"So you got a girl yet?"
Chris did not have an answer. The answer was "no" but to admit to that would seem like defeat. Chris had a good group of friends, built up over the years from old school friends, adding in work colleagues and their girlfriends along the way. In the past Chris' romantic failings had been a source of mirth, but no one mentioned it anymore, it became kind of sad. But Ashley wasn't to know, she had been away from the group for a while, and feeling her way back in. Chris didn't want to make her feel too bad, so he swallowed his pride, and answered the damn question.
"Nah, still living the bachelor dream."
He smiled, hoping the emptiness he felt wasn't obvious. Ashley laughed, and he was able to relax, knowing he had got away with it. He didn't want to embarrass himself in front of Ashley. She was the most beautiful of his friend's ex-girlfriends. How they managed to find, and then date such attractive women he would never know. Ashley had short blonde hair, big eyes and a dazzling smile, meaning to make her laugh was enough to melt him every time. The fact that her body was, and continued to be, something of an enigma to him, only added to his anxiety. Her slim physique, amble bosom, yet wide flared hips, constantly called to him. Today in her skin tight blue jeans, his eyes were drawn to her ass at every possible opportunity.
Yet Ashley was just another unattainable women in his social group. Aside from the fact that she was too attractive to stoop to his level, she was also his friend's ex-girlfriend. Although that didn't stop any of the others in the past. Tonight they had met at a local bar, just for a few drinks and to catch up. There was talk of heading on to somewhere louder, but Chris wasn't feeling all that up to it. The couple of drinks he'd sunk had yet to have any effect, other than to make him feel bloated. Chris made an effort to be social, he found it difficult, but he used the time speaking to the girls in the group to practice speaking to attractive women. He had fun conversations with both Lea and Hailee, who much like Ashley, seemed far too attractive and cool to tolerate his group of friends.
The night moved along, but they stayed in the bar, much to Chris' relief. The drink was having some effect, and somehow he again found himself in conversation with Ashley.
"So no luck then?"
"Not since we last spoke."
Ashley was sitting uncomfortably close. The bar had a home away from home aesthetic, but the couch they were on suddenly felt a little tight. Chris wasn't a big guy, but he wasn't slim, and for some reason Ashley seemed to be pressing against him. She seemed a little tipsy, but nothing more than a tired, slightly buzzed drunk.
"So, you're still, you know?"
Chris cringed. For the period whilst Ashley had been a constant in the group, Chris had been rather liberal with the information regarding his lack of a sex life. For some reason he got a buzz from telling people he was a virgin. Maybe it was the sympathy, maybe it was just the attention. It was unusual for a man in his mid twenties to be in this predicament.
"Afraid so," Chris replied, trying not to commit any further to this line of questioning.
"Why not just get a plane to Amsterdam and get it out the way?"
Once again Chris cringed, even the thought of this scenario put him on edge, and he told her as much. Ashley went a little quiet after that, and they sat awkwardly in silence for several minutes. At least, it was awkward for Chris, as he sat sipping another pint that wouldn't go down. Ashley spoke up again.
"I could, you know, as a friend?"
She didn't finish her sentence. "You know what?" Chris thought, "Give advice, find a girl... find a prostitute?"
"Well I mean, I know what I'm doing, that's the awkward part right now right? You hook up with a woman in her twenties, and she expects you to know what you're doing."
Chris' heart was starting to pick up speed, where the fuck was this going?
"I know that you're inexperienced, and wouldn't expect anything other than what I teach you. Just, as a favour to a friend. I'm not seeing anyone, so we spent the night, I give you the basics, and you take it from there."
Chris still hadn't spoken, on top of being terrified he had two thoughts. One, "what was happening?" and two, "where is the nearest bedroom?"
"You're joking right?" He finally managed to splutter. "I mean, you can't be serious?"
"Why not?" Ashley nonchalantly shot back. "Look it's just sex. I'll probably end up in bed with someone over the next couple of weeks, it might as well be someone I trust, and I'll be doing you a solid at the same time."
"A solid?" Chris went into automatically deflect by joking mode. Ashley didn't react.
"Look, it's there on the table as an option, if you're interested?"
Chris went quiet again, his mouth was dry. Now his pint went down with ease.
"You're not messing with me? You're actually offering? How would we, you know? Go about it?"
Ashley thought for a moment.
"Tonight's no good as we've both been drinking. I need you alert. When did you last masturbate?"
Chris was taken aback again, at some point this conversation had to stop surprising him.
"Uhh, yesterday," he eventually replied.
"Okay, that's good. Wait, how often do you get yourself off?"
"Every couple of days I guess?"
"Right, and do you think you could get it up again?"
To Chris this was getting surreal. It was a whole other world he only witnessed when it played out on his computer screen.
"Probably, I don't normally try again. There's no need."
"No I guess not." Ashley was back in thought. "You free tomorrow night, or the night after? Tomorrow is better."
Chris confirmed he could make the following night. He tried not to sound too keen, but his voice faded to a dry gasp as he finished his sentence.
"Okay, you head to my place. My roommates will probably be out as it's a Saturday night. I'll send you a message tomorrow to let you know if they are out. But until then, do not masturbate! Gives us more to work with."
Chris returned to the stunned silence, his mind torn between utter confusion, and the raging hard on tightly packed into his jeans.
"Okay, and you message me?"
Ashley grinned. "Yeah, and I'll supply the condoms. Not that I don't trust you, but again, I know what I'm doing."
Chris nodded.
"Okay, should be fun. I have to pee," and with that Ashley stood up and walked away. Chris watched her ass sway in her tight blue jeans. He was certain this was a joke, there was no way he would be given access to that heavenly body. His cock cried out at the sight, flexing, struggling for freedom. Chris moved and sat forward, legs spread, his arms on his knees. What the fuck had just happened?
Before Ashley could return, Chris was in a taxi and on the way home, trying to clear his head. When he got in, he found a text from Ashley, it read:
"Didn't see you before you left. Don't forget, don't wank!"
The effect of the alcohol was gone, suddenly Chris' world was upside down. He struggled to sleep that night, as his cock continued to cry out for attention.
***********
For Chris, the following morning and afternoon were a blur. He checked his phone every five minutes to see if Ashley had sent a message to apologise or back out. He found it difficult to occupy himself, so he went for a run, then played video games. Shortly before 4pm, he received a text.
"Hi Chris! Hows the hangover? The flat is empty, so come over say 8?"
Quickly his heart was racing, and his hands shook so much he could barely type his response.
"Feel OK. 8 sounds great, you sure?"
He forced himself to send the text before backing out. He quickly received a response.
"See you at 8."
Over the following hours Chris tried, and failed, to eat something. Then took a vigorous shower, bath, shower combo, then made sure everything was trim, deodorised, and presentable. He tried to do a little extra research online, but this didn't help for two reasons. It made him feel terrified and horny.
As Chris got in his car, you would not believe he was about to get laid. He was terrified, job interview, first date level terrified. As Ashley buzzed him up and he stood in the elevator, the whole building seemed to sway. He knew he had to get a grip, he realised this did seem to be happening.
As Chris stepped up to Ashley's front door, he noticed it was open, so he stepped inside and called out. Immediately he could smell burning candles, and noticed the lights were dim. Ashley called from the kitchen, offering wine. Chris accepted, anything that might make him relax, then Ashley stepped out in a cute red dress, holding two glasses. Ashley didn't need to dress provocatively, this was not a seduction, Chris did not need to be convinced or aroused any further.
She handed him a glass before adding with a laugh "looks like you need this."
Chris nervously laughed along, then they sat on opposite ends of the couch. Ashley started talking about everything he'd missed after he abruptly left the night before. Turns out one of the guys had a few too many, and got thrown out. Which was pretty surprising, as they knew all the bar staff, and generally got on pretty well. Chris focused on awkwardly laughing at the correct moments, but every time he started to relax, the evenings ulterior motives returned to his thoughts. When the conversation crumbled again, Ashley put her glass down, and the lesson began.
