• Home
  • /
  • Stories Hub
  • /
  • Transgender & Crossdressers
  • /
  • First Time

First Time

As the van pulled over I noticed three male occupants sitting in the front seats. Not sure what to do I waited for the driver to get out. He was dressed in workers clothes and had a broad Irish accent. "Hi I'm Jimmy he said you gonna have to climb in the back". I stumbled around in my wedge heels to the back of the van and with some assistance climbed into the back. With a slam of the door, I was now a willing prisoner.

It was dark but my senses very quickly picked up the strong odour of musty sweatiness, even I would say stale sex. There was also a hint of the smell of urine. This arousal only helped to the highly charged erotic blanket that engulfed me. As my eyes adjusted to the darkness I noticed a mattress on the floor. It was filthy and looked like it was dressed in many sexual encounters.

Here I was dressed in a long coat, heels, lippy and wig, with only a bra and knickers underneath in a van driving somewhere with three strangers. My skinny smooth body trembling in excitement. Oh how erotic it was as my cock swelled in agreement.

The journey was bouncy and despite the hesitation I knelt down on the mattress. The closer I got to it, the aroma of sexual encounters increased. Who were these people and what were they going to do to me, when, where and for how long.

My advert had said I was an experienced slut which could not have been further from the truth. I was a virgin stepping well outside of my comfort zone. Knowing that a submissive slut does not say no, meant I had to go along with everything on offer. The fear and adrenaline was forcing my heart to burst through my chest.

The day had been sunny and hot and it quickly started to become very hot in this enclosed space which only added to the tension as sweat droplets started to form over my skin. The foundation was melting over my face and my wig was causing my head to itch. I had to take of my coat but was worried that would leave me vulnerable sitting in a bra and knickers, but the heat was starting to become intense.

As I lay there the I succumbed to the heat and a journey which never seemed to end. I must have slipped asleep, as the next thing I knew the van was stationery and bright light was flooding into the back of the van. Standing at the back were two figures, whilst the third who I recognised as Jimmy was standing over me.

"We normally only do girls, but you looked far too sexy to ignore", Jimmy said, as he loosened his pants and dropped them around his knees, a chunky piece of manhood was before me. Apart from my own cock this was the first cock I had ever touched and euphoria gushed my body. I did not want to look inexperienced so recollecting all of those porn training films I had watched, I took hold of his growing member and placed it in my mouth. The rest seemed natural and wildly arousing. I supped and gurgled as saliva enveloped his shaft trickling down between his balls. I wasn't sure what the other two were doing, but I didn't really care. And then as quick as I had placed his cock in my mouth he pulled himself free, pushing me back onto the mattress, pulling my legs by the ankles up over his shoulders as he shuffled his body towards my pussy hole.

With my wedged heels dug firmly into the shoulders of Jimmy, he teased his hard soaked meat around my virgin lips. You are tight, he exclaimed, to his delight. Perhaps not a good time, or maybe it was to confess my virgin status. Before I could get a chance though to plead my innocence Jimmy's mate shoved his ample manhood into my mouth with the hey ho cry, suck on that baby. I duly did. It tasted sweaty and cloggy, as if it had not been washed in a while. Solidified man cheese was evident which was erotically repugnant.

As Jimmy teased his cock around my pussy hole I felt the need to relax to allow it to enter. Perhaps he knew I had never had a cock in there before, but a carnal enraged man does not worry about sensitivity, and it was not long before I felt my hole open as his solid cock entered its way in. The pain was excruciating but I could not react in shock as I had a piece of meat thumping at my tonsils, and to be honest it was a pain that was wrapped gorgeously in pretty ecstasy printed wrapping paper. After Jimmy had fully entered his head I was dancing with senses that had never been awoken before.

Oh wow this was the most erotic thing that had ever happened to me, but I had forgotten there was three of them until I felt a warm sensation flooding my torso. Opening my eyes that had started to roll in their sockets, I saw horny number three standing over me pissing over my naked tummy. As the warm piss quickly cooled it acted as a refreshment to my dehydrated body and soul. Oh wow I did not want this to end, but I knew inevitably it would end at some point.

The cock in my mouth was now pulsing as its owners voice became more a muffled moan, and then with an enhanced tremor I felt hot jizz hit the back of my throat. A second pulse bought more love juice. My mouth was full, but I could not swallow as his meat was still firmly shoved in. I gagged which caused him to pull out, as cum mixed saliva rolled down my chin onto my sweaty neck and down through my cleavage.

Now catching my breath, I cried out to Jimmy, "baby fuck me hard". He did not hesitate, pumping his manhood rhythmically with his balls slapping my cheeks. Ryan whose balls I had just emptied was now lying slumped and exhausted. Jimmy's other friend though was now straddling me across my chest with his ass in my face. As he lowered himself my tongue started to caress his stretched hole and he was now sucking my hard cock. Oh wow he looked far to alpha to be sucking another man's cock but seemed to know what he was doing.

All I can remember next was that we both came together. As Jimmy pumped my hole full with his juice I was likewise sharing my squirt into another man's throat.

So in one moment, after an advert placed, I sucked my first cock, tasted another man's gift, and shared my relief into another man's mouth. Who said dreams can't come true.

  • Index
  • /
  • Home
  • /
  • Stories Hub
  • /
  • Transgender & Crossdressers
  • /
  • First Time

All contents © Copyright 1996-2023. Literotica is a registered trademark.

Desktop versionT.O.S.PrivacyReport a ProblemSupport

Version ⁨1.0.2+795cd7d.adb84bd⁩

We are testing a new version of this page. It was made in 22 milliseconds