Sam and Helen

I could feel her bikini bottom rubbing the side of my cock. She put both of her hands on the edge of the hot tub, one on each side of my head. She closed her eyes and sat all of the way down, enveloping my cock. I could feel my foreskin being stretched downward and then I felt the sensitive head of my cock pass between her inner lips. That's one of the best feelings known to man, when a woman lips squeeze your penis right below the head.

"Fuck, this feels good," I moaned.

"Um-hm," Karen moaned affirmatively.

She just sat there, with me inside of her, for a minute. It felt so warm! Then she began to slowly move up and down. I put my hands on her hips and held on for the ride. I was afraid I'd cum soon, but I didn't want it to end yet because it felt so good. I watched her small tits jiggle as she pumped up and down on me.

"Suck on my tits!" she commanded.

I didn't have to be told twice. She slowed down a little, I captured her left breast in my mouth, began sucking on it, and swirled my tongue around her nipple and puffy areola. I was able to get her entire tit into my mouth. She began moving faster and moaning quietly again as I switched from one breast to the other.

To my left, I could hear Helen breathing as if she was running a race, and I could hear the water being stirred as she rubbed her clit faster and faster. I released Karen's boob from my mouth and put some pressure on her hips to slow her down.

She opened her eyes and whispered, "What?"

I tilted my head toward Helen. Karen stopped moving up and down and focused her attention on Helen.

"Helen, that is so hot!" said Karen.

Between harsh breaths, Helen said, "Uh...huh! Watching you guys...have sex...I mean...fucking...is...turning...me...on...so much!

Helen's mouth hung open and her eyes were tightly shut. At that moment, she was pinching and pulling her nipple so hard that her left breast was being pulled away from her body.

"Helen, are you close?" asked Karen, gleefully.

Helen groaned as she moved her hand faster, "Yes!"

"Slow down a little. We want to cum when you do."

Karen looked at me. "Don't we?"

"You damn right we do!" I said.

I was surprised I hadn't cum yet from the overstimulation of Karen fucking me and hearing and watching Helen masturbate. Thank god for "whiskey dick."

Helen didn't say anything, but she slowed down a little.

Karen began moving up and down again, quickening her pace in rhythm with Helen. Karen's eyes darted back and forth between Helen and me. My eyes darted back and forth between Karen and Helen. It was difficult to continually shift my focus with Karen's pussy sliding up and down my cock. However, I managed to do so because I wanted to see Helen's 'O' face when she orgasmed. There's nothing hotter than watching a woman's face when she cums. Helen continued to increase the speed of her hand.

Karen began moving up and down so fast that it was hard to focus on Helen. My balls and the tip of my cock began tingling, warning me of my impending orgasm.

Karen began breathing harder, but both us managed to keep our eyes open and watching Helen.

A low moan began emanating from Helen's mouth. Her other hand had joined her right hand below the water. From the way it was moving, I'm pretty sure she was fingering herself. I looked back at Karen, grabbed her hips and pushed her down as hard as I could on each downstroke.

"Oh, fuck! Oh, fuck! Oh, fuck!" Helen began whispering.

Her head was almost all of the way back on the edge of the hot tub and her mouth was hanging wide open.

Through ragged breaths, she said.

"I'm...about...to cum!"

Karen looked straight into my eyes. "Me, too!"

I only nodded as I quit trying to hold my orgasm back. I felt exquisite pleasure every time the tip of my cock passed between her inner lips and then back into her warm, wet pussy.

Helen moaned loudly, in spite of her earlier worries about being discovered out here.

"Yes, yes, yes! I'm cumming, I'm cumming!"

Karen followed, "Fuck, yes! Me, too! Me, too!"

I could feel her pussy contracting with her orgasm. I was so close to the edge. I looked back over at Helen—her head was hanging back, she was moaning, and her large, sagging, beautiful breasts were quivering.

She arched her back out of the water so far that I could see her furiously rubbing her clit with one hand and pumping in and out of her pussy with two fingers of her other hand. I looked back at Karen, watched her face as she orgasmed, and watched her tits bounce up and down.

Karen continued to slowly pump up and down as she looked into my eyes.

"Cum for me with your huge cock! I want to feel your cum shooting in me!"

That did it. I could feel the cum shooting out of my cock as I struggled to keep my eyes open and look at Karen's face.

I moaned, and then, "Ah! Oh, god! I'm cumming!"

I could feel the endorphins coursing through my body. Karen stopped moving up and down, her ass resting on my thighs. I was still rock hard inside of her.

"Still hard, I see," she said, smiling. She began swiveling her hips.

"Oh god, you have to stop," I said, "too sensitive."

She laughed. She stood up and I slipped out of her. Still hard, but beginning to soften. I saw my cum running down her leg as she pulled her bottoms back into place. She reached over me to grab her top from the edge of the hot tub and tied it back on.

Helen was sitting back in the water, her eyes closed as her breathing slowed down. She pulled her suit back up to cover her breasts. She looked very relaxed.

Karen smiled and asked me, "Did you enjoy the hot tub?

I smiled back. "Oh yes, that was very therapeutic," drawing out the last word.

***Part 3***

After we'd gotten out of the water, Karen went over to the controls and bent over them and pushed a couple of buttons—you're damn right I stared at her ass while she did it! I wrapped my towel around me and it started tenting outward, damned if I wasn't getting hard again!

I was really, really hoping for a round two with either woman. Does that make me sound like a pig? At that moment, I didn't care. I still had a healthy buzz, and I was thinking with only the little head.

The hot tub's lights faded away and the water stopped bubbling. I heard another noise and realized the hot tub was draining. Karen walked over to the gate where Helen and I were waiting. She looked down at my towel and smiled.

Apparently, she could see well enough in the dark to tell I was ready for more. She grabbed my cock through the towel and tugged a couple of times. I thought my knees were going to buckle before she let go.

"Too bad I don't have time to do this again, tonight. I have to be somewhere in the morning and it's already late." She looked disappointed.

"But I think Helen," she let it hang in the air for a moment, "could make use of a hard cock. Helen, I'm sure getting off in the hot tub felt good, but I know Sam's cock would feel even better. You'd be happy to help her, wouldn't you, Sam?"

I just nodded.

Helen looked embarrassed as she looked down at the lump in my towel. As I had observed before, her behavior was so out character compared to the Helen I had always know.

"I don't think that would be a good idea," she said, sounding almost sad.

"Helen, give Sam your keys so he can get into your apartment. Sam, you go ahead of us. We'll catch up with you in a few moments," said Karen.

Helen didn't look happy, but she put her keys in my hand. I opened the gate and as I walked back to her apartment, I tightly held onto the keys with one hand and my towel with the other. I could hear them whispering in a heated conversation that diminished in volume as the distance between us increased.

I let myself into Helen's apartment. My buzz had started wearing off, but I was so excited about potentially getting laid for a second time that night that I didn't care.

I went into bedroom to get dressed. I didn't want to put my clothes back on, but I also didn't want to sit on Helen's furniture while wrapped in a wet towel.

I finally decided to put only my shorts back on—once again with no underwear. Then I decided to put a T-shirt on since I didn't want to make Helen any more uncomfortable than she already was. It was almost midnight and I was tired, so I sat down on the couch to wait for them.

I jerked awake at the sound of the door opening. I must have fallen asleep. I looked at the clock and saw I'd been out for only about five minutes. Both women were quiet, but Karen gave me a little smile. Helen looked at me apprehensively and then looked down at my crotch.

My erection had gone away after I fell asleep, but my shorts still outlined my deflated penis. She looked away, walked into her room, and closed the door.

Karen came over and sat next to me. She was wearing her cover-up, but looking at her and remembering what was underneath and how it'd looked and felt, sent blood rushing into my cock, causing it to harden completely within about a minute. Karen looked at it and smiled.

"It looks like you're ready, even if she's not. Look, Helen really does need some dick, worse than I did! It's been about six years for her and, as much as I was ribbing her, I'm serious about this. She really needs to be able to trust who it is, and right now, there are no men she seems to trust other than you.

I was confused and it must have shown on my face.

"Helen's experience with sex has been limited and mostly unfulfilling from what she's told me," Karen explained.

"I've been teaching with Helen for about four years, she's now one of my closest friends, and definitely my best friend at the school. So over these four years, she's been telling me the details of her life and some of them are not pretty. I've also picked up details from some of her college that have come to visit.

"She's come a long way, but she needs to get over one big hurdle, and I'm hoping you can help with that. If you two do this, I want you to realize it will be more than just fucking and getting off, but I also want you to realize that it's not a relationship.

"It's very important that you listen, okay?"

I thought about it for a moment and then nodded. My brain was not at its optimal level because fatigue and all of the alcohol in my bloodstream.

After the mutual masturbation session, I'd been hoping that I might get to fuck both women that night, but if I could actually help Helen, I'd do it for that reason, too.

"Good. The Helen you know—the assertive one that you're probably used to—that's a fairly new thing for her. It's not a facade, it's very real, but it's not the way she's always been."

She paused for a moment and looked up, and expression of deep thought on her face. After a moment looked at me again and continued.

"As I said a minute ago, I've pieced this together from what Helen's told me over the last four years and from what I've learned from her college friends who have visited.

"There's no other way to say it, back when Helen was in college, she was fat. She told me she was around two hundred pounds at the beginning of college. You imagine how she looked considering how short he is. By the time of graduation, she was getting close to three hundred pounds. In fact, it's amazing that she graduated at all, given everything she's gone through.

"Helen had never had a serious boyfriend, and she most certainly hadn't ever had sex. So when Greg asked her out at the beginning of her sophomore year, she was on cloud nine. I've seen pictures of Greg and, while he wasn't Tom Cruise, he was pretty hot.

"And to be honest, he wasn't the kind of guy who'd date a girl as Helen big as was. Helen was still a virgin when they had sex for the first time. Greg, as it turned out, had lots of experience.

"They were fucking every day and, while it often seemed that Greg was just using her as a human masturbation aid, she was certain they were in love—that is, until she overheard him talking to a friend. Seems he was bragging about using the 'fat bitch' for fun until he got tired of her.

"Helen was crushed. She refused to talk to him after that and, true to his character, he never tried very hard to get in touch with her. After one or two feeble attempts he never talked to her again. Helen really began to put on weight after that."

Karen paused for a moment and her eyes began to water. Then she continued, not focusing on me but presumably seeing things play out in her mind.

"After she graduated and began focusing on herself, she buckled down, lost the weight, and quit feeling sorry for herself. However, in other areas, she needs a confidence booster.

She looked back in my eyes, staring intensely at me. I could tell this was important to her; that Helen was important to her. I could tell that she was very protective of Helen.

"Here's the deal. She isn't completely sold on this, but I convinced her this was as close as she's going to get to having sex with someone she can really trust but is also someone she's not in a relationship with. She says she trusts you, and frankly, she's been staring at your cock all evening. She needs to get over this wall, and I think having some no strings attached sex is just the way to give her the boost she needs.

"Okay...if she decides that she's going through with this, she'll come out of her bedroom wearing the only piece of lingerie she owns—a purple, silk, baby doll. If she's wearing anything else, she's decided against it."

"Okay. I really do want to help her, especially with something this important," I said.

"And honestly," I said with a stupid smile splitting my face," I wouldn't turn down getting laid again."

Karen smiled back at me, "So incorrigible, it must be nice being twenty." She reached down and squeezed my cock.

Karen got up to leave. She was halfway out of the door when she hesitated, then turned around and looked at me.

"Did you say you have six or seven weeks until you move away to college?"

"Yep, about that much," I replied.

"Well, you appear to be mature and not likely to get overly attached so, if you're interested, I think we could have some fun before you leave."

"I think you're right on all counts. Just let me know the next time you need some...help!" I said, laughing. "You know where I work."

She smiled and slammed the door as she walked out.

That must have been the signal. The door to Helen's bedroom slowly opened. There was no light behind her, only the dim lamp in the living room illuminating her. I held my breath, waiting to see what she was wearing. Honestly, I wanted to fuck her pretty badly, regardless of the reason.

She came into the living room wearing her negligee. It came to the top of her thighs. Her nipples tented the silky material and it clung to her belly.

"Sam, you don't have to do this," were the first words out of her mouth.

"Helen, I want to, really, " I said, trying not to sound eager. You know, trying not to sound like a hormone filled asshole, thinking with his cock instead of his emotions. I might even have been somewhat successful. My cock pushed insistently at my shorts.

Helen looked down at my crotch, took a deep a breath and said, "Okay. I want you to go into the room first I'm going to be out here for a minute. Don't turn on any lights and just lie down on the bed. I'll be in...in a moment."

"I can do that." I turned around to walk into her bathroom.

"And, Sam," she said, "I want you to realize that...

"...this isn't a relationship," I said, finishing her thought. "Everything is going to be okay, Helen This in one friend helping another, just in a slightly unusual way."

She smiled and looked relieved. I went into the bedroom, closing the door. I carefully found my way to the bed.

This whole situation seemed so odd, but it'd been an odd and exciting evening. I went over to her bed and laid down. Should I take off my clothes? I decided that would probably be okay since we were about to have sex. I stripped my shorts and t-shirt off, aimed for a corner and threw them.

I was laid on Helen's bed, waiting with anticipation. My cock was as hard as a rock. It laid on my belly like a lead weight, arrowing in the direction of my head.

The door opened and closed, a brief flash of lamp light revealing Helen's silhouette. I felt the side of the bed settle with a creak as Helen sat down. I could smell tequila— probably the reason she had lingered in the living room. She put a hand on me, trailing her finger back forth a couple of times from my chest to my cock, her fingernails scraping my skin, making me shiver. Her hand finally stopped, coming to rest on my cock. I involuntarily groaned and thrust my hips up into the air.

I felt the bed shift again as she laid down and scooted close to me. Then I felt the hem of her nightie brush my thighs as she climbed on top of me and sat on my legs. I could feel her pubic hair brushing my balls.

As apprehensive as she might've seemed, she did seem to be turned on. She rubbed her slick pussy lips back and forth over the pole laying on my belly. She raised herself up on her knees and hovered over my cock.

She grasped it in her hand and I could feel her guiding it between her pussy lips. I was feeling the delicious grip of a pussy for the second time that night. She moved downward until her pussy enveloped my entire cock. We both sighed. If I hadn't already cum twice in the last three hours, I think I would have filled her pussy at that very moment.

The darkness clung to us. There there wasn't enough light for me to make out anything. I felt her hands on my chest. Her weight shifted and she leaned forward. She began moving up and down, sliding a little farther up my cock each time she pushed up.

I could feel my cock stretching her pussy lips with each stroke. I placed my hands on her thighs and then moved them upward until they were under her nightie and gripping her hips.

Helen began speaking in a breathy voice, "Oh, god. This feels so good. Fuck, I needed this."

It was almost as if she'd forgotten I was there.

I took my hands out from under her nightie and slid them up the silky material until I reached her big, beautiful breasts. I felt her nipples bumping up the material. She stopped moving.

"Sam, I don't know if I'm ready for that."

I wanted to respect her wishes, but decided to take a risk. I began circling her nipples with my thumbs.

"Oh, Sam, don't..."

Her voice trailed off as she let out a small moan. I could tell that her resistance was crumbling. Deciding to push things further, I grasped the spaghetti straps of her nightie and pulled them down over her shoulders. I could feel her moving her arms to take the straps off, and then the material of the nightie slid down to her hips. This time, I grabbed her naked breasts, hefting them with my hands, getting a feel for their ponderous weight. I began softly squeezing them. She resumed sliding up and down my cock.

Breathing loudly, she said, "Oh, Sam! Oh, god! Suck on my nipples!"

"I will, Helen, but I want one thing," I said.

"What?" she said hesitantly.

"I want to see you while you're fucking me. I want to see your beautiful breasts swinging over me. I want to see your nipples grazing my chest. I want to see my cock stretching your lips every time you pull up... and most of all...I want to see your face when you cum"

The silence was palpable. Finally, one word, "Okay."

I could feel her leaning over toward the nightstand. The light came on and she moved back over me, her breasts resting on my chest. Our faces were so close. I lifted my head up and kissed her. She sat up.

"Raise your arms," I said.

I grabbed the negligee that had pooled around her hips and pulled it up and over her head. I was finally seeing Helen completely naked for the first time and I wasn't disappointed. Intense concentration gripped her face as she placed her arms on my chest and started savagely fucking me. Our pelvises slammed together with each downstroke.