Open Your Mind to Something New

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Cream pies enjoyed with an alluring shemale.
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Dazman
Dazman
365 Followers

Open minds create amazing experiences

This experience had its genesis in my early twenties when I unexpectedly began exploring my bi-side with my childhood buddy, Lyndon while both of us were studying at university (refer to my story Friends Satisfying Each Other for background context). This story takes place over a weekend, Friday evening to Sunday afternoon, and it took a whole day of seduction before any sexual activity took place. Hence, this story does take some time to get going before we encounter any hardcore action, but then it's non-stop.

*****

On this Friday night in the early 1990s, I had again travelled north to the industrial city of Leeds to spend the weekend with Lyndon and his university housemates on the hunt for pussy. Between my first bi-experience with Lyndon and this night in question, I had expanded my knowledge with fuck sessions involving his housemates, and a couple of foursomes on unsuccessful nights out. It was an exhilarating broadening of my sexual horizons by a small group of like-minded friends that kept the secret firmly in-house.

The rules of the game were simple. If we went out on the town, then the first priority was pussy. Those of us who lucked-out (rather too frequently as it turned out), could go home, drink beer and watch porn. Those of us who were so inclined could engage in gay sex; acts such as sucking cock, fucking arse; golden showers; and swallowing cum were all permitted if parties consented. Kissing, however, was strictly taboo; and the following morning, no one was to talk about what happened. It was all an elegant arrangement.

So, we all went about our usual routine: shower, shave, sculpture, aftershave, condom and a wallet full of cash. We took the bus to the city centre and hit the pub scene. This night was another balmy one in late-August, after what was a great summer holiday. A couple of us were contemplating heading back to university for our final year, while others were facing the job market as potential graduates. Regardless of our individual fate, the four of us were determined to enjoy what remained of the summer.

As was customary, there was nothing but a few small bites in the pubs but no commitment, so we inevitably ended up at a favourite nightclub, just before midnight to avoid paying the cover charge. Back in those days, smoking in pubs and clubs was still permitted, and as none of us partook in that particular vice, we found the cloying environment heavy going. In this specific club, the music was the familiar dirge of half-decent songs destroyed by accelerated, repetitive dance beats. Music to dance to it was not, despite many a maniac trying to do so.

At one point in the night, I can't remember when it was, this tall, pretty blonde sauntered across the dance floor and approached the bar. Our group was sitting on a row of stools against a balustrade area about a metre away. Lyndon and his housemates suddenly became animated and started yelling crude insults to this blonde girl, who promptly turned around and stuck her tongue out while, simultaneously, waving double birds in our directions. It appeared to me that both parties shared some animosity between them and so I asked Lyndon about it.

"Seems a bit rude?" I asked.

"Oh, it's not what it looks like. And there's very much more than meets the eye." He replied, with utter derision.

"What do you mean?" I asked incredulously.

"That's not a girl, Jason. That's a man that dresses up like a girl, acts like a girl, comes across like a girl, flirts like a girl but in reality, is a sick pervert!"

"Oh," I answered, with surprise, "So, he's a crossdresser?"

"More like a fucking poof!"

Then one of Lyndon's housemates piped in with another piece of information, "Goes by the name of Teresa. More like, Terry or Terrance!"

The three of them snidely laughed together in unison. I felt distinctly uncomfortable by this unseemly bullying, but then I didn't have the full context.

"Terry's notorious around here," continued the other flatmate, "He squats in this club and tries it on with unsuspecting students that don't know better. He gets them to buy him drinks all night with an offer of sex. They go off to the toilets, where he reveals his surprise!"

"Yeah," added Lyndon, "A mate of ours fell for that trick last year. He took her into one of the toilet cubicles and after he went for a fumble, came running out of the toilet and fucked off home."

"It wasn't till a few days later that he dared to tell us what happened." Said the second housemate.

"It's fucking not right what he does." Said Lyndon, with disgust.

"Someone should take him out the back and have a 'word'!" added another.

I didn't believe what I was hearing. Although I couldn't quite reconcile Terry's actions, dating in the nineties and beyond was a buyer's market. Caveat emptor! Perhaps, Terry's actions were deliberately misleading, but this level of scorn and abuse seemed over the top to me.

I looked over to Terry, purchasing a drink at the bar, and had to admire the lengths he went to appear convincing. He wore black high heels, had long, slender and smooth legs, wore a single, yellow dress and sported a large, and compelling bust - must be a lot of socks to achieve that bra cup! The face was made up like the real girls that were in this club. To all intents and purposes, Terry was his alter ego, Teresa, and that was his personal choice. Far be it for me to judge, but others didn't seem to see it through my lens.

Teresa took his drink and walked to another part of the club without looking in our direction, and, mercifully, the guys kept their insults under control. As the night wore on, the cigarette smoke, noise, dirge of mindless music and the alcohol were bringing on a headache. I was seriously contemplating retiring early, and sex was as afar from my mind as could be. Lyndon and one of his housemates were exploring promising leads with a couple of pretty girls while the other housemate and I were starring forlornly across the dancefloor yielding very few prospects. Suddenly, the other housemate stood up from his stool, grabbed his drink and announced he was going for a wander. For my part, I downed my beer and contemplated fighting my way to the bar for a refill.

I walked around the elliptically-shaped bar, looking for space where the crowd was thinnest and found an opening that was furthest away from we were sat. After this unusually tall and wide man grabbed his bevvy of drinks, I eased into the opening he left before anyone else could fill the void. I felt a surge of bodies against me as I strained over the bar to catch one of the bar staffs' eyes.

"So, you had fun with your friends then?" Came a female voice, heavy with scorn.

I struggled to turn my head left, amidst the crush of bodies vying for drinks, to see where the voice was coming from, and to whom it was directed. My eyes immediately locked onto the hazel-tinted eyes of Teresa, sat on a barstool and nursing some green liquid that passed for a cocktail.

"I'm sorry about that, but they don't speak for me," I yelled above the head-splitting din before turning back to the bar staff.

"Don't fucking lie!" Came an embittered response. "I saw you as clear as day."

I knew then what the term guilt by association meant.

"Yes, I was there, but I didn't yell any insults at you!" I replied. "Fuck! I don't even know you."

"They're your friends!" Was the indignant reply, and this exchange was attracting unwanted attention from other patrons close by that could hear this fiery exchange. Mercifully, a bartender took my order, and that enforced a temporary ceasefire. After I grabbed my beer, I thought about simply walking off to diffuse the situation, but something about this exchange indicated genuine hurt on Teresa's/Terry's part, and I found my friends' behaviour distasteful. I wasn't going to be cowardly and decided I would confront the issue head-on.

After I extricated myself from the sweaty mass of avid clubbers, I took a position in from of Teresa. She swung round on her barstool and faced me, face full of fury.

I leaned in slightly so she could hear me above the dirge. "How many times have you seen us together?"

"What do you mean?"

"Me with them?"

This placed her off balance for a second because she knew that she had never seen me before because the two of us were complete strangers.

"Doesn't matter." Came the evasive response. "You were all yelling at me."

"I wasn't because I don't know who you are."

"Your friends would have no doubt told you who I am?"

"They did after I asked why they were carrying on like they were."

"And?"

"And what?" I replied, becoming somewhat irritated by this circular back-and-forth. "I didn't make a judgement about you, and I found their behaviour to be juvenile and unworthy, to be honest."

Teresa/Terry was taken aback slightly by my forthrightness. He/She moved to respond but then appeared to take a second to gather some thoughts. I took this breather to analyse my antagonist up close. If Teresa were a real woman, rather than Terry, she would describe as stunning. She had light skin with high cheekbones. Her blonde hair was long and luxurious, falling in layers just below her shoulders. Her hazel eyes smoked with intensity, and there was a tight pair of lips rounded off by the most delicate aquiline nose. These rest of her body exuded femininity, particularly the amply sculpted breasts. She sat cross-legged, and those legs were tanned, smooth and supple. My analysis began making my cock stir in desire.

"So, you're ok with me?" Asked Teresa, interrupting my analysis, having concluded that for me, she could pass for a female (if that was her/his thing).

"They're your choices, not mine, and if you're comfortable in your own skin, then that's good with me." I hoped this would disarm the situation and let me get back to my friends. "I don't know your backstory, but I doubt you'll lose sleep with or without my approval?"

No! I won't." Teresa's look was as cold as ice, shooting down my attempt to lighten the mood. By now, I was itching to extricate myself and re-join my friends, assuming they were still at the club.

"Look, if you re-encounter them simply ignore them. Clearly, my friends aren't in your league, and you can do so much better. So hold your head high and be bold." I have no idea where those words came from, but I hoped they would be enough to conclude our tense interaction.

"Thanks, I will." She flashed me a broad smile, bristling with pearly whites, and now disarmed.

"Well, enjoy your night!" I said relieved and raised my beer to my lips before turning to walk away.

"Do you have to go?" I stopped dead straight. No, I suppose I didn't because my friends appeared to be occupied in their various pursuits, but I still had a thumping headache, and I felt a real desire to blow this shit hole of a club.

"No. I'm happy to stay just so long as you stop associating my friends' behaviour to me," I replied, with a laugh.

Teresa smiled at me again. It was a lovely smile.

"Would you like a drink?" She asked as her purse opened up. Lyndon and Co. told me that men always bought her drinks.

"Sure. Mine's a beer." I said, draining the last mouthful.

"Cheap drunk." She replied, laughing.

We grabbed our drinks, hers was another funny coloured cocktail, and she led to a dark recess, in the corner of the club. It was less smoky, and that music wasn't as thunderous. The changed atmosphere was conducive to talking.

"So, what's your name?" She asked, kicking off the conversation.

"I'm Jason. You?" I thought I may as well confirm the information given to me by my friends.

"I'm Sam, short for Samantha." So not Teresa or Terry then? She must have seen my confused expression.

"Why, what were you told it was?"

"Oh, they said your name was Teresa, or Terry or Terrance or something."

She snorted in laughter.

"That's because they are fuckwits!" Which was a statement that had a ring of truth to it.

Lyndon was my childhood friend, and my first love in some regard. I was jealous of the sexual experiences we had shared before university, despite us both having frequent liasons with the fairer sex. While I tolerated his friends, and enjoyed the fuck sessions, I found them to be tedious to hang out with.

"So why are you here then?"

I explained my friendship with Lyndon and how we were both at uni together, but I omitted the gay sex stuff.

"So you're single?"

"I am." Was my response, "I recently broke up with a sixth form girl whom I didn't see eye to eye with."

"Didn't give you what you wanted, eh?"

"Well, let's just say we had diverging sexual tastes."

Now this conversation was heading down dangerous territory. Lyndon and I watched pirated german/ French pornos together before we had sex. Many of those movies featured hard anal sex and golden showers. These were two kinks that got us both off, and that we partook in. I broached these delicate subjects with this sixth form girl, who had massive tits, but she turned the colour of bad shit and ran a mile, or one hundred, away from me.

"Do tell?"

"Well, let's just say, my tastes a little more 'European' than is normal."

We both laughed at the innuendo.

So Sam began probing me for more information, and this became a comedic game of cat and mouse. For the first time that evening, I thought I might get lucky with a man that looks like a woman.

"You fucked a man?" She asked at one point.

I didn't deny it.

"You let a man fuck you?"

Again, I kept a diplomatic silence, but gave away the game with a wide grin.

"Mmm, I like a man that's open minded." Better than being called a boy, as Lyndon's friends sometimes referred to me as.

At that point, Sam stood up, and, provactively, ran her hands over the svelte body. She cupped her breasts and leant opver to me, before whispering, " Would you be open to some of these?"

I was.

"Let's go!"

We left the club, mercifully for my lungs to recuperate, and as our eyes adjusted to the faint glow of morning light, the street still had a slackened level of activity.

Sam led the way.

"Are we getting a taxi?" I enquired.

"No need. My place is only ten minutes away, and besides, I'd rather walk."

In those heels? Sam was braver than I'd thought. In any case, the blast of the fresh, morning air was beginning to relieve my headache and reinvigorate my energy levels. We walked alongside a dun-coloured canal to a part of the city that I was not familiar with. I was walking into what looked like a redeveloped and upmarket area that was as far removed from Lyndon and co.'s student slum as you could imagine. The path we trod beside the canal was cobblestoned, and the street lights resembled lanterns, giving the urban space a feel of old times. The buildings were once linen warehouses from the Victorian age that had been converted into fashionable loft-style living spaces. Evidently, Sam's place was among this salubrious district.

"Here we are!" Sam announced.

We had arrived outside one of the said converted linen factories that were fiercely lit up against the lightening dawn. I couldn't quite make out the name of the place or the street that it was on, but I estimated that the walk from the city centre took no more than ten minutes.

"Come on up!" She asked as the elevator door slid open.

I stepped into the lift that was barely large enough for two people and thrust the two of us uncomfortably close to each other. Both of us stank of cigarette smoke primarily, but beyond that objectionable odour, I could detect the faint scent of Sam's perfume. It was a mildly erotic.

With a ding, the elevator doors opened to a dimly lit hallway. Sam exited the lift and directed me to the left. She reached into her bag and pulled out a key, and a moment later, we were in her magnificent apartment. For 'magnificent' was the only adjective that could describe this type of loft-style living!

Sam's was a one-bedroom top floor, corner apartment with a timber-beamed vaulted roof that accentuated the space so that it felt more substantial than it actually was. The two external walls were patterned in simple un-rendered brick with four large, eight-paned windows that let in swathes of natural light. The internal walls were simple white plasterboard that dazzled by the contrasting dark hues of the timbers that supported the ceiling. The place was fitted out simply but effectively, and felt warm and cosy. How was she financing this, I wondered internally?

"Take a seat," Sam declared. I complied, the couch looked and then felt embarrassingly expensive.

"Want a drink?"

"Sure. What do you have?"

"Everything!" came a confident reply.

I didn't doubt it for a second for Sam's place oozed wealth, and I was clearly overawed because I failed to reply.

"How about a gin and tonic?" Sam suggested, reacting to my stupefied silence.

"Ok," This was going to be a first for me.

"Ice and slice?"

"What?"

Sam laughed, "You're really new to this, aren't you?"

I felt this comment was directed towards my naivety, my countryside heritage and, by implication, my lack of sophistication. However, despite the apparent offence, I didn't want to be insulting towards my host.

"Tonight's been a slew of firsts for me." Which was true.

"I bet." Came an amused reply.

Seconds later, I was presented with a tall glass filled with translucent liquid and cubes of ice, topped off with lemon and lime slices and a pinch of mint. I took a sip and was pleased with the citrus burst, but found the bitter aftertaste somewhat of an adjustment. Sam saw my reaction and laughed at my bemusement. However, I soon became used to the taste and before long was knocking back the G&T with gusto.

Sam and I talked well into the morning, and I figured my chances of any sexual activity were diminishing by the second. My intuition was confirmed when Sam put down her glass on the table and said she was getting sleepy. Taking the hint, I rose from the couch and announced my intention to depart.

"There's no need to do that. You can sleep on the couch if you'd like as I've got spare blankets in the cupboard."

To be fair, I really didn't fancy trudging my way back across town and plus I wasn't quite sure of my surroundings or of the direction needed to get back to my mates' house. So, the offer of a bed for the night/morning was readily accepted. A few minutes later, after a platonic peck on the cheek, we said our goodnights and I was fast asleep.

****

I awoke, groggy, several hours later to a humming noise coming from somewhere. The light was streaming in through the large luxurious windows of Sam's loft apartment. I had the thirst of the Gobi Desert and needed to piss, badly. It was with some reluctance that I got up, but I remembered I was naked and it wouldn't do to be so brazen in a relative stranger's home. I reached over for my clothes, but I couldn't find them, they were nowhere in sight. I sat up on the couched, wrapped up in the blanket and looked around my surroundings.

"Ah, you're awake?" Came a sweet voice through the groggy haze.

"Yeah, but I can't find my clothes."

"Sorry," answered Sam, "I thought I would wash them to get rid of that awful cigarette smell."

How considerate.

"Thanks," I answered appreciatively, "That's very thoughtful."

"No trouble," Came a nonchalant reply, "I had a load to do anyway, and it's nearly done."

"Can I get a glass of water?"

"Of course," Sam responded, "I've also got some coffee brewing if you'd like some?"

That's what the aroma was that I detected through the slowly clearing, alcoholic fog. Being a young man from Yorkshire, I was brought up on copious amounts of strong tea. Coffee was something that was in fashion at University with the introduction of the disposable paper cups from cafes that littered campus everywhere. Coffee also came with a cornucopia of Italian names, a place that was as alien to me as the moon. Still, it had a pleasing smell, and I was in no way hostile to coffee, so I readily assented to Sam's offer.

Dazman
Dazman
365 Followers