope but decided to try doggystyle next. I got on all fours and readied myself for Steve. I was determined to make this work and finally have a satisfying experience. At one point Steve's very thick cock head slipped past my sphincter and it hurt so much I felt he had split me in half. I asked him to wait a minute to give me time to acclimate while the pain subsided but before we could get going he slipped out.

This time Steve became frustrated and gave up. I tried blowing him to get him back but he was over it. We both got dressed and hugged before parting ways. I went back to my hotel room upset and vowed to not let that happen again. I searched Google and learned how to take it in the ass without pain and learned alot. After that I began practicing on my wife's dildos. I never heard from Steve again.

We moved to Colorado not long after my last experience with Steve and I had to start all over in my search for a man. Eventually I met Bob. Bob was an older married man who was relocating to Colorado and would be in town for a week without his wife. We talked night and day until he arrived but I let my nerves get the best of me and was unable to get myself to meet him in person.

Some time went by and I began thinking of men again. I was browsing the classifieds seeking a safe low pressure situation to explore. I found a man named Eric. Eric had some experience and claimed to be married. Him and I talked and agreed he would come to my home for non-penetrative sex. He was going to "hot dog" me. I would lay in bed on my belly. He would climb on top of me and put his dick in my ass crack without penetrating me and hump me until he finished.

Eric did come over and the everything started as planned but after getting naked but before climbing on top he changed his mind and promptly left. I was now very horny and alone so I again hit the classifieds to see what was out there. I met a man named Greg who was gonna come over and let me give him a handjob but he flaked and did not show up.

Determined to have an experience. This time I posted my own ad seeking a volunteer who wanted a handjob. Bob who I had flaked on months before responded quickly. He was willing to come over and said he could be there in ten minutes. Horny as I was I sent him my address and waited for him to arrive.

Bob arrived like clockwork about ten minutes later as promised. I was peeking out my window when I saw him pull up. I greeted Bob at my frontdoor and quickly let him in. Still wearing my stretchy jeans that made my ass look sexy and my silverish sexy lace panties, I walked him to my bedroom then asked him to make himself comfortable. Bob kicked off his jeans and lay on his back on my bed and made himself comfortable.

The plan was just to give him a handjob but he looked so good nd I felt so bad about flaking on him earlier that I decided I was going to blow him instead. I lovingly began to take his dick in my mouth working his shaft and licking his balls. I felt him grow to full erection in my mouth. I sucked him gently at first but then I stopped to ask if I could briefly ride him but without penetration. Bob agreed and I peeled off my jeans leaving my undies on then climbed on top.

Feeling his rock hard yet very soft cock poking at my hole was extremely erotic to me and for a moment I lost myself in this lust. Bob tired of me riding and eventually asked me to suck his dick again. I did as expected and made my way back down to his package. This time I was full of lust and eagerly took his dick back in my mouth sucking him for my reward.

Before long Bob began thrusting at my throat. I could feel him tensing up and I knew he was getting close. I kept up my pace and continued sucking him. There was a brief moment where his body stiffend up as he arched his back and my mouth got wetter causing me to choke as if I inhaled liquid down a pipe meant for oxygen but I continued. Feeling him relax and slow down, his dick began to soften while I continued to suck, I now realized that Bob had just emptied himself in my throat. It was his cum I was choking on just prior. I had finally brought a man to orgasm and was able to swallow his load though I was a little disappointed it happened so fast I almost missed it.