Helen and Jim Vol. 02


"I want to really, but...it's...just that you might not like what you find...and...and I really like you..."

Helen leaned down, kissed his belly and pulled on his pants as she said,


Reluctantly he did. His mind was swirling with the possibilities of what her reaction would be to his lack of manhood. As his pants left his hips he closed his eyes. He couldn't bear to see the disappointment on her face. Cool air washed over his three angry inches and he steeled himself for the laughter he knew was coming. Instead he was covered by the hot wetness of her mouth. Helen gave out a MMMM that matched the ones she'd given for the pizza and proceed to give him a scorching blowjob. She sucked on and licked him like she was going to die if she couldn't have him. Jim was amazed. This had never happened before. Helen appeared to be completely unfazed and it was almost as if she hadn't even noticed the size of his penis. Jim began to relax and enjoy the menstruations of Helen's mouth. She looked up into his eyes as she bobbed her head over his tiny cock and it was the sexiest thing Jim had ever seen.

Helen was pulling out all of the hot sexy stops. Inside she was positively gleeful about the size of Jim's penis! Not because she was bigger than Jim, hell she was bigger than most of the men she hooked up with, but because his size might make him willing to be more understanding about her penis. If they could just get past that hurdle maybe they could make this more than an awkward one night stand. Helen was working Jim for all she was worth and paying close attention to his reactions. She wanted him close to an orgasm, but didn't want him to slip over the edge.

Jim was getting close to coming and reflexively grabbed Helen's head, but before he could come she popped him out of her mouth and pinched the head of his dick to kill his orgasm. Jim let out a little yelp and a whimper as Helen said,

"Not yet. We need to get you a little more wound up before you come."

She went back to work on him, sucking on his balls as she rubbed his spit slick prick between her hand and his belly. Jim writhed beneath her skilled hands and each time he drew close to an orgasm she would pinch him off.

"Please Helen! Let me come! I can't take anymore of this teetering on the edge! I'll do anything! Just please let me come!"

"I want you to come Jim, but first I want you in the right frame of mind. I want you so desperate to come that you can barely contain yourself."

"I'm there I tell you!"

"Ok. I'm going to show you something and I want you to be open minded."

Helen's heart was racing as she stood and unbuttoned her pants and then sexily wriggled them down over her hips. Jim watched her with eyes ablaze with lust. He followed her pants to the ground with his eyes then took the long leg express back up from the floor. When he got to her hips she could see the confusion in his eyes as his mind tried to reconcile her large penis with her curvy feminine body.

"Helen. I think there's a problem. You've got this great womanly shape, but my eyes seem to be broken because I see a rather large penis where there shouldn't be one."

Jim tore his gaze from her crotch and when he looked at her face he saw that she was blushing and biting her lower lip. God, was she sexy when she did that!

"I'm sorry Jim, but your eyes aren't broken. This is how I'm made. It's been there all evening during the car show, the pizza and the blow job. It's part of me."

Jim thought about how amazing she had looked all evening and how much he liked being around her. He didn't want to give that up, but he couldn't just ignore her large penis. He wasn't sure how he felt. Well maybe he was, horny, that was how he felt.

"So how am I going to make love to you? Are you going to let me stick it in your butt?"

This was a question she hadn't anticipated. Was she? If she really liked him shouldn't she let him? After all, she had every intention of sticking hers in his butt. She glanced down and he was still standing at attention. Fully erect and ready for action. That was a good sign. It meant that he was still interested in having sex. Helen made a snap decision to allow Jim to make love to her.

Helen reached out and took Jim by the hand. Pulling him to his feet she led him into his bedroom. She stopped at the foot of the bed and turned to pull him into her arms. She kissed him and held his naked body against hers. Jim returned the kiss and wondered at how good it felt to hold her body against his. One arm was around her thin waist and the other around her back with his hand on her head, pulling her deeper into the kiss. He could feel her firm breasts pressing into his chest and they felt so good, yet the feeling of her large cock pressing into his hip was very disconcerting.

He was wondering what the hell he was doing. A small part of him wanted to run screaming out the door, but other than the big dick she felt so much like a woman that he thought if he could focus on her breasts he could forget about the penis. Well almost, it was pretty damn big.

Helen broke the kiss and sat on the bed. She leaned down and took his still hard penis into her mouth to give it one final spit lube before she took him in her. She sucked him for about thirty seconds, then scooted back on the bed and pulled her legs up. She spread them and Jim's head swam with lust. Helen's dark hair spread out in a fan around her head and he could see her smoldering bedroom eyes beckoning him to her. Her breasts were rising and falling with shuddering breaths. Helen watched as he drank in the view and wondered what could be going through his head. She was about to find out.

Jim knelt on the foot of the bed and leaning down kissed her inner thigh. He kissed his way over toward her crotch and skipped over it to the other thigh. Helen slipped a hand down and pulled her balls up out of his way as he came back to her crotch. He kissed her taint area then slid down and found her tightly puckered sphincter. Even here she smelled of lavender. Tentatively he touched her with the tip of his tongue and ran it around the crinkled edges of her hole. He made several passes before testing the center. He could feel her quivering on the tip of his tongue. She tasted surprisingly good. He'd tasted a butt hole before, one of his girlfriends that didn't stick thought she could make do with rim jobs, but she never tasted this good.

Jim wriggled his tongue deeper into Helen's ass as he ran his hands up her sides to cup a breast in each hand. His fingers found her nipples and pinched them gently, then rolled them between his fingers and thumbs. Helen loved how Jim's tongue felt as he flicked, worked and plunged it in and around her little dark rose bud. Her cock was so hard it was aching with each throb of her heart. She couldn't take it any longer and reached down to grip his head with her hands and pulled him up on top of her.

Jim kissed her neck and face but avoided kissing her on the lips since he didn't know how she felt about having his mouth on hers after his tongue had been buried in her ass. Helen held his head steady and covered his mouth with hers. A second later her tongue filled his mouth and he knew exactly how she felt about him going from her butt to her mouth. As they kissed Jim poked and prodded around her butt until the tip of his penis found her hole. He pushed into her and Helen had to admit that it was rather uneventful. Certainly she could feel him inside of her, but it didn't hurt and if anything it felt kind of nice. What Jim did next stole Helen's heart.

Jim made love to her. He didn't just fuck her like some guy getting a piece of ass. He caressed her, kissed her, looked deeply into her eyes and made love to her. It was the most intense love making she'd ever had. Their whole world shrank until it became just the two of them. Jim was pouring his soul out to her though his eyes, giving everything he had to her.

Unfortunately, Jim had been too long without sex for the experience to last all night and Helen found that as he neared his orgasm she began to feel like she was too. This was a position that she'd only ever tired once before and that time had been such a total failure, she'd vowed to never do it again. But it was different with Jim. He made her feel like the woman she knew she was inside and that was flooding her with feelings that she had thought were gone forever. Finally the wave was built up too high and there was nothing left but for it to come crashing down over them. Jim arched up and began to come hard. Helen gripped his ass cheeks in both hands and pulling him tightly against her joined him by squirting ropy globs of her own come all over their stomachs and her breasts. They gasped and grunted, groaned and moaned until they were both spent.

Jim looked at Helen's beautiful face and into her dark eyes. In unison they said,

"That was incredible!"

They burst out laughing and Jim rolled off Helen to lie beside her on the bed as he tried to catch his breath. They chucked for a bit longer then Helen rolled onto her side and asked,

"You thought that was incredible?"

"Well...yea. I've never had anal sex before so that was cool and it felt so good and it was just so...so...new I guess or maybe it was because you're so tight, or...or...hell, I don't know. But you thought it was incredible too?"

"Yes, but for different reasons I think." She reached out and placed a hand on his chest where she could feel his heartbeat. It comforted her. Helen was thinking of where this was going next. She had enjoyed feeling like a woman and found it to be one hell of a turn on. So much so that now she wanted to fuck him more than ever. No, that wasn't exactly true. She wanted to make love to him like he had just done to her, she wanted more of that all consuming intensity that made his love making other worldly. Jim startled her with a question.

"So...what do we do about that?" He asked as he pointed to her penis. "I won't lie, I'm a little uncomfortable about it. After spending time with you today I'm struggling with how to deal with the fact that you have a penis. You are a beautiful pinup girl. You walk like a girl, talk like a girl, smell like a girl and kiss like a girl. In my mind that makes you a girl, but girls don't have penises. At least none of the other girls I've known have had one."

"Were any of them as much fun as me?"

"No. Not even close. And I'm not even taking into account the incredible sex we just shared."

"Do you think you could learn to over look my penis?"

Jim considered her words for a few moments. Could he overlook it? Pretend it's not there? Not likely, and he was pretty sure she wouldn't want it overlooked.

"Would you really want me to? Forgive me if I'm wrong Helen, but honey, you don't seem like the kind of girl who would want that big and important to be over looked. I think you would very much want to engage it. Am I wrong?"

Helen let out a sigh. She knew she needed to be honest, but damn it, she really liked Jim and didn't want to lose him! In the end, honesty won out.

"No. You're right." She moved her hand up his face and pulled his lips to hers. The kiss was hesitant. As if they were starting all over, and in a sense they were. Helen fell into her more natural role of taking charge of the situation. She kissed him gently, softly, sucking on his bottom lip and dipping her tongue into his mouth to tease his. She moved slow and steady, knowing that how she made love to him in the coming moments would have a direct impact on if they stayed together. She pulled him close and her hands explored his body, enjoying the feel of his muscles beneath his skin. Jim's free hand explored her and found its way to her nipple where it lingered to tease it erect. That wasn't the only thing on her body that was erect. Her cock was hard and throbbing, eager to have its way with Jim's virgin ass. Helen pulled his leg up onto her hip and slid her penis along his crotch. The tip brushed against Jim's sphincter as it went past and Jim tensed up, but as Helen continued kissing him he slowly relaxed again. Helen slipped an arm beneath Jim and cradled the back of his head in her hand. As she kissed him she let her free hand run along his hip and up onto his side, then down his back to the crack of his ass. Her fingers found his tight sphincter and she began to massage it. She worked it and rubbed it trying to make it relax. It was helping some, but she really needed some baby oil to slippery things up a bit.

Jim was thinking the same thing since he had an idea where this was going. He figured that she didn't want to break the mood, but he knew that if this was even going to be attempted there was going to have to be something used to lube things up. He remembered the night before on the dance floor with too many beers in him to care what happened. Now that he knew about Helen's penis the floor scene was a little clearer. He had pretended to let her do him last night. Tonight she had let him make love to her and that had been incredible so he felt he at least owed it to her a try. At that moment Helen slipped a finger into him.

"Whoa girl! I think I know where this is going. Are you planning on making love to me?"

Helen pulled back so she could look at him. Her heavy lidded bedroom eyes spoke volumes and she was trembling with desire, her bottom lip was pushed out in a pout as she nodded then averted her eyes. Jim knew that his next decision was immensely important if they were going to stay together. He didn't know if he could handle any cock in his ass let alone one the size Helen was sporting. But Jim did know he liked Helen more than any other woman he'd ever been with and decided to do his best to please her.

"Behind you in the night stand drawer is and old tube of KY. I think we're going to need it."

Helen's face broke into a huge grin and she planted a kiss on his lips. Twisting at the waist she reached back with her free hand to fumble the drawer open. Jim watched her breast bounce and jiggle as she searched for the tube. It only took a few seconds to find it and she rolled back to him. She opened the tube and applied some to her fingers and then went back to massaging Jim's sphincter. The lube worked wonders and made it easier for him to relax. She went back to kissing him as she explored his ass with her finger tips. Finally, Helen slipped a finger into him and as it turned out it went in pretty easily. She rubbed it back and forth and the feeling of his rectum gripping her finger made her cock throb with readiness. Jim's face was buried in her neck as she decided to try another finger. This time she heard a quick intake of breath, but that was all.

Things were going great so far. She'd been with any number of guys that had called it quits at two fingers and Jim had only gasped a bit. She pushed a third finger into him and he groaned into her neck. He was breathing harder and she could feel his anus squeezing and releasing her fingers. It was driving her crazy. Helen pulled her fingers out of the way and slipped them below the head of her penis and pushed the tip against Jim's asshole. Instinctively he clamped shut as Helen tried to push into him.

"Relax. You're doing great." She whispered.

She felt him relax a little and the tip began to penetrate him. The KY was making things very slippery, which was important if she was going to get inside him. Helen rolled her hips forward and pressed a couple of inches into Jim. Lying on their sides facing each other with his leg hooked over her hip she wasn't going to get very deep into him. That was probably for the best because she needed to go slowly, but she was so excited she didn't think she could. With a couple of inches in him she stopped and held still. Pulling his face from the crook of her neck she looked at him and asked, "Are you OK?" Jim nodded and Helen kissed him. She began to move her hips to pump the first few inches of her hungry cock in and out of his ass as she kissed him. She was breathing hard and the kisses were gaining in urgency with each passing moment.

Jim couldn't believe what was happening. He'd never considered doing something like this in a million years and yet he didn't feel all that odd about it. He could tell by how she was kissing him that she was super turned on and that, in turn, had him excited. He was eagerly kissing her as she worked her cock back and forth in his rectum. It hurt a little, but not too much which was a good thing. He'd always thought that anal sex was supposed to be really painful.

They stayed like that for several minutes. Letting the intensity build, they caressed and rubbed, kissed and licked each other until they were both panting with desire. Helen desperately wanted to roll over on top of Jim. She was getting as much as she could into him with each thrust, but it wasn't enough. Jim could feel her straining to get deeper into him and with her hand on his tail bone pulling his hips forward for a better angle he knew what he needed to do.

Jim's leg was still hooked over her hip so with a shove and a little grunting he rolled over onto Helen. He had no more than got into position straddling her when her hands came to his waist and her hips thrust up burying a two thirds of her raging cock in him before he could pull up and stop the intrusion.

"Ugh! Helen! Ugh! Hold on honey!"

She got a grip on herself and stopped pushing, but only just barely.

"Give me a few minutes. I need to adjust to you. Damn! You are one big girl!"

Helen let her hips settle back down onto the bed. As she pulled out of Jim he closed his eyes and let out a big sigh. He took a couple of deep breaths. When he opened his eyes he looked into Helen's. Her eyes were heavy lidded with lust and her chest rose and fell in little hitches that showed just how excited she was. Jim leaned forward and placed a hand under each of her breasts so that they lay in the crooks of his thumbs and forefingers. Leaning down he took her right nipple in his mouth and flicked it with his tongue. Helen arched her back in pleasure and moaned. Jim pushed his hips down slowly swallowing her throbbing member in his ass while he worked her nipple. Jim got to a point where things were hurting so he stopped and switched his mouth to her other breast as he let his ass get accustom to her size.

Helen was in a euphoric daze. She'd had guys straddle her before, but it was never their idea or on their first time. And then to have Jim working on her breasts was almost more than she could stand. Jim was wiggling his butt over her cock and finally he must have found a spot that worked for him because he slid down and engulfed the rest of her tormented prick. With one hand working on her breast rolling the nipple between his thumb and finger, her other breast in his mouth where he was sucking/biting/flicking her nipple and his other hand caressing up and down along her rib cage Helen knew she wasn't going to last long.

No guy had ever made love to her like this. Not ever. The intensity he'd brought to love making earlier was nothing compared to this. Jim pushed his feet under her legs which she raised to allow him to hook his behind hers. He pulled with his legs and began to grind his ass around her straining cock. That was all she could stand. Helen gripped his hips and pulled him against her. With a huge groan she exploded deep in Jim's bowels. After the first shot Jim sucked her tongue into his mouth as far as it would go and started to fuck her tongue with his lips. This new sensation made Helen's next several shots even more intense. Jim was making some groaning noises of his own, but Helen barely noticed. When the final convulsion shuddered to a stop Jim broke the kiss and collapsed onto her chest. They couldn't do anything for a few moments but lie together and pant.

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byruwild© 19 comments/ 66786 views/ 58 favorites

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