tagFirst TimeHell... What are Friends For?

Hell... What are Friends For?

byA_Non_A_Moose©

"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.

"Okay, first off, you can't be this nervous! You need to be confident!"

"I'm not confident."

"No one is, sex can be weird, especially the first time with a new partner. They all fit differently, there's no standard procedure."

With no warning Ashley lifted up her dress and stood in her underwear. Once again, nothing sexy, just a white bra and matching knickers. She did a turn to give Chris a good look at her gorgeous body. Chris' eyes zoned in on the slightest hint of camel toe, before his eyes darted back to her face.

"Now you," Ashley commanded matter of factly.

Chris carefully put down his glass, then began unbuttoning his shirt. He had been a large guy for most of his life, but had recently been trying to get in shape. There was a long way to go, but he had made progress. Ashley was pleasantly surprised when he revealed his top half. She knew if only he had more confidence, he would have no trouble finding a partner.

Chris took off his shoes and socks, then his trousers. All that were left were his boxers. As he placed his clothes to the side, he heard a snap and a rustle, then looked back to see Ashley had removed her bra. Her breasts seemed to be magically perky, with small, pink nipples. She had that smile again, as her fingers locked into her knickers.

"Same time, okay?"

Quickly Chris remembered something he had to mention.

"Hold on, just a second. There's something I need to tell you."

"Unshaved? Yeah I know I can tell," Ashley laughed.

"No, no, that as well, but. My cock, it's not small, but, it's kind of, bent."

Ashley tried not to laugh, most guys had a slight curve, she had never been with a guy who had a perfectly straight dick.

"Don't worry, that's normal," she was trying not to laugh. He seemed so concerned.

Chris' hands moved to the waistband of his boxer shorts, then Ashley nodded, and they revealed themselves to each other.

Chris stared at the small triangle that formed in the centre of her beautifully curved hips. Ashley stood upright with her legs together. His eyes didn't move from her sex, until she took a step forward, and bent down to get a closer look at his dick.

"Wow! It's big, but I get what you mean. That's a pretty odd shape."

Not only did Chris' cock bend upwards, but it also veered to the left. Ashley quickly took it in her hand, and tested the flexibility.

"Don't worry," she reassured him. "We can make this work."

Chris didn't hear her. The touch of her hands on his cock had sent him into overdrive, and he was either going to cum, or collapse. Ashley let go and sat him down.

"Okay, I'm getting a picture of what we're dealing with. First, you need to relax. Just sit back on the couch, and I'll take it from here. Don't worry about holding back, this is part of the plan."

Chris sat back, his breaths had never been so ragged. Ashley spread his legs and slipped to the floor. She reached back to a few supplies, grabbed a bottle of lube, and spread a large amount over her hands. Then, with what seemed like a forensic precision, she took hold of his dick, and transferred the sticky substance to his shaft.

What followed were (up to that moment) the most intense few minutes of Chris' life. Ashley expertly stroked him, and used tremendous skill to hold him back from full release. If Chris could have focused, he would have wondered quite how she was keeping him from exploding. Instead, he thought he had the hang of this, and was holding on of his own accord. That thought didn't last long, as Ashley pulled down on his cock, exposing the head, and took it in her mouth. Her lips hooked around the ridge as she sucked and licked the opening slit. Within seconds the base of his cock pulsed, and he passed the point of no return. Ashley had removed him from her mouth, and her hand stroked his stricken member, her thumb grazing over the underside, stimulating his frenulum. Chris' hips shuddered and writhed, then a large blast of cum shot into the air. Ashley slowed down and pulled down on his cock as a quick volley of cum burst forth, showering them both. She couldn't help but smile as her good friend groaned and shuddered at her touch. As the contractions slowed she resumed a gentle stroke, causing another quick burst, then Chris was spent.

As Chris regained his composure, he became self conscious of the fact that a woman had seen him cum for the first time, and not just any woman, but Ashley, his very attractive friend.

"Thank you," he gasped.

Ashley smiled, "Hell, what are friends for? Always happy to give a helping hand." She held up her hand and giggled, his semen was slowly dripping from her fingers. She observed it for a second, then stood up and walked to the bathroom to clean up. She pointed Chris to a pack of wipes on the side, but he was too busy watching her butt sway as she left the room. He knew then he would have no trouble going again.

When Ashley returned she looked again at Chris' semi-erect cock, then lay on the bed.

"It is a strange shape, I want to make sure I'm ready when you come at me with that thing. Can you grab my vibe from over there?" Ashley pointed to a small chest of drawers on the other side of the room. Chris did as told and opened the top draw. Inside he found her underwear. There were various styles, cute panties, lingerie, thongs, french knickers. It stopped him in his tracks.

Ashley grew impatient, "Oh get over it and dig in, it's there somewhere."

Chris reached in, feeling the soft fabrics rub against his hands. Then he felt something solid and pulled out a cute, purple vibrator.

"That's it" Ashley shouted, "bring it here!"

Chris was like a puppy on a leash as he walked over, so Ashley snatched the toy from his grasp, then quickly found the correct setting. Chris watched as she lay back and spread her legs, displaying her immaculately shaved pussy. Ashley ran her fingers over the outer lips, then fired up the device. She started gently hovering over her nipples, as her right hand nestled between her legs. Over the next minute or so, she switched between breasts, then called Chris over.

"Just play with my tits for a bit, focus on the nipples. Don't mash them into my chest, try and tease them, get a feel."

Chris didn't need persuading, he clambered over to her side, his cock was once again rock hard, and bounced as he moved. As he took one of her beautiful breasts into his grasp, he marvelled at their soft pertness. Chris had never got to second base before, and now he had Ashley's perfect bosom in his hands, he was a little lost.

"Gently rotate them a bit, and squeeze the nipples every now and then."

Chris did as she said, Ashley smiled and closed her eyes, then lowered the vibe to her pussy. Chris reached over with his right hand and began working on the other breast.

"One at a time sweetie, less is more."

Chris took note and removed his left hand, preferring to carry on with the globe he had yet to explore. Like before Chris gently rubbed and felt the flesh between his fingers. Ashley now had the vibrator buzzing over her pussy, occasionally grazing her clit. Chris felt her nipple harden against his hand. Feeling adventurous, he took it between his fingers and squeezed. Ashley smiled and moaned, she liked it. Chris grew more adventurous and switched back to his left hand, squeezed her other nipple, and over excitedly grabbed hold of her boob.

"Ow" she squealed, "remember, less is more!" Chris snatched his hand back in embarrassment.

"I need you down here now anyway, come on!"

Chris moved between her legs, barely remembering to breathe. Ashley's right hand continued to work on her breasts, the left holding the vibrator in place. Now Chris could see how wet she was, and he longed to bury himself between those glistening pink lips.

"Rub your hands over my thighs" Ashley ordered, "Now lean over me and kiss my neck."

Chris moved to kiss her neck, his warm, rock hard cock brushed against her hip causing the tremors from the vibrator to briefly buzz his balls. Chris did as she said, and kissed her neck gently, tasting her perfume, and a slight hint of sweat.

"Harder!"

Chris kissed her neck again, his left hand grabbing hold of her thigh.

"More!"

Chris sensed she was close, and began passionately kissing her neck, whilst rubbing her gorgeous thighs. Suddenly Ashley grabbed his left hand, pointed his index and middle fingers, and thrust them into her pussy.

"With your fingers, with your fingers" she gasped.

Chris could barely contain himself. It felt so warm, so wonderful, he needed his cock inside her.

"Faster" she cried, it was her last command. Seconds later Ashley's eyes rolled into the back of her head, the vibe buried into her clit, and Chris enthusiastically fingered her opening. Her back arched off the bedsheets, then she began to shake and gasp with each shudder.

As Ashley came down, she threw the vibrator aside, pulled Chris fingers from inside her, and positioned herself over his aching cock.

"How are you feeling? You close?" Chris shrugged, so she grabbed his dick. "Feels pretty close to me, we'll try it with me on top, but considering your shape, you may need to fuck me from behind."

Chris nodded, then Ashley raised her hips, and lowered herself onto his swollen member. As expected, it wasn't the smoothest fit, but her wetness helped. Chris lay back in stunned silence as his beautiful friend enveloped his cock in her warm pussy.

"You okay?" He nodded. "Feel good?" He nodded again with a pained expression, causing Ashley to let out a wicked laugh. She felt bad, he really didn't feel good inside her, it felt awkward. She tried grinding her hips, but that didn't help, and only took Chris closer to the edge. She tried simply running herself up and down his cock, but again it clumsily edged Chris towards orgasm.

"Okay," she stood up. "We'll have to try from behind, sorry."

Chris didn't care, as long as he was inside her. They moved into position, and Ashley aimed her ass at his crotch.

"You're in charge now okay. Cum inside me if you want, it's okay, I'm safe. Or cum on my ass, just try to avoid my hair."

Chris hadn't even thought about where he would finish, or the lack of a condom. Although he barely gave it another thought as he rubbed the head of his cock over Ashley's outer lips, a move he had seen in numerous porn videos. Ashley smiled, it was cute. Then she felt the head slip inside, quickly followed by almost his entire shaft.

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