Eve Helps Out

NOTE: This is a work of fiction. It contains sex between older women and of age teen boys, as well as lesbian sex. If these subject matters offend you, please stop reading now.

"So, what do you think?" Asked Sharon, my long time friend.

"I think you're crazy. I mean, how could you even ask?" I replied.

"Come on Eve, at least think about it."

Sharon and I became friends the day she started working where I worked. We had lunch that first day and sealed our friendship. Our lives were similar. Both married, both with two children, and both marriages struggling. Few years later I divorced my husband after catching him with an intern at his company. Shortly after, Sharons husband was always coming around to see if I needed anything. At first I thought he was just being nice, but it quickly became obvious, he just wanted to score with the new divorcee. I never told Sharon at the time. I didn't want to be part of their problem.

At 54, I've had a couple flings since the divorce, nothing serious. I guess part of the reason I've stayed off the market is my weight. I kind of let myself go when I was married and never bothered trying to get back to my old sexy self. I was fine with a couple extra pounds. Not really fat, but well past my model figure days. What the hell, I'm past my prime, if men can't handle a fuller figured woman, I don't need them. Since I hate the bar scene, that also limits the opportunity to find companionship. I tried a few of the dating sites, nothing but meat markets. They were just like the bar scene, but without the alcohol.

Sharons marriage dissolved a shortly after mine. She did a much better job of losing the married weight and happily jumped back into the dating scene. I'll give her credit, she tried several times to get me to join her on double dates. Where she is outgoing and carefree, I'm introverted and much more reserved. I really think the only thing that holds her back from really enjoying single life is her youngest son, Ben. He is still at home and shows no interest in moving out. This limits Sharon from bringing the guys home and her overnight stays.

Sharon and I try to get together once a week for girl time and a gab session. Tonight we are sitting nude in the hot tub at my house. We have long since lost the pretense of modesty around one another during these visits. Having an empty nest and a private yard, afforded us the ability to swim and sun ourselves in the nude.

Spending time together in the nude and drinking, has on more than one occasion led to more between us. Sharon was always the more outgoing between the two of us. It was a warm evening like tonight when she kissed me out of the blue. What started as a little friendly peck, led to a night of wild girl on girl sex. Something we repeated often since then.

"Okay Sharon, I'll think about it. Another glass of wine?" I offered, as I poured us both another.

"Thanks Eve. You would be perfect for this. You would really be helping us out. I know it sounds insane, but when you think about it, you'll see it's perfect."

"Yeah I agree, it's insane. Here is my best friend, drinking wine naked in my hot tub on a Friday evening. What does she blurt out? She wants me to seduce her youngest son and spend a night or two fucking him. Honestly Sharon, I don't even know how to wrap my head around it." I said as I sat next to my friend.

"Eve, You're the only one I know and trust. Ben is a good boy, but horribly shy. He's only had one girlfriend that I know of, and their relationship was so brief. All he does is go to work, come home and play video games all night. He has no confidence when it comes to girls, and gaming wont help that. You would be perfect to help him out. Teach him that women are more fun than a night of video games. Maybe I am crazy, but I don't know what else to do."

"Ever think, maybe it's not girls he's into?" I asked.

"Not with his porn stash I found. And for a healthy young man without allergies, he does go through a lot of tissues. No Eve, he's straight. He just needs a helpful push and you would be perfect. Actually it might be good for both of you, since you rarely date." She said as she dropped her free hand and caressed my leg under the bubbling water.

"Yeah, because that's what every woman wants, a weekend in bed with someone inexperienced."

"Inexperienced, yes. But you do remember what nineteen year old guys were like. They are ready to fuck again ten minutes after they cum. Besides, having a young guy banging away sure does wonders for our older egos."

"You're telling me you've had a teenager since being divorced?" I asked, now with my hand also caressing her smooth leg under water.

"Two actually. The first time, Ben was at his fathers for the weekend. I was having some work done around the house. Anyway, the apprentice was cute, I was horny and flirty. After the work was done, and the boss left, well that evening I enjoyed my first teenager since high school."

"Do tell." I said as my fingers were now on her inner thighs.

"Well Josh, the apprentice, actually left with his boss. But he came back a little while later, telling me he thought he left his tape measure in the bathroom. He did, but I think it was on purpose. Anyway he started to chat me up a bit, sure did make this old girl feel good. I don't even recall the lines he was trying to feed me, not that it mattered much. The lines were bad, but I was horny. Before long, Josh was getting more and more bold with his innuendos." Sharon said then she closed her eyes as my fingers now teased her clit.

"And? What happened next?"

"Mmmmm. Eve. That's nice. Don't stop Eve."

I instantly pulled my hand back. "No more. Not unless you tell me about this hot encounter with Josh the handyman."

"Handyman apprentice. Okay, I'll tell but you get your finger back on my button. Well Josh was big on the innuendos, but not making a move. So, I stepped close and kissed this teen boy. Soon I had my tongue in his mouth. He followed my lead, but never pushed further. I was groping his ass before he grabbed mine. Ohh Eve, it was nice to hold and squeeze his hard teen ass as we French kissed."

"Did he kiss you like this?" I said as I maneuvered myself into her lap and kissed her hard. Our tongues intertwining and dancing.

Sharon kissed like no other. Her lips are soft and smooth, always wet. Once you got Sharon kissing, she was yours to have.

"Ohh Fuck Eve, forget Josh, lets go to the bedroom." Sharon said as she kissed and fondled my tits.

"We have all night baby, I want to hear how you corrupted this young boy. Besides I might need ideas if I decide to seduce your son." I remarked as I got off of her lap.

"Ugh. You're bad Eve. Naughty tease. I knew if anything was going to happen, I had to lead. I asked him how often he puts the moves on clients. Josh confessed, in fantasies, a lot, but I was the first in real life. I dropped to my knees right there in the kitchen as pulled his cock out. I'll tell you Eve, for a teen, he had a nice cock, bigger and thicker than Mikes (her ex-husband). I only planned to suck on him for a few minutes then take him to the sofa. However before I could get us to the sofa, his cock exploded in my mouth with a huge load. I swallowed as fast and as much as I could, but some still wound up dribbling to my chest.

Eve, I'm getting heated in the hot water, hot story and your dancing fingers." Sharon said as she moved to the side of the tub to cool off in the evening air.

"Keep going Sharon. Did you get to fuck him?"

"Oh yes! When he finally stopped pumping cum in my mouth, I led him to the sofa, and told him to wait. I returned with a wash cloth and a towel. I told him he got his cum all over my tits, he had to clean them off. I laughed when he tried to dab the cum off my tits. I told him, ' You know Josh, that will probably be easier if you were to undress me.' He was very nervous, taking my blouse and bra off. For me, it was really exciting having him undress me." Sharon continued as she lazily fingered herself now. Under the water I had my fingers on my clit. Above the water, I was now kissing and licking her thighs.

"When he was done he said something like, 'I think I got it all off.' I told him he should taste and make sure. He was hesitant, until I guided his lips to my very hard nipples. That's all it took, his hands were grabbing and squeezing my tits as his mouth went from nipple to nipple. Josh was in MILF tit heaven. I let him enjoy my tits for a little while, then had him stand up so I could undress him. Let me tell you Eve, I felt like a dirty old cougar standing there topless undressing this teen boy. Ohh Fuck!"

Sharon had a small orgasm on her fingers. She clamped her legs closed trapping her own hand. I'm sure she had at least one finger deep in her pussy when she came. The story and the sight caused my orgasm to hit me.

"You dirty bitch, Ohh Fuck Sharon. Your a dirty slut." I said as I rode my long fingers to my own orgasm.

She recovered first, grabbing a handful of my hair, she pulled and encouraged me out of the hot water.

"I'll finish the story, in your bed Eve." Sharon said as she pulled me by my hair to my bedroom. Once there she pushed my back onto the bed. I was still dripping wet from the tub, but didn't care.

"Where was I? Oh yeah, I pulled his pants and underwear off him. His cock was hard and ready again. I swear it couldn't have been ten minutes since he came. Didn't matter, here was his cock in all its raging glory. I finally told him, 'You know Josh, this will be a lot more fun if I was wearing less too.' His nervous hands unbuttoned and unzipped my pants. I swayed my hips sensually to help him pull my pants down. Then came the panties, young nervous hands again, I even swayed my hips to help, even though it wasn't necessary for the panties. Finally we were standing there together naked. I laid back on the sofa, one leg over the back of the sofa the other on the floor. Josh moved between my legs as he was ready to sink his cock into me. I stopped him, 'don't you want to taste first?' He looked at me almost confused. 'You know honey, eat my pussy before you fuck me.'

That sounded like a wonderful idea to me, as I got between Sharon's legs. I started by lightly kissing her thighs, I didn't want to distract her from the story too much.

"Ohh that's nice Eve. I had to teach the boy how to properly eat a woman's pussy. He was eager, and only experimented with his girlfriend a couple time. After he ate me to a couple orgasms, I let him climb up and fuck me. Let me tell you Eve, what that boy lacked in technique, he made up for in power. He really slammed my pussy hard. Again, he didn't last long before he pumped a load into my pussy. When he calmed back down, we kissed for a while. After he finally got off me, I leaned over to suck his semi hard cock clean. I swear he never went soft. Try as I did, I could not get him to lick my pussy again after he fucked me. When he was fully hard, I had him fuck me doggy style. Took him a little longer to cum the third time, but still not too long."

"Sounds like you had a energetic afternoon with that young man." I said before moving my lips to her pussy.

"Mmmm, it sure was. I laid there nude and freshly fucked as he dressed. I kissed him goodbye at the door, still nude. Then I grabbed Charlie (the name she gave her big black dildo) and went out to the patio. I chuckled thinking how much Josh would probably have enjoyed seeing that show."

With my fingers joining my tongue on her pussy, Sharon lost the ability to continue talking about her adventure.

"Ohhh Fuck Eve. Don't stop, make my pussy cum Honey. Right there lick me, Ohhh Fuck Yessss!"

I spun around so Sharon could join in and bring my pussy some pleasure. She was quick to lick my pussy lips. We were soon grinding our pussys in each other's face. Sharon rolled us over so she was on top of me now. After Sharon came on my lips and tongue, she reached for Marvelous Mel (my favorite vibrating dildo). Sharon started to run the tip of Mel around my clit.

"Mmmmm. Yeah use Mel on me Baby. I'm ready."

Sharon just teased me, I felt the tip of Mel, then she would stop stimulating me, before flicking my clit with her tongue. She was driving me crazy with my building lust. I was so close and ready.

"Come on Sharon, let me cum baby. I want to fucking cum for you."

"Maybe in a minute Eve. First I want you to agree to an evening of sex with Kenny. Please Honey he needs this pussy of yours to help him. Just say you'll help guide my son into manhood, and I'll make you cum so good."

I would have reached down and fingered myself, but she was on top and had me pinned. My brain was in a fog of lust. Cumming was my only thought. Sharon keep toying with me, just enough to make me ride the edge of the climax I so desperately needed.

"Fucking tease. Let me cum then we'll talk about it more"

"It's not that easy Eve. I'll make you cum so hard and so good, but first you need to promise to get my son to fuck you. You want to be fucked, don't you? I'm ready to push Mel deep into you and clamp my lips on your clit till you quiver so hard. You need to cum Eve, and Kenny needs to be fucked. You get to cum, you get to fuck a teen boy and you get your own cougar story. What do you say Eve? Ready to cum? Ready to become a cougar with my son?"

"Ahh. Fuck. Anything. Fuck. Just make me cum."

"You agree to bedding my boy? You'll help Kenny?"

"Yes. Damn it YES!"

That's all Sharon needed to hear. Good to her word, she locked her lips over my clit and sucked on the throbbing bud. Slowly pushing Mel deep into my pussy. When she pushed the button making the vibrator come to life, I completely lost control of everything. I came so hard and screamed out with my orgasm. I must have blacked out when I regained some of senses, Sharon was over me rubbing her pussy back and forth on mine. Sharon was holding my leg as she scissored me. I grabbed her ass and guided her motions till we both came again. Pussy to pussy, clit to clit, wet and dripping girl sex. So much different than a hard cock, but just as incredible.

That is how the next hour went. Just two horny middle age women pleasuring one another.

******* Sitting back on the patio *******

"You do know that was blackmail. Holding me on the edge, not giving me any release until I agreed to your crazy plan." I told Sharon.

"I know. So what? You got to cum, and now you have to pay up."

"So how do we pull this off?" I asked.

Over the next bottle of wine, Sharon and I plotted, laughed and plotted some more. In the end, drunk and horny, I agreed to the crazy plan. Sharon gave me a soft kiss on my lips to 'seal the deal'. Next Friday was the agreed upon day. Sharon would set everything up on her end. I was to just show up for our weekly girls night at her place.

All week I thought up reasons and ways to cancel. The thoughts of sex with a young man, always made me horny and removed the thoughts of canceling.

******* The Night Arrives *******

While I was getting ready to head across town to visit and eventually seduces my best friends son, Sharon was putting the plan into action.

******* At Sharon and Bens House *******

"Come on Benny, help me out. I never asked for anything like this, I really need your help." Sharon said.

"But mom she's your friend, I don't see why you just don't call and cancel." Ben replied.

"Please, Mrs. Hill doesn't get out much. She really enjoys our visits. I made the dinner and everything is set. Getting called away on business wasn't my idea. Just have dinner with her and make some small talk. It'll be over in a couple hours and then you have the weekend to yourself. Be a good sport and do this for me please."

"Okay, but only dinner and a couple hours." Ben finally said.

******* The Time Is Now *******

Sharon opened the door as soon as I rang the bell. I noticed Ben sitting in the living room, looking a bit grumpy.

"I'm here, with wine and a swimsuit for the hot tub later." I said kissing Sharon on the cheek.

"I'm so sorry Eve, but there has been a change of plans. I have to go out of town on business tonight. But please stay and join Ben for dinner at least. I cooked a pot roast, which will go great with that wine. Have dinner with Ben and keep him company for a little bit. I promised him no more than a couple hours." Sharon said laying the groundwork.

"When do you have to leave?"

"Now actually. I'm so sorry, I'll make it up next week." And with that Sharon kissed my cheek again, kissed her son and walked out with an overnight bag.

"Are you okay with this Ben?" I asked.

"Sure." He really wasn't okay at all with it, but his mom gave him very stern warnings. He was told in no uncertain terms to make Mrs. Hill feel at home and be sure she enjoys herself.

Talk through dinner was strained. Ben was not very comfortable with small talk. So I carried much of the conversation. I excused myself to get more wine. Returning from the kitchen after refilling my wine glass, I brought a glass for him.

"Mrs. Hill, I'm still underage. I shouldn't have this."

"I'm not going to tell, besides, you seem like you could use some loosening up. A young man like you, starting the weekend, should relax. Please have it for me."

After dinner, I helped to clear the table. I poured more wine for myself and asked, "What would you like to do now?"

"Well, you mentioned the hot tub. Let me get my trunks on and we can chat there some if you'd like" Ben responded.

"Great I'll change and join you." I replied.

Ben was in the water by the time I finished getting my one piece on. Looking in the mirror, I really didn't look that bad for my age. My tit's were not sagging too terrible for my age, and while the few extra pounds showed, I'm still sexy. My legs have always been a great male attention grabber.

I stopped by the kitchen to grab another glass of wine and actually poured the rest of the bottle down the drain to make it look like we drank more than we actually did. Part of the plan was to appear to be to drunk to drive home. I opened a second bottle and poured another drink for both of us.

Before the evening would be over, we would have drank a bottle and a half, with Ben having two glasses.

I appreciate Bens stares on my legs and ass as I lowered myself into the tub.

"Thank you for spending your evening with one of your moms friends Ben. I know you would rather be out picking up girls your own age."

"I don't mind Mrs. Hill. I didn't really have any plans for tonight anyway."

"No plans, that's silly. I remember being your age. Friday and Saturday's were for dating. Those dates always wound up being very sexy. Always kissing and groping in the boys car. Sometimes more, sometimes a lot more. You know." I said.

"I don't date much."

"That's crazy Ben. You're a good looking young man with the house to himself this weekend. You should be sitting here with a cute you girl, giving her some wine, kissing on her neck. Your yard is pretty private like mine. You could peel away her bikini top and play with her young tit's. Bet she would be groping you while you did."

"Yeah like I said, I don't date much."

"I don't know why, like I said you're nice and all. Stand up, let me see your body."

"I don't think so, Mrs Hill."

"Call me Eve, and I insist. I want to know why the girls aren't all over you."

Ben stood up as I demanded. It was clear our evil plan was working by the sight of his hard cock in his trunks. When he noticed my eyes on his crotch, he sank back in the water.

"Sorry Ben. I didn't mean to embarrass you. Drinking always gets me a bit more amorous. I really didn't mean to stare, but DAMN. You shouldn't be entertaining this old broad, you should be holding some young slut, getting her hot and horny."