Twenty one years of of bisexual exploration

After my night with Ben I decided I needed to explore myself more and be honest about what turned me on and what I wanted.

Over the next couple of years I started to experiment with crossdressing by myself and came to terms that, yes, I did find men sexy and attractive and yes, I did want to submit to them and please them. I also started to realize I had a smoking fetish and my love for bad girls was really more about secretly wanting to be a bad girl. But I was still in a small town area and sexual progress would be slow. I ended up having a torrid affair with a younger woman who was the things I secretly wanted to be and we did a bit of clandestine partying (a story for another day) and that scratched that itch, but I still wanted men and I had a preference for older, hairy chested gay men. I also realized around this time that these men were not interested in my crossdressing bad girl fantasies, luckily though, they did like a cock sucking slut.

Once I understood what really turned me on I felt comfortable looking for experiences. A few years had passed and smart phones brought gay apps. I started with Scruff, it sounded like the right fit and there were a few decent local prospects. My work travels took me mainly to the bible belt America and not the kinds of places where you really feel safe on your knees. It was time to go local and hopefully find a discreet no strings attached friend.

Discretion was key when playing so close to home, so I tried to get to know guys first, no easy task on a hook up app. I got lucky and 2 sexy, hairy chested older men started chatting with me and didn't mind me taking it slow and being discreet. I ended up talking to them both off and on for quite a few weeks and one night found myself alone for a few hours and able to meet and lucky for me Walter was free.

Walter was a local real estate agent, he was in his early 50s, 6' 1", in shape with a bald head, a hairy chest and most important a hung cock that he liked to share pictures of. 

It was February and it was an extremely cold night, 14 degrees and a bitter wind. Walter was selling a small cafe a few blocks away from me that had been out of business for awhile, we met there. Once inside he turned and pulled me in for a kiss, I felt submissive to him immediately and the passion in his kiss turned me into a slut immediately. I kissed him back deeply and let my hand find his bulge, rubbing his hard on through his jeans for a few minutes as he grabbed my ass and made out with me. His stubble stinging my lips and reminding me with each movement that I was kissing a man, and I loved it. He was handsome, he had a great smile and his cock was even bigger than I imagined it, I wanted it in my mouth.

I pulled at the button of his jeans, pulled down the zipper and reached in and felt his throbbing cock as we kissed. I knelt down and freed his hard on and immediately took it in my eager mouth...one problem though. It was 14 degrees and this cafe was not heated, every time I took his cock out of my mouth even a little the cold air would hit my saliva and threaten his erection. After a couple minutes his thick, throbbing cock started to soften in my mouth and we had to admit it was just too cold to continue. I never saw Walter again, aside from his real estate ads. Another bust, or rather an unbusted nut.

Almost immediately I started talking more to another guy on Scruff, his name was Robert and ironically he had just opened a new cafe 2 towns over and I passed it on my way home often. About a month had passed since my frigid night with Walter and his cocksickle and I found myself with a couple hours of free time and met Robert at his little restaurant, which I made sure was heated.

Robert was the epitome of what I was looking for. He was 54 to my 34, he was very handsome with a salt and pepper beard and hair, his chest was hairy and he was very well hung. He met me at the door and invited me in, he had a sweet smile and was very sweet yet looked manly and rugged. He led me to a booth in the back where there were no windows and sat opposite of me. We chatted for a few minutes and then he said "you weren't kidding when you said you'd be nervous. Can I kiss you?" I had told him how I get really nervous until I start kissing and then lust takes over and he had remembered. "Yes" I said in a whisper and he leaned across the table and gave me a long kiss on the lips and then pulled back a few inches. I could still feel the sting if his beard on my lips when I leaned in and kissed him back, opening my mouth for his tongue. It was like lightning as he kissed me deeply, after about 20 seconds he broke the kiss and asked me to stand up, I did. He stood and then pushed me back a couple feet and pinned me to the wall, grabbing my ass and kissing me again as he squeezed my ass. "Mmmmmm" I moaned as he whispered "I remember you saying how you always wanted a man to pin you to a wall and make out with you" I pulled back and bit my lip nodding yes as I put my arms around his neck and pulled him back in for another kiss. Then I swung around and turned him toward the wall as I started to rub his cock through his gym pants and pull his sweater off to reveal his hairy chest. I started kissing his ear, then his neck, then his hairy chest, running my hand over it as I slid to my knees, kissing my way down his stomach until finally I was pulling his pants down.

When I got his cock free I had to stop and admire it, admire him. He had a thick, meaty 8 inch cock, like a porn star cock and he was rock hard. I looked up at him and licked my lips before sliding his mushroom head into my mouth. "Mmmmm" I moaned as I swirled my tongue on his cock head, working more of his shift into my mouth with each bob of my head. He had told me he loved slow, passionate blow jobs and I was doing my best to make him moan. He turned and sat in the booth and I slowly worked more and more of him into my mouth like a pro. After about 10 minutes I realized I was somehow deep throating his beautiful cock and couldn't believe it. I moaned and took him deep, slid his cock out of my mouth and licked his balls, rubbed my lips all over the shaft and slapped his cock against my tongue and face. "You really do become a slut" he said with a smile and I replied "mmmmmmmm hmmm" with his cock in my mouth.

He must have picked up on the hint because I felt his hand grab my hair and push me down deeper on his cock until I gagged, which made me wrap my lips tighter. After several thrusts and me gagging he let my head go and apologized, I looked up at home gasping and bit my lip "mmmmm, I kinda like it" and took his hand putting it on the back of my head and sliding him back in my mouth. I worshipped his cock for about 30 minutes and realized my free time was more than half gone and soon enough my wife would wonder why I'm not home. I explained and we both stood up, but I couldn't resist kissing him and then stroking him and sliding back to my knees. This happened twice and then my phone alarm went off. "Baby, I think that sound means our time is up" he said as I worked him faster and deeper with my mouth "I want your cum daddy" I panted "I never come from head baby, only fucking" he replied. I wanted him to fuck me so bad, I wanted him to take me, but he was right, I was out of time. 

"Next time I'll take you to my place and fuck you on my bed" he said as he pulled his sweater back on "yeah? There will be a next time?" I asked "of course there will, I want more of you" he said as he pulled me in for a kiss and slapped my ass, it made me feel so fucking sexy. We kissed a few more times on my way to the door and he walked me to my car and to my surprise leaned in the window and kissed me again. I was in lust and a month later we had it all worked out to meet at his place and he would take my virginity in a way I would never forget... unfortunately I chickened out and never met with him again. I guess mostly it was the feelings he gave me that scared me. I had honest lust for that man and found myself fantasizing about more than just sex with him. I didn't make him cum but it was the hottest time I'd had this far.

A few more months passed and I was working from home and chatting with a guy who lived just a couple miles away. We had some steamy exchanges in the morning and decided I would go to his apartment at lunch. Where Robert was everything that turned me on about men, Jeff was the opposite, he was very over weight, bald, no facial hair and barely average. Nevertheless I needed to taste and feel a man's cum. 

The experience was nothing worth even recounting for the most part. He lead me to the bedroom, we got naked, kissed and then I started sucking him. Three minutes into sucking him he said "slow down, you're going to make me cum" and I just moaned "mmmmmmmm hmmmmmm" and then I felt his cock squirt a thick, warm load of cum in my mouth. I moaned as I finally tasted a man's jizz, savored it and swallowed it, licking my lips. I wasn't really into Jeff, but tasting his cum made me want more. Other than this milestone the experience was pretty bland.

After Jeff I took a break from Scruff and went back to fantasies for awhile. It turned out that all 3 of these men were somehow connected to acquaintances and I really needed to stop local play. A year and a half later I took a job much closer to the city, but that's a different story for another day