Friend with Benefits Pans Out

The internet dating site had delivered. At last someone that had actually responded and had sincerely answered his requests for contact, and even though he was shy and reticent, her responses had been erratic at first, almost hesitant. The first message had been a month apart from the second, then another two weeks later.

Her photo was one that didn't give her beauty or identity away. Was she possibly a little scared too? Alex was now a little excited to be corresponding with her. At least they were talking. He flirted a little with her, not wanting to sound too arrogant or flippant. She responded again, and this time with her cell phone number, and they promptly began using IM on the phone to chat.

Alex had by now discovered that the beauty he was chatting with, her internet dating name had been SilverNymph, was in reality Jackie. And she lived in the same area that he did, in fact a matter of three or four streets distant. BONUS, china! he thought.

They chatted for a few days about nothing in particular, and then one evening they were chatting, again about nothing in particular when Jackie made a comment and Alex thought...What? Did she really say that?

He responded with a glib but funny comment, about how to compare a woman's breasts to a fruit as a measurement to which she replied, 'Hope you're not going to settle for the small stuff, babe...?'

Alex replied, 'why, how big ARE yours...?'

'You'll have to see for yourself.' Was her response.

'How am I to do that? When are we going to have coffee then?'

'Oh, I don't do coffee with strange men.'

'Oh, so now I'm a strange man, am I?'

And so the banter went on... and turned more sexual as it did...

'So, if I'm an orange what are you then, mister?'

'What would you suggest...?' Alex was now a little aroused and feeling himself through his shorts.

'Oh, I don't know... say a Vienna sausage?' Jackie was definitely wet and getting hornier by the text. She had her hand between her legs and she was stroking her lady. That's what she called her sleek and special pussy.

'I don't wish to boast either, babe, but more like a Russian, if I had to judge.' Alex was a little pained in his reply.

'I concede... Oh I am so sore from all the walking I did this past weekend.'

'Say, I have it on good authority that I can give a very good massage. I would love to give you one.'

'You would?' Jackie sounded a little shocked, a little excited. 'How about tonight?' (It was 2:30am)

'Right now?' Alex asked, almost too excited by the request.

'No, silly, after I get home from work at around 5 tonight, or is that tomorrow night, really...' Jackie said, as she rubbed her pussy pensively. Spreading the moisture she found there and rubbing her swelling pussy lips then slipping two fingers inside her hole and stroking them in and out.

Alex pulled up to the gate of Jackie's complex and signed in at the security before driving the few hundred meters to her house. She had sent him the details in the IM as they were ending the chat the previous evening/morning, and he had no problems finding parking next to her car. He climbed out of his car and walked to the front door up a well tended grass pathway. Jackie opened the door, with her little Yorkshire terrier in her arms, to prevent him from running outside in the excitement.

They greeted and hugged hello, as if they were long lost friends, and Alex played with the terrier a little as Jackie prepared coffee for both of them. They sat down in the lounge and chatted as first time meet and internet matches do, the usual questions, where are you from, what do you do, although more in depth than they could have on IM when chatting there. Alex sat on the same couch as Jackie in spite of there being a second couch, and Jackie had after all indicated that she wanted him to sit there...

Alex gave Jackie a compliment and as he did he patted her affectionately on the knee, and left his hand on her leg a little longer than was appropriate, more stories and teasing were happening now, as they both finished their coffee and continued chatting. The conversation and interaction already was a little sexual after their conversation from last night on the IM system.

Sitting on the couch chatting and breaking the ice as they drank their coffee, Alex again put his hand on Jackie's leg, gently touching it and stroking her leg lovingly, almost as if they had known each other for many months and years. She was wearing a black dress over a skin tight black leotard type shirt, and stockings and her shoes lay on the floor at the door where she had left them when she got home.

Alex and Jackie were talking about something when Alex leaned forward and kissed Jackie, cutting her sentence off. Her eyes closed and she responded warmly, and she started mewling soft noises in her throat that drove Alex over the edge. His hands started to explore her body. Her hands rose and caressed the back of his head as he kissed her. The kiss was long and drawn out and both were really enjoying it.

Alex felt a little nervous but was confident and assured. Jackie broke away from his lips briefly and asked...

"Would you like more coffee?"

"Yes, please that would be nice..." Alex answered.

They got up and moved back to the open kitchen area. Jackie busied herself boiling the kettle and making the coffee. Alex stood off to one side and watched, and both of them were still making small talk, teasing a little more.

Jackie finished the coffee, poured the milk into the cup and returned to the fridge with the bottle of milk. On her way back from the fridge to the cups of coffee, she passed Alex who simply reached out and took hold of her arm, turned her and gave her a hug and whispered in her ear, "Do you want that massage now...?"

Jackie melted into his arms, turned her head up and smiled into his face and he leant down and kissed her again, long and deep, his tongue snaking out and into her mouth which was slightly open and inviting. Jackie made small mewling noises as they kissed and their hands explored each other.

"I think it is time for that massage you promised, yeah." Jackie said, softly. And taking his hand she led him down the short passage to the bedroom and the large bed. She pulled a towel from the rail in the en suite bathroom and laid it on the bed.

"Do you want me naked or just stripped down to a minimum?" Jackie asked, a little nervously.

"I will put a towel over your body, so yes, take it all off, please." Alex asked. Jackie promptly removed all her clothes.

He pulled the bottle of oil he had taken from his bathroom before leaving home, out of the bag he had collected from the car and put it on the bedside table. He arranged the extra towel over Jackie's back and body, then began to warm his hands up and oil them a little.

He poured a generous pool of oil onto her back and began to work it into her muscles of Jackie's back and buttocks. Stroking her up and down, working the muscles and then out onto the shoulders, deeply massaging the knotted muscles. He poured more oil out and oiled up her legs all the way down to her ankles. Her back gleamed from all the oil he had spread on her. He worked her leg muscles from the bottom to the top, rubbing up into the large muscle of her butt.

Jackie was now really enjoying this massage, and she began to moan softly as she was totally immersed in the entire experience of it and could feel Alex's fingers as they passed mere inches away from the crease that hid her pussy from view. She lifted her hips to allow him access to her sweet valley, but he teased her and passed right on by with each pass. Alex knew she wanted his hands in that valley, but he deliberately did not go in there.

He rubbed her legs again and again, and each time she lifted her hips to give it to him and he passed over her offer.

"Mmmmmm... please, take your shirt off...?" and began to pull his shirt out of his jeans. Alex stopped rubbing her and removed his shirt. He dropped it onto the chair next to the bed.

She smiled up at Alex, her hand reached out and she said, "Why do you still have your jeans on...?" Alex stood up and unbuckled his jeans, letting them fall to the wooden floor with a loud bang as the buckle hit the wood. He straddled Jackie's calves and continued massaging the cheeks of her butt, opening them up and sliding his thumb into her pussy. She twitched and again lifted her hips for more attention from his amazing hands.

He lightly tapped her on the butt, "Turn over, please." He instructed Jackie.

He lifted the towel to allow for her to roll over, and Jackie quickly settled onto her back

Alex poured some more oil onto her tummy and started to spread it up and down her body and legs. He rubbed it up and over her big, gorgeous breasts and lightly pinched the nipples.

They were both naked now, and he rubbed her tummy gently, then again moved to her breasts and watched as the cool air made her nipples stand up and pull her areolas into peaks. Her body was now writhing a little more than when she was on her stomach. Her hands, she had been instructed to keep them away, were constantly moving and grabbing onto the bedding and it was clear that the sensations were driving her crazy.

Alex took this as a signal of sorts and began to spread the oil to her pussy mound and the valley between her legs, as if it wasn't wet enough already, and slid his hands up her legs with his thumbs on the inside of her thighs. As he passed close to the lips of her pussy he let his thumbs touch her lips and then slid his palm over the Mons and down the valley.

He slid his hand down over the mound of her Mons and slid a finger into the wetness of the lips of her pussy. "Do you like that?" He asked. And stroked her pussy another time, this time he slipped a finger into her pussy and sank it up to the second knuckle inside her. "Oh GOD that is so good...!!" Jackie said loudly.

She writhed and moaned as she shoved her hips at the hand inside her, while his other hand rubbed her breast and pinched her nipple, hard, making her pussy tingle even more, bringing her orgasm on faster, and she twitched and clamped down on his hand as she came.

"Make me cum, baby, make me cum..." She pleaded.

"I intend to, and a lot of times, if I can." Alex replied.

"You can, I promise you can..." Jackie breathed.

Her hips were now twisting and gyrating as his hands rubbed and manipulated her pussy lips and slipped over the outside with all the oil that had been applied. She writhed and moaned in ecstasy as his fingers played with her clit unintentionally. "Mmmmmm... more." She said softly.

Alex now began to take a more personal interest in the proceedings and with his hands already oiled up and working, he took hold of his cock that had now grown somewhat in the time that he had been massaging Jackie, and he "presented" it to Jackie to touch now for the first time.

Jackie took it in her hands and stroked it along the length... and moaned with a low, deep sound as she admired and appreciated it. "Good god, it is so big and beautiful, baby." She said.

"Baby, please fuck me with this gorgeous thing..." She asked.

"I will do just that, in a few minutes, baby." Alex replied. "I will, I promise."

He sipped his hands over her chest and again found her nipples, pinching them and pulling them. Jackie leapt with pleasure, and shoved her hips at Alex. "Fuck me, baby, fuck me now."

Alex put the head of his cock at the entrance to Jackie's pussy and she wiggled her hips, feeling him there... trying to get him to push inside of her. She felt him begin to push and the size was exciting her, and making her eyes start to grow in shock.

"Oh my GOD, you ARE huge. God that feels sooo good, you are filling me up, I love this..." Jackie moaned and swung her legs out and put her ankles on Alex's shoulders, giving him every chance to push deep inside her.

"Oh yeah, baby. This is fucking awesome!"

"Yeah baby, fuck me. Fuck me hard. I am going to cum. Make me cum baby, please..."

The sound of Alex's huge cock slipping in and out of Jackie's pussy was loud now, his hips bumping into the back of her thighs, the moisture they were making from the kissing that had now begun helped to make for a very noisy and wet sound as Alex shoved his cock into Jackie again and again, burying it deep inside her then pulling it back to almost pop out before he shoved it back into her.

Jackie could feel that she was now at the point where she was going to cum... and she threw her head back, moaning and mewling with pleasure as she started to cum.

"OH GOD, BABY, FUCK! BABY, FUCK ME. FUCK ME...OOOH"

Hearing her being so loud and openly expressive with her orgasm, Alex began to pump and thrust into her harder as he too now, began to cum.

"OOH UUHHH!! Ooh god. Yessss... baby!" Alex could feel his hot jism spurting into Jackie, coating the inside of her pussy with his warmth and the release of the tension making him fall onto her, and then they kissed and sucked each other for a few more minutes. They cuddled and held each other for a long time as they also stroked and touched each other all over.

During the rest of the night they kissed and cuddled, and then he would slip his hand into her pussy and finger fuck her to a host of further orgasms through the wee hours of that morning. They parted at sunrise for her to go to work and him to return home to his day and his responsibilities.