Crossing Over

Let's face it, relationships with women suck! I was so over them with my effort, time and energy not being reciprocated or having to play games! I had been single for about a year after several 2- or 4-year relationships and the only thing I was missing was the sex! I always thought it would be great to have that close mutual friendship along with the sex, but you just can't truly get that from women anymore these days. They always decide if you're going to "get" any and let's not even talk about their mood swings! Sure, there's Asian Massage Parlors and hookers, but they can get expensive and there's no relationship with either of those. It's just a temporary fix that leaves you still longing afterwards.

I think it was at first when during masturbation that I was trying to achieve that duel mutual feeling of being both the guy and the girl at the same time. Feeling my ass, my smooth skin and curves, trying to imagine it was "her" I was touching. I even started shaving my whole groin and ass. I wanted that feeling of fingering a pussy while I jacked off, so I started to finger my ass pretending it was a girl's pussy. It was tight, warm and wet just like a pussy. It felt good and that's when I remembered hearing about prostrate orgasms. So, I googled and researched about them. I bought a prostrate massager off Amazon, as to be discreet along with some KY liquid lube.

My first few explorations felt good and made me cum hard while I jerked off. I began wondered if I could cum without jacking off while using it. Again, I headed back to the internet and found a sissy sites with plenty of videos and audios. It was a combination of many things I discovered during that research that I would have to learn to get me to that holy grail of orgasms. A whole rewiring and different approach to my sexuality. This was going to take some time, dedication and some modifications on my part. First was the mindset, your cock isn't for sex anymore. Your ass is a sex organ, a pussy and you have to treat it that way. That means keeping it clean, shaved and played with. Getting used to tease it both inside and out! Yes dildos are made for pussies but let's face it, pussies are made for cock!

To get to that point I was going to have to feel more fem and to learn how to attract men. I would not only have to get them to desire me, but I would have to learn to desire them myself! Going from straight to gay wasn't going to be an easy task. If I really wanted fucked by cock, I'd have to accept I needed the alpha male's body to get to his cock. To adore his hairy chest, body, his shoulders, arms and butt. His strength, dominance and power, all things I seemed to be lacking when compared to him. But most importantly I'd have to accept the new feeling of desiring his cock for my own gratification! Thanks to the internet there's a lot of porn out there. I started with something I felt comfortable with and that was watching women sucking off men. That got me accustomed to see all kinds of cocks and learn how to work them. Then I went to close ups where you couldn't see they were women but rather just a hot mouth, a tongue working that hard meat stick and balls.

That was me I would have to accept. It was me worshipping that hard cock so it would want to fuck me. I started to get turned on and I would fuck my ass pussy while imagining sucking and swallowing another guy off. I had to stop jacking off, after all I had to start rewiring my brain completely so bought a cordless vibrating wand to use on my pathetic little prick while I fucked myself with the prostate massager. The vibrator always sent me over the edge pressing hard down on my limp little dick. I started tucking my shrinking little clit. I bought period/pee proof panties to help hold me snug and make me feel more girly. I was tucking so good by now I had a camel toe! Pushing my little balls up inside and pulling my little clit back covering it with my empty ball sack. Gaffs worked best but weren't all that comfortable at work and by now I was a 24/7 tuck and panty wearer! I started watching slide shows of cocks and naked men.

I started to get turned on looking at them and wondering what it would feel like to let another man make love to me. I broke down and bought a dual core realistic dildo and OMG it felt so different than my prostate toy. I was still using the vibrator and had stopped jacking off now for nearly a year. It was time to let go of that crutch and go for a full-blown P-spot orgasm. I would use it to edge and then pull it away while I continued to fuck my pussy. I gave myself time limits and if it didn't happen... well it was my own damn fault. I told myself it's the only way you can cum from now on so you better try harder! I forced myself to not use the vibrator anymore. The cum and agony built up and after two weeks it finally happened! OMG it was amazing! I shook for several minutes! I really could cum by just getting fucked!! I was hooked and watching sissy and gay porn quite a bit now while fucking myself into an orgasm on a regular basis.

It just wasn't enough, and I kept wondering if a real cock and man would truly make me cum? I needed a living and breathing man... a real man, an alpha male to take me and make me cum with his cock. I wanted to please him in every way so he would give me what I needed most of all. It was time to actually do it! I was finally ready to accept that I adored the male mind and his body. I was going to kiss him, fondle him, blow him, take his load wherever he wanted to dump it. First stop was craigslist and POF. It wasn't hard getting responses, but I was being picky. I wanted him taller and bigger than myself to make me feel more submissive and fem. I wanted to know he'd desire the fem side of me behind closed doors. I wanted to know he'd be willing to have a friendship and do things outside of the sex as well. It wasn't difficult finding my man to fit my physical requirements, you see I'm just 5'7" and 155lbs. So, there's a lot of guys out there bigger than me. I Look and act pretty straight out in public even if underneath my jeans I was tucked and wearing panties.

I met Dennis in the parking lot of an Apple Bees and we introduced ourselves. We both were comfortable with what we saw and decided to go in, have some drinks and talk to get to know one another. After about an hour and a half of straight male talk he asked if I would be okay going for a short ride to a park where we could continue talking while we walked. I agreed and we went to a state park with trails. We were about 10 minutes into walking and talking when he looked around to see if there was anyone even close... there wasn't, we were alone.

He walked up close to me and pulled me in by my ass, pressing me up against him. He was tall and he leaned down and gave me a kiss. He asked if I was okay, and I nodded. He kissed me again only deep this time. I reached down between his legs and rubbed his cock and balls over his jeans. I felt them grow hard in my grip as his tongue twirled in my mouth. I unbuckled his pants and slid my hand down the front of him to feel the stiff warmth of his cock, skin to skin. I began to slide my hand up and down his shaft as the palm of my hand rubbed his length. Every now and again I would graze his smooth balls tickling under them with my fingertips near his taint. All the while he continued to kiss my mouth and neck.

His breath grew heavy, and he began to squirm, I knew he was close. He loosened up his jeans and pulled them down. I looked down to see his dick exposed for the first time. He was trimmed and his balls were swollen! It all looked so amazing to me, and I was so turned on already imagining all the things I could do to it! He was so close to cumming and I am pretty sure he wanted me to go down on him. But this was our first time. I wanted more... I wanted him to want more. I decided he was only getting a hand job at this point, so I intensified my strokes and squeezed his aching cock to relieve him of his impending climax. I could feel it beginning to convulse as he sprayed his batter onto the ground. Some of his juice got on my hand and I couldn't help but to put it to my mouth and taste him. It was oh so good! That made me second guess about not having him nut in my mouth to eat it all! He grabbed my ass tight and pulled me in for one more kiss before he pulled up his pants.

He was quite happy to say the least as he was smiling ear to ear. I was happy too, after all I had finally taken that first hard step in crossing over to the real thing and well on my way to experiencing the ultimate orgasm. On the drive back he asked for another date and said next time we'd have a more private place to continue. Yes, there was another date of course. Many actually, but I'll leave that for another time and story.