Crossdressing and the Delivery man

Working from home had its perks, Chris thought, as he heard his parents leave for the day, heading to the specialist hospital for a regular check-up. He'd got the house to himself for the day, and what was best was he'd hardly got any meetings.

He focused on his work for part of the morning, getting what he needed to done, before his focus began to wane. Sighing, giving in to the inevitable, he locked his PC.

If asked, he wasn't really sure how it started. Over time he'd found that regular porn got dull, and his thoughts turned to gay porn. He'd become more and more intrigued what it would be like to be fucked by another guy, and so his fantasies turned in that direction.

Even that seemed to pale, and the next step seemed to take him into cross dressing. Still living at home, he'd started by trying on his mother's clothes, feeling a thrill as he slipped on a blouse or skirt when they were out. The global health crisis had curtailed these opportunities, but the easing of lockdown was beginning to give himself more opportunities.

Chris was blessed with a slender frame, he kept himself fit, but not to the extent he piled on the muscles. His naturally slim torso and waist gave him a vaguely feminine build. He was also blessed with a lack of body hair. Whilst some of his friends had thick hair all over their body, Chris's was almost smooth. Even his face barely grew any stubble, his shaving routine was once a week to keep the low-level growth in check. To complete the lack of hair, he kept his brown hair cut short.

It had been one time when home alone he found an old make up set of his mother. Using some hastily found you tube videos; he began to practice applying the foundation and eye shadow to his face until he became quite proficient at it. He also discovered several old lipsticks in a draw that were not being used, finding his favourite being a shimmering peach colour that went well with the foundation.

Walking across from his room to his parents, he opened the wardrobe, looking for an outfit to put on for the day. Firstly, he pulled out a long-sleeved satin blouse, baby blue in colour that had a ribbon trailing from the neckline. He then pulled out a calf length navy skirt with buttons running down the front. To complete the outfit, he found some beige lacy heeled sandals.

Heading back to his room, he quickly shed his clothes, and stood naked before his mirror. His cock was already hard, but he resisted playing with it. Instead, he opened a draw and pulled out a pair of black tights, with raised criss-cross patterns. These were an old pair he'd found when first experimenting, and there were the odd ladder and holes appearing. Sitting on his bed, he slowly rolled them up his legs, enjoying the feel of the soft material on his legs.

He decided against any other underwear, and so pulled on the skirt, and then buttoned up the blouse. He took in his reflection, satisfied with what he saw. His chest wasn't trim, he always joked that his breasts were bigger than some women, and he could make out the shape of them, nipples pressing against the blouse.

Deciding to go the whole hog, he took out the makeup kit and sorted his face. He'd shaved earlier in advance, and so his smooth face was soon made up. He took the peach lipstick, applying it liberally to his lips, and then finished the look with blue eye shadow. Finally, he took a wig, which had started life as a prop for an 80s fancy dress party, and put it in place. Whilst it might not pass muster on close inspection, the wig fell fairly naturally around his face, framing it in with blonde locks.

Looking in the mirror, he saw a vision of a young business lady, sophisticated blouse and skirt, rather than a young man. Satisfied, and feeling not just a little turned on, he sat back down at his desk. The thrill of being dressed like this whilst talking to people on chat was getting him more turned on, and he could start to feel pre-cum oozing from his dick. He continued to resist the urge to play with himself even when he had to take a voice call from a colleague.

It was early afternoon, and Chris was thinking he would soon have to change back to avoid being caught when his parents returned. He'd been idly starting out of the window at the glorious weather for a few minutes, lost in an erotic daydream, when suddenly the doorbell went.

Shocked, he panicked, his first thought to ignore it and let them come back later. But then he remembered his parents telling him there was going to be an urgent delivery of medical equipment for his mother that needed to be signed for.

Sighing, he realised he couldn't ignore it, and there wasn't time to change. He got up, and slowly walked downstairs to the front door, his heart pounding and blood rushing to his cheeks. At the bottom of the stairs, he could make out the silhouette of the courier outside.

Taking a deep breath, he reached out and opened the door. He took another as the warmth of the day hit him, and then a third as his eyes took in the courier before him.

The weather had obviously driven what the man was wearing. He was clad purely in a vest top, revealing well-tanned and powerfully muscled arms. His legs were similarly bare, the short cargo shorts hiding very little of his long-tanned legs. Chris realised he was unconsciously checking the guy out, and so moved his eyes back to meet the gaze of the other man, who was patiently waiting. He found himself looking into deep brown eyes, framed in an equally tanned face, hair shaved really short.

"Hi," he finally managed to say. People had always said he was softly spoken, but this was even more so as he struggled to speak in front of such a handsome guy. As he looked, he watched a bead of sweat roll down the side of the man's face, and drip down onto his t-shirt.

"Hi," the guy smiled back, his smile making his face warm and inviting. "I need your signature for this," he said, pointing the package by the door.

"Of course," Chris said, broken from the spell he was in, and reached for the machine, signing his name before handing it back.

What followed was a moment of awkward silence as they both stood there. Was it Chris's imagination, or was the guy looking him over?

"Sure, is a hot one today," the guy said, wiping the sweat from his brow with arm strong forearm. making no effort to leave.

"It is, you look hot" Chris replied, struggling to know what to say, "I mean, warm, erm, did you want a drink or something?"

"Thanks, that would be great," the guy said, laughing at Chris's state, following Chris into the kitchen, out from the oppressive heat, "I'm Greg by the way.

"Chris, I mean, Christine," Chris replied, reaching for two glasses. He filled them up with juice and then turned to hand one to Greg. This time, he saw that Greg really was checking him out, his gaze returning from where it had been looking at his legs and ass.

"Hopefully this will cool you off," he said, stepping close to Greg as he put it on the counter, brushing his hand across the man's arm as he did, making it clear he was interesting.

"Not sure I want to cool down," Greg said, taking the other drink from Chris's hand and putting it down before pulling him in close.

Their lips met, and Chris automatically opened his mouth, letting Greg's tongue invade his mouth. The man's stubble rubbed against his face as their mouths moved in time, their tongues dancing in their mouths. Chris felt Greg's hands running down his sides and un-tucking the blouse from the skirt, before reaching under and caressing his skin.

Moaning into the kiss, Chris revelled in the feel of the strong hands on his skin, as they traced upwards towards his chest. He felt one hand reach his nipple, the fingers gently teasing and caressing it before moving to the other.

"No bra," Greg murmured, "does someone want to be a bad girl?"

"Always," Chris breathed, feeling heady from the mans' touch. The fingers moved off his nipples and started to move downwards. Chris knew where they were heading, and with a hint of panic knew the game would be up as soon as they reached under the waistline.

He stepped back quickly, breaking their kiss, forcing Greg to pull his hands back from under his blouse. He briefly looked in the kitchen mirror, seeing his face which was covered in smudged lipstick from their kiss, no longer the sophisticated business women, now just a hussy who wanted more.

Without thinking he stepped back closer again, and knelt to the floor. With heart in mouth, he reached out and caressed Greg's growing member through the material of the shorts. Taking a deep breath he undid the shorts, tugging them and the boxers down and out of the way.

Greg's cock spring free, and whilst not massive, from where Chris was looking, at eye level it seemed big enough.

"Suck it," Greg whispered as Chris sat mesmerized by it. Hesitantly, taking it in one hand he slowly closed his smudged lips around the tip, feeling the warmth of the cock in his mouth. It tasted musky, the sweat of Greg's body giving it a manly smell and Chris slowly took more into his mouth. He managed about half the length before it hit the back of his mouth and he felt himself gagging. Pulling back, he took the cock out of his mouth, trailing saliva onto his chin.

"You can manage more than that," Greg said, and as Chris put it back into his mouth, he felt Greg's hands on the back of his head guiding him forward. He reached the same point as last time, and began to pull back, but Greg's hands were insistent and slowly, but surely forced more of his dick into Chris's mouth.

Chris thought he couldn't take it, but slowly he got used to the dick in his mouth, and the sensation of gagging receded. The pressure from Greg's hands on his head reduced, and he slowly took the dick out of his mouth, before taking it all back in again.

He was beginning to enjoy the sensation, having his mouth filled with dick, and let his tongue caress the shaft as it moved in and out of his mouth. He continued to bob up and down the shaft, enjoying it, when he felt Greg's hands on his head once more. This time they held his head in place, and rather than him sucking Greg's dick, he felt the other man slowly thrust his hips and back and forth, now fucking his mouth.

Greg started slowly, at the pace Chris has been sucking, before slowly increasing the pace of his thrusts. Chris's mouth was aching now as it stayed constantly open, allowing Greg to fuck it relentlessly. Each thrust forced Greg's crotch into Chris's face, the sweat that was dripping down rubbing across Chris's cheeks.

Chris was lost to everything but Greg's dick, s it was a shock when Greg shuddered, and with one final thrust began to cum. The warm goo splattered into Chris's throat, causing him to splutter, before Greg pulled his cock out of Chris's mouth and sprayed the last of his cum over Chris's cheeks, smearing it first one side then the other as it oozed out.

Chocking, Chris swallowed the cum, chocking on the bitter taste, as he looked up at the muscular man standing above him. Greg's dick was slowly shrinking now, but Chris didn't care. Shakily, he got up, and stood leaning against the kitchen counter.

"That's one hell of a mouth you got there," Greg said huskily, "let's see if that pussy of yours is as good?"

"No," Chris squealed, not wanting to give the game away. Greg looked disappointed at his reaction, a feeling that Chris mirrored, and so he added, "I'm not on any protection, can't risk anything."

"Ass it is then," Greg smiled, eyeing Chris's peachy ass through the skirt.

Stepping close he kissed Chris again, before reaching down to fondle Chris's ass. Smiling, Chris spun around so that Greg wouldn't see his erection, before allowing the other man to tug the skirt down over his tight, revealing his ass.

"Mm," Greg murmured, his hands roving over the satin class globes. Without warning he took the tights in both hands and ripped a hole in them, too impatient to pull them down.

Chris didn't care, he just wanted to be fucked by this hunk of a man. Greg stepped up close behind him, and with one hand started to massage Chris's ass, first a finger and then a thumb entering his asshole.

Greg was close up against Chris, trailing kisses on his neck as his fingers continued to widen and prepare Chris for what was to come. Chris could feel Greg's dick against his ass, already hardening again. His own dick was rock hard, leaking pre-cum, staining the front of his now ruined tights.

He ground his ass back against Greg's fingers, urge and wanting overtaking any rationality.

"Take me," he murmured, wanting to feel Greg's dick buried in his ass. He bent forward, his torso now resting on the counter top, his ass pointing upwards for Greg's attention.

Greg removed his finger from Chris's ass, and stepped closer, his dick now rubbing against Chris's hole. Pushing forward the hard cock forced its way into Chris's ass, causing him to moan in pleasurable pain. Slowly, he continued to force his dick up into Chris's ass.

"God you're tight," Greg whispered as his dick was finally impaled on Chris's ass.

Chris couldn't reply, he was panting as if he'd run a race, never had he felt so fulfilled.

Greg slowly removed his dick, and then thrust froward again, this time sliding in easier as Chris's ass accommodated the invasion. Satisfied that the ass could take it, he slowly increased his rhythm, pulling out almost entirely before slamming back into Chris's ass, his crotch slapping into Chris's ass with each thrust, pushing the other man hard against the counter top.

"Fuck," Chris moaned with pleasure as he felt himself being split in two, Greg's dick forcing against his prostate with every thrust, pushing him close and closer to his own orgasm. Greg's hands reached around Chris's waist, and with every thrust now pulled him back onto his dick, feeling to Chris as if he was thrusting ever deeper into him.

This was too much for Chris, and felt himself building to orgasm. With both hands resting on the counter for balance he wasn't able to grab his dick, but there was no need, with one particularly forceful slam of Greg's dick he felt himself coming, more powerfully and harder than he'd come before.

"Argghhh" he cried at full voice and his cum spurted forth in the tights, leaking down his legs and staining the material.

Greg continued to thrust forward, his breath coming in short pants as he continued to fuck Chris hard. Chris was lost in a post orgasm haze, the pleasure coursing through his body. He felt Greg speed up, his thrusts now short, sharp movements, and before he could realise what was happening, felt Greg tense. With one final thrust he pulled Chris deep onto his cock, and then came, spurting cum deep inside Chris. Chris felt wave after wave fill his ass up, before it died away. He felt Greg pull out of his ass, feeling empty without it stuck deep inside him. He was panting for breath, unable to move off the counter top, and so heard rather than saw Greg pulling his boxers and shorts back up, dressing himself once more.

"That's one fine ass," Greg said, "Maybe I'll have to deliver something here again." And with that, he stepped out of the kitchen, out of the hallway and back to his car.

Chris couldn't believe what had happened. For a minute or two he just lay there panting on the counter, before he felt able to stand. He looked down at his body, seeing the cum smeared all over the crotch of the tights, dribbles that had escaped run down his leg. Looking up at the mirror once more he saw his face was ruined. His mouth puffy from kissing, the lipstick smeared all over. The foundation was smeared everywhere, the sweat and the cum plastered all over his face. Amazingly the wig had stayed in place, a strand of cum stuck to one of the locks. He slowly peeled the blouse off, and held it up, seeing it was soaked with sweat, both his and Greg's and certainly needed washing before his parents returned.

Sighing with pleasure, he stated to peel the tights off, and made to throw them away, before deciding to keep them, cum stain and all, as a memento of the day.