Losing my virginity (trans, cheating) | 2016

I wanted to write about this desperately. I wanted to tell the whole world how I lost my virginity. This was an experience I had denied myself for far too long. So now I’ll share it with you.

I should probably prefix this by saying virginity might be a tiny bit misleading. I’ve been with plenty of women but never with a man.

I have been married for quite a while now (three plus years isn’t a “while” I understand, but it feels long) and I have been denied an experience with a man. We are no longer married, unrelated to this tale, but I suppose that doesn’t change what I did. My wife would have loved to see me with a man. To get bent over a table and fucked senseless or watch me top a man until he was putty in my hands. But I wanted something different for my first time. I didn’t want to be a show piece and so despite many opportunities to have a man in my bed I resisted.

Until this story happened.

A party. A subtle mixture of alcohol and weed. A short dress to accentuate my legs. If this was a stage I couldn’t set it more perfectly. Bonfires, beer pong, and tenting. It was sublime.

He was handsome. The body of a man that justifies those sculptures of heroes and Greek gods. Not the arms of a man who does nothing but lift but a post collegiate athlete who stayed in shape. Every muscle on his body was visible when he moved as if he were a lion on the hunt. His chest and stomach had curly black hair and his beard was cut super close. It would feel like sandpaper ripping at my makeup when I kissed him.

We flirted throughout the night. He was boisterous beyond belief. He came off like a frat boy trying to out bro the rest of the party and he easily claimed the gold medal where that was concerned. It started to get really heated when we played beer pong. We were both trying to show as much skin as possible to throw the other person’s game off. He would flash that marvelous “v” of his hips just to the base of his cock. I would drop the straps of my dress and lean over the table. My tits would barely cling to the fabric and not fall completely out. Just enough to tease and flirt. But not enough to cross the line.

He’d drop a ball and it would roll to my feet. He’d touch my knee while I’d lick my teeth dangerously. The line of being an adulterous wife was being blurred with each drink and every puff of smoke.

The party began to fall apart around three in the morning. Only a handful of people were still up and we had found ourselves on the couch. The radio was throbbing out sultry tunes; a fitting genre for these next moments. The distance between us was closing. His fingers had reached out and were gently stroking my ankle while my own fingers were running over his arms, tracing the tattoos that wound their way around his skin.

My heart was hammering. I was on such dangerous ground. I had him and he had me and at the forefront of my mind wasn’t this glorious moment but instead on my wife and the betrayal I was considering and the secret I guarded. I don’t like to tell people I’m trans, but I simply had to.

The distance closed further. His hand on my thigh, my hand on his chest. I had to tell him.

“I have to say something,” I whispered. He didn’t respond.

“I’m trans and I’m married.”

I waited for the bomb to drop.

“I knew one of those,” he said.

I looked up into his gorgeous dark eyes. “Which?”

“Trans. My friend and I guessed.”

Silence for a moment.

“To be honest, I used to be a complete homophobe,” he continued. “But I have really tried to get away from that. I’m actually really happy that I’m so attracted to you.”

“Well it isn’t gay,” I said. “I am all girl except one part of me.”

“Anyway this…” he gestured at both of us. “…is all in your hands.”

The next few moments dragged on for an eternity. I traced an earlobe with a scarlet painted fingernail and brought his mouth to mine. It was a kiss that lasted no more than a breath. The slightest touch of lips and the lightest press of his tongue into my mouth. It was I who broke the kiss.

“I’m sorry. I can’t.” I stared at him desperately. I wanted him to grab me and not let me go. To ask me to stop but he didn’t. I went outside and began to pace furtively. I was upset. Upset at myself for not letting that moment continue and upset at myself for betraying the golden band on my finger. I argued with myself for a few minutes until I went back in to use the restroom, but found it occupied. So I waited against a support column.

I felt him behind me before I saw him. I knew he was on the other side of the column and I reached out with a hand and he took it. He walked in front of me and we kissed again. I went weak into his arms and my fingers were tracing circles on his pecs. He had been shirtless all night and the feel of his muscles under my fingertips had me shivering in want.

I can’t emphasize this enough. The extremely gun-ho bro act of before had completely vanished. He wasn’t a different person but he wasn’t showing off. If anything I could still feel that ego simmering inside of him but it wasn’t what either of us needed at that moment. It was compassion and empathy.

“We don’t have to do anything. I really just like holding you,” he must have known what effect those words would have on me.

The kisses quickened in their intensity. Hands roamed and fingers caressed. The straps on my dress fell again and his fingers found my nipples and he pulled at them gently. I did my best to muffle my moans in his neck but the other partiers who had collapsed onto the floor to rest had to have heard.

“Where are you sleeping?” I asked breathlessly.

“I have a room with my friend.”

“Well, I have one all to myself,” I whispered dangerously. I took his hand and led him to where I was staying; a private space away from prying eyes.

The room was small but it didn’t matter. It had a large window with curtains pulled back and the night was without the light of the moon and stars or street lights. The room was black. We were covered in shadows and soon clad in nothing but.

We collapsed onto the small mattress. My dress was discarded quickly and his mouth found my breasts as I gripped his neck in a throw of passion.

“Do you have a condom?” I managed to get out.

“No. You don’t?” I could hear the edge of panic in his voice. Our predicament was real. We were the only two people still awake and had no idea where to begin to look.

We groaned in anxiety but we didn’t stop. My fingers grabbed his waistband and his gorgeous, easily eight inch cock sprung out to meet me. It was harder than diamonds and had a slight curve that would curl up to reach all of my spots. The balls were heavy in a gorgeous sack and the head was thick and purple with a drop of precum oozing out of the slit.

I have sucked a cock before, but never alone. And I had never been fucked by a man as I previously said and without the condom I didn’t think it would happen. Regardless of that dilemma I needed it in my mouth. I took hold of his perfect member and took him into my mouth. The briny flavor caused me to shiver in pleasure as he collapsed further into the mattress as his whole body relaxed as my mouth took over.

I was sloppy. My hand twisted around his cock and he moaned softly as I worked him with my mouth and tongue.

I paused for a minute to see him smiling at me.

“You are so gorgeous,” he said. He then reached for me and then I was on my back. His lips finding mine with apt longing but with a patience I found torturous. His hand had drifted down to my panties where my cock was tucked.

“You don’t have to,” I whispered. “I won’t be mad. There are other things I enjoy.” He seemed relieved and his fingers slipped not through the top of my panties, but the rear. He made his way to my tight pink hole and was circling it with his index finger. It was a shock of fire and bliss that all of my toys had never given me and I cried out instantly as the feeling crawled up my spine.

An hour this went on. Then two. We’d kiss, we’d suck, we’d touch, but we didn’t fuck. We would get close when his cock would press against me just so we could feel it, but he didn’t give in. The lack of a condom was killing both of us. But as the sun began to light up our window I gave in. We were spooning in a haze of pleasure. His cock was still hard hours into this rendezvous and it was tucked into the crease of my ass. I pressed back against him and the feel of it sent more tremors of pleasure into me. I wanted nothing more than him at that moment.

We grinded more, his cock finding my hole and pressing against it in the most pure form of pleasure I had known up to this moment. His body was hot behind mine and the eagerness had not left either of us. We continued to press against each other and it opened me like the Floridian sun was opening the flowers under the windowsill. The lack of lube and the slowness of it was causing my heart to hammer in my chest and my moans to fill the air.

And then he was in me. Inch after inch we grinded until he was as far as he would go from that angle and I was biting the back of my wrist to not cry out. I came almost instantly. Gone were the days of my cock spraying anything but a few drops and that didn’t change here, but the orgasm washed over me and I shook in his arms.

I slipped out of him and laid him flat on his back. “I want to ride you,” I moaned as I licked my fingers and gave myself the first and only lube I’d had that evening which was a shock to even to me. I hadn’t experienced even a pinch of pain.

“You will hear no complaints from –“ he broke off in a moan as I took his fat cock into my ass. We fucked. Hard. The beauty in the moment was replaced by our animal lust as we rutted in a wild heat. He took my tits in his hands as I moaned louder and louder and soon his hand was over my mouth to muffle my screams.

I came again in the most intense orgasm of my life. No words can truly explain how it ripped my world apart before my eyes. We collapsed in a sweaty heap and the softest of kisses were exchanged once again as I recovered.

We slept soon after. He didn’t get to cum, unfortunately. He blamed the drinking but I still felt bad. We tried for a while. I blew him. I jerked him, and despite how close it seemed to be he couldn’t. We gave up but he wasn’t disappointed. He had a smile on his face a mile wide, fully illuminated by a seaside sun.

We said our goodbyes in the morning. We didn’t exchange information. He knew my marriage couldn’t be compromised and just like the whole evening he was understanding and compassionate.

The last kiss was fleeting but much like the first, and all the ones in between, I shall never forget it.