Pushing the Limits Ch. 02 - Mariaxx

Author's note: This is the second instalment of this cross-category series and a follow up to 'Pushing the Limits'. While part of a series it is intended to also work as a standalone story.

Whereas the first story dealt with incest/taboo this is a crossdressing/transgender story. There are references to an incestuous encounter, but no incest sex is described here. There are also elements of non-consensual/reluctant sex in this story.

The next story after this will explore Jean's trip to Bangor and what happened when she met her friend.

Enjoy

* * * * *

Just 4 people remained in the factory building as the machines fell silent. Richard was now isolated in the security room. Nothing to do but monitor screens and perform hourly checks, inevitably he was bored.

Already Richard had his feet up on the desk and was scrolling on his phone. Having blown the balance on his online betting account and vented his anger at the world on Twitter, he decided to turn his attention to porn.

Richard had a broad palette when it came to porn, you name it he's jacked off to it. He had been through his lesbian porn phase, his bdsm phase and he had recently developed an interest in watersport porn. But without doubt his favourite category at this time was transgender or 'shemale' porn (the term he used).

Richard gave little thought to why he found trans porn so enticing, but he was blown away by these smoking hot women with an insatiable appetite for sex and a surprise between their legs. Flicking through videos on a free porn website, Richard stopped on bid of his favourite pornstar Dina Splendina. This video showed the buxom blonde Dina 69ing with a similar looking blonde female while a guy fucked her in the ass. He opened the belt of his trousers and opened his fly to give a bit of space to his already hardening cock.

Richard moved to another video, this showing Dina with three guys. She was getting fucked by one, giving a blowjob to another, and herself fucking the third guy, all at the same time. Richard couldn't resist anymore and slipped his thick 8-inch cock out through fly.

Richard kept skipping through videos and pulled away at his cock throughout. Each time he felt ready to cum he pulled back, edging along, sweating, drops of precum seeping onto his hand. He managed to keep this up for an hour. The skin on his cock was now getting red and sore, his balls were starting to ache. Richard needed to fuck someone, anyone, as soon as possible.

Richard did briefly think of his wife Elaine. By far the hottest woman he'd ever fucked, and he was married to her. But that cold bitch didn't interest him anymore. It had been months since they had sex and Richard was in no doubt that it was her fault. She thought she was so much better than him, better educated, healthier, smarter. All of her family were the same. He knew they looked down on him. He knew they never wanted him to marry Elaine. But they were teenage sweethearts.

Richard was quite a catch in his youth, tall, dark, handsome. Star of the football team, he had his pick of the girls. After getting married he gave up the sport, and while still physically imposing he let himself go a little bit. Things were good for quite a while; they inherited a fine house from Elaine's Dad and the kids arrived. But looking back he now felt he had walked into a trap. He was now stuck living in the same locality as Elaine's family, living under their scrutiny. His job options were limited, he had no real friends.

Richard logged into his account on funsexmeets.com, a hookup website. He's had some meetups with women on the site, but it wasn't just any woman he was looking for tonight, he wanted a transgirl.

Unfortunately for Richard full time transsexual girls were few and far between, in his area at least. The transsexual section of the site included Crossdressers, and in truth, nearly everybody there could be described as such. He scrolled through profile pics without paying much heed of the bio. One by one he ruled them out, 'too hairy', 'too old', 'too fat', he thought to himself. Every now and then he would come across a hot looking girl but inevitably they were far away. He considered leaving the site to check for escort listings when he spotted her.

'Maria xx', 'how on earth could that be a guy?' Richard wondered. Long slender but shapely smooth legs under black stockings. Black lace panties with suspenders which contrasted beautifully with pale skin. A flat toned midriff beneath a black lace bra. Actual real looking cleavage. Straight black hair draped over narrow feminine shoulders. And best of all, the app said she was less than 10 miles away.

Richard had one hand stroking his cock as he flicked through Maria's images. Such tempting poses. On the floor, on the bed, stood in a doorway, each time pushing out her assets for full view while deliberately covering her face. 'Interested in women and Crossdressers only' her profile read. 'Fuck that' thought Richard, 'wait till she sees my cock that will turn her'. He snapped a picture of his rigid, precum leaking cock and sent it to Maria with just two words 'hey baby'.

* * * * *

It was Monday night and Mark was relieved to have had work to distract him from what had happened the previous Friday night with his sister. He was experiencing a cocktail of emotions, confusion, shame, guilt, pride. Yes, pride. In reaction to his initial shame, he filled with pride for acting on his instincts. Why should he and Elaine be ashamed? What business was it if anybody else? They had been close since the day he was born, they knew each other better than anyone else knew either of them, why couldn't they have this secret to themselves? He knew he could keep it buried; he was good at that.

This was of course just a coping mechanism, an attempt to justify his actions to himself. Guilt was the overriding emotion, guilt for cheating on his wife Jean. He felt some guilt for involving Elaine, but not for causing her to cheat on her husband - if you were to ask Mark, Richard was an obnoxious, selfish dickhead with whom he maintained the facade of a friendship for the sake of the family.

Some further mental gymnastics helped Mark shift some of the blame. As much as he loved Jean, this really was a reaction to their own frustrating bedroom situation. Their sex life was never hectic, but in the last few months things had really dried up. He always suspected that there was something Jean wasn't telling him, something that was holding her back.

Of course, Jean could simply blame Mark, ever since she found out about his interests. About two years ago Jean had walked in to find a bra, panties, stockings, and suspenders lying on the bed - she had no underwear like that. She confronted Mark and he had to admit he had a fetish for wearing women's clothes.

Initially Mark naively thought this was an opportunity to spice up things in the bedroom, he pleaded with Jean to let him dress with her. But she never agreed, indeed she was disgusted. She asked Mark to stop altogether but he knew that he couldn't give that commitment. Instead, he kept it hidden. Jean knew he still dressed but he kept it to himself. They got on with their lives and Mark detached his Crossdressing life completely from the rest of his life.

Mark could easily go weeks, months even, without thinking about dressing. But once it came into his mind, it became an obsession. Sometimes all it took was to see a woman in a dress that he like or a pair of shoes, or tights, and his mind would switch over to thinking what it would be like to wear it. This would evolve to needing to wear it and would grow and grow until he got the opportunity to dress. When in that mind frame Crossdressing could dominate his every thought. It was for all intents and purposes an addiction, and now the feeling was coming back to him again.

This time Mark was in no doubt as to what started his mind racing - it was his encounter with Elaine and her silken underwear. She had looked so sexy in that bra and panties, Mark needed to feel that for himself.

The call came at 7.30 that night. Jean sounded quite relaxed, but the story she was telling sounded quite distressing. Rebecca was really struggling. She had been physically abused and was in fear for her safety. Jean said that Rebecca had been much better since she arrived, but she still wanted to wait for another week to make sure she was okay. Mark offered to drive to Bangor at the weekend and stay with them, but Jean refused the idea. Rebecca, she said, did not want to see any man at the moment.

That night Mark was alone again in his bed. Crossdressing was taking over his thoughts. But with the guilt of what happened with Elaine already hanging over him, he resolved not to anything else that might upset his wife, Jean.

* * * * *

Thursday night and Richard was back on night shift. After going through his usual gambling and porn routines Richard was back on funsexmeets.com. He checked his messages. Still nothing back from Maria xx. 'Another stuck up bitch' he thought to himself.

* * * * *

It was Thursday night and Mark could not sleep. He was now in full Crossdressing obsession mode. It haunted every thought. Coupled with the fact that with Jean being away for so long he may never get such a great chance to dress again, the urge to dress was stronger than ever.

He needed to scratch the itch, so he allowed himself a little indulgence. Last year he had created an account in funsexmeets.com with the hope that he might get to share his Crossdressing with someone there. Mark knew he was good at Crossdressing. He found his own photographs sexy and used them as porn material. But he had a desire to be seen by others. Mark wasn't necessarily looking for sex. His main interest was having someone to show his cute outfits. If something resulted, well he was open minded.

Up to now, it had been a futile exercise. Women who liked Crossdressers appeared to be non-existent while the only other Crossdressers in his area were just hairy men in their wives' panties. As far as he was concerned Mark had no attraction to guys, however when he was in female mode, as Maria, he had fantasies of being submissive, of a guy worshiping his girly body. Having watched porn over the years he had even come around to the idea of sucking a guy off. Cocks look nice he thought. And in his horniest moments he fantasised about the ultimate act of submission, being assfucked like a cheap whore.

These really were just fantasies, because looking at images of guys generally did nothing for him. Mark liked women, he liked femininity. The idea of hairy sweaty rough guys did absolutely nothing for him, but still sometimes he played along. And anyway, despite having chatted with several people at length, Mark had never actually met anybody from this site.

Having checked to see what Crossdressers were online, there were none worth talking about, Mark checked the message log. It had been a while since he checked in but still, he was surprised to see 23 unread new messages. He went through them one by one. 6 were from other Crossdressers, of which only 2 were passable and they both lived in a different country. The other 17 were from guys despite the fact that his profile specifically stated that he didn't want messages from guys.

Of the 17 messages, 12 included unsolicited dick pics. 'What the fuck?' He thought. 'Does this ever work?'

Ashamed for half the human race having gained an insight to the absolute bullshit that women have to face every day, Mark nonetheless kept checking of the messages.

The second last message, from thundercock85, caught his eye. It was from a guy in the same area as him, and yes there was yet another dick pic. The message was not quite prize-winning poetry 'hey babe', without capitalisation or punctuation, was all that it said. The profile pic, in case you are wondering, was also a dick pic.

Mark then noticed that the last message was also from thundercock85 and was sent just hours ago: 'fuck you snooty bitch where are you why wont u answer me??!!?'

Mark recognising a Grade A bollocks when he saw one, decided to play along. 'Are you okay big guy?' was the response to draw him out. Mark noticed that thundercock85 was still logged on. The response was almost immediate.

'Hi sexy send me ur WhatsApp'

'Mmm how about we just chat?'

'Sure, you wanna meet?'

'Maybe sometime, do you want to exchange pics?'

***dick pic sent***

... and so on. Mark kept it up for a while. He had no interest in thundercock85, but he loved the attention all the same. It did get him thinking even more about dressing though. The urge was stronger.

* * * * *

Friday night. The one-week anniversary of the night with Elaine and Mark had now gone from being riddled with guilt to being ready to explore a completely different sexual experience.

Funsexmeets.com got plenty of attention again from Mark, and Maria xx was getting plenty too. Again, there were plenty of unread messages, five from thundercock alone, but it was the messages from other crossdressers that interested him. Two in particular; a classy older blonde lady called Talita, and a cute young brunette named Belinda.

Mark struck up dialogues with both girls; they shared crossdressing experiences, swapped pics, talked about turn-ons, and then, discussed meeting up.

The thoughts were now all consuming, Mark had to scratch the itch. And so, he decided on a plan. Saturday would be a fund day for Maria xx.

* * * * *

'She's gone silent again' Richard thought to himself as he stared at his phone within minutes of taking up his overnight workstation. "Bitch", he mumbled to himself.

* * * * *

Saturday morning and Mark was busy getting the clothes, the makeup and the wigs back out of the attic. he then spent over an hour sorting through each of the items and remembering how each of them made him feel when he wore them.

it was still early, but Mark was going to have a bath. it was very rare that Mark would have a bath but this evening he was going to shave, and the bath always made it easier.

Jean had a big selection of bath products, mostly presents received over the years. Mark took a couple of bath bombs and plopped them in. Jean wouldn't miss them. Mark stripped down, stepped into the bath and let his body disappear under the bubbles. After a few minutes relaxing he got to work with the razor and shaving foam. And it wasn't hard work. Mark's body hair was light, fair and sparse. Lifting one long feminine leg above the foam, he started shaving just above his narrow feet. Line by line the razor glided over his body, revealing the smooth skin below. He worked his way up to his thighs, then switched to the other leg. Mark rubbed his hands over his legs to inspect for missed hairs, a feeling that started to get him a little excited.

Mark removed what few hairs there were on his upper body, his underarms and finally he moved to his pubic area. Carefully Mark shaved down to the base of his cock, removed the hair on his scrotum, then delicately removed any hair between his ass cheeks. Now, fully smooth, Mark relaxed again for a little while before stepping out and drying off again. Finally, Mark rubbed lotion over his shaven body, and he was ready, now time to for his plan.

Mark got dressed, in his normal male clothes. He picked up the suitcase he had packed, left the house, get into his car and started to drive. Late on Friday night Mark had booked a room in a hotel about halfway between his house and Bangor. Not too far to travel, but far enough that he would not be meeting people he knew. He was determined to have a meet, hopefully with Talita, or Belinda, or perhaps both, and he was not going to take the risk of bringing them to his home. He was going to stay anonymous.

The Park Manor Hotel was busy 4 star just off the motorway. It was mainly known for hosting business conferences, and the professional but impersonal service made it ideal for anonymous hook-ups.

Mark had little fuss checking in and made his way to room 216. The first thing Mark did was check his funsexmeets account. No message from Talita or Belinda. He sent them each another message. Recognising that they might not come through for him Mark took the initiative and changed his status message to 'In hotel room, looking to meet'.

Now it was time to dress. Mark stripped fully naked and brought his clothes into the bathroom. He started with makeup. Mark didn't know much about makeup but knew enough to keep it simple. First, he applied a liquid foundation a little darker than his pale skin tone. Then he applied a lighter powder foundation. Already his face looked smoother with softer lines.

Next it was eye makeup. He applied a little dark eyeshadow - he was unsure how to use it properly - some eyeliner and thick dark mascara. Finally, Mark applied scarlet red lipstick, pursed together his lips and smiled at the results in the mirror.

Mark opened the bag in which he kept his lingerie. What to wear? Why not the black lace set? He loved the feeling of the lace panties as he pulled them up his long smooth legs. Next, he took out the silicone strapless 'NuBra', a device designed for women with strapless dresses but loved by crossdressers creating cleavage.

Mark had a slim fit figure but was far from perfect. Throughout his life he was embarrassed by one problem - moobs. perhaps it was a hormonal issue, but he couldn't shake the admittedly small fatty deposits on his chest. ever since he started dressing though he grew to love this feature of his body.

Mark placed the two adhesive silicone pads on the sides of his chest, just covering his nipples. Then he leant forward and pulled the two clasps together until they met and linked. Next, he pulled on the black lace underwire push up bra and stuffed in a couple of foam pads to round off the look.

Mark loved the classic sexy look, and suspenders were part of that. He fixed them on then took out the light black stockings. One at a time he slipped the stockings up his graceful long legs. As he stared down at the smooth sexy legs beneath him, he could not help but get aroused. If these were the legs of a girl, he met he would be turned on, how fortunate that they were his own. Fixing the stockings to the suspenders he could feel his bum cheeks push up. He loved how suspenders made his bum stick out.

Time to complete the look. The shoulder length black wig with the slight wave, yes that will do. After some combing and brushing, moving and fixing, it was on.

Turning to the full length mirror the transformation was complete. Hair resting on her shoulder, sexy dark eyelashes, full red lips, round 'natural' breasts, flat smooth stomach, pert juicy bum and long graceful sexy legs - this was Maria xx.

Time to check back into funsexmeets. The status change had garnered attention, 15 new messages. Maria looked longingly through the messages. She needed go share this sexy body with somebody. But there were no girls and nobody nearby.

Then another message appeared, surprise, surprise it was thundercock. 'Please baby Im ready, where are you?'

Maria looked back in the mirror. Yes, she was turned on by her appearance. Her cock was hardening inside her panties. She needed to be made feel like a real woman. Could she do it with a guy?

Maria looked back at thundercock's pictures. What would she even do with that thing? It did look quite nice. She thought what it might be like to suck it. But this guy was clearly a bit of a douche. What if he wants to fuck you? What if he tries to rape you?

Maria was ashamed of herself as the thought of being overpowered and penetrated gave her a flush of excitement. She took a deep breath, picked up the phone and sent a message; "Park Manor Hotel, Bangor Road, Room 216. Go straight to the room, door will be ajar".