tagTransgender & CrossdressersCumming to Terms with Her Pt. 02

Cumming to Terms with Her Pt. 02

bycontactsteph77©

2) Balls Deep at the Ball

The Halloween ball was upon us. I had recently parted ways with my prudish girlfriend so this horny, bisexual crossdresser with a high heel boot fetish and the most recent increment of the student loan siting in his bank account was going all in.

Shiny black leather knee high boots with a slender four inch chrome heel were acquired along with a black leather mini skirt, white satin halter neck top, matching bra and thong panties as were the accessories required.

"So let me get this straight, you are going to the ball to pull a girl and get laid?" Mel summarised.

"That's about the gist of it," I replied confidently.

"Dressed as a girl?"

"When you put it that way," This was not how this conversation was supposed to go. Mel was probably my best friend, she was the only one who knew that I like to crossdress.

We had known each other since we were kids. Our Families liked to go on shared holidays to the south of France. It was one such holiday that my secrets were discovered by boisterous teenage Mel.

I had elected to stay in the tent while the rest of the families went to the beach. As a post pubescent sixteen year old boy my parents decided to give me my space. But Mel who was a few months older than me was curious as to why I didn't want to go to the beach.

She snuck back to the tent to find me reading a fashion magazine wearing her white linen dress.

Instead of the awful teenage laughter that I had expected Mel and I talked, and we have been talking ever since.

She was also the only person who knew that I was bisexual. Above all else I treasured her friendship. But my mind was made up.

She tried one last time to change my mind, "Look honey, I know you have all this mixed up shit going on in your wee head, not to mention what's going on in your cock and balls, but the Belfast students union isn't really renowned for being gay and tranny friendly. I don't know too many girls who would want to fuck a guy with better shoes than she does."

I took a deep breath and said, "We both know what I am like Mel. If I manage to get a girl at the ball, before you know it I'm in love with her. I don't know if this is a phase, or if deep down I actually want to be a girl. So I need to get this out of my system, before it's too late."

She knew I was right and reluctantly she agreed as always, to support me.

The next day Mel called round and we would get ready together. I have been dressing ever since I could remember. Although my opportunities were quite limited, I knew the basics.

So I shaved my legs, under arms, balls and ass. I sculpted my pubic bush into a landing strip and spent some time admiring myself in the mirror.

I stepped out of the bathroom smelling amazing, towel wrapped around my chest, Mel handed me a glass of rosé wine and we clinked glasses. I followed her into the bedroom and she sat me on a chair to do my makeup.

Once my foundation was blended, the blusher was blushing and the eye shadow and eye liner allured she made my lips kissable with gorgeous deep red lipstick.

I have short hair so there was no real difficulty putting on my Victoria Beckham style black haired wig. Long dangly golden ear rings were clipped to my ear lobes.

"Bloody hell," Mel said. Admiring her handy work. Mel worked in a beauty salon so her talents with a makeup brush were considerable.

"I'm guessing you don't need me here for the next bit?" she asked, referring to the fact that I had to get dressed.

"I'm sure I can manage to dress myself," I reassured her.

She clinked my glass again and waltz out of the room to get herself ready.

I had bought a stick on bra that when closed would give me a small amount of cleavage. I had done this countless times in the past but every time I pulled the two sides together it always made me gasp. Over this I pulled together the strapless Wonderbra and this heightened the appearance of tits.

The only reason I knew of this trick was that my ex-girlfriend Kerry did this to bulk up her pert little a cup boobies.

I then pulled my rather small willie between my legs and trapped it up against my undercarriage, my balls slipped easily back up inside me. I pulled the thong up to keep everything in place.

I find that in these sorts of stories girls like me on our maiden voyages would wear beautiful fully fashioned stockings and suspenders. They weren't for sale in Primark so I got a pair of skin coloured tights instead. For some reason I feel the need to apologise to you my dear reader for this. But it was a cold October in Belfast, and I kind of like tights (pantyhose).

I put on my halter neck top, and tucked it into my leather mini skirt. Now for the thing I love to do most.

I put on my boots. It always sends shivers down my spine as I pull up the zip, the sudden confinement of my calf muscles, for some reason rocks my world.

Now fully dressed I drained the last of the wine from my glass, and I venture forward to gauge my friend Mel's reaction. Instead of the laughter that I was expecting there was a gasp of what I could only assume was amazement. She praised me on my looks, paying special attention to my tits.

I explained how a skinny guy managed to have a decent cleavage and she seemed impressed. I expect that she was just being nice. She had a natural D cup so she would never need to use this trick.

It took me a few moments but eventually I realised that Mel was wearing a long white dress, and she had her long blonde hair tied up in two buns on either side of her head.

"Look at you princess Leia." She chuckled and made her way to fix us another drink.

We drank some more while we waited on a taxi to take us to the students union.

About thirty minutes later the old black taxi was pulling up Elmwood Avenue. I was having second, third, fourth and even fifth thoughts. There was a massive crowd waiting to get into the ball. I don't know what the actual breakdown of students at Belfast's prestigious Queens University but the crowd outside was largely made up of large stocky country folk. Mostly young men in sports tops, not what I was expecting for a Halloween ball.

"This is a really bad idea," I breathlessly whispered. Mel felt my hesitation and squeezed my hand.

"Honey, that's the line of people who don't have tickets. We have tickets so we don't need to wait." She said, before paying the taxi driver. Who said, "Have a great night girls." There didn't seem to be any element of sarcasm in his voice.

We approached the throngs of half cut wannabe revellers and glided past them up the steps toward the black bomber jacket wearing behemoth of a bouncer. Who was shouting, "Here love, if you have tickets this way." Mel was quite a bit behind me, was the door man talking to me?

Soon we slipped inside and made our way upstairs to the speakeasy bar. There was no chance of a seat so we found a suitable space to stand and Mel got us some drinks.

A few more cheeky vinos later and I really started to loosen up. We were now on the dance floor giving it "heeps" as the kids from Northern Ireland would say.

Now it is often claimed that white men can't dance, and a lot of the time this is indeed a factual racial stereotype. So if white men can't dance how about tipsy white men in three inch heels?

I am actually very good in heels, not quite swan lake but definitely not Bambi on ice, I tried to copy Mel and the other girls dance moves. I am not sure if it was an accurate portrayal of "Sexy back".

It was now my turn to get the drinks so I excused myself from the sweaty dance floor and made my way to the bar. It was about three or four people deep so I patiently waited my turn.

I am never going to claim that I was very passible. But Mel's makeup skills have made me quite pretty, especially in the low light of the night club. Soon I was at the front of the queue and an attractive bar man took my order.

I have mentioned before that I was bisexual. But while I thought that I would enjoy being on the receiving end of an eye watering ass fuck, I had never considered having a boyfriend. That was still the case when Josh tapped me on the shoulder.

"Hey, can I squeeze in?" he asked. Josh was doing his doctorate at the university, in my first year he assisted in a lab assessment in one of my chemistry classes. In a class of around sixty students. I'm sure he would be hard pressed to pick me out of a crowd, especially the way I was dressed tonight.

He was an American guy about six foot tall, he had a slim yet buffed build and his mixed race skin did nothing but accentuate his hansom features.

Of course I let him in, and when the barman served me my drinks I made sure that he saw to Josh next. We made small talk about how busy it was, how terrible the service was. He then shocked me by saying, "You look really great tonight," Did he recognise me? Or was he just flirting? Wait was he flirting with me? Bloody hell I was petrified.

We talked a while longer I finished my glass of wine, and was about to order another when Josh offered to buy me one. It was really nice talking to him, he made me feel at ease. We were just talking, however I did catch his gaze wandering down to my chest on a couple of occasions, which really excited me. I took him up on his offer, and he ordered me a Vodka and Coke, as it was being served out of the corner of my eye I noticed Princess Leia getting mauled by Chewbacca. I knew that my friend Mel was in trouble.

"Josh, I need to go, my friend is getting attacked by a wookie, thank you for the drink," I excused myself.

"Wait, do we know each other?" he asked. Wow he didn't recognise me and was talking to me because he was interested in me. I giggled into my straw.

"What makes you think that?" I asked. In my best impression of coy sexuality.

"I never told you my name? Somehow, you already knew it," He reasoned.

I blushed a little before admitting, "You were the lab assistant on my first year chem class,"

His eyes widened, "No I think I would remember a pretty face like yours. What is your name?" He asked?

"That's sweet, I'm Victoria," I offered him my hand to shake almost forgetting that I was Victoria not Stephen.

Josh took my hand and brought it to his lips and tenderly kissed it. He looked into my eyes still holding my manicured fingers and asked. "Like the Spice girl?"

"Like the queen," I gushed.

"Well my lady I simply must have your number," he said. In a failed attempt at sounding posh. I bit down on my lip while I contemplated my next move. Josh was really attractive and I'm sure he would be great in bed. But I'm not sure if he knew that I was a boy, I really didn't know what to do.

"What's wrong? You don't think I'm cute?" he pouted. He was cute, he passed me his phone and I entered my number into it.

I slid it back to him and he thanked me before adding, "I'm going to call you" then he leant in and kissed me on the neck and whispered in my ear, "You sure you need to help your friend?"

Breathlessly I answered, "I'd rather stay but she'd never forgive me." I broke away and confidently (which was difficult being fully aroused wearing a thong and a leather mini skirt) made my way back to Mel and her new friends who were also dressed as star wars characters.

The wookie was really behaving like an animal. As soon as I arrived he cupped my ass, and tried to pull open my top. Frantically I turned to the guy dressed as Han Solo and said, "You really want to get this walking carpet out of my tits."

He spoke to his furry friend and apologised to us both offering to buy us drinks. Mel had been waiting for some time for me to return with her wine, so as I handed her the plastic tumble filled with cheap Chardonnay she looked at my vodka and coke and said, "Well if I have to wait this long you two might as well go and get me another."

For quite some time the wookie and I exchanged small talk, with his mask on I had no idea what he looked like. He made it very obvious that he liked me. At one point during a slow song we were dancing together and as I ground my ass into his crotch I felt the unmistakable bulge of his erection.

By this stage in preceding's, I was quite drunk and very horny. Instead of being repulsed by the hardness I found myself drawn to it. I turned and lifted open the mouth of his mask and kissed the wookie on the lips. Rubbing his cock through the furry material of his costume.

"I really want you," He slurred into my ear. It was supposed to sound confident, it didn't. He followed it up with the equally drunken sounding, "Come back to mine and i will show you a good time!"

I should have laughed in his cheap plastic mask, but I was drunk and in my drunkenness I found him irresistible. Mel arrived back from the toilets with Han. They were both sporting massive grins, her lipstick was smeared and there was an unfortunate yellow stain on her dress just under her chin.

She cupped my ass, and shouted, "Get a room, or better yet the disabled toiled has a condom machine!" The wookie looked at her in surprise then to his mate who nodded they high fived and the wookie began to pull my had toward the toilets.

I was too drunk to fathom the implications of what was about to happen. The wookie had tried many times to put his hand up my skirt, each time I stopped him. He was as inebriated as I was so I'm not sure he could see straight enough to be able to make me as a boy. He hadn't felt my cock either so I was sure he thought I was a girl.

Despite the queues at the other toilets there was no one in the disabled toilets. We sealed ourselves in. He was all over me in seconds. I heard the ripping of the Velcro and Chewie suit fell to the floor. He moved to take his mask off, and I asked him not to. He pulled out his cock out of his cheap blue boxer shorts, it was slightly bigger than my own but only just, he tugged it a few times. I stepped closer and took it in my hand gently stroking it with one hand and cupping his balls with the other.

This wasn't my first experience with another person's cock. I first touched another man penis the day after my eighteenth birthday. Finally of legal age I had made my way to the local gay bar. I was a young looking man, and I was quite popular. Since that faithful night I have wanked and sucked off four cocks. My ass was still virgin territory. That was about to change.

I knelt over and kissed the tip of him, it had quite a nice odour well it was nicer than the smell of the toilets anyway. I sucked the tip into my wanting mouth and instantly tasted his pre-cum which was oozing out of him.

For a few moments I sucked on his hard cock still standing, in my drunkenness I didn't feel him reach behind me. It was only when his finger slipped into my ass that I realised what he was doing.

"Wait!" I pleaded. when I realised that he was only a few centimetres from finding out Victoria was really Stephen.

He tried to reassure me, "It's ok I know you're on your period, so I'm gonna use your butt," Very presumptuous I thought. He was right though. I was going to allow him into my backside.

"My period," I hesitated.

"Yea, you wouldn't let me touch your pussy so I knew," He reasoned.

Next thing he was pumping two pound coins into the machine and out dropped a little box with a condom in it. He held it up for me to see.

"Ribbed for your pleasure," he chuckled to himself. Tearing open the foil, with one eye closed he attempted to roll the condom along his shaft. God he was pissed, I could probably shove my own dick up his arse and chances are he would not notice.

I decided to take pity on him. Odd given that he was about to invade my tight asshole. I rolled the rubber onto his little penis. Holding my own cock out of the way I bent over and asked him to lube my ass up. Dutifully he did as he was asked and got down to the floor and began to lap away at by winking brown eye.

It was good and wet when he started to finger me. It was uncomfortable at first, but by the time there were a few fingers in me it started to feel almost enjoyable.

"I think it's time you slut," He said. Startling me as he stood up, pointing his winky at my ass.

Some fidgeting later and his tip was pushing its way past the first wall of muscle. I pushed back a little and he slid in fully.

Suddenly it struck me I was getting fucked by a stranger in a wookie mask. I had never seen his face, yet I had sucked his dick, and now he was inside me.

It was an odd scene as I looked at us in the full length mirror on the opposite wall. I was standing slightly bend over. My leather skirt was pulled up over my waist the gusset of my tights and the thong panties were gathered half way down my legs, and were spread between the top of my leather knee high boots. With one hand I was balancing myself on the wall with the other hand I was holding my cock out of the way hopefully out of sight.

Behind me was a pudgy guy wearing a rubber wookie mask, he was still wearing blue boxers his little ass invader stuck out through the slit in them and into my ass. He was staring down at my ass one hand on each hip and he trust quickly into and out of my ass.

There was no real depth or hardness to his pounding it was just rapid.

I found the whole experience rather disappointing. I looked amazing and I had settled for the first guy who paid me any attention. I felt his nails dig into my hips then he went ridged.

He called out, "Oh Mammy!" there was some fidgeting from behind me, as he slopped into me a few more times before he went flaccid and fell out of me.

He scurried about grabbing his things, and fled.

"What the fuck!" I thought. As the door slammed behind him. I quickly locked it before some other horny couple came in.

As I set about fixing myself up I noticed to pool of cum on the floor between my legs. I had not orgasmed (I think) but I leaked an amazing amount of pre-cum onto the floor.

I tidied my little cock back in place, fixing my skirt and made my way back out.

Mel was standing alone where I left her. It seems that chewie grabbed his mate and left.

"Well?" Mel asked. Wickedly smiling at me.

"That was awful," I responded. We gathered up our coats and bags, and made our way out to get a taxi home.

As we sat in the mini cab Mel ridiculed me about what had happened. Eventually saying, "You need to be pickier sweetie, you can't just jump the first guy who shows interest." Just as she said it my phone whistled indicating I got a message.

"Hi Victoria, it was lovely meeting you. I hope your friend was ok. Can't wait to see you again some time. Maybe we could meet in the parlour on Thursday? Lots of hugs... Josh"

"Maybe I should have just jumped on the first one," I said. Showing Mel the message.

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