Making Vee - Her First

Although I started laying the groundwork to become more feminine in my earlier years it wasn't until my mid-twenties when my world really opened up. My first time was an experience like no other further defining my desires and fantasies to this day.

The past few years living with the girls was great however I didn't realize how much that comfort limited me from taking the next steps becoming the girl I wanted to be. Although I was an excited and completely obsessed about giving myself to a man, I wasn't sure how or when it would happen. As it be, things just work out without even expecting them when you allow yourself to, especially when moving in with three gorgeous guys!

My new roommates obviously provided the best opportunity to experience a man and not just because they were attractive, always thinking of sex! On second thought that's exactly why, but not like you'd think. I was amazed how women gravitated toward these guys and I was no different. I wanted them, and all at once if the situation occurred. They were very charismatic and were always meeting different girls throughout our time together.

Shortly after they moved me in, we all went out together as they commonly did. After checking out the club the guys noticed a group of three women who were definitely looking our way. We approached them and after a little banter it was apparent my buddy was going to be the odd man out. Not feeling interested to compete with the guys over girls, I told my friends to say I was gay so he could swoop in. Although it was my suggestion, I was surprised how fast he jumped at the opportunity to call me out. It was the perfect excuse and everyone was happy.

The plan worked so well the guys joked about me becoming the designated gay guy more often. Without a second thought I told them I didn't mind feeling somewhat liberated. That night something clicked inside convincing me to become the woman I wanted to be. I quickly took my role to the next level growing my hair out longer and started wearing light makeup. It was becoming clear I enjoyed playing my role more and more as the guys started to question my transformation. Thinking it was just an act they obviously didn't mind but day by day I was becoming more feminine. It was bound to happen feeling more comfortable wearing feminine apparel over my panties I secretly wore daily.

A few months later, the girls we connected with that night wanted to meet up to spend the day together at a music festival. Unknowingly, one of the girls invited a friend she worked with to join us. It was a total set-up. She told me I was totally his type and I would be into him, thinking we'd be a good match. As he walked towards us, I couldn't keep my eyes off him. He was hot AF! A few inches taller, athletic build, pretty hair, an amazing smile and a beautiful face all wrapped up into a masculine package. Oh yeah, I was into him! He was the guy I've fantasized about for years, standing right in front of me. She introduced us and I was so nervous as he hugged me.

How was this going to play out, I thought as my friends knew I wasn't really gay. Quickly they jumped to my rescue blurting out, I have a boyfriend and I'm not available keeping their cover intact. It was all they could do and I appreciated them, but just couldn't let this opportunity slide. I was so attracted to him that I instantly I looked into his eyes, smiled and said it's nothing serious in excitement. I will always remember the look of disbelief my friends had killing their perfect alibi they had for me. Not fully comprehending the situation I just placed myself in I really didn't care, it was done! I just allowed myself to be set up with another man!

He and I hit it off instantly and flirted throughout the day. Sensing he was interested, I made sure without question he knew I wanted him. After the festival we left the group together. As soon as we walked around the corner out of sight, he pushed me against the building and started kissing me. I'll always remember his hands sliding down my back grabbing my ass. I felt adored with my arms hanging from his shoulders asking me to go home with him. Every inch of my body had goosebumps. I couldn't believe how quick this was happening becoming helpless to my fantasies with thoughts of being fucked.

Even obsessing for years I was still nervous to be with a man, but it was happening I thought, just go with it. My heart was beating out of my chest and I was speechless as he whispered again in my ear to go home with him. Trying not to appear desperate I told him I couldn't, although we both knew I was going to. Walking back to his apartment he took my hand as he led me away. I was oozing femininity and without discussion our roles were established. I was thrilled to be submissive looking to him for guidance.

Back at his place he made me a cocktail then sat together on his sofa with the lights dimmed low and music playing quietly in the background. I cozied into him as we talked for a minute before he took my glass and placed our drinks on the table. As he leaned forward my hand inadvertently landed below his waist. I felt his cock through his pants and he was already hard. Feeling validated knowing that's for me, I couldn't keep my hand from exploring his thigh defining the edge of his dick. I cupped my hand slowly stroking his cock back and forth through his jeans. I was amazed by his size, guessing at least seven inches comparing it to the length of my hand.

Seconds later he reached down, unbuckled and opened his zipper pushing everything down just enough. At that moment he knew he had me. The game was over thinking to myself, I couldn't back out realizing I was expected to pull him out and continue. Feeling the warmth of his dick, I accepted the opportunity in excitement grabbing his rock-hard cock from his boxers. He was trim and clean; his skin was so soft and smooth I thought taking his balls out to free them.

I touched and fondled his cock in wonder catching a slight aroma. His scent was subtle and I was extremely turned on from the masculine smell of a man. I could tell by his quite moans he liked how I handled him. He slipped his hand down my pants rubbing my ass while I lied across the sofa with my face above his cock. I was slightly embarrassed when he questioned if I was wearing a thong. I nodded yes, gripping his cock in enthusiasm as any embarrassment faded with his acceptance.

I was feeling so feminine and was completely committed to blow this man staring down at his manhood. Although I was ready, I started to worrying about gagging and looking pathetic as I lowered my head to suck his dick. I started slowly with little kisses all over the tip with one hand holding the base and the other cradling his balls. My heart was exploding out of my chest. I'm finally sucking a real cock I thought after years of fantasizing about it.

Quickly gaining confidence my lips divided sliding up and down his cock as my kisses became more pronounced. My tongue soon stretched around his dick catching the faint taste of salt as I licked his cock working my way back up to the top. I kissed his head again before opening my mouth sealing it with my lips. Sucking constantly and swirling my tongue around the tip, I felt him squirm in pleasure. Assured by my efforts knowing I had more to give, I took his dick a bit further. Sliding him across the inside of my cheek, each bob went further and further down my throat. Just like the videos I watched I started to stroke his dick in sync with my head as lubrication from saliva leaked from my tongue.

I was rock hard when I made my way onto my knees arching my back bringing my ass closer to his reach. He quickly stuck his hand down my panties rubbing my ass hole, I thought I was going to have an orgasm! It felt incredible to have a man touch me like that, even though I was more fixated with the cock in my mouth.

Wanting to go deep I buried my face into his lap. After about the fourth or fifth push without gagging, my throat relaxed enough to take him all the way clinching the base of his cock with my lips. I paused there for a second to reflect on my accomplishment. I was so proud and considered how much I loved sucking my first cock.

In that moment there was no way I was going to pass on the opportunity to taste cum. It became the only thing on my mind and was determined to make this man finish in my mouth as I continued to deep throat him until I was out of breath. Needing to come up for air, I kept him going by jerking him off while I caught my breath. I'll always remember looking up at him watching me and how good it I felt to hear him tell me I was amazing!

He wanted to take me back to his bedroom, but I just smiled declining his invite telling him I wasn't finished. I waved his hard dick back and forth smacking myself gently on the face before continuing to suck his cock preparing to receive him. My jaw was starting to tire and I seriously thought about stopping having no idea how much longer he'd need.

Tears started running down my face and combined with my spit, I was becoming a sloppy mess. I had enough and was about to quiet until I felt his hand press on the back of my head hearing him moan. Okay I thought, I knew it was happening soon! I immediately increased the intensity, sucking harder and faster slipping his cock in and out of my wet mouth forgetting about any pain in my jaw. He tensed and tasted pre-cum leak out, here it comes I said to myself as I wondered what to expect. With my eyes closed shut I could feel his cock pulsate around my lips as I felt a gush of warm, salty-sweet, thick goo explode in my mouth. It seemed liked forever as he continued to pump his seed into my mouth. The thrill of giving him an orgasm him took my breath away as I accidentally opened my mouth for a breath. Cum flowed all over his dick so I quickly closed my lips sucking it all back up again.

As I pulled my head from his dick, I swished him around my mouth feeling the texture and warmth letting the taste linger before swallowing. I slowly slide his cock down my throat a couple more times before finishing. I realized right there how sucking dick gave me so much pleasure while chasing my desire to become a woman. I loved it! With my head now lying in his lap, I gently caressed his beautiful cock watching it get soft. I couldn't help but wonder if he thought I was the best he's had thinking I'll never have to suck a dildo again to get off. I knew my life just changed forever as I was already looking forward to my next blowjob!

It was clear I wasn't getting fucked as he mentioned how tired he was and asked me to go to bed with him. I wasn't disappointed at all with the excitement of sucking cock fresh in my mind. I knew if I spent the night, my roommates would know I went home with him after the festival. It didn't matter and I didn't care, accepting this fate as I got up and walked into his bedroom. I undressed and crawled nude into his bed waiting for him to join me. Moments later he walked in completely naked stopping in the doorway, asking if I needed anything? Him, I thought obviously! I knew he was just showing me his body and cock swinging there in silhouette. How could I have been so lucky, I asked myself fantasizing this man fucking me someday. As I called him into bed, I was hoping someday was now. I was wide awake, super aroused and just ate his cum. I needed him inside me! He got under the covers, turned towards me and pulled me into spoon. He draped his arm over my body while I pressed my ass into his limp cock. He seemed tired but I wasn't sure what to do but within minutes I could tell he was sleeping already.

Alone with my thoughts, I questioned why I was spending the night at the cost of the guys catching in. Convinced I'd have to explain myself in the morning, I thought about leaving but eventually gave into his naked body cradling mine making it worthwhile. As I dozed off, I made sure to keep his dick propped in my ass as a way of letting him know I'm receptive if he woke.

Throughout the night I was up several times in disbelief lying naked in bed with a man. Not knowing if this was to end up as a one-night encounter I couldn't stop wishing he'd wake up and just fuck me already. As the sun rose his arm was still wrapped around me, he hardly moved all night with his cock still pressed in my ass. He rolled over on his back and I quickly threw my leg over his, placing my hand on his dick. He was still asleep but it was time for him to wake up! I could feel him getting firm so I sat up and straddled him as my clitty and his dick rubbing together.

I was giving him morning kisses on his chest and neck when his eyes opened. He aggressively pulled me towards him to make out as his hard cock sprung out behind my ass cheeks. I slide my ass back and forth on his cock grazing my hole with each pass while our tongues slipped into each other's mouth. I knew I was about going to get what I waited for all nigh! After a minute he rolled me onto my back as the sheets slide off me, I was completely exposed to him. My shaved clitty was standing straight up as he looked at me in surprise. I felt so insecure the way he observed me knowing I was much smaller than average. I was reassured to hear he preferred femboys and thought my clitty was really cute as he played with it in amusement. I never thought of myself as a femboy but here I was begging him back to make out with me.

It wasn't long before he was kissing my body working his way down my thighs, I was in ecstasy. My legs were spread wide with my knees bent supporting his head as he started to suck my clitty and lick my ass. I was so aroused and completely submissive having no idea what to then give myself up to be taken. Spreading me apart, I could feel him shift from gently rubbing my hole, flicking his tongue all over to wedging it in, while slowly inserting a finger. I wanted him so bad and he made me feel so good only stopping to ask if I could reach the bottle from his dresser drawer and hand it to him. Without warning I felt his hand smear cold lube between my ass. As it warmed quickly, I felt him massage my hole before inserting his finger again. At first just one, then shortly later another, then a third finger was stretching me out as I relaxed in anticipation. Again, I felt so feminine having a man go down and finger me. He had total control over me asking if I was comfortable.

I will always remember telling him he made me feel amazing right before he asked how bad I want it? I moaned, fuck me already! Instantly he stood and pulled my legs until I was on the edge of his bed. Rock-hard and ready to fuck, he grabbed a pillow from the floor and shoved it under my ass. He bent my knees into the fetal position as he stuffed his cock into my ass. I was familiar with the constant pressure needed before plugs or dildos slipped in and this was exactly that! I stared at him erotically as he concentrated, slowly working his cock into my tight ass. The pressure was intense but it didn't hurt, he took his time applying more lube. Suddenly I felt the tip of his cock break through inside me as the rest of his shaft followed, he felt amazing! Within moments he was balls deep fucking me. I felt stupid thinking it was going to be more romantic as he fucked me like a porn star destroying a pussy. I loved every part of it with his balls smacking me upon each thrust.

Lying on my back with him inside me I gave way to a sense helplessness, submitting myself for his pleasure. The intensity on his face hypnotized my body into a state of relaxation as he relentlessly pounded my ass. My soft moans of excitement turned to screams of pleasure, I had no control over what he was doing to me. My clitty was standing straight up and bouncing everywhere with each thrust driving me further into his bed. It was only a couple minutes before I started to leak, yelling I'm going to cum as I exploded over my tummy. He didn't even bother to slow down leaving me to think how long could he keep this up.

As he plowed through my orgasm, I was being stretched wide open and wasn't surprised when he slipped out. I quickly reached down to shove his cock back inside as he continued to drill me without skipping a beat. It seemed like several minutes passed by before he grunted loudly finally slowing his thrust pausing between each, he just came inside me! I was completely amazed knowing there was no way I could ever fuck like that. I felt totally worked over and completely satisfied. With all the stories my previous roomies told me about, none of them even came close to what I just experienced. He was a machine, leaving me without any trace of masculinity as the little I had was literally just fucked out of me.

As he pulled out, he walked away without saying a word. Although I wanted to be fucked, I felt completely used and abandoned lying there alone after the best time of my life. Petrified unable to move I felt foolish when he came back with a towel and started wiping me down. He laid down next to me as we stared at his ceiling in exhaustion. Feeling completely relaxed I thanked him profusely letting him know I've never been fucked like that before and he was unbelievable. He continued our conversation by asking me out and wanted to know me better. Instead of answering I just smiled and said I needed to get home. Even though he fulfilled all fantasy, reality quickly set in and I became confused. As much as I wanted to, there was no way I could date this man while living a straight lifestyle around my roommates. My mind was spinning and I was terrified about facing the guys having to explain where I was all night.

After dragging myself out his bed to get dressed, I stepped into my panties as he watched. Sensing he liked what he just saw I told him of my desire to become a woman. Hoping my confession may deter his attraction for me as a gay man, I would be able to easily continue my reality as it was solving the problem I was facing. I was completely blown away when he encouraged me to explore my femininity around him anytime. Seriously! Did this just happening, I questioned to myself, instantly thinking how I wish to make this will work. We finished dressing and gave him my number to call me. He insisted walking me home but because I needed to hide him from my roommates, I said No.

I kissed him and quickly walked out before he could changed my mind. Walking home I reflected on what just happened. For the longest time I felt the pinnacle of femininity would be giving myself to a man. It still wasn't enough, I needed more, I needed him! Approaching my apartment, I had no believable explanation where I was the night before. Still feeling exhilarated I really wanted to tell the guys how I sucked my first dick, swallowed his cum then had my brains fucked out until I was unable to move! They wouldn't believe even if I could tell them.

Unlocking the door, I convinced myself it was time. I was prepared to deal with any reaction I was about to face. Just the day before I met a man who not only satisfies my deepest fantasies but also supports discovering my femininity.

Turns out I just need to let things happen.