The Gift Ch. 01

Steve couldnt recall when it all started.

He always admired how sexy his girlfriends looked in their lingerie and loved the feel of nylon legs rubbing against his skin.

He also had a thing for older mature women rather than younger, it was something about the confidence they exuded and the style of their clothes that he found mesmerizing.

He was on several swinger sites and had enjoyed several hookups but was becoming bored with these somewhat vanilla experiences and so he started to browse cross dressers. Most were pretty awful, hairy panty wearers with no effort being made to look remotely feminine. Some however clearly did put a lot of effort into their appearance and looked very convincing. He loved the variety of their outfits, hair, makeup and of course the more explicit photos of them servicing male admirers.

Steve had never been with a man but liked the idea of being an object of desire and so decided he would spice up his life a little and create an alto ego and experiment with crossdressing.

He ordered a few items online and eagerly unpacked them when they arrived a few days later. Being naturally smooth and of slight build Steve was able to wear a short denim mini skirt and white knee length boots. He teamed this with a white low cut blouse exposing a pink padded bra that had a matching thong.

His hair was blonde and shoulder length so he simply brushed it forwards to cover his face and then looked in the mirror.

He was quite pleased with the results and so took a few photos and uploaded them to his new profile.

The next day Steve was surprised by the number of messages he received. Mainly from men describing what they wanted to do to him, some pleasant others less so.

However one caught his attention as it was from a attractive looking mature woman going by the username xxx who simply asked "Do you want to look like me?"

Intrigued Steve replied "Yes i would love to as you look amazing". Cheryl messaged saying that she could help complete his transformation and if he was genuinely interested then they could meet to discuss over a drink as they were within 10-15 miles of each other according to the site.

Excited and intrigued in equal measures Steve jumped at the opportunity and agreed to meet at a local bar that was about the same distance for them both.

The following evening Steve walked into the bar scanning the tables when he saw Cheryl sitting alone at a corner table.

"Cheryl?" he enquired.

"Yes Steve, pleased to meet you, take a seat".

Steve sat down and couldnt help gazing at Cheryls breasts which were enormous and her summer dress was fighting a losing battle to hold them in place.

"Eyes up here young man. Now lets down to business".

"Business?" Steve said perplexed by the statement.

"Yes. I said I can complete your transformation and give you a look like mine. However I will require a favour once you're happy with the results. Is that okay?"

"Um, yes I guess so..." Steve began as was about to ask what exactly she had in mind when Cheryl interrupted.

"Good. Now lets make a start. Join me in the ladies, its down that corridor. Theres no one in there at the moment but we need to be quick and discreet".

Cheryl got up first and headed down the corridor having picked up a small travel bag along with her handbag.

Steve left it a few moments then followed. Nervously he entered and saw

Cheryl in one of the cubicles. She beckond him over and closed the door.

"Okay, now lets make a start."

Cheryl reached into her bag and proceeded to expertly apply foundation, eye shadow, mascara, lip gloss to Steve's face.

Once completed she smiled. "Perfect. Now get out of those clothes and put these on. They should fit."

Steve looked at the ensemble. It was identical to what Cheryl was wearing, plus a wig that matched her flowing dark hair and a pair of heels that were big enough for Steve's size 7 feet.

Cheryl carefully folded Steve's discarded clothes into her bag and helped him get into the dress and sort the wig.

"Okay, lets take a look shall we?"

Cheryl opened the cubicle door and ushered Steve over to the mirror.

When he looked he was stunned. He looked almost identical to Cheryl. "Thats incredible. How on earth..."

The door opened and in walked a lady looking worse for wear. She barely glanced at them befoe heading into a cubicle and proceeded to throw up.

"Delightful" remarked Cheryl, "Right are you ready for your first test?"

"Test? What test?" asked Steve nervously.

"I've been flirting with a guy in the bar. Hes no oil painting but he's as horny as hell and also had quite a few beers so will be perfect for this."

"Perfect for what?" Steve was beginning to wonder where this was going.

"I'm going to go back into the bar and offer the guy a blow job in here. I will ask him to follow me in but I will be in the next cubicle and it will be you who he sees sitting on the seat with your door open. Don't speak just wave him over and deliver what he is expecting."

The cubicle door opened and the lady who had now finished throwing up walked to the sinks and took a paper towel ti wipe her face. She quizzically looked at them both "Twins?" she offered.

"Yes dear" replied Cheryl.

"Thank god. Thought i was seeing double but glad I'm not that drunk". With that she left returning to the bar.

Steve was stunned. "But I'm not gay. I've never been with a man before..."

"Well hun. I've got news for you. You're currently in the ladies, fully made up and wearing womans clothes. So you can protest but the reality is you know you want this so now is the time to take that first step"

With that Cheryl left the ladies and headed back to the bar.

Steve's head was spinning. How did he end up here like this?!

He looked in the mirror again and was still taken aback at how good he looked. He felt a stirring in his panties and realised he was actually very turned on.

The door opened suddenly jolting Steve back into the present. Cheryl went straight into the cubicle next to the one they had used to transform Steve. "He is on his way. I suggest you make a decision very quickly!"

Steve didn't think and instinctively went to his cubicle and sat down. The door opened and in walked a tall slightly rough looking man in his late twenties clearly feeling the effects of several pints.

He scanned around and then smiled as he saw Steve. Walking over he said "There you are you dirty little prick tease. I hope you're not going to disappoint."

Steve didnt say a word but put his finger to his lips and gestured for the man to close the cubicle door behind him.

Once closed Steve took a deep breath and unbuttoned the jeans of his drunken occupant and pulled them down and his briefs to reveal a semi errect dick that was already dripping presumably from whatever Cheryl had been teasing him with.

Steve was on autopilot as he lifted it towards his lips and then looked up at him as he slid his mouth over the head and down the thick long staff. The man groaned as Steve began to slowly pump his head up and down, working the shaft with his hands whilst concentrating his lips and tongue on the bulbous head.

It was clearly working judging by the sounds coming from his mouth and Steve could feel the man beginning to twitch with each swirl of his tongue.

As the noises grew ever louder Steve could sense his first blow job was about to come to an end and so tried to move his mouth away.

"No you don't you dirty slut. You said you'd swallow and so that's what you're going to do". With that Steve felt two powerful hands hold his head in place and he knew he had no escape.

A loud groan was accompanied by the first spurt of cum filling Steve's mouth. Another spurt erupted and Steve had to swallow to prevent the cum from dripping down his face and over his dress.

Two more bursts came in quick succession before he felt the dick soften.

"God that was great Cheryl. Best one you've given me for sometime."

With that the man pulled up his pants and jeans before heading back out to the bar.

Steve wiped his chin and looked up to see Cheryl smiling as she peered over the top.

"Well done. You've passed that with flying colours. If you can fool Pete then I'm confident you'll be able to fulfill the favour you owe me".

"What? Wasn't that it?!" Steve said incredulously.

"Honey that was just a test. Now get cleaned up as we're running late."

To be continued...