Hell... What are Friends For? Pt. 03

"How's the head?" Hailee asked as she grabbed a towel.

"A little fuzzy, not too bad though," Chris replied, his eyes wandering towards her glistening thighs.

"Well I hope that clears soon. It's my turn today and I don't want anything holding you back."

Hailee turned away from him slightly to dry her hair and in doing so gave Chris a view of her beautiful ass, her swimsuit buried in every crevice. "I'm sure you have nothing to worry about" he replied.

**************

The morning and early afternoon were spent hanging by the pool, chatting, sunbathing, and occasionally swimming, but everyone could sense the tension hanging in the air. Eventually Hailee announced she was going to take a shower, and it was clear to everyone that Chris should follow soon after.

Chris awkwardly excused himself then headed to his own en-suite to prepare for what was to come. When he was ready he gently knocked on Hailee's door and she called for him to come in. She was still in the bathroom as he entered so Chris sat in the chair in the corner to wait. Eventually Hailee emerged, wearing matching black bra and panties, underneath a sheer black negligee. Immediately Chris was drawn to her long black hair, draping over her shoulders and down her back. Then he focused on her beautiful, pale skin, she was so very different from Ashley, it was almost exotic.

"Fuck you're beautiful," he exhaled.

"Thank you," Hailee replied looking him over, noting his rather ostentatious robe, "Not too bad yourself. Care to join me?"

Hailee held out her hand, Chris kissed it and they both laughed as he stood up. Hailee untied his robe and let it fall from his shoulders, revealing his newly toned body, and a half-formed erection tenting his black boxers.

"Let's see what all the fuss is about."

Hailee dropped to her knees and hooked her fingers into his underwear. With a quick tug she uncovered the object of her fascinations. Being only half erect she wasn't immediately impressed, so she quickly took hold of him and began gently sucking his cock.

It didn't take long for his body to react and his shaft took up it's strange, rigid shape.

"Hmmm, that is quite an odd shape. It's bigger than I was expecting," Chris didn't reply, he was too busy reacting to the sudden feel of her mouth. "You okay?"

Chris snapped out of his reverie, "Sorry, I wasn't expecting it to feel so different. It's fucking amazing, but I want to try and make you cum first."

Hailee stood and smiled, "By all means, be my guest."

Chris quickly had her face in his hands and they were kissing passionately. His hands roamed her body as his warm, hard cock pressed onto her stomach. The negligee was discarded, soon followed by the bra. Much like Ashley, Hailee's breasts seemed impossibly pert, but with much larger, pinker areolae. He applied the lessons he had learnt with Ashley whilst feeling, and exploring her chest. Then he kissed back up her neck, and signalled for her to move to the bed.

As Hailee scooted up to the headboard, she impulsively removed her panties and spread her legs. Chris got the message and took his position in front of her visibly dripping sex. Unlike Ashley she was shaved bare, but her sensitive skin had suffered slightly from razor burn. He kissed each blemish then flipped her over to her hands and knees. Placing his hand over her entrance, she was radiating heat, he knew he didn't have to do much more. Quickly his erection found her opening, and pressed between her hot, wet folds.

Chris was immediately surprised at how different it all felt. Physically the sensations were the same as he sank himself deep inside her. The warm, wet, flesh that tightly surrounded his cock was familiar, but his other senses were reacting to the otherness of the situation. Most obvious was the sight of Hailee's jet black hair sprawling over her pale skin. Automatically he was aroused by the sight of another woman's body. Then there was the smell, it was familiar, but subtly different, and he was reminded of the first time he had noticed the intoxicating aroma of a woman's sex. Finally and crucially there was the sound of Hailee's cries and moans. As she spoke, an entirely different personality was reacting to his body, and he found this the most challenging. His body was enjoying this so much, his usual staying power was faltering. It wouldn't take much more to force him over the edge.

"Hold on Hailee, I need a second," he gasped as he removed himself, preventing a disaster.

"Noooo!" Hailee cried in response, reaching back to grab his cock and force him inside her, "I'm so close, you can't do this to me, it feels so fucking good! Cum if you need to, I don't care, we've got all day!"

Chris didn't need convincing, once again the otherness got to him as Ashley would never have said that. He plunged back inside her with a deep guttural moan, and proceeded to fuck Hailee with abandon.

Hailee wasn't lying, she was close and with each thrust Chris' miracle cock worked it's magic.

"I'm gonna cum, I'm gonna cum," she cried as every nerve in her body seemed to vibrate, and her loins exploded in orgasmic bliss.

Her cries were loud, and devastatingly sexy, Chris had no chance of holding back. In one last desperate response he let go of her ass, breathed through his nose and focused on the wallpaper. But at that moment Hailee slammed back into his crotch and took him past the point of no return. From that moment on he focused on her moans, her soft pale skin and long flowing black hair. He felt her hot, beautiful pussy working over his glans, and smelt the familiar yet exotic smell of sex. Then with a sudden grunt, he rigidly thrust forward, and powerfully ejaculated inside her.

Hailee's orgasm was in full flow when she felt his hot seed flood her womanhood. The sensation was intense enough to almost push her to the point of passing out, so she bit the inside of her mouth to stay awake. Chris' orgasm had been explosive, yet frustratingly short, still rule number one 'don't pull out until she's finished' ran through his mind, so he held onto her hips as his penis continued to twitch inside her. Eventually her body relaxed, and Chris was able to pull out and lie beside her. Still she whined at the sudden emptiness.

"I'm sorry Hailee, I usually last much longer," Chris gasped.

"What are you apologising for? That was so fucking hot I nearly passed out! Plus that wasn't really your fault, I was trying to make you cum"

Chris laughed with relief, it had been a while since Ashley had been able to exert that sort of control over him.

"How long until you can go again?" Hailee enquired.

Chris slid his hand up her thigh and grabbed a handful of flesh, "For you, no time at all!"

******************

By the third day Chris was slightly concerned as to whether he could engage in another session. Hailee had been almost unstoppable, her desire refused to diminish, and Chris found she was exceptionally skilled in maintaining his arousal. Her gorgeous, supple body finally elicited his forth orgasm just before midnight, after which he abruptly passed out. When he awoke the following morning he admired Hailee's enticing form, then forced himself away. He knew the rules, today was Lea's turn.

Chris cleaned up then ate a huge breakfast in an attempt to regain his strength. Of the three women, he was least familiar with Lea. They would chat at social gatherings and made each other laugh, but there wasn't much of a connection. This made him feel slightly anxious, he couldn't quite understand why she had joined them. He felt a little awkward when he eventually went to her room, but as he got closer he could hear an unmistakable sound coming from her room. Chris gently rapped on the door then peered round to find Lea sat in front of a giant TV. She was naked from the waist down, but still wore a pink tank top. Her mousy blonde hair was tied up in a pony tail that bobbed and swayed as she intensely watched the screen. Considering everything Chris had seen that weekend, he was still taken aback. Lea was masturbating, and watching some pretty hardcore porn.

As Chris stepped closer he caught Lea's attention, she looked up at him and patted the vacant space on the sofa next to her, then continued to touch herself. Chris sat and watched the porn with her for a while, until eventually he had an erection that was starting to feel uncomfortable.

"Is this what you're into?" he asked.

Lea shushed him without looking away. That's when he noticed the tension, she wasn't relaxed, and didn't appear to be enjoying herself. When the scene ended with a crescendo of fake cries and flying semen, Lea stopped and flopped back in her seat and sighed.

Chris squirmed in his seat, "You alright?"

Lea looked down and noticed his erection, as the next scene started she reached across and pulled his manhood free from his tracksuit pants, then slowly began to rub his shaft.

Chris took a deep breath, "As great as this feels, its probably not necessary, I'm ready if you are."

Lea continued to stroke, then pulled down on his shaft and ran her fingernails up and over his glands causing him to shudder and moan. Her handjob skills were exceptional, despite his irregular shape, she knew exactly how to touch him. In comparison her technique for touching herself seemed clumsy and fruitless; it didn't seem to generate the same feelings. Chris had to stop this and find out what was happening, so with every ounce of self control he could muster, he took hold of her hand and stood up.

"Lea, what's going on? You didn't travel all this way just to give me a handjob."

Lea sat back and sighed. "Chris, I need to trust you. I need to tell you something, but I want to know what you're after. I've never told anyone this before."

Chris pulled up his pants and covered his crude erection. "Lea, we're here to have fun, but you have no obligation to do anything."

Lea smiled, she seemed to be on the edge of tears. "It's all just silly really but, the thing is, I've had sex with lots of guys, you know that." Chris nodded and smiled. "But every time, even on my own, I don't think I've had an orgasm."

Chris didn't know how to respond, but as the tears emerged he reached across and hugged her.

"I've tried almost everything. Wanking, vibrators, dildos, sex, guys going down me. I even got one of those massage things, but nothing. All the guides say, you'll know when you've had one, and I don't think I have."

Chris sat and stroked her hair, letting her speak.

"I think I've been deliberately making guys blow before we get to sex. I like the control, but also most of the time I find sex pretty painful. I don't get very wet, and its embarrassing asking guys to use lube. I feel like my vagina is broken. I worry that, after everything Ashley has said, and hearing Hailee last night, if you can't make me cum, no one will."

"I'm so sorry you're been made to feel like that. From what I've seen you put too much emphasis on your partner's pleasure, and nothing into your own. How did you learn to masturbate?"

"Through porn mostly, I've tried to work it out myself."

Chris sighed, "Porn is total shit. From what I understand every woman is different, but hardly anyone masturbates the way they do in porn videos. Please speak to Ashley and Hailee, they can help, have you tried being with a woman?"

"I'm not attracted to women, I like guys."

"Don't think about it like that. I'm not attracted to my hand, but it's been getting me off for years." Finally Lea stopped crying and laughed. "I'm conscious that you're in a vulnerable position, and I think if I try going down on you, it's only going to make you anxious. But from my experience with Ashley and Hailee, I'm sure I can give you an orgasm. So I suggest we watch porn for a while, then when you're ready, we can give it a try, using as much lube as you want."

"Okay, that sounds alright," Ashley replied, "Can you take your clothes off, I want to see your body."

Chris smiled and did as she asked, in return Lea removed her tank top. She wasn't wearing a bra, and Chris noticed her breasts were much smaller than Ashley and Hailee's, but they were still gorgeous. He wanted to feel them, but knew he had to wait.

For the next half an hour they sat next to each other, touching themselves, and occasionally each other. The porn was starting to have a real affect on Chris, and he grew more adventurous, running his hand over Lea's thigh, then down onto her calf. She didn't object, so he moved round and with his left hand he finally got to touch her breasts. They may have been small, but they were pert, and deliciously sexy. Overcome by his arousal, Chris began kissing Lea's neck, and he noticed as she tried to swallow, it slightly caught in her throat.

"Do you feel ready to move this to the bed?" Chris asked.

"Okay, but please use lubricant, it's on the side," she replied.

As Lea stood Chris could admire her naked body properly. Her legs seemed to go on for ever, ending in a cute little ass he instantly wanted to grab. Chris applied a large amount of lubricant to his cock, then passed the bottle to Lea. She spread more over and inside her pussy, then awaited instructions.

"I need you to get on your hands and knees, and aim your butt towards me. This only works either doggy style, or reverse cowgirl, but doggy is more effective."

Lea nodded and followed his instructions. Chris felt slightly guilty, the image before him was of a vulnerable woman, in a gratuitously sexual position. Her cute butt raised in the air, her face pressed into the pillows, her long blonde hair billowed either side. Chris climbed onto the bed and approached her waiting sex, guiding his swollen member to her lubricated opening. The porn had replaced some of the concern for his partner with lust, but still this was the moment of truth.

Chris pressed himself through her opening, she was tight, but the lube helped. Despite his arousal Chris tried to be gentle, pulling out before halfway through. Then on the second descent, he pushed further, bottoming out with an inch to spare.

"Lea, are you okay?"

"I feel something, it's... different."

This was encouraging, but still Chris took it slowly. To him she felt wonderful. Her petit, yet tall frame accentuated the otherness he had felt with Hailee. He loved understanding that sex was not uniform, and adapted to the partner. Chris almost lost concentration when he heard a gasp.

"Did that hurt?"

Lea was smiling, that was not a gasp of pain. The feeling was familiar, but much stronger.

"Please keep going," she whimpered, "Something is happening."

Now Chris was smiling, but aware this was only the start, it meant nothing unless she came. Slowly he built up speed and intensity, hoping it was having an affect. It was certainly affecting him, he had never fucked like this before, every inch of Lea's pussy gently caressing his shaft, weakening his resolve.

"Lea, I need to go faster or I'm going to lose it, is that okay?"

"Yes, yes!" she mumbled.

Now Chris had a big stupid grin, taking hold of her sexy little butt, he started taking longer, harder strokes that made Lea whimper with pleasure. The thrusts soon grew faster, now there was a steady pace, his balls slapping against her pussy, and he noticed he was sliding with greater ease. Lea was wet, her previously unresponsive sex was welcoming his touch.

If Lea was going to cum, it was going to be a close thing. Chris' focus had shifted to his own pleasure and his hands ran over her warm skin. She felt soft, but underneath her muscles powerfully contracted. He lent forward and kissed up her back, noticing a red flush had enveloped her upper body. This made Chris briefly will her on, before an overenthusiastic thrust caused him to bump her cervix, forcing him past the point of no return.

"Oh fuck, oh fuck," he cried, "I can't... hold on!"

Chris cried out, focused on his breathing and held back all he could, but there was no stopping it, and with one final thrust he buried himself within her and forcefully released his seed.

Lea had been very quiet, but internally it felt like her body was awakening. She listened as Chris valiantly held back, before her body forced him over the edge, and his hot, fiery cum filled her tight pussy. Suddenly the familiar sensation intensified to an infinite degree, and she was crying out in pleasure. Her body writhed and wriggled above her and for just a moment, she felt every care in the world slip away. Milliseconds later the feeling flooded every inch of her body, and she cried into her pillow.

As Chris' ejaculation subsided, he realised Lea was cumming, and resumed his thrusts, ignoring the intense sensations telling him to stop. He continued for what seemed like hours, then eventually came to rest deep inside her.

As Lea's orgasm finished, Chris pulled out and lay beside her. Her skin was still flushed pink, but she was quite visibly weeping. Chris held her tight.

"Thank you, thank you so much," she whispered.

"I thought you weren't going to make it," Chris laughed, "You had me fighting back for so long!"

"I told you, I like the control. Feeling you give in and release your load made me cum."

"Did you notice the wetness? There's no way the lube caused that, that was all you!"

This caused a fresh round of tears from Lea, so Chris hugged her again. He felt bad that having her hot body pressed up against him was already helping him recover. He hoped she would want to go again.

"Can we try the reverse cowgirl?" Lea asked, wiping away tears.

Chris laughed hard, "Be my guest!"

Lea jumped up and Chris again scanned her beautiful long legs. She bounced across the room to a large mirror and pulled it up to the bed.

"Ashley was telling me you get frustrated because you can't see her face when you fuck, so I thought this might help. Also I want to know what I look like when I cum!"

"That is not going to help me with my staying power you know."

"Good, don't forget, that's how I like it!"

Lea took hold of his cock and sucked him back to attention, before spinning round and sinking onto his beautiful miracle dick. As they fucked she stared back at him, and as expected Chris was no match for her beautiful face. As he gave in and the first few shots fired off inside her, Lea focused on her own body as she reached her second, glorious orgasm.

Chris was exhausted, and luckily for him, Lea was more than happy to curl up and sleep. The days of anxiety and worry had tired her out. Plus her body was trying to recover from the previously unaccustomed riggers of orgasmic bliss. They slept for several hours, and were finally woken by a presence in the doorway.

"Tick tock."

Chris and Lea groggily rose from their slumber to find Ashley and Hailee, wearing very little, standing in the doorway. Chris looked over at the clock, and it was nearly midnight. Naturally he assumed that would be the end, but it seemed the women had other plans.

"What's going on?" Lea enquired.

"Hold on," Hailee was watching the clock, moments later it ticked over to midnight. "Times up, now it's free game!"

Ashley and Hailee entered the room, smiling, and removing what little clothing they wore. Chris wasn't sure if he could go again, he was feeling pretty sore, but as his beautiful friends revealed their naked bodies to him once again, he decided to play along, so he jumped up off the bed, and began to set the rules.

"Okay, I agree. But first I want you to make Lea cum."

Lea was a little surprised, but Ashley and Hailee thought nothing of it. Soon they had assumed their positions as Lea lay on her back, Ashley between her legs, and Hailee by her side. Chris stood back and admired the scene. Ashley's beautiful ass was the centrepiece of a sea of female flesh. Long legs writhing and interweaving. Hailee's breasts lightly bounced as she gently brushed over Lea's nipples. Then she moved down, kissing and licking her long neck, before Lea pulled her up to her lips, and they kissed.