*Note: This is a story where all parties involved are over the age of 18. There is a brief period of non-consent so if that is not your thing please feel free to skip. This story also involves Cross Dressing themes.
*
It was a kink of mine. Cross Dressing, that is. What started out as a funny thing to do every Halloween - dress up as a well-known female Horror character - and it grew from there.
At first it was secretly dressing in the wives' things, and while at times I thought I looked relatively okay, there were others where I looked like a stuffed sausage and quickly took the item of clothing off, never to be looked at again.
When watching pornography, I found that I had become more curious about what it was like being the female, admiring the outfits they at least started in and how good they looked, curiosity soon had me changing the categories of what videos I viewed, the new videos seemed to be more trans and cross dresser/sissy orientated.
My wife and I, having spent the last decade as swingers, had been with other couples, I had watched her with others and she had also watched me, knowing each other's fantasies and understanding we couldn't help each other with out bi-curious sides we had a bit of 'free roam' when it came to exploring that side - something we had both taken advantage of in the past.
All it took was a simple conversation with her one afternoon to have the 'green light' to experiment with dressing up for men. In fact, she seemed quite excited about the prospect and began scrolling online shopping places like Amazon and Shein for some clothing and accessories.
Flicking me through a couple of photographs from several websites offering me different opinions and options on a few wigs that she had found while browsing for the clothes, we selected three, a black, a pink and a brunette one.
Over the weeks that followed I began to shave, my wife taught me what she new about makeup, how to apply it, how to remove it, and what different bits did what. She offered advice on clothing; styles and what accessories went together. Before eventually leaving me on my own to practice and begin feeling comfortable.
--
I, at 39, was a little older than some of the other cross dressers I saw on the local websites and pages you could advertise. It was also immediately clear that many of these gurls were cute as hell, spending a long-time taking care of themselves and looking like they do.
Nervously I posted that I was a relatively new cross dresser, looking for someone understanding yet willing to provide me with my first experience as a Cross-Dressing Cock Sucker, then I attached a couple photos of me in my 'best' outfits.
It was only about half an hour later I received my first response, a man named Thomas, he was 36, had an average type of body but carried muscles, with a 6-inch uncut cock - as he showed me in the photo he sent.
"I'd be keen to try you out," he messaged as part of his introduction to me.
"Really?" I asked still doubting myself and how I looked.
"Sure baby, all you need to do is get on your knees and open your mouth - I can do the rest, no small talk nothing." He replied, while it sounded a little bit demeaning at the same time it sounded perfect, no small talk about me or us, nothing about dressing and not having to sound 'feminine' when speaking.
"Sounds perfect," I replied, before asking when he could make it to my place. We agreed on an hours' time so that he could shower, while also providing me with enough time to get ready.
--
Wanting to look as sexy and irresistible as possible I went for a short faux-leather outfit my wife had purchased me, I accompanied it with the black wig, but ensured to wear red lipstick as Thomas had requested.
It was an hour, almost on the dot, when I first heard the rumblings of his motorbike turn into my street. Shit! - I thought to myself, as we lived in a quiet cul-de-sac, my neighbours were all elderly who had lived in their properties for decades, we never had this type of noise in our street.
The rumbling soon stopped, nervously I heard the kickstand of the bike be put into place as it came to rest in my driveway. Thud... Thud... Thud... I could hear his footsteps towards the front door, growing louder the closer he got with every step that he took towards me.
The butterflies in my stomach began to flutter as I stood in the hallway just through the threshold of my front door listening to the strangers' steps come closer. I lowered to my knees as had been instructed, moments later I heard the knob of my front door begin to turn, the latch coming loose and the door opening from its frame.
"Mmmm," a low moan of approval came from Thomas the man who was entering my house, seemingly approving of what he saw as he slowly pushed the door to its closed position, clicking the lock on it once it was closed.
I blushed a little with the thought of him liking what he saw, Thomas, now taking the two or three steps towards where I was kneeling, was wearing a pair of black jeans and had a black singlet top on with his outfit topped off by wearing black leather boots.
He began to pull the zipper down on the fly of his jeans, I reached my hands up to help.
"NO HANDS," he commanded in a stern tone, scaring me a little and led me to dropping my hands to my side where they were previously. Once his fly was undone, he began to fiddle inside before pulling his uncut cock out into view through the opening.
He gave it a couple tugs back and forth, pulling his foreskin over his head and back. I was mesmerized and couldn't help but watch as he did this, my mind was spinning as I couldn't believe what was happening and just how quickly it was happening.
"Open," he said with a gruff, I didn't need to ask what he meant, I immediately parted my red lipstick covered lips as he took the last final minor step towards me, carefully lined the tip of his hard cock with my mouth and began to enter.
As his tip began to run across my tongue, he placed his hands on the back of my head and began to pull it towards his groin. It took me by surprise, although I suppose from our chats and the few words, he had spoken to me I should've known it was going to happen.
I began to gag a little, as internally I begged my throat to relax and welcome him in, my gagging didn't seem to stop him, he continued to slide himself in until his ball sack was resting against my chin, he stood there, me on my knees swallowing his sword while he held me in place, my stomach and throat beginning to convulse already as it struggled to get air, eventually he relented and pulled out, while gasping for air I noticed a fair chunk of my saliva already dripping from his rod.
I was only able to grab a couple quick breathes before he was pulling my head towards his junk once again, I quickly opened my mouth ready to receive as he slid in again, at first going deep into my slurp tube but not staying as long, this time pulling back but not completely out before entering again back until he was balls deep again.
He repeated this process again and again, fucking my face for his pleasure, all that was escaping my throat were deep muffled moans blocked by his cock as he slammed against by gag canal, and spit falling from my throat when he did his mini withdrawal before slamming back into my gullet.
"Oh, you're such a good cock sucking slut," he said as he continued his assault on my throat, I had to keep reminding myself to breath through my nose as he went to work like a jackhammer as he slammed himself in and out of me, his balls smashing into my chin with every thrust.
It was maybe five-minutes after he began using my throat as his personal fleshlight, that his groans and grunts began to escape more often, I knew he was getting close, I was getting quite turned on at the fact for the first time dressed up I was going to make someone cum very quickly.
I was right. Two or three thrusts later he clinched the back of my head, thrust himself forward as much as he could and began to shoot ropes of his white gold down my throat, I lost count at four different large ropes as I needed to swallow, but there were at least two more larger ropes after my initial swallow before each wave afterwards contained less and less.
Soon he began to go limp in my mouth, releasing my head, he pulled his manhood from my lips and quickly tucked it away. Zipping his jeans up.
"You'd do," he said, "I have a friend who'd absolutely love to meet you," he continued as he looked at me with a satisfied look on his face.
"Oh, nice - well next time maybe he could come around too?" I replied, flushed by the actions that we had just done and getting to my feet. He immediately began to chuckle at my reply.
"He'd like to meet you now, let's go for a ride?" he offered yet with a somewhat demanding tone to his voice.
"I have neighbours I can't go out like this," I said, kind of reminding him I am a cross dresser, and this was my first time doing this. My neighbours would get the pitch forks and burn my house down if they saw me dressed like this or had any idea what I was doing.
"Problem solved; I will grab my jacked. I am sure we could make it worth your while if you were to come for the ride." He seemed to have a solution, and make it worth my while? Was his friend going to pay me? I was curious... I relented and nodded.
He slid out my front door, I should've locked it, I obviously didn't, he came back in with a leather jacket and handed it to me to put on, cover up and hide as much as I could with nosey neighbours and an obviously noisy bike engine.
Something caught my eye as I went to put the jacket on, a patch. I looked at it and my heart sank. It was the gang patch for the Dead Man's Hand Motorcycle Club, an outlawed club that is responsible for the drugs and guns around the city.
They battle for turf against the Grim Pistons, sometimes it gets violent, even deadly.
Immediately my mind began to race for ways to get out of this, yet every excuse I could think of would either put me in danger for turning him down or just prolong the inevitable as he'd be back. I gave up and put the jacket on as he led me out the door and towards his bike, positioning me on the back before kicking it into action.
--
It was only a ten-minute bike ride before my heart sank even further, when the bike slowed down to turn into its destination, it simply wasn't a friends house it was the Club House. Here I was on the back of a motorbike of a gang member heading into their club house.
